Title of Invention

HERBICIDES BASED ON SUBSTITUTED THIEN-3-YL-SULPHONYLAMINO[THIO]-CARBONYLTRIAZOLIN[ETHI]ONES

Abstract Herbicides based on substituted thien-3-yl-sulphonylainino(thio)carbonyI-triazolin(ethi)ones Abstract The invention relates to synergistic herbicidal compositions, characterized in that they comprise an effective amount of an active compound combination comprising (a) one or more compounds of the formula (I) in which Q1, Q2, R', R2, R3 and R4 are as defmed in the description - and salts of the compounds of the formula (I) - and at least one of the known herbicides listed in the description and, if appropriate, a safener. The invention also reJates to the use of these compositions for controlïing unwanted vegetation and to a process for preparing the compositions according to the invention.
Full Text FORM 2
THE PATENTS ACT 1970 [39 OF 1970]
COMPLETE SPECIFÏCATION [See Section 10]
"HERBICIDES BASED ON SUBSTITUTED THIEN-3-YL-
SULPHONYLAMINO[THIO]-CARBONYLTRIAZOLIN[ETHI]ONES”
BAYER AKTIENGESELLSCHAFT, a body corporate organised under the laws of Germanv, of D-51368 Leverkusen, Gerrnany
The following specifïcation particularly describes the nature of the invention and the marmer in which it is to be performed:-


-l-
Herbicides based on substituted thien-3-yl-Sulphonvlamino('thio)carbonvl-triazolin(ethi)ones
The invention relates to novel herbicidal synergistic active compoundcombinations

comprising known substituted thien-3-yI-sulphonylamino(thio)carbonyltriazolin(ethi)-
ones and one or more known herbicidally active compounds and, if appropriate, additionally a crop-plant-compatibility-improving compound, which combinations can be used with particularly good results for controlling weeds in various crops of useful plants or else for controlling monocotyledonous and dicotyledonous weeds in the semi-and nonselective field.
Substituted thien-3-yl-sulphonylamino(thio)carbonyltriazolin(emi)ones are known to be effective herbicides (cf. WO-A-01/05788). However, the activity of these compounds is not always entirely satisfactory.
Surprisingly, it has now been found that a number of active compounds from the group of the substituted thien-3-yl-sulphonylamino(thio)carbonyltriazoIin(ethi)ones, when used together with certain herbicidally active compounds, show synergistic effects with respect to the activity against weeds and can be used particularly advantageously as broadly active combination preparations for the selective control of monocotyledonous and dicotyledonous weeds in crops of useful plants, such as, for example, in cotton, barley, potatoes, maize, oil seed rape, rice, rye, soy beans, sunflowers, wheat, sugar cane and sugar beet, but also for controlling monocotyledonous and dicotyledonous weeds in the semi- and nonselective field.
The invention provides herbicidal compositions, characterized by an effective amount of an active compound combination comprising
a) at least one substituted thien-3-yl-sulphonylamino(thio)-carbonyltriazolin(ethi)one of the general formula (I)

-2-

in which
Q1 represents O (oxygen) or S (sulphur),
Q2 represents O (oxygen) or S (sulphur),
R1 represents optionally cyano-, halogen- or C1-C4-aIkoxy-substituted alkyl having l to 6 carbon atoms, or represents in each case optionally cyano- or halo gen-substituted alkenyl or alkynyl having in each case 2 to 6 carbon atoms, or represents in each case optionally cyano-, halogen- or C1-C4-alkyl-substituted cycloalkyl or cycloalkylalkyl having in each case from 3 to 6 carbon atoms in the cycloalkyl group and, if appropriate, l 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, l 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 l to 4 nitrogen atoms and/or l or 2 oxygen or sulphur atoms in the heterocyclyl group and, if appropriate, l to 4 carbon atoms in the alkyl moiety,

-3-
R2 represents hydrogen, cyano, nitro, halogen, or represetits in each case
optionally cyano-, halogen- or C1-C4-alkoxy-substituted alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl having in
each case l 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,
R represents hydrogen, hydroxyl, mercapto, amino, cyano, fluorine, chlorine, bromine, iodine, represents optionally fluorine-, chlorine-, bromine-, cyano-, C1-C4-alkoxy-, C1-C4-alkyl-carbonyl- orC1-C4-alkoxy-carbonyl-substituted alkyl having l 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-, cyano-,C1-C4-alkoxy- or C1-C4-alkoxy-carbonyl-substituted alkoxy, alkylthio, alkyl-amino or alkylcarbonylamino having in each case l 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, or represents dialkyl-amino having in each case l to 4 carbon atoms in the alkyl groups, or represents in each case optionally methyl- and/or ethyl-substituted aziridino, pyrrolidino, piperidino or morpholino, or represents in each case optionally fluorine-, chlorine-, bromine-, cyano- and/or C1-C4 alkyl-substituted cycloalkyl, cycloalkenyl, cycloalkyloxy, cycloalkyl-thio, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy, cycloalkyl-alkylthio or cycloalkylalkylamino having in each case 3 to 6 carbon atoms in the cycloalkyl or cycloalkenyl group and, if appropriate, l 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-aIkoxy- and/or C1-C4-alkoxy-carbonyl-
-4-
substituted aryl, arylalkyl, aryloxy, arylalkoxy, arylthio, arylalkylthio, arylamino or arylalkylamino having in each case 6 or 10 carbon atoms in the aryl group and, if appropriate, l to 4 carbon atoms in the alkyl moiety,
R4 represents hydrogen, hydroxyl, amino, cyano, or represents C2-C10 alkylideneamino, or represents optionally fluorine-, chlorine-, bromine-, cyano-, C1-C4-alkoxy-, C1-C4-alkyl-carbonyl- or C1-C4-alkoxy-carbonyl-substituted alkyl having l to 6 carbon atoms, or represents in each case optionally fluorine-, chlorine- and/or bromine-substituted alkenyl or alkynyl having in each case 2 to 6 carbon atoms, or represents in each case optionally fluorine-, chlorine-, bromine-, cyano-,C1-C4-alkoxy- or C1-C4-alkoxy-carbonyI-substituted alkoxy, alkylamino or alkyl-carbonylamino having in each case l to 6 carbon atoms in the alkyl group, or represents alkenyloxy having 3 to 6 carbon atoms, or represents dialkylamino having in each case l to 4 carbon atoms in the alkyl groups, or represents in each case optionally fluorine-, chlorine-, bromine-, cyan- and/or C1-C4-aIkyl-substituted cycloalkyl, cycloalkylamino or cycloalkylalkyl having in each case 3 to 6 carbon atoms in the alkyl group and, if appropriate, l to 4 carbon atoms in the alkyl moiety, or represents in each case optionally fluorine-, chlorine-, bromine-, cyanc>-, nitro-, C1-C4-alkyl-, trifluoro-methyl- 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, l to 4 carbon atoms in the alkyl moiety, or
R3 and R4 together represent optionally branched alkanediyl having 3 to 6 carbon atoms,
- and salts of the compounds of the formula (j) -

-5-
("Active compounds of Group l") and
b) one or more compounds of a second group of herbicides consisting of
the active compounds below:
4,5-dihydro-3-methoxy-4-methyI-5-oxo-N-[(2-trifluoromethoxyphenyl)-sulphonyl]-l-H-l,2,4-triazole-l-carboxamide sodium salt (flucarbazone-sodium), 2-chloro-N-(ethoxymethyl)-N-(2-ethyl-6-methylphenyl)acetamide (acetochlor), 5-(2-chIoro-4-trifluoromethyIphenoxy)-2-nitrobenzoic acid (sodium salt) (acifluorfen (-sodium)), 2-chloro-6-nitro-3-phenoxybenzenamine (aclonifen), 2-chloro-N-(methoxymethyl)-N-(2,6-diethylphenyl)acetamide (alachlor), methyl 4-hydroxy-6,6-dimethyI-2-oxo-3-[l-[(2-propenyioxy)imino]butyl3-3-cycIohexene-l-carboxylate (sodium salt) (alloxydim (-sodium)), N-ethyl-N'-isopropyl-6-methylthio-l ,3,5-triazine-2,4-diamine (ametryn), 4-amino-N-(l,l-dimethylethyl)-4,5-dihydro-3-(l-methylethyl)-5-oxo-lH-l,2,4-triazole-l-carboxarnide (amicarbazone), N-(4,6-dimethoxypyrimidin-2-yl)-N'-(N-methyl-N-methylsulphonylsulphamoyl)urea (amidosulfuron), lH-l,2,4-triazole-3-amine (amitrole), S-[2-[(4-chlorophenyl)-(l-isopropyl)amino]-2-oxoethyl] O,O-dimethyl phosphoro-dithioate (anilofos), O-methyl N-(4-arninophenylsulphonyl)carbamate (asu-lam), 6-chloro-4-ethylamino-2-isopropylamino-l,3ï5-triazine (atrazine), 2-[2,4-dichloro-5-(2-propynyIoxy)phenyl]-5t6)7,8-tetrahydro-l,2,4-triazolo-[4,3-a]-pyridin-3(2H)-one (azafenidin), N-(4,6-dimethoxypyrimidin-2-yI)-N'-[l-methyl-4-(2-methyl-2H-tetrazol-5-yl)-lH-pyrazol-5-ylsulphonyl]urea (azimsulfuron), N-benzyl-2-(4-fluoro-3-trifluoromethylphenoxy)butanamide (beflubutamid), 4-chloro-2-oxo-3(2H)-benzothiazoleacetic acid (ethyl ester) (benazolin, (-ethyl)), N-butyI-N-ethyl-2,6-dinitro-4-trifluoromethylbenzen-amine (benfluralin), 2,3-dihydro-3,3-dimethyl-5-benzofuranylethane-sulphonate (benfuresate), N-(4,6-dimethoxypyrimidin-2-yl)-N'-(2-methoxy-

-6-
carbonylphenylmethylsulphonyl)urea (bensulfuron-methyl), +3-i-propyl-lH-2,l,3-benzothiadiazin-4(3H)-one 2,2-dioxide (bentazone),' S-[(4-

chlorophenyl)methyl] diethylthiocarbamate (benthiocarb, T Thiobencarb),
methyl 2-[2-[4-(3,6-dihydro-3-methyl-2,6-dioxo-4-trifluorpmethyl-l(2H)-
pyrimidinyIphenoxymethyI]-5-ethylphenoxypropanoate (benzfendizone), 3-
(2-chloro-4-methylsulphonylbenzoyl)-4-phenylthiobicyclo-[3.2.1]-oct-3-ene-
2-one (benzobicyclon), 2-[[4-(2,4-dichloro-3-methylbenzoyl)-l,3-dimethyl-
!H-pyrazoI-5-yl]oxy]-l-(4-methylphenyI)ethanone G^enzofenap), methyl 5-
(2,4-dichIorophenoxy)-2-nitrobenzoate (bifenox), 2,6-bis-(4,6-dimeth-
oxypyrimidin-2-yl-oxy)benzoic acid sodium salt (bispyribac-sodium), 5-
bromo-6-methyl-3-(l-methylpropyI)-2,4(lH,3H)-pyrimidinedione (bromacil),
2-bromo-3,3-dimethyl-N-(l-methyl-l-phenylethyl)butanainide (bromobutide),
3,5-dibromo-4-hydroxybenzaldehyde O-(2,4-dinitrophenyl) oxime (bromo-
fenoxim), 3,5-dibromo-4-hydroxybenzonitrile (bromoxynil), N-butoxy-
methyl-2-chloro-N-(2,6-diethylphenyl)acetamide (butachlor), l,l-dimethyl-2-
oxo-2-(2-propenyloxy)]ethyl 2-chlorO'5-(3ï6-dihydro-3-methyI-2,6-dioxo-4-
trifluoromethyl-l(2H)-pyrimidinyl)benzoate (butafenacil), 4-(l-t-butyl)-N-(s-
butyl)-2,6-dinitroaniline (butralin), 2-(l-ethoximinopropyl)-3-hydroxy-5-
[2,4,6-trimethyI-3-(l-oxobutyl)phenyl]-2-cyclohexene-l-one (butroxydim), S-
ethyl bis-(2-methylpropyl)thiocarbamate (butylate), N,N-diethyl-3-(2,4,6-
trimethylphenylsulphonyl)- 1H-1,2,4-triazole- 1-carboxamide (cafenstrole),
(R)-N-ethyl-2-[(phenylaminocarbonyl)oxy]propanamide (carbetamide), 2-(4-
chloro-2-fluoro-5-(2-chloro-2-ethoxycarbonylethyl)phenyl)-4-difluoromethyl-
5-methyl-2,4-dihydro-3H-l ,2,4-triazol-3-one (carfentrazone-ethyl), 2,4-
dichloro-l-(3-methoxy-4-nitrophenoxy)benzene (chlormethoxyfen), 5-amino
4-chloro-2-phenyl-3(2H)-pyridazinone (chloridazon), N-(4-chloro-6-
methoxypyrimidin-2-yl)-N'-(2-ethoxycarbonyIphenylsulphonyl)urea
(chlorimuron-ethyl), l,3,5-trich!oro-2-(4-nitrophenoxy)benzene
(chlornitrofen), N'-(3-chIoro-4-methylphenyl)-N,N-dimethylurea (chlorotol-
uron), N-(4-methoxy-6-methyl-l,3,5-triazin-2-yl)-N'-(2-chlorophenyl-
sulphonyl)urea (chlorsulfuron), ethyl 2-chloro-3-[2-chloro-5-(l,3,4,5,6,7-

-7-



hexahydro-l,3-dioxo-2H-isoindol-2-yl)phenyl]-2-propanoate (cinidon-ethyl),
exo-l-methyl-4-isopropyl-2-(2-methylphenylmethoxy)-7-oxabicycio-[2.2.1]-

heptane (cinmethylm), N-(4,6-dimethoxy-1,3,5-triazm-2-yl)-N-(2-(2-meth-

oxyethoxy)phenylsulphonyl)urea (cinosulfuron), 2-[l-[2-(4-chlorophen-
oxy)propoxyaminobutyl]-5-(tetrahydro-2H-thiopyran-3-yl)-l,3-cyclo-

hexanedione (clefoxydim), (E,E)-(+)-2-[l-[[(3-chloro-2-pro-
penyl)oxy]imino]propyl]-3-hydroxy-2-cycIohexen-l-one (clethodim), (R)-(2-
propyinyl) 2-[4-(5-chloro-3-fluoropyridin-2-yl-oxy)phenoxypropanoate (clo-
dinafop-propargyl), 2-[(2-chlorophenyl)methyl]-4,4-dimethyl-3-isoxazol-
idinone (clomazone), 2-(2,4-dichloro3-methylphenoxy)-N-phenylpropan-
amide (clomeprop), 3,6-dichloropyridin-2-carboxyIic acid (clopyralid),
methyl 3-chloro-2-[(5-ethoxy-7-fluoro[lï2,4]triazolo[l,5-c]pyrimidin-2-
ylsulphonyl)amino]benzoate (cloransulam-methyl), N-[(2-
chlorophenyl)methyl]-N'-(l-methyl-l-phenylethyl)urea (cumyluron), 2-chloro-4-ethylamino-6-(l-cyano-l-methylethyIamino)-l,3,5-triazine (cyan-azine), N-(4)6-dimethoxypyrimidin-2-yl)-N'-(2-cyclopropylcarbonylphenyl-sulphonyl)urea (cyclosulfamuron), 2-(l-ethoximinobutyl)-3-hydroxy-5-(tetra-hydro-2H-thiopyran-3-yl)-2-cyc!ohexen-l-one (cycloxydim), (R)-butyl 2-f4-(4-cyano-2-fluorophenoxy)phenoxy]propanoate (cyhalofop-butyl), 2,4-di-chlorophenoxyacetic acid (2,4-D), O-ethyl N-[3-(phenylaminocarbonyl-oxy)phenyl]carbamate (desmedipham), 3,6-dichloro-2-methoxybenzoic acid (dicamba), 2,6-dichIorobenzonitrile (dichlobenil), (R)-2-(2,4-dichIorophen-oxy)propanoic acid (dichlorprop-P), methyl 2-[4-(2,4-dichlorophenoxy)phen-oxy]propanoate (diclofop-methyl), N-(2,6-dichlorophenyI)-5-ethoxy-7-fIuoro-[l,2,4-triazolo-[1,5-c]-pyrimidine-2-sulphonamide (diclosulam), 1,2-di-methyl-3,5-diphenyl-lH-pyrazoIium methylsulphate (difenzoquat), N-(2,4-di-fluorophenyl)-2-(3-trifluoromethylphenox-y)pyridine-3-carboxamide (diflu-fenican), 2-[l-[(3,5-difluorophenyl)aminocarbonyIhydrazono]ethyl]pyridine-3-carboxylic acid (diflufenzopyr), N'-[3-chloro-4-(5-t-butyl-oxo-l,3,4-oxadi-azol-3(2H)-yl)phenyl]-N,N-dimethylurea (dimefuron), S-(l-methyl-l-phenylethyl) 1-piperidinecarbothioate (dimepiperate), 2-chloro-N-(2,6-

