DE3018866A1 - 1-hydroxyethyl-azol-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als pflanzenwachstumsregulatoren und fungizide - Google Patents
1-hydroxyethyl-azol-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als pflanzenwachstumsregulatoren und fungizideInfo
- Publication number
- DE3018866A1 DE3018866A1 DE19803018866 DE3018866A DE3018866A1 DE 3018866 A1 DE3018866 A1 DE 3018866A1 DE 19803018866 DE19803018866 DE 19803018866 DE 3018866 A DE3018866 A DE 3018866A DE 3018866 A1 DE3018866 A1 DE 3018866A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- carbon atoms
- alkyl
- optionally substituted
- halogen
- 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- Withdrawn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
- 239000000417 fungicide Substances 0.000 title claims abstract description 9
- 239000005648 plant growth regulator Substances 0.000 title claims abstract description 8
- GNBNHUUABUEZGZ-UHFFFAOYSA-N 1-(1h-pyrrol-2-yl)ethanol Chemical compound CC(O)C1=CC=CN1 GNBNHUUABUEZGZ-UHFFFAOYSA-N 0.000 title claims 11
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 title description 2
- 239000002243 precursor Substances 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract description 31
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 24
- 239000002253 acid Substances 0.000 claims abstract description 19
- 229910052751 metal Chemical class 0.000 claims abstract description 18
- 239000002184 metal Chemical class 0.000 claims abstract description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 13
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 7
- 125000002071 phenylalkoxy group Chemical group 0.000 claims abstract description 7
- 125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 25
- 238000002360 preparation method Methods 0.000 claims description 22
- 230000008569 process Effects 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002924 oxiranes Chemical class 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 12
- 230000008635 plant growth Effects 0.000 claims description 10
- 125000001188 haloalkyl group Chemical group 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 239000003085 diluting agent Substances 0.000 claims description 7
- 230000001105 regulatory effect Effects 0.000 claims description 7
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 6
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 239000004606 Fillers/Extenders Substances 0.000 claims description 4
- 150000003851 azoles Chemical class 0.000 claims description 4
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 4
- 241000233866 Fungi Species 0.000 claims description 3
- DKWOHBPRFZIUQL-UHFFFAOYSA-N dimethyl-methylidene-oxo-$l^{6}-sulfane Chemical compound C[S+](C)([CH2-])=O DKWOHBPRFZIUQL-UHFFFAOYSA-N 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 239000013543 active substance Substances 0.000 claims description 2
- 235000001674 Agaricus brunnescens Nutrition 0.000 claims 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims 1
- 230000009105 vegetative growth Effects 0.000 abstract description 7
- 235000013339 cereals Nutrition 0.000 abstract description 6
- UDPGUMQDCGORJQ-UHFFFAOYSA-N (2-chloroethyl)phosphonic acid Chemical compound OP(O)(=O)CCCl UDPGUMQDCGORJQ-UHFFFAOYSA-N 0.000 abstract description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 abstract description 4
- 230000035613 defoliation Effects 0.000 abstract description 4
- 241000221787 Erysiphe Species 0.000 abstract description 3
- 244000068988 Glycine max Species 0.000 abstract description 3
- 235000010469 Glycine max Nutrition 0.000 abstract description 2
- 244000043261 Hevea brasiliensis Species 0.000 abstract description 2
- 230000002401 inhibitory effect Effects 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 abstract description 2
- 239000004816 latex Substances 0.000 abstract description 2
- 229920000126 latex Polymers 0.000 abstract description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 2
- 230000005070 ripening Effects 0.000 abstract description 2
- 230000004936 stimulating effect Effects 0.000 abstract description 2
- 230000009885 systemic effect Effects 0.000 abstract description 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 3
- 235000016068 Berberis vulgaris Nutrition 0.000 abstract 1
- 241000335053 Beta vulgaris Species 0.000 abstract 1
- 230000001133 acceleration Effects 0.000 abstract 1
- 230000002411 adverse Effects 0.000 abstract 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
- 230000006698 induction Effects 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 description 53
- 239000004480 active ingredient Substances 0.000 description 41
- 239000000460 chlorine Chemical group 0.000 description 40
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- 239000003630 growth substance Substances 0.000 description 20
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- 230000012010 growth Effects 0.000 description 17
- 239000000126 substance Substances 0.000 description 17
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 16
- -1 methoxy, methylthio Chemical group 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 239000003995 emulsifying agent Substances 0.000 description 10
- 238000003306 harvesting Methods 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 235000013399 edible fruits Nutrition 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000002689 soil Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000001309 chloro group Chemical group Cl* 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 230000009036 growth inhibition Effects 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 230000017066 negative regulation of growth Effects 0.000 description 6
- 240000005979 Hordeum vulgare Species 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 4
- 241000221785 Erysiphales Species 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- 235000007340 Hordeum vulgare Nutrition 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 235000021536 Sugar beet Nutrition 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- ZDZOJEUYRFMJHH-UHFFFAOYSA-N 2-tert-butyl-2-[(4-chlorophenoxy)methyl]oxirane Chemical compound C=1C=C(Cl)C=CC=1OCC1(C(C)(C)C)CO1 ZDZOJEUYRFMJHH-UHFFFAOYSA-N 0.000 description 3
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 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 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 244000061176 Nicotiana tabacum Species 0.000 description 3
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 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
- 238000011161 development Methods 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 230000002538 fungal effect Effects 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- 239000011435 rock Substances 0.000 description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- 244000099147 Ananas comosus Species 0.000 description 2
- 235000007119 Ananas comosus Nutrition 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
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- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
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- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
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- 230000009471 action Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- UHZZMRAGKVHANO-UHFFFAOYSA-M chlormequat chloride Chemical compound [Cl-].C[N+](C)(C)CCCl UHZZMRAGKVHANO-UHFFFAOYSA-M 0.000 description 2
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- 239000010949 copper Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 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 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
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- 125000000623 heterocyclic group Chemical group 0.000 description 2
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- 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
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- ANXKZXRDXAZQJT-UHFFFAOYSA-M methyl sulfate;trimethylsulfanium Chemical compound C[S+](C)C.COS([O-])(=O)=O ANXKZXRDXAZQJT-UHFFFAOYSA-M 0.000 description 2
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OCQPZTCGZAFWSG-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethyl-2-(1,2,4-triazol-1-ylmethyl)butan-2-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)COC1=CC=C(Cl)C=C1 OCQPZTCGZAFWSG-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Epoxy Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (82)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19803018866 DE3018866A1 (de) | 1980-05-16 | 1980-05-16 | 1-hydroxyethyl-azol-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als pflanzenwachstumsregulatoren und fungizide |
AU69456/81A AU542623B2 (en) | 1980-05-16 | 1981-04-13 | 1-hydroxyethyl-azole derivatives |
EP81103322A EP0040345B1 (de) | 1980-05-16 | 1981-05-02 | 1-Hydroxyethyl-azol-Derivate, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Pflanzenwachstumsregulatoren und Fungizide |
AT83101614T ATE18666T1 (de) | 1980-05-16 | 1981-05-02 | 1-hydroxyethyl-azol-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als pflanzenwachstumsregulatoren und fungizide. |
EP82108279A EP0072580B1 (de) | 1980-05-16 | 1981-05-02 | 1-Hydroxyethyl-azol-Derivate, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Pflanzenwachstumsregulatoren und Fungizide |
DE8282108279T DE3175929D1 (en) | 1980-05-16 | 1981-05-02 | 1-hydroxyethyl-azole derivatives, process for their preparation and their use as plant growth regulators and fungicides |
EP83101614A EP0087148B1 (de) | 1980-05-16 | 1981-05-02 | 1-Hydroxyethyl-azol-Derivate, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Pflanzenwachstumsregulatoren und Fungizide |
AT81103322T ATE8391T1 (de) | 1980-05-16 | 1981-05-02 | 1-hydroxyethyl-azol-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als pflanzenwachstumsregulatoren und fungizide. |
AT82108279T ATE25522T1 (de) | 1980-05-16 | 1981-05-02 | 1-hydroxyethyl-azol-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als pflanzenwachstumsregulatoren und fungizide. |
DE8181103322T DE3164696D1 (en) | 1980-05-16 | 1981-05-02 | 1-hydroxyethyl-azole derivatives, process for their preparation and their use in the regulation of plant growth and as fungicides |
DE8383101614T DE3174162D1 (en) | 1980-05-16 | 1981-05-02 | 1-hydroxyethyl-azol derivatives, process for their preparation and their use as plant growth regulators and fungicides |
PT72979A PT72979B (en) | 1980-05-16 | 1981-05-06 | Process for the preparation of 1-hydroxyethyl-azole derivatives having fungicidal and plant growth regulating effect |
PH25615A PH17636A (en) | 1980-05-16 | 1981-05-11 | 1-hydroxyethyl-azole derivatives and the use thereof as plant growth regulators and fungicides |
EG259/81A EG14836A (en) | 1980-05-16 | 1981-05-12 | 1-hydroxyethyl-azole derivatives,a process for their preparation and their use as plant growth regulators and fungicides |
NZ207096A NZ207096A (en) | 1980-05-16 | 1981-05-13 | Oxirane derivatives |
DK213081A DK158152C (da) | 1980-05-16 | 1981-05-13 | 1-hydroxyethyl-triazol-derivater samt deres anvendelse som plantevaekstregulatorer og fungicider |
DD81244788A DD205602A5 (de) | 1980-05-16 | 1981-05-13 | Pflanzenwachstumsregulierende und fungizide mittel |
IL62863A IL62863A (en) | 1980-05-16 | 1981-05-13 | 1-hydroxyethyl-1,2,4-triazole derivatives,their preparation and their use as plant growth regulators and fungicides |
NZ209126A NZ209126A (en) | 1980-05-16 | 1981-05-13 | 1-hydroxyethylimidazoles |
DD81229911A DD158847A5 (de) | 1980-05-16 | 1981-05-13 | Pflanzenwachstumsregulierende und fungizide mittel |
NZ197083A NZ197083A (en) | 1980-05-16 | 1981-05-13 | 1-hydroxyethyltriazoles;fungicidal and plant growth regulating compositions |
FI861230A FI861230A7 (fi) | 1980-05-16 | 1981-05-13 | 1-hydroksietyyliatsolijohdannaiset, niiden valmistusmenetelmä ja käyttö kasvien kasvua säätelevänä aineenaja sienimyrkkynä. |
IL75521A IL75521A (en) | 1980-05-16 | 1981-05-13 | Oxirane derivatives and their preparation |
IL75519A IL75519A (en) | 1980-05-16 | 1981-05-13 | 3-(1-imidazolylmethyl)and(1,2,4-triazol-1-ylmethyl)-1-substituted phenyl)-1-alken-3-ol derivatives,their preparation and their use as plant growth regulators and fungicides |
FI811472A FI73421C (fi) | 1980-05-16 | 1981-05-13 | 1-hydroxietylazolderivat, deras framstaellningsfoerfarande och anvaendning som vaextlighet reglerande medel samt som fungicider. |
NZ207097A NZ207097A (en) | 1980-05-16 | 1981-05-13 | 1-hydroxyethylazoles |
TR2532/84A TR22396A (tr) | 1980-05-16 | 1981-05-14 | 1-hidroksietil-azol tuerevleri,bunlarin ihzarina mahsus bir usul ve bunlarin bitki bueyuemesini duezenleyici maddeler ve fungisidler olarak kullanimi |
ES502234A ES8203859A1 (es) | 1980-05-16 | 1981-05-14 | Procedimiento para la obtencion de derivados de 1-hidroxie- tilazol, de efecto regulador del crecimiento de las plantas y fungicida |
TR2531/84A TR22400A (tr) | 1980-05-16 | 1981-05-14 | 1-hidroksietil-azol tuerevleri,bunlarin ihzarina mah sus bir usul ve bunlarin bitkibueyuemesini duezenleyici maddeler ve fungisidler olarak kullanimi |
TR2530/84A TR22691A (tr) | 1980-05-16 | 1981-05-14 | 1-hidroksietil-azol tuerevleri,bunlarin ihzarina mahsus bir usul ve bunlarin bitki bueyuemesini duezenleyici maddeler ve fungisidler olarak kullanimi |
CS843394A CS241499B2 (cs) | 1980-05-16 | 1981-05-14 | Prostředek k regulaci růstu rostlin a fungicidní prostředek a způsob výroby účinné složky |
CS813576A CS339581A2 (en) | 1980-05-16 | 1981-05-14 | Zpusob vyroby novych oxiranu |
CS843394A CS241498B2 (en) | 1980-05-16 | 1981-05-14 | Plant growth regulation agent and fungicide and active component production method |
TR22042A TR22042A (tr) | 1980-05-16 | 1981-05-14 | 1-hidroksietil-azol tuerevleri,bunlarin ihzarina mahsus bir usul ve bunlarin bitki bue yuemesini duezenleyici maddeler ve fungisidler olarak kullanimi |
GR64959A GR78229B (enrdf_load_stackoverflow) | 1980-05-16 | 1981-05-14 | |
CS813576A CS241482B2 (en) | 1980-05-16 | 1981-05-14 | Plant growth regulation agent and fungicide and method of active component production |
BRPI8103049-5A BR8103049A (pt) | 1980-05-16 | 1981-05-15 | Processo para a preparacao de derivados de 1-hidroxietil-azol, composicoes reguladoras de crescimento de plantas e fungicidas,processos para regular o crescimento de plantas e para a preparacao das composicoes e processo para a preparacao de oxiranos |
KR1019810001681A KR840001771B1 (ko) | 1980-05-16 | 1981-05-15 | 1-하이드록시에틸-아졸 유도체의 제조방법 |
PL1981231191A PL128206B1 (en) | 1980-05-16 | 1981-05-15 | Fungicide acting simultaneously as a plant growth control agent and method of obtaining derivatives of 1-hydroxyethyl-azole |
IE957/86A IE52451B1 (en) | 1980-05-16 | 1981-05-15 | 1-hydroxyethyl-azole derivatives,a process for their preparation and their use as plant growth regulators and fungicides |
IE1093/81A IE52450B1 (en) | 1980-05-16 | 1981-05-15 | 1-hydroxyethyl-azole derivatives,a process for their preparation and their use as plant growth regulators and fungicides |
HU842227A HU191671B (en) | 1980-05-16 | 1981-05-15 | Regulating increase and fungicide preparates consisting of -as reagent - 1-hydroxi-ethil-azol derivatives and process for producing of reagents |
OA57402A OA06809A (fr) | 1980-05-16 | 1981-05-15 | Dérivés 1-hydroxyéthyl-azoliques, leur procédé de production ainsi que leur utilisation comme substances de croissance des plantes et comme fongicides. |
ZA00813252A ZA813252B (en) | 1980-05-16 | 1981-05-15 | 1-hydroxyethyl-azole-derivatives,a process for their preparation and their use as plant growth regulators and fungicides |
HU842226A HU191148B (en) | 1980-05-16 | 1981-05-15 | Fungicide compositions stimulating carbon dioxide fixing activity of plants containing 1-hydroxy-ethyl-azol derivatives and process for producing the active agents |
IE958/86A IE52452B1 (en) | 1980-05-16 | 1981-05-15 | 1-hydroxyethyl-azole derivatives,a process for their preparation and their use as plant growth regulators and fungicides |
PL1981235518A PL133247B1 (en) | 1980-05-16 | 1981-05-15 | Process for manufacturing novel oxiranes |
AR285338A AR227310A1 (es) | 1980-05-16 | 1981-05-15 | Derivados de 1-hidroxi-1-(fenoximetil o feniletil)-2-azolil-etano,procedimiento para su obtencion y composiciones reguladoras del crecimiento de las plantas y fungicidas que los contienen |
HU811362A HU188092B (en) | 1980-05-16 | 1981-05-15 | Plant growth regulating and fungicide compositions containing 1-hydroxy-ethyl-triazola derivatives as active substances and process for preparing the active substances |
CA000617114A CA1341164C (en) | 1980-05-16 | 1981-05-15 | 1-hydroxyethyl-azole derivatives, a process for their preparation and their use as plant growth regulators and fungicides |
JP7240681A JPS5716868A (en) | 1980-05-16 | 1981-05-15 | 1-hydroxyethyl-azole derivative,manufacture and use |
AR289367A AR229527A1 (es) | 1980-05-16 | 1982-05-11 | Derivados de 1-hidroxi-1-estiril-2-azolil-etano,procedimiento para su obtencion,composiciones reguladoras del crecimiento de las plantas y fungicidas que los contienen,asi como nuevos oxiranos,sustancias iniciales para la preparacion de dichos derivados y un procedimiento para su obtencion |
PH28115A PH24322A (en) | 1980-05-16 | 1982-11-09 | 1-hydroxyethyl-azole derivatives,a process for their preparation and their use as plant growth regulators and fungicides |
PH28114A PH25843A (enrdf_load_stackoverflow) | 1980-05-16 | 1982-11-09 | |
FI823893A FI71732C (fi) | 1980-05-16 | 1982-11-12 | 1-hydroxietylazolderivat, deras framstaellningsfoerfarande och anvaendning som tillvaextregulerande medel foer vaexter och som fungicider. |
PH28986A PH25782A (en) | 1980-05-16 | 1983-05-31 | 1-hydroxyethyl-azole derivatives, the use thereof as plant growth regulators, fungicides |
US06/499,679 US4532341A (en) | 1980-05-16 | 1983-06-06 | Oxirane compounds |
US06/549,867 US4897107A (en) | 1980-05-16 | 1983-11-08 | 1-hydroxyethyl-azole compounds and agricultural compositions |
CS843395A CS241500B2 (cs) | 1980-05-16 | 1984-05-08 | Způseb výroby nových oxiranů |
US06/621,968 US4723984A (en) | 1980-05-16 | 1984-06-18 | 1-hydroxyethyl-azole compounds and agricultural compositions |
KR1019840004251A KR840001772B1 (ko) | 1980-05-16 | 1984-07-19 | 1-하이드록시에틸-아졸 유도체의 제조방법 |
KR1019840004250A KR840001752B1 (ko) | 1980-05-16 | 1984-07-19 | 1-하이드록시에틸-아졸 유도체의 제조방법 |
AU36292/84A AU556515B2 (en) | 1980-05-16 | 1984-12-04 | 1-hydroxyethyl-azole derivatives and intermediates |
AU36293/84A AU560022B2 (en) | 1980-05-16 | 1984-12-04 | Oxiranes |
US06/695,610 US4626595A (en) | 1980-05-16 | 1985-01-28 | Oxirane intermediates of 1-hydroxyethyl azole compounds |
DK054185A DK163507C (da) | 1980-05-16 | 1985-02-06 | 1-hydroxyethyl-imidazol-derivater, plantevaekstregulerende og fungicide midler indeholdende disse, fremgangsmaade til fremstilling af derivaterne samt deres anvendelse som plantevaekstregulatorer og fungicider |
DK54285A DK54285D0 (da) | 1980-05-16 | 1985-02-06 | Oxiraner samt fremgangsmaade til fremstilling deraf |
DK54385A DK54385A (da) | 1980-05-16 | 1985-02-06 | 1-hydroxyethyl-azol-derivater, fremgangsmaade til fremstilling deraf samt deres anvendelse som plantevaekstregulatorer og fungicider |
US06/732,194 US4789672A (en) | 1980-05-16 | 1985-05-08 | 1-hydroxyethyl-azole compounds and agricultural compositions |
US06/732,193 US4871390A (en) | 1980-05-16 | 1985-05-08 | 1-hydroxyethyl-azole compounds and agricultural compositions |
US06/732,191 US4911746A (en) | 1980-05-16 | 1985-05-08 | 1-hydroxyethyl-azole compounds and agricultural compositions |
KE3529A KE3529A (en) | 1980-05-16 | 1985-05-21 | 1-hydroxyethyl-azole derivatives,a process for their preparation and their use as plant growth regulators and fungicides |
IL75521A IL75521A0 (en) | 1980-05-16 | 1985-06-14 | Oxirane derivatives and their preparation |
IL75520A IL75520A0 (en) | 1980-05-16 | 1985-06-14 | 1-hydroxyethyl-azole derivatives,their preparation and their use as plant growth regulators and fungicides |
IL75519A IL75519A0 (en) | 1980-05-16 | 1985-06-14 | 1-hydroxyethyl-azole derivatives,their preparation and their use as plant growth regulators and fungicides |
FI861206A FI75817C (fi) | 1980-05-16 | 1986-03-21 | Oxiranderivat och foerfarande foer deras framstaellning. |
FI861229A FI76329C (fi) | 1980-05-16 | 1986-03-24 | Oxiranderivat och foerfarande foer deras framstaellning. |
US07/058,479 US4904298A (en) | 1980-05-16 | 1987-06-05 | 1-Hydroxyethyl-azole compounds and agricultural compositions |
JP1302307A JPH02167273A (ja) | 1980-05-16 | 1989-11-22 | オキシラン類 |
JP1302308A JPH02167270A (ja) | 1980-05-16 | 1989-11-22 | 1―ヒドロキシエチル―アゾール誘導体 |
NL971022C NL971022I2 (nl) | 1980-05-16 | 1997-07-24 | 1-Hydroxyethylazoolderivaten, werkwijze ter bereiding daarvan, alsmede de toepassing daarvan als middelen voor het regelen van de plantengroei en fungiciden. |
CA000377689A CA1341521C (en) | 1980-05-16 | 2005-08-15 | 1-hydroxyethyl-azole derivatives, a process for their preparation and their use as plant growth regulators and fungicides |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19803018866 DE3018866A1 (de) | 1980-05-16 | 1980-05-16 | 1-hydroxyethyl-azol-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als pflanzenwachstumsregulatoren und fungizide |
Publications (1)
Publication Number | Publication Date |
---|---|
DE3018866A1 true DE3018866A1 (de) | 1981-11-26 |
Family
ID=6102658
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19803018866 Withdrawn DE3018866A1 (de) | 1980-05-16 | 1980-05-16 | 1-hydroxyethyl-azol-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als pflanzenwachstumsregulatoren und fungizide |
Country Status (7)
Country | Link |
---|---|
JP (1) | JPS5716868A (enrdf_load_stackoverflow) |
KR (3) | KR840001771B1 (enrdf_load_stackoverflow) |
CS (3) | CS339581A2 (enrdf_load_stackoverflow) |
DE (1) | DE3018866A1 (enrdf_load_stackoverflow) |
PH (1) | PH24322A (enrdf_load_stackoverflow) |
PL (2) | PL133247B1 (enrdf_load_stackoverflow) |
