DK172914B1 - Herbicide pyridin- og -quinolinforbindelser, mellemprodukter til fremstilling heraf, samt herbicid indeholdende forbindelse - Google Patents
Herbicide pyridin- og -quinolinforbindelser, mellemprodukter til fremstilling heraf, samt herbicid indeholdende forbindelse Download PDFInfo
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- DK172914B1 DK172914B1 DK198102404A DK240481A DK172914B1 DK 172914 B1 DK172914 B1 DK 172914B1 DK 198102404 A DK198102404 A DK 198102404A DK 240481 A DK240481 A DK 240481A DK 172914 B1 DK172914 B1 DK 172914B1
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- Denmark
- Prior art keywords
- formula
- mixture
- acid
- reaction
- methyl
- Prior art date
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- 238000002360 preparation method Methods 0.000 title description 58
- 150000001875 compounds Chemical class 0.000 title description 37
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title description 23
- 239000000543 intermediate Substances 0.000 title description 19
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title description 12
- 239000004009 herbicide Substances 0.000 title description 11
- 230000002363 herbicidal effect Effects 0.000 title description 7
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 136
- 238000006243 chemical reaction Methods 0.000 description 105
- 239000000203 mixture Substances 0.000 description 101
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 85
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 75
- -1 di-lower alkylimmo Chemical group 0.000 description 72
- 239000002253 acid Substances 0.000 description 66
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 64
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 54
- 229910052739 hydrogen Inorganic materials 0.000 description 53
- 239000001257 hydrogen Substances 0.000 description 51
- 239000000047 product Substances 0.000 description 48
- 239000000243 solution Substances 0.000 description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 46
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- 239000002904 solvent Substances 0.000 description 34
- 238000000034 method Methods 0.000 description 32
- 150000002148 esters Chemical class 0.000 description 31
- 150000002431 hydrogen Chemical group 0.000 description 31
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 30
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Substances CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 28
- 150000001768 cations Chemical class 0.000 description 27
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 25
- 239000011541 reaction mixture Substances 0.000 description 24
- 238000003756 stirring Methods 0.000 description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 22
- 238000010992 reflux Methods 0.000 description 22
- 239000007787 solid Substances 0.000 description 22
- 229910052757 nitrogen Inorganic materials 0.000 description 21
- BPPSPXOWNGOEGL-UHFFFAOYSA-N 2-(4,5-dihydro-1h-imidazol-2-yl)pyridine Chemical class N1CCN=C1C1=CC=CC=N1 BPPSPXOWNGOEGL-UHFFFAOYSA-N 0.000 description 20
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 20
- 229910052736 halogen Inorganic materials 0.000 description 20
- 150000002367 halogens Chemical class 0.000 description 20
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 18
- 239000002585 base Substances 0.000 description 18
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 17
- 125000000217 alkyl group Chemical group 0.000 description 17
- 239000008096 xylene Substances 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 16
- 238000007363 ring formation reaction Methods 0.000 description 16
- 125000001424 substituent group Chemical group 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- 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 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 15
- 150000007513 acids Chemical class 0.000 description 15
- 229910052783 alkali metal Inorganic materials 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 14
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 14
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 13
- 241000196324 Embryophyta Species 0.000 description 13
- 239000000284 extract Substances 0.000 description 13
- 239000003921 oil Substances 0.000 description 13
- 239000003960 organic solvent Substances 0.000 description 13
- 239000011734 sodium Substances 0.000 description 13
- OSUVWJGCKQEMHK-UHFFFAOYSA-N 2-(4,5-dihydro-1H-imidazol-2-yl)quinoline Chemical class N1CCN=C1C1=CC=C(C=CC=C2)C2=N1 OSUVWJGCKQEMHK-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 125000003282 alkyl amino group Chemical group 0.000 description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 12
- 235000001968 nicotinic acid Nutrition 0.000 description 12
- 239000011664 nicotinic acid Substances 0.000 description 12
- 150000003248 quinolines Chemical class 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 12
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 11
- 238000010438 heat treatment Methods 0.000 description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 11
- 229910052760 oxygen Inorganic materials 0.000 description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 10
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 10
- 150000001408 amides Chemical class 0.000 description 10
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- 239000001301 oxygen Substances 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- 229910052708 sodium Inorganic materials 0.000 description 10
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 10
- 125000003545 alkoxy group Chemical group 0.000 description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 9
- 125000004093 cyano group Chemical group *C#N 0.000 description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 9
- 150000003222 pyridines Chemical class 0.000 description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 8
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 229910000104 sodium hydride Inorganic materials 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical class O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 7
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 7
- 150000001204 N-oxides Chemical class 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- 229960000583 acetic acid Drugs 0.000 description 7
- 150000001299 aldehydes Chemical class 0.000 description 7
- 150000001340 alkali metals Chemical class 0.000 description 7
- 239000000010 aprotic solvent Substances 0.000 description 7
- 239000008346 aqueous phase Substances 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000012267 brine Substances 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 7
- 238000007254 oxidation reaction Methods 0.000 description 7
- 239000001632 sodium acetate Substances 0.000 description 7
- 235000017281 sodium acetate Nutrition 0.000 description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 6
- XHYKVHZGFAVDOB-UHFFFAOYSA-N CC#N.C1=CNC2=C3C=CN=C3C=CC2=C1 Chemical compound CC#N.C1=CNC2=C3C=CN=C3C=CC2=C1 XHYKVHZGFAVDOB-UHFFFAOYSA-N 0.000 description 6
- BCIRFFUCHHWXCQ-UHFFFAOYSA-N CC(N)=O.C1=CNC2=C3C=CN=C3C=CC2=C1 Chemical class CC(N)=O.C1=CNC2=C3C=CN=C3C=CC2=C1 BCIRFFUCHHWXCQ-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- 125000004414 alkyl thio group Chemical group 0.000 description 6
- 229910021529 ammonia Inorganic materials 0.000 description 6
- 229910002092 carbon dioxide Inorganic materials 0.000 description 6
- 125000001309 chloro group Chemical group Cl* 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000001569 carbon dioxide Substances 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 230000003197 catalytic effect Effects 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000012039 electrophile Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000012442 inert solvent Substances 0.000 description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 150000004702 methyl esters Chemical class 0.000 description 5
- 235000010755 mineral Nutrition 0.000 description 5
- 239000011707 mineral Substances 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 5
- 229910052721 tungsten Inorganic materials 0.000 description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- XWIYUCRMWCHYJR-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine Chemical compound C1=CC=C2NC=CC2=N1 XWIYUCRMWCHYJR-UHFFFAOYSA-N 0.000 description 4
- JHZLHZHHAFODPU-UHFFFAOYSA-N 4,5-dihydroimidazol-1-yl pyridine-3-carboxylate Chemical compound C=1C=CN=CC=1C(=O)ON1CCN=C1 JHZLHZHHAFODPU-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 150000001342 alkaline earth metals Chemical class 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 4
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 229960003512 nicotinic acid Drugs 0.000 description 4
- 125000002524 organometallic group Chemical group 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- SIOXPEMLGUPBBT-UHFFFAOYSA-M picolinate Chemical compound [O-]C(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-M 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 3
- RNFCDPPIXDJWBJ-UHFFFAOYSA-N 2-(4,5-dihydroimidazol-1-yl)pyridine-3-carboxylic acid Chemical class OC(=O)C1=CC=CN=C1N1C=NCC1 RNFCDPPIXDJWBJ-UHFFFAOYSA-N 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- KWPQTFXULUUCGD-UHFFFAOYSA-N 3,4,5,7,8,9,10,10a-octahydropyrido[1,2-a][1,4]diazepine Chemical compound C1CCN=CC2CCCCN21 KWPQTFXULUUCGD-UHFFFAOYSA-N 0.000 description 3
- CGQFFKULZYHFFK-UHFFFAOYSA-N 4,5-dihydro-1h-imidazol-2-yl quinoline-2-carboxylate Chemical class C=1C=C2C=CC=CC2=NC=1C(=O)OC1=NCCN1 CGQFFKULZYHFFK-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- TXTSUZLKJKLIQY-UHFFFAOYSA-N acetamide;1h-pyrrolo[3,2-b]pyridine Chemical compound CC(N)=O.C1=CC=C2NC=CC2=N1 TXTSUZLKJKLIQY-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical class [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
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- ZEXKKIXCRDTKBF-UHFFFAOYSA-N quinoline-2-carboxamide Chemical compound C1=CC=CC2=NC(C(=O)N)=CC=C21 ZEXKKIXCRDTKBF-UHFFFAOYSA-N 0.000 description 1
- GJAWHXHKYYXBSV-UHFFFAOYSA-N quinolinic acid Chemical compound OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000005932 reductive alkylation reaction Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000006894 reductive elimination reaction Methods 0.000 description 1
- 230000001850 reproductive effect Effects 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- FBWNMEQMRUMQSO-UHFFFAOYSA-N tergitol NP-9 Chemical compound CCCCCCCCCC1=CC=C(OCCOCCOCCOCCOCCOCCOCCOCCOCCO)C=C1 FBWNMEQMRUMQSO-UHFFFAOYSA-N 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- 244000082735 tidal marsh flat sedge Species 0.000 description 1
- 125000005208 trialkylammonium group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- ABVVEAHYODGCLZ-UHFFFAOYSA-N tridecan-1-amine Chemical compound CCCCCCCCCCCCCN ABVVEAHYODGCLZ-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- QFKMMXYLAPZKIB-UHFFFAOYSA-N undecan-1-amine Chemical compound CCCCCCCCCCCN QFKMMXYLAPZKIB-UHFFFAOYSA-N 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
- C07D207/444—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5
- C07D207/448—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide
- C07D207/452—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide with hydrocarbon radicals, substituted by hetero atoms, directly attached to the ring nitrogen atom
-
- 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
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
-
- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/24—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing heterocyclic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
- C07D207/444—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5
- C07D207/456—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Environmental Sciences (AREA)
- Dentistry (AREA)
- Zoology (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (12)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US15590980A | 1980-06-02 | 1980-06-02 | |
US15590880A | 1980-06-02 | 1980-06-02 | |
US15591080A | 1980-06-02 | 1980-06-02 | |
US15586780A | 1980-06-02 | 1980-06-02 | |
US15586580A | 1980-06-02 | 1980-06-02 | |
US15591080 | 1980-06-02 | ||
US15590880 | 1980-06-02 | ||
US15586580 | 1980-06-02 | ||
US15586780 | 1980-06-02 | ||
US15590980 | 1980-06-02 | ||
US25270481A | 1981-04-09 | 1981-04-09 | |
US25270481 | 1981-04-09 |
Publications (2)
Publication Number | Publication Date |
---|---|
DK240481A DK240481A (da) | 1981-12-03 |
DK172914B1 true DK172914B1 (da) | 1999-10-04 |
Family
ID=27558447
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DK198102404A DK172914B1 (da) | 1980-06-02 | 1981-06-01 | Herbicide pyridin- og -quinolinforbindelser, mellemprodukter til fremstilling heraf, samt herbicid indeholdende forbindelse |
Country Status (17)
Families Citing this family (66)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4769462A (en) * | 1980-06-02 | 1988-09-06 | American Cyanamid Co. | Novel 2-carbamoylnicotinic and 3-quinolinecarboxylic acids and esters |
WO1983004252A1 (en) * | 1982-05-25 | 1983-12-08 | American Cyanamid Company | Process for the preparation of pyridyl and quinolyl imidazolinones |
HU191626B (en) * | 1982-05-25 | 1987-03-30 | American Cyanamid Co | Process for preparing 2-/5,5-disubstituted-4-oxo-2-imidazolin-2-il/-benzoic acid, -nicotinic acid and -quinoline-3-carboxylic acid derivatives |
US4650514A (en) * | 1983-06-02 | 1987-03-17 | American Cyanamid Company | (2-imidazolin-2-yl)thieno- and furo[2,3-b] and [3,2-b]pyridines and intermediates for the preparation thereof, and use of said compounds as herbicidal agents |
ZA844134B (en) * | 1983-06-02 | 1985-01-30 | American Cyanamid Co | (2-imidazolin-2-yl)thieno-and furo(2,3,-b)and(3,2-b)-pyridines and intermediates for the preparation thereof,and use of said compounds as herbicidal agents |
US4701208A (en) * | 1983-08-02 | 1987-10-20 | American Cyanamid Company | Dihydroimidazopyrrolopyridine, quinoline, thieno- and furo[2,3-b]pyridine, dihydrothieno- and furo[2,3-b]-pyridine, thieno- and furo[3,2-b]pyridine and dihydrothieno- and furo[3,2-b]pyridine herbicides and method for preparation thereof |
EP0133310B1 (en) * | 1983-08-02 | 1988-09-14 | American Cyanamid Company | Imidazolidinones, and imidazolidinethiones, process for the preparation thereof, and use of said compounds as herbicidal agents |
ATE45351T1 (de) * | 1983-08-02 | 1989-08-15 | American Cyanamid Co | 5-thioxo-2-imidazolinyl-benzoesaeuren, deren estern, deren salze und verwandte verbindungen, deren anwendung als herbizide. |
EP0133311A3 (en) * | 1983-08-02 | 1987-12-23 | American Cyanamid Company | Substituted imidazolinyl benzoic acids, esters and salts and use thereof as herbicidal agents |
AR241812A1 (es) * | 1983-08-02 | 1992-12-30 | American Cyanamit Company | Nuevas hidroimidazo pirrolopirinas, o vinolinas, tieno-y furo¡2,3b¿ piridinas dihidrotieno-y furo ¡2,3b¿ piridinas, tieno-y furo ¡3,2b¿ piridinas tautomeros de las mismas. |
US4562257A (en) * | 1983-11-07 | 1985-12-31 | American Cyanamid Company | Preparation of substituted and unsubstituted 2-carbamoyl nicotinic and 3-quinolinecarboxylic acids |
US4719303A (en) * | 1983-11-21 | 1988-01-12 | American Cyanamid Company | Preparation of substituted and unsubstituted 2-[(1-carbamoyl-1,2-dimethylpropyl)-carbamoyl]-3-quinolinecarboxylic, nicotinic and benzoic acids |
DE3345901A1 (de) * | 1983-12-20 | 1985-06-27 | Hoechst Ag, 6230 Frankfurt | 1-acylimidazolinone, verfahren zu ihrer herstellung und ihre verwendung in der landwirtschaft |
DE3403730A1 (de) * | 1984-02-03 | 1985-08-08 | Hoechst Ag, 6230 Frankfurt | Isoindole, verfahren zu ihrer herstellung und ihre verwendung in der landwirtschaft |
US5304732A (en) * | 1984-03-06 | 1994-04-19 | Mgi Pharma, Inc. | Herbicide resistance in plants |
US4761373A (en) * | 1984-03-06 | 1988-08-02 | Molecular Genetics, Inc. | Herbicide resistance in plants |
DE3573511D1 (en) * | 1984-03-15 | 1989-11-16 | Ciba Geigy Ag | Use of quinoline derivatives to protect cultivated plants |
US4748244A (en) * | 1984-05-11 | 1988-05-31 | Ciba-Geigy Corporation | Process for the preparation of pyridine-2-3-dicarboxylic acid derivatives, and novel 1-amino-1,4-dihydropyridine-2-3-diarboxylic acid derivatives |
EP0166907A3 (en) * | 1984-06-04 | 1988-09-14 | American Cyanamid Company | Herbicidal 2-(2-imidazolin-2-yl)-fluoroalkoxy-, alkenyloxy- and alkynyloxypyridines and quinolines |
DE3520390A1 (de) * | 1984-07-07 | 1986-02-06 | Bayer Ag, 5090 Leverkusen | Imidazo-pyrrolo-pyridin-derivate |
US4749404A (en) * | 1984-07-16 | 1988-06-07 | American Cyanamid Company | Herbicidal liquid concentrate compositions |
US4754033A (en) * | 1984-08-10 | 1988-06-28 | Ciba-Geigy Corporation | Process for producing pyridine-2,3-dicarboxylic acid derivatives; and novel 1-amino-1,2,3,4-tetrahydropyridine-2,3-dicarboxylic acid derivatives and 1,4-dihydropyridine-2,3-dicarboxylic acid derivatives |
US6211439B1 (en) | 1984-08-10 | 2001-04-03 | Mgi Pharma, Inc | Herbicide resistance in plants |
AU574236B2 (en) * | 1984-11-12 | 1988-06-30 | Sumitomo Chemical Company, Limited | Herbicidal composition comprising 2-(4-chloro-2-fluoro-5-n-pentyloxycarbonylmethoxyphenyl) -4,5,6,7-tetrahydro-2h-isoindole-1,3-dione |
EP0183993A3 (de) * | 1984-11-16 | 1987-12-09 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | 2H-Imidazo[1',2':1,2]pyrrolo[3,4-b]pyridine und deren Verwendung als Unkrautbekämpfungsmittel |
FR2576308B1 (fr) * | 1985-01-18 | 1987-02-20 | Synthelabo | Derives de tetrahydroquinoleine, leur preparation et leur application en therapeutique |
FI860449A7 (fi) * | 1985-02-04 | 1986-08-05 | American Cyanamid Co | Komposition foer behandling av graesmatta. |
US5116403A (en) * | 1985-02-04 | 1992-05-26 | American Cyanamid Company | Turfgrass management composition using a 2-imidazole-2-yl nicotinic acid derivative composition |
EP0195745B1 (de) * | 1985-03-12 | 1990-09-12 | Ciba-Geigy Ag | Heterocyclisch kondensierte Pyridin-Verbindungen als Herbizide |
GB2172886A (en) * | 1985-03-26 | 1986-10-01 | Shell Int Research | Imidazoisoindole dione herbicides |
GR861747B (en) * | 1985-07-25 | 1986-09-23 | Nissan Chemical Ind Ltd | Pyridine derivatives process for their production and herbicidal compositions |
US4741763A (en) * | 1985-09-09 | 1988-05-03 | Ciba-Geigy Corporation | Heterocyclylalkyl esters of 2-imidazolinonenicotinic acids |
ES2001703A6 (es) * | 1985-09-24 | 1988-06-01 | Schering Ag | Procedimiento para la preparracion de derrrivados de acidos 2-(2-imidazolin -2-il)- piridin -3- carboxilicos. |
DE3534948A1 (de) * | 1985-10-01 | 1987-04-09 | Bayer Ag | Fungizide und wachstumsregulatorische mittel |
DE3623302A1 (de) * | 1985-11-09 | 1987-05-14 | Bayer Ag | Nicotinsaeurederivate |
DE3687516T2 (de) * | 1985-12-13 | 1993-07-29 | American Cyanamid Co | Neue kondensierte pyridinverbindungen, zwischenverbindungen fuer die herstellung und ihre verwendung als herbizide wirkstoffe. |
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DE4343922A1 (de) * | 1993-12-22 | 1995-06-29 | Basf Ag | Pyridin-2,3-dicarbonsäureimide, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung unerwünschten Pflanzenwuchses |
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EP2052615A1 (de) | 2007-10-24 | 2009-04-29 | Bayer CropScience AG | Herbizid-Kombination |
DE102008037628A1 (de) | 2008-08-14 | 2010-02-18 | Bayer Crop Science Ag | Herbizid-Kombination mit Dimethoxytriazinyl-substituierten Difluormethansulfonylaniliden |
AU2016282731B2 (en) * | 2015-06-22 | 2020-07-02 | Bayer Cropscience Aktiengesellschaft | New alkynyl-substituted 3-phenylpyrrolidine-2,4-diones and use thereof as herbicides |
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US3553217A (en) * | 1968-10-18 | 1971-01-05 | Aldrich Chem Co Inc | 2-(quinolinimido)glutarimide |
NL7017486A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1969-12-15 | 1971-06-17 | ||
US3940419A (en) * | 1973-04-05 | 1976-02-24 | American Cyanamid Company | Phthalimide derivatives and their use as plant growth regulants |
US4041045A (en) * | 1975-11-12 | 1977-08-09 | American Cyanamid Company | Dihydroimidaz oisoindolediones and the use thereof as herbicidal agents |
US4017510A (en) * | 1975-11-12 | 1977-04-12 | American Cyanamid Company | Imidazoisoindolediones and the use thereof as herbicidal agents |
NL7714092A (nl) * | 1976-12-22 | 1978-06-26 | Monsanto Co | Werkwijze voor het bereiden van nieuwe ftalamine- en nicotinezuren. |
US4188487A (en) * | 1977-08-08 | 1980-02-12 | American Cyanamid Company | Imidazolinyl benzoic acids, esters and salts and their use as herbicidal agents |
DE3162095D1 (en) * | 1980-06-02 | 1984-03-08 | American Cyanamid Co | Method to beneficially influence & alter the development & life cycle of agronomic and horticultural crops with certain imidazolinyl nicotinic acids and derivatives thereof |
-
1981
- 1981-05-05 IL IL62794A patent/IL62794A0/xx not_active IP Right Cessation
- 1981-05-12 EP EP81103638A patent/EP0041623B1/en not_active Expired
- 1981-05-14 GR GR64966A patent/GR75256B/el unknown
- 1981-05-19 CA CA000377772A patent/CA1187498A/en not_active Expired
- 1981-05-29 NZ NZ197247A patent/NZ197247A/xx unknown
- 1981-06-01 PH PH25697A patent/PH20756A/en unknown
- 1981-06-01 BR BR8103449A patent/BR8103449A/pt not_active IP Right Cessation
- 1981-06-01 TR TR21582A patent/TR21582A/xx unknown
- 1981-06-01 AU AU71214/81A patent/AU548174B2/en not_active Expired
- 1981-06-01 NO NO81811841A patent/NO162465C/no not_active IP Right Cessation
- 1981-06-01 FI FI811680A patent/FI76082C/fi not_active IP Right Cessation
- 1981-06-01 DK DK198102404A patent/DK172914B1/da not_active IP Right Cessation
- 1981-06-02 DD DD81230506A patent/DD160172A5/de unknown
- 1981-07-01 YU YU1381/81A patent/YU43768B/xx unknown
-
1983
- 1983-08-29 YU YU1767/83A patent/YU43836B/xx unknown
-
1988
- 1988-08-25 SG SG562/88A patent/SG56288G/en unknown
-
1989
- 1989-01-12 HK HK36/89A patent/HK3689A/en not_active IP Right Cessation
- 1989-01-27 JP JP1016537A patent/JPH01238571A/ja active Granted
-
1990
- 1990-11-16 AU AU66703/90A patent/AU636928B2/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
NO162465B (no) | 1989-09-25 |
JPH01238571A (ja) | 1989-09-22 |
IL62794A0 (en) | 1981-07-31 |
DK240481A (da) | 1981-12-03 |
GR75256B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-07-13 |
FI76082C (fi) | 1988-09-09 |
JPH0323544B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1991-03-29 |
YU176783A (en) | 1983-12-31 |
TR21582A (tr) | 1984-11-07 |
AU548174B2 (en) | 1985-11-28 |
NO811841L (no) | 1981-12-03 |
AU6670390A (en) | 1991-02-14 |
YU138181A (en) | 1983-12-31 |
AU7121481A (en) | 1981-12-10 |
CA1187498A (en) | 1985-05-21 |
SG56288G (en) | 1989-03-10 |
EP0041623A2 (en) | 1981-12-16 |
AU636928B2 (en) | 1993-05-13 |
PH20756A (en) | 1987-04-02 |
FI76082B (fi) | 1988-05-31 |
EP0041623A3 (en) | 1982-09-22 |
NO162465C (no) | 1990-01-10 |
BR8103449A (pt) | 1982-02-24 |
EP0041623B1 (en) | 1985-08-28 |
HK3689A (en) | 1989-01-20 |
YU43836B (en) | 1989-12-31 |
FI811680L (fi) | 1981-12-03 |
DD160172A5 (de) | 1983-05-11 |
NZ197247A (en) | 1985-11-08 |
YU43768B (en) | 1989-12-31 |
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B1 | Patent granted (law 1993) | ||
PUP | Patent expired |