CH622784A5 - Process for the preparation of 1,4-diphenyl-3-pyrazolin-5-ones - Google Patents
Process for the preparation of 1,4-diphenyl-3-pyrazolin-5-ones Download PDFInfo
- Publication number
- CH622784A5 CH622784A5 CH1520676A CH1520676A CH622784A5 CH 622784 A5 CH622784 A5 CH 622784A5 CH 1520676 A CH1520676 A CH 1520676A CH 1520676 A CH1520676 A CH 1520676A CH 622784 A5 CH622784 A5 CH 622784A5
- Authority
- CH
- Switzerland
- Prior art keywords
- alpha
- pyrazolin
- tolyl
- trifluoro
- methyl
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 13
- 238000000034 method Methods 0.000 title claims description 10
- XNWYPYFQYFUUTE-UHFFFAOYSA-N 2,4-diphenyl-1h-pyrazol-3-one Chemical class O=C1C(C=2C=CC=CC=2)=CNN1C1=CC=CC=C1 XNWYPYFQYFUUTE-UHFFFAOYSA-N 0.000 title claims description 4
- 241000196324 Embryophyta Species 0.000 claims description 61
- 150000001875 compounds Chemical class 0.000 claims description 55
- 239000000203 mixture Substances 0.000 claims description 35
- -1 alpha, alpha, alpha-trifluoro-m-tolyl Chemical group 0.000 claims description 25
- 239000004480 active ingredient Substances 0.000 claims description 22
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 11
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 claims description 11
- 239000000460 chlorine Chemical group 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 230000002363 herbicidal effect Effects 0.000 claims description 8
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 7
- 239000004009 herbicide Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 229910052731 fluorine Chemical group 0.000 claims description 5
- 239000011737 fluorine Chemical group 0.000 claims description 5
- 150000002431 hydrogen Chemical group 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- WSFDLWSPVFKKSK-UHFFFAOYSA-N 1-ethyl-2-phenyl-4-[3-(trifluoromethyl)phenyl]pyrazol-3-one Chemical compound O=C1N(C=2C=CC=CC=2)N(CC)C=C1C1=CC=CC(C(F)(F)F)=C1 WSFDLWSPVFKKSK-UHFFFAOYSA-N 0.000 claims description 4
- CJNKIEYRKCLFPH-UHFFFAOYSA-N 1-methyl-2-phenyl-4-[3-(trifluoromethyl)phenyl]pyrazol-3-one Chemical compound O=C1N(C=2C=CC=CC=2)N(C)C=C1C1=CC=CC(C(F)(F)F)=C1 CJNKIEYRKCLFPH-UHFFFAOYSA-N 0.000 claims description 4
- LCPGOQQXDPDPET-UHFFFAOYSA-N 2-(4-fluorophenyl)-1-methyl-4-[3-(trifluoromethyl)phenyl]pyrazol-3-one Chemical compound O=C1N(C=2C=CC(F)=CC=2)N(C)C=C1C1=CC=CC(C(F)(F)F)=C1 LCPGOQQXDPDPET-UHFFFAOYSA-N 0.000 claims description 4
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- KBRQEEHDWOQDES-UHFFFAOYSA-N 2,4-bis(3-chlorophenyl)-1-ethylpyrazol-3-one Chemical compound O=C1N(C=2C=C(Cl)C=CC=2)N(CC)C=C1C1=CC=CC(Cl)=C1 KBRQEEHDWOQDES-UHFFFAOYSA-N 0.000 claims description 3
- XPVYQRMQHBQDAJ-UHFFFAOYSA-N 2-(3-chlorophenyl)-1-methyl-4-[3-(trifluoromethyl)phenyl]pyrazol-3-one Chemical compound O=C1N(C=2C=C(Cl)C=CC=2)N(C)C=C1C1=CC=CC(C(F)(F)F)=C1 XPVYQRMQHBQDAJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000002168 alkylating agent Substances 0.000 claims description 3
