HUT60727A - Benzimidazole derivatives, herbicidal compositions comprising such compounds and process for producing such compounds - Google Patents
Benzimidazole derivatives, herbicidal compositions comprising such compounds and process for producing such compounds Download PDFInfo
- Publication number
- HUT60727A HUT60727A HU9201234A HU9201234A HUT60727A HU T60727 A HUT60727 A HU T60727A HU 9201234 A HU9201234 A HU 9201234A HU 9201234 A HU9201234 A HU 9201234A HU T60727 A HUT60727 A HU T60727A
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- group
- carbon atoms
- optionally substituted
- benzimidazol
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 131
- 239000000203 mixture Substances 0.000 title claims abstract description 59
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 31
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title claims abstract description 13
- 238000000034 method Methods 0.000 title claims description 19
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 title claims description 6
- -1 -NR4R5 Chemical group 0.000 claims abstract description 51
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 47
- 125000003118 aryl group Chemical group 0.000 claims abstract description 22
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 22
- 150000002367 halogens Chemical class 0.000 claims abstract description 22
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 21
- 150000003839 salts Chemical class 0.000 claims abstract description 20
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000001301 oxygen Substances 0.000 claims abstract description 17
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 10
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 9
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims abstract 4
- 241000196324 Embryophyta Species 0.000 claims description 61
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 238000002360 preparation method Methods 0.000 claims description 21
- 239000004480 active ingredient Substances 0.000 claims description 19
- 239000003085 diluting agent Substances 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 17
- 239000004094 surface-active agent Substances 0.000 claims description 14
- 238000009472 formulation Methods 0.000 claims description 13
- 239000007788 liquid Substances 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 9
- 150000001556 benzimidazoles Chemical class 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 239000011593 sulfur Substances 0.000 claims description 8
- 239000000843 powder Substances 0.000 claims description 7
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 6
- 239000011591 potassium Substances 0.000 claims description 6
- 229910052700 potassium Inorganic materials 0.000 claims description 6
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 239000011664 nicotinic acid Substances 0.000 claims description 5
- 235000001968 nicotinic acid Nutrition 0.000 claims description 5
- DJXNJVFEFSWHLY-UHFFFAOYSA-N quinoline-3-carboxylic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-N 0.000 claims description 5
- 239000004550 soluble concentrate Substances 0.000 claims description 5
- 239000004563 wettable powder Substances 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000012141 concentrate Substances 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- JJWLVOIRVHMVIS-UHFFFAOYSA-O isopropylaminium Chemical compound CC(C)[NH3+] JJWLVOIRVHMVIS-UHFFFAOYSA-O 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 239000004546 suspension concentrate Substances 0.000 claims description 3
- SILNNFMWIMZVEQ-UHFFFAOYSA-N 1,3-dihydrobenzimidazol-2-one Chemical class C1=CC=C2NC(O)=NC2=C1 SILNNFMWIMZVEQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 239000007900 aqueous suspension Substances 0.000 claims description 2
- 238000012272 crop production Methods 0.000 claims description 2
- 239000004495 emulsifiable concentrate Substances 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-M nicotinate Chemical compound [O-]C(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-M 0.000 claims description 2
- QAHVHSLSRLSVGS-UHFFFAOYSA-N sulfamoyl chloride Chemical compound NS(Cl)(=O)=O QAHVHSLSRLSVGS-UHFFFAOYSA-N 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000005605 benzo group Chemical group 0.000 claims 1
- 239000012050 conventional carrier Substances 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 5
- 239000005864 Sulphur Chemical group 0.000 abstract 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 125000000879 imine group Chemical group 0.000 abstract 1
- 125000005017 substituted alkenyl group Chemical group 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 36
- 239000002904 solvent Substances 0.000 description 30
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 238000009835 boiling Methods 0.000 description 18
- 238000005481 NMR spectroscopy Methods 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 238000006722 reduction reaction Methods 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 239000002689 soil Substances 0.000 description 11
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 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
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000000969 carrier Substances 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- 229910052708 sodium Inorganic materials 0.000 description 9
- 238000005507 spraying Methods 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- 229910052783 alkali metal Inorganic materials 0.000 description 7
- 150000001340 alkali metals Chemical class 0.000 description 7
- 229940125904 compound 1 Drugs 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- QKZQJBBZKDVVFI-UHFFFAOYSA-N 4-fluoro-2,1,3-benzoxadiazole Chemical compound FC1=CC=CC2=NON=C12 QKZQJBBZKDVVFI-UHFFFAOYSA-N 0.000 description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 5
- 244000038559 crop plants Species 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 239000004009 herbicide Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical class NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 4
- 241000209504 Poaceae Species 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- WGDRAVMHLDKGGA-UHFFFAOYSA-N prop-2-en-1-imine Chemical class [CH2]C=C[NH] WGDRAVMHLDKGGA-UHFFFAOYSA-N 0.000 description 4
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical class NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 3
- XNARZJQXBMWIQU-UHFFFAOYSA-N 3,4-dihydro-2h-pyrano[3,2-b]pyridine Chemical compound C1=CN=C2CCCOC2=C1 XNARZJQXBMWIQU-UHFFFAOYSA-N 0.000 description 3
- 240000006995 Abutilon theophrasti Species 0.000 description 3
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 3
- 244000237956 Amaranthus retroflexus Species 0.000 description 3
- 241000209764 Avena fatua Species 0.000 description 3
- 235000007320 Avena fatua Nutrition 0.000 description 3
- 235000008427 Brassica arvensis Nutrition 0.000 description 3
- 244000024671 Brassica kaber Species 0.000 description 3
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- 244000285774 Cyperus esculentus Species 0.000 description 3
- 235000005853 Cyperus esculentus Nutrition 0.000 description 3
- 244000058871 Echinochloa crus-galli Species 0.000 description 3
- 235000014820 Galium aparine Nutrition 0.000 description 3
- 240000005702 Galium aparine Species 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 3
- 241000207890 Ipomoea purpurea Species 0.000 description 3
- 240000007594 Oryza sativa Species 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- 235000011999 Panicum crusgalli Nutrition 0.000 description 3
- 240000003461 Setaria viridis Species 0.000 description 3
- 235000002248 Setaria viridis Nutrition 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- 244000098338 Triticum aestivum Species 0.000 description 3
- 244000067505 Xanthium strumarium Species 0.000 description 3
- 240000008042 Zea mays Species 0.000 description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 235000008504 concentrate Nutrition 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000012669 liquid formulation Substances 0.000 description 3
- YTGWKOHORKGMHD-UHFFFAOYSA-N n-(2,3-dinitrophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O YTGWKOHORKGMHD-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 235000009566 rice Nutrition 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 229910052979 sodium sulfide Inorganic materials 0.000 description 3
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 3
- 239000002562 thickening agent Substances 0.000 description 3
- XLPSQGZEHPWSDZ-UHFFFAOYSA-N 2-[1-(dimethylsulfamoyl)-4-prop-2-enoxybenzimidazol-2-yl]pyridine-3-carboxylic acid Chemical compound N=1C2=C(OCC=C)C=CC=C2N(S(=O)(=O)N(C)C)C=1C1=NC=CC=C1C(O)=O XLPSQGZEHPWSDZ-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- LLWQBRBGKOEJAM-UHFFFAOYSA-N 4-but-2-ynoxy-2,1,3-benzoxadiazole Chemical compound CC#CCOC1=CC=CC2=NON=C12 LLWQBRBGKOEJAM-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 241001621841 Alopecurus myosuroides Species 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 150000008061 acetanilides Chemical class 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- JXCGFZXSOMJFOA-UHFFFAOYSA-N chlorotoluron Chemical compound CN(C)C(=O)NC1=CC=C(C)C(Cl)=C1 JXCGFZXSOMJFOA-UHFFFAOYSA-N 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 150000005182 dinitrobenzenes Chemical class 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000003623 enhancer Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 238000003973 irrigation Methods 0.000 description 2
- 230000002262 irrigation Effects 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- PUIYMUZLKQOUOZ-UHFFFAOYSA-N isoproturon Chemical compound CC(C)C1=CC=C(NC(=O)N(C)C)C=C1 PUIYMUZLKQOUOZ-UHFFFAOYSA-N 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
- 235000014666 liquid concentrate Nutrition 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 125000005439 maleimidyl group Chemical class C1(C=CC(N1*)=O)=O 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- KLIXYSYBPXHSFU-UHFFFAOYSA-N methyl 2-(4-prop-2-enoxy-1h-benzimidazol-2-yl)pyridine-3-carboxylate Chemical compound COC(=O)C1=CC=CN=C1C1=NC2=C(OCC=C)C=CC=C2N1 KLIXYSYBPXHSFU-UHFFFAOYSA-N 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical class [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- 125000005936 piperidyl group Chemical group 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 244000062645 predators Species 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000003586 protic polar solvent Substances 0.000 description 2
- 150000003254 radicals Chemical group 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 150000003573 thiols Chemical class 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical class C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- WURBVZBTWMNKQT-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)C)OC1=CC=C(Cl)C=C1 WURBVZBTWMNKQT-UHFFFAOYSA-N 0.000 description 1
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- MKNDFEACGBGFKS-UHFFFAOYSA-N 2-[1-(dimethylsulfamoyl)-4-prop-2-enoxybenzimidazol-2-yl]quinoline-3-carboxylic acid Chemical compound C1=CC=C2C=C(C(O)=O)C(C=3N(C4=CC=CC(OCC=C)=C4N=3)S(=O)(=O)N(C)C)=NC2=C1 MKNDFEACGBGFKS-UHFFFAOYSA-N 0.000 description 1
- ULFQPBSHDLDEKQ-UHFFFAOYSA-N 2-[1-(dimethylsulfamoyl)-4-prop-2-ynoxybenzimidazol-2-yl]-5-ethylpyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC(CC)=CN=C1C1=NC2=C(OCC#C)C=CC=C2N1S(=O)(=O)N(C)C ULFQPBSHDLDEKQ-UHFFFAOYSA-N 0.000 description 1
- BYLVQCHIIIYCFH-UHFFFAOYSA-N 2-[1-(dimethylsulfamoyl)-4-prop-2-ynoxybenzimidazol-2-yl]-5-methylpyridine-3-carboxylic acid Chemical compound N=1C2=C(OCC#C)C=CC=C2N(S(=O)(=O)N(C)C)C=1C1=NC=C(C)C=C1C(O)=O BYLVQCHIIIYCFH-UHFFFAOYSA-N 0.000 description 1
- XWQANZLLZYYZSP-UHFFFAOYSA-N 2-[1-(dimethylsulfamoyl)-4-prop-2-ynoxybenzimidazol-2-yl]-6-methylpyridine-3-carboxylic acid Chemical compound N=1C2=C(OCC#C)C=CC=C2N(S(=O)(=O)N(C)C)C=1C1=NC(C)=CC=C1C(O)=O XWQANZLLZYYZSP-UHFFFAOYSA-N 0.000 description 1
- KGGDGHZWUYZIJC-UHFFFAOYSA-N 2-[1-(dimethylsulfamoyl)-4-prop-2-ynoxybenzimidazol-2-yl]pyridine-3-carboxylic acid Chemical compound N=1C2=C(OCC#C)C=CC=C2N(S(=O)(=O)N(C)C)C=1C1=NC=CC=C1C(O)=O KGGDGHZWUYZIJC-UHFFFAOYSA-N 0.000 description 1
- FVVDQKFCCJOANM-UHFFFAOYSA-N 2-[1-(dimethylsulfamoyl)-5-prop-2-ynoxybenzimidazol-2-yl]pyridine-3-carboxylic acid Chemical compound N=1C2=CC(OCC#C)=CC=C2N(S(=O)(=O)N(C)C)C=1C1=NC=CC=C1C(O)=O FVVDQKFCCJOANM-UHFFFAOYSA-N 0.000 description 1
- DYSVMELQCAITOB-UHFFFAOYSA-N 2-[4-but-2-ynoxy-1-(dimethylsulfamoyl)benzimidazol-2-yl]pyridine-3-carboxylic acid Chemical compound N=1C=2C(OCC#CC)=CC=CC=2N(S(=O)(=O)N(C)C)C=1C1=NC=CC=C1C(O)=O DYSVMELQCAITOB-UHFFFAOYSA-N 0.000 description 1
- KUCWUAFNGCMZDB-UHFFFAOYSA-N 2-amino-3-nitrophenol Chemical compound NC1=C(O)C=CC=C1[N+]([O-])=O KUCWUAFNGCMZDB-UHFFFAOYSA-N 0.000 description 1
- YFMAPGZWKVKHND-UHFFFAOYSA-N 2-nitro-4-prop-2-ynoxyaniline Chemical compound NC1=CC=C(OCC#C)C=C1[N+]([O-])=O YFMAPGZWKVKHND-UHFFFAOYSA-N 0.000 description 1
- JXSQCGRJGGIUDV-UHFFFAOYSA-N 2-nitro-6-prop-2-enoxyaniline Chemical compound NC1=C(OCC=C)C=CC=C1[N+]([O-])=O JXSQCGRJGGIUDV-UHFFFAOYSA-N 0.000 description 1
- SNKVUILILOTQDH-UHFFFAOYSA-N 2-nitro-6-prop-2-ynoxyaniline Chemical compound NC1=C(OCC#C)C=CC=C1[N+]([O-])=O SNKVUILILOTQDH-UHFFFAOYSA-N 0.000 description 1
- SEUOXNQCSYDBKF-UHFFFAOYSA-N 2-phenylmethoxy-1h-benzimidazole Chemical class N=1C2=CC=CC=C2NC=1OCC1=CC=CC=C1 SEUOXNQCSYDBKF-UHFFFAOYSA-N 0.000 description 1
- UPMXNNIRAGDFEH-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzonitrile Chemical compound OC1=C(Br)C=C(C#N)C=C1Br UPMXNNIRAGDFEH-UHFFFAOYSA-N 0.000 description 1
- BLCZXLGRKKRKJJ-UHFFFAOYSA-N 3-amino-2-nitrophenol Chemical compound NC1=CC=CC(O)=C1[N+]([O-])=O BLCZXLGRKKRKJJ-UHFFFAOYSA-N 0.000 description 1
- 244000291564 Allium cepa Species 0.000 description 1
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
- 241000219318 Amaranthus Species 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 241000209761 Avena Species 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 235000010662 Bidens pilosa Nutrition 0.000 description 1
- 244000104272 Bidens pilosa Species 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- 239000005489 Bromoxynil Substances 0.000 description 1
- XZPALDPWNZAWAU-UHFFFAOYSA-N C12=NC=CC=C2C(=O)N2C1=NC1=C2C(OCC=C)=CC=C1 Chemical compound C12=NC=CC=C2C(=O)N2C1=NC1=C2C(OCC=C)=CC=C1 XZPALDPWNZAWAU-UHFFFAOYSA-N 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
- 240000006122 Chenopodium album Species 0.000 description 1
- 235000009344 Chenopodium album Nutrition 0.000 description 1
- 239000005494 Chlorotoluron Substances 0.000 description 1
- 239000005946 Cypermethrin Substances 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- 235000002767 Daucus carota Nutrition 0.000 description 1
- 244000000626 Daucus carota Species 0.000 description 1
- 239000005504 Dicamba Substances 0.000 description 1
- LBGPXIPGGRQBJW-UHFFFAOYSA-N Difenzoquat Chemical compound C[N+]=1N(C)C(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 LBGPXIPGGRQBJW-UHFFFAOYSA-N 0.000 description 1
- 244000152970 Digitaria sanguinalis Species 0.000 description 1
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 1
- 239000001692 EU approved anti-caking agent Substances 0.000 description 1
- 235000001950 Elaeis guineensis Nutrition 0.000 description 1
- 244000127993 Elaeis melanococca Species 0.000 description 1
- 235000014716 Eleusine indica Nutrition 0.000 description 1
- 244000025670 Eleusine indica Species 0.000 description 1
- 239000005533 Fluometuron Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 235000021506 Ipomoea Nutrition 0.000 description 1
- 241000207783 Ipomoea Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 240000004658 Medicago sativa Species 0.000 description 1
- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 1
- YJLYANLCNIKXMG-UHFFFAOYSA-N N-Methyldioctylamine Chemical compound CCCCCCCCN(C)CCCCCCCC YJLYANLCNIKXMG-UHFFFAOYSA-N 0.000 description 1
- 239000005586 Nicosulfuron Substances 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000014676 Phragmites communis Nutrition 0.000 description 1
- 235000010582 Pisum sativum Nutrition 0.000 description 1
- 240000004713 Pisum sativum Species 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 241000533293 Sesbania emerus Species 0.000 description 1
- 235000005775 Setaria Nutrition 0.000 description 1
- 241000232088 Setaria <nematode> Species 0.000 description 1
- 241001355178 Setaria faberi Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 235000002594 Solanum nigrum Nutrition 0.000 description 1
- 244000061457 Solanum nigrum Species 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 235000010749 Vicia faba Nutrition 0.000 description 1
- 240000006677 Vicia faba Species 0.000 description 1
- 235000002098 Vicia faba var. major Nutrition 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 241001148683 Zostera marina Species 0.000 description 1
- CIRZURUTJRNCKH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[Mn+6] Chemical compound [O-2].[O-2].[O-2].[Mn+6] CIRZURUTJRNCKH-UHFFFAOYSA-N 0.000 description 1
- WREOTYWODABZMH-DTZQCDIJSA-N [[(2r,3s,4r,5r)-3,4-dihydroxy-5-[2-oxo-4-(2-phenylethoxyamino)pyrimidin-1-yl]oxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate Chemical compound O[C@@H]1[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@H]1N(C=C\1)C(=O)NC/1=N\OCCC1=CC=CC=C1 WREOTYWODABZMH-DTZQCDIJSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003302 alkenyloxy group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000005133 alkynyloxy group Chemical group 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002152 aqueous-organic solution Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 1
- 238000005422 blasting Methods 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- NEEDEQSZOUAJMU-UHFFFAOYSA-N but-2-yn-1-ol Chemical compound CC#CCO NEEDEQSZOUAJMU-UHFFFAOYSA-N 0.000 description 1
- 229920005551 calcium lignosulfonate Polymers 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229940125758 compound 15 Drugs 0.000 description 1
- 229940126142 compound 16 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000007799 cork Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- UVJHQYIOXKWHFD-UHFFFAOYSA-N cyclohexa-1,4-diene Chemical compound C1C=CCC=C1 UVJHQYIOXKWHFD-UHFFFAOYSA-N 0.000 description 1
- 229960005424 cypermethrin Drugs 0.000 description 1
- KAATUXNTWXVJKI-UHFFFAOYSA-N cypermethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000005489 dwarf bean Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000007590 electrostatic spraying Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- RZILCCPWPBTYDO-UHFFFAOYSA-N fluometuron Chemical compound CN(C)C(=O)NC1=CC=CC(C(F)(F)F)=C1 RZILCCPWPBTYDO-UHFFFAOYSA-N 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- ISXSFOPKZQZDAO-UHFFFAOYSA-N formaldehyde;sodium Chemical compound [Na].O=C ISXSFOPKZQZDAO-UHFFFAOYSA-N 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- RCFDIXKVOHJQPP-UHFFFAOYSA-N furo[2,3-b]pyridine Chemical compound C1=CN=C2OC=CC2=C1 RCFDIXKVOHJQPP-UHFFFAOYSA-N 0.000 description 1
- YRTCKZIKGWZNCU-UHFFFAOYSA-N furo[3,2-b]pyridine Chemical compound C1=CC=C2OC=CC2=N1 YRTCKZIKGWZNCU-UHFFFAOYSA-N 0.000 description 1
- NLVZUORLSQCGFQ-UHFFFAOYSA-N furo[3,4-b]quinoline-1,3-dione Chemical compound C1=CC=C2C=C3C(=O)OC(=O)C3=NC2=C1 NLVZUORLSQCGFQ-UHFFFAOYSA-N 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000000852 hydrogen donor Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 229910000473 manganese(VI) oxide Inorganic materials 0.000 description 1
- RBNIGDFIUWJJEV-UHFFFAOYSA-N methyl 2-(n-benzoyl-3-chloro-4-fluoroanilino)propanoate Chemical group C=1C=C(F)C(Cl)=CC=1N(C(C)C(=O)OC)C(=O)C1=CC=CC=C1 RBNIGDFIUWJJEV-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- JFCHSQDLLFJHOA-UHFFFAOYSA-N n,n-dimethylsulfamoyl chloride Chemical compound CN(C)S(Cl)(=O)=O JFCHSQDLLFJHOA-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 1
- RTCOGUMHFFWOJV-UHFFFAOYSA-N nicosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(=O)N(C)C)=N1 RTCOGUMHFFWOJV-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 229960000490 permethrin Drugs 0.000 description 1
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- YOTUNYOXGHRZDC-UHFFFAOYSA-N prop-2-ynyl 2-[1-(dimethylsulfamoyl)-4-prop-2-ynoxybenzimidazol-2-yl]-5-methylpyridine-3-carboxylate Chemical compound N=1C2=C(OCC#C)C=CC=C2N(S(=O)(=O)N(C)C)C=1C1=NC=C(C)C=C1C(=O)OCC#C YOTUNYOXGHRZDC-UHFFFAOYSA-N 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- UDJFFSGCRRMVFH-UHFFFAOYSA-N pyrido[2,3-d]pyrimidine Chemical compound N1=CN=CC2=CC=CN=C21 UDJFFSGCRRMVFH-UHFFFAOYSA-N 0.000 description 1
- FTVQJPGTLLVZLJ-UHFFFAOYSA-N pyrrolo[1,2-a]benzimidazol-5-one Chemical compound C1=CC=C2N=C3C(N21)=CC=CC3=O FTVQJPGTLLVZLJ-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- CMUCGJHILMSIQX-UHFFFAOYSA-N quinoline-2-carbonyl quinoline-2-carboxylate Chemical compound C1=CC=CC2=NC(C(OC(=O)C=3N=C4C=CC=CC4=CC=3)=O)=CC=C21 CMUCGJHILMSIQX-UHFFFAOYSA-N 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 229910021487 silica fume Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 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
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- SMZMHUCIDGHERP-UHFFFAOYSA-N thieno[2,3-b]pyridine Chemical compound C1=CN=C2SC=CC2=C1 SMZMHUCIDGHERP-UHFFFAOYSA-N 0.000 description 1
- DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical compound C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000004552 water soluble powder Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229940074411 xylene Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A01N43/52—1,3-Diazoles; Hydrogenated 1,3-diazoles condensed with carbocyclic rings, e.g. benzimidazoles
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)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB919108369A GB9108369D0 (en) | 1991-04-18 | 1991-04-18 | Compositions of matter |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HU9201234D0 HU9201234D0 (en) | 1992-07-28 |
| HUT60727A true HUT60727A (en) | 1992-10-28 |
Family
ID=10693555
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU9201234A HUT60727A (en) | 1991-04-18 | 1992-04-10 | Benzimidazole derivatives, herbicidal compositions comprising such compounds and process for producing such compounds |
Country Status (21)
| Country | Link |
|---|---|
| EP (1) | EP0509717A3 (enEXAMPLES) |
| JP (1) | JPH05112558A (enEXAMPLES) |
| KR (1) | KR920019774A (enEXAMPLES) |
| CN (1) | CN1065864A (enEXAMPLES) |
| AU (1) | AU647258B2 (enEXAMPLES) |
| BR (1) | BR9201458A (enEXAMPLES) |
| CA (1) | CA2065197A1 (enEXAMPLES) |
| CS (1) | CS110392A3 (enEXAMPLES) |
| FI (1) | FI921615A7 (enEXAMPLES) |
| GB (1) | GB9108369D0 (enEXAMPLES) |
| HU (1) | HUT60727A (enEXAMPLES) |
| IE (1) | IE921155A1 (enEXAMPLES) |
| IL (1) | IL101550A0 (enEXAMPLES) |
| MA (1) | MA22499A1 (enEXAMPLES) |
| MX (1) | MX9201652A (enEXAMPLES) |
| NO (1) | NO921400L (enEXAMPLES) |
| OA (1) | OA09576A (enEXAMPLES) |
| PL (1) | PL294187A1 (enEXAMPLES) |
| TR (1) | TR26619A (enEXAMPLES) |
| TW (1) | TW199154B (enEXAMPLES) |
| YU (1) | YU37892A (enEXAMPLES) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9107742D0 (en) * | 1991-04-11 | 1991-05-29 | Rhone Poulenc Agriculture | New compositions of matter |
| US5300478A (en) * | 1993-01-28 | 1994-04-05 | Zeneca Limited | Substituted fused pyrazolo compounds |
| US5451566A (en) * | 1993-11-17 | 1995-09-19 | Zeneca Limited | Herbicidal pyrrolopyridine compounds |
| AU5881394A (en) * | 1994-01-08 | 1995-08-01 | Rhone-Poulenc Agriculture Limited | Benzimidazolyl quinoline-3-carboxylate derivatives, intermediates thereto, and their use as herbicides |
| US6756383B2 (en) | 2000-09-01 | 2004-06-29 | Chiron Corporation | Heterocyclic derivatives of quinolinone benimidazoles |
| PL211125B1 (pl) | 2000-09-11 | 2012-04-30 | Novartis Vaccines & Diagnostic | Pochodne chinolinonu jako inhibitory kinazy tyrozynowej, kompozycje je zawierające i ich zastosowanie |
| GB0028105D0 (en) * | 2000-11-17 | 2001-01-03 | Smithkline Beecham Corp | Compounds |
| US7825132B2 (en) | 2002-08-23 | 2010-11-02 | Novartis Vaccines And Diagnostics, Inc. | Inhibition of FGFR3 and treatment of multiple myeloma |
| EP2573079A3 (en) | 2002-08-23 | 2015-03-11 | Novartis AG | Benzimidazole quinolinones and uses thereof |
| WO2004043389A2 (en) | 2002-11-13 | 2004-05-27 | Chiron Corporation | Methods of treating cancer and related methods |
| EP1718306A2 (en) | 2004-02-20 | 2006-11-08 | Chiron Corporation | Modulation of inflammatory and metastatic processes |
| SI1885187T1 (sl) | 2005-05-13 | 2013-12-31 | Novartis Ag | Postopki za zdravljenje raka, rezistentnega na zdravila |
| ES2376347T3 (es) | 2005-05-17 | 2012-03-13 | Novartis Ag | Métodos para sintetizar compuestos heteroc�?clicos. |
| MX2007014782A (es) | 2005-05-23 | 2008-02-19 | Novartis Ag | Formas cristalinas y otras formas de las sales de acido lactico de 4-amino-5-fluoro-3-[6-(4-metilpiperazin-1-il)-1h-bencimidazol-2 -il]-1h quinolin-2-ona. |
| JP5413557B2 (ja) * | 2008-06-17 | 2014-02-12 | Ｊｓｒ株式会社 | 液晶配向剤および液晶表示素子 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1805548A1 (de) * | 1968-10-26 | 1970-10-08 | Agfa Gevaert Ag | Benzimidazol-Derivate und ihre photographische Verwendung |
| US4895588A (en) * | 1987-07-01 | 1990-01-23 | Ciba-Geigy Corporation | Substituted imidazolones having herbicidal activity |
| FR2653432A1 (fr) * | 1989-10-20 | 1991-04-26 | Rhone Poulenc Agrochimie | Herbicides derives de 2-azolyl nicotinate. |
| GB9107742D0 (en) * | 1991-04-11 | 1991-05-29 | Rhone Poulenc Agriculture | New compositions of matter |
-
1991
- 1991-04-18 GB GB919108369A patent/GB9108369D0/en active Pending
-
1992
- 1992-04-06 CA CA002065197A patent/CA2065197A1/en not_active Abandoned
- 1992-04-09 AU AU14751/92A patent/AU647258B2/en not_active Ceased
- 1992-04-09 NO NO92921400A patent/NO921400L/no unknown
- 1992-04-09 IL IL101550A patent/IL101550A0/xx unknown
- 1992-04-09 TW TW081102727A patent/TW199154B/zh active
- 1992-04-10 CS CS921103A patent/CS110392A3/cs unknown
- 1992-04-10 HU HU9201234A patent/HUT60727A/hu unknown
- 1992-04-10 MX MX9201652A patent/MX9201652A/es unknown
- 1992-04-10 IE IE115592A patent/IE921155A1/en unknown
- 1992-04-10 YU YU37892A patent/YU37892A/sh unknown
- 1992-04-10 MA MA22781A patent/MA22499A1/fr unknown
- 1992-04-10 PL PL29418792A patent/PL294187A1/xx unknown
- 1992-04-10 EP EP19920303195 patent/EP0509717A3/en not_active Withdrawn
- 1992-04-10 FI FI921615A patent/FI921615A7/fi not_active Application Discontinuation
- 1992-04-10 OA OA60184A patent/OA09576A/fr unknown
- 1992-04-10 JP JP4091019A patent/JPH05112558A/ja active Pending
- 1992-04-11 KR KR1019920006069A patent/KR920019774A/ko not_active Withdrawn
- 1992-04-11 CN CN92102691A patent/CN1065864A/zh active Pending
- 1992-04-13 BR BR929201458A patent/BR9201458A/pt not_active Application Discontinuation
- 1992-04-17 TR TR92/0361A patent/TR26619A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| TR26619A (tr) | 1995-03-15 |
| YU37892A (sh) | 1994-06-24 |
| IL101550A0 (en) | 1992-12-30 |
| NO921400L (no) | 1992-10-19 |
| CS110392A3 (en) | 1992-11-18 |
| JPH05112558A (ja) | 1993-05-07 |
| MX9201652A (es) | 1992-10-01 |
| AU1475192A (en) | 1992-10-22 |
| IE921155A1 (en) | 1992-10-21 |
| EP0509717A3 (en) | 1993-03-24 |
| KR920019774A (ko) | 1992-11-20 |
| OA09576A (fr) | 1993-01-31 |
| GB9108369D0 (en) | 1991-06-05 |
| PL294187A1 (en) | 1993-07-26 |
| EP0509717A2 (en) | 1992-10-21 |
| BR9201458A (pt) | 1992-12-01 |
| CN1065864A (zh) | 1992-11-04 |
| AU647258B2 (en) | 1994-03-17 |
| MA22499A1 (fr) | 1992-12-31 |
| CA2065197A1 (en) | 1992-10-19 |
| NO921400D0 (no) | 1992-04-09 |
| TW199154B (enEXAMPLES) | 1993-02-01 |
| FI921615A7 (fi) | 1992-10-19 |
| HU9201234D0 (en) | 1992-07-28 |
| FI921615A0 (fi) | 1992-04-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP3078661B2 (ja) | 新規な除草剤 | |
| US4693741A (en) | N-phenylsulfonyl-N'-pyrimidinylureas | |
| CS20592A3 (en) | 2-cyano-1,3-dione derivatives, process of their preparation and herbicidalcompositions containing said derivatives | |
| US5104443A (en) | Heterocyclic 2-alkoxyphenoxysulfonylureas and the use thereof as herbicides or plant growth regulators | |
| SK82794A3 (en) | Pyrido £2,3-d|pyridazine derivatives, method of their production , compositions which contain them, and their using as herbicides | |
| CS20492A3 (en) | 2-cyano-1,3-dione derivatives, process of their preparation and herbicidalcompositions containing said derivatives | |
| HUT60727A (en) | Benzimidazole derivatives, herbicidal compositions comprising such compounds and process for producing such compounds | |
| JPS5989669A (ja) | 除草活性を有する尿素誘導体 | |
| HU212433B (en) | Herbicidal compositions containing 4-benzoylisoxazole derivatives, process for the production of active ingredients and their application | |
| HUT60728A (en) | Benzimidazole derivatives, herbicidal compositions comprising such compounds and process for producing such compounds | |
| EP0918755A1 (en) | 1-alkyl-4-benzoyl-5-hydroxypyrazole compounds and their use as herbicides | |
| HU198707B (en) | Herbicide compositions containing nicotinic acid derivatives as active agents and process for producing these compounds | |
| DK155302B (da) | N-phenylpyrazolderivater og herbicid med indhold deraf | |
| SI9300317A (sl) | N-substituirani pirazolni derivati | |
| SI9400058A (en) | Novel herbicidal 4-benzoylisoxazole derivatives | |
| US5139565A (en) | Substituted pyridinesulfonamide compounds, and herbicidal compositions containing them | |
| JPH08504781A (ja) | ４−ベンゾイルイソオキサゾール誘導体及び除草剤としてのその使用 | |
| WO1998042648A1 (en) | 2-benzoylcyclohexane-1,3-dione compounds and their use as herbicides | |
| AU659647B2 (en) | Substituted benzothiazole derivatives, their preparation and use as herbicides | |
| CA2090268A1 (en) | Selective herbicidal composition | |
| US4723989A (en) | Herbicidal imidazolinones | |
| US5536703A (en) | Herbicidal substituted benzoyl bicycloalkanediones | |
| PH26072A (en) | Heterocyclic-substituted phenylsulfamates processes for their preparation and their use as herbicides and plant growth regulators | |
| HUT59682A (en) | Herbicide compositions containing triazolo-pyridazine derivatives as active components and process for producing the active components | |
| JPH0356480A (ja) | 除草性スルホンアミド |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| DFA9 | Temporary protection cancelled due to abandonment | ||
| DFC4 | Cancellation of temporary protection due to refusal |