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HK1024141B - Selective herbicides based on arylsulphonylaminocarbonyltriazolinones - Google Patents

Selective herbicides based on arylsulphonylaminocarbonyltriazolinones Download PDF

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HK1024141B
HK1024141B HK00103483.8A HK00103483A HK1024141B HK 1024141 B HK1024141 B HK 1024141B HK 00103483 A HK00103483 A HK 00103483A HK 1024141 B HK1024141 B HK 1024141B
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Hong Kong
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methyl
chloro
phenyl
ethyl
methoxy
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HK00103483.8A
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Chinese (zh)
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HK1024141A1 (en
Inventor
P‧达门
D‧福伊希特
K‧H‧米勒
H‧J‧桑特
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Bayer Intellectual Property Gmbh
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Priority claimed from DE19638887A external-priority patent/DE19638887A1/en
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Publication of HK1024141A1 publication Critical patent/HK1024141A1/en
Publication of HK1024141B publication Critical patent/HK1024141B/en

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Selective herbicides based on arylsulfonylaminocarbonyl triazolinones
The present invention relates to novel herbicidal synergistic active compound combinations which contain, on the one hand, the known arylsulfonylaminocarbonyl triazolinones and, on the other hand, the known herbicidally active compounds and which are particularly successful for the selective control of weeds in crops of various useful plants.
The herbicides sulfonylaminocarbonyltriazolinones having a broad spectrum of action are the subject of a series of patent applications (cf. EP 341489, EP 422469, EP 425948, EP 431291, EP 507171, EP534266, WO96/11188, DE 19508118). However, the known sulfonylaminocarbonyltriazolinones have some disadvantages in their action.
Surprisingly, it was found that some known active compounds from a series of arylsulfonylaminocarbonyl triazolinones, when used together with known herbicidally active compounds from various substance classes, show a significant synergistic effect in respect of herbicidal activity and can be used particularly advantageously as broad-spectrum combination preparations for the selective control of weeds in crops of useful plants, for example wheat.
Accordingly, the present invention provides a selective herbicidal composition characterized by an effective amount of a combination of active compounds comprising: (a) an arylsulfonylaminocarbonyltriazolinone of the general formula (I) and/or a salt of a compound of the formula (I)Wherein R is1Represents hydrogen, hydroxyl, amino, alkyleneamino or represents in each case optionally substituted alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkylamino, dialkylamino, cycloalkyl, cycloalkylalkyl, cycloalkylamino, aryl or arylalkyl, R2Represents hydrogen, hydroxyl, mercapto, amino, cyano, halogen or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino, alkenyl, alkinyl, alkenyloxy, alkinyloxy, alkenylthio, alkinylthio, alkenylamino, alkinylamino, cycloalkyl, cycloalkyloxy, cycloalkylthio, cycloalkylamino, cycloalkylalkyl, aryl, aryloxy, arylthio, arylamino or arylalkyl, R3Represents nitro, cyano, halogen or represents in each case optionally substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, alkenyl, alkenyloxy, alkenylthio, alkenylamino, alkynyl, alkynyloxy, alkynylthio, cycloalkyl, cycloalkyloxy, cycloalkylthio, cycloalkylamino, aryl, aryloxy, arylthio, arylsulfinyl, arylsulfonyl or arylamino, R4Represents hydrogen, nitro, cyano, halogen or represents in each case optionally substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, alkenyl, alkenyloxy, alkenylthio, alkenylamino, alkynylalkylHydrocarbyloxy, alkynylthio, cycloalkyl, cycloalkyloxy, cycloalkylthio, cycloalkylamino, aryl, aryloxy, arylthio, arylsulfinyl, arylsulfonyl or arylamino, ("group 1 active compounds") and (b) one or more compounds selected from a second group of herbicides comprising the active compounds listed below: 2-chloro-N- (ethoxymethyl) -N- (2-ethyl-6-methyl-phenyl) -acetamide (acetochlor), 2-chloro-6-nitro-3-phenoxy-aniline (aclonifen), 2-chloro-N- (methoxymethyl) -N- (2, 6-diethyl-phenyl) -acetamide (alachlor), N- (4, 6-dimethoxy-pyrimidin-2-yl) -N- (N-methyl-N-methylsulfonyl-sulfamoyl) -urea (amidosulfuron), 6-chloro-4-ethylamino-2-isopropylamino-1, 3, 5-triazine (atrazine), 4-chloro-2-oxo-3 (2H) -benzothiazolylacetic acid (benazolin), N-benzoyl-N- (3, 4-dichloro-phenyl) -DL-alanine ethyl ester (neodelphinine), 3-isopropyl-1H-2, 1, 3-benzothiadiazin-4 (3H) -one (bentazone), 5- (2, 4-dichloro-phenoxy) -2-nitro-benzoic acid methyl ester (mefenpyr-ethyl), 2-bromo-3, 3-dimethyl-N- (1-methyl-1-phenyl-ethyl) -butyramide (bromobutyrolac), 3, 5-dibromo-4-hydroxy-benzaldehyde-O- (2, 4-dinitro-phenyl) oxime (bromophenol oxime), 3, 5-dibromo-4-hydroxy-benzonitrile (bromoxynil), N-butoxymethyl-2-chloro-N- (2, 6-diethyl-phenyl) -acetamide (butachlor), bis- (2-methyl-propyl) -thiocarbamic acid S-ethyl ester (butantp-late), 2- (4-chloro-2-fluoro-5- (2-chloro-2-ethoxycarbonyl-ethyl) -phenyl) -4-difluoromethyl-5-methyl-2, 4-dihydro-3H-1, 2, 4-triazol-3-one (carfentrazone-ethyl, f-8426), 2, 4-dichloro-1- (3-methoxy-4-nitro-phenoxy) -benzene (metoxyfen), 3-amino-2, 5-dichloro-benzoic acid (imazapine), 1, 3, 5-trichloro-2- (4-nitro-phenoxy) -benzene (cumyl ether), N- (4-methoxy-6-methyl-1, 3, 5-triazin-2-yl) -N- (2-chloro-phenylsulfonyl) -urea (chlorsulfuron), N- (3-amino-4-methylphenyl) -N, N-dimethylurea (chlortoluron), N- (4, 6-dimethoxy-1, 3, 5 triazin-2-yl) -N- (2- (2-methoxy-ethoxy) -phenylsulfonyl) -urea (ethersulfuron), 2- [4- (5-chloro-3-fluoro-pyridin-2-yl-oxy) -phenoxy ] -N- (2-methoxy-ethoxy) -phenylsulfonyl) -urea (ethofenone)]-propionic acid (R) - (2-propynyl) ester (clodinafop-propargyl), 3, 6-dichloro-pyridine-2-carboxylic acid (clopyralid), N- (4, 6-dimethoxy-pyrimidin-2-yl)) -N- (3-chloro-4-methoxycarbonyl-1-methylpyrazol-5-yl-sulfonyl) -urea (cycloplasulfuron, halosulfuron, NC-319), 3-chloro-2- [ (5-ethoxy-7-fluoro [1, 2, 4-d-luoro ] ne]Triazolo [1, 5-c]-pyrimidin-2-yl-sulfonyl) -amino]-benzoic acid methyl ester (cloransulam-methyl), 2-chloro-4-ethylamino-6- (1-cyano-1-methyl-ethylamino) -1, 3, 5-triazine (cyanazine), N- (4, 6-dimethoxy-pyrimidin-2-yl) -N- (2-cyclopropylcarbonyl-phenylsulfonyl) -urea (cyclosufmunon, AC-322140), 2, 4-dichloro-phenoxyacetic acid (2, 4-d), 3, 6-dichloro-2-methoxy-benzoic acid (dicamba), (R) -2- (2, 4-dichloro-phenoxyacetic acid (high 2, 4-d propionate), 2- [4- (2, 4-dichloro-phenoxy) -phenoxy]Methyl propionate (diclofop-methyl ester), 1, 2-dimethyl-3, 5-diphenyl-1H-pyrazolium methylsulfate (difenoconazole), N- (2, 4-difluoro-phenyl) -2- (3-trifluoromethyl-phenoxy) -pyridine-3-carboxamide (diflufenican), 2-chloro-N- (2, 4-dimethyl-3-thienyl) -N- (2-methoxy-1-methyl-ethyl) -acetamide (dimethenamide, SAN-582), 2-amino-4- (1-fluoro-1-methyl-ethyl) -6- (1-methyl-2- (3, 5-dimethyl-phenoxy) -ethylamino) -1, 3, 5-triazine (dimexyflam, IDH-1105), N3, N3-diethyl-2, 4-dinitro-6-trifluoromethyl-1, 3-diamino-benzene (aminofluanide), the sodium salt of N- (4, 6-dimethoxy-pyrimidin-2-yl) -N- (3-methoxycarbonyl-6-trifluoromethyl-pyridin-2-yl-sulfonyl) -urea (DPX-KE459), 6, 7-dihydro-bipyridine [1, 2-a: 2, 1-c]Pyrazinedinium (diquat), 2-difluoromethyl-4-isobutyl-6-trifluoromethyl-pyridine-3, 5-dithiocarboxylic acid