DE2618421A1 - Diphenylpyrazoliumsalze - Google Patents
DiphenylpyrazoliumsalzeInfo
- Publication number
- DE2618421A1 DE2618421A1 DE19762618421 DE2618421A DE2618421A1 DE 2618421 A1 DE2618421 A1 DE 2618421A1 DE 19762618421 DE19762618421 DE 19762618421 DE 2618421 A DE2618421 A DE 2618421A DE 2618421 A1 DE2618421 A1 DE 2618421A1
- Authority
- DE
- Germany
- Prior art keywords
- dimethyl
- diphenyl
- diphenylpyrazolium
- salt
- benzyl
- 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.)
- Withdrawn
Links
- LQUBXCVRJZGBLM-UHFFFAOYSA-O 2,5-diphenyl-1h-pyrazol-2-ium Chemical class C1=CC(C=2C=CC=CC=2)=N[NH+]1C1=CC=CC=C1 LQUBXCVRJZGBLM-UHFFFAOYSA-O 0.000 title claims description 9
- 241000196324 Embryophyta Species 0.000 claims description 38
- -1 carbethoxymethyl Chemical group 0.000 claims description 27
- 239000004480 active ingredient Substances 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 22
- 239000004009 herbicide Substances 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 16
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 15
- 239000007921 spray Substances 0.000 claims description 14
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 11
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims description 11
- 150000001450 anions Chemical group 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
- RCFITSMZCAIEOV-UHFFFAOYSA-M methyl sulfate;1,2,4-trimethyl-3,5-diphenylpyrazol-1-ium Chemical compound COS([O-])(=O)=O.CN1[N+](C)=C(C=2C=CC=CC=2)C(C)=C1C1=CC=CC=C1 RCFITSMZCAIEOV-UHFFFAOYSA-M 0.000 claims description 5
- NJEWCCAOEKSKET-UHFFFAOYSA-M 1,2-dimethyl-3,5-diphenyl-4-prop-2-ynylpyrazol-1-ium;hydron;sulfate Chemical compound OS([O-])(=O)=O.C[N+]=1N(C)C(C=2C=CC=CC=2)=C(CC#C)C=1C1=CC=CC=C1 NJEWCCAOEKSKET-UHFFFAOYSA-M 0.000 claims description 4
- ZOMSORPENUNIFS-UHFFFAOYSA-M 4-benzyl-1,2-dimethyl-3,5-diphenylpyrazol-1-ium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.C=1C=CC=CC=1C1=[N+](C)N(C)C(C=2C=CC=CC=2)=C1CC1=CC=CC=C1 ZOMSORPENUNIFS-UHFFFAOYSA-M 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 239000000575 pesticide Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- SFJCOYWIITVQKO-UHFFFAOYSA-M 1,2-dimethyl-4-pentyl-3,5-diphenylpyrazol-1-ium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.CN1[N+](C)=C(C=2C=CC=CC=2)C(CCCCC)=C1C1=CC=CC=C1 SFJCOYWIITVQKO-UHFFFAOYSA-M 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
- 150000001768 cations Chemical class 0.000 claims description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims description 3
- WECVTOUWBRBXCE-UHFFFAOYSA-N 1,2,4-trimethyl-3,5-diphenylpyrazol-1-ium Chemical compound CN1[N+](C)=C(C=2C=CC=CC=2)C(C)=C1C1=CC=CC=C1 WECVTOUWBRBXCE-UHFFFAOYSA-N 0.000 claims description 2
- GSOOPJTXVXTDSC-UHFFFAOYSA-N 4-benzyl-1,2-dimethyl-3,5-diphenylpyrazol-1-ium Chemical class C=1C=CC=CC=1C1=[N+](C)N(C)C(C=2C=CC=CC=2)=C1CC1=CC=CC=C1 GSOOPJTXVXTDSC-UHFFFAOYSA-N 0.000 claims description 2
- FOFDYCUPXAQIDN-UHFFFAOYSA-M 4-benzyl-1,2-dimethyl-3,5-diphenylpyrazol-1-ium;hydrogen sulfate Chemical compound OS([O-])(=O)=O.C=1C=CC=CC=1C1=[N+](C)N(C)C(C=2C=CC=CC=2)=C1CC1=CC=CC=C1 FOFDYCUPXAQIDN-UHFFFAOYSA-M 0.000 claims description 2
- OCXWPNUZUDNOAK-UHFFFAOYSA-N 1,2-dimethyl-3,5-diphenyl-4-propylpyrazol-1-ium Chemical class CN1[N+](C)=C(C=2C=CC=CC=2)C(CCC)=C1C1=CC=CC=C1 OCXWPNUZUDNOAK-UHFFFAOYSA-N 0.000 claims 2
- IFOABJNKSFBFNY-UHFFFAOYSA-N 1,2-dimethyl-4-pentyl-3,5-diphenylpyrazol-1-ium Chemical class CN1[N+](C)=C(C=2C=CC=CC=2)C(CCCCC)=C1C1=CC=CC=C1 IFOABJNKSFBFNY-UHFFFAOYSA-N 0.000 claims 2
- AVNFXPDZRFWBCL-UHFFFAOYSA-N 2-(1,2-dimethyl-3,5-diphenylpyrazol-1-ium-4-yl)acetic acid iodide Chemical compound [I-].C[N+]=1N(C)C(C=2C=CC=CC=2)=C(CC(O)=O)C=1C1=CC=CC=C1 AVNFXPDZRFWBCL-UHFFFAOYSA-N 0.000 claims 1
- PKWSFZHMPNCCFO-UHFFFAOYSA-M 4-ethyl-1,2-dimethyl-3,5-diphenylpyrazol-1-ium;methyl sulfate Chemical compound COS([O-])(=O)=O.CN1[N+](C)=C(C=2C=CC=CC=2)C(CC)=C1C1=CC=CC=C1 PKWSFZHMPNCCFO-UHFFFAOYSA-M 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 239000000417 fungicide Substances 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- 230000002363 herbicidal effect Effects 0.000 description 17
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 16
- 239000004094 surface-active agent Substances 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- 244000070406 Malus silvestris Species 0.000 description 11
- 240000007594 Oryza sativa Species 0.000 description 11
- 241000209140 Triticum Species 0.000 description 11
- 235000021307 Triticum Nutrition 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- 235000007164 Oryza sativa Nutrition 0.000 description 10
- 239000012141 concentrate Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 235000011430 Malus pumila Nutrition 0.000 description 9
- 201000010099 disease Diseases 0.000 description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 235000009566 rice Nutrition 0.000 description 9
- 235000015103 Malus silvestris Nutrition 0.000 description 8
- 125000005594 diketone group Chemical group 0.000 description 8
- 244000075850 Avena orientalis Species 0.000 description 7
- 235000007319 Avena orientalis Nutrition 0.000 description 7
- 229940100198 alkylating agent Drugs 0.000 description 7
- 239000002168 alkylating agent Substances 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 235000007340 Hordeum vulgare Nutrition 0.000 description 6
- 240000005979 Hordeum vulgare Species 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 239000002689 soil Substances 0.000 description 6
- 240000008067 Cucumis sativus Species 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- 239000008280 blood Substances 0.000 description 5
- 210000004369 blood Anatomy 0.000 description 5
- NZZIMKJIVMHWJC-UHFFFAOYSA-N dibenzoylmethane Chemical class C=1C=CC=CC=1C(=O)CC(=O)C1=CC=CC=C1 NZZIMKJIVMHWJC-UHFFFAOYSA-N 0.000 description 5
- 238000011835 investigation Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 244000052769 pathogen Species 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 231100000674 Phytotoxicity Toxicity 0.000 description 4
- 206010039509 Scab Diseases 0.000 description 4
- 235000013532 brandy Nutrition 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 3
- 244000078127 Eleusine coracana Species 0.000 description 3
- 235000013499 Eleusine coracana subsp coracana Nutrition 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 239000000010 aprotic solvent Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 3
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 3
- 239000000428 dust Substances 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 229960004592 isopropanol Drugs 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002736 nonionic surfactant Substances 0.000 description 3
- 230000001717 pathogenic effect Effects 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- AMANBMHGZZGKKL-UHFFFAOYSA-M 1,2,4-trimethyl-3,5-diphenylpyrazol-1-ium;iodide Chemical compound [I-].CN1[N+](C)=C(C=2C=CC=CC=2)C(C)=C1C1=CC=CC=C1 AMANBMHGZZGKKL-UHFFFAOYSA-M 0.000 description 2
- JHTKOUJDEUQFOB-UHFFFAOYSA-N 1h-pyrazol-1-ium;chloride Chemical compound Cl.C=1C=NNC=1 JHTKOUJDEUQFOB-UHFFFAOYSA-N 0.000 description 2
- 240000001592 Amaranthus caudatus Species 0.000 description 2
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- 241000217446 Calystegia sepium Species 0.000 description 2
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- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 2
- 235000009849 Cucumis sativus Nutrition 0.000 description 2
- 241000219122 Cucurbita Species 0.000 description 2
- 235000009854 Cucurbita moschata Nutrition 0.000 description 2
- 235000009804 Cucurbita pepo subsp pepo Nutrition 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 229920001213 Polysorbate 20 Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 244000062793 Sorghum vulgare Species 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 235000021016 apples Nutrition 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
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- 238000001704 evaporation Methods 0.000 description 2
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- 239000003456 ion exchange resin Substances 0.000 description 2
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- 239000010410 layer Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 235000019713 millet Nutrition 0.000 description 2
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N n-propyl alcohol Natural products CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 235000015136 pumpkin Nutrition 0.000 description 2
- 238000005956 quaternization reaction Methods 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- QDDRDURSDCEBKI-UHFFFAOYSA-M 1,2-dimethyl-3,5-diphenyl-4-propylpyrazol-1-ium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.CN1[N+](C)=C(C=2C=CC=CC=2)C(CCC)=C1C1=CC=CC=C1 QDDRDURSDCEBKI-UHFFFAOYSA-M 0.000 description 1
- YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 description 1
- LAVLWJYYMDUIEJ-UHFFFAOYSA-O 1h-pyrazol-1-ium;nitrate Chemical compound [O-][N+]([O-])=O.C1=CN[NH+]=C1 LAVLWJYYMDUIEJ-UHFFFAOYSA-O 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
- OBFPJGNSAPBZHO-UHFFFAOYSA-N 2-benzyl-1,3-diphenylpropane-1,3-dione Chemical compound C=1C=CC=CC=1C(=O)C(C(=O)C=1C=CC=CC=1)CC1=CC=CC=C1 OBFPJGNSAPBZHO-UHFFFAOYSA-N 0.000 description 1
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- QORHKIPSBFULHB-UHFFFAOYSA-N 2-pentyl-1,3-diphenylpropane-1,3-dione Chemical compound C=1C=CC=CC=1C(=O)C(CCCCC)C(=O)C1=CC=CC=C1 QORHKIPSBFULHB-UHFFFAOYSA-N 0.000 description 1
- WITMXBRCQWOZPX-UHFFFAOYSA-O 2-phenyl-1h-pyrazol-2-ium Chemical class C1=CN[N+](C=2C=CC=CC=2)=C1 WITMXBRCQWOZPX-UHFFFAOYSA-O 0.000 description 1
- ZYZSSOVHGXHCNG-UHFFFAOYSA-M 3,5-dicyclohexyl-1,2,4-trimethylpyrazol-1-ium;methyl sulfate Chemical compound COS([O-])(=O)=O.CN1[N+](C)=C(C2CCCCC2)C(C)=C1C1CCCCC1 ZYZSSOVHGXHCNG-UHFFFAOYSA-M 0.000 description 1
- NECLVWZKRMLOIG-UHFFFAOYSA-N 4-ethyl-1,2-dimethyl-3,5-diphenylpyrazol-1-ium Chemical compound CN1[N+](C)=C(C=2C=CC=CC=2)C(CC)=C1C1=CC=CC=C1 NECLVWZKRMLOIG-UHFFFAOYSA-N 0.000 description 1
- QDDLBKWGGGEPSV-UHFFFAOYSA-N 4-ethyl-1-methyl-3,5-diphenylpyrazole Chemical compound CCC=1C(C=2C=CC=CC=2)=NN(C)C=1C1=CC=CC=C1 QDDLBKWGGGEPSV-UHFFFAOYSA-N 0.000 description 1
- WVMBISZHWMJNNM-UHFFFAOYSA-N 4-propan-2-yl-1h-pyrazole Chemical compound CC(C)C=1C=NNC=1 WVMBISZHWMJNNM-UHFFFAOYSA-N 0.000 description 1
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- 235000005474 African couch grass Nutrition 0.000 description 1
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- 235000003129 Ambrosia artemisiifolia var elatior Nutrition 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 235000007320 Avena fatua Nutrition 0.000 description 1
- 241000209764 Avena fatua Species 0.000 description 1
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- 241000895523 Blumeria graminis f. sp. hordei Species 0.000 description 1
- 235000011292 Brassica rapa Nutrition 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 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
- 244000281762 Chenopodium ambrosioides Species 0.000 description 1
- 235000000509 Chenopodium ambrosioides Nutrition 0.000 description 1
- 235000005490 Chenopodium botrys Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- 244000152970 Digitaria sanguinalis Species 0.000 description 1
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 1
- 244000058871 Echinochloa crus-galli Species 0.000 description 1
- 241001520106 Eustachys Species 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 241000896246 Golovinomyces cichoracearum Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 206010061217 Infestation Diseases 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000209510 Liliopsida Species 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 240000000982 Malva neglecta Species 0.000 description 1
- 235000000060 Malva neglecta Nutrition 0.000 description 1
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
- 235000011999 Panicum crusgalli Nutrition 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- 241001337928 Podosphaera leucotricha Species 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000220324 Pyrus Species 0.000 description 1
- 235000014443 Pyrus communis Nutrition 0.000 description 1
- 240000001987 Pyrus communis Species 0.000 description 1
- 240000003461 Setaria viridis Species 0.000 description 1
- 235000002248 Setaria viridis Nutrition 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000228452 Venturia inaequalis Species 0.000 description 1
- 241000219094 Vitaceae Species 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229920003232 aliphatic polyester Polymers 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 238000005349 anion exchange Methods 0.000 description 1
- 235000003484 annual ragweed Nutrition 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 235000006263 bur ragweed Nutrition 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000004464 cereal grain Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000009194 climbing Effects 0.000 description 1
- 235000003488 common ragweed Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 241001233957 eudicotyledons Species 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 244000053095 fungal pathogen Species 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 235000021021 grapes Nutrition 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 208000006278 hypochromic anemia Diseases 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 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
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 230000036244 malformation Effects 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-N methyl sulfate Chemical compound COS(O)(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 150000002891 organic anions Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 235000021017 pears Nutrition 0.000 description 1
- 239000003415 peat Substances 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000056 polyoxyethylene ether Polymers 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- IKNCGYCHMGNBCP-UHFFFAOYSA-N propan-1-olate Chemical compound CCC[O-] IKNCGYCHMGNBCP-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 235000009736 ragweed Nutrition 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 230000000007 visual effect Effects 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
- C07D231/12—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/782—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/782—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
- C07C49/784—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic with all keto groups bound to a non-condensed ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/794—Ketones containing a keto group bound to a six-membered aromatic ring having unsaturation outside an aromatic ring
- C07C49/796—Ketones containing a keto group bound to a six-membered aromatic ring having unsaturation outside an aromatic ring polycyclic
-
- 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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/04—Sodium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/574,068 US4017298A (en) | 1975-05-02 | 1975-05-02 | 1,2,4-Trialkyl-3,5-diphenylpyrazolium salts as herbicides |
| US05/574,067 US3958001A (en) | 1975-05-02 | 1975-05-02 | 4-Alkyl-1,2-dimethyl-3,5-diphenylpyrazolium salts and derivatives thereof as fungicidal agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2618421A1 true DE2618421A1 (de) | 1976-11-18 |
Family
ID=27076277
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762618421 Withdrawn DE2618421A1 (de) | 1975-05-02 | 1976-04-27 | Diphenylpyrazoliumsalze |
Country Status (19)
| Country | Link |
|---|---|
| JP (1) | JPS51133265A (ru) |
| AR (1) | AR217400A1 (ru) |
| AU (1) | AU503523B2 (ru) |
| CA (1) | CA1078850A (ru) |
| CS (1) | CS191170B2 (ru) |
| DD (1) | DD127656A5 (ru) |
| DE (1) | DE2618421A1 (ru) |
| DK (1) | DK194476A (ru) |
| ES (1) | ES447515A1 (ru) |
| FI (1) | FI761159A (ru) |
| FR (1) | FR2309539A1 (ru) |
| GB (1) | GB1543338A (ru) |
| IL (1) | IL49410A (ru) |
| IT (1) | IT1060500B (ru) |
| NL (1) | NL7604597A (ru) |
| PL (1) | PL107282B1 (ru) |
| SE (1) | SE7605011L (ru) |
| SU (1) | SU683601A3 (ru) |
| TR (1) | TR18655A (ru) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3818096A (en) * | 1972-04-12 | 1974-06-18 | Schering Corp | Compositions of 1,2-dilower alkyl arylpyrazolium quaternary salts and method of lowering blood sugar levels with same |
| DE2404795C2 (de) * | 1974-02-01 | 1983-03-24 | Basf Ag, 6700 Ludwigshafen | 1,2-Dimethyl-3,5-diphenyl-pyrazoliumsalze und deren Verwendung als Herbizid |
| DE2524853A1 (de) * | 1975-06-04 | 1976-12-09 | Vulkan Werk Gmbh | Verfahren und vorrichtung zur herstellung von masten, insbesondere beleuchtungsmasten |
-
1976
- 1976-04-13 IL IL49410A patent/IL49410A/xx unknown
- 1976-04-14 AU AU12987/76A patent/AU503523B2/en not_active Expired
- 1976-04-21 CA CA250,620A patent/CA1078850A/en not_active Expired
- 1976-04-22 AR AR262970A patent/AR217400A1/es active
- 1976-04-22 GB GB16439/76A patent/GB1543338A/en not_active Expired
- 1976-04-27 DE DE19762618421 patent/DE2618421A1/de not_active Withdrawn
- 1976-04-27 FI FI761159A patent/FI761159A/fi not_active Application Discontinuation
- 1976-04-29 CS CS762833A patent/CS191170B2/cs unknown
- 1976-04-29 TR TR18655A patent/TR18655A/xx unknown
- 1976-04-29 NL NL7604597A patent/NL7604597A/xx not_active Application Discontinuation
- 1976-04-29 FR FR7612809A patent/FR2309539A1/fr not_active Withdrawn
- 1976-04-30 ES ES447515A patent/ES447515A1/es not_active Expired
- 1976-04-30 SE SE7605011A patent/SE7605011L/xx unknown
- 1976-04-30 IT IT49288/76A patent/IT1060500B/it active
- 1976-04-30 SU SU762354750A patent/SU683601A3/ru active
- 1976-04-30 DK DK194476A patent/DK194476A/da unknown
- 1976-04-30 PL PL1976189201A patent/PL107282B1/pl unknown
- 1976-04-30 DD DD192622A patent/DD127656A5/xx unknown
- 1976-05-04 JP JP51050052A patent/JPS51133265A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| IT1060500B (it) | 1982-08-20 |
| FI761159A (ru) | 1976-11-03 |
| AU1298776A (en) | 1977-10-20 |
| IL49410A0 (en) | 1976-06-30 |
| AR217400A1 (es) | 1980-03-31 |
| CS191170B2 (en) | 1979-06-29 |
| JPS51133265A (en) | 1976-11-18 |
| FR2309539A1 (fr) | 1976-11-26 |
| SE7605011L (sv) | 1976-11-03 |
| AU503523B2 (en) | 1979-09-06 |
| DK194476A (da) | 1976-11-03 |
| SU683601A3 (ru) | 1979-08-30 |
| DD127656A5 (ru) | 1977-10-05 |
| NL7604597A (nl) | 1976-11-04 |
| IL49410A (en) | 1980-06-30 |
| PL107282B1 (pl) | 1980-02-29 |
| TR18655A (tr) | 1977-06-23 |
| GB1543338A (en) | 1979-04-04 |
| ES447515A1 (es) | 1977-11-01 |
| CA1078850A (en) | 1980-06-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |