Title of Invention

SUBSTITUTED THIENE-3-YLSULPHONYLAMINO[THIO] CARBONYLTRIAZOLIN[ETHI] ONES

Abstract The invention relates to novel substituted thiene-3-ylsuphonylamino(thio)carbonyltriazolin(ethi)ones of the genral formula.
Full Text FORM 2
THE PATENTS ACT 1970
[39 OF 1970]
COMPLETE SPECIFICATION
[See Section 10]



"SUBSTITUTED THIENE-3-
YLSULPHONYLAMINO[THIO]CARBONYLTRIAZOLIN[ETHI]ONES"



BAYER AKTIENGESELLSCHAFT, a body corporate organised under the laws of Germany, of D-51368 Leverkusen, Germany,








Le A 35 696-Foreign Countries Lu/klu/NT
-1-Substituted thiene-3-ylsulphonyIamino(thio)carbonyItriazolin(ethi)ones
The invention relates to novel substituted tmene-3-ylsulphonylamino(thio)carbonyl-
5 triazolin(ethi)ones, to processes for their preparation and to their use as herbicides.
It is already known that certain substituted thienylsulphonylamino(thio)carbonyl-triazolin(ethi)ones, such as, for example, the compounds methyl 4-[[[(4,5-dihydro-3-ethoxy-4-methyl-5-oxo-lH-l,2,4-triazol-l-yl)carbonyl]amino]sulfonyl]-5-methyl-3-
10 thiophenecarboxylate, methyl 4-[[[(4,5-dihydro-3-methoxy-4-methyI-5-oxo-lH-
1,2,4-triazol-1 -yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate, meth¬
yl 4-[[[(4,5-dihydro-4-methyl-5-oxo-3-n-propoxy-1H-1,2,4-triazol-1 -yl)carbon-
yl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate, methyl" 4-[[[(4,5-dihydro-4-
methyl-5-oxo-3-isopropoxy- 1H-1,2,4-triazol-1 -yl)carbonyl]amino]sulfonyl]-5-meth-
15 yl-3-thiophenecarboxylate, methyl 4-[[[(4-cyclopropyl-4,5-dihydro-3-methoxy-5-
oxo-lH-1,2,4-triazol-l -yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarb-oxylate, methyl 4-[[[(4-cyclopropyl-4,5-dihydro-3-ethoxy-5-oxo-lH-l,2,4-triazol-1-yI)carbonyl]ammo]suIfonyl]-5-methyl-3-thiophenecarboxylate, methyl 4-[[[(4-cyclo-propyl-4,5-dihydro-5-oxo-3-n-propoxy-lH-l,2,4-triazol-l-yl)carbonyl]amino]sulf-
20 onyl]-5-methyl-3-thiophenecarboxylate, methyl 4-[[[(4-cyclopropyl-4,5-dihydro-5-
oxo-3-isopropoxy-lH-l,2,4-triazol-l-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thio-phenecarboxylate, methyl 4-[[[(3,4-dicyclopropyl-4,5-dihydro-5-oxo-lH-l,2,4-tri-azol-l-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate, methyl 4-[[[(4,5-dihydro-3,4-dimethyl-5-oxo- 1H-1,2,4-triazol-1 -yl)carbonyl]amino]sulfonyl]-
25 5-methyl-3-thiophenecarboxylate, methyl 4-[[[(4,5-dihydro-3-ethyl-4-methyl-5-oxo-
lH-l,2,4-triazol-l-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate, methyl 4-[[[(4,5-dihydro-4-methyl-3-methylthio-5-oxo-lH-l,2,4-triazol-l-yl)carb-onyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate, ethyl 4-[[[(4,5-dihydro-3,4-dimethoxy-5-oxo-lH-l,2,4"triazol-l-yl)carbonyl]amino]sulfonyl]-5-chloro-3-thio-
30 phenecarboxylate, methyl 4-[[[(4,5-dihydro-3-ethoxy-4-methyl-5-oxo-lH-l,2,4-tri-
azol-1 -yl)thioxocarbonyl] aminojsulfonyl] -5 -fluoro-3 -thiophenecarboxylate, methyl
2

Le A 35 696-Foreign Countries
-2-
4-[[[(4,5-dihydro-3-ethyl-4-methoxy-5-thioxo-lH-l,2,4-triazol-l-yl)carb-
ony 1] amino] sulfony 1] -5 -trifluoromethy 1-3 -thiophenecarboxy late, ethyl 4- [ [ [(4,5 -di-
hydro-4-ethyl-3-methoxy-5-oxo-lH-l,2,4-triazol-l-yl)carbonyl]-ammo]sulfonyl]-5-
methyl-3-thiophenecarboxylate and isopropyl 4-[[[(3,4-dimethyl-5-oxo-4,5-dihydro-
5 lH-l,2,4-triazol-l-yl)carbonyl]amino]sulfonyl]-5-ethyl-3-thiophenecarboxylate, have
herbicidal properties (cf. WO-A-01/05788, cf. also WO-A-97/16449, WO-A-98/24787). However, the activity of these compounds is not entirely satisfactory.
This invention now provides the novel substituted thiene-3-ylsulphonylamino(thio)-
10 carbonyltriazolin(ethi)ones of the general formula (I)


(I)

in which
15 Q1 represents O (oxygen) or S (sulphur),
■a
Q represents O (oxygen) or S (sulphur),
R represents optionally cyano-, halogen- or C1-C4-alkoxy-substituted alkyl
20 having 1 to 6 carbon atoms, represents in each case optionally cyano- or
halogen-substituted alkenyl or alkynyl having in each case 2 to 6 carbon
atoms, representing in each case optionally cyano-, halogen- or C1-C4-alkyl-
substituted cycloalkyl or cycloalkylalkyl having in each case 3 to 6 carbon
atoms in the cycloalkyl group and, if appropriate, 1 to 4 carbon atoms in the
25 alkyl moiety, represents in each case optionally nitro-, cyano-, halogen-,
C1-C4-alkyl- or C1-C4-alkoxy-substituted aryl or arylalkyl having in each case



3

Le A 35 696-Foreign Countries
-3-
6 or 10 carbon atoms in the aryl group and, if appropriate, 1 to 4 carbon atoms
in the alkyl moiety, or represents in each case optionally nitro-, cyano-,
halogen-, Ci-C4-alkyl- or Ci-C4-alkoxy-substituted heterocyclyl or hetero-
cyclylalkyl having in each case up to 6 carbon atoms and additionally 1 to 4
5 nitrogen atoms and/or 1 or 2 oxygen or sulphur atoms in the heterocyclyl
group and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety,
R2 represents hydrogen, cyano, nitro, halogen, represents in each case optionally,
cyano-, halogen- or Ci-C4-alkoxy-substituted alkyl, alkoxy, alkoxycarbonyl,
10 alkylthio, alkylsulfmyl or alkylsulfonyl having in each case 1 to 6 carbon
atoms in the alkyl group, or represents in each case optionally cyano- or halogen-substituted alkenyl, alkynyl, alkenyloxy or alkynyloxy having in each case 2 to 6 carbon atoms in the alkenyl or alkynyl group,
15 R3 represents hydrogen, hydroxyl, mercapto, amino, cyano, halogen, represents
optionally cyano-, halogen-, C;[-C4-alkoxy-, Ci-C4-alkyl-carbonyl- or C\-C4-alkoxy-carbonyl-substituted alkyl having 1 to 6 carbon atoms, represents in each case optionally fluorine-, chlorine- and/or bromine-substituted alkenyl or alkynyl having in each case 2 to 6 carbon atoms, represents in each case
20 optionally cyano-, halogen-, Ci-C4-alkoxy- or Ci-C4-alkoxy-carbonyl-
substituted alkoxy, alkylthio, alkylamino or alkylcarbonylamino having in each case 1 to 6 carbon atoms in the alkyl group, represents alkenyloxy, alkynyloxy, alkenylthio, alkynylthio, alkenylamino or alkynylamino having in each case 3 to 6 carbon atoms in the alkenyl or alkynyl group, represents
25 dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups,
represents in each case optionally methyl- and/or ethyl-substituted aziridino, pyrrolidino, piperidino or morpholino, represents in each case optionally fluorine-, chlorine-, bromine-, cyano- and/or Ci-C4-alkyl-substituted cycloalkyl, cycloalkenyl, cycloalkyloxy, cycloalkylthio, cycloalkylamino,
30 cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylthio or cycloalkylalkyl-
amino having in each case 3 to 6 carbon atoms in the cycloalkyl or
-M-

Le A 35 696-Foreign Countries
4-
cycloalkenyl group and, if appropriate, 1 to 4 carbon atoms in the alkyl
moiety, or represents in each case optionally fluorine-, chlorine-, bromine-,
cyano-, nitro-, C1-C4-alkyl-, trifluoromethyl-, C1-C4-alkoxy- and/or C1-C4-
alkoxy-carbonyl-substituted aryl, arylalkyl, aryloxy, arylalkoxy, arylthio,
5 arylalkylthio, arylamino or arylalkylamino having in each case 6 or 10 carbon
atoms in the aryl group and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety, and
R4 represents hydrogen, hydroxy, amino, cyano, represents C2-C10-
10 alkylideneamino, represents optionally fluorine-, chlorine-, bromine-, cyano-,
C1-C4-alkoxy-, C1-C4-alkyl-carbonyl- or C1-C4-alkoxy-carbonyl-substituted alkyl having 1 to 6 carbon atoms, represents in each case optionally fluorine-, chlorine- and/or bromine-substituted alkenyl or alkynyl having in each case 2 to 6 carbon atoms, represents in each case optionally fluorine-, chlorine-,
15 bromine-, cyano-, C1-C4-alkoxy- or C1-C4-alkoxy-carbonyl-substituted
alkoxy, alkylamino or alkylcarbonylamino having in each case i to 6 carbon atoms in the alkyl group, represents alkenyloxy having 3 to 6 carbon atoms, represents dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups, represents in each case optionally fluorine-, chlorine-, bromine-,
20 cyano- and/or C1-C4-alkyl-substituted cycloalkyl, cycloalkylamino or
cycloalkylalkyl having in each case 3 to 6 carbon atoms in the alkyl group and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety, or represents in each case optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, C1-C4-alkyl-, trifluoromethyl- and/or C1-C4-alkoxy-substituted aryl or arylalkyl
25 having in each case 6 or 10 carbon atoms in the aryl group and, if appropriate,
1 to 4 carbon atoms m the alkyl moiety, or together with R represents optionally branched and/or C1-C4-alkyl-substituted alkanediyl, oxaalkanediyl, thiaalkanediyl or azaalkanediyl having 3 to 6 carbon atoms, where the oxa, thia or aza components may be positioned at the beginning, at the end or
30 within the alkanediyl grouping,
5

Le A 35 696-Foreign Countries
-5-
- and salts of the compounds of the formula (I) -
except for the compounds methyl 4-[[[(4,5-dihydro-3-ethoxy-4-methyl-5-oxo-lH-
1,2,4-triazol-l-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate, meth-
5 yl 4-[[[(4,5-dihydro-3-methoxy-4-methyl-5-oxo-1H-1,2,4-triazol-1 -yl)carbonyl]ami-
no]sulfonyl]-5-methyl-3-thiophenecarboxylate, methyl 4-[[[(4,5-dihydro-4-methyl-5-oxo-3-n-propoxy- 1H-1,2,4-triazol-1 -yl)carbonyl]amino]sulfonyl]-5-methyl-3-thio-phenecarboxylate, methyl 4-[[[(4,5-dihydro-4-methyl-5-oxo-3-isopropoxy-lH-l ,2,4-triazol-l-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate, methyl 4-
10 [[[(4-cyclopropyl-4,5-dihydro-3-methoxy-5-oxo-lH-l,2,4-triazol-l-yl)carb-
onyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate, methyl 4-[[[(4-cyclopropyl-4,5-dihydro-3-ethoxy-5-oxo-lH-l,2,4-triazol-l-yl)carbonyl]amino]sulfonyl]-5-meth-yl-3-thiophenecarboxylate, methyl 4-[[[(4-cyclopropyl-4,5-dihydro-5-oxo-3-n-prop-oxy-lH-l,2,4-triazol-l-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarb-
15 oxylate, methyl 4-[[[(4-cyclopropyl-4,5-dihydro-5-oxo-3-isopropoxy-lH-l,2,4-tri-
azol-l-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate, methyl 4-[[[(3,4-dicyclopropyl-4,5-dihydro-5-oxo-1H-1,2,4-triazol-1 -yl)carbonyl] amino]-sulf-onyl]-5-methyl-3-thiophenecarboxylate, methyl 4-[[[(4,5-dihydro-3,4-dimethyl-5-oxo-1H-1,2,4-triazol-1 -yl)carbonyl] amino] sulfonyl]-5 -methyl-3 -thiophenecarb-
20 oxylate, methyl 4-[[[(4,5-dihydro-3-ethyl-4-methyl-5-oxo-lH-l,2,4-triazol-l-yl)carb-
onyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate, methyl 4-[[[(4,5-dihydro-4-methyl-3-methylthio-5-oxo-lH-l,2,4-triazol-l-yl)carbonyl]amino]sulfonyl]-5-meth-yl-3-thiophenecarboxylate, ethyl 4-[[[(4,5-dihydro-3,4-dimethoxy-5-oxo-lH-l,2,4-triazol-l-yl)carbonyl]amino]sulfonyl]-5-chloro-3-thiophenecarboxylate, methyl 4-
25 [[[(4,5-dihydro-3-ethoxy-4-methyl-5-oxo-lH-l,2,4-triazol-l-yl)thioxocarbonyl]-
amino]sulfonyl]-5-fluoro-3-thiophenecarboxylate, methyl 4-[[[(4,5-dihydro-3-ethyl-4-methoxy-5-thioxo-lH-l,2,4-triazol-l-yl)carbonyl]amino]sulfonyl]-5-trifluoro-methyl-3-thiophenecarboxylate, ethyl 4-[[[(4,5-dihydro-4-ethyl-3-methoxy-5-oxo-lH-l,2,4-triazol-l-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate
30 and isopropyl 4-[[[(3,4-dimethyl-5-oxo-4,5-dihydro-lH-l,2,4-triazol-l-yl)carb-
onyl]amino]sulfonyl]-5-ethyl-3-thiophenecarboxylate known from WO-A-01/05788,
6

Le A 35 696-Foreign Countries
which are excluded by disclaimer.
Saturated or unsaturated hydrocarbon groupings, such as alkyl, allkanediyl, alkenyl
5 or alkynyl, are in each case straight-chain or branched as far as this is possible -
including in combinations with heteroatoms, such as in alkoxy.
Optionally substituted radicals can be mono- or polysubstituted, and in the case of polysubstitution, the substituents can be identical or different.
10
Preferred substituents or ranges of the radicals present in the formulae listed above and below are defined below.
Q1 preferably represents O (oxygen) or S (sulphur).
15
Q2 preferably represents 0 (oxygen) or S (sulphur).
R1 preferably represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or isoproyl, n-, iso-, s- or t-
20 butyl, represents in each case optionally cyano-, fluorine- or chlorine-
substituted propenyl, butenyl, propynyl or butynyl, represents in each case optionally cyano-, fluorine-, chlorine-, methyl- or ethyl-substituted cyclo-propyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutyl-methyl, cyclopentylmethyl or cyclohexylmethyl, represents in each case
25 optionally cyano-, fluorine-, chlorine-, methyl-, ethyl-, n- or isopropyl-,
trifluoromethyl-, methoxy-, ethoxy-, n- or isopropoxy-, difluoromethoxy- or trifluoromethoxy-substituted phenyl, phenylmethyl or phenylethyl, or represents in each case optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or isopropyl-, methoxy-, ethoxy-, n- or isopropoxy-
30 substituted heterocyclyl or heterocyclylmethyl, where the heterocyclyl group
7

Le A 35 696-Foreign Countries
-7-
is in each case selected from the group consisting of oxetanyl, thietanyl, furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl.
R2 preferably represents hydrogen, cyano, fluorine, chlorine, bromine, represents
5 in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-
substituted methyl, ethyl, n- or isopropyl, n-, iso-, s- or t-butyl, methoxy,
ethoxy, n- or isopropoxy, methoxycarbonyl, ethoxycarbonyl, n- or iso-
propoxycarbonyl, methylthio, ethylthio, n- or isopropylthio, methylsulfinyl,
ethylsulfinyl, methylsulfonyl or ethylsulfonyl, or represents in each case
10 optionally cyano-, fluorine- or chlorine-substituted propenyl, butenyl,
propynyl, butynyl, propenyloxy, butenyloxy, propynyloxy or butynyloxy.
R3 preferably represents hydrogen, hydroxy, mercapto, amino, cyano, fluorine, , chlorine, bromine, represents in each case optionally fluorine-, chlorine-,
15 cyano-, methoxy-, ethoxy-, n- or isopropoxy-, acetyl-, propionyl-, n- or
isobutyroyl-, methoxycarbonyl-, ethoxycarbonyl-, n- or isopropoxycarbonyl-substituted methyl, ethyl, n- or isopropyl, n-, iso-, s- or t-butyl, n-, iso-, s- or t-pentyl or neopentyl, represents in each case optionally fluorine-, chlorine-and/or bromine-substituted ethenyl, propenyl, butenyl, ethynyl, propynyl or
20 butynyl, represents in each case optionally fluorine-, chlorine-, cyano-,
methoxy-, ethoxy-, n- or isopropoxy-, n-, iso-, s- or t-butoxy-, methoxy¬carbonyl-, ethoxycarbonyl-, n- or isopropoxycarbonyl-substituted methoxy, ethoxy, n- or isopropoxy, n-, iso-, s- or t-butoxy, n-, iso-, s- or t-pentyloxy or neopentyloxy, methylthio, ethylthio, n- or isopropylthio, n-, iso-, s- or t-
25 butylthio, methylamino, ethylamino, n- or isopropylamino, n-, iso-, s- or t-
butylamino, acetylamino or propionylamino, represents propenyloxy, butenyloxy, ethynyloxy, propynyloxy, butynyloxy, propenylthio, butenylthio, propynylthio, butynythio, propenylamino, butenylamino, propynylamino or butynylamino, represents dimethylamino, diethylamino or dipropylamino,
30 represents in each case optionally fluorine-, chlorine-, methyl- and/or ethyl-
substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl,



8

Le A 35 696-Foreign Countries
-8-
cyclohexenyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyl-
oxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclo-
propylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclo-
propylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl,
5 cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexyl-
methoxy, cyclopropylmethylthio, cyclobutylmethylthio, cyclopentylmethyl-
thio, cyclohexylmethylthio, cyclopropylmethylarnino, cyclobutylmethyl-
amino, cyclopentylmethylammo or cyclohexylmethylammo, or represents in
each case optionally fluorine-, chlorine-, bromine-, methyl-, trifluoromethyl-,
10 methoxy- or methoxycarbonyl-substituted phenyl, benzyl, phenoxy,
benzyloxy, phenylthio, benzylthio, phenylamino or benzylamino.
R4 preferably represents hydrogen, hydroxy, amino, represents in each case optionally fluorine-, chlorine-, cyano-, methoxy- or ethoxy-substituted
15 methyl, ethyl, n- or isopropyl, n-, iso-, s- or t-butyl, represents in each case
optionally fluorine-, chlorine- and/or bromine-substituted ethenyl, propenyl, butenyl, propynyl or butynyl, represents in each case optionally fluorine-, chlorine-, cyano-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or isopropoxy, n-, iso-, s- or t-butoxy, methylamino, ethylamino, n- or
20 isopropylamino, n-, iso-, s- or t-butylamino, represents propenyloxy or
butenyloxy, represents dimethylamino or diethylamino, represents in each case optionally fluorine-, chlorine-, methyl- and/or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylamino, cyclo¬butylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclo-
25 butylmethyl, cyclopentylmethyl or cyclohexylmethyl, or represents in each
case optionally fluorine-, chlorine-, methyl-, trifluoromethyl- and/or methoxy-substituted phenyl or benzyl.
R and R together preferably represent trimethylene (propane-1,3-diyl), 1-
30 oxatrimethylene, 1-thiatrimethylene, 1-azatrimethylene, tetramethylene
(butane-1,4-diyl), 1-oxatetramethylene, 1-thiatetramethylene, 1-azatetrameth-



9

Le A 35 696-Foreign Countries
ylene or pentamethylene (pentane-l,5-diyl), each of which is optionally mono- to trisubstituted by methyl and/or ethyl, where the position 1 is connected to the point of attachment of R3.
5 Q1 particularly preferably represents O (oxygen) or S (sulphur).
Q2 particularly preferably represents 0 (oxygen) or S (sulphur).
R1 particularly preferably represents in each case optionally fluorine-, chlorine-,
10 methoxy- or ethoxy-substituted methyl, ethyl, n- or isopropyl.
R2 particularly preferably represents fluorine, chlorine, bromine or represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or isopropyl.
15
R3 particularly preferably represents hydrogen, chlorine, bromine, represents in each case optionally fluorine-, chlorine-, methoxy-, ethoxy-, n- or isopropoxy-substituted methyl, ethyl, n- or isopropyl, n-, iso-, s- or t-butyl, n-, iso-, s- or t-pentyl or neopentyl, represents in each case optionally fluorine- or chlorine-
20 substituted ethenyl, propenyl, butenyl, propynyl or butynyl, represents in each
case optionally fluorine-, chlorine-, methoxy-, ethoxy-, n- or isopropoxy-substituted methoxy, ethoxy, n- or isopropoxy, n-, iso-, s- or t-butoxy, n-, iso-, s- or t-pentyloxy, neopentyloxy, methylthio, ethylthio, n- or isopropylthio, n-, iso-, s- or t-butylthio, methylamino, ethylamino, n- or isopropylamino,
25 represents propenyloxy, propynyloxy, propenylthio, propynylthio, propenyl-
amino or propynylamino, represents dimethylamino or diethylamino, represents in each case optionally fluorine-, chlorine- or methyl-substituted cyclopropyl, cyclopropyloxy, cyclopropylmethyl, cyclopropylmethoxy, cyclobutyloxy, cyclopentyloxy or cyclohexyloxy, or represents in each case
30 optionally fluorine-, chlorine- or methyl-substituted phenoxy or benzyloxy.
10

Le A 35 696-Foreign Countries
-10-
R4 particularly preferably represents in each case optionally fluorine-, chlorine-,
methoxy- or ethoxy-substituted methyl, ethyl, n- or isopropyl, represents in
each case optionally fluorine- or chlorine-substituted ethenyl, propenyl or
propynyl, represents in each case optionally fluorine-, chlorine-, methoxy- or
5 ethoxy-substituted methoxy, ethoxy, n- or isopropoxy, represents methyl-
amino, or represents cyclopropyl.
R3 and R4 together particularly preferably represent trimethylene (propane-l,3-diyl),
1-oxatrimethylene, 1-thiatrimethylene, 1-azatrimethylene, tetramethylene
10 (butane- 1,4-diyl), 1-oxatetramethylene, 1-thiatetramethylene, 1-
azatetramethylene or pentamethylene (pentane-l,5-diyl), each of which is optionally mono- or disubstituted by methyl, where the position 1 is connected to the point of attachment of R .
15 The invention preferably also provides the sodium, potassium, lithium, magnesium,
calcium, ammonium, C1-C4-alkylammonium, (where the alkyl radical is optionally substituted by hydroxyl), di(C1-C4-alkyl)ammonium, tri(C1-C4-alkyl)ammonium, tetra(C1-C4-alkyl)arnmonium, tri(C1-C4-alkyl)sulfonium, C5- or C6-cyclo-alkylammonium and di(C1-C2-alkyl)benzylarnmonium salt and also the di(C1-C2-
20 alkyl)pyridinylammonium salts and the pyrrolidinium salts of compounds of the
formula (I) in which Q1, Q2, R1, R2, R3 and R4 have the meanings given above as being preferred.
A very particularly preferred group are those compounds of formula (I) in which 25
R1 represents methyl and Ql and Q2 and R2, R3 and R4 have the meanings given above as being particularly preferred,
except for the prior-art compounds methyl 4-[[[(4,5-dihydro-3-ethoxy-4-methyl-5-
30 oxo-lH-l,2,4-triazol-l-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxyl-
ate, methyl 4-[[[(4,5-dihydro-3-methoxy-4-methyl-5-oxo-lH-l,2,4-triazol-l-yl)carb-

Le A 35 696-Foreign Countries
-11-
onyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate, methyl 4-[[[(4,5-dihydro-4-
methyl-5-oxo-3-n-propoxy-lH-l,2,4-triazol-l-yl)carbonyl]amino]sulfonyl]-5-
methyl-3-thiophenecarboxylate, methyl 4-[[[(4,5-dihydro-4-methyl-5-oxo-3-
isopropoxy-lH-l,2,4-triazol-l-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thio-
5 phenecarboxylate, methyl 4-[[[(4-cyclopropyl-4,5-dihydro-3-methoxy-5-oxo-lH-
l,2,4-triazol-l-yl)carbonyl]-amino]sulfonyl]-5-methyl-3-thiophenecarboxylate, methyl 4-[[[(4-cyclopropyl-4,5-dihydro-3-ethoxy-5-oxo-1H-1,2,4-triazol-1 -yl)carb-onyl]amino]sulfonyl]-5-methyl-3-thiopheneearboxylate, methyl 4-[[[(4-cyclopropyl-4,5-dihydro-5-oxo-3-n-propoxy-lH-l,2,4-triazol-l-yl)carbonyl]amino]sulfonyl]-5-
10 methyl-3-thiophenecarboxylate, methyl 4-[[[(4-cyclopropyl-4,5-dihydro-5-oxo-3-
isopropoxy-lH-l,234-triazol-l-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thio-phenecarboxylate, methyl 4-[[[(3,4-dicyclopropyl-4,5-dmydro-5-oxo-lH-l,2,4-tri-azol-l-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate, methyl 4-[[[(4,5-dihydro-3,4-dimethyl-5-oxo-lH-l,234-triazol-l-yl)carbonyl]amino]sulfonyl]-
15 5-methyl-3-thiophenecarboxylate, methyl 4-[[[(4,5-dihydro-3-ethyl-4-methyl-5-oxo-
lH-l,2,4-triazol-l-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate, methyl 4-[[[(4,5-dihydro-4-methyl-3-methylthio-5-oxo-lH-l,2,4-triazol-l-yl)carb-onyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate, methyl 4-[[[(4,5-dihydro-3-ethoxy-4-methyl-5-oxo-1H-1,2,4-triazol-1-yl)thioxocarbonyl] amino] sulfonyl]-5-
20 fluoro-3-thiophenecarboxylate and methyl 4-[[[(4,5-dihydro-3-ethyl-4-methoxy-5-
thioxo-lH-l,2,4-triazol-l-y1)carbonyl]amino]sulfonyl]-5-trifluoromethyl-3-thio-phenecarboxylate.
A further very particularly preferred group are those compounds of the formula (I) in
25 which
R1 represents ethyl and Q1 and Q2 and R2, R3 and R4 have the meanings given above as being particularly preferred,
30 except for the prior-art compounds ethyl 4-[[[(4,5-dihydro-3,4-dimethoxy-5-oxo-lH-
l,2,4-triazol-l-yl)carbonyl]amino]sulfonyl]-5-chloro-3-thiophenecarboxylate and
12

Le A 35 696-Foreign Countries
-12-
ethyl 4-[[[(4,5-dihydro-4-ethyl-3-methoxy-5-oxo-lH-l,2,4-triazol-l-yl)carbonyl]-amino]sulfonyl]-5-methyl-3-thiophenecarboxylate.
A further very particularly preferred group are those compounds of the formula (I) in
5 which
R1 represents n-propyl and Ql and Q2 and R2, R3, and R4 have the meanings given above as being particularly preferred.
10 A further very particularly preferred group are those compounds of the formula (I) in
which
R1 represents isopropyl and Q1 and Q2 and R2, R3 and R4 have the meanings given
above as being particularly preferred, except for the prior-art compound isopropyl 4-
15 [[[(3,4-dimethyl-5-oxo-4,5-dihydro-lH-l,2,4-triazol-l-yl)carbonyl]amino]sulfonyl]-
5-ethyl-3-thiophenecarboxylate.
A further very particularly preferred group are those compounds of the formula (I) in which
20
Q1 and Q2 and R1 and R2 have the meanings given above as being particularly preferred and R3 and R4 together represent trimethylene (propane- 1,3-diyl), 1-oxatrimethylene, 1-thiatrimethylene, 1-azatrimethylene, tetramethylene (butane-1,4-diyl), 1-oxatetramethylene, 1-thiatetramethylene, 1-azatetramethylene or
25 pentamethylene (pentane-l,5-diyl), each of which is optionally mono- or
disubstituted by methyl, where the position 1 is connected to the point of attachment ofR3.
Further groups which may be particularly emphasized are:
13

Le A 35 696-Foreign Countries
-13-
Group 1:
Compounds in which R3 represents halogen- or C1-C4-alkoxy-substituted alkoxy
5 having 1 to 6 carbon atoms.
Group 2:
Compounds in which R3 represents optionally methyl- and/or ethyl-substituted
10 cycloalkoxy having 3 to 6 carbon atoms.
Group 3:
Compounds in which R3 represents optionally fluorine-, chlorine-, bromine-, methyl-
15 , trifluoromethyl-, methoxy- or methoxycarbonyl-substituted phenoxy or benzyloxy.
The abovementioned general or preferred radical definitions apply both to the end
products of the formula (I) and, correspondingly, to the starting materials or
intermediates required in each case for the preparation. These radical definitions can
20 be combined with one another as desired, i.e. including combinations between the
given preferred ranges.
Preference according to the invention is given to those compounds of the formula (I) which contain a combination of the meanings listed above as being preferred. 25
Particular preference according to the invention is given to those compounds of the formula (I) which contain a combination of the meanings listed above as being particularly preferred.
14

Le A 35 696-Foreign Countries
-14-
Very particular preference according to the invention is given to those compounds of the formula (I) which contain a combination of the meanings listed above as being very particularly preferred.
5 The novel substituted thien-3-yl sulphonylamino(thio)carbonyl triazolin(ethi)ones of
the general formula (I) have interesting biological properties. In particular, they have strong herbicidal activity.
The novel substituted thien-3-yl sulphonylamino(thio)carbonyl triazolin(ethi)ones of
10 the general formula (I) are obtained when
(a) substituted thiophene-3-sulphonamides of the general formula (II)


(II)

15 in which
1 7
R and R are as defined above,
are reacted with substituted triazolin(ethi)ones of the general formula (III)
20


25

in which
Q1,Q2,R3andR4 are as defined above and
-15

Le A 35 696-Foreign Countries
15

5

Z represents halogen, alkoxy, aryloxy or arylalkoxy,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
or when
(b) substituted thien-3-yl sulphonyl iso(thio)cyanates of the general formula (IV)


10
Q1RlandR2 are as defined above,
15 are reacted with triazolin(ethi)ones of the general formula (V)

20 Q2, R4 and R5 are as defined above,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
25 or when
--16-

Le A 35 696-Foreign Countries
16
(c) substituted thiophene-3-sulphonyl chlorides of the general formula (VI)

R1 0 CI
, , (V|)
"/ \X0-# ,S02
s" *2

in which

,1 „„JT>2
R1 and Rz are as defined above,

are reacted with triazolin(ethi)ones of the general formula (V)
10

in which
Q2, R4 and R5 are as defined above,

15

and metal (thio)cyanates of the general formula (VII)
M-Q1-CN (VII)

20 in which
Q1 is as defined above,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence
25 of a diluent,
17

Le A 35 696-Foreign Countries
-17-
or when
(d) substituted thiophene-3-sulphonyl chlorides of the general formula (VI)
5

R1 P CI
C—\ S02
"/ ^
(VI)
s" *2

in which

10

R"andR2 are as defined above,
are reacted with triazolin(ethi)one (thio)carboxamides of the general formula (VIII)


in which
15
Q1, Q2,R3and R4 are as defined above,

20

if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
or when
(e) substituted thien-3-yl sulphonylamino(thio)carbonyl compounds of the general formula (IX)



25

18

Le A 35 696-Foreign Countries
-18



5

10
in which
Q2, R4 and R5 are each as defined above,
15 if appropriate in the presence of a reaction auxiliary and if appropriate in the presence
of a diluent,
and the compounds of the formula (I) obtained by the processes (a), (b), (c), (d) or (e) are, if appropriate, converted by customary methods into salts.
20
Using, for example, 2-bromo-4-ethoxycarbonyl thiophene-3-sulphonamide and 4,5-dimethoxy-2-phenoxycarbonyl-2,4-dihydro-3H-l,2,4-triazol-3-one as starting materi¬als, the course of the reaction in the process (a) according to the invention can be illustrated by the following formula scheme;
19

Le A 35 696-Foreign Countries
19





Using, for example, 2-dichloromethyl-4-methoxycarbonyl thien-3-yl-sulphonyl iso-thiocyanate and 5-ethoxy-4-methyl-2,4-dihydro-3H-l,2,4-triazol-3-one as starting materials, the course of the reaction in the process (b) according to the invention can be illustrated by the following formula scheme:




10 Using, for example, 4-ethoxycarbonyl-2-ethyl thiophene-3-sulphonyl chloride,
5-ethyl-4-methoxy-2,4-dihydro-3H-l,2,4-triazole-3-thione and potassium cyanate as starting materials, the course of the reaction in the process (c) according to the invention can be illustrated by the following formula scheme:
20

Le A 35 696-Foreign Countries
-20-



KOCN

Using, for example, 4-ethoxycarbonyl-2-trifluoromethyl thiophene-3-sulphonyl
chloride and 4-ethyl-5-methoxy-2,4~dihydro-3H-l,2,4-triazol-3-one-2-carboxarnide
5 as starting materials, the course of the reaction in the process (d) according to the
invention can be illustrated by the following formula scheme:




10 Using, for example, O-methyl N-(2-ethyl-4-isopropoxycarbonyl thien-3-yl-
sulphonyl)urethane and 4,5-dimethyl-2,4-dihydro-3H-l,2,4-triazol-3-one as starting materials, the course of the reaction in the process (e) according to the invention can be illustrated by the following formula scheme:
21

Le A 35 696-Foreign Countries
21

hH. H-.A.^CH
*d
S02 Vi-
2 + N-
(CH3)2CH,_ ft Hl\_ CH3 H-|>J-^fJ
CH
3
C„HC
S ^2M5 O
N" 3
°KX"CH
(CH3)2CH 9 Hi\ Vl
S02 CH3


10

The formula (II) provides a general definition of the substituted thiophene-3-sulphonamides to be used as starting materials in the process (a) according to the invention for preparing compounds of the general formula (I). In the general formula
1 9
(II), R1 and R" preferably or in particular have those meanings which have already been mentioned above, in connection with the description of the compounds of the general formula (I) according to the invention, as being preferred or particularly preferred for R1 and R2.
The substituted thiophene-3-sulphonamides of the general formula (II) are known and/or can be prepared by processes known per se (cf. J. Org. Chem. 45 (1980), 617-620, WO-A-01/05788).

15 The substituted thiophene-3-sulphonamides of the general formula (II) are obtained
when substituted thiophene-3-sulphonyl chlorides of the general formula (VI)

22
in which

Le A 35 696-Foreign Countries
-22-
R1and R" are as defined above,
are reacted with ammonia or ammonium salts, such as, for example, ammonium
5 acetate or ammonium carbonate, if appropriate in the presence of a diluent, such as,
for example, water or methylene chloride, at temperatures between 0°C and 100°C.
The formula (III) provides a general definition of the substituted triazolin(ethi)ones furthermore to be used as starting materials in the process (a) according to the
10 invention for preparing compounds of the general formula (I). In the general formula
(III), Q1, Q2, R3 and R4 preferably or in particular have those meanings which have already been mentioned above, in connection with the description of the compounds of the general formula (I) according to the invention, as being preferred or particularly preferred for Q1, Q2, R3 and R4.
15
The starting materials of the general formula (III) are known and/or can be prepared by processes known per se (cf. EP-A-341 489, EP-A-422 469, EP-A-425 948, EP-A-431 291, EP-A-507 171, EP-A-534 266).
20 The formula (IV) provides a general definition of the substituted thien-3-yl sulphonyl
iso(thio)cyanates to be used as starting materials in the process (b) according to the invention for preparing compounds of the general formula (I). In the general formula (IV), Q\ Rl and R^ preferably or in particular have those meanings which have already been mentioned above, in connection with the description of the compounds
25 of the general formula (I) according to the invention, as being preferred or
particularly preferred for Q1, R1 and R2.
The starting materials of the general formula (IV) are known and/or can be prepared by processes known per se (cf. US-A-47 01 535).
23

Le A 35 696-Foreign Countries
-23-
The formula (V) provides a general definition of the triazolin(ethi)ones to be used as
starting materials in the processes (b), (c) and (e) according to the invention for
preparing compounds of the general formula (I). In the general formula (V), Q2, R4
and R5 preferably or in particular have those meanings which have already been
5 mentioned above, in connection with the description of the compounds of the general
formula (I) according to the invention, as being preferred or particularly preferred for Q2,R4andR5.
The starting materials of the general formula (V) are known and/or can be prepared
10 by processes known per se (cf. EP-A-341 489, EP-A-422 469, EP-A-425 948, EP-A-
431 291, EP-A-507 171, EP-A-534 266).
The formula (VI) provides a general definition of the substituted thiophene-3-sulphonyl chlorides to be used as starting materials in the processes (c) and (d)
15 according to the invention for preparing compounds of the general formula (I). In the
general formula (VI), R1 and R2 preferably or in particular have those meanings which have already been mentioned above, in connection with the description of the compounds of the general formula (I) according to the invention, as being preferred or particularly preferred for R1 and R2.
20
The substituted thiophene-3-sulphonyl chlorides of the general formula (VI) are known and/or can be prepared by processes known per se (cf. J. Org. Chem. 45 (1980), 617-620, WO-A-01/05788).
HAj

Le A 35 696-Foreign Countries
-24-
The substituted thiophene-3-sulphonyl chlorides of the general formula (VI) are obtained when 3-amino-thiophene-4-carboxylic esters of the general formula (X)
(X)
in which 5
R1 and R2 are as defined above,
- or acid adducts of compounds of the formula (X), such as, for example, the hydrochlorides -
10
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 resulting diazonium salt solution is reacted with sulphur dioxide in the presence of a diluent, such as, for example, dichloromethane, 1,2-dichloroethane or acetic acid, and
15 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.
The intermediates of the general formula (X) are known and/or can be prepared by
processes known per se (cf. Austr. J. Chem. 48 (1995), 1907-1916; Preparation
20 Examples).
The formula (VIII) provides a general definition of the triazolin(ethi)one (thio)-
carboxamides to be used as starting materials in the process (d) according to the
invention for preparing compounds of the general formula (I). In the general formula
25 (VIII), Q1, Q2, R3 and R4 preferably or in particular have those meanings which have
already been mentioned above, in connection with the description of the compounds of the general formula (I) according to the invention, as being preferred or particularly preferred for Q1, Q2, R3 and R4.
25

Le A 35 696-Foreign Countries
-25-
The starting materials of the general formula (VIII) are known and/or can be prepared by processes known per se.
5 The formula (IX) provides a general definition of the substituted thien-3-yl-
sulphonylamino(thio)carbonyl compounds to be used as starting materials in the
process (e) accordmg to the invention for preparing compounds of the general
formula (I). In the general formula (IX), Q , R and R preferably or in particular
have those meanings which have already been mentioned above, in connection with
10 the description of the compounds of the general formula (I) according to the
11 9
invention, as being preferred or particularly preferred for Q , R and R .
The starting materials of the general formula (IX) are known and/or can be prepared by processes known per se.
15
The processes (a), (b), (c), (d) and (e) according to the invention for preparing the novel compounds of the formula (I) are preferably carried out using diluents. Suitable diluents are virtually all inert organic solvents. These preferably include aliphatic and aromatic, optionally halogenated hydrocarbons, such as pentane, hexane, heptane,
20 cyclohexane, petroleum ether, benzine, ligroin, benzene, toluene, xylene, methylene
chloride, ethylene chloride, chloroform, carbon tetrachloride, 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,
25 esters, such as methyl acetate and ethyl acetate, nitriles, such as, for example,
acetonitrile and propionitrile, amides, such as, for example, dimethylformarnide, dimethylacetamide and N-methylpyrrolidone, and also dimethyl sulphoxide, tetra-methylene sulphone and hexamethylphosphoric triamide.
30 Reaction auxiliaries suitable for the processes (a), (b), (c), (d) and (e) according to
the invention are all acid binders which are customarily used for such reactions.
26

Le A 35 696-Foreign Countries
-26-
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-
5 butoxide, furthermore basic nitrogen compounds, such as trimethylamine,
triethylamine, tripropylamine, tributylamine, diisobutylamine, dicyclohexylamine,
ethyldiisopropylamine, ethyldicyclohexylamine, N,N-dimethylbenzyIamine, N,N-
dimethyl-aniline, pyridine, 2-mefhyl-, 3-methyl-, 4-methyl-, 2,4-dimefhyl-, 2,6-
dimethyl-, 2-ethyl-, 4-ethyl- and 5-ethyl-2-methyl-pyridine, l,5-diazabicyclo[4.3.0]-
10 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) and (e) according to the
invention can be varied within a relatively wide range. In general, the processes are
15 carried out at temperatures between -20°C and +150°C, preferably at temperatures
between 0°C and +100°C.
The processes (a), (b), (c), (d) and (e) according to the invention are generally carried
out under atmospheric pressure. However, it is also possible to operate under
20 elevated or reduced pressure.
For carrying out the processes (a), (b), (c), (d) and (e) according to the invention, the starting materials required in each case are generally employed in approximately equimolar amounts. However, it is also possible to use a relatively large excess of
25 one of the components used in each case. The reactions are generally carried out in a
suitable diluent in the presence of an acid acceptor, and the reaction mixture is stirred for several hours at the temperature required in each case. Work-up in the processes (a), (b), (c), (d) and (e) according to the invention is in each case carried out by customary methods (cf. the Preparation Examples).
30
27

Le A 35 696-Foreign Countries
-27-
If appropriate, salts can be prepared from the compounds of the general formula (I)
according to the invention. Such salts are obtained in a simple manner by customary
methods for forming salts, for example by dissolving or dispersing a compound of
the formula (I) in a suitable solvent, such as, for example, methylene chloride,
5 acetone, tert-butyl methyl ether or toluene, and adding a suitable base. The salts can
then - if appropriate after prolonged stirring - be isolated by concentration or filtration with suction.
The active compounds according to the invention can be used as defoliants,
10 desiccants, haulm killers and, especially, as weedkillers. Weeds in the broadest sense
are to be understood as meaning 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.
15 The active compounds according to the invention can be used, for example, in
connection with the following plants:
Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea,
20 Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum,
Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Linderaia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea,
25 Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.
Dicotyledonous crops of the genera: Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia. 30
28

Le A 35 696-Foreign Countries
-28-
Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis, Alopecurus,
Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus,
Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa,
Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium,
5 Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria,
Scirpus, Setaria, Sorghum.
Monocotyledonous crops of the genera: Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea. 10
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.
Depending on the concentration, the active compounds according to the invention are
15 suitable for total weed control, for example on industrial sites and rail tracks and on
paths and areas with or without tree growth. Equally, the compounds according to the
invention can be employed for controlling weeds in perennial crops, for example
forests, ornamental tree plantings, orchards, vineyards, citrus groves, nut orchards,
banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm
20 plantations, cocoa plantations, soft fruit plantings and hop fields, on lawns and turf
and pastures and for selective weed control in annual crops.
The compounds of the formula (I) according to the invention have strong herbicidal
activity and a broad activity spectrum when applied on the soil and on above-ground
25 parts of plants. To a certain extent, they are also suitable for selective control of
monocotyledonous and dicotyledonous weeds in monocotyledonous and dicotyledonous crops, both by the pre-emergence and by the post-emergence method.
At certain concentrations or application rates, the active compounds according to the
30 invention can also be used for controlling animal pests and fungal or bacterial plant
29

Le A 35 696-Foreign Countries
-29-
diseases. If appropriate, they can also be employed as intermediates or precursors for the synthesis of further active compounds.
According to the invention, it is possible to treat all plants and parts of plants. By
5 plants are understood here all plants and plant populations such as desired and
undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants can be plants which can be obtained by conventional "breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including transgenic plants and including plant
10 varieties which may or may not be protectable by plant variety property rights. Parts
of plants are to be understood as meaning all above-ground and below-ground parts and organs of plants, such as shoot, leaf, flower and root, examples which may be mentioned being leaves, needles, stems, trunks, flowers, fruit bodies, fruits and seeds and also roots, tubers and rhizomes. Plant parts also include harvested goods and
15 vegetative and generative propagation material, for example seedlings, tubers,
rhizomes, cuttings and seeds.
The treatment of the plants and parts of plants according to the invention with the
active compounds is carried out directly or by action on their environment, habitat or
20 storage area according to customary treatment methods, for example by dipping,
spraying, evaporating, atomizing, broadcasting, brushing-on and, in the case of propagation materials, in particular in the case of seeds, furthermore by single- or multi-layer coating.
25 The active compounds can be converted into the customary formulations, such as
solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspo-emulsion concentrates, natural and synthetic substances impregnated with active compound, and microencapsulations in polymeric substances.
30
30

Le A 35 696-Foreign Countries
-30-
These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is to say liquid solvents and/or solid carriers, optionally with the use of surfactants, that is to say emulsifiers and/or dispersants and/or foam formers. 5
If the extender used is water, it is also possible to use, for example, organic solvents as auxiliary solvents. Liquid solvents which are mainly suitable are: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene
10 chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example
petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol, and also their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulphoxide, and water.
15
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
20 and fractionated natural rocks, such as calcite, marble, pumice, sepiolite, dolomite
and synthetic granules of inorganic and organic meals, and granules of organic material, such as sawdust, coconut shells, maize cobs and tobacco stalks; suitable emulsifiers and/or foam formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for
25 example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates,
arylsulphonates and protein hydrolysates; suitable dispersants are: for example lignosulphite waste liquors and methylcellulose.
Tackifiers, such as carboxymethylcellulose, natural and synthetic polymers in the
30 form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and
polyvinyl acetate, and also natural phospholipids, such as cephalins and lecithins, and
31

Le A 35 696-Foreign Countries
-31-
synthetic phospholipids can be used in the formulations. Other possible additives are mineral and vegetable oils.
It is possible to use dyestuffs, such as inorganic pigments, for example iron oxide,
5 titanium oxide, Prussian blue, and organic dyestuffs, such as alizarin dyestuffs, azo
dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients, such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
The formulations generally comprise between 0.1 and 95 per cent by weight of active
10 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
and/or with crop-plant compatibility-improving substances ("safeners"), finished
15 formulations or tank mixes being possible. Also possible are mixtures with weed-
killers comprising one or more known herbicides and a safener.
Possible components for the mixtures are known herbicides, for example
20 acetochlor, acifluorfen(-sodium), aclonifen, alachlor, alloxydim(-sodium), ametryne,
amicarbazone, amidochlor, amidosulfuron, anilofos, asulam, atrazine, azafenidin, azimsulfuron, beflubutamide, benazolin(-ethyl), benfuresate, bensulfuron(-methyl), bentazone, benzfendizone, benzobicyclon, benzofenap, benzoylprop(-ethyl), bialaphos, bifenox, bispyribac(-sodium), bromobutide, bromofenoxim, bromoxynil,
25 butachlor, butafenacil(-allyl), butroxydim, butylate, cafenstrole, caloxydim,
carbetamide, carfentrazone(-ethyl), chlomefhoxyfen, chloramben, chloridazon, chlorimuron(-ethyl), chlornitrofen, chlorsulfuron, chlorotoluron, cinidon(-ethyl), cinmethylin, cinosulfuron, clefoxydim, clethodim, clodinafop(-propargyl), clomazone, clomeprop, clopyralid, clopyrasulfuron(-methyl), cloransulam(-methyl),
30 cumyluron, cyanazine, cybutryne, cycloate, cyclosulfamuron, cycloxydim, cyhalo-
fop(-butyl), 2,4-D, 2,4-DB, 2,4-DP, desmedipham, diallate, dicamba,
32

Le A 35 696-Foreign Countries
-32-
dichloroprop(-P), diclofop(-methyl), diclosulam, diethatyl(-ethyl), difenzoquat,
diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn,
dimethenamid, dimexyflam, dinitramine, diphenamid, diquat, dithiopyr, diuron,
dymron, eproprodan, EPTC, esprocarb, ethalfluralin, ethametsulfuron(-methyl),
5 ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanid, fenoxaprop-(-P-ethyl),
fentrazamide, flamprop(-isopropyl), flamprop(-isopropyl-L), flamprop(-methyl), flazasulfuron, florasulam, fluazifop(-P-butyl), fluazolate, flucarbazone(-sodium), flufenacet, flufenpyr flumetsulam, flumiclorac(-pentyl), flumioxazin, flumipropyn, flumetsulam, fluometuron, fluorochloridone, fluoroglycofen(-ethyl), flupoxam,
10 flupropacil, flurpyrsulfuron(-methyl, -sodium), flurenol(-butyl), fiuridone,
fluroxypyr(-butoxypropyl, -meptyl), flurprimidol, flurtamone, fluthiacet(-methyl), fluthiamide, fomesafen, foramsulfuron, glufosinate(-ammonium), glyphosate-(-isopropylammonium), halosafen, haloxyfop(-ethoxyethyl-P-methyl), haloxy-fop(-ethoxyethyl, -P-methyl), hexazinone, imazamethabenz-(-methyl), imazameth-
15 apyr, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron,
iodosulfuron(-methyl, -sodium), ioxynil, isopropalin, isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, ketospiradox, lactofen, lenacil, linuron, MCPA, mecoprop, mefenacet, mesotrione, metamitron, metazachlor, methabenzthiazuron, metobenzuron, metobromuron, (alpha-)metolachlor,
20 metosulam, metoxuron, metribuzin, metsulfuron(-methyl), molinate, monolinuron,
naproanilide, napropamide, neburon, nicosulfuron, norflurazon, orbencarb, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat, pelargonic acid, pendimethalin, pendralin, penoxysulam, pentoxazone, pethoxamide, phenmedipham, picolinafen, piperophos, pretilachlor, primisulfuron(-methyl),
25 profluazol, profoxydim, prometryn, propachlor, propanil, propaquizafop, propiso-
chlor, propoxycarbazone(-sodium), propyzamide, prosulfocarb, prosulfuron, pyraflufen(-ethyl), pyrazogyl, pyrazolate, pyrazosulfuron(-ethyl), pyrazoxyfen, pyribenzoxim, pyributicarb, pyridate, pyridatol, pyriftalid, pyriminobac(-methyl), pyrithiobac(-sodium), quinchlorac, quinmerac, quinoclamine, quizalofop(-P-ethyl),
30 quizalofop(-P-tefuryl), rimsulfuron, sethoxydim, simazine, simetryn, sulcotrione,
sulfentrazone, sulfometuron(-methyl), sulfosate, sulfosulfuron, tebutam, tebuthiuron,
33

Le A 35 696-Foreign Countries
-33-
tepraloxydim, terbuthylazine, terbutryn, thenylchlor, fhiafluamide, thiazopyr, thi-diazimin, thifensulfuron(-methyl), thiobencarb, tiocarbazil, tralkoxydim, triallate, triasulfuron, tribenuron(-methyl), triclopyr, tridiphane, trifluralin, trifloxysulfuron, triflusulfuron(-methyl), and triflusulfuron. 5
Furthermore suitable for the mixtures are known safeners, for example
AD-67, BAS-145138, benoxacor, cloquintocet (-mexyl), cyometrinil, 2,4-D, DKA-
24, dichlormid, dymron, fenclorim, fenchlorazol (-ethyl), flurazole, fluxofenim,
10 furilazole, isoxadifen (-ethyl), MCPA, mecoprop (-P), mefenpyr (-diethyl), MG-191,
oxabetrinil, PPG-1292, R-29148.
A mixture with other known active compounds, such as fungicides, insecticides,
acaricides, nematicides, bird repellents, plant nutrients and agents which improve soil
15 structure, is 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
20 customary manner, for example by watering, spraying, atomizing, scattering.
The active compounds according to the invention can be applied both before and after emergence of the plants. They can also be incorporated into the soil before sowing. 25
The amount of active compound used can vary within a relatively wide 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.
34

Le A 35 696-Foreign Countries
-34-
As already mentioned above, it is possible to treat all plants and their parts according
to the invention. In a preferred embodiment, wild plant species and plant cultivars, or
those obtained by conventional biological breeding methods, such as crossing or
protoplast fusion, and parts thereof, are treated. In a further preferred embodiment,
5 transgenic plants and plant cultivars obtained by genetic engineering, if appropriate
in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated. The term "parts" or "parts of plants" or "plant parts" has been explained above.
10 Particularly preferably, plants of the plant cultivars which are in each case
commercially available or in use are treated according to the invention. Plant cultivars are to be understood as meaning plants having certain properties ("traits") and which have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. They can be cultivars, bio- or genotypes.
15
Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, vegetation period, diet), the treatment according to the invention may also result in superadditive ("synergistic") effects. Thus, for example, reduced application rates and/or a widening of the activity spectrum and/or an
20 increase in the activity of the substances and compositions to be used according to
the invention - also in combination with other agro-chemical active compounds -, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, better quality and/or
25 a higher nutritional value of the harvested products, better storage stability and/or
processability of the harvested products are possible which exceed the effects which were actually to be expected.
The transgenic plants or plant cultivars (i.e. those obtained by genetic engineering)
30 which are preferably treated according to the invention include all plants which, in
the genetic modification, received genetic material which imparted particularly
35

Le A 35 696-Foreign Countries
-35-
advantageous useful properties ("traits") to these plants. Examples of such properties
are better plant growth, increased tolerance to high or low temperatures, increased
tolerance to drought or to water or soil salt content, increased flowering performance,
easier harvesting, accelerated maturation, higher harvest yields, better quality and/or
5 a higher nutritional value of the harvested products, better storage stability and/or
processability of the harvested products. Further and particularly emphasized examples of such properties are a better defence of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and/or viruses, and also increased tolerance of the plants to certain herbicidally active
10 compounds. Examples of transgenic plants which may be mentioned are the
important crop plants, such as cereals (wheat, rice), maize, soya beans, potatoes, cotton, oilseed rape and also fruit plants (with the fruits apples, pears, citrus fruits and grapes), and particular emphasis is given to maize, soya beans, potatoes, cotton and oilseed rape. Traits that are emphasized are in particular increased defence of the
15 plants against insects by toxins formed in the plants, in particular those formed in the
plants by the genetic material from Bacillus thuringiensis (for example by the genes CrylA(a), CrylA(b), CrylA(c), CryllA, CrylllA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CrylF and also combinations thereof) (hereinbelow referred to as "Bt plants"). Traits that are also particularly emphasized are the increased defence of the plants to
20 fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin,
phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins. Traits that are furthermore particularly emphasized are the increased tolerance of the plants to certain herbicidally active compounds, for example imidazolinones, sulphonylureas, glyphosate or phosphinotricin (for example the
25 "PAT" gene). The genes which impart the desired traits in question can also be
present in combination with one another in the transgenic plants. Examples of "Bt plants" which may be mentioned are maize varieties, cotton varieties, soya bean varieties and potato varieties which are sold under the trade names YIELD GARD® (for example maize, cotton, soya beans), KnockOut® (for example maize),
30 StarLink® (for example maize), Bollgard® (cotton), Nucotn® (cotton) and
NewLeaf® (potato). Examples of herbicide-tolerant plants which may be mentioned
36

Le A 35 696-Foreign Countries
-36-
are maize varieties, cotton varieties and soya bean varieties which are sold under the
trade names Roundup Ready® (tolerance to glyphosate, for example maize, cotton,
soya bean), Liberty Link® (tolerance to phosphinotricin, for example oilseed rape),
IMI® (tolerance to imidazolinones) and STS® (tolerance to sulphonylurea, for
5 example maize). Herbicide-resistant plants (plants bred in a conventional manner for
herbicide tolerance) which may be mentioned include the varieties sold under the name Clearfield® (for example maize). Of course, these statements also apply to plant cultivars having these genetic traits or genetic traits still to be developed, which plants will be developed and/or marketed in the future.
10
The plants listed can be treated according to the invention in a particularly advantageous manner with the compounds of the general formula (I) or the active compound mixtures according to the invention, where in addition to the good control of weed plants, the abovementioned synergistic effects with the transgenic plants or
15 plant cultivars occur. The preferred ranges stated above for the active compounds or
mixtures also apply to the treatment of these plants. Particular emphasis is given to the treatment of plants with the compounds or mixtures specifically mentioned in the present text.
20 The following examples show the preparation and use of the active compounds
according to the invention:
37

Le A 35 696-Foreign Countries
37-
Preparation examples: Example 1

0.45 g (2.19 mmol) of 5-methoxy-4-methyl-2-phenoxycarbonyl-2,4-dihydro-3H-l,2,4-triazol-3-one is dissolved in 50 ml of acetonitrile and, at room temperature (about 20°C), mixed with stirring, a little at a time, with 0.60 g (2.41 mmol) of 4-
10 ethoxycarbonyl-2-methyl-thiophene-3-sulfonamide and with 0.37 g (2.41 mmol) of
l,8-diazabicyclo-[5.4.0]-undec-7-ene (DBU). The reaction mixture is stirred at room temperature for 12 hours and then concentrated under reduced pressure. The residue is taken up in methylene chloride and washed successively with IN hydrochloric acid and with water, dried with sodium sulphate and filtered. The filtrate is concentrated
15 under reduced pressure, the residue is digested with isopropanol and the resulting
crystalline product is isolated by filtration with suction.
This gives 0.60 g (68% of theory) of ethyl 4-[[[(3-methoxy-4-methyl-5-oxo-lH-
l,2,4-triazol-l-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate as a
20 pale yellow solid of melting point 176°C.
The sodium salt of the compound prepared according to Example 1 can be prepared, for example, as follows:
25 1.0 g (2.5 mmol) of ethyl 4-[[[(3-methoxy-4-methyl-5-oxo-lH-l,2,4-triazol-l-
yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate are taken up in 25 ml of methylene chloride, and 0.10 g (2.5 mmol) of sodium hydroxide (micropellets) are
38

Le A 35 696-Foreign Countries
-38
added. The mixture is stirred at room temperature (or 20°C) for 15 hours. The crystalline product is then isolated by filtration with suction.
This gives 1.0 g of ethyl 4-[[[(3-methoxy-4-methyl-5-oxo-lH-l,2,4-triazol-l-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate sodium salt of melting point 220°C.

10

Analogously to Example 1, and in accordance with the general description of the preparation process according to the invention, it is also possible to prepare, for example, the compounds of the general formula (I) listed in table 1 below.


(i)

Table 1: Examples of the compounds of the formula (I)

Ex.
No. Q1 Q2 R1 R2 R3 R4 Melting point (°C)
2 0 0 CH3 CH3 OCH3 CH3 229 (Na-Salz)
3 0 0 CH3 CH3 R3+R4: -S(CH2)2- 204
4 0 0 CH3 CH3 RJ+R4: -0(CH2)2- 225
5 0 0 CH3 CH3 R3+R4: -S(CH2)3- 182
6 0 0 CH3 CH3 R3+R4: -0(CH2)3- 239

Le A 35 696-Foreign Countries
-39-

Ex. Q1 Q2 R1 R2 R3 R4 Melting
No. point (°C)
7 0 0 CH3 CH3 219
8 0 0 CH3 CH3 CH3 163

9 0 0 CH3 CH3 CH3 170
10 0 0 CH3 CH3 CH3 154
11 0 0 CH3 CH3 CH3 165
12 0 0 CH3 CH3 220
13 0 0 CH3 CH3 CH3 203
14 0 0 CH3 CH3 CH3 143
15 0 0 CH3 CH3 C3H7-n CH3 154
16 0 0 CH3 CH3 C3H7-i CH3 155
40

Le A 35 696-Foreign Countries
-40-

Ex.
No. Q1 Q2 R1 R2 R3 R4 Melting point (°C)
17 0 0 CH3 CH3 C4H9-S CH3 156
18 0 0 CH3 CH3 CH2OCH3 CH3 157
19 0 0 CH3 CH3 1 CH3 114
20 0 0 CH3 CH3 SC2H5 CH3 162
21 0 0 CH3 CH3 C4Xl9-t CH3 99
22 0 0 CH3 CH3 CH3 180
23 0 0 CH3 CH3 CH3 C2H5 117
24 0 0 CH3 CH3 C3H7-n 151
25 0 0 CH3 CH3 C2H5 C2H5 147
26 0 0 CH3 CH3 C3H7-n C2H5 146
28 0 0 CH3 CH3 C2H5 150
29 0 0 CH3 CH3 CH3 C3H7-n 135
30 0 0 CH3 CH3 CH3 C3H7-i 147
31 0 0 CH3 CH3 C2H5 C3H7-n 159
32 0 0 CH3 CH3 C2H5 C3H7-i 142
33 0 0 CH3 CH3 C3H7-n C3H7-n 103
34 0 0 CH3 CH3 C3H7-i C3H7-n 116
35 0 0 CH3 CH3 C3H7-i C3H7-i 121
36 0 0 CH3 CH3 C3H7-i 126
^

Le A 35 696-Foreign Countries
-41-

Ex.
No. Q1 Q2 R1 R2 R3 R4 Melting point (°C)
37 0 0 CH3 CH3 C3H7-n C3H7-i 120
38 0 0 CH3 CH3 OC2H5 C2H5 124
39 0 0 CH3 CH3 C2H5 OC2H5 183
40 0 0 CH3 CH3 Br CH3 189
41 0 0 CH3 CH3 OCH2CF3 CH3 197
42 0 0 CH3 CH3 C3H7-n OCH3 106
43 0 0 CH3 CH3 OCH2CF3 117
44 0 0 CH3 CH3 Br 166
45 0 0 CH3 CH3 CH2OCH3 185
46 0 0 CH3 CH3 CH3 206
47 0 0 CH3 CH3 C2Hs 175
48 0 0 CH3 CH3 C3H7-n ■ 149
49 0 0 CH3 CH3 C3H7-i 214
50 0 0 CH3 CH3 C4H9-t 175
51 0 0 CH3 CH3 C4H9-S 205
52 0 0 CH3 CH3 H 201
42

Le A 35 696-Foreign Countries
-42-

Ex.
No. Q1 Q2 R1 R2 R3 R4 Melting point (°C)
53 0 0 CH3 CH3 H CH3 170
54 0 0 CH3 CH3 CH3 N(CH3)2 166
55 0 0 C2H5 CH3 OC2H5 CH3 172
56 0 0 C2H5 CH3 OCH3 173
57 s 0 CH3 CH3 OCH3 CH3 159
58 s 0 CH3 CH3 OC2H5 CH3 133
59 s 0 CH3 CH3 OC3H7-n CH3 60
60 s 0 CH3 CH3 OC3H7-i CH3 182
61 s 0 CH3 CH3 OCH3 201
62 s 0 CH3 CH3 OC2H5 181
63 s 0 CH3 CH3 OC3H7-n 137
64 s 0 CH3 CH3 127
65 s 0 CH3 CH3 CH3 CH3 147
66 s 0 CH3 CH3 C2H5 CH3 117
67 s 0 CH3 CH3 SCH3 CH3 138
68 0 0 C3H7-i CH3 OCH3 CH3 190
69 0 0 C3H7-i CH3 OC2H5 CH3 193
70 0 0 C3H7-i CH3 OC3H7-n CH3 189
71 0 0 C3H7-i CH3 OC3H7-i CH3 184
72 0 0 C3H7-i CH3 OCH3 189
43

Le A 35 696-Foreign Countries
-43-

Ex.
No. Q1 Q2 R1 R2 R3 R4 Melting point (°C)
73 0 0 C3H7-i CH3 OC2H5 115
74 0 0 C3H7-i CH3 OC3H7-n 127
75 0 0 C3H7-i CH3 OC3H7-i 251
76 0 0 C3H7-i CH3 117
77 0 0 C3H7-i CH3 SCH3 CH3 185
78 0 0 C3H7-11 CH3 OCH3 CH3 161
79 0 0 C3H7-n CH3 OC2H5 CH3 95
80 0 0 C3H7-n CH3 OC3H7-n CH3 156
81 0 0 C3H7-n CH3 OC3H7-i CH3 197
82 0 0 C3H7-n CH3 OCH3 169
83 0 0 C3H7-n CH3 OC2H5 150
84 0 0 C3H7-n CH3 OC3H7-n 88
85 0 0 C3H7-n CH3 OC3H7-i 95
86 0 0 C3H7-n CH3 192
87 0 0 C3H7-n CH3 C2H5 CH3 110
88 0 0 C3H7-n CH3 SC H3 CH3 188
Uv

Le A 35 696-Foreign Countries
-44-

Ex. Ql Q2 R1 R2 R3 R4 Melting
No. point (°C)
89 0 0 C3H7-i CH3 R3+R 4. 194
-S(CH2)2-
90 0 0 C3H7-i CH3 R3+R 4. 188
-0(CH2)2-
91 0 0 C3H7-i CH3 CH2OCH3 CH3 122
92 0 0 C3H7-i CH3 R3+R 4. 205
-OCH2-C(CH3)2-CH2-
93 0 0 C3H7-i CH3 CH3 183

94 0 0 C3H7-i CH3 CH3 54
95 0 0 C3H7-i CH3 CH3 159
96 0 0 C3H7-i CH3 CH3 208
97 0 0 C3H7-i CH3 CH3 115
98 0 0 C3H7-i CH3 C3H7-n CH3 105
99 0 0 C3H7-i CH3 C3H7-i CH3 106
100 0 0 C3H7-i CH3 C4H9-S CH3 103
45

Le A 35 696-Foreign Countries
-45-

Ex.
No. Q1 Q2 R1 R2 R3 R4 Melting point (°C)
101 0 0 C3H7-i CH3 SC2H5 CH3 113
102 0 0 C3H7-i CH3 C4H9-t CH3 131
103 0 0 C3H7-i CH3 CH3 159
104 0 0 C3H7-i CH3 CH3 C3H7-i 165
105 s 0 C3H7-i CH3 OCH3 CH3 145
106 s 0 C3H7-i CH3 OC2H5 CH3 175
107 s 0 C3H7-i CH3 OC3H7-n CH3 166
108 s 0 C3H7-i CH3 OC3H7-i CH3 168
109 s 0 C3H7-i CH3 OCH3 137
110 s 0 C3H7-i CH3 OC2H5 150
111 s 0 C3H7-i CH3 OC3H7-n 136
112 s 0 C3H7-n CH3 OCH3 CH3 137
113 s 0 C3H7-n CH3 OC2H5 CH3 160
114 s 0 C3H7-n CH3 OC3H7-n CH3 160
115 0 0 C3H7-i CH3 OC2H5 C2H5 123
116 0 0 C3H7-i CH3 C2H5 OC2H5 132
117 0 0 C3H7-i CH3 OCH2CF3 CH3 188
118 0 0 C3H7-i CH3 C3H7-n OCH3 245
119 0 0 C3H7-i CH3 OCH2CF3 255
120 0 0 C3H7-i CH3 CH2OCH3 164
46

Le A 35 696-Foreign Countries
-46-

Ex.
No. Q1 Q2 R1 R2 R3 R4 Melting point (°C)
121 s 0 C3H7-n CH3 OC3H7-i CH3 172
122 s 0 C3H7-11 CH3 OCH3 140
123 s 0 C3H7-n CH3 OC2H5 139
124 s 0 C3H7-11 CH3 OC3H7-n 219
125 s 0 C3H7-n CH3 OC3H7-i 120
126 s 0 CH3 CH3 OC3H7-i 144
127 0 0 C3H7-i CH3 Br 156
128 0 0 C3H7-i CH3 C2H5 143
129 0 0 C3H7-i CH3 C3H7-i 160
130 0 0 C3H7-i CH3 H 183
131 0 0 C3H7-i CH3 H CH3 167
132 s 0 C2H5 CH3 OCH3 CH3 165
133 s 0 C2H5 CH3 OC2H5 CH3 158
134 s 0 C2H5 CH3 OC3H7-n CH3 150
135 s 0 C2H5 CH3 OC3H7-i CH3 176
136 s 0 C2H5 CH3 OCH3 159
47

Le A 35 696-Foreign Countries
-47-

Ex. Q1 Q2 R1 R2 R3 R4 Melting
No. point (°C)
137 s 0 C2H5 CH3 OC2H5 162
138 s 0 C2H5 CH3 OC3H7-11 156
139 s 0 C2H5 CH3 OC3H7-i 135
140 0 0 C2H5 CH3 R3+R4: -S(CH2)2- 189
141 0 0 C2H5 CH3 R3+R4: -S(CH2)3- 181
142 0 0 C2H5 CH3 R3+R4: -OCH2-C(CH3)2-CH2- 212
143 0 0 C2H5 CH3 CH3 174

144 0 0 C2H5 CH3 CH2OCH3 CH3 116
145 0 0 C2H5 CH3 CH3 131
146 0 0 C2H5 CH3 CH3 171
147 0 0 C2H5 CH3 CH3 210
148 0 0 C2H5 CH3 C3H7-i CH3 175
^

Le A 35 696-Foreign Countries
-48-

Ex.
No. Q1 Q2 R1 R2 R3 R4 Melting point (°C)
149 0 0 C2H5 CH3 SC2H5 CH3 131
150 0 0 C2H5 CH3 C^g-t CH3 129
151 0 0 C2H5 CH3 CH3 195
152 0 0 C2H5 CH3 CH3 C2H5 140
153 0 0 C2H5 CH3 "
C3H7-n 118
154 0 0 C2H5 CH3 C2H5 C2H5 117
155 0 0 C2H5 CH3 C3H7-n C2H5 165
156 0 0 C2H5 CH3 C3H7-i C2H5 136
157 0 0 C2H5 CH3 C2H5 148
158 0 0 C2H5 CH3 CH3 C3H7-n 135
159 0 0 C2H5 CH3 CH3 C3H7-i 135
160 0 0 C2H5 CH3 C2H5 C3H7-i 142
161 0 0 C2H5 CH3 C3H7-i 147
162 0 0 C2H5 CH3 OC2H5 C2H5 127
163 0 0 C2H5 CH3 C2H5 OC2H5 145
164 0 0 C2H5 CH3 OCH2CF3 CH3 175
165 0 0 C2H5 CH3 C3H7-11 OCH3 112
166 0 0 C2H5 CH3 OCH2CF3 147
167 0 0 C2H5 CH3 CH2OCH3 147
49

Le A 35 696-Foreign Countries
-49-

Ex.
No. Q1 Q2 R1 R2 R3 R4 Melting point (°C)
168 0 0 C2H5 CH3 CH3 152
169 0 0 C2H5 CH3 C2H5 159
170 0 0 C2H5 CH3 C3H7-11 129
171 0 0 C2H5 CH3 C3H7-i A
158
172 0 0 C2H5 CH3 C4H9-t 164
173 0 0 C2H5 CH3 C4H9-S 149
174 0 0 C2H5 CH3 H 184
175 0 0 C2H5 CH3 H CH3 170
176 0 0 C2H5 CH3 CH3 N(CH3)2 130
177 0 0 C2H5 CH3 C4H9-i 147
178 0 0 C2H5 CH3 C4H9-11 123
179 0 0 C3H7-n CH3 R3+R4: -S(CH2)2- 182
180 0 o C3H7-n CH3 R3+R4: -S(CH2)3- 198
50

Le A 35 696-Foreign Countries
-50-

Ex.
No. Q1 Q2 R1 R2 R3 R4 Melting point (°C)
181 0 0 C3H7-n CH3 1 CH3 153
182 0 0 C3H7-n CH3 CH3 145
183 0 0 C3H7-11 CH3 CH3 183
184 0 0 C3H7-11 CH3 CH3 170
185 0 0 C3H7-n CH3 C3H7-n CH3 127
186 0 0 C3H7-11 CH3 C3H7-i CH3 132
187 0 0 C3H7-11 CH3 C4H9-S CH3 125
188 0 0 C3H7-n CH3 CH2OCH3 CH3 110
189 0 0 C3H7-11 CH3 SC2H5 CH3 142
190 0 0 C3H7-n CH3 CH3 CH3 145
191 0 0 C3H7-11 CH3 CH3 C3H7-i 174
192 0 0 C3H7-n CH3 C2H5 C3H7-i 120
193 0 0 C3H7-11 CH3 OC2H5 C2H5 121
194 0 0 C3H7-11 CH3 C2H5 OC2H5 120
195 0 0 C3H7-n CH3 OCH2CF3 CH3 140
196 0 0 C3H7-n CH3 C3H7-n OCH3 112
197 0 0 C3H7-n CH3 OCH2CF3 122
51

Le A 35 696-Foreign Countries
-51-

Ex.
No. Q1 Q2 R1 R2 R3 R4 Melting point (°C)
198 0 0 C3H7-I1 CH3 CH2OCH3 117
199 0 0 C3H7-I1 CH3 C2H5 180
200 0 0 C3H7-I1 CH3 C3H7-i 183
201 0 0 C3H7-11 CH3 H / 197
202 0 0 C3H7-I1 CH3 H CH3 125
203 0 0 C2H5 CH3 OC3H7-n CH3 139
204 0 0 C2H5 CH3 OC3H7-i CH3 180
205 0 0 C2H5 CH3 OC2H5 140
206 0 0 C2H5 CH3 OC3H7-n 145
207 0 0 C2H5 CH3 OC3H7-i 160
208 0 0 C2H5 CH3 171
209 0 0 C2H5 CH3 CH3 CH3 155
210 0 0 C2H5 CH3 C2H5 CH3 107
211 0 0 C2H5 CH3 SCH3 CH3 156
212 0 0 C3H7-i CH3 C2H5 C3H7-i 251
213 0 0 CH3 C2H5 OC3H7-i 152
214 0 0 CH3 C2H5 SC2H5 CH3 145
52

Le A 35 696-Foreign Countries
-52-

Ex.
No. Ql Q2 R1 R2 R3 R4 Melting point (°C)
215 0 0 CH3 C2H5 OC2H5 C2H5 138
216 0 0 CH3 C2H5 C2H5 OC2H5 141
217 0 0 CH3 C2H5 OCH2CF3 CH3 163
218 0 0 CH3 C2H5 C3H7-n OCH3 105
219 0 0 CH3 C2H5 OCH2CF3 161
220 0 0 CH3 CH3 OCH3 CH3 146
(Triethyl-
ammonium
salt)
221 0 0 CH3 C2H5 OCH3 CH3 236
(Lithium
salt)
222 0 0 CH3 C2H5 OCH3 CH3 154
(Triethyl-
ammonium
salt)
223 0 0 CH3 C2H5 OCH3 CH3 162
(N,N-di-
methylpyrid
in-4-yl-
ammonium
salt)
53

Le A 35 696-Foreign Countries
-53-

Ex.
No. Q1 Q2 R1 R2 R3 R4 Melting point (°C)
224 0 0 CH3 C2H5 OCH3 CH3 150
(1-hydroxy-
methyl-
propyl-
propyl-
ammonium
salt)
225 0 0 CH3 CH3 OCH3 CH3 151
(Diethyl-
ammonium
salt)
226 0 0 CH3 CH3 OCH3 CH3 115
(Pyrroli-
dinium salt)
227 0 0 CH3 CH3 OCH3 CH3 159
(1-hydroxy-
methyl-
propyl-
ammonium
salt)
54

Le A 35 696-Foreign Countries
54
Use examples:
In the use examples, the following prior-art compounds (all known from WO-A-01/05788) are used for comparison:


O—C3H7-n
(A)

methyl 4-[[[(4,5-dihydro-4-methyl-5-oxo-3-n-propoxy- IH-1,2,4-triazol-1 -yl)carbonyl]-amino] sulfonyl]-5-methyl-3-thiophenecarboxylate (A)
10


L%A^
^S^N
O—C3H7-n
H N=

(B)

methyl 4-[[[(4-cyclopropyl-4,5-dihydro-5-oxo-3-n-propoxy-IH-1,2,4-triazol-1-yl)-carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate(B)
15


UXi
♦S^*N
H N= 0-C3H7-

(C)

f^

Le A 35 696-Foreign Countries
-55
methyl 4-[[[(4-cyclopropyl-4,5-dihydro-5-oxo-3-isopropoxy-lH-l,2,4-triazol-l-yl)-carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate (C)


(D)

methyl 4-[[[(3,4-dicyclopropyl-4,5-dihydro-5-oxo-lH-l,2,4-triazol-l-yl)carbonyl]-amino]sulfonyl]-5-methyl-3-thiophenecarboxylate (D)

10



(E)
methyl 4-[[[(4,5-dihydro-3,4-dimethyl-5-oxo-lH-l,2,4-triazol-l-yl)carbonyl]-amino]sulfonyl]-5-methyl-3-thiophenecarboxylate (E)


(F)

56

Le A 35 696-Foreign Countries
-57-Example A
Post-emergence test
5 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
10 emulsifier is added and the concentrate is diluted with water to the desired
concentration.
Test plants of a height of 5-15 cm are sprayed with the preparation of active
compound such that the particular amounts of active compound desired are applied
15 per unit area. The concentration of the spray liquor is chosen such 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. 20
The figures denote:
0% = no effect (like untreated control) 100% = total destruction 25
In this test, for example, the compounds of Preparation Examples 1, 15, 18, 20, 22, 39, 42, 45, 46, 47, 48, 55 and 56 show a considerably stronger activity against weeds and a substantially better compatibility with crop plants such as, for example, maize, oilseed rape and wheat than the known compounds (A) and (B).
58

Le A 35 696-Foreign Countries
-58-Example B
Pre-emergence test
5 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
10 emulsifier is added and the concetrate is diluted with water to the desired
concentration.
Seeds of the test plants are sown in normal soil. After 24 hours, the soil is sprayed
with the preparation of active compound such that the particular amount of active
15 compound desired is applied per unit area. The concentration of active compound in
the spray liquor is chosen such that the particular amount of active compound desired is applied in 1000 litres of water per hectare.
After three weeks, the degree of damage to the plants is rated in % damage in
20 comparison to the development of the untreated control. The figures denote:
0% = no effect (like untreated control) 100% = total destruction
25 In this test, for example, the compounds of Preparation Examples 1, 15, 18, 20, 22,
38, 39, 41, 42, 43, 45, 46, 47, 48, 55 and 56 exhibit considerably stronger activity against weeds than the known compounds (A), (B), (C), (D), (E), (F) and (G), and substantially, they are tolerated well by crop plants, such as, for example, maize, soyabean and wheat.
30
59

Table A1: Post-emergence-Test/greenhouse

Compound of Preparation
Example No. application rate (g ai/ha) wheat Avena fatua Bromus Echino-chloa Lolium Datura Viola Xanthium
(B) 15 30 50 50 - 60 80 - 50
(A) 15 0 30 50 60 30 50 30 70
(56) 15 0 90 90 95 90 90 95 95
Table A2: Post-emergence-Test/greenhouse

60


Compound of Preparation Example No. application rate (g ai/ha) maize Alope-curus Bromus Echino-chloa Lolium Datura Poly¬gonum Xanthium
(B) 15 90 0 50 - 60 80 70 50
(A) 15 30 70 50 60 30 50 50 70
(55) 15 0 90 90 90 90 95 90 95

Table A3: Post-emergence-Test/greenhouse

Compound of Preparation Example No. application rate (g
ai/ha) wheat maize Echino-chloa Lolium Datura Poly¬gonum Viola Xanthium
(B) 15 30 90 - 60 80 70 - 50
(A) 15 0 30 60 30 50 50 30 70
(1) 15 0 0 90 90 95 95 95 95

t-1
CD >
UQ\ V£> ON. i
o >-t
a
i—»■
n
o

CD Co

61

ON o

Table A4: Post-emergence-Test/greenhouse

Compound of Preparation Example No. application rate (g ai/ha) wheat maize Alope-curus Avena fatua Bromus Digitaria Setaria
(B) 15 30 90 0 50 50 20 60
(A) 15 0 30 70 30 50 10 30
(22) 15 0 0 99 80 95 95 90
Table A5: Post-emergence-Test/greenhouse

Compound of Preparation Example No. application rate (g ai/ha) wheat Alope-curus Bromus Echino-chloa Viola
(B) 15 30 0 50 - -
(A) 15 0 70 50 60 30
(20) 15 0 90 80 100 100

Table A6: Post-emergence-Test/greenhouse

Compound of Preparation Example No. application rate (g ai/ha) maize Alope-curus Avena fatua Bromus Digitaria Echino-chloa Lolium Setaria
(B) 15 90 0 50 50 20 - 60 60
(A) 15 30 70 30 50 10 60 30 30
(18) 15 0 95 95 80 95 95 95 100
Table A7: Post-emergence-Test/greenhouse

Compound of Preparation Example No. application rate (g ai/ha) Alope-curus Avena fatua Bromus Digitaria Echino-
chloa Lolium Setaria
(B) 15 0 50 50 20 - 60 60
(A) 15 70 30 50 10 60 30 30
(15) 15 95 90 80 100 90 80 90

Table A8: Post-emergence-Tesfgreenhouse

Compound of Preparation Example No. application rate (g ai/ha) Avena fatua Bromus Digitaria Echino-
chloa Lolium Setaria
(A) 15 30 50 10 60 30 30
(39) 15 90 95 95 100 95 95
(45) 15 90 90 100 100 95 90
Table A9: Post-emergence-Test/greenhouse

Compound of Preparation Example No. application rate (g
ai/ha) rape Alope-curus Echrno-chloa Lolium Cheno-podium
(A) 15 95 70 60 30 80
(42) 15 0 90 90 90 95
Table A10: Post-emergence-Test/greenhouse

Compound of Preparation Example No. application rate (g ai/ha) Avena fatua Digitaria Echino-chloa Lolium Setaria Viola Xanthium
(A) 15 30 10 60 30 30 30 70
(47) 15 95 90 95 100 90 100 -
(48) 15 90 90 95 100 80 95 90

Table All: Post-emergence-Test/greenhouse

Compound of Preparation
Example No. application rate (g ai/ha) Avena fatua Bromus Digitaria Lolium Setaria Xantbium
(B) 15 50 50 20 60 60 50
(39) 15 90 95 95 95 95 -
(45) 15 90 90 100 95 90 -
(47) 15 95 80 90 100 90 80
Table A12: Post-emergence-Test/greenhouse

Compound of Preparation
Example No. application rate (g ai/ha) Alope-curus Avena fatua Digitaria Lolium Xanthium
(B) 15 0 50 20 60 50
(46) 15 80 80 90 95 -
(48) 15 - 90 90 100 90

;-Test/greenhouse
Table Bl: Pre-emergence-


^


Compound of Preparation Example No. application rate (g ai/ha) wheat maize Bromus Lolium Ama-ranthus Matri¬caria Solanum Stellaria Xanthium
(G) 15 0 0 - 60 40 70 80 80 40
(F) 15 0 0 70 40 40 20 80 70 0
(E) 15 0 0 20 0 10 20 70 40 0
(D) 15 0 20 10 20 80 10 80 60 0
(Q 15 0 0 70 50 80 80 - 80 0
(B) 15 0 0 40 20 80 40 80 60 0
(A) 15 0 0 60 0 - 50 80 80 0
(56) 15 0 0 95 95 100 100 100 100 95
(1) 15 0 0 95 90 100 100 100 100 95

65

Table B2: Pre-emergence-Test/greenhouse

Compound of Preparation Example No. application rate (g ai/ha) wheat maize soy beans Alope-curus Lolium Ama-ranthus Matricaria Solanum Stellaria
(G) 15 0 0 50 - 60 40 70 80 80
(F) 15 0 0 10 70 40 40 20 80 70
(E) 15 0 0 0 20 0 10 20 70 40
(D) 15 0 20 0 0 20 80 10 80 60
(C) 15 0 0 0 0 50 80 80 - 80
(B) 15 0 0 0 20 20 80 40 80 60
(A) 15 0 0 0 60 0 - 50 80 80
(20) 15 0 0 0 90 95 95 100 100 100

0
67

Table B3: Pre-emergence-Test/greenhouse


Compound of Preparation Example No. application rate (g ai/ha) wheat maize Alope-curus Bromus Lolium Poly¬gonum Solanum Stellaria Xanthrum
(G) 15 0 0 - - 60 - 80 80 40
(F) 15 0 0 70 70 40 50 80 70 0
(E) 15 0 0 20 20 0 20 70 40 0
(D) 15 0 20 0 10 20 10 80 60 0
(C) 15 0 0 0 70 50 60 - 80 0
(B) 15 0 0 20 40 20 50 80 60 0
(A) 15 0 0 60 60 0 0 80 80 0
(55) 15 0 0 95 95 90 95 100 100 95
(22) 15 0 0 95 100 95 95 100 100 -
(15) 15 0 0 100 90 95 90 95 100 95

67

Table B4: Pre-emergence-Test/greenhouse

Compound of Preparation Example No. application rate (g
ai/ha) wheat maize soy beans Alope-curus Setaria Ama-ranthus Matricaria Stellaria
(G) 15 0 0 50 - 70 40 70 80
(F) 15 0 0 10 70 30 40 20 70
(E) 15 0 0 0 20 20 10 20 40
(D) 15 0 20 0 0 10 80 10 60
(C) 15 0 0 0 0 50 80 80 80
(B) 15 0 0 0 20 40 80 40 60
(A) 15 0 0 0 60 0 - 50 80
(18) 15 0 0 0 95 95 95 100 95

CD
>
o
CD
o
o
CD Vi



69

0\ OO

Table B5: Pre-emergence-Test/greenhouse



Compound of Preparation Example No. application rate (g ai/ha) maize soy beans Lolium Setaria Ama-ranthus Cheno-podium Solanum Stellaria
(G) 15 0 50 60 70 40 50 80 80
(F) 15 0 10 40 30 40 0 80 70
(E) 15 0 0 0 20 10 0 70 40
(D) 15 20 0 20 10 80 0 80 60
(C) 15 0 0 50 50 80 40 - 80
(B) 15 0 0 20 40 80 40 80 60
(A) 15 0 0 0 0 - 50 80 80
(38) 15 0 0 80 95 100 95 100 100


s

Table B6: Pre-emergence-Test/greenhouse



Compound of Preparation Example No. application rate (g ai/ha) wheat maize Alope-curus Setaria Ama-ranthus Cheno-podium Solanum Stellaria
(G) 15 0 0 - 70 40 50 80 80
(F) 15 0 0 70 30 40 0 80 70
(E) 15 0 0 20 20 10 0 70 40
(D) 15 0 20 0 10 80 0 80 60
(C) 15 0 0 0 50 80 40 - 80
(B) 15 0 0 20 40 80 40 80 60
(A) 15 0 0 60 0 - 50 80 80
(41) 15 0 0 100 95 100 100 100 100

^

70

Table B7: Pre-emergence-Test/greenhouse



Compound of Preparation Example No. application rate (g ai/ha) wheat Digitaria Lolium Setaria Ama-ranthus Solanum Stellaria
(G) 15 0 50 60 70 40 80 80
(F) 15 0 60 40 30 40 80 70
(E) 15 0 0 0 20 10 70 40
(D) 15 0 20 20 10 80 80 60
(C) 15 0 20 50 50 80 - 80
(B) 15 0 0 20 40 80 80 60
(A) 15 0 0 0 0 - 80 80
(39) 15 0 100 95 100 100 95 100

71

Table B8: Pre-emeigence-Test/gieenhouse



Compound of Preparation Example No. application rate (g ai/ha) wheat maize soy
beans Alope-curus Lolium Matricaria Stellaria
(G) 15 0 0 50 - 60 70 80
(F) 15 0 0 10 70 40 20 70
(E) 15 0 0 0 20 0 20 40
(D) 15 0 20 0 0 20 10 60
(C) 15 0 0 0 0 50 80 80
(B) 15 0 0 0 20 20 40 60
(A) 15 0 0 0 60 0 50 80
(46) 15 50 0 0 95 90 100 100





Table B9: Pre-emergence-Test/greenhouse

Compound of Preparation Example No. application rate (g ai/ha) Avena fatua Loliura Setaria Ama-
ranthus Matricaria Polygonum Stellaria
(G) 15 50 60 70 40 70 70 80
(F) 15 60 40 30 40 20 50 70
(E) 15 0 0 20 10 20 20 40
(D) 15 70 20 10 80 10 10 60
(Q 15 50 50 50 80 80 60 80
(B) 15 10 20 40 80 40 50 60
(A) 15 0 0 0 - 50 0 80
(43) 15 - 95 95 100 100 100 100
(45) 15 95 100 100 100 100 95 100
(47) 15 95 80 95 100 100 90 100
(48) 15 95 95 - 100 95 95 100

Table BIO: Pre-emergence-Test/greenhouse



Compound of Preparation Example No. application rate (g ai/ha) Avena fatua Bromus Lolium Setaria Ama-ranthus Galium Stellaria
(G) 15 50 - 60 70 40 30 80
(F) 15 60 70 40 30 40 10 70
(E) 15 0 20 0 20 10 0 40
(D) 15 70 10 20 10 80 0 60
(C) 15 50 70 50 50 80 70 80
(B) 15 10 40 20 40 80 20 60
(A) 15 0 60 0 0 - 10 80
(42) 15 90 95 95 95 100 100 100

75
^

WE CLAIM:
1. Compounds of the general formula (I)
in which
Q1 represents O (oxygen) or S (sulphur),
Q2 represents O (oxygen) or S (sulphur),
R1 represents optionally cyano-, halogen- or Ci-C4-alkoxy- substituted alkyl having 1 to 6 carbon atoms, represents in each case optionally cyano- or halogen-substituted alkenyl or alkynyl having in each case 2 to 6 carbon atoms, representing in each case optionally cyano-, halogen or C1-C4-alkyl-substituted cycloalkyl or cycloalkylalkyl having in each case 3 to 6 carbon atoms in the cycloalkyl group and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety, represents in each case optionally nitro-, cyano-, halogen-, C1-C4-alkyl- or C1-C4-alkoxy-substituted aryl or arylalkyl having in each case 6 or 10 carbon atoms in the aryl group and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety, or represents in each case optionally nitro-, cyano-, halogen C1-C4-alkyl- or C1-C4-alkoxy-substituted heterocyclyl or heterocyclylalkyl having in each case up to 6 carbon atoms and additionally 1 to 4 nitrogen atoms and/or 1 or 2 oxygen or sulphur atoms in the heterocyclyl group and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety,
76

R2 represents hydrogen, cyano, nitro, halogen, represents in each case optionally, cyano-, halogen- or C1-C4-alkoxy-substituted alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl or alkylsulfonyl having in each case 1 to 6 carbon atoms in the alkyl group, or represents in each case optionally cyano or halogen-substituted alkenyl, alkynyl, alkenyloxy or alkynyloxy having in each case 2 to 6 carbon atoms in the alkenyl or alkynyl group,
R3 represents halogen-substituted alkoxy having 1 to 6 carbon atoms, and
R4 represents hydrogen, hydroxy, amino, cyano, represents C2-C10 alkylideneamino, represents optionally fluorine-chlorine-, bromine-, cyano-, C1-C4-alkoxy-, C1-C4-alkyl-carbonyl- or C1-C4-alkoxy-carbonyl-substituted alkyl having 1 to 6 carbon atoms, represents in each case optionally fluorine, chlorine- and/or bromine-substituted alkenyl or alkynyl having in each case 2 to 6 carbon atoms, represents in each case optionally fluorine-, chlorine-, bromine-, cyano-, Ci-C4-alkoxy- or C1-C4-alkoxy-carbonyl-substituted alkoxy, alkylamino or alkylcarbonylamino having in each case 1 to 6 carbon atoms in the alkyl groups, represents alkenyloxy having 3 to 6 carbon atoms, represents dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups, represents in each case optionally fluorine-, chlorine-, bromine-, cyano- and/or C1-C4-alkyl-substituted cycloalkyl, cyolbalkylamino or cycloalkylalkyl having in each case 3 to 6 carbon atoms in the alkyl group and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety, or represents in each case optionally fluorine-, chlorine-, bromine-, cyano-. nitro-, C1-C4-alkyl-, trifluoromethyl- and/or C1-C4-alkoxy-substituted aryl or arylalkyl having in each case 6 or 10 carbon atoms in the aryl group and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety, or together with R represents optionally branched and/or C1-C4-alkyl-substituted alkanedlyl, oxaalkanediyl, thiaalkanediyl or azaalkanediyl having 3 to 6 carbon atoms where the oxa, thia or aza components may be positioned at the beginning, at the end or within the alkanediyl grouping, and salts of the compounds of the formula (I).
2. Compounds as claimed in claim 1, wherein
R1 represents in each case optionally cyano-, fluorine-, chlorine-,
methoxy- or ethoxy-substituted methyl, ethyl, n- or isoproyl, n-, iso-, s-
or t-butyl, represents in each case optionally cyano-, fluorine- or
chlorine-substituted propenyl, butenyl, propynyl or butynyl, represents
in each case optionally cyano-, fluorine-, chlorine-, methyl- .or ethyl-
substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,
cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or
cyclohexylmethyl, represents in each case optionally cyano-, fluorine-,
77

chlorine-, methyl- ethyl-, n- or isopropyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or isopropoxy-, difluoromethoxy- or trifluoromethoxy-substituted phenyl, phenylmethyl or phenylethyl, or represents in each case optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n-or isopropyl-, methoxy-, ethoxy-, n- or isopropoxysubstituted heterocydyl or heterocyclylmethyl, where the heterocyclyl group is in each case selected from the group consisting of oxetartyl, thietanyl, furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl,
R2 represents hydrogen, cyano, fluorine, chlorine, bromine, represents
in each case optionally cyano-, fluorine-, chlorine-, methoxy- or
ethoxysubstituted methyl, ethyl, n- or isopropyl, n-, iso-, s or t-butyl,
methoxy, ethoxy, n- or isopropoxy, methoxycarbonyl, ethoxycarbonyl, n-
or isopropoxycarbonyl, methylthio, ethylthio, n- or isopropylthio,
methylsulfinyl ethylsulfinyl, methylsulfonyl or ethylsulfonyl, or
represents in each case optionally cyano-, fluorine- or chlorine-
substituted propenyl, butenyl, propynyl, burynyl,
propenyloxy, butenyloxy, propynyloxy or butynyloxy,
R3 represents fluorine- or chlorine-substituted methoxy, ethoxy, n- or i-propoxy, n-. i-, s-, or t-butoxy, n-, i-, s-, or to pentyloxy or - neo-pentyloxy, and
R4 represents hydrogen, hydroxy, amino, represents in each case
optionally fluorine-, chlorine-, cyano-, methoxy- or ethoxy-substituted
methyl, ethyl, n- or isopropyl, n-, iso-, s- or t-butyl, represents in each
case optionally fluorine, chlorine- and/or bromine-substituted ethenyl,
propenyl, butenyl, propynyl or butynyl represents in each case
optionally fluorine-, chlorine-, cyano , methoxy- or ethoxysubstituted
methoxy, ethoxy, n- or isopropoxy, n-, iso-, s- or t-butoxy, methylamino,
ethylamino, n- or isopropylarnino, n-, iso-, s- or t-burylamino, represents
propenyloxy or butenyloxy, represents dimethylamlno or diethylamino,
represents in each case optionally fluorine-, chlorine-, methyl- and/or
ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cydohexyl,
cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino,
cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or
cyclohexylmethyl, or represents in each case optionally fluorine-, chlorine-, methyl-, trifluoromethyl- and/or methoxy-substituted phenyl or ben2yl.
3. Compounds as claimed in claim 1, wherein
R1 represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or isopropyl,







78






R2 represents fluorine, chlorine, bromine or represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxysubstituted methyl, ethyl, n- or isopropyl,
R3 represents fluorine- or chlorine-substituted methoxy, ethoxy, n- or i-propoxy, n-. i-, s-, or t-butoxy, n-, i-, s-, or- to-pentyloxy, or nec-pentyloxy, and
R4 represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or isopropyl, represents in each case optionally fluorine- or chlorine- substituted ethenyl, propenyl or propynyl, represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxysubstituted methoxy, ethoxy, n- or isopropoxy, represents - methylamino, or represents cyclopropyl.
4. Compounds as claimed in claim 3, wherein R1 represents methyl.
5. Compounds as claimed in claim 3, wherein R1 represents ethyl.
6. Compounds as claimed in claim 3, wherein R1 represents n-propyl.
7. Compounds as claimed in claim 3, wherein R1 represents isopropyl.
8. Process for preparing the compounds as claimed in claim 1,
wherein
(a) substituted thiophene-3-sulphonamides of the general formula (II)

in which
79

R1 and R2 are as defined in Claim 1.
are reacted with substituted triazolin(ethi)ones of the general formula (111)

in which
Q1, Q2, R3 and R4 are as defined in claim 1 and
Z represents halogen, alkoxy, aryloxy or arylalkoxy,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
or that
(b) substituted thiene-3-ylsulphonyl iso(thio)cyanates of the general formula (IV)

in which
Q1, R1 and R2 are as defined in Claim 1
are reacted with triazolin(ethi)ones of the general formula (V)




80





in which


are reacted with triazolin(ethi)ones of the general formula (V)

in which
Q2, R4 and R3 are as defined in Claim 1
and metal (thio)cyanates of the general formula (VII)
81

M-Q1-CN (VII)
in which
Q1 is as defined above,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
or that
(d) substituted thiophene-3-sulphonyl chlorides of the general formula (VI)
in which
R1 and R2 are as defined in claim 1
are reacted with triazolin(ethi)one (thio)carboxamides of the general formula (VIII)

in which
Q1, Q2, R3 and R4 are as defined in claim 1,
82

if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
or that
(e) substituted thiene-3-yl- sulphonylamino(thio)carbonyl compounds of the general formula (IX)

in which
Q1, R1 and R2 are s defined in Claim 1,
Z represents halogen, alkoxy, aryloxy or arylalkoxy are reacted with triazolin(ethi)ones of the general formula (V)

if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
and the compounds of the formula (I) obtained by process (a), (b), (c), (d) or (e) are, if appropriate, converted by customary methods in salts.


83


9. Herbicidal composition wherein said composition comprises between 0.1 to 95 % by weight of active compound of formula (I) as claimed in any of Claims 1 to 7 and customary extenders and/or surfactants.

Dated this 17th day of October,
#FORM 2
THE PATENTS ACT 1970
[39 OF 1970]
COMPLETE SPECIFICATION
[See Section 10]



"SUBSTITUTED THIENE-3-
YLSULPHONYLAMINO[THIO]CARBONYLTRIAZOLIN[ETHI]ONES"



BAYER AKTIENGESELLSCHAFT, a body corporate organised under the laws of Germany, of D-51368 Leverkusen, Germany,








Le A 35 696-Foreign Countries Lu/klu/NT
-1-Substituted thiene-3-ylsulphonyIamino(thio)carbonyItriazolin(ethi)ones
The invention relates to novel substituted tmene-3-ylsulphonylamino(thio)carbonyl-
5 triazolin(ethi)ones, to processes for their preparation and to their use as herbicides.
It is already known that certain substituted thienylsulphonylamino(thio)carbonyl-triazolin(ethi)ones, such as, for example, the compounds methyl 4-[[[(4,5-dihydro-3-ethoxy-4-methyl-5-oxo-lH-l,2,4-triazol-l-yl)carbonyl]amino]sulfonyl]-5-methyl-3-
10 thiophenecarboxylate, methyl 4-[[[(4,5-dihydro-3-methoxy-4-methyI-5-oxo-lH-
1,2,4-triazol-1 -yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate, meth¬
yl 4-[[[(4,5-dihydro-4-methyl-5-oxo-3-n-propoxy-1H-1,2,4-triazol-1 -yl)carbon-
yl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate, methyl" 4-[[[(4,5-dihydro-4-
methyl-5-oxo-3-isopropoxy- 1H-1,2,4-triazol-1 -yl)carbonyl]amino]sulfonyl]-5-meth-
15 yl-3-thiophenecarboxylate, methyl 4-[[[(4-cyclopropyl-4,5-dihydro-3-methoxy-5-
oxo-lH-1,2,4-triazol-l -yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarb-oxylate, methyl 4-[[[(4-cyclopropyl-4,5-dihydro-3-ethoxy-5-oxo-lH-l,2,4-triazol-1-yI)carbonyl]ammo]suIfonyl]-5-methyl-3-thiophenecarboxylate, methyl 4-[[[(4-cyclo-propyl-4,5-dihydro-5-oxo-3-n-propoxy-lH-l,2,4-triazol-l-yl)carbonyl]amino]sulf-
20 onyl]-5-methyl-3-thiophenecarboxylate, methyl 4-[[[(4-cyclopropyl-4,5-dihydro-5-
oxo-3-isopropoxy-lH-l,2,4-triazol-l-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thio-phenecarboxylate, methyl 4-[[[(3,4-dicyclopropyl-4,5-dihydro-5-oxo-lH-l,2,4-tri-azol-l-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate, methyl 4-[[[(4,5-dihydro-3,4-dimethyl-5-oxo- 1H-1,2,4-triazol-1 -yl)carbonyl]amino]sulfonyl]-
25 5-methyl-3-thiophenecarboxylate, methyl 4-[[[(4,5-dihydro-3-ethyl-4-methyl-5-oxo-
lH-l,2,4-triazol-l-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate, methyl 4-[[[(4,5-dihydro-4-methyl-3-methylthio-5-oxo-lH-l,2,4-triazol-l-yl)carb-onyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate, ethyl 4-[[[(4,5-dihydro-3,4-dimethoxy-5-oxo-lH-l,2,4"triazol-l-yl)carbonyl]amino]sulfonyl]-5-chloro-3-thio-
30 phenecarboxylate, methyl 4-[[[(4,5-dihydro-3-ethoxy-4-methyl-5-oxo-lH-l,2,4-tri-
azol-1 -yl)thioxocarbonyl] aminojsulfonyl] -5 -fluoro-3 -thiophenecarboxylate, methyl
2

Le A 35 696-Foreign Countries
-2-
4-[[[(4,5-dihydro-3-ethyl-4-methoxy-5-thioxo-lH-l,2,4-triazol-l-yl)carb-
ony 1] amino] sulfony 1] -5 -trifluoromethy 1-3 -thiophenecarboxy late, ethyl 4- [ [ [(4,5 -di-
hydro-4-ethyl-3-methoxy-5-oxo-lH-l,2,4-triazol-l-yl)carbonyl]-ammo]sulfonyl]-5-
methyl-3-thiophenecarboxylate and isopropyl 4-[[[(3,4-dimethyl-5-oxo-4,5-dihydro-
5 lH-l,2,4-triazol-l-yl)carbonyl]amino]sulfonyl]-5-ethyl-3-thiophenecarboxylate, have
herbicidal properties (cf. WO-A-01/05788, cf. also WO-A-97/16449, WO-A-98/24787). However, the activity of these compounds is not entirely satisfactory.
This invention now provides the novel substituted thiene-3-ylsulphonylamino(thio)-
10 carbonyltriazolin(ethi)ones of the general formula (I)


(I)

in which
15 Q1 represents O (oxygen) or S (sulphur),
■a
Q represents O (oxygen) or S (sulphur),
R represents optionally cyano-, halogen- or C1-C4-alkoxy-substituted alkyl
20 having 1 to 6 carbon atoms, represents in each case optionally cyano- or
halogen-substituted alkenyl or alkynyl having in each case 2 to 6 carbon
atoms, representing in each case optionally cyano-, halogen- or C1-C4-alkyl-
substituted cycloalkyl or cycloalkylalkyl having in each case 3 to 6 carbon
atoms in the cycloalkyl group and, if appropriate, 1 to 4 carbon atoms in the
25 alkyl moiety, represents in each case optionally nitro-, cyano-, halogen-,
C1-C4-alkyl- or C1-C4-alkoxy-substituted aryl or arylalkyl having in each case



3

Le A 35 696-Foreign Countries
-3-
6 or 10 carbon atoms in the aryl group and, if appropriate, 1 to 4 carbon atoms
in the alkyl moiety, or represents in each case optionally nitro-, cyano-,
halogen-, Ci-C4-alkyl- or Ci-C4-alkoxy-substituted heterocyclyl or hetero-
cyclylalkyl having in each case up to 6 carbon atoms and additionally 1 to 4
5 nitrogen atoms and/or 1 or 2 oxygen or sulphur atoms in the heterocyclyl
group and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety,
R2 represents hydrogen, cyano, nitro, halogen, represents in each case optionally,
cyano-, halogen- or Ci-C4-alkoxy-substituted alkyl, alkoxy, alkoxycarbonyl,
10 alkylthio, alkylsulfmyl or alkylsulfonyl having in each case 1 to 6 carbon
atoms in the alkyl group, or represents in each case optionally cyano- or halogen-substituted alkenyl, alkynyl, alkenyloxy or alkynyloxy having in each case 2 to 6 carbon atoms in the alkenyl or alkynyl group,
15 R3 represents hydrogen, hydroxyl, mercapto, amino, cyano, halogen, represents
optionally cyano-, halogen-, C;[-C4-alkoxy-, Ci-C4-alkyl-carbonyl- or C\-C4-alkoxy-carbonyl-substituted alkyl having 1 to 6 carbon atoms, represents in each case optionally fluorine-, chlorine- and/or bromine-substituted alkenyl or alkynyl having in each case 2 to 6 carbon atoms, represents in each case
20 optionally cyano-, halogen-, Ci-C4-alkoxy- or Ci-C4-alkoxy-carbonyl-
substituted alkoxy, alkylthio, alkylamino or alkylcarbonylamino having in each case 1 to 6 carbon atoms in the alkyl group, represents alkenyloxy, alkynyloxy, alkenylthio, alkynylthio, alkenylamino or alkynylamino having in each case 3 to 6 carbon atoms in the alkenyl or alkynyl group, represents
25 dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups,
represents in each case optionally methyl- and/or ethyl-substituted aziridino, pyrrolidino, piperidino or morpholino, represents in each case optionally fluorine-, chlorine-, bromine-, cyano- and/or Ci-C4-alkyl-substituted cycloalkyl, cycloalkenyl, cycloalkyloxy, cycloalkylthio, cycloalkylamino,
30 cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylthio or cycloalkylalkyl-
amino having in each case 3 to 6 carbon atoms in the cycloalkyl or
-M-

Le A 35 696-Foreign Countries
4-
cycloalkenyl group and, if appropriate, 1 to 4 carbon atoms in the alkyl
moiety, or represents in each case optionally fluorine-, chlorine-, bromine-,
cyano-, nitro-, C1-C4-alkyl-, trifluoromethyl-, C1-C4-alkoxy- and/or C1-C4-
alkoxy-carbonyl-substituted aryl, arylalkyl, aryloxy, arylalkoxy, arylthio,
5 arylalkylthio, arylamino or arylalkylamino having in each case 6 or 10 carbon
atoms in the aryl group and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety, and
R4 represents hydrogen, hydroxy, amino, cyano, represents C2-C10-
10 alkylideneamino, represents optionally fluorine-, chlorine-, bromine-, cyano-,
C1-C4-alkoxy-, C1-C4-alkyl-carbonyl- or C1-C4-alkoxy-carbonyl-substituted alkyl having 1 to 6 carbon atoms, represents in each case optionally fluorine-, chlorine- and/or bromine-substituted alkenyl or alkynyl having in each case 2 to 6 carbon atoms, represents in each case optionally fluorine-, chlorine-,
15 bromine-, cyano-, C1-C4-alkoxy- or C1-C4-alkoxy-carbonyl-substituted
alkoxy, alkylamino or alkylcarbonylamino having in each case i to 6 carbon atoms in the alkyl group, represents alkenyloxy having 3 to 6 carbon atoms, represents dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups, represents in each case optionally fluorine-, chlorine-, bromine-,
20 cyano- and/or C1-C4-alkyl-substituted cycloalkyl, cycloalkylamino or
cycloalkylalkyl having in each case 3 to 6 carbon atoms in the alkyl group and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety, or represents in each case optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, C1-C4-alkyl-, trifluoromethyl- and/or C1-C4-alkoxy-substituted aryl or arylalkyl
25 having in each case 6 or 10 carbon atoms in the aryl group and, if appropriate,
1 to 4 carbon atoms m the alkyl moiety, or together with R represents optionally branched and/or C1-C4-alkyl-substituted alkanediyl, oxaalkanediyl, thiaalkanediyl or azaalkanediyl having 3 to 6 carbon atoms, where the oxa, thia or aza components may be positioned at the beginning, at the end or
30 within the alkanediyl grouping,
5

Le A 35 696-Foreign Countries
-5-
- and salts of the compounds of the formula (I) -
except for the compounds methyl 4-[[[(4,5-dihydro-3-ethoxy-4-methyl-5-oxo-lH-
1,2,4-triazol-l-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate, meth-
5 yl 4-[[[(4,5-dihydro-3-methoxy-4-methyl-5-oxo-1H-1,2,4-triazol-1 -yl)carbonyl]ami-
no]sulfonyl]-5-methyl-3-thiophenecarboxylate, methyl 4-[[[(4,5-dihydro-4-methyl-5-oxo-3-n-propoxy- 1H-1,2,4-triazol-1 -yl)carbonyl]amino]sulfonyl]-5-methyl-3-thio-phenecarboxylate, methyl 4-[[[(4,5-dihydro-4-methyl-5-oxo-3-isopropoxy-lH-l ,2,4-triazol-l-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate, methyl 4-
10 [[[(4-cyclopropyl-4,5-dihydro-3-methoxy-5-oxo-lH-l,2,4-triazol-l-yl)carb-
onyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate, methyl 4-[[[(4-cyclopropyl-4,5-dihydro-3-ethoxy-5-oxo-lH-l,2,4-triazol-l-yl)carbonyl]amino]sulfonyl]-5-meth-yl-3-thiophenecarboxylate, methyl 4-[[[(4-cyclopropyl-4,5-dihydro-5-oxo-3-n-prop-oxy-lH-l,2,4-triazol-l-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarb-
15 oxylate, methyl 4-[[[(4-cyclopropyl-4,5-dihydro-5-oxo-3-isopropoxy-lH-l,2,4-tri-
azol-l-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate, methyl 4-[[[(3,4-dicyclopropyl-4,5-dihydro-5-oxo-1H-1,2,4-triazol-1 -yl)carbonyl] amino]-sulf-onyl]-5-methyl-3-thiophenecarboxylate, methyl 4-[[[(4,5-dihydro-3,4-dimethyl-5-oxo-1H-1,2,4-triazol-1 -yl)carbonyl] amino] sulfonyl]-5 -methyl-3 -thiophenecarb-
20 oxylate, methyl 4-[[[(4,5-dihydro-3-ethyl-4-methyl-5-oxo-lH-l,2,4-triazol-l-yl)carb-
onyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate, methyl 4-[[[(4,5-dihydro-4-methyl-3-methylthio-5-oxo-lH-l,2,4-triazol-l-yl)carbonyl]amino]sulfonyl]-5-meth-yl-3-thiophenecarboxylate, ethyl 4-[[[(4,5-dihydro-3,4-dimethoxy-5-oxo-lH-l,2,4-triazol-l-yl)carbonyl]amino]sulfonyl]-5-chloro-3-thiophenecarboxylate, methyl 4-
25 [[[(4,5-dihydro-3-ethoxy-4-methyl-5-oxo-lH-l,2,4-triazol-l-yl)thioxocarbonyl]-
amino]sulfonyl]-5-fluoro-3-thiophenecarboxylate, methyl 4-[[[(4,5-dihydro-3-ethyl-4-methoxy-5-thioxo-lH-l,2,4-triazol-l-yl)carbonyl]amino]sulfonyl]-5-trifluoro-methyl-3-thiophenecarboxylate, ethyl 4-[[[(4,5-dihydro-4-ethyl-3-methoxy-5-oxo-lH-l,2,4-triazol-l-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate
30 and isopropyl 4-[[[(3,4-dimethyl-5-oxo-4,5-dihydro-lH-l,2,4-triazol-l-yl)carb-
onyl]amino]sulfonyl]-5-ethyl-3-thiophenecarboxylate known from WO-A-01/05788,
6

Le A 35 696-Foreign Countries
which are excluded by disclaimer.
Saturated or unsaturated hydrocarbon groupings, such as alkyl, allkanediyl, alkenyl
5 or alkynyl, are in each case straight-chain or branched as far as this is possible -
including in combinations with heteroatoms, such as in alkoxy.
Optionally substituted radicals can be mono- or polysubstituted, and in the case of polysubstitution, the substituents can be identical or different.
10
Preferred substituents or ranges of the radicals present in the formulae listed above and below are defined below.
Q1 preferably represents O (oxygen) or S (sulphur).
15
Q2 preferably represents 0 (oxygen) or S (sulphur).
R1 preferably represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or isoproyl, n-, iso-, s- or t-
20 butyl, represents in each case optionally cyano-, fluorine- or chlorine-
substituted propenyl, butenyl, propynyl or butynyl, represents in each case optionally cyano-, fluorine-, chlorine-, methyl- or ethyl-substituted cyclo-propyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutyl-methyl, cyclopentylmethyl or cyclohexylmethyl, represents in each case
25 optionally cyano-, fluorine-, chlorine-, methyl-, ethyl-, n- or isopropyl-,
trifluoromethyl-, methoxy-, ethoxy-, n- or isopropoxy-, difluoromethoxy- or trifluoromethoxy-substituted phenyl, phenylmethyl or phenylethyl, or represents in each case optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or isopropyl-, methoxy-, ethoxy-, n- or isopropoxy-
30 substituted heterocyclyl or heterocyclylmethyl, where the heterocyclyl group
7

Le A 35 696-Foreign Countries
-7-
is in each case selected from the group consisting of oxetanyl, thietanyl, furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl.
R2 preferably represents hydrogen, cyano, fluorine, chlorine, bromine, represents
5 in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-
substituted methyl, ethyl, n- or isopropyl, n-, iso-, s- or t-butyl, methoxy,
ethoxy, n- or isopropoxy, methoxycarbonyl, ethoxycarbonyl, n- or iso-
propoxycarbonyl, methylthio, ethylthio, n- or isopropylthio, methylsulfinyl,
ethylsulfinyl, methylsulfonyl or ethylsulfonyl, or represents in each case
10 optionally cyano-, fluorine- or chlorine-substituted propenyl, butenyl,
propynyl, butynyl, propenyloxy, butenyloxy, propynyloxy or butynyloxy.
R3 preferably represents hydrogen, hydroxy, mercapto, amino, cyano, fluorine, , chlorine, bromine, represents in each case optionally fluorine-, chlorine-,
15 cyano-, methoxy-, ethoxy-, n- or isopropoxy-, acetyl-, propionyl-, n- or
isobutyroyl-, methoxycarbonyl-, ethoxycarbonyl-, n- or isopropoxycarbonyl-substituted methyl, ethyl, n- or isopropyl, n-, iso-, s- or t-butyl, n-, iso-, s- or t-pentyl or neopentyl, represents in each case optionally fluorine-, chlorine-and/or bromine-substituted ethenyl, propenyl, butenyl, ethynyl, propynyl or
20 butynyl, represents in each case optionally fluorine-, chlorine-, cyano-,
methoxy-, ethoxy-, n- or isopropoxy-, n-, iso-, s- or t-butoxy-, methoxy¬carbonyl-, ethoxycarbonyl-, n- or isopropoxycarbonyl-substituted methoxy, ethoxy, n- or isopropoxy, n-, iso-, s- or t-butoxy, n-, iso-, s- or t-pentyloxy or neopentyloxy, methylthio, ethylthio, n- or isopropylthio, n-, iso-, s- or t-
25 butylthio, methylamino, ethylamino, n- or isopropylamino, n-, iso-, s- or t-
butylamino, acetylamino or propionylamino, represents propenyloxy, butenyloxy, ethynyloxy, propynyloxy, butynyloxy, propenylthio, butenylthio, propynylthio, butynythio, propenylamino, butenylamino, propynylamino or butynylamino, represents dimethylamino, diethylamino or dipropylamino,
30 represents in each case optionally fluorine-, chlorine-, methyl- and/or ethyl-
substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl,



8

Le A 35 696-Foreign Countries
-8-
cyclohexenyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyl-
oxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclo-
propylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclo-
propylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl,
5 cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexyl-
methoxy, cyclopropylmethylthio, cyclobutylmethylthio, cyclopentylmethyl-
thio, cyclohexylmethylthio, cyclopropylmethylarnino, cyclobutylmethyl-
amino, cyclopentylmethylammo or cyclohexylmethylammo, or represents in
each case optionally fluorine-, chlorine-, bromine-, methyl-, trifluoromethyl-,
10 methoxy- or methoxycarbonyl-substituted phenyl, benzyl, phenoxy,
benzyloxy, phenylthio, benzylthio, phenylamino or benzylamino.
R4 preferably represents hydrogen, hydroxy, amino, represents in each case optionally fluorine-, chlorine-, cyano-, methoxy- or ethoxy-substituted
15 methyl, ethyl, n- or isopropyl, n-, iso-, s- or t-butyl, represents in each case
optionally fluorine-, chlorine- and/or bromine-substituted ethenyl, propenyl, butenyl, propynyl or butynyl, represents in each case optionally fluorine-, chlorine-, cyano-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or isopropoxy, n-, iso-, s- or t-butoxy, methylamino, ethylamino, n- or
20 isopropylamino, n-, iso-, s- or t-butylamino, represents propenyloxy or
butenyloxy, represents dimethylamino or diethylamino, represents in each case optionally fluorine-, chlorine-, methyl- and/or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylamino, cyclo¬butylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclo-
25 butylmethyl, cyclopentylmethyl or cyclohexylmethyl, or represents in each
case optionally fluorine-, chlorine-, methyl-, trifluoromethyl- and/or methoxy-substituted phenyl or benzyl.
R and R together preferably represent trimethylene (propane-1,3-diyl), 1-
30 oxatrimethylene, 1-thiatrimethylene, 1-azatrimethylene, tetramethylene
(butane-1,4-diyl), 1-oxatetramethylene, 1-thiatetramethylene, 1-azatetrameth-



9

Le A 35 696-Foreign Countries
ylene or pentamethylene (pentane-l,5-diyl), each of which is optionally mono- to trisubstituted by methyl and/or ethyl, where the position 1 is connected to the point of attachment of R3.
5 Q1 particularly preferably represents O (oxygen) or S (sulphur).
Q2 particularly preferably represents 0 (oxygen) or S (sulphur).
R1 particularly preferably represents in each case optionally fluorine-, chlorine-,
10 methoxy- or ethoxy-substituted methyl, ethyl, n- or isopropyl.
R2 particularly preferably represents fluorine, chlorine, bromine or represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or isopropyl.
15
R3 particularly preferably represents hydrogen, chlorine, bromine, represents in each case optionally fluorine-, chlorine-, methoxy-, ethoxy-, n- or isopropoxy-substituted methyl, ethyl, n- or isopropyl, n-, iso-, s- or t-butyl, n-, iso-, s- or t-pentyl or neopentyl, represents in each case optionally fluorine- or chlorine-
20 substituted ethenyl, propenyl, butenyl, propynyl or butynyl, represents in each
case optionally fluorine-, chlorine-, methoxy-, ethoxy-, n- or isopropoxy-substituted methoxy, ethoxy, n- or isopropoxy, n-, iso-, s- or t-butoxy, n-, iso-, s- or t-pentyloxy, neopentyloxy, methylthio, ethylthio, n- or isopropylthio, n-, iso-, s- or t-butylthio, methylamino, ethylamino, n- or isopropylamino,
25 represents propenyloxy, propynyloxy, propenylthio, propynylthio, propenyl-
amino or propynylamino, represents dimethylamino or diethylamino, represents in each case optionally fluorine-, chlorine- or methyl-substituted cyclopropyl, cyclopropyloxy, cyclopropylmethyl, cyclopropylmethoxy, cyclobutyloxy, cyclopentyloxy or cyclohexyloxy, or represents in each case
30 optionally fluorine-, chlorine- or methyl-substituted phenoxy or benzyloxy.
10

Le A 35 696-Foreign Countries
-10-
R4 particularly preferably represents in each case optionally fluorine-, chlorine-,
methoxy- or ethoxy-substituted methyl, ethyl, n- or isopropyl, represents in
each case optionally fluorine- or chlorine-substituted ethenyl, propenyl or
propynyl, represents in each case optionally fluorine-, chlorine-, methoxy- or
5 ethoxy-substituted methoxy, ethoxy, n- or isopropoxy, represents methyl-
amino, or represents cyclopropyl.
R3 and R4 together particularly preferably represent trimethylene (propane-l,3-diyl),
1-oxatrimethylene, 1-thiatrimethylene, 1-azatrimethylene, tetramethylene
10 (butane- 1,4-diyl), 1-oxatetramethylene, 1-thiatetramethylene, 1-
azatetramethylene or pentamethylene (pentane-l,5-diyl), each of which is optionally mono- or disubstituted by methyl, where the position 1 is connected to the point of attachment of R .
15 The invention preferably also provides the sodium, potassium, lithium, magnesium,
calcium, ammonium, C1-C4-alkylammonium, (where the alkyl radical is optionally substituted by hydroxyl), di(C1-C4-alkyl)ammonium, tri(C1-C4-alkyl)ammonium, tetra(C1-C4-alkyl)arnmonium, tri(C1-C4-alkyl)sulfonium, C5- or C6-cyclo-alkylammonium and di(C1-C2-alkyl)benzylarnmonium salt and also the di(C1-C2-
20 alkyl)pyridinylammonium salts and the pyrrolidinium salts of compounds of the
formula (I) in which Q1, Q2, R1, R2, R3 and R4 have the meanings given above as being preferred.
A very particularly preferred group are those compounds of formula (I) in which 25
R1 represents methyl and Ql and Q2 and R2, R3 and R4 have the meanings given above as being particularly preferred,
except for the prior-art compounds methyl 4-[[[(4,5-dihydro-3-ethoxy-4-methyl-5-
30 oxo-lH-l,2,4-triazol-l-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxyl-
ate, methyl 4-[[[(4,5-dihydro-3-methoxy-4-methyl-5-oxo-lH-l,2,4-triazol-l-yl)carb-

Le A 35 696-Foreign Countries
-11-
onyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate, methyl 4-[[[(4,5-dihydro-4-
methyl-5-oxo-3-n-propoxy-lH-l,2,4-triazol-l-yl)carbonyl]amino]sulfonyl]-5-
methyl-3-thiophenecarboxylate, methyl 4-[[[(4,5-dihydro-4-methyl-5-oxo-3-
isopropoxy-lH-l,2,4-triazol-l-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thio-
5 phenecarboxylate, methyl 4-[[[(4-cyclopropyl-4,5-dihydro-3-methoxy-5-oxo-lH-
l,2,4-triazol-l-yl)carbonyl]-amino]sulfonyl]-5-methyl-3-thiophenecarboxylate, methyl 4-[[[(4-cyclopropyl-4,5-dihydro-3-ethoxy-5-oxo-1H-1,2,4-triazol-1 -yl)carb-onyl]amino]sulfonyl]-5-methyl-3-thiopheneearboxylate, methyl 4-[[[(4-cyclopropyl-4,5-dihydro-5-oxo-3-n-propoxy-lH-l,2,4-triazol-l-yl)carbonyl]amino]sulfonyl]-5-
10 methyl-3-thiophenecarboxylate, methyl 4-[[[(4-cyclopropyl-4,5-dihydro-5-oxo-3-
isopropoxy-lH-l,234-triazol-l-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thio-phenecarboxylate, methyl 4-[[[(3,4-dicyclopropyl-4,5-dmydro-5-oxo-lH-l,2,4-tri-azol-l-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate, methyl 4-[[[(4,5-dihydro-3,4-dimethyl-5-oxo-lH-l,234-triazol-l-yl)carbonyl]amino]sulfonyl]-
15 5-methyl-3-thiophenecarboxylate, methyl 4-[[[(4,5-dihydro-3-ethyl-4-methyl-5-oxo-
lH-l,2,4-triazol-l-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate, methyl 4-[[[(4,5-dihydro-4-methyl-3-methylthio-5-oxo-lH-l,2,4-triazol-l-yl)carb-onyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate, methyl 4-[[[(4,5-dihydro-3-ethoxy-4-methyl-5-oxo-1H-1,2,4-triazol-1-yl)thioxocarbonyl] amino] sulfonyl]-5-
20 fluoro-3-thiophenecarboxylate and methyl 4-[[[(4,5-dihydro-3-ethyl-4-methoxy-5-
thioxo-lH-l,2,4-triazol-l-y1)carbonyl]amino]sulfonyl]-5-trifluoromethyl-3-thio-phenecarboxylate.
A further very particularly preferred group are those compounds of the formula (I) in
25 which
R1 represents ethyl and Q1 and Q2 and R2, R3 and R4 have the meanings given above as being particularly preferred,
30 except for the prior-art compounds ethyl 4-[[[(4,5-dihydro-3,4-dimethoxy-5-oxo-lH-
l,2,4-triazol-l-yl)carbonyl]amino]sulfonyl]-5-chloro-3-thiophenecarboxylate and
12

Le A 35 696-Foreign Countries
-12-
ethyl 4-[[[(4,5-dihydro-4-ethyl-3-methoxy-5-oxo-lH-l,2,4-triazol-l-yl)carbonyl]-amino]sulfonyl]-5-methyl-3-thiophenecarboxylate.
A further very particularly preferred group are those compounds of the formula (I) in
5 which
R1 represents n-propyl and Ql and Q2 and R2, R3, and R4 have the meanings given above as being particularly preferred.
10 A further very particularly preferred group are those compounds of the formula (I) in
which
R1 represents isopropyl and Q1 and Q2 and R2, R3 and R4 have the meanings given
above as being particularly preferred, except for the prior-art compound isopropyl 4-
15 [[[(3,4-dimethyl-5-oxo-4,5-dihydro-lH-l,2,4-triazol-l-yl)carbonyl]amino]sulfonyl]-
5-ethyl-3-thiophenecarboxylate.
A further very particularly preferred group are those compounds of the formula (I) in which
20
Q1 and Q2 and R1 and R2 have the meanings given above as being particularly preferred and R3 and R4 together represent trimethylene (propane- 1,3-diyl), 1-oxatrimethylene, 1-thiatrimethylene, 1-azatrimethylene, tetramethylene (butane-1,4-diyl), 1-oxatetramethylene, 1-thiatetramethylene, 1-azatetramethylene or
25 pentamethylene (pentane-l,5-diyl), each of which is optionally mono- or
disubstituted by methyl, where the position 1 is connected to the point of attachment ofR3.
Further groups which may be particularly emphasized are:
13

Le A 35 696-Foreign Countries
-13-
Group 1:
Compounds in which R3 represents halogen- or C1-C4-alkoxy-substituted alkoxy
5 having 1 to 6 carbon atoms.
Group 2:
Compounds in which R3 represents optionally methyl- and/or ethyl-substituted
10 cycloalkoxy having 3 to 6 carbon atoms.
Group 3:
Compounds in which R3 represents optionally fluorine-, chlorine-, bromine-, methyl-
15 , trifluoromethyl-, methoxy- or methoxycarbonyl-substituted phenoxy or benzyloxy.
The abovementioned general or preferred radical definitions apply both to the end
products of the formula (I) and, correspondingly, to the starting materials or
intermediates required in each case for the preparation. These radical definitions can
20 be combined with one another as desired, i.e. including combinations between the
given preferred ranges.
Preference according to the invention is given to those compounds of the formula (I) which contain a combination of the meanings listed above as being preferred. 25
Particular preference according to the invention is given to those compounds of the formula (I) which contain a combination of the meanings listed above as being particularly preferred.
14

Le A 35 696-Foreign Countries
-14-
Very particular preference according to the invention is given to those compounds of the formula (I) which contain a combination of the meanings listed above as being very particularly preferred.
5 The novel substituted thien-3-yl sulphonylamino(thio)carbonyl triazolin(ethi)ones of
the general formula (I) have interesting biological properties. In particular, they have strong herbicidal activity.
The novel substituted thien-3-yl sulphonylamino(thio)carbonyl triazolin(ethi)ones of
10 the general formula (I) are obtained when
(a) substituted thiophene-3-sulphonamides of the general formula (II)


(II)

15 in which
1 7
R and R are as defined above,
are reacted with substituted triazolin(ethi)ones of the general formula (III)
20


25

in which
Q1,Q2,R3andR4 are as defined above and
-15

Le A 35 696-Foreign Countries
15

5

Z represents halogen, alkoxy, aryloxy or arylalkoxy,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
or when
(b) substituted thien-3-yl sulphonyl iso(thio)cyanates of the general formula (IV)


10
Q1RlandR2 are as defined above,
15 are reacted with triazolin(ethi)ones of the general formula (V)

20 Q2, R4 and R5 are as defined above,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
25 or when
--16-

Le A 35 696-Foreign Countries
16
(c) substituted thiophene-3-sulphonyl chlorides of the general formula (VI)

R1 0 CI
, , (V|)
"/ \X0-# ,S02
s" *2

in which

,1 „„JT>2
R1 and Rz are as defined above,

are reacted with triazolin(ethi)ones of the general formula (V)
10

in which
Q2, R4 and R5 are as defined above,

15

and metal (thio)cyanates of the general formula (VII)
M-Q1-CN (VII)

20 in which
Q1 is as defined above,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence
25 of a diluent,
17

Le A 35 696-Foreign Countries
-17-
or when
(d) substituted thiophene-3-sulphonyl chlorides of the general formula (VI)
5

R1 P CI
C—\ S02
"/ ^
(VI)
s" *2

in which

10

R"andR2 are as defined above,
are reacted with triazolin(ethi)one (thio)carboxamides of the general formula (VIII)


in which
15
Q1, Q2,R3and R4 are as defined above,

20

if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
or when
(e) substituted thien-3-yl sulphonylamino(thio)carbonyl compounds of the general formula (IX)



25

18

Le A 35 696-Foreign Countries
-18



5

10
in which
Q2, R4 and R5 are each as defined above,
15 if appropriate in the presence of a reaction auxiliary and if appropriate in the presence
of a diluent,
and the compounds of the formula (I) obtained by the processes (a), (b), (c), (d) or (e) are, if appropriate, converted by customary methods into salts.
20
Using, for example, 2-bromo-4-ethoxycarbonyl thiophene-3-sulphonamide and 4,5-dimethoxy-2-phenoxycarbonyl-2,4-dihydro-3H-l,2,4-triazol-3-one as starting materi¬als, the course of the reaction in the process (a) according to the invention can be illustrated by the following formula scheme;
19

Le A 35 696-Foreign Countries
19





Using, for example, 2-dichloromethyl-4-methoxycarbonyl thien-3-yl-sulphonyl iso-thiocyanate and 5-ethoxy-4-methyl-2,4-dihydro-3H-l,2,4-triazol-3-one as starting materials, the course of the reaction in the process (b) according to the invention can be illustrated by the following formula scheme:




10 Using, for example, 4-ethoxycarbonyl-2-ethyl thiophene-3-sulphonyl chloride,
5-ethyl-4-methoxy-2,4-dihydro-3H-l,2,4-triazole-3-thione and potassium cyanate as starting materials, the course of the reaction in the process (c) according to the invention can be illustrated by the following formula scheme:
20

Le A 35 696-Foreign Countries
-20-



KOCN

Using, for example, 4-ethoxycarbonyl-2-trifluoromethyl thiophene-3-sulphonyl
chloride and 4-ethyl-5-methoxy-2,4~dihydro-3H-l,2,4-triazol-3-one-2-carboxarnide
5 as starting materials, the course of the reaction in the process (d) according to the
invention can be illustrated by the following formula scheme:




10 Using, for example, O-methyl N-(2-ethyl-4-isopropoxycarbonyl thien-3-yl-
sulphonyl)urethane and 4,5-dimethyl-2,4-dihydro-3H-l,2,4-triazol-3-one as starting materials, the course of the reaction in the process (e) according to the invention can be illustrated by the following formula scheme:
21

Le A 35 696-Foreign Countries
21

hH. H-.A.^CH
*d
S02 Vi-
2 + N-
(CH3)2CH,_ ft Hl\_ CH3 H-|>J-^fJ
CH
3
C„HC
S ^2M5 O
N" 3
°KX"CH
(CH3)2CH 9 Hi\ Vl
S02 CH3


10

The formula (II) provides a general definition of the substituted thiophene-3-sulphonamides to be used as starting materials in the process (a) according to the invention for preparing compounds of the general formula (I). In the general formula
1 9
(II), R1 and R" preferably or in particular have those meanings which have already been mentioned above, in connection with the description of the compounds of the general formula (I) according to the invention, as being preferred or particularly preferred for R1 and R2.
The substituted thiophene-3-sulphonamides of the general formula (II) are known and/or can be prepared by processes known per se (cf. J. Org. Chem. 45 (1980), 617-620, WO-A-01/05788).

15 The substituted thiophene-3-sulphonamides of the general formula (II) are obtained
when substituted thiophene-3-sulphonyl chlorides of the general formula (VI)

22
in which

Le A 35 696-Foreign Countries
-22-
R1and R" are as defined above,
are reacted with ammonia or ammonium salts, such as, for example, ammonium
5 acetate or ammonium carbonate, if appropriate in the presence of a diluent, such as,
for example, water or methylene chloride, at temperatures between 0°C and 100°C.
The formula (III) provides a general definition of the substituted triazolin(ethi)ones furthermore to be used as starting materials in the process (a) according to the
10 invention for preparing compounds of the general formula (I). In the general formula
(III), Q1, Q2, R3 and R4 preferably or in particular have those meanings which have already been mentioned above, in connection with the description of the compounds of the general formula (I) according to the invention, as being preferred or particularly preferred for Q1, Q2, R3 and R4.
15
The starting materials of the general formula (III) are known and/or can be prepared by processes known per se (cf. EP-A-341 489, EP-A-422 469, EP-A-425 948, EP-A-431 291, EP-A-507 171, EP-A-534 266).
20 The formula (IV) provides a general definition of the substituted thien-3-yl sulphonyl
iso(thio)cyanates to be used as starting materials in the process (b) according to the invention for preparing compounds of the general formula (I). In the general formula (IV), Q\ Rl and R^ preferably or in particular have those meanings which have already been mentioned above, in connection with the description of the compounds
25 of the general formula (I) according to the invention, as being preferred or
particularly preferred for Q1, R1 and R2.
The starting materials of the general formula (IV) are known and/or can be prepared by processes known per se (cf. US-A-47 01 535).
23

Le A 35 696-Foreign Countries
-23-
The formula (V) provides a general definition of the triazolin(ethi)ones to be used as
starting materials in the processes (b), (c) and (e) according to the invention for
preparing compounds of the general formula (I). In the general formula (V), Q2, R4
and R5 preferably or in particular have those meanings which have already been
5 mentioned above, in connection with the description of the compounds of the general
formula (I) according to the invention, as being preferred or particularly preferred for Q2,R4andR5.
The starting materials of the general formula (V) are known and/or can be prepared
10 by processes known per se (cf. EP-A-341 489, EP-A-422 469, EP-A-425 948, EP-A-
431 291, EP-A-507 171, EP-A-534 266).
The formula (VI) provides a general definition of the substituted thiophene-3-sulphonyl chlorides to be used as starting materials in the processes (c) and (d)
15 according to the invention for preparing compounds of the general formula (I). In the
general formula (VI), R1 and R2 preferably or in particular have those meanings which have already been mentioned above, in connection with the description of the compounds of the general formula (I) according to the invention, as being preferred or particularly preferred for R1 and R2.
20
The substituted thiophene-3-sulphonyl chlorides of the general formula (VI) are known and/or can be prepared by processes known per se (cf. J. Org. Chem. 45 (1980), 617-620, WO-A-01/05788).
HAj

Le A 35 696-Foreign Countries
-24-
The substituted thiophene-3-sulphonyl chlorides of the general formula (VI) are obtained when 3-amino-thiophene-4-carboxylic esters of the general formula (X)
(X)
in which 5
R1 and R2 are as defined above,
- or acid adducts of compounds of the formula (X), such as, for example, the hydrochlorides -
10
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 resulting diazonium salt solution is reacted with sulphur dioxide in the presence of a diluent, such as, for example, dichloromethane, 1,2-dichloroethane or acetic acid, and
15 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.
The intermediates of the general formula (X) are known and/or can be prepared by
processes known per se (cf. Austr. J. Chem. 48 (1995), 1907-1916; Preparation
20 Examples).
The formula (VIII) provides a general definition of the triazolin(ethi)one (thio)-
carboxamides to be used as starting materials in the process (d) according to the
invention for preparing compounds of the general formula (I). In the general formula
25 (VIII), Q1, Q2, R3 and R4 preferably or in particular have those meanings which have
already been mentioned above, in connection with the description of the compounds of the general formula (I) according to the invention, as being preferred or particularly preferred for Q1, Q2, R3 and R4.
25

Le A 35 696-Foreign Countries
-25-
The starting materials of the general formula (VIII) are known and/or can be prepared by processes known per se.
5 The formula (IX) provides a general definition of the substituted thien-3-yl-
sulphonylamino(thio)carbonyl compounds to be used as starting materials in the
process (e) accordmg to the invention for preparing compounds of the general
formula (I). In the general formula (IX), Q , R and R preferably or in particular
have those meanings which have already been mentioned above, in connection with
10 the description of the compounds of the general formula (I) according to the
11 9
invention, as being preferred or particularly preferred for Q , R and R .
The starting materials of the general formula (IX) are known and/or can be prepared by processes known per se.
15
The processes (a), (b), (c), (d) and (e) according to the invention for preparing the novel compounds of the formula (I) are preferably carried out using diluents. Suitable diluents are virtually all inert organic solvents. These preferably include aliphatic and aromatic, optionally halogenated hydrocarbons, such as pentane, hexane, heptane,
20 cyclohexane, petroleum ether, benzine, ligroin, benzene, toluene, xylene, methylene
chloride, ethylene chloride, chloroform, carbon tetrachloride, 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,
25 esters, such as methyl acetate and ethyl acetate, nitriles, such as, for example,
acetonitrile and propionitrile, amides, such as, for example, dimethylformarnide, dimethylacetamide and N-methylpyrrolidone, and also dimethyl sulphoxide, tetra-methylene sulphone and hexamethylphosphoric triamide.
30 Reaction auxiliaries suitable for the processes (a), (b), (c), (d) and (e) according to
the invention are all acid binders which are customarily used for such reactions.
26

Le A 35 696-Foreign Countries
-26-
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-
5 butoxide, furthermore basic nitrogen compounds, such as trimethylamine,
triethylamine, tripropylamine, tributylamine, diisobutylamine, dicyclohexylamine,
ethyldiisopropylamine, ethyldicyclohexylamine, N,N-dimethylbenzyIamine, N,N-
dimethyl-aniline, pyridine, 2-mefhyl-, 3-methyl-, 4-methyl-, 2,4-dimefhyl-, 2,6-
dimethyl-, 2-ethyl-, 4-ethyl- and 5-ethyl-2-methyl-pyridine, l,5-diazabicyclo[4.3.0]-
10 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) and (e) according to the
invention can be varied within a relatively wide range. In general, the processes are
15 carried out at temperatures between -20°C and +150°C, preferably at temperatures
between 0°C and +100°C.
The processes (a), (b), (c), (d) and (e) according to the invention are generally carried
out under atmospheric pressure. However, it is also possible to operate under
20 elevated or reduced pressure.
For carrying out the processes (a), (b), (c), (d) and (e) according to the invention, the starting materials required in each case are generally employed in approximately equimolar amounts. However, it is also possible to use a relatively large excess of
25 one of the components used in each case. The reactions are generally carried out in a
suitable diluent in the presence of an acid acceptor, and the reaction mixture is stirred for several hours at the temperature required in each case. Work-up in the processes (a), (b), (c), (d) and (e) according to the invention is in each case carried out by customary methods (cf. the Preparation Examples).
30
27

Le A 35 696-Foreign Countries
-27-
If appropriate, salts can be prepared from the compounds of the general formula (I)
according to the invention. Such salts are obtained in a simple manner by customary
methods for forming salts, for example by dissolving or dispersing a compound of
the formula (I) in a suitable solvent, such as, for example, methylene chloride,
5 acetone, tert-butyl methyl ether or toluene, and adding a suitable base. The salts can
then - if appropriate after prolonged stirring - be isolated by concentration or filtration with suction.
The active compounds according to the invention can be used as defoliants,
10 desiccants, haulm killers and, especially, as weedkillers. Weeds in the broadest sense
are to be understood as meaning 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.
15 The active compounds according to the invention can be used, for example, in
connection with the following plants:
Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea,
20 Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum,
Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Linderaia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea,
25 Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.
Dicotyledonous crops of the genera: Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia. 30
28

Le A 35 696-Foreign Countries
-28-
Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis, Alopecurus,
Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus,
Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa,
Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium,
5 Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria,
Scirpus, Setaria, Sorghum.
Monocotyledonous crops of the genera: Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea. 10
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.
Depending on the concentration, the active compounds according to the invention are
15 suitable for total weed control, for example on industrial sites and rail tracks and on
paths and areas with or without tree growth. Equally, the compounds according to the
invention can be employed for controlling weeds in perennial crops, for example
forests, ornamental tree plantings, orchards, vineyards, citrus groves, nut orchards,
banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm
20 plantations, cocoa plantations, soft fruit plantings and hop fields, on lawns and turf
and pastures and for selective weed control in annual crops.
The compounds of the formula (I) according to the invention have strong herbicidal
activity and a broad activity spectrum when applied on the soil and on above-ground
25 parts of plants. To a certain extent, they are also suitable for selective control of
monocotyledonous and dicotyledonous weeds in monocotyledonous and dicotyledonous crops, both by the pre-emergence and by the post-emergence method.
At certain concentrations or application rates, the active compounds according to the
30 invention can also be used for controlling animal pests and fungal or bacterial plant
29

Le A 35 696-Foreign Countries
-29-
diseases. If appropriate, they can also be employed as intermediates or precursors for the synthesis of further active compounds.
According to the invention, it is possible to treat all plants and parts of plants. By
5 plants are understood here all plants and plant populations such as desired and
undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants can be plants which can be obtained by conventional "breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including transgenic plants and including plant
10 varieties which may or may not be protectable by plant variety property rights. Parts
of plants are to be understood as meaning all above-ground and below-ground parts and organs of plants, such as shoot, leaf, flower and root, examples which may be mentioned being leaves, needles, stems, trunks, flowers, fruit bodies, fruits and seeds and also roots, tubers and rhizomes. Plant parts also include harvested goods and
15 vegetative and generative propagation material, for example seedlings, tubers,
rhizomes, cuttings and seeds.
The treatment of the plants and parts of plants according to the invention with the
active compounds is carried out directly or by action on their environment, habitat or
20 storage area according to customary treatment methods, for example by dipping,
spraying, evaporating, atomizing, broadcasting, brushing-on and, in the case of propagation materials, in particular in the case of seeds, furthermore by single- or multi-layer coating.
25 The active compounds can be converted into the customary formulations, such as
solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspo-emulsion concentrates, natural and synthetic substances impregnated with active compound, and microencapsulations in polymeric substances.
30
30

Le A 35 696-Foreign Countries
-30-
These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is to say liquid solvents and/or solid carriers, optionally with the use of surfactants, that is to say emulsifiers and/or dispersants and/or foam formers. 5
If the extender used is water, it is also possible to use, for example, organic solvents as auxiliary solvents. Liquid solvents which are mainly suitable are: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene
10 chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example
petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol, and also their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulphoxide, and water.
15
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
20 and fractionated natural rocks, such as calcite, marble, pumice, sepiolite, dolomite
and synthetic granules of inorganic and organic meals, and granules of organic material, such as sawdust, coconut shells, maize cobs and tobacco stalks; suitable emulsifiers and/or foam formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for
25 example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates,
arylsulphonates and protein hydrolysates; suitable dispersants are: for example lignosulphite waste liquors and methylcellulose.
Tackifiers, such as carboxymethylcellulose, natural and synthetic polymers in the
30 form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and
polyvinyl acetate, and also natural phospholipids, such as cephalins and lecithins, and
31

Le A 35 696-Foreign Countries
-31-
synthetic phospholipids can be used in the formulations. Other possible additives are mineral and vegetable oils.
It is possible to use dyestuffs, such as inorganic pigments, for example iron oxide,
5 titanium oxide, Prussian blue, and organic dyestuffs, such as alizarin dyestuffs, azo
dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients, such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
The formulations generally comprise between 0.1 and 95 per cent by weight of active
10 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
and/or with crop-plant compatibility-improving substances ("safeners"), finished
15 formulations or tank mixes being possible. Also possible are mixtures with weed-
killers comprising one or more known herbicides and a safener.
Possible components for the mixtures are known herbicides, for example
20 acetochlor, acifluorfen(-sodium), aclonifen, alachlor, alloxydim(-sodium), ametryne,
amicarbazone, amidochlor, amidosulfuron, anilofos, asulam, atrazine, azafenidin, azimsulfuron, beflubutamide, benazolin(-ethyl), benfuresate, bensulfuron(-methyl), bentazone, benzfendizone, benzobicyclon, benzofenap, benzoylprop(-ethyl), bialaphos, bifenox, bispyribac(-sodium), bromobutide, bromofenoxim, bromoxynil,
25 butachlor, butafenacil(-allyl), butroxydim, butylate, cafenstrole, caloxydim,
carbetamide, carfentrazone(-ethyl), chlomefhoxyfen, chloramben, chloridazon, chlorimuron(-ethyl), chlornitrofen, chlorsulfuron, chlorotoluron, cinidon(-ethyl), cinmethylin, cinosulfuron, clefoxydim, clethodim, clodinafop(-propargyl), clomazone, clomeprop, clopyralid, clopyrasulfuron(-methyl), cloransulam(-methyl),
30 cumyluron, cyanazine, cybutryne, cycloate, cyclosulfamuron, cycloxydim, cyhalo-
fop(-butyl), 2,4-D, 2,4-DB, 2,4-DP, desmedipham, diallate, dicamba,
32

Le A 35 696-Foreign Countries
-32-
dichloroprop(-P), diclofop(-methyl), diclosulam, diethatyl(-ethyl), difenzoquat,
diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn,
dimethenamid, dimexyflam, dinitramine, diphenamid, diquat, dithiopyr, diuron,
dymron, eproprodan, EPTC, esprocarb, ethalfluralin, ethametsulfuron(-methyl),
5 ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanid, fenoxaprop-(-P-ethyl),
fentrazamide, flamprop(-isopropyl), flamprop(-isopropyl-L), flamprop(-methyl), flazasulfuron, florasulam, fluazifop(-P-butyl), fluazolate, flucarbazone(-sodium), flufenacet, flufenpyr flumetsulam, flumiclorac(-pentyl), flumioxazin, flumipropyn, flumetsulam, fluometuron, fluorochloridone, fluoroglycofen(-ethyl), flupoxam,
10 flupropacil, flurpyrsulfuron(-methyl, -sodium), flurenol(-butyl), fiuridone,
fluroxypyr(-butoxypropyl, -meptyl), flurprimidol, flurtamone, fluthiacet(-methyl), fluthiamide, fomesafen, foramsulfuron, glufosinate(-ammonium), glyphosate-(-isopropylammonium), halosafen, haloxyfop(-ethoxyethyl-P-methyl), haloxy-fop(-ethoxyethyl, -P-methyl), hexazinone, imazamethabenz-(-methyl), imazameth-
15 apyr, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron,
iodosulfuron(-methyl, -sodium), ioxynil, isopropalin, isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, ketospiradox, lactofen, lenacil, linuron, MCPA, mecoprop, mefenacet, mesotrione, metamitron, metazachlor, methabenzthiazuron, metobenzuron, metobromuron, (alpha-)metolachlor,
20 metosulam, metoxuron, metribuzin, metsulfuron(-methyl), molinate, monolinuron,
naproanilide, napropamide, neburon, nicosulfuron, norflurazon, orbencarb, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat, pelargonic acid, pendimethalin, pendralin, penoxysulam, pentoxazone, pethoxamide, phenmedipham, picolinafen, piperophos, pretilachlor, primisulfuron(-methyl),
25 profluazol, profoxydim, prometryn, propachlor, propanil, propaquizafop, propiso-
chlor, propoxycarbazone(-sodium), propyzamide, prosulfocarb, prosulfuron, pyraflufen(-ethyl), pyrazogyl, pyrazolate, pyrazosulfuron(-ethyl), pyrazoxyfen, pyribenzoxim, pyributicarb, pyridate, pyridatol, pyriftalid, pyriminobac(-methyl), pyrithiobac(-sodium), quinchlorac, quinmerac, quinoclamine, quizalofop(-P-ethyl),
30 quizalofop(-P-tefuryl), rimsulfuron, sethoxydim, simazine, simetryn, sulcotrione,
sulfentrazone, sulfometuron(-methyl), sulfosate, sulfosulfuron, tebutam, tebuthiuron,
33

Le A 35 696-Foreign Countries
-33-
tepraloxydim, terbuthylazine, terbutryn, thenylchlor, fhiafluamide, thiazopyr, thi-diazimin, thifensulfuron(-methyl), thiobencarb, tiocarbazil, tralkoxydim, triallate, triasulfuron, tribenuron(-methyl), triclopyr, tridiphane, trifluralin, trifloxysulfuron, triflusulfuron(-methyl), and triflusulfuron. 5
Furthermore suitable for the mixtures are known safeners, for example
AD-67, BAS-145138, benoxacor, cloquintocet (-mexyl), cyometrinil, 2,4-D, DKA-
24, dichlormid, dymron, fenclorim, fenchlorazol (-ethyl), flurazole, fluxofenim,
10 furilazole, isoxadifen (-ethyl), MCPA, mecoprop (-P), mefenpyr (-diethyl), MG-191,
oxabetrinil, PPG-1292, R-29148.
A mixture with other known active compounds, such as fungicides, insecticides,
acaricides, nematicides, bird repellents, plant nutrients and agents which improve soil
15 structure, is 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
20 customary manner, for example by watering, spraying, atomizing, scattering.
The active compounds according to the invention can be applied both before and after emergence of the plants. They can also be incorporated into the soil before sowing. 25
The amount of active compound used can vary within a relatively wide 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.
34

Le A 35 696-Foreign Countries
-34-
As already mentioned above, it is possible to treat all plants and their parts according
to the invention. In a preferred embodiment, wild plant species and plant cultivars, or
those obtained by conventional biological breeding methods, such as crossing or
protoplast fusion, and parts thereof, are treated. In a further preferred embodiment,
5 transgenic plants and plant cultivars obtained by genetic engineering, if appropriate
in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated. The term "parts" or "parts of plants" or "plant parts" has been explained above.
10 Particularly preferably, plants of the plant cultivars which are in each case
commercially available or in use are treated according to the invention. Plant cultivars are to be understood as meaning plants having certain properties ("traits") and which have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. They can be cultivars, bio- or genotypes.
15
Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, vegetation period, diet), the treatment according to the invention may also result in superadditive ("synergistic") effects. Thus, for example, reduced application rates and/or a widening of the activity spectrum and/or an
20 increase in the activity of the substances and compositions to be used according to
the invention - also in combination with other agro-chemical active compounds -, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, better quality and/or
25 a higher nutritional value of the harvested products, better storage stability and/or
processability of the harvested products are possible which exceed the effects which were actually to be expected.
The transgenic plants or plant cultivars (i.e. those obtained by genetic engineering)
30 which are preferably treated according to the invention include all plants which, in
the genetic modification, received genetic material which imparted particularly
35

Le A 35 696-Foreign Countries
-35-
advantageous useful properties ("traits") to these plants. Examples of such properties
are better plant growth, increased tolerance to high or low temperatures, increased
tolerance to drought or to water or soil salt content, increased flowering performance,
easier harvesting, accelerated maturation, higher harvest yields, better quality and/or
5 a higher nutritional value of the harvested products, better storage stability and/or
processability of the harvested products. Further and particularly emphasized examples of such properties are a better defence of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and/or viruses, and also increased tolerance of the plants to certain herbicidally active
10 compounds. Examples of transgenic plants which may be mentioned are the
important crop plants, such as cereals (wheat, rice), maize, soya beans, potatoes, cotton, oilseed rape and also fruit plants (with the fruits apples, pears, citrus fruits and grapes), and particular emphasis is given to maize, soya beans, potatoes, cotton and oilseed rape. Traits that are emphasized are in particular increased defence of the
15 plants against insects by toxins formed in the plants, in particular those formed in the
plants by the genetic material from Bacillus thuringiensis (for example by the genes CrylA(a), CrylA(b), CrylA(c), CryllA, CrylllA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CrylF and also combinations thereof) (hereinbelow referred to as "Bt plants"). Traits that are also particularly emphasized are the increased defence of the plants to
20 fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin,
phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins. Traits that are furthermore particularly emphasized are the increased tolerance of the plants to certain herbicidally active compounds, for example imidazolinones, sulphonylureas, glyphosate or phosphinotricin (for example the
25 "PAT" gene). The genes which impart the desired traits in question can also be
present in combination with one another in the transgenic plants. Examples of "Bt plants" which may be mentioned are maize varieties, cotton varieties, soya bean varieties and potato varieties which are sold under the trade names YIELD GARD® (for example maize, cotton, soya beans), KnockOut® (for example maize),
30 StarLink® (for example maize), Bollgard® (cotton), Nucotn® (cotton) and
NewLeaf® (potato). Examples of herbicide-tolerant plants which may be mentioned
36

Le A 35 696-Foreign Countries
-36-
are maize varieties, cotton varieties and soya bean varieties which are sold under the
trade names Roundup Ready® (tolerance to glyphosate, for example maize, cotton,
soya bean), Liberty Link® (tolerance to phosphinotricin, for example oilseed rape),
IMI® (tolerance to imidazolinones) and STS® (tolerance to sulphonylurea, for
5 example maize). Herbicide-resistant plants (plants bred in a conventional manner for
herbicide tolerance) which may be mentioned include the varieties sold under the name Clearfield® (for example maize). Of course, these statements also apply to plant cultivars having these genetic traits or genetic traits still to be developed, which plants will be developed and/or marketed in the future.
10
The plants listed can be treated according to the invention in a particularly advantageous manner with the compounds of the general formula (I) or the active compound mixtures according to the invention, where in addition to the good control of weed plants, the abovementioned synergistic effects with the transgenic plants or
15 plant cultivars occur. The preferred ranges stated above for the active compounds or
mixtures also apply to the treatment of these plants. Particular emphasis is given to the treatment of plants with the compounds or mixtures specifically mentioned in the present text.
20 The following examples show the preparation and use of the active compounds
according to the invention:
37

Le A 35 696-Foreign Countries
37-
Preparation examples: Example 1

0.45 g (2.19 mmol) of 5-methoxy-4-methyl-2-phenoxycarbonyl-2,4-dihydro-3H-l,2,4-triazol-3-one is dissolved in 50 ml of acetonitrile and, at room temperature (about 20°C), mixed with stirring, a little at a time, with 0.60 g (2.41 mmol) of 4-
10 ethoxycarbonyl-2-methyl-thiophene-3-sulfonamide and with 0.37 g (2.41 mmol) of
l,8-diazabicyclo-[5.4.0]-undec-7-ene (DBU). The reaction mixture is stirred at room temperature for 12 hours and then concentrated under reduced pressure. The residue is taken up in methylene chloride and washed successively with IN hydrochloric acid and with water, dried with sodium sulphate and filtered. The filtrate is concentrated
15 under reduced pressure, the residue is digested with isopropanol and the resulting
crystalline product is isolated by filtration with suction.
This gives 0.60 g (68% of theory) of ethyl 4-[[[(3-methoxy-4-methyl-5-oxo-lH-
l,2,4-triazol-l-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate as a
20 pale yellow solid of melting point 176°C.
The sodium salt of the compound prepared according to Example 1 can be prepared, for example, as follows:
25 1.0 g (2.5 mmol) of ethyl 4-[[[(3-methoxy-4-methyl-5-oxo-lH-l,2,4-triazol-l-
yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate are taken up in 25 ml of methylene chloride, and 0.10 g (2.5 mmol) of sodium hydroxide (micropellets) are
38

Le A 35 696-Foreign Countries
-38
added. The mixture is stirred at room temperature (or 20°C) for 15 hours. The crystalline product is then isolated by filtration with suction.
This gives 1.0 g of ethyl 4-[[[(3-methoxy-4-methyl-5-oxo-lH-l,2,4-triazol-l-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate sodium salt of melting point 220°C.

10

Analogously to Example 1, and in accordance with the general description of the preparation process according to the invention, it is also possible to prepare, for example, the compounds of the general formula (I) listed in table 1 below.


(i)

Table 1: Examples of the compounds of the formula (I)

Ex.
No. Q1 Q2 R1 R2 R3 R4 Melting point (°C)
2 0 0 CH3 CH3 OCH3 CH3 229 (Na-Salz)
3 0 0 CH3 CH3 R3+R4: -S(CH2)2- 204
4 0 0 CH3 CH3 RJ+R4: -0(CH2)2- 225
5 0 0 CH3 CH3 R3+R4: -S(CH2)3- 182
6 0 0 CH3 CH3 R3+R4: -0(CH2)3- 239

Le A 35 696-Foreign Countries
-39-

Ex. Q1 Q2 R1 R2 R3 R4 Melting
No. point (°C)
7 0 0 CH3 CH3 219
8 0 0 CH3 CH3 CH3 163

9 0 0 CH3 CH3 CH3 170
10 0 0 CH3 CH3 CH3 154
11 0 0 CH3 CH3 CH3 165
12 0 0 CH3 CH3 220
13 0 0 CH3 CH3 CH3 203
14 0 0 CH3 CH3 CH3 143
15 0 0 CH3 CH3 C3H7-n CH3 154
16 0 0 CH3 CH3 C3H7-i CH3 155
40

Le A 35 696-Foreign Countries
-40-

Ex.
No. Q1 Q2 R1 R2 R3 R4 Melting point (°C)
17 0 0 CH3 CH3 C4H9-S CH3 156
18 0 0 CH3 CH3 CH2OCH3 CH3 157
19 0 0 CH3 CH3 1 CH3 114
20 0 0 CH3 CH3 SC2H5 CH3 162
21 0 0 CH3 CH3 C4Xl9-t CH3 99
22 0 0 CH3 CH3 CH3 180
23 0 0 CH3 CH3 CH3 C2H5 117
24 0 0 CH3 CH3 C3H7-n 151
25 0 0 CH3 CH3 C2H5 C2H5 147
26 0 0 CH3 CH3 C3H7-n C2H5 146
28 0 0 CH3 CH3 C2H5 150
29 0 0 CH3 CH3 CH3 C3H7-n 135
30 0 0 CH3 CH3 CH3 C3H7-i 147
31 0 0 CH3 CH3 C2H5 C3H7-n 159
32 0 0 CH3 CH3 C2H5 C3H7-i 142
33 0 0 CH3 CH3 C3H7-n C3H7-n 103
34 0 0 CH3 CH3 C3H7-i C3H7-n 116
35 0 0 CH3 CH3 C3H7-i C3H7-i 121
36 0 0 CH3 CH3 C3H7-i 126
^

Le A 35 696-Foreign Countries
-41-

Ex.
No. Q1 Q2 R1 R2 R3 R4 Melting point (°C)
37 0 0 CH3 CH3 C3H7-n C3H7-i 120
38 0 0 CH3 CH3 OC2H5 C2H5 124
39 0 0 CH3 CH3 C2H5 OC2H5 183
40 0 0 CH3 CH3 Br CH3 189
41 0 0 CH3 CH3 OCH2CF3 CH3 197
42 0 0 CH3 CH3 C3H7-n OCH3 106
43 0 0 CH3 CH3 OCH2CF3 117
44 0 0 CH3 CH3 Br 166
45 0 0 CH3 CH3 CH2OCH3 185
46 0 0 CH3 CH3 CH3 206
47 0 0 CH3 CH3 C2Hs 175
48 0 0 CH3 CH3 C3H7-n ■ 149
49 0 0 CH3 CH3 C3H7-i 214
50 0 0 CH3 CH3 C4H9-t 175
51 0 0 CH3 CH3 C4H9-S 205
52 0 0 CH3 CH3 H 201
42

Le A 35 696-Foreign Countries
-42-

Ex.
No. Q1 Q2 R1 R2 R3 R4 Melting point (°C)
53 0 0 CH3 CH3 H CH3 170
54 0 0 CH3 CH3 CH3 N(CH3)2 166
55 0 0 C2H5 CH3 OC2H5 CH3 172
56 0 0 C2H5 CH3 OCH3 173
57 s 0 CH3 CH3 OCH3 CH3 159
58 s 0 CH3 CH3 OC2H5 CH3 133
59 s 0 CH3 CH3 OC3H7-n CH3 60
60 s 0 CH3 CH3 OC3H7-i CH3 182
61 s 0 CH3 CH3 OCH3 201
62 s 0 CH3 CH3 OC2H5 181
63 s 0 CH3 CH3 OC3H7-n 137
64 s 0 CH3 CH3 127
65 s 0 CH3 CH3 CH3 CH3 147
66 s 0 CH3 CH3 C2H5 CH3 117
67 s 0 CH3 CH3 SCH3 CH3 138
68 0 0 C3H7-i CH3 OCH3 CH3 190
69 0 0 C3H7-i CH3 OC2H5 CH3 193
70 0 0 C3H7-i CH3 OC3H7-n CH3 189
71 0 0 C3H7-i CH3 OC3H7-i CH3 184
72 0 0 C3H7-i CH3 OCH3 189
43

Le A 35 696-Foreign Countries
-43-

Ex.
No. Q1 Q2 R1 R2 R3 R4 Melting point (°C)
73 0 0 C3H7-i CH3 OC2H5 115
74 0 0 C3H7-i CH3 OC3H7-n 127
75 0 0 C3H7-i CH3 OC3H7-i 251
76 0 0 C3H7-i CH3 117
77 0 0 C3H7-i CH3 SCH3 CH3 185
78 0 0 C3H7-11 CH3 OCH3 CH3 161
79 0 0 C3H7-n CH3 OC2H5 CH3 95
80 0 0 C3H7-n CH3 OC3H7-n CH3 156
81 0 0 C3H7-n CH3 OC3H7-i CH3 197
82 0 0 C3H7-n CH3 OCH3 169
83 0 0 C3H7-n CH3 OC2H5 150
84 0 0 C3H7-n CH3 OC3H7-n 88
85 0 0 C3H7-n CH3 OC3H7-i 95
86 0 0 C3H7-n CH3 192
87 0 0 C3H7-n CH3 C2H5 CH3 110
88 0 0 C3H7-n CH3 SC H3 CH3 188
Uv

Le A 35 696-Foreign Countries
-44-

Ex. Ql Q2 R1 R2 R3 R4 Melting
No. point (°C)
89 0 0 C3H7-i CH3 R3+R 4. 194
-S(CH2)2-
90 0 0 C3H7-i CH3 R3+R 4. 188
-0(CH2)2-
91 0 0 C3H7-i CH3 CH2OCH3 CH3 122
92 0 0 C3H7-i CH3 R3+R 4. 205
-OCH2-C(CH3)2-CH2-
93 0 0 C3H7-i CH3 CH3 183

94 0 0 C3H7-i CH3 CH3 54
95 0 0 C3H7-i CH3 CH3 159
96 0 0 C3H7-i CH3 CH3 208
97 0 0 C3H7-i CH3 CH3 115
98 0 0 C3H7-i CH3 C3H7-n CH3 105
99 0 0 C3H7-i CH3 C3H7-i CH3 106
100 0 0 C3H7-i CH3 C4H9-S CH3 103
45

Le A 35 696-Foreign Countries
-45-

Ex.
No. Q1 Q2 R1 R2 R3 R4 Melting point (°C)
101 0 0 C3H7-i CH3 SC2H5 CH3 113
102 0 0 C3H7-i CH3 C4H9-t CH3 131
103 0 0 C3H7-i CH3 CH3 159
104 0 0 C3H7-i CH3 CH3 C3H7-i 165
105 s 0 C3H7-i CH3 OCH3 CH3 145
106 s 0 C3H7-i CH3 OC2H5 CH3 175
107 s 0 C3H7-i CH3 OC3H7-n CH3 166
108 s 0 C3H7-i CH3 OC3H7-i CH3 168
109 s 0 C3H7-i CH3 OCH3 137
110 s 0 C3H7-i CH3 OC2H5 150
111 s 0 C3H7-i CH3 OC3H7-n 136
112 s 0 C3H7-n CH3 OCH3 CH3 137
113 s 0 C3H7-n CH3 OC2H5 CH3 160
114 s 0 C3H7-n CH3 OC3H7-n CH3 160
115 0 0 C3H7-i CH3 OC2H5 C2H5 123
116 0 0 C3H7-i CH3 C2H5 OC2H5 132
117 0 0 C3H7-i CH3 OCH2CF3 CH3 188
118 0 0 C3H7-i CH3 C3H7-n OCH3 245
119 0 0 C3H7-i CH3 OCH2CF3 255
120 0 0 C3H7-i CH3 CH2OCH3 164
46

Le A 35 696-Foreign Countries
-46-

Ex.
No. Q1 Q2 R1 R2 R3 R4 Melting point (°C)
121 s 0 C3H7-n CH3 OC3H7-i CH3 172
122 s 0 C3H7-11 CH3 OCH3 140
123 s 0 C3H7-n CH3 OC2H5 139
124 s 0 C3H7-11 CH3 OC3H7-n 219
125 s 0 C3H7-n CH3 OC3H7-i 120
126 s 0 CH3 CH3 OC3H7-i 144
127 0 0 C3H7-i CH3 Br 156
128 0 0 C3H7-i CH3 C2H5 143
129 0 0 C3H7-i CH3 C3H7-i 160
130 0 0 C3H7-i CH3 H 183
131 0 0 C3H7-i CH3 H CH3 167
132 s 0 C2H5 CH3 OCH3 CH3 165
133 s 0 C2H5 CH3 OC2H5 CH3 158
134 s 0 C2H5 CH3 OC3H7-n CH3 150
135 s 0 C2H5 CH3 OC3H7-i CH3 176
136 s 0 C2H5 CH3 OCH3 159
47

Le A 35 696-Foreign Countries
-47-

Ex. Q1 Q2 R1 R2 R3 R4 Melting
No. point (°C)
137 s 0 C2H5 CH3 OC2H5 162
138 s 0 C2H5 CH3 OC3H7-11 156
139 s 0 C2H5 CH3 OC3H7-i 135
140 0 0 C2H5 CH3 R3+R4: -S(CH2)2- 189
141 0 0 C2H5 CH3 R3+R4: -S(CH2)3- 181
142 0 0 C2H5 CH3 R3+R4: -OCH2-C(CH3)2-CH2- 212
143 0 0 C2H5 CH3 CH3 174

144 0 0 C2H5 CH3 CH2OCH3 CH3 116
145 0 0 C2H5 CH3 CH3 131
146 0 0 C2H5 CH3 CH3 171
147 0 0 C2H5 CH3 CH3 210
148 0 0 C2H5 CH3 C3H7-i CH3 175
^

Le A 35 696-Foreign Countries
-48-

Ex.
No. Q1 Q2 R1 R2 R3 R4 Melting point (°C)
149 0 0 C2H5 CH3 SC2H5 CH3 131
150 0 0 C2H5 CH3 C^g-t CH3 129
151 0 0 C2H5 CH3 CH3 195
152 0 0 C2H5 CH3 CH3 C2H5 140
153 0 0 C2H5 CH3 "
C3H7-n 118
154 0 0 C2H5 CH3 C2H5 C2H5 117
155 0 0 C2H5 CH3 C3H7-n C2H5 165
156 0 0 C2H5 CH3 C3H7-i C2H5 136
157 0 0 C2H5 CH3 C2H5 148
158 0 0 C2H5 CH3 CH3 C3H7-n 135
159 0 0 C2H5 CH3 CH3 C3H7-i 135
160 0 0 C2H5 CH3 C2H5 C3H7-i 142
161 0 0 C2H5 CH3 C3H7-i 147
162 0 0 C2H5 CH3 OC2H5 C2H5 127
163 0 0 C2H5 CH3 C2H5 OC2H5 145
164 0 0 C2H5 CH3 OCH2CF3 CH3 175
165 0 0 C2H5 CH3 C3H7-11 OCH3 112
166 0 0 C2H5 CH3 OCH2CF3 147
167 0 0 C2H5 CH3 CH2OCH3 147
49

Le A 35 696-Foreign Countries
-49-

Ex.
No. Q1 Q2 R1 R2 R3 R4 Melting point (°C)
168 0 0 C2H5 CH3 CH3 152
169 0 0 C2H5 CH3 C2H5 159
170 0 0 C2H5 CH3 C3H7-11 129
171 0 0 C2H5 CH3 C3H7-i A
158
172 0 0 C2H5 CH3 C4H9-t 164
173 0 0 C2H5 CH3 C4H9-S 149
174 0 0 C2H5 CH3 H 184
175 0 0 C2H5 CH3 H CH3 170
176 0 0 C2H5 CH3 CH3 N(CH3)2 130
177 0 0 C2H5 CH3 C4H9-i 147
178 0 0 C2H5 CH3 C4H9-11 123
179 0 0 C3H7-n CH3 R3+R4: -S(CH2)2- 182
180 0 o C3H7-n CH3 R3+R4: -S(CH2)3- 198
50

Le A 35 696-Foreign Countries
-50-

Ex.
No. Q1 Q2 R1 R2 R3 R4 Melting point (°C)
181 0 0 C3H7-n CH3 1 CH3 153
182 0 0 C3H7-n CH3 CH3 145
183 0 0 C3H7-11 CH3 CH3 183
184 0 0 C3H7-11 CH3 CH3 170
185 0 0 C3H7-n CH3 C3H7-n CH3 127
186 0 0 C3H7-11 CH3 C3H7-i CH3 132
187 0 0 C3H7-11 CH3 C4H9-S CH3 125
188 0 0 C3H7-n CH3 CH2OCH3 CH3 110
189 0 0 C3H7-11 CH3 SC2H5 CH3 142
190 0 0 C3H7-n CH3 CH3 CH3 145
191 0 0 C3H7-11 CH3 CH3 C3H7-i 174
192 0 0 C3H7-n CH3 C2H5 C3H7-i 120
193 0 0 C3H7-11 CH3 OC2H5 C2H5 121
194 0 0 C3H7-11 CH3 C2H5 OC2H5 120
195 0 0 C3H7-n CH3 OCH2CF3 CH3 140
196 0 0 C3H7-n CH3 C3H7-n OCH3 112
197 0 0 C3H7-n CH3 OCH2CF3 122
51

Le A 35 696-Foreign Countries
-51-

Ex.
No. Q1 Q2 R1 R2 R3 R4 Melting point (°C)
198 0 0 C3H7-I1 CH3 CH2OCH3 117
199 0 0 C3H7-I1 CH3 C2H5 180
200 0 0 C3H7-I1 CH3 C3H7-i 183
201 0 0 C3H7-11 CH3 H / 197
202 0 0 C3H7-I1 CH3 H CH3 125
203 0 0 C2H5 CH3 OC3H7-n CH3 139
204 0 0 C2H5 CH3 OC3H7-i CH3 180
205 0 0 C2H5 CH3 OC2H5 140
206 0 0 C2H5 CH3 OC3H7-n 145
207 0 0 C2H5 CH3 OC3H7-i 160
208 0 0 C2H5 CH3 171
209 0 0 C2H5 CH3 CH3 CH3 155
210 0 0 C2H5 CH3 C2H5 CH3 107
211 0 0 C2H5 CH3 SCH3 CH3 156
212 0 0 C3H7-i CH3 C2H5 C3H7-i 251
213 0 0 CH3 C2H5 OC3H7-i 152
214 0 0 CH3 C2H5 SC2H5 CH3 145
52

Le A 35 696-Foreign Countries
-52-

Ex.
No. Ql Q2 R1 R2 R3 R4 Melting point (°C)
215 0 0 CH3 C2H5 OC2H5 C2H5 138
216 0 0 CH3 C2H5 C2H5 OC2H5 141
217 0 0 CH3 C2H5 OCH2CF3 CH3 163
218 0 0 CH3 C2H5 C3H7-n OCH3 105
219 0 0 CH3 C2H5 OCH2CF3 161
220 0 0 CH3 CH3 OCH3 CH3 146
(Triethyl-
ammonium
salt)
221 0 0 CH3 C2H5 OCH3 CH3 236
(Lithium
salt)
222 0 0 CH3 C2H5 OCH3 CH3 154
(Triethyl-
ammonium
salt)
223 0 0 CH3 C2H5 OCH3 CH3 162
(N,N-di-
methylpyrid
in-4-yl-
ammonium
salt)
53

Le A 35 696-Foreign Countries
-53-

Ex.
No. Q1 Q2 R1 R2 R3 R4 Melting point (°C)
224 0 0 CH3 C2H5 OCH3 CH3 150
(1-hydroxy-
methyl-
propyl-
propyl-
ammonium
salt)
225 0 0 CH3 CH3 OCH3 CH3 151
(Diethyl-
ammonium
salt)
226 0 0 CH3 CH3 OCH3 CH3 115
(Pyrroli-
dinium salt)
227 0 0 CH3 CH3 OCH3 CH3 159
(1-hydroxy-
methyl-
propyl-
ammonium
salt)
54

Le A 35 696-Foreign Countries
54
Use examples:
In the use examples, the following prior-art compounds (all known from WO-A-01/05788) are used for comparison:


O—C3H7-n
(A)

methyl 4-[[[(4,5-dihydro-4-methyl-5-oxo-3-n-propoxy- IH-1,2,4-triazol-1 -yl)carbonyl]-amino] sulfonyl]-5-methyl-3-thiophenecarboxylate (A)
10


L%A^
^S^N
O—C3H7-n
H N=

(B)

methyl 4-[[[(4-cyclopropyl-4,5-dihydro-5-oxo-3-n-propoxy-IH-1,2,4-triazol-1-yl)-carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate(B)
15


UXi
♦S^*N
H N= 0-C3H7-

(C)

f^

Le A 35 696-Foreign Countries
-55
methyl 4-[[[(4-cyclopropyl-4,5-dihydro-5-oxo-3-isopropoxy-lH-l,2,4-triazol-l-yl)-carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate (C)


(D)

methyl 4-[[[(3,4-dicyclopropyl-4,5-dihydro-5-oxo-lH-l,2,4-triazol-l-yl)carbonyl]-amino]sulfonyl]-5-methyl-3-thiophenecarboxylate (D)

10



(E)
methyl 4-[[[(4,5-dihydro-3,4-dimethyl-5-oxo-lH-l,2,4-triazol-l-yl)carbonyl]-amino]sulfonyl]-5-methyl-3-thiophenecarboxylate (E)


(F)

56

Le A 35 696-Foreign Countries
-57-Example A
Post-emergence test
5 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
10 emulsifier is added and the concentrate is diluted with water to the desired
concentration.
Test plants of a height of 5-15 cm are sprayed with the preparation of active
compound such that the particular amounts of active compound desired are applied
15 per unit area. The concentration of the spray liquor is chosen such 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. 20
The figures denote:
0% = no effect (like untreated control) 100% = total destruction 25
In this test, for example, the compounds of Preparation Examples 1, 15, 18, 20, 22, 39, 42, 45, 46, 47, 48, 55 and 56 show a considerably stronger activity against weeds and a substantially better compatibility with crop plants such as, for example, maize, oilseed rape and wheat than the known compounds (A) and (B).
58

Le A 35 696-Foreign Countries
-58-Example B
Pre-emergence test
5 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
10 emulsifier is added and the concetrate is diluted with water to the desired
concentration.
Seeds of the test plants are sown in normal soil. After 24 hours, the soil is sprayed
with the preparation of active compound such that the particular amount of active
15 compound desired is applied per unit area. The concentration of active compound in
the spray liquor is chosen such that the particular amount of active compound desired is applied in 1000 litres of water per hectare.
After three weeks, the degree of damage to the plants is rated in % damage in
20 comparison to the development of the untreated control. The figures denote:
0% = no effect (like untreated control) 100% = total destruction
25 In this test, for example, the compounds of Preparation Examples 1, 15, 18, 20, 22,
38, 39, 41, 42, 43, 45, 46, 47, 48, 55 and 56 exhibit considerably stronger activity against weeds than the known compounds (A), (B), (C), (D), (E), (F) and (G), and substantially, they are tolerated well by crop plants, such as, for example, maize, soyabean and wheat.
30
59

Table A1: Post-emergence-Test/greenhouse

Compound of Preparation
Example No. application rate (g ai/ha) wheat Avena fatua Bromus Echino-chloa Lolium Datura Viola Xanthium
(B) 15 30 50 50 - 60 80 - 50
(A) 15 0 30 50 60 30 50 30 70
(56) 15 0 90 90 95 90 90 95 95
Table A2: Post-emergence-Test/greenhouse

60


Compound of Preparation Example No. application rate (g ai/ha) maize Alope-curus Bromus Echino-chloa Lolium Datura Poly¬gonum Xanthium
(B) 15 90 0 50 - 60 80 70 50
(A) 15 30 70 50 60 30 50 50 70
(55) 15 0 90 90 90 90 95 90 95

Table A3: Post-emergence-Test/greenhouse

Compound of Preparation Example No. application rate (g
ai/ha) wheat maize Echino-chloa Lolium Datura Poly¬gonum Viola Xanthium
(B) 15 30 90 - 60 80 70 - 50
(A) 15 0 30 60 30 50 50 30 70
(1) 15 0 0 90 90 95 95 95 95

t-1
CD >
UQ\ V£> ON. i
o >-t
a
i—»■
n
o

CD Co

61

ON o

Table A4: Post-emergence-Test/greenhouse

Compound of Preparation Example No. application rate (g ai/ha) wheat maize Alope-curus Avena fatua Bromus Digitaria Setaria
(B) 15 30 90 0 50 50 20 60
(A) 15 0 30 70 30 50 10 30
(22) 15 0 0 99 80 95 95 90
Table A5: Post-emergence-Test/greenhouse

Compound of Preparation Example No. application rate (g ai/ha) wheat Alope-curus Bromus Echino-chloa Viola
(B) 15 30 0 50 - -
(A) 15 0 70 50 60 30
(20) 15 0 90 80 100 100

Table A6: Post-emergence-Test/greenhouse

Compound of Preparation Example No. application rate (g ai/ha) maize Alope-curus Avena fatua Bromus Digitaria Echino-chloa Lolium Setaria
(B) 15 90 0 50 50 20 - 60 60
(A) 15 30 70 30 50 10 60 30 30
(18) 15 0 95 95 80 95 95 95 100
Table A7: Post-emergence-Test/greenhouse

Compound of Preparation Example No. application rate (g ai/ha) Alope-curus Avena fatua Bromus Digitaria Echino-
chloa Lolium Setaria
(B) 15 0 50 50 20 - 60 60
(A) 15 70 30 50 10 60 30 30
(15) 15 95 90 80 100 90 80 90

Table A8: Post-emergence-Tesfgreenhouse

Compound of Preparation Example No. application rate (g ai/ha) Avena fatua Bromus Digitaria Echino-
chloa Lolium Setaria
(A) 15 30 50 10 60 30 30
(39) 15 90 95 95 100 95 95
(45) 15 90 90 100 100 95 90
Table A9: Post-emergence-Test/greenhouse

Compound of Preparation Example No. application rate (g
ai/ha) rape Alope-curus Echrno-chloa Lolium Cheno-podium
(A) 15 95 70 60 30 80
(42) 15 0 90 90 90 95
Table A10: Post-emergence-Test/greenhouse

Compound of Preparation Example No. application rate (g ai/ha) Avena fatua Digitaria Echino-chloa Lolium Setaria Viola Xanthium
(A) 15 30 10 60 30 30 30 70
(47) 15 95 90 95 100 90 100 -
(48) 15 90 90 95 100 80 95 90

Table All: Post-emergence-Test/greenhouse

Compound of Preparation
Example No. application rate (g ai/ha) Avena fatua Bromus Digitaria Lolium Setaria Xantbium
(B) 15 50 50 20 60 60 50
(39) 15 90 95 95 95 95 -
(45) 15 90 90 100 95 90 -
(47) 15 95 80 90 100 90 80
Table A12: Post-emergence-Test/greenhouse

Compound of Preparation
Example No. application rate (g ai/ha) Alope-curus Avena fatua Digitaria Lolium Xanthium
(B) 15 0 50 20 60 50
(46) 15 80 80 90 95 -
(48) 15 - 90 90 100 90

;-Test/greenhouse
Table Bl: Pre-emergence-


^


Compound of Preparation Example No. application rate (g ai/ha) wheat maize Bromus Lolium Ama-ranthus Matri¬caria Solanum Stellaria Xanthium
(G) 15 0 0 - 60 40 70 80 80 40
(F) 15 0 0 70 40 40 20 80 70 0
(E) 15 0 0 20 0 10 20 70 40 0
(D) 15 0 20 10 20 80 10 80 60 0
(Q 15 0 0 70 50 80 80 - 80 0
(B) 15 0 0 40 20 80 40 80 60 0
(A) 15 0 0 60 0 - 50 80 80 0
(56) 15 0 0 95 95 100 100 100 100 95
(1) 15 0 0 95 90 100 100 100 100 95

65

Table B2: Pre-emergence-Test/greenhouse

Compound of Preparation Example No. application rate (g ai/ha) wheat maize soy beans Alope-curus Lolium Ama-ranthus Matricaria Solanum Stellaria
(G) 15 0 0 50 - 60 40 70 80 80
(F) 15 0 0 10 70 40 40 20 80 70
(E) 15 0 0 0 20 0 10 20 70 40
(D) 15 0 20 0 0 20 80 10 80 60
(C) 15 0 0 0 0 50 80 80 - 80
(B) 15 0 0 0 20 20 80 40 80 60
(A) 15 0 0 0 60 0 - 50 80 80
(20) 15 0 0 0 90 95 95 100 100 100

0
67

Table B3: Pre-emergence-Test/greenhouse


Compound of Preparation Example No. application rate (g ai/ha) wheat maize Alope-curus Bromus Lolium Poly¬gonum Solanum Stellaria Xanthrum
(G) 15 0 0 - - 60 - 80 80 40
(F) 15 0 0 70 70 40 50 80 70 0
(E) 15 0 0 20 20 0 20 70 40 0
(D) 15 0 20 0 10 20 10 80 60 0
(C) 15 0 0 0 70 50 60 - 80 0
(B) 15 0 0 20 40 20 50 80 60 0
(A) 15 0 0 60 60 0 0 80 80 0
(55) 15 0 0 95 95 90 95 100 100 95
(22) 15 0 0 95 100 95 95 100 100 -
(15) 15 0 0 100 90 95 90 95 100 95

67

Table B4: Pre-emergence-Test/greenhouse

Compound of Preparation Example No. application rate (g
ai/ha) wheat maize soy beans Alope-curus Setaria Ama-ranthus Matricaria Stellaria
(G) 15 0 0 50 - 70 40 70 80
(F) 15 0 0 10 70 30 40 20 70
(E) 15 0 0 0 20 20 10 20 40
(D) 15 0 20 0 0 10 80 10 60
(C) 15 0 0 0 0 50 80 80 80
(B) 15 0 0 0 20 40 80 40 60
(A) 15 0 0 0 60 0 - 50 80
(18) 15 0 0 0 95 95 95 100 95

CD
>
o
CD
o
o
CD Vi



69

0\ OO

Table B5: Pre-emergence-Test/greenhouse



Compound of Preparation Example No. application rate (g ai/ha) maize soy beans Lolium Setaria Ama-ranthus Cheno-podium Solanum Stellaria
(G) 15 0 50 60 70 40 50 80 80
(F) 15 0 10 40 30 40 0 80 70
(E) 15 0 0 0 20 10 0 70 40
(D) 15 20 0 20 10 80 0 80 60
(C) 15 0 0 50 50 80 40 - 80
(B) 15 0 0 20 40 80 40 80 60
(A) 15 0 0 0 0 - 50 80 80
(38) 15 0 0 80 95 100 95 100 100


s

Table B6: Pre-emergence-Test/greenhouse



Compound of Preparation Example No. application rate (g ai/ha) wheat maize Alope-curus Setaria Ama-ranthus Cheno-podium Solanum Stellaria
(G) 15 0 0 - 70 40 50 80 80
(F) 15 0 0 70 30 40 0 80 70
(E) 15 0 0 20 20 10 0 70 40
(D) 15 0 20 0 10 80 0 80 60
(C) 15 0 0 0 50 80 40 - 80
(B) 15 0 0 20 40 80 40 80 60
(A) 15 0 0 60 0 - 50 80 80
(41) 15 0 0 100 95 100 100 100 100

^

70

Table B7: Pre-emergence-Test/greenhouse



Compound of Preparation Example No. application rate (g ai/ha) wheat Digitaria Lolium Setaria Ama-ranthus Solanum Stellaria
(G) 15 0 50 60 70 40 80 80
(F) 15 0 60 40 30 40 80 70
(E) 15 0 0 0 20 10 70 40
(D) 15 0 20 20 10 80 80 60
(C) 15 0 20 50 50 80 - 80
(B) 15 0 0 20 40 80 80 60
(A) 15 0 0 0 0 - 80 80
(39) 15 0 100 95 100 100 95 100

71

Table B8: Pre-emeigence-Test/gieenhouse



Compound of Preparation Example No. application rate (g ai/ha) wheat maize soy
beans Alope-curus Lolium Matricaria Stellaria
(G) 15 0 0 50 - 60 70 80
(F) 15 0 0 10 70 40 20 70
(E) 15 0 0 0 20 0 20 40
(D) 15 0 20 0 0 20 10 60
(C) 15 0 0 0 0 50 80 80
(B) 15 0 0 0 20 20 40 60
(A) 15 0 0 0 60 0 50 80
(46) 15 50 0 0 95 90 100 100





Table B9: Pre-emergence-Test/greenhouse

Compound of Preparation Example No. application rate (g ai/ha) Avena fatua Loliura Setaria Ama-
ranthus Matricaria Polygonum Stellaria
(G) 15 50 60 70 40 70 70 80
(F) 15 60 40 30 40 20 50 70
(E) 15 0 0 20 10 20 20 40
(D) 15 70 20 10 80 10 10 60
(Q 15 50 50 50 80 80 60 80
(B) 15 10 20 40 80 40 50 60
(A) 15 0 0 0 - 50 0 80
(43) 15 - 95 95 100 100 100 100
(45) 15 95 100 100 100 100 95 100
(47) 15 95 80 95 100 100 90 100
(48) 15 95 95 - 100 95 95 100

Table BIO: Pre-emergence-Test/greenhouse



Compound of Preparation Example No. application rate (g ai/ha) Avena fatua Bromus Lolium Setaria Ama-ranthus Galium Stellaria
(G) 15 50 - 60 70 40 30 80
(F) 15 60 70 40 30 40 10 70
(E) 15 0 20 0 20 10 0 40
(D) 15 70 10 20 10 80 0 60
(C) 15 50 70 50 50 80 70 80
(B) 15 10 40 20 40 80 20 60
(A) 15 0 60 0 0 - 10 80
(42) 15 90 95 95 95 100 100 100

75
^

WE CLAIM:
1. Compounds of the general formula (I)
in which
Q1 represents O (oxygen) or S (sulphur),
Q2 represents O (oxygen) or S (sulphur),
R1 represents optionally cyano-, halogen- or Ci-C4-alkoxy- substituted alkyl having 1 to 6 carbon atoms, represents in each case optionally cyano- or halogen-substituted alkenyl or alkynyl having in each case 2 to 6 carbon atoms, representing in each case optionally cyano-, halogen or C1-C4-alkyl-substituted cycloalkyl or cycloalkylalkyl having in each case 3 to 6 carbon atoms in the cycloalkyl group and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety, represents in each case optionally nitro-, cyano-, halogen-, C1-C4-alkyl- or C1-C4-alkoxy-substituted aryl or arylalkyl having in each case 6 or 10 carbon atoms in the aryl group and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety, or represents in each case optionally nitro-, cyano-, halogen C1-C4-alkyl- or C1-C4-alkoxy-substituted heterocyclyl or heterocyclylalkyl having in each case up to 6 carbon atoms and additionally 1 to 4 nitrogen atoms and/or 1 or 2 oxygen or sulphur atoms in the heterocyclyl group and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety,
76

R2 represents hydrogen, cyano, nitro, halogen, represents in each case optionally, cyano-, halogen- or C1-C4-alkoxy-substituted alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl or alkylsulfonyl having in each case 1 to 6 carbon atoms in the alkyl group, or represents in each case optionally cyano or halogen-substituted alkenyl, alkynyl, alkenyloxy or alkynyloxy having in each case 2 to 6 carbon atoms in the alkenyl or alkynyl group,
R3 represents halogen-substituted alkoxy having 1 to 6 carbon atoms, and
R4 represents hydrogen, hydroxy, amino, cyano, represents C2-C10 alkylideneamino, represents optionally fluorine-chlorine-, bromine-, cyano-, C1-C4-alkoxy-, C1-C4-alkyl-carbonyl- or C1-C4-alkoxy-carbonyl-substituted alkyl having 1 to 6 carbon atoms, represents in each case optionally fluorine, chlorine- and/or bromine-substituted alkenyl or alkynyl having in each case 2 to 6 carbon atoms, represents in each case optionally fluorine-, chlorine-, bromine-, cyano-, Ci-C4-alkoxy- or C1-C4-alkoxy-carbonyl-substituted alkoxy, alkylamino or alkylcarbonylamino having in each case 1 to 6 carbon atoms in the alkyl groups, represents alkenyloxy having 3 to 6 carbon atoms, represents dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups, represents in each case optionally fluorine-, chlorine-, bromine-, cyano- and/or C1-C4-alkyl-substituted cycloalkyl, cyolbalkylamino or cycloalkylalkyl having in each case 3 to 6 carbon atoms in the alkyl group and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety, or represents in each case optionally fluorine-, chlorine-, bromine-, cyano-. nitro-, C1-C4-alkyl-, trifluoromethyl- and/or C1-C4-alkoxy-substituted aryl or arylalkyl having in each case 6 or 10 carbon atoms in the aryl group and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety, or together with R represents optionally branched and/or C1-C4-alkyl-substituted alkanedlyl, oxaalkanediyl, thiaalkanediyl or azaalkanediyl having 3 to 6 carbon atoms where the oxa, thia or aza components may be positioned at the beginning, at the end or within the alkanediyl grouping, and salts of the compounds of the formula (I).
2. Compounds as claimed in claim 1, wherein
R1 represents in each case optionally cyano-, fluorine-, chlorine-,
methoxy- or ethoxy-substituted methyl, ethyl, n- or isoproyl, n-, iso-, s-
or t-butyl, represents in each case optionally cyano-, fluorine- or
chlorine-substituted propenyl, butenyl, propynyl or butynyl, represents
in each case optionally cyano-, fluorine-, chlorine-, methyl- .or ethyl-
substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,
cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or
cyclohexylmethyl, represents in each case optionally cyano-, fluorine-,
77

chlorine-, methyl- ethyl-, n- or isopropyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or isopropoxy-, difluoromethoxy- or trifluoromethoxy-substituted phenyl, phenylmethyl or phenylethyl, or represents in each case optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n-or isopropyl-, methoxy-, ethoxy-, n- or isopropoxysubstituted heterocydyl or heterocyclylmethyl, where the heterocyclyl group is in each case selected from the group consisting of oxetartyl, thietanyl, furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl,
R2 represents hydrogen, cyano, fluorine, chlorine, bromine, represents
in each case optionally cyano-, fluorine-, chlorine-, methoxy- or
ethoxysubstituted methyl, ethyl, n- or isopropyl, n-, iso-, s or t-butyl,
methoxy, ethoxy, n- or isopropoxy, methoxycarbonyl, ethoxycarbonyl, n-
or isopropoxycarbonyl, methylthio, ethylthio, n- or isopropylthio,
methylsulfinyl ethylsulfinyl, methylsulfonyl or ethylsulfonyl, or
represents in each case optionally cyano-, fluorine- or chlorine-
substituted propenyl, butenyl, propynyl, burynyl,
propenyloxy, butenyloxy, propynyloxy or butynyloxy,
R3 represents fluorine- or chlorine-substituted methoxy, ethoxy, n- or i-propoxy, n-. i-, s-, or t-butoxy, n-, i-, s-, or to pentyloxy or - neo-pentyloxy, and
R4 represents hydrogen, hydroxy, amino, represents in each case
optionally fluorine-, chlorine-, cyano-, methoxy- or ethoxy-substituted
methyl, ethyl, n- or isopropyl, n-, iso-, s- or t-butyl, represents in each
case optionally fluorine, chlorine- and/or bromine-substituted ethenyl,
propenyl, butenyl, propynyl or butynyl represents in each case
optionally fluorine-, chlorine-, cyano , methoxy- or ethoxysubstituted
methoxy, ethoxy, n- or isopropoxy, n-, iso-, s- or t-butoxy, methylamino,
ethylamino, n- or isopropylarnino, n-, iso-, s- or t-burylamino, represents
propenyloxy or butenyloxy, represents dimethylamlno or diethylamino,
represents in each case optionally fluorine-, chlorine-, methyl- and/or
ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cydohexyl,
cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino,
cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or
cyclohexylmethyl, or represents in each case optionally fluorine-, chlorine-, methyl-, trifluoromethyl- and/or methoxy-substituted phenyl or ben2yl.
3. Compounds as claimed in claim 1, wherein
R1 represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or isopropyl,







78






R2 represents fluorine, chlorine, bromine or represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxysubstituted methyl, ethyl, n- or isopropyl,
R3 represents fluorine- or chlorine-substituted methoxy, ethoxy, n- or i-propoxy, n-. i-, s-, or t-butoxy, n-, i-, s-, or- to-pentyloxy, or nec-pentyloxy, and
R4 represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or isopropyl, represents in each case optionally fluorine- or chlorine- substituted ethenyl, propenyl or propynyl, represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxysubstituted methoxy, ethoxy, n- or isopropoxy, represents - methylamino, or represents cyclopropyl.
4. Compounds as claimed in claim 3, wherein R1 represents methyl.
5. Compounds as claimed in claim 3, wherein R1 represents ethyl.
6. Compounds as claimed in claim 3, wherein R1 represents n-propyl.
7. Compounds as claimed in claim 3, wherein R1 represents isopropyl.
8. Process for preparing the compounds as claimed in claim 1,
wherein
(a) substituted thiophene-3-sulphonamides of the general formula (II)

in which
79

R1 and R2 are as defined in Claim 1.
are reacted with substituted triazolin(ethi)ones of the general formula (111)

in which
Q1, Q2, R3 and R4 are as defined in claim 1 and
Z represents halogen, alkoxy, aryloxy or arylalkoxy,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
or that
(b) substituted thiene-3-ylsulphonyl iso(thio)cyanates of the general formula (IV)

in which
Q1, R1 and R2 are as defined in Claim 1
are reacted with triazolin(ethi)ones of the general formula (V)




80





in which


are reacted with triazolin(ethi)ones of the general formula (V)

in which
Q2, R4 and R3 are as defined in Claim 1
and metal (thio)cyanates of the general formula (VII)
81

M-Q1-CN (VII)
in which
Q1 is as defined above,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
or that
(d) substituted thiophene-3-sulphonyl chlorides of the general formula (VI)
in which
R1 and R2 are as defined in claim 1
are reacted with triazolin(ethi)one (thio)carboxamides of the general formula (VIII)

in which
Q1, Q2, R3 and R4 are as defined in claim 1,
82

if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
or that
(e) substituted thiene-3-yl- sulphonylamino(thio)carbonyl compounds of the general formula (IX)

in which
Q1, R1 and R2 are s defined in Claim 1,
Z represents halogen, alkoxy, aryloxy or arylalkoxy are reacted with triazolin(ethi)ones of the general formula (V)

if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
and the compounds of the formula (I) obtained by process (a), (b), (c), (d) or (e) are, if appropriate, converted by customary methods in salts.


83


9. Herbicidal composition wherein said composition comprises between 0.1 to 95 % by weight of active compound of formula (I) as claimed in any of Claims 1 to 7 and customary extenders and/or surfactants.

Dated this 17th day of October,
#

Documents:

904-mum-2002-cancelled pages(11-10-2007).pdf

904-mum-2002-claims(granted)-(11-10-2007).doc

904-mum-2002-claims(granted)-(11-10-2007).pdf

904-mum-2002-correspondence(11-10-2007).pdf

904-mum-2002-correspondence(ipo)-(18-10-2006).pdf

904-mum-2002-form 1(11-10-2007).pdf

904-mum-2002-form 13(11-10-2007).pdf

904-mum-2002-form 18(22-12-2005).pdf

904-mum-2002-form 2(granted)-(11-10-2007).doc

904-mum-2002-form 2(granted)-(11-10-2007).pdf

904-mum-2002-form 3(11-10-2007).pdf

904-mum-2002-form 3(17-10-2002).pdf

904-mum-2002-form 3(21-11-2002).pdf

904-mum-2002-form 5(17-10-2002).pdf

904-mum-2002-petition under rule 137(11-10-2007).pdf

904-mum-2002-petition under rule 138(11-10-2007).pdf

904-mum-2002-power of authority(11-10-2007).pdf

904-mum-2002-power of authority(17-10-2002).pdf


Patent Number 216381
Indian Patent Application Number 904/MUM/2002
PG Journal Number 13/2008
Publication Date 28-Mar-2008
Grant Date 12-Mar-2008
Date of Filing 17-Oct-2002
Name of Patentee BAYER AKTIENGESELLSCHAFT
Applicant Address D-51368 LEVERKUSEN, GERMANY.
Inventors:
# Inventor's Name Inventor's Address
1 ERNST RUDOLF GESING TRILLSER GRABEN 4, 40699 ERKRATH, GERMANY
2 MARK WILHELM DREWES GOETHESTR. 38, 40764 LANGENFELD, GERMANY
3 PETER DAHMEN ALTBRUCKER STR. 61, 41470 NEUSS, GERMANY
4 DEITER FEUCHT ACKERWEG 9, 40789 MONHEIM, GERMANY.
5 ROLF PONTZEN AN KLOSTER. 69, 42799 LANGENFELD GERMANY
PCT International Classification Number A01N 47/38
PCT International Application Number N/A
PCT International Filing date
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 10154074.4 2001-11-02 Germany