-8-
dimethylphenyl)-N-(2-methoxyethyl)acetamide (dimethachlor), N-(l,2-di-
methylpropyl)-N>-ethyl-6-methylthio-l,3,5-triazine-2,4-diamine (dimetha-
metryn), (S-) 2-chloro-N-(2,4-dimethyl-3-thienyl)-N-(2-methoxy-l-
methylethyl)acetamide ((S-) (dimethenamid)), 2-amino-4-(l-fluoro-l-
methylethyl)-6-(l-methyl-2-(3,5-dimethylphenoxy)ethylamino)-l,3,5-triazine
(dimexyflam), 6,7-dihydrodipyrido[ l ,2-a:2', 1-c]pyrazinediium dibromide
(diquat-dibromide), S,S-dimethyl 2-difluoromethyl-4-isobutyl-6-trifluorome-
thylpyridine-3,5-dicarbothioate (dithiopyr), N'-(3,4-dichlorophenyl)-N,N-di-
methylurea (diuron), N-(4-methylphenyl)-Nï-(l-methyl-l-phenylethyl)urea
(dymron, daimuron), S-ethyl dipropylthiocarbamate (EPTC), S-(phenyl-
methyl) N-ethyl-N-(l,2-dimethyIpropyl)thiocarbamate (Esprocarb), N-ethyl-
N-(2-methyl-2-propenyl)-2,6-dinitro-4-trifluoromethylbenzeneamine (ethal-
fluralin), methyl 2-[[[[(4-ethoxy-6-methylamino-l,3,5-triazin-2-
yl)amino]carbonyl]amino]sulphonyl]benzoate (ethametsulfuron-methyl), 2-
ethoxy-2,3-dihydro-3,3-dimethyl-5-benzofuraTiylmethanesulphonate (etho-
fumesate), (S)-(2-ethoxy-l-methyl-2-oxoethyl) 2-chIoro-5-(2-chloro-4-tri-
fiuoromethylphenoxy)benzoate (ethoxyfen), N-(4,6-dimethoxypyrimidin-2-
yl)-N'-(2-ethoxyphenoxysulphonyI)urea (ethoxysulfuron), N-(2,3-di-
chlorophenyl)-4-ethoxymethoxybenzamide (etobenzanide), (R)-ethyl 2-[4-(6-
chlorobenzoxazol-2-yloxy)phenoxy]propanoate (Fenoxaprop-(P)-ethyl), 4-(2-
chIorophenyI)-N-cyclohexyl-N-ethyl-4,5-dihydro-5-oxo-lH-tetrazole-l-
carboxamide (fentrazamide), isopropyl N-benzoyl-N-(3-chloro-4-
fluorophenyl)-D-alaninate (flamprop-M-isopropyl), methyl N-benzoy]-N-(3-
ch!oro-4-fluorophenyl)-D-aIaninate (flamprop-M-methyl), N-[[(4,6-dimeth-
oxy-2-pyrimidinyl)amino]carbonyl]-3-trifluoromethyI-2-pyridinesuIphon-
amide (flazasulfuron), N-(2,6-difluorophenyl)-8-fluoro-5-methoxy-[l,2,4]-
triazoIo-[l,5-c]-pyrimidine-2-sulphonamide (florasulam), (R)-butyl 2-[4-(5-
trifluoromethylpyridin-2-yloxy)phenoxy]propanoate (fluazifop-P-butyl),
isopropyl 5-(4-bromo-l-methyI-5-trifIuoromethyI-lH-pyrazol-3-yl)-2-chloro-4-fluorobenzoate (fluazolate), N-(4-fluorophenyI)-N-isopropyI-2-(5-trifluoro-methyl-l,3,4-thiadiazoI-2-yl-oxy)acetamide (flufenacet), ethyl [2-chloro-4-

-9-
fluoro-5-(5-methyl-6-oxo-4-trifluoromethyI-l(6H)-pyridazinyl)phènoxy]-
acetate (flufenpyr), N-(2,6-dif3uorophenyI)-5-methyl-l,2,4-triazolo[l,5-a]-
pyrirnidme-2-sulphonamide (flumetsulam), pentyl [2-chloro-4-fluoro-5-
(1,3,4,5,6 J-hexahydro-l,3niioxo-2H-isoindol-2-yl)phenoxy]acetate (flumi-
clorac-pentyl), 2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-l,4-benzox-
azin-6-yI]-4,5,6,7-tetrahydro-lH-isoindole-l,3-dione (flumioxazin), 2-[4-
chloro-2-fluoro-5-[(l-methyl-2-propynyl)oxy]phenyl]-4,5,6,7-tetrahydro-lH-
isoindole-l,3(2H)-dione (flumipropyn), N,N-dimethyl-N'-(3-
trifluoromethylphenyl)urea (fluometuron), 3-chloro-4-chloromethyl-l-(3-
trifIuoromethylphenyl)-2-pyrrolidinone (fluorochloridone), ethoxycarbonyl-
methyl 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoate (fluoroglyco-
fen-ethyl), l-(4-chloro-3-(2,2,3,3,3-pentafIuoropropoxymethyl)phenyl)-5-
phenyl-lH-l,2,4-triazol-S-carboxamide (flupoxam), l-isopropyl-2-chloro-5-
(3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-l(2H)-pyrimidyl)benzoate
(flupropacil), N-(4,6-dimethoxypyrimidin-2-yl)-N'-(3-methoxycarbonyI-6-
trifluoromethylpyridin-2-ylsulphonyl)urea sodium salt (flupyrsulfuron-
methyl-sodium), 9-hydroxy-9H-fluorene-9-carboxylic acid (flurenol), (4-
amino-3,5-dichloro-6-fIuoropyridin-2-yloxy)acetic acid (2-butoxy-l-
methylethyl ester, 1-methylheptyl ester) (fluroxypyr, -butoxypropyl, -meptyl),
5-methylamino-2-phenyl-4-(3-trifluoromethylphenyl)-3(2H)-furanone (flurta-
mone), methyl [(2-chloro-4-fluoro-5-(tetrahydro-3-oxo-lH,3H-[l,3,4]-thiadi-
azolo-[3,4-a]-pyridazin-l-yliden)aminophenyl]thioacetate (fluthiacet-methyl),
5-(2-chloro-4-trifluoromethylphenoxy)-N-methylsulphonyl-2-nitrobenzamide
(fomesafen), 2-[[[[(4,6-dijnethoxy-2-pyrimidinyl)ainino]carb-
onyl]amino]suIphonyI]-4-formylamino-N,N-diinethylbenzamide (foramsulf-uron), 2-amino-4-(hydroxymethylphosphinyl)butanoic acid (ammonium salt) (glufosinate (ammonium)), N-phosphonomethylglycine (isopropylammonium salt) (glyphosate, isopropylammonium), methyl 3-chloro-5-[[[[(4,6-dimeth-oxy-2-pyrimidinyl)amino]carbonyl]amino]sulphonyl]-l-methyl-lH-pyrazole-4-carboxylate (halosulfuron -methyl), (R)-2-[4-(3-chloro-5-trifluoro-methylpyridin-2-yloxy)phenoxy]propanoic acid (methyl ester, 2-ethoxyethyl

- 10-
ester, butyl ester) (haloxyfop, -methyl, -P-p^thyl, -ethoxyethyl, -butyl), 3-cyclohexyl-6-dimethylamino-l-methyl-l)3,5-triazine-2'4(1H'3H)-dione (hex-
azinone), methyl 2-(4ï5-dihydro-4-methyl-4-is°ProPy1-5-ox°-1H-imidazo1-2-yI)-4-methylbenzoate (imazamethabenz-methy1), 2-(4,5-dihydro-4-methyl-4-isopropyl-5-oxo-lH-imidazol-2-yl)-5-methoxtOethy1Pyridine-3-carboxylic acid(imazamox), 2-(4,5-dihydro-4-methyl-4-isoProPy1-5-oxo-1H-imidazo1-2-yl)-5-methylpyridine-3-carboxylic acid (imazaPic)' 2-(4,5-dihydro-4-methyI-
4-(isopropyl)-5-oxo-lH-imidazol-2-yl)-3-pyridinecarboxylic acid (imazapyr), 2-(4,5-dihydro-4-methyl-4-isopropyl-5-oxo-lH-imidazol-2-y1)quinoIine-3-
carboxylic acid (imazaquin), 2-(4,5-dihydro-4-methy1-4-isoProPy1-5-oxo-1H-imidazol-2-yl)-5-ethylpyridine-3-carboxylic acid (imazethapyr), N-(4,6-dimethoxyp>dmidin-2-yl)-N1K2-chloroimidazol[1,2-a]pyridin-3-ylsulphony1)-urea (imazosulfuron), 2-[2-(3-chlorophnyl)oxiranylmethyI]-2-ethyl-lH-
indene-l,3(2H)-dione (indanofan), N-(4-riiethoxy-6-methy1-1'3'5-triazin-2-yl)-N'-(5-iodo-2-methoxycarbonylphenylsulphony)urea sodium salt (iodo-
sulfuron-methyl-sodium), 4-hydroxy-3,5-diic7dobenzonitrile (ioxynil), N,N-di-methyl-N'-(4-isopropylphenyI)urea (isoproturon)-6-N-(5-t-butyl-3-isoxazolyI)-N'^'-dimethylurea (isouron), N-(3-(l-ethy-I-methylpropyl)isoxazoï-5-yl)-2,6-dimethoxybenzamide(isoxaben), (4-chloro-2-methylsulPhony1Pheny1)-(5-
cyclopropylisoxazol-4-yl)methanone (isox^chlortole)' (5-cyclopropyIisox-azol-4-yl)-(2-methylsulphonyI-4-trifIuoromett1y1Pheny1)methanone (isoxa-
flutole), 2-[(2>3-dihydro-5,8-dimethyl-l,l-dioxidosPiro-[4H-1-benzothio-
pyran-4-yl)-[1,3]-dioxolan-ó-yOcarbonyn-l,3-cyclohexanediaone (ketospira-
dox), (2-ethoxy-l-methyl-2-oxoethyl)5-(2-ctiloro-4-trifluoromethyIphenoxy)-
2-nitrobenzoate (lactofen), 3-cycioh^xyl-6,7-dihydro-lH-cyclopenta-pyrimidine-2,4-(3H,5H)-dione (lenacil), N'-(3»4-dichlorophenyl)-N-inethoxy-N-methylurea (linuron), (4-chloro-2-methy)Phenoxy)acetic acid (MCPA), (R)-2-(4-chloro-2-methylphenoxy)propionic acid (mecoprop-P), 2-(2-benz-othiazoIyIoxy)-N-methyl-N-phenylacetamide (mefenacet), methyl 2-[[[[(4,6-dimethoxy-2-pyrimidinyl)arnino]carbonyl]amin°]sulPhony1]-4-[[(methylsulphonyl)amino]methyl]benzoate (mesosulfuron), 2-(4-methyl-

-11-
sulphonyl-2-nitrobenzoyl)-l,3-cycIohexanedione (mesotrione), 4-amino-3-
methyl-6-phenyl-l,2,4-triazin-5(4H)-one (metamitron), 2-chloro-N-(2,6-
dimethylphenyl)-N-(lH-pyrazol-l-ylmethyl)acetamide (metazachlor), N-(2-
benzodiiazolyl)-N,N'-dimethyIurea (methabenzthiazuron), N'-(4-
bromophenyl)-N-methoxy-N-methylurea (metobromuron), (S)-2-chIoro-N-(2-
ethyl-6-methylphenyl)-N-(2-methoxy-l-methyIethyl)acetamide (metolachlor,
S-metolachlor), N-(2,6-dichloro-3-methylphenyI)-5I7-dimethoxy-l,2,4-tri-
azolo[lJ5-a]-pyrimidine-2-sulphonamide (metosulam), N'-(3-chloro-4-
methoxyphenyl)-N,N-di methyl urea (metoxuron), 4-amino-6-tert-butyl-3-
methylthio-1,2,4-triazin-5(4H)-one (metribuzin), N-(4-methoxy-6-methyl-
l,3,5-triazin-2-yl)-Nï-(2-methoxycarbonylphenylsulphonyl)urea (metsulf-
uron-methyl), S-ethyl hexahydro-lH-azepine-1-carbothioate (molinate), 2-(2-
naphthyloxy)-N-phenylpropanamide (naproanilide), N,N-diethyl-2-(l-
naphthalenyloxy)propanamide (napropamide), N-butyl-N'-(3,4-di-
chlorophenyl)-N-methylurea (neburon), N-(4,6-dimethoxypyrimidin-2-yl)-N'-(3-dimethyIcarbamoylpyridin-2-yIsulphonyl)urea (nicosulfuron), 4-chloro-5-methylamino-2-(3-trifluoromethylphenyl)-3(2H)pyridazinone (norflurazon), S-(2-chlorobenzyl) N,N-diethylthiocarbamate (orbencarb), 4-dipropylamino-3,5-dinitrobenzenesuIphonamide (oryzalin), 3-[2,4-dichloro-5-(2-propynyl-oxy)phenyl]-5-(t-butyl)-l,3,4-oxadiazol-2(3H)-one (oxadiargyl), 3-[2,4-dichloro-5-(l-methylethoxy)phenyl]-5-(t-butyl)-l,3,4-oxadiazol-2(3H)-one (oxadiazon), N-(4,6-dimethylpyrimidin-2-yl)-N'-(2-oxetan-3-yl-oxycarb-onylphenylsulphonyl)urea (oxasulfuron), 3-[l-(3,5-dichlorophenyl)-l-isopropyl]-2,3-dihydro-6-methyl-5-phenyl-4H-l,3-oxazin-4-one (oxaziclo-mefone), 2-chloro-l-(3-ethoxy-4-nitrophenoxy)-4-trifIuoromethylbenzene (oxyfluorfen), l,r-dimethyl-4,4'-bipyridinium (paraquat), l-amino-N-(l-ethy!propyl)-3,4-dimethyl-2,6-dinitrobenzene (pendimethalin), 4-(t-buty])-N-(l-ethylpropyl)-2,6-dinitrobenzenamine (pendralin), 2-(2,2-difluoroethoxy)-N-CS^-dimethoxytl^^triazolotl.S-clpyrimidin^-yO-ö-trifluor-omethylbenzenesulphonamide (penoxsulam), 3-(4-chloro-5-cyclopentyloxy-2-fluorophenyI)-5-(l-methylethylidene)-2,4-oxazoIidinedione (pentoxazone),

-12-
2-chloro-N-(2-ethoxyethyl)-N-(2-methyl-l-phenyl-l-propenyl)acetamide
(pethoxamid), O-methyl N-[3-(3-methylphenylaminocarbonyI-
oxy)phenyl]carbamide (phenmedipham), 4-amino-3,5,6-trichIoropyridine-2-
carboxylic acid (picloram), N-(4-fluorophenyl)-6-(3-trifluoromethylphen-
oxy)pyridine-2-carboxamide (picolinafen), S-[2-(2-methyl-l-piperidinyl)-2-
oxoethyl] O,O-dipropyl phosphorodithioate (piperophos), 2-chIoro-N-(2,6-di-
ethylphenyl)-N-(2-propoxyethyl)acetamide (pretilachlor), N-(4,6-bis-difluoro-
methoxypyrimidin-2-yI)-N'-(2-methoxycarbonylphenylsulphonyl)urea (primi-
sulfuron-methyl), l-chloro-N-[2-chloro-4-fluoro-5-[(6S,7aR)-6-fluorotetra-
hydro-l,3-dioxo-lH-pyrrolo[l,2-c]imidazol-2(3H)yl]phenyl]methanesulphon-
amide (profluazol), 2-[l-[[2-(4-chIorophenoxy)propoxy]imino]butyl]-3-
hydroxy-5-(tetrahydro-2H-thiopyranyl)-2-cyclohexen-l-one (profoxydim),
N,N'-bis-isopropyl-6-methylthio-l,3,5-triazine-2,4-diamine (prometryn), 2-
chloro-N-isopropyl-N-phenylacetamid (propachlor), N-(3,4-di-
chlorophenyl)propanamide (propanil), (R)-[2-[[(l-methylethyli-
dene)amino]oxy]ethyl] 2-[4-(6-chloro-2-quinoxalinyloxy)phenoxy]pro-
panoate (propaquizafop), 2-chloro-N-(2-ethyl-6-methylphenyl)-N-[(l-methylethoxy)methyl]acetamide (propisochlor), methyl 2-[[[(4,5-dihydro-4-methyl-5-oxo-3-propoxy-lH-l,2,4-triazol-l-yl)carbonyl]amino]suIph-onyljbenzoate sodium salt (propoxycarbazone-sodium), 3,5-dichloro-N-(l,l-dimethyl-2-propynyl)benzamide (propyzamide), S-phenylmethyl N,N-di-propylthiocarbamate (prosulfocarb), N-(4-methoxy-6-methyl-l,3>5-triazin-2-yl)-N'-(2-(3,3,3-trifluoropropyl)phenylsulphonyl)urea (prosulfuron), l-(3-chloro-4)5T6,7-tetrahydropyrazolo[l,5-a]pyridin-2-yI)-5-(methyl-2-propynyl-amino)-lH-pyrazol-4-carbonitrile (pyraclonil), ethyl [2-chloro-5-(4-chloro-5-difluoromethoxy-l-methyl-lH-pyrazol-3-yl)-4-fluoro-phenoxy]acetate (pyra-flufen-ethyl), 4-(2,4-dichlorobenzoyl)-l,3-dimethyI-5-(4-methylphenylsulph-onyloxy)pyrazole (pyrazolate), N-(4,6-dimethoxypyrimidin-2-yl)-Ni-(4-eth-oxycarbonyl-l-methylpyrazol-5-ylsulphonyl)urea (pyrazosulfuron-ethyl), 4-(2,4-dichlorobenzoyl)-l,3-dimethyl-5-(phenylcarbonylmethoxy)pyrazole (pyr-azoxyfen), diphenylmethanone O-[2,6-bis-(4,6-dimethoxypyrimidin-2-yl-

-13-
oxy)benzoyl] oxime (pyribenzoxim), O-[3-(l,l-dimethylethyl)phenyl] (6-
methoxy-2-pyridinyl)methylthiocarbamate (pyributicarb), 6-chloro-3-phenyl-
4-pyridazino] (pyridafol), O-(6-chloro-3-phenylpyridazin-4-yl) S-octyl thio-
carbonate (pyridate), 6-chloro-3-phenylpyridazin-4-oI (pyridatol), 7-[(4,6-di-
methoxy-2-pyrimidinyl)thio]-3-methyl-l(3H)-isobenzofuranone (pyriftalid),
methyl 2-(4,6-dimethoxypyrimidin-2-yloxy)benzoate (pyriminobac-methyl),
2-chloro-6-(4,6-dimethoxypyrimidin-2-ylthio)benzoic acid sodium salt (pyri-
thiobac-sodium), 3,7-dichloroquinoline-8-carboxylic acid (quinchlorac), 7-
chloro-3-methylquinoline-8-carboxylic acid (quinmerac), 2-amino-3-chloro-
1,4-naphthalenedione (quinoclamine), (R)-2-[4-(6-chloro-2-quinoxaIinyl-
oxy)phenoxy]propanoic acid (ethyl ester, tetrahydro-2-furanylmethyl ester)
(quizalofop, -ethyl, -P-ethyl, -P-tefuryl), N-(4,6-dimethoxypyrimidin-2-yl)-
N'-(3-ethylsulphonylpyridin-2-yl-sulphonyl)urea (rimsulfuron), 2-(l-ethox-
iminobutyl)-5-(2-ethy!thiopropyl)-3-hydroxy-2-cyclohexen-l-one (sethoxy-
dim), 6-chloro-2,4-bis-ethylamino-lï3,5-triazine (simazine), 2-(2-chloro-4-
methylsulphonylbenzoyl)cyclohexane-l,3-dione (sulcotrione), 2-(2,4-di-
chloro-S-methylsulphonylaminophenyl)-4-difluoromethyl-5-methyl-2,4-di-
hydro-3H-l,2,4-triazol-3-one (sulfentrazone), methyl 2-[[[[(4,6-dimethyl-2-
pyrimidinyl)amino]carbonyl]amino]sulphonyl]benzoate (sulfometuron-
methyl), N-phosphonomethylglycine trimethylsulphonium (sulfosate), N-(4,6-dimethoxypyrimidin-2-yl)-Nï-(2-ethylsuIphonyl)imidazo[l,2-a]pyridine-3-sulphonamide (sulfosulfuron), N-(5-t-butyl-l,3,4-thiadiazol-2-yl)-N,N'-dimethylurea (tebuthiuron), 2-[l-[(3-chloro-2-propenyI)oxyimino]propyI]-3-hydroxy-5-(tetrahydro-2H-pyran-4-yl)-2-cyclohexen-l-one (tepraloxydim), 6-chloro-4-ethylamino-2-t-butyIamino-l,3,5-triazine (terbuthylazine), 2-t-butyI-amino-4-ethylamino-6-methylthio-l,3,5-triazine (terbutryn), 2-chloro-N-(2,6-dimethyIphenyl)-N-(3-methoxy-2-thienylmethyl)acetamide (thenylchlor), 2-difluoromethyl-5-(4,5-dihydrothiazol-2-yl)-4-(2-methylpropyl)-6-trifluoromethylpyridine-3-carboxyIate (thiazopyr), N-(4-methoxy-6-methyl-l,3,5-triazin-2-yl)-N'-(2-methoxycarbonyIthien-3-ylsulphonyl)urea (thifen-sulfuron-methyl), S-phenylmethyl bis-s-butylcarbamothioate (tiocarbazil), 2-

