CA1133492A - 1-(2-aryl-2-r-ethyl)-1h-1,2,4-triazoles - Google Patents
1-(2-aryl-2-r-ethyl)-1h-1,2,4-triazolesInfo
- Publication number
- CA1133492A CA1133492A CA283,776A CA283776A CA1133492A CA 1133492 A CA1133492 A CA 1133492A CA 283776 A CA283776 A CA 283776A CA 1133492 A CA1133492 A CA 1133492A
- Authority
- CA
- Canada
- Prior art keywords
- triazole
- acid addition
- acceptable acid
- phenyl
- group
- 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
- 150000001875 compounds Chemical class 0.000 claims abstract description 68
- -1 trifluoromethylphenyl Chemical group 0.000 claims abstract description 57
- 150000003839 salts Chemical class 0.000 claims abstract description 53
- 239000002253 acid Substances 0.000 claims abstract description 48
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 34
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 8
- 125000001424 substituent group Chemical group 0.000 claims abstract description 8
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 125000004802 cyanophenyl group Chemical group 0.000 claims abstract description 4
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 4
- 125000006501 nitrophenyl group Chemical group 0.000 claims abstract description 4
- 125000005037 alkyl phenyl group Chemical group 0.000 claims abstract 3
- 125000001475 halogen functional group Chemical group 0.000 claims abstract 3
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 claims description 20
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 238000010992 reflux Methods 0.000 claims description 8
- 159000000000 sodium salts Chemical class 0.000 claims description 8
- LFLBHTZRLVHUQC-UHFFFAOYSA-N butyl methanesulfonate Chemical compound CCCCOS(C)(=O)=O LFLBHTZRLVHUQC-UHFFFAOYSA-N 0.000 claims description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 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 description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 239000003495 polar organic solvent Substances 0.000 claims description 3
- KPQNSPKZPKKJBS-UHFFFAOYSA-N 2-(2,4-dibromophenyl)hexyl methanesulfonate Chemical compound CCCCC(COS(C)(=O)=O)C1=CC=C(Br)C=C1Br KPQNSPKZPKKJBS-UHFFFAOYSA-N 0.000 claims description 2
- FMGOPNNYXMJSQP-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)hexyl methanesulfonate Chemical compound CCCCC(COS(C)(=O)=O)C1=CC=C(Cl)C=C1Cl FMGOPNNYXMJSQP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004188 dichlorophenyl group Chemical group 0.000 claims description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- NSPMIYGKQJPBQR-CVMUNTFWSA-N 1h-1,2,4-triazole Chemical class [13CH]=1[15N]=[13CH][15NH][15N]=1 NSPMIYGKQJPBQR-CVMUNTFWSA-N 0.000 claims 3
- GIDULHOTKAIVFM-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)-4-(4-methylphenyl)butyl]-1,2,4-triazole Chemical compound C1=CC(C)=CC=C1CCC(C=1C=CC(F)=CC=1)CN1N=CN=C1 GIDULHOTKAIVFM-UHFFFAOYSA-N 0.000 claims 2
- XRTGEXMHEJYFCR-UHFFFAOYSA-N 1-[2-cyclohexyl-2-(2,4-dichlorophenyl)ethyl]-1,2,4-triazole Chemical compound ClC1=CC(Cl)=CC=C1C(C1CCCCC1)CN1N=CN=C1 XRTGEXMHEJYFCR-UHFFFAOYSA-N 0.000 claims 2
- RXUKNHVFFYHSRK-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)-2-(4-fluorophenyl)butyl]-1,2,4-triazole Chemical compound C1=CC(F)=CC=C1C(CN1N=CN=C1)CCC1=CC=C(Cl)C=C1 RXUKNHVFFYHSRK-UHFFFAOYSA-N 0.000 claims 2
- QTYNSYDZEQPZQG-UHFFFAOYSA-N 1-[2-(2,4-dibromophenyl)hexyl]-1,2,4-triazole Chemical compound C=1C=C(Br)C=C(Br)C=1C(CCCC)CN1C=NC=N1 QTYNSYDZEQPZQG-UHFFFAOYSA-N 0.000 claims 1
- OKFNDRAXJVLCSI-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)-3-methylbutyl]-1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(C(C)C)CN1C=NC=N1 OKFNDRAXJVLCSI-UHFFFAOYSA-N 0.000 claims 1
- SXMLWBVZPDZWTG-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)-3-methylpentyl]-1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(C(C)CC)CN1C=NC=N1 SXMLWBVZPDZWTG-UHFFFAOYSA-N 0.000 claims 1
- PINPXQLXNURYOJ-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)-4-methylpentyl]-1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CC(C)C)CN1C=NC=N1 PINPXQLXNURYOJ-UHFFFAOYSA-N 0.000 claims 1
- NDHFVCRNFBYCBC-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)heptyl]-1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCCCC)CN1C=NC=N1 NDHFVCRNFBYCBC-UHFFFAOYSA-N 0.000 claims 1
- NEDKLHZEQYTKIX-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)hexyl]-1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCCC)CN1C=NC=N1 NEDKLHZEQYTKIX-UHFFFAOYSA-N 0.000 claims 1
- BIFSIDIOXLCEQE-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)-2-(4-methylphenyl)butyl]-1,2,4-triazole Chemical compound C1=CC(C)=CC=C1C(CN1N=CN=C1)CCC1=CC=C(Cl)C=C1 BIFSIDIOXLCEQE-UHFFFAOYSA-N 0.000 claims 1
- CIZMWWFUVMGBEL-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)heptyl methanesulfonate Chemical compound CCCCCC(COS(C)(=O)=O)C1=CC=C(Cl)C=C1Cl CIZMWWFUVMGBEL-UHFFFAOYSA-N 0.000 claims 1
- GOWRHDOMJQAPCM-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-4-methylpentane-1-sulfonic acid Chemical compound CC(C)C(CCS(=O)(=O)O)C1=C(C=C(C=C1)Cl)Cl GOWRHDOMJQAPCM-UHFFFAOYSA-N 0.000 claims 1
- HTWYQTSMFXYLKB-UHFFFAOYSA-N [2-(2,4-dichlorophenyl)-3-methylpentyl] methanesulfonate Chemical compound CS(=O)(=O)OCC(C(C)CC)C1=CC=C(Cl)C=C1Cl HTWYQTSMFXYLKB-UHFFFAOYSA-N 0.000 claims 1
- QBFOWCNEHHYGGI-UHFFFAOYSA-N [2-(2,4-dichlorophenyl)-4-methylpentyl] methanesulfonate Chemical compound CS(=O)(=O)OCC(CC(C)C)C1=CC=C(Cl)C=C1Cl QBFOWCNEHHYGGI-UHFFFAOYSA-N 0.000 claims 1
- DPHPEEKNASPCHI-UHFFFAOYSA-N [2-cyclohexyl-2-(2,4-dichlorophenyl)ethyl] methanesulfonate Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(COS(=O)(=O)C)C1CCCCC1 DPHPEEKNASPCHI-UHFFFAOYSA-N 0.000 claims 1
- PEASYXLOQMURPR-UHFFFAOYSA-N [4-(4-chlorophenyl)-2-(4-fluorophenyl)butyl] methanesulfonate Chemical compound C=1C=C(F)C=CC=1C(COS(=O)(=O)C)CCC1=CC=C(Cl)C=C1 PEASYXLOQMURPR-UHFFFAOYSA-N 0.000 claims 1
- 125000005948 methanesulfonyloxy group Chemical group 0.000 claims 1
- 230000000855 fungicidal effect Effects 0.000 abstract description 4
- 230000008635 plant growth Effects 0.000 abstract description 4
- 230000001105 regulatory effect Effects 0.000 abstract description 4
- 125000000304 alkynyl group Chemical group 0.000 abstract description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 52
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 44
- 239000000203 mixture Substances 0.000 description 36
- 238000000034 method Methods 0.000 description 35
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 30
- 229910002651 NO3 Inorganic materials 0.000 description 30
- 239000000243 solution Substances 0.000 description 29
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- 239000000047 product Substances 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 24
- 238000003756 stirring Methods 0.000 description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 21
- 150000002148 esters Chemical class 0.000 description 20
- 239000000284 extract Substances 0.000 description 20
- 241000196324 Embryophyta Species 0.000 description 17
- 239000006185 dispersion Substances 0.000 description 16
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 14
- 239000012312 sodium hydride Substances 0.000 description 14
- 229910000104 sodium hydride Inorganic materials 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- 239000003480 eluent Substances 0.000 description 13
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000002585 base Substances 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 10
- 229940076134 benzene Drugs 0.000 description 9
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 9
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- 241000233866 Fungi Species 0.000 description 8
- 241000896246 Golovinomyces cichoracearum Species 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 7
- 240000008067 Cucumis sativus Species 0.000 description 7
- 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 7
- 229960001701 chloroform Drugs 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 150000002823 nitrates Chemical class 0.000 description 7
- 230000000069 prophylactic effect Effects 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 6
- 238000005187 foaming Methods 0.000 description 6
- 230000002538 fungal effect Effects 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 239000012258 stirred mixture Substances 0.000 description 6
- 150000003852 triazoles Chemical class 0.000 description 6
- LDZLXQFDGRCELX-UHFFFAOYSA-N 4-phenylbutan-1-ol Chemical compound OCCCCC1=CC=CC=C1 LDZLXQFDGRCELX-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 235000009075 Cucumis anguria Nutrition 0.000 description 5
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 239000000306 component Substances 0.000 description 5
- 229910001873 dinitrogen Inorganic materials 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 150000004678 hydrides Chemical class 0.000 description 5
- 150000002825 nitriles Chemical class 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 description 4
- 241001480061 Blumeria graminis Species 0.000 description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 241000221577 Uromyces appendiculatus Species 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 230000000843 anti-fungal effect Effects 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 208000015181 infectious disease Diseases 0.000 description 4
- 229940083608 sodium hydroxide Drugs 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- OBKXEAXTFZPCHS-UHFFFAOYSA-N 4-phenylbutyric acid Chemical compound OC(=O)CCCC1=CC=CC=C1 OBKXEAXTFZPCHS-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 240000005979 Hordeum vulgare Species 0.000 description 3
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- 244000046052 Phaseolus vulgaris Species 0.000 description 3
- 208000036366 Sensation of pressure Diseases 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000001246 bromo group Chemical group Br* 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 230000012010 growth Effects 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 3
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 239000002674 ointment Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 125000003944 tolyl group Chemical group 0.000 description 3
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 2
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 2
- NXTLYFWOLCJOAM-UHFFFAOYSA-N 2-(2,4-dibromophenyl)acetonitrile Chemical compound BrC1=CC=C(CC#N)C(Br)=C1 NXTLYFWOLCJOAM-UHFFFAOYSA-N 0.000 description 2
- VJARIBGMDPJLCL-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)acetonitrile Chemical compound ClC1=CC=C(CC#N)C(Cl)=C1 VJARIBGMDPJLCL-UHFFFAOYSA-N 0.000 description 2
- BJUWNNAXAGUNQF-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)propyl methanesulfonate Chemical compound CS(=O)(=O)OCC(C)C1=CC=C(Cl)C=C1Cl BJUWNNAXAGUNQF-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- KARLFCIZLBGGPJ-UHFFFAOYSA-N [2-(2,4-dichlorophenyl)-3-methylbutyl] methanesulfonate Chemical compound CS(=O)(=O)OCC(C(C)C)C1=CC=C(Cl)C=C1Cl KARLFCIZLBGGPJ-UHFFFAOYSA-N 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 229940121375 antifungal agent Drugs 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000004799 bromophenyl group Chemical group 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 125000000068 chlorophenyl group Chemical group 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000010410 dusting Methods 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- SRCVNBFTEARRJY-UHFFFAOYSA-N methyl 2-(2,4-dichlorophenyl)acetate Chemical compound COC(=O)CC1=CC=C(Cl)C=C1Cl SRCVNBFTEARRJY-UHFFFAOYSA-N 0.000 description 2
- 150000002790 naphthalenes Chemical class 0.000 description 2
- IKOJJEGSGBXSMM-UHFFFAOYSA-N nitric acid;2h-triazole Chemical class O[N+]([O-])=O.C=1C=NNN=1 IKOJJEGSGBXSMM-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- CEGRHPCDLKAHJD-UHFFFAOYSA-N 1,1,1-propanetricarboxylic acid Chemical compound CCC(C(O)=O)(C(O)=O)C(O)=O CEGRHPCDLKAHJD-UHFFFAOYSA-N 0.000 description 1
- FKRVRTNDBKCDEZ-UHFFFAOYSA-N 1,3,5-tribromo-2-(3-bromopropoxy)benzene Chemical compound BrCCCOC1=C(Br)C=C(Br)C=C1Br FKRVRTNDBKCDEZ-UHFFFAOYSA-N 0.000 description 1
- VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 description 1
- SRGBSEMMGLSUMI-UHFFFAOYSA-N 1-bromo-4-(2-bromoethoxy)benzene Chemical compound BrCCOC1=CC=C(Br)C=C1 SRGBSEMMGLSUMI-UHFFFAOYSA-N 0.000 description 1
- BASMANVIUSSIIM-UHFFFAOYSA-N 1-chloro-2-(chloromethyl)benzene Chemical compound ClCC1=CC=CC=C1Cl BASMANVIUSSIIM-UHFFFAOYSA-N 0.000 description 1
- 125000006021 1-methyl-2-propenyl group Chemical group 0.000 description 1
- DGBNUTJYQXQLSV-UHFFFAOYSA-N 1h-triazol-1-ium;chloride Chemical class Cl.C1=CNN=N1 DGBNUTJYQXQLSV-UHFFFAOYSA-N 0.000 description 1
- PLVGCBPOBWFEAR-UHFFFAOYSA-N 2,4-bis(2,4-dichlorophenyl)butyl methanesulfonate Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(COS(=O)(=O)C)CCC1=CC=C(Cl)C=C1Cl PLVGCBPOBWFEAR-UHFFFAOYSA-N 0.000 description 1
- XTHNUJFYJSGINE-UHFFFAOYSA-N 2,4-bis(4-bromophenyl)butyl methanesulfonate Chemical compound C=1C=C(Br)C=CC=1C(COS(=O)(=O)C)CCC1=CC=C(Br)C=C1 XTHNUJFYJSGINE-UHFFFAOYSA-N 0.000 description 1
- NVEATUSTYIXFDQ-UHFFFAOYSA-N 2,4-bis(4-chlorophenyl)butyl methanesulfonate Chemical compound C=1C=C(Cl)C=CC=1C(COS(=O)(=O)C)CCC1=CC=C(Cl)C=C1 NVEATUSTYIXFDQ-UHFFFAOYSA-N 0.000 description 1
- JIJGKPVJAALUQQ-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)ethanol Chemical compound OCCC1=CC=C(Cl)C=C1Cl JIJGKPVJAALUQQ-UHFFFAOYSA-N 0.000 description 1
- OZRBFNLBFFCPMS-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)hex-5-enyl methanesulfonate Chemical compound CS(=O)(=O)OCC(CCC=C)C1=CC=C(Cl)C=C1Cl OZRBFNLBFFCPMS-UHFFFAOYSA-N 0.000 description 1
- KAIVOIMLFWQCSQ-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)pentyl methanesulfonate Chemical compound CS(=O)(=O)OCC(CCC)C1=CC=C(Cl)C=C1Cl KAIVOIMLFWQCSQ-UHFFFAOYSA-N 0.000 description 1
- SMXITDRKFGMUMI-UHFFFAOYSA-N 2-(3-bromopropoxy)-1,5-dichloro-3-methylbenzene Chemical compound CC1=CC(Cl)=CC(Cl)=C1OCCCBr SMXITDRKFGMUMI-UHFFFAOYSA-N 0.000 description 1
- KWHVBVJDKLSOTB-UHFFFAOYSA-N 2-(3-methylphenyl)ethanol Chemical compound CC1=CC=CC(CCO)=C1 KWHVBVJDKLSOTB-UHFFFAOYSA-N 0.000 description 1
- IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 description 1
- QEKIAXFRNIXHKL-UHFFFAOYSA-N 2-bromo-1-(3-bromopropoxy)-4-methylbenzene Chemical compound CC1=CC=C(OCCCBr)C(Br)=C1 QEKIAXFRNIXHKL-UHFFFAOYSA-N 0.000 description 1
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- 125000006040 2-hexenyl group Chemical group 0.000 description 1
- LODHFNUFVRVKTH-ZHACJKMWSA-N 2-hydroxy-n'-[(e)-3-phenylprop-2-enoyl]benzohydrazide Chemical compound OC1=CC=CC=C1C(=O)NNC(=O)\C=C\C1=CC=CC=C1 LODHFNUFVRVKTH-ZHACJKMWSA-N 0.000 description 1
- PZMKMCFRTKGVOL-UHFFFAOYSA-N 2-methylpropyl methanesulfonate Chemical compound CC(C)COS(C)(=O)=O PZMKMCFRTKGVOL-UHFFFAOYSA-N 0.000 description 1
- PKRSYEPBQPFNRB-UHFFFAOYSA-N 2-phenoxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1OC1=CC=CC=C1 PKRSYEPBQPFNRB-UHFFFAOYSA-N 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 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
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- SXQWXHJXOKISFD-UHFFFAOYSA-N 4-(3-bromopropoxy)-1-chloro-2-methylbenzene Chemical compound CC1=CC(OCCCBr)=CC=C1Cl SXQWXHJXOKISFD-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- XRUKSARUAXTNEA-UHFFFAOYSA-N 4-amino-2-hydroxybenzoic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1.NC1=CC=C(C(O)=O)C(O)=C1 XRUKSARUAXTNEA-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- 101100087530 Caenorhabditis elegans rom-1 gene Proteins 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000221785 Erysiphales Species 0.000 description 1
- 241000896222 Erysiphe polygoni Species 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 241000896218 Golovinomyces orontii Species 0.000 description 1
- 241000251953 Leucotrichia Species 0.000 description 1
- 239000012448 Lithium borohydride Substances 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 101100400378 Mus musculus Marveld2 gene Proteins 0.000 description 1
- 101100305983 Mus musculus Rom1 gene Proteins 0.000 description 1
- 241000498271 Necator Species 0.000 description 1
- FAIIFDPAEUKBEP-UHFFFAOYSA-N Nilvadipine Chemical compound COC(=O)C1=C(C#N)NC(C)=C(C(=O)OC(C)C)C1C1=CC=CC([N+]([O-])=O)=C1 FAIIFDPAEUKBEP-UHFFFAOYSA-N 0.000 description 1
- 241000896242 Podosphaera Species 0.000 description 1
- 241001580842 Podosphaera mors-uvae Species 0.000 description 1
- 241000896203 Podosphaera pannosa Species 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241001597359 Septoria apiicola Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
- CFUYPFHGVIZBNG-UHFFFAOYSA-N [2-(2,4-dichlorophenyl)-5-naphthalen-2-yloxypentyl] methanesulfonate Chemical compound C=1C=C2C=CC=CC2=CC=1OCCCC(COS(=O)(=O)C)C1=CC=C(Cl)C=C1Cl CFUYPFHGVIZBNG-UHFFFAOYSA-N 0.000 description 1
- SOJOUISBGFCXIN-UHFFFAOYSA-N [2-(4-bromophenyl)-4-(4-chlorophenyl)butyl] methanesulfonate Chemical compound C=1C=C(Br)C=CC=1C(COS(=O)(=O)C)CCC1=CC=C(Cl)C=C1 SOJOUISBGFCXIN-UHFFFAOYSA-N 0.000 description 1
- ZPPXGUKUUNPNRG-UHFFFAOYSA-N [2-(4-fluorophenyl)-4-(4-methylphenyl)butyl] methanesulfonate Chemical compound C1=CC(C)=CC=C1CCC(COS(C)(=O)=O)C1=CC=C(F)C=C1 ZPPXGUKUUNPNRG-UHFFFAOYSA-N 0.000 description 1
- NVAQYUIEXLXBAN-UHFFFAOYSA-N [3-(2-bromophenyl)-2-(2,4-dichlorophenyl)propyl] methanesulfonate Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(COS(=O)(=O)C)CC1=CC=CC=C1Br NVAQYUIEXLXBAN-UHFFFAOYSA-N 0.000 description 1
- BTWDXSOKSWYHNJ-UHFFFAOYSA-N [3-(4-chlorophenyl)-2-(2,4-dichlorophenyl)propyl] methanesulfonate Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(COS(=O)(=O)C)CC1=CC=C(Cl)C=C1 BTWDXSOKSWYHNJ-UHFFFAOYSA-N 0.000 description 1
- LWXDUEGUHGRQMF-UHFFFAOYSA-N [3-cyclohexyl-2-(2,4-dichlorophenyl)propyl] methanesulfonate Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(COS(=O)(=O)C)CC1CCCCC1 LWXDUEGUHGRQMF-UHFFFAOYSA-N 0.000 description 1
- ZEEDMELSUHKMOX-UHFFFAOYSA-N [4-cyclohexyl-2-(2,4-dichlorophenyl)butyl] methanesulfonate Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(COS(=O)(=O)C)CCC1CCCCC1 ZEEDMELSUHKMOX-UHFFFAOYSA-N 0.000 description 1
- SMAYOTHUGIGDHZ-UHFFFAOYSA-N [4-cyclopentyl-2-(2,4-dichlorophenyl)butyl] methanesulfonate Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(COS(=O)(=O)C)CCC1CCCC1 SMAYOTHUGIGDHZ-UHFFFAOYSA-N 0.000 description 1
- SGVZKVHIUASKBY-UHFFFAOYSA-N [5-(2,4-dichloro-6-methylphenoxy)-2-(2,4-dichlorophenyl)pentyl] methanesulfonate Chemical compound CC1=CC(Cl)=CC(Cl)=C1OCCCC(COS(C)(=O)=O)C1=CC=C(Cl)C=C1Cl SGVZKVHIUASKBY-UHFFFAOYSA-N 0.000 description 1
- XUHGVEOZTJPYTG-UHFFFAOYSA-N [5-(2-bromo-4-methylphenoxy)-2-(2,4-dichlorophenyl)pentyl] methanesulfonate Chemical compound BrC1=CC(C)=CC=C1OCCCC(COS(C)(=O)=O)C1=CC=C(Cl)C=C1Cl XUHGVEOZTJPYTG-UHFFFAOYSA-N 0.000 description 1
- IUFHHUFKFSIOEB-UHFFFAOYSA-N [5-(4-chloro-2-methylphenoxy)-2-(2,4-dichlorophenyl)pentyl] methanesulfonate Chemical compound CC1=CC(Cl)=CC=C1OCCCC(COS(C)(=O)=O)C1=CC=C(Cl)C=C1Cl IUFHHUFKFSIOEB-UHFFFAOYSA-N 0.000 description 1
- SWLZTPBPAFEDJV-UHFFFAOYSA-N [5-(4-chloro-3-methylphenoxy)-2-(2,4-dichlorophenyl)pentyl] methanesulfonate Chemical compound C1=C(Cl)C(C)=CC(OCCCC(COS(C)(=O)=O)C=2C(=CC(Cl)=CC=2)Cl)=C1 SWLZTPBPAFEDJV-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000005002 aryl methyl group Chemical group 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- UUWSLBWDFJMSFP-UHFFFAOYSA-N bromomethylcyclohexane Chemical compound BrCC1CCCCC1 UUWSLBWDFJMSFP-UHFFFAOYSA-N 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000007799 cork Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 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