S, S-dimethyl ester (dithiopyr), the sodium salt of N- (4, 6-dimethoxy-pyrimidin-2-yl) -N- (3-methoxycarbonyl-6-trifluoromethyl-pyridin-2-yl-sulfonyl) -urea (DPX-KE459), dipropylthiocarbamate S-ethyl Ester (EPTC), N-ethyl-N- (1, 2-dimethyl-propyl) -thiocarbamic acid S- (phenylmethyl) ester (dicamba), [ 2-chloro-5- (4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazole -3-yl) -4-fluoro-phenoxy]-ethyl acetate (ET-751), 2-chloro-5- (2-chloro-4-trifluoromethyl-phenoxy) -benzoic acid (S) - (2-ethoxy-1-methyl-2-oxoethyl) ester (ethoxyyfen), N- (4, 6-dimethoxy-pyrimidin-2-yl) -N- (2-ethoxy-phenoxysulfonyl) -urea (ethoxyysulofuron, HOE-095404), 2- [4- (6-chloro-benzoxazol-2-yl-oxy) -phenoxy ] -phenoxy]-CEthyl acid ester (fenoxaprop-ethyl ester), N-benzoyl-N- (3-chloro-4-fluoro-phenyl) -DL-isopropyl alaninate (ryegrass-isopropyl ester), N-benzoyl-N- (3-chloro-4-fluoro-phenyl) -L-isopropyl alaninate (ryegrass-isopropyl ester-L), N-benzoyl-N- (3-chloro-4-fluoro-phenoxy) -DL-methyl alaninate (ryegrass-methyl ester), N- (2, 6-difluorophenyl) -5-methyl-1, 2, 4-triazolo [1, 5-a ] methyl ester]-pyrimidine-2-sulfonamide (DE-498), [ 2-chloro-4-fluoro-5- (1, 3, 4, 5, 6, 7-hexahydro-1, 3-dioxo-2H-isoindol-2-yl) -phenoxy]Pentyl acetate (flumiclorac-type), 2- [ 4-chloro-2-fluoro-5- [ (1-methyl-2-propynyl) -oxy]-phenyl radical]-4, 5, 6, 7-tetrahydro-IH-isoindole-1, 3(2H) -dione (flunipropyln), 5- (2-chloro-4-trifluoromethyl-phenoxy) -2-nitro-benzoic acid ethoxycarbonyl methyl ester (fluoroglycofen-ethyl ester), 1- (4-chloro-3- (2, 2, 3, 3, 3-pentafluoro-propoxymethyl) -phenyl) -5-phenyl-1H-1, 2, 4-triazole-3-carboxamide (fenchlorazole), 1-isopropyl-2-chloro-5- (3, 6-dihydro-3-methyl-2, 6-dioxo-4-trifluoromethyl-1 (2H) -pyrimidinyl) -benzoic acid 1-isopropyl ester (flupropacil) ) 9-hydroxy-9H-fluorene-9-carboxylic acid (fluorenylbutyric acid), (4-amino-3, 5-dichloro-6-fluoro-pyridin-2-yl-oxy) -acetic acid (fluroxypyr), 5-methylamino-2-phenyl-4- (3-trifluoromethyl-phenyl) -3(2H) -furanone (flurtamone), [ (2-chloro-4-fluoro-5- (tetrahydro-3-oxo-1H, 3H- [1, 3, 4 ] f]Thiadiazolo- [3, 4-a]-pyridazin-1-ylidene) -amino-phenyl]-methyl thioacetate (fluthiacet-methyl, KIH-9201), 2-amino-4- (hydroxymethyl-phosphinyl) -butyric acid (ammonium salt) (glufosinate- (ammonium salt)), N-phosphonomethyl-glycine (-isopropylammonium salt) (glyphosate, -isopropylammonium salt), methyl 2- (4, 5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl) -4-methyl-benzoate (imazamethapyr), 2- (4, 5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl) -5-methyl-pyridine-3-carboxylic acid (imazamethapyr), 2- (4, 5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl) -5-methoxymethyl-pyridine-3-carboxylic acid (imazanox), 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-ethyl-pyridine-3-carboxylic acid (imazethapyr), n- (4, 6-dimethoxy-pyrimidin-2-yl) -N- (2-chloro-imidazo [1,2-a]-pyridin-3-yl-sulfonyl) -urea (azosulfuron), 4-hydroxy-3, 5-diiodo-benzonitrile (ioxybenzonitrile), N-dimethyl-N- (4-isopropyl-phenyl) -urea (isoproturon), N- (3- (1-ethyl-1-methyl-propyl) -isoxazol-5-yl) -2, 6-dimethoxy-benzamide (isoxaben), (5-cyclopropyl-isoxazol-4-yl) - (2-methylsulfonyl-4-trifluoromethyl-phenyl) -methanone (isoxaflutole, RPA-201772), 2- [2- [4- [3, 5-dichloro-2-pyridinyl.]-oxy radical]-phenoxy group]-1-oxo-propyl]-isoxazolidine (oxazapyr), N- (3, 4-dichloro-phenyl) -N-methoxy-N-methylurea (linuron), (4-chloro-2-methyl-phenoxy) -acetic acid (2 m 4 chloro), 2- (4-chloro-2-methyl-phenoxy) -propionic acid (2 m 4 chloropropionic acid), 2-chloro-N- (2, 6-dimethyl-phenyl) -N- (1H-pyrazol-1-yl-methyl) -acetamide (metazachlor), N- (4- (3, 4-dihydro-2-methoxy-2, 4, 4-trimethyl-2H-1-benzopyran-7-yl-oxy) -phenyl) -N-methoxy -N-methyl-urea (metobenzuron, UMP-488), N- (4-bromo-phenyl) -N-methoxy-N-methylurea (xigluron), 2-chloro-N- (2-ethyl-6-methyl-phenyl) -N- (2-methoxy-1-methyl-ethyl) -acetamide (propranolol), N- (2, 6-dichloro-3-methyl-phenyl) -5, 7-dimethoxy-1, 2, 4-triazolo [1, 5-a ]]-pyrimidine-2-sulfonamide (metosulam, DE-511), N- (3-chloro-4-methoxy-phenyl) -N, N-dimethyl-urea (metoxuron), 4-amino-6-tert-butyl-3-methylsulfanyl-1, 2, 4-triazin-5- (4H) -one (metribuzin), N- (4-methoxy-6-methyl-1, 3, 5-triazin-2-yl) -N- (2-methoxycarbonyl-phenylsulfonyl) -urea (metsulfuron-methyl), 2- (2-naphthyloxy) -N-phenylpropionamide (naphthylpropylamine), N-butyl-N- (3, 4-dichloro-phenyl) -N-methyl-urea (glufosinate), N- (4, 6-dimethoxy-pyrimidin-2-yl) -N- (3-dimethylcarbamoyl-pyridin-2-yl-sulfonyl) -urea (nicosulfuron), S- (2-chlorobenzyl) -N, N-diethyl-thiocarbamate (prosulfocarb), N- (4, 6-dimethyl-pyrimidin-2-yl) -N- (2-oxetan-3-yl-oxycarbonyl-phenylsulfonyl) -urea (oxasulfuron), 1, 1-dimethyl-4, 4-bipyridinium salt (paraquat), 1-amino-N- (1-ethyl-propyl) -3, 4-dimethyl-2, 6-dinitro-benzene (pendimethalin), N- (4, 6-bis-difluoromethoxy-pyrimidin-2-yl) -N- (2-methoxycarbonyl-phenylsulfonyl) -urea (primisulfuron-methyl ester), N-dipropyl-thiocarbamic acid S-phenylmethyl ester (prosulfocarb), N- (4-methoxy-propyl) -benzene (mepiquat chloride)-6-methyl-1, 3, 5-triazin-2-yl) -N- (2- (3, 3, 3-trifluoropropyl) -phenylsulfonyl) -urea (prosulfuron), 2-chloro-N- (2, 6-diethyl-phenyl) -N- (2-propoxy-ethyl) -acetamide (pretilachlor), 2-chloro-N-isopropyl-N-phenyl-acetamide (propamol), thiocarbonate O- (6-chloro-3-phenyl-pyridazin-4-yl) ester S-octyl ester (pyridate), 4- (2, 4-dichloro-benzoyl) -1, 3-dimethyl-5- (4-methyl-phenylsulfonyloxy) -pyrazole (pyrazolate), 4- (2, 4-dichloro-benzoyl-1, 3-dimethyl-5- (phenylcarbonylmethoxy) -pyrazole (benzoxazole), N- (4, 6-dimethoxy-pyrimidin-2-yl) -N- (4-ethoxycarbonyl-1-methyl-pyrazol-5-yl-sulfonyl) -urea (pyrazosulfuron-ethyl), 7-chloro-3-methyl-quinoline-8-carboxylic acid (quinmerac acid), N- (4, 6-dimethoxy-pyrimidin-2-yl) -N- (3-ethylsulfonyl-pyridin-2-yl-sulfonyl) -urea (rimsuluron), 6-chloro-2, 4-bis-ethylamino-1, 3, 5-triazine (simazine), 2- (2-chloro-4-methylsulfonyl-benzoyl) -cyclohexane-1, 3-dione (sulcotrione), 2- (2, 4-dichloro-5-methylsulfonylamino-phenyl) -4-difluoromethyl-5-methyl-2, 4-dihydro-3H-1, 2, 4-triazol-3-one (sulfentrazone, F-6285), N-phosphonomethyl-glycine-trimethylsulfonium salt (glyphosate), N- (4, 6-dimethoxy-pyrimidin-2-yl) -N- (2-ethylsulfonyl-imidazo [1, 2-a]Pyridine-3-sulfonamide (sulfofuron, MON-37500), 6-chloro-4-ethylamino-2-tert-butylamino-1, 3, 5-triazine (terbuthylazine), 2-tert-butylamino-4-ethylamino-6-methylsulfanyl-1, 3, 5-triazine (terbutrine), 2-chloro-N- (2, 6-dimethyl-phenyl) -N- (3-methoxy-2-thienyl-methyl) -acetamide (thenylchloride), 6- (6, 7-dihydro-6, 6-dimethyl-3H, 5H-pyrrolo [2, 1-c ] pyrrole]-1, 2, 4-thiadiazol-3-ylideneamino) -7-fluoro-4- (2-propynyl) -2H-1, 4-benzoxazin-3 (4H) -one (thizimin), N- (4-methoxy-6-methyl-1, 3, 5-triazin-2-yl) -N- (2-methoxycarbonyl-thiophen-3-yl-sulfonyl) -urea (thifensulfuron-methyl), 2- (ethoxyimino-propyl) -3-hydroxy-5- (2, 4, 6-trimethyl-phenyl) -2-cyclohexen-1-one (tralkoxydim), S- (2, 3, 3-trichloro-2-propenyl) di-isopropylthiocarbamate (bisfenvinphos), N- (4-methoxy-6-methyl-1, 3, 5-triazin-2-yl) -N- [2- (2-chloro-ethoxy) -phenylsulfonyl]Urea (triasulfuron), N-methyl-N- (4-methoxy-6-methyl-13, 5-triazin-2-yl) -N- (2-methoxycarbonyl-phenylsulfonyl) -urea (tribenuron-methyl), 2- (3, 5-dichloro-phenyl) -2- (2, 2, 2-trichloro-ethyl) -oxirane (mesoxycarb-on), 1-amino-2, 6-dinitro-N, N-dipropyl-4-trifluoromethyl-benzene (trifluralin) - ("active compound of group 2"), where 0.01 to 1000 parts by weight of active compound of group 2 are generally used per part by weight of active compound of group 1 (i.e. compound of formula (1).
Of particular interest are the selective herbicidal compositions according to the invention, which are characterized by containing active compound combinations comprising: (a) an arylsulfonylaminocarbonyltriazolinone of the general formula (I) and/or a salt of a compound of the formula (I), wherein R1Represents hydrogen, hydroxy, amino, C2-C6-alkyleneamino, represents in each case optionally cyano-, halogen-or C1-C4Alkoxy-substituted alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkylamino or dialkylamino in each case optionally substituted by cyano, halogen or C1-C4Alkyl-substituted cycloalkyl, cycloalkylalkyl or cycloalkylamino having in each case 3 to 6 carbon atoms in the cycloalkyl radical and if appropriate 1 to 4 carbon atoms in the alkyl moiety, or represents optionally in each case cyano-, nitro-, halogen-, C1-C4-alkyl-, C1-C4-haloalkyl-, C1-C4-alkoxy-or C1-C4-haloalkoxy-substituted phenyl or phenyl-C1-C4-alkyl, R2Represents hydrogen, hydroxy, mercapto, amino, cyano, halogen, represents in each case optionally cyano-, halogen-or C1-C4-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino, alkenyl, alkinyl, alkenyloxy, alkinyloxy, alkenylthio or alkinylthio, alkenylamino or alkinylamino, in each case optionally cyano-, halogen-or C-substituted1-C4Alkyl-substituted in each case cycloalkanesCycloalkyl, cycloalkyloxy, cycloalkylthio, cycloalkylamino or cycloalkylalkyl having from 3 to 6 carbon atoms in the radical and, if appropriate, from 1 to 4 carbon atoms in the alkyl moiety, or represents in each case optionally cyano-, nitro-, halogen-, C1-C4-alkyl-, C1-C4-haloalkyl-, C1-C4-alkoxy-or C1-C4Halogenoalkoxy-substituted phenyl, phenoxy, phenylthio, phenylamino or phenyl-C1-C4-alkyl, R3Represents nitro, cyano, halogen, represents in each case optionally cyano-, halogen-or C1-C4-alkoxy-substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, alkenyl, alkenyloxy, alkenylthio, alkenylamino, alkynyloxy, alkynylthio, representing in each case optionally cyano-, halogen-or C-substituted by one or more radicals1-C4-alkyl-substituted cycloalkyl, cycloalkyloxy, cycloalkylthio, cycloalkylamino, in each case having from 3 to 6 carbon atoms in the cycloalkyl radical, or represents in each case optionally cyano-, nitro-, halogen-, C1-C4-alkyl-, C1-C4-haloalkyl-, C1-C4-alkoxy-or C1-C4-haloalkoxy-substituted phenyl, phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl or phenylamino, and R4Represents hydrogen, nitro, cyano, halogen, represents in each case optionally cyano-, halogen-or C1-C4-alkoxy-substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, alkenyl, alkenyloxy, alkenylthio, alkenylamino, alkynyloxy or alkynylthio, in each case optionally substituted by cyano-, halogen-or C1-C4Alkyl-substituted cycloalkyl having in each case 3 to 6 carbon atoms in the cycloalkyl radical, cycloalkylOxy, cycloalkylthio, cycloalkylamino, or represents in each case optionally cyano, nitro-, halogen-, C1-C4-alkyl-, C1-C4-haloalkyl-, C1-C4-alkoxy-or C1-C4-haloalkoxy-substituted phenyl, phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl or phenylamino, ("active compounds of group 1") and (b) one to three compounds selected from herbicides of group 2 comprising the active compounds listed below: 2-chloro-N- (ethoxymethyl) -N- (2-ethyl-6-methyl-phenyl) -acetamide (acetochlor), 2-chloro-6-nitro-3-phenoxy-aniline (aclonifen), 2-chloro-N- (methoxymethyl) -N- (2, 6-diethyl-phenyl) -acetamide (alachlor), N- (4, 6-dimethoxy-pyrimidin-2-yl) -N- (N-methyl-N-methylsulfonyl-sulfamoyl) -urea (amidosulfuron), 6-chloro-4-ethylamino-2-isopropylamino-1, 3, 5-triazine (atrazine), N-benzoyl-N- (3, 4-dichloro-phenyl) -DL-alanine ethyl ester (neodelphinine), 3-isopropyl-1H-2, 1, 3-benzothiadiazin-4 (3H) -one (bentazone), 5- (2, 4-dichloro-phenoxy) -2-nitro-benzoic acid methyl ester (bifenox), 2-bromo-3, 3-dimethyl-N- (1-methyl-1-phenyl-ethyl) -butyramide (bromobutylachlor), 3, 5-dibromo-4-hydroxy-benzaldehyde-O- (2, 4-dinitrophenyl) oxime (bromophenol oxime), 3, 5-dibromo-4-hydroxy-benzonitrile (bromoxynil), N-butoxymethyl-2-chloro-N- (2, 6-diethyl-phenyl) -acetamide (butachlor), bis- (2-methyl-propyl) -thiocarbamic acid S-ethyl ester (butachlor), 2- (4-chloro-2-fluoro-5- (2-chloro-2-ethoxycarbonyl-ethyl) -phenyl) -4-difluoromethyl-5-methyl-2, 4-dihydro-3H-1, 2, 4-triazol-3-one (carfentrazone-ethyl, F-8426), 2, 4-dichloro-1- (3-methoxy-4-nitro-phenoxy) -benzene (metoxyfen), 3-amino-2, 5-dichloro-benzoic acid (bentazon), 1, 3, 5-trichloro-2- (4-nitro-phenoxy) -benzene (cumyl ether), N- (4-methoxy-6-methyl-1, 3, 5-triazin-2-yl) -N- (2-chloro-phenylsulfonyl) -urea (chlorsulfuron), N- (3-chloro-4-methylphenyl) -N, N-dimethylurea (chlortoluron), N- (4, 6-dimethoxy-1, 3, 5-triazin-2-yl) -N- (2- (2-methoxy-ethoxy) -phenylsulfonyl) -urea (ethoferruron), 2- [4- (5-chloro-3-fluoro-pyridin-2-yl-oxy) -phenoxy ] -phenoxy]-propionic acid (R)) - (2-propynyl) ester (clodinafop-propargyl), 3, 6-dichloro-pyridine-2-carboxylic acid (clopyralid), N- (4, 6-dimethoxy-pyrimidin-2-yl) -N- (3-chloro-4-methoxycarbonyl-1-methylpyrazol-5-yl-sulfonyl) -urea (cycloparasulfuron, halosulfuron, NC-319), 3-chloro-2- [ (5-ethoxy-7-fluoro [1, 2, 4-fluoro-)]Triazolo [1, 5-c]-pyrimidin-2-yl-sulfonyl) -amino]-benzoic acid methyl ester (cloransulam-methyl), 2-chloro-4-ethyl-amino-6- (1-cyano-1-methyl-ethylamino) -1, 3, 5-triazine (cyanazine), N- (4, 6-dimethoxy-pyrimidin-2-yl) -N- (2-cyclopropylcarbonyl-phenylsulfonyl) -urea (cyclosufmunon, AC-322140), 3, 6-dichloro-2-methoxy-benzoic acid (dicamba), (R) -2- (2, 4-dichloro-phenoxy) -propionic acid (high 2, 4-d-propionate), 2- [4- (2, 4-dichloro-phenoxy) -phenoxy.]Methyl propionate (diclofop-methyl ester), 1, 2-dimethyl-3, 5-diphenyl-1H-pyrazolium methylsulfate (difenoconazole), N- (2, 4-difluoro-phenyl) -2- (3-trifluoromethyl-phenoxy) -pyridine-3-carboxamide (diflufenican), 2-chloro-N- (2, 4-dimethyl-3-thienyl) -N- (2-methoxy-1-methyl-ethyl) -acetamide (dimethenamide, SAN-582), 2, 4-dichloro-phenoxyacetic acid (2, 4-d), 2-amino-4- (1-fluoro-1-methyl-ethyl) -6- (1-methyl-2- (3, 5-dimethyl-phenoxy) -ethylamino) -1, 3, 5-triazine (dimexyflam, IDH-1105), the sodium salt of N- (4, 6-dimethoxy-pyrimidin-2-yl) -N- (3-methoxycarbonyl-6-trifluoromethyl-pyridin-2-yl-sulfonyl) -urea (DPX-KE459), 6, 7-dihydro-bipyridino [1, 2-a: 2, 1-c]Pyrazinedinium (diquat), 2-difluoromethyl-4-isobutyl-6-trifluoromethyl-pyridine-3, 5-dithiocarboxylic acid S, S-dimethyl ester (dithiopyr), the sodium salt of N- (4, 6-dimethoxy-pyrimidin-2-yl) -N- (3-methoxycarbonyl-6-trifluoromethyl-pyridin-2-yl-sulfonyl) -urea (DPX-KE459), dipropylthiocarbamate S-ethyl Ester (EPTC), N-ethyl-N- (1, 2-dimethyl-propyl) -thiocarbamic acid S- (phenylmethyl) ester (dicamba), [ 2-chloro-5- (4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazole -3-yl) -4-fluoro-phenoxy]-ethyl acetate (ET-751), 2-chloro-5- (2-chloro-4-trifluoromethyl-phenoxy) -benzoic acid (S) - (2-ethoxy-1-methyl-2-oxoethyl) ester (ethoxyfen), N- (4, 6-dimethoxy-pyrimidin-2-yl) -N- (2-ethoxy-phenoxysulfonyl) -urea (ethoxyysulofuron, HOE-095404), 2- [4- (6-chloro-4-phenoxy) -benzoic acid (S) - (2-ethoxy-1-methyl-2-oxoethyl) -urea (HOE-095404)-benzoxazol-2-yl-oxy) -phenoxy]-ethyl propionate (fenoxaprop-ethyl), N-benzoyl-N- (3-chloro-4-fluoro-phenyl) -DL-alanine isopropyl ester (ryegrass-isopropyl ester), N-benzoyl-N- (3-chloro-4-fluoro-phenyl) -L-alanine isopropyl ester (ryegrass-isopropyl ester-L), N-benzoyl-N- (3-chloro-4-fluoro-phenoxy) -DL-alanine methyl ester (ryegrass-methyl ester), [ 2-chloro-4-fluoro-5- (1, 3, 4, 5, 6, 7-hexahydro-1, 3-dioxo-2H-isoindol-2-yl) -phenoxy.]Amyl acetate (flumiclorac-pentyl), 5- (2-chloro-4-trifluoromethyl-phenoxy) -2-nitro-benzoic acid ethoxycarbonyl methyl ester (fluoroglycofen-ethyl ester), 1- (4-chloro-3- (2, 2, 3, 3, 3-pentafluoro-propoxymethyl) -phenyl) -5-phenyl-1H-1, 2, 4-triazole-3-carboxamide (imazalil), 1-isopropyl-2-chloro-5- (3, 6-dihydro-3-methyl-2, 6-dioxo-4-trifluoromethyl-1 (2H) -pyrimidinyl) -benzoate (fluprolil), 9-hydroxy-9H-fluorene-9-carboxylic acid (fluorenylbutyric acid), (4-amino-3, 5-dichloro-6-fluoro-pyridin-2-yl-oxy) -acetic acid (fluroxypyr), N- (2, 6-difluorophenyl) -5-methyl-1, 2, 4-triazolo [1, 5-a [ ]]Pyrimidine-2-sulfonamides (DE-498), [ (2-chloro-4-fluoro-5- (tetrahydro-3-oxo-1H, 3H- [1, 3, 4)]Thiadiazolo- [3, 4-a]-pyridazin-1-ylidene) -amino-phenyl]-methyl thioacetate (fluthiacet-methyl, KIH-9201), 2-amino-4- (hydroxymethyl-phosphinyl) -butyric acid (ammonium salt) (glufosinate- (ammonium salt)), N-phosphonomethyl-glycine (-isopropylammonium salt) (glyphosate, -isopropylammonium salt), methyl 2- (4, 5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl) -4-methyl-benzoate (imazamethapyr), 2- (4, 5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl) -5-methyl-pyridine-3-carboxylic acid (imazamethapyr), 2- (4, 5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl) -5-methoxymethyl-pyridine-3-carboxylic acid (imazamox), 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-ethyl-pyridine-3-carboxylic acid (imazethapyr), n- (4, 6-dimethoxy-pyrimidin-2-yl) -N- (2-chloro-imidazo [1, 2-a)]-pyridin-3-yl-sulfonyl) -urea (azosulfuron), 4-hydroxy-3, 5-diiodo-benzonitrile (iodobenzonitrile), N-dimethyl-N- (4-isopropyl-phenyl) -urea (isoproturon), N- (3- (1-ethyl-1-ol)-methyl-propyl) -isoxazol-5-yl) -2, 6-dimethoxy-benzamide (isoxaben), (5-cyclopropyl-isoxazol-4-yl) - (2-methylsulfonyl-4-trifluoromethyl-phenyl) -methanone (isoxaflutole, RPA-201772), N- (3, 4-dichloro-phenyl) -N-methoxy-N-methylurea (linuron), (4-chloro-2-methyl-phenoxy) -acetic acid (2 m 4 chloro), 2- (4-chloro-2-methyl-phenoxy) -propionic acid (2 m 4 chloropropionic acid), 2-chloro-N- (2, 6-dimethyl-phenyl) -N- (1H-pyrazol-1-yl) -acetic acid (2 m 4 chloro-2-methyl-phenoxy) -propionic acid (2 m 4 chloropropionic acid), 2-chloro-N- (2, 6-dimethyl-phenyl) -N- ( -methyl) -acetamide (metazachlor), N- (4- (3, 4-dihydro-2-methoxy-2, 4, 4-trimethyl-2H-1-benzopyran-7-yl-oxy) -phenyl) -N-methoxy-N-methyl-urea (metobenzuron, UMP-488), N- (4-bromo-phenyl) -N-methoxy-N-methylurea (cumuron), 2-chloro-N- (2-ethyl-6-methyl-phenyl) -N- (2-methoxy-1-methyl-ethyl) -acetamide (propranolol), N- (2, 6-dichloro-3-methyl-phenyl) -5, 7-dimethoxy-1, 2, 4-triazolo [1, 5-a]-pyrimidine-2-sulfonamide (metosulam, DE-511), N- (3-chloro-4-methoxy-phenyl) -N, N-dimethyl-urea (metoxuron), 4-amino-6-tert-butyl-3-methylsulfanyl-1, 2, 4-triazin-5- (4H) -one (metribuzin), N- (4-methoxy-6-methyl-1, 3, 5-triazin-2-yl) -N- (2-methoxycarbonyl-phenylsulfonyl) -urea (metsulfuron-methyl), 2- (2-naphthyloxy) -N-phenylpropionamide (naphthylpropylamine), N-butyl-N- (3, 4-dichloro-phenyl) -N-methyl-urea (glufosinate), N- (4, 6-dimethoxy-pyrimidin-2-yl) -N- (3-dimethylcarbamoyl-pyridin-2-yl-sulfonyl) -urea (nicosulfuron), N- (4, 6-dimethyl-pyrimidin-2-yl) -N- (2-oxetan-3-yl-oxycarbonyl-phenylsulfonyl) -urea (oxasulfuron), 1, 1-dimethyl-4, 4-bipyridinium salt (paraquat), 1-amino-N- (1-ethyl-propyl) -3, 4-dimethyl-2, 6-dinitro-benzene (pendimethalin), N- (4, 6-bis-difluoromethoxy-pyrimidin-2-yl) -N- (2-methoxycarbonyl-phenylsulfonyl) -urea (primisulfuron-methyl ester), S-phenylmethyl N, N-dipropyl-thiocarbamate (prosulfocen), N- (4-methoxy-6-methyl-1, 3, 5-triazin-2-yl) -N- (2- (3, 3, 3-trifluoropropyl) -phenylsulfonyl) -urea (prosulfuron), 2-chloro-N- (2, 6-diethyl-phenyl) -N- (2-propoxy-ethyl) -acetamide (pretilachlor), 2-chloro-N-isopropyl-N-phenyl-acetamide (propamocarb), O- (6-chloro-3-phenyl-pyridazin-4-yl) thiocarbonate S-octyl ester (pyridate), 4- (2, 4-dichloro-benzoyl) -1,3-dimethyl-5- (4-methyl-phenylsulfonyloxy) -pyrazole (pyrazolate), 4- (2, 4-dichloro-benzoyl-1, 3-dimethyl-5- (phenylcarbonylmethoxy) -pyrazole (benzoxazole), N- (4, 6-dimethoxy-pyrimidin-2-yl) -N- (4-ethoxycarbonyl-1-methyl-pyrazol-5-yl-sulfonyl) -urea (pirimibenone-ethyl ester), 7-chloro-3-methyl-quinoline-8-carboxylic acid (quinaldic acid), N- (4, 6-dimethoxy-pyrimidin-2-yl) -N- (3-ethylsulfonyl-pyridin-2-yl-sulfo-N-propyl-5- (phenylmethyl-pyrimidin-2-yl) -urea (pyr-idinium-ethyl ester) Acyl) -urea (rimsulfuron), 6-chloro-2, 4-bis-ethylamino-1, 3, 5-triazine (simazine), 2- (2-chloro-4-methylsulfonyl-benzoyl) -cyclohexane-1, 3-dione (sulcotrione), 2- (2, 4-dichloro-5-methylsulfonylamino-phenyl) -4-difluoromethyl-5-methyl-2, 4-dihydro-3H-1, 2, 4-triazol-3-one (sulfentrazone, F-6285), N-phosphonomethyl-glycine-trimethylsulfonium salt (glyphosate), N- (4, 6-dimethoxy-pyrimidin-2-yl) -N- (2-ethylsulfonyl-imidazo [1, 2-a]Pyridine-3-sulfonamide (sulfofuron, MON-37500), 6-chloro-4-ethylamino-2-tert-butylamino-1, 3, 5-triazine (terbuthylazine), 2-tert-butylamino-4-ethylamino-6-methylsulfanyl-1, 3, 5-triazine (terbutrine), 2-chloro-N- (2, 6-dimethyl-phenyl) -N- (3-methoxy-2-thienyl-methyl) -acetamide (thenylchloride), 6- (6, 7-dihydro-6, 6-dimethyl-3H, 5H-pyrrolo [2, 1-c ] pyrrole]-1, 2, 4-thiadiazol-3-ylideneamino) -7-fluoro-4- (2-propynyl) -2H-1, 4-benzoxazin-3 (4H) -one (thizimin), N- (4-methoxy-6-methyl-1, 3, 5-triazin-2-yl) -N- (2-methoxycarbonyl-thiophen-3-yl-sulfonyl) -urea (thifensulfuron-methyl), 2- (ethoxyimino-propyl) -3-hydroxy-5- (2, 4, 6-trimethyl-phenyl) -2-cyclohexen-1-one (tralkoxydim), S- (2, 3, 3-trichloro-2-propenyl) di-isopropyl (thiocarbamate) (bisfenvinphos), N- (4-methoxy-6-methyl-1, 3, 5-triazin-2-yl) -N- [2- (2-chloro-ethoxy) -phenylsulfonyl]-urea (triasulfuron), N-methyl-N- (4-methoxy-6-methyl-1, 3, 5-triazin-2-yl) -N- (2-methoxycarbonyl-phenylsulfonyl) -urea (tribenuron-methyl), 2- (3, 5-dichloro-phenyl) -2- (2, 2, 2-trichloro-ethyl) -oxirane (imazalil), 1-amino-2, 6-dinitro-N, N-dipropyl-4-trifluoromethyl-benzene (trifluralin) - ("active compound of group 2").
