Title of Invention

"SUBSTITUTED SULFONYLAMINO(THIO)CARBONYL COMPOUNDS"

Abstract The present invention relates to sulphonylamino(thio)carbonyl compounds of the general formula (I): in which n, A, Q and R1 to R3 are as described in the specification.
Full Text Substituted sulfonylamino(thio)carbonyl compounds
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.
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.
This invention, then, provides the novel sulfonylamino(thio)carbonyl compounds of the general formula (1)
(Figure Remove) 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,
R1 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,
R2 represents cyano or halogen or represents respectively optionally substituted

alkyl, alkoxy, alkylthio, alkylsulfinyl, alkenyl, alkinyl, alkenyloxy or alkinyloxy

alkylsulfonyl, dialkylaminosulfonyl, and

3 represents respectively optionally subsiituted heterocyclyl having 5 ring

, sulfur or nitrogen and from one to
members of which at least one is oxygen
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)
(Figure Remove)
n, A, R1 and R' are each as defined above
with (thio)carboxylic acid derivatives of the general formula (III) (Figure Remove)

which
Q and R3 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)
(Figure Remove)n, A, Q, R1 and R2 are each as defined above
with heterocycles of the general formula (V)
H-R3 (V) in which
R3 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)

(Figure Remove)
n, A, R1 and R2 are each as defined above
with heterocycles of the general formula (V)
H-R3 (V)
in which R3 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) (Figure Remove)
which
Q and R3 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)
(Figure Remove)
Z represents halogen, alkoxy, aryloxy or arylalkoxy,
with heterocycles of the general formula .(V)
H-R3 (V)
in which
R3 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-R3 (V)
in which
R3 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)
(Figure Remove)in which
n, A, R1 and R2 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,-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl or C3-C6-cycloalkyl,
Q represents oxygen or sulfur,
R1 represents hydrogen or formyl or represents respectively optionally cyano-, fluoro-, chloro-, bromo-, phenyl- or C,-C4-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,-C4-alkyl-substituted C3-C6-cycloalkyl, C3-C5-cycloalkyl-carbonyl or C3-C6-cycloalkyl-sulfonyl,
R2 represents cyano, fluoro, chloro or bromo or represents respectively optionally cyano-, fluoro-, chloro-, bromo- or C,-C4-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, dialkylaminosulfonyl, alkenyl, alkinyl,
alkenyloxy or alkinyloxy having in each case up to 6 carbon atoms, and
R3 represents respectively optionally substituted heterocyclyl of the formulae below,

(Figure Remove)Q1, Q2 and Q3 each represent oxygen or sulfur, and
R4 represents hydrogen, hydroxyl, amino or cyano, or represents C2-C10-alkylideneamino, or represents optionally fluoro-, chloro-, bromo-, cyano-, C,-C4-alkoxy-, C,-C4-alkyl-carbonyl- or C,-C4-alkoxy-carbonyl-substituted C,-C6-alkyl, or represents respectively optionally fluoro-, chloro- and/or bromo-substituted C2-C6-alkenyl or C2-C6-alkinyl, or represents respectively optionally fluoro-, chloro-, bromo-, cyano-, C,-C4-alkoxy- or C,-C4-alkoxy-carbonyl-substituted C,-C6-alkoxy, C,-C6-alkylamino or C,-C6-alkyl-carbonylammo, or represents C3-C6-alkenyloxy, or represents di-(C,-C4-alkyl)-amino, or represents respectively optionally fluoro-, chloro-, bromo-, cyano- and/or C,-C4-alkyl-substituted C3-C6-cycloalkyl, C3-C6-cycloalkylamino or C3-C6-cycloalkyl-C,-C4-alkyl, or represents respectively optionally fluoro-, chloro-, bromo-, cyano-, nitro-, C,-C4-alkyl-, trifluoromethyl- and/or C,-C4-alkoxy-substituted phenyl or phenyl-C,-C4-alkyl,
R5 represents hydrogen, hydroxyl, mercapto, amino, cyano, fluoro, chloro, bromo or iodo, or represents optionally fluoro-, chloro-, bromo-, cyano-, C,-C4-alkoxy-, C,-C4-alkyl-carbonyl- or C,-C4-alkoxy-carbonyl-substituted C,-C6-alkyl, or represents respectively optionally fluoro-, chloro- and/or bromo-substituted C2-

C6-alkenyl or C2-C6-alkinyl, or represents respectively optionally fluoro-, chloro-, cyano-, C,-C4-alkoxy- or C,-C4-alkoxy-carbonyl-substituted C,-C5-alkoxy, C,-C6-alkylthio, C,-C6-alkylamino or C,-C6-alkylcarbonylamino, or represents C3-C6-alkenyloxy, C3-C6-alkinyloxy, C3-C6-alkenylthio, C3-C6-alkinylthio, C3-C6-alkenylamino or C3-C6-alkinylamino, or represents di-(C,-C4-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,-C4-alkyl-substituted C3-C6-cycloalkyl, C5-C6-cycloalkenyl, C3-C6-cycloalkyloxy, C3-C6-cycloalkylthio, C3-C6-cycloalkylamino, C3-C6-cycloalkyl-C,-C4-alkyl, C3-C6-cycloalkyl-C,-C4-alkoxy, C3-C6-cycloalkyl-C,-C4-alkylthio or C3-C6-cycloalkyl-C,-C4-alkylamino, or represents respectively optionally fluoro-, chloro-, bromo-, cyano-, nitro-, C,-C4-alkyl-, trifluoromethyl-, C,-C4-alkoxy- and/or C,-C4-alkoxy-carbonyl-substituted phenyl, phenyl-C,-C4-alkyl, phenoxy, phenyl-C,-C4-alkoxy, phenylthio, phenyl-C,-C4-alkylthio, phenylamino or phenyl-C,-C4-alkylamino, or
R4 and R5 together represent optionally branched alkanediyl having 3 to 11 carbon atoms, and
R6, R7 and R8 are identical or different and each represent hydrogen, cyano, fluoro, chloro, bromo, or represent respectively optionally fluoro-, chloro-, bromo- or C,-C4-alkoxy-substituted alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio, alkenylthio, alkinylthio, alkylsulfinyl or alkylsulfonyl having in each case up to 6 carbon atoms, or represent optionally cyano-, fluoro-, chloro-, bromo- or C,-C4-alkyl-substituted cycloalkyl having 3 to 6 carbon atoms.
The invention further preferably provides the sodium, potassium, magnesium, calcium, ammonium, CYC4-alkyl-ammonium, di-(C,-C4-alkyl)-ammonium, tri-(C,-C4-alkyl)-ammonium, tetra-(C1-C4-alkyl)-ammonium, tri-(C,-C4-alkyl)-sulfonium, C5- or C6-cycloalkyl-ammonium and di-(C,-C2-alkyl)-benzyl-ammonium salts of compounds of the formula (I) in which n, A, Q, R1, R2 and R3 each have the meanings indicated above as preferred.

The invention relates in particular to compounds of the formula (I) in which
n represents the numbers 0, 1 or 2,
A represents a single bond, or oxygen or the grouping N-R, in which R represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, propenyl, butenyl, propinyl, butinyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl,
Q represents oxygen or sulfur,
R1 represents hydrogen or formyl, or represents respectively optionally fluoro-, chloro-, bromo-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, methoxyamino, ethoxyamino, n- or i-propoxyamino, n-, i-, s- or t-butoxyamino, dimethylamino, diethylamino, N-methoxy-N-methyl-amino, acetyl, propionyl, butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, n-, i-, s- or t-butylsulfonyl, propenyl, butenyl, propinyl or butinyl, or represents respectively optionally fluoro-, chloro- or methyl-substituted cyclopropyl, cyclopropylcarbonyl or cyclopropylsulfonyl,
R2 represents cyano, fluoro, chloro or bromo, or represents respectively optionally fluoro-, chloro-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i- or s-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, dimethylaminosulfonyl or diethylaminosulfonyl, or represents propenyl, butenyl, propinyl, butinyl, propenyl oxy, butenyloxy, propinyloxy or butinyloxy, and
R3 represents respectively optionally substituted heterocyclyl of the formulae
below:

(Figure Remove)
Q1, Q2 and Q' each represent oxygen or sulfur, and
R4 represents hydrogen, hydroxyl or amino, or represents C3-C8-alkylideneamino, or represents respectively optionally fluoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or represents respectively optionally fluoro-, chloro- or bromo-substituted propenyl, butenyl, propinyl or butinyl, or represents respectively optionally fluoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, or represents propenyloxy or butenyloxy, or represents dimethylamino or diethylamino, or represents respectively optionally fluoro-, chloro-, methyl- and/or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or represents respectively optionally fluoro-, chloro-, methyl-, trifluoromethyl- and/or methoxy-substituted phenyl or benzyl,
R3 represents hydrogen, hydroxyl, mercapto, amino, fluoro, chloro or bromo, or represents respectively optionally fluoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or represents respectively optionally fluoro-, chloro- or bromo-substituted ethenyl, propenyl, butenyl, propinyl or butinyl, or represents respectively optionally fluoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s-or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-
butylamino, or represents propenyloxy, butenyloxy, propinyloxy, butinyloxy, propenylthio, propadienylthio, butenylthio, propinylthio, butinylthio, propenylamino, butenylamino, propinylamino or butinylamino, or represents dimethylamino, diethylamino or dipropylamino, or represents respectively optionally fluoro-, chloro-, methyl- and/or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopropylmethylthio, cyclobutylmethylthio, cyclopentylmethylthio, cyclohexylmethylthio, cyclopropylmethylamino, cyclobutylmethylamino, cyclopentylmethylamino or cyclohexylmethylamino, or represents respectively optionally fluoro-, chloro-, methyl-, trifluoromethyl-, methoxy- and/or methoxycarbonyl-substituted phenyl, benzyl, phenoxy, benzyloxy, phenylthio, benzylthio, phenylamino or benzylamino, or
I4 and R5 together represent optionally branched alkanediyl having 3 to 11 carbon atoms, furthermore
I6, R7 and R8 are identical or different and each represent hydrogen, cyano, fluoro, chloro or bromo, or represent respectively optionally fluoro-, chloro-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, propenyl, butenyl, propinyl, butinyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, propenyloxy, butenyloxy, propinyloy, butinyloxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, propenylthio, butenylthio, propinylthio, butinylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, or represent cyclopropyl.
A very particularly preferred group of compounds according to the invention are those

compounds of the formula (I) in which
n represents the numbers 0, 1 or 2, A represents a single bond, Q represents oxygen or sulfur,
R' represents respectively optionally fluoro- and/or chloro-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,
R2 represents fluoro, chloro or bromo, or represents respectively optionally fluoro-, and/or chloro-substituted methyl, ethyl, methoxy, ethoxy, methylthio or ethylthio - in each case in position 6 -, and
R3 represents optionally substituted triazolinyl of the formula below,
(Figure Remove)
Q' represents oxygen or sulfur, and
R4 represents respectively optionally fluoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, or represents propenyl or propinyl, or represents methoxy, ethoxy, n- or i-propoxy, or represents cyclopropyl, and
R5 represents hydrogen, chloro or bromo, or represents respectively optionally fluoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-

propyl, or represents respectively optionally fluoro- and/or chloro-substituted propenyl or propinyl, or represents respectively optionally fluoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, or represents propenyloxy or cyclopropyl.
The radical definitions listed above, whether general or listed in ranges of preference, apply not only to the end products of the formula (I) but also, correspondingly, to the starting materials and/or intermediates required in each case for the preparation. These radical definitions can be combined as desired with one another, thus including combinations between the preferred ranges indicated.
Using, for example, 2-fluoro-6-memylthio-benzenesulfonamide and 5-ethoxy-4-methyl-2-phenoxycarbonyl-2,4-dihydro-3H-l,2,4-triazole-3-thione as starting materials, the course of reaction in the process (a) according to the invention can be illustrated by the following equation:
(Figure Remove)
Using, for example, 2-ethylthio-6-methyl-phenylsulfonyl isothiocyanate and 5-ethyl-4-methoxy-2,4-dihydro-3H-l,2,4-triazol-3-one as starting materials, the course of reaction in the process (b) according to the invention can be illustrated by the following equation:
- 16-


