DE3048266A1 - Substituierte 1-azolyl-butan-2one, verfahren zu ihrer herstellung und ihre verwendung als fungizide sowie als zwischenprodukte - Google Patents
Substituierte 1-azolyl-butan-2one, verfahren zu ihrer herstellung und ihre verwendung als fungizide sowie als zwischenprodukteInfo
- Publication number
- DE3048266A1 DE3048266A1 DE19803048266 DE3048266A DE3048266A1 DE 3048266 A1 DE3048266 A1 DE 3048266A1 DE 19803048266 DE19803048266 DE 19803048266 DE 3048266 A DE3048266 A DE 3048266A DE 3048266 A1 DE3048266 A1 DE 3048266A1
- Authority
- DE
- Germany
- Prior art keywords
- carbon atoms
- optionally substituted
- alkyl
- formula
- stands
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- SWMBAEIZFIXVTB-UHFFFAOYSA-N 1-(1h-pyrrol-2-yl)butan-2-one Chemical class CCC(=O)CC1=CC=CN1 SWMBAEIZFIXVTB-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 238000000034 method Methods 0.000 title claims description 39
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 239000000417 fungicide Substances 0.000 title claims description 7
- 239000013067 intermediate product Substances 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 55
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 49
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 29
- 239000001257 hydrogen Substances 0.000 claims abstract description 28
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- 239000002253 acid Substances 0.000 claims abstract description 21
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 20
- 125000001424 substituent group Chemical group 0.000 claims abstract description 15
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 15
- 229910052751 metal Chemical class 0.000 claims abstract description 13
- 239000002184 metal Chemical class 0.000 claims abstract description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 9
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims abstract description 8
- 150000002367 halogens Chemical class 0.000 claims abstract description 8
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 7
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims abstract description 7
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
- 239000001301 oxygen Substances 0.000 claims abstract description 7
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims abstract description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000001401 1,2,4-triazol-4-yl group Chemical group N=1N=C([H])N([*])C=1[H] 0.000 claims abstract description 5
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 4
- 125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 3
- 239000000460 chlorine Substances 0.000 claims description 157
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 91
- 150000001875 compounds Chemical class 0.000 claims description 49
- -1 methyl cyclohexyl Chemical group 0.000 claims description 24
- 238000002360 preparation method Methods 0.000 claims description 13
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 239000011230 binding agent Substances 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 5
- 239000002168 alkylating agent Substances 0.000 claims description 5
- 229940100198 alkylating agent Drugs 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- 239000004606 Fillers/Extenders Substances 0.000 claims description 4
- 241000233866 Fungi Species 0.000 claims description 4
- 150000003851 azoles Chemical class 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000005283 haloketone group Chemical group 0.000 claims description 3
- 239000003444 phase transfer catalyst Substances 0.000 claims description 3
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 3
- 241000251730 Chondrichthyes Species 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 claims description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 abstract description 9
- 150000002431 hydrogen Chemical class 0.000 abstract description 9
- 125000005843 halogen group Chemical group 0.000 abstract description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 3
- 125000003545 alkoxy group Chemical group 0.000 abstract description 2
- 125000004414 alkyl thio group Chemical group 0.000 abstract description 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract description 2
- 125000004663 dialkyl amino group Chemical group 0.000 abstract description 2
- 125000004438 haloalkoxy group Chemical group 0.000 abstract description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 abstract 1
- 239000005864 Sulphur Chemical group 0.000 abstract 1
- 125000006193 alkinyl group Chemical group 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- 239000000203 mixture Substances 0.000 description 23
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 239000002904 solvent Substances 0.000 description 21
- 241000196324 Embryophyta Species 0.000 description 19
- 239000004480 active ingredient Substances 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
- 229910052938 sodium sulfate Inorganic materials 0.000 description 11
- 235000011152 sodium sulphate Nutrition 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- 238000009835 boiling Methods 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 241000221785 Erysiphales Species 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 206010061217 Infestation Diseases 0.000 description 8
- 239000003995 emulsifying agent Substances 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 238000009472 formulation Methods 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 240000005979 Hordeum vulgare Species 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 235000007340 Hordeum vulgare Nutrition 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 230000001681 protective effect Effects 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 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 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
- 241000220225 Malus Species 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 125000002877 alkyl aryl group Chemical group 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 230000000855 fungicidal effect Effects 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 125000000468 ketone group Chemical group 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 239000007800 oxidant agent Substances 0.000 description 4
- 238000005554 pickling Methods 0.000 description 4
- 229920000151 polyglycol Polymers 0.000 description 4
- 239000010695 polyglycol Substances 0.000 description 4
- 239000011814 protection agent Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- DYAWMXSWDGPGOI-UHFFFAOYSA-N 4-hydroxy-3,3-dimethylbutan-2-one Chemical compound CC(=O)C(C)(C)CO DYAWMXSWDGPGOI-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
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241001480061 Blumeria graminis Species 0.000 description 3
- 241000221787 Erysiphe Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 206010037888 Rash pustular Diseases 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 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
- 239000012141 concentrate Substances 0.000 description 3
- 238000002845 discoloration Methods 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 150000008282 halocarbons Chemical class 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000011081 inoculation Methods 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 208000029561 pustule Diseases 0.000 description 3
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- 239000007787 solid Substances 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 150000003852 triazoles Chemical class 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- YJKMBNPDFLFHLJ-UHFFFAOYSA-N 1-bromo-4-(4-chlorophenyl)sulfanyl-3,3-dimethylbutan-2-one Chemical compound BrCC(=O)C(C)(C)CSC1=CC=C(Cl)C=C1 YJKMBNPDFLFHLJ-UHFFFAOYSA-N 0.000 description 2
- JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 description 2
- FMWWRALTYIWZEB-UHFFFAOYSA-N 3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound CC(C)(C)C(=O)CN1C=NC=N1 FMWWRALTYIWZEB-UHFFFAOYSA-N 0.000 description 2
- YLLXPAMYBJZDGK-UHFFFAOYSA-N 3-(4-chlorophenoxy)-3-methylbutan-2-one Chemical compound CC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 YLLXPAMYBJZDGK-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- XHCWDDGZFBAXRT-UHFFFAOYSA-N 3-bromo-3-methylbutan-2-one Chemical compound CC(=O)C(C)(C)Br XHCWDDGZFBAXRT-UHFFFAOYSA-N 0.000 description 2
- LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
- KINCUWTUXNNMJG-UHFFFAOYSA-N 4-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound C1=NC=NN1CC(=O)C(C)(C)COC1=CC=C(Cl)C=C1 KINCUWTUXNNMJG-UHFFFAOYSA-N 0.000 description 2
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- 241000895523 Blumeria graminis f. sp. hordei Species 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-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
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- 241000896242 Podosphaera Species 0.000 description 2
- 241001337928 Podosphaera leucotricha Species 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
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- 150000003460 sulfonic acids Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 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
- 230000008016 vaporization Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—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
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/16—Saturated compounds containing keto groups bound to acyclic carbon atoms 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)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Analysing Materials By The Use Of Radiation (AREA)
- Coloring (AREA)
Priority Applications (19)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803048266 DE3048266A1 (de) | 1980-12-20 | 1980-12-20 | Substituierte 1-azolyl-butan-2one, verfahren zu ihrer herstellung und ihre verwendung als fungizide sowie als zwischenprodukte |
| PT74109A PT74109B (pt) | 1980-12-20 | 1981-12-10 | Process for the preparation of a fungicidal composition contai-ning substituted 1-azolyl-butan-2-ones |
| AT81110365T ATE18213T1 (de) | 1980-12-20 | 1981-12-11 | Substituierte 1-azolyl-butan-2-one, verfahren zu ihrer herstellung und ihre verwendung als fungizide sowie als zwischenprodukte. |
| EP81110365A EP0054865B1 (de) | 1980-12-20 | 1981-12-11 | Substituierte 1-Azolyl-butan-2-one, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide sowie als Zwischenprodukte |
| DE8181110365T DE3173926D1 (en) | 1980-12-20 | 1981-12-11 | Substituted 1-azolyl-butan-2-ones, their preparation and their application as fungicides as well as intermediates |
| IL64572A IL64572A (en) | 1980-12-20 | 1981-12-17 | Substituted 1-azolyl-butan-2-ones,their preparation and their use as fungicides and as intermediate products |
| ZA818757A ZA818757B (en) | 1980-12-20 | 1981-12-18 | Substituted 1-azolyl-butan-2-ones,processes for their preparation and their use as fungicides and as intermediate products |
| CA000392632A CA1178587A (en) | 1980-12-20 | 1981-12-18 | Substituted 1-azolyl-butan-2-ones, processes for their preparation and their use as fungicides and as intermediate products |
| ES508134A ES508134A0 (es) | 1980-12-20 | 1981-12-18 | Procedimiento para la obtencion de 1-azolil-butan-2-onas. |
| BR8108274A BR8108274A (pt) | 1980-12-20 | 1981-12-18 | Processo para a preparacao de 1-azolilbutano-2-onas,substituidas,composicoes fungicidas,processo para o combate afungos e para a preparacao de composicoes |
| AR287857A AR228764A1 (es) | 1980-12-20 | 1981-12-18 | 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 |
| JP56203841A JPS57128676A (en) | 1980-12-20 | 1981-12-18 | Substituted 1-azolyl-butane-2-ones, manufacture and use as plant protecting agent and intermediate product |
| HU813865A HU189549B (en) | 1980-12-20 | 1981-12-18 | Fungicide compositions containing 1-azolyl-butan-2-one derivatives as active substances and process for preparing the active substances |
| GR66841A GR77634B (OSRAM) | 1980-12-20 | 1981-12-18 | |
| DK563081A DK563081A (da) | 1980-12-20 | 1981-12-18 | Substituerede 1-azolyl-butan-2-oner fremgangsmaade til fremstilling heraf samt deres anvendelse som fungicider samt som mellemprodukter |
| EG759/81A EG15306A (en) | 1980-12-20 | 1981-12-20 | Substituted 1-azolyl-butan-2-ones,processes for their preparation and their use as fungicides and as intermediates products |
| AU78690/81A AU547689B2 (en) | 1980-12-20 | 1981-12-21 | Substituted 1-azolyl-butan-2-ones, their starting compounds and their intermediates |
| US06/481,615 US4549900A (en) | 1980-12-20 | 1983-04-04 | Combating fungi with substituted 1-azolyl-butan-2-ones and -2-ols |
| US07/169,912 US4904297A (en) | 1980-12-20 | 1988-03-18 | Combating fungi with substituted 1-azolyl-butan-2-ones and -2-ols |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803048266 DE3048266A1 (de) | 1980-12-20 | 1980-12-20 | Substituierte 1-azolyl-butan-2one, verfahren zu ihrer herstellung und ihre verwendung als fungizide sowie als zwischenprodukte |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3048266A1 true DE3048266A1 (de) | 1982-07-29 |
Family
ID=6119802
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803048266 Withdrawn DE3048266A1 (de) | 1980-12-20 | 1980-12-20 | Substituierte 1-azolyl-butan-2one, verfahren zu ihrer herstellung und ihre verwendung als fungizide sowie als zwischenprodukte |
| DE8181110365T Expired DE3173926D1 (en) | 1980-12-20 | 1981-12-11 | Substituted 1-azolyl-butan-2-ones, their preparation and their application as fungicides as well as intermediates |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8181110365T Expired DE3173926D1 (en) | 1980-12-20 | 1981-12-11 | Substituted 1-azolyl-butan-2-ones, their preparation and their application as fungicides as well as intermediates |
Country Status (15)
| Country | Link |
|---|---|
| EP (1) | EP0054865B1 (OSRAM) |
| JP (1) | JPS57128676A (OSRAM) |
| AT (1) | ATE18213T1 (OSRAM) |
| AU (1) | AU547689B2 (OSRAM) |
| BR (1) | BR8108274A (OSRAM) |
| CA (1) | CA1178587A (OSRAM) |
| DE (2) | DE3048266A1 (OSRAM) |
| DK (1) | DK563081A (OSRAM) |
| EG (1) | EG15306A (OSRAM) |
| ES (1) | ES508134A0 (OSRAM) |
| GR (1) | GR77634B (OSRAM) |
| HU (1) | HU189549B (OSRAM) |
| IL (1) | IL64572A (OSRAM) |
| PT (1) | PT74109B (OSRAM) |
| ZA (1) | ZA818757B (OSRAM) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0129798A1 (de) * | 1983-06-23 | 1985-01-02 | BASF Aktiengesellschaft | Fungizide Azolverbindungen, ihre Herstellung und Verwendung |
| US4877446A (en) * | 1987-01-31 | 1989-10-31 | Bayer Aktiengesellschaft | Pesticides based on pyrimidine derivatives |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| DE3229274A1 (de) * | 1982-08-05 | 1984-02-09 | Bayer Ag, 5090 Leverkusen | Substituierte azolylvinyl-ketone und -carbinole |
| DE3229273A1 (de) * | 1982-08-05 | 1984-02-09 | Bayer Ag, 5090 Leverkusen | Substituierte azolylallyl-ketone und -carbinole |
| 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 |
| DE3329128A1 (de) * | 1983-08-11 | 1985-02-28 | Bayer Ag, 5090 Leverkusen | 3-cycloalkyl-1-(1,3-dioxan-5-yl)-2-(1,2,4-triazol-1-yl)-propan-1-one und -propan-1-ole |
| DE3336861A1 (de) * | 1983-10-11 | 1985-04-25 | Bayer Ag, 5090 Leverkusen | Azolyl-tetrahydrofuran-2-yliden-methan-derivate |
| DE3434158A1 (de) * | 1984-09-18 | 1986-03-20 | Bayer Ag, 5090 Leverkusen | Substituierte 1,1-bis-azolyl-butan-2-one und -ole |
| DE3725397A1 (de) * | 1987-07-31 | 1989-02-09 | Bayer Ag | 1,4-disubstituierte 1-azolyl-3,3-dimethylbutan-derivate |
| DE3813253A1 (de) * | 1988-04-20 | 1989-11-02 | Bayer Ag | Substituierte triazolylmethylcarbinole |
| FR2686084B1 (fr) * | 1992-01-10 | 1995-12-22 | Bioprojet Soc Civ | Nouveaux derives de l'imidazole, leur preparation et leurs applications therapeutiques. |
| USRE37303E1 (en) * | 1992-01-10 | 2001-07-31 | Institut National Del La Sante Et De La Recherche Medicale | Imidazole compounds and their therapeutic applications |
| DE4222542A1 (de) * | 1992-07-09 | 1994-01-13 | Bayer Ag | Triazolyl-butan-Derivate |
| DE4222541A1 (de) * | 1992-07-09 | 1994-01-13 | Bayer Ag | Triazolyl-butan-Derivate |
| DE4318916A1 (de) * | 1993-06-07 | 1994-12-08 | Bayer Ag | Cyclobutylazole |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| DE2951164A1 (de) * | 1979-12-19 | 1981-07-16 | Bayer Ag, 5090 Leverkusen | Substituierte triazolylmethyl-tert.-butyl-ketone, verfahren zu ihrer herstellung und ihre verwendung als pflanzenschutzmittel sowie als zwischenprodukte |
-
1980
- 1980-12-20 DE DE19803048266 patent/DE3048266A1/de not_active Withdrawn
-
1981
- 1981-12-10 PT PT74109A patent/PT74109B/pt unknown
- 1981-12-11 AT AT81110365T patent/ATE18213T1/de not_active IP Right Cessation
- 1981-12-11 EP EP81110365A patent/EP0054865B1/de not_active Expired
- 1981-12-11 DE DE8181110365T patent/DE3173926D1/de not_active Expired
- 1981-12-17 IL IL64572A patent/IL64572A/xx unknown
- 1981-12-18 JP JP56203841A patent/JPS57128676A/ja active Pending
- 1981-12-18 ZA ZA818757A patent/ZA818757B/xx unknown
- 1981-12-18 ES ES508134A patent/ES508134A0/es active Granted
- 1981-12-18 BR BR8108274A patent/BR8108274A/pt unknown
- 1981-12-18 GR GR66841A patent/GR77634B/el unknown
- 1981-12-18 DK DK563081A patent/DK563081A/da not_active Application Discontinuation
- 1981-12-18 HU HU813865A patent/HU189549B/hu not_active IP Right Cessation
- 1981-12-18 CA CA000392632A patent/CA1178587A/en not_active Expired
- 1981-12-20 EG EG759/81A patent/EG15306A/xx active
- 1981-12-21 AU AU78690/81A patent/AU547689B2/en not_active Ceased
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0129798A1 (de) * | 1983-06-23 | 1985-01-02 | BASF Aktiengesellschaft | Fungizide Azolverbindungen, ihre Herstellung und Verwendung |
| US4877446A (en) * | 1987-01-31 | 1989-10-31 | Bayer Aktiengesellschaft | Pesticides based on pyrimidine derivatives |
| US4939155A (en) * | 1987-01-31 | 1990-07-03 | Bayer Aktiengesellschaft | Pesticides based on pyrimidine derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| BR8108274A (pt) | 1982-10-05 |
| EP0054865A1 (de) | 1982-06-30 |
| EP0054865B1 (de) | 1986-02-26 |
| AU547689B2 (en) | 1985-10-31 |
| GR77634B (OSRAM) | 1984-09-25 |
| EG15306A (en) | 1986-09-30 |
| JPS57128676A (en) | 1982-08-10 |
| PT74109B (pt) | 1983-05-16 |
| IL64572A (en) | 1985-05-31 |
| ZA818757B (en) | 1982-11-24 |
| IL64572A0 (en) | 1982-03-31 |
| AU7869081A (en) | 1982-07-01 |
| ATE18213T1 (de) | 1986-03-15 |
| ES8300712A1 (es) | 1982-11-01 |
| DE3173926D1 (en) | 1986-04-03 |
| CA1178587A (en) | 1984-11-27 |
| ES508134A0 (es) | 1982-11-01 |
| HU189549B (en) | 1986-07-28 |
| PT74109A (en) | 1982-01-01 |
| DK563081A (da) | 1982-06-21 |
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