DE2833274C2 - - Google Patents
Info
- Publication number
- DE2833274C2 DE2833274C2 DE2833274A DE2833274A DE2833274C2 DE 2833274 C2 DE2833274 C2 DE 2833274C2 DE 2833274 A DE2833274 A DE 2833274A DE 2833274 A DE2833274 A DE 2833274A DE 2833274 C2 DE2833274 C2 DE 2833274C2
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- oxo
- isopropyl
- imidazolin
- formula
- 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.)
- Expired
Links
- 241000196324 Embryophyta Species 0.000 claims description 38
- -1 methylcyclohexyl Chemical group 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 22
- 239000004480 active ingredient Substances 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 20
- GCFBDIVEVTXDJZ-UHFFFAOYSA-N pyrrolo[3,4-e]benzimidazole-2,4-dione Chemical compound O=C1C2=NC(=O)N=C2C2=CN=CC2=C1 GCFBDIVEVTXDJZ-UHFFFAOYSA-N 0.000 claims description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- QWKWVHKVAFMGCQ-UHFFFAOYSA-N 4,5-dihydroimidazol-1-yl benzoate Chemical class C=1C=CC=CC=1C(=O)ON1CCN=C1 QWKWVHKVAFMGCQ-UHFFFAOYSA-N 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 239000004009 herbicide Substances 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- 239000011541 reaction mixture Substances 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- HQUZQJGGHDJRBK-UHFFFAOYSA-N 2-(4,5-dihydroimidazol-1-yl)benzamide Chemical class NC(=O)C1=CC=CC=C1N1C=NCC1 HQUZQJGGHDJRBK-UHFFFAOYSA-N 0.000 claims description 7
- RCVABMZVLZNJAG-UHFFFAOYSA-N 2-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)benzoic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=CC=CC=C1C(O)=O RCVABMZVLZNJAG-UHFFFAOYSA-N 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- 125000002636 imidazolinyl group Chemical group 0.000 claims description 6
- 239000003586 protic polar solvent Substances 0.000 claims description 6
- 229910000102 alkali metal hydride Inorganic materials 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000002689 soil Substances 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000008046 alkali metal hydrides Chemical class 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 230000002363 herbicidal effect Effects 0.000 claims description 4
- 210000000056 organ Anatomy 0.000 claims description 4
- 230000001850 reproductive effect Effects 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000011261 inert gas Substances 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 3
- VSGNJFMJPJJRTQ-UHFFFAOYSA-N 2-(4,5-dihydroimidazol-1-yl)benzoic acid Chemical class OC(=O)C1=CC=CC=C1N1C=NCC1 VSGNJFMJPJJRTQ-UHFFFAOYSA-N 0.000 claims description 2
- 241000209504 Poaceae Species 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- AJYGRXHBUHSMGM-UHFFFAOYSA-N n,n-dimethyl-2-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)benzamide Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=CC=CC=C1C(=O)N(C)C AJYGRXHBUHSMGM-UHFFFAOYSA-N 0.000 claims description 2
- ASABJKPCGJIDPA-UHFFFAOYSA-N n-methyl-2-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)benzamide Chemical compound CNC(=O)C1=CC=CC=C1C1=NC(=O)C(C)(C(C)C)N1 ASABJKPCGJIDPA-UHFFFAOYSA-N 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 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 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 2
- 239000000460 chlorine Chemical group 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 230000003287 optical effect Effects 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 150000003254 radicals Chemical group 0.000 claims 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 1
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- GGCPXJNERJTHHL-UHFFFAOYSA-N 2-(4-ethyl-4-methyl-5-oxo-1h-imidazol-2-yl)benzoic acid Chemical compound O=C1C(CC)(C)NC(C=2C(=CC=CC=2)C(O)=O)=N1 GGCPXJNERJTHHL-UHFFFAOYSA-N 0.000 claims 1