SO2-N=C=S
CH3

SC2H5

N:

,SC2H5

Using, for example, 2-methylthio-3-methyl-benzenesulfonyl chloride, 5-ethyl-thio-4-methoxy-2,4-dihydro-3H-l,2,4-triazol-3-one and potassium cyanate as starting materials, the course of reaction in the process (c) according to the invention can be illustrated by the following equation:



SCH,
,SCH
N:
SO2CI

0
N:

SC2H5

KOCN

CH,

SC2H5

Using, for example, 2-ethylthio-4-fluoro-benzenesulfonyl chloride and 5-methyl-l,2,4-oxadiazole-3-carboxamide as starting materials, the course of reaction in the process (d) according to the invention can be illustrated by the following equation:



-SC2H5
SC2H5
H2N
-HCI
S02CI

O

N:

CH,

Using, for example, N-(2-chloro-6-propylthio-phenylsulfonyl)-O-methylurethane and 4-methyl-5-methylthio-2,4-dihydro-3H-l,2,4-triazol-3-one as starting materials, the course of reaction in the process (e) according to the invention can be illustrated by the following equation:

- 17-


S02-NH-COOCH3
SC3H7

U
H-.kl/\,
N:

SCH,

- HOCH,

Cl

SC3H7
SO,

O
-NH
SCH,
Using, for example, 5-chloro-4-ethyl-2,4-dihydro-3H-l,2,4-triazol-3-one and chlorosulfonyl isocyanate and then 2-ethylthio-6-methyl-aniline as starting materials, the course of reaction in the process (f) according to the invention can be illustrated by the following equation:

u CI-SO,-N=C=O + H^N N--C2H5

O






SC2H5

N:

Cl

Cl

N:

Cl

A general definition of the aminosulfonyl compounds to be used as starting materials in the process (a) according to the invention for the preparation of compounds of the formula (I) is given by the formula (II). In the formula (II), n, A, R1 and R2 preferably or in particular have that meaning which has already been indicated above, in connection with the description of the compounds of the formula (I) according to the invention, as being preferable or, respectively, particularly preferable for n, A, R1 and R2.
With the exception of the compound 2,6-bis-methylthio-benzenesulfonamide (cf. EP 135332, US 4604131), the starting materials of the formula (II) have to date not been disclosed in the literature; with the exception of 2,6-bis-methylthio-benzenesulfonamide, they are novel substances and likewise form part of the subject matter of the present application.

- 18-
The novel aminosulfonyl compounds of the formula (II) in which n represents zero, A represents a single bond and R1 represents respectively optionally substituted alkyl, alkenyl, alkinyl or cycloalkyl are obtained when t-butylaminosulfonyl compounds of the general formula (XI)


(XI) -NHC(CH3)3

in which
A and R2 are each as defined above
are metallated - i.e. the hydrogen atom shown in the formula (XI) is replaced by a metal atom - with an organometallic compound, such as for example butyl lithium in hexane, if appropriate in the presence of a (further) inert diluent, such as for example tetrahydrofuran, and under an inert gas atmosphere, such as for example under argon, at temperatures between -50°C and +20°C, and then, in the same reaction medium, reacted with sulfur at temperatures between -30°C and +30°C - i.e. the metal atom is replaced by sulfur -, and then, in the same reaction medium, reacted with an alkylating agent of the general formula (XII)
X'-R1 (XII)
in which
R! represents respectively optionally substituted alkyl, alkenyl, alkinyl or cycloalkyl and
X' represents halogen, preferably chlorine, bromine or iodine
at temperatures between 0°C and 100°C, and the thus-obtained t-butylaminosulfonyl compounds of the general formula (XIII)

- 19-


(XIII) •NHC(CH3)3

in which
A, R1 and R2 are each as defined above
are then - preferably after intermediate isolation - reacted with a strong acid, such as for example trifluoroacetic acid, if appropriate in the presence of a diluent, such as for example methylene chloride, at temperatures between 0°C and 50°C (cf. the preparation examples).
The novel compounds of the formula (II) in which n represents zero, A represents a single bond and R1 represents H are obtained when the t-butylaminosulfonyl compounds of the general formula (XI) are, as described above, reacted with sulfur after metallation, and the product formed of the general formula (XIV)


,S02.
(XIV) A' '^NHC(CH3)3

in which
A and R2 are each as defined above
is then - if appropriate after intermediate isolation - reacted with a strong acid, such as for example trifluoroacetic acid, if appropriate in the presence of a diluent, such as for example methylene chloride, at temperatures between 0°C and 50°C, and the thus-obtained isomerization product of the general formula (XV)

-20-


-NH,

(XV)

in which
A and R2 are each as defined above
is - if appropriate after intermediate isolation - reacted with a Lewis acid, such as for example boron(III) bromide, in the presence of a diluent, such as for example methylene chloride, at temperatures between 0°C and 50°C (cf. the preparation examples).
The novel compounds of the formula (II) in which n represents zero, A represents a single bond and R1 represents hydrogen or respectively optionally substituted alkyl, alkenyl, alkinyl or cycloalkyl are obtained when the t-butylaminosulfonyl compounds of the general formula (XI) are, as described above, reacted with sulfur after metallation, and the products formed of the general formula (XIV) - above - are then -if appropriate after intermediate isolation - reacted with a suitable oxidizing agent, such as for example dimethyl sulfoxide, at temperatures between 20°C and 120°C, and the disulfides formed of the general formula (XVI)


R
-NHC(CH,),
-NHC(CH3)3

(XVI)

in which

-21 -
A and R2 are each as defined above
are then - if appropriate after intermediate isolation - reacted with a strong acid, such as for example trifluoroacetic acid, if appropriate in the presence of a diluent, such as for example methylene chloride, at temperatures between 0°C and 50°C, and the disulfides formed of the general formula (XVII)


R
(XVII)

in which
A and R2 are each as defined above
are then - if appropriate after intermediate isolation - reacted with a reducing agent, such as for example sodium tetrahydridoborate (sodium borohydride), if appropriate in the presence of a diluent, such as for example methanol, at temperatures between 0°C and 50°C, and the thus-obtained compounds of the formula (II) in which R1 represents hydrogen are then, if appropriate, reacted with an alkylating agent of the general formula (XII)
X'-R1 (XII)
in which
R1 represents respectively optionally substituted alkyl, alkenyl, alkinyl or cycloalkyl and
X1 represents halogen, preferably chlorine, bromine or iodine

-22-at temperatures between 0°C and 100°C (cf. the preparation examples).
The novel aminosulfonyl compounds of the formula (II) in which A represents a single bond, R1 represents respectively optionally substituted alkyl, alkenyl, alkinyl or cycloalkyl and R2 represents respectively optionally substituted alkyl, alkenyl or alkinyl - in position 6 - are obtained when t-butylaminosulfonyl compounds of the general formula (XVIII)

(XVIII) A' '^NHC(CH3)3

in which
A is as defined above
are metallated - i.e. the hydrogen atom shown in the formula (XVIII) is replaced by a metal atom - with a metalloorganic compound, such as for example butyllithium in hexane, if appropriate in the presence of a (further) inert diluent, such as for example tetrahydrofuran, and under an inert gas atmosphere, such as for example argon, at temperatures between -50°C and +20°C, and then, in the same reaction medium, reacted with sulfur - i.e. the metal atom is replaced by sulfur - at temperatures between -30°C and +30°C, and then, in the same reaction medium, reacted with an alkylating agent of the general formula (XII)
X'-R1 (XII)
in which
R1 represents respectively optionally substituted alkyl, alkenyl, alkinyl or cycloalkyl and
X1 represents halogen, preferably chlorine, bromine or iodine

-23 -
at temperatures between 0°C and 100°C and the thus-obtained t-butylaminosulfonyl compounds of the general formula (XIX)


3'3
A' 2^NHC(CHA

(XIX)

in which
A and R1 are each as defined above,
are then - preferably after intermediate isolation - metallated with an organometallic compound, such as for example butyllithium in hexane, if appropriate in the presence of a (further) inert diluent, such as for example tetrahydrofuran, and under an inert gas atmosphere, such as for example under argon, at temperatures between -50°C and +20°C and then, in the same reaction medium, reacted with an alkylating agent of the general formula (XX)
X2-R2 (XX)
in which
R2 represents respectively optionally substituted alkyl, alkenyl or alkinyl and
X2 represents halogen, preferably chloro, bromo or iodo
at temperatures between 0°C and 100°C (cf. the preparation examples).
The compounds of the formula (II) in which n represents zero can be converted in a conventional manner into the corresponding compounds of the formula (II) in which n represents 1 or 2 by reaction with suitable oxidizing agents, such as for example 3-chloro-perbenzoic acid (cf. the preparation examples).

-24-
Some of the n-butylaminosulfonyl compounds of the formula (XIII) - above - required as precursors can also be obtained by reacting suitable disulfides of the formula (XVI) -above - with suitable alkylating agents of the formula (XII) - above - in the presence of sodium hydroxymethanesulfmate dihydrate and in the presence of disodium hydrogen phosphate and in the presence of a diluent, such as for example N,N-dimethyl-formamide (cf. the preparation examples).
A general definition of the (thio)carboxylic acid derivatives also to be used as starting materials in the process (a) according to the invention for the preparation of compounds of the formula (I) is given by the formula (III). In the formula (III), Q and R3 preferably or in particular have that meaning which has already been indicated above, in connection with the description of the compounds of the formula (I) according to the invention, as being preferable or, respectively, particularly preferable for Q and R3; Z preferably represents fluoro, chloro, bromo, C,-C4-alkoxy, phenoxy or benzyloxy, and in particular chloro, methoxy, ethoxy or phenoxy.
The starting materials of the formula (III) are known and/or can be prepared by methods known per se (cf. EP 459244, EP 341489, EP 422469, EP 425948, EP 431291, EP 507171, EP 534266).
A general definition of the sulfonyl iso(thio)cyanates to be used as starting materials in the process (b) according to the invention for the preparation of the compounds of the formula (I) is given by the formula (IV). In the formula (IV), n, A, Q, R1 and R2 preferably or in particular have that meaning which has already been indicated above, in connection with the description of the compounds of the formula (I) according to the invention, as being preferable or particularly preferable for n, A, Q, R1 and R2.
With the exception of the compound 2,6-bis-methylthio-phenylsulfonyl isocyanate (cf. EP 135332), the starting materials of the formula (IV) have not to date been disclosed in the literature; with the exception of 2,6-bis-methylthio-phenylsulfonyl isocyanate, they are novel substances and likewise form part of the subject matter of the present application.