- 229940100198 alkylating agent Drugs 0.000 claims description 3
- WOPTXLRXPDWIIS-UHFFFAOYSA-N 2-(3-bromophenyl)-1-ethyl-4-[3-(trifluoromethyl)phenyl]pyrazol-3-one Chemical compound O=C1N(C=2C=C(Br)C=CC=2)N(CC)C=C1C1=CC=CC(C(F)(F)F)=C1 WOPTXLRXPDWIIS-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 238000010992 reflux Methods 0.000 description 26
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- 238000004458 analytical method Methods 0.000 description 20
- 239000000155 melt Substances 0.000 description 20
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
- 239000000047 product Substances 0.000 description 20
- XBYRMPXUBGMOJC-UHFFFAOYSA-N 1,2-dihydropyrazol-3-one Chemical compound OC=1C=CNN=1 XBYRMPXUBGMOJC-UHFFFAOYSA-N 0.000 description 17
- 239000011541 reaction mixture Substances 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000002689 soil Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 244000062793 Sorghum vulgare Species 0.000 description 10
- 235000019713 millet Nutrition 0.000 description 10
- 229910000027 potassium carbonate Inorganic materials 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 6
- 229940067157 phenylhydrazine Drugs 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- 240000001592 Amaranthus caudatus Species 0.000 description 4
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 4
- ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 240000008042 Zea mays Species 0.000 description 4
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 4
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 4
- 240000003307 Zinnia violacea Species 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 235000005822 corn Nutrition 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 235000015097 nutrients Nutrition 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- CRRIAWUJYMLJOE-UHFFFAOYSA-N (3-chlorophenyl)hydrazine;hydron;chloride Chemical compound Cl.NNC1=CC=CC(Cl)=C1 CRRIAWUJYMLJOE-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000003905 agrochemical Substances 0.000 description 3
- 239000000010 aprotic solvent Substances 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000004495 emulsifiable concentrate Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 150000007529 inorganic bases Chemical class 0.000 description 3
- 239000013067 intermediate product Substances 0.000 description 3
- 238000011835 investigation Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- VLLGNJRXOIPQLA-UHFFFAOYSA-N 1-methyl-2-(3-methylphenyl)-4-[3-(trifluoromethyl)phenyl]pyrazol-3-one Chemical compound CC1=CC=CC(N2C(C(C=3C=C(C=CC=3)C(F)(F)F)=CN2C)=O)=C1 VLLGNJRXOIPQLA-UHFFFAOYSA-N 0.000 description 2
- SONQGXBYMUCWNC-UHFFFAOYSA-N 2,4-bis[3-(trifluoromethyl)phenyl]-1h-pyrazol-3-one Chemical compound FC(F)(F)C1=CC=CC(C=2C(N(C=3C=C(C=CC=3)C(F)(F)F)NC=2)=O)=C1 SONQGXBYMUCWNC-UHFFFAOYSA-N 0.000 description 2
