HERBICIDES CONTAINING SUBSTITUTED THIEN-3-YL-SULPHONYLAMINO(THIO)CARBONYL-TRIAZOLIN(ETHI)ONES

Information

  • Patent Application
  • 20100261680
  • Publication Number
    20100261680
  • Date Filed
    June 28, 2010
    14 years ago
  • Date Published
    October 14, 2010
    14 years ago
Abstract
The invention relates to herbicidal compositions, their preparation, and their use for controlling unwanted vegetation. The compositions include an effective amount of an active compound combination that includes:
Description

The invention relates to novel herbicidal synergistic active compound combinations comprising known substituted thien-3-yl-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(ethi)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)carbonyltriazolin(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)









    • 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 1 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, 1 to 4 carbon atoms in the alkyl moiety, represents in each case optionally nitro-, cyano-, halogen-, C1-C4-alkyl- or C1-C4-alkoxy-substituted aryl or arylalkyl having in each case 6 or 10 carbon atoms in the aryl group and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety, or represents in each case optionally nitro-, cyano-, halogen-, C1-C4-alkyl- or C1-C4-alkoxy-substituted heterocyclyl or heterocyclylalkyl having in each case up to 6 carbon atoms and additionally 1 to 4 nitrogen atoms and/or 1 or 2 oxygen or sulphur atoms in the heterocyclyl group and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety,

    • R2 represents hydrogen, cyano, nitro, halogen, or represents in each case optionally cyano-, halogen- or C1-C4-alkoxy-substituted alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atoms in the alkyl group, or represents in each case optionally cyano- or halogen-substituted alkenyl, alkynyl, alkenyloxy or alkynyloxy having in each case 2 to 6 carbon atoms in the alkenyl or alkynyl group,

    • R3 represents hydrogen, hydroxyl, mercapto, amino, cyano, fluorine, chlorine, bromine, iodine, represents optionally fluorine-, chlorine-, bromine-, cyano-, C1-C4-alkoxy-, C1-C4-alkyl-carbonyl- or C1-C4-alkoxy-carbonyl-substituted alkyl having 1 to 6 carbon atoms, represents in each case optionally fluorine-, chlorine- and/or bromine-substituted alkenyl or alkynyl having in each case 2 to 6 carbon atoms, represents in each case optionally fluorine-, chlorine-, cyano-, C1-C4-alkoxy- or C1-C4-alkoxy-carbonyl-substituted alkoxy, alkylthio, alkylamino or alkylcarbonylamino having in each case 1 to 6 carbon atoms in the alkyl group, represents alkenyloxy, alkynyloxy, alkenylthio, alkynylthio, alkenylamino or alkynylamino having in each case 3 to 6 carbon atoms in the alkenyl or alkynyl group, or represents dialkylamino having in each case 1 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, cycloalkylthio, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylthio or cycloalkylalkylamino having in each case 3 to 6 carbon atoms in the cycloalkyl or cycloalkenyl group and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety, or represents in each case optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, C1-C4-alkyl-, trifluoromethyl-, C1-C4-alkoxy- and/or C1-C4-alkoxy-carbonyl-substituted aryl, arylalkyl, aryloxy, arylalkoxy, arylthio, arylalkylthio, arylamino or arylalkylamino having in each case 6 or 10 carbon atoms in the aryl group and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety,

    • 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 1 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 1 to 6 carbon atoms in the alkyl group, or represents alkenyloxy having 3 to 6 carbon atoms, or represents dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups, or represents in each case optionally fluorine-, chlorine-, bromine-, cyano- and/or C1-C4-alkyl-substituted cycloalkyl, cycloalkylamino or cycloalkylalkyl having in each case 3 to 6 carbon atoms in the alkyl group and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety, or represents in each case optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, C1-C4-alkyl-, trifluoromethyl- and/or C1-C4-alkoxy-substituted aryl or arylalkyl having in each case 6 or 10 carbon atoms in the aryl group and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety, or

    • R3 and R4 together represent optionally branched alkanediyl having 3 to 6 carbon atoms,
      • and salts of the compounds of the formula (I)—





(“Active Compounds of Group 1”)

