FI59194C - Pyrazolier som svampgifter - Google Patents
Pyrazolier som svampgifter Download PDFInfo
- Publication number
- FI59194C FI59194C FI760174A FI760174A FI59194C FI 59194 C FI59194 C FI 59194C FI 760174 A FI760174 A FI 760174A FI 760174 A FI760174 A FI 760174A FI 59194 C FI59194 C FI 59194C
- Authority
- FI
- Finland
- Prior art keywords
- methyl
- dimethyl
- sulfate
- plants
- perchlorate
- Prior art date
Links
- 241000196324 Embryophyta Species 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 11
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 241000233866 Fungi Species 0.000 claims description 8
- 150000001450 anions Chemical group 0.000 claims description 7
- 235000013339 cereals Nutrition 0.000 claims description 7
- 235000013399 edible fruits Nutrition 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 6
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims description 6
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- 229910002651 NO3 Inorganic materials 0.000 claims description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 3
- 229910019142 PO4 Inorganic materials 0.000 claims description 3
- 229940077388 benzenesulfonate Drugs 0.000 claims description 3
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 3
- 239000010452 phosphate Substances 0.000 claims description 3
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 3
- 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 claims description 2
- 240000008042 Zea mays Species 0.000 claims description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 2
- 235000005822 corn Nutrition 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims 1
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 239000004474 valine Substances 0.000 claims 1
- -1 ethylcarboxymethyl Chemical group 0.000 description 24
- 239000000203 mixture Substances 0.000 description 18
- 201000010099 disease Diseases 0.000 description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000007921 spray Substances 0.000 description 9
- 239000004094 surface-active agent Substances 0.000 description 9
- 241000220225 Malus Species 0.000 description 8
- 235000011430 Malus pumila Nutrition 0.000 description 7
- 240000007594 Oryza sativa Species 0.000 description 7
- 235000007164 Oryza sativa Nutrition 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 240000005979 Hordeum vulgare Species 0.000 description 6
- 235000007340 Hordeum vulgare Nutrition 0.000 description 6
- 235000009566 rice Nutrition 0.000 description 6
- 206010035148 Plague Diseases 0.000 description 5
- 241000209140 Triticum Species 0.000 description 5
- 235000021307 Triticum Nutrition 0.000 description 5
- 241000607479 Yersinia pestis Species 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 240000008067 Cucumis sativus Species 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- 240000003768 Solanum lycopersicum Species 0.000 description 4
- 230000029936 alkylation Effects 0.000 description 4
- 238000005804 alkylation reaction Methods 0.000 description 4