-25-
The novel sulfonyl iso(thio)cyanates of the formula (IV) are obtained when aminosulfonyl compounds of the general formula (II) - above - are reacted with phosgene or thiophosgene, if appropriate in the presence of an alkyl isocyanate, such as for example butyl isocyanate, if appropriate in the presence of a reaction auxiliary, such as for example diazabicyclo[2.2.2]octane, and in the presence of a diluent, such as for example toluene, xylene or chlorobenzene, at temperatures between 80°C and 150°C, and, after the reaction has ended, the volatile components are distilled off under reduced pressure.
A general definition of the heterocycles also to be used as starting materials in the processes (b), (c), (e) and (f) according to the invention for preparing the compounds of the formula (I) is given by the formula (V). In the formula (V), R3 preferably or in particular has that meaning which has already been indicated above, in connection with the description of the compounds of the formula (I) according to the invention, as being preferable or particularly preferable for R3.
The starting materials of the formula (V) are known and/or can be prepared by methods known per se (cf. EP 341489, EP 422469, EP 425948, EP 431291, EP 507171, EP 534266).
A general definition of the chlorosulfonyl compounds to be used as starting materials in the processes (c) and (d) according to the invention for preparing compounds of the formula (I) is given by the formula (VI). In the formula (VI), n, A, R1 and R2 preferably or in particular have that meaning which has already been indicated above, in connection with the description of the compounds of the formula (I) according to the invention, as being preferable or particularly preferable for n, A, R1 and R2.
The starting materials of the formula (VI) have not to date been disclosed in the literature; as novel substances they are likewise part of the subject matter of the present application.
The novel chlorosulfonyl compounds of the formula (VI) are obtained when the

-26-corresponding amino compounds of the general formula (XXI)


(XXI)

in which
n. A, R1 and R2 are as defined above
are reacted with an alkali metal nitrite, such as for example sodium nitrite, in the presence of hydrochloric acid at temperatures between -10°C and +10°C and the diazonium salt solution thus obtained is reacted with sulfur dioxide in the presence of a diluent, such as for example dichloromethane, 1,2-dichloro-ethane or acetic acid, and in the presence of a catalyst, such as for example copper(I) chloride and/or copper(II) chloride, at temperatures between -10°C and +50°C.
A general definition of the (thio)carboxamides to be used as starting materials in the process (d) according to the invention for the preparation of the compounds of the formula (I) is given by the formula (VIII). In the formula (VIII), Q and R3 preferably or in particular have that meaning which has already been indicated above, in connection with the description of the compounds of the formula (I) according to the invention, as being preferable or particularly preferable for Q and R3.
The starting materials of the formula (VIII) are known and/or can be prepared by methods known per se (cf. EP 459244).
A general definition of the sulfonylamino(thio)carbonyl compounds to be used as starting materials in the process (e) according to the invention for the preparation of the compounds of the formula (I) is given by the formula (IX). In the formula (IX), n, A,

-27-
Q, R1 and R2 preferably or in particular have that meaning which has already been indicated above, in connection with the description of the compounds of the formula (I) according to the invention, as being preferable or particularly preferable for n, A, Q, R1 and R2; Z preferably represents fluoro, chloro, bromo, C,-C4-alkoxy, phenoxy or benzyloxy, and in particular represents chloro, methoxy, ethoxy or phenoxy.
The starting materials of the formula (IX) are known and/or can be prepared by methods known per se.
A general definition of the benzene derivatives to be used as starting materials in the process (f) according to the invention for the preparation of the compounds of the formula (I) is given by the formula (X). In the formula (X), n, A, R1 and R2 preferably or in particular have that meaning which has already been indicated above, in connection with the description of the compounds of the formula (I) according to the invention, as being preferable or particularly preferable for n, A, R1 and R2.
The starting materials of the formula (X) are known and/or can be prepared by methods known per se.
The processes (a), (b), (c), (d), (e) and (f) according to the invention for the preparation of the novel compounds of the formula (I) are preferably carried out using diluents. Suitable diluents in this context are virtually all inert organic solvents. These include, preferably, aliphatic and aromatic, optionally halogenated hydrocarbons such as pentane, hexane, heptane, cyclohexane, petroleum ether, benzine, ligroin, benzene, toluene, xylene, methylene chloride, ethylene chloride, chloroform, tetrachloromethane, chlorobenzene and o-dichlorobenzene; ethers such as diethyl ether and dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, tetrahydrofuran and dioxane; ketones such as acetone, methyl ethyl ketone, methyl isopropyl ketone and methyl isobutyl ketone; esters such as methyl acetate and ethyl acetate; nitriles, for example acetonitrile and propionitrile; amides, for example dimethylformamide, dimethylacetamide and N-methylpyrrolidone, and also dimethyl sulfoxide, tetramethylene sulfone and hexamethylphosphoric triamide.

-28-
Suitable reaction auxiliaries and/or acid acceptors for the processes (a), (b), (c), (d), (e) and (f) according to the invention are all acid-binding agents which are conventionally used for such reactions. Preference is given to alkali metal hydroxides, such as for example sodium hydroxide and potassium hydroxide, alkaline earth metal hydroxides, such as for example calcium hydroxide, alkali metal carbonates and alkoxides, such as sodium carbonate and potassium carbonate, sodium tert-butoxide and potassium tert-butoxide, and also basic nitrogen compounds, such as trimethylamine, triethylamine, tripropylamine, tributylamine, diisobutylamine, dicyclohexylamine, ethyldiisopropylamine, ethyldicyclohexylamine, N,N-dimethylbenzylamine, N,N-dimethyl-aniline, pyridine, 2-methyl-, 3-methyl-, 4-methyl-, 2,4-dimethyl-, 2,6-dimethyl-, 2-ethyl-, 4-ethyl- and 5-ethyl-2-methyl-pyridine, l,5-diazabicyclo[4.3.0]-non-5-ene (DBN), l,8-diazabicyclo[5.4.0]-undec-7-ene (DBU) and 1,4-diazabicyclo-[2.2.2]-octane (DABCO).
The reaction temperatures in the processes (a), (b), (c), (d), (e) and (f) according to the invention can be varied within a relatively wide range. The processes are in general carried out at temperatures of between -20°C and +150°C, preferably at temperatures between 0°C and +100°C.
The processes (a), (b), (c), (d), (e) and (f) according to the invention are generally carried out under atmospheric pressure. However, it is also possible to operate under elevated or reduced pressure.
For carrying out processes (a), (b), (c), (d), (e) and (f) according to the invention, the starting materials required in each case are in general employed in approximately equimolar quantities. However, it is also possible to use one of the components employed in each case in a relatively large excess. The reactions are in general carried out in a suitable diluent in the presence of an acid acceptor, and the reaction mixture is stirred for a number of hours at the particular temperature required. Work-up in the case of the processes (a), (b), (c), (d), (e) and (f) according to the invention is in each case carried out by customary methods (cf. the Preparation Examples).

-29-
Salts of the compounds of the general formula (I) according to the invention can be prepared if desired. Such salts are obtained in a simple manner by customary methods of forming salts, for example by dissolving or dispersing a compound of the formula (I) in an appropriate solvent, for example methylene chloride, acetone, tert-butyl methyl ether or toluene, and adding an appropriate base. The salts can then - if desired after prolonged stirring - be isolated by concentration or filtration with suction.
The active compounds according to the invention can be used as defoliants, desiccants, haulm killers and, especially, as weed-killers. By weeds, in the broadest sense, there are to be understood all plants which grow in locations where they are not wanted. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.
The active compounds according to the invention can be used, for example, in connection with the following plants:
Dicotyledonous weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindemia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus and Taraxacum.
Dicotyledonous cultures of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita.
Monocotyledonous weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus and Apera.

-30-
Monocotvledonous cultures of the genera: Oryza, Zea, Triticum, Hordeum, A vena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus and Allium.
However, the use of the active compounds according to the invention is in no way restricted to these genera, but also extends in the same manner to other plants.
The compounds are suitable, depending on the concentration, for the total control of weeds, for example on industrial terrain and rail tracks, and on paths and squares with or without tree plantings. Equally, the compounds can be employed for controlling weeds in perennial cultures, for example afforestations, decorative tree plantings, orchards, vineyards, citrus groves, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, soft fruit plantings and hopfields, in lawns, turf and pasture-land, and for the selective control of weeds in annual cultures.
The compounds of the formula (I) according to the invention are suitable for controlling monocotyledonous and dicotyledonous weeds, both pre-emergence and post-emergence. They exhibit strong herbicidal action and a broad spectrum of activity when used on the soil and on aerial parts of the plants.
The active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, pastes, soluble powders, granules, suspo-emulsion concentrates, natural and synthetic materials impregnated with active compound, and very fine capsules in polymeric substances.
These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is liquid solvents and/or solid carriers, optionally with the use of surface-active agents, that is emulsifying agents and/or dispersing agents and/or foam-forming agents.
In the case of the use of water as an extender, organic solvents can, for example, also be used as auxiliary solvents. As liquid solvents, there are suitable in the main:

-31 -
aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulfoxide, as well as water.
Suitable solid carriers are:
for example ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and silicates, suitable solid carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks; suitable emulsifying and/or foam-forming agents are: for example non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates as well as protein hydrolyzates; suitable dispersing agents are: for example lignin-sulfite waste liquors and methylcellulose.
Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latexes, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids, can be used in the formulations. Further additives can be mineral and vegetable oils.
It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyes, such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

-32-
The formulations in general contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
For controlling weeds, the active compounds according to the invention, as such or in the form of their formulations, can also be used as mixtures with known herbicides, finished formulations or tank mixes being possible.
Possible components for the mixtures are known herbicides, for example anilides, such as diflufenican and propanil; arylcarboxylic acids, such as dichloropicolinic acid, dicamba and picloram; aryloxyalkanoic acids, such as 2,4-D, 2,4-DB, 2,4-DP, fluroxypyr, MCPA, MCPP and triclopyr; aryloxy-phenoxy-alkanoic esters, such as diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl and quizalofop-ethyl; azinones, such as chloridazon and norflurazon; carbamates, such as chlorpropham, desmedipham, phenmedipham and propham; chloroacetanilides, such as alachlor, acetochlor, butachlor, metazachlor, metolachlor, pretilachlor and propachlor; dinitroanilines, such as oryzalin, pendimethalin and trifluralin; diphenyl ethers, such as acifluorfen, bifenox, fluoroglycofen, fomesafen, halosafen, lactofen and oxyfluorfen; ureas, such as chlorotoluron, diuron, fluometuron, isoproturon, linuron and methabenzthiazuron; hydroxylamines, such as alloxydim, clethodim, cycloxydim, sethoxydim and tralkoxydim; imidazolinones, such as imazethapyr, imazamethabenz, imazapyr and imazaquin; nitriles, such as bromoxynil, dichlobenil and ioxynil; oxyacetamides, such as mefenacet; sulfonylureas, such as amidosulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, metsulfuron-methyl, nicosulfuron, primisulfuron, pyrazosulfuron-ethyl, thifensulfuron-methyl, triasulfuron and tribenuron-methyl; thiocarbamates, such as butylate, cycloate, diallate, EPTC, esprocarb, molinate, prosulfocarb, thiobencarb and triallate; triazines, such as atrazine, cyanazine, simazine, simetryne, terbutryne and terbutylazine; triazinones, such as hexazinone, metamitron and metribuzin; and others, such as aminotriazole, benfuresate, bentazone, cinmethylin, clomazone, clopyralid, difenzoquat, dithiopyr, ethofumesate, fluorochloridone, glufosinate, glyphosate, isoxaben, pyridate, quinchlorac, quinmerac, sulphosate and tridiphane.
Mixtures with other known active compounds, such. as fungicides, insecticides, acaricides, nematicides, bird repellents, plant nutrients and agents which improve soil structure, are also possible.
The active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the customary manner, for example by watering, spraying, atomizing or scattering.
The active compounds according to the invention can be applied either before or after emergence of the plants. They can also be incorporated into the soil before sowing.
The amount of active compound used can vary within a substantial range. It depends essentially on the nature of the desired effect. In general, the amounts used are between 1 g and 10 kg of active compound per hectare of soil surface, preferably between 5 g and 5 kg per ha.
Accordingly, the present invention relates to sulphonylamino(thio)carbonyl compounds of the general formula (I):
(Formula Removed)
in which
a, represents the numbers Q, 1 or 2,
A represents a single bond,
Q represents oxygen or sulphur,
Rl represents hydrogen, formyl, represents in each case optionally cyano-, fluorine-, chlorine-, bromine-, phenyl- or C1-C4-alkoxy-substituted alkyl, alkoxy, alkylamino, alkoxyamino, dialkylamino, N-alkoxy-N-alkylamino, alkylcarbonyl, alkoxycarbonyl, alkylsulphonyl, alkemyl or alkynyl having

in each case up to 6 carbon atoms, or represents in each case optionally cyano-, fluorine-, chlorine-, bromine- or C1-C4alkyl-substituted C3-C6-cycloalkyl, C3-C6-cycloalkyl-carbonyl or C3-C6-cycloalkylsulphonyl,
represents cyano, fluorine, chlorine, bromine or represents in each case optionally cyano-, fluorine-, chlorine-, bromine- or Ci-d-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylsulpMnyl, aJfcylsulphonyl,
dialkylamioosulphonyl, alkenyl, alkynyl, alkenyloxy or alkynyfoxy having in each case up to 6 carbon atoms and
represents optionally substituted heterocyclyl of the formula below
(Formula Removed)
in -which
Q1 represents oxygen or sulphur and
R4 represents hydrogen, hydroxyl, amino, cyano, represents C2-C10-alkylideneanMno, represents optionally fluorine-, chlorine-, bromine-, cyano-, C1-C4-alkcxy-, C1-C4-alkyl-carbonyJ- or C1-C4-aIkoxy-carbonyi-substituted C1-C6-alkyI, represents in each case optionally fluorine-, chlorine- and/or brormne-substituted C2-C6-alkenyl or C2-C6-alkynyl, represents in each case optionally fluorine-, chlorine-, bromine-, cyano-, C1-C4-alkoxy- or C1-C4-aIkoxy-carbonyl-substituted C1-C6-alkoxy, C1-C4 alkylamino or C1-C6-alkyl-carbonylamino, represents C3-C6-alkeailyloxy, represents di-(C1-C4-alfcyl)-amino, represents in each case optionally fluorine-, chlorine-, bromine-, cyano- and/or C1-C4-a!kyi-substituted C3-C5-cycloalkyl, C1-C4-cycloakylamino or C3-C6-cycloalkyl-C1-C4-alkyl, or represents in each case optionally fluorine-, chlorine-, bromine-, cyano-, nitra-, C1-C4-alkyl-, trifluoromethyl- and/or C1-C4-alkoxy-substituted phenyl or phenyl-C1-C4-alkyl,
R5 represents hydrogen, hydroxy!, mercapto, amino, cyano, fluorine, chlorine, bromine, iodine, represents optionally fluorine-, chlorine-, bromine-, cyano-, C1-C4-alkoxy-, C1-C4alkyl-carbonyl- or C1-C4-alkoxy-carbonyl-substituted C1-C6-alkyl, represents in each case optionally fluorine-, chlorine- and/or bromine-substituted C2-C6-alkenyl or C2-C6-alkynyl, represents in each case optionally fluorine-, chlorine-, cyano-, C1-C4-alkoxy- or C1-C4-alkoxy-carbonyl-substituted C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylamino or C1-C4-alkyl-carboirylamino, represents C3-C6-alkenyloxy, C3-C6-aIkynyloxy, C3-C6-alkenyltbio, C3-C6-alkynylthio,

C3-C6-alkenylamino or C3-C6alkynylamino, represents di-(C1-C4-alkyl)-amino, represents in each case optionally methyl- and/or ethyl-substituted aziridino, pyrrolidino, piperidino or morpholino, represents in each case optionally fluorine-, chlorine-, broxnine-, cyano- and/or C1-C4-alkyl-substituted C3-C6-cycioaJkyl, C5-C6cycloalkenyl, GrCs-cycloalkyloxy, C3-C6-cycloalkylthio, C3-C6-cycloalkylamino, C3-C6-cycloalkyl-C1-C4-alkyl, C3-C6-cycloalkyl-C1-C4-alkoxy, C3-C6-cycloalkyl~C1-C4-alkylthio or C3-C6-cycloalkyl-C1-C4-alkylamino, or represents in each case optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, C1-C4-alkyl-, trifluoiomethyl-3 C1-C4-alkoxy- and/or C1-C4alkoxycarbonyl-substituted phenyl, phenyl-C1-C4-alkyl, phenoxy, phenyl-C1-C4-alkoxy, phenylthio, phenyl-C1-C4-alkylthio: phenylamino orphenyl-C1-C4-alkylamino, or
E.4 and R5 together represent optionally branched alkanediyl having 3 to 11 carbon atoms,
and the salts of compounds of the formula (T).
The preparation and use of the active compounds according to the invention can be seen from the following examples.


Preparation Examples: Example 1

-34-




N-CH3
0-C2H5


A solution of 3.3 g (14 mmol) of 2-chloro-6-methylthio-benzenesulfonamide, 3.7 g (14 mmol) of 5-ethoxy-4-methyl-2-phenoxycarbonyl-2,4-dihydro-3H-l,2,4-triazol-3-one and 2.3 g (15.4 mmol) of diazabicyclo[5.4.0]undecene (DBU) in 30 ml of acetonitrile is stirred at room temperature (about 20°C) for six hours. The solvent is then removed using water pump vacuum and the oily residue is taken up in 100 ml of methylene chloride. The solution is washed successively with IN hydrochloric acid and saturated brine, dried over sodium sulfate and freed from the solvent using water pump vacuum. 6.6 g of an oily residue are obtained, which crystallizes when stirred with 30 ml of ethanol. After filtration and drying under reduced pressure at 25°C, 3.15 g (55.4 % of theory) of 5-ethoxy-4-methyl-2-(2-chloro-6-methylthio-phenylsulfonyl-aminocarbonyl)-2,4-dihydro-3H-l,2,4-triazol-3-one of melting point 144°C are obtained.
Similar to Preparation Example 1 and in accordance with the general description of the preparation processes according to the invention, it is also possible to prepare for example the compounds of the formula (I) listed in Table 1 below.


(I)

-35 -Table 1: Examples of the compounds of the formula (I)
Ex. n A Q R1 (Position-) R3 Melting point
No. R2 (°C)
0 - O CjTs (6-)OCH3 " j^ 89
\ /
N CH,
53 0 - O C2H5 (6-)OCF3 ^ 111
/ (pyridine salt)
N—(
CH,
O C2H5 (6-)OCF3 NX H2
CH3
O N(CH3)2 (4-)SO2N(CH3)2 o 189

0-C2H5
0 C2H5 (6-)OCF3 o 127

O C2H5 (6-)OCH3 o 149

0-C2H5

Table 1 - continued - - 36 -
Ex. n A Q R1 (Position-) R3 Melting point

No. R

2



8 0 - O C2H5 (6-)OCH3 o 140
V
N
0 - O C,H5 (6-)F o 139
K
0-C2H5
10 0 - O C,H. (6-)Cl o 114



0-C2H5

1 0 - O C2H5 (6-)CF3 o 119



0-C2H5

5 12 2-0 C,H5 (6-)CF3 o 142
0-C2H5
13 0-0 C2H5 (6-)CF3 o 146
OCH3

Table 1 - continued - - 37 -
Ex. n A Q R1 (Position-) R3 Melting point
No. R2 (°C)
__ _ _ _ _ (-
\ N:
SCH3
15 0 0 C2H5 (6-)CF3 o 135
\ N:
16 0 O C2H5 (6-)F o 130

N:

OCH3

17 0 O C2HS (6-)F o 120
-^../V.^CH.
N:
SCH3
5 18 0 O i-C3H7 (6-)OCH3 o 145
0-C2H6

Table 1 - continued - - 38 -
Ex. n A Q R1 (Position-) R3 Melting point
No. R2 (°C)
"19 0 -OOft(60C1 o 133
OCH3
20 0 - 0 CH3 (6-)OCH3 o 113

0-C2H5
21 0 - O CH3 (6-)OCH3 o 168
\ N:
OCH3
22 0 - O CH3 (6-)OCH3 o 122
\ N:
C2H5
5 23 0-0 i-C3H7 (6-)OCH3 o 146

Table 1 - continued - - 39 -
Ex. n A Q R1 (Position-) R3 Melting point
No. R2 (°C)
"24 0 - Oi-C3H7 (6-)OCH3 o175
\ N:
OCH3
25 0 - O i-C3H7 (6-)OCF3 o 125
0-C2H5
26 0 - 0 i-C3H7 (6-)CH3 o 133
\ N:
27 0 - O i-C3H7 (6-)CH3 o 144
\ N:
OCH3
5 28 0 - O i-C3H7 (6-)CH3 o 131
0-C2H5

Table 1 - continued - - 40 -
Ex. n A Q R1 (Position-) R3 Melting point
No. R2 (°C)
(6_)CHj
\ N:
SCH3
30 0 - O C2H5 (6-)OCH3 o 173
\ N:
OCH3
31 0 - O C2H5 (6-)OCH3 o 113
\ N:
SCH3
32 0 - O CH3 (6-)OCF3 o 148
OCH3
5 33 0 O CH3 (6-)OCF3 o 147
\ N:
SCH3

Table 1 - continued - - 41 -
Ex. n A Q R1 (Position-) R3 Melting point
No. R2 (°C)
_ _ __ _ (6.)OCF3 o 127
\ N:
35 0 - O CH3 (6-)OCF3 o 138
K
0-C2H5
36 0 - O i-C3H7 (6-)C2H5 o 141
0-C2H6
37 0 O i-C3H7 (6-)SCH3 o 163
\ N:
5 38 0 O i-C3H7 (6-)SCH3 o 143
0-C2H5
39 0 - O C2H5 (6-)OCF3 o 101
N=

Le A 31 803 - Foreign countries
Table 1 - continued - - 42 -
Ex. n A Q R1 (Position-) R3 Melting point
No. R2 (°C)
"40 0 - O CJ15 (6-)OCF3 oH6

OCH3
41 0-0 C2H5 (6-)OCF3 o 115

N

SCH3

42 0 - O i-C3H7 (6-)OCH3 o >230 (d.)
SCH3
43 0 - O C2H5 (6-)SC2H5 o 134

5 44 0-0 C2H5 (6-)SC2H5 0 153
C2H5

Le A 31 803 - Foreign countries
Table 1 - continued - - 43 -
Ex. n A Q R1 (Position-) R3 Melting point
No. R2 (°C)
__ _ ._ _ (6.)Sc2H5 o 150
\ N=H
SCH,
46 0 - O C2H5 (6-)SC2H5 o 168
\ N=H
OCH,
47 0 - O -C2H4O- (6-)SC2H5 o 162
COCF3 --N
N =

48 0 - O CH3 (6-)CH3 o 165
A.,
b-c2H5
-M-CH
IN N
\ /

5 49 0 - O CH3 (6-)CH3 o 141
^•CH,

Le A 31 803 - Foreign countries
Table 1 - continued - - 44 -
Ex. n A Q R1 (Position-) R3 Melting point
No. R2 (°C)
__ _ _ _ _ ( -
OCH3
51 0 - 0 CH3 (6-)SCH3 o 162
\ N:
SCH3
52 0 - O CH3 (6-)SCH3 o 183
0-C2H6
53 0 - O C2H5 (6-)CH3 o 157

N:

OCH3

5 54 0 - O C2H5 (6-)CH3 o 126
— /X _CH
\ N:
SCH3

Le A 31 803 - Foreign countries
Table 1 - continued - - 45 -
Ex. n A Q R1 (Position-) R3 Melting point
No. R2 (°C)
_ _ _ _ _ (6_)CH3 0 149
\ N:
56 0 - O C2H5 (6-)CH3 o 154
57 0 - O CH2CH2F (6-)OCH3 O 192
N:
OCH3
58 0 - O CH2CH2F (6-)OCH3 O 147
-N \ N:
5 59 0 - O CH2CH2F (6-)OCH3 o 171
-hAN-CH3
K
0~C2H5
60 0 - O t-C4H9 (6-)CF3 o 141
j-CH3
b-c2H5

Le A 31 803 - Foreign countries
Table 1 - continued - - 46 -
Ex. n A Q R1 (Position-) R3 Melting point
No. R2 (°C)
"61 0 -OCti, (6^CFi 5 157

N:

OCH3

62 0 - O CH3 (6-)CF3 o 173
\ N:
SCH3
63 0 - O CH3 (6-)CF3 o 165
N:
64 0 - O CH3 (6-)CF3 o 165
/x. ni-j
0-C2H5
5 65 0 - O CH2CH2F (6-)OCF3 o 112

N=

OCH3

Le A 31 803 - Foreign countries
Table 1 - continued - - 47 -
Ex. n A Q R1 (Position-) R3 Melting point
No. R2 (°C)
__ _ . _ CH2CH2F (6-)OCF3 o125
\ N:
SCH3
67 0 - O CH2CH2F (6-)OCF3 o 95
\ N:
68 0 - O CH2CH2F (6-)OCF3 o 137
K
0-C2H5
69 0 - 0 CH2CH2F (6-)CF3 o 151
~-^../\..^-CH.
\ N:
OCH3
5 70 0-0 CH2CH2F (6-)CF3 o 139
N:

Le A 3 1 803 - Foreign countries
Table 1 - continued - - 48 -
Ex. n A Q R1 (Position-) R3 Melting point
No. R2 (°C)
CH2CH2F (6-)CF3 o 158
0-C2H5
72 0 - O i-C3H7 (6-)CF3 o 150
•N \ N:
OCH3
73 0 - O i-C3H7 (6-)CF3 o 149
/^. _ru
\ N:
"SCH
74 0 - O i-C3H7 (6-)CF3 o 166
— ^^ ^CH
V N:
5 75 0 - O i-C3H7 (6-)CF3 o 152

Le A 31 803 - Foreign countries Table 1 - continued -
Ex.
No.
n A Q R1

-49-
(Position-) R2

R3

Melting point



76 0

O

(6-)OCF3

149

OCH

77 0

O

(6-)OCF3

o

152


SCH

78 0

O

(6-)OCF3

o

145



79 0

O

(6-)OCF3

o

138





0-C2H5



5 80 0

O

(6-)OCF3

117

OCH,

Le A 31 803 - Foreign countries
Table 1 - continued - - 50 -
Ex. n A Q R1 (Position-) R3 Melting point
No. R2 (°C)
~T\ 0 ' 6 Cft(6-)OCF3 o 124

OCH3
82 0 - O C2H5 (6-)OCH3 o 183

N=

OCH3

83 0 - O CH3 (6-)Cl o 147

OCH3
84 0 - O CH3 (6-)OCF3 o 186
OCH3

5 85 0 - O CH3 (6-)OCH3 p 166
'N'^
\ N:
i
OCH,

Le A 31 803 - Foreign countries
Table 1 - continued - - 51 -
Ex. n A Q R1 (Position-) R3 Melting point
No. R2 (°C)
"86 0 ~ 0 CH2CH2F (6-)OCH3 o196
\ N^H
OCH3
87 0 - 0 CH3 (6-)CF3 o 140
OCH3
88 0 - O CH3 (6-)SCH3 o 165
OCH3
89 0 - O CH2CH2F (6-)OCF3 o 126
OCH3
5 90 1-0 C2H5 (6-)CF3 o 132
K
0-C2H5
91 0 - O CF3 (6-)OCF3 o 167
0~C2H5

Le A 31 803 - Foreign countries
Table 1 - continued - - 52 -
Ex. n A Q R1 (Position-) R3 Melting point
No. R2 (°C)
_ _ __ (CHF (£)cp o141
\ N:
OCH3
93 0 - 0 (CH2)3F (6-)CF3 o 134
\ N:
SCH3
94 0 - O (CH2)3F (6-)CF3 o 119
0-C2H5
95 0-0 CH2F (6-)OCF3 o 119
0-C2H5
5 96 0 - O CH2F (6-)OCF3 o 133
\ N:
OCH3

Le A 31 803 - Foreign countries
Table 1 - continued -53 -
Ex. n A Q R1 (Position-) R3 Melting point
No. R2 (°C)
97 0 0 CH2F (6-)OCF3 o 147
OCH3
98 0 - O CH2CHF2 (6-)CF3 o 116
0-C2H5
99 0 - 0 CH2CHF2 (6-)CF3 o (log P
cH3 =2.59)
N:
OCH3
100 0 - O CH2CHF2 (6-)CF3 o (log P
OCH3
5 101 0 - O CH2CHF2 (6-)CH3 o (log P
-CH =2.73)
N:
SCH3

Le A 31 803 - Foreign countries
Table 1 - continued - - 54 -
Ex. n A Q R1 (Position-) R3 Melting point
No. R2 (°C)
T02 2 - ON(CH3)2 (6-)CH3 Q 203 (d.)
N:
103 2 - O N(CH3)2 (6-)CH3 o 146
OC2H5
104 2 - O N(CH3)2 (6-)CH3 o 208
"N N~" 3
K
SCH,
105 2 - O N(CH3)2 (6-)CH3 o 137
OC2H6
5 106 2 - 0 N(CH3)2 (6-)CH3 o 137
CH2OCH3

Le A 31 803 - Foreign countries
Table 1 - continued - - 55 -
Ex. n A Q R1 (Position-) R3 Melting point
No. R2 (°C)
107 2 -ON(CH3)2 (6-)CH3 o182 (d.)
OCH3
108 2 - O N(CH3)2 (6-)CH3 o 113
C3H7-n
109 2 - O N(CH3)2 (6-)CH3 o 80
\ N:
C3H7-i
110 2 - 0 N(CH3)2 (6-)CH3 o H4
OC2H5
5 111 2 - O N(CH3)2 (6-)CH3 o 138
- -H
OC3H7-n

Le A 31 803 - Foreign countries
Table 1 - continued - - 56 -
Ex. n A Q R1 (Position-) R3 Melting point
No. R2 (°C)
N(CH3)2 (6-)CH3 o 161
'
113 0 - O CH3 (6-)CF3 o >210(d.)
SCH3
114 0 - O CF3 (6-)CF3 o 169
OCH3
115 0 - O CF3 (6-)CF3 o 159
N:
5 116 0 - O CF3 (6-)CF3 o 161

Le A 31 803 - Foreign countries
Table 1 - continued - - 57 -
Ex. n A Q R1 (Position-) R3 Melting point
No. R2 (°C)
__ ._ _ ____ _
OC2HS
118 0 - O CF3 (6-)CF3 o 158
A
OCH3
119 0 - O CH3 (6-)C2H5 o 142
XX _rw
OC2H5
120 0 - O CH2CH2F (6-)OC3H7-n o 133
OCH3
5 121 0 - O CH2CH2F (6-)OC3H7-n 0
_ A ,CH3 ^N N 3
N:

Le A 31 803 - Foreign countries
Table 1 - continued - - 58 -
Ex. n A Q R1 (Position-) R3 Melting point
No. R2 (°C)
CH2CH2p (6.)oc3H7-n o
N:
123 0 - O CH2CH2F (6-)OC3H7-n o 144
^ A
^N N
N
OCH,
124 0 - O CH2CH2F (6-)OC3H7-i o 153
OCH3
125 0 - 0 CH2CH2F (6-)OC3H7-i o 152
SCH3
5 126 0 - O CH2CH2F (6-)OC3H7-i o 157
'N' 3

Le A 31 803 - Foreign countries
Table 1 - continued - - 59 -
Ex. n A Q R1 (Position-) R3 Melting point
No. R2 (°C)
_ _ - _ CH2CH2F (6-)OC3H7-i
OC2H5
128 0 - O CH2CH2F (6-)OC3H7-i o 142
-A^
N=^
OCH,
129 0 - O CH2CH2F (6-)OCH3 o 140
-^ ^>. ^nw
SCH3
130 0 - O CH3 (6-)CF3 o 216
— -/^» -OH
OC2H5

-60-Comments (for Table 1):
" The group denoting the radical R1 in the Examples 76-80 represents -CH,-C=CH (propargyl).

2)

d. = decomposition.

3) log P = logarithm to base ten of the partition coefficient (P) of the
dissolved substance in the two-phase system n-octanol/water, determined by the HPLC method (at pH 2; eluent: acetonitrile containing 1 % of H3PO4 [cf. for example Official Journal of the European Communities, No. L 383A, 35, pages 63 ff, dated 29.12.1992].

-61 -The compound listed as Example 3 in Table 1 can be prepared, for example, as follows:
2.1 g (0.014 mol) of the sodium salt of 5-methyl-l,2,4-oxadiazole-3-carboxylic acid are refluxed with 80 ml of thionyl chloride and 5 drops of dimethylformamide, for 3 hours. The excess thionyl chloride is then distilled off under reduced pressure and the residue is taken up in 50 ml of pyridine while cooling. 4.2 g (0.014 mol) of 2-ethylmercapto-6-trifluoromethoxy-benzenesulfonamide are then added, and the reaction mixture is stirred at room temperature for 15 hours. The pH is adjusted to 1 using hydrochloric acid, and the product is filtered off under suction and washed with IN hydrochloric acid.
After drying, 5.6 g (81 % of theory) of N-(2-ethylmercapto-6-trifluoromethoxy-phenylsulfonyl)-5-methyl-l,2,4-oxadiazole-3-carboxamide are obtained as the pyridinium salt of melting point 111°C.
The compound listed as Example 4 in Table 1 can be prepared, for example, as follows:
3 g of the pyridinium salt prepared by the method of Example 3 are stirred with 60 ml of 10 % strength aqueous potassium hydrogen carbonate solution for 12 hours. The solid formed is filtered off under suction, stirred with 50 ml of IN hydrochloric acid, filtered off under suction, washed with water and dried.
2.3 g (76 % of theory) of N-(2-ethylmercapto-6-trifluoromethoxy-phenylsulfonyl)-5-methyl-l,2,4-oxadiazole-3-carboxamide of melting point 112°C are obtained.

-62 Starting materials of the formula (II):
Example (II-1) Steo 1
P-CF,

SO, CH, \2 / 3 NH-f-CH3
CH3
At 5°C, 38.9 g (0.384 mol) of triethylamine and 28.0 g (0.384 mol) of tert-butylamine are added dropwise in succession to a solution of 99.0 g (0.384 mol) of 2-trifluoromethoxy-benzenesulfonyl chloride in 400 ml of acetonitrile. The reaction mixture is stirred at room temperature (about 20°C) for 16 hours and then concentrated using water pump vacuum. The oily residue is dissolved in dichloromethane and the solution is washed with 2N hydrochloric acid, dried over magnesium sulfate and filtered. Using water pump vacuum, the solvent is carefully distilled off from the filtrate.
107.6 g (95.3 % of theory) of N-tert-butyl-2-trifluoromethoxy-benzenesulfonamide are obtained as a crystalline residue of melting point 137°C.
Step 2

S—C2H5 CH3
Under argon, 30.8 g (0.104 mol) of N-tert-butyl-2-trifluoromethoxy-benzenesulfonamide

-63 -
are dissolved in 280 ml of (anhydrous) tetrahydrofuran, cooled to -5°C and treated with 156 ml (0.26 mol) of 15 % strength n-butyllithium solution in hexane. After the solution has been stirred for 3 hours at from 0°C to -5°C, 3.64 g (0.114 mol) of sulfur are added, and the solution is stirred for a further 3 hours at room temperature (about 20°C). The reaction mixture is then treated with 18.0 g (0.115 mol) of iodoethane, stirred at room temperature for 16 hours and then treated with 560 ml of dichloromethane The solution is washed with 2N hydrochloric acid, dried over magnesium sulfate and concentrated using water pump vacuum. The crude product obtained as a residue is stirred with petroleum ether, filtered off under suction and dried under reduced pressure.
31.4 g (84.6 % of theory) of N-tert-butyl-2-ethylthio-6-trifluoromethoxy-benzenesulfonamide of melting point 77°C are obtained.
Step 3

S — C2H5
At room temperature (about 20°C), 163 ml (2.13 mol) of trifluoroacetic acid are added dropwise to a solution of 30.4 g (0.085 mol) of N-tert-butyl-2-ethylthio-6-trifluoromethoxy-benzenesulfonamide in 160 ml of dichloromethane. The reaction mixture is stirred at room temperature for about 24 hours, diluted with 300 ml of dichloromethane, washed two times with 300 ml of water, dried over magnesium sulfate and concentrated using water pump vacuum. The crude product obtained as a residue is stirred with petroleum ether, filtered off under suction and dried under reduced pressure.
21.7 g (84.7 % of theory) of 2-ethylthio-6-trifluoromethoxy-benzenesulfonamide of

-64 melting point 146°C are obtained.
Example (II-2) Step 1

Under argon, 163.1 g (0.58 mol) of N-tert-butyl-2-trifluoromethyl-benzenesulfonamide are dissolved in 1 liter of (anhydrous) tetrahydrofuran, cooled to -10°C and treated with 884 ml (1.45 mol) of 15 % strength n-butyllithium solution in hexane. After the solution has been stirred for 3 hours at from 0°C to -5°C, 30.7 g (0.96 mol) of sulfur are added, and the solution is stirred at room temperature (about 20°C) for a further 20 hours. While cooling to about 20°C, the reaction mixture is then treated with 100 ml of 2N hydrochloric acid, 1 liter of water and 1 liter of dichloromethane. The aqueous phase is adjusted to pH 1 using 2N hydrochloric acid, and the organic phase is separated off, washed with water, dried over magnesium sulfate and concentrated using water pump vacuum. The crude product obtained as a residue is stirred with petroleum ether, filtered off under suction and dried under reduced pressure.
160.4 g (84.6 % of theory) of N-tert-butyl-2-mercapto-6-trifluoromethyl-benzenesulfonamide of melting point 139°C are obtained.

-65 -Step 2

At room temperature (about 20°C), 104 ml (1.36 mol) of trifluoroacetic acid are added dropwise to a solution of 17.0 g (0.054 mol) of N-tert-butyl-2-mercapto-6-trifluoromethyl-benzenesulfonamide in 100 ml of dichloromethane. The reaction mixture is stirred at room temperature for about 24 hours, diluted with 300 ml of dichloromethane, washed two times with 200 ml of water, dried over magnesium sulfate and concentrated using water pump vacuum. The crude product obtained as a residue is stirred with petroleum ether, filtered off under suction and dried under reduced pressure.
13.8 g (81.2 % of theory) of 2-tert-butylthio-6-trifluoromethyl-benzenesulfonamide of melting point 91°C are obtained.
Step 3

At room temperature (about 20°C), 23.3 ml (0.023 mol) of a 1M boron tribromide solution in dichloromethane are added dropwise to a solution of 7.3 g (0.023 mol) of N-tert-butyl-2-tert-butylthio-6-trifluoromethyl-benzenesulfonamide in 80 ml of

-66-
dichloromethane. The reaction mixture is stirred at room temperature for 4 hours, diluted with 100 ml of dichloromethane, washed two times with 100 ml of water, dried over magnesium sulfate and filtered. The solvent is carefully distilled off from the filtrate using water pump vacuum.
5.3 g (88.7 % of theory) of 2-mercapto-6-trifluoromethyl-benzenesulfonamide of melting point 155°C are obtained.
Example (II-3)
Step 1
0—CH3

Under argon, 108 g (0.444 mol) of N-tert-butyl-2-methoxy-benzenesulfonamide are dissolved in 759 ml of (anhydrous) tetrahydrofuran, cooled to -10°C and treated with 678 ml (1.11 mol) of 15 % strength n-butyllithium solution in hexane. After the solution has been stirred for 3 hours at from 0°C to -5°C, 23.4 g (0.73 mol) of sulfur are added, and the mixture is stirred at room temperature (about 20°C) for a further 20 hours. While cooling to about 20°C, the reaction mixture is then adjusted to pH 1 using 2N hydrochloric acid. The solid precipitate is isolated by filtration under suction, washed with water and dried at 50°C using water pump vacuum.
72 g (59 % of theory) of N-tert-butyl-2-methoxy-6-mercapto-benzenesulfonamide of melting point 210°C are obtained.
The filtrate is admixed with 1 liter of water and 1.5 liters of dichloromethane, and the organic phase is separated off, washed with water, dried over magnesium sulfate and freed from the solvent using water pump vacuum. A further 35.5 g (29 % of theory) of

-67-
N-tert-butyl-2-methoxy-6-mercapto-benzenesulfonamide are obtained.
Step 2
0-CH
CH

\ S

CH

—' 2
70 g (0.255 mol) of N-tert-butyl-2-methoxy-6-mercapto-benzenesulfonamide are suspended in 180 ml of dimethyl sulfoxide and heated to 90°C for 22 hours. After cooling, the suspension is poured into about 1 liter of water. The solid precipitate is isolated by filtration under suction, washed with water and dried at 60°C using water pump vacuum.
67.1 g (98 % of theory) of bis-(2-tert-butylsulfamoyl-3-methoxy-phenyl) disulflde of melting point 275°C are obtained.
Step 3
O—CH,
so2
NH,
S —
—I 2
At room temperature (about 20°C), 71 ml (0.93 mol) of trifluoroacetic acid are added dropwise to a suspension of 20.4 g (0.037 mol) of bis-(2-tert-butylsulfamoyl-3-methoxy-phenyl) disulflde in 70 ml of dichloromethane. The reaction mixture is stirred for about

-68-
23 hours at room temperature, filtered off under suction, washed with dichloromethane and dried at 60°C under reduced pressure.
16.0 g (81 % of theory) of bis-(3-methoxy-2-sulfamoyl-phenyl) disulfide of melting point 263°C are obtained.
Step 4
O-CH3

Under an atmosphere of nitrogen, 12.7 g (0.334 mol) of solid sodium borohydride are added a little at a time to a suspension of 19.2 g (0.044 mol) of bis-(3-methoxy-2-sulfamoyl-phenyl) disulfide in 180 ml of methanol. After the addition has ended, the reaction mixture is stirred for 24 hours at room temperature (about 20°C) and admixed dropwise with about 100 ml of IN hydrochloric acid. The major part of the methanol is removed using water purnp vacuum, the solid residue is stirred with 0.5N hydrochloric acid, filtered off under suction and dried at 60°C under reduced pressure.
13.8 g (72 % of theory) of 2-methoxy-6-mercapto-benzenesulfonamide of melting point 166°C are obtained.
Step 5
p-CH,


-69-
A solution of 7.5 g (34 mmol) of 2-methoxy-6-mercapto-benzenesulfonamide in 70 ml of (anhydrous) acetonitrile is treated with 9.45 g (68.5 mmol) of (anhydrous) potassium carbonate, and the mixture is stirred at room temperature (about 20°C) for 2 hours. 4.93 g (37.7 mmol) of 1-bromo-2-fluoro-ethane are then added dropwise, and stirring is continued at room temperature for a further 24 hours. The reaction mixture is diluted with 150 ml of dichloromethane, washed with IN hydrochloric acid, dried over magnesium sulfate and filtered. The solvent is carefully distilled off from the filtrate using water pump vacuum.
8.6 g (95 % of theory) of 2~(2-fluoro-ethylthio)-6-methoxy-benzenesulfonamide of melting point 127°C are obtained.
Example (II-4)
Step 1
S~C2H5
SO- CH,
\2 / 3
NH—(—CH,
\ 3
CH3
Under an atmosphere of argon, 30 g (0.14 mol) of N-tert-butyl-benzenesulfonamide are dissolved in 400 ml of (anhydrous) tetrahydrofuran, cooled to -5°C and treated with 210 ml (0.35 mol) of 15 % strength n-butyllithium solution in hexane. After the solution has been stirred for 3 hours at from 0°C to -5°C, 4.9 g (0.153 mol) of sulfur are added, and the mixture is stirred for a further 3 hours at room temperature (about 20°C). The reaction mixture is then treated with 24.2 g (0.155 mol) of iodoethane, stirred at room temperature for 24 hours and then admixed with 800 ml of dichloromethane. The solution is washed with IN hydrochloric acid, dried over magnesium sulfate and concentrated using water pump vacuum. The crude product obtained as a residue is stirred with petroleum ether, filtered off under suction and dried at 40°C under reduced pressure.

-70-
34.1 g (89 % of theory) of N-tert-butyl-2-ethylthio-benzenesulfonamide of melting point 88°C are obtained.
Step 2
S—C2H5

Under an atmosphere of nitrogen, 25 g (0.092 mol) of N-tert-butyl-2-ethylthio-benzenesulfonamide are dissolved in 200 ml of (anhydrous) tetrahydrofuran, cooled to -10°C and treated with 140 ml (0.23 mol) of 15 % strength n-butyllithium solution in hexane. After the solution has been stirred for 3 hours at from -10°C to -15°C, the reaction mixture is treated with 15.6 g (0.11 mol) of iodomethane. The solution is stirred for a further 2 hours at from -15°C to -20°C, and the temperature is then allowed to increase slowly to room temperature (about 20°C). After 24 hours, the solution is mixed with 800 ml of dichloromethane, washed with 2N hydrochloric acid, dried over magnesium sulfate and concentrated using water pump vacuum. The crude product obtained as a residue is stirred with petroleum ether, filtered off under suction and dried at 40°C under reduced pressure.
20.1 g (76.5 % of theory) of N-tert-butyl-2-ethylthio-6-methyl-benzenesulfonamide of melting point 94°C are obtained.
Similarly to Examples (II-l) to (II-4), it is also possible to prepare for example the compounds of the formula (II) listed in Table 2 below.
R1

-71 -Table 2: Examples of the compounds of the formula (II)
Ex.No. n A R1 (Position-) R2 Melting point (°Q
II-5 0 CH3 (6-)C2H5
II-6 0 C2H5 (6-)OCH3 154
II-7 0 C2H5 (6-)F 132
II-8 0 C2H5 (6-)Cl 124
II-9 0 C2H5 (6-)CF3 120
11-10 1 C2H5 (6-)CF3 112
11-11 2 C2H5 (6-)CF3 193
11-12 0 i-C3H7 (6-)OCH3 128
11-13 0 i-C3H7 (6-)Cl 83
11-14 0 CH3 (6-)Cl 127
11-15 0 CH3 (6-)OCH3 155
11-16 0 CH3 (6-)OCF3 160
11-17 0 i-C3H7 (6-)OCF3 135
11-18 0 i-C3H7 (6-)CH3 87
11-19 0 i-C3H7 (6-)C2H5 146
11-20 0 i-C3H7 (6-)SCH3 129
11-21 0 C2H5 (6-)SC2H5 105
11-22 0 C2H4OCOCF3 (6-)OCH3 135
11-23 0 CH3 (6-)SCH3 120
11-24 0 C2H5 (6-)CH3 192
11-25 0 CH3 (6-)CH3 164
11-26 0 CH3 (6-)CF3 130
11-27 0 H (6-)OCF3 146
11-28 0 C2H4F (6-)OCF3
11-29 0 C2H4F (6-)CF3 131

laoie / - contmuea - - 72 -
Ex.No. n A R1 (Position-) R2 Melting point
11-30 0 i-C3H7 (6-)CF3 138
11-31 0 CH2OCH (6-)OCF3 105
11-32 0 CF3 (6-)OCF3 85
11-33 0 C2H3F2 (6-)CF3 110
11-34 0 C3H6F (6-)CF3 112
11-35 0 CH2F (6-)OCF3 163
11-36 0 CF3 (6-)CF3
11-37 0 CF3 (6-)OCH3

- 73 -
Use Examples: Example A
Pre-emergence test
Solvent: 5 parts by weight of acetone
Emulsifier: 1 part by weight of alkylaryl polyglycol ether
To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
Seeds of the test plants are sown in normal soil. After about 24 hours, the soil is sprayed with the preparation of the active compound in such a way as to apply the particular amounts of active compound desired per unit area. The concentration of the spray liquor is chosen so that the particular amounts of active compound desired are applied in 1000 1 of water/ha.
After three weeks, the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control.
The figures denote:
0% = no action (like untreated control) 100% = total destruction
In this test, a very strong activity against weeds (cf. Tables A-l to A-5) is shown, for example, by the compounds of Preparation Examples 1, 6, 7, 8, 11, 13, 14, 20, 21, 22, 24, 25, 30, 32, 33, 34, 35, 40, 41, 57, 59, 60, 61, 62 and 63, combined with good tolerance of some compounds by crop plants, such as for example maize, wheat, cotton and soya beans.
ai." = active ingredient

Table A-l: Pre-emergence test/greenhouse

Active compound g ai./ha Maize as per Preparation Ex. No.

Alopecurus Lolium Sorghum

Amaranthus

Chenopodium Matricaria Solanum


6 125 0 100 100 80 100 100 100 100
*7 / 125 0 100 100 90 100 100 70 100
8 125 0 100 80 - 100 100 - 60
11 125 10 100 90 100 100 100 100 100
13 125 0 90 90 100 100 100 100 100
14 125 0 100 - 90 70 100 100 100
1 125 0 95 70 90 90 60 70 100
20 60 0 100 95 100 100 100 100 100
21 60 20 100 100 100 100 100 90 100
22 125 30 100 100 80 100 - 60 100
30 60 0 100 100 95 95 90 95 95
32 30 5 90 100 90 100 100 90 95
33 125 10 100 100 100 100 100 100 100
34 60 20 100 80 90 90 90 - 95
57 125 _ 100 100 100 100 100 _ .

Table A-l (continued)
Active compound as per Preparation Ex. No. g ai./ha Maize Alopecurus Lolium Sorghum Amaranthus Chenopodium Matricaria Solanurr
59 125 100 100 100 100 100 100 100
62 60 10 100 100 90 100 100 100
63 60 0 100 70 100 100 100 100

Table A-2: Pre-emergence/greenhouse
Active compound g ai./ha Wheat Alopecurus Lolium Sorghum Amaranthus Chenopodium Solanum Veronica
as per Preparation Ex. No.
35 60 10 100 95 90 100 100 95 100
Table A-3: Pre-emergence/greenhouse
Active compound g ai./ha Maize Cotton Alopecurus Sorghum Amaranthus Chenopodium Matricaria Viola as per Preparation Ex. No.
24 125 00 95 70 100 100 70 100

Table A-4: Pre-emergence/greenhouse
Active compound g ai./ha Maize Soya Alopecurus Lolium Sorghum Amaranthus Chenopodium Matricaria Solanum
as per Preparation beans
Ex. No.

25 125 0 20 100 70 80 95 100 95 100
40 125 5 20 100 95 100 100 100 100 100
41 125 10 20 100 80 90 100 100 100 100
Table A-5: Pre-emergence/greenhouse
Active compound as per Preparation Ex. No. g ai./ha Wheat Cotton Alopecurus Bromus Echinochloa Amaranthus Chenopodium Veronica
60 125 0 20 90 95 100 100 100 100
61 60 30 0 95 100 100 100 100 80

-78-Example B
Post-emergence test
Solvent: 5 parts by weight of acetone
Emulsifier: 1 part by weight of alkylaryl polyglycol ether
To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
Test plants which have a height of 5-15 cm are sprayed with the preparation of the active compound in such a way as to apply the particular amounts of active compound desired per unit area. The concentration of the spray liquor is chosen so that the particular amounts of active compound desired are applied in 1000 1 of water/ha.
After three weeks, the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control.
The figures denote:
0% = no action (like untreated control) 100% - total destruction
In this test, a very strong activity against weeds (cf. Tables B-l to B-4) is shown, for example, by the compounds of Preparation Examples 6,7, 11, 13, 20, 21, 22, 24, 30, 34, 39, 40, 43, 44, 46, 48, 49, 50, 51, 52, 53, 55, 56 and 59, combined with good tolerance of some compounds by crops, such as for example wheat; "ai." = active ingredient.

Table B-l: Post-emergence test/greenhouse
Active compound g ai./ha Wheat Alopecurus Lolium Sorghum Ipomoea Solanum Stellaria Xanthium as per Preparation Ex. No.

20 60 20 95 90 100 95 100 100 95
21 60 100 95 100 90 100 100 -
22 60 90 90 95 80 80 90 -
24 60 15 90 60 90 90 95 95 -
30 125 95 90 100 90 100 100 100
34 60 20 90 70 100 80 95 80 95
6 60 5 60 50 70 90 95 95 95
7 60 10 95 95 95 95 95 100 -
52 60 90 60 100 90 95 95 95

Table B-2: Post-emergence/greenhouse
Active compound as g ai./ha Wheat Sorghum Ipomoea Solatium Stellaria Xanthium per Preparation Ex.
No.

11 60 0 - 90 70 90 90
13 60 0 80 90 95 95 -
39 60 20 80 80 95 90 95
40 60 20 80 90 95 95 100
43 60 20 70 95 95 90 100
44 60 10 70 95 95 80 100
46 60 - 70 95 95 95 100
48 60 5 100 90 90 60 95
49 60 20 90 90 90 70 95
53 125 20 95 95 59 90 100

oo o

Table B-3: Post-emcrgence/grecnhouse
Active compound as g ai./ha Wheat Amaranthus Matricaria Solanum Xanthium
per Preparation Ex.
No.

55 60 20 95 95 90 100
56 125 10 100 100 100 100
51 125 20 95 95 95 95
Table B-4: Post-emergence/greenhouse
Active compound as g ai./ha Echinochloa Sorghum Amaranthus Solanum Xanthium
per Preparation Ex.
No.

59 60 100 100 100 90 95
49 60 - 90 95 90 95
50 60 80 95 95 95 95








WE CLAIM:
1. Sulphonylamino(thio)carbonyl compounds of the general formula (I):
(Formula Removed)
in which
n r^essnts tiie numbers 0, 1 or 2,
Q represents oxygen or sulphur,
R1 represents hydrogea, fonnyl, represeots in each case optionally cyano-, fluorine-, chlorine-, bromine-, phenyl- or C1-C4-alkoxy-substitirted alkyl, aikoxy, alkylamino, alkoxyamino, dialkylamino, N-alkoxy-N-aikylamino, alkylcaibonyl, alkoxycarbonyl, alfcylsuiphonyi, alkenyl or alkynyl having in each case up to 6 carbon atoms, or represents in each case optionally cyano-j fluorine-, chlorine-, bromiae- or C1-C4-alkyl-substituted C3-C6-cycloalfcyl, C3-C6-cycloalkyl-carbojiyl or C3-C6-cycloalkylsuIphonyl,
R^ represents cyano, fluorine, chlorine, bromine or represents in each case optionally cyano-, fluorine-, chloiine-, bromine- or C1-C4'alkosy-substituted alkyl, aikoxy, alkylthio, aliylsulpMnyl, aJkylsulphonyl,
dialkylaminosulphonyl, alkenyl, alkynyi, alkenyloxy or alkynyloxy having in each case up to 6 carbon atoms and
R3 represeots optionally substituted heterocyclyl of the formula below
(Formula Removed)
1 represents oxygea or sulpiiur and
R4 represents hydrogen, hydroxyij amino, cyano, represeots C2-C10-alkylideneanino;, represents optiomlly fluorine-, clilorine-, bromine-, cyaao-, C1-C4-alkyoxy-, C1-C4-alkyl-carboiiyl- or C1-C4-aIkoxy-carrbosyl-substituted C1-C6-alkyl, represents in each case optionally fluorine-, oillorine- and/or bromine-substituted C2-C6-aikenyl or C2-C6-alfcynyl, represents in each case optionsLlly fluorine-, chlorine-, bioinine-, cyano-, C1-C4-aIkoxy- or C1-C4-aBcoxy-carbonyl-substituted C1-C6-alkoxy, C1-C6-alkylamino or C1-C5-alkyl-carbonylamiao, represents C3-C6-alkenyloxy, represents di-(C1-C4~alkyI)-aniino, represents in each case optionally fluofiae- chlorine-, brwnine-, cyano- and'cr C1-C4aikyl-Substitiited C3-C6 cycioalkyl, C3-C6-cycloalkylamino or C3-C6-cycloalkyl-C1-C4-alkyi, or represents in each case optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, C1-C4-alkyl-, trifluoromethyl' and/or C1-C4-alkoxy-stibstituted phenyl orphenyl -C1-C4-a]tyl,
R5 represents hydrogen, hydroxy!, mercapto, amino, cyano, fluorine, chlorine, bromine, iodine, represents optionally fluorine-, chlorine-, bromine-, cyano-, C1-C4-alkoxy", C1-C4-aHsyl-carbonyl- ox CrC4-ali:oxy-carbony]-substituted C1-C5-alkyl, represents in each case optionally fluorine-, chlorine- and/or bromine-substied C2-C6-alkenyI or C2-C-alkynyl, represesats in each case optionally fluorine-, chlorine-, cyano-, C1-C4-alkoxy- or C1-C4-alkoxy-carbonyl-substituted C1-C6-alkoxy, C1-C6-aliylthio, C1-C6-alkylamino or C1-C6-alkyl-carbonyIamino, represents C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-alkenylthio, C3-C6-alkynylthio,
3-C60-alkenylainiiio or C3-C6-aikynylamino, represents di-(C1-C4-alkyl)-amino, represents in each case optionally methyl- and/or ethyl-substituted aziridino, pyrrolidino, pipK'idino or morphoHno, represents in eacb case optionally fluorine, cMorine-, bromine-, cyaao- and/or C1-C4-aliyi-substituted C3-C5cydoalkyl, C5-C6-cycloaltenyl, C3-Cs-cycloalkyloxy, C3-C6-cycloalkylthio, C3-C6-cycloalkylamino, C3-C6-cycloalkcyl-C1-C4-alkylj C3-C5-cycloalkyI-C1-C4-aIkoxy, C3-C6-cloalkyl~C1-C4-alkylthio or C3-C6-C7cloalkyi-C1-C4-aJky]ammo, or represents m. each case optioimlly fluorine-, chlorine-, bromme-, cyano-, nitro, C1-C4-alkyl-, trifluoiomethyl-, C1-C4-aIkoxy- and/or C1-C4-alkoxy-carboiiyl-substituted phenyl, phenyl-C1-C4-aIkyl, phsnoxy, phenyl-C1-C4-alkoxy, phenylthio, phenyl-C}-C4-alfcylthio: phenylamirto orpiienyl-C1-C4-aIkylammo, or
R4 and R5 together represent optionally bianclied altanediyl having 3 to 11 carbon atoms,
and the salts of compoxmds of the fonnula (I).
2. Compounds of the general formula (I) as claimed in claim 1, wherein n represents the numbers 0,1 or 2,
A represents a single bond,
Q represents oxygen or sulphur,
R1 represents hydrogen, fortnyi, represents in each case optionally fluorine-, cUorin©-, bromine-j methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl^ n-, i- or s-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, meihykmino, ethylamino, n- or i-propylanaino, n-, i-, s- or t-butylainiao, mefhoxyamino, ethoxyamino, n- or i-propoxyamino, n-, i-, s-or t-butoxyamino, dimethylarmno^ diethylamino, N-methoxy-N-raethyl-amino, acetyl, propionyl, butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyi, methylsiilphonyi, ethylsulphonyl, n- or i-propyl-sulphonyl, n-, i-, s- or t-butylsulphonyl, propenyl, bntenyl, propynyl or butyayL, or represents in each case optionally fluorine-, chlorine- or methyi-substimted cyclopropyl, cydopropylcarbonyl or cyclopropylsulphonyi,
R2 represents cyaco, fluorine, chiorine, biomiiie, or represeots in eaci case optionally fltiorine-, ciilorme-, metboxy- or ethoxy-stibstituted methyl, etiyl n- or i-propyl, n-, i- or s-butyl, metloxy, ethoxy, n- or i-propoxy, a-, i- or s-butoxy, metiiyltliio, ethyltisio, a- or i-propyltfaio, D-, i~, s- or t-butylthlo, methylsulpliijiyi, etbyisuJpfciayi, methylsulpiionyl, ethylsuipjhoiiyl, dimeiliylaminosulpionyi or diethylamiaosulphoiiyi, xepresents propenyl, butenyl, propyayl, butyayl, pmpenyloxy, hmmylox/, propynyloxy or butynj'Ioxy and
R3 represcssts optionally substitJatsd hsterocydyl of the fornajla bdow
m which
(Formula Removed)
Q1 rqjresaGts oxygen or sulphur and
R4 represents feydrogen hydroxyl, anino, represents C3-C8-aJiylideaeaaiino, represents hx each case optionally fluorine-, chlorine-, cyano-, methaxy- or ethoxy-subsdtuted raethyl, ethyl, n- or i-propyi, a-, i-, s- or t-biotyl, represents in each case optionlly fluorine-, chlorine- or bromine-substitited propenyl, butenyl, propynyl or btitynyl, represents in each case optjonally fluorine-, chlorine-, cyano- methoxy- or ethosy-substituted methoxy, ethoxy, Q- or i-proposy, n-, i-, s- or t-butoxy, methylainino, ethylamlao, n- or 1-propylamino, n-, i-, s- or t-butylajaino, represents propeayloxy or butenyfoxy, rqprcsects dimethylamino or diethylaiaiiio, or represents in each case optionally fluorine-, cMorice-, naethyl- mdfor ethyl-sub stituted cyclopropyl, cyclobutyl, cyclopentyl cyclohexyl, cyclopiopylamino, cyctobutyiamino, cyclopeatylaniino, cyclohexylamino, cydopxopylmethyi, cyclobutylmethyi, cyclopentyknethyl or cyclohexylmethyl, or represents in each case optioiaally fluorine-, chlorine-, methyl-, trifluoromethyl- and/or methojcj'-substituted phenyl or benzyl,
3 represents hydrogen, hydroxy], marcapto, amino, fluorine, chlorine,
bromine, represents in each case optionally fluorine-, chlorine-, cyano-,
methoxy- or ethoxy-substituted methyl, ethyl, n- or i-piopylj n-, i-, s- or t-
butyl, represents in each case optionally fhiorine-, chorine- ot bromine-
substituted ethenyl, propenyl, butenyL, propynyl or butynyl, represents in
each case optionally fluorine-, chlorine-, cyaoo-, methoxy- or ethoxy-
substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy',
methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio,
methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino,
reqreseaits propenyloxy, butenyloxy, propynyloxy, butynyloxy,
propenylthio, propadienyltMo, butenylthio, propynylthio, butynylthio,
propenylamino, birtenylamino, propynylamino or butylamino, represents
dimethylamdno, diethylaroino or dipropyhratao, represeirts in each case
optionally fluorine-, chlorine-, methyl- and/or ethyl-substituted
cyclopropyi, cyclobutyl, cyclopentyl, cyclofaexyl, cyclopentenyl,
cyclohexenyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclo-
hcsyloxy, cyclopropylthio, cyclobutyithio, cyclopentylthio, cyclohexylthio,
cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino,
cyclopropyhnethyl, cyclobtitylmethyl, oyclopentylmethyl,
cyclohexyimethyl, cyclopropylmethosy, cyclobutylmethoxy,
cyclop entylmethoxy, cyclohesyhnethoxy, cyclopropylmethylThio, cyclobutylmethylthio, cyclopentylmethylthio, cycIohexylraethylthiOj cyclopropylmethylamino, cyclobutyknethylamino, cyclopentylmethyl-amino or cyclohexyknethylandno, or represents in each case optionally fluorine-, chlorine-, methyl-, trifluoromethyl-, methoxy- and/or methojjycarbonyl-substituted phenyl, benzyl, phenoxy, benzyloxy, phenyithio, benzylthio'^ phenylamino or benzylamino, Of
R** and R^ together r^resent optionally branched alkanediyl ha-ving 3 to 11 carbon atoms.
3. Compounds of the formula (I) as claimed in claim 1, wherein
n represents the numbers 0,1 or 2, A represents a single bond,
Q represents oxygen or suiphin,
R1 represesotis in each case optionally fiuonne- and/or chlorine-substituted mcthyl, ethyL, n- or i-propyl, n-, i-, s- or t-butyl,
R2 represents fluorine, chlorine, bromiae, or represents in each case optionaliv fluorine- ami/or cMorme-anbstituted methyij ethyl, methoxy, ctlioxy, methyltbio or ethylthio - in each case in the 6-position - and
R represents optionaliy substituted triazolinyl of the formula below
(Formula Removed)
in which
Q1 represents oxygen or sulphur and
R4 represents in each case optionally fhiorine-, chlorme-, cyano-, methoxy- or ethoxy-substitiited metliyi, ethyl, n- or i-propyl, represents propenyl or propynyl, represents methoxy, ethoxy, n- or i-propoxy, or represents cyclopropyl,
R5 represents hydrogeso, chlorine, bromine, represents in each case optionally fluorine-, chlorine-, cyano-, metlwxy- or ethoxy^substitnted methyl, ethyl, n- or i-propyl, represents in each case optionally fluorine- and/or chlorine-substituted propenyl or propynyl, repressits in each case optionally fluonns-, chlorine-, cyano-, methoxy- or ethoxy-substituted methoxy, cthoxy, n- or i-propoxy, mediyithio, ethyhhio, n- ori-prtopyltMo, represents propenylcxy orcyclopropyl.
4. Process for preparing compounds of the formula (I) as claimed in claim 1 and salts thereof, wherein
aminosulphonyl compounds of the general formula (II)
(Formula Removed)
iawlucla
n, A, R1 and R2 are as defined in Claim 1
are reacted with (thio)carboxylic acid derivatives of the general formula (III)
ia -wliich
Q and R3 are as defmed in Claim 1 and
Z represents halogen, alkoxy, aryloxy or aryalkoxy,
if appropriate in the presexice of an acid acceptor and if appropriate in tiie presence of adilueent.
5. Herbicidal compositions, comprising at least one compound of the formula (I) or a salt thereof as claimed in claim 1.
6. Method for controlling weeds, wherein compounds of the general formula (I) or salts thereof as claimed in claim 1 are allowed to act on the weeds or their habitat.
7. Process for preparing herbicidal compositions, wherein compounds of the general formula (I) or salts thereof as claimed in claim 1 are mixed with extenders and/or surfactants.


Documents:

1281-DEL-1997-Abstract-(11-06-2009).pdf

1281-DEL-1997-Abstract-(26-06-2009).pdf

1281-del-1997-abstract.pdf

1281-DEL-1997-Claims-(11-06-2009).pdf

1281-DEL-1997-Claims-(26-06-2009).pdf

1281-del-1997-claims.pdf

1281-DEL-1997-Correspondence-Others-(11-06-2009).pdf

1281-DEL-1997-Correspondence-Others-(26-06-2009).pdf

1281-del-1997-correspondence-others.pdf

1281-DEL-1997-Description (Complete)-(11-06-2009).pdf

1281-del-1997-description (complete).pdf

1281-del-1997-form-1.pdf

1281-del-1997-form-18.pdf

1281-del-1997-form-2.pdf

1281-DEL-1997-Form-3-(11-06-2009).pdf

1281-del-1997-form-4.pdf

1281-del-1997-form-6.pdf

1281-DEL-1997-GPA-(11-06-2009).pdf

1281-del-1997-gpa.pdf

1281-DEL-1997-Others-Documents-(11-06-2009).pdf

1281-DEL-1997-Petition-137-(11-06-2009).pdf

1281-DEL-1997-Petition-138-(11-06-2009).pdf

abstract.jpg


Patent Number 237649
Indian Patent Application Number 1281/DEL/1997
PG Journal Number 2/2010
Publication Date 08-Jan-2010
Grant Date 31-Dec-2009
Date of Filing 15-May-1997
Name of Patentee BAYER AKTIENGESELLSCHAFT
Applicant Address D-51368 LEVERKUSEN, GERMANY.
Inventors:
# Inventor's Name Inventor's Address
1 MARK-WILHELM DREWES GOETHESTR.38, 40764 LANGENFELD, GERMANY.
2 ERNST-RUDOLF GESING TRILLSER GRABEN 4, 40699 ERKRATH, GERMANY.
3 JOHANNES-RUDOLF JASEN KNIPPRATHER-STR.47, 40789 MONHEIM, GERMANY.
4 ROLF KIRSTEN CARL-LANGHANS-STR.27, 40789 MONHEIM, GERMANY.
5 KLAUS-HELMUT MULLER SOLFSTR.19,40593 DUSSELDORF, GERMANY.
6 KLAUS KONIG ZUM HAHNENBERG 40, 51519 ODENTHAL, GERMANY.
7 PETER ANDRES FELDSTR.12A, 40764 LANGENFELD, GERMANY.
8 MARKUS DOLLINGER BURSCHEIDER STR.154B, 51381 LEVERKUSEN, GERMANY.
9 OTTO SCHALLNER NOLDEWEG 22, 40789 MONHEIM, GERMANY.
10 KURT FINDEISEN DUNFELDER STR.28, 51375 LEVERKUSEN, GERMANY.
11 JOACHIM KLUTH VIRNEBURGSTR.69, 40764 LANGENFELD, GERMANY.
12 ULRICH PHILIPP HOCHSTADENSTR.1-3,50674 KOLN, GERMANY.
13 HANS-JOCHEM RIEBEL IN DER BEEK 92, 42113 WUPPERTAL, GERMANY.
PCT International Classification Number C07D 207/30
PCT International Application Number N/A
PCT International Filing date
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 NA