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000002704 decyl group Chemical group [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])* 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- BAQKJENAVQLANS-UHFFFAOYSA-N fenbutrazate Chemical compound C=1C=CC=CC=1C(CC)C(=O)OCCN(C1C)CCOC1C1=CC=CC=C1 BAQKJENAVQLANS-UHFFFAOYSA-N 0.000 description 1
- 229960002533 fenbutrazate Drugs 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000005059 halophenyl group Chemical group 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 150000004324 hydroxyarenes Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- UPZGJLYTRBYTLM-UHFFFAOYSA-M lithium;iodide;dihydrate Chemical compound [Li+].O.O.[I-] UPZGJLYTRBYTLM-UHFFFAOYSA-M 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- YZPNYLPAGHAAPJ-UHFFFAOYSA-N methyl 2-(2,4-dibromophenyl)acetate Chemical compound COC(=O)CC1=CC=C(Br)C=C1Br YZPNYLPAGHAAPJ-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- IKNKDLLISLGISM-UHFFFAOYSA-N nitric acid 2-propan-2-yloxypropane Chemical compound C(C)(C)OC(C)C.[N+](=O)(O)[O-] IKNKDLLISLGISM-UHFFFAOYSA-N 0.000 description 1
- ZFVNPQBTVHWDOK-UHFFFAOYSA-N nitric acid;1h-1,2,4-triazole Chemical compound O[N+]([O-])=O.C=1N=CNN=1 ZFVNPQBTVHWDOK-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 231100000194 ovacidal Toxicity 0.000 description 1
- 230000003151 ovacidal effect Effects 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- GZQUFIUZBLOTMM-UHFFFAOYSA-N pentyl methanesulfonate Chemical compound CCCCCOS(C)(=O)=O GZQUFIUZBLOTMM-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- IPNPIHIZVLFAFP-UHFFFAOYSA-N phosphorus tribromide Chemical compound BrP(Br)Br IPNPIHIZVLFAFP-UHFFFAOYSA-N 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229960003975 potassium Drugs 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
- HJHVQCXHVMGZNC-JCJNLNMISA-M sodium;(2z)-2-[(3r,4s,5s,8s,9s,10s,11r,13r,14s,16s)-16-acetyloxy-3,11-dihydroxy-4,8,10,14-tetramethyl-2,3,4,5,6,7,9,11,12,13,15,16-dodecahydro-1h-cyclopenta[a]phenanthren-17-ylidene]-6-methylhept-5-enoate Chemical compound [Na+].O[C@@H]([C@@H]12)C[C@H]3\C(=C(/CCC=C(C)C)C([O-])=O)[C@@H](OC(C)=O)C[C@]3(C)[C@@]2(C)CC[C@@H]2[C@]1(C)CC[C@@H](O)[C@H]2C HJHVQCXHVMGZNC-JCJNLNMISA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 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
- 229940099259 vaseline Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- 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
- C07D231/12—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
- C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
- C07C309/66—Methanesulfonates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/40—Halogenated unsaturated alcohols
- C07C33/50—Halogenated unsaturated alcohols containing six-membered aromatic rings and other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US71330876A | 1976-08-10 | 1976-08-10 | |
| US713,308 | 1976-08-10 | ||
| US79163277A | 1977-04-27 | 1977-04-27 | |
| US791,632 | 1977-04-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1133492A true CA1133492A (en) | 1982-10-12 |
Family
ID=27108969
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA283,776A Expired CA1133492A (en) | 1976-08-10 | 1977-07-29 | 1-(2-aryl-2-r-ethyl)-1h-1,2,4-triazoles |
Country Status (25)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8658564B2 (en) | 2007-06-06 | 2014-02-25 | Bayer Cropscience Ag | Fungicide active ingredient combinations |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2547953A1 (de) * | 1975-10-27 | 1977-04-28 | Bayer Ag | (1-phenyl-2-triazolyl-aethyl)-aether- derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| NZ196075A (en) * | 1980-02-04 | 1982-12-07 | Janssen Pharmaceutica Nv | Agent to protect wood coatings and detergents from micro-organisms using a triazole |
