CH631710A5 - Verfahren zur herstellung von neuen azolyl-carbonsaeure-derivaten. - Google Patents
Verfahren zur herstellung von neuen azolyl-carbonsaeure-derivaten. Download PDFInfo
- Publication number
- CH631710A5 CH631710A5 CH951077A CH951077A CH631710A5 CH 631710 A5 CH631710 A5 CH 631710A5 CH 951077 A CH951077 A CH 951077A CH 951077 A CH951077 A CH 951077A CH 631710 A5 CH631710 A5 CH 631710A5
- Authority
- CH
- Switzerland
- Prior art keywords
- keto
- alkyl
- acid derivatives
- optionally substituted
- dimethyl
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 3
- XEKOZEPEJUTTDN-UHFFFAOYSA-N 1h-pyrrol-2-yl hydrogen carbonate Chemical class OC(=O)OC1=CC=CN1 XEKOZEPEJUTTDN-UHFFFAOYSA-N 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims description 39
- 150000001875 compounds Chemical class 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- WRHZVMBBRYBTKZ-UHFFFAOYSA-N pyrrole-2-carboxylic acid Chemical class OC(=O)C1=CC=CN1 WRHZVMBBRYBTKZ-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000001188 haloalkyl group Chemical group 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 150000007513 acids Chemical class 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 7
- 125000002837 carbocyclic group Chemical group 0.000 claims description 6
- 125000000468 ketone group Chemical group 0.000 claims description 6
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 239000011230 binding agent Substances 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 150000003851 azoles Chemical class 0.000 claims description 2
- 102000016726 Coat Protein Complex I Human genes 0.000 claims 1
- 108010092897 Coat Protein Complex I Proteins 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 description 46
- -1 4-Bromo-4- (2,4,5-trichlorophenoxy) -2,2-dimethyl-3-keto-butanoic acid Chemical compound 0.000 description 45
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
- 241000196324 Embryophyta Species 0.000 description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- 239000000460 chlorine Substances 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 239000013543 active substance Substances 0.000 description 23
- 239000000203 mixture Substances 0.000 description 21
- 206010061217 Infestation Diseases 0.000 description 20
- 239000002904 solvent Substances 0.000 description 20
- 239000007921 spray Substances 0.000 description 20
- 208000015181 infectious disease Diseases 0.000 description 17
- 125000004432 carbon atom Chemical group C* 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 230000001681 protective effect Effects 0.000 description 15
- 241000209219 Hordeum Species 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 210000005069 ears Anatomy 0.000 description 12
- 235000007340 Hordeum vulgare Nutrition 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 125000002877 alkyl aryl group Chemical group 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 238000005554 pickling Methods 0.000 description 7
- 229920000151 polyglycol Polymers 0.000 description 7
- 239000010695 polyglycol Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 240000008067 Cucumis sativus Species 0.000 description 6
- 241000221785 Erysiphales Species 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 235000013339 cereals Nutrition 0.000 description 6
- 239000012141 concentrate Substances 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- 241000221787 Erysiphe Species 0.000 description 5