- PMEFSPXRONLUJE-UHFFFAOYSA-N 2-(3-methylphenyl)-1h-pyrazol-3-one Chemical compound CC1=CC=CC(N2C(C=CN2)=O)=C1 PMEFSPXRONLUJE-UHFFFAOYSA-N 0.000 description 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 2
- QRXXROXHMWWNGU-UHFFFAOYSA-N 4-(3-chlorophenyl)-1-methyl-2-phenylpyrazol-3-one Chemical compound O=C1N(C=2C=CC=CC=2)N(C)C=C1C1=CC=CC(Cl)=C1 QRXXROXHMWWNGU-UHFFFAOYSA-N 0.000 description 2
- USJPTCZHVYLMEE-UHFFFAOYSA-N 4-(3-fluorophenyl)-1-methyl-2-phenylpyrazol-3-one Chemical compound O=C1N(C=2C=CC=CC=2)N(C)C=C1C1=CC=CC(F)=C1 USJPTCZHVYLMEE-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 2
- 244000056139 Brassica cretica Species 0.000 description 2
- 235000003351 Brassica cretica Nutrition 0.000 description 2
- 235000003343 Brassica rupestris Nutrition 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 240000008067 Cucumis sativus Species 0.000 description 2
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- 240000000982 Malva neglecta Species 0.000 description 2
- 235000000060 Malva neglecta Nutrition 0.000 description 2
- 240000004658 Medicago sativa Species 0.000 description 2
- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 2
- CRZQGDNQQAALAY-UHFFFAOYSA-N Methyl benzeneacetate Chemical compound COC(=O)CC1=CC=CC=C1 CRZQGDNQQAALAY-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- 235000021536 Sugar beet Nutrition 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 244000098338 Triticum aestivum Species 0.000 description 2
- 240000006064 Urena lobata Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- VEQOALNAAJBPNY-UHFFFAOYSA-N antipyrine Chemical group CN1C(C)=CC(=O)N1C1=CC=CC=C1 VEQOALNAAJBPNY-UHFFFAOYSA-N 0.000 description 2
- 239000003849 aromatic solvent Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000004459 forage Substances 0.000 description 2
- XVVBLYYGZHLQDX-UHFFFAOYSA-N hydron;[3-(trifluoromethyl)phenyl]hydrazine;chloride Chemical compound Cl.NNC1=CC=CC(C(F)(F)F)=C1 XVVBLYYGZHLQDX-UHFFFAOYSA-N 0.000 description 2
- GQTXKEVAUZYHGE-UHFFFAOYSA-N methyl 2-phenylprop-2-enoate Chemical compound COC(=O)C(=C)C1=CC=CC=C1 GQTXKEVAUZYHGE-UHFFFAOYSA-N 0.000 description 2
- 235000010460 mustard Nutrition 0.000 description 2
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- ZLMJMSJWJFRBEC-OUBTZVSYSA-N potassium-40 Chemical compound [40K] ZLMJMSJWJFRBEC-OUBTZVSYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- 150000003738 xylenes Chemical class 0.000 description 2
- GQTKYLQYHPTULY-UHFFFAOYSA-N (3-chlorophenyl) acetate Chemical compound CC(=O)OC1=CC=CC(Cl)=C1 GQTKYLQYHPTULY-UHFFFAOYSA-N 0.000 description 1
- SKVGLOFWEJFQKU-UHFFFAOYSA-N (3-fluorophenyl)hydrazine;hydron;chloride Chemical compound Cl.NNC1=CC=CC(F)=C1 SKVGLOFWEJFQKU-UHFFFAOYSA-N 0.000 description 1
