KR840001771B1 - 1-하이드록시에틸-아졸 유도체의 제조방법 - Google Patents
1-하이드록시에틸-아졸 유도체의 제조방법 Download PDFInfo
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- KR840001771B1 KR840001771B1 KR1019810001681A KR810001681A KR840001771B1 KR 840001771 B1 KR840001771 B1 KR 840001771B1 KR 1019810001681 A KR1019810001681 A KR 1019810001681A KR 810001681 A KR810001681 A KR 810001681A KR 840001771 B1 KR840001771 B1 KR 840001771B1
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- South Korea
- Prior art keywords
- growth
- carbon atoms
- plants
- alkyl
- general formula
- Prior art date
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- GNBNHUUABUEZGZ-UHFFFAOYSA-N 1-(1h-pyrrol-2-yl)ethanol Chemical class CC(O)C1=CC=CN1 GNBNHUUABUEZGZ-UHFFFAOYSA-N 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title description 7
- 238000000034 method Methods 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 12
- 229910052751 metal Inorganic materials 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 96
- 241000196324 Embryophyta Species 0.000 description 55
- 239000000203 mixture Substances 0.000 description 30
- -1 alkyl radical Chemical group 0.000 description 28
- 230000012010 growth Effects 0.000 description 25
- 239000003630 growth substance Substances 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000000243 solution Substances 0.000 description 12
- 239000003995 emulsifying agent Substances 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- 238000009472 formulation Methods 0.000 description 10
- 230000009036 growth inhibition Effects 0.000 description 10
- 230000008635 plant growth Effects 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 235000013339 cereals Nutrition 0.000 description 8
- 238000003306 harvesting Methods 0.000 description 8
- 241000233866 Fungi Species 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 235000015097 nutrients Nutrition 0.000 description 7
- 239000002689 soil Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 6
- 240000005979 Hordeum vulgare Species 0.000 description 6
- 235000007340 Hordeum vulgare Nutrition 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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 5
- 244000068988 Glycine max Species 0.000 description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 5
- 230000000844 anti-bacterial effect Effects 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 238000012217 deletion Methods 0.000 description 5
- 230000037430 deletion Effects 0.000 description 5
- 235000013399 edible fruits Nutrition 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 208000015181 infectious disease Diseases 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 229910052725 zinc Inorganic materials 0.000 description 5
- 239000011701 zinc Substances 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 241000221785 Erysiphales Species 0.000 description 4
- 235000010469 Glycine max Nutrition 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 230000033228 biological regulation Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 239000005648 plant growth regulator Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000007858 starting material Substances 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
- 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
- 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
- 229920001213 Polysorbate 20 Polymers 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- UHZZMRAGKVHANO-UHFFFAOYSA-M chlormequat chloride Chemical compound [Cl-].C[N+](C)(C)CCCl UHZZMRAGKVHANO-UHFFFAOYSA-M 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
- 239000003085 diluting agent Substances 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 239000004088 foaming agent Substances 0.000 description 3
- 239000000417 fungicide Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 3
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 244000099147 Ananas comosus Species 0.000 description 2
- 235000007119 Ananas comosus Nutrition 0.000 description 2
- 235000016068 Berberis vulgaris Nutrition 0.000 description 2
- 241000335053 Beta vulgaris Species 0.000 description 2
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 2
- 241001480061 Blumeria graminis Species 0.000 description 2
- 0 CCC[C@@](C)C=NC=*C Chemical compound CCC[C@@](C)C=NC=*C 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 241000219146 Gossypium Species 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 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
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 240000000111 Saccharum officinarum Species 0.000 description 2
- 235000007201 Saccharum officinarum Nutrition 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- 235000021536 Sugar beet Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 2
- 150000008052 alkyl sulfonates Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000001276 controlling effect Effects 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- DKWOHBPRFZIUQL-UHFFFAOYSA-N dimethyl-methylidene-oxo-$l^{6}-sulfane Chemical compound C[S+](C)([CH2-])=O DKWOHBPRFZIUQL-UHFFFAOYSA-N 0.000 description 2
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- 150000007529 inorganic bases Chemical class 0.000 description 2
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- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 2
- 238000002844 melting Methods 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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- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical class O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 description 2
- 125000003884 phenylalkyl group Chemical group 0.000 description 2
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- 239000011780 sodium chloride Substances 0.000 description 2
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
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- 239000002699 waste material Substances 0.000 description 2
- UDPGUMQDCGORJQ-UHFFFAOYSA-N (2-chloroethyl)phosphonic acid Chemical compound OP(O)(=O)CCCl UDPGUMQDCGORJQ-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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- AWXNMHWYMZEWLE-UHFFFAOYSA-N 2,2-dimethyl-3-(1,2,4-triazol-1-ylmethyl)pentan-3-ol Chemical compound CCC(O)(C(C)(C)C)CN1C=NC=N1 AWXNMHWYMZEWLE-UHFFFAOYSA-N 0.000 description 1
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- 229910021532 Calcite Inorganic materials 0.000 description 1
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- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- UAEPNZWRGJTJPN-UHFFFAOYSA-N Methylcyclohexane Natural products CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
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- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
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- 235000013980 iron oxide Nutrition 0.000 description 1
- VBMVTYDPPZVILR-UHFFFAOYSA-N iron(2+);oxygen(2-) Chemical class [O-2].[Fe+2] VBMVTYDPPZVILR-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
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- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 230000017066 negative regulation of growth Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 235000003715 nutritional status Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- SOQBVABWOPYFQZ-UHFFFAOYSA-N oxygen(2-);titanium(4+) Chemical class [O-2].[O-2].[Ti+4] SOQBVABWOPYFQZ-UHFFFAOYSA-N 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 230000003071 parasitic effect Effects 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
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 230000008659 phytopathology Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
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- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
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- 230000009885 systemic effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000005068 transpiration Effects 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- BPLKQGGAXWRFOE-UHFFFAOYSA-M trimethylsulfoxonium iodide Chemical compound [I-].C[S+](C)(C)=O BPLKQGGAXWRFOE-UHFFFAOYSA-M 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1019840004250A KR840001752B1 (ko) | 1980-05-16 | 1984-07-19 | 1-하이드록시에틸-아졸 유도체의 제조방법 |
| KR1019840004251A KR840001772B1 (ko) | 1980-05-16 | 1984-07-19 | 1-하이드록시에틸-아졸 유도체의 제조방법 |
Applications Claiming Priority (2)
| 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 |
| DE3018866 | 1980-05-16 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019840004251A Division KR840001772B1 (ko) | 1980-05-16 | 1984-07-19 | 1-하이드록시에틸-아졸 유도체의 제조방법 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR830006239A KR830006239A (ko) | 1983-09-20 |
| KR840001771B1 true KR840001771B1 (ko) | 1984-10-19 |
Family
ID=6102658
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019810001681A Expired KR840001771B1 (ko) | 1980-05-16 | 1981-05-15 | 1-하이드록시에틸-아졸 유도체의 제조방법 |
| KR1019840004251A Expired KR840001772B1 (ko) | 1980-05-16 | 1984-07-19 | 1-하이드록시에틸-아졸 유도체의 제조방법 |
| KR1019840004250A Expired KR840001752B1 (ko) | 1980-05-16 | 1984-07-19 | 1-하이드록시에틸-아졸 유도체의 제조방법 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019840004251A Expired KR840001772B1 (ko) | 1980-05-16 | 1984-07-19 | 1-하이드록시에틸-아졸 유도체의 제조방법 |
| KR1019840004250A Expired KR840001752B1 (ko) | 1980-05-16 | 1984-07-19 | 1-하이드록시에틸-아졸 유도체의 제조방법 |
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) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA817473B (en) * | 1980-11-19 | 1982-10-27 | Ici Plc | Triazole and imidazole compounds |
| EP0158741A3 (en) * | 1980-11-19 | 1986-02-12 | Imperial Chemical Industries Plc | Intermediates for fungicidal 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 |
| DE3202604A1 (de) * | 1982-01-27 | 1983-08-04 | Bayer Ag, 5090 Leverkusen | Ether-derivate von substituierten 1-hydroxyalkyl-azolen, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide und pflanzenwachstumsregulatoren |
| 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 |
| DE3242252A1 (de) * | 1982-11-15 | 1984-05-17 | Bayer Ag, 5090 Leverkusen | Heterocyclisch substituierte hydroxyalkyl-azolyl-derivate |
| DE3242236A1 (de) * | 1982-11-15 | 1984-05-17 | Bayer Ag, 5090 Leverkusen | "antimykotische mittel" |
| DE3242222A1 (de) * | 1982-11-15 | 1984-05-17 | Bayer Ag, 5090 Leverkusen | Hydroxyalkinyl-azolyl-derivate |
| DE3245504A1 (de) * | 1982-12-09 | 1984-06-14 | Bayer Ag, 5090 Leverkusen | Fungizide mittel, deren herstellung und verwendung |
| DE3334409A1 (de) * | 1983-09-23 | 1985-04-18 | Bayer Ag, 5090 Leverkusen | Triazolylmethyl-pyridyloxymethyl-carbinol-derivate |
| DE3407005A1 (de) * | 1983-09-26 | 1985-04-04 | Bayer Ag, 5090 Leverkusen | Hydroxyethylazolyl-oxim-derivate |
| DE3440112A1 (de) * | 1984-11-02 | 1986-05-07 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung optisch aktiver azolylcarbinol-derivate |
| DE3508909A1 (de) * | 1985-03-13 | 1986-09-18 | Bayer Ag, 5090 Leverkusen | Piperazinylmethyl-1,2,4-triazolylmethyl-carbinole |
| 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 |
| DE19829113A1 (de) | 1998-06-10 | 1999-12-16 | Bayer Ag | Mittel zur Bekämpfung von Pflanzenschädlingen |
| JP2008194697A (ja) * | 2008-05-26 | 2008-08-28 | Daicen Membrane Systems Ltd | 分離膜モジュール |
| EA201590002A1 (ru) * | 2009-07-08 | 2015-04-30 | Байер Кропсайенс Аг | Производные фенил(окси/тио)алканола |
| WO2011003528A2 (de) * | 2009-07-08 | 2011-01-13 | Bayer Cropscience Aktiengesellschaft | Substituierte phenyl(oxy/thio)alkanol-derivate |
| US11185548B2 (en) | 2016-12-23 | 2021-11-30 | Helmholtz Zentrum Munchen—Deutsches Forschungszentrum Für Gesundheit Und Umwelt (Gmbh) | Inhibitors of cytochrome P450 family 7 subfamily B member 1 (CYP7B1) for use in treating diseases |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE45765B1 (en) * | 1976-08-19 | 1982-11-17 | Ici Ltd | Triazoles and imidazoles useful as plant fungicides and growth regulating agents |
| US4123542A (en) * | 1977-01-19 | 1978-10-31 | Syntex (U.S.A.) Inc. | Derivatives of N-alkyl imidazoles |
| DE2736122A1 (de) * | 1977-08-11 | 1979-02-22 | Basf Ag | Fungizide |
-
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 CS843394A patent/CS241498B2/cs unknown
- 1981-05-14 CS CS813576A patent/CS241482B2/cs unknown
- 1981-05-15 PL PL1981235518A patent/PL133247B1/pl unknown
- 1981-05-15 JP JP7240681A patent/JPS5716868A/ja active Granted
- 1981-05-15 KR KR1019810001681A patent/KR840001771B1/ko not_active Expired
- 1981-05-15 PL PL1981231191A patent/PL128206B1/pl unknown
- 1981-05-15 ZA ZA00813252A patent/ZA813252B/xx unknown
-
1982
- 1982-11-09 PH PH28115A patent/PH24322A/en unknown
-
1984
- 1984-07-19 KR KR1019840004251A patent/KR840001772B1/ko not_active Expired
- 1984-07-19 KR KR1019840004250A patent/KR840001752B1/ko not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| KR840001772B1 (ko) | 1984-10-19 |
| PH24322A (en) | 1990-05-29 |
| PL231191A1 (enrdf_load_stackoverflow) | 1982-08-16 |
| PL128206B1 (en) | 1984-01-31 |
| CS339581A2 (en) | 1985-07-16 |
| KR830006239A (ko) | 1983-09-20 |
| CS357681A2 (en) | 1985-07-16 |
| CS241498B2 (en) | 1986-03-13 |
| ZA813252B (en) | 1982-05-26 |
| DE3018866A1 (de) | 1981-11-26 |
| PL133247B1 (en) | 1985-05-31 |
| PL235518A1 (enrdf_load_stackoverflow) | 1982-11-22 |
| JPH0224823B2 (enrdf_load_stackoverflow) | 1990-05-30 |
| KR840001752B1 (ko) | 1984-10-19 |
| JPS5716868A (en) | 1982-01-28 |
| CS241482B2 (en) | 1986-03-13 |
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