- 241000233866 Fungi Species 0.000 description 5
- 241000220225 Malus Species 0.000 description 5
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 241001480061 Blumeria graminis Species 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- UFHWPMKFZCGMSM-UHFFFAOYSA-N ethyl 4-(4-chlorophenoxy)-4-imidazol-1-yl-2,2-dimethyl-3-oxobutanoate Chemical compound C1=CN=CN1C(C(=O)C(C)(C)C(=O)OCC)OC1=CC=C(Cl)C=C1 UFHWPMKFZCGMSM-UHFFFAOYSA-N 0.000 description 4
- KGWHJNQBENEMQD-UHFFFAOYSA-N ethyl 4-bromo-4-(4-chlorophenoxy)-2,2-dimethyl-3-oxobutanoate Chemical compound CCOC(=O)C(C)(C)C(=O)C(Br)OC1=CC=C(Cl)C=C1 KGWHJNQBENEMQD-UHFFFAOYSA-N 0.000 description 4
- 125000004494 ethyl ester group Chemical group 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 230000000855 fungicidal effect Effects 0.000 description 4
- 238000011081 inoculation Methods 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 3
- 239000004606 Fillers/Extenders Substances 0.000 description 3
- 206010017533 Fungal infection Diseases 0.000 description 3
- 241000489964 Fusicladium Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 241000221576 Uromyces Species 0.000 description 3
- 241000221577 Uromyces appendiculatus Species 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 208000024386 fungal infectious disease Diseases 0.000 description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
- 244000052769 pathogen Species 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- VDWMVYYKURFKGC-UHFFFAOYSA-N 3,3-dimethyl-1-phenoxy-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)C)OC1=CC=CC=C1 VDWMVYYKURFKGC-UHFFFAOYSA-N 0.000 description 2
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 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
- 239000006004 Quartz sand Substances 0.000 description 2
- 206010037888 Rash pustular Diseases 0.000 description 2
- 206010039509 Scab Diseases 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 241001617088 Thanatephorus sasakii Species 0.000 description 2
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- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
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- FPASGAFVNIAGEZ-UHFFFAOYSA-N ethyl 4-(4-chlorophenoxy)-2,2-dimethyl-3-oxobutanoate Chemical compound CCOC(=O)C(C)(C)C(=O)COC1=CC=C(Cl)C=C1 FPASGAFVNIAGEZ-UHFFFAOYSA-N 0.000 description 2
- 230000002538 fungal effect Effects 0.000 description 2
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- 230000002464 fungitoxic effect Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
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- 230000003071 parasitic effect Effects 0.000 description 2
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- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
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- 239000011435 rock Substances 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- GIZSHQYTTBQKOQ-UHFFFAOYSA-N threo-Syringoylglycerol Chemical compound COC1=CC(C(O)C(O)CO)=CC(OC)=C1O GIZSHQYTTBQKOQ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- UWOQPVONOBFTJW-UHFFFAOYSA-N 1-bromo-1-(2,4-dichlorophenoxy)-3,3-dimethylbutan-2-one Chemical compound CC(C)(C)C(=O)C(Br)OC1=CC=C(Cl)C=C1Cl UWOQPVONOBFTJW-UHFFFAOYSA-N 0.000 description 1
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 1
- QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 description 1
- LCMQISSCHHGCLN-UHFFFAOYSA-N 2-[2-(4-chlorophenoxy)-2-imidazol-1-ylacetyl]-2-methylhexanoic acid Chemical compound C1=CN=CN1C(C(=O)C(C)(C(O)=O)CCCC)OC1=CC=C(Cl)C=C1 LCMQISSCHHGCLN-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- LTQUTJCKROQLDQ-UHFFFAOYSA-N 4-(4-chlorophenoxy)-2,2-dimethyl-3-oxo-4-(1,2,4-triazol-1-yl)butanoic acid Chemical compound C1=NC=NN1C(C(=O)C(C)(C(O)=O)C)OC1=CC=C(Cl)C=C1 LTQUTJCKROQLDQ-UHFFFAOYSA-N 0.000 description 1
- RFGNKZFJDMZHDU-UHFFFAOYSA-N 4-(4-chlorophenoxy)-4-imidazol-1-yl-2,2-dimethyl-3-oxobutanoic acid Chemical compound C1=CN=CN1C(C(=O)C(C)(C(O)=O)C)OC1=CC=C(Cl)C=C1 RFGNKZFJDMZHDU-UHFFFAOYSA-N 0.000 description 1
- BLGDHSGGUAHHBJ-UHFFFAOYSA-N 4-(4-fluorophenoxy)-2,2-dimethyl-3-oxo-4-(1,2,4-triazol-1-yl)butanoic acid Chemical compound C1=NC=NN1C(C(=O)C(C)(C(O)=O)C)OC1=CC=C(F)C=C1 BLGDHSGGUAHHBJ-UHFFFAOYSA-N 0.000 description 1
- BNMVOGWYCVYLOR-UHFFFAOYSA-N 4-bromo-2,2-dimethyl-3-oxo-4-(2-phenylphenoxy)butanoic acid Chemical compound OC(=O)C(C)(C)C(=O)C(Br)OC1=CC=CC=C1C1=CC=CC=C1 BNMVOGWYCVYLOR-UHFFFAOYSA-N 0.000 description 1
- UNOSSLBBQKWKOY-UHFFFAOYSA-N 4-bromo-4-(4-chlorophenoxy)-2,2-dimethyl-3-oxo-n-phenylbutanamide Chemical compound C=1C=C(Cl)C=CC=1OC(Br)C(=O)C(C)(C)C(=O)NC1=CC=CC=C1 UNOSSLBBQKWKOY-UHFFFAOYSA-N 0.000 description 1
- WEASSJHSWOCZMB-UHFFFAOYSA-N 4-bromo-4-(4-chlorophenoxy)-2,2-dimethyl-3-oxobutanamide Chemical compound NC(=O)C(C)(C)C(=O)C(Br)OC1=CC=C(Cl)C=C1 WEASSJHSWOCZMB-UHFFFAOYSA-N 0.000 description 1
- RYWLNWDDHHMZAL-UHFFFAOYSA-N 4-bromo-4-(4-chlorophenoxy)-2,2-dimethyl-3-oxobutanoic acid Chemical compound OC(=O)C(C)(C)C(=O)C(Br)OC1=CC=C(Cl)C=C1 RYWLNWDDHHMZAL-UHFFFAOYSA-N 0.000 description 1
- PPTWEUNXVSHEMP-UHFFFAOYSA-N 4-bromo-4-(4-chlorophenoxy)-2-ethyl-2-methyl-3-oxobutanoic acid Chemical compound CCC(C)(C(O)=O)C(=O)C(Br)OC1=CC=C(Cl)C=C1 PPTWEUNXVSHEMP-UHFFFAOYSA-N 0.000 description 1
- PELNDUGCVZSQTJ-UHFFFAOYSA-N 4-bromo-4-(4-chlorophenoxy)-n,2,2-trimethyl-3-oxobutanamide Chemical compound CNC(=O)C(C)(C)C(=O)C(Br)OC1=CC=C(Cl)C=C1 PELNDUGCVZSQTJ-UHFFFAOYSA-N 0.000 description 1
- PXQUBDFWSKJDDE-UHFFFAOYSA-N 4-bromo-4-(4-chlorophenoxy)-n,n,2,2-tetramethyl-3-oxobutanamide Chemical compound CN(C)C(=O)C(C)(C)C(=O)C(Br)OC1=CC=C(Cl)C=C1 PXQUBDFWSKJDDE-UHFFFAOYSA-N 0.000 description 1
- OUHZJNWKNXHQBH-UHFFFAOYSA-N 4-bromo-4-(4-fluorophenoxy)-2,2-dimethyl-3-oxobutanoic acid Chemical compound OC(=O)C(C)(C)C(=O)C(Br)OC1=CC=C(F)C=C1 OUHZJNWKNXHQBH-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 1
- 125000001054 5 membered carbocyclic group Chemical group 0.000 description 1
- 125000004008 6 membered carbocyclic group Chemical group 0.000 description 1
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- UGCHJPOGMKUCGF-UHFFFAOYSA-N ethyl 4-bromo-2,2-dimethyl-3-oxo-4-[3-(trifluoromethyl)phenoxy]butanoate Chemical compound CCOC(=O)C(C)(C)C(=O)C(Br)OC1=CC=CC(C(F)(F)F)=C1 UGCHJPOGMKUCGF-UHFFFAOYSA-N 0.000 description 1
- XHIXCENTXGJBFA-UHFFFAOYSA-N ethyl 4-bromo-2,2-dimethyl-3-oxobutanoate Chemical compound CCOC(=O)C(C)(C)C(=O)CBr XHIXCENTXGJBFA-UHFFFAOYSA-N 0.000 description 1
- HHXTVPCBQTWNSD-UHFFFAOYSA-N ethyl 4-bromo-2,2-dimethyl-4-(4-nitrophenoxy)-3-oxobutanoate Chemical compound CCOC(=O)C(C)(C)C(=O)C(Br)OC1=CC=C([N+]([O-])=O)C=C1 HHXTVPCBQTWNSD-UHFFFAOYSA-N 0.000 description 1
- DHXVNXSYWZISRK-UHFFFAOYSA-N ethyl 4-bromo-4-(4-bromophenoxy)-2,2-dimethyl-3-oxobutanoate Chemical compound CCOC(=O)C(C)(C)C(=O)C(Br)OC1=CC=C(Br)C=C1 DHXVNXSYWZISRK-UHFFFAOYSA-N 0.000 description 1
- TWMIUYRMVNEVRV-UHFFFAOYSA-N ethyl 4-bromo-4-(4-chlorophenoxy)-2-(4-chlorophenyl)-2-methyl-3-oxobutanoate Chemical compound C=1C=C(Cl)C=CC=1C(C)(C(=O)OCC)C(=O)C(Br)OC1=CC=C(Cl)C=C1 TWMIUYRMVNEVRV-UHFFFAOYSA-N 0.000 description 1
- ICPGIANMDJFCHS-UHFFFAOYSA-N ethyl 4-bromo-4-(4-chlorophenoxy)-2-methyl-3-oxo-2-propan-2-ylbutanoate Chemical compound CCOC(=O)C(C)(C(C)C)C(=O)C(Br)OC1=CC=C(Cl)C=C1 ICPGIANMDJFCHS-UHFFFAOYSA-N 0.000 description 1
- VESOFRFROIOCEC-UHFFFAOYSA-N ethyl 4-bromo-4-(4-cyanophenoxy)-2,2-dimethyl-3-oxobutanoate Chemical compound CCOC(=O)C(C)(C)C(=O)C(Br)OC1=CC=C(C#N)C=C1 VESOFRFROIOCEC-UHFFFAOYSA-N 0.000 description 1
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- 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
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- 229910052901 montmorillonite Inorganic materials 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
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- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
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- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
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- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
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- OWWWINQMSXUHJT-UHFFFAOYSA-N propyl 4-bromo-4-(4-chlorophenoxy)-2,2-dimethyl-3-oxobutanoate Chemical compound CCCOC(=O)C(C)(C)C(=O)C(Br)OC1=CC=C(Cl)C=C1 OWWWINQMSXUHJT-UHFFFAOYSA-N 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
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- 241000894007 species Species 0.000 description 1
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- 230000009897 systematic effect Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- FZYHTUUGFAYRPH-UHFFFAOYSA-N tert-butyl 4-(4-chlorophenoxy)-4-imidazol-1-yl-2,2-dimethyl-3-oxobutanoate Chemical compound C1=CN=CN1C(C(=O)C(C)(C)C(=O)OC(C)(C)C)OC1=CC=C(Cl)C=C1 FZYHTUUGFAYRPH-UHFFFAOYSA-N 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
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
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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
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762635663 DE2635663A1 (de) | 1976-08-07 | 1976-08-07 | Azolyl-carbonsaeure-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH631710A5 true CH631710A5 (de) | 1982-08-31 |
Family
ID=5984990
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH951077A CH631710A5 (de) | 1976-08-07 | 1977-08-02 | Verfahren zur herstellung von neuen azolyl-carbonsaeure-derivaten. |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US4331674A (en, 2012) |
| JP (1) | JPS6026110B2 (en, 2012) |
| AT (1) | AT358872B (en, 2012) |
| AU (1) | AU512557B2 (en, 2012) |
| BE (1) | BE857519A (en, 2012) |
| BR (1) | BR7705203A (en, 2012) |
| CA (1) | CA1092130A (en, 2012) |
| CH (1) | CH631710A5 (en, 2012) |
| CS (1) | CS194815B2 (en, 2012) |
| DD (1) | DD133391A5 (en, 2012) |
| DE (1) | DE2635663A1 (en, 2012) |
| DK (1) | DK150595C (en, 2012) |
| EG (1) | EG12805A (en, 2012) |
| FI (1) | FI772360A7 (en, 2012) |
| FR (1) | FR2360579A1 (en, 2012) |
| GB (1) | GB1532140A (en, 2012) |
| HU (1) | HU177167B (en, 2012) |
| IL (1) | IL52663A (en, 2012) |
| IT (1) | IT1085152B (en, 2012) |
| NL (1) | NL7708658A (en, 2012) |
| NZ (1) | NZ184848A (en, 2012) |
| PL (1) | PL103472B1 (en, 2012) |
| PT (1) | PT66886B (en, 2012) |
| SE (1) | SE7708895L (en, 2012) |