- MJIOKNVFAISNKW-UHFFFAOYSA-N 2-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)-n-prop-2-ynylbenzamide Chemical compound O=C1C(C(C)C)(C)NC(C=2C(=CC=CC=2)C(=O)NCC#C)=N1 MJIOKNVFAISNKW-UHFFFAOYSA-N 0.000 claims 1
- VRCWMVAZCHCQOK-UHFFFAOYSA-N 2-chloro-6-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)benzoic acid Chemical compound O=C1C(C(C)C)(C)NC(C=2C(=C(Cl)C=CC=2)C(O)=O)=N1 VRCWMVAZCHCQOK-UHFFFAOYSA-N 0.000 claims 1
- NQGJPFVVEXLXLP-UHFFFAOYSA-N 2-imidazolidin-1-ylbenzamide Chemical compound N1(CNCC1)C1=C(C(=O)N)C=CC=C1 NQGJPFVVEXLXLP-UHFFFAOYSA-N 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- YHSJKUNHKAONQP-UHFFFAOYSA-N 3-chloro-2-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)benzoic acid Chemical compound O=C1C(C(C)C)(C)NC(C=2C(=CC=CC=2Cl)C(O)=O)=N1 YHSJKUNHKAONQP-UHFFFAOYSA-N 0.000 claims 1
- DYUWOEUKAVJUDA-UHFFFAOYSA-N 3-methyl-4-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)benzoic acid Chemical class N1C(=O)C(C(C)C)(C)N=C1C1=CC=C(C(O)=O)C=C1C DYUWOEUKAVJUDA-UHFFFAOYSA-N 0.000 claims 1
- DICZSROBUFDHMN-UHFFFAOYSA-N 4-methyl-3-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)benzoic acid Chemical class N1C(=O)C(C(C)C)(C)N=C1C1=CC(C(O)=O)=CC=C1C DICZSROBUFDHMN-UHFFFAOYSA-N 0.000 claims 1
- LYJHVEDILOKZCG-UHFFFAOYSA-N Allyl benzoate Chemical compound C=CCOC(=O)C1=CC=CC=C1 LYJHVEDILOKZCG-UHFFFAOYSA-N 0.000 claims 1
- QSFHVFFHOGLSNS-UHFFFAOYSA-N CC(C)C1(C(=O)NC(=N1)C2=CC=CC=C2C(=O)C(C3=CC=CC=C3)O)C Chemical compound CC(C)C1(C(=O)NC(=N1)C2=CC=CC=C2C(=O)C(C3=CC=CC=C3)O)C QSFHVFFHOGLSNS-UHFFFAOYSA-N 0.000 claims 1
- QPJVMBTYPHYUOC-UHFFFAOYSA-N Methyl benzoate Natural products COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000012050 conventional carrier Substances 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- VZZHETXUUPYYHK-UHFFFAOYSA-N methyl 3-methyl-4-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)benzoate Chemical class CC1=CC(C(=O)OC)=CC=C1C1=NC(C)(C(C)C)C(=O)N1 VZZHETXUUPYYHK-UHFFFAOYSA-N 0.000 claims 1
- AOYFCVMCWIATKW-UHFFFAOYSA-N methyl 4-methyl-3-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)benzoate Chemical compound COC(=O)C1=CC=C(C)C(C=2NC(=O)C(C)(C(C)C)N=2)=C1 AOYFCVMCWIATKW-UHFFFAOYSA-N 0.000 claims 1
- 229940095102 methyl benzoate Drugs 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- BZJVAJQORNKATD-UHFFFAOYSA-N pent-3-en-2-yl 2-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)benzoate Chemical compound CC=CC(C)OC(=O)C1=CC=CC=C1C1=NC(C)(C(C)C)C(=O)N1 BZJVAJQORNKATD-UHFFFAOYSA-N 0.000 claims 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims 1
- 210000004994 reproductive system Anatomy 0.000 claims 1
- UWGRCKWVHUFXSH-UHFFFAOYSA-M sodium;2-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)benzoate Chemical compound [Na+].N1C(=O)C(C(C)C)(C)N=C1C1=CC=CC=C1C([O-])=O UWGRCKWVHUFXSH-UHFFFAOYSA-M 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000155 melt Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 244000062793 Sorghum vulgare Species 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 244000025254 Cannabis sativa Species 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- 240000005979 Hordeum vulgare Species 0.000 description 4
- 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 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
- 244000098338 Triticum aestivum Species 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- IRZIRPLBWVYQDJ-UHFFFAOYSA-N 3-methyl-3-propan-2-ylimidazo[1,2-b]isoindole-2,5-dione Chemical compound C1=CC=C2C3=NC(=O)C(C(C)C)(C)N3C(=O)C2=C1 IRZIRPLBWVYQDJ-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 240000008042 Zea mays Species 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 3
- BQTTUSNEYLQOEW-UHFFFAOYSA-N prop-2-ynyl 2-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)benzoate Chemical compound O=C1C(C(C)C)(C)NC(C=2C(=CC=CC=2)C(=O)OCC#C)=N1 BQTTUSNEYLQOEW-UHFFFAOYSA-N 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 240000006995 Abutilon theophrasti Species 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 244000075850 Avena orientalis Species 0.000 description 2
- 241001251296 Carex pendula Species 0.000 description 2
- 241001273783 Carex scoparia Species 0.000 description 2
- 241000234653 Cyperus Species 0.000 description 2
- 235000002848 Cyperus flabelliformis Nutrition 0.000 description 2
- 244000075634 Cyperus rotundus Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 244000299507 Gossypium hirsutum Species 0.000 description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 244000081757 Phalaris arundinacea Species 0.000 description 2
- 235000014676 Phragmites communis Nutrition 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 235000007230 Sorghum bicolor Nutrition 0.000 description 2
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000009969 flowable effect Effects 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910000103 lithium hydride Inorganic materials 0.000 description 2
- 235000019713 millet Nutrition 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- JOTLWQUUMCNABN-UHFFFAOYSA-N n-(4,5-dihydroimidazol-1-yl)benzamide Chemical class C=1C=CC=CC=1C(=O)NN1CCN=C1 JOTLWQUUMCNABN-UHFFFAOYSA-N 0.000 description 2
- 229920005552 sodium lignosulfonate Polymers 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- LAFRKWDMWGHGPG-UHFFFAOYSA-N 1,3-dioxoisoindole-2-carboxamide Chemical compound C1=CC=C2C(=O)N(C(=O)N)C(=O)C2=C1 LAFRKWDMWGHGPG-UHFFFAOYSA-N 0.000 description 1
- PXFFXNAOZWBKFX-UHFFFAOYSA-N 2-(4,4-diethyl-5-oxo-1h-imidazol-2-yl)-n,n-diethylbenzamide Chemical compound CCN(CC)C(=O)C1=CC=CC=C1C1=NC(=O)C(CC)(CC)N1 PXFFXNAOZWBKFX-UHFFFAOYSA-N 0.000 description 1
- RCDZKMLNHXMMRK-UHFFFAOYSA-N 2-(4-cyclohexyl-4-methyl-5-oxo-1h-imidazol-2-yl)-n-prop-2-ynylbenzamide Chemical compound N=1C(=O)C(C)(C2CCCCC2)NC=1C1=CC=CC=C1C(=O)NCC#C RCDZKMLNHXMMRK-UHFFFAOYSA-N 0.000 description 1
- IWQONEPXLXVQOB-UHFFFAOYSA-N 2-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)-n-propan-2-ylbenzamide Chemical compound CC(C)NC(=O)C1=CC=CC=C1C1=NC(C)(C(C)C)C(=O)N1 IWQONEPXLXVQOB-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- OPNZQLLYCURAKN-UHFFFAOYSA-N 3-but-1-ynyl-2-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)benzamide Chemical compound CCC#CC1=CC=CC(C(N)=O)=C1C1=NC(C)(C(C)C)C(=O)N1 OPNZQLLYCURAKN-UHFFFAOYSA-N 0.000 description 1
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 1
- 240000001592 Amaranthus caudatus Species 0.000 description 1
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 1
- 244000237956 Amaranthus retroflexus Species 0.000 description 1
- 244000036975 Ambrosia artemisiifolia Species 0.000 description 1
- 235000003133 Ambrosia artemisiifolia Nutrition 0.000 description 1
- 235000007320 Avena fatua Nutrition 0.000 description 1
- 241000209764 Avena fatua Species 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 244000056139 Brassica cretica Species 0.000 description 1
- 244000024671 Brassica kaber Species 0.000 description 1
- 235000014750 Brassica kaber Nutrition 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- 241000217446 Calystegia sepium Species 0.000 description 1
- 235000000509 Chenopodium ambrosioides Nutrition 0.000 description 1
- 244000098897 Chenopodium botrys Species 0.000 description 1
- 235000005490 Chenopodium botrys Nutrition 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241000234646 Cyperaceae Species 0.000 description 1
- 241001110525 Cyperus strigosus Species 0.000 description 1
- 241000208296 Datura Species 0.000 description 1
- 240000008853 Datura stramonium Species 0.000 description 1
- 244000152970 Digitaria sanguinalis Species 0.000 description 1
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 1
- 244000058871 Echinochloa crus-galli Species 0.000 description 1
- 244000078127 Eleusine coracana Species 0.000 description 1
- 235000013499 Eleusine coracana subsp coracana Nutrition 0.000 description 1
- 235000009432 Gossypium hirsutum Nutrition 0.000 description 1
- 241000207890 Ipomoea purpurea Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241001290529 Kyllinga clade Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 235000011999 Panicum crusgalli Nutrition 0.000 description 1
- 235000014968 Peltiphyllum peltatum Nutrition 0.000 description 1
- 244000104677 Peltiphyllum peltatum Species 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 244000275012 Sesbania cannabina Species 0.000 description 1
- 241000533293 Sesbania emerus Species 0.000 description 1
- 240000003461 Setaria viridis Species 0.000 description 1
- 235000002248 Setaria viridis Nutrition 0.000 description 1
- 240000006410 Sida spinosa Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 235000007244 Zea mays Nutrition 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical class CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- ZEGHYVCQGVNWME-UHFFFAOYSA-N n-benzyl-2-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)benzamide Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=CC=CC=C1C(=O)NCC1=CC=CC=C1 ZEGHYVCQGVNWME-UHFFFAOYSA-N 0.000 description 1
- OQPOZZCJABQTCS-UHFFFAOYSA-N n-but-2-enyl-2-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)benzamide Chemical compound CC=CCNC(=O)C1=CC=CC=C1C1=NC(=O)C(C)(C(C)C)N1 OQPOZZCJABQTCS-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
- C07D233/70—One oxygen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US82245877A | 1977-08-08 | 1977-08-08 | |
| US05/822,459 US4122275A (en) | 1977-08-08 | 1977-08-08 | Imidazolinyl benzamides as herbicidal agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2833274A1 DE2833274A1 (de) | 1979-02-22 |
| DE2833274C2 true DE2833274C2 (en, 2012) | 1989-07-13 |
Family
ID=27124643
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19782833274 Granted DE2833274A1 (de) | 1977-08-08 | 1978-07-28 | Imidazolinylbenzoate |
Country Status (24)
| Country | Link |
|---|---|
| JP (1) | JPS5464637A (en, 2012) |
| AR (1) | AR222973A1 (en, 2012) |
| AT (1) | AT364571B (en, 2012) |
| AU (1) | AU518293B2 (en, 2012) |
| BG (1) | BG32411A3 (en, 2012) |
| BR (1) | BR7805062A (en, 2012) |
| CA (1) | CA1109878A (en, 2012) |
| CH (1) | CH639957A5 (en, 2012) |
| CS (1) | CS204033B2 (en, 2012) |
| DD (1) | DD138595A5 (en, 2012) |
| DE (1) | DE2833274A1 (en, 2012) |
| DK (1) | DK157927C (en, 2012) |
| ES (2) | ES472433A1 (en, 2012) |
| FR (1) | FR2400018A1 (en, 2012) |
| GB (1) | GB2004537B (en, 2012) |
| GR (1) | GR72789B (en, 2012) |
| HU (1) | HU181841B (en, 2012) |
| IL (1) | IL55064A (en, 2012) |
| IT (1) | IT1107482B (en, 2012) |
| NL (1) | NL7808228A (en, 2012) |
| NZ (1) | NZ187812A (en, 2012) |
| SE (1) | SE448729B (en, 2012) |
| UA (1) | UA6015A1 (en, 2012) |
| YU (2) | YU41316B (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991007089A1 (de) * | 1989-11-21 | 1991-05-30 | Hoechst Aktiengesellschaft | Herbizide mittel |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3474020D1 (en) * | 1983-08-02 | 1988-10-20 | American Cyanamid Co | Imidazolidinones, and imidazolidinethiones, process for the preparation thereof, and use of said compounds as herbicidal agents |
| EP0133311A3 (en) * | 1983-08-02 | 1987-12-23 | American Cyanamid Company | Substituted imidazolinyl benzoic acids, esters and salts and use thereof as herbicidal agents |
| DE3340595A1 (de) * | 1983-11-10 | 1985-05-23 | Hoechst Ag, 6230 Frankfurt | Imidazolinone, verfahren zu ihrer herstellung und ihre verwendung im pflanzenschutz |
| DE3340594A1 (de) * | 1983-11-10 | 1985-05-23 | Hoechst Ag, 6230 Frankfurt | 2-arylsubstituierte imidazolinone, verfahren zu ihrer herstellung und ihre verwendung im pflanzenschutz |
| DE3345901A1 (de) * | 1983-12-20 | 1985-06-27 | Hoechst Ag, 6230 Frankfurt | 1-acylimidazolinone, verfahren zu ihrer herstellung und ihre verwendung in der landwirtschaft |
| ATE64597T1 (de) * | 1984-02-10 | 1991-07-15 | American Cyanamid Co | Regio und optische isomere von imidazolinyltoluols|ure, deren ester und salze, verfahren zu deren herstellung und deren anwendung als herbizide. |
| GB8507808D0 (en) * | 1985-03-26 | 1985-05-01 | Shell Int Research | Heterocyclic herbicides |
| US4726835A (en) * | 1985-12-02 | 1988-02-23 | Idemitsu Kosan Company Limited | Herbicidal and plant growth regulating imidazoline derivatives |
| EP0412577A1 (de) | 1986-05-09 | 1991-02-13 | Hoechst Aktiengesellschaft | Herbizide Mittel |
| US4895588A (en) * | 1987-07-01 | 1990-01-23 | Ciba-Geigy Corporation | Substituted imidazolones having herbicidal activity |
| US5525578A (en) * | 1989-11-21 | 1996-06-11 | Hoechst Aktiengesellschaft | Herbicidal agents containing imidazole herbicide and ether sulfate surfactants |
| US5062881A (en) * | 1989-12-20 | 1991-11-05 | American Cyanamid Company | 2-(1-substituted-2-imidazolin-2-yl)benzoic and nicotinic acids and a method for their preparation |
| US8367669B2 (en) | 2005-06-15 | 2013-02-05 | Vanderbilt University | Inhibitors of hemeprotein-catalyzed lipid peroxidation |
| US9133212B1 (en) | 2005-06-15 | 2015-09-15 | Vanderbilt University | Inhibitors of hemeprotein-catalyzed lipid peroxidation |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1176660B (de) * | 1963-07-05 | 1964-08-27 | Beiersdorf & Co A G P | Verfahren zur Herstellung von triaryl-substituierten Imidazolinonen-4(5) |
| US3645965A (en) * | 1967-10-23 | 1972-02-29 | Sankyo Co | Stabilization of synthetic polymers with imidazolidine compounds |
| US3687971A (en) * | 1970-06-22 | 1972-08-29 | Merck & Co Inc | 4-(pyrrolyl)-salicylic acid derivatives |
-
1978
- 1978-07-03 IL IL55064A patent/IL55064A/xx active IP Right Grant
- 1978-07-07 AU AU37867/78A patent/AU518293B2/en not_active Expired
- 1978-07-07 GR GR56732A patent/GR72789B/el unknown
- 1978-07-10 NZ NZ187812A patent/NZ187812A/xx unknown
- 1978-07-17 AR AR272981A patent/AR222973A1/es active
- 1978-07-20 CA CA307,740A patent/CA1109878A/en not_active Expired
- 1978-07-24 YU YU1758/78A patent/YU41316B/xx unknown
- 1978-07-25 IT IT50457/78A patent/IT1107482B/it active Protection Beyond IP Right Term
- 1978-07-26 GB GB7831112A patent/GB2004537B/en not_active Expired
- 1978-07-28 DE DE19782833274 patent/DE2833274A1/de active Granted
- 1978-08-03 CH CH828978A patent/CH639957A5/de not_active IP Right Cessation
- 1978-08-04 NL NL787808228A patent/NL7808228A/xx unknown
- 1978-08-07 SE SE7808451A patent/SE448729B/sv not_active IP Right Cessation
- 1978-08-07 BR BR7805062A patent/BR7805062A/pt unknown
- 1978-08-07 DK DK348278A patent/DK157927C/da not_active IP Right Cessation
- 1978-08-07 BG BG040610A patent/BG32411A3/xx unknown
- 1978-08-08 ES ES472433A patent/ES472433A1/es not_active Expired
- 1978-08-08 DD DD78207175A patent/DD138595A5/xx not_active IP Right Cessation
- 1978-08-08 UA UA2646369A patent/UA6015A1/uk unknown
- 1978-08-08 CS CS785182A patent/CS204033B2/cs unknown
- 1978-08-08 JP JP9658178A patent/JPS5464637A/ja active Granted
- 1978-08-08 HU HU78AE540A patent/HU181841B/hu unknown
- 1978-08-08 FR FR7823383A patent/FR2400018A1/fr active Granted
- 1978-08-08 AT AT0577478A patent/AT364571B/de active
-
1979
- 1979-04-10 ES ES479467A patent/ES479467A1/es not_active Expired
-
1982
- 1982-10-07 YU YU2255/82A patent/YU40967B/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991007089A1 (de) * | 1989-11-21 | 1991-05-30 | Hoechst Aktiengesellschaft | Herbizide mittel |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8128 | New person/name/address of the agent |
Representative=s name: SPOTT, G., DIPL.-CHEM. DR.RER.NAT., PAT.-ANW., 800 |
|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition |