JPS6129347B2 - - Google Patents
Info
- Publication number
- JPS6129347B2 JPS6129347B2 JP52095211A JP9521177A JPS6129347B2 JP S6129347 B2 JPS6129347 B2 JP S6129347B2 JP 52095211 A JP52095211 A JP 52095211A JP 9521177 A JP9521177 A JP 9521177A JP S6129347 B2 JPS6129347 B2 JP S6129347B2
- Authority
- JP
- Japan
- Prior art keywords
- triazole
- acid addition
- physiologically acceptable
- acceptable acid
- dichlorophenyl
- 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 description 53
- 239000002253 acid Substances 0.000 claims description 47
- 150000003839 salts Chemical class 0.000 claims description 46
- 125000000217 alkyl group Chemical group 0.000 claims description 39
- -1 dibromophenyl Chemical group 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 34
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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 19
- 239000004480 active ingredient Substances 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 14
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical class N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 claims description 13
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 11
- 150000002148 esters Chemical group 0.000 claims description 11
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- 239000012876 carrier material Substances 0.000 claims description 10
- 150000003852 triazoles Chemical class 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 238000010992 reflux Methods 0.000 claims description 8
- 230000000855 fungicidal effect Effects 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- LFLBHTZRLVHUQC-UHFFFAOYSA-N butyl methanesulfonate Chemical compound CCCCOS(C)(=O)=O LFLBHTZRLVHUQC-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000005059 halophenyl group Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 159000000000 sodium salts Chemical class 0.000 claims description 6
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 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 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 125000004188 dichlorophenyl group Chemical group 0.000 claims description 3
- 239000003495 polar organic solvent Substances 0.000 claims description 3
- 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 description 2
- 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 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
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 239000000417 fungicide Substances 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
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 claims description 2
- 230000000845 anti-microbial effect Effects 0.000 claims 4
- MDUSUFIKBUMDTJ-UHFFFAOYSA-N sodium;1h-1,2,4-triazole Chemical compound [Na].C=1N=CNN=1 MDUSUFIKBUMDTJ-UHFFFAOYSA-N 0.000 claims 2
- 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
- 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 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 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
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 238000002844 melting Methods 0.000 description 50
- 230000008018 melting Effects 0.000 description 50
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 238000009835 boiling Methods 0.000 description 24
- 238000003756 stirring Methods 0.000 description 24
- 239000000284 extract Substances 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- 239000000203 mixture Substances 0.000 description 20
- 239000011541 reaction mixture Substances 0.000 description 20
- 239000000047 product Substances 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 12
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 229910002651 NO3 Inorganic materials 0.000 description 11
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 11
- 239000012312 sodium hydride Substances 0.000 description 11
- 229910000104 sodium hydride Inorganic materials 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 238000001816 cooling Methods 0.000 description 10
- 239000006185 dispersion Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 241000233866 Fungi Species 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 5
- 229910001873 dinitrogen Inorganic materials 0.000 description 5
- 230000002538 fungal effect Effects 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 150000002825 nitriles Chemical class 0.000 description 5
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 5
- GZQUFIUZBLOTMM-UHFFFAOYSA-N pentyl methanesulfonate Chemical compound CCCCCOS(C)(=O)=O GZQUFIUZBLOTMM-UHFFFAOYSA-N 0.000 description 5
- 239000012258 stirred mixture Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 230000005587 bubbling Effects 0.000 description 4
- 229960001701 chloroform Drugs 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 4
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- NXTLYFWOLCJOAM-UHFFFAOYSA-N 2-(2,4-dibromophenyl)acetonitrile Chemical compound BrC1=CC=C(CC#N)C(Br)=C1 NXTLYFWOLCJOAM-UHFFFAOYSA-N 0.000 description 3
- VJARIBGMDPJLCL-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)acetonitrile Chemical compound ClC1=CC=C(CC#N)C(Cl)=C1 VJARIBGMDPJLCL-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 3
- 240000008067 Cucumis sativus Species 0.000 description 3
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- 239000003208 petroleum Substances 0.000 description 3
- 230000008635 plant growth Effects 0.000 description 3
- 230000003449 preventive effect Effects 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000003944 tolyl group Chemical group 0.000 description 3
- LUZWEUJONGDDQD-UHFFFAOYSA-N 1,3-dichlorobenzene;methyl acetate Chemical compound COC(C)=O.ClC1=CC=CC(Cl)=C1 LUZWEUJONGDDQD-UHFFFAOYSA-N 0.000 description 2
- COGZDFNIMRTUNF-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)propyl]-1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(C)CN1C=NC=N1 COGZDFNIMRTUNF-UHFFFAOYSA-N 0.000 description 2
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 2
- 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 2
- PUZLVQJXUAYVOW-UHFFFAOYSA-N 2-(2,4-dibromophenyl)hexanenitrile Chemical compound CCCCC(C#N)C1=CC=C(Br)C=C1Br PUZLVQJXUAYVOW-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
- 125000006040 2-hexenyl group Chemical group 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- BGBHYEMEEAZPCO-UHFFFAOYSA-N 3-cyclohexyl-2-(2,4-dichlorophenyl)propan-1-ol Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CO)CC1CCCCC1 BGBHYEMEEAZPCO-UHFFFAOYSA-N 0.000 description 2
- ZKDMQLAMGYCCSC-UHFFFAOYSA-N 4-(4-bromophenoxy)-2-(2,4-dichlorophenyl)butan-1-ol Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CO)CCOC1=CC=C(Br)C=C1 ZKDMQLAMGYCCSC-UHFFFAOYSA-N 0.000 description 2
- CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-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
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- 240000005979 Hordeum vulgare Species 0.000 description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 description 2
- 206010061217 Infestation Diseases 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-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
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- 241000221577 Uromyces appendiculatus Species 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
- 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 2
- 239000000443 aerosol Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 230000008952 bacterial invasion Effects 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000000068 chlorophenyl group Chemical group 0.000 description 2
- WBYWAXJHAXSJNI-UHFFFAOYSA-N cinnamic acid Chemical compound OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000010410 dusting Methods 0.000 description 2
- 230000008029 eradication Effects 0.000 description 2
- 230000035784 germination Effects 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 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 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
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- 239000000463 material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
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- 239000011734 sodium Substances 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
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- 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
- 230000003287 optical effect Effects 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
- 239000003960 organic solvent Substances 0.000 description 1
- GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 235000019271 petrolatum Nutrition 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
- 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
- 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
- 239000000843 powder Substances 0.000 description 1
- 239000012254 powdered material Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 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
- 239000002689 soil Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229960005137 succinic acid Drugs 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000271 synthetic detergent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 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
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 229940024986 topical antifungal imidazole and triazole derivative Drugs 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
- 238000005406 washing 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 (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US71330876A | 1976-08-10 | 1976-08-10 | |
US79163277A | 1977-04-27 | 1977-04-27 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5321168A JPS5321168A (en) | 1978-02-27 |
JPS6129347B2 true JPS6129347B2 (de) | 1986-07-05 |
Family
ID=27108969
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP9521177A Granted JPS5321168A (en) | 1976-08-10 | 1977-08-10 | 11*22aryll22rrethyl**1hh1*2*44triazoles* its preparation and their use |
Country Status (25)
Country | Link |
---|---|
JP (1) | JPS5321168A (de) |
AR (1) | AR222142A1 (de) |
AT (1) | AT361918B (de) |
AU (1) | AU515134B2 (de) |
BR (1) | BR7705266A (de) |
CA (1) | CA1133492A (de) |
CH (1) | CH630231A5 (de) |
CY (1) | CY1204A (de) |
DE (1) | DE2735872A1 (de) |
DK (1) | DK159551C (de) |
ES (1) | ES461526A1 (de) |
FR (1) | FR2361375A1 (de) |
GB (1) | GB1589852A (de) |
GR (1) | GR58202B (de) |
HK (1) | HK60683A (de) |
IE (1) | IE45462B1 (de) |
IL (1) | IL52692A (de) |
IT (1) | IT1080109B (de) |
KE (1) | KE3299A (de) |
MY (1) | MY8500032A (de) |
NL (1) | NL181431C (de) |
NZ (1) | NZ184835A (de) |
PT (1) | PT66902B (de) |
SE (1) | SE437267B (de) |
SG (1) | SG34683G (de) |
Families Citing this family (24)
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 |
ATE16702T1 (de) * | 1981-03-10 | 1985-12-15 | Ciba Geigy Ag | Verfahren zur herstellung von phenylaethyltriazolen. |
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 . |
EP0097617B1 (de) * | 1982-06-18 | 1986-01-29 | Ciba-Geigy Ag | Verfahren zur Herstellung von 1-(2-(2,4-Dichlorphenyl)pentyl)-1H-1,2,4-triazol und neue Hydrazon- oder Hydrazinderivate |
DE3484023D1 (de) * | 1983-03-03 | 1991-03-07 | Basf Ag | 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 |
US8754009B2 (en) | 2005-06-09 | 2014-06-17 | Bayer Cropscience Ag | Active compound combinations |
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 |
EP2000028A1 (de) | 2007-06-06 | 2008-12-10 | Bayer CropScience Aktiengesellschaft | Fungizide Wirkstoffkombinationen |
DE102007045920B4 (de) | 2007-09-26 | 2018-07-05 | Bayer Intellectual Property Gmbh | Synergistische Wirkstoffkombinationen |
EP2453750A2 (de) | 2009-07-16 | 2012-05-23 | Bayer CropScience AG | Synergistische wirkstoffkombinationen mit phenyltriazolen |
EP2910126A1 (de) | 2015-05-05 | 2015-08-26 | Bayer CropScience AG | Wirkstoffkombinationen mit insektiziden eigenschaften |
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 CY CY1204A patent/CY1204A/xx unknown
- 1977-07-27 GB GB31630/77A patent/GB1589852A/en not_active Expired
- 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 DK DK355477A patent/DK159551C/da 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 IE IE1664/77A patent/IE45462B1/en not_active IP Right Cessation
- 1977-08-09 DE DE19772735872 patent/DE2735872A1/de active Granted
- 1977-08-09 SE SE7709016A patent/SE437267B/xx not_active IP Right Cessation
- 1977-08-09 AT AT581377A patent/AT361918B/de not_active IP Right Cessation
- 1977-08-09 NL NLAANVRAGE7708764,A patent/NL181431C/xx not_active IP Right Cessation
- 1977-08-09 BR BR7705266A patent/BR7705266A/pt unknown
- 1977-08-10 JP JP9521177A patent/JPS5321168A/ja active Granted
- 1977-08-10 CH CH982877A patent/CH630231A5/de not_active IP Right Cessation
- 1977-08-10 GR GR54132A patent/GR58202B/el unknown
- 1977-08-10 ES ES461526A patent/ES461526A1/es not_active Expired
-
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/xx not_active IP Right Cessation
-
1985
- 1985-12-30 MY MY32/85A patent/MY8500032A/xx unknown
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