CS110392A3 - Benzimidazolyl derivatives, process of their preparation and herbicidalcompositions containing said derivatives - Google Patents

Benzimidazolyl derivatives, process of their preparation and herbicidalcompositions containing said derivatives Download PDF

Info

Publication number: CS110392A3
Authority: CS; Czechoslovakia
Prior art keywords: group; different; carbon atoms; ring; formula
Prior art date: 1991-04-18

Application number

CS921103A

Other languages

Czech (cs)

English (en)

Inventor

Michael Colin Cramp

Christopher John Pearson

Original Assignee

Rhone Poulenc Agriculture

Priority date (The priority date 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 date listed.)

1991-04-18

Filing date

1992-04-10

Publication date

1992-11-18

1992-04-10 Application filed by Rhone Poulenc Agriculture filed Critical Rhone Poulenc Agriculture

1992-11-18 Publication of CS110392A3 publication Critical patent/CS110392A3/cs

Links

125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 title claims description 23
238000000034 method Methods 0.000 title claims description 22
238000002360 preparation method Methods 0.000 title claims description 17
230000008569 process Effects 0.000 title claims description 3
150000001875 compounds Chemical class 0.000 claims description 134
239000000203 mixture Substances 0.000 claims description 60
241000196324 Embryophyta Species 0.000 claims description 50
230000002363 herbicidal effect Effects 0.000 claims description 46
125000004432 carbon atom Chemical group C* 0.000 claims description 43
-1 -NRR Chemical group 0.000 claims description 38
125000000217 alkyl group Chemical group 0.000 claims description 27
150000003839 salts Chemical class 0.000 claims description 21
239000004094 surface-active agent Substances 0.000 claims description 21
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 20
239000003085 diluting agent Substances 0.000 claims description 20
229910052739 hydrogen Inorganic materials 0.000 claims description 19
125000005843 halogen group Chemical group 0.000 claims description 17
239000007788 liquid Substances 0.000 claims description 17
125000003118 aryl group Chemical group 0.000 claims description 16
238000006243 chemical reaction Methods 0.000 claims description 15
229910052757 nitrogen Inorganic materials 0.000 claims description 15
125000003710 aryl alkyl group Chemical group 0.000 claims description 14
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
229910052736 halogen Inorganic materials 0.000 claims description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
229910052760 oxygen Inorganic materials 0.000 claims description 13
239000001301 oxygen Chemical group 0.000 claims description 13
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
239000004480 active ingredient Substances 0.000 claims description 11
150000002367 halogens Chemical class 0.000 claims description 11
229910052717 sulfur Inorganic materials 0.000 claims description 11
239000002253 acid Substances 0.000 claims description 10
239000012141 concentrate Substances 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
239000000843 powder Substances 0.000 claims description 10
125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 9
125000000753 cycloalkyl group Chemical group 0.000 claims description 9
UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical group [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 9
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical group [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 8
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
125000005842 heteroatom Chemical group 0.000 claims description 8
PVNIIMVLHYAWGP-UHFFFAOYSA-M nicotinate Chemical compound [O-]C(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-M 0.000 claims description 8
239000011593 sulfur Chemical group 0.000 claims description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
125000003342 alkenyl group Chemical group 0.000 claims description 6
125000000304 alkynyl group Chemical group 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
235000001968 nicotinic acid Nutrition 0.000 claims description 6
239000011664 nicotinic acid Substances 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
239000008187 granular material Substances 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 4
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 4
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 4
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
125000004429 atom Chemical group 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
229910052731 fluorine Inorganic materials 0.000 claims description 4
125000002541 furyl group Chemical group 0.000 claims description 4
125000000623 heterocyclic group Chemical group 0.000 claims description 4
230000007062 hydrolysis Effects 0.000 claims description 4
238000006460 hydrolysis reaction Methods 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
125000004430 oxygen atom Chemical group O* 0.000 claims description 4
125000005936 piperidyl group Chemical group 0.000 claims description 4
239000011591 potassium Chemical group 0.000 claims description 4
229910052700 potassium Chemical group 0.000 claims description 4
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 4
239000004550 soluble concentrate Substances 0.000 claims description 4
125000000335 thiazolyl group Chemical group 0.000 claims description 4
125000001544 thienyl group Chemical group 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
239000007900 aqueous suspension Substances 0.000 claims description 3
239000011230 binding agent Substances 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
229910052740 iodine Inorganic materials 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
125000006413 ring segment Chemical group 0.000 claims description 3
125000004434 sulfur atom Chemical group 0.000 claims description 3
239000004546 suspension concentrate Substances 0.000 claims description 3
239000004563 wettable powder Substances 0.000 claims description 3
SILNNFMWIMZVEQ-UHFFFAOYSA-N 1,3-dihydrobenzimidazol-2-one Chemical compound C1=CC=C2NC(O)=NC2=C1 SILNNFMWIMZVEQ-UHFFFAOYSA-N 0.000 claims description 2
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 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
NAYFQDVGAZMKLL-UHFFFAOYSA-N 5-ethylpyridine-3-carboxylic acid Chemical compound CCC1=CN=CC(C(O)=O)=C1 NAYFQDVGAZMKLL-UHFFFAOYSA-N 0.000 claims description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
125000001931 aliphatic group Chemical group 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 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
JJWLVOIRVHMVIS-UHFFFAOYSA-O isopropylaminium Chemical group CC(C)[NH3+] JJWLVOIRVHMVIS-UHFFFAOYSA-O 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
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 claims 1
108090000623 proteins and genes Proteins 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 35
239000002904 solvent Substances 0.000 description 31
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
238000005481 NMR spectroscopy Methods 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
238000010992 reflux Methods 0.000 description 20
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
239000007787 solid Substances 0.000 description 18
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
239000000243 solution Substances 0.000 description 14
230000009467 reduction Effects 0.000 description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 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 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
239000000969 carrier Substances 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 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
238000009835 boiling Methods 0.000 description 9
235000008504 concentrate Nutrition 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 8
239000002689 soil Substances 0.000 description 8
229910052783 alkali metal Inorganic materials 0.000 description 7
229940125904 compound 1 Drugs 0.000 description 7
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
239000003960 organic solvent Substances 0.000 description 7
229910000027 potassium carbonate Inorganic materials 0.000 description 7
238000005507 spraying Methods 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
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 6
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
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235000019198 oils Nutrition 0.000 description 6
239000011734 sodium Substances 0.000 description 6
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WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
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150000008064 anhydrides Chemical class 0.000 description 4
MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 description 4
238000000227 grinding Methods 0.000 description 4
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
238000005580 one pot reaction Methods 0.000 description 4
239000007858 starting material Substances 0.000 description 4
DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 3
240000006995 Abutilon theophrasti Species 0.000 description 3
235000013479 Amaranthus retroflexus Nutrition 0.000 description 3
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244000025254 Cannabis sativa Species 0.000 description 3
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150000002823 nitrates Chemical class 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
239000012044 organic layer Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
235000020232 peanut Nutrition 0.000 description 1
230000035515 penetration Effects 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives 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
159000000001 potassium salts Chemical class 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
WGDRAVMHLDKGGA-UHFFFAOYSA-N prop-2-en-1-imine Chemical compound [CH2]C=C[NH] WGDRAVMHLDKGGA-UHFFFAOYSA-N 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
230000001681 protective effect Effects 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
230000008707 rearrangement Effects 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
239000003352 sequestering agent Substances 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
239000011877 solvent mixture Substances 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
238000009331 sowing Methods 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000001119 stannous chloride Substances 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
238000003756 stirring Methods 0.000 description 1
YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 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
230000000007 visual effect Effects 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)

CS921103A 1991-04-18 1992-04-10 Benzimidazolyl derivatives, process of their preparation and herbicidalcompositions containing said derivatives CS110392A3 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB919108369A GB9108369D0 (en)	1991-04-18	1991-04-18	Compositions of matter

Publications (1)

Publication Number	Publication Date
CS110392A3 true CS110392A3 (en)	1992-11-18

Family

ID=10693555

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS921103A CS110392A3 (en)	1991-04-18	1992-04-10	Benzimidazolyl derivatives, process of their preparation and herbicidalcompositions containing said derivatives

Country Status (21)

Country	Link
EP (1)	EP0509717A3 (fr)
JP (1)	JPH05112558A (fr)
KR (1)	KR920019774A (fr)
CN (1)	CN1065864A (fr)
AU (1)	AU647258B2 (fr)
BR (1)	BR9201458A (fr)
CA (1)	CA2065197A1 (fr)
CS (1)	CS110392A3 (fr)
FI (1)	FI921615A7 (fr)
GB (1)	GB9108369D0 (fr)
HU (1)	HUT60727A (fr)
IE (1)	IE921155A1 (fr)
IL (1)	IL101550A0 (fr)
MA (1)	MA22499A1 (fr)
MX (1)	MX9201652A (fr)
NO (1)	NO921400L (fr)
OA (1)	OA09576A (fr)
PL (1)	PL294187A1 (fr)
TR (1)	TR26619A (fr)
TW (1)	TW199154B (fr)
YU (1)	YU37892A (fr)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
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
WO1995018801A1 (fr) *	1994-01-08	1995-07-13	Rhone-Poulenc Agriculture Ltd.	Derives de quinoline-3-carboxylate benzimidazoyle, leurs intermediaires ainsi que leur utilisation en tant qu'herbicides
ATE448226T1 (de)	2000-09-01	2009-11-15	Novartis Vaccines & Diagnostic	Aza heterocyclische derivate und ihre therapeutische verwendung
DE60115069T2 (de)	2000-09-11	2006-08-03	Chiron Corp., Emeryville	Chinolinonderivate als tyrosin-kinase inhibitoren
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
EP1539754A4 (fr)	2002-08-23	2009-02-25	Novartis Vaccines & Diagnostic	Quinolinones de benzimidazole et leurs utilisations
SG148864A1 (en)	2002-11-13	2009-01-29	Chiron Corp	Methods of treating cancer and related methods
EP1718306A2 (fr)	2004-02-20	2006-11-08	Chiron Corporation	Modulation de processus inflammatoires et metastatiques
EP1885187B1 (fr)	2005-05-13	2013-09-25	Novartis AG	Procedes pour traiter un cancer pharmacoresistant
EP2465857B1 (fr)	2005-05-17	2014-06-04	Novartis AG	Procédés de synthèse de composés hétérocycliques
BRPI0611375A2 (pt)	2005-05-23	2010-08-31	Novartis Ag	formas cristalinas e outras de sais de ácido láctico de 4-amino-5-flúor-3-[6-(4-metilpiperazin-1-il)-1h-benzimid azol-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)

* Cited by examiner, † Cited by third party
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
EP0298029B1 (fr) *	1987-07-01	1992-12-02	Ciba-Geigy Ag	Imidazolones substituées à activité herbicide
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/fr not_active Abandoned
- 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
- 1992-04-09 AU AU14751/92A patent/AU647258B2/en not_active Ceased
- 1992-04-10 FI FI921615A patent/FI921615A7/fi not_active Application Discontinuation
- 1992-04-10 PL PL29418792A patent/PL294187A1/xx unknown
- 1992-04-10 CS CS921103A patent/CS110392A3/cs unknown
- 1992-04-10 IE IE115592A patent/IE921155A1/en unknown
- 1992-04-10 JP JP4091019A patent/JPH05112558A/ja active Pending
- 1992-04-10 MX MX9201652A patent/MX9201652A/es unknown
- 1992-04-10 YU YU37892A patent/YU37892A/sh unknown
- 1992-04-10 HU HU9201234A patent/HUT60727A/hu unknown
- 1992-04-10 EP EP19920303195 patent/EP0509717A3/en not_active Withdrawn
- 1992-04-10 OA OA60184A patent/OA09576A/fr unknown
- 1992-04-10 MA MA22781A patent/MA22499A1/fr unknown
- 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
CA2065197A1 (fr)	1992-10-19
IL101550A0 (en)	1992-12-30
MA22499A1 (fr)	1992-12-31
AU647258B2 (en)	1994-03-17
FI921615A0 (fi)	1992-04-10
YU37892A (sh)	1994-06-24
IE921155A1 (en)	1992-10-21
HUT60727A (en)	1992-10-28
JPH05112558A (ja)	1993-05-07
FI921615A7 (fi)	1992-10-19
HU9201234D0 (en)	1992-07-28
NO921400D0 (no)	1992-04-09
MX9201652A (es)	1992-10-01
KR920019774A (ko)	1992-11-20
AU1475192A (en)	1992-10-22
BR9201458A (pt)	1992-12-01
CN1065864A (zh)	1992-11-04
OA09576A (fr)	1993-01-31
GB9108369D0 (en)	1991-06-05
NO921400L (no)	1992-10-19
TR26619A (tr)	1995-03-15
EP0509717A3 (en)	1993-03-24
TW199154B (fr)	1993-02-01
EP0509717A2 (fr)	1992-10-21
PL294187A1 (en)	1993-07-26

Publication	Publication Date	Title
EP0470856B1 (fr)	1995-10-11	Dérivés d'isoxazole, procédés pour leur fabrication et leurs applications comme herbicides
JP3078661B2 (ja)	2000-08-21	新規な除草剤
CZ282743B6 (cs)	1997-09-17	2-kyano-1,3-dionové deriváty, způsob jejich přípravy a herbicidní kompozice tyto deriváty obsahující
EP0634413A1 (fr)	1995-01-18	Herbicides
CZ282742B6 (cs)	1997-09-17	2-kyano-1,3-dionové deriváty, způsob jejich přípravy a herbicidní kompozice tyto deriváty obsahující
CZ13293A3 (en)	1994-01-19	Herbicidal composition
CS110392A3 (en)	1992-11-18	Benzimidazolyl derivatives, process of their preparation and herbicidalcompositions containing said derivatives
HU212433B (en)	1996-06-28	Herbicidal compositions containing 4-benzoylisoxazole derivatives, process for the production of active ingredients and their application
CS110592A3 (en)	1992-10-14	Benzimidazolyl derivatives, process of their preparation and herbicidalcompositions containing said derivatives
EP0786937A2 (fr)	1997-08-06	Compositions herbicides
JP3557230B2 (ja)	2004-08-25	新規な除草剤
SI9400058A (en)	1994-09-30	Novel herbicidal 4-benzoylisoxazole derivatives
US5405826A (en)	1995-04-11	Herbicidal pyridopyridazinones and pyridopyridazinethiones
CZ418097A3 (cs)	1998-07-15	Deriváty 1,3-oxazin-4-onu, způsob jejich přípravy a herbicidní prostředky které je obsahují
US20010029239A1 (en)	2001-10-11	New herbicidal compositions
JPH0356480A (ja)	1991-03-12	除草性スルホンアミド
HK1003790B (en)	1998-11-06	4-benzoylisoxazole derivatives and their use as herbicides