Is very specialOf interest are the selective herbicidal compositions according to the invention, which are characterized by containing active compound combinations comprising: (a) an arylsulfonylaminocarbonyltriazolinone of the general formula (I) and/or a salt of a compound of the formula (I), wherein R1Represents hydrogen, amino, represents in each case optionally cyano-, fluorine-, chlorine-, methoxy-or ethoxy-substituted methyl, ethyl, n-or i-propyl, n-, i-, s-or t-butyl, ethenyl, propenyl, butenyl, ethynyl, propynyl, butynyl, methoxy, ethoxy, n-or i-propoxy, n-, i-, s-or t-butoxy, propenyloxy, butenyloxy, methylamino, ethylamino, n-or i-propylamino, n-, i-, s-or t-butylamino, dimethylamino or diethylamino, represents in each case optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n-or i-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylamino, cyclobutylamino, cyclopentylamino or cyclohexylamino, or represents in each case optionally cyano-, nitro-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n-or i-propyl-, n-, i-, s-or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, difluoromethoxy-or trifluoromethoxy-substituted phenyl or benzyl, R2Represents hydrogen, hydroxyl, mercapto, amino, cyano, fluorine, chlorine, bromine, represents methyl, ethyl, n-or i-propyl, n-, i-, s-or t-butyl, methoxy, ethoxy, n-or i-propoxy, n-, i-, s-or t-butoxy, methylthio, ethylthio, n-or i-propylthio, n-, i-, s-or t-butylthio, methylamino, ethylamino, n-or i-propylamino, n-, i-, s-or t-butylamino, dimethylamino, diethylamino, vinyl, propenyl, butenyl, ethynyl, propynyl, butynyl, propenyloxy, butenyloxy, propynyl, butynyl oxy, propenylthio, butenylthio, propynyl thio, butynyl thioPropenylamino, butenylamino, propynylamino or butynylamino, represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl or cyclohexylmethyl, in each case optionally substituted by cyano, nitro, fluoro, chloro, bromo, methyl, ethyl, n-or i-propyl, n-, iso-, sec-or tert-butyl-, trifluoromethyl-, methoxy-, ethoxy-, difluoromethoxy-or trifluoromethoxy-substituted phenyl, phenoxy, phenylthio, phenylamino or benzyl, R3Represents nitro, cyano, fluorine, chlorine, bromine, represents in each case optionally cyano-, fluorine-, chlorine-, methoxy-or ethoxy-substituted methyl, ethyl, n-or i-propyl, n-, i-, s-or t-butyl, acetyl, propionyl, n-or i-butyryl, methoxy, ethoxy, n-or i-propoxy, n-, i-, s-or t-butoxy, methoxycarbonyl, ethoxycarbonyl, n-or i-propoxycarbonyl, methylthio, ethylthio, n-or i-propylthio, n-, i-, s-or t-butylthio, methylsulfinyl, ethylsulfinyl, n-or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n-or i-propylsulfonyl, methylamino, ethylamino, n-or i-propylamino, n-, i-, s-or t-butylamino, ethenyl, propenyl, butenyl, propenyloxy, butenyloxy, propenylthio, butenylthio, propenylamino, butenylamino, ethynyl, propynyl, butynyl oxy, propynyl thio or butynyl thio, represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutanesAlkylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopentylamino or cyclohexylamino, or represents in each case optionally cyano-, nitro-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n-or i-propyl-, n-, i-, s-or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n-or i-propyloxy, n-, i-, s-or t-butyloxy, difluoromethoxy-or trifluoromethoxy-substituted phenyl, phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl or phenylamino, and R4Represents hydrogen, nitro, cyano, fluorine, chlorine, bromine, represents in each case optionally cyano-, fluorine-, chlorine-, methoxy-or ethoxy-substituted methyl, ethyl, n-or i-propyl, n-, i-, s-or t-butyl, acetyl, propionyl, n-or i-butyryl, methoxy, ethoxy, n-or i-propoxy, n-, i-, s-or t-butoxy, methoxycarbonyl, ethoxycarbonyl, n-or i-propoxycarbonyl, methylthio, ethylthio, n-or i-propylthio, n-, i-, s-or t-butylthio, methylsulfinyl, ethylsulfinyl, n-or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n-or i-propylsulfonyl, methylamino, ethylamino, n-or i-propylamino, n-, i-, s-or t-butylamino, ethenyl, propenyl, butenyl, propenyloxy, butenyloxy, propenylthio, butenylthio, propenylamino, butenylamino, ethynyl, propynyl, butynyl oxy, propynyl thio or butynyl thio, represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopentylamino or cyclohexylamino, or represents in each case optionally cyano-, nitro-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n-or i-propyl-, trifluoromethyl-, methoxy-, ethoxy-, n-or i-propyl-)Aryloxy, n-, iso-, sec-or tert-butyloxy, difluoromethoxy-or trifluoromethoxy-substituted phenyl, phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl or phenylamino ("active compounds of group 1") and (b) one or two compounds selected from the group of herbicides of group 2 comprising the active compounds listed below: 2-chloro-N- (ethoxymethyl) -N- (2-ethyl-6-methyl-phenyl) -acetamide (acetochlor), 2-chloro-6-nitro-3-phenoxy-aniline (aclonifen), 2-chloro-N- (methoxymethyl) -N- (2, 6-diethyl-phenyl) -acetamide (alachlor), N- (4, 6-dimethoxy-pyrimidin-2-yl) -N- (N-methyl-N-methylsulfonyl-sulfamoyl) -urea (amidosulfuror), 6-chloro-4-ethylamino-2-isopropylamino-1, 3, 5-triazine (atrazine), N-benzoyl-N- (3, 4-dichloro-phenyl) -DL-alanine ethyl ester (neodelphinine), 3-isopropyl-1H-2, 1, 3-benzothiadiazin-4 (3H) -one (bentazone), 5- (2, 4-dichloro-phenoxy) -2-nitro-benzoic acid methyl ester (bifenox), 2-bromo-3, 3-dimethyl-N- (1-methyl-1-phenyl-ethyl) -butyramide (bromobutylachlor), 3, 5-dibromo-4-hydroxy-benzaldehyde-O- (2, 4-dinitrophenyl) oxime (bromophenol oxime), 3, 5-dibromo-4-hydroxy-benzonitrile (bromoxynil), N-butoxymethyl-2-chloro-N- (2, 6-diethyl-phenyl) -acetamide (butachlor), bis- (2-methyl-propyl) -thiocarbamic acid S-ethyl ester (butachlor), 2- (4-chloro-2-fluoro-5- (2-chloro-2-ethoxycarbonyl-ethyl) -phenyl) -4-difluoromethyl-5-methyl-2, 4-dihydro-3H-1, 2, 4-triazol-3-one (carfentrazone-ethyl, F-8426), 2, 4-dichloro-1- (3-methoxy-4-nitro-phenoxy) -benzene (metoxyfen), 3-amino-2, 5-dichloro-benzoic acid (bentazon), 1, 3, 5-trichloro-2- (4-nitro-phenoxy) -benzene (cumyl ether), N- (4-methoxy-6-methyl-1, 3, 5-triazin-2-yl) -N- (2-chloro-phenylsulfonyl) -urea (chlorsulfuron), N- (3-chloro-4-methylphenyl) -N, N-dimethylurea (chlortoluron), N- (4, 6-dimethoxy-1, 3, 5-triazin-2-yl) -N- (2- (2-methoxy-ethoxy) -phenylsulfonyl) -urea (ethoferruron), 2- [4- (5-chloro-3-fluoro-pyridin-2-yl-oxy) -phenoxy ] -phenoxy]-propionic acid (R) - (2-propynyl) ester (clodinafop-propargyl), 3, 6-dichloro-pyridine-2-carboxylic acid (clopyralid), N- (4, 6-dimethoxy-pyrimidin-2-yl) -N- (3-chloro-4-methoxycarbonyl-1-methylpyrazol-5-yl-sulfonyl) -urea (R: (R) - (2-propynyl) -ureacycloparasulfuron, halosulfuron, NC-319), 3-chloro-2- [ (5-ethoxy-7-fluoro [1, 2, 4 ] -fluoro]Triazolo [1, 5-c]-pyrimidin-2-yl-sulfonyl) -amino]-benzoic acid methyl ester (cloransulam-methyl), 2-chloro-4-ethyl-amino-6- (1-cyano-1-methyl-ethylamino) -1, 3, 5-triazine (cyanazine), N- (4, 6-dimethoxy-pyrimidin-2-yl) -N- (2-cyclopropylcarbonyl-phenylsulfonyl) -urea (cyclosufmunon, AC-322140), 3, 6-dichloro-2-methoxy-benzoic acid (dicamba), (R) -2- (2, 4-dichloro-phenoxy) -propionic acid (high 2, 4-d-propionate), 2- [4- (2, 4-dichloro-phenoxy) -phenoxy.]Methyl propionate (diclofop-methyl ester), 1, 2-dimethyl-3, 5-diphenyl-1H-pyrazolium methylsulfate (difenoconazole), N- (2, 4-difluoro-phenyl) -2- (3-trifluoromethyl-phenoxy) -pyridine-3-carboxamide (diflufenican), 2-chloro-N- (2, 