JPH0121147B2 - - Google Patents
Info
- Publication number
- JPH0121147B2 JPH0121147B2 JP57079811A JP7981182A JPH0121147B2 JP H0121147 B2 JPH0121147 B2 JP H0121147B2 JP 57079811 A JP57079811 A JP 57079811A JP 7981182 A JP7981182 A JP 7981182A JP H0121147 B2 JPH0121147 B2 JP H0121147B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- carbon atoms
- formula
- alkyl group
- phenyl
- Prior art date
- 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
Links
- 125000004432 carbon atom Chemical group C* 0.000 claims description 242
- 125000000217 alkyl group Chemical group 0.000 claims description 172
- 150000001875 compounds Chemical class 0.000 claims description 160
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 112
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 110
- 125000005843 halogen group Chemical group 0.000 claims description 95
- 150000003839 salts Chemical class 0.000 claims description 88
- -1 CF 3 Chemical group 0.000 claims description 74
- 239000004480 active ingredient Substances 0.000 claims description 73
- 125000003545 alkoxy group Chemical group 0.000 claims description 60
- 239000002253 acid Substances 0.000 claims description 58
- 241000196324 Embryophyta Species 0.000 claims description 52
- 238000000034 method Methods 0.000 claims description 49
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 41
- 229910052751 metal Chemical class 0.000 claims description 31
- 239000002184 metal Chemical class 0.000 claims description 31
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
- 238000004519 manufacturing process Methods 0.000 claims description 25
- 241000233866 Fungi Species 0.000 claims description 20
- 125000003342 alkenyl group Chemical group 0.000 claims description 20
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 17
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 239000001301 oxygen Substances 0.000 claims description 15
- 239000007787 solid Substances 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
- 125000004434 sulfur atom Chemical group 0.000 claims description 15
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 14
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 14
- 239000007788 liquid Substances 0.000 claims description 13
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 12
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 12
- 230000000855 fungicidal effect Effects 0.000 claims description 12
- 239000004094 surface-active agent Substances 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 150000004696 coordination complex Chemical class 0.000 claims description 9
- 239000000417 fungicide Substances 0.000 claims description 9
- 125000001624 naphthyl group Chemical group 0.000 claims description 9
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 7
- 239000000654 additive Substances 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 150000001721 carbon Chemical group 0.000 claims description 7
- 150000001768 cations Chemical class 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 244000005700 microbiome Species 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 229910052727 yttrium Inorganic materials 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 229910052770 Uranium Inorganic materials 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- KALBJJADLJSROW-UHFFFAOYSA-N 1-[[4-methyl-2-(4-phenoxyphenyl)-1,3-dioxolan-2-yl]methyl]-1,2,4-triazole Chemical compound O1C(C)COC1(C=1C=CC(OC=2C=CC=CC=2)=CC=1)CN1N=CN=C1 KALBJJADLJSROW-UHFFFAOYSA-N 0.000 claims description 3
- CQMMDEJDZIVXAN-UHFFFAOYSA-N 2-[[2-[4-(4-chlorophenoxy)phenyl]-4-ethyl-1,3-dioxolan-2-yl]methyl]-1h-imidazole Chemical compound O1C(CC)COC1(C=1C=CC(OC=2C=CC(Cl)=CC=2)=CC=1)CC1=NC=CN1 CQMMDEJDZIVXAN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052786 argon Inorganic materials 0.000 claims description 3
- 230000000269 nucleophilic effect Effects 0.000 claims description 3
- BQCVXMIBPSTYAX-UHFFFAOYSA-N 1-[[4-methyl-2-(4-phenoxyphenyl)-1,3-dioxan-2-yl]methyl]-1,2,4-triazole Chemical compound O1C(C)CCOC1(C=1C=CC(OC=2C=CC=CC=2)=CC=1)CN1N=CN=C1 BQCVXMIBPSTYAX-UHFFFAOYSA-N 0.000 claims description 2
- KJUNVBSMCCDGCL-UHFFFAOYSA-N 2-[[2-[4-(2,4-dimethylphenoxy)phenyl]-4-ethyl-1,3-dioxolan-2-yl]methyl]-1h-imidazole Chemical compound O1C(CC)COC1(C=1C=CC(OC=2C(=CC(C)=CC=2)C)=CC=1)CC1=NC=CN1 KJUNVBSMCCDGCL-UHFFFAOYSA-N 0.000 claims description 2