| TR (1) | TR19257A (en, 2012) |
| ZA (1) | ZA774737B (en, 2012) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3721022A (en) * | 1971-01-15 | 1973-03-20 | J Mercorelli | Design device |
| EP0002331A3 (en) * | 1977-12-07 | 1979-06-27 | Imperial Chemical Industries Plc | Imidazole and triazole compounds, fungicidal and plant growth regulating compositions, method of combating fungal infections in plants and method of regulating plant growth |
| DE2811919A1 (de) * | 1978-03-18 | 1979-09-27 | Bayer Ag | Acylierte 1-azolyl-2-hydroxy-butan- derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| DE2827968A1 (de) * | 1978-06-26 | 1980-01-10 | Bayer Ag | Sulfenylierte carbamoyl-triazolyl- o,n-acetale, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| DE2846038A1 (de) * | 1978-10-23 | 1980-05-08 | Basf Ag | 1,2,4-triazolderivate, ihre herstellung und verwendung |
| DE3021551A1 (de) * | 1980-06-07 | 1981-12-24 | Bayer Ag, 5090 Leverkusen | 4-substituierte 1-azolyl-1-phenoxy-3,3-dimethyl-butan-2-one und -ole, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| EP0046633A1 (en) * | 1980-08-22 | 1982-03-03 | Imperial Chemical Industries Plc | Heterocyclic compounds useful as pesticides and processes for making them |
| DE3032326A1 (de) | 1980-08-27 | 1982-04-08 | Bayer Ag, 5090 Leverkusen | Azolylalkyl-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| JPS5758671A (en) * | 1980-09-25 | 1982-04-08 | Ishihara Sangyo Kaisha Ltd | Phenoxyalkylazole type compound and agricultural and gardening fungicide comprising it |
| AR228764A1 (es) * | 1980-12-20 | 1983-04-15 | Bayer Ag | 1-azolil-3,3-dimetilalcan(c3-4)-2-onas y-2-oles,sustituidos,procedimiento para su produccion y composiciones protectoras de plantas fungicidas y reguladoras del crecimiento de las plantas a base de dichos compuestos |
| GB2104065B (en) * | 1981-06-04 | 1985-11-06 | Ciba Geigy Ag | Heterocyclyl-substituted mandelic acid compounds and mandelonitriles and their use for combating microorganisms |
| DE3200414A1 (de) * | 1982-01-09 | 1983-07-21 | Bayer Ag, 5090 Leverkusen | Azolyl-thioether-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide und pflanzenwachstumsregulatoren |
| US4517194A (en) * | 1982-06-25 | 1985-05-14 | Ciba-Geigy Corporation | Azolylmandelic acid derivatives and use thereof for controlling microorganisms |
| US4584008A (en) * | 1982-07-14 | 1986-04-22 | Chevron Research Company | Aldol adducts containing triazole groups |
| PH19347A (en) * | 1982-09-30 | 1986-04-02 | Pfizer | Triazole derivatives,pharmaceutical composition containing same and method of use thereof |
| DE3313941A1 (de) * | 1983-04-15 | 1984-10-18 | Schering AG, 1000 Berlin und 4709 Bergkamen | 4-azolyl-pentannitrile, verfahren zur herstellung dieser verbundungen sowie diese enthaltende biozide mittel |
| GB8322983D0 (en) * | 1983-08-26 | 1983-09-28 | Pfizer Ltd | Triazole antifungal agents |
| DE3508909A1 (de) * | 1985-03-13 | 1986-09-18 | Bayer Ag, 5090 Leverkusen | Piperazinylmethyl-1,2,4-triazolylmethyl-carbinole |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH531516A (de) * | 1969-05-21 | 1972-12-15 | Bayer Ag | Verfahren zur Herstellung neuer Phenylimidazolyl-fettsäure-derivate |
| DE2105490C3 (de) * | 1971-02-05 | 1979-06-13 | Bayer Ag, 5090 Leverkusen | 1 -Imidazolylketonderivate |
| US4036966A (en) * | 1972-09-26 | 1977-07-19 | Bayer Aktiengesellschaft | 1,2,4-Triazole antimycotic compositions and use thereof |
| DE2324010C3 (de) * | 1973-05-12 | 1981-10-08 | Bayer Ag, 5090 Leverkusen | 1-Substituierte 2-Triazolyl-2-phenoxyäthanol-Verbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von Pilzen |
| DE2423987C2 (de) * | 1974-05-17 | 1986-01-16 | Bayer Ag, 5090 Leverkusen | Metallkomplexe von Azolyläthern, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Fungizide |
| DE2455955A1 (de) * | 1974-11-27 | 1976-08-12 | Bayer Ag | Fungizide mittel |
| DE2455953A1 (de) * | 1974-11-27 | 1976-08-12 | Bayer Ag | Fungizide mittel |
-
1976
- 1976-08-07 DE DE19762635663 patent/DE2635663A1/de active Granted
-
1977
- 1977-07-27 US US05/819,533 patent/US4331674A/en not_active Expired - Lifetime
- 1977-08-02 GB GB32386/77A patent/GB1532140A/en not_active Expired
- 1977-08-02 CH CH951077A patent/CH631710A5/de not_active IP Right Cessation
- 1977-08-03 DD DD77200422A patent/DD133391A5/xx unknown
- 1977-08-03 EG EG457/77A patent/EG12805A/xx active
- 1977-08-04 NL NL7708658A patent/NL7708658A/xx not_active Application Discontinuation
- 1977-08-04 SE SE7708895A patent/SE7708895L/xx unknown
- 1977-08-04 FI FI772360A patent/FI772360A7/fi not_active Application Discontinuation
- 1977-08-04 IL IL7752663A patent/IL52663A/xx unknown
- 1977-08-04 PT PT66886A patent/PT66886B/pt unknown
- 1977-08-04 NZ NZ184848A patent/NZ184848A/xx unknown
- 1977-08-05 JP JP52093448A patent/JPS6026110B2/ja not_active Expired
- 1977-08-05 IT IT26562/77A patent/IT1085152B/it active
- 1977-08-05 TR TR19257A patent/TR19257A/xx unknown
- 1977-08-05 PL PL1977200093A patent/PL103472B1/pl unknown
- 1977-08-05 HU HU77BA3566A patent/HU177167B/hu unknown
- 1977-08-05 CA CA284,241A patent/CA1092130A/en not_active Expired
- 1977-08-05 BE BE179932A patent/BE857519A/xx not_active IP Right Cessation
- 1977-08-05 BR BR7705203A patent/BR7705203A/pt unknown
- 1977-08-05 DK DK352377A patent/DK150595C/da not_active IP Right Cessation
- 1977-08-05 FR FR7724262A patent/FR2360579A1/fr active Granted
- 1977-08-05 CS CS775201A patent/CS194815B2/cs unknown
- 1977-08-05 AU AU27649/77A patent/AU512557B2/en not_active Expired
- 1977-08-05 AT AT576477A patent/AT358872B/de not_active IP Right Cessation
- 1977-08-05 ZA ZA00774737A patent/ZA774737B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA774737B (en) | 1978-06-28 |
| BR7705203A (pt) | 1978-06-06 |
| CS194815B2 (en) | 1979-12-31 |
| PT66886B (en) | 1979-01-25 |
| IL52663A0 (en) | 1977-10-31 |
| DD133391A5 (de) | 1979-01-03 |
| DK150595C (da) | 1987-11-02 |
| FR2360579B1 (en, 2012) | 1981-01-09 |
| NZ184848A (en) | 1978-12-18 |
| AU512557B2 (en) | 1980-10-16 |
| DE2635663A1 (de) | 1978-02-09 |
| SE7708895L (sv) | 1978-02-08 |
| IT1085152B (it) | 1985-05-28 |
| IL52663A (en) | 1981-02-27 |
| JPS6026110B2 (ja) | 1985-06-21 |
| GB1532140A (en) | 1978-11-15 |
| PT66886A (en) | 1977-09-01 |
| FR2360579A1 (fr) | 1978-03-03 |
| US4331674A (en) | 1982-05-25 |
| AT358872B (de) | 1980-10-10 |
| BE857519A (fr) | 1978-02-06 |
| PL200093A1 (pl) | 1978-04-10 |
| NL7708658A (nl) | 1978-02-09 |
| AU2764977A (en) | 1979-02-15 |
| DE2635663C2 (en, 2012) | 1988-08-11 |
| HU177167B (en) | 1981-08-28 |
| ATA576477A (de) | 1980-02-15 |
| PL103472B1 (pl) | 1979-06-30 |
| EG12805A (en) | 1979-09-30 |
| TR19257A (tr) | 1978-08-15 |
| DK352377A (da) | 1978-02-08 |
| DK150595B (da) | 1987-04-06 |
| CA1092130A (en) | 1980-12-23 |
| JPS5321163A (en) | 1978-02-27 |
| FI772360A7 (en, 2012) | 1978-02-08 |
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