CA1185981A - Substituted azolyl-phenoxy derivatives, processes for their preparation, and their use as fungicides - Google Patents
Substituted azolyl-phenoxy derivatives, processes for their preparation, and their use as fungicidesInfo
- Publication number
- CA1185981A CA1185981A CA000409518A CA409518A CA1185981A CA 1185981 A CA1185981 A CA 1185981A CA 000409518 A CA000409518 A CA 000409518A CA 409518 A CA409518 A CA 409518A CA 1185981 A CA1185981 A CA 1185981A
- Authority
- CA
- Canada
- Prior art keywords
- group
- compound
- alkyl
- formula
- butan
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- -1 azolyl-phenoxy Chemical class 0.000 title claims abstract description 25
- 238000000034 method Methods 0.000 title claims description 26
- 230000008569 process Effects 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title description 10
- 239000000417 fungicide Substances 0.000 title description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 24
- 239000002253 acid Substances 0.000 claims abstract description 19
- 150000003839 salts Chemical class 0.000 claims abstract description 17
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 15
- 125000005843 halogen group Chemical group 0.000 claims abstract description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 15
- 229910052751 metal Inorganic materials 0.000 claims abstract description 12
- 239000002184 metal Substances 0.000 claims abstract description 12
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 11
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 11
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
- 125000006193 alkinyl group Chemical group 0.000 claims abstract description 5
- 125000000468 ketone group Chemical group 0.000 claims abstract description 5
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 83
- 238000006243 chemical reaction Methods 0.000 claims description 40
- 239000000460 chlorine Chemical group 0.000 claims description 34
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 239000003085 diluting agent Substances 0.000 claims description 18
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
- 239000011737 fluorine Substances 0.000 claims description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
- 239000011230 binding agent Substances 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 239000002689 soil Substances 0.000 claims description 8
- 241000233866 Fungi Species 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical group 0.000 claims description 6
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 150000003254 radicals Chemical class 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- XBMQBGQLUVPOPF-UHFFFAOYSA-N 1-imidazol-1-yl-1-(4-methoxyimino-2-methylcyclohexa-1,5-dien-1-yl)oxy-3,3-dimethylbutan-2-one Chemical compound CC(C(C(OC1=C(CC(C=C1)=NOC)C)N1C=NC=C1)=O)(C)C XBMQBGQLUVPOPF-UHFFFAOYSA-N 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 231100001184 nonphytotoxic Toxicity 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 229910052740 iodine Chemical group 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 9
- 201000010099 disease Diseases 0.000 abstract description 7
- 230000000855 fungicidal effect Effects 0.000 abstract description 5
- 206010039509 Scab Diseases 0.000 abstract description 4
- 235000013339 cereals Nutrition 0.000 abstract description 4
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 abstract description 2
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 38
- 241000196324 Embryophyta Species 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 239000003921 oil Substances 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 241000209219 Hordeum Species 0.000 description 8