| DE3267642D1 (en) * | 1981-03-10 | 1986-01-09 | Ciba Geigy Ag | Process for the preparation of phenylethyl triazoles |
| MA19798A1 (fr) * | 1982-06-08 | 1983-12-31 | Novartis Ag | Agent de lutte contre les maladies des plantes ; sa preparation et son application a la protection des plantes . |
| DE3362000D1 (en) * | 1982-06-18 | 1986-03-13 | Ciba Geigy Ag | Method for the production of 1-(2-(,4-dichlorphenyl)pentyl)-1h-1,2,4-triazole and hydrazone- or hydrazine-derivatives |
| EP0121081B1 (de) * | 1983-03-03 | 1991-01-30 | BASF Aktiengesellschaft | Azolylmethylcycloalkane, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| DE3310830A1 (de) * | 1983-03-24 | 1984-09-27 | Bayer Ag, 5090 Leverkusen | Substituierte phenethyl-triazolyl-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
| EP0126430B1 (de) * | 1983-05-19 | 1991-08-28 | Ciba-Geigy Ag | Verfahren zur Herstellung von 1-Triazolylethylether-Derivaten, sowie mikrobizide Mittel enthaltende neue 1-triazolyl-phenoxyphenylethylether-derivate als Wirkstoffe und deren Verwendung |
| GB8405368D0 (en) * | 1984-03-01 | 1984-04-04 | Ici Plc | Heterocyclic compounds |
| IT1204773B (it) * | 1986-01-23 | 1989-03-10 | Montedison Spa | Azolilderivati fungicidi |
| GB8818561D0 (en) * | 1988-08-04 | 1988-09-07 | Ici Plc | Diphenylethane derivatives |
| GB8818791D0 (en) * | 1988-08-08 | 1988-09-07 | Ici Plc | Azole derivatives |
| JPH03125676A (ja) * | 1989-10-12 | 1991-05-29 | Deele Raumu:Kk | 自動車 |
| DE19829113A1 (de) | 1998-06-10 | 1999-12-16 | Bayer Ag | Mittel zur Bekämpfung von Pflanzenschädlingen |
| DE10347090A1 (de) | 2003-10-10 | 2005-05-04 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
| DE10349501A1 (de) | 2003-10-23 | 2005-05-25 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
| DE102005026482A1 (de) | 2005-06-09 | 2006-12-14 | Bayer Cropscience Ag | Wirkstoffkombinationen |
| EP2255650A3 (de) | 2005-06-09 | 2011-04-27 | Bayer CropScience AG | Wirkstoffkombinationen |
| DE102005035300A1 (de) | 2005-07-28 | 2007-02-01 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
| DE102006023263A1 (de) | 2006-05-18 | 2007-11-22 | Bayer Cropscience Ag | Synergistische Wirkstoffkombinationen |
| DE102007045920B4 (de) | 2007-09-26 | 2018-07-05 | Bayer Intellectual Property Gmbh | Synergistische Wirkstoffkombinationen |
| BR112012001080A2 (pt) | 2009-07-16 | 2015-09-01 | Bayer Cropscience Ag | Combinações de substâncias ativas sinérgicas contendo feniltriazóis |
| EP2910126A1 (en) | 2015-05-05 | 2015-08-26 | Bayer CropScience AG | Active compound combinations having insecticidal properties |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU557755A3 (ru) * | 1968-08-19 | 1977-05-05 | Янссен Фармасьютика Н.В. (Фирма) | Способ получени производных имидазола |
| US3647814A (en) * | 1969-07-03 | 1972-03-07 | Rohm & Haas | Method for preparing 4-substituted-1 2 4-triazoles |
| US3658813A (en) * | 1970-01-13 | 1972-04-25 | Janssen Pharmaceutica Nv | 1-(beta-aryl-beta-(r-oxy)-ethyl)-imidazoles |
| DE2009020C3 (de) * | 1970-02-26 | 1979-09-13 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von N-(l,l,l-trisubstituierten)-Methylazolen |
| US3821394A (en) * | 1970-07-29 | 1974-06-28 | H Timmler | Antimycotic composition and method employing a substituted benzyl-azoles |
| US3927017A (en) * | 1974-06-27 | 1975-12-16 | Janssen Pharmaceutica Nv | 1-({62 -Aryl-{62 -R-ethyl)imidazoles |
| DE2431407C2 (de) * | 1974-06-29 | 1982-12-02 | Bayer Ag, 5090 Leverkusen | 1,2,4-Triazol-1-yl-alkanone und -alkanole, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Fungizide |
-
1977
- 1977-07-26 AU AU27326/77A patent/AU515134B2/en not_active Expired
- 1977-07-27 GB GB31630/77A patent/GB1589852A/en not_active Expired
- 1977-07-27 CY CY1204A patent/CY1204A/xx unknown
- 1977-07-29 CA CA283,776A patent/CA1133492A/en not_active Expired
- 1977-07-29 FR FR7723528A patent/FR2361375A1/fr active Granted
- 1977-08-03 NZ NZ184835A patent/NZ184835A/xx unknown
- 1977-08-08 IT IT50599/77A patent/IT1080109B/it active
- 1977-08-08 PT PT66902A patent/PT66902B/pt unknown
- 1977-08-09 BR BR7705266A patent/BR7705266A/pt unknown
- 1977-08-09 AT AT581377A patent/AT361918B/de not_active IP Right Cessation
- 1977-08-09 DK DK355477A patent/DK159551C/da not_active IP Right Cessation
- 1977-08-09 NL NLAANVRAGE7708764,A patent/NL181431C/xx not_active IP Right Cessation
- 1977-08-09 DE DE19772735872 patent/DE2735872A1/de active Granted
- 1977-08-09 IE IE1664/77A patent/IE45462B1/en not_active IP Right Cessation
- 1977-08-09 IL IL52692A patent/IL52692A/xx unknown
- 1977-08-09 AR AR268726A patent/AR222142A1/es active
- 1977-08-09 SE SE7709016A patent/SE437267B/xx not_active IP Right Cessation
- 1977-08-10 JP JP9521177A patent/JPS5321168A/ja active Granted
- 1977-08-10 GR GR54132A patent/GR58202B/el unknown
- 1977-08-10 ES ES461526A patent/ES461526A1/es not_active Expired
- 1977-08-10 CH CH982877A patent/CH630231A5/de not_active IP Right Cessation
-
1983
- 1983-06-17 SG SG346/83A patent/SG34683G/en unknown
- 1983-06-23 KE KE3299A patent/KE3299A/xx unknown
- 1983-11-24 HK HK606/83A patent/HK60683A/en not_active IP Right Cessation
-
1985
- 1985-12-30 MY MY32/85A patent/MY8500032A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8658564B2 (en) | 2007-06-06 | 2014-02-25 | Bayer Cropscience Ag | Fungicide active ingredient combinations |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1133492A (en) | 1-(2-aryl-2-r-ethyl)-1h-1,2,4-triazoles | |
| US4598085A (en) | Fungicidal 1-(2-aryl-2-R-ethyl)-1H-1,2,4-triazoles | |
| US4772623A (en) | Triazolyl-alkanones or triazolyl-alkanols | |
| US3940414A (en) | 1-Phenoxy-[imidazolyl-(1)]-2-hydroxy-alkanes | |
| CA1212952A (en) | 1-phenyl-2-triazolyl-ethyl ether derivatives and their use as fungicides | |
| EP0000752A2 (de) | Alpha-azolysulfide, -sulfoxide und -sulfone, deren Salze und Metallkomplexe, Verfahren zu ihrer Herstellung, sowie sie enthaltende Mittel zur Pilzbekämpfung | |
| US3940415A (en) | 1-(Imidazolyl-1)-2-aryloxy-3-hydroxy-alkanes | |
| CA1092128A (en) | Combatting fungi with 1-(azol-1-yl)-4-halo-1-phenoxy- butan-2-ones and -ols | |
| EP0111711A2 (de) | Heterocyclisch substituierte Hydroxyalkyl-azolyl-Derivate | |
| US3972892A (en) | 1-[1,2,4-triazolyl-(1)]-2-aryloxy-3-hydroxy-alkanes | |
| EP0019189B1 (de) | Fungizide Mittel, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Fungizide | |
| EP0104549B1 (de) | Azolylbutanole | |
| US4151287A (en) | Combating fungi with 1-diaryloxy-1-triazolyl-3,3-dimethyl-butan-2-ones and butan-2-ols | |
| CA1330564C (en) | Azole derivatives, process for producing the same, and preparation for controlling plant diseases containing the same | |
| DE3032326A1 (de) | Azolylalkyl-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide | |
| DD151864A5 (de) | Fungizide mittel | |
| DE2908323A1 (de) | Azolsubstituierte atropasaeurederivate, verfahren zu ihrer herstellung und ihre verwendung als pflanzenschutzmittel | |
| EP0023286B1 (de) | Azolyl-alkenole, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Fungizide | |
| EP0061794A1 (en) | Antimicrobial imidazole derivatives | |
| US4524110A (en) | Antimicrobial imidazole derivatives | |
| DD158848A5 (de) | Substituierte phenyl-trazolyl-vinyl-ketone,verfahren zu ihrer herstellung sowie ihre verwendung als fungizide | |
| EP0096801B1 (de) | Azolylmethyl-ketone, Verfahren zu ihrer Herstellung und ihre Verwendung als Zwischenprodukte | |
| CA1213592A (en) | Substituted azolylether-ketones and -carbinols | |
| DE2705678A1 (de) | 2,4-dichlorphenyl-triazolyl-aethan-one (-ole), verfahren zu ihrer herstellung sowie ihre verwendung als fungizide | |
| DD220216A5 (de) | Fungizide mittel |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |