TW536387B - Pyrazolinone compound - Google Patents
Pyrazolinone compound Download PDFInfo
- Publication number
- TW536387B TW536387B TW088106396A TW88106396A TW536387B TW 536387 B TW536387 B TW 536387B TW 088106396 A TW088106396 A TW 088106396A TW 88106396 A TW88106396 A TW 88106396A TW 536387 B TW536387 B TW 536387B
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- compound
- allyl
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- -1 Pyrazolinone compound Chemical class 0.000 title claims abstract description 150
- 150000001875 compounds Chemical class 0.000 claims abstract description 214
- 125000005843 halogen group Chemical group 0.000 claims abstract description 33
- 201000010099 disease Diseases 0.000 claims abstract description 31
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 31
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 17
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 10
- 239000004480 active ingredient Substances 0.000 claims abstract description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 5
- 238000011049 filling Methods 0.000 claims description 106
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 90
- 239000000203 mixture Substances 0.000 claims description 62
- 230000002079 cooperative effect Effects 0.000 claims description 51
- 125000003545 alkoxy group Chemical group 0.000 claims description 27
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 25
- 125000004414 alkyl thio group Chemical group 0.000 claims description 21
- 241000196324 Embryophyta Species 0.000 claims description 20
- XBYRMPXUBGMOJC-UHFFFAOYSA-N 1,2-dihydropyrazol-3-one Chemical class OC=1C=CNN=1 XBYRMPXUBGMOJC-UHFFFAOYSA-N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 15
- 125000005108 alkenylthio group Chemical group 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 241000219112 Cucumis Species 0.000 claims description 4
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 7
- 125000003302 alkenyloxy group Chemical group 0.000 claims 4
- 125000005133 alkynyloxy group Chemical group 0.000 claims 4
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 claims 3
- RBIIKVXVYVANCQ-CUWPLCDZSA-N (2s,4s,5s)-5-amino-n-(3-amino-2,2-dimethyl-3-oxopropyl)-6-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]-4-hydroxy-2-propan-2-ylhexanamide Chemical compound C1C(C)(C)N(C[C@H](N)[C@@H](O)C[C@@H](C(C)C)C(=O)NCC(C)(C)C(N)=O)CC(=O)N1C1=CC=CC=C1Cl RBIIKVXVYVANCQ-CUWPLCDZSA-N 0.000 claims 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- HUTNOYOBQPAKIA-UHFFFAOYSA-N 1h-pyrazin-2-one Chemical class OC1=CN=CC=N1 HUTNOYOBQPAKIA-UHFFFAOYSA-N 0.000 claims 1
- 241000894006 Bacteria Species 0.000 claims 1
- 230000001276 controlling effect Effects 0.000 claims 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims 1
- 150000007857 hydrazones Chemical class 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 abstract description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 180
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 122
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 95
- 239000000543 intermediate Substances 0.000 description 86
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 60
- 238000006243 chemical reaction Methods 0.000 description 57
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 53
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 51
- 238000004519 manufacturing process Methods 0.000 description 48
- 238000010992 reflux Methods 0.000 description 43
- 239000002904 solvent Substances 0.000 description 42
- 239000012044 organic layer Substances 0.000 description 37
- 238000003756 stirring Methods 0.000 description 34
- 239000000243 solution Substances 0.000 description 32
- 239000000706 filtrate Substances 0.000 description 31
- 125000000217 alkyl group Chemical group 0.000 description 30
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium;hydroxide;hydrate Chemical compound [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 29
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 25
- 229940125782 compound 2 Drugs 0.000 description 24
- 238000000605 extraction Methods 0.000 description 23
- 238000001816 cooling Methods 0.000 description 21
- 238000002844 melting Methods 0.000 description 21
- 230000008018 melting Effects 0.000 description 21
- 239000003960 organic solvent Substances 0.000 description 21
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
- PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 20
- 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 20
- 230000018044 dehydration Effects 0.000 description 19
- 238000006297 dehydration reaction Methods 0.000 description 19
- 238000010898 silica gel chromatography Methods 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 239000012046 mixed solvent Substances 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 125000001309 chloro group Chemical group Cl* 0.000 description 16
- 125000001188 haloalkyl group Chemical group 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 15
- 229910000103 lithium hydride Inorganic materials 0.000 description 15
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 14
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 13
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 12
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000000460 chlorine Substances 0.000 description 12
- 229940125904 compound 1 Drugs 0.000 description 12
- 125000004093 cyano group Chemical group *C#N 0.000 description 12
- 229910052783 alkali metal Inorganic materials 0.000 description 11
- KVGZZAHHUNAVKZ-UHFFFAOYSA-N 1,4-Dioxin Chemical compound O1C=COC=C1 KVGZZAHHUNAVKZ-UHFFFAOYSA-N 0.000 description 10
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 10
- 230000002378 acidificating effect Effects 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 10
- 239000003153 chemical reaction reagent Substances 0.000 description 10
- 229940126214 compound 3 Drugs 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 125000004995 haloalkylthio group Chemical group 0.000 description 10
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
- 235000019341 magnesium sulphate Nutrition 0.000 description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
- 239000008096 xylene Substances 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 125000000304 alkynyl group Chemical group 0.000 description 9
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 9
- 229910052801 chlorine Inorganic materials 0.000 description 9
- 230000035484 reaction time Effects 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 101150085479 CHS2 gene Proteins 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 125000002723 alicyclic group Chemical group 0.000 description 8
- 229940125898 compound 5 Drugs 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 125000003342 alkenyl group Chemical group 0.000 description 7
- 150000002170 ethers Chemical class 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 235000012149 noodles Nutrition 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 229910000104 sodium hydride Inorganic materials 0.000 description 7
- 125000006519 CCH3 Chemical group 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
- 240000008067 Cucumis sativus Species 0.000 description 5
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- 101100113485 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) chs-3 gene Proteins 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 230000000844 anti-bacterial effect Effects 0.000 description 4
- BQWQGEBNCNNFCI-UHFFFAOYSA-N butan-2-yl methanesulfonate Chemical compound CCC(C)OS(C)(=O)=O BQWQGEBNCNNFCI-UHFFFAOYSA-N 0.000 description 4
- 239000007810 chemical reaction solvent Substances 0.000 description 4
- 239000004927 clay Substances 0.000 description 4
- 239000013256 coordination polymer Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- CAEWJEXPFKNBQL-UHFFFAOYSA-N prop-2-enyl carbonochloridate Chemical compound ClC(=O)OCC=C CAEWJEXPFKNBQL-UHFFFAOYSA-N 0.000 description 4
- SWWHCQCMVCPLEQ-UHFFFAOYSA-N propan-2-yl methanesulfonate Chemical compound CC(C)OS(C)(=O)=O SWWHCQCMVCPLEQ-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- QCMHWZUFWLOOGI-UHFFFAOYSA-N s-ethyl chloromethanethioate Chemical compound CCSC(Cl)=O QCMHWZUFWLOOGI-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000005995 Aluminium silicate Substances 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- 241000221785 Erysiphales Species 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 3
- 125000005109 alkynylthio group Chemical group 0.000 description 3
- 235000012211 aluminium silicate Nutrition 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- LFLBHTZRLVHUQC-UHFFFAOYSA-N butyl methanesulfonate Chemical compound CCCCOS(C)(=O)=O LFLBHTZRLVHUQC-UHFFFAOYSA-N 0.000 description 3
- 239000001768 carboxy methyl cellulose Substances 0.000 description 3
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 3
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 3
- 230000006837 decompression Effects 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 230000036571 hydration Effects 0.000 description 3
- 238000006703 hydration reaction Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 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 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000005017 substituted alkenyl group Chemical group 0.000 description 3
- 125000000547 substituted alkyl group Chemical group 0.000 description 3
- 125000004426 substituted alkynyl group Chemical group 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 2
- 241000213004 Alternaria solani Species 0.000 description 2
- 101150041968 CDC13 gene Proteins 0.000 description 2
- 101100274581 Caenorhabditis elegans chc-1 gene Proteins 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000222199 Colletotrichum Species 0.000 description 2
- 235000009075 Cucumis anguria Nutrition 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 241000896246 Golovinomyces cichoracearum Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- 241000233679 Peronosporaceae Species 0.000 description 2
- 241000233622 Phytophthora infestans Species 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 241000221662 Sclerotinia Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 244000269722 Thea sinensis Species 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 125000005083 alkoxyalkoxy group Chemical group 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000004659 aryl alkyl thio group Chemical group 0.000 description 2
- 239000012752 auxiliary agent Substances 0.000 description 2
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- LAYPMCGIWDGYKX-UHFFFAOYSA-N trichloromethyl hydrogen carbonate Chemical compound OC(=O)OC(Cl)(Cl)Cl LAYPMCGIWDGYKX-UHFFFAOYSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 210000004916 vomit Anatomy 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000010457 zeolite Substances 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/16—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof the nitrogen atom being part of a heterocyclic ring
-
- 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
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
- C07D231/52—Oxygen atom in position 3 and nitrogen atom in position 5, or vice versa
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
- Photoreceptors In Electrophotography (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11329098 | 1998-04-23 | ||
| JP28248798 | 1998-10-05 | ||
| JP33944198 | 1998-11-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW536387B true TW536387B (en) | 2003-06-11 |
Family
ID=27312474
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW088106396A TW536387B (en) | 1998-04-23 | 1999-04-21 | Pyrazolinone compound |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US6294567B1 (enExample) |
| EP (1) | EP1072598B9 (enExample) |
| JP (1) | JP5152129B2 (enExample) |
| KR (1) | KR100583216B1 (enExample) |
| CN (1) | CN1247546C (enExample) |
| AT (1) | ATE327979T1 (enExample) |
| AU (1) | AU755953B2 (enExample) |
| BE (1) | BE2014C061I2 (enExample) |
| BR (1) | BR9909841B1 (enExample) |
| DE (1) | DE69931623T2 (enExample) |
| ES (1) | ES2260908T3 (enExample) |
| FR (1) | FR15C0027I2 (enExample) |
| IL (1) | IL139013A (enExample) |
| PT (1) | PT1072598E (enExample) |
| TW (1) | TW536387B (enExample) |
| WO (1) | WO1999054307A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE60007651T2 (de) * | 1999-10-21 | 2004-11-11 | Sumitomo Chemical Co., Ltd. | Zusammensetzungen und verfahren zur bekämpfung von pflanzenkrankheiten |
| AU2005220260B2 (en) * | 2004-10-27 | 2010-07-01 | Sumitomo Chemical Company, Limited | Granular pesticidal composition |
| BRPI0611370A2 (pt) * | 2005-05-23 | 2010-08-31 | Sagami Chem Res | derivados de pirazol-1-carboxilato, processos para a producão destes e processos para a producão de derivados de pirazol |
| WO2007025880A2 (en) * | 2005-08-31 | 2007-03-08 | F. Hoffmann-La Roche Ag | Pyrazolone derivatives as 11-beta hsd1 inhibitors |
| JP5365041B2 (ja) * | 2008-03-25 | 2013-12-11 | 住友化学株式会社 | 植物病害防除組成物および植物病害防除方法 |
