JPS6363542B2 - - Google Patents

Info

Publication number: JPS6363542B2
Authority: JP; Japan
Prior art keywords: compound; test; solution; solvent; phenyl
Prior art date: 1984-02-15
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

JP59027905A

Other languages

English (en)

Japanese (ja)

Other versions

JPS60172970A (ja

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1984-02-15

Filing date

1984-02-15

Publication date

1988-12-07

1984-02-15 Application filed filed Critical

1984-02-15 Priority to JP59027905A priority Critical patent/JPS60172970A/ja

1985-01-21 Priority to CA000472516A priority patent/CA1249832A/fr

1985-01-24 Priority to AU38057/85A priority patent/AU574126B2/en

1985-02-01 Priority to EP85101066A priority patent/EP0152031B1/fr

1985-02-01 Priority to KR1019850000636A priority patent/KR900001160B1/ko

1985-02-01 Priority to DE8585101066T priority patent/DE3577554D1/de

1985-02-01 Priority to BR8500473A priority patent/BR8500473A/pt

1985-02-01 Priority to ES540048A priority patent/ES8605783A1/es

1985-02-04 Priority to GB08502761A priority patent/GB2153355B/en

1985-09-06 Publication of JPS60172970A publication Critical patent/JPS60172970A/ja

1988-12-07 Publication of JPS6363542B2 publication Critical patent/JPS6363542B2/ja

1990-05-31 Priority to US07/531,347 priority patent/US5091539A/en

Status Granted legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims description 57
-1 magnesium halide Chemical group 0.000 claims description 18
239000000417 fungicide Substances 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
230000000855 fungicidal effect Effects 0.000 claims description 7
229910052783 alkali metal Chemical group 0.000 claims description 5
QCRFMSUKWRQZEM-UHFFFAOYSA-N cycloheptanol Chemical compound OC1CCCCCC1 QCRFMSUKWRQZEM-UHFFFAOYSA-N 0.000 claims description 5
239000011777 magnesium Substances 0.000 claims description 5
229910052749 magnesium Inorganic materials 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
125000002648 azanetriyl group Chemical group *N(*)* 0.000 claims description 4
125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 4
239000004480 active ingredient Substances 0.000 claims description 3
150000001340 alkali metals Chemical group 0.000 claims description 3
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
239000000243 solution Substances 0.000 description 36
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
239000002904 solvent Substances 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
240000008067 Cucumis sativus Species 0.000 description 16
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 16
238000000034 method Methods 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 13
201000010099 disease Diseases 0.000 description 13
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
230000000694 effects Effects 0.000 description 12
239000000284 extract Substances 0.000 description 12
238000003756 stirring Methods 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
235000009849 Cucumis sativus Nutrition 0.000 description 8
235000010799 Cucumis sativus var sativus Nutrition 0.000 description 8
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 8
230000000844 anti-bacterial effect Effects 0.000 description 7
238000004440 column chromatography Methods 0.000 description 7
239000000203 mixture Substances 0.000 description 7
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
238000005507 spraying Methods 0.000 description 7
241000221785 Erysiphales Species 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
239000002689 soil Substances 0.000 description 6
241000233866 Fungi Species 0.000 description 5
239000007818 Grignard reagent Substances 0.000 description 5
230000000903 blocking effect Effects 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
239000007789 gas Substances 0.000 description 5
150000004795 grignard reagents Chemical class 0.000 description 5
230000003902 lesion Effects 0.000 description 5
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 5
238000010992 reflux Methods 0.000 description 5
239000007921 spray Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
238000005406 washing Methods 0.000 description 5
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 4
238000001816 cooling Methods 0.000 description 4
238000001035 drying Methods 0.000 description 4
238000011081 inoculation Methods 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
230000003449 preventive effect Effects 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000011734 sodium Substances 0.000 description 4
230000001225 therapeutic effect Effects 0.000 description 4
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
125000005037 alkyl phenyl group Chemical group 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
229940125782 compound 2 Drugs 0.000 description 3
239000013078 crystal Substances 0.000 description 3
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 3
ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 3
239000000843 powder Substances 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
BSMNRTOWHBVFBP-UHFFFAOYSA-N 2-(1,2,4-triazol-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1N1N=CN=C1 BSMNRTOWHBVFBP-UHFFFAOYSA-N 0.000 description 2
CUQMEFPOLZFWDR-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)cyclohexan-1-ol Chemical compound OC1CCCCC1C1=NC=CN1 CUQMEFPOLZFWDR-UHFFFAOYSA-N 0.000 description 2
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 2
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 2
MLOZFLXCWGERSM-UHFFFAOYSA-N 8-oxabicyclo[5.1.0]octane Chemical compound C1CCCCC2OC21 MLOZFLXCWGERSM-UHFFFAOYSA-N 0.000 description 2
244000075850 Avena orientalis Species 0.000 description 2
235000007319 Avena orientalis Nutrition 0.000 description 2
239000005711 Benzoic acid Substances 0.000 description 2
241000196324 Embryophyta Species 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
230000000843 anti-fungal effect Effects 0.000 description 2
125000003943 azolyl group Chemical group 0.000 description 2
230000001580 bacterial effect Effects 0.000 description 2
235000010233 benzoic acid Nutrition 0.000 description 2
239000004927 clay Substances 0.000 description 2
229940125773 compound 10 Drugs 0.000 description 2
238000000921 elemental analysis Methods 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
239000004210 ether based solvent Substances 0.000 description 2
238000000605 extraction Methods 0.000 description 2
239000004744 fabric Substances 0.000 description 2
239000008187 granular material Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
239000000750 industrial fungicide Substances 0.000 description 2
238000011835 investigation Methods 0.000 description 2
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
239000003973 paint Substances 0.000 description 2
230000035515 penetration Effects 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
239000002994 raw material Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
239000004094 surface-active agent Substances 0.000 description 2
125000001425 triazolyl group Chemical group 0.000 description 2
239000008096 xylene Substances 0.000 description 2
CDYTZWUKBPTGMI-RKDXNWHRSA-N (1r,2s)-2-(1h-imidazol-2-yl)cycloheptan-1-ol Chemical compound O[C@@H]1CCCCC[C@H]1C1=NC=CN1 CDYTZWUKBPTGMI-RKDXNWHRSA-N 0.000 description 1
SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 1
GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
OXEOAIYVQBYMAX-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(1,2,4-triazol-1-yl)cyclohexan-1-ol Chemical compound C=1C=C(Cl)C=CC=1C1(O)CCCCC1N1C=NC=N1 OXEOAIYVQBYMAX-UHFFFAOYSA-N 0.000 description 1
UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 1
NHDODQWIKUYWMW-UHFFFAOYSA-N 1-bromo-4-chlorobenzene Chemical compound ClC1=CC=C(Br)C=C1 NHDODQWIKUYWMW-UHFFFAOYSA-N 0.000 description 1
AITNMTXHTIIIBB-UHFFFAOYSA-N 1-bromo-4-fluorobenzene Chemical compound FC1=CC=C(Br)C=C1 AITNMTXHTIIIBB-UHFFFAOYSA-N 0.000 description 1
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
PNKASMATOJUVNA-UHFFFAOYSA-N 2-(1,2,4-triazol-1-yl)cycloheptan-1-one Chemical compound O=C1CCCCCC1N1N=CN=C1 PNKASMATOJUVNA-UHFFFAOYSA-N 0.000 description 1
YFKNIPUUQKOTMJ-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)cycloheptan-1-one Chemical compound O=C1CCCCCC1C1=NC=CN1 YFKNIPUUQKOTMJ-UHFFFAOYSA-N 0.000 description 1
DXSNBNQPESMZHW-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=NC=CN1 DXSNBNQPESMZHW-UHFFFAOYSA-N 0.000 description 1
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
CFPZDVAZISWERM-UHFFFAOYSA-N 4-bromo-1,2-dichlorobenzene Chemical compound ClC1=CC=C(Br)C=C1Cl CFPZDVAZISWERM-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
241000123650 Botrytis cinerea Species 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
229940126062 Compound A Drugs 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical group CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
229920001732 Lignosulfonate Polymers 0.000 description 1
241001141857 Morganella fuliginea Species 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
241001123561 Puccinia coronata Species 0.000 description 1
235000014443 Pyrus communis Nutrition 0.000 description 1
241000813090 Rhizoctonia solani Species 0.000 description 1
241000221696 Sclerotinia sclerotiorum Species 0.000 description 1
241001558929 Sclerotium <basidiomycota> Species 0.000 description 1
241000579741 Sphaerotheca <fungi> Species 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
238000002441 X-ray diffraction Methods 0.000 description 1
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SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
229940041514 candida albicans extract Drugs 0.000 description 1
239000000969 carrier Substances 0.000 description 1
229920006184 cellulose methylcellulose Polymers 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
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239000002036 chloroform fraction Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
235000013985 cinnamic acid Nutrition 0.000 description 1
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229940126543 compound 14 Drugs 0.000 description 1
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238000007796 conventional method Methods 0.000 description 1
238000012258 culturing Methods 0.000 description 1
ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 description 1
ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 1
FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
239000000645 desinfectant Substances 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
238000007865 diluting Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
235000013399 edible fruits Nutrition 0.000 description 1
HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000012458 free base Substances 0.000 description 1
230000002538 fungal effect Effects 0.000 description 1
239000008103 glucose Substances 0.000 description 1
239000006455 gy-medium Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
229940071870 hydroiodic acid Drugs 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000002054 inoculum Substances 0.000 description 1
239000002917 insecticide Substances 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
150000007517 lewis acids Chemical class 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
239000002609 medium Substances 0.000 description 1
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
239000002736 nonionic surfactant Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000035699 permeability Effects 0.000 description 1
230000002688 persistence Effects 0.000 description 1
NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 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
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000012488 sample solution Substances 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
238000002791 soaking Methods 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
238000010998 test method Methods 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1
239000012138 yeast extract Substances 0.000 description 1

JP59027905A 1984-02-03 1984-02-15 シス−アゾリルシクロアルカノ−ル誘導体およびその製造法ならびに農業用殺菌剤 Granted JPS60172970A (ja)

Priority Applications (10)

Application Number	Priority Date	Filing Date	Title
JP59027905A JPS60172970A (ja)	1984-02-15	1984-02-15	シス−アゾリルシクロアルカノ−ル誘導体およびその製造法ならびに農業用殺菌剤
CA000472516A CA1249832A (fr)	1984-02-03	1985-01-21	Derives d'azolylcycloalcanol, fongicides agricoles
AU38057/85A AU574126B2 (en)	1984-02-03	1985-01-24	Imidazolyl and triazolyl derivatives
DE8585101066T DE3577554D1 (de)	1984-02-03	1985-02-01	Azolyl-zykloalkanol-derivate und landwirtschaftliche fungizide.
KR1019850000636A KR900001160B1 (ko)	1984-02-03	1985-02-01	아졸릴 시클로알카놀 유도체의 제조방법
EP85101066A EP0152031B1 (fr)	1984-02-03	1985-02-01	Dérivés azolyl cycloalkanols et fongicides agricoles
BR8500473A BR8500473A (pt)	1984-02-03	1985-02-01	Processo para preparacao de um composto,fungicida agricola e industrial,e composto
ES540048A ES8605783A1 (es)	1984-02-03	1985-02-01	Procedimiento para la fabricacion de derivados de azolil ci-cloalcanol
GB08502761A GB2153355B (en)	1984-02-03	1985-02-04	Fungicidal azolyl-cycloalkanol derivatives
US07/531,347 US5091539A (en)	1984-02-03	1990-05-31	Azolyl cycloalkanol derivatives and agricultural fungicides

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP59027905A JPS60172970A (ja)	1984-02-15	1984-02-15	シス−アゾリルシクロアルカノ−ル誘導体およびその製造法ならびに農業用殺菌剤

Publications (2)

Publication Number	Publication Date
JPS60172970A JPS60172970A (ja)	1985-09-06
JPS6363542B2 true JPS6363542B2 (fr)	1988-12-07

Family

ID=12233898

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP59027905A Granted JPS60172970A (ja)	1984-02-03	1984-02-15	シス−アゾリルシクロアルカノ−ル誘導体およびその製造法ならびに農業用殺菌剤

Country Status (1)

Country	Link
JP (1)	JPS60172970A (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NZ580429A (en)	2007-05-31	2012-04-27	Sepracor Inc	Phenyl substituted cycloalkylamines as monoamine reuptake inhibitors

Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS58189171A (ja) *	1982-04-22	1983-11-04	インペリアル・ケミカル・インダストリ−ズ・ピ−エルシ−	脂環式アルコール化合物、その製造法及び該化合物を含有する、製薬学的、獣医学的、農学的又は園芸学的抗菌剤

1984
- 1984-02-15 JP JP59027905A patent/JPS60172970A/ja active Granted

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS58189171A (ja) *	1982-04-22	1983-11-04	インペリアル・ケミカル・インダストリ−ズ・ピ−エルシ−	脂環式アルコール化合物、その製造法及び該化合物を含有する、製薬学的、獣医学的、農学的又は園芸学的抗菌剤

Also Published As

Publication number	Publication date
JPS60172970A (ja)	1985-09-06

Publication	Publication Date	Title
KR900001160B1 (ko)	1990-02-27	아졸릴 시클로알카놀 유도체의 제조방법
JPS6128668B2 (fr)	1986-07-01
JPH0625140B2 (ja)	1994-04-06	新規アゾール誘導体、その製造方法及び該誘導体の農園芸用薬剤
GB2180236A (en)	1987-03-25	Azole derivatives useful as fungicides and plant growth regulators
JPH0749379B2 (ja)	1995-05-31	置換ベンゼン誘導体およびそれを有効成分とする農園芸用殺菌剤
JPH0739396B2 (ja)	1995-05-01	新規アゾール置換シクロアルカノール誘導体、その製造法及び該誘導体の農園芸用殺菌剤としての利用
JP2680319B2 (ja)	1997-11-19	新規アゾール誘導体、その製造法及び該誘導体を活性成分として含有する農園芸用殺菌剤
JPH0463071B2 (fr)	1992-10-08
KR890001547B1 (ko)	1989-05-08	치환된 아졸린-페녹시 유도체의 제조방법
JPH0819108B2 (ja)	1996-02-28	新規アゾ−ル誘導体、その製造法及び該誘導体を活性成分として含有する農園芸用殺菌剤
JPH064598B2 (ja)	1994-01-19	アゾ−ル誘導体、およびそれを含有する植物病害防除剤
JPH0533949B2 (fr)	1993-05-20
JPS6363542B2 (fr)	1988-12-07
JPH04244066A (ja)	1992-09-01	ハロゲノアルキル−アゾリル誘導体類
US5889027A (en)	1999-03-30	3(2H)-furanone derivatives
EP0368749B1 (fr)	1994-01-05	Acides carboxyliques substitués, leur préparation et leur application
JPS6344154B2 (fr)	1988-09-02
JPH0510345B2 (fr)	1993-02-09
JPS6026109B2 (ja)	1985-06-21	新規１−アシルオキシ−１−フエニル−２−アゾリル−エタンまたはその塩、その製造方法およびそれを活性成分として含有する殺菌剤若しくは殺線虫剤組成物
US4326881A (en)	1982-04-27	Phenylpyrol derivatives
EP0195414B1 (fr)	1991-02-27	Dérivés 2-azolylpropionate et fongicides les contenant
US4920142A (en)	1990-04-24	Fungicidal imidazole derivatives
JPS6072870A (ja)	1985-04-24	トリアゾールエタノール類
KR100501146B1 (ko)	2005-07-18	트리아졸 유도체, 그의 제조 방법 및 그를 포함하는농원예용 살균제 조성물
JPH06104643B2 (ja)	1994-12-21	シクロペンタノン誘導体