- VZDHFZKYKSNMIR-UHFFFAOYSA-N 2-[[2-[4-(2,5-dichlorophenoxy)phenyl]-4-ethyl-1,3-dioxolan-2-yl]methyl]-1h-imidazole Chemical compound O1C(CC)COC1(C=1C=CC(OC=2C(=CC=C(Cl)C=2)Cl)=CC=1)CC1=NC=CN1 VZDHFZKYKSNMIR-UHFFFAOYSA-N 0.000 claims description 2
- ITTPRHJUWOKCNF-UHFFFAOYSA-N 2-[[2-[4-(3-chlorophenoxy)phenyl]-4-ethyl-1,3-dioxolan-2-yl]methyl]-1h-imidazole Chemical compound O1C(CC)COC1(C=1C=CC(OC=2C=C(Cl)C=CC=2)=CC=1)CC1=NC=CN1 ITTPRHJUWOKCNF-UHFFFAOYSA-N 0.000 claims description 2
- RSZOQUJOVPTYJC-UHFFFAOYSA-N 2-[[2-[4-(4-fluorophenoxy)phenyl]-4,5-dimethyl-1,3-dioxolan-2-yl]methyl]-1H-imidazole Chemical compound FC1=CC=C(OC2=CC=C(C=C2)C2(OC(C(O2)C)C)CC=2NC=CN2)C=C1 RSZOQUJOVPTYJC-UHFFFAOYSA-N 0.000 claims description 2
- UKXGWZQTWKLISO-UHFFFAOYSA-N 2-[[4-ethyl-2-[4-(4-fluorophenoxy)phenyl]-1,3-dioxolan-2-yl]methyl]-1H-imidazole Chemical compound FC1=CC=C(OC2=CC=C(C=C2)C2(OCC(O2)CC)CC=2NC=CN2)C=C1 UKXGWZQTWKLISO-UHFFFAOYSA-N 0.000 claims description 2
- JSTAUFDKTZOOKF-UHFFFAOYSA-N 2-[[4-ethyl-2-[4-[3-(trifluoromethyl)phenoxy]phenyl]-1,3-dioxolan-2-yl]methyl]-1H-imidazole Chemical compound FC(C=1C=C(OC2=CC=C(C=C2)C2(OCC(O2)CC)CC=2NC=CN2)C=CC1)(F)F JSTAUFDKTZOOKF-UHFFFAOYSA-N 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 3
- 230000000996 additive effect Effects 0.000 claims 2
- ZSUCKIYMPYBWIP-UHFFFAOYSA-N 1-[[2-[4-(4-fluorophenoxy)phenyl]-1,3-dioxan-2-yl]methyl]-1,2,4-triazole Chemical compound C1=CC(F)=CC=C1OC1=CC=C(C2(CN3N=CN=C3)OCCCO2)C=C1 ZSUCKIYMPYBWIP-UHFFFAOYSA-N 0.000 claims 1
- PSDXWJUGKAUIKY-UHFFFAOYSA-N 1-[[4-ethyl-2-(4-phenoxyphenyl)-1,3-dioxan-2-yl]methyl]-1,2,4-triazole Chemical compound O1C(CC)CCOC1(C=1C=CC(OC=2C=CC=CC=2)=CC=1)CN1N=CN=C1 PSDXWJUGKAUIKY-UHFFFAOYSA-N 0.000 claims 1
- CWQSHBVVQYSKMP-UHFFFAOYSA-N 2-[[2-[4-(4-chloro-2-methylphenoxy)phenyl]-4-(methoxymethyl)-1,3-dioxolan-2-yl]methyl]-1h-imidazole Chemical compound O1C(COC)COC1(C=1C=CC(OC=2C(=CC(Cl)=CC=2)C)=CC=1)CC1=NC=CN1 CWQSHBVVQYSKMP-UHFFFAOYSA-N 0.000 claims 1
- CILFPIPSQVGVMR-UHFFFAOYSA-N 2-[[2-[4-(4-chloro-3-methylphenoxy)phenyl]-4-ethyl-1,3-dioxolan-2-yl]methyl]-1H-imidazole Chemical compound ClC1=C(C=C(OC2=CC=C(C=C2)C2(OCC(O2)CC)CC=2NC=CN2)C=C1)C CILFPIPSQVGVMR-UHFFFAOYSA-N 0.000 claims 1
- MWHVHILNHIFUMY-UHFFFAOYSA-N 2-[[4-ethyl-2-(2-methyl-4-phenoxyphenyl)-1,3-dioxolan-2-yl]methyl]-1H-imidazole Chemical compound O(C1=CC=CC=C1)C1=CC(=C(C=C1)C1(OCC(O1)CC)CC=1NC=CN1)C MWHVHILNHIFUMY-UHFFFAOYSA-N 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- XKTYXVDYIKIYJP-UHFFFAOYSA-N 3h-dioxole Chemical compound C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 0.000 claims 1
- SMNRFWMNPDABKZ-WVALLCKVSA-N [[(2R,3S,4R,5S)-5-(2,6-dioxo-3H-pyridin-3-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4S,5R,6R)-4-fluoro-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)C2C=CC(=O)NC2=O)[C@H](O)[C@@H](F)[C@@H]1O SMNRFWMNPDABKZ-WVALLCKVSA-N 0.000 claims 1
- 229910000365 copper sulfate Inorganic materials 0.000 claims 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 claims 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims 1
- 238000003898 horticulture Methods 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
- 150000002926 oxygen Chemical class 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 108
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 90
- 239000000203 mixture Substances 0.000 description 82
- 239000002904 solvent Substances 0.000 description 63
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 51
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 31
- 239000011541 reaction mixture Substances 0.000 description 31
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 30
- 229910052938 sodium sulfate Inorganic materials 0.000 description 29
- 235000011152 sodium sulphate Nutrition 0.000 description 29
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 26
- 239000000243 solution Substances 0.000 description 25
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- 239000000741 silica gel Substances 0.000 description 24
- 229910002027 silica gel Inorganic materials 0.000 description 24
- 239000000284 extract Substances 0.000 description 23
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Inorganic materials [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 23
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 22
- 239000000047 product Substances 0.000 description 22
- 238000012360 testing method Methods 0.000 description 21
- 238000001704 evaporation Methods 0.000 description 20
- 230000008020 evaporation Effects 0.000 description 20
- 235000014113 dietary fatty acids Nutrition 0.000 description 19
- 239000000194 fatty acid Substances 0.000 description 19
- 229930195729 fatty acid Natural products 0.000 description 19
- 238000003756 stirring Methods 0.000 description 19
- 239000000725 suspension Substances 0.000 description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 18
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 18
- 208000015181 infectious disease Diseases 0.000 description 17
- 239000007921 spray Substances 0.000 description 17
- 229920001223 polyethylene glycol Polymers 0.000 description 16
- 238000004440 column chromatography Methods 0.000 description 15
- 238000002844 melting Methods 0.000 description 15
- 230000008018 melting Effects 0.000 description 15
- BXWNKGSJHAJOGX-UHFFFAOYSA-N n-hexadecyl alcohol Natural products CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 15
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 239000002585 base Substances 0.000 description 13
- 239000013078 crystal Substances 0.000 description 13
- 239000000839 emulsion Substances 0.000 description 13
- 238000009472 formulation Methods 0.000 description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
- 239000003921 oil Substances 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 13
- 239000000126 substance Substances 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 235000019198 oils Nutrition 0.000 description 12
- 239000012044 organic layer Substances 0.000 description 12
- 239000000843 powder Substances 0.000 description 12
- 239000003826 tablet Substances 0.000 description 12
- 235000019441 ethanol Nutrition 0.000 description 11
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- 239000002202 Polyethylene glycol Substances 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 239000000825 pharmaceutical preparation Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 229920002472 Starch Polymers 0.000 description 9
- 239000003995 emulsifying agent Substances 0.000 description 9
- 239000008187 granular material Substances 0.000 description 9
- 239000003208 petroleum Substances 0.000 description 9
- 159000000000 sodium salts Chemical class 0.000 description 9
- 235000019698 starch Nutrition 0.000 description 9
- 239000000454 talc Substances 0.000 description 9
- 229910052623 talc Inorganic materials 0.000 description 9
- 235000012222 talc Nutrition 0.000 description 9
- 238000011282 treatment Methods 0.000 description 9
- 240000005979 Hordeum vulgare Species 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 8
- 230000000843 anti-fungal effect Effects 0.000 description 8
- 230000003197 catalytic effect Effects 0.000 description 8
- 229960000541 cetyl alcohol Drugs 0.000 description 8
- 239000006071 cream Substances 0.000 description 8
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical group OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 8
- 150000004665 fatty acids Chemical class 0.000 description 8
- 239000008101 lactose Substances 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- 235000009518 sodium iodide Nutrition 0.000 description 8
- 239000002689 soil Substances 0.000 description 8
- 239000004563 wettable powder Substances 0.000 description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 230000002538 fungal effect Effects 0.000 description 7
- 229930195733 hydrocarbon Natural products 0.000 description 7
- 150000002430 hydrocarbons Chemical class 0.000 description 7
- 150000002576 ketones Chemical class 0.000 description 7
- 230000007935 neutral effect Effects 0.000 description 7
- 239000002674 ointment Substances 0.000 description 7
- 230000001681 protective effect Effects 0.000 description 7
- 239000008107 starch Substances 0.000 description 7
- 239000008096 xylene Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 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 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 241000209140 Triticum Species 0.000 description 6
- 239000003905 agrochemical Substances 0.000 description 6
- 230000000844 anti-bacterial effect Effects 0.000 description 6
- 230000000949 anxiolytic effect Effects 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- 239000000969 carrier Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 239000003925 fat Substances 0.000 description 6
- 235000019197 fats Nutrition 0.000 description 6
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 235000019359 magnesium stearate Nutrition 0.000 description 6
- 150000007522 mineralic acids Chemical class 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 230000000699 topical effect Effects 0.000 description 6
- 238000006418 Brown reaction Methods 0.000 description 5
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 5
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 5
- 239000005662 Paraffin oil Substances 0.000 description 5
- 229920001214 Polysorbate 60 Polymers 0.000 description 5
- 235000021355 Stearic acid Nutrition 0.000 description 5
- 230000001773 anti-convulsant effect Effects 0.000 description 5
- 239000001961 anticonvulsive agent Substances 0.000 description 5
- 229960003965 antiepileptics Drugs 0.000 description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 239000008298 dragée Substances 0.000 description 5
- 239000012156 elution solvent Substances 0.000 description 5
- 150000002191 fatty alcohols Chemical class 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
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- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid group Chemical class S(N)(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 244000045561 useful plants Species 0.000 description 1
- 229910052720 vanadium Inorganic materials 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
- 239000003981 vehicle Substances 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH3066/81-2 | 1981-05-12 | ||
CH306681 | 1981-05-12 | ||
CH2428/82-1 | 1982-04-21 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5823687A JPS5823687A (ja) | 1983-02-12 |
JPH0121147B2 true JPH0121147B2 (es) | 1989-04-19 |
Family
ID=4247864
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP57079811A Granted JPS5823687A (ja) | 1981-05-12 | 1982-05-12 | 新規アリールフェニルエーテル誘導体、その製法及び該化合物を含有する農園芸用殺菌剤 |
Country Status (6)
Country | Link |
---|---|
JP (1) | JPS5823687A (es) |
BR (1) | BR8202743A (es) |
MX (1) | MX5807A (es) |
SU (1) | SU1148564A3 (es) |
TR (1) | TR21964A (es) |
ZA (1) | ZA823225B (es) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3144318A1 (de) * | 1981-11-07 | 1983-05-19 | Bayer Ag, 5090 Leverkusen | 2-imidazolylmethyl-2-phenyl-1, 3-dioxolane, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
KR100743255B1 (ko) * | 2006-05-04 | 2007-07-27 | 한국과학기술연구원 | T-형 칼슘 채널에 활성을 지닌 신규1,3-다이옥소아이소인돌 유도체 |
JP5958905B2 (ja) * | 2011-10-20 | 2016-08-02 | 公立大学法人秋田県立大学 | 植物成長調節剤 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5175073A (en) * | 1974-11-18 | 1976-06-29 | Janssen Pharmaceutica Nv | 11* beeta ariiru * echiru 1hh1 2 4to toriazooruketaaru oyobi sonosanfukaen no seizoho |
JPS5536478A (en) * | 1978-07-24 | 1980-03-14 | Janssen Pharmaceutica Nv | Novel azole compound*its manufacture and use |
JPS5555183A (en) * | 1978-07-25 | 1980-04-22 | Janssen Pharmaceutica Nv | Novel azole compound*its manufacture and use |
JPS5646880A (en) * | 1979-09-12 | 1981-04-28 | Janssen Pharmaceutica Nv | Bactericidal dioxolanyll and dioxanyll methylazalium derivative |
-
1982
- 1982-05-11 TR TR2196482A patent/TR21964A/xx unknown
- 1982-05-11 ZA ZA823225A patent/ZA823225B/xx unknown
- 1982-05-12 BR BR8202743A patent/BR8202743A/pt not_active IP Right Cessation
- 1982-05-12 JP JP57079811A patent/JPS5823687A/ja active Granted
- 1982-12-27 SU SU823528400A patent/SU1148564A3/ru active
-
1986
- 1986-12-01 MX MX580786A patent/MX5807A/es unknown
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5175073A (en) * | 1974-11-18 | 1976-06-29 | Janssen Pharmaceutica Nv | 11* beeta ariiru * echiru 1hh1 2 4to toriazooruketaaru oyobi sonosanfukaen no seizoho |
JPS5536478A (en) * | 1978-07-24 | 1980-03-14 | Janssen Pharmaceutica Nv | Novel azole compound*its manufacture and use |
JPS5555183A (en) * | 1978-07-25 | 1980-04-22 | Janssen Pharmaceutica Nv | Novel azole compound*its manufacture and use |
JPS5646880A (en) * | 1979-09-12 | 1981-04-28 | Janssen Pharmaceutica Nv | Bactericidal dioxolanyll and dioxanyll methylazalium derivative |
Also Published As
Publication number | Publication date |
---|---|
MX5807A (es) | 1993-10-01 |
SU1148564A3 (ru) | 1985-03-30 |
ZA823225B (en) | 1983-03-30 |
TR21964A (tr) | 1985-12-11 |
JPS5823687A (ja) | 1983-02-12 |
BR8202743A (pt) | 1983-04-19 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
EXPY | Cancellation because of completion of term |