HU191635B - Herbicide compositions containing benzimidazolyl-and benztriazolyl-phenoxy-alkane-carboxylic acid derivatives and process for producing the active agents - Google Patents
Herbicide compositions containing benzimidazolyl-and benztriazolyl-phenoxy-alkane-carboxylic acid derivatives and process for producing the active agents Download PDFInfo
- Publication number
- HU191635B HU191635B HU833234A HU323483A HU191635B HU 191635 B HU191635 B HU 191635B HU 833234 A HU833234 A HU 833234A HU 323483 A HU323483 A HU 323483A HU 191635 B HU191635 B HU 191635B
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- Hungary
- Prior art keywords
- formula
- compound
- ethyl
- methyl
- phenoxy
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 45
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 11
- 238000000034 method Methods 0.000 title claims description 8
- 239000004009 herbicide Substances 0.000 title description 3
- 239000013543 active substance Substances 0.000 title 1
- -1 azol-1-yl Chemical group 0.000 claims abstract description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
- 239000001257 hydrogen Substances 0.000 claims abstract description 21
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 17
- 239000004480 active ingredient Substances 0.000 claims abstract description 15
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical group 0.000 claims abstract description 6
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims abstract description 4
- 150000003949 imides Chemical class 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 94
- 238000002360 preparation method Methods 0.000 claims description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- 239000007787 solid Substances 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 23
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 17
- 125000003943 azolyl group Chemical group 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 9
- 239000004094 surface-active agent Substances 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 5
- 239000000969 carrier Substances 0.000 claims description 5
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 229920002125 Sokalan® Polymers 0.000 claims description 2
- 125000005605 benzo group Chemical group 0.000 claims description 2
- 239000004927 clay Substances 0.000 claims description 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 2
- 239000000194 fatty acid Substances 0.000 claims description 2
- 229930195729 fatty acid Natural products 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 239000004584 polyacrylic acid Substances 0.000 claims 1
- 150000002148 esters Chemical class 0.000 abstract description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 4
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 4
- 150000003839 salts Chemical class 0.000 abstract description 4
- 229910052783 alkali metal Inorganic materials 0.000 abstract description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000004970 halomethyl group Chemical group 0.000 abstract 1
- 150000002500 ions Chemical class 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 abstract 1
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 abstract 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 48
- 239000000243 solution Substances 0.000 description 32
- 239000011541 reaction mixture Substances 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- 239000003921 oil Substances 0.000 description 17
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 229910002027 silica gel Inorganic materials 0.000 description 13
- 239000000741 silica gel Substances 0.000 description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- 241000196324 Embryophyta Species 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 12
- 239000000284 extract Substances 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- 239000002689 soil Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 235000010288 sodium nitrite Nutrition 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- SJAWBKPVXVNSIE-UHFFFAOYSA-N ethyl 2-[4-[5-(trifluoromethyl)benzimidazol-1-yl]phenoxy]propanoate Chemical compound C1=CC(OC(C)C(=O)OCC)=CC=C1N1C2=CC=C(C(F)(F)F)C=C2N=C1 SJAWBKPVXVNSIE-UHFFFAOYSA-N 0.000 description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 description 4
- QALWMIGUNKKUAZ-UHFFFAOYSA-N 2-[4-(5-fluorobenzotriazol-1-yl)phenoxy]propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1N1C2=CC=C(F)C=C2N=N1 QALWMIGUNKKUAZ-UHFFFAOYSA-N 0.000 description 4
- WVKOPVGLJVMNKG-UHFFFAOYSA-N 2-[4-[5-(trifluoromethyl)benzimidazol-1-yl]phenoxy]butanoic acid Chemical compound C1=CC(OC(CC)C(O)=O)=CC=C1N1C2=CC=C(C(F)(F)F)C=C2N=C1 WVKOPVGLJVMNKG-UHFFFAOYSA-N 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- LNJDEGFOFQXVSE-UHFFFAOYSA-N 3-methoxy-2-[4-[5-(trifluoromethyl)benzotriazol-1-yl]phenoxy]propanoic acid Chemical compound C1=CC(OC(COC)C(O)=O)=CC=C1N1C2=CC=C(C(F)(F)F)C=C2N=N1 LNJDEGFOFQXVSE-UHFFFAOYSA-N 0.000 description 3
- XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 description 3
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- 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 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229940125890 compound Ia Drugs 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000012259 ether extract Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 229940035044 sorbitan monolaurate Drugs 0.000 description 3
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 2
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 2
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 2
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- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 2
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 2
- 229920001213 Polysorbate 20 Polymers 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
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- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
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- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 2
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- RZHBMYQXKIDANM-UHFFFAOYSA-N dioctyl butanedioate;sodium Chemical compound [Na].CCCCCCCCOC(=O)CCC(=O)OCCCCCCCC RZHBMYQXKIDANM-UHFFFAOYSA-N 0.000 description 2
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D249/18—Benzotriazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
- C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
- C07C205/37—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
-
- 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
- C07D235/08—Radicals containing only hydrogen and carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/419,865 US4439226A (en) | 1982-09-20 | 1982-09-20 | Herbicidal 4-((benzimidazol-1-yl)phenoxy)alkanoic acids, esters and salts |
| US06/419,860 US4452626A (en) | 1982-09-20 | 1982-09-20 | Herbicidal 4-(benzotriazol-1-yl)phenoxy)alkanoic acids, esters and salts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU191635B true HU191635B (en) | 1987-03-30 |
Family
ID=27024650
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU833234A HU191635B (en) | 1982-09-20 | 1983-09-19 | Herbicide compositions containing benzimidazolyl-and benztriazolyl-phenoxy-alkane-carboxylic acid derivatives and process for producing the active agents |
Country Status (19)
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4883901A (en) * | 1988-03-21 | 1989-11-28 | Hoechst Celanese Corporation | Synthesis of 2-(4-aminophenoxy)alkanoic acids and esters and their derivatives |
| IL91997A0 (en) * | 1988-11-03 | 1990-07-12 | American Cyanamid Co | Aryloxy benzotriazole herbicidal agents and methods for the preparation thereof |
| US5324711A (en) * | 1988-11-03 | 1994-06-28 | American Cyanamid Company | Aryloxy benzotriazole herbicidal agents and methods for the preparation thereof |
| US5786301A (en) * | 1993-04-28 | 1998-07-28 | Zeneca Limited | N-benzotriazoles |
| US5369086A (en) * | 1993-04-28 | 1994-11-29 | Zeneca Limited | N-benzotriazoles |
| RU2183628C1 (ru) * | 2001-06-22 | 2002-06-20 | Ярославский государственный технический университет | Гетероциклические о-дикарбонитрилы |
| RU2185378C1 (ru) * | 2001-06-22 | 2002-07-20 | Ярославский государственный технический университет | Гетероциклические о-дикарбонитрилы |
| RU2326873C1 (ru) * | 2006-12-18 | 2008-06-20 | Государственное образовательное учреждение высшего профессионального образования "Ивановский государственный химико-технологический университет" (ИГХТУ) | 4-(1-бензотриазолил)-5-(нафтокси)фталодинитрилы |
| CN110372618B (zh) * | 2019-08-30 | 2021-10-01 | 南通大学 | 一种含苯并三氮唑苯基单元的氰基丙烯酸酯化合物的制备方法及其应用 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3856812A (en) * | 1971-03-15 | 1974-12-24 | Merck Patent Gmbh | Pyrrole phenoxyacetic acid derivatives |
-
1983
- 1983-09-12 DE DE8383201306T patent/DE3366608D1/de not_active Expired
- 1983-09-12 EP EP83201306A patent/EP0107216B1/en not_active Expired
- 1983-09-16 TR TR21874A patent/TR21874A/xx unknown
- 1983-09-16 PT PT77346A patent/PT77346B/pt not_active IP Right Cessation
- 1983-09-16 DD DD83254887A patent/DD218828A5/de not_active IP Right Cessation
- 1983-09-19 NO NO833369A patent/NO161854C/no unknown
- 1983-09-19 DK DK426883A patent/DK160424C/da not_active IP Right Cessation
- 1983-09-19 AU AU19251/83A patent/AU555945B2/en not_active Ceased
- 1983-09-19 ZW ZW199/83A patent/ZW19983A1/xx unknown
- 1983-09-19 BR BR8305090A patent/BR8305090A/pt not_active IP Right Cessation
- 1983-09-19 FI FI833337A patent/FI833337A7/fi not_active Application Discontinuation
- 1983-09-19 ES ES525714A patent/ES8606302A1/es not_active Expired
- 1983-09-19 NZ NZ205640A patent/NZ205640A/en unknown
- 1983-09-19 CS CS836831A patent/CS244429B2/cs unknown
- 1983-09-19 HU HU833234A patent/HU191635B/hu unknown
- 1983-09-19 IE IE2195/83A patent/IE55945B1/xx unknown
- 1983-09-19 PL PL1983243818A patent/PL140149B1/pl unknown
- 1983-09-19 GR GR72472A patent/GR79676B/el unknown
- 1983-09-20 OA OA58101A patent/OA07532A/xx unknown
-
1985
- 1985-09-02 ES ES546650A patent/ES8606294A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BR8305090A (pt) | 1984-05-08 |
| TR21874A (tr) | 1985-10-03 |
| DK426883A (da) | 1984-03-21 |
| EP0107216B1 (en) | 1986-10-01 |
| DK160424C (da) | 1991-08-19 |
| NO833369L (no) | 1984-03-21 |
| IE55945B1 (en) | 1991-02-27 |
| NO161854C (no) | 1989-10-04 |
| FI833337A0 (fi) | 1983-09-19 |
| AU555945B2 (en) | 1986-10-16 |
| FI833337A7 (fi) | 1984-03-21 |
| DK426883D0 (da) | 1983-09-19 |
| PT77346A (pt) | 1983-10-01 |
| NO161854B (no) | 1989-06-26 |
| EP0107216A1 (en) | 1984-05-02 |
| GR79676B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-10-31 |
| ZW19983A1 (en) | 1983-12-14 |
| IE832195L (en) | 1984-03-20 |
| ES8606302A1 (es) | 1986-04-01 |
| OA07532A (en) | 1985-03-31 |
| DD218828A5 (de) | 1985-02-20 |
| ES546650A0 (es) | 1986-04-16 |
| CS244429B2 (en) | 1986-07-17 |
| PT77346B (pt) | 1986-04-21 |
| AU1925183A (en) | 1984-03-29 |
| ES8606294A1 (es) | 1986-04-16 |
| PL140149B1 (en) | 1987-03-31 |
| NZ205640A (en) | 1985-08-30 |
| PL243818A1 (en) | 1985-01-16 |
| DE3366608D1 (en) | 1986-11-06 |
| DK160424B (da) | 1991-03-11 |
| ES525714A0 (es) | 1986-04-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 |