Title of Invention

SELECTIVE HERBICIDES BASED ON SUBSTITUTED ARYLSULPHONYLAMINOCARBONYL TRIAZOLINONES AND SAFENERS

Abstract Compositions, characterized in that they comprise an effective amount of an active compound combination comprising (a) one or more substituted arylsulphonylaminocarbonyl-triazolinones of the formula (I) (b) at least one compound which improves crop plant compatibility, from the group of compounds of the general formula (II) below (II) 8 JUN 2007 72-
Full Text FORM 2
THE PATENTS ACT 1970
[39 OF 1970]
COMPLETE SPECIFICATION
[See Section 10]
"SELECTIVE HERBICIDES BASED ON -SUBSTITUTED
ARYLSULPHONYLAMINOCARBONYL TRIAZOLINONES AND SAFENERS"
BAYER AKTIENGESELLSCHAFT, a German company, of D-51368 Leverkusen, Germany
The following specification particularly describes the nature of the invention and the manner in which it is to be performed :-
8-6-2007


The invention relates to novel selective herbicidal active compound combinations comprising substituted arylsulphonylaminocarbonyl-triazolinones and/or salts thereof and at least one compound which improves crop plant compatibility, which combinations can be used with particularly good results for the selective control of weeds in various crops of useful plants.
Substituted arylsulphonylaminocarbonyl-triazolinones are already known as effective herbicides (cf. EP-A-341489, EP-A-422469, EP-A-425948, EP-A-431291, EP-A-507171, EP-A-534266, WO-A-96/11188, WO-A-96/27590, WO-A-96/27591, WO-A-97/03056). However, the activity of these compounds and/or their compatibility with crop plants are not under all conditions entirely satisfactory.
Also known are combinations of substituted arylsulphonylaminocarbonyl-triazolinones and other herbicidally active compounds to obtain a synergistic effect (cf. WO-A-98/12923). Combinations of substituted arylsulphonylaminocarbonyl-triazolinones and safeners, too, are already known (cf. DE-A-19940859, DE-A-19940860, US-A-6162762). However, in these combination products, too, the use properties are not under all conditions entirely satisfactory. Furthermore, combinations of substituted arylsulphonylaminocarbonyl-triazolinones and further herbicidally active compounds, if appropriate with the additional use of safeners, also form part of the subject-matter of an earlier, but not prior published patent application
Surprisingly, it has now been found that certain substituted arylsulphonylamino-carbonyl-triazolinones, when used together with the crop-plant-compatibility-improving compounds (safeners/antidotes) described below, prevent damage to the crop plants extremely well and can be used particularly advantageously as broad-

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2-
spectrum combination preparations for the selective control of weeds in crops of useful plants, such as, for example, in cereals, maize and rice.
The invention provides selective herbicidal compositions, characterized by an effective
5 amount of an active compound combination comprising
(a) one or more substituted arylsulphonylaminocarbonyl-triazolinones of the formula (I)


10

in which
R1 represents hydrogen, hydroxyl, amino, C2-C6-alkylideneamino, represents in
15 each case optionally cyano-, halogen- or C1-C4--alkoxy-substituted alkyl,
alkenyl, alkynyl, alkoxy, alkenyloxy, alkylamino or dialkylamino having in
each case up to 6 carbon atoms, represents in each case optionally cyano-,
halogen- or C1-C4--alkyl-substituted cycloalkyl, cycloalkylalkyl or cycloalkyl-
amino having in each case 3 to 6 carbon atoms in the cycloalkyl group and, if
20 appropriate, 1 to 4 carbon atoms in the alkyl moiety, or represents in each
case optionally cyano-, nitro-, halogen-, C1-C4--alkyl-, C1-C4-4-haloalkyl-, C1-C4--alkoxy- or C1-C4--haloalkoxy-substituted phenyl or phenyl-C1-C4---alkyl,
R2 represents hydrogen, hydroxyl, mercapto, amino, cyano, halogen, represents
25 in each case optionally cyano-, halogen- or C1-C4--alkoxy-substituted alkyl,
alkoxy, alkylthio, alkylamino, dialkylamino, alkenyl, alkynyl, alkenyloxy,
alkynyloxy, alkenylthio, alkynyjthio, alkenylamino or alkynylamino having in each case up to 6 carbon atoms, represents in each case optionally cyano-,

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halogen- or C1-C4--alkyl-substituted cycloalkyl, cycloalkyloxy, cycloalkylthio, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylthio or cycloalkylalkylamino 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, or represents in each case optionally cyano-, nitro-, halogen-, C1-C4--alkyl-, C1-C4--haloalkyl-, C1-C4--alkoxy- or Cj:-C4-haloalkoxy-substituted phenyl, phenoxy, phenylthio, phenylamino or phenyl-C1-C4--alkyl,
,3
R represents nitro, cyano, halogen, represents in each case optionally cyano-,
10 halogen- or C1-C4--alkoxy-substituted alkyl, alkylcarbonyl, alkoxy, alkoxy-
carbonyl, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, alkenyl, alkenyloxy, alkenylthio, alkenylamino, alkynyl, alkynyloxy, alkynylthio having in each case up to 6 carbon atoms, represents in each case optionally cyano-, halogen- orC1-C4--alkyl-substituted cycloalkyl, cycloalkyloxy, cyclo-
15 alkylthio, cycloalkylamino having in each case 3 to 6 carbon atoms in the
cycloalkyl groups, or represents in each case optionally cyano-, nitro-, halogen-, C1-C4--alkyl-, C1-C4--haloalkyl-, C1-C4--alkoxy- or C1-C4-haloalkoxy-substituted phenyl, phenoxy, phenylthio, phenylsulphinyl, phenyl-sulphonyl or phenylamino, and
20
R4 represents hydrogen, nitro, cyano, halogen, represents in each case optionally cyano-, halogen- or C1-C4--alkoxy-substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, alkenyl, alkenyloxy, alkenylthio, alkenylamino, alkynyl, alkynyloxy or
25 alkynylthio having in each case up to 6 carbon atoms, represents in each case
optionally cyano-, halogen- or Ci-C4-alkyl-substituted cycloalkyl, cycloalkyl¬oxy, cycloalkylthio, cycloalkylamino having in each case 3 to 6 carbon atoms in the cycloalkyl groups, or represents in each case optionally cyano-, nitro-, halogen-, C1-C4--alkyl-, C1-C4--haloalkyl-, C1-C4--alkoxy- or C1-C4-
30 haloalkoxy-substituted phenyl, phenoxy, phenylthio. phenyl sulphinyl, phenyl-
sulphonyl or phenylamino,

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-4
- including all possible tautomeric forms of the compounds of the general formula (I) and salts formed by compounds of the general formula (I) and basic compounds -
("active compounds of group 1")
and
(b) at least one compound which improves crop plant compatibility, from the
10 group of compounds of the general formula (II) below

in which 15
m represents the numbers 0 to 5,
n represents the numbers 0 to 4,
20 X represents nitro, cyano, carboxyl, carbamoyl, formyl, sulfamoyl,
hydroxyl, amino, halogen, or represents in each case optionally cyano-, halogen- or Ci-C4-alkoxy-substituted alkyl, alkoxy, alkoxy-carbonyl, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, alkyl-aminocarbonyl having in each case 1 to 6 carbon atoms in the alkyl
25 groups, or represents dialkylamino, dialkylaminocarbonyl or dialkyl-
aminosulphonyl having in each case 1 to 6 carbon atoms in the alkyl groups.

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Y represents nitro, cyano, carboxyl, carbamoyl, formyl, sulfamoyl, hydroxyl, amino, halogen, or represents in each case optionally cyano-, halogen- or C1-C4--alkoxy-substituted alkyl or alkoxy having in each case 1 to 6 carbon atoms, and
Z represents one of the groupings below

10 in which
R5 represents hydrogen, represents optionally cyano-, halogen- or C1-C4--alkoxy-substituted alkyl having 1 to 6 carbon atoms, represents in each case optionally halogen-substituted alkenyl
15 or alkynyl having in each case 3 to 6 carbon atoms, or
represents in each case optionally halogen- orC1-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,
20
R6 represents hydrogen, represents in each case optionally cyano-, halogen-, Ci-C4-alkoxy- or Ci-C4-alkylthio-substituted alkyl, alkoxy or alkylthio having in each case 1 to 6 carbon atoms, represents in each case optionally halogen-substituted alkenyl,
25 alkenyloxy, alkenylthio, alkynyl, alkynyloxy or alkynylthio
having in each case up to 6 carbon atoms, represents in each case optionally halogen- orC1-C4--alkyl-substituted cycloalkyl or cycloalkylalkyl having in each case 3 to 6 carbon atoms in
4

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-6-
the cycloalkyl group and, if appropriate, 1 to 4 carbon atoms in
the alkyl moiety, represents in each case optionally nitro-,
cyano-, halogen-, Ci-Q-alkyl-, Ci-Grhaloalkyl-, C]-C4-
alkoxy- or Ci-C4-haloalkoxy-substituted aryl, aryloxy, arylthio,
5 arylalkyl, arylalkoxy or arylalkylthio 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-, C]-C4-alkyl-, Q-C4-haloalkyl-, Ci-C4-alkoxy- or Ci-C4-haloalkoxy-substituted
10 heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclyl-
alkyl, heterocyclylalkoxy or heterocyclylalkylthio having in each case up to 10 carbon atoms, 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, and
15
R7 represents hydrogen, represents optionally cyano-, halogen- or C]-C4-alkoxy-substituted alkyl having 1 to 6 carbon atoms, represents alkoxy having 1 to 6 carbon atoms, represents in each case optionally halogen-substituted alkenyl or alkynyl
20 having in each case 3 to 6 carbon atoms, represents alkenyloxy
having 3 to 6 carbon atoms, represents in each case optionally halogen- or Ci-C4-alkyl-substituted cycloalkyl or cycloalkyl -alkyl having 3 to 6 carbon atoms in the cycloalkyl group and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety, or
25 represents in each case optionally nitro-, cyano-, halogen-, Ci-
C4-alkyl-, C]-C4-haloalkyl-, CrC4-alkoxy- or C1-C4-haloalkoxy-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 R5
30 represent? in each case optionally C]-0-alky]-substituted

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5

alkanediyl having 2 to 6 carbon atoms or oxaalkanediyl having 2 to 5 carbon atoms
("active compounds of group 2").
In the definitions, the hydrocarbon chains, such as in alkyl or alkanediyl, are in each case straight-chain or branched - including in combination with heteroatoms, such as in alkoxy.

10 Preferred meanings of the groups listed above in connection with the general formula
(I) are defined below.
R1 preferably represents hydrogen, amino, propylideneamino, butylideneamino, represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or
15 ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, ethenyl,
propenyl, butenyl, ethynyl, propynyl, butynyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, propenyloxy, butenyloxy, methylamino, ethyl-amino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino, represents in each case optionally cyano-, fluorine-, chlorine-,
20 bromine-, methyl-, ethyl-, n- or i-propyl-substituted cyclopropyl, cyclobutyl,
cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentyl-methyl, cyclohexylmethyl, cyclopropylamino, cyclobutylamino, cyclopentyl-amino or cyclohexylamino, or represents in each case optionally cyano-, nitro-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s-
25 or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, difluoromethoxy- or
trifluoromethoxy-substituted phenyl or benzyl.
R2 preferably represents hydrogen, hydroxyl, mercapto, amino, cyano, fluorine, chlorine, bromine, represents in each case optionally cyano-, fluorine-,
30 chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl. n-. j-.
s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methyl-

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thio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethyl¬
amino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethyl-
amino, ethenyl, propenyl, butenyl, ethynyl, propynyl, butynyl, propenyloxy,
butenyloxy, propynyloxy, butynyloxy, propenylthio, butenylthio, propynyl-
5 thio, butynylthio, propenyl amino, butenylamino, propynylamino or butynyl-
amino, represents in each case optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexyl-
10 thio, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexyl-
amino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexyl-methyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclo-hexylmethoxy, cyclopropylmethyl thio, cyclobutylmethylthio, cyclopentyl-methylthio, cyclohexylmethylthio, cyclopropylmethylamino, cyclobutyl-
15 methylamino, cyclopentylmethylamino or cyclohexylmethylamino, or
represents in each case optionally cyano-, nitro-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, trifluoro-methyl-, methoxy-, ethoxy-, difluoromethoxy- or trifluoromethoxy-substituted phenyl, phenoxy, phenylthio, phenylamino or benzyl.
20
R3 preferably represents nitro, cyano, fluorine, chlorine, bromine, represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, acetyl, propionyl, n- or i-butyroyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy,
25 methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethyl-
thio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl, ethyl-sulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, ethenyl, propenyl, butenyl, propenyloxy, butenyloxy, propenyl-
30 thio. butenylthio. propenyl amino, butenylamino. ethynyl, propynyl. butynyl.
propynyloxy, butynyloxy, propynylthio or butynylthio, represents in each case

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9-
optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or
i-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclo-
propyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio,
cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclo-
5 butylamino, cyclopentylamino or cyclohexylamino, or represents in each case
optionally cyano-, nitro-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or
i-propyl-, n-, i-, s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-
propoxy-, n-, i-, s- or t-butoxy-, difluoromethoxy- or trifluoromethoxy-
substituted phenyl, phenoxy, phenylthio, phenylsulphinyl, phenyl sulphonyl or
10 phenylamino.
R4 preferably represents hydrogen, nitro, cyano, fluorine, chlorine, bromine, represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, acetyl,
15 propionyl, n- or i-butyroyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or
t-butoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methyl-thio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or
20 t-butylamino, ethenyl, propenyl, butenyl, propenyloxy, butenyloxy, propenyl-
thio, butenylthio, propenylamino, butenylamino, ethynyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylthio or butynylthio, represents in each case optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclo-
25 propyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio,
cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclo-butylamino, cyclopentylamino or cyclohexylamino, or represents in each case optionally cyano-, nitro-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, n-, i-, s- or t-
30 butoxy-. difluoromethoxy- or trifluoromeThoxy-substifuted phenyl phenoxy.
phenylthio, phenylsulphinyl, phenylsulphonyl or phenylamino.

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10-
R particularly preferably represents hydrogen, amino, represents in each case
optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl,
ethenyl, propenyl, ethynyl, propynyl, methoxy, ethoxy, n- or i-propoxy,
5 methylamino or ethylamino, represents dimethylamino, or represents
optionally fluorine-, chlorine- or methyl-substituted cyclopropyl.
R particularly preferably represents hydrogen, chlorine, bromine, represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted
10 methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, methoxy, ethoxy, n- or
i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethylamino, ethenyl, propenyl, butenyl, ethynyl, propynyl, butynyl, propenyloxy, butenyloxy, propynyloxy, butynyl-oxy, propenylthio, butenylthio, propynylthio, butynylthio, propenylamino,
15 butenylamino, propynylamino or butynylamino, or represents in each case
optionally fluorine-, chlorine- or methyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexyl-thio, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexyl-
20 amino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexyl-
methyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclo-hexylmethoxy, cyclopropylmethylthio, cyclobutylmethylthio, cyclopentyl-methylthio, cyclohexylmethylthio, cyclopropylmethylamino, cyclobutyl-methylamino, cyclopentylmethylamino and cyclohexylmethylamino.
25
R3 particularly preferably represents nitro, cyano, fluorine, chlorine, bromine, represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethyl-
30 thio. n- or i-propylthio. methylsulphinyl. ethylsulpbiny]. methyl sulphonyl or
ethylsulphonyl, represents in each case optionally fluorine-, chlorine- or

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11-
methyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclo-
propyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio,
cyclobutylthio, cyclopentylthio or cyclohexylthio, or represents in each case
optionally cyano-, nitro-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or
5 i-propyl-, n-, i-, s- or t-butyl, trifluoromethyl-, methoxy-, ethoxy-, n- or i-
propoxy-, difluoromethoxy- or trifluoromethoxy-substituted phenyl, phenoxy, phenylthio, phenylsulphinyl or phenylsulphonyl.
R4 particularly preferably represents hydrogen, nitro, cyano, fluorine, chlorine,
10 bromine, or represents in each case optionally fluorine-, chlorine-, methoxy-
or ethoxy-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl. 15
R1 very particularly preferably represents hydrogen, represents in each
case optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted
methyl, ethyl, ethenyl, methoxy, ethoxy, methylamino or ethylamino,
represents dimethylamino, or represents optionally fluorine-, chlorine-
20 or methyl-substituted cyclopropyl.
R2 very particularly preferably represents hydrogen, chlorine, bromine, represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl,
25 methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propyl-
thio, methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethylamino, ethenyl, propenyl, butenyl, ethynyl, propynyl, butynyl, propenyloxy, butenyloxy, propynyloxy, butynyloxy, propenylthio, butenylthio, propynylthio, butynylthio, or represents in each case
30 optionally fluorine-, chlorine- or methyl-substituted cyclopropyl.

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12
cyclopropyloxy, cyclopropylthio, cyclopropylmethyl, cyclopropyl-methoxy or cyclopropylmethylthio.
R3 very particularly preferably represents nitro, cyano, fluorine, chlorine,
5 bromine, represents in each case optionally fluorine-, chlorine-,
methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, methoxy,
ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-
propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methyl-
sulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl, or
10 represents in each case optionally cyano-, nitro-, fluorine-, chlorine-,
bromine-, methyl-, ethyl-, trifluoromethyl-, methoxy-, ethoxy-, difluoromethoxy- or trifluoromethoxy-substituted phenyl or phenoxy.
R4 very particularly preferably represents hydrogen, nitro, cyano, fluorine,
15 chlorine, bromine, or represents in each case optionally fluorine-,
chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl. 20
Instead of the pure active compounds of the formula (I), it is also possible to use salts of the compounds of the formula (I) with metals and/or with basic nitrogen compounds in the active compound combinations according to the invention.
25 Here, preference is given to salts of the compounds of the formula (I) with alkali
metals, such as, for example, lithium, sodium, potassium, rubidium or caesium, in particular with sodium or potassium, with alkaline earth metals, such as, for example, magnesium, calcium or barium, in particular with calcium, or with earth metals, such as, for example, aluminium.
30

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R preferably represents hydrogen, represents in each case optionally
cyano-, halogen-, methoxy-, ethoxy-, n- or i-propoxy-, n-, i-, s- or t-
butoxy-, methylthio-, ethylthio-, n- or i-propylthio-, n-, i-, s- or t-butyl-
thio-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-,
5 s- or t-pentyl, or neo-pentyl, methoxy, ethoxy, n- or i-propoxy, n-, i-,
s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, represents in each case optionally halogen-substituted propenyl, butenyl, pentenyl, propenyloxy, butenyloxy, pentenyloxy, propenylthio, butenylthio, pentenylthio, propynyl, butynyl, pentynyl,
10 propynyloxy, butynyloxy, pentynyloxy, propynylthio, butynylthio or
pentynylthio, represents in each case optionally halogen-, methyl-, ethyl-, n- or i-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, represents in each case optionally nitro-, cyano-,
15 halogen-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, trifluoro-
methyl-, methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy- or trifluoromethoxy-substituted phenyl, naphthyl, phenoxy, phenylthio, benzyl, phenylethyl, phenylmethoxy, phenylethoxy or phenylmethyl-thio, or represents in each case optionally nitro-, cyano-, halogen-,
20 methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, trifluoromethyl-,
methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy- or trifluoro¬methoxy-substituted heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylmethyl, heterocyclylmethoxy or heterocyclylmethylthio, where the heterocyclyl group is preferably selected from the group
25 consisting of furyl, thienyl, pyrazolyl, pyridinyl, pyrimidinyl,
R7 preferably represents hydrogen, represents in each case optionally cyano-, halogen-, methoxy-, ethoxy-, n- or i-propoxy-, n-, i-, s- or t-butoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-,
30 i-. s- or t-pentyl. or neo-pentyl. represents methoxy. ethoxy. n- or i-
propoxy, n-, i-, s- or t-butoxy, represents in each case optionally

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Table A2
Post emergence test / greenhouse

Active compound (+ safener) Application rate (g of a.i./ha) Damage Winter barley
(in %)
flucarbazone-sodium 8 40
flucarbazone-sodium + Ex. No. Ha-101 8+100 20
Table Al
Post emergence test / greenhouse

Safener Application rate (g of a.i./ha) Damage Winter barley
(in %)
Ex. No. Ha-101 100
.__.. 30 ... 0 0

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18
halogen-substituted propenyl, butenyl, pentenyl, propynyl, butynyl or
pentynyl, represents propenyloxy, butenyloxy or pentenyloxy,
represents in each case optionally halogen-, methyl-, ethyl-, n- or i-
propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,
5 cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclo-
hexylmethyl, or represents in each case optionally nitro-, cyano-,
halogen-, methyl-, ethyl-, n- or i-propyl, n-, i-, s- or t-butyl-, trifluoro-
methyl-, methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy- or tri-
fluoromethoxy-substituted phenyl, naphthyl, benzyl or phenylethyl, or
10 together with R5 represents in each case optionally methyl- or ethyl-
substituted butane-l,4-diyl (tetramethylene), l-oxabutan-l,4-diy], pentane-l,5-diyl, l-oxapentane-l,5-diyl or 3-oxapentane-l,5-diyl.
15 m particularly preferably represents the number 1 or 2.
n particularly preferably represents the number 0.
X particularly preferably represents nitro, cyano, fluorine, chlorine, bromine,
20 represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxy-
substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy,
methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethyl-
thio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl,
ethylsulphonyl, methylamino, ethylamino, n- or i-propylamino, methylamino-
25 carbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, or represents
dimethylamino, dimethylaminocarbonyl or dimethylaminosulphonyl.
Z particularly preferably represents one of the groupings below

Le A 35 662-Foreign Countries
-19-

in which
5 R particularly preferably represents hydrogen, represents in each case
optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or
i-propoxy-substituted methyl, ethyl, n- or i-propyl, n- or i-butyl,
represents in each case optionally fluorine- and/oder chlorine-
substituted propenyl, butenyl, propynyl or butynyl, or represents in
10 each case optionally fluorine-, chlorine-, methyl- or ethyl-substituted
cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl,
R6 particularly preferably represents hydrogen, represents in each case
15 optionally cyano-, fluorine-, chlorine-, bromine-, methoxy-, ethoxy-,
n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-substituted
methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, or
neo-pentyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy,
methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio,
20 represents in each case optionally fluorine- and/oder chlorine-
substituted propenyl, butenyl, pentenyl, propenyloxy, butenyloxy,
pentenyloxy, propenylthio, butenylthio, pentenylthio, propynyl,
butynyl, pentynyl, propynyloxy, butynyloxy, pentynyloxy, propynyl-
thio, butynylthio or pentynylthio, represents in each case optionally
25 fluorine-, chlorine-, methyl- or ethyl-substituted cyclopropyl, cyclo-
butyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, represents in each case optionally nitro-, cyano-, fluorine-, chlorine-, bromine-, methyl-,

Le A 35 662-Foreign Countries
-20-
ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, trifluoromethyl-, methoxy-,
ethoxy-, n- or i-propoxy-, difluoromethoxy- or trifluoromethoxy-
substituted phenyl, phenoxy, phenylthio, benzyl, phenylethyl, phenyl-
methoxy, phenylethoxy or phenylmethylthio, or represents in each
5 case optionally nitro-, cyano-, halogen-, methyl-, ethyl-, n- or i-
propyl-, n-, i-, s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or
i-propoxy-, difluoromethoxy- or trifluoromethoxy-substituted hetero-
cyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylmethyl, hetero-
cyclylmethoxy or heterocyclylmethylthio, where the heterocyclyl
10 group is preferably selected from the group consisting of furyl, thienyl,
pyrazolyl, pyridinyl and pyrimidinyl, and
R particularly preferably represents hydrogen, represents in each case optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-
15 propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,
n-, i-, s- or t-pentyl, or neo-pentyl, represents methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, represents in each case optionally fluorine- and/oder chlorine-substituted propenyl, butenyl, pentenyl, propynyl, butynyl or pentynyl, represents propenyloxy, butenyloxy or
20 pentenyloxy, represents in each case optionally fluorine-, chlorine-,
methyl- or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or represents in each case optionally nitro-, cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-,
25 n-, i-, s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-
propoxy-, difluoromethoxy- or trifluoromethoxy-substituted phenyl, benzyl or phenylethyl, or together with R5 represents in each case optionally methyl- or ethyl-substituted butane-1,4-diyl (tetra-methylene), 1-oxabutane-1,4-diyl, pentane-l,5-diyl, l-oxapentane-1,5-
30 diy] or 3-oxapentane-1.5-diy].'

Le A 35 662-Foreign Countries
-21-
A very particularly preferred group of safeners to be used according to the invention are the compounds of the general formula (Ha)
(Ha)
in which
m, n, R5,R6,XandY have the meanings given above as being preferred or as being
10 particularly preferred.
Examples of the compounds of the formula (Ha) which are very particularly preferred as safeners to be used according to the invention are listed in Table 1 below.
X2


9-4


1$


•>

XT




09


30




32.


33





4/


4*


^


hH


4r


Le A 35 662-Foreign Countries

k&


Le A 35 662-Foreign Countries

4'7

We Claim:
Compositions, characterized in that they comprise an effective amount of an active compound combination comprising
(a) one or more substituted arylsulphonylaminocarbonyl-triazolinones of the formula (I)

wherein,
R1 represents hydrogen, hydroxyl, amino, C2-C6-aTkylideneamino, represents in each case optionally cyano-, halogen- or C1-C4-alkoxy-substituted alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkylamino or dialkylamino having in each case up to 6 carbon atoms, represents in each case optionally cyano-, halogen- orC1-C4--alkyl-substituted cycloalkyl, cycloalkylalkyl or cycloalkylamino 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, or represents in each case optionally cyano-, nitro-, halogen-,C1-C4-alkyl-, C1-C4--haloalkyl-, C1-C4--alkoxy- or C1-C4--haloalkoxy-substituted phenyl or phenyl-C1-C4-- alkyl,
R2 represents hydrogen, hydroxyl, mercapto, amino, cyano,
halogen, represents in each case optionally cyano-, halogen- or Ci-C4-alkoxy- substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino, alkenyl alkynyl, alkenyloxy, alkynyloxy, alkenylthio, alkynylthio, alkenyl amino or alkynylamino having
54

in each case up to 6 carbon atoms, represents in each case optionally cyano-, halogen- or C1-C4--alkyl- substituted cycloalkyl, cycloalkyloxy, cycloalkylthio, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylthio or cycloalkyl alkylamino 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, or represents in each case optionally cyano-, nitro-, halogen-, C1-C4-alkyl-, C1-C4--haloalkyl-, C1-C4--alkoxy- or C1-C4--haloalkoxy-substituted phenyl, phenoxy, phenylthio, phenylamino or phenyl-C1-C4--alkyl,
represents nitro, cyano, halogen, represents in each case optionally cyano-, halogen- or C1-C4--alkoxy-substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, alkenyl, alkenyloxy, alkenylthio, alkenylamino, alkynyl, alkynyloxy, alkynylthio having in each case up to 6 carbon atoms, represents in each case optionally cyano-, halogen- or C1-C4--alkyl- substituted cycloalkyl, cycloalkyloxy, cycloalkylthio, cycloalkylamino having in each case 3 to 6 carbon atoms in the cycloalkyl groups, or represents in each case optionally cyano-, nitro-, halogen-, C1-C4--alkyl-, C1-C4--haloalkyl-, C1-C4--alkoxy- or C1-C4--haloalkoxy- substituted phenyl, phenoxy, phenylthio, phenylsulphinyl, phenylsulphonyl or phenylamino, and
represents hydrogen, nitro, cyano, halogen, represents in each case optionally cyano-, halogen- or C1-C4--alkoxy-substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, alkenyl, alkenyloxy, alkenylthio, alkenylamino, alkynyl, alkynyloxy or alkynylthio having in each case up to 6 carbon atoms, represents in each case optionally cyano-, halogen- or C1-C4--alkyl-substituted cycloalkyl, cycloalkyloxy, cycloalkylthio,
55

cycloalkyl amino having in each case 3 to 6 carbon atoms in the
cycloalkyl groups, or represents in each case optionally cyano-,
nitro-, halogen-, C1-C4-alkyl-, C1-C4--haloalkyl-, C1-C4--alkoxy- or
C1-C4- haloalkoxy-substituted phenyl, phenoxy, phenylthio,
phenylsulphinyl, phenylsulphonyl or .phenylamino,
- including all possible tautomeric forms of the compounds of the general formula (I) and salts formed by compounds of the general formula (I) and basic compounds
and
(b) at least one compound which improves crop plant compatibility, from the group of compounds of the general formula (II) below


wherein,
m represents the numbers 0 to 5,
n represents the numbers 0 to 4,
X represents nitro, cyano, carboxyl, carbamoyl, formyl, sulfamoyl, hydroxyl, amino, halogen, or represents in each case optionally cyano-, halogen- or Ci-C4-alkoxy-substituted alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl,
56

alkylsulphonyl, alkylaminp, alkylaminocarbonyl having in each case 1 to 6 carbon atoms in the alkyl groups, or represents dialkylamino, dialkylaminocarbonyl or dialkylaminosulphonyl having in each case 1 to 6 carbon atoms in the alkyl groups,
Y represents nitro, cyano, carboxyl, carbamoyl, formyl, sulfamoyl, hydroxyl, amino, halogen, or represents in each case optionally cyano-, halogen- or C1-C4-alkoxy-substituted alkyl or alkoxy having in each case 1 to 6 carbon atoms, and
Z represents one of the groupings below

wherein
R5 represents hydrogen, represents optionally cyano-,
halogen- orC1-C4-alkoxy-substituted alkyl having 1 to 6 carbon atoms, represents in each case optionally halogen-substituted alkenyl or alkynyl having in each case 3 to 6 carbon atoms, or represents in each case optionally 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,
57

represents hydrogen, represents in each case optionally cyano-,
halogen-, C1-C4-alkoxy- or C1-C4-alkylthio- substituted alkyl,
alkoxy or alkylthio having in each case 1 to 6 carbon atoms,
represents in each case optionally halogen-substituted alkenyl,
alkenyloxy, alkenylthio, alkynyl, alkynyloxy or alkynylthio having
in each case up to 6 carbon atoms, represents in each case
optionally 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-C4alkyl-, C1-C4-haloalkyl-,
C1-C4-alkoxy or C1-C4-haloalkoxy-substituted aryl, aryloxy,
arylthio, arylalkyl, arylalkoxy or arylalkylthio 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-, C1-C4-
haloalkyl-, C1-C4-alkoxy or C1-C4-haloalkoxy-substituted heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylalkyl, heterocyclylalkoxy or heterocyclylalkylthio having in each case up to 10 carbon atoms, 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, and
represents hydrogen, represents optionally cyano-,
halogen- or C1-C4-alkoxy- substituted alkyl having 1 to 6 carbon atoms, represents alkoxy having 1 to 6 carbon atoms, represents in each case optionally halogen-substituted alkenyl or alkynyl having in each case 3 to 6 carbon atoms, represents alkenyloxy having 3 to 6 carbon atoms, represents in each case optionally halogen- or C1-C4-alkyl-substituted cycloalkyl or cyclo alkylalkyl having 3 to 6 carbon atoms in the cycloalkyl group and, if appropriate, 1 to 4 carbon atoms in the alkyl
58

moiety, or represents in each case optionally nitro-, cyano-, halogen-, C1-C4-alkyl-, C1-C4-haloalkyl-, C1-C4-alkoxy- or C1-C4 haloalkoxy-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 R5 represents in each case optionally C1-C4alkyl-substituted alkanediyl having 2 to 6 carbon atoms or oxaalkanediyl having 2 to 5 carbon atoms
2. Compositions as claimed in Claim 1, wherein
R1 represents hydrogen, amino, propylideneamino, butylideneamino, represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, ethenyl, propenyl, butenyl, ethynyl, propynyl, butynyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, propenyloxy, butenyloxy, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino, represents in each case optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexyl methyl, cyclopropylamino, cyclobutylamino, cyclopentylamino or cyclohexylamino, or represents in each case optionally cyano-, nitro-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s-or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, difluoromethoxy- or trifluoromethoxy-substituted phenyl or benzyl,
R2 represents hydrogen, hydroxyl, mercapto, amino, cyano,
fluorine, chlorine, bromine, represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or
59

i-propylammo, n-, i-, s- or t-butylamino, dime thy lamino,
diethylamino, ethenyl, propenyl, butenyl, ethynyl, propynyl,
butynyl, propenyloxy, butenyloxy, propynyloxy, butynyloxy,
propenylthio, butenylthio, propynyl thio, butynylthio,
propenylamino, butenylamino, propynylamino or butynylamino, represents in each case optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclo
pentylthio, cyclohexyl thio, cyclopropylamino, cyclobuty lamino,
cyclopentylamino, cyclohexylamino, cyclopropylmethyl,
cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl,
cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy,
cyclohexylmethoxy, cyclopropylmethyl thio, cycloburylmethylthio,
cyclopentylmethylthio, cyclohexyl methylthio,
cyclopropylmethylamino, cyclobuty lme thy lamino,
cyclopentylmethylamino or cyclohexylmethylamino, or represents in each case optionally cyano-, nitro-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, difluoromethoxy- or trifluoromethoxy-substituted phenyl, phenoxy, phenylthio. phenylamino or benzyl.
represents nitro, cyano, fluorine, chlorine, bromine, represents
in each case optionally cyano-, fluorine-, chlorine, methoxy- or
ethoxysubstituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,
acetyl, propionyl, n- or i-butyroyl, methoxy, ethoxy, n- or i-
propoxy, n-, i-, s- or t-butoxy, methoxycarbonyl, ethoxycarbonyl,
n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio,
n-, i-, s- or t-butylthio, methylsulphinyl, ethylsulphinyl, n- or i-
propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-
propylsulphonyl, methylamino, ethylamino, n- or i-propylamino, n-
, i-, s- or t-butylamino, ethenyl, propenyl, butenyl, propenyloxy,
butenyloxy, propenylthio, butenylthio, propenylamino,
60

butenylammo, ethynyl, propynyl, butynyl, propynyloxy,
butynyloxy, propynylthio or butynylthio, represents in each case
optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n-
or i-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl,
cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy,
cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio,
cyclohexylthio, cyclopropylamino, cyclobutylamino,
cyclopentylamino or cyclohexylamino, or represents in each case optionally cyano-, nitro-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, n-, i-, s-or t-butoxy-, difluoromethoxy- or trifluoromethoxy-substituted phenyl, phenoxy, phenylthio, phenylsulphinyl, phenylsulphonyl or phenylamino, and
represents hydrogen, nitro, cyano, fluorine, chlorine, bromine,
represents in each case optionally cyano-, fluorine-, chlorine-,
methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-,
or t-butyl, acetyl, propionyl, n- or i-butyroyl, methoxy, ethoxy, n-
or i-propoxy n-, i-, s- or t-butoxy, methoxycarbonyl,
ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n
or i-propylthio, n-, i-, s-or t-butylthio, methylsulphinyl,
ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl,
ethylsulphonyl, n- or i-propylsulphonyl, methyl amino ethylamino,
n- or i-propylamino, n-, i-, s- or t-butylamino,
ethenyl, propenyl, butenyl, propenyloxy, butenyloxy, propenylthio,
butenylthio, propenylamino, butenylamino, ethynyl, propynyl,
butynyl, propynyloxy, butynyloxy, propynylthio or butynylthio,
represents in each case optionally cyano-, fluorine-, chlorine-,
bromine-, methyl-, ethyl-, n- or i-propyl-substituted cyclopropyl,
cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy,
cyclopentyloxy, cyclo-hexyloxy cyclopropylthio, cyclobutylthio,
cyclopentylthio, cyclohexylthio, cyclopropylamino,
cyclobutylamino, cyclopentylamino or cyclohexylamino, or represents in each case optionally cyano-, nitro-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-,
61

trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, n-, i-, s- or t-butoxy- difluoromethoxy- or trifluoromethoxy-substituted phenyl, phenoxy, phenylthio, phenylsulphinyl, phenylsulphonyl or phenyl amino.
Compositions as claimed in Claim 1, wherein
represents hydrogen, amino, represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, ethenyl, propenyl, ethynyl, propynyl, methoxy, ethoxy, n- or i propoxy methylamino or ethylamino, represents dime thy lamino, or represents optionally fluorine-, chlorine- or methyl-substituted cyclo-propyl,
represents hydrogen, chlorine, bromine, represents in each case
optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted
methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, methoxy, ethoxy, n-
or i-propoxy, methylthio ethylthio. n- or i-propylthio, methylamino,
ethylamino, n-or i-propylamino, dimethylamino, diethylamino,
ethenyl, propenyl, butenyl, ethynyl, propynyl, butynyl,
propenyloxy, butenyloxy, propynyloxy, butynyloxy, propenylthio,
butenylthio, propynylthio, butynylthio, propenylamino,
butenylamino, propynylamino or butynylamino, or represents in
each case optionally fluorine-, chlorine- or methyl-substituted
cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy,
cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio,
cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino,
cyclobutylamino, cyclopentylamino, cyclohexylamino,
cyelopropylmethyl, cyclobutylmethyl, cyclopenrylmethyl, cyclohexyl
methyl, cyclopropylmethoxy, cyclobutylmethoxy,
cyclopenrylmethoxy, cyclohexylmethoxy, cyclopropylmethylthio,
cyclobutylmethylthio, cyclopentylmethylthio, cyclohexylmethylthio,
cyclopropylmethylamino, cyclobutylmethylamino,
cyclopentylmethylamino and cyclohexylmethylamino,
62

R3 represents nitro, cyano, fluorine, chlorine, bromine, represents in
each case optionally fluorine-, chlorine-, methoxy- or ethoxy-
substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-
propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-
propoxycarbonyl, methyl-thio, ethylthio, n- or i-propylthio,
methylsulphinyl, ethylsulphinyl, methylsulphonyl or
ethylsulphonyl, represents in each case optionally fluorine-,
chlorine- or methyl-substituted cyclopropyl, cyclobutyl,
cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy,
cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio or cyclohexylthio, or represents in each case optionally cyano-, nitro-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, sor t-butyl, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy- or trifluoromethoxy-substituted phenyl, phenoxy, phenylthio, phenylsulphinyl or phenylsulphonyl, and
R4 represents hydrogen, nitro, cyano, fluorine, chlorine, bromine, or
represents in each case optionally fluorine-, chlorine-, methoxy- or
ethoxy-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy,
n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-
propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio,
methylsulphinyl, ethylsulphinyl, methylsulphonyl or
ethylsulphonyl.
4. Compositions as claimed in Claim 1, wherein
R1 represents hydrogen, represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, ethenyl, methoxy, ethoxy, methylamino or ethylamino, represents dimethylamino, or represents optionally fluorine-, chlorine- or methyl- substituted cyclopropyl,
R2 represents hydrogen, chlorine, bromine, represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted
63

methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, methoxy, ethoxy, n-or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n or i-propylamino, dimethylamino, diethylamino, ethenyl, propenyl, butenyl, ethynyl, propynyl, burynyl, propenyloxy, butenyloxy, propynyloxy, butynyloxy, propenylthio, butenylthio, propynylthio, butynylthio, or represents in each case optionally fluorine-, chlorine or methyl-substituted cyclopropyl, cyclopropyloxy, cyclopropylthio, cyclopropylmethyl, cyclopropylmethoxy or cyclopropylmethylthio,
represents nitro, cyano, fluorine, chlorine, bromine, represents in
each case optionally fluorine-, chlorine-, methoxy- or ethoxy-
substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-
propoxy, methoxycarbonyl, ethoxycarbonyl. n- or i-
propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio,
methylsulphinyl, ethylsulphinyl, methylsulphonyl or
ethylsulphonyl, or represents in each case
optionally cyano-, nitro-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, trifluoromethyl-, methoxy-, ethoxy-, difluoromethoxy- or tri fluoromethoxy-substitute phenyl or phenoxy, and
represents hydrogen, nitro, cyano, fluorine, chlorine, bromine, or represents in each case optionally fluorine-, chlorine-, methoxy-or ethoxy-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethyl sulphinyl methylsulphonyl or ethylsulphonyl.
Compositions as claimed in Claim 1, wherein
m represents the number 0, 1,2, 3 or 4,
n represents the number 0, 1, 2 or 3,
64

X represents nitro, cyano, carboxyl, carbamoyl, formyl,
sulfamoyl, hydroxy, amino, halogen, represents in each case
optionally cyano-, halogen-, methoxy-, ethoxy-, n- or i-
propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or
t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-
butoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-
propoxycarbonyl, n-, i-, s- or t-butoxycarbonyl, methylthio,
ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio,
methylsulphinyl, ethylsulphinyl, n or i-propylsulphinyl,
methylsulphonyl, ethylsulphonyl, methylamino, ethylamino,
n- or i-propylamino, n-, i-, s- or t-butylamino,
methylaminocarbonyl, ethylaminocarbonyl, n- or i-
propylaminocarbonyl, or represents dimethylamino,
diethylamino, dime thy laminocarbonyl or
dimethylaminosulphonyl,
represents nitro, cyano, carboxyl, carbamoyl, formyl, sulphamoyl, hydroxyl, amino, halogen, or represents in each case optionally cyano-, halogen-, methoxy-, ethoxy-, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, and
represents one of the groupings below

wherein
R5 represents hydrogen, represents in each case optionally
cyano-, halogen-, methoxy-, ethoxy-, n- or i-propoxy-, n-, i-, s- or t-butoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, or neo-pentyl, represents
65

m each case optionally halogen-substituted propenyl, butenyl, pentenyl, propynyl, butynyl or pentynyl, or represents in each case optionally halogen-, methyl-, ethyl-, n- or i-propyl substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl,
represents hydrogen, represents in each case optionally
cyano-, halogen-, methoxy-, ethoxy-, n- or i-propoxy-, n-, i-,
s- or t-butoxy- methylthio-, ethylthio-, n- or i-propylthio-, n-,
i-, s- or t-butylthio-substituted methyl, ethyl, n- or i-propyl,
n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, or neo-pentyl,
methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy,
methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-
butylthio, represents in each case
optionally halogen-substituted propenyl, butenyl, pentenyl,
propenyloxy, butenyloxy, pentenyloxy, propenylthio, butenyl
thio, pentenylthio, propynyl, butynyl, pentynyl, propynyloxy,
butynyloxy, pentynyloxy, propynylthio, butynylthio or
pentynylthio, represents in each case optionally halogen-,
methyl-, ethyl-, n- or i-propyl-substituted cyclopropyl, cyclo
butyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutyl
methyl, cyclopentylmethyl or cyclohexylmethyl, represents in
each case optionally nitro-, cyano-, halogen-, methyl-, ethyl-,
n or i-propyl-, n-, i-, s- or t-butyl-, trifluoromethyl-, methoxy-
, ethoxy-, n- or i-propoxy-, difluoromethoxy- or
trifluoromethoxy- substituted phenyl, naphthyl, phenoxy,
phenylthio, ben2yl, phenylethyl, phenylmethoxy,
phenylethoxy or phenylmethylthio, or represents in each case optionally nitro-, cyano-, halogen-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy- or trifluoromethoxy-substituted heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylmethyl, heterocyclylmethoxy or
66

heterocyclylmethylthio, where the heterocyclyl group is selected from the group consisting of furyl, thienyl, pyrazolyl, pyridinyl, pyrimidinyl,
R7 represents hydrogen, represents in each case optionally
cyano-, halogen-, methoxy-, ethoxy-, n- or i-propoxy-, n-, i-,
s- or t-butoxy-substitute methyl, ethyl, n- or i-propyl, n-, i-,
s- or t-butyl n-, i-, s- or t-pentyl, or neo-pentyl, represents
methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy,
represents in each case optionally halogen-substituted
propenyl, butenyl, pentenyl, propynyl, butynyl or pentynyl,
represents propenyloxy, butenyloxy or pentenyloxy,
represents in each case optionally halogen-, methyl-, ethyl-,
n- or i-propyl-substituted cyclopropyl, cyclobutyl,
cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl,
cyclopentylmethyl or cyclohexyl methyl, or represents in
each case optionally nitro-, cyano-,
halogen-, methyl-, ethyl-, n- or i-propyl, n-, i-, s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy- or trifluoromethoxy-substituted phenyl, naphthyl, benzyl or phenylethyl, or together with R5 represents in each case optionally methyl- or ethyl-substituted butane- 1,4-diyl (tetramethylene), 1 -oxabutan- 1 ,4-diyl, pentane- 1,5-diyl, 1 -oxapentane- 1,5-diyl or 3-oxapentane-1,5-diyl.
6. Compositions as claimed in Claim 1, wherein
m represents the number 1 or 2,
n represents the number 0,
X represents nitro, cyano, fluorine, chlorine, bromine,
represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl,
67

methoxy, ethoxy, n- or i-propoxy,
methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl,
methyl thio, ethylthio, n- or i-propylthio, methylsulphinyl,
ethylsulphinyl, methylsulphonyl, ethylsulphonyl,
methylamino, ethylamino, n- or i- propylamino methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl or represents dimethylamino, dimethylamino carbonyl or dimethylaminosulphonyl, and
represents one of the groupings below

represents hydrogen, represents in each case optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy substitute methyl, ethyl, n- or i-propyl, n- or i-butyl, represents in each case optionally fluorine- and/oder chlorine- substituted propenyl, butenyl, propynyl or butynyl, or represents in each case optionally fluorine-, chlorine-, methyl- or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl cyclopropylmethyl, cyclobutylmethyl, cyclopentyl methyl or cyclohexylmethyl,
represents hydrogen, represents in each case optionally cyano-, fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n-or i- propoxy- methylthio-, ethylthio-, n- or i-propylthio-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, or neo-pentyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n~, i-, s- or t-butylthio, represents in each case optionally fluorine and/oder chlorine-substituted propenyl, butenyl, pentenyl, propenyloxy, butenyloxy, pentenyloxy,
68

propenylthio, butenylthio, pentenylthio, propynyl, butynyl,
pentynyl, propynyloxy, butynyloxy, pentynyloxy,
propynylthio, butynylthio or
pentynylthio, represents in each case optionally fluorine-,
chlorine-, methyl- or ethyl-substituted cyclopropyl,
cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl,
cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl,
represents in each case optionally nitro-, cyano-, fluorine-,
chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s-
or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-
propoxy-, difluoromethoxy or trifluoromethoxy-substituted
phenyl, phenoxy, phenylthio, benzyl, phenylethyl,
phenylmethoxy, phenylethoxy or phenylmethylthio, or
represents in each case optionally nitro-, cyano-, halogen-,
methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-,
trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-,
difluoromethoxy- or trifluoromethoxy-substituted
heterocyclyl, heterocyclyloxy, heterocyclylthio,
heterocyclylmethyl, heterocyclylmethoxy or
heterocyclylmethylthio, where the heterocyclyl group is selected from the group consisting of furyl, thienyl, pyrazolyl, pyridinyl and pyrimidinyl, and
represents hydrogen, represents in each case optionally
cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-
propoxy substitute methyl, ethyl, n- or i-propyl, n-, i-, s- or
t-butyl, n-, i-, s- or t-pentyl, or neo-pentyl, represents
methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy,
represents in each case optionally fluorine- and/oder
chlorine-substituted propenyl, butenyl, pentenyl, propynyl,
butynyl or pentynyl, represents propenyloxy, butenyloxy or
pentenyloxy, represents in each case optionally fluorine-,
chlorine-, methyl- or ethyl-substituted
cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyl methyl cyclobutylmethyl, cyclopentylmethyl or cyclohexyl
69

methyl or represents in each case optionally nitro-, cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n-or i-propoxy-, difluoromethoxy- or trifluoromethoxy-substituted phenyl, benzyl or phenylethyl, or together with R5 represents in each case optionally methyl- or ethyl-substituted butane-1,4-diyl (tetramethylene), 1-oxabutane-1,4-diyl, pentane-l,5-diyl, l-oxapentane-l,5-diyl or 3-oxapentane-1,5-diyl.
7. Composition as claimed in any of claims 1 to 6, wherein the compound of the formula (I) is one or more compounds selected from the compounds 2-(2-methoxycarbonyl-pheylsulphonylaminocarbonyl)-4-methyl-5-n-propoxy-2,4-dihydro-3H-1,2,4-triazol-3-one (propoxycarbazone), 2-(2-trifluoromethoxy-phenylsulphonylaminocarbonyl)-4-methyl-5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one (flucarbazone) and the corresponding sodium salts (propoxycarbazone-sodium and flucarbazone-sodium).
8. Compositions as claimed in any of claims 1 to 6, wherein the compound of the formula (II) is 2-methoxy-N-(4-(2-methoxybenzoyl- sulphamoyl) phenyl) acetamide.
9. Process for preparing a herbicidal composition, characterized in that a composition as claimed in any of claims 1 to 8 is mixed with surfactants and/or extenders.
10. Compositions substantially as herein described with reference to the foregoing description.
70

11. Process for preparing a herbicidal composition substantially as herein described with reference to the foregoing description.
Dated this 19th day of August, 2002
RANJNA MEHTA-DUTT OF REMFRY & SAGAR AGENT FOR THE APPLICANTS
71

Documents:

750-mum-2002-abstract(8-7-2007).doc

750-mum-2002-abstract(8-7-2007).pdf

750-mum-2002-cancelled pages(8-6-2007).pdf

750-mum-2002-claims(granted)-(8-6-2007).doc

750-mum-2002-claims(granted)-(8-6-2007).pdf

750-mum-2002-correspondence(14-6-2007).pdf

750-mum-2002-correspondence(ipo)-(12-6-2006).pdf

750-mum-2002-form 1(19-8-2002).pdf

750-MUM-2002-FORM 16(8-9-2011).pdf

750-mum-2002-form 18(30-11-2005).pdf

750-mum-2002-form 2(granted)-(8-6-2007).doc

750-mum-2002-form 2(granted)-(8-6-2007).pdf

750-mum-2002-form 3(8-6-2007).pdf

750-mum-2002-form 5(19-8-2002).pdf

750-mum-2002-form 5(8-6-2007).pdf

750-mum-2002-form-pct-isa-210(8-6-2007).pdf

750-mum-2002-petition under rule 137(8-6-2007).pdf

750-mum-2002-petition under rule 138(8-6-2007).pdf

750-mum-2002-power of authority(19-8-2002).pdf

750-mum-2002-power of authority(8-6-2007).pdf


Patent Number 215219
Indian Patent Application Number 750/MUM/2002
PG Journal Number 13/2008
Publication Date 31-Mar-2008
Grant Date 22-Feb-2008
Date of Filing 19-Aug-2002
Name of Patentee BAYER AKTIENGESELLSCHAFT
Applicant Address D-51368 LEVERKUSEN, GERMANY.
Inventors:
# Inventor's Name Inventor's Address
1 DIETER FEUCHT ACKERWEG 9, 40789 MONHEIM,
2 PETER DAHMEN ALTEBRUCKER STR. 61, 41470 NEUSS,
3 ROLF PONTZEN 69, 42799 LEICHLINGEN,
4 KLAUS-HELMUT MULLER SOLFSTR. 19, 40593 DUSSELDORF,
5 DIETER FEUCHT ACKERWEG 9, 40789 MONHEIM, GERMANY.
6 MARK WILHELM DREWES GOETHESTR. 38, 40764 LANGENFELD,
7 HANS-GEORG SCHWARZ HEINENBUSH 19E, 40764 LANGENFELD,
PCT International Classification Number A01N 53/00
PCT International Application Number N/A
PCT International Filing date
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 10143083.3 2001-09-03 Germany