4-dimethyl-3-thienyl) -N- (2-methoxy-1-methyl-ethyl) -acetamide (dimethenamide, SAN-582), 2, 4-dichloro-phenoxyacetic acid (2, 4-d), 2-amino-4- (1-fluoro-1-methyl-ethyl) -6- (1-methyl-2- (3, 5-dimethyl-phenoxy) -ethylamino) -1, 3, 5-triazine (dimexyflam, IDH-1105), 6, 7-dihydro-bipyridine [1, 2-a: 2, 1-c]Pyrazinedinium (diquat), 2-difluoromethyl-4-isobutyl-6-trifluoromethyl-pyridine-3, 5-dithiocarboxylic acid S, S-dimethyl ester (dithiopyr), the sodium salt of N- (4, 6-dimethoxy-pyrimidin-2-yl) -N- (3-methoxycarbonyl-6-trifluoromethyl-pyridin-2-yl-sulfonyl) -urea (DPX-KE459), dipropylthiocarbamate S-ethyl Ester (EPTC), N-ethyl-N- (1, 2-dimethyl-propyl) -thiocarbamic acid S- (phenylmethyl) ester (dicamba), [ 2-chloro-5- (4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazole -3-yl) -4-fluoro-phenoxy]-ethyl acetate (ET-751), 2-chloro-5- (2-chloro-4-trifluoromethyl-phenoxy) -benzoic acid (S) - (2-ethoxy-1-methyl-2-oxoethyl) ester (ethoxyyfen), N- (4, 6-dimethoxy-pyrimidin-2-yl) -N- (2-ethoxy-phenoxysulfonyl) -urea (ethoxyysulofuron, HOE-095404), 2- [4- (6-chloro-benzoxazol-2-yl-oxy) -phenoxy ] -phenoxy]-ethyl propionate (fenoxaprop-ethyl), N-benzoyl-N- (3-chloro-4-fluoro-phenyl) -DL-alanine isopropyl ester (mevalonate-isopropyl ester), N-benzoyl-N- (3-chloro-4-fluoro-phenyl) -L-alanine isopropyl ester (mevalonate-isopropyl ester-L), N-benzoyl-N- (3-chloro-4-fluoro-phenoxy) -DL-alanine methyl ester (mevalonate-isopropyl ester-L)Mefenpyr-methyl ester), [ 2-chloro-4-fluoro-5- (1, 3, 4, 5, 6, 7-hexahydro-1, 3-dioxo-2H-isoindol-2-yl) -phenoxy]-pentyl acetate (flumiclorac-pentyl), 5- (2-amino-4-trifluoromethyl-phenoxy) -2-nitro-benzoic acid ethoxycarbonyl methyl ester (fluoroglycofen-ethyl ester), 1- (4-chloro-3- (2, 2, 3, 3, 3-pentafluoro-propoxymethyl) -phenyl) -5-phenyl-1H-1, 2, 4-triazole-3-carboxamide (imazalil), 1-isopropyl-2-chloro-5- (3, 6-dihydro-3-methyl-2, 6-dioxo-4-trifluoromethyl-1 (2H) -pyrimidinyl) -benzoic acid 1-isopropyl ester (flupropacil), 9-hydroxy-9H-fluorene-9-carboxylic acid (fluorenylbutyric acid), (4-amino-3, 5-dichloro-6-fluoro-pyridin-2-yl-oxy) -acetic acid (fluroxypyr), N- (2, 6-difluorophenyl) -5-methyl-1, 2, 4-triazolo [1, 5-a [ ] -methyl-acetic acid]Pyrimidine-2-sulfonamides (DE-498), [ (2-chloro-4-fluoro-5- (tetrahydro-3-oxo-1H, 3H- [1, 3, 4)]Thiadiazolo- [3, 4-a]-pyridazin-1-ylidene) -amino-phenyl]-methyl thioacetate (fluthiacet-methyl, KIH-9201), 2-amino-4- (hydroxymethyl-phosphinyl) -butyric acid (ammonium salt) (glufosinate- (ammonium salt)), N-phosphonomethyl-glycine (-isopropylammonium salt) (glyphosate, -isopropylammonium salt), methyl 2- (4, 5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl) -4-methyl-benzoate (imazamethapyr), 2- (4, 5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl) -5-methyl-pyridine-3-carboxylic acid (imazamethapyr), 2- (4, 5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl) -5-methoxymethyl-pyridine-3-carboxylic acid (imazamox), 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-ethyl-pyridine-3-carboxylic acid (imazethapyr), n- (4, 6-dimethoxy-pyrimidin-2-yl) -N- (2-chloro-imidazo [1, 2-a)]-pyridin-3-yl-sulfonyl) -urea (azosulfuron), 4-hydroxy-3, 5-diiodo-benzonitrile (ioxybenzonitrile), N, N-dimethyl-N- (4-isopropyl-phenyl) -urea (isoproturon), N- (3- (1-ethyl-1-methyl-propyl) -isoxazol-5-yl) -2, 6-dimethoxy-benzamide (isoxaben), (5-cyclopropyl-isoxazol-4-yl) - (2-methylsulfonyl-4-trifluoromethyl-phenyl) -methanone (isoxaflutole, RPA-201772), N- (3, 4-dichloro-phenyl) -N-methoxy-N-methylurea (linuron), (4-chloro-2-methyl-phenoxy) -acetic acid (2-methyl-4-chloro), 2- (4-chloro-2-methyl-phenoxy) -propionic acid (2 m-4-chloropropionic acid), 2-chloro-N- (2, 6-dimethyl-phenyl) -N- (1H-pyrazol-1-yl-methyl) -acetamide (metazachlor), N- (4- (3, 4-dihydro-2-methoxy-2, 4, 4-trimethyl-2H-1-benzopyran-7-yl-oxy) -phenyl) -N-methoxy-N-methyl-urea (metobenzuron, UMP-488), N- (4-bromo-phenyl) -N-methoxy-N-methylurea (cumuron), 2-chloro-N- (2-ethyl-6-methyl-phenyl) - N- (2-methoxy-1-methyl-ethyl) -acetamide (propranolol), N- (2, 6-dichloro-3-methyl-phenyl) -5, 7-dimethoxy-1, 2, 4-triazolo [1, 5-a [ ]]-pyrimidine-2-sulfonamide (metosulam, DE-511), N- (3-chloro-4-methoxy-phenyl) -N, N-dimethyl-urea (metoxuron), 4-amino-6-tert-butyl-3-methylsulfanyl-1, 2, 4-triazin-5- (4H) -one (metribuzin), N- (4-methoxy-6-methyl-1, 3, 5-triazin-2-yl) -N- (2-methoxycarbonyl-phenylsulfonyl) -urea (metsulfuron-methyl), 2- (2-naphthyloxy) -N-phenylpropionamide (naphthylpropylamine), N-butyl-N- (3, 4-dichloro-phenyl) -N-methyl-urea (glufosinate), N- (4, 6-dimethoxy-pyrimidin-2-yl) -N- (3-dimethylcarbamoyl-pyridin-2-yl-sulfonyl) -urea (nicosulfuron), N- (4, 6-dimethyl-pyrimidin-2-yl) -N- (2-oxetan-3-yl-oxycarbonyl-phenylsulfonyl) -urea (oxasulfuron), 1, 1-dimethyl-4, 4-bipyridinium salt (paraquat), 1-amino-N- (1-ethyl-propyl) -3, 4-dimethyl-2, 6-dinitro-benzene (pendimethalin), N- (4, 6-bis-difluoromethoxy-pyrimidin-2-yl) -N- (2-methoxycarbonyl-phenylsulfonyl) -urea (primisulfuron-methyl ester), S-phenylmethyl N, N-dipropyl-thiocarbamate (prosulfocen), N- (4-methoxy-6-methyl-1, 3, 5-triazin-2-yl) -N- (2- (3, 3, 3-trifluoropropyl) -phenylsulfonyl) -urea (prosulfuron), 2-chloro-N- (2, 6-diethyl-phenyl) -N- (2-propoxy-ethyl) -acetamide (pretilachlor), 2-chloro-N-isopropyl-N-phenyl-acetamide (propamocarb), O- (6-chloro-3-phenyl-pyridazin-4-yl) thiocarbonate S-octyl ester (pyridate), 4- (2, 4-dichloro-benzoyl) -1, 3-dimethyl-5- (4-methyl-phenylsulfonyloxy) -pyrazole (pyrazolate), 4- (2, 4-dichloro-benzoyl-1, 3-dimethyl-5- (phenylcarbonylmethoxy) -pyrazole (benzoxazole), N- (4, 6-dimethoxy-pyrimidin-2-yl) -N- (4-ethoxycarbonyl-1-methyl-pyrazol-5-yl-sulfonyl) - Urea (pyrazosulfuron-ethyl), 7-chloro-3-methyl-quinoline-8-carboxylic acid(quinmerac acid), N- (4, 6-dimethoxy-pyrimidin-2-yl) -N- (3-ethylsulfonyl-pyridin-2-yl-sulfonyl) -urea (rimsulfuron), 6-chloro-2, 4-bis-ethylamino-1, 3, 5-triazine (simazine), 2- (2-chloro-4-methylsulfonyl-benzoyl) -cyclohexane-1, 3-dione (sulcotrione), 2- (2, 4-dichloro-5-methylsulfonylamino-phenyl) -4-difluoromethyl-5-methyl-2, 4-dihydro-3H-1, 2, 4-triazol-3-one (sulfentrazone, f-6285), N-phosphonomethyl-glycine-trimethylsulfonium salt (glyphosate), N- (4, 6-dimethoxy-pyrimidin-2-yl) -N- (2-ethylsulfonyl-imidazo [1, 2-a ]]Pyridine-3-sulfonamide (sulfofuron, MON-37500), 6-chloro-4-ethylamino-2-tert-butylamino-1, 3, 5-triazine (terbuthylazine), 2-tert-butylamino-4-ethylamino-6-methylsulfanyl-1, 3, 5-triazine (terbutrine), 2-chloro-N- (2, 6-dimethyl-phenyl) -N- (3-methoxy-2-thienyl-methyl) -acetamide (thenylchloride), 6- (6, 7-dihydro-6, 6-dimethyl-3H, 5H-pyrrolo [2, 1-c ] pyrrole]-1, 2, 4-thiadiazol-3-ylideneamino) -7-fluoro-4- (2-propynyl) -2H-1, 4-benzoxazin-3 (4H) -one (thizimin), N- (4-methoxy-6-methyl-1, 3, 5-triazin-2-yl) -N- (2-methoxycarbonyl-thiophen-3-yl-sulfonyl) -urea (thifensulfuron-methyl), 2- (ethoxyimino-propyl) -3-hydroxy-5- (2, 4, 6-trimethyl-phenyl) -2-cyclohexen-1-one (tralkoxydim), S- (2, 3, 3-trichloro-2-propenyl) di-isopropyl (thiocarbamate) (bisfenvinphos), N- (4-methoxy-6-methyl-1, 3, 5-triazin-2-yl) -N- [2- (2-chloro-ethoxy) -phenylsulfonyl]-urea (triasulfuron), N-methyl-N- (4-methoxy-6-methyl-1, 3, 5-triazin-2-yl) -N- (2-methoxycarbonyl-phenylsulfonyl) -urea (tribenuron-methyl), 2- (3, 5-dichloro-phenyl) -2- (2, 2, 2-trichloro-ethyl) -oxirane (imazalil), 1-amino-2, 6-dinitro-N, N-dipropyl-4-trifluoromethyl-benzene (trifluralin) - ("active compound of group 2").
Instead of the pure active compounds of the formula (I), it is also possible to use salts of the compounds of the formula (I) with metals and/or basic nitrogen compounds in the active compound combinations according to the invention.
Preference is given here to salts of the compounds of the formula (I) with alkali metals, such as lithium, sodium, potassium, rubidium or cesium, very particularly with sodium or potassium, with alkaline earth metals, such as magnesium, calcium or barium, very particularly with calcium, or with earth metals, such as aluminum.
Furthermore, preference is given to salts of the compounds of the formula (I) with ammonia, with C1-C6Salts of alkyl-amines, e.g. with methylamine, ethylamine, n-or i-propylamine, n-, i-, s-or t-butylamine, n-, i-, s-or t-pentylamine, with di- (C)1-C6Salts of alkyl) -amines such as dimethylamine, diethylamine, dipropylamine, diisopropylamine, dibutylamine, diisobutylamine, di-sec-butylamine, dipentylamine, diisopentylamine, di-sec-pentylamine and dihexylamine with tri- (C)1-C4Salts of alkyl amines, such as trimethylamine, triethylamine, tripropylamine, tributylamine and N-ethyl-diisopropylamine, with C3-C6Salts of cycloalkylamines, e.g. cyclopentylamine or cyclohexylamine, with di- (C)3-C6Salts of-cycloalkyl) -amines, e.g. dicyclopentylamine or dicyclohexylamine, with N-C1-C4-alkyl-C3-C6Salts of cycloalkylamines, e.g. N-methyl-cyclopentylamine, N-ethyl-cyclopentylamine, N-methylcyclohexylamine or N-ethyl-cyclohexylamine, with N, N-di- (C)1-C4-alkyl) -C3-C6Salts of cycloalkyl-amines, e.g. N, N-dimethyl-cyclopentylamine, N, N-diethyl-cyclopentylamine, N, N-dimethyl-cyclohexylamine or N, N-diethyl-cyclohexylamine, with N-C1-C4-alkyl-di- (C)3-C6Salts of cycloalkyl) -amines, e.g. N-methyl-dicyclopentylamine, N-ethyl-dicyclopentylamine, N-methyl-dicyclohexylamine or N-ethyl-dicyclohexylamine, with phenyl-C1-C4Salts of alkyl-amines, e.g. benzylamine, 1-phenyl-ethylamine or 2-phenyl-ethylamine, with N-C1-C4-alkyl-phenyl-C1-C4Salts of alkyl-amines, e.g. N-methyl-benzylamine or N-ethyl-benzylamine, or with N, N-di- (C)1-C4-alkyl) -phenyl-C1-C4Salts of alkyl-amines, e.g. with N, N-dimethyl-benzylamine or N, N-diethylbenzylamine, orWith optionally condensed and/or C1-C4Salts of alkyl-substituted azines such as pyridine, quinoline, 2-methyl-pyridine, 3-methyl-pyridine, 4-methyl-pyridine, 2, 4-dimethylpyridine, 2, 5-dimethyl-pyridine, 2, 6-dimethylpyridine or 5-ethyl-2-methylpyridine.
Mention may be made, as basic compounds which can be used according to the invention for preparing the salts of the compounds of formula (I): alkali metal or alkaline earth metal acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkoxides, for example sodium acetate, potassium acetate or calcium acetate, lithium amide, sodium amide, potassium amide or calcium amide, sodium carbonate, potassium carbonate or calcium carbonate, sodium bicarbonate, potassium bicarbonate or calcium bicarbonate, lithium hydride, sodium hydride, potassium hydride or calcium hydride, lithium hydroxide, sodium hydroxide, potassium hydroxide or calcium hydroxide, sodium methoxide or potassium methoxide, sodium ethoxide or potassium ethoxide, sodium n-or i-propoxide or potassium n-or i-propoxide, sodium n-, i-, s-or t-butoxide or potassium n-, i-, s-or t-butoxide.
Examples of compounds of the formula (I) which can be used as mixing partners according to the invention are: 2- (2-chloro-phenylsulfonylaminocarbonyl) -, 2- (2-bromo-phenylsulfonylaminocarbonyl) -, 2- (2-methyl-phenylsulfonylaminocarbonyl) -, 2- (2-ethyl-phenylsulfonylaminocarbonyl) -, 2- (2-n-propyl-phenylsulfonylaminocarbonyl) -, 2- (2-isopropyl-phenylsulfonylaminocarbonyl) -, 2- (2-trifluoromethyl-phenylsulfonylaminocarbonyl) -, 2- (2-methoxy-phenylsulfonylaminocarbonyl) -, 2- (2-ethoxy-phenylsulfonylaminocarbonyl) -, 2- (2-n-propoxy-phenylsulfonylaminocarbonyl) -, 2- (2-isopropoxy-phenylsulfonylaminocarbonyl) -, 2- (2-difluoromethoxy-phenylsulfonylaminocarbonyl) -, 2- (2-trifluoromethoxy-phenylsulfonylaminocarbonyl) -, 2- (2-methoxycarbonyl-phenylsulfonylaminocarbonyl) -, 2- (2-ethoxycarbonyl-phenylsulfonylaminocarbonyl) -, 2- (2-n-propoxycarbonyl-phenylsulfonylaminocarbonyl) -, 2- (2-isopropoxycarbonyl-phenylsulfonylaminocarbonyl) -and 2- (2-chloro-6-methyl-phenylsulfonylaminocarbonyl) -4-methyl-5-methoxy-2, 4-dihydro-3H-1, 2, 4-triazol-3-one, -4-methyl-5-ethoxy-2, 4-dihydro-3H-1, 2, 4-triazol-3-one, -4-methyl-5-n-propoxy-2, 4-dihydro-3H-1, 2, 4-triazol-3-one, -4-methyl-5-isopropoxy-2, 4-dihydro-3H-1, 2, 4-triazol-3-one, -4-methyl-5-trifluoroethoxy-2, 4-dihydro-3H-1, 2, 4-triazol-3-one, -4-methyl-5-methylsulfanyl-2, 4-dihydro-3H-1, 2, 4-triazol-3-one, -4-methyl-5-ethylsulfanyl-2, 4-dihydro-3H-1, 2, 4-triazol-3-one, -4-methoxy-5-methyl-2, 4-dihydro-3H-1, 2, 4-triazol-3-one, -4-methoxy-5-ethyl-2, 4-dihydro-3H-1, 2, 4-triazol-3-one, -4-cyclopropyl-5-methoxy-2, 4-dihydro-3H-1, 2, 4-triazol-3-one, -4-methoxy-5-n-propyl-2, 4-dihydro-3H 1, 2, 4-triazol-3-one, -4-cyclopropyl-5-ethoxy-2, 4-dihydro-3H-1, 2, 4-triazol-3-one, -4-cyclopropyl-5-n-propoxy-2, 4-dihydro-3H-1, 2, 4-triazol-3-one, -4-cyclopropyl-5-isopropoxy-2, 4-dihydro-3H-1, 2, 4-triazol-3-one and-4-cyclopropyl-5-trifluoroethoxy-2, 4-dihydro-3H-1, 2, 4-triazol-3-one, and also the sodium and potassium salts of these compounds.
Mixed components of the formula (I) which may be particularly emphasized are the compounds 2- (2-methoxycarbonyl-phenylsulphonylaminocarbonyl) -4-methyl-5-n-propoxy-2, 4-dihydro-3H-1, 2, 4-triazol-3-one (I-1) and 2- (2-trifluoromethoxy-phenylsulphonylaminocarbonyl) -4-methyl-5-methoxy-2, 4-dihydro-3H-1, 2, 4-triazol-3-one (I-2) and their sodium salts (I-1, Na salts), (I-2, Na salts).
Compounds of formula (I) are described in the above-mentioned patent applications or patent specifications.
Active compounds of group 2 which may be particularly emphasized as mixed components are: amidosulfuron, bentazon, bromoxynil, carfentrazone (-ethyl), clodinafop (-propagyl), clopyralid, chlorsulfuron, chlortoluron, cyclosufuron, 2, 4-D, diclofop (-methyl ester), diconazole, diflufenican, DPX-KE459, ET-751, ethoxfen, fenoxaprop (-ethyl ester), fluoroglycofen (-ethyl ester), flupapacil, fluroxypyr, isoproturon, 2-methyl-4-chloropropionic acid, metasulam, metribuzin, metsulfuron (-methyl ester), pendimethalin, prosulfon (-methyl ester), oxime, triasulfuron, tribenuron (-methyl ester) or trifluralin.
Of this group, metribuzin is of particular interest as a blending component.
It has surprisingly been found that the active compound combinations of arylsulfonylaminocarbonyltriazolinone of the formula (I) as described above and the active compounds of group 2 above, in addition to being well tolerated by useful plants, have particularly high herbicidal activity and can be used for a wide variety of crop plants, in particular wheat, and in addition also for corn, barley and rice, for the selective control of weeds.
Surprisingly, the herbicidal activity of the active compound combinations according to the invention of the compounds of the abovementioned groups 1 and 2 is much higher than the sum of the effects of the individual compounds.
This means that not only a complementary effect but also an unexpected synergistic effect is present. The novel active compound combinations are well tolerated by a wide variety of crop plants and are also effective in controlling difficult-to-control weeds. The novel active compound combinations are therefore valuable supplements to selective herbicides. For example, the active compound combinations according to the invention can be used in connection with the following plants:dicotyledonous weed species: mustard (Sinapis), striga (Lepidium), cleavers (Galium), chickweed (Stellaria), Matricaria (Matricaria), camomile (anthuria), moleplant (antheria), pepperweed (galinoga), Chenopodium (Chenopodium), nettle (Urtica), Senecio (Senecio), Amaranthus (Amaranthus), Portulaca (Portulaca), Xanthium (Xanthium), spiranthes (convolulus), sweetpotato (ipoea), Polygonum (Polygonum), Sesbania (Sesbania), Ambrosia (Ambrosia), thistle (Cirsium), thistle (Carduus), picea (sonchushu), Solanum (Solanum), weldwort (ropria), pinus (Rotala), lindera (lindera), meadowfoam (vetiveria), meadowfoam (vetiver), vetiver (Viola), treta (violacea (alopoecio), vetiveria (Viola), treta (vetiveria (Viola), trex (vetiveria (rodaula), treta (treta), tremula (tremula), tremula) and vetiver (tremula)Genus (Centaurea), Trifolium (Trifolium), Ranunculus (Ranunculus) and Taraxacum (Taraxacuum).Dicotyledonous crop species: cotton (Gossypium), soybean (Glycine), Beta, carrot (Daucus), Phaseolus (Phaseolus), Pisum, Solanum (Solanum), flax (Linum), Ipomoea (Ipomoea), Brassica (Vicia), Nicotiana (Nicotiana), Lycopersicon (Lycopersicon), peanut (Arachis), mustard (Brassica), lettuce (Lactuca), cantaloupe (cucum) and cantaloupe (Cucurbita).Monocotyledonous weed species: echinochloa (Echinochloa), Setaria (Setaria), Panicum (Panicum), Digitaria (Digitaria), Phleum (Phleum), Poa (Poa), Festuca (Festuca), Gryllus (Eleusine), Brachiaria (Brachiaria), Lolium (Lolium), Bromus (Bromus), Avena (Avena), Cyperus (Cyperus), Phalaris (Solomon), Agropyron (Agropyron), Cygnon, Populus (Monchoria), Fimbristylis (Fimbristylis), Phaeocharia (Sagittaria), Eleocharis (Eleocharis), Bromus (Scissus), Paspalum (Paalum), Isemun, Spirochaeta (Sphaera), Sphacelaria (Agrocybe), Echinochloaria (Agropyron), Agropyron (Agropyron) and Aleuropa (Aleuropa).Monocotyledonous crop species: oryza (Oryza), Zea (Zea), Triticum (Triticum), Hordeum (Hordeum), Avena (Avena), Secale (Secale), Zea (Sorghum), Panicum (Panicum), Saccharum (Saccharum), Ananas (Ananas), Asparagus (Asparagus) and Allium (Allium).
However, the use of the active compound combinations according to the invention is not limited in any way by these species, but extends in the same way to other plants.
The synergistic action of the active compound combinations according to the invention is particularly pronounced at specific concentration ratios. However, the weight ratio of active compound in the active compound combination can be varied within a relatively wide range. In general, from 0.01 to 1000 parts by weight, preferably from 0.05 to 500 parts by weight, particularly preferably from 0.1 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 active compound combinations can be converted into the customary formulations, for example solutions, emulsions, wettable powders, suspensions, dusts, fine powders, pastes, soluble powders, granules, suspended emulsifiable concentrates, natural and synthetic materials impregnated with active compound, and microencapsulations in polymeric substances. These formulations can be 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. If water is used as extender, it is also possible to use, for example, organic solvents as auxiliary solvents. Suitable as liquid solvents are mainly: aromatic compounds, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic compounds and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example mineral oil fractions, mineral and vegetable oils, alcohols, such as butanol or ethylene glycol and ethers and esters thereof, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulfoxide, and water. Suitable solid carriers are: for example ammonium salts and ground natural minerals such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as highly disperse silica, alumina and silicates; suitable solid carriers for granules are: for example crushed and crushed natural minerals such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of organic and inorganic powders, and granules of organic substances such as: such as sawdust, coconut shells, corn cobs and tobacco stems; suitable as emulsifiers and/or foaming agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates and protein hydrolysates; suitable dispersants are: such as lignin sulfite waste liquor and methyl cellulose. In the formulation, binders such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or emulsions, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, and natural phospholipids such as cephalins and lecithins, and synthetic phospholipids may be used. 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 dyes, such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and micronutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc. In general, the preparations contain 0.1 to 95% by weight, preferably 0.5 to 90% by weight, of active compound.
The active compound combinations according to the invention are generally used in the form of ready-prepared mixtures, but the active compounds contained in the active compound combinations can also be formulated individually and mixed at the time of use, i.e. used in the form of container mixtures.
The novel active compound combinations can be used as such or in their formulations, and also as mixtures with other known herbicides, either as ready-prepared formulations or container mixtures. They may also be mixed with other known active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellents, growth substances, plant nutrients and agents for improving soil structure. For special application purposes, in particular when applied post-emergently, it is furthermore advantageous to incorporate into the formulation mineral or vegetable oils (for example the commercial product "Oleo DuPont 11E") or ammonium salts, for example ammonium sulphate or ammonium thiocyanate, which are tolerated by plants as further additives.
These novel active compound combinations can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They can be used in a conventional manner, for example by pouring, spraying, atomizing, dusting or scattering.
The active compound combinations according to the invention can be applied pre-or post-emergence to the plants. That is to say by pre-and post-emergence methods. It may also be incorporated into the soil prior to cultivation.
The good herbicidal activity of the novel active compound combinations can be illustrated by the following examples. Although each active compound showed a weak point with respect to herbicidal activity, the combinations showed very good herbicidal activity without exception, which exceeded the simple addition effect.
If the herbicidal activity of the active compound combinations is greater than the activity of the respective active compound applied, then there is always a synergistic effect in the herbicide.
The expected activity for a given combination of two herbicides can be calculated as follows (see COLBY, s.r.: calculate the synergistic and antagonistic effect of the herbicidal combination),weed (Haw)Pages 15, 20-22, 1967): if X is the percentage of damage caused by the herbicide a (active compound of formula I) at an application rate of p kg/ha, and Y is the percentage of damage caused by the herbicide B (active compound of formula II) at an application rate of q kg/ha, and E is the expected degree of damage of the herbicides a and B at application rates of p and q kg/ha, then E is X + Y- (X · Y/100).
If the actual damage is greater than the calculated value, the activity of the combination is more than additive, i.e. it shows a synergistic effect.
The following examples show that the herbicidal activity of the active compound combinations according to the invention against weeds is found to exceed the calculated activity, i.e. the novel active compound combinations act synergistically.
Example a post-emergence test solvents: 5 parts by weight of acetone emulsifier: 1 part by weight of alkylaryl polyglycol ether
To prepare a suitable formulation of the active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added, and the emulsifiable concentrate is diluted with water to the desired concentration.
The test plants, which are 5-15cm high, are sprayed with the active compound preparation in such a way that a specific desired amount of active compound is applied per unit area. The concentration of the spray liquor is chosen so that the amount of the specifically desired active compound is applied at 1000L of water per hectare. After three weeks, the degree of injury to the plants was visually assessed as the percentage injury compared to the growth of untreated controls. Description of the data:
0% no effect (as in untreated control)
Complete destruction of 100%
The active compounds, the application rates, the test plants and the results are given in the following tables A-1 and A-2, the abbreviations used in the tables having the following meanings: (I-1, Na salt) ═ sodium salt of 2- (2-methoxycarbonyl-phenylsulfonylaminocarbonyl) -4-methyl-5-n-propoxy-2, 4-dihydro-3H-1, 2, 4-triazol-3-one (I-1); (I-2, Na salt) ═ sodium salt of 2- (2-trifluoromethoxy-phenylsulfonylaminocarbonyl) -4-methyl-5-methoxy-2, 4-dihydro-3H-1, 2, 4-triazol-3-one (I-2); measured injury or effect (in%); calculated value-injury or effect (in%) calculated using Colby s formula. TABLE A-1: post-emergence test/greenhouse
Active compound or active compound combination Application ratio g/ha (active compound) Injury or Effect on test plants%
Wind grass (Aperaspica-Venti) Black brome (Bromusececlinus)
Measured value Calculated value Measured value Calculated value
Metribuzin-known- 60 20 0
(I-1, Na salt) -known- 15 70 60
Metribuzin + (I-1, Na salt) -the invention- 60+15 95 76 80 60
Table A-2: post-emergence test/greenhouse
Active compound or active compound combination Application ratio g/ha (active compound) Injury or Effect on test plants%
Wind grass (Aperaspica-Venti) Setaria viridis (Setariaviridis)
Measured value Calculated value Measured value Calculated value
Metribuzin-known- 60 20 50
(I-2, Na salt) -known- 15 60 90
Metribuzin + (I-2, Na salt) -the invention- 60+15 98 68 100 95

Claims (4)

1. Herbicidal composition, characterized in that it contains an effective amount of an active compound combination comprising:
(a)2- (2-methoxycarbonyl-phenylsulfonylaminocarbonyl) -4-methyl-5-n-propoxy-2, 4-dihydro-3H-1, 2, 4-triazol-3-one (I-1) or 2- (2-trifluoromethoxy-phenylsulfonylaminocarbonyl) -4-methyl-5-methoxy-2, 4-dihydro-3H-1, 2, 4-triazol-3-one (I-2) or the sodium salts of these compounds- "active compounds of group 1", and
(b)
4-amino-6-tert-butyl-3-methylsulfanyl-1, 2, 4-triazin-5 (4H) -one-metribuzin- "active compound of group 2",
wherein 0.1 to 100 parts by weight of the active compound of group 2 are used per part by weight of the active compound of formula (I).
2. A method for controlling weeds, characterized in that active compound combinations according to claim 1 are allowed to act on weeds or their habitat.
3. Use of active compound combinations according to claim 1 for controlling weeds.
4. A process for preparing herbicidal compositions, characterized in that active compound combinations according to claim 1 are mixed with extenders and/or surfactants.
HK00103483.8A 1996-09-23 1997-09-10 Selective herbicides based on arylsulphonylaminocarbonyltriazolinones HK1024141B (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19638887.2 1996-09-23
DE19638887A DE19638887A1 (en) 1996-09-23 1996-09-23 Selective herbicides based on arylsulfonylaminocarbonyltriazolinones
PCT/EP1997/004947 WO1998012923A1 (en) 1996-09-23 1997-09-10 Selective herbicides based on arylsulphonylaminocarbonyltriazolinones

Publications (2)

Publication Number Publication Date
HK1024141A1 HK1024141A1 (en) 2000-10-05
HK1024141B true HK1024141B (en) 2004-12-31

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