| JP5365047B2 (ja) * | 2008-03-28 | 2013-12-11 | 住友化学株式会社 | 植物病害防除組成物および植物病害防除方法 |
| AU2013228008B2 (en) * | 2008-03-28 | 2015-06-18 | Sumitomo Chemical Company, Limited | Plant disease controlling composition and method for controlling plant disease |
| EP2306832A2 (en) * | 2008-06-05 | 2011-04-13 | Basf Se | Synergistic fungicidal mixtures |
| JP2011016790A (ja) * | 2009-06-08 | 2011-01-27 | Sumitomo Chemical Co Ltd | ピラゾリノン誘導体の精製方法 |
| JP5811736B2 (ja) | 2010-11-12 | 2015-11-11 | 住友化学株式会社 | ピラゾリノン誘導体の製造方法 |
| JP6011045B2 (ja) | 2012-06-12 | 2016-10-19 | 住友化学株式会社 | 植物病害防除組成物及び植物病害防除方法 |
| BR112015023270A2 (pt) | 2013-03-15 | 2017-07-18 | Kaken Pharma Co Ltd | derivado de pirazolinona policíclico e herbicida compreendendo o mesmo como componente efetivo |
| CN113575594B (zh) | 2013-10-03 | 2022-10-04 | 先正达参股股份有限公司 | 杀真菌组合物 |
| WO2017085057A1 (en) * | 2015-11-17 | 2017-05-26 | Sabic Global Technologies B.V. | Polymer composition having improved impact strength |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2319281A1 (de) * | 1973-04-17 | 1974-11-07 | Bayer Ag | Diuretisches und antihypertensives mittel |
| DE3738963A1 (de) * | 1987-11-17 | 1989-05-24 | Bayer Ag | 3-aminopyrazolin-5-one |
| JP3780541B2 (ja) | 1994-03-30 | 2006-05-31 | 住友化学株式会社 | 植物病害防除剤 |
| BG61811B1 (en) | 1994-03-30 | 1998-06-30 | Sumitomo Chemical Company, Limited | Preparation for plant disease control |
| JPH08301867A (ja) | 1995-05-12 | 1996-11-19 | Sumitomo Chem Co Ltd | ピラゾリン誘導体、その用途およびその製造中間体 |
| WO1996036229A1 (en) | 1995-05-17 | 1996-11-21 | E.I. Du Pont De Nemours And Company | Fungicidal cyclic amides |
| CZ394097A3 (cs) | 1995-06-20 | 1998-09-16 | E. I. Du Pont De Nemours And Company | Artropodicidní a fungicidní amidy |
| WO1998023155A1 (en) | 1996-11-26 | 1998-06-04 | E.I. Du Pont De Nemours And Company | Arthropodicidal and fungicidal cyclic amides |
| JP4123542B2 (ja) | 1997-07-07 | 2008-07-23 | 住友化学株式会社 | ピラゾリノン誘導体の製造法 |
-
1999
- 1999-04-21 TW TW088106396A patent/TW536387B/zh active
- 1999-04-22 CN CNB998053783A patent/CN1247546C/zh not_active Expired - Lifetime
- 1999-04-22 PT PT99917106T patent/PT1072598E/pt unknown
- 1999-04-22 AU AU35348/99A patent/AU755953B2/en not_active Expired
- 1999-04-22 IL IL13901399A patent/IL139013A/xx not_active IP Right Cessation
- 1999-04-22 BR BRPI9909841-5A patent/BR9909841B1/pt not_active IP Right Cessation
- 1999-04-22 ES ES99917106T patent/ES2260908T3/es not_active Expired - Lifetime
- 1999-04-22 EP EP99917106A patent/EP1072598B9/en not_active Expired - Lifetime
- 1999-04-22 AT AT99917106T patent/ATE327979T1/de active
- 1999-04-22 US US09/673,888 patent/US6294567B1/en not_active Expired - Lifetime
- 1999-04-22 DE DE69931623T patent/DE69931623T2/de not_active Expired - Lifetime
- 1999-04-22 WO PCT/JP1999/002147 patent/WO1999054307A1/ja not_active Ceased
- 1999-04-22 KR KR1020007011659A patent/KR100583216B1/ko not_active Expired - Lifetime
-
2009
- 2009-08-31 JP JP2009199775A patent/JP5152129B2/ja not_active Expired - Lifetime
-
2014
- 2014-10-02 BE BE2014C061C patent/BE2014C061I2/fr unknown
-
2015
- 2015-03-19 FR FR15C0027C patent/FR15C0027I2/fr active Active
Also Published As
| Publication number | Publication date |
|---|---|
| FR15C0027I1 (enExample) | 2015-05-15 |
| AU755953B2 (en) | 2003-01-02 |
| EP1072598B9 (en) | 2007-01-24 |
| DE69931623D1 (de) | 2006-07-06 |
| PT1072598E (pt) | 2006-09-29 |
| KR20010042882A (ko) | 2001-05-25 |
| BE2014C061I2 (enExample) | 2018-09-04 |
| ES2260908T3 (es) | 2006-11-01 |
| EP1072598A1 (en) | 2001-01-31 |
| IL139013A0 (en) | 2001-11-25 |
| DE69931623T2 (de) | 2006-09-21 |
| FR15C0027I2 (fr) | 2016-04-15 |
| JP2009280615A (ja) | 2009-12-03 |
| JP5152129B2 (ja) | 2013-02-27 |
| BR9909841A (pt) | 2000-12-19 |
| CN1247546C (zh) | 2006-03-29 |
| IL139013A (en) | 2005-09-25 |
| ATE327979T1 (de) | 2006-06-15 |
| US6294567B1 (en) | 2001-09-25 |
| KR100583216B1 (ko) | 2006-05-24 |
| EP1072598B1 (en) | 2006-05-31 |
| BR9909841B1 (pt) | 2010-12-14 |
| AU3534899A (en) | 1999-11-08 |
| WO1999054307A1 (en) | 1999-10-28 |
| CN1298395A (zh) | 2001-06-06 |
| EP1072598A4 (en) | 2002-07-17 |
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Legal Events
| Date | Code | Title | Description |
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| GD4A | Issue of patent certificate for granted invention patent |