    • 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]-1-H-1,2,4-triazole-1-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-chloro-6-nitro-3-phenoxybenzenamine (aclonifen), 2-chloro-N-(methoxymethyl)-N-(2,6-diethylphenyl)acetamide (alachlor), methyl 4-hydroxy-6,6-dimethyl-2-oxo-3-[1-[(2-propenyloxy)imino]butyl]-3-cyclohexene-1-carboxylate (sodium salt) (alloxydim (sodium)), N-ethyl-N′-isopropyl-6-methylthio-1,3,5-triazine-2,4-diamine (ametryn), 4-amino-N-(1,1-dimethylethyl)-4,5-dihydro-3-(1-methylethyl)-5-oxo-1H-1,2,4-triazole-1-carboxamide (amicarbazone), N-(4,6-dimethoxypyrimidin-2-yl)-N′-(N-methyl-N-methylsulphonylsulphamoyl)urea (amidosulfuron), 1H-1,2,4-triazole-3-amine (amitrole), S-[2-[(4-chlorophenyl)-(1-isopropyl)amino]-2-oxoethyl] O,O-dimethyl phosphorodithioate (anilofos), O-methyl N-(4-aminophenylsulphonyl)carbamate (asulam), 6-chloro-4-ethylamino-2-isopropylamino-1,3,5-triazine (atrazine), 2-[2,4-dichloro-5-(2-propynyloxy)phenyl]-5,6,7,8-tetrahydro-1,2,4-triazolo-[4,3-a]-pyridin-3(2H)-one (azafenidin), N-(4,6-dimethoxypyrimidin-2-yl)-N′-[1-methyl-4-(2-methyl-2H-tetrazol-5-yl)-1H-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-butyl-N-ethyl-2,6-dinitro-4-trifluoromethylbenzenamine (benfluralin), 2,3-dihydro-3,3-dimethyl-5-benzofuranylethanesulphonate (benfuresate), N-(4,6-dimethoxypyrimidin-2-yl)-N′-(2-methoxy-carbonylphenylmethylsulphonyl)urea (bensulfuron-methyl), 3-i-propyl-1H-2,1,3-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-1(2H)pyrimidinylphenoxymethyl]-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)-1,3-dimethyl-1H-pyrazol-5-yl]oxy]-1-(4-methylphenyl)ethanone (benzofenap), methyl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate (bifenox), 2,6-bis-(4,6-dimethoxypyrimidin-2-yl-oxy)benzoic acid sodium salt (bispyribac-sodium), 5-bromo-6-methyl-3-(1-methylpropyl)-2,4(1H,3H)-pyrimidinedione (bromacil), 2-bromo-3,3-dimethyl-N-(1-methyl-1-phenylethyl)butanamide (bromobutide), 3,5-dibromo-4-hydroxybenzaldehyde O-(2,4-dinitrophenyl) oxime (bromofenoxim), 3,5-dibromo-4-hydroxybenzonitrile (bromoxynil), N-butoxymethyl-2-chloro-N-(2,6-diethylphenyl)acetamide (butachlor), 1,1-dimethyl-2-oxo-2-(2-propenyloxy)]ethyl 2-chloro-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-1(2H)-pyrimidinyl)benzoate (butafenacil), 4-(1-t-butyl)-N-(s-butyl)-2,6-dinitroaniline (butralin), 2-(1-ethoximinopropyl)-3-hydroxy-5-[2,4,6-trimethyl-3-(1-oxobutyl)phenyl]-2-cyclohexene-1-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-1,2,4-triazol-3-one (carfentrazone-ethyl), 2,4-dichloro-1-(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-ethoxycarbonylphenylsulphonyl)urea (chlorimuron-ethyl), 1,3,5-trichloro-2-(4-nitrophenoxy)benzene (chlornitrofen), N′-(3-chloro-4-methylphenyl)-N,N-dimethylurea (chlorotoluron), N-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-N′-(2-chlorophenylsulphonyl)urea (chlorsulfuron), ethyl 2-chloro-3-[2-chloro-5-(1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl)phenyl]-2-propanoate (cinidon-ethyl), exo-1-methyl-4-isopropyl-2-(2-methylphenylmethoxy)-7-oxabicyclo-[2.2.1]-heptane (cinmethylin), N-(4,6-dimethoxy-1,3,5-triazin-2-yl)-N′-(2-(2-methoxyethoxy)phenylsulphonyl)urea (cinosulfuron), 2-[1-[2-(4-chlorophenoxy)propoxyaminobutyl]-5-(tetrahydro-2H-thiopyran-3-yl)-1,3-cyclohexanedione (clefoxydim), (E,E)-(+)-2-[1-[[(3-chloro-2-propenyl)oxy]imino]propyl]-3-hydroxy-2-cyclohexen-1-one (clethodim), (R)-(2-propylnyl) 2-[4-(5-chloro-3-fluoropyridin-2-yl-oxy)phenoxypropanoate (clodinafop-propargyl), 2-[(2-chlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone (clomazone), 2-(2,4-dichloro3-methylphenoxy)-N-phenylpropanamide (clomeprop), 3,6-dichloropyridin-2-carboxylic acid (clopyralid), methyl 3-chloro-2-[(5-ethoxy-7-fluoro[1,2,4]triazolo[1,5-c]pyrimidin-2-ylsulphonyl)amino]benzoate (cloransulam-methyl), N-[(2-chlorophenyl)methyl]-N′-(1-methyl-1-phenylethyl)urea (cumyluron), 2-chloro-4-ethylamino-6-(1-cyano-1-methylethylamino)-1,3,5-triazine (cyanazine), N-(4,6-dimethoxypyrimidin-2-yl)-N′-(2-cyclopropylcarbonylphenylsulphonyl)urea (cyclosulfamuron), 2-(1-ethoximinobutyl)-3-hydroxy-5-(tetrahydro-2H-thiopyran-3-yl)-2-cyclohexen-1-one (cycloxydim), (R)-butyl 2-[4-(4-cyano-2-fluorophenoxy)phenoxy]propanoate (cyhalofop-butyl), 2,4-dichlorophenoxyacetic acid (2,4-D), O-ethyl N-[3-(phenylaminocarbonyloxy)phenyl]carbamate (desmedipham), 3,6-dichloro-2-methoxybenzoic acid (dicamba), 2,6-dichlorobenzonitrile (dichlobenil), (R)-2-(2,4-dichlorophenoxy)propanoic acid (dichlorprop-P), methyl 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoate (diclofop-methyl), N-(2,6-dichlorophenyl)-5-ethoxy-7-fluoro-[1,2,4]-triazolo-[1,5-c]-pyrimidine-2-sulphonamide (diclosulam), 1,2-dimethyl-3,5-diphenyl-1H-pyrazolium methylsulphate (difenzoquat), N-(2,4-difluorophenyl)-2-(3-trifluoromethylphenoxy)pyridine-3-carboxamide (diflufenican), 2-[1-[(3,5-difluorophenyl)aminocarbonylhydrazono]ethyl]pyridine-3-carboxylic acid (diflufenzopyr), N′-[3-chloro-4-(5-t-butyl-oxo-1,3,4-oxadiazol-3(2H)-yl)phenyl]-N,N-dimethylurea (dimefuron), S-(1-methyl-1-phenylethyl) 1-piperidinecarbothioate (dimepiperate), 2-chloro-N-(2,6-dimethylphenyl)-N-(2-methoxyethyl)acetamide (dimethachlor), N-(1,2-dimethylpropyl)-N′-ethyl-6-methylthio-1,3,5-triazine-2,4-diamine (dimethametryn), (S-)2-chloro-N-(2,4-dimethyl-3-thienyl)-N-(2-methoxy-1-methylethyl)acetamide ((S-)(dimethenamid)), 2-amino-4-(1-fluoro-1-methylethyl)-6-(1-methyl-2-(3,5-dimethylphenoxy)ethylamino)-1,3,5-triazine (dimexyflam), 6,7-dihydrodipyrido[1,2-a:2′,1′-c]pyrazinediium dibromide (diquat-dibromide), S,S-dimethyl 2-difluoromethyl-4-isobutyl-6-trifluoromethylpyridine-3,5-dicarbothioate (dithiopyr), N′-(3,4-dichlorophenyl)-N,N-dimethylurea (diuron), N-(4-methylphenyl)-N′-(1-methyl-1-phenylethyl)urea (dymron, daimuron), S-ethyl dipropylthiocarbamate (EPTC), S-(phenylmethyl) N-ethyl-N-(1,2-dimethylpropyl)thiocarbamate (Esprocarb), N-ethyl-N-(2-methyl-2-propenyl)-2,6-dinitro-4-trifluoromethylbenzeneamine (ethalfluralin), methyl 2-[[[[(4-ethoxy-6-methylamino-1,3,5-triazin-2-yl)amino]carbonyl]amino]sulphonyl]benzoate (ethametsulfuron-methyl), 2-ethoxy-2,3-dihydro-3,3-dimethyl-5-benzofuranylmethanesulphonate (ethofumesate), (S)-(2-ethoxy-1-methyl-2-oxoethyl) 2-chloro-5-(2-chloro-4-trifluoromethylphenoxy)benzoate (ethoxyfen), N-(4,6-dimethoxypyrimidin-2-yl)-N′-(2-ethoxyphenoxysulphonyl)urea (ethoxysulfuron), N-(2,3-dichlorophenyl)-4-ethoxymethoxybenzamide (etobenzanide), (R)-ethyl 2-[4-(6-chlorobenzoxazol-2-yloxy)phenoxy]propanoate (Fenoxaprop-(P)-ethyl), 4-(2-chlorophenyl)-N-cyclohexyl-N-ethyl-4,5-dihydro-5-oxo-1H-tetrazole-1-carboxamide (fentrazamide), isopropyl N-benzoyl-N-(3-chloro-4-fluorophenyl)-D-alaninate (flamprop-M-isopropyl), methyl N-benzoyl-N-(3-chloro-4-fluorophenyl)-D-alaninate (flamprop-M-methyl), N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-3-trifluoromethyl-2-pyridinesulphonamide (flazasulfuron), N-(2,6-difluorophenyl)-8-fluoro-5-methoxy-[1,2,4]-triazolo-[1,5-c]-pyrimidine-2-sulphonamide (florasulam), (R)-butyl 2-[4-(5-trifluoromethylpyridin-2-yloxy)phenoxy]propanoate (fluazifop-P-butyl), isopropyl 5-(4-bromo-1-methyl-5-trifluoromethyl-1H-pyrazol-3-yl)-2-chloro-4-fluorobenzoate (fluazolate), N-(4-fluorophenyl)-N-isopropyl-2-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl-oxy)acetamide (flufenacet), ethyl[2-chloro-4-fluoro-5-(5-methyl-6-oxo-4-trifluoromethyl-1(6H)-pyridazinyl)phenoxy]-acetate (flufenpyr), N-(2,6-difluorophenyl)-5-methyl-1,2,4-triazolo[1,5-a]-pyrimidine-2-sulphonamide (flumetsulam), pentyl[2-chloro-4-fluoro-5-(1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl)phenoxy]acetate (flumiclorac-pentyl), 2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazin-6-yl]-4,5,6,7-tetrahydro-1H-isoindole-1,3-dione (flumioxazin), 2-[4-chloro-2-fluoro-5-[(1-methyl-2-propynyl)oxy]phenyl]-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione (flumipropyn), N,N-dimethyl-N′-(3-trifluoromethylphenyl)urea (fluometuron), 3-chloro-4-chloromethyl-1-(3-trifluoromethylphenyl)-2-pyrrolidinone (fluorochloridone), ethoxycarbonylmethyl 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoate (fluoroglycofen-ethyl), 1-(4-chloro-3-(2,2,3,3,3-pentafluoropropoxymethyl)phenyl)-5-phenyl-1H-1,2,4-triazol-3-carboxamide (flupoxam), 1-isopropyl-2-chloro-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-1(2H)-pyrimidyl)benzoate (flupropacil), N-(4,6-dimethoxypyrimidin-2-yl)-N′-(3-methoxycarbonyl-6-trifluoromethylpyridin-2-ylsulphonyl)urea sodium salt (flupyrsulfuron-methyl-sodium), 9-hydroxy-9H-fluorene-9-carboxylic acid (flurenol), (4-amino-3,5-dichloro-6-fluoropyridin-2-yloxy)acetic acid (2-butoxy-1-methylethyl ester, 1-methylheptyl ester) (fluoroxypyr, -butoxypropyl, -meptyl), 5-methylamino-2-phenyl-4-(3-trifluoromethylphenyl)-3(2H)-furanone (flurtamone), methyl[(2-chloro-4-fluoro-5-(tetrahydro-3-oxo-1H,3H-[1,3,4]-thiadiazolo-[3,4-a]-pyridazin-1-yliden)aminophenyl]thioacetate (fluthiacet-methyl), 5-(2-chloro-4-trifluoromethylphenoxy)-N-methylsulphonyl-2-nitrobenzamide (fomesafen), 2-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulphonyl]-4-formylamino-N,N-dimethylbenzamide (foramsulfuron), 2-amino-4-(hydroxymethylphosphinyl)butanoic acid (ammonium salt) (glufosinate (ammonium)), N-phosphonomethylglycine (isopropylammonium salt) (glyphosate, isopropylammonium), methyl 3-chloro-5-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulphonyl]-1-methyl-1H-pyrazole-4-carboxylate (halosulfuron-methyl), (R)-2-[4-(3-chloro-5-trifluoromethylpyridin-2-yloxy)phenoxy]propanoic acid (methyl ester, 2-ethoxyethyl ester, butyl ester) (haloxyfop, -methyl, —P-methyl, -ethoxyethyl, -butyl), 3-cyclohexyl-6-dimethylamino-1-methyl-1,3,5-triazine-2,4(1H,3H)-dione (hexazinone), methyl 2-(4,5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl)-4-methylbenzoate (imazamethabenz-methyl), 2-(4,5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl)-5-methoxymethylpyridine-3-carboxylic acid (imazamox), 2-(4,5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl)-5-methylpyridine-3-carboxylic acid (imazapic), 2-(4,5-dihydro-4-methyl-4-(isopropyl)-5-oxo-1H-imidazol-2-yl)-3-pyridinecarboxylic acid (imazapyr), 2-(4,5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl)quinoline-3-carboxylic acid (imazaquin), 2-(4,5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl)-5-ethylpyridine-3-carboxylic acid (imazethapyr), N-(4,6-dimethoxypyrimidin-2-yl)-N′-(2-chloroimidazo[1,2-a]pyridin-3-ylsulphonyl)urea (imazosulfuron), 2-[2-(3-chlorophenyl)oxiranylmethyl]-2-ethyl-1H-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-isopropylphenyl)urea (isoproturon), N-(5-t-butyl-3-isoxazolyl)N′,N′-dimethylurea (isouron), N-(3-(1-ethyl-1-methylpropyl)isoxazol-5-yl)-2,6-dimethoxybenzamide (isoxaben), (4-chloro-2-methylsulphonylphenyl)-(5-cyclopropylisoxazol-4-yl)methanone (isoxachlortole), (5-cyclopropylisoxazol-4-yl)-(2-methylsulphonyl-4-trifluoromethylphenyl)methanone (isoxaflutole), 2-[(2,3-dihydro-5,8-dimethyl-1,1-dioxidospiro-[4H-1-benzothiopyran-4,2′-[1,3]-dioxolan-6-yl)carbonyl]-1,3-cyclohexanedione (ketospiradox), (2-ethoxy-1-methyl-2-oxoethyl) 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoate (lactofen), 3-cyclohexyl-6,7-dihydro-1H-cyclopenta-pyrimidine-2,4-(3H,5H)-dione (lenacil), N′-(3,4-dichlorophenyl)-N-methoxy-N-methylurea (linuron), (4-chloro-2-methylphenoxy)acetic acid (MCPA), (R)-2-(4-chloro-2-methylphenoxy)propionic acid (mecoprop-P), 2-(2-benzothiazolyloxy)-N-methyl-N-phenylacetamide (mefenacet), methyl 2-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulphonyl]-4-[[(methylsulphonyl)amino]methyl]benzoate (mesosulfuron), 2-(4-methylsulphonyl-2-nitrobenzoyl)-1,3-cyclohexanedione (mesotrione), 4-amino-3-methyl-6-phenyl-1,2,4-triazin-5(4H)-one (metamitron), 2-chloro-N-(2,6-dimethylphenyl)-N-(1H-pyrazol-1-ylmethyl)acetamide (metazachlor), N-(2-benzothiazolyl)-N,N′-dimethylurea (methabenzthiazuron), N′-(4-bromophenyl)-N-methoxy-N-methylurea (metobromuron), (S)-2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2-methoxy-1-methylethyl)acetamide (metolachlor, S-metolachlor), N-(2,6-dichloro-3-methylphenyl)-5,7-dimethoxy-1,2,4-triazolo[1,5-a]-pyrimidine-2-sulphonamide (metosulam), N′-(3-chloro-4-methoxyphenyl)-N,N-dimethylurea (metoxuron), 4-amino-6-tert-butyl-3-methylthio-1,2,4-triazin-5(4H)-one (metribuzin), N-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-N′-(2-methoxycarbonylphenylsulphonyl)urea (metsulfuron-methyl), S-ethyl hexahydro-1H-azepine-1-carbothioate (molinate), 2-(2-naphthyloxy)-N-phenylpropanamide (naproanilide), N,N-diethyl-2-(1-naphthalenyloxy)propanamide (napropamide), N-butyl-N′-(3,4-dichlorophenyl)-N-methylurea (neburon), N-(4,6-dimethoxypyrimidin-2-yl)-N′-(3-dimethylcarbamoylpyridin-2-ylsulphonyl)urea (nicosulfuron), 4-chloro-5-methylamino-2-(3-trifluoromethylphenyl)-3(2H)pyridazinone (norflurazon), S-(2-chlorobenzyl) N,N-diethylthiocarbamate (orbencarb), 4-dipropylamino-3,5-dinitrobenzenesulphonamide (oryzalin), 3-[2,4-dichloro-5-(2-propynyloxy)phenyl]-5-(t-butyl)-1,3,4-oxadiazol-2(3H)-one (oxadiargyl), 3-[2,4-dichloro-5-(1-methylethoxy)phenyl]-5-(t-butyl)-1,3,4-oxadiazol-2(3H)-one (oxadiazon), N-(4,6-dimethylpyrimidin-2-yl)-N′-(2-oxetan-3-yl-oxycarbonylphenylsulphonyl)urea (oxasulfuron), 3-[1-(3,5-dichlorophenyl)-1-isopropyl]-2,3-dihydro-6-methyl-5-phenyl-4H-1,3-oxazin-4-one (oxaziclomefone), 2-chloro-1-(3-ethoxy-4-nitrophenoxy)-4-trifluoromethylbenzene (oxyfluorfen), 1,1′-dimethyl-4,4′-bipyridinium (paraquat), 1-amino-N-(1-ethylpropyl)-3,4-dimethyl-2,6-dinitrobenzene (pendimethalin), 4-(t-butyl)-N-(1-ethylpropyl)-2,6-dinitrobenzenamine (pendralin), 2-(2,2-difluoroethoxy)-N-(5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)-6-trifluoromethylbenzenesulphonamide (penoxsulam), 3-(4-chloro-5-cyclopentyloxy-2-fluorophenyl)-5-(1-methylethylidene)-2,4-oxazolidinedione (pentoxazone), 2-chloro-N-(2-ethoxyethyl)-N-(2-methyl-1-phenyl-1-propenyl)acetamide (pethoxamid), O-methyl N-[3-(3-methylphenylaminocarbonyloxy)phenyl]carbamide (phenmedipham), 4-amino-3,5,6-trichloropyridine-2-carboxylic acid (picloram), N-(4-fluorophenyl)-6-(3-trifluoromethylphenoxy)pyridine-2-carboxamide (picolinafen), S-[2-(2-methyl-1-piperidinyl)-2-oxoethyl] O,O-dipropylphosphorodithioate (piperophos), 2-chloro-N-(2,6-diethylphenyl)-N-(2-propoxyethyl)acetamide (pretilachlor), N-(4,6-bis-difluoromethoxypyrimidin-2-yl)-N′-(2-methoxycarbonylphenylsulphonyl)urea (primisulfuron-methyl), 1-chloro-N-[2-chloro-4-fluoro-5-[(6S,7aR)-6-fluorotetrahydro-1,3-dioxo-1H-pyrrolo[1,2-c]imidazol-2(3H)yl]phenyl]methanesulphonamide (profluazol), 2-[1-[[2-(4-chlorophenoxy)propoxy]imino]butyl]-3-hydroxy-5-(tetrahydro-2H-thiopyranyl)-2-cyclohexen-1-one (profoxydim), N,N′-bis-isopropyl-6-methylthio-1,3,5-triazine-2,4-diamine (prometryn), 2-chloro-N-isopropyl-N-phenylacetamid (propachlor), N-(3,4-dichlorophenyl)propanamide (propanil), (R)-[2-[[(1-methylethylidene)amino]oxy]ethyl]2-[4-(6-chloro-2-quinoxalinyloxy)phenoxy]propanoate (propaquizafop), 2-chloro-N-(2-ethyl-6-methylphenyl)-N-[(1-methylethoxy)methyl]acetamide (propisochlor), methyl 2-[[[(4,5-dihydro-4-methyl-5-oxo-3-propoxy-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulphonyl]benzoate sodium salt (propoxycarbazone-sodium), 3,5-dichloro-N-(1,1-dimethyl-2-propynyl)benzamide (propyzamide), S-phenylmethyl N,N-dipropylthiocarbamate (prosulfocarb), N-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-N′-(2-(3,3,3-trifluoropropyl)phenylsulphonyl)urea (prosulfuron), 1-(3-chloro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-2-yl)-5-(methyl-2-propynylamino)-1H-pyrazol-4-carbonitrile (pyraclonil), ethyl[2-chloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)-4-fluorophenoxy]acetate (pyraflufen-ethyl), 4-(2,4-dichlorobenzoyl)-1,3-dimethyl-5-(4-methylphenylsulphonyloxy)pyrazole (pyrazolate), N-(4,6-dimethoxypyrimidin-2-yl)-N′-(4-ethoxycarbonyl-1-methylpyrazol-5-ylsulphonyl)urea (pyrazosulfuron-ethyl), 4-(2,4-dichlorobenzoyl)-1,3-dimethyl-5-(phenylcarbonyl-methoxy)pyrazole (pyrazoxyfen), diphenylmethanone O-[2,6-bis-(4,6-dimethoxypyrimidin-2-yl-oxy)benzoyl]oxime (pyribenzoxim), 0-[3-(1,1-dimethylethyl)phenyl] (6-methoxy-2-pyridinyl)methylthiocarbamate (pyributicarb), 6-chloro-3-phenyl-4-pyridazinol (pyridafol), O-(6-chloro-3-phenylpyridazin-4-yl) S-octyl thiocarbonate (pyridate), 6-chloro-3-phenylpyridazin-4-ol (pyridatol), 7-[(4,6-dimethoxy-2-pyrimidinyl)thio]-3-methyl-1(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 (pyrithiobac-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-quinoxalinyloxy)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-ylsulphonyl)urea (rimsulfuron), 2-(1-ethoximinobutyl)-5-(2-ethylthiopropyl)-3-hydroxy-2-cyclohexen-1-one (sethoxydim), 6-chloro-2,4-bis-ethylamino-1,3,5-triazine (simazine), 2-(2-chloro-4-methylsulphonylbenzoyl)cyclohexane-1,3-dione (sulcotrione), 2-(2,4-dichloro-5-methylsulphonylaminophenyl)-4-difluoromethyl-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one (sulfentrazone), methyl 2-[[[[(4,6-dimethyl-2-pyrimidinyl)amino]carbonyl]amino]sulphonyl]benzoate (sulfometuron-methyl), N-phosphonomethylglycine trimethyl-sulphonium (sulfosate), N-(4,6-dimethoxypyrimidin-2-yl)-N′-(2-ethylsulphonyl)imidazo[1,2-a]pyridine-3-sulphonamide (sulfosulfuron), N-(5-t-butyl-1,3,4-thiadiazol-2-yl)-N,N′-dimethylurea (tebuthiuron), 2-[1-[(3-chloro-2-propenyl)oxyimino]propyl]-3-hydroxy-5-(tetrahydro-2H-pyran-4-yl)-2-cyclohexen-1-one (tepraloxydim), 6-chloro-4-ethylamino-2-t-butylamino-1,3,5-triazine (terbuthylazine), 2-t-butylamino-4-ethylamino-6-methylthio-1,3,5-triazine (terbutryn), 2-chloro-N-(2,6-dimethylphenyl)-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-1,3,5-triazin-2-yl)-N′-(2-methoxycarbonylthien-3-ylsulphonyl)urea (thifensulfuron-methyl), S-phenylmethyl bis-s-butylcarbamothioate (tiocarbazil), 2-(ethoximinopropyl)-3-hydroxy-5-(2,4,6-trimethylphenyl)-2-cyclohexen-1-one (tralkoxydim), S-(2,3,3-trichloro-2-propenyl) diisopropylcarbamothioate (triallate), N-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-N′-[2-(2-chloroethoxy)phenylsulphonyl]urea (triasulfuron), N-methyl-N-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-N′-(2-methoxycarbonylphenylsulphonyl)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-pyridinesulphonamide sodium salt (trifloxysulfuron), 1-amino-2,6-dinitro-N,N-dipropyl-4-trifluoromethylbenzene (trifluralin), N-[4-dimethylamino-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl]-N′-(2-methoxycarbonylphenylsulphonyl)urea (triflusulfuron-methyl), N-(4-methoxy-6-trifluoromethoxy-1,3,5-triazin-2-yl)-N′-(2-trifluoromethylphenylsulphonyl)urea (tritosulfuron), N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-3-(N-methyl-N-methylsulphonylamino)-2-pyridinesulphonamide (cf. WO-A-91/10660), N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-3-(N-methyl-N-methylsulphonylamino)-2-pyridinesulphonamide (cf. WO-A-91/10660), 4-(4,5-dihydro-4-methyl-5-oxo-3-trifluoromethyl-1H-1,2,4-triazol-1-yl)-2-(ethylsulphonylamino)-5-fluorobenzenecarbothioamide (HWH4991, cf. WO-A-95/30661), 2-chloro-N-[1-(2,6-dichloro-4-difluoromethylphenyl)-4-nitro-1H-pyrazol-5-yl]propanecarboxamide (SLA5599, cf. EP-A-303153), [2-chloro-3-(4,5-dihydro-3-isoxazolyl)-4-methylsulphonylphenyl]-(5-hydroxy-1-methyl-1H-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-1-methyl-1H-pyrazol-4-yl)methanone (cf. WO-A-96/26206, WO-A-98/31681), [3-[2-chloro-3-[(2,6-dioxocyclohexyl)carbonyl]-6-ethylsulphonylphenyl]-5-isoxazolyl]acetonitrile (cf. WO-A-01/28341), 2-[2-chloro-4-methylsulphonyl-3-[(2,2,2-trifluoroethoxy)methyl]benzoyl]-1,3-cyclohexanedione (cf. WO-A-01/28341), 2-[[5,8-dimethyl-1,1-dioxido-4-(2-pyrimidinyloxy)-3,4-dihydro-2H-thiochromen-6-yl]carbonyl]-1,3-cyclohexanedione (cf. WO-A-01/28341)


(“Active Compounds of Group 2”),

    • and, if appropriate, definitely
    • c) a compound that improves compatibility with crop plants, from the following group of compounds:
    • 4-dichloroacetyl-1-oxa-4-azaspiro[4.5]decane (AD-67), 1-dichloroacetyl-hexahydro-3,3,8a-trimethylpyrrolo[1,2-a]pyrimidin-6(2H)-one (BAS-145138), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine (benoxacor), 1-methylhexyl 5-chloroquinoxalin-8-oxyacetate (cloquintocet-mexyl), α-(cyanomethoximino)phenylacetonitrile (cyometrinil), 2,4-dichlorophenoxyacetic acid (2,4-D), 2,2-dichloro-N-(2-oxo-2-(2-propenylamino)ethyl)-N-(2-propenyl)acetamide (DKA-24), 2,2-dichloro-N,N-di-2-propenylacetamide (dichlormid), N-(4-methylphenyl)-N′-(1-methyl-1-phenylethyl)urea (daimuron, dymron), 4,6-dichloro-2-phenylpyrimidine (fenclorim), 1-(2,4-dichlorophenyl)-5-trichloromethyl-1H-1,2,4-triazole-3-carboxylate (fenchlorazol-ethyl), phenylmethyl 2-chloro-4-trifluoromethylthiazole-5-carboxylate (flurazole), 4-chloro-N-(1,3-dioxolan-2-ylmethoxy)-α-trifluoroacetophenone oxime (fluxofenim), 3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyloxazolidine (furilazole, MON-13900), ethyl 4,5-dihydro-5,5-diphenyl-3-isoxazolcarboxylate (isoxadifen-ethyl), (4-chloro-2-methylphenoxy)acetic acid (MCPA), (+-)-2-(4-chloro-2-methylphenoxy)propanoic acid (mecoprop), diethyl 1-(2,4-dichlorophenyl)-4,5-dihydro-5-methyl-1H-pyrazol-3,5-dicarboxylate (mefenpyr-diethyl), 2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191), 1,8-naphthalic anhydride, α-(1,3-dioxolan-2-ylmethoximino)phenylacetonitrile (oxabetrinil), 2,2-dichloro-N-(1,3-dioxolan-2-ylmethyl)-N-(2-propenyl)acetamide (PPG-1292), 3-dichloroacetyl-2,2,5-trimethyloxazolidine (R-29148), N-cyclopropyl-4-[[(2-methoxy-5-methylbenzoyl)amino]sulphonyl]benzamide, N-[[(4-methoxyacetylamino)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”).


Preferred meanings of the groups listed above in connection with the formula (I) are defined 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 cyclohexylmethyl, 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 each case selected from the group consisting of oxetanyl, thietanyl, furyl, tetrahydrofuryl, thienyl and tetrahydrothienyl.
    • 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, propenyloxy, 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-, 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-butylamino, acetylamino or propionylamino, or represents propenyloxy, butenyloxy, ethynyloxy, propinyloxy, butinyloxy, propenylthio, butenylthio, propinylthio, butinylthio, propenylamino, butenylamino, propinylamino or butinylamino, or represents dimethylamino, diethylamino 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, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopropylmethylthio, cyclobutylmethylthio, cyclopentylmethylthio, cyclohexylmethylthio, cyclopropylmethylamino, cyclobutylmethylamino, cyclopentylmethylamino or cyclohexylmethylamino, or represents in each case optionally fluorine-, chlorine-, bromine-, methyl-, trifluoromethyl-, methoxy- or methoxycarbonyl-substituted phenyl, benzyl, phenoxy, benzyloxy, phenylthio, benzylthio, phenylamino or benzylamino,
    • R4 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-butoxy, methylamino, ethylamino, n- or isopropylamino, n-, iso-, s- or t-butylamino, represents propenyloxy or butenyloxy, represents dimethylamino or diethylamino, represents in each case optionally fluorine-, chlorine-methyl- and/or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or represents in each case optionally fluorine-, chlorine-, methyl-, trifluoromethyl- and/or methoxy-substituted phenyl or benzyl.
    • R3 and R4 together preferably represent trimethylene (propane-1,3-diyl), tetramethylene (butane-1,4-diyl) or pentamethylene (pentane-1,5-diyl).
    • 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- or 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 dimethylamino or diethylamino, represents in each case optionally fluorine-, chlorine- or methyl-substituted cyclopropyl, cyclopropyloxy, cyclopropylmethyl or cyclopropylmethoxy, 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 methoxy, ethoxy, n- or isopropoxy, represents methylamino, or represents cyclopropyl.


Preferred active compound components of Group 1 are in particular also the sodium, potassium, magnesium, calcium, ammonium, C1-C4-alkylammonium, di-(C1-C4-alkyl)ammonium, tri-(C1-C4-alkyl)ammonium, 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.


Examples of compounds of the formula (I) which are very particularly preferred as active compound components according to the invention are listed in Table 1 below. The sodium salts of the compounds of Table 1, and in particular the sodium salts of the compounds I-1 and 1-2, are likewise particularly emphasized as active compound components according to the invention.














TABLE 1







Examples of compounds of the formula (I)














Ex.






Melting


No.
Q1
Q2
R1
R2
R3
R4
point (° C.)





