HU186884B - Fungicide compositions with activity of controlling growth of plants containing azole compounds as active agents, and process for producing the active agents - Google Patents
Fungicide compositions with activity of controlling growth of plants containing azole compounds as active agents, and process for producing the active agents Download PDFInfo
- Publication number
- HU186884B HU186884B HU811407A HU140781A HU186884B HU 186884 B HU186884 B HU 186884B HU 811407 A HU811407 A HU 811407A HU 140781 A HU140781 A HU 140781A HU 186884 B HU186884 B HU 186884B
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- HU
- Hungary
- Prior art keywords
- formula
- alkyl
- active ingredient
- plants
- choh
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims description 37
- 238000000034 method Methods 0.000 title claims description 12
- 239000000417 fungicide Substances 0.000 title claims description 11
- 230000008569 process Effects 0.000 title claims description 10
- 230000000855 fungicidal effect Effects 0.000 title claims description 6
- 150000003851 azoles Chemical class 0.000 title claims 2
- 230000000694 effects Effects 0.000 title description 12
- 239000013543 active substance Substances 0.000 title description 5
- 230000008635 plant growth Effects 0.000 title description 5
- 239000004480 active ingredient Substances 0.000 claims description 44
- -1 azole compound Chemical class 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 32
- 239000002904 solvent Substances 0.000 claims description 23
- 239000000460 chlorine Substances 0.000 claims description 19
- 239000003085 diluting agent Substances 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 150000002576 ketones Chemical class 0.000 claims description 11
- 239000005648 plant growth regulator Substances 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 239000003995 emulsifying agent Substances 0.000 claims description 7
- 150000002431 hydrogen Chemical group 0.000 claims description 7
- 150000007529 inorganic bases Chemical class 0.000 claims description 7
- 150000007530 organic bases Chemical class 0.000 claims description 6
- 239000002798 polar solvent Substances 0.000 claims description 6
- 239000000843 powder Substances 0.000 claims description 6
- 150000003333 secondary alcohols Chemical class 0.000 claims description 6
- 150000003509 tertiary alcohols Chemical class 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 150000001340 alkali metals Chemical class 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- 239000002168 alkylating agent Substances 0.000 claims description 3
- 229940100198 alkylating agent Drugs 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 239000002270 dispersing agent Substances 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 239000011630 iodine Substances 0.000 claims description 3
- 239000003208 petroleum Substances 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 229910000102 alkali metal hydride Inorganic materials 0.000 claims 2
- 150000008046 alkali metal hydrides Chemical class 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 210000004185 liver Anatomy 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- 239000000080 wetting agent Substances 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 37
- 239000003795 chemical substances by application Substances 0.000 description 37
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 230000012010 growth Effects 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 239000000463 material Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 208000015181 infectious disease Diseases 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 235000013339 cereals Nutrition 0.000 description 8
- 125000001309 chloro group Chemical group Cl* 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 8
- 241000209140 Triticum Species 0.000 description 7