- FEKUXLUOKFSMRO-UHFFFAOYSA-N (4-fluorophenyl)hydrazine;hydron;chloride Chemical compound Cl.NNC1=CC=C(F)C=C1 FEKUXLUOKFSMRO-UHFFFAOYSA-N 0.000 description 1
- DGUUZCCXBBGXNZ-UHFFFAOYSA-N 1-ethyl-2,4-bis[3-(trifluoromethyl)phenyl]pyrazol-3-one Chemical compound O=C1N(C=2C=C(C=CC=2)C(F)(F)F)N(CC)C=C1C1=CC=CC(C(F)(F)F)=C1 DGUUZCCXBBGXNZ-UHFFFAOYSA-N 0.000 description 1
- QBLDLMCRCHEYKK-UHFFFAOYSA-N 1-ethyl-2-(3-fluorophenyl)-4-(3-methylphenyl)pyrazol-3-one Chemical compound O=C1N(C=2C=C(F)C=CC=2)N(CC)C=C1C1=CC=CC(C)=C1 QBLDLMCRCHEYKK-UHFFFAOYSA-N 0.000 description 1
- WMKQEHKVIJAMTP-UHFFFAOYSA-N 1-ethyl-2-(3-fluorophenyl)-4-[3-(trifluoromethyl)phenyl]pyrazol-3-one Chemical compound O=C1N(C=2C=C(F)C=CC=2)N(CC)C=C1C1=CC=CC(C(F)(F)F)=C1 WMKQEHKVIJAMTP-UHFFFAOYSA-N 0.000 description 1
- FSHLCZQBEHMEBA-UHFFFAOYSA-N 1-ethyl-2-(4-fluorophenyl)-4-[3-(trifluoromethyl)phenyl]pyrazol-3-one Chemical compound O=C1N(C=2C=CC(F)=CC=2)N(CC)C=C1C1=CC=CC(C(F)(F)F)=C1 FSHLCZQBEHMEBA-UHFFFAOYSA-N 0.000 description 1
- DIYDSENGHGGDSE-UHFFFAOYSA-N 1-ethyl-4-(3-methylphenyl)-2-phenylpyrazol-3-one Chemical compound O=C1N(C=2C=CC=CC=2)N(CC)C=C1C1=CC=CC(C)=C1 DIYDSENGHGGDSE-UHFFFAOYSA-N 0.000 description 1
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 description 1
- IUQOKWNOIOTMFA-UHFFFAOYSA-N 2,4-bis(3-bromophenyl)-1-methylpyrazol-3-one Chemical compound O=C1N(C=2C=C(Br)C=CC=2)N(C)C=C1C1=CC=CC(Br)=C1 IUQOKWNOIOTMFA-UHFFFAOYSA-N 0.000 description 1
- LSRUOHOVDCISNX-UHFFFAOYSA-N 2,4-bis(3-chlorophenyl)-1h-pyrazol-3-one Chemical compound ClC1=CC=CC(C=2C(N(C=3C=C(Cl)C=CC=3)NC=2)=O)=C1 LSRUOHOVDCISNX-UHFFFAOYSA-N 0.000 description 1
- XONCUSHUPCWMEJ-UHFFFAOYSA-N 2-(2-chlorophenyl)-1-methyl-4-[3-(trifluoromethyl)phenyl]pyrazol-3-one Chemical compound O=C1N(C=2C(=CC=CC=2)Cl)N(C)C=C1C1=CC=CC(C(F)(F)F)=C1 XONCUSHUPCWMEJ-UHFFFAOYSA-N 0.000 description 1
- DYJNGTJFZXIDEX-UHFFFAOYSA-N 2-(3-bromophenyl)-1-methyl-4-(3-methylphenyl)pyrazol-3-one Chemical compound CC1=CC=CC(C=2C(N(C=3C=C(Br)C=CC=3)N(C)C=2)=O)=C1 DYJNGTJFZXIDEX-UHFFFAOYSA-N 0.000 description 1
- ADODRSVGNHNKAT-UHFFFAOYSA-N 2-Chlorophenylhydrazine hydrochloride Chemical compound Cl.NNC1=CC=CC=C1Cl ADODRSVGNHNKAT-UHFFFAOYSA-N 0.000 description 1
- BLXXCCIBGGBDHI-UHFFFAOYSA-N 2-[3-(trifluoromethyl)phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC(C(F)(F)F)=C1 BLXXCCIBGGBDHI-UHFFFAOYSA-N 0.000 description 1
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
- ONPJWQSDZCGSQM-UHFFFAOYSA-N 2-phenylprop-2-enoic acid Chemical compound OC(=O)C(=C)C1=CC=CC=C1 ONPJWQSDZCGSQM-UHFFFAOYSA-N 0.000 description 1
- PEYRTTTVVPKAID-UHFFFAOYSA-N 4,4-diphenyl-1H-pyrazol-5-one Chemical class C1(=CC=CC=C1)C1(C(NN=C1)=O)C1=CC=CC=C1 PEYRTTTVVPKAID-UHFFFAOYSA-N 0.000 description 1
- AEQHHAAJRUTDRR-UHFFFAOYSA-N 4-(3-bromophenyl)-1-methyl-2-phenylpyrazol-3-one Chemical compound O=C1N(C=2C=CC=CC=2)N(C)C=C1C1=CC=CC(Br)=C1 AEQHHAAJRUTDRR-UHFFFAOYSA-N 0.000 description 1