-14-
(ethoximinopropyI)-3-hydroxy-5-(2,4,6-trimethylphenyl)-2-cyclohexen-l-one
'
(tralkoxydim), S-(2,3,3-trichloro-2-propenyl) diisopropylcarbamothiöate
(triallate), N-(4-methoxy-6-methyl-l,3,5-triazin-2-yl)-N'-[2-(2-chloroeth-

oxy)phenylsulphonyl]urea (triasulfuron), N-methyl-N-(4-mëthoxy-6-methyl-
.
l ,3,5-triazin-2-yl)-N'-(2-methoxycarbonylphenyIsulphonyl)urea . (tribenuron-
methyl), (3,5,6-trichloro)pyridin-2-yloxyacetic acid (triclopyr), 2-(3,5-
dichlorophenyl)-2-(2,2,2-trichloroethyl)oxirane (tridiphane), N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-3-(2,2}2-trifluoroethoxy)-2-pyri-dinesulphonamide sodium salt (trifloxysulfuron), l-amino-2,6-dinitro-N,N-dipropyl-4-trifluoromethylbenzene (trifluralin), N-[4-dimethylamino-6-(2,2,2-trifluoroethoxy)-l,3,5-triazin-2-yl]-N'-(2-methoxycarbonylphenylsulph-onyl)urea (triflusulfuron-methyl), N-(4-methoxy-6-trifluoromethoxy-l ,3,5-tri-azin-2-yl)-N'-(2-trifluoromethylphenylsulphonyl)urea (tritosulfuron), N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-3-(N-methyl-N-methyl-sulphonylamino)-2-pyridinesulphonamide (cf. WO-A-92/10660), N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-3-(N-methyl-N-methylsulph-onylamino)-2-pyridinesulphonamide (cf. WO-A-92/10660), 4-(4,5-dihydro-4-methyl-5-oxo-3-trifluoromethyl-lH-l?2,4-triazol-l-yl)-2-(ethylsulphonyl-amino)-5-fluorobenzenecarbothioamide (HWH4991, cf. WO-A-95/30661), 2-chloro-N-[l-(2,6-dichloTO-4-difluoromethylphenyl)-4-nitro-!H-pyrazol-5-yl]propanecarboxamide (SLA5599, cf. EP-A-303153), [2-chloro-3-(4,5-dihydro-3-isoxazolyl)-4-methylsulphonylphenyl]-(5-hydroxy-l-methyl-lH-pyrazol-4-yl)methanone (cf. WO-A-96/26206, WO-A-98/31681), [3-(4,5-dihydro-3-isoxazolyl)-2-methyl-4-methylsulphonylphenyI]-(5-hydroxy-l-methyl-lH-pyrazol-4-yl)methanone (cf. WO-A-96/26206, WO-A-98/31681), [3-[2-chloro-3-[(2,6-dioxocyclohexyl)carbonyl3-6-ethylsulphonylphenyl]-5-is-oxazolyljacetonitrile (cf. WO-A-01/28341), 2-[2-chloro-4-methylsulphonyl-3-[(2,2T2-trifluoroethoxy)methyl]benzoyI]-l,3-cyclohexanedione (cf. WO-A-01/28341), 2-[[5,8-dimethyl-l,l-dioxido-4-(2-pyrimidinyloxy)-3,4-dihydro-2H-thiochromen-6-yl]carbonyl]-l,3-cyclohexanedione(cf. WO-A-01/28341)

-15-
("Active compounds of group 2"), and, if appropriate, definitely
c) a compound that improves compatibility with erop plants, from the following group of compounds:
4-dichloroacetyI-l-oxa-4-azaspiro[4.5]decane (AD-67), 1-dichloroacetylhexa-hydro-33,8a-trimethyIpyrroIo[l,2-a]pyrimidin-6(2H)-one (BAS-145138), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-l,4~benzoxazine (benoxacor), 1-methylhexyl 5-chloroquinoxalin-8-oxyacetate (cloquintocet-mexyl),
-16-
[[(4-methylaminocarbonyIamino)phenyI]suIphonyl]-2-methoxybenzamide (the latter are in each case known from WO-A-99/66795)
("Active compounds of Group 3")-
Preferred meanings of the groups listed above in connection with the formula (I) are defmed below.
Q1 preferably represents O (oxygen) or S (sulphur). Q2 preferably represents O (oxygen) or S (sulphur).
R1 preferably represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or isopropyl, 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 cyclohexyl methyl, represents in each case optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or isopropyl-, tri-fluoromethyl-, methoxy-, ethoxy-, n- or isopropoxy-, difluoro-methoxy- 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-substituted heterocyclyl or heterocyclylmethyl, where the heterocyclyl group is in each case selected from the group consisting of oxetanyl, thietanyl, furyl, tetra-hydrofuryl, thienyl and tetrahydrothienyl.

-17-
R2 preferably represents hydrogen, cyano, fluorine, chlorine, bromine, represents 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 isopropoxycarbonyl, methylthio, ethylthio, n- or isopropylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl, or represents in each case optionally cyano-, fluorine-or chlorine-substituted propenyl, butenyl, propynyl, butinyl, propenyl-oxy, butenyloxy, propinyloxy or butinyloxy.
R3 preferably represents hydrogen, hydroxyl, mercapto, amino, cyano, fluorine, chlorine, bromine, or represents in each case optionally fluorine-, chlorine-, cyano-, methoxy-, ethoxy-, n- or isopropoxy-, acetyl-, propionyl-, n- or isobutyroyl-, methoxycarbonyl-, ethoxy¬carbonyl-, n- or isopropoxycarbonyl-substituted methyl, ethyl, n- or isopropyl, n-, iso-, s- or t-butyl, or represents in each case optionally fluorine-, chlorine-, and/or bromine-substituted ethenyl, propenyl, butenyl, ethynyl, propinyl or butinyl, represents in each case optionally fluorine-, chlorine-, cyano-, methoxy-, ethoxy-, n- or isopropoxy-, methoxycarbonyl-, ethoxycarbonyl-, n- or isopropoxycarbonyl-substituted methoxy, ethoxy, n- or isopropoxy, n-, iso-, s- or t-butoxy, methylthio, ethylthio, n- or isopropylthio, n-, iso-, s- or t-butylthio, methylamino, ethylamino, n- or isopropylamino, n-, iso-, s- or t-butyl-amino, acetylamino or propionylamino, or represents propenyloxy, butenyloxy, ethynyloxy, propinyloxy, butinyloxy, propenylthio, butenylthio, propinylthio, butinylthio, propenyl amino, butenylamino, propinylamino or butinylamino, or represents dimethyl amino, diethyl-amino or dipropylamino, represents in each case optionally fluorine-, chlorine-, methyl- and/or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclo-

-18-
butylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclo-butylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclophentylmethyl,cyclohexylmethyl, cyclopropyl methoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexyl-tnethoxy, cyclopropylmethylthio, cyclobutylmethylthio, cyclopentyl-hiethylthio, cyclohexylmethylthio, cyclopropylmethylamino, cyclo-Wylmethylamino, cyclopentylmethylamino or cyclohexylmethyl-amino, or represents in each case optionally fluorine-, chlorine-, bromine-, methyl-, trifluoromethyl-, methoxy- or methoxycarbonyl-substituted phenyl, benzyl, phenoxy, benzyloxy, phenylthio, benzyl-Ihio, phenylamino or benzylamino,
R preferably represents hydrogen, hydroxyl, amino, or 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, propinyl or butynyl, represents in each case optionally fluorine-, chlorine-, cyano-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or isopropoxy, n-, iso-, s- or t-Hutoxy, metn'yïamiho, effiyrarruho, n- or isopropyfaimno, n-, iso-, s- or t-butylamino, represents propenyloxy or butenyloxy, represents di-methylamino or diethylamino, represents in each case optionally fluorine-, chlorine- methyl- and/or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylamino, cyclobutyl-amino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or represents in each case optionally fluorine-, chlorine-, mtehyl-, tri-fluoromethyl- and/or methoxy-substituted phenyl or benzyl.
R and R4 together preferably represent trimethylene (propane-l,3-diyl), tetra-"lethylene (butane-l,4-diyl) or pentamethylene (pentane-l,5-diyl).

-19-
Q1 particularly preferably represents O (oxygen), Q2 particularly preferably represents O (oxygen).
R1 particularly preferably represents in each case optionally fluorine-, chlorine-, 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- of iso-propyl.
R3 particularly preferably represents hydrogen, chlorine, bromine, or represents in each case optionally fluorine-, chlorine-, methoxy-, ethoxy-, n- or isopropoxy-substituted methyl, ethyl, n- or isopropyl, or represents in each case optionally fluorine- or chlorine-substituted ethenyl, propenyl, butenyl, propinyl or butynyl, or represents in each case optionally fluorine-, chlorine-, methoxy-, ethoxy-, n- or isopropoxy-substituted methoxy, ethoxy, n- or isopropoxy, methylthio, ethylthio, n- or isopropylthio, methylamino, ethylamino, n- or isopropylamino, represents propenyloxy, propynyloxy, propenylthio, propynylthio, propenylamino or propynylamino, represents dimethyl-amino or diethylamino, represents in each case optionally fluorine-, chlorine- or methyl-substituted cyclopropyl, cyclopropyloxy, cyclo-propylmethyl or cyclopropyl methoxy, and
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 ethoxy-substituted

-20-
methoxy, ethoxy, n- or isopropoxy, represents methylamino, or represents cylopropyl.
Preferred active compound components of Group l are in particular also the sodium, potassium, magnesium, calcium, ammonium, C1-C4-alkylammonium, di-(C1-C4-alkyl)ammonium, tri-(C1-C4-alkyl)arnmonium, tetra-(C1-C4-alkyl)ammonium, tri-(C1-C4-alkyl)sulphonium, C5- or C6-cycloalkylammonium and di-(C1-C2-alkyl)benzylammonium salts of compounds of the formula (I) in which Q1, Q2, R1, R2, R3 and R4 have the meanings given above as being preferred.
Table 1: Examples of compounds of the formula (I)
Examples of compounds of the formula (I) which are very particularly preferred as active compound components according to the invention are listed in Table l below. The sodium salts of the compounds of Table l, and in particular the sodium salts of the compounds 1-1 and 1-2, are likewise particularly emphasized as active compound components according to the invention.



-21-

According to their chemical structure, the compounds of Group 2 can be assigned to the following classes of active compounds:
Amides (for example isoxaben, picolinafen, propanil), arylheterocycles (for example azafenidin, benzfendizone, butafenacil-allyl, carfentrazone-ethyl, cinidon-ethy], flu-azolate, flumiclorac-pentyl, flurnioxazin, flupropacil, fluthiacet-methyl, oxadiazon, oxadiargyl, profluazol, pyraflufen-ethyl, pyridate, pyridafol, sulphentrazone, 4-[4,5-dihydro^-methyl-5-oxo-(3-trifluoromethyl)-lH-l,2,4-triazol-l-yl]-2-[(ethylsulph-onyl)amino]-5-fluorobenzenecarbothioamide), aryloxyphenoxypropionate (for example clodinafop-propargyl, cyhalofop-butyl, diclofop-methyl, fenoxaprop-P-ethyl, fluazifop-P-butyl, haloxyfop-P-methyl, quizalofop-P-ethyl), carboxylic acid

-22-
derivatives (for example clopyralid, dicamba, fluroxypyr, picloram, triclopyr), benzo-
thiadiazole (for example bentazone), chloroacetamides (for example acetochlór, ala-
chlor, butachlor, (S-) dimethenamid, metazachlor, metolachlor, pretilachlor, propa
-
chlor, propisochlor), cyclohexanedione (for example butroxydim, clefoxydim,
cycloxydim, sethoxydim, tralkoxydim), dinitroanilines (for example benfiuralin,
ethalfluralin, oryzalin, pendimethalin, trifluralin), diphenyl ethers (for example aci-

fluorfen-sodium, aclonifen, bifenox, fluoroglycofen-ethyl, fomesafen, lactofen, óxy-


fluorfen), ureas (for example chlorotoluron, diuron, isoproturon, linuron, metobrom-
uron, metoxuron), imidazolinones (for example imazamethabenz-methyl, imazamox,
imazaquin, imazethapyr), isoxazole (for example isoxaflutole), nicotinanilides (for
example diflufenican), nitriles (for example bromoxynil, ioxynil), organophosphorus
compounds (for example anilofos, glufosinate-ammonium, glyphosate-isopropyl-
ammonium, sulphosate), oxyacetamides (for example flufenacet, mefenacet), phen-
oxycarboxylic acid derivatives (for example 2,4-D, dichloroprop-P, MCPA, MCPB,
mecoprop), pyrazoles (for example pyrazolate, pyrazoxyfen), pyridazinones (for
example norflurazon), pyridines (for example dithiopyr, thiazopyr), pyrimidinyl-
(thio)benzoates (for example bispyribac, pyribenzoxim, pyrithiobac, pyriminobac),
sulphonyl ureas (for example amidosulfuron, azimsulfuron, bensulfuron-methyl,
chloroimuron-ethyl, chlorosulfuron, cinosulfuron, cyclosulfamuron, ethoxysulfuron,
flupyrsulfuron-methyl-sodium, foramsulfuron, iodosulfuron-methyl-sodium, imazo-
sulfuron, metsulfuron-methyl, nicosulfuron, oxasulfuron, primisulfuron-methyl, pro-
sulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron-methyl, sulfosulfuron, thi-
fensulfuron-methyl, triasulfuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron-
methyl, tritosulfuron), tetrazolinones (for example fentrazamide), thiocarbamates (for
example butylate, dimepiperate, EPTC, esprocarb, molinate, orbencarb, prosulfocarb,
triallate), triazines (for example ametryn, atrazine, cyanazine, dimexyflam, simazine,
terbuthylazine, terbutryn), triazinones (for example hexazinone, metamitron, metri-
buzin), triazoles (for example amitrole), triazolinones (for example amicarbazone,
flucarbazone-sodium, propoxycarbazone-sodium), triazolopyrimidines (for example
cloransulam-methyl, diclosulam, florasulam, flumetsulam, metosulam), triketones
(for example mesotrione, sulcotrione), uracils (for example bromacil).

-23-
Mixing components from the active compounds of the Group 2 which are particularly emphasized are:
flucarbazone-sodium, acetochlor, aclonifen, alachlor, amicarbazone, amidosulfuron, amitrole, anilofos, asulam, atrazine, beflubutamid, benazolin (-ethyl), benfuresate, bentazone, bifenox, bispyribac-sodium, bromoxynil, butylate, carfentrazone-ethyl, chlorotoluron, chlorosulfuron, cinidon-ethyl, clodinafop-propargyl, clopyralid, cyan-azine, 2,4-D, desmedipham, dicamba, dichlorprop-P, diclofop-methyl, difenzoquat, diflufenican, diflufenzopyr, dimethenamid, S-dimethenamid, EPTC, ethofumesate, ethoxysulfuron, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fentrazamide, flamprop-M-isopropyl, flamprop-M-methyl, florasulam, fluazifop-P-butyl, fluazolate, flufenacet, flumetsulam, fluoroglycofen-ethyl, flupyrsulfuron-methyl-sodium, fluroxypyr, -butoxypropyl, -meptyl, flurtamone, fluthiacet-methyl, foramsulfuron, glufosinate, glufosinate-ammonium, halosulfuron-methyl, haloxyfop-P-methyl, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, iodosulfuron-methyl-sodium, ioxynil, isoproturon, isoxaben, isoxachlortole, isoxaflutole, lactofen, linuron, MCPA, mecoprop-P, mefenacet, mesosulfuron, mesotrione, metamitron, metazachlor, methabenzthiazuron, metolachlor, S-metolachlor, metosulam, metri-buzin, metsulfuron-methyl, naproanilide, neburon, nicosulfuron, oxadiargyl, oxadi-azon, oxaziclomefone, oxyfluorfen, pendimethalin, penoxsulam, phenmedipham, picolinafen, primisulfuron-methyl, profluazol, propanil, propoxycarbazone-sodium, prosulfocarb, prosulfuron, pyraclonil, pyraflufen-ethyl, pyribenzoxim, pyridafol, pyri-date, qinclorac, quinmerac, rimsulfuron, sulcotrione, sulfosate, sulfosulfuron, ter-buthylazine, thifensulfuron-methyl, tralkoxydim, triallate, triasulfuron, tribenuron-methyl, tritosulfuron, 4-(4,5-dihydro-4-methyl-5-oxo-3-trifIuoromethyl-lH-l,2,4-tri-azol-l-yl)-2-(ethyIsulphonylamino)-5-fIuoro-benzenecarbothiamide (HWH4991), 2-chloro-N-[l-(2,6-dichloro-4-difluoromethylphenyl)-4-nitro-lH-pyrazol-5-yljpropanecarboxamide (SLA5599).

-24-
The compositions according to the invention preferably comprise one or two active compounds of Group l, one to three active compounds of Group 2 and, if appropriate, one active compound of Group 3.
In particular, the compositions according to the invention comprise one active compound of Group l, one or two active compounds of Group 2 and, if appropriate, one active compound of Group 3.
Examples of combinations according to the invention of in each case one active compound of Group l and one or two active compounds of Group 2 - or of in each case one active compound of Group l, one or two active compounds of Group 2 and one compound of Group 3 - are listed below in Table 2. Here, the names of the active compounds of the formula (I) (active compounds of Group 1) are in each case taken from Table 1.