- 239000000417 fungicide Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 244000052769 pathogen Species 0.000 description 4
- 235000007688 Lycopersicon esculentum 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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 235000008504 concentrate Nutrition 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 230000000855 fungicidal effect Effects 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- LLIOTGIXSUTUJW-UHFFFAOYSA-K 1,2-dimethyl-3,5-diphenylpyrazol-1-ium phosphate Chemical compound P(=O)([O-])([O-])[O-].C[N+]=1N(C(=CC1C1=CC=CC=C1)C1=CC=CC=C1)C.C[N+]=1N(C(=CC1C1=CC=CC=C1)C1=CC=CC=C1)C.C[N+]=1N(C(=CC1C1=CC=CC=C1)C1=CC=CC=C1)C LLIOTGIXSUTUJW-UHFFFAOYSA-K 0.000 description 2
- TWUBOZYAXNVYGS-UHFFFAOYSA-M 1,2-dimethyl-3,5-diphenylpyrazol-1-ium;iodide Chemical compound [I-].C[N+]=1N(C)C(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 TWUBOZYAXNVYGS-UHFFFAOYSA-M 0.000 description 2
- KPKVEKQHMRDJSA-UHFFFAOYSA-M 1,2-dimethyl-3-(2-methylphenyl)-5-(4-methylphenyl)pyrazol-1-ium iodide Chemical compound [I-].C[N+]=1N(C(=CC1C1=C(C=CC=C1)C)C1=CC=C(C=C1)C)C KPKVEKQHMRDJSA-UHFFFAOYSA-M 0.000 description 2
- SVDTUJAQNAQGGW-UHFFFAOYSA-N 1-methyl-3,5-diphenylpyrazole Chemical compound CN1N=C(C=2C=CC=CC=2)C=C1C1=CC=CC=C1 SVDTUJAQNAQGGW-UHFFFAOYSA-N 0.000 description 2
- JXHKUYQCEJILEI-UHFFFAOYSA-N 3,5-diphenyl-1h-pyrazole Chemical compound C=1C(C=2C=CC=CC=2)=NNC=1C1=CC=CC=C1 JXHKUYQCEJILEI-UHFFFAOYSA-N 0.000 description 2
- 235000009849 Cucumis sativus Nutrition 0.000 description 2
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-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
- 231100000674 Phytotoxicity Toxicity 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000220324 Pyrus Species 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 235000021016 apples Nutrition 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 125000005594 diketone group Chemical group 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 230000002538 fungal effect Effects 0.000 description 2
- 235000021017 pears Nutrition 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- AQRAUYUNVFXIPS-UHFFFAOYSA-L 1,2-dimethyl-3,5-bis(2-methylphenyl)pyrazol-1-ium sulfate Chemical compound S(=O)(=O)([O-])[O-].C[N+]=1N(C(=CC1C1=C(C=CC=C1)C)C1=C(C=CC=C1)C)C.C[N+]=1N(C(=CC1C1=C(C=CC=C1)C)C1=C(C=CC=C1)C)C AQRAUYUNVFXIPS-UHFFFAOYSA-L 0.000 description 1
- LSPWBCMNEQSDEI-UHFFFAOYSA-N 1,2-dimethyl-3,5-diphenylpyrazol-1-ium nitrate Chemical compound [N+](=O)([O-])[O-].C[N+]=1N(C(=CC1C1=CC=CC=C1)C1=CC=CC=C1)C LSPWBCMNEQSDEI-UHFFFAOYSA-N 0.000 description 1
- MTCQFVYEKGHUGI-UHFFFAOYSA-M 1,2-dimethyl-3,5-diphenylpyrazol-1-ium;4-methylbenzenesulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.C[N+]=1N(C)C(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 MTCQFVYEKGHUGI-UHFFFAOYSA-M 0.000 description 1
- QPHPWHYLXYFPHZ-UHFFFAOYSA-M 1,2-dimethyl-3,5-diphenylpyrazol-1-ium;bromide Chemical compound [Br-].C[N+]=1N(C)C(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 QPHPWHYLXYFPHZ-UHFFFAOYSA-M 0.000 description 1
- QTVMXZDRWOUJRU-UHFFFAOYSA-M 1,2-dimethyl-3,5-diphenylpyrazol-1-ium;chloride Chemical compound [Cl-].C[N+]=1N(C)C(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 QTVMXZDRWOUJRU-UHFFFAOYSA-M 0.000 description 1
- ASLUVPLUYLXSPY-UHFFFAOYSA-M 1,2-dimethyl-3-(3-methylphenyl)-5-(4-methylphenyl)pyrazol-2-ium methyl sulfate Chemical compound S(=O)(=O)(OC)[O-].C[N+]=1N(C(=CC1C1=CC=C(C=C1)C)C=1C=C(C=CC1)C)C ASLUVPLUYLXSPY-UHFFFAOYSA-M 0.000 description 1
- KJBWGQAKZBGIID-UHFFFAOYSA-M 1,2-dimethyl-3-(3-methylphenyl)-5-phenylpyrazol-2-ium iodide Chemical compound [I-].C[N+]=1N(C(=CC1C=1C=C(C=CC1)C)C1=CC=CC=C1)C KJBWGQAKZBGIID-UHFFFAOYSA-M 0.000 description 1
- WHCFKMBJNRBGMM-UHFFFAOYSA-M 1-methyl-3,5-diphenyl-2-prop-2-ynylpyrazol-1-ium methyl sulfate Chemical compound S(=O)(=O)(OC)[O-].C[N+]=1N(C(=CC1C1=CC=CC=C1)C1=CC=CC=C1)CC#C WHCFKMBJNRBGMM-UHFFFAOYSA-M 0.000 description 1
- JIJBWYXJIKAYLT-UHFFFAOYSA-N 1h-pyrazol-1-ium;iodide Chemical compound [I-].C1=CN[NH+]=C1 JIJBWYXJIKAYLT-UHFFFAOYSA-N 0.000 description 1
- JEOVEEPACZXTPL-UHFFFAOYSA-N 1h-pyrazol-1-ium;perchlorate Chemical compound C1=CN[NH+]=C1.[O-]Cl(=O)(=O)=O JEOVEEPACZXTPL-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
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-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
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- WFRBNLOVCBTMOF-UHFFFAOYSA-M 3,5-bis(4-chlorophenyl)-1,2-dimethylpyrazol-1-ium methyl sulfate Chemical compound S(=O)(=O)(OC)[O-].ClC1=CC=C(C=C1)C=1N([N+](=C(C1)C1=CC=C(C=C1)Cl)C)C WFRBNLOVCBTMOF-UHFFFAOYSA-M 0.000 description 1
- PAXZDEPFZRPHJT-UHFFFAOYSA-M 3-(2,3-dimethylphenyl)-1,2-dimethyl-5-phenylpyrazol-1-ium perchlorate Chemical compound Cl(=O)(=O)(=O)[O-].C[N+]=1N(C(=CC1C1=C(C(=CC=C1)C)C)C1=CC=CC=C1)C PAXZDEPFZRPHJT-UHFFFAOYSA-M 0.000 description 1
- AUTGVEUNHZHVFQ-UHFFFAOYSA-M 3-(2,4-dichlorophenyl)-1,2-dimethyl-5-phenylpyrazol-1-ium methyl sulfate Chemical compound S(=O)(=O)(OC)[O-].ClC1=C(C=CC(=C1)Cl)C=1N([N+](=C(C1)C1=CC=CC=C1)C)C AUTGVEUNHZHVFQ-UHFFFAOYSA-M 0.000 description 1
- ZIQUOBUWCBBSTH-UHFFFAOYSA-M 3-(2,5-dimethylphenyl)-1,2-dimethyl-5-phenylpyrazol-1-ium perchlorate Chemical compound Cl(=O)(=O)(=O)[O-].C[N+]=1N(C(=CC1C1=C(C=CC(=C1)C)C)C1=CC=CC=C1)C ZIQUOBUWCBBSTH-UHFFFAOYSA-M 0.000 description 1
- MCGVAQMAZQRCGY-UHFFFAOYSA-M 3-(2-fluorophenyl)-1,2-dimethyl-5-phenylpyrazol-1-ium methyl sulfate Chemical compound S(=O)(=O)(OC)[O-].FC1=C(C=CC=C1)C=1N([N+](=C(C1)C1=CC=CC=C1)C)C MCGVAQMAZQRCGY-UHFFFAOYSA-M 0.000 description 1
- WRDCSPNUSXMKGF-UHFFFAOYSA-M 3-(3-iodophenyl)-1,2-dimethyl-5-phenylpyrazol-2-ium iodide Chemical compound [I-].IC=1C=C(C=CC1)C=1C=C(N([N+]1C)C)C1=CC=CC=C1 WRDCSPNUSXMKGF-UHFFFAOYSA-M 0.000 description 1
- RAVDNJJYQJMFJB-UHFFFAOYSA-M 3-(4-butoxyphenyl)-1,2-dimethyl-5-phenylpyrazol-1-ium perchlorate Chemical compound Cl(=O)(=O)(=O)[O-].C(CCC)OC1=CC=C(C=C1)C=1N([N+](=C(C1)C1=CC=CC=C1)C)C RAVDNJJYQJMFJB-UHFFFAOYSA-M 0.000 description 1
- MGZLGERQMWHVOV-UHFFFAOYSA-M 3-(4-fluorophenyl)-1,2-dimethyl-5-phenylpyrazol-1-ium iodide Chemical compound [I-].FC1=CC=C(C=C1)C=1N([N+](=C(C1)C1=CC=CC=C1)C)C MGZLGERQMWHVOV-UHFFFAOYSA-M 0.000 description 1
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- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
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- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
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- 101500021169 Aplysia californica Myomodulin-G Proteins 0.000 description 1
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- 241000895523 Blumeria graminis f. sp. hordei Species 0.000 description 1
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
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- GUMRJSAXGBIVKR-UHFFFAOYSA-M Cl(=O)(=O)(=O)[O-].C[N+]=1N(C(=CC1C1=C(C=C(C=C1)C)C)C1=CC=CC=C1)C Chemical compound Cl(=O)(=O)(=O)[O-].C[N+]=1N(C(=CC1C1=C(C=C(C=C1)C)C)C1=CC=CC=C1)C GUMRJSAXGBIVKR-UHFFFAOYSA-M 0.000 description 1
- JCKSULMEQCDNCW-UHFFFAOYSA-M Cl(=O)(=O)(=O)[O-].C[N+]=1N(C(=CC1C1=C(C=CC=C1)C)C1=CC=C(C=C1)C)C Chemical compound Cl(=O)(=O)(=O)[O-].C[N+]=1N(C(=CC1C1=C(C=CC=C1)C)C1=CC=C(C=C1)C)C JCKSULMEQCDNCW-UHFFFAOYSA-M 0.000 description 1
- NQPLCNVYALLPRU-UHFFFAOYSA-M Cl(=O)(=O)(=O)[O-].C[N+]=1N(C(=CC1C1=CC=C(C=C1)C)C1=CC=C(C=C1)C)C Chemical compound Cl(=O)(=O)(=O)[O-].C[N+]=1N(C(=CC1C1=CC=C(C=C1)C)C1=CC=C(C=C1)C)C NQPLCNVYALLPRU-UHFFFAOYSA-M 0.000 description 1
- JCFGGRNJJUOOOS-UHFFFAOYSA-M Cl(=O)(=O)(=O)[O-].C[N+]=1N(C(=CC1C1=CC=C(C=C1)C)C=1C=C(C=CC1)C)C Chemical compound Cl(=O)(=O)(=O)[O-].C[N+]=1N(C(=CC1C1=CC=C(C=C1)C)C=1C=C(C=CC1)C)C JCFGGRNJJUOOOS-UHFFFAOYSA-M 0.000 description 1
- DKGPKSXWLRVIPU-UHFFFAOYSA-M Cl(=O)(=O)(=O)[O-].ClC1=CC(=C(C=C1)C)C=1N([N+](=C(C1)C1=CC=C(C=C1)C)C)C Chemical compound Cl(=O)(=O)(=O)[O-].ClC1=CC(=C(C=C1)C)C=1N([N+](=C(C1)C1=CC=C(C=C1)C)C)C DKGPKSXWLRVIPU-UHFFFAOYSA-M 0.000 description 1
- XJBXWYGJTDZSQP-UHFFFAOYSA-M Cl(=O)(=O)(=O)[O-].ClC1=CC=C(C=C1)C=1N([N+](=C(C1)C1=CC=C(C=C1)OC)C)C Chemical compound Cl(=O)(=O)(=O)[O-].ClC1=CC=C(C=C1)C=1N([N+](=C(C1)C1=CC=C(C=C1)OC)C)C XJBXWYGJTDZSQP-UHFFFAOYSA-M 0.000 description 1
- YGJGHXCOGATDFG-UHFFFAOYSA-M Cl(=O)(=O)(=O)[O-].ClC=1C(=C(C=CC1)C)C=1C=C(N([N+]1C)C)C1=CC=C(C=C1)CC Chemical compound Cl(=O)(=O)(=O)[O-].ClC=1C(=C(C=CC1)C)C=1C=C(N([N+]1C)C)C1=CC=C(C=C1)CC YGJGHXCOGATDFG-UHFFFAOYSA-M 0.000 description 1
- 240000004244 Cucurbita moschata Species 0.000 description 1
- 235000009854 Cucurbita moschata Nutrition 0.000 description 1
- 235000009852 Cucurbita pepo Nutrition 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- 241000221787 Erysiphe Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000896246 Golovinomyces cichoracearum Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 244000070406 Malus silvestris Species 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- RSPISYXLHRIGJD-UHFFFAOYSA-N OOOO Chemical compound OOOO RSPISYXLHRIGJD-UHFFFAOYSA-N 0.000 description 1
- KUGRPPRAQNPSQD-UHFFFAOYSA-N OOOOO Chemical compound OOOOO KUGRPPRAQNPSQD-UHFFFAOYSA-N 0.000 description 1
- 241000233679 Peronosporaceae Species 0.000 description 1
- 241000233622 Phytophthora infestans Species 0.000 description 1
- 241001337928 Podosphaera leucotricha Species 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- 101000798993 Pseudomonas putida (strain ATCC 700007 / DSM 6899 / BCRC 17059 / F1) 2-hydroxy-6-oxo-2,4-heptadienoate hydrolase Proteins 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-O Pyrazolium Chemical compound C1=CN[NH+]=C1 WTKZEGDFNFYCGP-UHFFFAOYSA-O 0.000 description 1
- XTOSNYJOYPWBPL-UHFFFAOYSA-M S(=O)(=O)(OC)[O-].C[N+]=1N(C(=CC1C1=CC(=C(C=C1)C)C)C1=CC=CC=C1)C Chemical compound S(=O)(=O)(OC)[O-].C[N+]=1N(C(=CC1C1=CC(=C(C=C1)C)C)C1=CC=CC=C1)C XTOSNYJOYPWBPL-UHFFFAOYSA-M 0.000 description 1
- NGMPDONLQCPUOU-UHFFFAOYSA-M S(=O)(=O)(OC)[O-].C[N+]=1N(C(=CC1C1=CC=C(C=C1)C)C1=CC=C(C=C1)C)C Chemical compound S(=O)(=O)(OC)[O-].C[N+]=1N(C(=CC1C1=CC=C(C=C1)C)C1=CC=C(C=C1)C)C NGMPDONLQCPUOU-UHFFFAOYSA-M 0.000 description 1
- BOYCWGXXIHBYJC-UHFFFAOYSA-M S(=O)(=O)(OC)[O-].C[N+]=1N(C(=CC1C1=CC=CC=C1)C1=CC(=CC(=C1)C)C)C Chemical compound S(=O)(=O)(OC)[O-].C[N+]=1N(C(=CC1C1=CC=CC=C1)C1=CC(=CC(=C1)C)C)C BOYCWGXXIHBYJC-UHFFFAOYSA-M 0.000 description 1
- ODUNVZSVVQPNBR-UHFFFAOYSA-M S(=O)(=O)(OC)[O-].FC1=C(C=CC=C1)C=1N([N+](=C(C1)C=1C=C(C=CC1)C)C)C Chemical compound S(=O)(=O)(OC)[O-].FC1=C(C=CC=C1)C=1N([N+](=C(C1)C=1C=C(C=CC1)C)C)C ODUNVZSVVQPNBR-UHFFFAOYSA-M 0.000 description 1
- JIDQUDGCMIIIJA-UHFFFAOYSA-L S(=O)(=O)([O-])[O-].C[N+]=1N(C(=CC1C1=CC=CC=C1)C1=CC=CC=C1)C.C[N+]=1N(C(=CC1C1=CC=CC=C1)C1=CC=CC=C1)C Chemical compound S(=O)(=O)([O-])[O-].C[N+]=1N(C(=CC1C1=CC=CC=C1)C1=CC=CC=C1)C.C[N+]=1N(C(=CC1C1=CC=CC=C1)C1=CC=CC=C1)C JIDQUDGCMIIIJA-UHFFFAOYSA-L 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 235000002560 Solanum lycopersicum Nutrition 0.000 description 1
- 244000062793 Sorghum vulgare Species 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 235000005373 Uvularia sessilifolia Nutrition 0.000 description 1
- 241000228452 Venturia inaequalis Species 0.000 description 1
- 241000219094 Vitaceae Species 0.000 description 1
- OGMNRDSDKHRBTB-UHFFFAOYSA-M [I-].COC=1C=C(C=CC1OC)C=1C=C(N([N+]1C)C)C1=CC(=C(C=C1)C)C Chemical compound [I-].COC=1C=C(C=CC1OC)C=1C=C(N([N+]1C)C)C1=CC(=C(C=C1)C)C OGMNRDSDKHRBTB-UHFFFAOYSA-M 0.000 description 1
- MSOXAPSUVODCEL-UHFFFAOYSA-M [I-].C[N+]=1N(C(=CC1C1=C(C(=CC=C1)C)C)C1=CC=CC=C1)C Chemical compound [I-].C[N+]=1N(C(=CC1C1=C(C(=CC=C1)C)C)C1=CC=CC=C1)C MSOXAPSUVODCEL-UHFFFAOYSA-M 0.000 description 1
- GDBUCXDXAAMRLK-UHFFFAOYSA-M [I-].C[N+]=1N(C(=CC1C1=C(C=C(C=C1)C)C)C1=CC=CC=C1)C Chemical compound [I-].C[N+]=1N(C(=CC1C1=C(C=C(C=C1)C)C)C1=CC=CC=C1)C GDBUCXDXAAMRLK-UHFFFAOYSA-M 0.000 description 1
- QGQAYLYFJMCTER-UHFFFAOYSA-M [I-].FC1=CC=C(C=C1)C=1N([N+](=C(C1)C1=CC=C(C=C1)F)C)C Chemical compound [I-].FC1=CC=C(C=C1)C=1N([N+](=C(C1)C1=CC=C(C=C1)F)C)C QGQAYLYFJMCTER-UHFFFAOYSA-M 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 229920003232 aliphatic polyester Polymers 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910001916 chloryl Inorganic materials 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- NZZIMKJIVMHWJC-UHFFFAOYSA-N dibenzoylmethane Chemical compound C=1C=CC=CC=1C(=O)CC(=O)C1=CC=CC=C1 NZZIMKJIVMHWJC-UHFFFAOYSA-N 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
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 235000021021 grapes Nutrition 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 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
- ICIHDUSPYJNBRL-UHFFFAOYSA-N methyl sulfate;1h-pyrazol-1-ium Chemical compound [NH2+]1C=CC=N1.COS([O-])(=O)=O ICIHDUSPYJNBRL-UHFFFAOYSA-N 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 235000014571 nuts Nutrition 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 239000003415 peat Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 239000003586 protic polar solvent 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
- 238000007363 ring formation reaction Methods 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 235000020354 squash Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 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
- 238000010998 test method Methods 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 238000009736 wetting Methods 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
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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US546654A US3930011A (en) | 1975-02-03 | 1975-02-03 | Pyrazolium fungicides |
| US54665475 | 1975-02-03 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI760174A FI760174A (de) | 1976-08-04 |
| FI59194B FI59194B (fi) | 1981-03-31 |
| FI59194C true FI59194C (fi) | 1981-07-10 |
Family
ID=24181410
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI760174A FI59194C (fi) | 1975-02-03 | 1976-01-26 | Pyrazolier som svampgifter |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US3930011A (de) |
| JP (1) | JPS51104031A (de) |
| AR (1) | AR217624A1 (de) |
| AT (1) | AT347178B (de) |
| AU (1) | AU500653B2 (de) |
| BE (1) | BE838171R (de) |
| BR (1) | BR7600646A (de) |
| CA (1) | CA1058517A (de) |
| CH (1) | CH594354A5 (de) |
| CS (1) | CS199651B2 (de) |
| DD (1) | DD124703A6 (de) |
| DE (1) | DE2602964A1 (de) |
| DK (1) | DK139833B (de) |
| FI (1) | FI59194C (de) |
| FR (1) | FR2298949A2 (de) |
| GB (1) | GB1534866A (de) |
| IE (1) | IE42949B1 (de) |
| IL (1) | IL48708A (de) |
| IT (1) | IT1053334B (de) |
| NL (1) | NL7600700A (de) |
| NO (1) | NO145039C (de) |
| SE (1) | SE420888B (de) |
| SU (1) | SU644359A3 (de) |
| TR (1) | TR18706A (de) |
| ZA (1) | ZA757951B (de) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4207326A (en) * | 1979-05-21 | 1980-06-10 | Cilag-Chemie A.G. | Antimicrobial quaternary pyrazole derivatives |
| US5470869A (en) * | 1994-01-31 | 1995-11-28 | American Cyanamid Company | Pyrazolium fungicidal compositions |
| GB2294640A (en) * | 1994-11-07 | 1996-05-08 | American Cyanamid Co | Synergistic fungicidal difenzoquat compositions |
| EP4173485A1 (de) * | 2021-10-27 | 2023-05-03 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. | Proteinaggregation-hemmende verbindungen zur bekämpfung von pflanzenkrankheiten |
-
1975
- 1975-02-03 US US546654A patent/US3930011A/en not_active Expired - Lifetime
- 1975-12-22 ZA ZA00757951A patent/ZA757951B/xx unknown
- 1975-12-23 IL IL48708A patent/IL48708A/xx unknown
- 1975-12-24 AU AU87903/75A patent/AU500653B2/en not_active Expired
- 1975-12-30 GB GB53214/75A patent/GB1534866A/en not_active Expired
-
1976
- 1976-01-09 CA CA243,287A patent/CA1058517A/en not_active Expired
- 1976-01-13 AR AR261918A patent/AR217624A1/es active
- 1976-01-19 IT IT47683/76A patent/IT1053334B/it active
- 1976-01-23 NL NL7600700A patent/NL7600700A/xx not_active Application Discontinuation
- 1976-01-26 DK DK29676AA patent/DK139833B/da not_active IP Right Cessation
- 1976-01-26 FI FI760174A patent/FI59194C/fi not_active IP Right Cessation
- 1976-01-27 DE DE19762602964 patent/DE2602964A1/de not_active Withdrawn
- 1976-01-27 TR TR18706A patent/TR18706A/xx unknown
- 1976-01-29 CS CS76580A patent/CS199651B2/cs unknown
- 1976-02-02 BR BR7600646A patent/BR7600646A/pt unknown
- 1976-02-02 AT AT69776A patent/AT347178B/de not_active IP Right Cessation
- 1976-02-02 BE BE164007A patent/BE838171R/xx not_active IP Right Cessation
- 1976-02-02 SU SU762319208A patent/SU644359A3/ru active
- 1976-02-02 SE SE7601095A patent/SE420888B/xx unknown
- 1976-02-02 NO NO760343A patent/NO145039C/no unknown
- 1976-02-02 CH CH124376A patent/CH594354A5/xx not_active IP Right Cessation
- 1976-02-03 JP JP51010777A patent/JPS51104031A/ja active Pending
- 1976-02-03 DD DD191070A patent/DD124703A6/xx unknown
- 1976-02-03 FR FR7602975A patent/FR2298949A2/fr active Granted
- 1976-02-03 IE IE218/76A patent/IE42949B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS51104031A (de) | 1976-09-14 |
| IL48708A0 (en) | 1976-02-29 |
| NO145039B (no) | 1981-09-21 |
| SU644359A3 (ru) | 1979-01-25 |
| FR2298949B2 (de) | 1979-03-30 |
| FI59194B (fi) | 1981-03-31 |
| IL48708A (en) | 1978-07-31 |
| US3930011A (en) | 1975-12-30 |
| FI760174A (de) | 1976-08-04 |
| IE42949B1 (en) | 1980-11-19 |
| SE7601095L (sv) | 1976-08-03 |
| TR18706A (tr) | 1977-08-10 |
| FR2298949A2 (fr) | 1976-08-27 |
| AR217624A1 (es) | 1980-04-15 |
| CH594354A5 (de) | 1978-01-13 |
| CS199651B2 (en) | 1980-07-31 |
| NO145039C (no) | 1982-01-04 |
| DK139833B (da) | 1979-04-30 |
| IT1053334B (it) | 1981-08-31 |
| CA1058517A (en) | 1979-07-17 |
| DK29676A (de) | 1976-08-04 |
| SE420888B (sv) | 1981-11-09 |
| AT347178B (de) | 1978-12-11 |
| DE2602964A1 (de) | 1976-08-05 |
| BR7600646A (pt) | 1976-08-31 |
| IE42949L (en) | 1976-08-03 |
| NL7600700A (nl) | 1976-08-05 |
| DD124703A6 (de) | 1977-03-09 |
| NO760343L (de) | 1976-08-04 |
| ZA757951B (en) | 1976-12-29 |
| BE838171R (fr) | 1976-08-02 |
| AU500653B2 (en) | 1979-05-31 |
| AU8790375A (en) | 1977-06-30 |
| GB1534866A (en) | 1978-12-06 |
| ATA69776A (de) | 1978-04-15 |
| DK139833C (de) | 1979-10-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: AMERICAN CYANAMID COMPANY |