KR100311195B1 - 옥심기를 가교로 하는, 불소화 비닐기가 치환된 프로페노익 에스테르 및 아미드 화합물, 이의 제조방법 및 이를 포함하는 살균제 조성물 - Google Patents
옥심기를 가교로 하는, 불소화 비닐기가 치환된 프로페노익 에스테르 및 아미드 화합물, 이의 제조방법 및 이를 포함하는 살균제 조성물 Download PDFInfo
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- KR100311195B1 KR100311195B1 KR1019990033722A KR19990033722A KR100311195B1 KR 100311195 B1 KR100311195 B1 KR 100311195B1 KR 1019990033722 A KR1019990033722 A KR 1019990033722A KR 19990033722 A KR19990033722 A KR 19990033722A KR 100311195 B1 KR100311195 B1 KR 100311195B1
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- South Korea
- Prior art keywords
- formula
- compound
- substituted
- methyl
- phenyl
- Prior art date
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- -1 amide compound Chemical class 0.000 title claims abstract description 66
- 150000002148 esters Chemical class 0.000 title claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 title description 6
- 239000012871 anti-fungal composition Substances 0.000 title 1
- 239000000203 mixture Substances 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 14
- 238000000034 method Methods 0.000 claims abstract description 13
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 125000003544 oxime group Chemical group 0.000 claims abstract description 8
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical class 0.000 claims abstract description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 63
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 239000000417 fungicide Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 230000000855 fungicidal effect Effects 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 14
- 239000003899 bactericide agent Substances 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 75
- 238000002360 preparation method Methods 0.000 description 58
- 238000006243 chemical reaction Methods 0.000 description 36
- 239000002904 solvent Substances 0.000 description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 27
- 238000005160 1H NMR spectroscopy Methods 0.000 description 22
- 238000012360 testing method Methods 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- 239000007788 liquid Substances 0.000 description 17
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
- 239000000543 intermediate Substances 0.000 description 15
- 239000003480 eluent Substances 0.000 description 14
- 239000012044 organic layer Substances 0.000 description 14
- 238000010898 silica gel chromatography Methods 0.000 description 14
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 241000209094 Oryza Species 0.000 description 12
- 235000007164 Oryza sativa Nutrition 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 235000009566 rice Nutrition 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 238000001035 drying Methods 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
- 125000001841 imino group Chemical group [H]N=* 0.000 description 9
- 230000003902 lesion Effects 0.000 description 9
- 229940049953 phenylacetate Drugs 0.000 description 9
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 201000010099 disease Diseases 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 241000209219 Hordeum Species 0.000 description 7
- 235000007340 Hordeum vulgare Nutrition 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
- 125000003944 tolyl group Chemical group 0.000 description 7
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 6
- 229920001817 Agar Polymers 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 241000209140 Triticum Species 0.000 description 6
- 235000021307 Triticum Nutrition 0.000 description 6
- 239000008272 agar Substances 0.000 description 6
- 230000008878 coupling Effects 0.000 description 6
- 238000010168 coupling process Methods 0.000 description 6
- 238000005859 coupling reaction Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 5
- OQZMPAGXCRTMIZ-UHFFFAOYSA-N 6-ethenyl-5,5-difluorocyclohexa-1,3-diene Chemical compound FC1(F)C=CC=CC1C=C OQZMPAGXCRTMIZ-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 241000196324 Embryophyta Species 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 238000011081 inoculation Methods 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- VNOMEAQPOMDWSR-UHFFFAOYSA-N 2,2,2-trifluoro-1-phenylethanol Chemical compound FC(F)(F)C(O)C1=CC=CC=C1 VNOMEAQPOMDWSR-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- 240000008067 Cucumis sativus Species 0.000 description 4
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
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- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 230000001954 sterilising effect Effects 0.000 description 4
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- GIZBYELHYIBHIR-UHFFFAOYSA-N (1-chloro-2,2,2-trifluoroethyl)benzene Chemical compound FC(F)(F)C(Cl)C1=CC=CC=C1 GIZBYELHYIBHIR-UHFFFAOYSA-N 0.000 description 3
- QSSXJPIWXQTSIX-UHFFFAOYSA-N 1-bromo-2-methylbenzene Chemical compound CC1=CC=CC=C1Br QSSXJPIWXQTSIX-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- JAICGBJIBWDEIZ-UHFFFAOYSA-N 3-phenylmethoxybenzaldehyde Chemical compound O=CC1=CC=CC(OCC=2C=CC=CC=2)=C1 JAICGBJIBWDEIZ-UHFFFAOYSA-N 0.000 description 3
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- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 3
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- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- 241000227653 Lycopersicon Species 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
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- BLEMRRXGTKTJGT-UHFFFAOYSA-N methyl 2-(2-methylphenyl)acetate Chemical compound COC(=O)CC1=CC=CC=C1C BLEMRRXGTKTJGT-UHFFFAOYSA-N 0.000 description 3
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- QMJRGFDWGOXABE-UHFFFAOYSA-N methyl 2-(2-methylphenyl)-2-oxoacetate Chemical compound COC(=O)C(=O)C1=CC=CC=C1C QMJRGFDWGOXABE-UHFFFAOYSA-N 0.000 description 2
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- RIGZIGSLGOTINN-UHFFFAOYSA-N Strobilurin C Natural products COC=C(C(=O)OC)C(C)=CC=CC1=CC=CC(OCC=C(C)C)=C1 RIGZIGSLGOTINN-UHFFFAOYSA-N 0.000 description 1
- STSCVKRWJPWALQ-UHFFFAOYSA-N TRIFLUOROACETIC ACID ETHYL ESTER Chemical compound CCOC(=O)C(F)(F)F STSCVKRWJPWALQ-UHFFFAOYSA-N 0.000 description 1
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- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
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- 150000004677 hydrates Chemical class 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
- YPGCWEMNNLXISK-UHFFFAOYSA-N hydratropic acid Chemical compound OC(=O)C(C)C1=CC=CC=C1 YPGCWEMNNLXISK-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 1
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- 239000002054 inoculum Substances 0.000 description 1
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- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 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
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
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- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- RIGZIGSLGOTINN-MSOZMUFPSA-N methyl (2e,3z,5e)-2-(methoxymethylidene)-3-methyl-6-[3-(3-methylbut-2-enoxy)phenyl]hexa-3,5-dienoate Chemical compound CO\C=C(\C(=O)OC)/C(/C)=C\C=C\C1=CC=CC(OCC=C(C)C)=C1 RIGZIGSLGOTINN-MSOZMUFPSA-N 0.000 description 1
- BSDQITJYKQHXQR-UHFFFAOYSA-N methyl prop-2-eneperoxoate Chemical compound COOC(=O)C=C BSDQITJYKQHXQR-UHFFFAOYSA-N 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- JSCQSBGXKRTPHZ-SYKZHUKTSA-N mucidin Chemical compound CO\C=C(\C(=O)OC)/C(/C)=C\C=C\C1=CC=CC=C1 JSCQSBGXKRTPHZ-SYKZHUKTSA-N 0.000 description 1
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- 230000003449 preventive effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
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- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 238000011272 standard treatment Methods 0.000 description 1
- ZDIQYKMDNQULMX-PJUQCDRASA-N strobilurin B Chemical compound CO\C=C(\C(=O)OC)/C(/C)=C\C=C\C1=CC=C(Cl)C(OC)=C1 ZDIQYKMDNQULMX-PJUQCDRASA-N 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
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- 239000011701 zinc Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C207/00—Compounds containing nitroso groups bound to a carbon skeleton
- C07C207/04—Compounds containing nitroso groups bound to a carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen 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
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds
- A01N33/24—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds only one oxygen atom attached to the nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (5)
- 하기 화학식 1로 표시되고, 옥심기를 가교로 하고 불소화 비닐기가 치환된 프로페노익 에스테르 및 아미드 화합물:화학식 1상기 식에서, X는 CH 또는 N이고, Y는 O 또는 NH이며, R1은 수소, C1-4알킬 또는 할로겐으로 치환된 C1-4알킬이고, R2는 페닐; C1-4알킬, 할로겐으로 치환된 C1-4알킬, C1-4알콕시, 메틸렌디옥시 또는 할로겐으로 하나이상이 치환된 페닐; 또는 나프탈렌이다.
- 제 1 항에 있어서,R1이 수소 또는 메틸이고 R2가 페닐 또는, Cl 또는 F로 치환된 페닐인 화합물.
- 하기 화학식 2의 브롬화물을 염기 존재하에 하기 화학식 3의 옥심계 화합물과 반응시켜 하기 화학식 4의 화합물을 얻고 이를 탈벤질화하여 하기 화학식 5a의 페놀성 에스테르계 화합물을 얻은 후 이를 하기 화학식 6의 불소화 비닐계 화합물과 염기존재 하에 반응시키는 단계를 포함하는, 하기 화학식 1a의 화합물의 제조 방법:화학식 2화학식 3화학식 4화학식 5a화학식 6화학식 1a상기 식에서, X, R1및 R2는 제 1 항에서 정의한 바와 같다.
- 하기 화학식 2의 브롬화물을 염기 존재하에 하기 화학식 3의 옥심계 화합물과 반응시켜 하기 화학식 4의 화합물을 얻고 이를 탈벤질화하여 하기 화학식 5a의 페놀성 에스테르계 화합물을 얻은 후 이를 아민과 반응시켜 하기 화학식 5b의 페놀성 아미드계 화합물을 얻고 이를 하기 화학식 6의 불소화 비닐계 화합물과 염기 존재하에 반응시키는 단계를 포함하는, 하기 화학식 1b의 화합물의 제조 방법:화학식 2화학식 3화학식 4화학식 5a화학식 5b화학식 6화학식 1b상기 식에서, X, R1및 R2는 제 1 항에서 정의한 바와 같다.
- 제 1 항에 따른 화학식 1의 화합물 유효량 및 약제학적으로 허용가능한 담체를 포함하는 살균제 조성물.
Priority Applications (12)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1019990033722A KR100311195B1 (ko) | 1999-08-16 | 1999-08-16 | 옥심기를 가교로 하는, 불소화 비닐기가 치환된 프로페노익 에스테르 및 아미드 화합물, 이의 제조방법 및 이를 포함하는 살균제 조성물 |
US10/049,412 US6552080B1 (en) | 1999-08-16 | 2000-08-16 | Fungicidal compounds having a fluorovinyl-or fluoropropenyl-oxyphenyloxime moiety and process for the preparation thereof |
EP00952045A EP1204632B1 (en) | 1999-08-16 | 2000-08-16 | Fungicidal compounds having a fluorovinyl- or fluoropropenyl-oxyphenyloxime moiety and process for the preparation thereof |
BRPI0013409-0A BR0013409B1 (pt) | 1999-08-16 | 2000-08-16 | compostos fungicidas possuindo uma porção flúorvinil ou fluorpropenil-oxifeniloxima e processo para preparação dos mesmos. |
JP2001516886A JP3739703B2 (ja) | 1999-08-16 | 2000-08-16 | フルオロビニル−またはフルオロプロペニル−オキシフェニルオキシム残基を有する殺菌化合物およびその製造方法 |
CNB008117403A CN1178897C (zh) | 1999-08-16 | 2000-08-16 | 具有氟乙烯基-或氟丙烯基-氧基苯基肟结构部分的杀真菌化合物和它们的制备方法 |
DE60023909T DE60023909T2 (de) | 1999-08-16 | 2000-08-16 | Fungizide mit einer fluorovinyl-oder fluoropropenyloxyphenyloxim-einheit und ein verfahren zu ihrer herstellung. |
PCT/KR2000/000906 WO2001012585A1 (en) | 1999-08-16 | 2000-08-16 | Fungicidal compounds having a fluorovinyl- or fluoropropenyl-oxyphenyloxime moiety and process for the preparation thereof |
AT00952045T ATE309198T1 (de) | 1999-08-16 | 2000-08-16 | Fungizide mit einer fluorovinyl-oder fluoropropenyloxyphenyloxim-einheit und ein verfahren zu ihrer herstellung. |
CA002380864A CA2380864C (en) | 1999-08-16 | 2000-08-16 | Fungicidal compounds having a fluorovinyl- or fluoropropenyl-oxyphenyloxime moiety and process for the preparation thereof |
AU64807/00A AU753165B2 (en) | 1999-08-16 | 2000-08-16 | Fungicidal compounds having a fluorovinyl- or fluoropropenyl-oxyphenyloxime moiety and process for the preparation thereof |
ZA200200570A ZA200200570B (en) | 1999-08-16 | 2002-01-22 | Fungicidal compounds having a fluorovinyl-or fluoropropenyl-oxyphenyloxime moiety and process for the preparation thereof. |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1019990033722A KR100311195B1 (ko) | 1999-08-16 | 1999-08-16 | 옥심기를 가교로 하는, 불소화 비닐기가 치환된 프로페노익 에스테르 및 아미드 화합물, 이의 제조방법 및 이를 포함하는 살균제 조성물 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR20010017960A KR20010017960A (ko) | 2001-03-05 |
KR100311195B1 true KR100311195B1 (ko) | 2001-10-18 |
Family
ID=19607373
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019990033722A KR100311195B1 (ko) | 1999-08-16 | 1999-08-16 | 옥심기를 가교로 하는, 불소화 비닐기가 치환된 프로페노익 에스테르 및 아미드 화합물, 이의 제조방법 및 이를 포함하는 살균제 조성물 |
Country Status (2)
Country | Link |
---|---|
KR (1) | KR100311195B1 (ko) |
ZA (1) | ZA200200570B (ko) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100379761B1 (ko) * | 2000-11-23 | 2003-04-11 | 한국화학연구원 | 옥심기를 측쇄로 하는 신규의 프로페노익 에스테르 및아미드 유도체, 이의 제조방법 그리고 이를 함유하는살균제 조성물 |
WO2005002336A1 (en) * | 2003-07-02 | 2005-01-13 | Korea Research Institute Of Chemical Technology | Adjuvant formulation for enhancing the fungicidal efficacy and fungicidal composition containing same |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0307103A2 (en) * | 1987-09-09 | 1989-03-15 | Zeneca Limited | Fungicides |
EP0370629A1 (en) * | 1988-11-21 | 1990-05-30 | Zeneca Limited | Fungicides |
WO1996006072A1 (en) * | 1994-08-19 | 1996-02-29 | Ciba-Geigy Ag | Oxime ethers and their use as pesticides |
US5723473A (en) * | 1992-10-14 | 1998-03-03 | Zeneca Limited | Propenoic acid derivatives useful as fungicides |
KR100229440B1 (ko) * | 1997-05-16 | 1999-11-01 | 김충섭 | 플루오르비닐기를 갖는 신규의 프로페노익 에스테르 및 아미드 유도체 |
-
1999
- 1999-08-16 KR KR1019990033722A patent/KR100311195B1/ko not_active IP Right Cessation
-
2002
- 2002-01-22 ZA ZA200200570A patent/ZA200200570B/en unknown
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0307103A2 (en) * | 1987-09-09 | 1989-03-15 | Zeneca Limited | Fungicides |
EP0370629A1 (en) * | 1988-11-21 | 1990-05-30 | Zeneca Limited | Fungicides |
US5723473A (en) * | 1992-10-14 | 1998-03-03 | Zeneca Limited | Propenoic acid derivatives useful as fungicides |
WO1996006072A1 (en) * | 1994-08-19 | 1996-02-29 | Ciba-Geigy Ag | Oxime ethers and their use as pesticides |
KR100229440B1 (ko) * | 1997-05-16 | 1999-11-01 | 김충섭 | 플루오르비닐기를 갖는 신규의 프로페노익 에스테르 및 아미드 유도체 |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100379761B1 (ko) * | 2000-11-23 | 2003-04-11 | 한국화학연구원 | 옥심기를 측쇄로 하는 신규의 프로페노익 에스테르 및아미드 유도체, 이의 제조방법 그리고 이를 함유하는살균제 조성물 |
WO2005002336A1 (en) * | 2003-07-02 | 2005-01-13 | Korea Research Institute Of Chemical Technology | Adjuvant formulation for enhancing the fungicidal efficacy and fungicidal composition containing same |
KR100537946B1 (ko) * | 2003-07-02 | 2005-12-21 | 한국화학연구원 | 살균제의 약효증진제 조성물 및 이를 함유하는 살균제조성물 |
Also Published As
Publication number | Publication date |
---|---|
KR20010017960A (ko) | 2001-03-05 |
ZA200200570B (en) | 2003-06-25 |
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