I-1 
O
O
CH3
CH3
OC2H5
CH3
163


I-2 
O
O
CH3
CH3
OCH3
CH3
201


I-3 
O
O
CH3
CH3
OC3H7-n
CH3
156


I-4 
O
O
CH3
CH3
OC3H7—I
CH3
150





I-5 
O
O
CH3
CH3
OCH3





218





I-6 
O
O
CH3
CH3
OC2H5





170





I-7 
O
O
CH3
CH3
OC3H7-n





156





I-8 
O
O
CH3
CH3
OC3H7-i





188





I-9 
O
O
CH3
CH3










200





I-10
O
O
CH3
CH3
CH3
CH3
178


I-11
O
O
CH3
CH3
C2H5
CH3
161


I-12
O
O
CH3
CH3
SCH3
CH3
183









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-ethyl, fluazolate, flumiclorac-pentyl, flumioxazin, flupropacil, fluthiacet-methyl, oxadiazon, oxadiargyl, profluazol, pyraflufen-ethyl, pyridate, pyridafol, sulphentrazone, 4-[4,5-dihydro-4-methyl-5-oxo-(3-trifluoromethyl)-1H-1,2,4-triazol-1-yl]-2-[(ethylsulphonyl)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 derivatives (for example clopyralid, dicamba, fluoroxypyr, picloram, triclopyr), benzothiadiazole (for example bentazone), chloroacetamides (for example acetochlor, alachlor, butachlor, (S-) dimethenamid, metazachlor, metolachlor, pretilachlor, propachlor, propisochlor), cyclohexanedione (for example butroxydim, clefoxydim, cycloxydim, sethoxydim, tralkoxydim), dinitroanilines (for example benfluralin, ethalfluralin, oryzalin, pendimethalin, trifluralin), diphenyl ethers (for example acifluorfen-sodium, aclonifen, bifenox, fluoroglycofen-ethyl, fomesafen, lactofen, oxyfluorfen), ureas (for example chlorotoluron, diuron, isoproturon, linuron, metobromuron, 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-isopropylammonium, sulphosate), oxyacetamides (for example flufenacet, mefenacet), phenoxycarboxylic 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, imazosulfuron, metsulfuron-methyl, nicosulfuron, oxasulfuron, primisulfuron-methyl, prosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron-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, metribuzin), 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).


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, cyanazine, 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, fluoroxypyr, -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, metribuzin, metsulfuron-methyl, naproanilide, neburon, nicosulfuron, oxadiargyl, oxadiazon, ox-aziclomefone, oxyfluorfen, pendimethalin, penoxsulam, phenmedipham, picolinafen, primisulfuron-methyl, profluazol, propanil, propoxycarbazone-sodium, prosulfocarb, prosulfuron, pyraclonil, pyraflufen-ethyl, pyribenzoxim, pyridafol, pyridate, qinclorac, quinmerac, rimsulfuron, sulcotrione, sulfosate, sulfosulfuron, terbuthylazine, thifensulfuron-methyl, tralkoxydim, triallate, triasulfuron, tribenuron-methyl, tritosulfuron, 4-(4,5-dihydro-4-methyl-5-oxo-3-trifluoromethyl-1H-1,2,4-triazol-1-yl)-2-(ethylsulphonylamino)-5-fluoro-benzenecarbothiamide (HWH4991), 2-chloro-N-[1-(2,6-dichloro-4-difluoromethylphenyl)-4-nitro-1H-pyrazol-5-yl]propanecarboxamide (SLA5599).


The compositions according to the invention preferably comprise one or two active compounds of Group 1, 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 1, 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 1 and one or two active compounds of Group 2- or of in each case one active compound of Group 1, 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.









TABLE 2







Examples of combinations comprising one active compound


of Group 1 and one or two active compounds of Group 2


(and, if appropriate, additionally a safener)










Active compound




from Group 1
Active compound from Group 2







(I-1)
aclonifen



(I-1)
amicarbazone



(I-1)
amidosulfuron



(I-1)
amitrole



(I-1)
anilofos



(I-1)
asulam



(I-1)
benazolin-ethyl



(I-1)
benfuresate



(I-1)
bifenox



(I-1)
bispyribac-sodium



(I-1)
bromoxynil



(I-1)
desmedipham



(I-1)
diclofop-methyl



(I-1)
diflufenican



(I-1)
ethofumesate



(I-1)
ethoxysulfuron



(I-1)
fenoxaprop-ethyl



(I-1)
fenoxaprop-P-ethyl



(I-1)
fentrazamide



(I-1)
fluazifop-P-butyl



(I-1)
fluazolate



(I-1)
flucarbazone-sodium



(I-1)
flufenacet



(I-1)
flurtamone



(I-1)
foramsulfuron



(I-1)
glufosinate



(I-1)
glufosinate-ammonium



(I-1)
iodosulfuron



(I-1)
ioxynil



(I-1)
isoproturon



(I-1)
isoxachlortole



(I-1)
isoxaflutole



(I-1)
lactofen



(I-1)
linuron



(I-1)
mefenacet



(I-1)
mesosulfuron



(I-1)
metamitron



(I-1)
methabenzthiazuron



(I-1)
metribuzin



(I-1)
neburon



(I-1)
oxadiargyl



(I-1)
oxadiazon



(I-1)
oxaziclomefone



(I-1)
phenmedipham



(I-1)
propanil



(I-1)
propoxycarbazone-sodium



(I-1)
pyraclonil



(I-1)
pyraflufen-ethyl



(I-1)
sulcotrione



(I-2)
aclonifen



(I-2)
amicarbazone



(I-2)
amidosulfuron



(I-2)
amitrole



(I-2)
anilofos



(I-2)
asulam



(I-2)
benazolin-ethyl



(I-2)
benfuresate



(I-2)
bifenox



(I-2)
bispyribac-sodium



(I-2)
bromoxynil



(I-2)
desmedipham



(I-2)
diclofop-methyl



(I-2)
diflufenican



(I-2)
ethofumesate



(I-2)
ethoxysulfuron



(I-2)
fenoxaprop-ethyl



(I-2)
fenoxaprop-P-ethyl



(I-2)
fentrazamide



(I-2)
fluazifop-P-butyl



(I-2)
fluazolate



(I-2)
flucarbazone-sodium



(I-2)
flufenacet



(I-2)
flurtamone



(I-2)
foramsulfuron



(I-2)
glufosinate



(I-2)
glufosinate-ammonium



(I-2)
iodosulfuron



(I-2)
ioxynil



(I-2)
isoproturon



(I-2)
isoxachlortole



(I-2)
isoxaflutole



(I-2)
lactofen



(I-2)
linuron



(I-2)
mefenacet



(I-2)
mesosulfuron



(I-2)
metamitron



(I-2)
methabenzthiazuron



(I-2)
metribuzin



(I-2)
neburon



(I-2)
oxadiargyl



(I-2)
oxadiazon



(I-2)
oxaziclomefone



(I-2)
phenmedipham



(I-2)
propanil



(I-2)
propoxycarbazone-sodium



(I-2)
pyraclonil



(I-2)
pyraflufen-ethyl



(I-2)
sulcotrione



(I-3)
aclonifen



(I-3)
amicarbazone



(I-3)
amidosulfuron



(I-3)
amitrole



(I-3)
anilofos



(I-3)
asulam



(I-3)
benazolin-ethyl



(I-3)
benfuresate



(I-3)
bifenox



(I-3)
bispyribac-sodium



(I-3)
bromoxynil



(I-3)
desmedipham



(I-3)
diclofop-methyl



(I-3)
diflufenican



(I-3)
ethofumesate



(I-3)
ethoxysulfuron



(I-3)
fenoxaprop-ethyl



(I-3)
fenoxaprop-P-ethyl



(I-3)
fentrazamide



(I-3)
fluazifop-P-butyl



(I-3)
fluazolate



(I-3)
flucarbazone-sodium



(I-3)
flufenacet



(I-3)
flurtamone



(I-3)
foramsulfuron



(I-3)
glufosinate



(I-3)
glufosinate-ammonium



(I-3)
iodosulfuron



(I-3)
ioxynil



(I-3)
isoproturon



(I-3)
isoxachlortole



(I-3)
isoxaflutole



(I-3)
lactofen



(I-3)
linuron



(I-3)
mefenacet



(I-3)
mesosulfuron



(I-3)
metamitron



(I-3)
methabenzthiazuron



(I-3)
metribuzin



(I-3)
neburon



(I-3)
oxadiargyl



(I-3)
oxadiazon



(I-3)
oxaziclomefone



(I-3)
phenmedipham



(I-3)
propanil



(I-3)
propoxycarbazone-sodium



(I-3)
pyraclonil



(I-3)
pyraflufen-ethyl



(I-3)
sulcotrione



(I-4)
aclonifen



(I-4)
amicarbazone



(I-4)
amidosulfuron



(I-4)
amitrole



(I-4)
anilofos



(I-4)
asulam



(I-4)
benazolin-ethyl



(I-4)
benfuresate



(I-4)
bifenox



(I-4)
bispyribac-sodium



(I-4)
bromoxynil



(I-4)
desmedipham



(I-4)
diclofop-methyl



(I-4)
diflufenican



(I-4)
ethofumesate



(I-4)
ethoxysulfuron



(I-4)
fenoxaprop-ethyl



(I-4)
fenoxaprop-P-ethyl



(I-4)
fentrazamide



(I-4)
fluazifop-P-butyl



(I-4)
fluazolate



(I-4)
flucarbazone-sodium



(I-4)
flufenacet



(I-4)
flurtamone



(I-4)
foramsulfuron



(I-4)
glufosinate



(I-4)
glufosinate-ammonium



(I-4)
iodosulfuron



(I-4)
ioxynil



(I-4)
isoproturon



(I-4)
isoxachlortole



(I-4)
isoxaflutole



(I-4)
lactofen



(I-4)
linuron



(I-4)
mefenacet



(I-4)
mesosulfuron



(I-4)
metamitron



(I-4)
methabenzthiazuron



(I-4)
metribuzin



(I-4)
neburon



(I-4)
oxadiargyl



(I-4)
oxadiazon



(I-4)
oxaziclomefone



(I-4)
phenmedipham



(I-4)
propanil



(I-4)
propoxycarbazone-sodium



(I-4)
pyraclonil



(I-4)
pyraflufen-ethyl



(I-4)
sulcotrione



(I-5)
aclonifen



(I-5)
amicarbazone



(I-5)
amidosulfuron



(I-5)
amitrole



(I-5)
anilofos



(I-5)
asulam



(I-5)
benazolin-ethyl



(I-5)
benfuresate



(I-5)
bifenox



(I-5)
bispyribac-sodium



(I-5)
bromoxynil



(I-5)
desmedipham



(I-5)
diclofop-methyl



(I-5)
diflufenican



(I-5)
ethofumesate



(I-5)
ethoxysulfuron



(I-5)
fenoxaprop-ethyl



(I-5)
fenoxaprop-P-ethyl



(I-5)
fentrazamide



(I-5)
fluazifop-P-butyl



(I-5)
fluazolate



(I-5)
flucarbazone-sodium



(I-5)
flufenacet



(I-5)
flurtamone



(I-5)
foramsulfuron



(I-5)
glufosinate



(I-5)
glufosinate-ammonium



(I-5)
iodosulfuron



(I-5)
ioxynil



(I-5)
isoproturon



(I-5)
isoxachlortole



(I-5)
isoxaflutole



(I-5)
lactofen



(I-5)
linuron



(I-5)
mefenacet



(I-5)
mesosulfuron



(I-5)
metamitron



(I-5)
methabenzthiazuron



(I-5)
metribuzin



(I-5)
neburon



(I-5)
oxadiargyl



(I-5)
oxadiazon



(I-5)
oxaziclomefone



(I-5)
phenmedipham



(I-5)
propanil



(I-5)
propoxycarbazone-sodium



(I-5)
pyraclonil



(I-5)
pyraflufen-ethyl



(I-5)
sulcotrione



(I-6)
aclonifen



(I-6)
amicarbazone



(I-6)
amidosulfuron



(I-6)
amitrole



(I-6)
anilofos



(I-6)
asulam



(I-6)
benazolin-ethyl



(I-6)
benfuresate



(I-6)
bifenox



(I-6)
bispyribac-sodium



(I-6)
bromoxynil



(I-6)
desmedipham



(I-6)
diclofop-methyl



(I-6)
diflufenican



(I-6)
ethofumesate



(I-6)
ethoxysulfuron



(I-6)
fenoxaprop-ethyl



(I-6)
fenoxaprop-P-ethyl



(I-6)
fentrazamide



(I-6)
fluazifop-P-butyl



(I-6)
fluazolate



(I-6)
flucarbazone-sodium



(I-6)
flufenacet



(I-6)
flurtamone



(I-6)
foramsulfuron



(I-6)
glufosinate



(I-6)
glufosinate-ammonium



(I-6)
iodosulfuron



(I-6)
ioxynil



(I-6)
isoproturon



(I-6)
isoxachlortole



(I-6)
isoxaflutole



(I-6)
lactofen



(I-6)
linuron



(I-6)
mefenacet



(I-6)
mesosulfuron



(I-6)
metamitron



(I-6)
methabenzthiazuron



(I-6)
metribuzin



(I-6)
neburon



(I-6)
oxadiargyl



(I-6)
oxadiazon



(I-6)
oxaziclomefone



(I-6)
phenmedipham



(I-6)
propanil



(I-6)
propoxycarbazone-sodium



(I-6)
pyraclonil



(I-6)
praflufen-ethyl



(I-6)
sulcotrione



(I-7)
aclonifen



(I-7)
amicarbazone



(I-7)
amidosulfuron



(I-7)
amitrole



(I-7)
anilofos



(I-7)
asulam



(I-7)
benazolin-ethyl



(I-7)
benfuresate



(I-7)
bifenox



(I-7)
bispyribac-sodium



(I-7)
bromoxynil



(I-7)
desmedipham



(I-7)
diclofop-methyl



(I-7)
diflufenican



(I-7)
ethofumesate



(I-7)
ethoxysulfuron



(I-7)
fenoxaprop-ethyl



(I-7)
fenoxaprop-P-ethyl



(I-7)
fentrazamide



(I-7)
fluazifop-P-butyl



(I-7)
fluazolate



(I-7)
flucarbazone-sodium



(I-7)
flufenacet



(I-7)
flurtamone



(I-7)
foramsulfuron



(I-7)
glufosinate



(I-7)
glufosinate-ammonium



(I-7)
iodosulfuron



(I-7)
ioxynil



(I-7)
isoproturon



(I-7)
isoxachlortole



(I-7)
isoxaflutole



(I-7)
lactofen



(I-7)
linuron



(I-7)
mefenacet



(I-7)
mesosulfuron



(I-7)
metamitron



(I-7)
methabenzthiazuron



(I-7)
metribuzin



(I-7)
neburon



(I-7)
oxadiargyl



(I-7)
oxadiazon



(I-7)
oxaziclomefone



(I-7)
phenmedipham



(I-7)
propanil



(I-7)
propoxycarbazone-sodium



(I-7)
pyraclonil



(I-7)
pyraflufen-ethyl



(I-7)
sulcotrione



(I-8)
aclonifen



(I-8)
amicarbazone



(I-8)
amidosulfuron



(I-8)
amitrole



(I-8)
anilofos



(I-8)
asulam



(I-8)
benazolin-ethyl



(I-8)
benfuresate



(I-8)
bifenox



(I-8)
bispyribac-sodium



(I-8)
bromoxynil



(I-8)
desmedipham



(I-8)
diclofop-methyl



(I-8)
diflufenican



(I-8)
ethofumesate



(I-8)
ethoxysulfuron



(I-8)
fenoxaprop-ethyl



(I-8)
fenoxaprop-P-ethyl



(I-8)
fentrazamide



(I-8)
fluazifop-P-butyl



(I-8)
fluazolate



(I-8)
flucarbazone-sodium



(I-8)
flufenacet



(I-8)
flurtamone



(I-8)
foramsulfuron



(I-8)
glufosinate



(I-8)
glufosinate-ammonium



(I-8)
iodosulfuron



(I-8)
ioxynil



(I-8)
isoproturon



(I-8)
isoxachlortole



(I-8)
isoxaflutole



(I-8)
lactofen



(I-8)
linuron



(I-8)
mefenacet



(I-8)
mesosulfuron



(I-8)
metamitron



(I-8)
methabenzthiazuron



(I-8)
metribuzin



(I-8)
neburon



(I-8)
oxadiargyl



(I-8)
oxadiazon



(I-8)
oxaziclomefone



(I-8)
phenmedipham



(I-8)
propanil



(I-8)
propoxycarbazone-sodium



(I-8)
pyraclonil



(I-8)
pyraflufen-ethyl



(I-8)
sulcotrione



(I-9)
aclonifen



(I-9)
amicarbazone



(I-9)
amidosulfuron



(I-9)
amitrole



(I-9)
anilofos



(I-9)
asulam



(I-9)
benazolin-ethyl



(I-9)
benfuresate



(I-9)
bifenox



(I-9)
bispyribac-sodium



(I-9)
bromoxynil



(I-9)
desmedipham



(I-9)
diclofop-methyl



(I-9)
diflufenican



(I-9)
ethofumesate



(I-9)
ethoxysulfuron



(I-9)
fenoxaprop-ethyl



(I-9)
fenoxaprop-P-ethyl



(I-9)
fentrazamide



(I-9)
fluazifop-P-butyl



(I-9)
fluazolate



(I-9)
flucarbazone-sodium



(I-9)
flufenacet



(I-9)
flurtamone



(I-9)
foramsulfuron



(I-9)
glufosinate



(I-9)
glufosinate-ammonium



(I-9)
iodosulfuron



(I-9)
ioxynil



(I-9)
isoproturon



(I-9)
isoxachlortole



(I-9)
isoxaflutole



(I-9)
lactofen



(I-9)
linuron



(I-9)
mefenacet



(I-9)
mesosulfuron



(I-9)
metamitron



(I-9)
methabenzthiazuron



(I-9)
metribuzin



(I-9)
neburon



(I-9)
oxadiargyl



(I-9)
oxadiazon



(I-9)
oxaziclomefone



(I-9)
phenmedipham



(I-9)
propanil



(I-9)
propoxycarbazone-sodium



(I-9)
pyraclonil



(I-9)
pyraflufen-ethyl



(I-9)
sulcotrione



(I-10)
aclonifen



(I-10)
amicarbazone



(I-10)
amidosulfuron



(I-10)
amitrole



(I-10)
anilofos



(I-10)
asulam



(I-10)
benazolin-ethyl



(I-10)
benfuresate



(I-10)
bifenox



(I-10)
bispyribac-sodium



(I-10)
bromoxynil



(I-10)
desmedipham



(I-10)
diclofop-methyl



(I-10)
diflufenican



(I-10)
ethofumesate



(I-10)
ethoxysulfuron



(I-10)
fenoxaprop-ethyl



(I-10)
fenoxaprop-P-ethyl



(I-10)
fentrazamide



(I-10)
fluazifop-P-butyl



(I-10)
fluazolate



(I-10)
flucarbazone-sodium



(I-10)
flufenacet



(I-10)
flurtamone



(I-10)
foramsulfuron



(I-10)
glufosinate



(I-10)
glufosinate-ammonium



(I-10)
iodosulfuron



(I-10)
ioxynil



(I-10)
isoproturon



(I-10)
isoxachlortole



(I-10)
isoxaflutole



(I-10)
lactofen



(I-10)
linuron



(I-10)
mefenacet



(I-10)
mesosulfuron



(I-10)
metamitron



(I-10)
methabenzthiazuron



(I-10)
metribuzin



(I-10)
neburon



(I-10)
oxadiargyl



(I-10)
oxadiazon



(I-10)
oxaziclomefone



(I-10)
phenmedipham



(I-10)
propanil



(I-10)
propoxycarbazone-sodium



(I-10)
pyraclonil



(I-10)
pyraflufen-ethyl



(I-10)
sulcotrione



(I-11)
aclonifen



(I-11)
amicarbazone



(I-11)
amidosulfuron



(I-11)
amitrole



(I-11)
anilofos



(I-11)
asulam



(I-11)
benazolin-ethyl



(I-11)
benfuresate



(I-11)
bifenox



(I-11)
bispyribac-sodium



(I-11)
bromoxynil



(I-11)
desmedipham



(I-11)
diclofop-methyl



(I-11)
diflufenican



(I-11)
ethofumesate



(I-11)
ethoxysulfuron



(I-11)
fenoxaprop-ethyl



(I-11)
fenoxaprop-P-ethyl



(I-11)
fentrazamide



(I-11)
fluazifop-P-butyl



(I-11)
fluazolate



(I-11)
flucarbazone-sodium



(I-11)
flufenacet



(I-11)
flurtamone



(I-11)
foramsulfuron



(I-11)
glufosinate



(I-11)
glufosinate-ammonium



(I-11)
iodosulfuron



(I-11)
ioxynil



(I-11)
isoproturon



(I-11)
isoxachlortole



(I-11)
isoxaflutole



(I-11)
lactofen



(I-11)
linuron



(I-11)
mefenacet



(I-11)
mesosulfuron



(I-11)
metamitron



(I-11)
methabenzthiazuron



(I-11)
metribuzin



(I-11)
neburon



(I-11)
oxadiargyl



(I-11)
oxadiazon



(I-11)
oxaziclomefone



(I-11)
phenmedipham



(I-11)
propanil



(I-11)
propoxycarbazone-sodium



(I-11)
pyraclonil



(I-11)
pyraflufen-ethyl



(I-11)
sulcotrione



(I-12)
aclonifen



(I-12)
amicarbazone



(I-12)
amidosulfuron



(I-12)
amitrole



(I-12)
anilofos



(I-12)
asulam



(I-12)
benazolin-ethyl



(I-12)
benfuresate



(I-12)
bifenox



(I-12)
bispyribac-sodium



(I-12)
bromoxynil



(I-12)
desmedipham



(I-12)
diclofop-methyl



(I-12)
diflufenican



(I-12)
ethofumesate



(I-12)
ethoxysulfuron



(I-12)
fenoxaprop-ethyl



(I-12)
fenoxaprop-P-ethyl



(I-12)
fentrazamide



(I-12)
fluazifop-P-butyl



(I-12)
fluazolate



(I-12)
flucarbazone-sodium



(I-12)
flufenacet



(I-12)
flurtamone



(I-12)
foramsulfuron



(I-12)
glufosinate



(I-12)
glufosinate-ammonium



(I-12)
iodosulfuron



(I-12)
ioxynil



(I-12)
isoproturon



(I-12)
isoxachlortole



(I-12)
isoxaflutole



(I-12)
lactofen



(I-12)
linuron



(I-12)
mefenacet



(I-12)
mesosulfuron



(I-12)
metamitron



(I-12)
methabenzthiazuron



(I-12)
metribuzin



(I-12)
neburon



(I-12)
oxadiargyl



(I-12)
oxadiazon



(I-12)
oxaziclomefone



(I-12)
phenmedipham



(I-12)
propanil



(I-12)
propoxycarbazone-sodium



(I-12)
pyraclonil



(I-12)
pyraflufen-ethyl



(I-12)
sulcotrione



(I-1)
fenoxaprop-P-ethyl + mefenpyr-diethyl



(I-2)
fenoxaprop-P-ethyl + mefenpyr-diethyl



(I-3)
fenoxaprop-P-ethyl + mefenpyr-diethyl



(I-4)
fenoxaprop-P-ethyl + mefenpyr-diethyl



(I-5)
fenoxaprop-P-ethyl + mefenpyr-diethyl



(I-6)
fenoxaprop-P-ethyl + mefenpyr-diethyl



(I-7)
fenoxaprop-P-ethyl + mefenpyr-diethyl



(I-8)
fenoxaprop-P-ethyl + mefenpyr-diethyl



(I-9)
fenoxaprop-P-ethyl + mefenpyr-diethyl



(I-10)
fenoxaprop-P-ethyl + mefenpyr-diethyl



(I-11)
fenoxaprop-P-ethyl + mefenpyr-diethyl



(I-12)
fenoxaprop-P-ethyl + mefenpyr-diethyl



(I-1)
fenoxaprop-P-ethyl + isoxadifen-ethyl



(I-2)
fenoxaprop-P-ethyl + isoxadifen-ethyl



(I-3)
fenoxaprop-P-ethyl + isoxadifen-ethyl



(I-4)
fenoxaprop-P-ethyl + isoxadifen-ethyl



(I-5)
fenoxaprop-P-ethyl + isoxadifen-ethyl



(I-6)
fenoxaprop-P-ethyl + isoxadifen-ethyl



(I-7)
fenoxaprop-P-ethyl + isoxadifen-ethyl



(I-8)
fenoxaprop-P-ethyl + isoxadifen-ethyl



(I-9)
fenoxaprop-P-ethyl + isoxadifen-ethyl



(I-10)
fenoxaprop-P-ethyl + isoxadifen-ethyl



(I-11)
fenoxaprop-P-ethyl + isoxadifen-ethyl



(I-12)
fenoxaprop-P-ethyl + isoxadifen-ethyl










Surprisingly, it has now been found that the above-defined active compound combinations of the substituted thien-3-yl-sulphonylamino(thio)carbonyltriazolin(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 crop 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 1 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 mixing components from amongst the active compounds of Group 3:


1-methylhexyl 5-chloroquinoxalin-8-oxyacetate (cloquintocet-mexyl), ethyl 4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxylate (isoxadifen-ethyl) and diethyl 1-(2,4-dichlorophenyl)-4,5-dihydro-5-methyl-1H-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-1-oxa-4-azaspiro[4.5]-decane (AD-67), 1-dichloroacetyl-hexahydro-3,3,8a-trimethylpyrrolo[1,2-a]-pyrimidin-6(2H)-one (BAS-145138), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine (benoxacor), 2,2-dichloro-N,N-di-2-propenylacetamide (dichlormid), 3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyloxazolidine (furilazole, MON-13900) and 3-dichloroacetyl-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 crop plants, it is precisely the abovementioned compounds of Group 3 which are capable of almost completely compensating the harmful effect, on the crop 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, for example, its esters.


Surprisingly, it has also been found that the herbicidally 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 1-(2,4-dichlorophenyl)-4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate (mefenpyr-diethyl), 1-methylhexyl[(5-chloro-8-quinolinyl)oxy]acetate (cloquintocet-mexyl) and ethyl 1-(2,4-dichlorophenyl)-5-(trichloromethyl)-1H-1,2,4-triazole-3-carboxylate (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 crop plant compatibility of the active compound combinations according to the invention is likewise particularly 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 1000 parts by weight, preferably from 0.01 to 100 parts by weight and particularly preferably from 0.1 to 10 parts by weight of one of the crop 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 plants and plant populations such as desired and undesired wild plants or crop plants (inclusive of naturally occurring crop 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, inclusive of the transgenic plants and inclusive 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, leaf, flower and root, examples which may be mentioned being leaves, needles, stalks, trunks, 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:


Dicotyledonous 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.


Dicotyledonous crops of the genera: Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia.


Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.


Monocotyledonous crops of the genera: Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea.


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, 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 paraffins, 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 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 trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.


The formulations generally comprise between 0.1 and 95 percent 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.


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 II) at an application rate of q kg/ha





and






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 found in the literature mentioned above.







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 figures denote:

    • 0%=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 ingredient (active compound).












TABLE A-1








Calculated


Active compound or
Application
Activity against
activity


active compound
rate(s)

Chenopodium

according to


combination
(g of a.i./ha)

album (%)

Colby (%)


















(I-2)
 8
70



bromoxynil
250
80


(I-2) +
8 + 250
100
94


bromoxynil





















TABLE A-2





Active


Calculated

Calculated


compound
Application

activity

activity


or active
rate(s)
Activity against
according
Activity against
according


compound
(g of

Abutilon

to Colby

Xanthium

to Colby


combination
a.i./ha)

theophrasti (%)

(%)

strumarum (%)

(%)




















(I-2)
8
70





metosulam
25
70

90


metosulam
12.5
60

60


(I-2) +
8 + 25  
95
91
100
97


metosulam


(I-2) +
8 + 12.5
95
88
100
88


metosulam




















TABLE A-1-1







Application

Bromus


Bromus




rate

secalinus


secalinus




g of ai/ha
observed
calculated*



















I-2
15
70




4
70


flucarbazone-sodium
60
70


I-2 +
15 + 60
100
91


flucarbazone-sodium
 4 + 60
100
91




















TABLE A-1-2







Application

Veronica


Veronica




rate

persicaria


persicaria




g of ai/ha
observed
calculated*



















I-2
15
60



flucarbazone-sodium
60
60



30
20


I-2 +
15 + 60
98
84


flucarbazone-sodium
15 + 30
80
68





*Values calculated according to Colby

















TABLE A-1-3







Application

Viola


Viola




rate

arvensis


arvensis




g of ai/ha
observed
calculated*



















I-2
8
50




4
40


flucarbazone-sodium
15 
30


I-2 +
8 + 15
80
65


flucarbazone-sodium
4 + 15
80
58




















TABLE A-1-4







Application

Setaria


Setaria




rate

viridis


viridis




g of ai/ha
observed
calculated*





















I-2
8
90





4
80



amidosulfuron
15 
30




8
0



I-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-1-5







Application





rate

Avena fatua


Avena fatua




g of ai/ha
observed
calculated*





















I-2
4
80




amidosulfuron
15 
0




8
0



I-2 +
4 + 15
90
80



amidosulfuron
4 + 8 
90
80





















TABLE A-1-6







Application

Bromus


Bromus




rate

secalinus


secalinus




g of ai/ha
observed
calculated*





















I-2
15
70




amidosulfuron
 8
0



I-2 +
15 + 8
90
70



amidosulfuron







*Values calculated according to Colby

















TABLE A-1-7







Application

Alopecurus


Alopecurus




rate

myosuroides


myosuroides




g of ai/ha
observed
calculated*



















I-2
15 
90




8
90



4
70


carfentrazone-ethyl
8
0


I-2 +
15 + 8 
98
90


carfentrazone-ethyl
8 + 8
95
90



4 + 8
80
70




















TABLE A-1-8







Application

Cyperus


Cyperus




rate

esculentus


esculentus




g of ai/ha
observed
calculated*



















I-2
15 
70



carfentrazone-ethyl
8
30



4
0


I-2 +
15 + 8
100
79


carfentrazone-ethyl
15 + 4
90
70





*Values calculated according to Colby

















TABLE A-1-9







Application

Chenopodium


Chenopodium




rate

album


album




g of ai/ha
observed
calculated*



















I-2
8
85




4
70


carfentrazone-ethyl
8
50



4
30



2
0


I-2 +
8 + 8
98
92.5


carfentrazone-ethyl
4 + 8
95
85



8 + 4
98
89.5



4 + 4
90
79



8 + 2
98
85



4 + 2
80
70




















TABLE A-1-10







Application

Alopecurus


Alopecurus




rate

myosuroides


myosuroides




g of ai/ha
observed
calculated*





















I-2
15
90




dicamba
60
0




30
0



I-2 +
15 + 60
98
90



dicamba
15 + 30
95
90







*Values calculated according to Colby

















TABLE A-1-11







Application

Cyperus


Cyperus




rate

esculentus


esculentus




g of ai/ha
observed
calculated*





















I-2
15
70




dicamba
125 
0




30
0



I-2 +
 15 + 125
95
70



dicamba
15 + 30
90
70





















TABLE A-1-12







Application

Veronica


Veronica




rate

persicaria


persicaria




g of ai/ha
observed
calculated*





















I-2
15
40





 8
0



dicamba
60
40



I-2 +
15 + 60
80
64



dicamba
 8 + 60
60
40







*Values calculated according to Colby

















TABLE A-1-13







Application

Alopecurus


Alopecurus




rate

myosuroides


myosuroides




g of ai/ha
observed
calculated*





















I-2
15
80




diflufenican
125 
70




60
50




30
50



I-2 +
 15 + 125
100
94



diflufenican
15 + 60
95
90




15 + 30
95
90





















TABLE A-1-14







Application





rate

Avena fatua


Avena fatua




g of ai/ha
observed
calculated*





















I-2
15
70





8
70




4
70



diflufenican
125
50



I-2 +
15 + 125 
95
85



diflufenican
8 + 125
95
85




4 + 125
95
85







*Values calculated according to Colby

















TABLE A-1-15







Application

Bromus


Bromus




rate

secalinus


secalinus




g of ai/ha
observed
calculated*





















I-2
 4
80




diflufenican
30
10



I-2 +
4 + 30
95
82



diflufenican





















TABLE A-1-16







Application

Alopecurus


Alopecurus




rate

myosuroides


myosuroides




g of ai/ha
observed
calculated*





















I-2
15
80





8
80



dichlorprop-P
250
20




125
0




60
0



I-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 calculated according to Colby

















TABLE A-1-17







Application

Avena


Avena




rate

fatua


fatua




g of ai/ha
observed
calculated*





















I-2
15
70





8
70




4
70



dichlorprop-P
250
10




125
0



I-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

















TABLE A-1-18







Application

Matricaria


Matricaria




rate

inodora


inodora




g of ai/ha
observed
calculated*





















I-2
15
95





4
70



dichlorprop-P
250
0




125
0




60
0



I-2 +
15 + 250
100
95



dichlorprop-P
 4 + 250
95
70




15 + 125
100
95




 4 + 125
90
70




15 + 60 
100
95




4 + 60
90
70





















TABLE A-1-19







Application

Bromus


Bromus




rate

secalinus


secalinus




g of ai/ha
observed
calculated*





















I-2
8
80





4
70




2
70



bifenox
250
10




125
0




60
0



I-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

















TABLE A-1-20







Application

Avena


Avena




rate

fatua


fatua




g of ai/ha
observed
calculated*





















I-2
4
80





2
70



bifenox
250
10




125
10




60
10



I-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-1-21







Application

Xanthium


Xanthium




rate

strumarium


strumarium




g of ai/ha
observed
calculated*





















I-2
8
70




bifenox
250
70




125
60




60
60



I-2 +
8 + 250
98
91



bifenox
8 + 125
98
88




8 + 60 
98
88







*Values calculated according to Colby

















TABLE A-1-22







Application

Alopecurus


Alopecurus




rate

myosuroides


myosuroides




g of ai/ha
observed
calculated*





















I-2
4
80





2
70



2,4-D ester
250
0




125
0



I-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

















TABLE A-1-23







Application

Bromus


Bromus




rate

secalinus


secalinus




g of ai/ha
observed
calculated*





















I-2
8
80





4
70




2
70



2,4-D ester
250
0




125
0




60
0



I-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-1-24







Application

Cassia


Cassia




rate

tora


tora




g of ai/ha
observed
calculated*





















I-2
2
20




2,4-D ester
250
50




125
50




60
50



I-2 +
2 + 250
80
60



2,4-D ester
2 + 125
70
60




2 + 60 
70
60







*Values calculated according to Colby

















TABLE A-1-25







Application

Bromus


Bromus




rate

secalinus


secalinus




g of ai/ha
observed
calculated*



















I-2
2
90



fenoxaprop-(P)-ethyl
30
0



15
0



8
0


I-2 +
2 + 30
95
90


fenoxaprop-(P)-ethyl
2 + 15
95
90



2 + 8 
95
90




















TABLE A-1-26







Application

Ipomoea


Ipomoea




rate

hederacea


hederacea




g of ai/ha
observed
calculated*



















I-2
4
80




2
80


fenoxaprop-(P)-ethyl
30 
0


I-2 +
4 + 30
90
80


fenoxaprop-(P)-ethyl
2 + 30
90
80





*Values calculated according to Colby

















TABLE A-1-27







Application

Veronica


Veronica




rate

persicaria


persicaria




g of ai/ha
observed
calculated*



















I-2
8
40



fenoxaprop-(P)-ethyl
30
0



15
0



8
0


I-2 +
8 + 30
98
40


fenoxaprop-(P)-ethyl
8 + 15
70
40



8 + 8 
70
40




















TABLE A-1-28







Application

Bromus


Bromus




rate

secalinus


secalinus




g of ai/ha
observed
calculated*





















I-2
8
80





4
80



flupyrsulfuron
4
0




2
0



I-2 +
8 + 4
95
80



flupyrsulfuron
4 + 4
90
80




8 + 2
95
80




4 + 2
90
80







*Values calculated according to Colby

















TABLE A-1-29







Application

Digitaria


Digitaria




rate

sanguinalis


sanguinalis




g of ai/ha
observed
calculated*





















I-2
8
80





4
60




2
30



flupyrsulfuron
4
20



I-2 +
8 + 4
99
84



flupyrsulfuron
4 + 4
80
68




2 + 4
80
44





















TABLE A-1-30







Application

Polygonum


Polygonum




rate

convolvolus


convolvolus




g of ai/ha
observed
calculated*





















I-2
4
70





2
70



flupyrsulfuron
4
80




2
70



I-2 +
4 + 4
98
94



flupyrsulfuron
2 + 4
98
94




4 + 2
98
91




2 + 2
95
91







*Values calculated according to Colby

















TABLE A-1-31







Application

Bromus


Bromus




rate

secalinus


secalinus




g of ai/ha
observed
calculated*





















I-2
8
80





4
80




2
80



fluroxypyr
125
0




60
0



I-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-1-32







Application

Matricaria


Matricaria




rate

inodora


inodora




g of ai/ha
observed
calculated*





















I-2
2
50




fluroxypyr
125
70




60
30



I-2 +
2 + 125
100
85



fluroxypyr
2 + 60 
95
65







*Values calculated according to Colby

















TABLE A-1-33







Application

Veronica


Veronica




rate

persicaria


persicaria




g of ai/ha
observed
calculated*





















I-2
4
30





2
0



fluroxypyr
125
90



I-2 +
4 + 125
98
93



fluroxypyr
2 + 125
98
90





















TABLE A-1-34







Application

Bromus


Bromus




rate

secalinus


secalinus




g of ai/ha
observed
calculated*





















I-2
8
80





4
80



glyphosate
250
80




125
20



I-2 +
8 + 250
100
96



glyphosate
4 + 250
100
96




8 + 125
98
84




4 + 125
98
84







*Values calculated according to Colby

















TABLE A-1-35







Application

Eriochloa


Eriochloa




rate

villosa


villosa




g of ai/ha
observed
calculated*





















I-2
8
70





4
40




2
20



glyphosate
250
70



I-2 +
8 + 250
100
91



glyphosate
4 + 250
100
82




2 + 250
95
76





















TABLE A-1-36







Application

Veronica


Veronica




rate

persicaria


persicaria




g of ai/ha
observed
calculated*





















I-2
4
30





2
0



glyphosate
250
50



I-2 +
4 + 250
100
65



glyphosate
2 + 250
100
50







*Values calculated according to Colby

















TABLE A-1-37







Application

Bromus


Bromus




rate

secalinus


secalinus




g of ai/ha
observed
calculated*





















I-2
8
80





4
80



imazamox
8
60



I-2 +
8 + 8
100
92



imazamox
4 + 8
100
92





















TABLE A-1-38







Application

Matricaria


Matricaria




rate

inodora


inodora




g of ai/ha
observed
calculated*





















I-2
2
50




imazamox
15
50




8
30



I-2 +
2 + 15
100
75



imazamox
2 + 8 
100
65







*Values calculated according to Colby

















TABLE A-1-39







Application

Digitaria


Digitaria




rate

sanguinalis


sanguinalis




g of ai/ha
observed
calculated*





















I-2
8
80





4
60




2
30



imazamox
8
30



I-2 +
8 + 8
98
86



imazamox
4 + 8
98
72




2 + 8
80
51





















TABLE A-1-40







Application

Bromus


Bromus




rate

secalinus


secalinus




g of ai/ha
observed
calculated*





















I-2
8
80





4
80



iodosulfuron
4
0




2
0



I-2 +
8 + 4
100
80



iodosulfuron
4 + 4
100
80




8 + 2
98
80




4 + 2
98
80







*Values calculated according to Colby

















TABLE A-1-41







Application

Veronica


Veronica




rate

persicaria


persicaria




g of ai/ha
observed
calculated*





















I-2
4
30





2
0



iodosulfuron
2
90



I-2 +
4 + 2
100
93



iodosulfuron
2 + 2
100
90





















TABLE A-1-42







Application

Setaria


Setaria




rate

viridis


viridis




g of ai/ha
observed
calculated*





















I-2
4
90




iodosulfuron
4
0




2
0



I-2 +
4 + 4
98
90



iodosulfuron
4 + 2
95
90







*Values calculated according to Colby

















TABLE A-1-43







Application

Bromus


Bromus




rate

secalinus


secalinus




g of ai/ha
observed
calculated*





















I-2
8
80





4
80



isoxaflutole
4
0




2
0



I-2 +
8 + 4
100
80



isoxaflutole
4 + 4
98
80




8 + 2
100
80




4 + 2
98
80





















TABLE A-1-44







Application

Alopecurus


Alopecurus




rate

myosuroides


myosuroides




g of ai/ha
observed
calculated*





















I-2
8
90




isoxaflutole
4
0




2
0



I-2 +
8 + 4
98
90



isoxaflutole
8 + 2
98
90







*Values calculated according to Colby

















TABLE A-1-45







Application

Matricaria


Matricaria




rate

inodora


inodora




g of ai/ha
observed
calculated*





















I-2
2
50




isoxaflutole
4
70



I-2 +
2 + 4
100
85



isoxaflutole





















TABLE A-1-46







Application

Matricaria


Matricaria




rate

inodora


inodora




g of ai/ha
observed
calculated*





















I-2
 2
50




mecoprop-P
250
0




125
0



I-2 +
2 + 250
100
50



mecoprop-P
2 + 125
98
50







*Values calculated according to Colby

















TABLE A-1-47







Application

Galium


Galium




rate

aparine


aparine




g of ai/ha
observed
calculated*





















I-2
 4
80




mecoprop-P
250
40




125
20



I-2 +
4 + 250
98
88



mecoprop-P
4 + 125
95
84





















TABLE A-1-48







Application

Digitaria


Digitaria




rate

sanguinalis


sanguinalis




g of ai/ha
observed
calculated*





















I-2
 8
80




mecoprop-P
250
70




125
40



I-2 +
8 + 250
100
94



mecoprop-P
8 + 125
98
88







*Values calculated according to Colby

















TABLE A-1-49







Application

Bromus


Bromus




rate

secalinus


secalinus




g of ai/ha
observed
calculated*





















I-2
8
80





4
80




2
80



mesotrione
30
0




15
0



I-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-1-50







Application

Polygonum


Polygonum




rate

convolvolus


convolvolus




g of ai/ha
observed
calculated*





















I-2
4
70





2
70



mesotrione
15
50



I-2 +
4 + 15
98
85



mesotrione
2 + 15
95
85







*Values calculated according to Colby

















TABLE A-1-51







Application

Alopecurus


Alopecurus




rate

myosuroides


myosuroides




g of ai/ha
observed
calculated*





















I-2
8
90





2
70



mesotrione
30
0




15
0



I-2 +
8 + 30
95
90



mesotrione
2 + 30
95
70




8 + 15
95
90




2 + 15
80
70





















TABLE A-1-52







Application

Cassia


Cassia




rate

tora


tora




g of ai/ha
observed
calculated*





















I-2
8
0




florasulam
4
0



I-2 +
8 + 4
98
0



florasulam







*Values calculated according to Colby

















TABLE A-1-53







Application

Bromus


Bromus




rate

secalinus


secalinus




g of ai/ha
observed
calculated*





















I-2
2
70




florasulam
4
30




2
30



I-2 +
2 + 4
95
79



florasulam
2 + 2
95
79





















TABLE A-1-54







Application

Veronica


Veronica




rate

persicaria


persicaria




g of ai/ha
observed
calculated*





















I-2
8
0




florasulam
4
70



I-2 +
8 + 4
98
70



florasulam







*Values calculated according to Colby

















TABLE A-1-55







Application

Ipomoea


Ipomoea




rate

hederacea


hederacea




g of ai/ha
observed
calculated*





















I-2
8
80




foramsulfuron
15
80



I-2 +
8 + 15
100
96



foramsulfuron





















TABLE A-1-56







Application

Cyperus


Cyperus




rate

esculentus


esculentus




g of ai/ha
observed
calculated*





















I-2
4
20




foramsulfuron
8
80



I-2 +
4 + 8
90
84



foramsulfuron







*Values calculated according to Colby

















TABLE A-1-57







Application

Eriochloa


Eriochloa




rate

villosa


villosa




g of ai/ha
observed
calculated*





















I-2
4
40





2
0



foramsulfuron
15
60



I-2 +
4 + 15
80
76



foramsulfuron
2 + 15
70
60





















TABLE A-1-58







Application

Bromus


Bromus




rate

secalinus


secalinus




g of ai/ha
observed
calculated*





















I-2
2
70




flurtamone
60
30



I-2 +
2 + 60
95
79



flurtamone







*Values calculated according to Colby

















TABLE A-1-59







Application

Matricaria


Matricaria




rate

inodora


inodora




g of ai/ha
observed
calculated*





















I-2
2
80




flurtamone
30
30



I-2 +
2 + 30
95
86



flurtamone





















TABLE A-1-60







Application

Cyperus


Cyperus




rate

esculentus


esculentus




g of ai/ha
observed
calculated*





















I-2
4
20





2
0



mesosulfuron
15
70




8
70



I-2 +
4 + 15
90
76



mesosulfuron
2 + 15
90
70




4 + 8 
90
76




2 + 8 
90
70







*Values calculated according to Colby

















TABLE A-1-61







Application

Bromus


Bromus




rate

secalinus


secalinus




g of ai/ha
observed
calculated*





















I-2
2
70




mesosulfuron
8
0



I-2 +
2 + 8
90
70



mesosulfuron





















TABLE A-1-62







Application

Avena


Avena




rate

fatua


fatua




g of ai/ha
observed
calculated*





















I-2
8
90





4
90




2
50



metosulam
8
0



I-2 +
8 + 8
98
90



metosulam
4 + 8
95
90




2 + 8
90
50







*Values calculated according to Colby

















TABLE A-1-63







Application

Veronica


Veronica




rate

persicaria


persicaria




g of ai/ha
observed
calculated*





















I-2
8
0





4
0



metosulam
4
80



I-2 +
8 + 4
100
80



Metosulam
4 + 4
100
80





















TABLE A-1-64







Application

Digitaria


Digitaria




rate

sanguinalis


sanguinalis




g of ai/ha
observed
calculated*





















I-2
2
70




metosulam
8
30



I-2 +
2 + 8
90
79



metosulam







*Values calculated according to Colby

















TABLE A-1-65







Application

Matricaria


Matricaria




rate

inodora


inodora




g of ai/ha
observed
calculated*





















I-2
2
80




metribuzin
30
0



I-2 +
2 + 30
95
80



metribuzin





















TABLE A-1-66







Application

Xanthium


Xanthium




rate

strumarium


strumarium




g of ai/ha
observed
calculated*





















I-2
4
90




metribuzin
30
40



I-2 +
4 + 30
98
94



metribuzin







*Values calculated according to Colby

















TABLE A-1-67







Application

Lolium


Lolium




rate

perenne


perenne




g of ai/ha
observed
calculated*





















I-2
2
70




metsulfuron
2
70



I-2 +
2 + 2
100
91



metsulfuron





















TABLE A-1-68







Application

Bromus


Bromus




rate

secalinus


secalinus




g of ai/ha
observed
calculated*





















I-2
2
80




metsulfuron
4
0




2
0



I-2 +
2 + 4
95
80



metsulfuron
2 + 2
95
80







*Values calculated according to Colby

















TABLE A-1-69







Application

Cyperus


Cyperus




rate

esculentus


esculentus




g of ai/ha
observed
calculated*





















I-2
8
80





4
60




2
40



metsulfuron
4
30



I-2 +
8 + 4
95
86



metsulfuron
4 + 4
90
72




2 + 4
80
58





















TABLE A-1-70







Application

Eriochloa


Eriochloa




rate

villosa


villosa




g of ai/ha
observed
calculated*





















I-2
2
0




nicosulfuron
30
90



I-2 +
2 + 30
95
90



nicosulfuron







*Values calculated according to Colby

















TABLE A-1-71







Application

Eriochloa


Eriochloa




rate

villosa


villosa




g of ai/ha
observed
calculated*





















I-2
8
60





4
30




2
0



picolinafen
30
80




15
30



I-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-1-72







Application

Lolium


Lolium




rate

perenne


perenne




g of ai/ha
observed
calculated*





















I-2
2
70




picolinafen
30
20




15
0



I-2 +
2 + 30
95
76



picolinafen
2 + 15
95
70







*Values calculated according to Colby

















TABLE A-1-73







Application

Cassia


Cassia




rate

tora


tora




g of ai/ha
observed
calculated*





















I-2
8
0





4
0



picolinafen
30
70



I-2 +
8 + 30
100
70



picolinafen
4 + 30
80
70





















TABLE A-1-74







Application

Veronica


Veronica




rate

persicaria


persicaria




g of ai/ha
observed
calculated*



















I-2
4
0



propoxycarbazone-sodium
60
40


I-2 +
4 + 60
100
40


propoxycarbazone-sodium





*Values calculated according to Colby

















TABLE A-1-75







Application

Cassia


Cassia




rate

tora


tora




g of ai/ha
observed
calculated*



















I-2
8
0




4
0


propoxycarbazone-sodium
30 
30


I-2 +
8 + 30
80
30


propoxycarbazone-sodium
4 + 30
70
30




















TABLE A-1-76







Application

Polygonum


Polygonum




rate

convolvolus


convolvolus




g of ai/ha
observed
calculated*



















I-2
4
80




2
70


propoxycarbazone-sodium
60
0



30
0


I-2 +
4 + 60
90
80


propoxycarbazone-sodium
2 + 60
90
70



4 + 30
90
80



2 + 30
90
70





*Values calculated according to Colby

















TABLE A-1-77







Application

Cassia


Cassia




rate

tora


tora




g of ai/ha
observed
calculated*





















I-2
8
0




rimsulfuron
8
80




4
60



I-2 +
8 + 8
100
80



rimsulfuron
8 + 4
80
60





















TABLE A-1-78







Application

Abutilon


Abutilon




rate

theophrasti


theophrasti




g of ai/ha
observed
calculated*





















I-2
4
70





2
60



rimsulfuron
4
70



I-2 +
4 + 4
95
91



rimsulfuron
2 + 4
95
88







*Values calculated according to Colby

















TABLE A-1-79







Application

Avena


Avena




rate

fatua


fatua




g of ai/ha
observed
calculated*





















I-2
2
70




rimsulfuron
8
70




4
70



I-2 +
2 + 8
95
91



rimsulfuron
2 + 4
95
91





















TABLE A-1-80







Application

Bromus


Bromus




rate

secalinus


secalinus




g of ai/ha
observed
calculated*





















I-2
8
80





4
70



sulcotrione
120
30




60
0



I-2 +
8 + 120
98
86



sulcotrione
4 + 120
90
79




8 + 60 
98
80




4 + 60 
90
70







*Values calculated according to Colby

















TABLE A-1-81







Application

Bromus


Bromus




rate

secalinus


secalinus




g of ai/ha
observed
calculated*





















I-2
8
80





4
70




2
70



terbuthylazine
500
50



I-2 +
8 + 500
100
90



terbuthylazine
4 + 500
100
85




2 + 500
100
85





















TABLE A-1-82







Application

Setaria


Setaria




rate

viridis


viridis




g of ai/ha
observed
calculated*



















I-2
8
95



thifensulfuron-methyl
15
0



8


I-2 +
8 + 15
100
95


thifensulfuron-methyl
8 + 8 
100
95





*Values calculated according to Colby

















TABLE A-1-83







Application

Bromus


Bromus




rate

secalinus


secalinus




g of ai/ha
observed
calculated*



















I-2
8
80




4
70


thifensulfuron-methyl
15
0



8
0


I-2 +
8 + 15
98
80


thifensulfuron-methyl
4 + 15
98
70



8 + 8 
98
80



4 + 8 
98
70




















TABLE A-1-84







Application

Eriochloa


Eriochloa




rate

villosa


villosa




g of ai/ha
observed
calculated*



















I-2
8
90



thifensulfuron-methyl
15 
10


I-2 +
8 + 15
98
91


thifensulfuron-methyl





*Values calculated according to Colby

















TABLE A-1-85







Application

Bromus


Bromus




rate

secalinus


secalinus




g of ai/ha
observed
calculated*





















I-2
8
80





4
70




2
70



tribenuron-methyl
8
0




4
0



I-2 +
8 + 8
95
80



tribenuron-methyl
4 + 8
95
70




2 + 8
90
70




8 + 4
95
80




4 + 4
90
70




2 + 4
90
70





















TABLE A-1-86







Application

Cyperus


Cyperus




rate

esculentus


esculentus




g of ai/ha
observed
calculated*





















I-2
8
70





4
60




2
40



tribenuron-methyl
8
0




4
0



I-2 +
8 + 8
90
70



tribenuron-methyl
4 + 8
70
60




2 + 8
70
40




8 + 4
80
70




4 + 4
70
60




2 + 4
70
40







*Values calculated according to Colby

















TABLE A-1-87







Application

Veronica


Veronica




rate

persicaria


persicaria




g of ai/ha
observed
calculated*





















I-2
8
30





4
30



tribenuron-methyl
4
90



I-2 +
8 + 4
98
93



tribenuron-methyl
4 + 4
98
93





















TABLE A-1-88







Application

Bromus


Bromus




rate

secalinus


secalinus




g of ai/ha
observed
calculated*





















I-2
8
80





4
70




2
70



HWH 4991
60
30




30
20



I-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

















TABLE A-1-89







Application

Veronica


Veronica




rate

persicaria


persicaria




g of ai/ha
observed
calculated*





















I-2
8
30





4
30




2
0



HWH 4991
30 
90



I-2 +
8 + 30
100
93



HWH 4991
4 + 30
100
93




2 + 30
100
90





















TABLE A-1-90







Application

Lolium


Lolium




rate

perenne


perenne




g of ai/ha
observed
calculated*





















I-2
 2
80




HWH 4991
60
60




30
20



I-2 +
2 + 60
98
92



HWH 4991
2 + 30
95
84







*Values calculated according to Colby

















TABLE A-1-91







Application

Alopecurus


Alopecurus




rate

myosuroides


myosuroides




g of ai/ha
observed
calculated*





















I-2
4
80





2
80



sulfosate
250 
30



I-2 +
4 + 250
95
86



sulfosate
2 + 250
95
86





















TABLE A-1-92







Application

Lolium


Lolium




rate

perenne


perenne




g of ai/ha
observed
calculated*





















I-2
4
70





2
70



sulfosate
250 
70



I-2 +
4 + 250
98
91



sulfosate
2 + 250
98
91







*Values calculated according to Colby

















TABLE A-1-93







Application

Lolium


Lolium




rate

perenne


perenne




g of ai/ha
observed
calculated*





















I-2
8
90





4
70




2
70



tritosulfuron
30
0




15
0



I-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-1-94







Application

Setaria


Setaria




rate

viridis


viridis




g of ai/ha
observed
calculated*





















I-2
8
95





4
90




2
90



tritosulfuron
30 
0



I-2 +
8 + 30
99
95



tritosulfuron
4 + 30
95
90




2 + 30
95
90







*Values calculated according to Colby

















TABLE A-1-95







Application

Digitaria


Digitaria




rate

sanguinalis


sanguinalis




g of ai/ha
observed
calculated*





















I-2
 8
90




tritosulfuron
30
40




15
30



I-2 +
8 + 30
98
94



tritosulfuron
8 + 15
98
93





















TABLE A-1-96







Application

Lolium


Lolium




rate

perenne


perenne




g of ai/ha
observed
calculated*





















I-2
8
90





4
70




2
70



SLA 5599
60
30




30
0



I-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

















TABLE A-1-97







Application

Avena


Avena




rate

fatua


fatua




g of ai/ha
observed
calculated*





















I-2
4
90





2
80



SLA 5599
60
0




30
0



I-2 +
4 + 60
95
90



SLA 5599
2 + 60
90
80




4 + 30
95
90




2 + 30
90
80





















TABLE A-1-98







Application

Veronica


Veronica




rate

persicaria


persicaria




g of ai/ha
observed
calculated*





















I-2
8
40





4
0



SLA 5599
30
80



I-2 +
8 + 30
100
88



SLA 5599
4 + 30
98
80







*Values calculated according to Colby

















TABLE A-1-99







Application

Bromus


Bromus




rate

secalinus


secalinus




g of ai/ha
observed
calculated*





















I-2
4
90





2
80



pyraflufen-ethyl
4
30




2
30



I-2 +
4 + 4
98
93



pyraflufen-ethyl
2 + 4
98
86




4 + 2
98
93




2 + 2
95
86





















TABLE A-1-100







Application

Lolium


Lolium




rate

perenne


perenne




g of ai/ha
observed
calculated*





















I-2
8
90





4
70




2
70



pyraflufen-ethyl
4
30




2
0



I-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

















TABLE A-1-101







Application

Setria


Setria




rate

viridis


viridis




g of ai/ha
observed
calculated*





















I-2
4
90





2
90



pyraflufen ethyl
4
40




2
40



I-2 +
4 + 4
98
94



pyraflufen ethyl
2 + 4
98
94




4 + 2
98
94




2 + 2
98
94





















TABLE A-1-102







Application

Bromus


Bromus




rate

secalinus


secalinus




g of ai/ha
observed
calculated*





















I-2
8
80




flufenacet
125
40




60
20




30
0



I-2 +
 8 + 125
100
88



flufenacet
8 + 60
99
84




8 + 30
99
80







*Values calculated according to Colby

















TABLE A-1-103







Application

Polygonum


Polygonum




rate

convolvolus


convolvolus




g of ai/ha
observed
calculated*





















I-2
8
90





4
80




2
70



flufenacet
125
0




60
0




30
0



I-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

















TABLE A-1-104







Application

Chenopodium


Chenopodium




rate

album


album




g of ai/ha
observed
calculated*





















I-2
2
70




flufenacet
125
0




60
0




30
0



I-2 +
 2 + 125
95
70



flufenacet
2 + 60
95
70




2 + 30
90
70







*Values calculated according to Colby





Claims
  • 1. A herbicidal composition comprising an active compound combination comprising: (a) a substituted thien-3-yl-sulphonylaminocarbonyltriazolinone of formula (I-2)
  • 2. The composition according to claim 1, wherein at least one compound (c) is included.
  • 3. The composition according to claim 2, wherein the compound (c) comprises at least one compound selected from the group consisting of cloquintocet-mexyl, isoxadifen-ethyl, mefenpyr-diethyl, AD-67, BAS-145138, benoxacor, dichlormide, furilazole, and R-29148.
  • 4. The composition according to claim 1, wherein the substituted thien-3-yl-sulphonylamino(thio)carbonyltriazolin(ethi)one of formula (I-2) is in the form of a sodium, potassium, magnesium, calcium, ammonium, C1-C4-alkylammonium, di-(C1-C4-alkyl)ammonium, tri-(C1-C4-alkyl)ammonium, tetra-(C1-C4-alkyl)ammonium, tri(C1-C4-alkyl)sulphonium, C5- or C6-cycloalkylammonium, or di-(C1-C2-alkyl)benzylammonium salt.
  • 5. The composition according to claim 1, wherein the substituted thien-3-yl-sulphonylamino(thio)carbonyltriazolin(ethi)one of formula (I-2) is in the form of a sodium salt.
  • 6. The composition according to claim 1, wherein the weight ratio of the compound (a) of formula (I-2) to the compound (b) is from 1:1 to 1:250.
  • 7. The composition according to claim 1, wherein the weight ratio of the compound (a) or the mixture of compound (a) and compound (b) to the compound (c) is from 1:10 to 1:100.
  • 8. The composition according to claim 1, wherein compound (b) comprises at least one compound selected from the group consisting of aclonifen, amicarbazone, amitrole, anilofos, asulam, benazolin-ethyl, benfuresate, bispyribac-sodium, desmedipham, diclofop-methyl, ethofumesate, ethoxysulfuron, fenoxaprop-ethyl, fentrazamide, fluazifog-P-butyl, fluazolate, glufosinate, ioxynil, isoproturon, isoxachlortole, lactofen, linuron, mefenacet, metamitron, methabenzthiazuron, neburon, oxadiargyl, ozadiazon, oxaziclomefone, phenmedipham, propanil, and pyraclonil.
  • 9. A method for controlling unwanted plants, the method comprising allowing an effective amount of a composition according to claim 1 to act on the unwanted plants and/or their habitat.
  • 10. A process for preparing a herbicidal composition comprising mixing a composition according to claim 1 with one or more surfactants and/or extenders.
  • 11. A method for selective, semi-selective, and/or nonselective control of monocotyledonous and/or dicotyledonous plants comprising allowing an effective amount of a composition according to claim 1 to act on the monocotyledonous and/or dicotyledonous plants and/or their habitat wherein said compound of formula (I-2) is applied in an amount from 2-15 g/ha and said compound from said second group of compounds (b) is applied in an amount of from 2-500 g/ha.
  • 12. The method of claim 11, wherein: said plants comprise at least one selected from the group consisting of Chenopodium, Abutilon, Bromus, Veronica, Viola, Setaria, Avena, Alopecurus, Cyperus, Matricaria, Xanthium, Cassia, Ipomoea, Digitaria, Polygonum, Eriochloa, Galium Eriochloa, and Lolium; andsaid method is used to protect at least one crop selected from the group consisting of cotton, barley, potatoes, maize, oil seed, rape seed, rice, rye, soy beans, sunflower, wheat, sugarcane, and sugar beet.
Priority Claims (1)
Number Date Country Kind
101 46 591.2 Sep 2001 DE national
Parent Case Info

This application is a divisional application of U.S. patent application Ser. No. 10/489,086 (the entire disclosure of which is incorporated herein by reference), filed on Aug. 12, 2004, which was filed under 35 U.S.C. 371 as a national stage application of PCT/EP02/10103, filed Sep. 10, 2002, which was published in German as International Patent Publication WO 03/026426 on Apr. 3, 2003, which is entitled to the right of priority of German Patent Application 101 46 591.2, filed Sep. 21, 2001.

Divisions (1)
Number Date Country
Parent 10489086 Aug 2004 US
Child 12824951 US