JPS61152661A - １，２，４‐トリアゾール誘導体 - Google Patents
１，２，４‐トリアゾール誘導体Info
- Publication number
- JPS61152661A JPS61152661A JP60287611A JP28761185A JPS61152661A JP S61152661 A JPS61152661 A JP S61152661A JP 60287611 A JP60287611 A JP 60287611A JP 28761185 A JP28761185 A JP 28761185A JP S61152661 A JPS61152661 A JP S61152661A
- Authority
- JP
- Japan
- Prior art keywords
- triazole
- trifluoromethylphenyl
- methyl
- formula
- chlorophenyl
- 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.)
- Pending
Links
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical class C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 title claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 86
- 239000000203 mixture Substances 0.000 claims description 66
- -1 o-trifluoromethylphenyl Chemical group 0.000 claims description 51
- 239000002253 acid Substances 0.000 claims description 43
- 238000000034 method Methods 0.000 claims description 33
- 150000003839 salts Chemical class 0.000 claims description 33
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 claims description 19
- 241000607479 Yersinia pestis Species 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 238000009472 formulation Methods 0.000 claims description 10
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 9
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 125000004970 halomethyl group Chemical group 0.000 claims description 4
- 230000002140 halogenating effect Effects 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- PAIMHPXIPYGIAP-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-prop-1-enyl-5-[2-(trifluoromethyl)phenyl]-1,2,4-triazole Chemical compound CC=CN1N=C(C=2C(=CC=CC=2)Cl)N=C1C1=CC=CC=C1C(F)(F)F PAIMHPXIPYGIAP-UHFFFAOYSA-N 0.000 claims description 2
- XZLXHCQHHSKSPX-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-propyl-5-[2-(trifluoromethyl)phenyl]-1,2,4-triazole Chemical compound CCCN1N=C(C=2C(=CC=CC=2)Cl)N=C1C1=CC=CC=C1C(F)(F)F XZLXHCQHHSKSPX-UHFFFAOYSA-N 0.000 claims description 2
- RIWFBWVDTAHEQI-UHFFFAOYSA-N 3-[5-(2-chlorophenyl)-2-methyl-1,2,4-triazol-3-yl]-4-(trifluoromethyl)pyridine Chemical compound CN1N=C(C=2C(=CC=CC=2)Cl)N=C1C1=CN=CC=C1C(F)(F)F RIWFBWVDTAHEQI-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 5
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims 2
- KQFWCLXBSYYOLD-UHFFFAOYSA-N 3-(2-bromophenyl)-1-methyl-5-[2-(trifluoromethyl)phenyl]-1,2,4-triazole Chemical compound CN1N=C(C=2C(=CC=CC=2)Br)N=C1C1=CC=CC=C1C(F)(F)F KQFWCLXBSYYOLD-UHFFFAOYSA-N 0.000 claims 2
- BJHCLGQSXJGZLB-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-methyl-5-[2-(trifluoromethyl)phenyl]-1,2,4-triazole Chemical compound CN1N=C(C=2C(=CC=CC=2)Cl)N=C1C1=CC=CC=C1C(F)(F)F BJHCLGQSXJGZLB-UHFFFAOYSA-N 0.000 claims 2
- LDHUTBZKAPDSNX-UHFFFAOYSA-N 5-(2-chlorophenyl)-1-methyl-3-[2-(trifluoromethyl)phenyl]-1,2,4-triazole Chemical compound CN1N=C(C=2C(=CC=CC=2)C(F)(F)F)N=C1C1=CC=CC=C1Cl LDHUTBZKAPDSNX-UHFFFAOYSA-N 0.000 claims 2
- FIFQOFCNAJALHT-UHFFFAOYSA-N 1-(2-chloroethyl)-3-(2-chlorophenyl)-5-[2-(trifluoromethyl)phenyl]-1,2,4-triazole Chemical compound FC(F)(F)C1=CC=CC=C1C1=NC(C=2C(=CC=CC=2)Cl)=NN1CCCl FIFQOFCNAJALHT-UHFFFAOYSA-N 0.000 claims 1
- MMSRDWICMFZQNC-UHFFFAOYSA-N 1-ethyl-3-(2-fluorophenyl)-5-[2-(trifluoromethyl)phenyl]-1,2,4-triazole Chemical compound CCN1N=C(C=2C(=CC=CC=2)F)N=C1C1=CC=CC=C1C(F)(F)F MMSRDWICMFZQNC-UHFFFAOYSA-N 0.000 claims 1
- RAUSBLQSLZOIEF-UHFFFAOYSA-N 1-ethyl-5-(2-fluorophenyl)-3-[2-(trifluoromethyl)phenyl]-1,2,4-triazole Chemical compound CCN1N=C(C=2C(=CC=CC=2)C(F)(F)F)N=C1C1=CC=CC=C1F RAUSBLQSLZOIEF-UHFFFAOYSA-N 0.000 claims 1
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 claims 1
- QTDZFVDOLSFVCW-UHFFFAOYSA-N 2-[1-methyl-5-[2-(trifluoromethyl)phenyl]-1,2,4-triazol-3-yl]benzonitrile Chemical compound CN1N=C(C=2C(=CC=CC=2)C#N)N=C1C1=CC=CC=C1C(F)(F)F QTDZFVDOLSFVCW-UHFFFAOYSA-N 0.000 claims 1
- GFTGENBVHRFBPK-UHFFFAOYSA-N 2-[1-methyl-5-[2-(trifluoromethyl)phenyl]-1,2,4-triazol-3-yl]pyridine Chemical compound CN1N=C(C=2N=CC=CC=2)N=C1C1=CC=CC=C1C(F)(F)F GFTGENBVHRFBPK-UHFFFAOYSA-N 0.000 claims 1
- PTXSBNHOMZCURE-UHFFFAOYSA-N 3-(2,3-dichlorophenyl)-1-methyl-5-[2-(trifluoromethyl)phenyl]-1,2,4-triazole Chemical compound CN1N=C(C=2C(=C(Cl)C=CC=2)Cl)N=C1C1=CC=CC=C1C(F)(F)F PTXSBNHOMZCURE-UHFFFAOYSA-N 0.000 claims 1
- IXZIYTUWSFJNBG-UHFFFAOYSA-N 3-(2,5-dichlorophenyl)-1-methyl-5-[2-(trifluoromethyl)phenyl]-1,2,4-triazole Chemical compound CN1N=C(C=2C(=CC=C(Cl)C=2)Cl)N=C1C1=CC=CC=C1C(F)(F)F IXZIYTUWSFJNBG-UHFFFAOYSA-N 0.000 claims 1
- ITKYDSGLQISEKW-UHFFFAOYSA-N 3-(2-chloro-4-fluorophenyl)-1-methyl-5-[2-(trifluoromethyl)phenyl]-1,2,4-triazole Chemical compound CN1N=C(C=2C(=CC(F)=CC=2)Cl)N=C1C1=CC=CC=C1C(F)(F)F ITKYDSGLQISEKW-UHFFFAOYSA-N 0.000 claims 1
- IRSQHHDFKIMNIU-UHFFFAOYSA-N 3-(2-chloro-6-fluorophenyl)-1-methyl-5-[2-(trifluoromethyl)phenyl]-1,2,4-triazole Chemical compound CN1N=C(C=2C(=CC=CC=2F)Cl)N=C1C1=CC=CC=C1C(F)(F)F IRSQHHDFKIMNIU-UHFFFAOYSA-N 0.000 claims 1
- RNUGBIUWOLWNRS-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-(2,2,2-trifluoroethyl)-5-[2-(trifluoromethyl)phenyl]-1,2,4-triazole Chemical compound FC(F)(F)CN1N=C(C=2C(=CC=CC=2)Cl)N=C1C1=CC=CC=C1C(F)(F)F RNUGBIUWOLWNRS-UHFFFAOYSA-N 0.000 claims 1
- MDTZRYNDVJQCLB-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-ethyl-5-[2-(trifluoromethyl)phenyl]-1,2,4-triazole Chemical compound CCN1N=C(C=2C(=CC=CC=2)Cl)N=C1C1=CC=CC=C1C(F)(F)F MDTZRYNDVJQCLB-UHFFFAOYSA-N 0.000 claims 1
- JRILOOGTJVGXOZ-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-propan-2-yl-5-[2-(trifluoromethyl)phenyl]-1,2,4-triazole Chemical compound CC(C)N1N=C(C=2C(=CC=CC=2)Cl)N=C1C1=CC=CC=C1C(F)(F)F JRILOOGTJVGXOZ-UHFFFAOYSA-N 0.000 claims 1
- TVNAUZBXNZFQTD-UHFFFAOYSA-N 3-(2-fluorophenyl)-1-methyl-5-[2-(trifluoromethyl)phenyl]-1,2,4-triazole Chemical compound CN1N=C(C=2C(=CC=CC=2)F)N=C1C1=CC=CC=C1C(F)(F)F TVNAUZBXNZFQTD-UHFFFAOYSA-N 0.000 claims 1
- BUMXNPHXGGCNRH-UHFFFAOYSA-N 3-(2-iodophenyl)-1-methyl-5-[2-(trifluoromethyl)phenyl]-1,2,4-triazole Chemical compound CN1N=C(C=2C(=CC=CC=2)I)N=C1C1=CC=CC=C1C(F)(F)F BUMXNPHXGGCNRH-UHFFFAOYSA-N 0.000 claims 1
- XRLUXNQQFBBSSS-UHFFFAOYSA-N 3-(3-chloro-2-fluorophenyl)-1-methyl-5-[2-(trifluoromethyl)phenyl]-1,2,4-triazole Chemical compound CN1N=C(C=2C(=C(Cl)C=CC=2)F)N=C1C1=CC=CC=C1C(F)(F)F XRLUXNQQFBBSSS-UHFFFAOYSA-N 0.000 claims 1
- CLJOSDRDHJCNLF-UHFFFAOYSA-N 3-(4-chloro-2-fluorophenyl)-1-methyl-5-[2-(trifluoromethyl)phenyl]-1,2,4-triazole Chemical compound CN1N=C(C=2C(=CC(Cl)=CC=2)F)N=C1C1=CC=CC=C1C(F)(F)F CLJOSDRDHJCNLF-UHFFFAOYSA-N 0.000 claims 1
- MYTZCGQCTCBJOA-UHFFFAOYSA-N 3-[(2-methoxyphenyl)methyl]-1-methyl-5-[2-(trifluoromethyl)phenyl]-1,2,4-triazole Chemical compound COC1=CC=CC=C1CC1=NN(C)C(C=2C(=CC=CC=2)C(F)(F)F)=N1 MYTZCGQCTCBJOA-UHFFFAOYSA-N 0.000 claims 1
- PXXMTCDOTYXESV-UHFFFAOYSA-N 3-[1-methyl-5-[2-(trifluoromethyl)phenyl]-1,2,4-triazol-3-yl]pyridine Chemical compound CN1N=C(C=2C=NC=CC=2)N=C1C1=CC=CC=C1C(F)(F)F PXXMTCDOTYXESV-UHFFFAOYSA-N 0.000 claims 1
- HLZIJXHOMXFWHY-UHFFFAOYSA-N 4-[1-methyl-5-[2-(trifluoromethyl)phenyl]-1,2,4-triazol-3-yl]pyridine Chemical compound CN1N=C(C=2C=CN=CC=2)N=C1C1=CC=CC=C1C(F)(F)F HLZIJXHOMXFWHY-UHFFFAOYSA-N 0.000 claims 1
- XZICFTVWQVQMBO-UHFFFAOYSA-N 5-(2-chlorophenyl)-1-ethyl-3-[2-(trifluoromethyl)phenyl]-1,2,4-triazole Chemical compound CCN1N=C(C=2C(=CC=CC=2)C(F)(F)F)N=C1C1=CC=CC=C1Cl XZICFTVWQVQMBO-UHFFFAOYSA-N 0.000 claims 1
- TVSSOEOVMTTWGK-UHFFFAOYSA-N 5-(2-chlorophenyl)-1-prop-1-enyl-3-[2-(trifluoromethyl)phenyl]-1,2,4-triazole Chemical compound CC=CN1N=C(C=2C(=CC=CC=2)C(F)(F)F)N=C1C1=CC=CC=C1Cl TVSSOEOVMTTWGK-UHFFFAOYSA-N 0.000 claims 1
- RNSKKKQBVOLGES-UHFFFAOYSA-N 5-(2-chlorophenyl)-1-propan-2-yl-3-[2-(trifluoromethyl)phenyl]-1,2,4-triazole Chemical compound CC(C)N1N=C(C=2C(=CC=CC=2)C(F)(F)F)N=C1C1=CC=CC=C1Cl RNSKKKQBVOLGES-UHFFFAOYSA-N 0.000 claims 1
- HZWYLKSIUZHSGY-UHFFFAOYSA-N 5-(2-chlorophenyl)-1-propyl-3-[2-(trifluoromethyl)phenyl]-1,2,4-triazole Chemical compound CCCN1N=C(C=2C(=CC=CC=2)C(F)(F)F)N=C1C1=CC=CC=C1Cl HZWYLKSIUZHSGY-UHFFFAOYSA-N 0.000 claims 1
- HUJUBANPLITKPV-UHFFFAOYSA-N 5-(2-chlorophenyl)-1h-1,2,4-triazole Chemical compound ClC1=CC=CC=C1C1=NC=NN1 HUJUBANPLITKPV-UHFFFAOYSA-N 0.000 claims 1
- LBGFXKGXICXEID-UHFFFAOYSA-N 5-(2-fluorophenyl)-1-methyl-3-[2-(trifluoromethyl)phenyl]-1,2,4-triazole Chemical compound CN1N=C(C=2C(=CC=CC=2)C(F)(F)F)N=C1C1=CC=CC=C1F LBGFXKGXICXEID-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 239000012752 auxiliary agent Substances 0.000 claims 1
- 125000005059 halophenyl group Chemical group 0.000 claims 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 claims 1
- 239000007858 starting material Substances 0.000 description 47
- 238000002844 melting Methods 0.000 description 34
- 230000008018 melting Effects 0.000 description 34
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 25
- 239000013543 active substance Substances 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 18
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 17
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- 238000005160 1H NMR spectroscopy Methods 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 239000000843 powder Substances 0.000 description 14
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 11
- 239000003995 emulsifying agent Substances 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- MXIUWSYTQJLIKE-UHFFFAOYSA-N 2-(trifluoromethyl)benzoyl chloride Chemical compound FC(F)(F)C1=CC=CC=C1C(Cl)=O MXIUWSYTQJLIKE-UHFFFAOYSA-N 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 239000007921 spray Substances 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 7
- 239000012876 carrier material Substances 0.000 description 7
- 239000002270 dispersing agent Substances 0.000 description 7
- 239000002612 dispersion medium Substances 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 241000238876 Acari Species 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
- 238000001819 mass spectrum Methods 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 230000002829 reductive effect Effects 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 230000001804 emulsifying effect Effects 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 239000012262 resinous product Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 241000258937 Hemiptera Species 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 4
- 150000004292 cyclic ethers Chemical class 0.000 description 4
- 238000010410 dusting Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 239000003701 inert diluent Substances 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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Landscapes
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH610584 | 1984-12-21 | ||
| CH6105/84-0 | 1984-12-21 | ||
| CH4151/85-4 | 1985-09-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS61152661A true JPS61152661A (ja) | 1986-07-11 |
Family
ID=4304347
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60287611A Pending JPS61152661A (ja) | 1984-12-21 | 1985-12-20 | １，２，４‐トリアゾール誘導体 |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS61152661A (en, 2012) |
| BR (1) | BR8506390A (en, 2012) |
| GR (1) | GR853049B (en, 2012) |
| ZA (1) | ZA859576B (en, 2012) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994024110A1 (en) * | 1993-04-16 | 1994-10-27 | Kumiai Chemical Industry Co., Ltd. | Triazole derivative, insecticidal/acaricidal agent, and process for producing the same |
| JPH08176125A (ja) * | 1994-12-27 | 1996-07-09 | Chisso Corp | トリフルオロメチル基を有するオキサジアゾール誘導体 |
| WO1999002518A1 (fr) * | 1997-07-11 | 1999-01-21 | Nippon Soda Co., Ltd. | Composes pyridyltriazole, procedes de production associes, et germicides agricoles et horticoles |
| JP2002528451A (ja) * | 1998-10-23 | 2002-09-03 | ダウ・アグロサイエンス・エル・エル・シー | ３−（置換フェニル）−５−（置換ヘテロシクリル）−１，２，４−トリアゾール化合物 |
| JP2002528449A (ja) * | 1998-10-23 | 2002-09-03 | ダウ・アグロサイエンス・エル・エル・シー | コナジラミに対する活性を有する３−（置換されたフェニル）−５−チエニル−１，２，４−トリアゾール化合物 |
| JP2002528447A (ja) * | 1998-10-23 | 2002-09-03 | ダウ・アグロサイエンス・エル・エル・シー | 殺虫性１−（置換ピリジル）−１，２，４−トリアゾール |
| JP2002528450A (ja) * | 1998-10-23 | 2002-09-03 | ダウ・アグロサイエンス・エル・エル・シー | ３−（置換フェニル）−５−チエニル又はフリル）−１，２，４−トリアゾールの製造法及びそこで用いられる新規な中間体 |
| WO2014017516A1 (ja) * | 2012-07-25 | 2014-01-30 | 株式会社富士薬品 | ４－［５－（ピリジン－４－イル）－１ｈ－１，２，４－トリアゾール－３－イル］ピリジン－２－カルボニトリルの製造方法および中間体 |
| JP2017511378A (ja) * | 2014-03-28 | 2017-04-20 | シンジェンタ パーティシペーションズ アーゲー | 硫黄含有置換基を有する殺有害生物的に活性な複素環式誘導体 |
| JP2017110003A (ja) * | 2015-12-16 | 2017-06-22 | 日本曹達株式会社 | ジアリールトリアゾール化合物および有害生物防除剤 |
| JP2019513739A (ja) * | 2016-04-07 | 2019-05-30 | シンジェンタ パーティシペーションズ アーゲー | 硫黄含有置換基を有する殺有害生物的に活性な複素環式誘導体 |
-
1985
- 1985-12-13 ZA ZA859576A patent/ZA859576B/xx unknown
- 1985-12-18 GR GR853049A patent/GR853049B/el unknown
- 1985-12-19 BR BR8506390A patent/BR8506390A/pt unknown
- 1985-12-20 JP JP60287611A patent/JPS61152661A/ja active Pending
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994024110A1 (en) * | 1993-04-16 | 1994-10-27 | Kumiai Chemical Industry Co., Ltd. | Triazole derivative, insecticidal/acaricidal agent, and process for producing the same |
| JPH08176125A (ja) * | 1994-12-27 | 1996-07-09 | Chisso Corp | トリフルオロメチル基を有するオキサジアゾール誘導体 |
| WO1999002518A1 (fr) * | 1997-07-11 | 1999-01-21 | Nippon Soda Co., Ltd. | Composes pyridyltriazole, procedes de production associes, et germicides agricoles et horticoles |
| JP2002528451A (ja) * | 1998-10-23 | 2002-09-03 | ダウ・アグロサイエンス・エル・エル・シー | ３−（置換フェニル）−５−（置換ヘテロシクリル）−１，２，４−トリアゾール化合物 |
| JP2002528449A (ja) * | 1998-10-23 | 2002-09-03 | ダウ・アグロサイエンス・エル・エル・シー | コナジラミに対する活性を有する３−（置換されたフェニル）−５−チエニル−１，２，４−トリアゾール化合物 |
| JP2002528447A (ja) * | 1998-10-23 | 2002-09-03 | ダウ・アグロサイエンス・エル・エル・シー | 殺虫性１−（置換ピリジル）−１，２，４−トリアゾール |
| JP2002528450A (ja) * | 1998-10-23 | 2002-09-03 | ダウ・アグロサイエンス・エル・エル・シー | ３−（置換フェニル）−５−チエニル又はフリル）−１，２，４−トリアゾールの製造法及びそこで用いられる新規な中間体 |
| WO2014017516A1 (ja) * | 2012-07-25 | 2014-01-30 | 株式会社富士薬品 | ４－［５－（ピリジン－４－イル）－１ｈ－１，２，４－トリアゾール－３－イル］ピリジン－２－カルボニトリルの製造方法および中間体 |
| JP5827407B2 (ja) * | 2012-07-25 | 2015-12-02 | 株式会社富士薬品 | ４−［５−（ピリジン−４−イル）−１ｈ−１，２，４−トリアゾール−３−イル］ピリジン−２−カルボニトリルの製造方法および中間体 |
| US9428488B2 (en) | 2012-07-25 | 2016-08-30 | Fujiyakuhin Co., Ltd. | Method for producing 4-[5-(pyridin-4-yl)-1H-1,2,4-triazol-3-yl]pyridine-2-carbonitrile, and intermediate thereof |
| JP2017511378A (ja) * | 2014-03-28 | 2017-04-20 | シンジェンタ パーティシペーションズ アーゲー | 硫黄含有置換基を有する殺有害生物的に活性な複素環式誘導体 |
| JP2017110003A (ja) * | 2015-12-16 | 2017-06-22 | 日本曹達株式会社 | ジアリールトリアゾール化合物および有害生物防除剤 |
| JP2019513739A (ja) * | 2016-04-07 | 2019-05-30 | シンジェンタ パーティシペーションズ アーゲー | 硫黄含有置換基を有する殺有害生物的に活性な複素環式誘導体 |
Also Published As
| Publication number | Publication date |
|---|---|
| GR853049B (en, 2012) | 1986-04-22 |
| ZA859576B (en) | 1986-08-27 |
| BR8506390A (pt) | 1986-09-02 |
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