- 239000003630 growth substance Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000002689 soil Substances 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 241000233866 Fungi Species 0.000 description 6
- 235000010469 Glycine max Nutrition 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 244000038559 crop plants Species 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 208000031888 Mycoses Diseases 0.000 description 5
- 235000021307 Triticum Nutrition 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 235000013399 edible fruits Nutrition 0.000 description 5
- 150000002170 ethers Chemical class 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 230000001105 regulatory effect Effects 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000002023 wood Substances 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- 206010017533 Fungal infection Diseases 0.000 description 4
- 240000005979 Hordeum vulgare Species 0.000 description 4
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- 244000070406 Malus silvestris Species 0.000 description 4
- 235000015103 Malus silvestris Nutrition 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 240000007594 Oryza sativa Species 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical class OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 230000001276 controlling effect Effects 0.000 description 4
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- 238000002474 experimental method Methods 0.000 description 4
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- 239000000741 silica gel Substances 0.000 description 4
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- 238000005507 spraying Methods 0.000 description 4
- 230000009105 vegetative growth Effects 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- 241000221785 Erysiphales Species 0.000 description 3
- 244000299507 Gossypium hirsutum Species 0.000 description 3
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- PKHNEWPCMVEDAM-UHFFFAOYSA-N N1(N=CN=C1)C(C(CC1=CC=C(C=C1)Cl)=O)C(C)(C)C Chemical compound N1(N=CN=C1)C(C(CC1=CC=C(C=C1)Cl)=O)C(C)(C)C PKHNEWPCMVEDAM-UHFFFAOYSA-N 0.000 description 3
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- 230000009471 action Effects 0.000 description 3
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- 150000001350 alkyl halides Chemical class 0.000 description 3
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
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- 150000004678 hydrides Chemical class 0.000 description 3
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- PZBPKYOVPCNPJY-UHFFFAOYSA-N 1-[2-(allyloxy)-2-(2,4-dichlorophenyl)ethyl]imidazole Chemical compound ClC1=CC(Cl)=CC=C1C(OCC=C)CN1C=NC=C1 PZBPKYOVPCNPJY-UHFFFAOYSA-N 0.000 description 2
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- CKAPSXZOOQJIBF-UHFFFAOYSA-N hexachlorobenzene Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl CKAPSXZOOQJIBF-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-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
- DWKPPFQULDPWHX-VKHMYHEASA-N l-alanyl ester Chemical compound COC(=O)[C@H](C)N DWKPPFQULDPWHX-VKHMYHEASA-N 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 230000002015 leaf growth Effects 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 1
- 229910001623 magnesium bromide Inorganic materials 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
- CRGZYKWWYNQGEC-UHFFFAOYSA-N magnesium;methanolate Chemical compound [Mg+2].[O-]C.[O-]C CRGZYKWWYNQGEC-UHFFFAOYSA-N 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 235000019988 mead Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 150000005451 methyl sulfates Chemical class 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OYRIKLVYHTWHCZ-UHFFFAOYSA-N n-cyclohexyl-2,5-dimethylfuran-3-carboxamide Chemical compound O1C(C)=CC(C(=O)NC2CCCCC2)=C1C OYRIKLVYHTWHCZ-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 235000014571 nuts Nutrition 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- RCCYSVYHULFYHE-UHFFFAOYSA-N pentanediamide Chemical compound NC(=O)CCCC(N)=O RCCYSVYHULFYHE-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000004476 plant protection product Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 238000007086 side reaction Methods 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
- 238000001694 spray drying Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 230000007103 stamina Effects 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- ILERPRJWJPJZDN-UHFFFAOYSA-N thioquinox Chemical compound C1=CC=C2N=C(SC(=S)S3)C3=NC2=C1 ILERPRJWJPJZDN-UHFFFAOYSA-N 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical class CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
- 125000006000 trichloroethyl group Chemical group 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 230000008511 vegetative development Effects 0.000 description 1
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 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
-
- 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
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Pest Control & Pesticides (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Fertilizers (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pretreatment Of Seeds And Plants (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803019049 DE3019049A1 (de) | 1980-05-19 | 1980-05-19 | Neue azolverbindungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU186884B true HU186884B (en) | 1985-10-28 |
Family
ID=6102758
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU811407A HU186884B (en) | 1980-05-19 | 1981-05-18 | Fungicide compositions with activity of controlling growth of plants containing azole compounds as active agents, and process for producing the active agents |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4380546A (en, 2012) |
| EP (1) | EP0040350B1 (en, 2012) |
| JP (1) | JPS5716870A (en, 2012) |
| KR (1) | KR850000494B1 (en, 2012) |
| AT (1) | ATE4710T1 (en, 2012) |
| AU (1) | AU539440B2 (en, 2012) |
| BR (1) | BR8103029A (en, 2012) |
| CA (1) | CA1163638A (en, 2012) |
| CS (1) | CS225838B2 (en, 2012) |
| DD (1) | DD158845A5 (en, 2012) |
| DE (2) | DE3019049A1 (en, 2012) |
| DK (1) | DK160937C (en, 2012) |
| HU (1) | HU186884B (en, 2012) |
| IL (1) | IL62749A (en, 2012) |
| NZ (1) | NZ197127A (en, 2012) |
| PH (1) | PH17873A (en, 2012) |
| PL (1) | PL127553B2 (en, 2012) |
| ZA (1) | ZA813281B (en, 2012) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3126022A1 (de) * | 1981-07-02 | 1983-01-13 | Basf Ag, 6700 Ludwigshafen | Azolverbindungen, verfahren zu ihrer herstellung und diese enthaltende fungizide |
| 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 |
| DE3209431A1 (de) * | 1982-03-16 | 1983-09-22 | Bayer Ag, 5090 Leverkusen | Phenoxypropyltriazolyl-ketone und -carbinole, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| DE3211850A1 (de) * | 1982-03-31 | 1983-10-06 | Basf Ag | Triazolverbindungen, verfahren zu ihrer herstellung und diese enthaltende fungizide |
| ATE24900T1 (de) * | 1982-04-22 | 1987-01-15 | Ici Plc | Antifungische azolyl-phenyl substituierte alicyclische alkohole. |
| DE3321023A1 (de) * | 1983-06-10 | 1984-12-13 | Basf Ag, 6700 Ludwigshafen | Triazolylalkohole, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| US4648988A (en) * | 1983-12-21 | 1987-03-10 | Janssen Pharmaceutica, N.V. | Water-dilutable wood-preserving liquids |
| DE3400829A1 (de) * | 1984-01-12 | 1985-07-18 | Basf Ag, 6700 Ludwigshafen | Alpha-halogen-phenoxyalkylketone, phenoxyalkylketone, verfahren zu ihrer herstellung, sowie ihre verwendung als zwischenprodukte zur herstellung von fungiziden |
| CA1249832A (en) * | 1984-02-03 | 1989-02-07 | Shionogi & Co., Ltd. | Azolyl cycloalkanol derivatives and agricultural fungicides |
| DE3511922A1 (de) | 1985-04-01 | 1986-10-09 | Basf Ag, 6700 Ludwigshafen | Azolverbindungen, verfahren zu ihrer herstellung und mittel zur regulierung des pflanzenwachstums |
| DE3415486A1 (de) * | 1984-04-26 | 1985-10-31 | Basf Ag, 6700 Ludwigshafen | Azolverbindungen, verfahren zu ihrer herstellung und diese enthaltende fungizide |
| DE3416444A1 (de) * | 1984-05-04 | 1985-11-07 | Basf Ag, 6700 Ludwigshafen | Verfahren zur diastereoselektiven reduktion von (alpha)-triazolylketonen zu ss-triazolylcarbinolen |
| IL75017A (en) * | 1984-05-04 | 1989-07-31 | Basf Ag | Diastereoselective reduction of alpha-triazolylketones to beta-triazolylcarbinols |
| DE3420227A1 (de) * | 1984-05-30 | 1985-12-05 | Basf Ag, 6700 Ludwigshafen | Vinylazole, verfahren zu ihrer herstellung und ihre verwendung bei der bekaempfung von pilzen |
| DE3437919A1 (de) * | 1984-10-17 | 1986-04-17 | Basf Ag, 6700 Ludwigshafen | Benzyloxyalkylazole und diese enthaltende fungizide |
| DE3515309A1 (de) * | 1985-04-27 | 1986-10-30 | Basf Ag, 6700 Ludwigshafen | 1,3-dioxan-5-yl-alkyltriazole, ihre herstellung, ihre verwendung zur regulierung des pflanzenwachstums und mittel dafuer |
| DE3702301A1 (de) * | 1986-03-06 | 1987-09-10 | Bayer Ag | 2-hydroxyethyl-azol-derivate |
| ATE54312T1 (de) * | 1986-03-06 | 1990-07-15 | Bayer Ag | 2-hydroxyethyl-azol-derivate. |
| DE3642632A1 (de) * | 1986-12-13 | 1988-06-23 | Basf Ag | Verfahren zur herstellung von phenoxysubstituierten estern und zwischenprodukte hierfuer |
| DE3709806A1 (de) * | 1987-03-25 | 1988-10-06 | Basf Ag | Mittel zur regulierung des pflanzenwachstums |
| DE3721695A1 (de) * | 1987-07-01 | 1989-01-12 | Bayer Ag | 1-phenoxy-3-triazolyl-1-hexen-derivate |
| DE3813129A1 (de) * | 1987-07-01 | 1989-01-12 | Bayer Ag | Hydroxyethyl-azolyl-derivate |
| DE3800306A1 (de) * | 1988-01-08 | 1989-07-20 | Basf Ag | Tert.-butylalkinole, verfahren zu ihrer herstellung und deren verwendung |
| WO2010029028A1 (de) * | 2008-09-09 | 2010-03-18 | Basf Se | Imidazolverbindungen, ihre verwendung sowie sie enthaltende mittel |
| US20110160056A1 (en) * | 2008-09-09 | 2011-06-30 | Basf Se | Triazole compounds, the use thereof and preparations containing these compounds |
| WO2010029003A1 (de) * | 2008-09-09 | 2010-03-18 | Basf Se | Triazolverbindungen, ihre verwendung sowie sie enthaltende mittel |
| BRPI0918230A2 (pt) * | 2008-09-09 | 2015-12-08 | Basf Se | composto, composição de composto ativo, método para controlar fungos fitopatogênicos, medicamento, e, método para preparar um antimicótico |
| JP2012502003A (ja) * | 2008-09-09 | 2012-01-26 | ビーエーエスエフ ソシエタス・ヨーロピア | トリアゾール化合物、その使用およびこれらの化合物を含む製剤 |
| JP2012501997A (ja) * | 2008-09-10 | 2012-01-26 | ビーエーエスエフ ソシエタス・ヨーロピア | 殺菌剤としてのイミダゾールおよびトリアゾール化合物 |
| WO2010028974A1 (de) * | 2008-09-10 | 2010-03-18 | Basf Se | Imidazol- und triazolverbindungen, ihre verwendung sowie sie enthaltende mittel |
| US20110172097A1 (en) * | 2008-09-22 | 2011-07-14 | Basf Se | Imidazole and Triazole Compounds, Their Use and Agents Containing The Same |
| BRPI0918548A2 (pt) * | 2008-09-22 | 2015-09-22 | Basf Se | composto, combinação de ingrediente ativo, semente, método para combater fungos fitopatogênicos, medicamentos, e, método para preparar um antimicótico. |
| US20110177950A1 (en) * | 2008-09-22 | 2011-07-21 | Basf Se | Imidazole and Triazole Compounds, Their Use and Agents Containing the Same |
| WO2010040717A1 (de) * | 2008-10-07 | 2010-04-15 | Basf Se | Triazol- und imidazolverbindungen, ihre verwendung sowie sie enthaltende mittel |
| MX2011003401A (es) * | 2008-10-07 | 2011-04-26 | Basf Se | Compuestos de triazol e imidazol, uso de los mismos y agentes que los contienen. |
| JP2013056832A (ja) * | 2010-01-12 | 2013-03-28 | Univ Of Tokyo | ストリゴラクトン生合成阻害剤 |
| WO2011110583A2 (en) * | 2010-03-10 | 2011-09-15 | Basf Se | Fungicidal mixtures comprising triazole derivatives |
| CN116082245B (zh) * | 2022-12-26 | 2024-11-22 | 武汉工程大学 | 一种恩康唑晶体及其制备方法和应用 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3658813A (en) * | 1970-01-13 | 1972-04-25 | Janssen Pharmaceutica Nv | 1-(beta-aryl-beta-(r-oxy)-ethyl)-imidazoles |
| 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 |
| DE2429513A1 (de) * | 1974-06-20 | 1976-01-15 | Bayer Ag | Eckige klammer auf 1-imidazolyl-(1) eckige klammer zu-eckige klammer auf 2-(4'(4''-chlorphenyl)-phenoxy eckige klammer zu -4,4-dimethyl-pentan-3-on und seine salze, ein verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| DE2431073A1 (de) * | 1974-06-28 | 1976-01-15 | Bayer Ag | Fungizides mittel |
| GB1535777A (en) * | 1975-08-26 | 1978-12-13 | Ici Ltd | Imidazole and 1,2,4-triazole compounds and their use as pesticides |
| DE2600799A1 (de) * | 1976-01-10 | 1977-07-14 | Bayer Ag | Acylierte triazolyl-0,n-acetale, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| GB1601453A (en) * | 1977-05-05 | 1981-10-28 | Ici Ltd | Triazole and imidazole derivatives useful in agriculture |
| DE2720949A1 (de) * | 1977-05-10 | 1978-11-23 | Bayer Ag | Azolylaether-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
| DE2738725A1 (de) * | 1977-08-27 | 1979-03-08 | Basf Ag | Azolylalkohole |
| JPS6053018B2 (ja) * | 1977-09-07 | 1985-11-22 | 住友化学工業株式会社 | アゾ−ル系化合物、その製造法および該化合物からなる殺菌剤 |
| DE2800544A1 (de) * | 1978-01-07 | 1979-07-19 | Bayer Ag | Carbamoyl-triazolyl-o,n-acetale, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| DE2832234A1 (de) * | 1978-07-21 | 1980-01-31 | Bayer Ag | Alpha -azolyl-keto-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| DE2842137A1 (de) * | 1978-09-28 | 1980-04-17 | Bayer Ag | Halogenierte 1-azolyl-1-fluorphenoxy- butan-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
-
1980
- 1980-05-19 DE DE19803019049 patent/DE3019049A1/de not_active Withdrawn
-
1981
- 1981-04-29 IL IL62749A patent/IL62749A/xx not_active IP Right Cessation
- 1981-04-29 US US06/258,789 patent/US4380546A/en not_active Expired - Lifetime
- 1981-04-29 CA CA000376539A patent/CA1163638A/en not_active Expired
- 1981-05-04 EP EP81103348A patent/EP0040350B1/de not_active Expired
- 1981-05-04 DE DE8181103348T patent/DE3160937D1/de not_active Expired
- 1981-05-04 AT AT81103348T patent/ATE4710T1/de not_active IP Right Cessation
- 1981-05-13 KR KR1019810001650A patent/KR850000494B1/ko not_active Expired
- 1981-05-15 PL PL1981231192A patent/PL127553B2/xx unknown
- 1981-05-15 BR BR8103029A patent/BR8103029A/pt unknown
- 1981-05-15 DD DD81229998A patent/DD158845A5/de not_active IP Right Cessation
- 1981-05-18 NZ NZ197127A patent/NZ197127A/xx unknown
- 1981-05-18 DK DK217681A patent/DK160937C/da not_active IP Right Cessation
- 1981-05-18 CS CS813671A patent/CS225838B2/cs unknown
- 1981-05-18 HU HU811407A patent/HU186884B/hu unknown
- 1981-05-18 ZA ZA00813281A patent/ZA813281B/xx unknown
- 1981-05-18 PH PH25647A patent/PH17873A/en unknown
- 1981-05-18 JP JP7362181A patent/JPS5716870A/ja active Granted
- 1981-05-18 AU AU70673/81A patent/AU539440B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| ZA813281B (en) | 1982-06-30 |
| NZ197127A (en) | 1983-04-12 |
| CS225838B2 (en) | 1984-02-13 |
| IL62749A (en) | 1984-11-30 |
| JPH0420911B2 (en, 2012) | 1992-04-07 |
| IL62749A0 (en) | 1981-06-29 |
| DE3019049A1 (de) | 1981-12-03 |
| US4380546A (en) | 1983-04-19 |
| DK217681A (da) | 1981-11-20 |
| KR850000494B1 (ko) | 1985-04-11 |
| KR830006225A (ko) | 1983-09-20 |
| EP0040350B1 (de) | 1983-09-21 |
| PL127553B2 (en) | 1983-11-30 |
| PL231192A2 (en, 2012) | 1982-01-18 |
| EP0040350A1 (de) | 1981-11-25 |
| JPS5716870A (en) | 1982-01-28 |
| AU7067381A (en) | 1981-11-26 |
| DK160937C (da) | 1991-10-21 |
| DK160937B (da) | 1991-05-06 |
| BR8103029A (pt) | 1982-02-09 |
| DD158845A5 (de) | 1983-02-09 |
| ATE4710T1 (de) | 1983-10-15 |
| DE3160937D1 (en) | 1983-10-27 |
| AU539440B2 (en) | 1984-09-27 |
| CA1163638A (en) | 1984-03-13 |
| PH17873A (en) | 1985-01-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 |