- 235000007340 Hordeum vulgare Nutrition 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 239000003995 emulsifying agent Substances 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 150000002576 ketones Chemical class 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical group [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000002170 ethers Chemical class 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 230000001681 protective effect Effects 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 239000000969 carrier Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 241000221577 Uromyces appendiculatus Species 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 238000011081 inoculation Methods 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000012279 sodium borohydride Substances 0.000 description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 241000520648 Pyrenophora teres Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000004411 aluminium Substances 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 235000008504 concentrate Nutrition 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-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
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000228454 Pyrenophora graminea Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 241000228452 Venturia inaequalis Species 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- DKEKURXRUXRNES-UHFFFAOYSA-N bis(1h-pyrrol-2-yl)methanone Chemical compound C=1C=CNC=1C(=O)C1=CC=CN1 DKEKURXRUXRNES-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 2
- 238000010410 dusting Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 2
- 239000003595 mist Substances 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011814 protection agent Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- 229940001593 sodium carbonate Drugs 0.000 description 2
- 238000009331 sowing Methods 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- 238000009827 uniform distribution Methods 0.000 description 2
- FMHTVPHLNRBKCJ-UHFFFAOYSA-N 1-(5-methoxyimino-6-methylcyclohexa-1,3-dien-1-yl)oxy-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound CC(C(C(N1N=CN=C1)OC=1C(C(C=CC=1)=NOC)C)=O)(C)C FMHTVPHLNRBKCJ-UHFFFAOYSA-N 0.000 description 1
- KIVDZERHEZTUGL-UHFFFAOYSA-N 1-bromo-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound CC(C)(C)C(=O)C(Br)N1C=NC=N1 KIVDZERHEZTUGL-UHFFFAOYSA-N 0.000 description 1
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 1
- DBFWHMRLUANEKP-UHFFFAOYSA-N 1-fluoro-1-(4-methoxyimino-2-methylcyclohexa-1,5-dien-1-yl)oxy-3,3-dimethylbutan-2-one Chemical compound CC(C(C(OC1=C(CC(C=C1)=NOC)C)F)=O)(C)C DBFWHMRLUANEKP-UHFFFAOYSA-N 0.000 description 1
- LJDXNLFMULXTGJ-UHFFFAOYSA-N 1-imidazol-1-yl-1-(4-methoxyimino-2-methylcyclohexa-1,5-dien-1-yl)oxy-3,3-dimethylbutan-2-ol Chemical compound CC(C(C(OC1=C(CC(C=C1)=NOC)C)N1C=NC=C1)O)(C)C LJDXNLFMULXTGJ-UHFFFAOYSA-N 0.000 description 1
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 1
- LGGLKPFTYFIQSY-UHFFFAOYSA-N 3-(benzenesulfonyl)thiophene Chemical compound C=1C=CC=CC=1S(=O)(=O)C=1C=CSC=1 LGGLKPFTYFIQSY-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
- 244000215068 Acacia senegal Species 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- RGCKGOZRHPZPFP-UHFFFAOYSA-N Alizarin Natural products C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 1
- 241000235349 Ascomycota Species 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 241000221198 Basidiomycota Species 0.000 description 1
- 241001480061 Blumeria graminis Species 0.000 description 1
- 241000895523 Blumeria graminis f. sp. hordei Species 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 229910021532 Calcite Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 241000760356 Chytridiomycetes Species 0.000 description 1
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- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- 241000221785 Erysiphales Species 0.000 description 1
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical group O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000228456 Leptosphaeria Species 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 240000001931 Ludwigia octovalvis Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
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- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
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- 239000012320 chlorinating reagent Substances 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 239000012973 diazabicyclooctane Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 235000005489 dwarf bean Nutrition 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- IYRWEQXVUNLMAY-UHFFFAOYSA-N fluoroketone group Chemical group FC(=O)F IYRWEQXVUNLMAY-UHFFFAOYSA-N 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 150000003948 formamides Chemical class 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
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- 239000001023 inorganic pigment Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- DCYOBGZUOMKFPA-UHFFFAOYSA-N iron(2+);iron(3+);octadecacyanide Chemical compound [Fe+2].[Fe+2].[Fe+2].[Fe+3].[Fe+3].[Fe+3].[Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] DCYOBGZUOMKFPA-UHFFFAOYSA-N 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
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- 238000002156 mixing Methods 0.000 description 1
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- 239000011733 molybdenum Substances 0.000 description 1
- VOVZXURTCKPRDQ-CQSZACIVSA-N n-[4-[chloro(difluoro)methoxy]phenyl]-6-[(3r)-3-hydroxypyrrolidin-1-yl]-5-(1h-pyrazol-5-yl)pyridine-3-carboxamide Chemical compound C1[C@H](O)CCN1C1=NC=C(C(=O)NC=2C=CC(OC(F)(F)Cl)=CC=2)C=C1C1=CC=NN1 VOVZXURTCKPRDQ-CQSZACIVSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 229960003351 prussian blue Drugs 0.000 description 1
- 239000013225 prussian blue Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 208000029561 pustule Diseases 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
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- ORIHZIZPTZTNCU-YVMONPNESA-N salicylaldoxime Chemical compound O\N=C/C1=CC=CC=C1O ORIHZIZPTZTNCU-YVMONPNESA-N 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 229960004249 sodium acetate Drugs 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- 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
- C07D233/60—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 with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms
-
- 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
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3132335.9 | 1981-08-17 | ||
| DE19813132335 DE3132335A1 (de) | 1981-08-17 | 1981-08-17 | Substituierte azolyl-phenoxy-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1185981A true CA1185981A (en) | 1985-04-23 |
Family
ID=6139410
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000409518A Expired CA1185981A (en) | 1981-08-17 | 1982-08-16 | Substituted azolyl-phenoxy derivatives, processes for their preparation, and their use as fungicides |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4472416A (en, 2012) |
| EP (1) | EP0076370B1 (en, 2012) |
| JP (1) | JPS5839670A (en, 2012) |
| KR (1) | KR890001547B1 (en, 2012) |
| AR (1) | AR231833A1 (en, 2012) |
| AT (1) | ATE20058T1 (en, 2012) |
| AU (1) | AU549479B2 (en, 2012) |
| BR (1) | BR8204776A (en, 2012) |
| CA (1) | CA1185981A (en, 2012) |
| CS (1) | CS228938B2 (en, 2012) |
| DD (1) | DD206528A5 (en, 2012) |
| DE (2) | DE3132335A1 (en, 2012) |
| DK (1) | DK168818B1 (en, 2012) |
| EG (1) | EG15752A (en, 2012) |
| ES (1) | ES515031A0 (en, 2012) |
| GR (1) | GR76255B (en, 2012) |
| HU (1) | HU190409B (en, 2012) |
| IE (1) | IE53871B1 (en, 2012) |
| IL (1) | IL66542A0 (en, 2012) |
| NZ (1) | NZ201578A (en, 2012) |
| PL (1) | PL133290B1 (en, 2012) |
| PT (1) | PT75398B (en, 2012) |
| TR (1) | TR21372A (en, 2012) |
| ZA (1) | ZA825912B (en, 2012) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3237400A1 (de) * | 1982-10-08 | 1984-04-12 | Bayer Ag, 5090 Leverkusen | Substituierte 1-hydroxyethyl-triazolyl-derivate |
| US4690942A (en) * | 1983-12-20 | 1987-09-01 | Ciba-Geigy Corporation | 1-aryl-2-fluoro-2-azolyl alkanones, alkanols, esters, and ethers, composition containing them, and use of them to control phytopathogenic microorganisms |
| DE3427844A1 (de) * | 1984-07-27 | 1986-02-06 | Bayer Ag, 5090 Leverkusen | Substituierte hydroxyalkyl-azole, verfahren zu ihrer herstellung sowie diese enthaltende antimykotische mittel |
| DE3545034A1 (de) * | 1985-12-19 | 1987-06-25 | Bayer Ag | Diastereomeres (a) des 3,3-dimethyl-1-(4-methoximinomethyl-phenoxy)-1-(1,2,4-triazol-1-yl)-butan-2-ols |
| DE3618379A1 (de) * | 1986-05-31 | 1987-12-03 | Bayer Ag | Verfahren zur herstellung eines azol-derivates |
| DE3620166A1 (de) * | 1986-06-14 | 1987-12-17 | Bayer Ag | Verfahren zur herstellung von hydroxybenzaldoxim-o-ethern |
| DE3701715A1 (de) * | 1987-01-22 | 1988-08-04 | Bayer Ag | Fungizide wirkstoffkombinationen |
| AUPQ105499A0 (en) * | 1999-06-18 | 1999-07-08 | Biota Scientific Management Pty Ltd | Antiviral agents |
| AUPR213700A0 (en) * | 2000-12-18 | 2001-01-25 | Biota Scientific Management Pty Ltd | Antiviral agents |
| US20030165413A1 (en) * | 2001-07-18 | 2003-09-04 | Benjamin Scharifker | Process to recover vanadium contained in acid solutions |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1571C (de) * | 1877-12-14 | OHM, Apotheker in Chemnitz und Dr. LANG in j Leer | Einric htungen anDampf-Zerstäubungs-Apparaten | |
| US4147791A (en) * | 1972-01-11 | 1979-04-03 | Bayer Aktiengesellschaft | 1-Substituted-1,2,4-triazole fungicidal compositions and methods for combatting fungi that infect or attack plants |
| 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 |
| DE2325156A1 (de) * | 1973-05-18 | 1974-12-05 | Bayer Ag | Fungizide und mikrobizide mittel |
| DE2333354C2 (de) * | 1973-06-30 | 1983-12-15 | Bayer Ag, 5090 Leverkusen | 2-Aryloxy-2-(imidazol-1-yl)-äthanole sowie deren Salze, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide |
| DE2600799A1 (de) * | 1976-01-10 | 1977-07-14 | Bayer Ag | Acylierte triazolyl-0,n-acetale, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| DE2745827A1 (de) * | 1977-10-12 | 1979-04-26 | Basf Ag | Phenylazophenyloxy-triazolylverbindungen |
-
1981
- 1981-08-17 DE DE19813132335 patent/DE3132335A1/de not_active Withdrawn
-
1982
- 1982-07-16 AU AU86077/82A patent/AU549479B2/en not_active Ceased
- 1982-08-02 US US06/403,988 patent/US4472416A/en not_active Expired - Fee Related
- 1982-08-05 EP EP82107071A patent/EP0076370B1/de not_active Expired
- 1982-08-05 DE DE8282107071T patent/DE3271363D1/de not_active Expired
- 1982-08-05 AT AT82107071T patent/ATE20058T1/de not_active IP Right Cessation
- 1982-08-09 PT PT75398A patent/PT75398B/pt not_active IP Right Cessation
- 1982-08-13 DK DK364682A patent/DK168818B1/da not_active IP Right Cessation
- 1982-08-13 AR AR290311A patent/AR231833A1/es active
- 1982-08-13 IL IL66542A patent/IL66542A0/xx not_active IP Right Cessation
- 1982-08-13 NZ NZ201578A patent/NZ201578A/en unknown
- 1982-08-13 JP JP57139986A patent/JPS5839670A/ja active Granted
- 1982-08-13 GR GR69039A patent/GR76255B/el unknown
- 1982-08-13 DD DD82242510A patent/DD206528A5/de unknown
- 1982-08-16 ES ES515031A patent/ES515031A0/es active Granted
- 1982-08-16 EG EG82499A patent/EG15752A/xx active
- 1982-08-16 BR BR8204776A patent/BR8204776A/pt unknown
- 1982-08-16 CA CA000409518A patent/CA1185981A/en not_active Expired
- 1982-08-16 TR TR21372A patent/TR21372A/xx unknown
- 1982-08-16 PL PL1982237928A patent/PL133290B1/pl unknown
- 1982-08-16 IE IE1978/82A patent/IE53871B1/en unknown
- 1982-08-16 ZA ZA825912A patent/ZA825912B/xx unknown
- 1982-08-17 HU HU822636A patent/HU190409B/hu not_active IP Right Cessation
- 1982-08-17 KR KR8203681A patent/KR890001547B1/ko not_active Expired
- 1982-08-17 CS CS826052A patent/CS228938B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU8607782A (en) | 1983-02-24 |
| ZA825912B (en) | 1983-06-29 |
| DK364682A (da) | 1983-02-18 |
| PT75398B (en) | 1984-12-10 |
| JPS5839670A (ja) | 1983-03-08 |
| DE3132335A1 (de) | 1983-03-03 |
| DE3271363D1 (en) | 1986-07-03 |
| KR890001547B1 (ko) | 1989-05-08 |
| GR76255B (en, 2012) | 1984-08-04 |
| IL66542A0 (en) | 1982-12-31 |
| ATE20058T1 (de) | 1986-06-15 |
| EP0076370B1 (de) | 1986-05-28 |
| IE53871B1 (en) | 1989-03-29 |
| PL237928A1 (en) | 1984-02-27 |
| NZ201578A (en) | 1985-01-31 |
| AU549479B2 (en) | 1986-01-30 |
| PL133290B1 (en) | 1985-05-31 |
| ES8306480A1 (es) | 1983-06-01 |
| IE821978L (en) | 1983-02-17 |
| US4472416A (en) | 1984-09-18 |
| HU190409B (en) | 1986-09-29 |
| CS228938B2 (en) | 1984-05-14 |
| DK168818B1 (da) | 1994-06-20 |
| JPS6146474B2 (en, 2012) | 1986-10-14 |
| ES515031A0 (es) | 1983-06-01 |
| BR8204776A (pt) | 1983-08-02 |
| EP0076370A1 (de) | 1983-04-13 |
| AR231833A1 (es) | 1985-03-29 |
| KR840001141A (ko) | 1984-03-28 |
| EG15752A (en) | 1986-06-30 |
| TR21372A (tr) | 1984-04-25 |
| PT75398A (en) | 1982-09-01 |
| DD206528A5 (de) | 1984-02-01 |
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