CA1047502A - Substituted pyrazoles - Google Patents
Substituted pyrazolesInfo
- Publication number
- CA1047502A CA1047502A CA221,039A CA221039A CA1047502A CA 1047502 A CA1047502 A CA 1047502A CA 221039 A CA221039 A CA 221039A CA 1047502 A CA1047502 A CA 1047502A
- Authority
- CA
- Canada
- Prior art keywords
- spp
- phenyl
- substituted
- alkyl
- parts
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000003217 pyrazoles Chemical class 0.000 title claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 25
- 150000001875 compounds Chemical class 0.000 claims abstract description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
- 239000001257 hydrogen Substances 0.000 claims abstract description 17
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 6
- 125000001246 bromo group Chemical group Br* 0.000 claims abstract description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 4
- 125000002252 acyl group Chemical group 0.000 claims abstract description 3
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 3
- 125000005059 halophenyl group Chemical group 0.000 claims abstract description 3
- 125000005843 halogen group Chemical group 0.000 claims abstract 2
- NEELEVWEBRBBBE-UHFFFAOYSA-N 5-phenyl-3-phenylsulfanyl-1h-pyrazole Chemical group C=1C=CC=CC=1SC(=NN1)C=C1C1=CC=CC=C1 NEELEVWEBRBBBE-UHFFFAOYSA-N 0.000 claims description 9
- UIHAJLQDDKTZAI-UHFFFAOYSA-N 3-benzylsulfanyl-5-phenyl-1h-pyrazole Chemical group C=1C=CC=CC=1CSC(=NN1)C=C1C1=CC=CC=C1 UIHAJLQDDKTZAI-UHFFFAOYSA-N 0.000 claims description 3
- SGQJJVBDXMHQIO-UHFFFAOYSA-N 5-(3,5-dimethylphenyl)-3-phenylsulfanyl-1h-pyrazole Chemical group CC1=CC(C)=CC(C=2NN=C(SC=3C=CC=CC=3)C=2)=C1 SGQJJVBDXMHQIO-UHFFFAOYSA-N 0.000 claims description 3
- POBMFNPLFSOSRO-UHFFFAOYSA-N 1-(3-phenyl-5-phenylsulfanylpyrazol-1-yl)ethanone Chemical group CC(=O)N1N=C(C=2C=CC=CC=2)C=C1SC1=CC=CC=C1 POBMFNPLFSOSRO-UHFFFAOYSA-N 0.000 claims description 2
- -1 dichlorophenoxy Chemical group 0.000 abstract description 34
- 239000004480 active ingredient Substances 0.000 abstract description 23
- 239000004009 herbicide Chemical class 0.000 abstract description 7
- 230000012010 growth Effects 0.000 abstract description 4
- 150000003839 salts Chemical class 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 150000001408 amides Chemical class 0.000 description 15
- 239000000203 mixture Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- 241000196324 Embryophyta Species 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 12
- 239000003921 oil Substances 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 150000007513 acids Chemical class 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 244000038559 crop plants Species 0.000 description 8
- 230000006378 damage Effects 0.000 description 8
- 239000006185 dispersion Substances 0.000 description 8
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 230000002363 herbicidal effect Effects 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 235000021533 Beta vulgaris Nutrition 0.000 description 5
- 241000335053 Beta vulgaris Species 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical class CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 235000007340 Hordeum vulgare Nutrition 0.000 description 4
- 240000005979 Hordeum vulgare Species 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- 239000004359 castor oil Substances 0.000 description 4
- 235000019438 castor oil Nutrition 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 244000100545 Lolium multiflorum Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 244000098338 Triticum aestivum Species 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 235000012054 meals Nutrition 0.000 description 3
- 150000002790 naphthalenes Chemical class 0.000 description 3
- 239000006072 paste Substances 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- XQEMNBNCQVQXMO-UHFFFAOYSA-M 1,2-dimethyl-3,5-diphenylpyrazol-1-ium;methyl sulfate Chemical compound COS([O-])(=O)=O.C[N+]=1N(C)C(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 XQEMNBNCQVQXMO-UHFFFAOYSA-M 0.000 description 2
- OBTZDIRUQWFRFZ-UHFFFAOYSA-N 2-(5-methylfuran-2-yl)-n-(4-methylphenyl)quinoline-4-carboxamide Chemical compound O1C(C)=CC=C1C1=CC(C(=O)NC=2C=CC(C)=CC=2)=C(C=CC=C2)C2=N1 OBTZDIRUQWFRFZ-UHFFFAOYSA-N 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- 241001621841 Alopecurus myosuroides Species 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- 241000208173 Apiaceae Species 0.000 description 2
- 241000208838 Asteraceae Species 0.000 description 2
- 235000005781 Avena Nutrition 0.000 description 2
- 244000075850 Avena orientalis Species 0.000 description 2
- 235000011331 Brassica Nutrition 0.000 description 2
- 241000219198 Brassica Species 0.000 description 2
- 235000008427 Brassica arvensis Nutrition 0.000 description 2
- 244000024671 Brassica kaber Species 0.000 description 2
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 2
- 241000219193 Brassicaceae Species 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 241000871189 Chenopodiaceae Species 0.000 description 2
- 244000000626 Daucus carota Species 0.000 description 2
- 235000002767 Daucus carota Nutrition 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 244000058871 Echinochloa crus-galli Species 0.000 description 2
- 241000220485 Fabaceae Species 0.000 description 2
- 241000208822 Lactuca Species 0.000 description 2
- 241000801118 Lepidium Species 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241000219071 Malvaceae Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 241000209117 Panicum Species 0.000 description 2
- 235000011999 Panicum crusgalli Nutrition 0.000 description 2
- 235000006443 Panicum miliaceum subsp. miliaceum Nutrition 0.000 description 2
- 235000009037 Panicum miliaceum subsp. ruderale Nutrition 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 241000013557 Plantaginaceae Species 0.000 description 2
- 244000292693 Poa annua Species 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- 241000220259 Raphanus Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 241000208292 Solanaceae Species 0.000 description 2
- 235000002634 Solanum Nutrition 0.000 description 2
- 241000207763 Solanum Species 0.000 description 2
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 2
- 244000062793 Sorghum vulgare Species 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- 241000219793 Trifolium Species 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 230000001464 adherent effect Effects 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000000729 antidote Substances 0.000 description 2
- 229940075522 antidotes Drugs 0.000 description 2
- 239000003899 bactericide agent Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000003337 fertilizer Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 230000001069 nematicidal effect Effects 0.000 description 2
- 239000005645 nematicide Substances 0.000 description 2
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- OHPMGIYXBRVIES-UHFFFAOYSA-N (3,5-diphenyl-1H-pyrazol-4-yl) hydrogen sulfate Chemical compound C1(=CC=CC=C1)C1=NNC(=C1OS(=O)(=O)O)C1=CC=CC=C1 OHPMGIYXBRVIES-UHFFFAOYSA-N 0.000 description 1
- FTDGDIFUDKDKAW-UHFFFAOYSA-N 1,1a,5,5a,6,6a-hexahydrocyclopropa[a]indene Chemical group C12C(CC3CC=CC=C13)C2 FTDGDIFUDKDKAW-UHFFFAOYSA-N 0.000 description 1
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical group C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 1
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical group C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 description 1
- LTQKIFCNCIFEHG-UHFFFAOYSA-N 1,2-oxazole 1H-pyrimidin-2-one Chemical group C=1C=NOC=1.O=C1N=CC=CN1 LTQKIFCNCIFEHG-UHFFFAOYSA-N 0.000 description 1
- MFVFDTCSVFBOTL-UHFFFAOYSA-N 1,3-diazetidine Chemical class C1NCN1 MFVFDTCSVFBOTL-UHFFFAOYSA-N 0.000 description 1
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
- RZXQLBGBKXHJOI-UHFFFAOYSA-N 1,3-diphenyl-5-phenylsulfanylpyrazole Chemical compound C=1C=CC=CC=1SC1=CC(C=2C=CC=CC=2)=NN1C1=CC=CC=C1 RZXQLBGBKXHJOI-UHFFFAOYSA-N 0.000 description 1
- FKKAGFLIPSSCHT-UHFFFAOYSA-N 1-dodecoxydodecane;sulfuric acid Chemical compound OS(O)(=O)=O.CCCCCCCCCCCCOCCCCCCCCCCCC FKKAGFLIPSSCHT-UHFFFAOYSA-N 0.000 description 1
- ZLOTYHZOJPLLGG-UHFFFAOYSA-N 1-sulfanylidenethiadiazinane Chemical class S=S1CCCNN1 ZLOTYHZOJPLLGG-UHFFFAOYSA-N 0.000 description 1
- XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- NOIXNOMHHWGUTG-UHFFFAOYSA-N 2-[[4-[4-pyridin-4-yl-1-(2,2,2-trifluoroethyl)pyrazol-3-yl]phenoxy]methyl]quinoline Chemical compound C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C1=NN(CC(F)(F)F)C=C1C1=CC=NC=C1 NOIXNOMHHWGUTG-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 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
- REEXLQXWNOSJKO-UHFFFAOYSA-N 2h-1$l^{4},2,3-benzothiadiazine 1-oxide Chemical class C1=CC=C2S(=O)NN=CC2=C1 REEXLQXWNOSJKO-UHFFFAOYSA-N 0.000 description 1
- MBKHEMXBDRVDBR-UHFFFAOYSA-N 3-(4-chlorophenyl)sulfanyl-5-phenyl-1h-pyrazole Chemical compound C1=CC(Cl)=CC=C1SC1=NNC(C=2C=CC=CC=2)=C1 MBKHEMXBDRVDBR-UHFFFAOYSA-N 0.000 description 1
- GWFPTEIQBSEGIF-UHFFFAOYSA-N 3-methylsulfanyl-5-phenyl-1h-pyrazole Chemical compound N1N=C(SC)C=C1C1=CC=CC=C1 GWFPTEIQBSEGIF-UHFFFAOYSA-N 0.000 description 1
- CKHYKYQGFFEGBU-UHFFFAOYSA-N 3-phenylsulfanyl-5-propan-2-yl-1h-pyrazole Chemical compound N1C(C(C)C)=CC(SC=2C=CC=CC=2)=N1 CKHYKYQGFFEGBU-UHFFFAOYSA-N 0.000 description 1
- HHIBCYLSYGZQIZ-UHFFFAOYSA-N 3-phenylsulfanyl-5-thiophen-2-yl-1h-pyrazole Chemical compound C=1C=CC=CC=1SC(=NN1)C=C1C1=CC=CS1 HHIBCYLSYGZQIZ-UHFFFAOYSA-N 0.000 description 1
- QZBOTZOIKVJOIE-UHFFFAOYSA-N 4-bromo-5-phenyl-3-phenylsulfanyl-1h-pyrazole Chemical compound N=1NC(C=2C=CC=CC=2)=C(Br)C=1SC1=CC=CC=C1 QZBOTZOIKVJOIE-UHFFFAOYSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
- RQMWVVBHJMUJNZ-UHFFFAOYSA-N 4-chloropyridin-2-amine Chemical group NC1=CC(Cl)=CC=N1 RQMWVVBHJMUJNZ-UHFFFAOYSA-N 0.000 description 1
- HQQTZCPKNZVLFF-UHFFFAOYSA-N 4h-1,2-benzoxazin-3-one Chemical class C1=CC=C2ONC(=O)CC2=C1 HQQTZCPKNZVLFF-UHFFFAOYSA-N 0.000 description 1
- MUFPPPCYJCUQIX-UHFFFAOYSA-N 5-(3-methylphenyl)-3-phenylsulfanyl-1h-pyrazole Chemical compound CC1=CC=CC(C=2NN=C(SC=3C=CC=CC=3)C=2)=C1 MUFPPPCYJCUQIX-UHFFFAOYSA-N 0.000 description 1
- RIGRAJDBGUIFKT-UHFFFAOYSA-N 5-(4-bromophenyl)-3-phenylsulfanyl-1h-pyrazole Chemical compound C1=CC(Br)=CC=C1C1=CC(SC=2C=CC=CC=2)=NN1 RIGRAJDBGUIFKT-UHFFFAOYSA-N 0.000 description 1
- HCPQVOLAULQJHW-UHFFFAOYSA-N 5-(4-chlorophenyl)-3-phenylsulfanyl-1h-pyrazole Chemical compound C1=CC(Cl)=CC=C1C1=CC(SC=2C=CC=CC=2)=NN1 HCPQVOLAULQJHW-UHFFFAOYSA-N 0.000 description 1
- YFBHYKFQBIQDJG-UHFFFAOYSA-N 5-cyclohexyl-3-phenylsulfanyl-1h-pyrazole Chemical compound C1CCCCC1C1=CC(SC=2C=CC=CC=2)=NN1 YFBHYKFQBIQDJG-UHFFFAOYSA-N 0.000 description 1
- 241000219144 Abutilon Species 0.000 description 1
- 241000206486 Adonis Species 0.000 description 1
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- YDCVQGAUCOROHB-UHFFFAOYSA-N oxadiazolidine-4,5-dione Chemical class O=C1NNOC1=O YDCVQGAUCOROHB-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical class C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 239000001377 petroselinum spp. Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- REJGOFYVRVIODZ-UHFFFAOYSA-N phosphanium;chloride Chemical group P.Cl REJGOFYVRVIODZ-UHFFFAOYSA-N 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical group [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 150000004892 pyridazines Chemical group 0.000 description 1
- 150000005299 pyridinones Chemical class 0.000 description 1
- 150000003230 pyrimidines Chemical group 0.000 description 1
- 150000008318 pyrimidones Chemical group 0.000 description 1
- NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical class OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 description 1
- 150000003235 pyrrolidines Chemical group 0.000 description 1
- 150000004040 pyrrolidinones Chemical group 0.000 description 1
- 150000003246 quinazolines Chemical group 0.000 description 1
- 150000003248 quinolines Chemical group 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003440 styrenes Chemical group 0.000 description 1
- 150000003871 sulfonates Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 150000003566 thiocarboxylic acids Chemical class 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 150000003918 triazines Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000002023 wood 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2409753A DE2409753A1 (de) | 1974-03-01 | 1974-03-01 | Substituierte pyrazole |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1047502A true CA1047502A (en) | 1979-01-30 |
Family
ID=5908770
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA221,039A Expired CA1047502A (en) | 1974-03-01 | 1975-02-28 | Substituted pyrazoles |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4008249A (en, 2012) |
| JP (1) | JPS50117936A (en, 2012) |
| AT (1) | AT340199B (en, 2012) |
| BE (1) | BE826074A (en, 2012) |
| BG (1) | BG26354A3 (en, 2012) |
| CA (1) | CA1047502A (en, 2012) |
| CH (1) | CH593609A5 (en, 2012) |
| CS (1) | CS185676B2 (en, 2012) |
| DD (1) | DD117977A5 (en, 2012) |
| DE (1) | DE2409753A1 (en, 2012) |
| DK (1) | DK139474C (en, 2012) |
| ES (1) | ES435199A1 (en, 2012) |
| FR (1) | FR2262663B1 (en, 2012) |
| GB (1) | GB1488285A (en, 2012) |
| HU (1) | HU171228B (en, 2012) |
| IL (1) | IL46563A (en, 2012) |
| IT (1) | IT1044124B (en, 2012) |
| NL (1) | NL7502416A (en, 2012) |
| NO (1) | NO142800C (en, 2012) |
| PL (1) | PL92447B1 (en, 2012) |
| SE (1) | SE413026B (en, 2012) |
| SU (1) | SU569268A3 (en, 2012) |
| ZA (1) | ZA751242B (en, 2012) |
Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5436648B2 (en, 2012) * | 1974-03-28 | 1979-11-10 | ||
| US4123252A (en) * | 1976-01-16 | 1978-10-31 | E. I. Du Pont De Nemours And Company | Methoxy substituted cycloalkanapyrazole herbicides |
| US4124374A (en) * | 1976-02-06 | 1978-11-07 | E. I. Du Pont De Nemours And Company | Alkyl-substituted cycloalkanapyrazole herbicides |
| US4230481A (en) * | 1977-08-12 | 1980-10-28 | Ishihara Sangyo Kaisha Limited | Pyrazole derivatives useful as a herbicidal component |
| DE2747531A1 (de) * | 1977-10-22 | 1979-04-26 | Basf Ag | Substituierte 3-aminopyrazole |
| EP0014810A3 (en) * | 1979-01-18 | 1980-11-26 | Fbc Limited | Pesticidal pyrazoles, their production, compositions and uses, as well as intermediates and their preparation |
| FR2460299A1 (fr) * | 1979-07-05 | 1981-01-23 | Bellon Labor Sa Roger | Nouveaux derives du pyrazole et leur application therapeutique |
| DE3332271A1 (de) * | 1983-09-07 | 1985-03-21 | Bayer Ag, 5090 Leverkusen | Herbizide mittel enthaltend metribuzin in kombination mit substituierten azolyl-derivaten |
| US4620865A (en) * | 1983-11-07 | 1986-11-04 | Eli Lilly And Company | Herbicidal and algicidal 1,5-disubstituted-1H-pyrazole-4-carboxamides |
| GB2161160B (en) * | 1984-07-06 | 1989-05-24 | Fisons Plc | Heterocyclic sulphinyl compounds |
| US4666507A (en) * | 1985-01-16 | 1987-05-19 | Nippon Kayaku Kabushiki Kaisha | Herbicidal 5-halo-1-[5-(N-substituted sulfonylamino)phenyl]pyrazole derivatives |
| DE3529829A1 (de) * | 1985-08-21 | 1987-02-26 | Bayer Ag | 1-arylpyrazole |
| US6372774B1 (en) | 1985-12-20 | 2002-04-16 | Rhone-Poulenc Agriculture Ltd. | Derivatives of N-phenylpyrazoles |
| US5232940A (en) * | 1985-12-20 | 1993-08-03 | Hatton Leslie R | Derivatives of N-phenylpyrazoles |
| US5547974A (en) * | 1985-12-20 | 1996-08-20 | Rhone-Poulenc Agriculture Ltd. | Derivatives of N-phenylpyrazoles |
| DE3704359A1 (de) * | 1987-02-12 | 1988-08-25 | Basf Ag | Azolhalbaminal-derivate und ihre verwendung als nitrifikationsinhibitoren |
| CA1340284C (en) * | 1987-03-19 | 1998-12-22 | Zeneca Inc. | Herbicidal substituted cyclic diones |
| US4964895A (en) * | 1987-06-08 | 1990-10-23 | Monsanto Company | Substituted 4-(4-nitrophenoxy) pyrazoles and their use as herbicides |
| KR930004672B1 (ko) * | 1988-08-31 | 1993-06-03 | 니혼 노야꾸 가부시끼가이샤 | 3-치환 페닐피라졸 유도체 또는 이의 염 및 이의 제조방법, 이의 용도 및 이의 사용 방법 |
| ES2118060T3 (es) * | 1990-02-21 | 1998-09-16 | Nihon Nohyaku Co Ltd | Derivados de 3-(fenil sustituido)pirazol, sus sales, sus herbicidas; y los procedimientos de preparacion de estos derivados o de sus sales. |
| TR24287A (tr) * | 1990-03-13 | 1991-09-01 | Nihon Nohyaku Co Ltd | 3-(ikameli feniluepirazol tuerevleri,bunlarin tuzla- ri,bunlardan elde edilen herb |
| WO1992002509A1 (en) * | 1990-08-06 | 1992-02-20 | Monsanto Company | Herbicidal substituted aryl alkylsulfonyl pyrazoles |
| US5281571A (en) * | 1990-10-18 | 1994-01-25 | Monsanto Company | Herbicidal benzoxazinone- and benzothiazinone-substituted pyrazoles |
| EP0493925B1 (en) | 1990-12-17 | 1997-11-05 | Sankyo Company Limited | Pyrazole derivatives having herbicidal activity, their preparation and their use |
| US5532416A (en) * | 1994-07-20 | 1996-07-02 | Monsanto Company | Benzoyl derivatives and synthesis thereof |
| FR2690440B1 (fr) * | 1992-04-27 | 1995-05-19 | Rhone Poulenc Agrochimie | Arylpyrazoles fongicides. |
| AU653299B2 (en) * | 1993-02-06 | 1994-09-22 | Nihon Nohyaku Co., Ltd. | A herbicidal composition having a reduced phytotoxicity |
| US5880290A (en) * | 1994-01-31 | 1999-03-09 | Monsanto Company | Preparation of substituted 3-aryl-5-haloalkyl-pyrazoles having herbicidal activity |
| DE4417837A1 (de) | 1994-05-20 | 1995-11-23 | Basf Ag | Substituierte 3-Phenylpyrazole |
| DE4419517A1 (de) * | 1994-06-03 | 1995-12-07 | Basf Ag | Substituierte 3-Phenylpyrazole |
| US5869688A (en) * | 1994-07-20 | 1999-02-09 | Monsanto Company | Preparation of substituted 3-aryl-5-haloalkyl-pyrazoles having herbicidal activity |
| US6103667A (en) * | 1995-06-15 | 2000-08-15 | Novartis Corporation | Phenylpyrazole herbicides |
| AU6221796A (en) * | 1995-06-15 | 1997-01-15 | Ciba-Geigy Ag | Novel herbicides |
| EP0802191A4 (en) * | 1995-10-13 | 2001-08-01 | Otsuka Kagaku Kk | PYRAZOLE DERIVATIVES AND INSECTICIDE COMPOSITIONS CONTAINING SUCH DERIVATIVES AS ACTIVE INGREDIENTS |
| AU7579696A (en) * | 1995-11-15 | 1997-06-05 | Zeneca Limited | Herbicidal substituted pyrazole compounds |
| US5698495A (en) * | 1995-11-15 | 1997-12-16 | Zeneca Limited | Herbicidal substituted pyrazole compounds |
| DE19602404A1 (de) * | 1996-01-24 | 1997-07-31 | Basf Ag | Sulfoxid- und Sulfon-substituierte Heterocyclen, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide |
| US5698708A (en) * | 1996-06-20 | 1997-12-16 | Monsanto Company | Preparation of substituted 3-aryl-5-haloalkyl-pyrazoles having herbicidal activity |
| DE19645313A1 (de) | 1996-11-04 | 1998-05-07 | Basf Ag | Substituierte 3-Benzylpyrazole |
| DE19751943A1 (de) * | 1997-11-24 | 1999-05-27 | Hoechst Schering Agrevo Gmbh | 1-Methyl-5-alkylsulfonyl-, 1-Methyl-5-alkylsulfinyl- und 1-Methyl-5-alkylthio-substituierte Pyrazolylpyrazole, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide |
| WO2002066439A1 (fr) * | 2001-02-20 | 2002-08-29 | Sagami Chemical Research Center | Derives de pyrazole, intermediaires associes, procedes de production associes et herbicide contenant lesdits derives en tant qu'ingredient actif |
| NZ718622A (en) * | 2010-03-30 | 2018-03-23 | Verseon Corp | Multisubstituted aromatic compounds as inhibitors of thrombin |
| LT2968297T (lt) | 2013-03-15 | 2019-01-10 | Verseon Corporation | Multipakeistieji aromatiniai junginiai kaip serino proteazės inhibitoriai |
| AU2014238478B2 (en) | 2013-03-15 | 2018-07-19 | Verseon Corporation | Halogenopyrazoles as inhibitors of thrombin |
| JP2017528486A (ja) | 2014-09-17 | 2017-09-28 | ヴァーセオン コーポレイション | セリンプロテアーゼ阻害剤としてのピラゾリル置換ピリドン化合物 |
| BR112017018092A2 (pt) | 2015-02-27 | 2018-04-10 | Verseon Corp | composto, composição farmacêutica, e, método para tratar e/ou prevenir uma doença ou distúrbio. |
-
1974
- 1974-03-01 DE DE2409753A patent/DE2409753A1/de not_active Withdrawn
-
1975
- 1975-02-04 IL IL46563A patent/IL46563A/xx unknown
- 1975-02-18 JP JP50019515A patent/JPS50117936A/ja active Pending
- 1975-02-21 BG BG029043A patent/BG26354A3/xx unknown
- 1975-02-24 SU SU7502107330A patent/SU569268A3/ru active
- 1975-02-26 CH CH241575A patent/CH593609A5/xx not_active IP Right Cessation
- 1975-02-26 CS CS7500001290A patent/CS185676B2/cs unknown
- 1975-02-27 BE BE153824A patent/BE826074A/xx unknown
- 1975-02-27 US US05/553,496 patent/US4008249A/en not_active Expired - Lifetime
- 1975-02-27 IT IT48351/75A patent/IT1044124B/it active
- 1975-02-27 DD DD184466A patent/DD117977A5/xx unknown
- 1975-02-28 SE SE7502300A patent/SE413026B/xx unknown
- 1975-02-28 CA CA221,039A patent/CA1047502A/en not_active Expired
- 1975-02-28 GB GB8386/75A patent/GB1488285A/en not_active Expired
- 1975-02-28 ZA ZA00751242A patent/ZA751242B/xx unknown
- 1975-02-28 PL PL1975178380A patent/PL92447B1/xx unknown
- 1975-02-28 NL NL7502416A patent/NL7502416A/xx not_active Application Discontinuation
- 1975-02-28 ES ES435199A patent/ES435199A1/es not_active Expired
- 1975-02-28 FR FR7506323A patent/FR2262663B1/fr not_active Expired
- 1975-02-28 NO NO750690A patent/NO142800C/no unknown
- 1975-02-28 AT AT159275A patent/AT340199B/de not_active IP Right Cessation
- 1975-02-28 DK DK79975A patent/DK139474C/da active
- 1975-02-28 HU HU75BA00003219A patent/HU171228B/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL46563A (en) | 1978-04-30 |
| JPS50117936A (en, 2012) | 1975-09-16 |
| FR2262663A1 (en, 2012) | 1975-09-26 |
| DK139474C (da) | 1979-08-13 |
| US4008249A (en) | 1977-02-15 |
| SU569268A3 (ru) | 1977-08-15 |
| IT1044124B (it) | 1980-03-20 |
| NL7502416A (nl) | 1975-09-03 |
| CS185676B2 (en) | 1978-10-31 |
| CH593609A5 (en, 2012) | 1977-12-15 |
| NO142800C (no) | 1980-10-22 |
| NO750690L (en, 2012) | 1975-09-02 |
| DK79975A (en, 2012) | 1975-11-03 |
| BG26354A3 (bg) | 1979-03-15 |
| NO142800B (no) | 1980-07-14 |
| DE2409753A1 (de) | 1975-09-11 |
| PL92447B1 (en, 2012) | 1977-04-30 |
| SE7502300L (en, 2012) | 1975-09-02 |
| HU171228B (hu) | 1977-12-28 |
| IL46563A0 (en) | 1975-04-25 |
| DD117977A5 (en, 2012) | 1976-02-12 |
| ZA751242B (en) | 1976-02-25 |
| DK139474B (da) | 1979-02-26 |
| AT340199B (de) | 1977-11-25 |
| GB1488285A (en) | 1977-10-12 |
| BE826074A (fr) | 1975-08-27 |
| SE413026B (sv) | 1980-03-31 |
| ATA159275A (de) | 1977-03-15 |
| FR2262663B1 (en, 2012) | 1978-07-13 |
| ES435199A1 (es) | 1977-04-16 |
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