-25-
Table 2: Examples of combinations comprising one active compound of Group l and
one or two active compounds of Group 2 (and, if appropriate, additionally a safener)


-26-


-27-


-28-


-29-


-30-


-31-


-32-


-33-


-34-


-35-


-36-


-37-


-38-


-39-


-40-


-41 -


-42-


-43-


-44-


-45-


-46-


-47-
Surprisingly, it has now been found that the above-defined active compound combinations of the substituted thien-3-yl-sulphonyIamino(thio)carbonyltriazoIin-(ethi)ones of the formula (I) and/or their salts and the abovementioned active compounds of Group 2 exhibit a particularly high herbicidal activity combined with very good erop plant compatibility and can be used for the selective control of monocotyledonous and dicotyledonous weeds in a variety of crops, in particular in cotton, barley, potatoes, maize, oilseed rape, rice, rye, soya beans, sunflowers, wheat, sugar cane and sugar beet, especially in barley, maize, rice and wheat, and additionally also for controlling monocotyledonous and dicotyledonous weeds in the semi- and nonselective field.
Surprisingly, the herbicidal activity of the active compound combinations according to the invention of compounds of the abovementioned Groups l and 2 exceeds the total of the action of the individual active compounds considerably.
Thus, not just a complementation of actions but a synergistic effect is present which could not have been predicted. The new active compound combinations are well tolerated in a variety of crops, also effecting good control of weeds which are usually difficult to control. Thus, the novel active compound combinations are a valuable addition to the herbicides.
The synergistic effect of the active compound combinations according to the invention is particularly strongly pronounced in certain concentration ratios. However, the weight ratios of the active compounds in the active compound combinations may be varied within relatively wide ranges. In general, from 0.001 to 1000 parts by weight, preferably from 0.002 to 500 parts by weight and particularly preferably from 0.01 to 100 parts by weight of active compound of Group 2 are used per part by weight of active compound of the formula (I).
The following may be particularly emphasised as mjxing components from amongst the active compounds of Group 3:

-48-
l -methylhexyl 5-chIoroquinoxalin-8-oxyacetate (cloquintocet-mexyl), ethyl 4,5-
dihydro-5,5-diphenyl-3-isoxazo]ecarboxy!ate (isoxadifen-ethyl) and diethyl l-(2,4-
dichlorophenyl)4,5-dihydro-5-methyl-lH-pyrazole-3,5-dicarboxylate (mefenpyr-
diethyl), which are particularly suitable for improving the compatibility in barley and
wheat and, to a certain extent, also in maize and rice, and 4-dichloroacetyl-l-oxa-4-
azaspiro[4.5]-decane (AD-67), l-dichloroacetyl-hexahydro-3,3»8a-
trimethylpyirolo[l,2-a]-pyrimidin-ó(2H)-one (BAS-145138), 4-dichloroacetyl-3,4-
dihydro-3-methyl-2H-l,4-benzoxazine (benoxacor), 2,2-dichloro-N,N-di-2-
propenylacetamide (dichlormid), 3-dichloroacetyl-5-(2-furanyl)-2,2-
dimethyloxazolidine (furilazole, MON-13900) and 3-dichIoroacetyl-2,2,5-trimethyloxazolidine (R-29148), which are particularly suitable for improving the compatibility in maize.
It must be considered as surprising that, from amongst a multiplicity of known safeners or antidotes capable of antagonizing the harmful effects of a herbicide on the erop plants, it is precisely the abovementioned compounds of Group 3 which are capable of almost completely compensating the harmful effect, on the erop plants, of active compounds of the formula (I) and their salts, if appropriate also in combination with one or more of the abovementioned active compounds of Group 2, without adversely affecting the herbicidal efficacy towards the weeds.
Surprisingly, it has also been found that the herbicidally active substance 2,4-dichlorophenoxyacetic acid (2,4-D) and its derivatives, too, can play the safener role described above.
Accordingly, a preferred embodiment is also a mixture comprising a compound of the formula (I) and/or salts thereof on the one hand, and 2,4-D and/or its derivatives on the other hand, if appropriate in combination with one or more of the active compounds of Group 2 listed above. Typical derivatives of 2,4-D are, forexample, its esters.

-49-
Surprisingly, it has also been found that the herbicida.lly active substances (4-chloro-2-methylphenoxy)acetic acid (MCPA) and (+-)-2-(4-chloro-2-methylphenoxy)propanoic acid (mecoprop) can also play a safener role. The compounds mentioned are described in the following patent applications: JP.63 072 605 and GB 00 820 180.
The compounds diethyl l-(2,4-dichloropheny])-4,5-dihydro-5-methyl-lH-pyrazole-3,5-dicarboxyIate (mefenpyr-diethyl), l-methylhexyl [(5-chloro-8-quinolinyl)-oxy]acetate (cloquintocet-mexyl) and ethyl l-(2,4-dichlorophenyl)-5-(trichloro-methyl)-lH-l,2,4-triazole-3-carboxyIate (fenchlorazole-ethyl) are described in the following patent applications: DE-A-39 39 503, EP-A-191 736 and DE-A-35 25 205. 2,4-D is a known herbicide.
The advantageous effect of the erop plant compatibility of the active compound combinations according to the invention is likewise piarticularly strongly pronounced at certain concentration ratios. However, the weight ratios of the active compounds in the active compound combinations can be varied within relatively wide ranges. In general, from 0.001 to lOOO parts by weight, preferably from 0.01 to lOO parts by weight and particularly preferably from 0.1 to lO parts by w^ght of one of the erop plant compatibility-improving compounds mentioned above under (c) (antidotes/safeners) are used per part by weight of active compound of the formula (I) or its mixtures with active compounds of Group 2.
All plants and plant parts can be treated in accordance with the invention. Plants are to be understood as meaning in the present context all pla.nts and plant populations such as desired and undesired wild plants or erop plants (inclüsive of naturally occurring erop plants). Crop plants can be plants which can be obtained by conventional plant breeding and optimisation methods or by biotechnological and recombinant methods or by combinations of these methods, inclüsive of the transgenic plants and inclüsive of the plant varieties protectable or not protectable by plant breeders' rights. Plant parts are to be understood as meaning all aerial and subterranean plant parts and organs of the plants such as shoot, Jeaf, flower and root, examples which may be mentioned being

-50-
leaves, needies, stalks, trvmks, flowers, fruiting bodies, fruits, seeds, roots, tubers and rhizomes, The plant parts also include vegetative and generative propagation material, for example cuttings, tubers, rhizomes, seedlings and seeds.
The treatment according to the invention of the plant and plant parts with the active compounds is carried out directly or by allowing the compounds to act on their surroundings, environment or storage space by the customary treatment methods, for example by immersion, spraying, evaporation, fogging, scattering, painting on and, in the case of propagation material, in particular in the case of seeds, also by applying one or more coats.
Amongst the plants obtained by biotechnological and recombinant methods, or by combining these methods, plants which are emphasized are those which tolerate so-called ALS, 4-HPPD, EPSP and/or PPO inhibitors, such as, for example, Acuron plants.
The active compounds according to the invention can be used, for example, in the following plants:
Picotvledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.
Dicotvledonous crops of the genera: Arachis, Bèta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia.

-51-
Monocotvledonous 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, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.
Monocotvledonous crops of the genera: Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea.
However, the use of the active compound combinations according to the invention is in no way restricted to these genera, but also extends in the same manner to other plants.
The active compound combinations to be used in accordance with the invention can be employed not only in conventional cultivation methods (suitably spaced row crops), in plantation crops (for example grapevines, fruit, citrus) and in industrial plants and railtracks, on paths and squares, but also for stubble treatment and in the minimum tillage method. They are furthermore suitable as dessicants (haulm killing in, for example, potatoes) or as defoliants (for example in cotton). They are furthermore suitable for use on non-crop areas. Other fields of application are nurseries, forests, grassland and the production of ornamentals.
The active compound combinations 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 materials impregnated with active compound, and microencapsulations in polymeric materials.
These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is, liquid solvents and/or solid carriers,

-52-
optionally with the use of surfactants, that is, emulsifiers and/or dispersants and/or foam formers.
In the case of the use of water as an extender, organic solvents can, for example, also be used as cosolvents. The following are essentially suitable as liquid solvents: aromatics such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffms, for example mineral oil fractions, mineral and vegetable oils, alcohols such as butanol or glycol and 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, or else water.
Solid carriers which are suitable are:
for example ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic materials such as highly-dispersed silica, alumina and silicates; suitable solid carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, or else 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 example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates, or else protein hydrolysates; suitable dispersants are: for example lignosulphite waste liquors and methylcellulose.
Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins and

-53-
synthetic phospholipids can be used in the formulations. Other possible additives are mineral and vegetable oils.
It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and tracé 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 compounds, preferably between 0.5 and 90%.
The active compound combinations according to the invention are generally applied in the form of ready mixes. However, the active compounds contained in the active compound combinations may also be applied in the form of individual formulations which are mixed upon use, that is, in the form of tank mixes.
The new active compound combinations, as such or in their formulations, may furthermore also be used as a mixture with other known herbicides, again with ready mixes or tank mixes being possible. A mixture with other known active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellants, growth substances, plant nutrients and soil conditioners is also possible. It may furthermore be advantageous for specific applications, in particular for the post-emergence method, to incorporate into the formulations plant-tolerated mineral or vegetable oils (for example the commercial product "Rako Binol") or ammonium salts such as, for example, ammonium sulphate or ammonium thiocyanate, as further additives.
The new active compound combinations can be used as such, in the form of their formulations or the use forms which can be prepared from these formulations by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. Application is effected in the customary manner, for example by pouring, spraying, atomizing, dusting or broadcasting.

-54-
The active compound combinations according to the invention can be applied before and after emergence of the plants, that is to say by the pre- and post-emergence method. They may also be incorporated into the soil prior to sowing.
The good herbicidal action of the new active compound combinations can be seen from the examples which follow. While the individual active compounds show weaknesses with regard to their herbicidal action, the combinations all show a very good herbicidal action which exceeds a simple sum of actions.
A synergistic effect in herbicides is always present when the herbicidal action of the active compound combination exceeds the action of the active compounds when applied individually.
The expected action for a given combination of two herbicides can be calculated as follows (cf. COLBY, S.R.: "Calculating synergistic and antagonistic responses of herbicide combinations", Weeds 15, pages 20-22, 1967):
If
X = % damage by herbicide A (active compound of the formula I) at an application rate of p kg/ha
and
Y = % damage by herbicide B (active compound of the formula U) at an application rate of q kg/ha
and

-55-
E = the expected damage of herbicides A + B at an application rate of p + q kg/ha,
then
E= X + Y-(X*Y/100).
If the actual damage exceeds the calculated value, the combination has a superadditive effect, that is to say a synergistic effect.
The theoretically expected activity for a given combination of three herbicides can likewise be foutid in the literature tnentioned above.

-56-
Use Examples; Example A
Post-emergence test/greenhouse
Test plants are grown under control conditions (temperature and light). Once the plants have reached a height of 5 to 15 cm, the test compound or the combination of test compounds is applied by spraying such that the particular amounts of active compound desired are applied per unit area. The concentration of the spray liquor is chosen so that the particular amounts of active compound desired are applied in 500 litres of water/ha.
Following the spray application, the plant containers are kept in the greenhouse under constant light and temperature conditions.
After three weeks, the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control.
The fïgures denote:
O % = no effect (like untreated control) 100 % = total destruction
Active compounds, application rates, test plants and results are shown in the tables below.
Here, a.i. denotes active ingrediënt (active compound).



Table A-l
Table A-2

-57-



Table A-l-1
Table A-l-2
* Values calculated according to Colby

-58-

-59-
Table A-l-3

Application rate g of ai/ha Vioïa arvensis
observed Viola
arvensis
calculated*
1-2 8 50
4 40
fl ucarbazone-sodium 15 30
1-2 + 8+15 80 65
fl ucarbazone-sodium 4+15 80 58
Table A-l-4

Application rate g of ai/ha Setaria viridis
observed Setaria viridis
calculated*
1-2 8 90
4 80
amidosulfuron 15 30
8 0
1-2 + 8+15 98 93
amidosulfuron 4+15 98 86
8+8 98 90
4+8 95 80
* Values calculated according to Colby



Table A-l-5
Table A-l-6
* Values calculated according to Colby

-60-



Table A-l-7
Table A-l-8
* Values calculated according to Colby

-61-



Table A-l-9
Table A-l-10
* Values calculated according to Colby

-62-

-63-
TableA-1-11

Applicati on rate g of ai/ha Cyperus
esculentus observed Cyperus esculentus
calculated*
1-2 15 70
dicamba 125 0
30 0
1-2 + 15+125 95 70
dicamba 15+30 90 70
Table A-l-12

Application rate g of ai/ha Veronica persicaria
observed Veronica persicaria
calculated*
1-2 15 40
8 0
dicamba 60 40
1-2 + 15+60 80 64
dicamba 8+60 60 40
* Values calculated according to Colby

-64-
TableA-1-13

Application rate g of ai/ha Alopecurus myosuroides
observed Alopecurus myosuroides calculated*
1-2 15 80
diflufenican 125 70
60 50
30 50
1-2 + 15+125 100 94
diflufenican 15+60 95 90
15+30 95 90
TabIeA-1-14

Application rate g of ai/ha Avena fatua
observed Avena fatua
calculated*
1-2 15 70
8 70
4 70
diflufenican 125 50
1-2 + 15+125 95 85
diflufenican 8+125 95 85
4+125 95 85
* Values calculated according to Colby

-65-
TableA-MS

f i Application rate g of ai/ha Bromus secalinus
observed Bromus
secalinus
calcuïated*
1-2 4 80
diflufenican 30 10
1-2 + diflufenican 4+30 95 82
TableA-1-16

Application rate g of ai/ha Alopecurus myosuroides
observed Alopecurus myosuroides
calcuïated*
1-2 15 80
8 80
dichlorprop-P 250 20
f 125 0
60 0
1-2 + 15+250 98 84
dichlorprop-P 8+250 98 84
15+125 98 80
8+125 95 80
15+60 90 80
8+60 90 80
* Values calcuïated according to Colby

-66-
TableA-1-17

Application rate g of ai/ha Avena
fatua
observed Avena fatua
calculated*
1-2 15 70
8 70
4 70
dichlorprop-P 250 10
125 0
1-2 + 15+250 98 73
dichlorprop-P 8+250 98 73
4+250 95 73
15+125 95 70
8+125 95 70
- 4+125
95
70

* Values calculated according to Colby

-67-
TableA-1-18

Application rate g of ai/ha Matricaria inodora
observed Matricaria inodora
calculated*
1-2 15 4 95 70
dichlorprop-P 250 125 60 0 0 0
1-2 + dichlorprop-P 15+250
4+250 15+125 4+125 15+60 4+60 100 95 100 90 100 90 95 70 95 70 95 70
Table A-l-19

Application Bromus Bromus
rate seealinus seealinus
g of ai/ha observed calculated*
1-2 8 80
4 70
2 70
bifenox 250 10
125 0
60 0
1-2 + 8+250 95 82
bifenox 4+250 90 73
2+250 90 73
8+125 95 80
4+125 90 70
2+125 90 70
8+60 90 80
4+60 90 70
2+60 90 70
* Values calculated according to Colby

-68-
Table A-1-2Q

Application rate g of ai/ha Avena fatua
observed Avena fatua
calculated*
1-2 4 80
2 70
bifenox 250 10
125 10
60 10
1-2 + 4+250 90 82
bifenox 2+250 90 73
4+125 90 82
2+125 90 73
4+60 90 82
2+60 90 73
Table A-l-21

Application rate g of ai/ha Xanthium strumarium
observed Xanthium strumarium
calculated*
1-2 8 70
bifenox 250 70
125 60
60 60
1-2 + 8+250 98 91
bifenox 8+125 98 88
8+60 98 88
* Values calculated according to Colby

-69-
Table A-l-22

Application ra te g of ai/ha Alopecurus myosuroides
observed Alopecurus myosuroides
calculated*
1-2 4 80
2 70
2,4-D ester 250 0
125 0
1-2 + 4+250 90 80
2,4-D ester 2+250 90 70
4+125 90 80
2+125 90 70
* Values calculated according to Colby

-70-
Table A-l-23

Application Bromus Bromus
rate secalinus secalinus
g of ai/ha observed calculated*
1-2 8 80
4 70
2 70
2,4-D ester 250 0
125 0
60 0
1-2 + 8+250 98 80
2,4-D ester 4+250 90 70
2+250 80 70
8+125 98 80
4+125 80 70
2+125 80 70
8+60 90 80
4+60 80 70
2+60 80 70
Table A-l-24

Application rate g of ai/ha Cassia tora
observed Cassia
tora
calculated*
1-2 2 20
2,4-D ester 250 125 60 50 50 50
1-2 + 2,4-D ester 2+250 2+125 2+60 80 70
70 60 60 60
* Values calculated according to Colby

-71-
Table A-l-25

Application rate g of ai/ha Bromus secalinus
observed Bromus secalinus
calculated*
1-2 2 90
fenoxaprop-(P)-ethyl 30 0
15 0
8 0
1-2 + 2+30 95 90
fenoxaprop-(P)-ethyl 2+15 95 90
2+8 95 90
Table A-l-26

Application rate g of ai/ha Ipomoea hederacea
observed Ipomoea hederacea
calculated*
1-2 4 80
2 80
fenoxaprop-(P)-ethyl 30 0
1-2 + 4+30 90 80
fenoxaprop-(P)-ethyI 2+30 90 80
* Values calculated according to Colby

-72-
TableA-1-27

Application rate g of ai/ha Veronica persicaria
observed Veronica persicaria
calculated*
1-2 8 40
fenoxaprop-(P)-ethyl 30 0
15 0
8 0
1-2 + 8+30 98 40
fenoxaprop-(P)-ethyl 8+15 70 40
8+8 70 40
Table A-l-28

Application rate g of ai/ha Bromus secalinus
observed Bromus secalinus
calculated*
1-2 8 80
4 80
flupyrsulfuron 4 0
2 0
1-2 + 8+4 95 80
flupyrsulfuron 4+4 90 80
8+2 95 80
4+2 90 80
* Values calculated according to Colby

-73-
Table A-l-29

Application rate g of ai/ha Digitaria sanguinalis
observed Digitaria sanguinalis
calculated*
1-2 8 80
4 60
2 30
flupyrsulfuron 4 20
1-2 + 8+4 99 84
flupyrsulfuron 4+4 80 68
2+4 80 44
Table A-l-30

Application rate g of ai/ha Polygonum convolvolus
observed Polygonum convolvolus
calculated*
1-2 4 70
2 70
flupyrsulfuron 4 80
2 70
1-2 + 4+4 98 94
flupyrsulfuron 2+4 98 94
4+2 98 91
2+2 95 91
* Values calculated according to Colby

-74-
TableA-1-31

Application rate S of ai/ha Bromus secalinus
observed Bromus secalinus
calculated*
1-2 8 80
4 80
2 80
fluroxypyr 125 0
60 0
1-2 + 8+125 100 80
fluroxypyr 4+125 90 80
2+125 90 80
8+60 98 80
4+60 90 80
2+60 90 80
Table A-l-32

Application rate g of ai/ha Matricaria inodora
observed Matricaria inodora
calculated*
1-2 2 50
fluroxypyr 125 70
60 30
1-2 + 2+125 100 85
fluroxypyr 2+60 95 65
* Values calculated according to Colby

-75-
Table A-l-33

Application rate g of ai/ha Veronica persicaria
observed Veronica persicaria
calculated*
1-2 4 30
2 0
fluroxypyr 125 90
1-2 + 4+125 98 93
fluroxypyr 2+125 98 90
Table A-l-34

Application rate g of ai/ha Bromus secalinus
observed Bromus secalinus
calculated*
1-2 8 80
4 80
glyphosate 250 80
125 20
1-2 + 8+250 100 96
glyphosate 4+250 100 96
8+125 98 84
4+125 98 84
* Values calculated according to Colby

-76-
TableA-1-35

Application rate g of ai/ha Eriochloa villosa
observed Eriochloa villosa
calculated*
1-2 8 70
4 40
2 20
glyphosate 250 70
1-2 + 8+250 100 91
glyphosate 4+250 100 82
2+250 95 76
Table A-l-36

Application rate g of ai/ha Veronica persicaria
observed Veronica persicaria
calculated*
1-2 4 30
2 0
glyphosate 250 50
1-2 + 4+250 100 65
glyphosate 2+250 100 50
* Values calculated according to Colby





-77-
Table A-l-37

Application rate g of ai/ha Bromus secalinus
observed Bromus secalinus
calculated*
1-2 8 80
4 80
imazamox 8 60
1-2 + 8+8 100 92
imazamox 4+8 100 92
Table A-l-38

Application rate g of ai/ha Matricaria inodora
observed Matricaria inodora
calculated*
1-2 2 50
imazamox 15 50
8 30 75
1-2 + 2+15 100

imazamox 2+8 100 65
* Values calculated according to Colby

-78-
Table A-l-39

Application rate g of ai/ha Digitaria sanguinalis
observed Digitaria sanguinalis
calculated*
1-2 8 80
4 60
2 30
imazamox 8 30
1-2 + 8+8 98 86
imazamox 4+8 98 72
2+8 80 51
TableA-1-40

Application rate g of ai/ha Bromus secalinus
observed Bromus secalinus
calculated*
1-2 8 80
4 80
iodosulfuron 4 0
2 0
1-2 + 8+4 100 80
iodosulfuron 4+4 100 80
8+2 98 80
4+2 98 80
* Values calculated according to Colby

-79-
Tabïe A-l-41

Application rate g of ai/ha Veronica persicaria observed Veronica persicaria
calculated*
1-2 4 30
2 0
iodosulfuron 2 90
1-2 + 4+2 100 93
iodosulfuron 2+2 100 90
Table A-l-42

Application rate g of ai/ha Setaria
viridis observed Setaria
viridis calculated*
1-2 4 90
iodosulfuron 4 0
2 0
1-2 + 4+4 98 90
iodosulfuron 4+2 95 90
Values calculated according to Colby

-80-
TableA-1-43

Application rate g of ai/ha Bromus secalinus
observed Bromus secalinus
calculated*
1-2 8 80
4 80
isoxaflutole 4 0
2 0
1-2 + 8+4 100 80
isoxaflutole 4+4 98 80
8+2 100 80
4+2 98 80
Table A-l-44

Application rate g of ai/ha Alopecurus myosuroides observed Alopecurus
myosuroides calculated*
1-2 8 90
isoxaflutole 4 0
2 0
1-2 + 8+4 98 90
isoxaflutole 8+2 98 90
* Values calculated according to Colby

-81-
TableA-1-45

Application rate g of ai/ha Matricaria inodora observed Matricaria inodora
calculated*
1-2 2 50
isoxaflutole 4 70
1-2 + 2+4 100 85
isoxaflutole
Table A-l-46

Application rate g of ai/ha Matricaria inodora observed Matricaria inodora calculated*
1-2 2 50
mecoprop-P 250 0
125 0
1-2 + 2+250 100 50
mecoprop-P 2+125 98 50
* Values calculated according to Colby

-82-
Table A-l-47

Application rate g of ai/ha GaJium aparine
observed GaJium aparine calculated*
1-2 4 80
mecoprop-P 250 40
125 20
1-2 + 4+250 98 88
mecoprop-P 4+125 95 84
Table A-l-48

Application rate g of ai/ha Digitaria sanguinalis observed Digitaria sanguinalis
calculated*
1-2 8 80
mecoprop-P 250 70
125 40
1-2 + 8+250 100 94
mecoprop-P 8+125 98 88
* Values calculated according to Colby

-83-
Table A-l-49

1 Appllication rate g of ai/ha 'Bromus
secalinus observed Bromus
secalinus calculated*
1-2 8 80
4 80
2 80
mesotrione 30 0
15 0
1-2 + 8+30 100 80
mesotrione 4+30 98 80
2+30 95 80
8+15 99 80
4+15 98 80
2+15 95 80
Table A-l-50

1 Appllication rate g of ai/ha Polygonum convolvolus observed Polygonum convolvolus
calculated*
1-2 4 70
2 70
mesotrione 15 50
1-2 + 4+15 98 85
mesotrione 2+15 95 85
Values calculated according to Colby

-84-
Table A-l-51

Application rate g of ai/ha Alopecurus myosuroides observed Alopecurus myosuroides calculated*
1-2 8 90
2 70
mesotrione 30 0
15 0
1-2 + 8+30 95 90
mesotrione 2+30 95 70
8+15 95 90
2+15 80 70
Table A-l-52

Application rate g of ai/ha Cassia tora
observed Cassia tora
calculated*
1-2 8 0
florasulam 4 0
1-2 + 8+4 98 0
florasulam
* Values calculated according to Colby

-85-
TableA-1-53

Application rate g of ai/ha Bromus secalinus
observed Bromus secalinus
calculated*
1-2 2 70
florasulam 4 30
2 30
1-2 + 244 95 79
florasulam 2+2 95 79
TableA-1-54

Application rate g of ai/ha Veronica persicaria
observed Veronica persicaria
calculated*
1-2 S 0
florasulam 4 70
1-2 + 8+4 98 70
florasulam
* Values calculated according to Colby

-86-
Table A-l-55

Application rate g of ai/ha Ipomoea hederacea
observed Ipomoea hederacea
calculated*
1-2 8 80
foramsulfuron 15 80
1-2 + foramsulfuron 8+15 100 96
Table A-l-56

Application rate Cyperus esculentus Cyperus esculentus
g of ai/ha observed calculated*
1-2 4 20
foramsulfuron 8 80
1-2 + 4+8 90 84
foramsulfuron
* Values calculated according to Colby

-87-
Table A-l-57

Application rate g of ai/ha Eriochloa villosa
observed Eriofhloa villosa
calculated*
1-2 4 40
2 0
foramsulfuron 15 60
1-2 + 4+15 80 76
foramsulfuron 2+15 70 60
Table A-l-58

Application rate g of ai/ha Bromus secalinus
observed Bromus secalinus
calculated*
1-2 2 70
flurtamone 60 30
1-2 +
flurtamone
2+60 95 79
* Values calculated according to Colby

-88-
TableA-1-59

Appllicatio n rate g of ai/ha Matricaria inodora
observed Matricaria inodora
calculated*
1-2 2 80
flurtamone 30 30
1-2 + flurtamone 2+30 95 86
Table A-l-60

Application rate g of ai/ha Cyperus esculentus
observed Cyperus esculentus
calculated*
1-2 4 20
2 0
mesosulfuron 15 70
8 70
1-2 + 4+15 90 76
mesosulfuron 2+15 90 70
4+8 90 76
2+8 90 70
* Values calculated according to Colby

-89-
Table A-l-61

Application rate g of ai/ha Bromus secalinus
observed Bromus secalinus
calculated*
1-2 2 70
mesosulfuron 8 0
1-2 + 2+8 90 70
mesosulfuron
Table A-l-62

Application rate g of ai/ha Avena fatua
observed Avena
fatua
calculated*
1-2 8 90
4 90
2 50
metosulam 8 0
1-2 + 8+8 98 90
metosulam 4+8 95 90
2+8 90 50
* Values calculated according to Colby

-90-
Table A-l-63

Application rate g of ai/ha Veronica persicaria
observed Veronica persicaria
calcuïated*
1-2 8 0
4 0
metosulam 4 80
1-2 + 8+4 100 80
Metosulam 4+4 100 80
Table A-l-64

Application rate g of ai/ha Digitaria sanguinalis
observed Digitaria
sanguinalis calcuïated*
1-2 2 70
metosulam 8 30
1-2 + 2+8 90 79
metosulam
* Values calcuïated according to Colby

-91-
Table A-l-65

Application rate g of ai/ha Matricaria inodora
observed Matricaria inodora
calculated*
1-2 2 80
metribuzin 30 0
1-2 + 2+30 95 80
metribuzin
Table A-l-66

Application rate g of ai/ha Xanthium strumarium
observed Xanthium strumarium
calculated*
1-2 4 90
metribuzin 30 40
1-2 +
metribuzin 4+30 98 94
* Values calculated according to Colby

-92-
Table A-l-67

Application rate g of ai/ha Lolium perenne
observed Lolium perenne
calculated*
1-2 2 70
metsulfuron 2 70
1-2 + 2+2 100 91
metsulfuron
Table A-l-68

Application rate g of ai/ha Bromus secalinus
observed Bromus
secalinus
calculated*
1-2 2 80
metsulfuron 4 0
2 0
1-2 + 2+4 95 80
metsulfuron 2+2 95 80
* Values calculated according to Colby

-93-
Table A-l-69

Application rate g of ai/ha Cyperus esculentus
observed Cyperus esculentus
calculated*
1-2 8 80
4 60
2 40
metsulfuron 4 30
1-2 + 8+4 95 86
metsulfuron 4+4 90 72
2+4 80 58
Table A-l-70

Application rate g of ai/ha Eriochloa villosa
observed Eriochloa villosa
calculated*
1-2 2 0
nicosulfuron 30 90
1-2 + nicosulfuron 2+30 95 90
* Values calculated according to Colby

-94-
TableA-1-71

Application rate g of ai/ha Eriochloa villosa
observed Eriochloa villosa
calculated*
1-2 8 60
4 30
2 0
picolinafen 30 80
15 30
1-2 + 8+30 98 92
picolinafen 4+30 95 86
2+30 90 80
8+15 95 72
4+15 90 51
2+15 90 30
Table A-l-72

Application rate g of ai/ha Lolium perenne
observed Lolium perenne
calculated*
1-2 2 70
picolinafen 30 20
15 0
1-2 + 2+30 95 76
picolinafen 2+15 95 70
* Values calculated according to Colby

-95-
Table A-l-73

Application rate g of ai/ha Cassia tora
observed Cassia tora
calculated*
1-2 8 0
4 0
picolinafen 30 70
1-2 + 8+30 100 70
picolinafen 4+30 80 70
Table A-l-74

Application rate g of ai/ha Veronica persicaria
observed Veronica persicaria
calculated*
1-2 4 0
propoxycarbazone-sodium 60 40
1-2 + 4+60 100 40
propoxycarbazone-sodium
* Values calculated according to Colby

-96-
TableA-1-75

Application Cassia Cassia
rate tora tora
g of ai/ha observed calculated*
1-2 8 0 -
4 0
propoxycarbazone-sodium 30 30
1-2 + propoxycarbazone-sodium 8+30 4+30 80 70 30 30
TabIeA-1-76

Application Polygonum Polygonum
rate convolvolus convolvolus
g of ai/ha observed calculated*
1-2 4 80
2 70
propoxycarbazone-sodium 60 0
30 0
1-2 + 4+60 90 80
propoxycarbazone-sodium 2+60 90 70
4+30 90 80
2+30 90 70
* Values calculated according to Colby

-97-
TableA-1-77

1 Apptöcation Cassia Casssia
rate tora tora
g of ai/ha observe calculated*
d
1-2 8 0
rimsulfuron 8 4 80 60
1-2 + 8+8 100 80
rimsulfuron 8+4 80 60
Table A-l-78

Application rate g of ai/ha Abutilon theophrasti
observed Abutilon theophrasti
calculated*
1-2 4 70
2 60
rimsulfuron 4 70
1-2 + 4+4 95 91
rimsulfuron 2+4 95 88
* Values calcul^ed according to Colby

-98-
Table A-l-79

Application rate g of ai/ha Avena fatua
observed Avena fatua
calculated*
1-2 2 70
rimsulfuron 8 70
4 70
J-2 + 2+8 95 91
rimsulfuron 244 95 91
Table A-l-80

Application rate g of ai/ha Bromus secalinus
observed Bromus
secalinus
calculated*
1-2 8 80
4 70
sulcotrione 120 30
60 0
1-2 + 8+120 98 86
sulcotrione 4+120 90 79
8+60 98 80
4+60 90 70
* Values calculated according to Colby

-99-
Table A-l-81

Application rate g of ai/ha Bromus secalinus
observed Bromus
secalinus
calculated*
1-2 8 80
4 70
2 70
terbuthylazine 500 50
1-2 + 8+500 100 90
terbuthylazine 4+500 100 85
2+500 100 85
Table A-l-82

Application rate g of ai/ha Setaria viridis
observed Setaria
viridis
calculated*
1-2 8 95
thifensulfuron-methyl 15 0
8
1-2 + 8+15 100 95
thifensulfuron-methyl 8+8 100 95
* Values calculated according to Colby

-100-
Table A-l-83

Application rate g of ai/ha Bromus secalinus
observed Bromus secalinus
calculated*
1-2 8 80
4 70
thifensulfuron-methyl 15 0
8 0
1-2 + 8+15 98 80
th i f en s ui furon-methyl 4+15 98 70
8+8 98 80
4+8 98 70
Table A-l-84

Application rate g of ai/ha Eriochloa villosa
observed Eriochloa villosa
calculated*
1-2 8 90
thifensulfuron-methyl 15 10
1-2 +
thifensulfuron-methyl 8+15 98 91
* Values calculated according to Colby

-101-
Table A-l-85

Application rate g of ai/ha Bromus secalinus
observed Bromus secalinus
calculated*
1-2 8 80
4 70
2 70
tribenuron-methyl 8 4 0 0
1-2 + 8+8 95 80
tribenuron-methyl 4+8 2+8 95 90 70 70
8+4 95 80
4+4 90 70
2+4 90 70
Table A-l-86

Application rate g of ai/ha Cyperus esculentus
observed Cyperus esculentus
calculated*
1-2 8 70
4 60
2 40
tribenuron-methyl 8 4 0 0
1-2 + 8+8 90 70
tribenuron-methyl 4+8 2+8 70 70 60 40
8+4 80 70
4+4 70 60
2+4 70 40
* Values calculated according to Colby

-102-
Table A-l-87

Application rate g of ai/ha Veronica persicaria
observed Veronica persicaria
calculated*
1-2 8 30
4 30
tribenuron-methyl 4 90
1-2 + 844 98 93
tri ben uron-methyl 4+4 98 93
Table A-l-88

Application rate g of ai/ha Bromus secalinus
observed Bromus secalinus
calculated*
1-2 8 80
4 70
2 70
HWH 4991 60 30
30 20
1-2 + 8+60 100 86
HWH 4991 4+60 100 79
2+60 95 79
8+30 99 84
4+30 99 76
2+30 95 76
* Values calculated according to Colby

-103-
Table A-l-89

Application rate g of ai/ha Veronica persicaria
observed Veronica persicaria
calculated*
1-2 8 30
4 30
2 0
HWH 4991 30 90
1-2 + 8+30 100 93
HWH 4991 4+30 100 93
2+30 100 90
Table A-l-90

Application rate g of ai/ha Lol i um perenne
observed Lolium perenne
calculated*
1-2 2 80
HWH 4991 60 60
30 20
1-2 + 2+60 98 92
HWH 4991 2+30 95 84
Values calculated according to Colby

- 104-
TableA-l-9l

Application rate g of ai/ha Aloperurus myosuroides
observed Aloperurus myosuroides
calculated*
1-2 4 80
2 80
sulfosate 250 30
1-2 + 4+250 95 86
sulfosate 2+250 95 86
Table A-l-92

Application rate g of ai/ha Lolium perenne
observed Lolium perenne
calculated*
1-2 4 70
2 70
sulfosate 250 70
1-2 + 4+250 98 91
sulfosate 2+250 98 91
* Values calculated according to Colby

-105-
Table A-l-93

Application rate g of ai/ha Lolium perenne
observed Lolium perenne
calculated*
1-2 8 90
4 70
2 70
tritosulfuron 30 0
15 0
1-2 + 8+30 98 90
tritosulfuron 4+30 98 70
2+30 90 70
8+15 98 90
4+15 95 70
2+15 95 70
Table A-l-94

Application rate g of ai/ha Setaria viridis
observed Setaria viridis
calculated*
1-2 8 95
4 90
2 90
tritosulfuron 30 0
1-2 + 8+30 99 95
tritosulfuron 4+30 95 90
2+30 95 90
* Values calculated according to Colby

-106-
Table A-1-95

Application rate g of ai/ha Digitaria sanguinalis
observed Digitaria sanguinalis
calculated*
1-2 8 90
tritosulfuron 30 40
15 30
1-2 + 8+30 98 94
tritosulfuron 8+15 98 93
Table A-l-96

Application rate g of ai/ha Lolium perenne
observed Lolium perenne
calculated*
1-2 8 90
4 70
2 70
SLA 5599 60 30
30 0
1-2 + 8+60 99 93
SLA 5599 4+60 98 79
2+60 95 79
8+30 99 90
4+30 98 70
2+30 90 70
* Values calculated according to Colby

-107 -
Table A-l-97

Application rate g of ai/ha Avena fatua
observed Avena fatua
calculated*
1-2 4 90
2 80
SLA 5599 60 0
30 0
1-2 + 4+60 95 90
SLA 5599 2+60 90 80
4+30 95 90
2+30 90 80
Table A-l-98

Application rate g of ai/ha Veronica persicaria
observed Veronica persicaria
calculated*
1-2 8 40
4 0
SLA 5599 30 80
1-2 + 8+30 100 88
SLA 5599 4+30 98 80
* Values calculated according to Colby

-108-
Table A-l-99

Application rate g of ai/ha Bromus secalinus
observed Bromus secalinus
calculated*
1-2 4 90
2 80
pyraflufen -ethyl 4 30
2 30
1-2 + 444 98 93
pyraflufen-ethyl 2+4 98 86
4+2 98 93
2+2 95 86
Table A-l-100

Application rate g of ai/ha Lol i u m perenne
observed Lolium perenne
calculated*
1-2 8 90
4 70
2 70
pyraflufen-ethyl 4 30
2 0
1-2 + 8+4 99 93
pyraflufen-ethyl 4+4 95 79
2+4 95 79
8+2 99 90
4+2 95 70
2+2 90 70
* Values calculated according to Colby

-109-
Table A-l-101

Application rate g of ai/ha Setria viridis
observed Setria viridis
calculated*
1-2 4 90
2 90
pyraflufen ethyl 4 40
2 40
1-2 + 4+4 98 94
pyraflufen ethyl 244 98 94
4+2 98 94
2+2 98 94
Table A-l-102

Application rate g of ai/ha Bromus secalinus
observed Bromus secalinus
calculated*
1-2 S 80
flufenacet 125 40
60 20
30 0
1-2+ 8+125 100 88
flufenacet 8+60 99 84
8+30 99 80
* Values calculated according to Colby

-110-
Table A-l-103

Application rate g of ai/ha Polygonum convolvolus
observed Polygonum convolvolus
calculated*
1-2 8 90
4 80
2 70
flufenacet 125 0
60 0
30 0
1-2+ 8+125 98 90
flufenacet 4+125 90 80
2+125 80 70
8+60 98 90
4+60 90 80
2+60 80 70
8+30 98 90
4+30 90 80
2+30 80 70
* Values calculated according to Colby

-111-
TableA-1-104

Application rate Chenopodium album Chenopodium album
g of ai/ha observed calculated*
1-2 2 70
flufenacet 125 0
60 0
30 0
1-2+ 2+125 95 70
flufenacet 2+60 95 ..70
2+30 90 70
* Values calculated according to Colby

-112-
Patent Claims
1. Composition, comprising an active compound combination comprisihg:
a) a substituted thien-3-yl-suIphonylamino(thio)carbonyItriazolin(ethi)one 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 C1-C4-alkoxy-substituted alkyl having l to 6 carbon atoms, or represents in each case optionally cyano- or halogen-substituted alkenyl or alkynyl having in each case 2 to 6 carbon atoms, or represents in each case optionally cyano-, halogen- or C1-C4-alkyl-substituted cycloalkyl or cycloalkylalkyl having in each case from 3 to 6 carbon atoms in the cycloalkyl group and, if appropriate, l to 4 carbon atoms in the alkyl moiety, represents in each case optionally nitro-, cyano-, halogen-, C1-C4-aIkyl- or C1-C4-alkoxy-substituted aryl or arylalkyl having in each case 6 or 10 carbon atoms in the aryl group and, if appropriate, l to 4 carbon atoms in the alkyl moiety, or represents in each case optionally nitro-, cyano-,

-113-
halogen-, C1-C4-alkyl- or C1-C4alkoxy-substituted heterocyclyl or heterocyclylalkyl having in each case up to 6 carbon atoms and additionally l to 4 nitrogen atoms and/or l or 2 oxygen or sulphur atoms in the heterocyclyl group and, if appropriate, l to 4 carbon atoms in the alkyl moiety,
R2 represents hydrogen, cyano, nitro, hülogen, or represents in each case optionally cyano-, halogen- or C1-C4-aïkoxy-substituted alkyï, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case l 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 hydrogen, hydroxyl, mercapto, amino, cyano, fluorine, chlorine, bromine, iodine, represents optionally fluorine-, chlorine-, bromine-, cyano-, C1-C4-alkoxy-, C1-C4-alkyI-carbonyl- or C1-C4-alkoxy-carbonyl-substituted alkyl having l to 6 carbon atoms, represents in each case optionally fluorine-, chlorine- and/or bromine-substitvrted alkenyl or alkvnvl having in each case 2 to 6 carbon atoms, represents in each case optionally fluorine-, chlorine-, cyano-,C1-C4-aïkoxy- or C1-C4-alkoxy-carbonyl-substituted alkoxy, alkylthio, alkyl-amino or alkyl carbon yl amino having in each case l 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, or represents dialkyl-amino having in each case l to 4 carbon atoms in the alkyl groups, or represents in each case optionally methyl- and/or ethyl-substituted aziridino, pyrrolidino, piperidino or morpholino, or represents in each case optionally fluorine-, chlorine-, bromine-, cyano- and/or C1-C4-alkyl-substituted cycloalkyl, cycloalkenyl, cycloalkyloxy, cycloalkyl-

-114-
thio, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy, cycloalkyl-alkylthio or cycloalkylalkylamino having in each case 3 to 6' carbon atoms in the cycloalkyl or cycloalkenyl group and, if appropriate, l 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, arylalkylthio, arylamino or arylalkylamino having in each case 6 or 10 carbon atoms in the aryl group and, if appropriate, l to 4 carbon atoms in the alkyl moiety,
R4 represents hydrogen, hydroxyl, amino, cyano, or represents C2-C10-alkylideneamino, or represents optionally fluorine-, chlorine-, bromine-, cyano-, C1-C4-alkoxy-, C1-C4-alkyl-carbonyl- or C1-C4-alkoxy-carbonyl-substituted alkyl having l to 6 carbon atoms, or represents in each case optionally fluorine-, chlorine- and/or bromine-substituted alkenyl or alkynyl having in each case 2 to 6 carbon atoms, or represents in each case optionally fluorine-, chlorine-, bromine-, cyano-, C1-C4-alkoxy- or C1-C4-alkoxy-carbonyl-substituted alkoxy, alkylamino or alkyl-carbonylamino having in each case l to 6 carbon atoms in the alkyl group, or represents alkenyloxy having 3 to 6 carbon atoms, or represents dialkylamino having in each case l to 4 carbon atoms in the alkyl groups, or represents in each case optionally fluorine-, chlorine-, bromine-, cyano- and/orC1-C4-alkyl-substituted cycloalkyl, cycloalkylamino or cycloalkylalkyl having in each case 3 to 6 carbon atoms in the alkyl group and, if appropriate, l to 4 carbon atoms in the alkyl moiety, or represents in each case optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, C1-C4-alkyl-, trifluoro¬methyl- 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, l to 4 carbon atoms in the alkyl moiety, or

-115-
R3 and R4 together represent optionally branched alkanediyl having 3 to 6
carbon atoms,
- and salts of the compounds of the formula CO -("Active compounds of Group l")
and
b) one or more compounds of a second group of herbicides consisting of the active compounds below:
4,5-dihydro-3-methoxy-4-methyl-5-oxo-N-[(2-trifluoromethoxyphenyl)-sulphonyl]-l-H-l,2,4-triazole-l-carboxamide sodium salt (flucarbazone-sodium), 2-chloro-N-(ethoxymethyl)-N-(2-ethyl-6-methylphenyl)acetamide (acetochlor), 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoic acid (sodium salt) (acifluorfen (-sodium)), 2-chIoro-6-nitro-3-phenoxybenzenamine (aclonifen), 2-chloro-N-(methoxymethyI)-N-(2,6-diethylpheny])acetamide (alachlor), methyl 4-hydroxy-6,6-dimethyI-2-oxo-3-[l-[(2-propeny!oxy)imino]butyl]-3-cyclohexene-l-carboxylate (sodium salt) (alloxydim (-sodium)), N-ethyl-N'-isopropyï-6-methylthio-l,3,5-triazine-2,4-diamine (ametryn), 4-amino-N-(l,l-dimethylethyI)-4,5-dihydro-3-(l-methylethyl)-5-oxo-lH-l,2,4-triazoIe-l-carboxamide (amicarbazone), N-(4,6-dimethoxypyrimidin-2-yl)-N'-(N-methyl-N-methylsulphonylsulphamoyl)urea (amidosulfuron), lH-l,2,4-triazole-3-ariiine (amitrole), S-[2-[(4-chlorophenyl)-(l-isopropyl)amino]-2-oxoethyn O,O-dimethyl phosphoro-dithioate (anilofos), O-methyl N-(4-aminophenylsulphonyI)carbamate (asu-lam), 6-chloro-4-ethylamino-2-isopropylamino-l,3,5-triazine (atrazine), 2-[2,4-dichloro-5-(2-propynyloxy)phenyl]-5,6,7,8-tetrahydro-l,2,4-triazolo-[4,3-a]-pyridin-3(2H)-one (azafenidin), N-(4,6-dimethoxypyrimidin-2-yI)-N'-

-116-
[l-methyI-4-(2-methyl-2H-tetrazol-5-yl)-lH-pyrazol-5-ylsulphonyllurea
(azimsulfuron), N-benzyI-2-(4-fluoro-3-trifIuoromethylphenoxy)butanamide (beflubutamid), 4-chIoro-2-oxo-3(2H)-benzothiazoleacetic acid (ethyl ester) (benazolin, (-ethyl)), N-butyl-N-ethyl-2,6-dinitro-4-trifluoromethylbenzen-amine (benfluralin), 2,3-dihydro-3,3-dimethyl-5-benzofuranylethane-sulphonate (benfuresate), N-(4,6-dimethoxypyrimidin-2-yl)-N'-(2-methoxy-carbonylphenylmethylsulphonyl)urea (bensulfuron-methyl), 3-i-propyMH-2,l,3-benzothiadiazin-4(3H)-one 2,2-dioxide (bentazone), S-[(4-chlorophenyl)methyl] diethylthiocarbamate (benthiocarb, Thiobencarb), methyl 2-[2-[4-(3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-l(2H)-pyrimidinylphenoxymethyIJ-5-ethylphenoxypropanoate (benzfendizone), 3-(2-chloro-4-methylsulphonylbenzoyl)-4-phenylthiobicyclo-[3.2.1]-oct-3-ene-2-one (benzobicyclon), 2-[[4-(2,4-dichloro-3-methylbenzoyl)-l,3-dimethyl-lH-pyrazol-5-yl]oxy]-l-(4-methylphenyl)ethanone (benzofenap), methyl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate (bifenox), 2,6-bis-(4,6-dimeth-oxypyrimidin-2-yl-oxy)benzoic acid sodium salt (bispyribac-sodium), 5-bromo-6-methyI-3-(l-methylpropyl)-2,4(lH,3H)-pyrimidinedione (bromacil), 2-bromo-3,3-dimethyl-N-(l-methyl-l-phenyIethyl)butanamide (bromobutide), 3,5-dibromo-4-hydroxybenzaldehyde O-(2,4-dinitrophenyI) oxime (bromo-fenoxim), 3,5-dibromo-4-hydroxybenzonitrile (bromoxynil), N-butoxy-methyl-2-chloro-N-(2,6-diethylphenyl)acetamide (butachlor), l,l-dimethyl-2-oxo-2-(2-propenyloxy)]ethyl 2-chloro-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-l(2H)-pyrimidinyl)benzoate (butafenacil), 4-(l-t-butyl)-N-(s-butyl)-2,6-dinitroaniline (butralin), 2-(l-ethoximinopropyl)-3-hydroxy-5-[2,4,6-trimethyl-3-(l-oxobutyl)phenyl]-2-cyclohexene-l-one (butroxydim), S-ethyl bis-(2-methylpropyl)thiocarbamate (butylate), N,N-diethyl-3-(2J4,6-trimethylphenylsulphonyl)-lH-l,2,4-triazole-l-carboxamide (cafenstrole), (R)-N-ethyl-2-[(phenylaminocarbonyl)oxy]propanamide (carbetamide), 2-(4-chloro-2-fluoro-5-(2-chloro-2-ethoxycarbonylethyl)phenyl)-4-difluoromethyl-5-methyl-2,4-dihydro-SH-l,2,4-triazoI-3-one (carfentrazone-ethyl), 2,4-dichloro-l-(3-methoxy-4-nitrophenoxy)benzene (chlormethoxyfen), 5-amino-

-117-
4-chloro-2-phenyI-3(2H)-pyridazinone (chloridazon), N-(4-chloro-6-
methoxypyrimidin-2-yl)-N'-(2-ethoxycarbonylphenylsulphonyl)urea
(chlorimuron-ethyl), l,3,5-trichloro-2-(4-nitrophenoxy)benzehe
(chlomitrofen), N'-(3-chloro-4-methylphenyl)-N,N-dimethylurea. (chlorotol-
uron), N-(4-methoxy-6-methyI-l,3I5-triazin-2-yl)-N'-(2-chlorophenyl-
sulphonyl)urea (chlorsulfuron), ethyl 2-chloro-3-[2-chloro-5-(l,3,4,5,6,7-
hexahydro-13-dioxo-2H-isomdol-2-yl)phenyl]-2-propanoate (cinidon-ethyl),
exo-l-methyI-4-isopropyl-2-(2-methylphenyImethoxy)-7-oxabicyclo-[2.2.1]-
heptane (cinmethylin), N-(4,6-dimethoxy-l,3,5-triazin-2-yl)-N'-(2-(2-meth-
oxyethoxy)phenylsulphonyl)urea (cinosulfuron), 2-[l-[2-(4-chlorophen-
oxy)propoxyaminobutyl]-5-(tetrahydro-2H-thiopyran-3-yl)-l,3-cycIo-
hexanedione (clefoxydim), (E,E)-(+)-2-[l-[[(3-chIoro-2-pro-
penyl)oxy]imino]propyl]-3-hydroxy-2-cyclohexen-l-one (clethodim), (R)-(2-
propyinyl) 2-[4-(5-chloro-3-f!uoropyridin-2-yl-oxy)phenoxypropanoate (clo-
dinafop-propargyl), 2-[(2-chlorophenyl)methyl]-4,4-dimethyl-3-isoxazol-
idinone (clomazone), 2-(2,4-dichloro3-methylphenoxy)-N-phenylpropan-
amide (clomeprop), 3,6-dichloropyridin-2-carboxylic acid (clopyralid),
methyl 3-chloro-2-[(5-ethoxy-7-fluoro[l,2,4]triazolo[l,5-c]pyrimidin-2-
ylsulphonyl)amino]benzoate (cloransulam-methyl), N-[(2-
chlorophenyOmethy^-N'-Cl-methyl-l-phenylethyOurea (cumyluron), 2-chloro-4-ethylamino-6-(l-cyano-l-methylethylamino)-l,3ï5-tria2ine (cyan-azine), N-(4,6-dimethoxypyrimidin-2-yl)-N*-(2-cyclopropylcarbonylphenyl-sulphonyl)urea (cyclosulfamuron), 2-(l-ethoximinobutyl)-3-hydroxy-5-(tetra-hydro-2H-thiopyran-3-yl)-2-cyclohexen-l-one (cycloxydim), (R)-butyl 2-[4-(4-cyatio-2-fluorophenoxy)phenoxy]propanoate (cyhalofop-butyl), 2,4-di-chlorophenoxyacetic acid (2,4-D), O-ethyl N-[3-(phenylaminocarbonyl-oxy)phenyl]carbamate (desmedipham), 3,6-dichIoro-2-methoxybenzoic acid (dicamba), 2,6-dichlorobenzonitrile (dichlobenil), (R)-2-(2,4-dichlorophen-oxy)propanoic acid (dichlorprop-P), methyl 2-[4-(2,4-dichIorophenoxy)phen-oxyjpropanoate (diclofop-methyl), N-(2,6-dichIorophenyl)-5-ethoxy-7-fluoro-[l,2I4]-triazolo-[lï5-c]-pyrimidine-2-sulphonamide (diclosulam), 1,2-di-

-118-
methyl-3,5-diphenyl-lH-pyrazoIium methylsulphate (difenzoquat), N-(2,4-di-
fluoropheny])-2-(3-trifluoromethy]phenoxy)pyridine-3-carboxamide (diflu-
fenican), 2-[l-[(3,5-difluorophenyI)aminocarbonylhydrazono]ethyl]pyridine-
3-carboxylic acid (diflufenzopyr), N'-[3-chloro-4-(5-t-butyl-oxo-l,3,4-oxadi-
azol-3(2H)-yl)phenyI]-N,N-dimethylurea (dimefuron), S-(l-methyl-l-
phenylethyl) 1-piperidinecarbothioate (dimepiperate), 2-chloro-N-(2,6-
dimethylphenyI)-N-(2-methoxyethyI)acetamide (dimethachlor), N-( l ,2-di-
methylpropyl)-N'-ethyI-6-methyIthio-l ,3,5-triazine-2,4-diamine (dimetha-
metryn), (S-) 2-chloro-N-(2,4-dimethyl-3-thienyl)-N-(2-methoxy-1 -
methylethyl)acetamide ((S-) (dimethenamid)), 2-amino-4-(l-fluoro-l-
methylethyl)-6-(l-methyl-2-(3,5-dimethylphenoxy)ethylamino)-l,3,5-triazine
(dimexyflam), 6,7"dihydrodipyrido[l,2-a:2',r-c]pyrazinediium dibromide
(diquat-dibromide), S,S-dimethyl 2-difluoromethyl-4-isobutyl-6-trifluorome-
thylpyridine-3,5-dicarbothioate (dithiopyr), N'-(3,4-dichlorophenyl)-N,N-di-
methylurea (diuron), N-(4-methylphenyl)-N'-(l-methyl-l-phenylethyl)urea
(dymron, daimuron), S-ethyl dipropylthiocarbamate (EPTC), S-(phenyl-
methyl) N-ethyl-N-(l,2-dimethylpropyI)thiocarbamate (Esprocarb), N-ethyl-
N-(2-methyI-2-propenyl)-2,6-dinitro-4-trifluoromethylbenzeneamine (ethal-
fluralin), methyl 2-[[[[(4-ethoxy-6-methylamino-l,3,5-triazin-2-
yl)amino]carbonyl]amino]sulphonyl]benzoate (ethametsulfuron-methyl), 2-ethoxy-2,3-dihydro-3,3-dimethyl-5-benzofuranylmethanesuIphonate (etho-fumesate), (S)-(2-ethoxy-l-methyl-2-oxoethyl) 2-chloro-5-(2-chloro-4-tri-fluoromethylphenoxy)benzoate (ethoxyfen), N-(4,6-dimethoxypyrimidin-2-y])-N'-(2-ethoxyphenoxysu!phonyl)urea (ethoxysulfuron), N-(2,3-di-chlorophenyl)-4-ethoxymethoxybenzamide (etobenzanide), (R)-ethyl 2-[4-(6-chlorobenzoxazol-2-yloxy)phenoxy]propanoate (Fenoxaprop-(P)-ethyl), 4-(2-chlorophenyO-N-cyclohexyl-N-ethyl^^-dihydro-S-oxo-lH-tetrazole-l-carboxamide (fentrazamide), isopropyl N-benzoyl-N-(3-chloro-4-fluorophenyl)-D-alaninate (flamprop-M-isopropyl), methyl N-benzoyl-N-(3-chloro-4-f]uorophenyl)-D-aIaninate (flamprop-M-methyl), N-[[(4,6-dimeth-oxy-2-pyrimidinyl)amino]carbonyl]-3-trifluoromethyl-2-pyridinesuIphon-

-119-
amide (flazasulfuron), N-(2,6-difluorophenyl)-8-fluoro-5-methoxy-[ 1,2,4]-
triazolo-[l,5-c]-pyrimidine-2-sulphonamide (florasulam), (R)-butyl 2-[4-(5-
trifluoromethylpyridin-2-yloxy)phenoxy]propanoate (fluazifop-P-butyl),
isopropyl 5-(4-bromo-l-methyl-5-trifluoromethyl-lH-pyrazol-3-yl)-2-chloro-
4-fluorobenzoate (fluazolate), N-(4-fluorophenyl)-N-isopropyl-2-(5-trifluoro-
methyl-l,3,4-thiadiazol-2-yl-oxy)acetamide (flufenacet), ethyl [2-chloro-4-
fluoro-5-(5-methyl-6-oxo-4-trifluoromethyl-l(6H)-pyridazinyl)phenoxy]-
acetate (flufenpyr), N-(2,6-difluorophenyl)-5-methyl-l,2,4-triazolo[l,5-a]-
pyrimidine-2-suIphonamide (flumetsulam), pentyl [2-chloro-4-fluoro-5-
(l,3,4,5,6J-hexahydro-l,3-dioxo-2H-isoindol-2-yl)phenoxy]acetate (flumi-
clorac-pentyl), 2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-l,4-benzox-
azin-6-yl]-4,5,6,7-tetrahydro-!H-isoindole-l,3-dione (flumioxazin), 2-[4-
chIoro-2-fluoro-5-[(l-methyl-2-propynyl)oxy]phenyl]-4,5,6,7-tetrahydro-lH-
isoindole-l,3(2H)-dione (flumipropyn), N,N-dimethyl-N'-(3-
trifluoromethylphenyl)urea (fluometuron), 3-chloro-4-chloromethyl-l-(3-
trifluoromethylphenyl)-2-pyrrolidinone (fluorochloridone), ethoxycarbonyl-
methyl 5-(2-chloro-4-trifiuoromethylphenoxy)-2-nitrobenzoate (fluoroglyco-
fen-ethyl), l-(4-chloro-3-(2,2,3,3,3-pentafluoropropoxymethyl)phenyl)-5-
phenyl-lH-l,2,4-triazol-3-carboxamide (flupoxam), l-isopropyl-2-chloro-5-
(3,6-dihydro-3-methyI-2,6-dioxo-4-trif]uoromethyl-l(2H)-pyrimidyl)benzoate
(flupropacil), N-(4,6-dimethoxypyrimidin-2-yl)-N'-(3-methoxycarbonyl-6-
trifluoromethylpyridii\-2-ylsulphonyl)urea sodium salt (flupyrsulfuron-
methyl-sodium), 9-hydroxy-9H-fIuorene-9-carboxylic acid (flurenol), (4-
amino-3,5-dichloro-6-fluoropyridin-2-yloxy)acetic acid (2-butoxy-1 -
methylethyl ester, 1-methylheptyl ester) (fluroxypyr, -butoxypropyl, -meptyl),
5-methylamino-2-phenyl-4-(3-trifluoromethylphenyl)-3(2H)-furanone (flurta-
mone), methyl [(2-chloro-4-fluoro-5-(tetrahydro-3-oxo-lH,3H-[l,3,4]-thiadi-
azolo-[3,4-a]-pyridazin-l-yliden)aminophenyl]thioacetate (fluthiacet-methyl),
5-(2-chloro-4-trifluoromethylphenoxy)-N-methylsulphonyl-2-nitrobenzamide
(fomesafen), 2-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carb-
onyI]amino]sulphonyl]-4-formylamino-N,N-dimethyIbenzamide (foramsulf-

-120-
uron), 2-amino^-(hydroxyrnethylphosphinyl)butanoic acid (ammonium salt) (glufosinate (ammonium)), N-phosphonomethylglycine (isopropylammonium salt) (glyphosate, isopropylammonium), methyl 3-chloro-5-[[[[(4,6-dimeth-oxy-2-pyrimidinyl)amino]carbonyl]amino]sulphoTiyl]-l-methyl-lH-pyra2ole-4-carboxyIate (halosul furon-methyl), (R)-2-[4-(3-chloro-5-trifluoro-methylpyridin-2-yloxy)phenoxy]propanoic acid (methyl ester, 2-ethoxyethyI ester, butyl ester) (haloxyfop, -methyl, -P-methyl, -ethoxyethyl, -bütyl), 3-cycIohexyl-6-dimethylamino-l-methyI-l,3,5-triazine-2,4(lH,3H)-dione (hex-azinone), methyl 2-(4,5-dihydro-4-methyl-4-isopropyl-5-oxo-lH-imidazol-2-yl)-4-methylbenzoate (imazamethabenz-methyl), 2-(4,5-dihydro-4-methyl-4-isopropyl-5-oxo-lH-imidazol-2-yl)-5-methoxymethyIpyridine-3-carboxylic acid (imazamox), 2-(4,5-dihydro-4-methyl-4-isopropyl-5-oxo-lH-imidazol-2-yl)-5-methyIpyridine-3-carboxylic acid (imazapic), 2-(4,5-dihydro-4-methyI-4-(isopropyl)-5-oxo-lH-imidazol-2-yl)-3-pyridinecarboxylic acid (imazapyr), 2-(4,5-dihydro-4-methyl-4-isopropyI-5-oxo-lH-imidazol-2-yl)quinoline-3-carboxylic acid (imazaquin), 2-(4,5-dihydro-4-methyl-4-isopropyI-5-oxo-lH-imida2ol-2-yl)-5-ethylpyridine-3-carboxylic acid (imazethapyr), N-(4,6-dimethoxypyrimidin-2-yl)-N'-(2-chloroimidazo[l,2-a]-pyridin-3-ylsulphonyl)urea (imazosulfuron), 2-[2-(3-chlorophenyl)oxiranylmethyl]-2-ethyl-IH-indene-1,3(2H)-dione (indanofan), N-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-N'-(5-iodo-2-methoxycarbonylphenylsulphonyl)urea sodium salt (iodosulfuron-methyl-sodium), 4-hydroxy-3,5-diiodobenzonitrile (ioxynil), N,N-dimethyl-N'-(4-isopropylpheriyl)urea (isoproturon), N-(5-t-butyl-3-isox-azo!yl)-N',N'-dimethylurea(isouron), N-(3-(l-ethyl-l-rhethylpropyl)isoxazol-5-yl)-2,6-dimethoxybenzamide (isoxaben), (4-chloro-2-methylsulph-onylphenyl)-(5-cyclopropyIisoxazol-4-yl)methanone (isoxachlortole), (5-cyclopropylisoxazoI-4-yl)-(2-methylsulphonyl-4-trifluoro-methylphenyl)methanone (isoxaflutole), 2-[(2,3-dihydro-5,8-dimethyl-lJl-di-oxidospiro-[4H-l-benzothiopyran-4,2'-[l,3]-dioxolan-6-yl)carbonyl]-l,3-cyclohexanedione (ketospiradox), (2-ethoxy-l-methyl-2-oxoethyl) 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoate (lactofen), 3-cyclohexyl-

-121-
6,7-dihydro-lH-cyclopenta-pyrimidine-2,4-(3H,5H)-dione (lenacil), N'-(3,4-
dichlorophenyl)-N-methoxy-N-methylurea (linuron), (4-chIorb-2-methylphen-
oxy)acetic acid (MCPA), (R)-2-(4-chloro-2-methylphenoxy)propionic acid
(mecoprop-P), 2-(2-benzothiazolyIoxy)-N-methyl-N-phenylacetamide (me-
fenacet), methyl 2-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carb-
onyl]amino]su]phonyl]-4^[[(methylsulphonyl)amino]methyl]benzoate (meso-
sulfuron), 2-(4-methylsulphonyl-2-nitrobenzoyl)-lï3-cyclohexanedione
(mesotrione), 4-amino-3-methyl-6-phenyl-l,2,4-triazin-5(4H)-one (meta-
mitron), 2-chloro-N-(2,6-dimethyIphenyl)-N-(lH-pyrazol-l-ylmethyl)acet-
amide (metazachlor), N-(2-benzothiazolyl)-N,N'-dimethylurea (methabenz-
thiazuron), Ni-(4-bromophenyI)-N-methoxy-N-methylurea (metobromuron),
(S)-2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2-methoxy-l-
methylethyl)acetamide (metolachlor, S-metolachlor), N-(2,6-dichloro-3-
methylphenyl)-5,7-dimethoxy-l,2,4-triazolo[l,5-a]-pyrimidine-2-sulphon-
amide (metosulam), N'-(3-chloro-4-methoxyphenyl)-N,N-dimethylurea (met-
oxuron), 4-amino-6-tert-butyl-3-methylthio-l,2,4-triazin-5(4H)-one (metri-
buzin), N-(4-methoxy-6-methy]-l,3,5-triazin-2-yl)-N'-(2-methoxycarb-
onylphenylsulphonyl)urea (metsulfuron-methyl), S-ethyl hexahydro-lH-azepine-1-carbothioate (molinate), 2-(2-naphthyIoxy)-N-phenylpropanamide (naproanilide), N,N-diethyI-2-(l-naphthalenyIoxy)propanamide (naprop-amide), N-butyl-N'-(3,4-dichlorophenyl)-N-methylurea (neburon), N-(4,6-di-methoxypyrimidin-2-yl)-N'-(3-dimethylcarbamoylpyridin-2-yIsulphonyl)urea (nicosulfuron), 4-chloro-5-methylamino-2-(3-trifluoromethylphenyl)-3(2H)-pyridazinone (norflurazon), S-(2-chlorobenzyl) N,N-diethylthiocarbamate (orbencarb), 4"dipropylamino-3,5-dinitrobenzenesulphoTiamide (oryzalin), 3-[2,4-dichloro-5-(2-propynyloxy)phenyl]-5-(t-butyl)-l,3,4-oxadiazol-2(3H)-one (oxadiargyl), 3-[2,4-dichloro-5-(l-methylethoxy)phenyl]-5-(t-butyI)-l,3,4-oxadiazol-2(3H)-one (oxadiazon), N-(4,6-dimethylpyrimidin-2-yl)-N'-(2-oxetan-3-yl-oxycarbonylphenylsulphonyl)urea (oxasulfuron), 3-[l-(3,5-di-chloropheny])-l-isopropyl]-2,3-dihydro-6-methyl-5-phenyl-4H-l,3-oxazin-4-one (oxaziclomefone), 2-chloro-l-(3-ethoxy-4-nitrophenoxy)-4-trifluoro-

-122-
methylbenzene (oxyfluorfen), l,l'-dimethyl-4,4'-bipyridinium (paraquat), 1-amino-N-(l-ethylpropyl)-3,4-dimethyl-2,6-dinitrobenzene (pendimethalin), 4-(t-butyl)-N-(l-ethylpropyl)-2,6-dinitrobenzenamine (pendralin), 2-(2,2-di-fluoroethoxy)-N-(5,8-dimethoxy [ l ,2,4]triazolo[ l ,5-c]pyrimidin-2-yl)-6-tri-fluoromethylbenzenesulphonamide (penoxsulam), 3-(4-chloro-5-cyclopentyl-oxy-2-fluorophenyl)-5-(l-methylethylidene)-2,4-oxazolidinedione (pent-oxazone), 2-chloro-N-(2-ethoxyethyl)-N-(2-methyl-l-phenyl-l-propenyl)acet-amide (pethoxamid), O-methyl N-[3-(3-methyIphenylaminocarbonyl-oxy)phenyl]carbamide (phenmedipham), 4-amino-3,5,6-trichloropyridine-2-carboxylic acid (picloram), N-(4-fluorophenyl)-6-(3-trifluoromethylphen-oxy)pyridine-2-carboxamide (picolinafen), S-[2-(2-methyl-l-piperidinyl)-2-oxoethyl] O,O-dipropyl phosphorodithioate (piperophos), 2-chloro-N-(2,6-di-ethyIphenyl)-N-(2-propoxyethyl)acetamide (pretilachlor), N-(4,6-bis-difluoro-methoxypyrimidin-2-yl)-N'-(2-inethoxycarbonylphenylsuIphonyl)urea (primi-
sulfuron-methyl), Uchloro-N-[2-chloro-4-fIuoro-5-[(6S,7aR)-6-fluorotetra-

hydro-l,3-dioxo-lH-pyrrolo[l,2-c]imidazol-2(3H)yI]phenyl]methanesulphon-
amide (profluazol),, 2-[l-[[2-(4-chlorophenoxy)propoxy]imino]butyl]-3-
hydroxy-5-(tetrahydro-2H-thiopyranyl)-2-cyclohexen-l-one (profoxydim),
N,N'-bis-isopropyl-6-rnethylthio-l,3,5-triazine-2,4-diamine (prometryn), 2-
chloro-N-isopropyl-N-phenylacetamid (propachlor), N-(3,4-di-
chlorophenyl)propanamide (propanil), (R)-[2-[[(l-methylethyli-
dene)amino]oxy]ethyl] 2-[4-(6-chloro-2-quinoxalinyIoxy)phenoxy]pro-
panoate (propaquizafop), 2-chloro-N-(2-ethyl-6-methylphenyl)-N-[(l-methylethoxy)methyj]acetamide (propisochlor), methyl 2-[[[(4,5-dihydro-4-methyl-5-oxo-3-propoxy-lH-l,2,4-triazol-l-yI)carbonyl]amino]sulph-

onyljbenzoate sodium
salt (propoxycarbazone-sodium), 3,5-dichloro-N-(l,l-
dimethyl-2-propynyl)benzamide (propyzamide), S-phenylmethyl N,N-di-propylthiocarbamate (orosulfocarb), N-(4-methoxy-6-methyl-l,3,5-triazin-2-yl)-N'-(2-(3,3,3-trifluoropropyl)phenyIsulphonyl) urea (prosulfuron), l-(3-chIoro-4,5,6,7-tetrahyd-opyrazoIo[l,5-a]pyridin-2-yl)-5-(methyl-2-propynyl-amino)-iH-pyrazol-4-carbonitrile (pyraclonil), ethyl [2-chloro5-(4-chloro-5-

-123-
difluoromethoxy-l-methyl-lH-pyrazol-3-yl)'4-fluoro-phenoxy]acetate (pyra-
flufen-ethyl), 4-(2,4-dichlorobenzoyl)-l,3-dimethyl-5-(4-methylphenylsuIph-
onyloxy)pyrazole (pyrazolate), N-(4,6-dimethoxypyrimidin-2-yl)-N'-(4-eth-
oxycarbonyl-l-methylpyrazol-5-ylsulphonyl)urea (pyrazosulfuron-ethyl), 4-"
(2,4-dichlorobenzoyl)-l,3-dimethyl-5-(phenylcarbonylmethoxy)pyrazoIe (pyr-
azoxyfen), diphenylmethanone O-[2,6-bis-(4,6-dimethoxypyrimidin-2-yl-
oxy)benzoyl] oxime (pyribenzoxim), O-[3-(l,l-dimethylethyl)phenyl] (6-
methoxy-2-pyridinyl)methylthiocarbamate (pyributicarb), 6-chloro-3-phenyl-
4-pyridazinol (pyridafol), O-(6-chloro-3-phenylpyridazin-4-yl) S-octyl thio
carbonate (pyridate), 6-chIoro-3-pheny]pyridazin-4-ol (pyridatol), 7-[(4,6-di-
methoxy-2-pyrimidinyl)thio]-3-methyl-l(3H)-isobenzofuranone (pyriftalid),
methyl 2-(4,6-dimethoxypyrimidin-2-yIoxy)benzoate (pyriminobac-methyl),
2-chloro-6-(4,6-dimethoxypyrimidin-2-ylthio)benzoic acid sodium salt (pyri-
thiobac-sodium), 3,7-dichloroquinoline-8-carboxylic acid (quinchlorac), 7-
chloro-3-methylquino!ine-8-carboxylic acid (quinmerac), 2-amino-3-chloro-
1,4-naphthalenedione (quinoclamine), (R)-2-[4-(6-chloro-2-quinoxaIinyl-
oxy)phenoxy]propanoic acid (ethyl ester, tetrahydro-2-furanylmethyl ester)
(quizalofop, -ethyl, -P-ethyl, -P-tefuryl), N-(4,6-dimethoxypyrimidin-2-yI)-
N'-(3-ethylsulphonylpyridin-2-yl-sulphonyl)urea (rimsulfuron), 2-(l-ethox-
iminobutyl)-5-(2-ethylthiopropyl)-3-hydroxy-2-cyclohexen-l-one (sethoxy-
dim), 6-chloro-2,4-bis-ethyIamino-l,3ï5-triazine (simazine), 2-(2-chloro-4-
methylsulphonylbenzoyl)cyclohexane-l,3-dione (sulcotrione), 2-(2,4-di-
chloro-5-methylsulphonylaminophenyl)-4-difluoromethyl-5-methyl-2J4-di-
hydro-3H-l,2,4-triazol-3-one (sulfentrazone), methyl 2-[[[[(4,6-dimethyl-2-
pyrimidinyl)amino]carbonyl]amino]sulphonyl]benzoate (sulfometuron-
methyl), N-phosphonomethylglycine trimethylsulphonium (sulfosate), N-(4,6-dimethoxypyrimidin-2-yl)-N'-(2-ethyIsulphonyl)imidazo[l,2-a]pyridine-3-sulphonamide (sulfosulfuron), N-(5-t-butyl-1,3,4-thiadiazol-2-yI)-N,N' -dimethylurea (tebuthiuron), 2-[l-[(3-chloro-2-propenyl)oxyimino]propyl]-3-hydroxy-5-(tetrahydro-2H-pyran-4-yl)-2-cyclohexen-l-one (tepraloxydim), 6-chloro-4-ethy!amino-2-t-butylamino-l,3,5-triazine (terbuthylazine), 2-t-butyl-

-124-
amino-4-ethylarmno-6-methylthio-l,3,5-triazine (terbutryn), 2-chloro-N-(2,6-
dimemylphenyl)-N-(3-methoxy-2-thienylmethyl)acetamide (thenylchlor), 2-
difluoromethyl-5-(4,5-dihydrothiazol-2-yl)-4-(2-methylpropyl)-6-
trifluoromethylpyridine-3-carboxylate (thiazopyr), N-(4-methoxy-6-methyl-l,3ï5-triazin-2-yl)-N'-(2-methoxycarbonylthien-3-ylsulphonyl)urea (thifen-sulfuron-methyl), S-phenyl methyl bis-s-butylcarbamothioate (tiocarbazil), 2-(ethoximinopropyl)-3-hydroxy-5-(2,4,6-trimethyIphenyI)-2-cyclohexen-l-one (tralkoxydim), S-(2,3,3-trichIoro-2-propenyI) diisopropylcarbamothioate (triallate), N-(4-methoxy-6-methyl-l,3,5-triazin-2-yl)-N'-[2-(2-chloroeth-oxy)phenylsulphony]]urea (triasulfuron), N-methyl-N-(4-methoxy-6-methyl-l,3,5-triazin-2-yl)-N'-(2-methoxycarbonylphenylsulphonyl)urea (tribenuron-methyl), (3t5,6-trichloro)pyridin-2-yloxyacetic acid (triclopyr), 2-(3,5-dichlorophenyl)-2-(2,2,2-trichloroethyl)oxirane (tridiphane), N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-3-(2,2,2-trifluoroethoxy)-2-pyri-dinesulphonamide sodium salt (trifloxysulfuron), l-amino-2)6-dinitro-NJN-dipropyl-4-trifluoromethylbenzene (trifluralin), N-[4-dimethylamino-6-(2,2,2-trifluoroethoxy)-l,3I5-triazin-2-yl]-N'-(2-methoxycarbonylphenylsulphonyl)-urea (triflusulfuron-methyl), N-(4-methoxy-6-trifIuoromethoxy-l ,3,5-triazin-2-yI)-N>-(2-trifluoromethylphenylsulphonyl)urea (tritosulfuron), N-[[(4,6-dimethoxy-2-pyrimidinyI)amino]carbonyl]-3-(N-methyl-N-methyl-sulphonylamino)-2-pyridinesuIphonamide (cf. WO-A-92/10660), N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-3-(N-methyl-N-methylsulph-onylamino)-2-pyridinesulphonamide (cf. WO-A-92/10660), 4-(4,5-dihydro-4-methyl-5-oxo-3-trifluoromethyl-lH-l,2,4-triazol-l-yI)-2-(ethylsulphonyl-amino)-5-fluorobenzenecarbothioamide (HWH4991, cf. WO-A-95/30661), 2-chloro-N-[l-(2,6-dichloro-4-difluoromethylphenyl)-4-nitro-lH-pyrazoI-5-yljpropanecarboxamide (SLA5599, cf. EP-A-303153), [2-chloro-3-(4,5-dihydro-3-isoxazolyl)-4-methylsuIphonyIphenyl]-(5-hydroxy-l-methyl-lH-pyrazol-4-yl)methanone (cf. WO-A-96/26206, WO-A-98/31681), [3-(4,5-dihydro-3-isoxazolyl)-2-methyl-4-methylsulphonylphenyl]-(5-hydroxy-l-methyl-lH-pyrazol-4-yl)methanone (cf. WO-A-96/26206, WO-A-98/31681),

-125-
[3-[2-chloro-3-[(2,6-dioxocyclohexyl)carbonyl]-6-ethylsulphonylphenyl]-5-is-oxazolyl]acetonitrile (cf. WO-A-01/28341), 2-[2-chloro-4-metnylsulphonyl-3-[(2,2J2^riftuoroethoxy)methyllbenzoyl]-1,3-cyclohexanedione (cf. WO-A-01/28341), 2-[[5,8-dimethyl-l)l-dioxido-4-(2-pyrimidinyloxy)-3,4-dihydro-2H-thiochromen-6-yl]carbonyl]-l,3-cyclohexanedione(cf. WO-A-01/28341)
("Active compounds of group 2"), and, if appropriate, definitely
c) a compound that improves compatibility with erop plants, from the following group of compounds:
4-dichloroacetyl-l-oxa-4-azaspiro[4.5]decane (AD-67), l-dichloroacetylhexa-hydro-3,3,8a-trimethylpyirolo[l,2-a]pyrimidin-6(2H)-one (BAS-145138), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-l,4-benzoxazine (benoxacor), 1-methylhexyl 5-chloroquinoxalin-8-oxyacetate (cloquintocet-mexyl), a-(cyano-methoximino)phenylacetonitrile (cyometrinil), 2,4-dichlorophenoxy acetic acid (2,4-D), 2,2-dichloro-N-(2-oxo-2-(2-propenylamino)ethyl)-N-(2-propeny\)acetamide (DKA-24), 2,2-dichlorO"N,N-di-2-propenylacetamide (di-chlormid), N-(4-methylphenyl)-N'-(l-methyl-l-phenylethyI)urea (daimuron, dymron), 4,6-dichloro-2-phenylpyrimidine (fenclorim), l-(2,4-di-chlorophenyl)-5-trichloromethy]-lH-l,2,4-triazole-3-carboxylate (fenchlor-azol-ethyl), phenylmethyl 2-chloro-4-trifluoromethylthiazole-5-carboxylate (flurazole), 4-chloro-N-(l,3-dioxoIan-2-yImethoxy)-a-trifluoroacetophenone oxime (fluxofenim), 3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyloxazoIidine (furilazole, MON-13900), ethyl 4,5-dihydro-5,5-diphenyI-3-isoxazolcarb-oxylate (isoxadifen-ethyl), (4-chloro-2-methylphenoxy)acetic acid (MCPA), (+-)-2-(4-chloro-2-methyIphenoxy)propanoic acid (mecoprop), diethyl l-(2,4-dichlorophenyl)-4,5-dihydro-5-methyl-lH-pyrazo]-3,5-dicarboxylate (mefen-pyr-diethyl), 2-dichloromethyl-2-methyI-l,3-dioxolane (MG-191), 1,8-

-126-
naphthalic anhydride, a-(l,3-dioxolan-2-ylmethoximino)phenylacetonitrile (oxabetrimï), 2,2-dichloro-N-(l,3-dioxolan-2-ylmethyl)-N-(2-propenyl)acet-amide (PPG-1292), 3-dichloroacetyl-2,2,5-trimethyIoxazolidine (R-29148), N-cyclopropyl-4-[[(2-methoxy-5-methylbenzoyl)amino]sulphonyl]benzamide, N-[[(4-methoxyacetylarriino)phenyl]sulphonyl]-2-methoxybenzamide and N-[[(4-methylaminocarbonylamino)phenyl]sulphonyl]-2-methoxybenzamide (the latter are in each case known from WO-A-99/66795)
("Active compounds of Group 3").
2. Compositions according to Claim l, characterized in that Q1 represents O (oxygen) or S (sulphur), Q2 represents O (oxygen) or S (sulphur),
R1 represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or isopropyl, 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, cyclo-propylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexyl-methyl, represents in each case optionally cyano-, fluorine-, chlorine-, bromine-, 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-substituted heterocyclyl or heterocyclylmethyl, where the heterocyclyl group is in

-127-
each case selected from the group consisting of oxetanyl, thietanyl, furyl, tetrahydrofuryl, thienyl and tetrahydrothienyl,
R2 represents hydrogen, cyano, fluorine, chlorine, brominé, represents in

each case optionally cyano-, fluorine-, chlorine-, jnethóxy- or ethoxy-

substituted methyl, ethyl, n- or isopropyl, n-, iso-, s- or t-butyl, methoxy, ethoxy, n- or isopropoxy, methoxycarbonyl- ethoxycarbonyl' n- or isopropoxycarbonyl, methylthio, ethylthio, n- br isbpropylthio, methyl sulphinyl, ethylsulphinyl, methylsulphonyl or ethyïsulphonyl, or represents in each case optionally cyano-, fluorine- or chlorine-substituted propenyl, butenyl, propynyl, butinyl, propenyloxy, butenyl-oxy, propinyloxy or butinyloxy,
R3 represents hydrogen, hydroxyl, mercapto, amino, cyano, fluorine,
chlorine, brominé, or represents in each case optionally fluorine-,
chlorine-, 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, or represents in each case optionally fluorine-,
chlorine-, and/or bromine-substituted ethenyl, propenyl, butenyl,
ethynyl, propinyl or butinyl, represents in each case optionally
fluorine-, chlorine-, cyano-, methoxy-, ethoxy-, n- or isopropoxy-,
methoxycarbonyl-, ethoxycarbonyl-, n- or isopropoxycarbonyl-
substituted methoxy, ethoxy, n- or isopropoxy, n-, iso-, s- or t-butoxy,
methylthio, ethylthio, n- or isopropylthio, n-, iso-, s- or t-butylthio,
methylamino, ethylamino, n- or isopropylamino, n-, iso-, s- or t-butyl-
amino, acetylamino or propionylamino, or represents propenyloxy,
butenyloxy, ethynyloxy, propinyloxy, butinyloxy, propenylthio,
butenylthio, propinylthio, butinylthio, propenyl amino, butenylamino,
propinylamino or butinylamino, or represents dimethylamino, diethyl-
amino or dipropylamino, represents in each case optionally fluorine-,
-128-
chlorine-, methyl- and/or ethyl-substituted cyclopropyl, cyclobutyl,
cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cyclopropyloxy,

cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclo-
butylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclo-

butylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl,
cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropyl-
methoxy, cyclobutylmethoxy, cyclopentylmethoxyX cyclohexyl-
methoxy, cyclopropylmethylthio, cyclobutylmethyltHio, cycloperityl-
methylthio, cyclohexylmethylthio, cyclopropylmethylamino, cyclo¬butylmethyl amino, cyclopentylmethylamino or cyclohexylmethyl-amino, or represents in each case optionally fluorine-, chlorine-, bromine-, methyl-, trifluoromethyl-, methoxy- or methoxycarbonyl-substituted phenyl, benzyl, phenoxy, benzyloxy, phenylthio, benzyl-thio, phenylamino or benzylamino, and
R4 represents hydrogen, hydroxyl, amino, or 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, propinyl 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, methyl-amino, ethylamino, n- or isopropylamino, n-, iso-, s- or t-butylamino, represents propenyloxy or butenyloxy, represents dimethylamino or di-ethylamino, represents in each case optionally fluorine-, chlorine-methyl- and/or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylamino, cyclobutylamino, cyclopentyl amino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentyl¬methyl or cyclohexylmethyl, or represents in each case optionally fluorine-, chlorine-, mtehyl-, trifluoromethyl- and/or methoxy-substituted phenyl or benzyl, or

-129-

R3 and R together represent trimethylene (propane-l,3-diyl), tetramethylene

(butane-l,4-diyl) or pentamethylene (pentane-l,5-diyl)/

3. Compositions according to Claim l, characterized in that'
Q1 represents O (oxygen), Q2 represents O (oxygen),
R1 represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or isopropyl,

R2 represents fluorine, chlorine, bromine or represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or iso-propyl,
R3 represents hydrogen, chlorine, bromine, or represents in each case optionally fluorine-, chlorine-, methoxy-, ethoxy-, n- or isopropoxy-substituted methyl, ethyl, n- or isopropyl, or represents in each case optionally fluorine- or chlorine-substituted ethenyl, propenyl, butenyl, propinyl or butynyl, or represents in each case optionally fluorine-, chlorine-, methoxy-, ethoxy-, n- or isopropoxy-substituted methoxy, ethoxy, n- or isopropoxy, methylthio, ethylthio, n- or isopropylthio, methylamino, ethylamino, n- or isopropylamino, represents propenyl-oxy, propynyloxy, propenylthio, propynylthio, propenylamino or propynylamino, represents dimethylamino or diethylamino, represents in each case optionally fluorine-, chlorine- or methyl-substituted cyclopropyl, cyclopropyloxy, cyclopropylmethyl or cyclopropyl-methoxy, and
-130-
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-, meth-

oxy- or ethoxy-substituted methoxy, ethoxy, n-or isopropoxy,
represents methylamino, or represents cylopropyl.


4. Compositions according to Claim l, characterized in that the active compound from the second group of herbicides is one or more active compounds selected from the group consisting of flucarbazone-sodium, aceto-chlor, aclonifen, alachlor, amicarbazone, amidosulfuron, amitrole, anilofos, asulam, atrazine, beflubutamid, benazolin (-ethyl), benfuresate, bentazone, bi-fenox, bispyribac-sodium, bromoxynil, butylate, carfentrazone-ethyl, chloro-toluron, chlorosulphuron, c i ni don-ethyl, clodinafop-propargyl, clopyralid, cyanazine, 2,4-D, desmedipham, dicamba, dichlorprop-P, diclofop-methyl, di-fenzoquat, diflufenican, diflufenzopyr, dimethenamid, S-dimethenamid, EPTC, ethofumesate, ethoxysulfuron, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fentrazamide, flamprop-M-isopropyl, flamprop-M-methyl, florasulam, fluazi-fop-P-butyl, fluazolate, flufenacet, flumetsulam, fluoroglycofen-ethyl, flupyr-suÏÏ\iron-meXby\-sodium, fluroxypyr, -butoxypiopyl, -meply), flunamone, flu-thiacet-methyl, foramsulfuron, glufosinate, glufosinate-ammonium, halosulf-uron-methyl, haloxyfop-P-methyl, imazamethabenz-methyl, imazamox, im-azapic, imazapyr, imazaquin, imazethapyr, iodosulfuron-methyl-sodium, ioxynil, isoproturon, isoxaben, isoxachlortole, isoxaflutole, lactofen, linuron, MCPA, mecoprop-P, mefenacet, mesosulfuron, mesotrione, metamitron, met-azachloi", methabenzthiazuron, metolachlor, S-metolachlor, metosulam, metri-buzin, metsulfuron-methyl, naproanilide, neburon, nicosulfuron, oxadiargyl, oxadiazon, oxaziclomefone, oxyfluorfen, pendimethalin, penoxsulam, phen-medipham, picolinafen, primisulfuron-methyl, profluazol, propanil, propoxy-carbazone-sodium, prosulfocarb, prosulfuron, pyraclonil, pyraflufen-ethyl, pyribenzoxim, pyridafol, pyridate, qinclorac, quinmerac, rimsulfuron, sulco-

-131-
trione, sulfosate, sulfosulfuron, terbuthylazine, thifensulfuron-methyl, tral-


koxydim, triallate, triasulfuron, tribenuron-methyl, tritösulfuron, 4-(4,5-di-
hydro-4-methyl-5-oxo-3-trifluoromethyl-lH-l,2,4-triazol-l-yl)-2-(ethylsulf-

onylamino)-5-fluorobenzenecarbothiomide (HWH4991X 2-chIoro-N-[l-(2,6-
dichloro-4-difluoromethylphenyl)-4-nitro-lH-pyrazol-5- yl]propanecarboxamide (SLA5599).
5. Compositions according to Claim l, characterized in that the active
compound from the second group of herbicides is bromoxynil or metosulam.
6. Compositions according to any of Claims l to 4, characterized in that the
crop-plant-compatibility-improving compound is selected from the group
consisting of 1-methylhexyl 5-chIoroquinoxaline-8-oxyacetate (cloquintocet-
mexyl), ethyl 4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxylate (isoxadifen-
ethyl) and diethyl l-(2,4-dichlorophenyI)-4J5-dihydro-5-methyl-lH-pyrazole-
3,5-dicarboxylate (mefenpyr-diethyl), and also 4-dichloroacetyl-l-oxa-4-
azaspiro[4.5]decane (AD-67), l-dichloroacetylhexahydro-3,3,8a-trimethyl-
pyrrolo[l,2-a]-pyrimidin-6(2H)-one (BAS-145138), 4-dichloroacetyI-3,4-di-
hydro-3-methyl-2H-l,4-benzoxazine (benoxacor), 2,2-dichloro-N,N-di-2-
propenylacetamide (dichloromide), 3-dichloroacety]-5-(2-furanyl)-2,2-
dimethyloxazolidine (furilazole, MON-13900) and 3-dichlqroacetyl-2,2,5-tri-
methyloxazolidine (R-29148).
7. Use of a composition according to Claim l for controlling unwanted plants.
8. Method for controlling unwanted plants, characterized in that Compositions
according to Claim l are allowed to act on the unwanted plants and/or their
habitat.
9. Process for preparing a herbicidal composition characterized in that a
composition according to Claim l is mixed with surfactants and/or extenders.

- 132 -
10 Composition substantially as hereinbefore described with reference

to the foregoing examples.

11 Process for preparing a herbicidal cotnposition substantially as
hereinbefore described with reference to the foregoing examples.
Dated this 6/9/2002




Documents:

811-mum-2002-abstract(6-9-2002).doc

811-mum-2002-abstract(6-9-2002).pdf

811-mum-2002-abstract(granted)-(5-3-2009).doc

811-mum-2002-abstract(granted)-(5-3-2009).pdf

811-mum-2002-cancelled pages(4-5-2007).pdf

811-mum-2002-claims(6-9-2002).doc

811-mum-2002-claims(6-9-2002).pdf

811-mum-2002-claims(amended)-(4-5-2007).pdf

811-mum-2002-claims(granted)-(5-3-2009).doc

811-mum-2002-claims(granted)-(5-3-2009).pdf

811-mum-2002-correspondence(21-5-2007).pdf

811-mum-2002-correspondence(ipo)-(25-3-2009).pdf

811-mum-2002-description(complete)-(6-9-2002).pdf

811-mum-2002-description(granted)-(5-3-2009).pdf

811-mum-2002-form 1(6-9-2002).pdf

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

811-mum-2002-form 2(6-9-2002).doc

811-mum-2002-form 2(6-9-2002).pdf

811-mum-2002-form 2(granted)-(5-3-2009).doc

811-mum-2002-form 2(granted)-(5-3-2009).pdf

811-mum-2002-form 2(title page)-(6-9-2002).pdf

811-mum-2002-form 2(title page)-(granted)-(5-3-2009).pdf

811-mum-2002-form 3(3-5-2007).pdf

811-mum-2002-form 3(6-11-2002).pdf

811-mum-2002-form 3(6-9-2002).pdf

811-mum-2002-form 5(6-9-2002).pdf

811-mum-2002-petition under rule 137(18-5-2007).pdf

811-mum-2002-petition under rule 138(3-5-2007).pdf

811-mum-2002-power of authority(3-5-2007).pdf

811-mum-2002-power of authority(6-9-2002).pdf

811-mum-2002-specification(amended)-(4-5-2007).pdf


Patent Number 231521
Indian Patent Application Number 811/MUM/2002
PG Journal Number 13/2009
Publication Date 27-Mar-2009
Grant Date 05-Mar-2009
Date of Filing 06-Sep-2002
Name of Patentee BAYER AKTIENGESELLSCHAFT
Applicant Address D-51368 Leverkusen
Inventors:
# Inventor's Name Inventor's Address
1 DIETER FEUCHT Ackerweg 9, 40789 Monheim
2 PETER DAHMEN Altebrucker Str. 61, 41470 Neuss
3 MARK WILHELM DREWES Goethest. 38, 40754 Langenfeld
4 ROLF PONTZEN Am Kloster 69, 42799 Leichlingen
5 ERNST-RUDOLF F GESING Trillser Graben 4, 40699 Erkarath
PCT International Classification Number C07D249/12
PCT International Application Number N/A
PCT International Filing date
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 10146591.2 2001-09-21 Germany