DE10143083A1 - Selektive Herbizide auf Basis von substituierten Arylsulfonylaminocarbonyltriazolinonen und Safenern - Google Patents
Selektive Herbizide auf Basis von substituierten Arylsulfonylaminocarbonyltriazolinonen und SafenernInfo
- Publication number
- DE10143083A1 DE10143083A1 DE10143083A DE10143083A DE10143083A1 DE 10143083 A1 DE10143083 A1 DE 10143083A1 DE 10143083 A DE10143083 A DE 10143083A DE 10143083 A DE10143083 A DE 10143083A DE 10143083 A1 DE10143083 A1 DE 10143083A1
- Authority
- DE
- Germany
- Prior art keywords
- cyano
- methoxy
- ethoxy
- methyl
- halogen
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 239000004009 herbicide Substances 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 44
- 239000004480 active ingredient Substances 0.000 claims abstract description 24
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims abstract description 5
- -1 hydroxy, amino Chemical group 0.000 claims description 446
- 229910052736 halogen Inorganic materials 0.000 claims description 121
- 150000002367 halogens Chemical group 0.000 claims description 120
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 97
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 90
- 239000000460 chlorine Chemical group 0.000 claims description 90
- 229910052801 chlorine Inorganic materials 0.000 claims description 90
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 90
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 82
- 125000004432 carbon atom Chemical group C* 0.000 claims description 70
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 70
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 68
- 125000000217 alkyl group Chemical group 0.000 claims description 48
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 43
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 43
- 229910052794 bromium Inorganic materials 0.000 claims description 43
- CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical group FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims description 42
- 239000001257 hydrogen Substances 0.000 claims description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims description 42
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 42
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 40
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 40
- 229910052731 fluorine Inorganic materials 0.000 claims description 39
- 239000011737 fluorine Substances 0.000 claims description 39
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 37
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 37
- 125000001725 pyrenyl group Chemical group 0.000 claims description 36
- 125000001153 fluoro group Chemical group F* 0.000 claims description 34
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 31
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 29
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 25
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 25
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 25
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 24
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 24
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 24
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 24
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 24
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 23
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 20
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 19
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 18
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 17
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 17
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 16
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 16
- 125000003282 alkyl amino group Chemical group 0.000 claims description 15