- AHDBTBAKZWGZQW-UHFFFAOYSA-N 4-(3-chlorophenyl)-1-methyl-2-(2-methylphenyl)pyrazol-3-one Chemical compound CC1=CC=CC=C1N1C(=O)C(C=2C=C(Cl)C=CC=2)=CN1C AHDBTBAKZWGZQW-UHFFFAOYSA-N 0.000 description 1
- XPEISPYOFMSZKN-UHFFFAOYSA-N 4-(3-chlorophenyl)-2-(2-fluorophenyl)-1-propylpyrazol-3-one Chemical compound O=C1N(C=2C(=CC=CC=2)F)N(CCC)C=C1C1=CC=CC(Cl)=C1 XPEISPYOFMSZKN-UHFFFAOYSA-N 0.000 description 1
- PBEMXBIJVNPFDL-UHFFFAOYSA-N 4-(3-chlorophenyl)-2-[3-(trifluoromethyl)phenyl]-1h-pyrazol-3-one Chemical compound FC(F)(F)C1=CC=CC(N2C(C(C=3C=C(Cl)C=CC=3)=CN2)=O)=C1 PBEMXBIJVNPFDL-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- RLFWWDJHLFCNIJ-UHFFFAOYSA-N Aminoantipyrine Natural products CN1C(C)=C(N)C(=O)N1C1=CC=CC=C1 RLFWWDJHLFCNIJ-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 240000006122 Chenopodium album Species 0.000 description 1
- 235000011498 Chenopodium album var missouriense Nutrition 0.000 description 1
- 235000013328 Chenopodium album var. album Nutrition 0.000 description 1
- 235000014052 Chenopodium album var. microphyllum Nutrition 0.000 description 1
- 235000014050 Chenopodium album var. stevensii Nutrition 0.000 description 1
- 235000013012 Chenopodium album var. striatum Nutrition 0.000 description 1
- 235000000509 Chenopodium ambrosioides Nutrition 0.000 description 1
- 244000098897 Chenopodium botrys Species 0.000 description 1
- 235000005490 Chenopodium botrys Nutrition 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 240000008853 Datura stramonium Species 0.000 description 1
- 240000003173 Drymaria cordata Species 0.000 description 1
- 244000078127 Eleusine coracana Species 0.000 description 1
- 235000013499 Eleusine coracana subsp coracana Nutrition 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- 244000171263 Ribes grossularia Species 0.000 description 1
- 235000002357 Ribes grossularia Nutrition 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 241000208292 Solanaceae Species 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 1
- MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 244000038559 crop plants Species 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- CRPOUZQWHJYTMS-UHFFFAOYSA-N dialuminum;magnesium;disilicate Chemical compound [Mg+2].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-] CRPOUZQWHJYTMS-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- SHTBTGXNVWYODU-UHFFFAOYSA-N hydron;(3-methylphenyl)hydrazine;chloride Chemical compound Cl.CC1=CC=CC(NN)=C1 SHTBTGXNVWYODU-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 235000019357 lignosulphonate Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- OXYLCGRXCQARQV-UHFFFAOYSA-N methyl 2-(3-fluorophenyl)acetate Chemical compound COC(=O)CC1=CC=CC(F)=C1 OXYLCGRXCQARQV-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 238000004452 microanalysis Methods 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229960005222 phenazone Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000008318 pyrimidones Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
- C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US63974475A | 1975-12-11 | 1975-12-11 | |
| US05/724,502 US4075003A (en) | 1975-12-11 | 1976-09-20 | Novel herbicidal method utilizing 1,4-diphenyl-3-pyrazolin-5-ones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH622784A5 true CH622784A5 (en) | 1981-04-30 |
Family
ID=27093389
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1520676A CH622784A5 (en) | 1975-12-11 | 1976-12-02 | Process for the preparation of 1,4-diphenyl-3-pyrazolin-5-ones |
Country Status (28)
| Country | Link |
|---|---|
| JP (1) | JPS6033112B2 (cs) |
| AR (1) | AR218861A1 (cs) |
| AT (1) | AT354434B (cs) |
| AU (1) | AU507882B2 (cs) |
| BG (1) | BG27547A3 (cs) |
| CA (1) | CA1067907A (cs) |
| CH (1) | CH622784A5 (cs) |
| CS (1) | CS186746B2 (cs) |
| DD (1) | DD129326A5 (cs) |
| DE (1) | DE2651008A1 (cs) |
| DK (1) | DK550876A (cs) |
| ES (1) | ES454061A1 (cs) |
| FR (1) | FR2334674A1 (cs) |
| GB (1) | GB1570623A (cs) |
| GR (1) | GR63123B (cs) |
| IE (1) | IE43807B1 (cs) |
| IL (1) | IL50792A (cs) |
| IT (1) | IT1123686B (cs) |
| MX (1) | MX3832E (cs) |
| NL (1) | NL7613810A (cs) |
| NZ (1) | NZ182530A (cs) |
| PH (1) | PH13076A (cs) |
| PL (1) | PL106071B1 (cs) |
| PT (1) | PT65890B (cs) |
| RO (1) | RO72400B (cs) |
| SE (1) | SE430413B (cs) |
| SU (1) | SU643083A3 (cs) |
| ZA (1) | ZA766561B (cs) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK529378A (da) * | 1978-01-09 | 1979-07-10 | Shell Int Research | Anilidderivater |
| NZ213630A (en) * | 1984-10-19 | 1990-02-26 | Ici Plc | Acrylic acid derivatives and fungicidal compositions |
| DE3527157A1 (de) | 1985-07-30 | 1987-02-12 | Bayer Ag | 1-heteroaryl-4-aryl-pyrazol-derivate |
| DE102008020113A1 (de) | 2008-04-23 | 2009-10-29 | Bayer Schering Pharma Aktiengesellschaft | Substituierte Dihydropyrazolone und ihre Verwendung |
| DE102005019712A1 (de) | 2005-04-28 | 2006-11-09 | Bayer Healthcare Ag | Dipyridyl-dihydropyrazolone und ihre Verwendung |
| DE102006050516A1 (de) | 2006-10-26 | 2008-04-30 | Bayer Healthcare Ag | Substituierte Dihydropyrazolone und ihre Verwendung |
| DE102006050513A1 (de) | 2006-10-26 | 2008-04-30 | Bayer Healthcare Ag | Substitiuierte Dihydropyrazolone und ihre Verwendung |
| DE102006050515A1 (de) | 2006-10-26 | 2008-04-30 | Bayer Healthcare Ag | Substituierte Dipyridiyl-dihydropyrazolone und ihre Verwendung |
| DE102007044032A1 (de) | 2007-09-14 | 2009-03-19 | Bayer Healthcare Ag | Substituierte heterocyclische Verbindungen und ihre Verwendung |
| DE102007048447A1 (de) | 2007-10-10 | 2009-04-16 | Bayer Healthcare Ag | Substituierte Dihydropyrazolthione und ihre Verwendung |
| DE102010044131A1 (de) | 2010-11-18 | 2012-05-24 | Bayer Schering Pharma Aktiengesellschaft | Substituiertes Natrium-1H-pyrazol-5-olat |
-
1976
- 1976-10-25 GR GR52014A patent/GR63123B/el unknown
- 1976-10-28 IL IL50792A patent/IL50792A/xx unknown
- 1976-10-29 CA CA264,490A patent/CA1067907A/en not_active Expired
- 1976-11-01 IE IE2429/76A patent/IE43807B1/en unknown
- 1976-11-02 ZA ZA00766561A patent/ZA766561B/xx unknown
- 1976-11-04 NZ NZ182530A patent/NZ182530A/xx unknown
- 1976-11-05 PH PH19097A patent/PH13076A/en unknown
- 1976-11-08 DE DE19762651008 patent/DE2651008A1/de not_active Withdrawn
- 1976-11-25 SE SE7613239A patent/SE430413B/xx unknown
- 1976-11-25 PT PT65890A patent/PT65890B/pt unknown
- 1976-11-26 AR AR265630A patent/AR218861A1/es active
- 1976-12-02 CH CH1520676A patent/CH622784A5/de not_active IP Right Cessation
- 1976-12-02 ES ES454061A patent/ES454061A1/es not_active Expired
- 1976-12-04 RO RO88642A patent/RO72400B/ro unknown
- 1976-12-06 FR FR7636699A patent/FR2334674A1/fr active Granted
- 1976-12-06 GB GB50713/76A patent/GB1570623A/en not_active Expired
- 1976-12-06 MX MX765189U patent/MX3832E/es unknown
- 1976-12-07 CS CS7600007973A patent/CS186746B2/cs unknown
- 1976-12-08 DK DK550876A patent/DK550876A/da not_active Application Discontinuation
- 1976-12-08 DD DD7600196193A patent/DD129326A5/xx unknown
- 1976-12-09 BG BG034872A patent/BG27547A3/xx unknown
- 1976-12-09 AT AT911876A patent/AT354434B/de not_active IP Right Cessation
- 1976-12-09 AU AU20436/76A patent/AU507882B2/en not_active Expired
- 1976-12-10 SU SU762427094A patent/SU643083A3/ru active
- 1976-12-10 PL PL1976194292A patent/PL106071B1/pl unknown
- 1976-12-10 IT IT30299/76A patent/IT1123686B/it active
- 1976-12-11 JP JP51149321A patent/JPS6033112B2/ja not_active Expired
- 1976-12-13 NL NL7613810A patent/NL7613810A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| ZA766561B (en) | 1978-06-28 |
| PT65890A (en) | 1976-12-01 |
| RO72400B (ro) | 1983-04-30 |
| FR2334674B1 (cs) | 1980-11-07 |
| IL50792A0 (en) | 1976-12-31 |
| BG27547A3 (en) | 1979-11-12 |
| JPS5273868A (en) | 1977-06-21 |
| JPS6033112B2 (ja) | 1985-08-01 |
| AT354434B (de) | 1979-01-10 |
| CA1067907A (en) | 1979-12-11 |
| GB1570623A (en) | 1980-07-02 |
| CS186746B2 (en) | 1978-12-29 |
| MX3832E (es) | 1981-08-04 |
| SE430413B (sv) | 1983-11-14 |
| GR63123B (en) | 1979-09-11 |
| DE2651008A1 (de) | 1977-06-23 |
| FR2334674A1 (fr) | 1977-07-08 |
| NL7613810A (nl) | 1977-06-14 |
| IL50792A (en) | 1979-05-31 |
| AR218861A1 (es) | 1980-07-15 |
| IE43807L (en) | 1977-06-11 |
| DD129326A5 (de) | 1978-01-11 |
| ATA911876A (de) | 1979-06-15 |
| AU507882B2 (en) | 1980-02-28 |
| IT1123686B (it) | 1986-04-30 |
| PT65890B (en) | 1978-05-18 |
| PH13076A (en) | 1979-11-23 |
| ES454061A1 (es) | 1978-03-01 |
| SU643083A3 (ru) | 1979-01-15 |
| IE43807B1 (en) | 1981-06-03 |
| NZ182530A (en) | 1978-06-20 |
| RO72400A (ro) | 1983-04-29 |
| DK550876A (da) | 1977-06-12 |
| AU2043676A (en) | 1978-06-15 |
| SE7613239L (sv) | 1977-06-12 |
| PL106071B1 (pl) | 1979-11-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |