DE1670716A1 - Herbizide Zusammensetzungen - Google Patents
Herbizide ZusammensetzungenInfo
- Publication number
- DE1670716A1 DE1670716A1 DE19661670716 DE1670716A DE1670716A1 DE 1670716 A1 DE1670716 A1 DE 1670716A1 DE 19661670716 DE19661670716 DE 19661670716 DE 1670716 A DE1670716 A DE 1670716A DE 1670716 A1 DE1670716 A1 DE 1670716A1
- Authority
- DE
- Germany
- Prior art keywords
- trifluoromethylbenzimidazole
- nitro
- bromo
- chloro
- azole
- 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.)
- Pending
Links
- 230000002363 herbicidal effect Effects 0.000 title claims description 19
- 239000000203 mixture Substances 0.000 title claims description 14
- 150000003839 salts Chemical class 0.000 claims description 15
- 150000001556 benzimidazoles Chemical class 0.000 claims description 11
- 239000000080 wetting agent Substances 0.000 claims description 9
- 239000003701 inert diluent Substances 0.000 claims description 6
- CKEKFQLHCAZGSP-UHFFFAOYSA-N 2-(trifluoromethyl)-3h-benzimidazol-5-amine Chemical compound NC1=CC=C2N=C(C(F)(F)F)NC2=C1 CKEKFQLHCAZGSP-UHFFFAOYSA-N 0.000 claims description 3
- IPVBKOUKUCKNIK-UHFFFAOYSA-N 4,6-dibromo-2-(trifluoromethyl)-1h-benzimidazole Chemical compound C1=C(Br)C=C2NC(C(F)(F)F)=NC2=C1Br IPVBKOUKUCKNIK-UHFFFAOYSA-N 0.000 claims description 3
- 239000004009 herbicide Substances 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- GYDGKROMMMZLQI-UHFFFAOYSA-N 4,6,7-tribromo-2-(trifluoromethyl)-1h-benzimidazole Chemical compound C1=C(Br)C(Br)=C2NC(C(F)(F)F)=NC2=C1Br GYDGKROMMMZLQI-UHFFFAOYSA-N 0.000 claims description 2
- GQUMVBCXDLOULU-UHFFFAOYSA-N 6-bromo-4-chloro-2-(trifluoromethyl)-1h-benzimidazole Chemical compound C1=C(Br)C=C2NC(C(F)(F)F)=NC2=C1Cl GQUMVBCXDLOULU-UHFFFAOYSA-N 0.000 claims description 2
- ZZRMDPMUZKDLTO-UHFFFAOYSA-N 6-fluoro-2-(trifluoromethyl)-1h-benzimidazole Chemical compound FC1=CC=C2N=C(C(F)(F)F)NC2=C1 ZZRMDPMUZKDLTO-UHFFFAOYSA-N 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 7
- PMISAFNVEGVLSS-UHFFFAOYSA-N 2-(trifluoromethyl)-3h-benzimidazole-5-carbonitrile Chemical compound C1=C(C#N)C=C2NC(C(F)(F)F)=NC2=C1 PMISAFNVEGVLSS-UHFFFAOYSA-N 0.000 claims 1
- CIFIVCCKVZFJFT-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-(2-imidazol-1-yl-1-phenylethyl)benzamide Chemical compound C1=CC(Cl)=CC=C1C1=CC=C(C(=O)NC(CN2C=NC=C2)C=2C=CC=CC=2)C=C1 CIFIVCCKVZFJFT-UHFFFAOYSA-N 0.000 claims 1
- MWSWJWXZVTVPEQ-UHFFFAOYSA-N 4-bromo-2-(trifluoromethyl)-1h-benzimidazole Chemical compound C1=CC=C2NC(C(F)(F)F)=NC2=C1Br MWSWJWXZVTVPEQ-UHFFFAOYSA-N 0.000 claims 1
- LUKWKKYXNIHSRJ-UHFFFAOYSA-N 4-bromo-6-chloro-2-(trifluoromethyl)-1h-benzimidazole Chemical compound C1=C(Cl)C=C2NC(C(F)(F)F)=NC2=C1Br LUKWKKYXNIHSRJ-UHFFFAOYSA-N 0.000 claims 1
- RJHWHAVCPNBCTM-UHFFFAOYSA-N 4-bromo-6-nitro-2-(trifluoromethyl)-1h-benzimidazole Chemical compound [O-][N+](=O)C1=CC(Br)=C2N=C(C(F)(F)F)NC2=C1 RJHWHAVCPNBCTM-UHFFFAOYSA-N 0.000 claims 1
- XHHVZQKTSKYLQH-UHFFFAOYSA-N 4-nitro-2-(trifluoromethyl)-1h-benzimidazole Chemical compound [O-][N+](=O)C1=CC=CC2=C1N=C(C(F)(F)F)N2 XHHVZQKTSKYLQH-UHFFFAOYSA-N 0.000 claims 1
- JLNGJAVPDRIMBL-UHFFFAOYSA-N 5,6-dibromo-2-(trifluoromethyl)-1h-benzimidazole Chemical compound BrC1=C(Br)C=C2NC(C(F)(F)F)=NC2=C1 JLNGJAVPDRIMBL-UHFFFAOYSA-N 0.000 claims 1
- DCCVVWRWIMIAHK-UHFFFAOYSA-N 5,6-dichloro-4-nitro-2-(trifluoromethyl)-1h-benzimidazole Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=CC2=C1N=C(C(F)(F)F)N2 DCCVVWRWIMIAHK-UHFFFAOYSA-N 0.000 claims 1
- USUPLSWSXSTERT-UHFFFAOYSA-N 6-bromo-4-nitro-2-(trifluoromethyl)-1h-benzimidazole Chemical compound [O-][N+](=O)C1=CC(Br)=CC2=C1N=C(C(F)(F)F)N2 USUPLSWSXSTERT-UHFFFAOYSA-N 0.000 claims 1
- VWPQFAPZLPFZDE-UHFFFAOYSA-N 6-iodo-2-(trifluoromethyl)-1h-benzimidazole Chemical compound C1=C(I)C=C2NC(C(F)(F)F)=NC2=C1 VWPQFAPZLPFZDE-UHFFFAOYSA-N 0.000 claims 1
- GPYQJBAVCKSQTJ-UHFFFAOYSA-N 6-methoxy-2-(trifluoromethyl)-1h-benzimidazole Chemical compound COC1=CC=C2N=C(C(F)(F)F)NC2=C1 GPYQJBAVCKSQTJ-UHFFFAOYSA-N 0.000 claims 1
- AOWYBSYMYIAJEV-UHFFFAOYSA-N 6-tert-butyl-2-(trifluoromethyl)-1h-benzimidazole Chemical compound CC(C)(C)C1=CC=C2N=C(C(F)(F)F)NC2=C1 AOWYBSYMYIAJEV-UHFFFAOYSA-N 0.000 claims 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 11
- -1 amine salts Chemical class 0.000 description 7
- 241000196324 Embryophyta Species 0.000 description 6
- 235000004426 flaxseed Nutrition 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 241000219198 Brassica Species 0.000 description 5
- 235000003351 Brassica cretica Nutrition 0.000 description 5
- 235000003343 Brassica rupestris Nutrition 0.000 description 5
- 240000005979 Hordeum vulgare Species 0.000 description 5
- 240000004713 Pisum sativum Species 0.000 description 5
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 5
- 235000010460 mustard Nutrition 0.000 description 5
- 238000005507 spraying Methods 0.000 description 5
- 240000006240 Linum usitatissimum Species 0.000 description 4
- 235000004431 Linum usitatissimum Nutrition 0.000 description 4
- 235000010582 Pisum sativum Nutrition 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 3
- MXFMPTXDHSDMTI-UHFFFAOYSA-N 2-(trifluoromethyl)-1h-benzimidazole Chemical class C1=CC=C2NC(C(F)(F)F)=NC2=C1 MXFMPTXDHSDMTI-UHFFFAOYSA-N 0.000 description 3
- 235000007340 Hordeum vulgare Nutrition 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Chemical class 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 235000021537 Beetroot Nutrition 0.000 description 2
- 244000140786 Brassica hirta Species 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 240000008620 Fagopyrum esculentum Species 0.000 description 2
- 235000009419 Fagopyrum esculentum Nutrition 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical compound CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000002361 compost Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 1
- HABAPWZXRLIZDL-UHFFFAOYSA-N 2-chloro-2-phenoxyacetic acid Chemical compound OC(=O)C(Cl)OC1=CC=CC=C1 HABAPWZXRLIZDL-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- OLLDPPSRICPSTA-UHFFFAOYSA-N 6-methyl-2-(trifluoromethyl)-1h-benzimidazole Chemical compound CC1=CC=C2N=C(C(F)(F)F)NC2=C1 OLLDPPSRICPSTA-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 235000021533 Beta vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 235000006463 Brassica alba Nutrition 0.000 description 1
- 244000178993 Brassica juncea Species 0.000 description 1
- 235000011293 Brassica napus Nutrition 0.000 description 1
- 240000008100 Brassica rapa Species 0.000 description 1
- 235000000540 Brassica rapa subsp rapa Nutrition 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229920005682 EO-PO block copolymer Polymers 0.000 description 1
- 241000209219 Hordeum Species 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- DRFDPXKCEWYIAW-UHFFFAOYSA-M Risedronate sodium Chemical compound [Na+].OP(=O)(O)C(P(O)([O-])=O)(O)CC1=CC=CN=C1 DRFDPXKCEWYIAW-UHFFFAOYSA-M 0.000 description 1
- 241000220261 Sinapis Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000003939 benzylamines Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 229940125878 compound 36 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 238000005649 metathesis reaction Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 238000009736 wetting Methods 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
- 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
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/10—Radicals substituted by halogen atoms or nitro radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2958565A GB1147183A (en) | 1965-07-13 | 1965-07-13 | Substituted 2-trifluoromethyl benzimidazoles and their use as herbicides |
| GB3288565 | 1965-07-31 | ||
| GB4498765 | 1965-10-23 | ||
| GB4659465 | 1965-11-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1670716A1 true DE1670716A1 (de) | 1970-12-03 |
Family
ID=27448769
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661670716 Pending DE1670716A1 (de) | 1965-07-13 | 1966-07-08 | Herbizide Zusammensetzungen |
Country Status (9)
| Country | Link |
|---|---|
| AT (1) | AT279264B (enrdf_load_stackoverflow) |
| BE (1) | BE683812A (enrdf_load_stackoverflow) |
| BR (1) | BR6680830D0 (enrdf_load_stackoverflow) |
| DE (1) | DE1670716A1 (enrdf_load_stackoverflow) |
| ES (1) | ES329015A2 (enrdf_load_stackoverflow) |
| GB (1) | GB1147183A (enrdf_load_stackoverflow) |
| IL (1) | IL26043A (enrdf_load_stackoverflow) |
| NL (1) | NL6609821A (enrdf_load_stackoverflow) |
| NO (1) | NO115276B (enrdf_load_stackoverflow) |
-
1965
- 1965-07-13 GB GB2958565A patent/GB1147183A/en not_active Expired
-
1966
- 1966-06-27 IL IL2604366A patent/IL26043A/xx unknown
- 1966-06-30 BR BR18083066A patent/BR6680830D0/pt unknown
- 1966-07-05 NO NO16379066A patent/NO115276B/no unknown
- 1966-07-07 BE BE683812D patent/BE683812A/xx unknown
- 1966-07-08 DE DE19661670716 patent/DE1670716A1/de active Pending
- 1966-07-11 AT AT663266A patent/AT279264B/de not_active IP Right Cessation
- 1966-07-12 ES ES0329015A patent/ES329015A2/es not_active Expired
- 1966-07-13 NL NL6609821A patent/NL6609821A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL26043A (en) | 1970-05-21 |
| NO115276B (enrdf_load_stackoverflow) | 1968-09-09 |
| AT279264B (de) | 1970-02-25 |
| GB1147183A (en) | 1969-04-02 |
| BR6680830D0 (pt) | 1973-12-04 |
| NL6609821A (enrdf_load_stackoverflow) | 1967-01-16 |
| ES329015A2 (es) | 1967-09-01 |
| BE683812A (enrdf_load_stackoverflow) | 1967-01-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE970425C (de) | Unkrautbekaempfungsmittel | |
| EP0048436A1 (de) | Herbizide Mittel | |
| DE2135768B2 (de) | Synergistisches herbizides mittel | |
| EP0132512A1 (de) | Verwendung von in 2-Stellung mit (substituierten) Aminogruppen substituierten 4-DL-Alkylester-alpha-alaninyl-6-chlor-s-Triazinen als Herbizide, insbesondere gegen Flughafer | |
| DD259562A5 (de) | Verfahren zur bekaempfung von bakteriellen erkrankungen bei pflanzen | |
| DE1670716A1 (de) | Herbizide Zusammensetzungen | |
| DE2265312B2 (de) | 2-Amino-4-hydroxy-pyrimidüi-sulfaminsäureester | |
| DD252115A5 (de) | Fungizides mittel und seine verwendung | |
| DE1177407B (de) | Mittel zur Bekaempfung von Pflanzenrosterregern | |
| DE1642274A1 (de) | Mittel zur selektiven Unkrautbekaempfung in Getreide | |
| DE948652C (de) | Mittel zur Beeinflussung des Pflanzenwachstums | |
| DE951181C (de) | Unkrautvertilgungsmittel | |
| DE2021822A1 (de) | Acylierte Triflourmethylharnstoffcarbamate und deren Verwendung als Herbizide | |
| DE2150107C3 (de) | Herbizide Mittel enthaltend Benzothiazolverbindungen | |
| DE2329401A1 (de) | Herbizide mischung | |
| DE1668081A1 (de) | Verfahren zur Herstellung von neuen Mucononitrilen und diese enthaltende pesticide Zusammensetzungen sowie neue Muconitrile | |
| DE959419C (de) | Schaedlingsbekaempfungsmittel | |
| DE2265663C2 (de) | Herbizid | |
| DE1642273C3 (de) | Mittel zur selektiven Unkrautbekämpfung in Rüben | |
| AT362958B (de) | Herbizide zusammensetzungen zur bekaempfung von unerwuenschtem pflanzenwachstum, insbesondere von grasartigen und breit- blaetterigen unkraeutern | |
| DE3116020A1 (de) | Mittel insbesondere zur entblaetterung von pflanzen | |
| DE2308102A1 (de) | Herbizide zusammensetzungen | |
| DE2252724A1 (de) | Herbizide zusammensetzungen | |
| CH344259A (de) | Verfahren und Mittel zur Beeinflussung des Pflanzenwachstums | |
| DD210191A5 (de) | Verfahren und mittel zur regulierung des pflanzenwachstums |