WO1997012875A1 - DERIVES HETEROCYCLIQUES D'α-ALCOXY-IMINOBENZYLE, INTERMEDIAIRES POUR LEUR PREPARATION, ET PRODUITS CHIMIQUES AGRICOLES CONTENANT LESDITS DERIVES EN TANT QUE PRINCIPE ACTIF - Google Patents
DERIVES HETEROCYCLIQUES D'α-ALCOXY-IMINOBENZYLE, INTERMEDIAIRES POUR LEUR PREPARATION, ET PRODUITS CHIMIQUES AGRICOLES CONTENANT LESDITS DERIVES EN TANT QUE PRINCIPE ACTIF Download PDFInfo
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- WO1997012875A1 WO1997012875A1 PCT/JP1996/002766 JP9602766W WO9712875A1 WO 1997012875 A1 WO1997012875 A1 WO 1997012875A1 JP 9602766 W JP9602766 W JP 9602766W WO 9712875 A1 WO9712875 A1 WO 9712875A1
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- Prior art keywords
- compound
- phenyl
- methyl
- alkyl
- compound according
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- 239000004480 active ingredient Substances 0.000 title claims abstract description 9
- 239000003905 agrochemical Substances 0.000 title claims abstract description 5
- 239000000543 intermediate Substances 0.000 title abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 184
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 43
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 30
- 239000000203 mixture Substances 0.000 claims abstract description 30
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 15
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 12
- 125000005843 halogen group Chemical group 0.000 claims abstract description 11
- -1 isoxoxolinyl Chemical group 0.000 claims description 62
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 230000000855 fungicidal effect Effects 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 125000002950 monocyclic group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 239000000417 fungicide Substances 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 125000003367 polycyclic group Chemical group 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 230000026030 halogenation Effects 0.000 claims description 4
- 238000005658 halogenation reaction Methods 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 0.000 claims description 4
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 239000002917 insecticide Substances 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 238000004659 sterilization and disinfection Methods 0.000 claims description 2
- 125000001984 thiazolidinyl group Chemical group 0.000 claims description 2
- 241000894006 Bacteria Species 0.000 claims 2
- 241000270666 Testudines Species 0.000 claims 2
- 230000003032 phytopathogenic effect Effects 0.000 claims 2
- 125000003944 tolyl group Chemical group 0.000 claims 2
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- 102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 claims 1
- 101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 claims 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims 1
- 230000001548 androgenic effect Effects 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 125000005493 quinolyl group Chemical group 0.000 claims 1
- 230000001954 sterilising effect Effects 0.000 claims 1
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 66
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 49
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 42
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 34
- 239000002904 solvent Substances 0.000 description 34
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 239000002585 base Substances 0.000 description 20
- 239000000243 solution Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 241000196324 Embryophyta Species 0.000 description 16
- 230000035484 reaction time Effects 0.000 description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 13
- 238000001953 recrystallisation Methods 0.000 description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000004440 column chromatography Methods 0.000 description 12
- 229910052751 metal Inorganic materials 0.000 description 12
- 239000002184 metal Substances 0.000 description 12
- 239000012046 mixed solvent Substances 0.000 description 12
- 239000008096 xylene Substances 0.000 description 12
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 11
- 238000007796 conventional method Methods 0.000 description 11
- 150000002170 ethers Chemical class 0.000 description 11
- 150000008282 halocarbons Chemical class 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 240000008067 Cucumis sativus Species 0.000 description 9
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 9
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- 150000002430 hydrocarbons Chemical class 0.000 description 9
- 230000000749 insecticidal effect Effects 0.000 description 9
- 238000010898 silica gel chromatography Methods 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 240000007594 Oryza sativa Species 0.000 description 8
- 235000007164 Oryza sativa Nutrition 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- 235000013312 flour Nutrition 0.000 description 8
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 235000009566 rice Nutrition 0.000 description 8
- 238000005507 spraying Methods 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
- 241000209140 Triticum Species 0.000 description 7
- 235000021307 Triticum Nutrition 0.000 description 7
- 150000001298 alcohols Chemical class 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 201000010099 disease Diseases 0.000 description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 244000052769 pathogen Species 0.000 description 7
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 6
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 235000010469 Glycine max Nutrition 0.000 description 6
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 6
- 230000000844 anti-bacterial effect Effects 0.000 description 6
- 239000012230 colorless oil Substances 0.000 description 6
- 238000011081 inoculation Methods 0.000 description 6
- 229910052740 iodine Inorganic materials 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- 244000068988 Glycine max Species 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 150000001350 alkyl halides Chemical class 0.000 description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 229910052744 lithium Inorganic materials 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- 229910052749 magnesium Inorganic materials 0.000 description 5
- 150000002825 nitriles Chemical class 0.000 description 5
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- 230000001717 pathogenic effect Effects 0.000 description 5
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- 238000000746 purification Methods 0.000 description 5
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- 239000002689 soil Substances 0.000 description 5
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
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- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 235000019270 ammonium chloride Nutrition 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
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- 235000011181 potassium carbonates Nutrition 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
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- 229910000104 sodium hydride Inorganic materials 0.000 description 4
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- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
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- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
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- 241001330975 Magnaporthe oryzae Species 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000004703 alkoxides Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 239000006187 pill Substances 0.000 description 3
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- 239000000843 powder Substances 0.000 description 3
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- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 3
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- 238000003786 synthesis reaction Methods 0.000 description 3
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- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 2
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- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- UKFPAGCSDWQXFT-UHFFFAOYSA-N 3-phenyl-4,5-dihydro-1,2-oxazole Chemical compound O1CCC(C=2C=CC=CC=2)=N1 UKFPAGCSDWQXFT-UHFFFAOYSA-N 0.000 description 2
- 125000003341 7 membered heterocyclic group Chemical group 0.000 description 2
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- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 239000005046 Chlorosilane Substances 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
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- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- HASGOCLZFTZSTN-UHFFFAOYSA-N cyclohexane;hexane Chemical compound CCCCCC.C1CCCCC1 HASGOCLZFTZSTN-UHFFFAOYSA-N 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 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 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- 229940120124 dichloroacetate Drugs 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- WHFKIZXBVFEJGA-UHFFFAOYSA-L dihydroxy(dioxo)chromium;pyridine Chemical compound O[Cr](O)(=O)=O.C1=CC=NC=C1.C1=CC=NC=C1 WHFKIZXBVFEJGA-UHFFFAOYSA-L 0.000 description 1
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 244000013123 dwarf bean Species 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000001999 effect on insects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- KIWBPDUYBMNFTB-UHFFFAOYSA-M ethyl sulfate Chemical compound CCOS([O-])(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-M 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- QHFNOSFIKJEMNP-UHFFFAOYSA-N gold trihydride Chemical class [AuH3] QHFNOSFIKJEMNP-UHFFFAOYSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 235000021331 green beans Nutrition 0.000 description 1
- 229920000591 gum Polymers 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 239000010903 husk Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 125000004501 isothiazol-5-yl group Chemical group S1N=CC=C1* 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
- 229920005610 lignin Polymers 0.000 description 1
- 235000014666 liquid concentrate Nutrition 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- CJPQIRJHIZUAQP-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(phenylacetyl)alaninate Chemical compound CC=1C=CC=C(C)C=1N(C(C)C(=O)OC)C(=O)CC1=CC=CC=C1 CJPQIRJHIZUAQP-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- ZAEQTGTVGUJEFV-UHFFFAOYSA-N phenylmethanesulfonate;pyridin-1-ium Chemical compound C1=CC=[NH+]C=C1.[O-]S(=O)(=O)CC1=CC=CC=C1 ZAEQTGTVGUJEFV-UHFFFAOYSA-N 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 239000010665 pine oil Substances 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 229920001223 polyethylene glycol Chemical class 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000021395 porridge Nutrition 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000004300 potassium benzoate Substances 0.000 description 1
- 235000010235 potassium benzoate Nutrition 0.000 description 1
- 229940103091 potassium benzoate Drugs 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 description 1
- 125000004497 pyrazol-5-yl group Chemical group N1N=CC=C1* 0.000 description 1
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- 125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical group [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- SXPUVBFQXJHYNS-UHFFFAOYSA-N α-furil Chemical compound C=1C=COC=1C(=O)C(=O)C1=CC=CO1 SXPUVBFQXJHYNS-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Definitions
- the present invention relates to a novel ⁇ -alkoxyimino benzyl heterocyclic derivative, an intermediate for producing the same, and a drug containing the same as an active ingredient.
- An object of the present invention is to provide a compound having utility such as better bactericidal activity and insecticidal activity. Disclosure of the invention
- the present inventors have conducted intensive studies to achieve the above object, and as a result, have found that the ⁇ -alkoxyimino benzyl heterocyclic derivative described below has excellent bactericidal and insecticidal activities. Was completed.
- R ′ is a substituted or unsubstituted heterocyclic group
- R 2 is a substituted or unsubstituted or substituted heterocyclic group
- R 3 is a substituted or unsubstituted heterocyclic group
- alkyl is a hydrogen atom, an alkyl, alkoxy, b Gen atom, two Bok port, Shiano or b plasminogen reduction Anorekiru
- Micromax one ⁇ C (R 5) -
- R s is a hydrogen atom, an alkyl, halogenated It represents an alkyl or a cycloalkyl, indicating that the form of the R 2 and R gar cord of connexion, adjacent carbon atoms to the monitor hetero atoms may be included monocyclic or condensed polycyclic ] or an A- (CR P R:)
- n - and R 7 are each independently hydrogen atom, alkyl, Xia Roh or halogenation alkyl
- A is an oxygen atom
- lower refers to a group having 1 to 8 carbon atoms, preferably 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms. Represent.
- the optionally substituted heterocyclic group represented by R 1 includes a substituted heterocyclic group in addition to an unsubstituted heterocyclic group.
- These heterocyclic groups include, for example, a 5- to 7-membered heterocyclic group containing 1 to 4 heteroatoms selected from a nitrogen atom, an oxygen atom and a sulfur atom in the ring, specifically
- a pyridyl eg, pyridin-2-yl, pyridin-13-yl, etc.
- a pyrimidell eg, pyrimidine-12-yl, pyridyl
- isosozozoline e.g., isosozozoru 3-yl, isosozozororu 4-jinore, isosozozororu 5-yl
- isosozozolinil e.g.
- oxaziaziryl eg, 1, 3, 4-oxaziaziolinol (eg, 1, 3, 4-oxaziazol-2-yl, etc.), 1,, 2,4—oxaziazione (eg, 1,2,4 And triazoles (eg, 1, 2, 4 — triazolinoles (eg, 1H—1, 2, 4, 4_ triazols) Noreichi 1 Or 4H—1,2,4-triazole 4—yl, 1H—1,2,4—triazole 5—yl), or pyramid Which
- heterocyclic groups may form a condensed ring with a carbocyclic ring or another heterocyclic ring.
- condensed ring examples include benzoxazolyl (eg, benzoxazole-2-yl), benzothiazole (eg, benzothiazol-2-yl), benzoisoxazolinole (eg, Benzoi soxazolu 3-yl, etc., tetramethylenisoxazolyl (for example, 3, 4-1 ⁇ ⁇ — — — — —, 4, 5 ⁇ tetra) Methylene dioxoxazole-1 -yl).
- benzoxazolyl eg, benzoxazole-2-yl
- benzothiazole eg, benzothiazol-2-yl
- benzoisoxazolinole eg, Benzoi soxazolu 3-yl, etc., tetramethylenisoxazolyl (for example, 3, 4-1 ⁇ ⁇ — — — — —, 4, 5 ⁇ tetra) Methylene dio
- heterocyclic groups and their condensed rings may be located at any position where a bond is possible, c
- Examples of the substituent of the substituted heterocyclic group represented by R 1 include lower alkyl (eg, methyl, ethyl, propyl, butyl, etc.) and lower alkenyl (eg, butyl, aryl) Alkynyl (e.g., ethur, 2 -probyl, 3 -butur, etc.), cycloalkyl (e.g., cyclopropinole, cyclobenchinole, cyclohexinole, etc.), Cyclo anole kenyl (eg, cycloventur, cyclohexenyl, etc.), halogenated lower alkyl (eg, trifluoromethyl, trichloromethyl, difluoromethyltinole, chloromethylinole) , 2—bromoethyl, 1,2—dichlorobenzene pill, etc.), halogen atoms (eg, fluorine, chlorine, bro
- R 9 is a hydrogen atom, a lower ⁇ alkyl (e.g., methylation, Echiru, full b arsenide Le ), Lower alkenyl (eg, vinyl, aryl, 2-butyr, etc.), lower alkynyl (eg, ethur, 2—Probul, 3—Butyl, etc.)] and lower alkylsulfonyl (eg, mesyl).
- lower alkyl or halogenated lower alkyl is preferred, and methyl is particularly preferred.
- R 1 is preferably an optionally substituted isosoxazole 13-yl, isosoxazole 4-inole, isosoxazoline 1-5-yl, 2—isosoxazoline 13-inole , 2 — Isosoxazoline 1 5 — Ill, Imidazol 1 2 — Ill, Franc 1 2 — Ignore, 1, 2, 2, 4 — Oxaziazolo 3 — Ignore, 1 , 3, 4 — oxaziazolou 2 — yl.
- R ' is more preferably 3'-yl, 5'-methyl-isoxazo-l- 3'-inole, 3_-methyl-isoxazole-l--5-yl, 2--isoxazoline-l-3 — It ’s an ill.
- ⁇ Li Lumpur also be ⁇ Li Lumpur represented by R 2, 6 to 1 4 ⁇ Li Lumpur carbon, for example phenyl, naphthyl (e.g., 1 over Na off chill , 2-naphthyl).
- the optionally substituted heterocyclic group represented by R 2 includes a substituted heterocyclic group in addition to an unsubstituted heterocyclic group.
- these heterocyclic groups include, for example, a 5- to 7-membered heterocyclic group containing 1 to 4 heteroatoms selected from a nitrogen atom, an oxygen atom and a sulfur atom in a ring; Include pyridyl (eg, pyridin-2-yl, pyridin-13-yl, pyridin-14-yl), pyrimidinyl (eg, pyrimidine-12-yl) , Pyrimidine, 14-yl, pyrimidine, 1-5-yl), isosozozo-linole (ex.
- the substituent of the substituted aryl and the substituted heterocyclic group represented by R 2 is the same as the substituent exemplified for the substituted heterocyclic group represented by R 1 above.
- phenyl, phenyl (lower) alkyl eg, benzyl, phenethyl, etc.
- phenyl, and the phenyl in the phenyl (lower) alkyl and the phenyl include, as an unsubstituted or substituted group, a halogen atom, a lower alkyl, a halogenated lower alkyl, and a lower alkoxy.
- C may have 1 to 3 substituents selected from the group
- substituents for the substituted aryl and the substituted heterocyclic group represented by R 2 a halogen atom, lower alkyl, halogenated lower alkyl, lower alkoxy, phenyl and phenoxy are preferred. New These substituents may be located at any substitutable position of the ring.
- the substituent is 1 to 5, preferably 1 to 4, and more preferably 1 to 3, and these may be the same or different, c
- R 2 preferably has 1 to 3 substituents selected from the group consisting of a halogen atom, lower alkyl, lower alkyl halide, lower alkoxy, phenyl and phenyl.
- An optional phenyl or heterocyclic group includes:
- R ' include phenyl; lower alkoxy (preferred). Methoxy), lower alkyl halides (preferably trifluoromethyl), halogen atoms (preferably fluorine, chlorine, bromine) and lower alkyls (preferably methyl).
- alkyl represented by R examples include alkyl having 1 to 4 carbon atoms, preferably 1 to 3 carbon atoms, and specific examples include methyl, ethyl, propyl, and isopropyl. In particular, methyl is preferred.
- Examples of the alkyl represented by R 1 include the same as those exemplified as the alkyl represented by R :
- the alkoxy represented by 'is for example, an alkoxy having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, specifically, methoxy, ethoxy, propoxy, isopropoxy, butoxy, Isobutoxy, sec-butoxy, tert-butoxy, etc. are available.
- halogen atom represented by R 1 examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom:
- the alkyl halide represented by R ′ is, for example, an alkyl having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, and specifically, for example, methyl, ethyl, bropinole, isoflur
- At least one halogen atom eg, fluorine, chlorine, bromine, iodine
- alkyls such as pills and butinoles
- halogen atom eg, fluorine, chlorine, bromine, iodine
- Jifuruoro methyl Application Benefits Furuo Russia main Chinore, click B B methylation, 1, 2 - Axis B port propyl, etc. Chi cormorants this c include Bok Li Furuoro methyl favored arbitrariness.
- R 1 is preferably hydrogen.
- Examples of the alkyl represented by R 5 to R H include the same alkyls as those exemplified above for the alkyl represented by R. Of these, methyl or ethyl is preferred, respectively.
- Examples of the alkyl halide represented by R 5 to R 7 include the same ones as those exemplified as the alkyl halide represented by R ′ above. Of these, trifluoromethyl is preferable. .
- Examples of the acyl represented by R ⁇ include, for example, alkanol and arylonole.
- the alkanol is, for example, an alkanol having an alkyl group having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, specifically, for example, formyl, acetyl, triethyl Examples include phenolic acetyl, propionyl, and butylyl. Of these, acetyl is preferred.
- As the aryl for example, an aryl having 7 to 15 carbon atoms, specifically, for example, benzoyl, naphthoyl and the like can be mentioned: Of these, benzoyl is preferred.
- VI is one ⁇ - C (R ⁇ ) - R L ' and R 5 are bonded to good c
- the also form a good monocyclic or condensed polycyclic also include heteroatoms in the case of As a monocyclic ring, a 4- to 8-membered ring which is formed together with R and R5 and the carbon atom to which they are bonded, and which may contain a hetero atom (eg, a nitrogen atom, an oxygen atom, a sulfur atom, etc.)
- the monocyclic ring is fused with another ring to form a fused polycyclic ring. It may be formed.
- monocyclic ring and the condensed polycyclic ring include cyclopentane, cyclohexane, indane, 1,2,3,4—tetrahydronaphtalene, 5,6, 7, 8—Tetrahydroquinoline, 4, 5, 6, 7—Tetrahydrobenzo [b] franc.
- one N C (CH :,) one, one O—CH (CH 3 ) —
- the compound of the present invention has two isomers, E-form and Z-isomer due to the R : 'oxymino moiety, and the present invention relates to these isomers and mixtures of these isomers in any ratio. Is included. In this specification, this is indicated by using a wavy line (-) in the general formula.
- Specific examples of the compound represented by the general formula (I) of the present invention include the compounds shown in Examples described later.
- the following compounds are preferable (compound numbers are shown in Examples described later). Is shown in the above).
- R 1 force; 3 methinolay soxazole-5—yl, R 2 force; 41-port phenyl, R: 'is methyl, R 1 is hydrogen and M is —O—CH (CH 3 ) — (Compound No. C-17),
- a compound (Compound No. C-130), R 1 force; 3 — methyl soxazolone 5 — dinole, R 2 is 4 — black phenyl, R 3 is methyl, R is hydrogen and M is N C (CH 3 ) — A compound (Compound No. C-67),
- is methylinole, R 4 is hydrogen and M is N C (CH :,) A compound (compound number C—82),
- Y represents a halogen atom (eg, chlorine atom, bromine atom, iodine atom, etc.)
- p represents a hydroxyl-protecting group, and other symbols have the same meanings as described above. That is, compound (III) can be produced by protecting the hydroxyl group of compound (II), which is commercially available, with an appropriate protecting group: a group represented by p:
- This protection of the hydroxyl groups can be, for example, Green (T.W. Green), "Protective Groups-In 'Organic Synthesis”! ⁇ 113 pages, John 'Willy' and 'Son's (John Willy & Sons) (19981); C.B.R. ) "Protective 'Groups'in' Organic 'Chemistry, JF' Matsukomi. Omie), ed., Pages 95-143, Plenum Breath (Plenum Press) (1973), etc. Can be done.
- Tetrahydridroviranil Tetrahydrodrovillaninore, Tetrahydrodrofuranoninore, Tetrahydrodrochiofraninole, 1-etoxyshecil and i-mesh Chilled 1-methoxed compound
- (III) can be obtained by reacting the corresponding olefin with compound (II) in the presence of an acid catalyst in a suitable solvent or without solvent.
- the corresponding orthofins are 3,4—dihydro 2H—pyran, 2,3—dihydro 4 H—thiine, dihydrofuran, dihydrothiofuran, and ethyl butyl, respectively.
- O reflex fin 1-3 equivalents relative to compound (II), and rather is preferred a] to 2 equivalents c
- the acid catalyst examples include hydrogen chloride, oxylin chloride, p-toluenesulfonate, p-toluenesulfonic acid pyridine salt, montmorinite, bismethyl sulfate, acetic acid, and the like.
- p Polyvinyl pyridinium toluenesulfonate, acetic acid in trifluorene, borane trifluoride (BF, ⁇ OE t and acidic ion exchange resins.
- non-alcoholic solvents can be used.
- hydrocarbons eg, benzene, toluene, xylene, etc.
- halogenated hydrocarbons eg, black mouth form, dichloromethane, etc.
- ethers eg, Ter, tetrahydrofuran, dioxane, etc.
- esters eg, ethyl sulphate
- N, N-dimethylformamide and mixed solvents thereof
- the reaction temperature is from 130 to 100: preferably from 0 to 60 °.
- the reaction time is usually about 15 minutes to 24 hours.
- the silyl ether type compound (III) can be obtained by reacting the compound (II) with an appropriate silylating agent. Generally, it is obtained by reacting compound (II) with a suitable solvent using chlorosilane as a silylating agent in the presence of a base.
- Chlorsilane can be used as a commercially available product or produced by a known method.
- Examples of usable bases include organic bases (eg, N, N-dimethylaniline, pyridine, triethylamine, imidazole, etc.), metal carbonates (eg, carbonate) Sodium, potassium carbonate, etc., metal hydrides (eg, sodium hydride, potassium hydride, etc.), metal bicarbonates (eg, sodium bicarbonate, hydrogen bicarbonate) And one equivalent or more, preferably 1 to 2 equivalents can be used.
- organic bases eg, N, N-dimethylaniline, pyridine, triethylamine, imidazole, etc.
- metal carbonates eg, carbonate
- Sodium, potassium carbonate, etc. metal hydrides (eg, sodium hydride, potassium hydride, etc.)
- metal bicarbonates eg, sodium bicarbonate, hydrogen bicarbonate
- one equivalent or more, preferably 1 to 2 equivalents can be used.
- Solvents that can be used include hydrocarbons (eg, hexane, benzene, tonolene, xylene, etc.), halogenated hydrocarbons (eg, black form, dichloromethan) Etc.), ethers (eg, getyl ether, tetrahedral) Ketones (eg, acetone, methylethylketone, etc.), nitriles (eg, acetonitrile, etc.), N, N-dimethyl Examples include formamide, dimethyl sulfoxide and a mixed solvent thereof.
- the reaction temperature is 120 ° C .: preferably 0.60 t.
- the reaction time is 5 minutes to 30 hours, preferably 30 minutes to 15 hours.
- the compound (III) protected with 1-ethoxyshetyl is obtained by reacting the corresponding halide with the compound (II) in the presence of a base.
- the corresponding halogenated compounds are, respectively, /, methyl methyl ether, triphenyl methyl halide, 2-halotetrahydrofuran and 1-hydroxyethyl ether, which are commercially available products. It can be used or manufactured by a known method.
- Chloride or bromide can be used as a chromogen.
- a suitable catalyst eg, phosphorus pentoxide, etc.
- the obtained compound (I I 1) may be used as a reaction mixture or in a crude form, or in a conventional manner.
- Z represents a lithium or magnesium halide (eg, one MgBr, —Mgl, etc.), and other symbols have the same meanings as described above. ]
- the compound (IV) can be usually produced by reacting the compound (III) with lithium or magnesium in a suitable solvent to give the compound (III). 1-4 equivalents for, rather then favored reacting lithium or magnesium 1-2 equivalents c
- solvent to be used examples include ether solvents such as dried tetrahydrofuran, getyl ether, dibutyl ether and the like. These solvents may be used alone or hydrocarbons (eg, toluene, etc.). ), And amines (eg, triethylamine) may be used as a mixed solvent with other solvents.
- the reaction temperature is between room temperature and 150 ° C, preferably between 40 and 100 ° C.
- the reaction time is from 10 minutes to 48 hours, preferably from 30 minutes to 6 hours. If needed iodine to the reaction of the activating agent, Jiburomuetan, Echirubu b e the amount of using a small amount of such Mi de is 0.0 0 1 to 0.4 equivalents, it is preferred and rather 0.0 0 5 ⁇ 0.2 equivalents.
- the obtained compound (IV) can be used in the next step as a reaction solution or as a crude product.
- L is a halogen atom (eg, a chlorine atom, a bromine atom, an iodine atom, etc.), an alkoxy (eg, a lower alkoxy such as methoxy, ethoxy, propoxy, etc.) It represents Dazoru 1-yl or N-methyl-1-N-methoxyamino, and the other symbols have the same meanings as above. ]
- halogen atom eg, a chlorine atom, a bromine atom, an iodine atom, etc.
- an alkoxy eg, a lower alkoxy such as methoxy, ethoxy, propoxy, etc.
- the compound represented by the general formula (VI) can be produced by reacting the compound (IV) with the compound (V) in a suitable solvent (single or mixed).
- compound (V) can be used in an amount of 1 equivalent or more, preferably 1 to 3 equivalents, relative to compound (IV).
- Solvents that can be used include aromatic hydrocarbons (eg, toluene, benzene, xylene, etc.), saturated hydrocarbons (eg, cyclohexane, hexane, etc.), Examples thereof include ters (eg, tetrahydrofuran, getyl ether, dioxane, etc.), triethylamine, and a mixed solvent thereof.
- aromatic hydrocarbons eg, toluene, benzene, xylene, etc.
- saturated hydrocarbons eg, cyclohexane, hexane, etc.
- ters eg, tetrahydrofuran, getyl ether, dioxane, etc.
- triethylamine ethylamine
- the reaction temperature is from 100 to 100, preferably from -80 to 40.
- the reaction time varies depending on the compound, but the reaction may be carried out for 0.5 to 80 hours.
- the resulting compound (VI) can be purified as a crude product or by a conventional method (eg, column chromatography, recrystallization, etc.) and used in the next step.
- compound (VII1) can be produced by reacting compound (VI) with a salt of compound (VII) in a suitable solvent in the presence of a base.
- Compound (VII) is used in 1 to 4 equivalents, preferably 1 to 2.5 equivalents, relative to compound (VI).
- Examples of the salt of the compound (VII) include mineral acid salts such as hydrochloride and sulfate. ⁇
- Examples of the base that can be used include amines (triethylamine, pyridine, etc.), and the amount used is based on the amount of the salt of compound (VII). It is 1-3 equivalents, preferably 1-2 equivalents.
- Solvents that can be used include, for example, hydrocarbons (eg, benzene, toluene, xylene, etc.) and halogenated hydrocarbons (eg, chloroform, 1,2-dichloroethane) Etc.), ethers (eg, tetrahydrofuran, dioxane, etc.), alcohols (eg, methanol, ethanol, n- lobanol, isopropanol) ), Water and a mixed solvent thereof.
- hydrocarbons eg, benzene, toluene, xylene, etc.
- halogenated hydrocarbons eg, chloroform, 1,2-dichloroethane
- ethers eg, tetrahydrofuran, dioxane, etc.
- alcohols eg, methanol, ethanol, n- lobanol, isopropanol
- the reaction temperature is from 0 to 150: preferably from 20 to 120 °.
- the reaction time is usually about 15 minutes to 24 hours.
- the obtained compound (VIII) may be used as is in the next step after purification as a reaction solution or in crude form, or by a conventional method (eg, column chromatography, recrystallization, etc.). It can be.
- the benzaldehyde derivative represented by the general formula (IX) can be produced by oxidizing the compound (VIII) with various oxidizing agents.
- Oxidizing agents that can be used include, for example, pyridinium chromate, tert-butyl chromate, nickel peroxide, activated dimethyl sulfoxide and the like. No.
- Various activated dimethyl sulfoxide oxidation methods using activated dimethyl sulfoxide are known, and when the method is used for production by Swer.n oxidation, dimethyl sulfoxide and dimethyl sulfoxide are required.
- the oxalyl chloride used as an electronic agent can be used in an amount of 1 equivalent or more, preferably 1 to 4 equivalents, to the compound (VIII), respectively.
- Examples of the solvent that can be used include halogenated hydrocarbons such as dichloromethane.
- the reaction temperature is from 178 to 120 X :, preferably from 178 to 400 :.
- the reaction time varies depending on the compound, but it is sufficient to carry out the reaction for 15 minutes to 3 hours. Subsequently, a base such as triethylamine is added to form a sulfodiimide.
- the reaction time varies depending on the compound, but it is recommended that the reaction be performed for 15 minutes to 3 hours.
- water is added and the product is extracted with a solvent.
- the obtained compound (IX) is a novel compound and is included in the present invention. If necessary, compound (IX) can be purified by a conventional method (eg, column chromatography, recrystallization, etc.).
- the compound of the present invention represented by the general formula (I) is a compound of the formula (IX), a hydrazone represented by the compound (X), an o-substituted hydroxylamine, a hydrazine derivative and a hydrazine derivative.
- a salt eg, hydrochloride, sulfate
- suitable solvent solvent
- compound (X) can be used in an amount of 1 equivalent or more, preferably 1 to 3 equivalents, relative to compound (IX).
- solvents examples include aromatic hydrocarbons (eg, toluene, benzene, xylene, etc.), saturated hydrocarbons (eg, cyclohexane, hexane, etc.), and alcohols. (Eg, methanol, ethanol, etc.), ethers (eg, tetrahydrofuran, dioxane, etc.), water and a mixed solvent thereof.
- aromatic hydrocarbons eg, toluene, benzene, xylene, etc.
- saturated hydrocarbons eg, cyclohexane, hexane, etc.
- alcohols eg, methanol, ethanol, etc.
- ethers eg, tetrahydrofuran, dioxane, etc.
- the reaction temperature is from 0 to 160, preferably from 20 to 130. C.
- the reaction time varies depending on the compound, but the reaction may be carried out for 0.5 to 90 hours. Five
- the desired compound (I) thus obtained can be purified by a conventional method (eg, column chromatography, recrystallization, etc.), if necessary.
- the hydrazone derivative represented by the compound (X) used as a raw material in this reaction can be produced by reacting the corresponding ketone derivative with hydrazine.
- the o-substituted hydroxylamin derivatives represented by the compound (X) are known in the art, and are known from Houben-Weyl's “Met-Ten-Tenole Onoreganischen”. Mi - (M ethodender O rganischen C hemie ) "XZ l Certificates c that can have a this to produce Ri by the known method similar to the method described in
- the hydrazine derivative represented by the compound (X) is a known hydrazine derivative of H. ouben-Weyl (Methodenender Oranischen Chemie). ) j XZ It can be manufactured by a known method similar to the method described in the second volume.
- compound (XI) can be produced by reacting compound (IX) with hydroxylamine or a salt thereof in a suitable solvent. 1-4 equivalents to (IX), preferred Or 1 to 2.5 equivalents can be used.
- Examples of the salts of hydroxylaminate include mineral salts such as hydrochloride and sulfate. When the salt is used, it may be neutralized with a base and reacted.
- bases that can be used include metal hydroxides (eg, sodium hydroxide, potassium hydroxide, etc.) and metal carbonates (eg, sodium carbonate, carbonate) Potassium, etc.), metal alkoxides (eg, sodium methoxide, sodium ethoxide, etc.), pyridine, etc., and the amount of use is the amount of hydroxylamine salt. 1 to 3 equivalents, preferably 1 to 2 equivalents.
- Solvents that can be used include, for example, hydrocarbons (eg, benzene, toluene, xylene, etc.), halogenated hydrocarbons (eg, macro-form, 1,2-dichloroethane, etc.), Ethers (eg, tetrahydrofuran, dioxane, etc.), alcohols (eg, methanol, ethanol, n-propanol, isopropanol, etc.), water and their mixed solvents And so on.
- hydrocarbons eg, benzene, toluene, xylene, etc.
- halogenated hydrocarbons eg, macro-form, 1,2-dichloroethane, etc.
- Ethers eg, tetrahydrofuran, dioxane, etc.
- alcohols eg, methanol, ethanol, n-propanol, isopropanol, etc.
- the reaction temperature is from 0 to 150 °: preferably from 20 to 100 °.
- the reaction time is usually about 15 minutes to 24 hours.
- the resulting compound (XI) can be used as is in the reaction mixture or in crude form, or purified by a conventional method (eg, column chromatography, recrystallization, etc.) and used in the next step.
- a conventional method eg, column chromatography, recrystallization, etc.
- the compound of the present invention represented by the general formula (Ia) is produced by reacting compound (XI) and compound (XII) in the presence of a base without solvent or in a suitable solvent (single or mixed). can do.
- compound (XII) can be used in an equivalent amount or more to compound (XI).
- bases examples include metal hydrides (eg, sodium hydride, potassium hydride, etc.), metal hydroxides (eg, sodium hydroxide, potassium hydroxide).
- Metal carbonates eg, sodium carbonate, potassium carbonate, etc.
- metal alkoxides eg, sodium methoxide, sodium ethoxide, potassium tert-
- Butoxide etc.
- one or more equivalents, preferably one to two equivalents, of compound (XI) can be used.
- Examples of usable solvents include N, N-dimethylformamide, dimethylsulfoxide, aromatic hydrocarbons (eg, toluene, benzene, xylene, etc.), and saturated hydrocarbons (eg, cyclohexane Hexane, hexane, etc.), halogenated hydrocarbons (eg, dichloromethane, 1,2-dichloroethane, etc.), ethers (eg, tetrahydrofuran, dioxane, etc.), ketone (Eg, acetone, methylethylketone, etc.), nitriles (eg, acetonitrile, etc.), water and a mixed solvent thereof.
- the reaction temperature is from 130 to 120, preferably from 0 to 90.
- the reaction time varies depending on the compound, but the reaction may be carried out for 0.5 to 90 hours.
- the desired compound (Ia) thus obtained can be purified by a conventional method (eg, column chromatography, recrystallization, etc.), if necessary.
- the compound represented by the general formula (XIV) can be produced by halogenating the methyl group of the benzene ring of the compound (XIV) by a known method.
- halogenating agents such as succinic acid, if necessary, using a mercury lamp under light irradiation, or a, Q'-azoisopeptylyl nitrile, a radical initiator such as dibenzoyl peroxide, etc.
- the halogenating agent can be used in one or more equivalents, preferably 1 to 1.5 equivalents, relative to compound (XIII).
- the radical initiator can be used in an amount of 0.01 equivalent or more, preferably 0.05 to 0.5 equivalent, relative to the compound (XIII):
- the reaction temperature is from 20 to 120 ° C, preferably from 50 to 90 ° C.
- reaction time varies depending on the compound, but the reaction may be performed for 5 minutes to 3 hours:
- the desired compound (XIV) thus obtained is used as it is in the next step after being purified as it is or in the form of a crude reaction solution, or by a conventional method (eg, column chromatography, recrystallization, etc.). can do.
- the compound (XIII) used as a starting material in this reaction can be produced according to Example 2 using 2-bromotoluene as a starting material.
- the compound represented by the general formula (XVI) can be obtained by benzoyloxylation of the compound (XIV) without solvent or in an appropriate solvent (single or mixed) (even if the phenyl group in the benzoyloxy group is substituted). Good) or alkanoyloxylation (the alkyl group in the alkanoyloxy group may be substituted).
- Benzoyloxylation and alkanoyloxylation can be carried out by reacting compound (XIV) with the general formula (XV):
- R ′ represents an optionally substituted alkyl group or an optionally substituted phenyl group:
- a metal salt of a carboxylic acid represented by eg, lithium, sodium
- the reaction is carried out by reacting the carboxylic acid in the presence of a force for reacting an alkali metal such as calcium; an alkaline earth metal such as magnesium or potassium, or in the presence of a base.
- the metal salt is preferably sodium phosphate, potassium acetate, sodium benzoate, potassium benzoate.
- the amount of the metal salt of the carboxylic acid or the carboxylic acid to be used is 1 equivalent or more, preferably 1 to 3 equivalents, relative to compound (XIV).
- Examples of the base include metal hydroxides (eg, sodium hydroxide, potassium hydroxide, etc.) and gold hydrides (eg, sodium hydride, lithium hydride, etc.) , Metal carbonates (eg, sodium carbonate, potassium carbonate, etc.), gold bicarbonates (eg, sodium hydrogen carbonate, potassium hydrogen carbonate, etc.), and the like.
- Examples of usable solvents include N, N-dimethylformamide, dimethylsulfoxide, aromatic hydrocarbons (eg, toluene, benzene, xylene, etc.), and saturated hydrocarbons (eg, , Cyclohexane, hexane, etc.), halogenated hydrocarbons (eg, dichloromethane, 1,2-dichloroethane, etc.), ethers (eg, tetrahydrofuran, dioxane, etc.) ), Ketones (eg, acetone, methylethyl ketone, etc.), nitriles (eg, acetonitril, etc.), water and mixed solvents thereof.
- the reaction temperature is from 130 to 120 :, preferably from 0 to 90 :.
- the reaction time varies depending on the compound, but the reaction may be carried out for 0.5 to 90 hours.
- the desired compound (XVI) obtained may be used as is in the next step, either as a reaction mixture or as a crude product, or purified by a conventional method (eg, column chromatography, recrystallization, etc.). It can be.
- compound (XVII) can be produced by reacting compound (XVI) with a salt of compound (VII) in a suitable solvent in the presence of a base.
- Compound (VII) is used in 1 to 4 equivalents, preferably 1 to 2.5 equivalents, relative to compound (XVI).
- Examples of the salt of the compound (VII) include mineral acid salts such as hydrochloride and sulfate. When using the salt, neutralize with a base and react
- Examples of the base that can be used include, for example, amines (eg, pyridine), and the amount of the base to be used is 1 to 3 equivalents, preferably 1 equivalent to the salt of the compound (VII). Or 1-2 equivalents.
- amines eg, pyridine
- the amount of the base to be used is 1 to 3 equivalents, preferably 1 equivalent to the salt of the compound (VII). Or 1-2 equivalents.
- Solvents that can be used include, for example, hydrocarbons (eg, benzene, toluene, xylene, etc.), halogenated hydrocarbons (eg, chloroform, 1,2-dichlorobenzene) Etc.), ethers (eg, tetrahydrofuran, dioxane, etc.), alcohols (eg, methanol, ethanol, n-probanol, i And water and a mixed solvent thereof.
- hydrocarbons eg, benzene, toluene, xylene, etc.
- halogenated hydrocarbons eg, chloroform, 1,2-dichlorobenzene
- ethers eg, tetrahydrofuran, dioxane, etc.
- alcohols eg, methanol, ethanol, n-probanol, i And water and a mixed solvent thereof.
- the reaction temperature is from 0 to 150, preferably from 20 to 120 °.
- the reaction time is usually about 15 minutes to 24 hours:
- the obtained compound (XVII) can be used as it is in the form of a reaction mixture or a crude product, or purified by a conventional method (eg, column chromatography, recrystallization, etc.) and used in the next step. it can.
- reaction formula 1 2 Reaction formula 1 2
- the compound (VIII) can be produced by reacting the compound (XVII) in a suitable solvent in the presence of a base.
- Bases that can be used include, for example, metal hydroxides (eg, sodium hydroxide, potassium hydroxide, etc.), metal carbonates (eg, sodium carbonate) , Potassium carbonate, etc.), metal alkoxides (eg, sodium methoxide, sodium ethoxide, potassium tert-butoxide, etc.), and the compound (XVII) 0.01 equivalents or more, preferably 0.05 to 0.5 equivalents can be used.
- metal hydroxides eg, sodium hydroxide, potassium hydroxide, etc.
- metal carbonates eg, sodium carbonate
- Potassium carbonate e.
- metal alkoxides eg, sodium methoxide, sodium ethoxide, potassium tert-butoxide, etc.
- compound (XVII) 0.01 equivalents or more, preferably 0.05 to 0.5 equivalents can be used.
- Solvents that can be used include, for example, hydrocarbons (eg, benzene, toluene, xylene, etc.), and halogenated hydrocarbons (eg, chloroform, 1,2-dichloroethane, etc.) ), Ethers (eg, tetrahydrofuran, dioxane, etc.), alcohols (eg, methanol, ethanol, n- propanol, isopropanol) ), Water and their mixed solvents, etc.
- hydrocarbons eg, benzene, toluene, xylene, etc.
- halogenated hydrocarbons eg, chloroform, 1,2-dichloroethane, etc.
- Ethers eg, tetrahydrofuran, dioxane, etc.
- alcohols eg, methanol, ethanol, n- propanol, isopropanol
- Water and their mixed solvents etc.
- the reaction temperature is from 0 to 150, preferably from 20 to 120.
- Reaction times are typically on the order of 5 minutes to 24 hours:
- the obtained compound (VIII) may be used as is in the next step after purification as it is, in crude form, or by a conventional method (eg, column chromatography, recrystallization, etc.). You can: (Reaction formula 13)
- compound (VIII) can be produced by reacting compound (XVI) with a salt of compound (VII) in a suitable solvent.
- Compound (VII) is from 1 to 4 equivalents relative to compound (XVI), and preferred rather is 1 to 2.5 equivalents using c
- Examples of the salt of the compound (VII) include mineral acid salts such as hydrochloride and sulfate.
- Solvents that can be used include, for example, hydrocarbons (eg, benzene, toluene, xylene, etc.), halogenated hydrocarbons (eg, black form, 1,2-dichloroethane) ), Ethers (eg, tetrahydrofuran, dioxane, etc.), alcohols (eg, methanol, ethanol, n -propanol, isopropanol, etc.), Examples thereof include water and a mixed solvent thereof.
- hydrocarbons eg, benzene, toluene, xylene, etc.
- halogenated hydrocarbons eg, black form, 1,2-dichloroethane
- Ethers eg, tetrahydrofuran, dioxane, etc.
- alcohols eg, methanol, ethanol, n -propanol, isopropanol, etc.
- Examples thereof include water and a mixed solvent
- the reaction temperature is from 0 to 150, preferably from 20 to: 120.
- the reaction time is usually about 15 minutes to 24 hours.
- the obtained compound (VIII) can be used as is in the reaction solution or in crude form, or purified by a conventional method (eg, column chromatography, recrystallization, etc.) and used in the next step. it can.
- the compound (I) of the present invention may be a cultivated plant or a seed thereof, for example, rice, wheat, rye, rye, corn, millet, buckwheat, soybean, soybean, and soybean.
- the compound of the present invention is particularly useful for rice blast fungus (Pyricularia oryzae), rice sheath blight fungus (Rhizoc toni a so1ani), and wheat powdery mildew fungus.
- the compound (I) of the present invention has excellent insecticidal activity against plant pests. In particular, it shows an excellent control effect on insects such as Myzus persicae which damage various plants. Therefore, the compound (I) of the present invention is also useful as a biocide.
- the compound (I) of the present invention is used as a fungicide
- the compound is applied by spraying, spraying, or applying an active substance to the plant, or by treating the plant seed, or the soil around the plant, or the seed. This can be achieved by treating the soil, rice paddy, and water for hydroponic cultivation with active substances.
- the application can be made before or after the plant is infected with the pathogen.
- the compound (I) of the present invention When used as an insecticide, it is applied to insects.
- the active substance is treated by spraying, spraying, or applying. It is applied to plants by fogging, spraying, and application to prevent pest damage. Alternatively, it may be applied to plant seeds, soil around the plant, soil to sow seeds, and paddy fields.
- the compound may be used in the usual pharmaceutical form, for example, liquid, wettable powder, emulsifier, suspension, liquid concentrate, tablet, granule, aerosol, powder, paste, smoker, etc. It can be used as a chemical suitable for widespread disinfection and pesticides.
- Such embodiments may be useful for improving at least one compound of the present invention and suitable solid or liquid carriers and, if desired, the dispersibility of the active substance and other properties. It can be obtained by usual methods of mixing with suitable auxiliaries (eg surfactants, spreading agents, dispersants, stabilizers).
- suitable auxiliaries eg surfactants, spreading agents, dispersants, stabilizers.
- solid carriers or diluents include botanicals such as cereal flour, tobacco stalk flour, soy flour, walnut husk flour, vegetable flour, canna flour, bran, bark flour, fiber flour, Vegetable extract residue), fibrous substances (eg, paper, cardboard, rags), artificial plastic powders, clay (eg, kaolin, bentonite, clay), talc and inorganic substances (leaf leaves)
- botanicals such as cereal flour, tobacco stalk flour, soy flour, walnut husk flour, vegetable flour, canna flour, bran, bark flour, fiber flour, Vegetable extract residue
- fibrous substances eg, paper, cardboard, rags
- artificial plastic powders eg, clay (eg, kaolin, bentonite, clay), talc and inorganic substances (leaf leaves)
- clay eg, kaolin, bentonite, clay
- talc and inorganic substances leaf leaves
- examples include calcite, sericite, pumice, sulfur powder
- Liquid carriers and diluents include water, alcohols (eg, methanol, ethanol), ketones (eg, acetate, methylethylketone), ethers (eg, , Getyl ether, dioxane, cellosolve, tetrahydrofuran), aromatic hydrocarbons (eg, benzene, toluene, xylene, methyl naphthalene), aliphatic hydrocarbons (eg, gasoline) Lin, kerosene, kerosene), esters, nitriles, acid amides (eg, N, N-dimethylformamide, N, N-dimethylacetamide), halogenation Hydrocarbons (eg For example, dichloroethane, carbon tetrachloride).
- alcohols eg, methanol, ethanol
- ketones eg, acetate, methylethylketone
- ethers eg, Getyl
- surfactants include alkyl sulfates, alkyl sulfonates, alkynoleyl sulfonates, polyethylene glycols, and polyhydric alcohol esters.
- spreading or dispersing agents include casein, gelatin, starch powder, carboxymethyl cellulose, arabia gum, alginic acid, lignin, bentonite, molasses, poly (vinyl alcohol), pine oil and agar. And so on.
- Stabilizers include PAP (isopropyl pyrinate mixture), tricresyl phosphate (TCP), tall oil, epoxy oil, surfactants, fatty acids and their esters. Is mentioned.
- formulations of the present invention can be used in admixture with other fungicides, insecticides, herbicides, or fertilizers.
- the above-mentioned preparations contain at least one compound represented by the general formula (I) of the present invention in an amount of 0.1 to 95% by weight, preferably 1.0 to 80% by weight. These preparations can be used alone or in a diluted form.
- the compound of the present invention about 1 g to 5.0 Kg / hectare, preferably about 10 g to 1.0 Kg / h. Hector is usually used at a concentration of about 1 to 5,000 ppm, preferably about 100 to 1,000 ppm.
- 1-bromo-2-(-) was added to a suspension of 2.63 g (0.108 mo1) of magnesium, 0.2 ml of bromoethane and 5 ml of tetrahydrofuran. 1 Add a mixture of 18.6 g (0.072 mo1) of ethoxymethylbenzene and 67 ml of tetrahydrofuran at 50-55 over 30 minutes.
- the mixture was stirred at 50-55 for 1 hour to prepare a Grignard reagent: the Grignard reagent was added to the N-meth Xy N—Methyl 1—2—Sosoxazoline 1—3-Rubonic acid amide 7.59 g (0.048 mol) and a mixture of 70 ml of tetrahydrofuran The solution was dropped at a rate of 16 or less. After the dropwise addition, the mixture was stirred for 1.5 hours at ⁇ 50 to 10 ° C. After adding 200 ml of water, a saturated aqueous solution of ammonium chloride was added until the insoluble material was dissolved, and the mixture was extracted twice with 100 ml of ether. did.
- test solution was prepared by dissolving the compound in a small amount of NN-dimethylformamide and diluting it to a predetermined concentration with distilled water containing an adhesive.
- the test liquid was sprayed on the test plant, and 24 hours later, the pathogen was inoculated by the method described below.
- the control rate was calculated by the following formula.
- the seedlings were sown on plastic cups with a diameter of 9 cm and raised for 2 to 3 weeks.
- the compound solution or suspension solution was applied to the surface of the first true leaf of the seedlings (variety: Tsukuba Shirobo).
- the pathogen was inoculated by spraying a conidia suspension of the powdery mildew fungus (Sphaerotheca ful iginea) cultured on the leaves of Cucumber. After inoculation, the plants were kept in 20 greenhouses for 10 days, and the area occupied by the signs that appeared on the inoculated leaves was investigated to determine the control rate.
- A-one 6 7 1 0 0
- the seedlings were seeded on a plastic cup with a diameter of 9 cm and raised for 2 to 3 weeks.
- the compound solution or suspension was sprayed on the surface of the first true leaves of the cucumber (variety: Tsukuba Shirobo).
- the pathogen was inoculated by spraying a suspension of zoospores of cucumber and Pseudoperonospora cubens is cultivated on green leaves and a solution or suspension of arsenic compound. It was performed by dropping on the surface of the leaves. After inoculation, they were kept for 10 days in the wet room of No. 2 and the extent of lesions appearing around the inoculated area was investigated to determine the control rate.
- A-one 6 7 1 0 0
- the seeds were sown on plastic cups with a diameter of 9 cm and seedlings were raised for 2 to 3 weeks.
- the pathogen was inoculated by removing conidia of the wheat powdery mildew (Erysiphe graminis f. Sp. Tritici) cultured on the wheat leaves from the test plant. After inoculation, the plants were kept in a greenhouse of 20 m2 for 10 days, and then the area occupied by the signs that appeared on the inoculated leaves was investigated to determine the control rate.
- Chinese cabbage leaf pieces having a diameter of 3 cm were placed on a 0.3% agar gel with the back side facing up, and inoculated with wingless adults, kept at 25 for 1 day, and the number of litters was counted. Subsequently, the adult was removed, and a test solution at a predetermined level was sprayed on the larvae on the Chinese cabbage leaf pieces.
- test solution was prepared by dissolving the compound in a small amount of N, N-dimethylformamide and diluting it with distilled water containing a surfactant to a predetermined concentration.
- the present invention provides a novel ⁇ -alkoxyiminobenzyl heterocyclic derivative having excellent bactericidal and insecticidal activities, an intermediate for the production thereof, and an agricultural chemical containing the same as an active ingredient.
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- 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)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU70951/96A AU7095196A (en) | 1995-09-29 | 1996-09-25 | Alpha-alkoxyiminobenzyl heterocyclic derivatives, intermediates for preparing the same, and agricultural chemicals containing the same as active ingredient |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP7/277211 | 1995-09-29 | ||
JP27721195 | 1995-09-29 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1997012875A1 true WO1997012875A1 (fr) | 1997-04-10 |
Family
ID=17580365
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP1996/002766 WO1997012875A1 (fr) | 1995-09-29 | 1996-09-25 | DERIVES HETEROCYCLIQUES D'α-ALCOXY-IMINOBENZYLE, INTERMEDIAIRES POUR LEUR PREPARATION, ET PRODUITS CHIMIQUES AGRICOLES CONTENANT LESDITS DERIVES EN TANT QUE PRINCIPE ACTIF |
Country Status (2)
Country | Link |
---|---|
AU (1) | AU7095196A (fr) |
WO (1) | WO1997012875A1 (fr) |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1994022844A1 (fr) * | 1993-04-07 | 1994-10-13 | Zeneca Limited | Derives fongicides d'oxazolyle et d'oxadiazolyle |
-
1996
- 1996-09-25 AU AU70951/96A patent/AU7095196A/en not_active Abandoned
- 1996-09-25 WO PCT/JP1996/002766 patent/WO1997012875A1/fr active Application Filing
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1994022844A1 (fr) * | 1993-04-07 | 1994-10-13 | Zeneca Limited | Derives fongicides d'oxazolyle et d'oxadiazolyle |
Also Published As
Publication number | Publication date |
---|---|
AU7095196A (en) | 1997-04-28 |
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