- 125000004414 alkyl thio group Chemical group 0.000 claims description 15
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 15
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 15
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 14
- 125000000304 alkynyl group Chemical group 0.000 claims description 14
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 13
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 13
- 125000005108 alkenylthio group Chemical group 0.000 claims description 12
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 12
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 11
- JVJQPDTXIALXOG-UHFFFAOYSA-N nitryl fluoride Chemical compound [O-][N+](F)=O JVJQPDTXIALXOG-UHFFFAOYSA-N 0.000 claims description 11
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Chemical group C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 10
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 10
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 10
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 10
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 10
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 claims description 10
- 125000005981 pentynyl group Chemical group 0.000 claims description 10
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 10
- 125000006323 alkenyl amino group Chemical group 0.000 claims description 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 9
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 9
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 9
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 9
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 9
- 239000011734 sodium Substances 0.000 claims description 9
- 229910052708 sodium Inorganic materials 0.000 claims description 9
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 8
- 125000005109 alkynylthio group Chemical group 0.000 claims description 8
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 8
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 244000038559 crop plants Species 0.000 claims description 7
- 230000002363 herbicidal effect Effects 0.000 claims description 7
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 7
- 125000004468 heterocyclylthio group Chemical group 0.000 claims description 7
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 5
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- 239000005601 Propoxycarbazone Substances 0.000 claims description 4
- 125000006263 dimethyl aminosulfonyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])S(*)(=O)=O 0.000 claims description 4
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 4
- 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 claims description 4
- JTHMVYBOQLDDIY-UHFFFAOYSA-N methyl 2-[(4-methyl-5-oxo-3-propoxy-1,2,4-triazole-1-carbonyl)sulfamoyl]benzoate Chemical compound O=C1N(C)C(OCCC)=NN1C(=O)NS(=O)(=O)C1=CC=CC=C1C(=O)OC JTHMVYBOQLDDIY-UHFFFAOYSA-N 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical group [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 4
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 239000004606 Fillers/Extenders Substances 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims description 3
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 3
- 125000005110 aryl thio group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 150000007514 bases Chemical class 0.000 claims description 3
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 3
- 125000000131 cyclopropyloxy group Chemical group C1(CC1)O* 0.000 claims description 3
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 3
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 3
- GINFBXXYGUODAT-UHFFFAOYSA-N flucarbazone Chemical compound O=C1N(C)C(OC)=NN1C(=O)NS(=O)(=O)C1=CC=CC=C1OC(F)(F)F GINFBXXYGUODAT-UHFFFAOYSA-N 0.000 claims description 3
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000006319 alkynyl amino group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 21
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 2
- 241000927721 Tritia Species 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000006311 cyclobutyl amino group Chemical group [H]N(*)C1([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- JRQGDDUXDKCWRF-UHFFFAOYSA-M sodium;n-(2-methoxycarbonylphenyl)sulfonyl-4-methyl-5-oxo-3-propoxy-1,2,4-triazole-1-carboximidate Chemical compound [Na+].O=C1N(C)C(OCCC)=NN1C(=O)[N-]S(=O)(=O)C1=CC=CC=C1C(=O)OC JRQGDDUXDKCWRF-UHFFFAOYSA-M 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 abstract description 18
- 230000008635 plant growth Effects 0.000 abstract 1
- 244000045561 useful plants Species 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 description 21
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 16
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 15
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 11
- 238000009472 formulation Methods 0.000 description 10
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 9
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 8
- 125000006193 alkinyl group Chemical group 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000008187 granular material Substances 0.000 description 5
- 229910052700 potassium Inorganic materials 0.000 description 5
- 239000011591 potassium Substances 0.000 description 5
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
- 241000209094 Oryza Species 0.000 description 4
- 240000008042 Zea mays Species 0.000 description 4
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241000209219 Hordeum Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 235000013339 cereals Nutrition 0.000 description 3
- 235000005822 corn Nutrition 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000009566 rice Nutrition 0.000 description 3
- 239000011435 rock Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
- 239000008158 vegetable oil Substances 0.000 description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 2
- JYYNAJVZFGKDEQ-UHFFFAOYSA-N 2,4-Dimethylpyridine Chemical compound CC1=CC=NC(C)=C1 JYYNAJVZFGKDEQ-UHFFFAOYSA-N 0.000 description 2
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2,5-dimethylpyridine Chemical compound CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 2
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 235000005781 Avena Nutrition 0.000 description 2
- 244000075850 Avena orientalis Species 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 description 2
- 235000021506 Ipomoea Nutrition 0.000 description 2
- 241000207783 Ipomoea Species 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical class [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 241000209117 Panicum Species 0.000 description 2
- 235000006443 Panicum miliaceum subsp. miliaceum Nutrition 0.000 description 2
- 235000009037 Panicum miliaceum subsp. ruderale Nutrition 0.000 description 2
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 241000209056 Secale Species 0.000 description 2
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 2
- 244000062793 Sorghum vulgare Species 0.000 description 2
- 241000209140 Triticum Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
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- JNMBQGIZTCTCRT-UHFFFAOYSA-N n-cyclopentyl-n-methylcyclopentanamine Chemical compound C1CCCC1N(C)C1CCCC1 JNMBQGIZTCTCRT-UHFFFAOYSA-N 0.000 description 1
- FUUUBHCENZGYJA-UHFFFAOYSA-N n-cyclopentylcyclopentanamine Chemical compound C1CCCC1NC1CCCC1 FUUUBHCENZGYJA-UHFFFAOYSA-N 0.000 description 1
- AGVKXDPPPSLISR-UHFFFAOYSA-N n-ethylcyclohexanamine Chemical compound CCNC1CCCCC1 AGVKXDPPPSLISR-UHFFFAOYSA-N 0.000 description 1
- SRTHFWNTKVOSBA-UHFFFAOYSA-N n-ethylcyclopentanamine Chemical compound CCNC1CCCC1 SRTHFWNTKVOSBA-UHFFFAOYSA-N 0.000 description 1
- PXSXRABJBXYMFT-UHFFFAOYSA-N n-hexylhexan-1-amine Chemical compound CCCCCCNCCCCCC PXSXRABJBXYMFT-UHFFFAOYSA-N 0.000 description 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- KKTBUCVHSCATGB-UHFFFAOYSA-N n-methylcyclopentanamine Chemical compound CNC1CCCC1 KKTBUCVHSCATGB-UHFFFAOYSA-N 0.000 description 1
- ZZJKGVPMLGIOTF-UHFFFAOYSA-N n-pentan-2-ylpentan-2-amine Chemical compound CCCC(C)NC(C)CCC ZZJKGVPMLGIOTF-UHFFFAOYSA-N 0.000 description 1
- JACMPVXHEARCBO-UHFFFAOYSA-N n-pentylpentan-1-amine Chemical compound CCCCCNCCCCC JACMPVXHEARCBO-UHFFFAOYSA-N 0.000 description 1
- 229940042880 natural phospholipid Drugs 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Substances [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/12—Oxygen or sulfur atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (20)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10143083A DE10143083A1 (de) | 2001-09-03 | 2001-09-03 | Selektive Herbizide auf Basis von substituierten Arylsulfonylaminocarbonyltriazolinonen und Safenern |
| CNA2008101664714A CN101480183A (zh) | 2001-09-03 | 2002-08-21 | 基于取代的芳基磺酰基氨基羰基三唑啉酮类化合物和安全剂的选择性除草剂 |
| AU2002333488A AU2002333488B2 (en) | 2001-09-03 | 2002-08-21 | Selective herbicides based on substituted arylsulfonylaminocarbonyl triazolinones and safeners |
| HU0401490A HUP0401490A3 (en) | 2001-09-03 | 2002-08-21 | Selective herbicides based on substituted arylsulfonylaminocarbonyl triazolinones and safeners |
| UA2004042513A UA76511C2 (en) | 2001-09-03 | 2002-08-21 | Agent and a method to control undesired plants |
| KR1020107008409A KR20100044929A (ko) | 2001-09-03 | 2002-08-21 | 치환된 아릴설포닐아미노카보닐 트리아졸리논 및 약해 완화제를 기본으로 하는 선택적 제초제 |
| MXPA04002002A MXPA04002002A (es) | 2001-09-03 | 2002-08-21 | Herbicidas selectivos a base de arilsulfonilaminocarbonil-triazolinonas substituidas y de protectores. |
| US10/488,037 US7615514B2 (en) | 2001-09-03 | 2002-08-21 | Selective herbicides based on substituted arylsulphonylaminocarbonyl-triazolinones and safeners |
| CA2458922A CA2458922C (en) | 2001-09-03 | 2002-08-21 | Selective herbicides based on substituted arylsulphonylaminocarbonyl-triazolinones and safeners |
| PCT/EP2002/009329 WO2003020692A1 (de) | 2001-09-03 | 2002-08-21 | Selektive herbizide auf basis von substituierten arylsulfonylaminocarbonyltriazolinonen und safenern |
| AT02797547T ATE518831T1 (de) | 2001-09-03 | 2002-08-21 | Selektive herbizide auf basis von substituierten arylsulfonylaminocarbonyltriazolinonen und safenern |
| EP02797547A EP1427699B1 (de) | 2001-09-03 | 2002-08-21 | Selektive herbizide auf basis von substituierten arylsulfonylaminocarbonyltriazolinonen und safenern |
| CNA028216997A CN1578763A (zh) | 2001-09-03 | 2002-08-21 | 基于取代的芳基磺酰基氨基羰基三唑啉酮类化合物和安全剂的选择性除草剂 |
| BR0212271-5A BR0212271A (pt) | 2001-09-03 | 2002-08-21 | Herbicidas seletivos na base de arilsulfonilaminocarbonil-triazolinonas substituìdas e protetores |
| KR10-2004-7002811A KR20040029047A (ko) | 2001-09-03 | 2002-08-21 | 치환된 아릴설포닐아미노카보닐 트리아졸리논 및 약해완화제를 기본으로 하는 선택적 제초제 |
| RU2004110236/04A RU2289926C2 (ru) | 2001-09-03 | 2002-08-21 | Гербицидное средство, способ борьбы с сорными растениями |
| PL02368860A PL368860A1 (en) | 2001-09-03 | 2002-08-21 | Selective herbicides based on substituted arylsulfonylaminocarbonyl triazolinones and safeners |
| JP2003524963A JP2005501900A (ja) | 2001-09-03 | 2002-08-21 | 置換アリールスルホニルアミノカルボニル−トリアゾリノン及び薬害軽減剤に基づく選択的除草剤 |
| ARP020103192A AR036673A1 (es) | 2001-09-03 | 2002-08-26 | Composiciones herbicidas selectivas a base de arilsulfonilaminocarboniltriazolinonas substituidas y protectores, su empleo para la lucha contra las plantas indeseables, procedimientos para la lucha contra las plantas indeseables, y procedimiento para la obtencion de composicion herbicida |
| JP2010177354A JP2011006430A (ja) | 2001-09-03 | 2010-08-06 | 置換アリールスルホニルアミノカルボニル−トリアゾリノン及び薬害軽減剤に基づく選択的除草剤 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10143083A DE10143083A1 (de) | 2001-09-03 | 2001-09-03 | Selektive Herbizide auf Basis von substituierten Arylsulfonylaminocarbonyltriazolinonen und Safenern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE10143083A1 true DE10143083A1 (de) | 2003-03-20 |
Family
ID=7697517
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE10143083A Withdrawn DE10143083A1 (de) | 2001-09-03 | 2001-09-03 | Selektive Herbizide auf Basis von substituierten Arylsulfonylaminocarbonyltriazolinonen und Safenern |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US7615514B2 (https=) |
| EP (1) | EP1427699B1 (https=) |
| JP (2) | JP2005501900A (https=) |
| KR (2) | KR20100044929A (https=) |
| CN (2) | CN101480183A (https=) |
| AR (1) | AR036673A1 (https=) |
| AT (1) | ATE518831T1 (https=) |
| AU (1) | AU2002333488B2 (https=) |
| BR (1) | BR0212271A (https=) |
| CA (1) | CA2458922C (https=) |
| DE (1) | DE10143083A1 (https=) |
| HU (1) | HUP0401490A3 (https=) |
| MX (1) | MXPA04002002A (https=) |
| PL (1) | PL368860A1 (https=) |
| RU (1) | RU2289926C2 (https=) |
| UA (1) | UA76511C2 (https=) |
| WO (1) | WO2003020692A1 (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102026545A (zh) * | 2008-02-12 | 2011-04-20 | 北美爱利思达生命科学有限责任公司 | 控制多余植物的方法 |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5599944A (en) * | 1987-03-24 | 1997-02-04 | Bayer Aktiengesellschaft | Intermediates for herbicidal sulphonylaminocarbonyltriazolinones having substituents which are bonded via sulphur |
| US5380863A (en) * | 1989-10-12 | 1995-01-10 | Bayer Aktiengesellschaft | Herbicidal sulphonylaminocarbonyltriazolinones having substituents which are bonded via sulphur |
| US5085684A (en) * | 1988-05-09 | 1992-02-04 | Bayer Aktiengesellschaft | Herbicidal sulphonylaminocarbonyltriazolinones having substituents which are bonded via sulphur |
| US5149356A (en) * | 1988-05-09 | 1992-09-22 | Bayer Aktiengesellschaft | Herbicidal sulphonylaminocarbonyltriazolinones having substituents which are bonded via sulphur |
| US5276162A (en) * | 1988-05-09 | 1994-01-04 | Bayer Aktiengesellschaft | Herbicidal sulphonylaminocarbonyltriazolinones having substituents which are bonded via sulphur |
| US5541337A (en) * | 1989-04-13 | 1996-07-30 | Bayer Aktiengesellschaft | Substituted 5-alkoxy-1,2,4-triazol-3-(thi)ones |
| US5094683A (en) * | 1988-05-09 | 1992-03-10 | Bayer Aktiengesellschaft | Sulphonylaminocarbonyltriazolinones |
| US5057144A (en) * | 1988-05-09 | 1991-10-15 | Bayer Aktiengesellschaft | Sulphonylaminocarbonyltriazolinones |
| US5241074A (en) * | 1988-05-09 | 1993-08-31 | Bayer Aktiengesellschaft | Sulphonylaminocarbonyltriazolinones |
| US5300480A (en) * | 1989-04-13 | 1994-04-05 | Bayer Aktiengesellschaft | Herbicidal sulphonylaminocarbonyltriazolinones having two substituents bonded via oxygen |
| US5534486A (en) * | 1991-04-04 | 1996-07-09 | Bayer Aktiengesellschaft | Herbicidal sulphonylaminocarbonyl triazolinones having substituents bonded via oxygen |
| CA2201596A1 (en) | 1994-10-05 | 1996-04-18 | Klaus Helmut Muller | Sulfonylaminocarbonyltriazolinones with substituents bound by oxygen and sulphur |
| DE19508119A1 (de) * | 1995-03-08 | 1996-09-12 | Bayer Ag | Sulfonylaminocarbonyltriazolinone mit Halogenalkylthio-Substituenten |
| DE19508118A1 (de) * | 1995-03-08 | 1996-09-12 | Bayer Ag | Sulfonylaminocarbonyltriazoline mit Halogenalkoxy-Substituenten |
| DE19525162A1 (de) * | 1995-07-11 | 1997-01-16 | Bayer Ag | Sulfonylamino(thio)carbonylverbindungen |
| DE19621522A1 (de) * | 1996-05-29 | 1997-12-04 | Hoechst Schering Agrevo Gmbh | Neue N-Acylsulfonamide, neue Mischungen aus Herbiziden und Antidots und deren Verwendung |
| DE19638887A1 (de) * | 1996-09-23 | 1998-03-26 | Bayer Ag | Selektive Herbizide auf Basis von Arylsulfonylaminocarbonyltriazolinonen |
| DE19742951A1 (de) * | 1997-09-29 | 1999-04-15 | Hoechst Schering Agrevo Gmbh | Acylsulfamoylbenzoesäureamide, diese enthaltende nutzpflanzenschützende Mittel und Verfahren zu ihrer Herstellung |
| AU719657B2 (en) * | 1998-01-21 | 2000-05-11 | Syngenta Participations Ag | Herbicidal composition |
| DE19827855A1 (de) * | 1998-06-23 | 1999-12-30 | Hoechst Schering Agrevo Gmbh | Kombinationen aus Herbiziden und Safenern |
| DE19940860A1 (de) * | 1999-08-27 | 2001-03-01 | Bayer Ag | Selektive Herbizide auf Basis eines substituierten Phenylsulfonyl aminocarbonyltriazolinons und Safenern II |
| DE19940859A1 (de) | 1999-08-27 | 2001-03-01 | Bayer Ag | Selektive Herbizide auf Basis eines substituierten Phenylsulfonylaminocarbonyltriazolinons und Safenern |
| AU775959B2 (en) * | 1999-11-17 | 2004-08-19 | Bayer Cropscience Ag | Selective herbicides based upon 2,6-disubstituted pyridine derivatives |
| DE10031825A1 (de) * | 2000-06-30 | 2002-01-10 | Bayer Ag | Selektive Herbizide auf Basis von Arylsulfonylaminocarbonyltriazolinonen |
| DE10112104A1 (de) * | 2001-03-14 | 2002-09-26 | Bayer Ag | Herbizide auf Basis von substituierten Arylketonen |
| DE10142334A1 (de) * | 2001-08-30 | 2003-03-20 | Bayer Cropscience Ag | Herbizide auf Basis von substituierten Arylketonen |
| DE10142333A1 (de) * | 2001-08-30 | 2003-03-20 | Bayer Cropscience Ag | Herbizide Mischungen auf Basis von substituierten Arylketonen |
-
2001
- 2001-09-03 DE DE10143083A patent/DE10143083A1/de not_active Withdrawn
-
2002
- 2002-08-21 BR BR0212271-5A patent/BR0212271A/pt not_active Application Discontinuation
- 2002-08-21 KR KR1020107008409A patent/KR20100044929A/ko not_active Ceased
- 2002-08-21 MX MXPA04002002A patent/MXPA04002002A/es active IP Right Grant
- 2002-08-21 WO PCT/EP2002/009329 patent/WO2003020692A1/de not_active Ceased
- 2002-08-21 UA UA2004042513A patent/UA76511C2/uk unknown
- 2002-08-21 HU HU0401490A patent/HUP0401490A3/hu unknown
- 2002-08-21 US US10/488,037 patent/US7615514B2/en not_active Expired - Lifetime
- 2002-08-21 JP JP2003524963A patent/JP2005501900A/ja not_active Withdrawn
- 2002-08-21 CA CA2458922A patent/CA2458922C/en not_active Expired - Lifetime
- 2002-08-21 EP EP02797547A patent/EP1427699B1/de not_active Expired - Lifetime
- 2002-08-21 PL PL02368860A patent/PL368860A1/xx unknown
- 2002-08-21 KR KR10-2004-7002811A patent/KR20040029047A/ko not_active Ceased
- 2002-08-21 AT AT02797547T patent/ATE518831T1/de active
- 2002-08-21 AU AU2002333488A patent/AU2002333488B2/en not_active Expired
- 2002-08-21 RU RU2004110236/04A patent/RU2289926C2/ru active
- 2002-08-21 CN CNA2008101664714A patent/CN101480183A/zh active Pending
- 2002-08-21 CN CNA028216997A patent/CN1578763A/zh active Pending
- 2002-08-26 AR ARP020103192A patent/AR036673A1/es not_active Application Discontinuation
-
2010
- 2010-08-06 JP JP2010177354A patent/JP2011006430A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| JP2005501900A (ja) | 2005-01-20 |
| MXPA04002002A (es) | 2004-06-07 |
| BR0212271A (pt) | 2004-10-19 |
| HUP0401490A2 (hu) | 2004-12-28 |
| KR20040029047A (ko) | 2004-04-03 |
| ATE518831T1 (de) | 2011-08-15 |
| RU2004110236A (ru) | 2005-10-20 |
| RU2289926C2 (ru) | 2006-12-27 |
| CN1578763A (zh) | 2005-02-09 |
| US20060234864A1 (en) | 2006-10-19 |
| WO2003020692A1 (de) | 2003-03-13 |
| JP2011006430A (ja) | 2011-01-13 |
| CA2458922A1 (en) | 2003-03-13 |
| US7615514B2 (en) | 2009-11-10 |
| AR036673A1 (es) | 2004-09-29 |
| HUP0401490A3 (en) | 2005-10-28 |
| KR20100044929A (ko) | 2010-04-30 |
| UA76511C2 (en) | 2006-08-15 |
| CN101480183A (zh) | 2009-07-15 |
| CA2458922C (en) | 2012-04-17 |
| PL368860A1 (en) | 2005-04-04 |
| EP1427699B1 (de) | 2011-08-03 |
| EP1427699A1 (de) | 2004-06-16 |
| AU2002333488B2 (en) | 2008-11-20 |
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