ZA (1) | ZA813252B (enrdf_load_stackoverflow) |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4507140A (en) * | 1980-11-19 | 1985-03-26 | Imperial Chemical Industries Plc | Triazole and imidazole compounds useful as fungicides and plant growth regulators |
US4584308A (en) * | 1982-12-09 | 1986-04-22 | Bayer Aktiengesellschaft | Substituted hydroxyalkyl-azole fungicidal agents, their preparation and their use |
EP0141205A3 (en) * | 1983-09-26 | 1986-12-10 | Bayer Ag | Hydroxyethylazolyl oxime derivatives |
US4631288A (en) * | 1983-09-23 | 1986-12-23 | Bayer Aktiengesellschaft | Triazolylmethyl-pyridyloxymethyl-carbinol fungicides |
US4632932A (en) * | 1982-11-15 | 1986-12-30 | Bayer Aktiengesellschaft | Antimycotic agents |
US4639462A (en) * | 1982-11-15 | 1987-01-27 | Bayer Aktiengesellschaft | Heterocyclo-hydroxyalkyl-azolyl derivatives and use as fungicides |
US4818762A (en) * | 1982-11-15 | 1989-04-04 | Bayer Aktiengesellschaft | Fungicidal novel hydroxyalkynyl-azolyl derivatives |
EP0198191B1 (de) * | 1985-03-13 | 1989-09-06 | Bayer Ag | Piperazinylmethyl-1,2,4-triazolylmethyl-carbinole |
US4868196A (en) * | 1982-01-27 | 1989-09-19 | Bayer Aktiengesellschaft | Ether derivatives of substituted 1-hydroxyalkyl- azoles as fungicides and plant growth regulators |
EP2298076A1 (de) | 1998-06-10 | 2011-03-23 | Bayer CropScience AG | Mittel zur Bekämpfung von Pflanzenschädlingen |
WO2018115319A2 (en) | 2016-12-23 | 2018-06-28 | Helmholtz Zentrum München - Deutsches Forschungszentrum für Gesundheit und Umwelt (GmbH) | Inhibitors of cytochrome p450 family 7 subfamily b member 1 (cyp7b1) for use in treating diseases |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ZA817473B (en) * | 1980-11-19 | 1982-10-27 | Ici Plc | Triazole and imidazole compounds |
JPS57165370A (en) * | 1981-03-18 | 1982-10-12 | Ici Ltd | Triazole or imidazole compounds, manufacture and fungicidal or plant growth regulant agent |
DE3232647A1 (de) * | 1982-09-02 | 1984-03-08 | Bayer Ag, 5090 Leverkusen | Substituierte tert.-butanol-derivate, verfahren zu ihrer herstellung und diese enthaltende antimykotische mittel |
DE3440112A1 (de) * | 1984-11-02 | 1986-05-07 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung optisch aktiver azolylcarbinol-derivate |
DE3621494A1 (de) * | 1986-06-27 | 1988-01-07 | Bayer Ag | Verwendung von 1-aryl-3-hydroxy-3-alkyl-4-(1,2,4-triazol-1-yl) -butan-derivaten als mikrobizide fuer den materialschutz |
JPH0625140B2 (ja) | 1986-11-10 | 1994-04-06 | 呉羽化学工業株式会社 | 新規アゾール誘導体、その製造方法及び該誘導体の農園芸用薬剤 |
JPH0511263A (ja) * | 1991-07-06 | 1993-01-19 | Ii & S:Kk | Lcdパネル用tab接続装置 |
GB9202378D0 (en) * | 1992-02-05 | 1992-03-18 | Sandoz Ltd | Inventions relating to fungicidal compositions |
JP2008194697A (ja) * | 2008-05-26 | 2008-08-28 | Daicen Membrane Systems Ltd | 分離膜モジュール |
EP2451784A1 (de) * | 2009-07-08 | 2012-05-16 | Bayer CropScience AG | Phenyl(oxy/thio)alkanol-derivate |
KR20120046242A (ko) * | 2009-07-08 | 2012-05-09 | 바이엘 크롭사이언스 아게 | 치환된 페닐(옥시/티오)알칸올 유도체 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2737489A1 (de) * | 1976-08-19 | 1978-02-23 | Ici Ltd | Triazol- und imidazolverbindungen |
DE2736122A1 (de) * | 1977-08-11 | 1979-02-22 | Basf Ag | Fungizide |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4123542A (en) * | 1977-01-19 | 1978-10-31 | Syntex (U.S.A.) Inc. | Derivatives of N-alkyl imidazoles |
-
1980
- 1980-05-16 DE DE19803018866 patent/DE3018866A1/de not_active Withdrawn
-
1981
- 1981-05-14 CS CS813576A patent/CS339581A2/cs unknown
- 1981-05-14 CS CS813576A patent/CS241482B2/cs unknown
- 1981-05-14 CS CS843394A patent/CS241498B2/cs unknown
- 1981-05-15 JP JP7240681A patent/JPS5716868A/ja active Granted
- 1981-05-15 ZA ZA00813252A patent/ZA813252B/xx unknown
- 1981-05-15 PL PL1981235518A patent/PL133247B1/pl unknown
- 1981-05-15 KR KR1019810001681A patent/KR840001771B1/ko not_active Expired
- 1981-05-15 PL PL1981231191A patent/PL128206B1/pl unknown
-
1982
- 1982-11-09 PH PH28115A patent/PH24322A/en unknown
-
1984
- 1984-07-19 KR KR1019840004250A patent/KR840001752B1/ko not_active Expired
- 1984-07-19 KR KR1019840004251A patent/KR840001772B1/ko not_active Expired
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2737489A1 (de) * | 1976-08-19 | 1978-02-23 | Ici Ltd | Triazol- und imidazolverbindungen |
DE2736122A1 (de) * | 1977-08-11 | 1979-02-22 | Basf Ag | Fungizide |
Non-Patent Citations (1)
Title |
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C.A., 90, 147016b, 1979 * |
Cited By (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4845250A (en) * | 1980-11-19 | 1989-07-04 | Imperial Chemical Industries Plc | Triazole and imidazole compounds |
US4507140A (en) * | 1980-11-19 | 1985-03-26 | Imperial Chemical Industries Plc | Triazole and imidazole compounds useful as fungicides and plant growth regulators |
US4868196A (en) * | 1982-01-27 | 1989-09-19 | Bayer Aktiengesellschaft | Ether derivatives of substituted 1-hydroxyalkyl- azoles as fungicides and plant growth regulators |
US4632932A (en) * | 1982-11-15 | 1986-12-30 | Bayer Aktiengesellschaft | Antimycotic agents |
US4639462A (en) * | 1982-11-15 | 1987-01-27 | Bayer Aktiengesellschaft | Heterocyclo-hydroxyalkyl-azolyl derivatives and use as fungicides |
US4818762A (en) * | 1982-11-15 | 1989-04-04 | Bayer Aktiengesellschaft | Fungicidal novel hydroxyalkynyl-azolyl derivatives |
US4584308A (en) * | 1982-12-09 | 1986-04-22 | Bayer Aktiengesellschaft | Substituted hydroxyalkyl-azole fungicidal agents, their preparation and their use |
US4631288A (en) * | 1983-09-23 | 1986-12-23 | Bayer Aktiengesellschaft | Triazolylmethyl-pyridyloxymethyl-carbinol fungicides |
EP0141205A3 (en) * | 1983-09-26 | 1986-12-10 | Bayer Ag | Hydroxyethylazolyl oxime derivatives |
EP0198191B1 (de) * | 1985-03-13 | 1989-09-06 | Bayer Ag | Piperazinylmethyl-1,2,4-triazolylmethyl-carbinole |
EP2298076A1 (de) | 1998-06-10 | 2011-03-23 | Bayer CropScience AG | Mittel zur Bekämpfung von Pflanzenschädlingen |
EP2298077A1 (de) | 1998-06-10 | 2011-03-23 | Bayer CropScience AG | Mittel zur Bekämpfung von Pflanzenschädlingen |
EP2301353A1 (de) | 1998-06-10 | 2011-03-30 | Bayer CropScience AG | Mittel zur Bekämpfung von Pflanzenschädlingen |
EP2305031A1 (de) | 1998-06-10 | 2011-04-06 | Bayer CropScience AG | Mittel zur Bekämpfung von Pflanzenschädlingen |
EP2305035A1 (de) | 1998-06-10 | 2011-04-06 | Bayer CropScience AG | Mittel zur Bekämpfung von Pflanzenschädlingen |
WO2018115319A2 (en) | 2016-12-23 | 2018-06-28 | Helmholtz Zentrum München - Deutsches Forschungszentrum für Gesundheit und Umwelt (GmbH) | Inhibitors of cytochrome p450 family 7 subfamily b member 1 (cyp7b1) for use in treating diseases |
Also Published As
Publication number | Publication date |
---|---|
PL231191A1 (enrdf_load_stackoverflow) | 1982-08-16 |
CS241498B2 (en) | 1986-03-13 |
PL133247B1 (en) | 1985-05-31 |
PL235518A1 (enrdf_load_stackoverflow) | 1982-11-22 |
KR840001771B1 (ko) | 1984-10-19 |
KR830006239A (ko) | 1983-09-20 |
ZA813252B (en) | 1982-05-26 |
CS357681A2 (en) | 1985-07-16 |
JPH0224823B2 (enrdf_load_stackoverflow) | 1990-05-30 |
KR840001752B1 (ko) | 1984-10-19 |
KR840001772B1 (ko) | 1984-10-19 |
JPS5716868A (en) | 1982-01-28 |
CS339581A2 (en) | 1985-07-16 |
PH24322A (en) | 1990-05-29 |
PL128206B1 (en) | 1984-01-31 |
CS241482B2 (en) | 1986-03-13 |
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