JPS626547B2 - - Google Patents
Info
- Publication number
- JPS626547B2 JPS626547B2 JP15123578A JP15123578A JPS626547B2 JP S626547 B2 JPS626547 B2 JP S626547B2 JP 15123578 A JP15123578 A JP 15123578A JP 15123578 A JP15123578 A JP 15123578A JP S626547 B2 JPS626547 B2 JP S626547B2
- Authority
- JP
- Japan
- Prior art keywords
- aminoquinazoline
- ethyl
- chloro
- methylphenoxy
- methyl
- 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- -1 methylene, ethylene, methylmethylene, trimethylene, ethylmethylene Chemical group 0.000 description 143
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 53
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- 150000001875 compounds Chemical class 0.000 description 25
- CZAAKPFIWJXPQT-UHFFFAOYSA-N quinazolin-2-amine Chemical compound C1=CC=CC2=NC(N)=NC=C21 CZAAKPFIWJXPQT-UHFFFAOYSA-N 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 241000607479 Yersinia pestis Species 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 239000013078 crystal Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 8
- 238000000921 elemental analysis Methods 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 241001454293 Tetranychus urticae Species 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- GVRRXASZZAKBMN-UHFFFAOYSA-N 4-chloroquinazoline Chemical compound C1=CC=C2C(Cl)=NC=NC2=C1 GVRRXASZZAKBMN-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 241001454295 Tetranychidae Species 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 241000238631 Hexapoda Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 241000219977 Vigna Species 0.000 description 3
- 235000010726 Vigna sinensis Nutrition 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- 125000004806 1-methylethylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- DXVQSHRBALIFBC-UHFFFAOYSA-N 3-phenoxypropan-1-amine Chemical compound NCCCOC1=CC=CC=C1 DXVQSHRBALIFBC-UHFFFAOYSA-N 0.000 description 2
- HCLZWPBFBUYJCS-UHFFFAOYSA-N 4-[2-(2-methoxyphenoxy)ethyl]-6-methylquinazolin-2-amine Chemical compound COC1=CC=CC=C1OCCC1=NC(N)=NC2=CC=C(C)C=C12 HCLZWPBFBUYJCS-UHFFFAOYSA-N 0.000 description 2
- IUMGQQSACZRCLC-UHFFFAOYSA-N 6-nitro-n-(3-phenoxypropyl)quinazolin-4-amine Chemical compound C12=CC([N+](=O)[O-])=CC=C2N=CN=C1NCCCOC1=CC=CC=C1 IUMGQQSACZRCLC-UHFFFAOYSA-N 0.000 description 2
- 241001600408 Aphis gossypii Species 0.000 description 2
- 241001674044 Blattodea Species 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 241000255925 Diptera Species 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 241000257159 Musca domestica Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000013601 eggs Nutrition 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- OFTCIAFFGMUPJQ-UHFFFAOYSA-N n-(5-phenoxypentyl)quinazolin-4-amine Chemical compound N=1C=NC2=CC=CC=C2C=1NCCCCCOC1=CC=CC=C1 OFTCIAFFGMUPJQ-UHFFFAOYSA-N 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- DRYRBWIFRVMRPV-UHFFFAOYSA-N quinazolin-4-amine Chemical class C1=CC=C2C(N)=NC=NC2=C1 DRYRBWIFRVMRPV-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- 125000004812 1-ethylethylene group Chemical group [H]C([H])([H])C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000004816 2,2-dimethylethylene group Chemical group [H]C([H])([H])C([*:2])(C([H])([H])[H])C([H])([H])[*:1] 0.000 description 1
- TUQSVSYUEBNNKQ-UHFFFAOYSA-N 2,4-dichloroquinazoline Chemical compound C1=CC=CC2=NC(Cl)=NC(Cl)=C21 TUQSVSYUEBNNKQ-UHFFFAOYSA-N 0.000 description 1
- NAPNYPMMDVRKGM-UHFFFAOYSA-N 2-(2-chlorophenoxy)ethanamine Chemical compound NCCOC1=CC=CC=C1Cl NAPNYPMMDVRKGM-UHFFFAOYSA-N 0.000 description 1
- CKJRKLKVCHMWLV-UHFFFAOYSA-N 2-(2-methoxyphenoxy)ethanamine Chemical compound COC1=CC=CC=C1OCCN CKJRKLKVCHMWLV-UHFFFAOYSA-N 0.000 description 1
- 125000006516 2-(benzyloxy)ethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- LDLQAZSCDCCPKY-UHFFFAOYSA-N 2-chloro-4-(2-ethylsulfanylethyl)quinazolin-5-amine Chemical compound ClC1=NC2=CC=CC(=C2C(=N1)CCSCC)N LDLQAZSCDCCPKY-UHFFFAOYSA-N 0.000 description 1
- FWOPDDVTKFDWAK-UHFFFAOYSA-N 2-chloro-4-(2-phenoxyethyl)quinazolin-5-amine Chemical compound ClC1=NC2=CC=CC(=C2C(=N1)CCOC1=CC=CC=C1)N FWOPDDVTKFDWAK-UHFFFAOYSA-N 0.000 description 1
- HEZJPKCQRBVNNS-UHFFFAOYSA-N 2-chloro-4-[2-methyl-2-(4-methylphenoxy)propyl]quinazolin-5-amine Chemical compound C1=CC(C)=CC=C1OC(C)(C)CC1=NC(Cl)=NC2=CC=CC(N)=C12 HEZJPKCQRBVNNS-UHFFFAOYSA-N 0.000 description 1
- VGGCNHDGBPHGQO-UHFFFAOYSA-N 2-chloro-n-(1-phenoxypropan-2-yl)quinazolin-4-amine Chemical compound N=1C(Cl)=NC2=CC=CC=C2C=1NC(C)COC1=CC=CC=C1 VGGCNHDGBPHGQO-UHFFFAOYSA-N 0.000 description 1
- PXNXJTMWCVTICU-UHFFFAOYSA-N 2-chloro-n-(2-phenoxypropyl)quinazolin-4-amine Chemical compound N=1C(Cl)=NC2=CC=CC=C2C=1NCC(C)OC1=CC=CC=C1 PXNXJTMWCVTICU-UHFFFAOYSA-N 0.000 description 1
- WGWZXDNTMLJJMP-UHFFFAOYSA-N 2-chloro-n-(2-phenylsulfanylethyl)quinazolin-4-amine Chemical compound C=12C=CC=CC2=NC(Cl)=NC=1NCCSC1=CC=CC=C1 WGWZXDNTMLJJMP-UHFFFAOYSA-N 0.000 description 1
- PBKUZRISJOHTOU-UHFFFAOYSA-N 2-chloro-n-(3-phenoxypropyl)quinazolin-4-amine Chemical compound C=12C=CC=CC2=NC(Cl)=NC=1NCCCOC1=CC=CC=C1 PBKUZRISJOHTOU-UHFFFAOYSA-N 0.000 description 1
- CGBWDWWKBLWVRV-UHFFFAOYSA-N 2-chloro-n-(3-phenylsulfanylpropyl)quinazolin-4-amine Chemical compound C=12C=CC=CC2=NC(Cl)=NC=1NCCCSC1=CC=CC=C1 CGBWDWWKBLWVRV-UHFFFAOYSA-N 0.000 description 1
- XSBDPIDHKNRXFB-UHFFFAOYSA-N 2-chloro-n-[1-(4-chlorophenoxy)propan-2-yl]quinazolin-4-amine Chemical compound N=1C(Cl)=NC2=CC=CC=C2C=1NC(C)COC1=CC=C(Cl)C=C1 XSBDPIDHKNRXFB-UHFFFAOYSA-N 0.000 description 1
- KPAIUUKLLIVALG-UHFFFAOYSA-N 2-chloro-n-[2-(2,6-dimethylphenoxy)ethyl]quinazolin-4-amine Chemical compound CC1=CC=CC(C)=C1OCCNC1=NC(Cl)=NC2=CC=CC=C12 KPAIUUKLLIVALG-UHFFFAOYSA-N 0.000 description 1
- MCTVUZWKPDEVLN-UHFFFAOYSA-N 2-chloro-n-[2-(2-chlorophenoxy)ethyl]quinazolin-4-amine Chemical compound C=12C=CC=CC2=NC(Cl)=NC=1NCCOC1=CC=CC=C1Cl MCTVUZWKPDEVLN-UHFFFAOYSA-N 0.000 description 1
- AUUAALSVNZVXEY-UHFFFAOYSA-N 2-chloro-n-[2-(2-methylphenoxy)ethyl]quinazolin-4-amine Chemical compound CC1=CC=CC=C1OCCNC1=NC(Cl)=NC2=CC=CC=C12 AUUAALSVNZVXEY-UHFFFAOYSA-N 0.000 description 1
- VKDAXSYSTFNULN-UHFFFAOYSA-N 2-chloro-n-[2-(2-methylphenoxy)propyl]quinazolin-4-amine Chemical compound N=1C(Cl)=NC2=CC=CC=C2C=1NCC(C)OC1=CC=CC=C1C VKDAXSYSTFNULN-UHFFFAOYSA-N 0.000 description 1
- QUTKYVZUEAICBN-UHFFFAOYSA-N 2-chloro-n-[2-(2-methylphenyl)sulfanylethyl]quinazolin-4-amine Chemical compound CC1=CC=CC=C1SCCNC1=NC(Cl)=NC2=CC=CC=C12 QUTKYVZUEAICBN-UHFFFAOYSA-N 0.000 description 1
- AUKAEXPXWUKXLP-UHFFFAOYSA-N 2-chloro-n-[2-(3-methylphenoxy)ethyl]quinazolin-4-amine Chemical compound CC1=CC=CC(OCCNC=2C3=CC=CC=C3N=C(Cl)N=2)=C1 AUKAEXPXWUKXLP-UHFFFAOYSA-N 0.000 description 1
- OCTCATOEYBDSGD-UHFFFAOYSA-N 2-chloro-n-[2-(3-methylphenyl)sulfanylethyl]quinazolin-4-amine Chemical compound CC1=CC=CC(SCCNC=2C3=CC=CC=C3N=C(Cl)N=2)=C1 OCTCATOEYBDSGD-UHFFFAOYSA-N 0.000 description 1
- FWFAPCDAUHGTNM-UHFFFAOYSA-N 2-chloro-n-[2-(4-methylphenoxy)ethyl]quinazolin-4-amine Chemical compound C1=CC(C)=CC=C1OCCNC1=NC(Cl)=NC2=CC=CC=C12 FWFAPCDAUHGTNM-UHFFFAOYSA-N 0.000 description 1
- ILVIHNGEHDAKSI-UHFFFAOYSA-N 2-chloro-n-[2-(4-methylphenoxy)propyl]quinazolin-4-amine Chemical compound N=1C(Cl)=NC2=CC=CC=C2C=1NCC(C)OC1=CC=C(C)C=C1 ILVIHNGEHDAKSI-UHFFFAOYSA-N 0.000 description 1
- FJSNSQLAVGSXNP-UHFFFAOYSA-N 2-chloro-n-[2-(4-methylphenyl)sulfanylethyl]quinazolin-4-amine Chemical compound C1=CC(C)=CC=C1SCCNC1=NC(Cl)=NC2=CC=CC=C12 FJSNSQLAVGSXNP-UHFFFAOYSA-N 0.000 description 1
- VMWSJVKSVCXIAT-UHFFFAOYSA-N 2-chloro-n-[2-methyl-2-(2-methylphenoxy)propyl]quinazolin-4-amine Chemical compound CC1=CC=CC=C1OC(C)(C)CNC1=NC(Cl)=NC2=CC=CC=C12 VMWSJVKSVCXIAT-UHFFFAOYSA-N 0.000 description 1
- KSURBIPKSWPVNL-UHFFFAOYSA-N 2-chloro-n-[2-methyl-2-(3-methylphenoxy)propyl]quinazolin-4-amine Chemical compound CC1=CC=CC(OC(C)(C)CNC=2C3=CC=CC=C3N=C(Cl)N=2)=C1 KSURBIPKSWPVNL-UHFFFAOYSA-N 0.000 description 1
- KYSYWKJEBWDCDU-UHFFFAOYSA-N 2-chloro-n-[3-(3-methylphenoxy)propyl]quinazolin-4-amine Chemical compound CC1=CC=CC(OCCCNC=2C3=CC=CC=C3N=C(Cl)N=2)=C1 KYSYWKJEBWDCDU-UHFFFAOYSA-N 0.000 description 1
- AGBOJSWWYRLMST-UHFFFAOYSA-N 2-chloro-n-[3-(3-methylphenyl)sulfanylpropyl]quinazolin-4-amine Chemical compound CC1=CC=CC(SCCCNC=2C3=CC=CC=C3N=C(Cl)N=2)=C1 AGBOJSWWYRLMST-UHFFFAOYSA-N 0.000 description 1
- FVKAZSRHRNCAOA-UHFFFAOYSA-N 2-chloro-n-[3-(4-chlorophenoxy)propyl]quinazolin-4-amine Chemical compound C1=CC(Cl)=CC=C1OCCCNC1=NC(Cl)=NC2=CC=CC=C12 FVKAZSRHRNCAOA-UHFFFAOYSA-N 0.000 description 1
- XBBNIHGATQMFIZ-UHFFFAOYSA-N 2-methyl-2-(4-methylphenoxy)propan-1-amine Chemical compound CC1=CC=C(OC(C)(C)CN)C=C1 XBBNIHGATQMFIZ-UHFFFAOYSA-N 0.000 description 1
- SGDXNOSKUZAPFC-UHFFFAOYSA-N 2-methyl-n-(3-phenoxypropyl)quinazolin-4-amine Chemical compound C=12C=CC=CC2=NC(C)=NC=1NCCCOC1=CC=CC=C1 SGDXNOSKUZAPFC-UHFFFAOYSA-N 0.000 description 1
- 125000004807 2-methylethylene group Chemical group [H]C([H])([H])C([H])([*:2])C([H])([H])[*:1] 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- XJGVVOAKITWCAB-UHFFFAOYSA-N 2-phenylmethoxyethanamine Chemical compound NCCOCC1=CC=CC=C1 XJGVVOAKITWCAB-UHFFFAOYSA-N 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
- JEBCOVKUVLFOGR-UHFFFAOYSA-N 4,6-dichloroquinazoline Chemical compound N1=CN=C(Cl)C2=CC(Cl)=CC=C21 JEBCOVKUVLFOGR-UHFFFAOYSA-N 0.000 description 1
- WUYHRIGOKRBYJI-UHFFFAOYSA-N 4-(2-phenoxypropyl)quinazolin-2-amine Chemical compound CC(CC1=NC(=NC2=CC=CC=C12)N)OC1=CC=CC=C1 WUYHRIGOKRBYJI-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- YGZNQHHYTWOYCF-UHFFFAOYSA-N 4-[2-(2-chlorophenoxy)ethyl]quinazolin-2-amine Chemical compound ClC1=C(OCCC2=NC(=NC3=CC=CC=C23)N)C=CC=C1 YGZNQHHYTWOYCF-UHFFFAOYSA-N 0.000 description 1
- YWEIFJARHGLEEL-UHFFFAOYSA-N 4-[2-(2-ethylphenoxy)ethyl]quinazolin-2-amine Chemical compound C(C)C1=C(OCCC2=NC(=NC3=CC=CC=C23)N)C=CC=C1 YWEIFJARHGLEEL-UHFFFAOYSA-N 0.000 description 1
- FYYVKIAIPURPPF-UHFFFAOYSA-N 4-[2-(2-methoxyphenoxy)propyl]quinazolin-2-amine Chemical compound CC(CC1=NC(=NC2=CC=CC=C12)N)OC1=C(C=CC=C1)OC FYYVKIAIPURPPF-UHFFFAOYSA-N 0.000 description 1
- VQLBYGXUGMXDKX-UHFFFAOYSA-N 4-[2-(2-methylphenoxy)ethyl]quinazolin-2-amine Chemical compound CC1=C(OCCC2=NC(=NC3=CC=CC=C23)N)C=CC=C1 VQLBYGXUGMXDKX-UHFFFAOYSA-N 0.000 description 1
- RUBATUZFPXRXAZ-UHFFFAOYSA-N 4-[2-(3-chlorophenoxy)ethyl]-6-methylquinazolin-2-amine Chemical compound CC=1C=C2C(=NC(=NC2=CC=1)N)CCOC1=CC(=CC=C1)Cl RUBATUZFPXRXAZ-UHFFFAOYSA-N 0.000 description 1
- FKFLQZQFOYSELF-UHFFFAOYSA-N 4-[2-(3-methylphenoxy)ethyl]quinazolin-2-amine Chemical compound CC=1C=C(OCCC2=NC(=NC3=CC=CC=C23)N)C=CC=1 FKFLQZQFOYSELF-UHFFFAOYSA-N 0.000 description 1
- WDTQVAHRPRZLQE-UHFFFAOYSA-N 4-[2-(4-chlorophenoxy)ethyl]quinazolin-2-amine Chemical compound ClC1=CC=C(OCCC2=NC(=NC3=CC=CC=C23)N)C=C1 WDTQVAHRPRZLQE-UHFFFAOYSA-N 0.000 description 1
- HYANARCCPKQQAE-UHFFFAOYSA-N 4-[2-(4-chlorophenoxy)propyl]quinazolin-2-amine Chemical compound CC(CC1=NC(=NC2=CC=CC=C12)N)OC1=CC=C(C=C1)Cl HYANARCCPKQQAE-UHFFFAOYSA-N 0.000 description 1
- RGODHSAQTNRFMY-UHFFFAOYSA-N 4-[2-(4-methylphenoxy)ethyl]quinazolin-2-amine Chemical compound CC1=CC=C(OCCC2=NC(=NC3=CC=CC=C23)N)C=C1 RGODHSAQTNRFMY-UHFFFAOYSA-N 0.000 description 1
- DLSCGOLGMJZMMZ-UHFFFAOYSA-N 4-chloro-5-nitroquinazoline Chemical compound C1=NC(Cl)=C2C([N+](=O)[O-])=CC=CC2=N1 DLSCGOLGMJZMMZ-UHFFFAOYSA-N 0.000 description 1
- XNILKVADCMYCQT-UHFFFAOYSA-N 4-chloro-6-methylquinazoline Chemical compound N1=CN=C(Cl)C2=CC(C)=CC=C21 XNILKVADCMYCQT-UHFFFAOYSA-N 0.000 description 1
- WXFMHWZCFFQMAP-UHFFFAOYSA-N 5-phenoxypentan-1-amine Chemical compound NCCCCCOC1=CC=CC=C1 WXFMHWZCFFQMAP-UHFFFAOYSA-N 0.000 description 1
- SPLKKZCQFPVUOM-UHFFFAOYSA-N 6-chloro-4-(2-phenoxyethyl)quinazolin-2-amine Chemical compound ClC=1C=C2C(=NC(=NC2=CC=1)N)CCOC1=CC=CC=C1 SPLKKZCQFPVUOM-UHFFFAOYSA-N 0.000 description 1
- VTRWNRDEOAWHEO-UHFFFAOYSA-N 6-chloro-4-[2-(2-chlorophenoxy)ethyl]quinazolin-2-amine Chemical compound ClC=1C=C2C(=NC(=NC2=CC=1)N)CCOC1=C(C=CC=C1)Cl VTRWNRDEOAWHEO-UHFFFAOYSA-N 0.000 description 1
- JMJOOHVEEGSSOM-UHFFFAOYSA-N 6-chloro-n-(2-naphthalen-1-yloxyethyl)quinazolin-4-amine Chemical compound C1=CC=C2C(OCCNC3=NC=NC4=CC=C(C=C43)Cl)=CC=CC2=C1 JMJOOHVEEGSSOM-UHFFFAOYSA-N 0.000 description 1
- VNNFUIBNMMJLPF-UHFFFAOYSA-N 6-chloro-n-[2-(2,4,5-trichlorophenoxy)ethyl]quinazolin-4-amine Chemical compound C12=CC(Cl)=CC=C2N=CN=C1NCCOC1=CC(Cl)=C(Cl)C=C1Cl VNNFUIBNMMJLPF-UHFFFAOYSA-N 0.000 description 1
- MUZJWJVEXOGRJK-UHFFFAOYSA-N 6-chloro-n-[2-(2,4,6-trichlorophenoxy)ethyl]quinazolin-4-amine Chemical compound C12=CC(Cl)=CC=C2N=CN=C1NCCOC1=C(Cl)C=C(Cl)C=C1Cl MUZJWJVEXOGRJK-UHFFFAOYSA-N 0.000 description 1
- OTAAMJUAYAUOLX-UHFFFAOYSA-N 6-chloro-n-[2-(2,4-dichlorophenoxy)ethyl]quinazolin-4-amine Chemical compound ClC1=CC(Cl)=CC=C1OCCNC1=NC=NC2=CC=C(Cl)C=C12 OTAAMJUAYAUOLX-UHFFFAOYSA-N 0.000 description 1
- QUVRJFFSYPLXLB-UHFFFAOYSA-N 6-chloro-n-[2-(2,5-dimethylphenoxy)ethyl]quinazolin-4-amine Chemical compound CC1=CC=C(C)C(OCCNC=2C3=CC(Cl)=CC=C3N=CN=2)=C1 QUVRJFFSYPLXLB-UHFFFAOYSA-N 0.000 description 1
- IDDYAZLPZXUSFI-UHFFFAOYSA-N 6-chloro-n-[2-(2-ethoxyphenoxy)ethyl]quinazolin-4-amine Chemical compound CCOC1=CC=CC=C1OCCNC1=NC=NC2=CC=C(Cl)C=C12 IDDYAZLPZXUSFI-UHFFFAOYSA-N 0.000 description 1
- WUICERNGXBYIEC-UHFFFAOYSA-N 6-chloro-n-[2-(2-methylphenoxy)ethyl]quinazolin-4-amine Chemical compound CC1=CC=CC=C1OCCNC1=NC=NC2=CC=C(Cl)C=C12 WUICERNGXBYIEC-UHFFFAOYSA-N 0.000 description 1
- WYQPSTPMQXODRN-UHFFFAOYSA-N 6-chloro-n-[2-(2-phenylphenoxy)ethyl]quinazolin-4-amine Chemical compound C12=CC(Cl)=CC=C2N=CN=C1NCCOC1=CC=CC=C1C1=CC=CC=C1 WYQPSTPMQXODRN-UHFFFAOYSA-N 0.000 description 1
- ORUIHCIVCSXCNY-UHFFFAOYSA-N 6-chloro-n-[2-(3,5-dimethylphenoxy)ethyl]quinazolin-4-amine Chemical compound CC1=CC(C)=CC(OCCNC=2C3=CC(Cl)=CC=C3N=CN=2)=C1 ORUIHCIVCSXCNY-UHFFFAOYSA-N 0.000 description 1
- LJMJWTCYISOEJB-UHFFFAOYSA-N 6-methyl-4-(2-phenoxyethyl)quinazolin-2-amine Chemical compound CC=1C=C2C(=NC(=NC2=CC=1)N)CCOC1=CC=CC=C1 LJMJWTCYISOEJB-UHFFFAOYSA-N 0.000 description 1
- CYJHXWYMNQWPLV-UHFFFAOYSA-N 6-methyl-4-(4-phenoxybutyl)quinazolin-2-amine Chemical compound CC=1C=C2C(=NC(=NC2=CC=1)N)CCCCOC1=CC=CC=C1 CYJHXWYMNQWPLV-UHFFFAOYSA-N 0.000 description 1
- YDDHVZHHCAQAOH-UHFFFAOYSA-N 6-methyl-n-(1-phenoxypropan-2-yl)quinazolin-4-amine Chemical compound N=1C=NC2=CC=C(C)C=C2C=1NC(C)COC1=CC=CC=C1 YDDHVZHHCAQAOH-UHFFFAOYSA-N 0.000 description 1
- UMCBYMXVQCNQAP-UHFFFAOYSA-N 6-methyl-n-(3-phenoxypropyl)quinazolin-4-amine Chemical compound C12=CC(C)=CC=C2N=CN=C1NCCCOC1=CC=CC=C1 UMCBYMXVQCNQAP-UHFFFAOYSA-N 0.000 description 1
- UNJGTOGPVYYXDI-UHFFFAOYSA-N 6-methyl-n-(3-phenylsulfanylpropyl)quinazolin-4-amine Chemical compound C12=CC(C)=CC=C2N=CN=C1NCCCSC1=CC=CC=C1 UNJGTOGPVYYXDI-UHFFFAOYSA-N 0.000 description 1
- ZLESCGUCBAZVLR-UHFFFAOYSA-N 6-methyl-n-[2-(2-methylphenoxy)ethyl]quinazolin-4-amine Chemical compound C12=CC(C)=CC=C2N=CN=C1NCCOC1=CC=CC=C1C ZLESCGUCBAZVLR-UHFFFAOYSA-N 0.000 description 1
- WFZMWYBGTQKAFE-UHFFFAOYSA-N 6-methyl-n-[2-(4-methylphenoxy)ethyl]quinazolin-4-amine Chemical compound C1=CC(C)=CC=C1OCCNC1=NC=NC2=CC=C(C)C=C12 WFZMWYBGTQKAFE-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 240000008067 Cucumis sativus Species 0.000 description 1
- 235000009849 Cucumis sativus Nutrition 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 206010016952 Food poisoning Diseases 0.000 description 1
- 208000019331 Foodborne disease Diseases 0.000 description 1
- PCBLKYPHGNELHI-UHFFFAOYSA-N N-[2-(3,4-dimethylphenyl)sulfanylethyl]quinazolin-4-amine Chemical compound CC=1C=C(SCCNC2=NC=NC3=CC=CC=C23)C=CC1C PCBLKYPHGNELHI-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000238675 Periplaneta americana Species 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 241001674048 Phthiraptera Species 0.000 description 1
- 241000500439 Plutella Species 0.000 description 1
- 241000500437 Plutella xylostella Species 0.000 description 1
- 241000500441 Plutellidae Species 0.000 description 1
- 235000005733 Raphanus sativus var niger Nutrition 0.000 description 1
- 244000155437 Raphanus sativus var. niger Species 0.000 description 1
- 241000258242 Siphonaptera Species 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229940013688 formic acid Drugs 0.000 description 1
- 230000012447 hatching Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 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 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N iso-butene Natural products CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- PQQJBPCPSUBJPX-UHFFFAOYSA-N n-(2-benzylsulfanylethyl)-2-chloroquinazolin-4-amine Chemical compound C=12C=CC=CC2=NC(Cl)=NC=1NCCSCC1=CC=CC=C1 PQQJBPCPSUBJPX-UHFFFAOYSA-N 0.000 description 1
- XMQBEMLUHFJOKC-UHFFFAOYSA-N n-(2-benzylsulfanylethyl)quinazolin-4-amine Chemical compound N=1C=NC2=CC=CC=C2C=1NCCSCC1=CC=CC=C1 XMQBEMLUHFJOKC-UHFFFAOYSA-N 0.000 description 1
- HUMYOYKIIRWSIL-UHFFFAOYSA-N n-(2-ethylsulfanylethyl)quinazolin-4-amine Chemical compound C1=CC=C2C(NCCSCC)=NC=NC2=C1 HUMYOYKIIRWSIL-UHFFFAOYSA-N 0.000 description 1
- CLCPYRAOAUEQAE-UHFFFAOYSA-N n-(2-methyl-2-phenoxypropyl)quinazolin-4-amine Chemical compound N=1C=NC2=CC=CC=C2C=1NCC(C)(C)OC1=CC=CC=C1 CLCPYRAOAUEQAE-UHFFFAOYSA-N 0.000 description 1
- IVZSAHGGJJEJAT-UHFFFAOYSA-N n-(2-naphthalen-1-yloxyethyl)quinazolin-4-amine Chemical compound C1=CC=C2C(NCCOC=3C4=CC=CC=C4C=CC=3)=NC=NC2=C1 IVZSAHGGJJEJAT-UHFFFAOYSA-N 0.000 description 1
- POBBTQVYPYBJEF-UHFFFAOYSA-N n-(2-phenoxyethyl)quinazolin-4-amine Chemical compound N=1C=NC2=CC=CC=C2C=1NCCOC1=CC=CC=C1 POBBTQVYPYBJEF-UHFFFAOYSA-N 0.000 description 1
- TUENXMAJHUUVBX-UHFFFAOYSA-N n-(2-phenylmethoxyethyl)quinazolin-4-amine Chemical compound N=1C=NC2=CC=CC=C2C=1NCCOCC1=CC=CC=C1 TUENXMAJHUUVBX-UHFFFAOYSA-N 0.000 description 1
- CZAVAEQAPXVXCR-UHFFFAOYSA-N n-(2-phenylsulfanylethyl)quinazolin-4-amine Chemical compound N=1C=NC2=CC=CC=C2C=1NCCSC1=CC=CC=C1 CZAVAEQAPXVXCR-UHFFFAOYSA-N 0.000 description 1
- PECHJOQEZBBWEK-UHFFFAOYSA-N n-(3-naphthalen-1-yloxypropyl)quinazolin-4-amine Chemical compound C1=CC=C2C(OCCCNC=3C4=CC=CC=C4N=CN=3)=CC=CC2=C1 PECHJOQEZBBWEK-UHFFFAOYSA-N 0.000 description 1
- BXGDZWFSWMHCJQ-UHFFFAOYSA-N n-(3-phenoxypropyl)quinazolin-4-amine Chemical compound N=1C=NC2=CC=CC=C2C=1NCCCOC1=CC=CC=C1 BXGDZWFSWMHCJQ-UHFFFAOYSA-N 0.000 description 1
- MIHUJJIVLQSXFM-UHFFFAOYSA-N n-(3-phenylsulfanylpropyl)quinazolin-4-amine Chemical compound N=1C=NC2=CC=CC=C2C=1NCCCSC1=CC=CC=C1 MIHUJJIVLQSXFM-UHFFFAOYSA-N 0.000 description 1
- ISHOLTWULYBRSH-UHFFFAOYSA-N n-(7-phenoxyheptyl)quinazolin-4-amine Chemical compound N=1C=NC2=CC=CC=C2C=1NCCCCCCCOC1=CC=CC=C1 ISHOLTWULYBRSH-UHFFFAOYSA-N 0.000 description 1
- PTPUBIPGKCPPLF-UHFFFAOYSA-N n-(8-phenoxyoctyl)quinazolin-4-amine Chemical compound N=1C=NC2=CC=CC=C2C=1NCCCCCCCCOC1=CC=CC=C1 PTPUBIPGKCPPLF-UHFFFAOYSA-N 0.000 description 1
- JJDCRFKGWQEDRT-UHFFFAOYSA-N n-[1-(2-methoxyphenoxy)propan-2-yl]quinazolin-4-amine Chemical compound COC1=CC=CC=C1OCC(C)NC1=NC=NC2=CC=CC=C12 JJDCRFKGWQEDRT-UHFFFAOYSA-N 0.000 description 1
- QBZNWENZZZIWIG-UHFFFAOYSA-N n-[1-(2-methylphenoxy)propan-2-yl]quinazolin-4-amine Chemical compound N=1C=NC2=CC=CC=C2C=1NC(C)COC1=CC=CC=C1C QBZNWENZZZIWIG-UHFFFAOYSA-N 0.000 description 1
- GVPGHXGGFNXBED-UHFFFAOYSA-N n-[1-(3-chlorophenoxy)propan-2-yl]quinazolin-4-amine Chemical compound N=1C=NC2=CC=CC=C2C=1NC(C)COC1=CC=CC(Cl)=C1 GVPGHXGGFNXBED-UHFFFAOYSA-N 0.000 description 1
- CEBFPLSOZRFFMJ-UHFFFAOYSA-N n-[1-(3-methylphenoxy)propan-2-yl]quinazolin-4-amine Chemical compound N=1C=NC2=CC=CC=C2C=1NC(C)COC1=CC=CC(C)=C1 CEBFPLSOZRFFMJ-UHFFFAOYSA-N 0.000 description 1
- IGYUEABSVNKMGI-UHFFFAOYSA-N n-[1-(4-chlorophenoxy)propan-2-yl]quinazolin-4-amine Chemical compound N=1C=NC2=CC=CC=C2C=1NC(C)COC1=CC=C(Cl)C=C1 IGYUEABSVNKMGI-UHFFFAOYSA-N 0.000 description 1
- DWFJPOCTAPFYLX-UHFFFAOYSA-N n-[1-(4-methylphenoxy)propan-2-yl]quinazolin-4-amine Chemical compound N=1C=NC2=CC=CC=C2C=1NC(C)COC1=CC=C(C)C=C1 DWFJPOCTAPFYLX-UHFFFAOYSA-N 0.000 description 1
- BLERWGGXWLMOBN-UHFFFAOYSA-N n-[12-(2-methylphenoxy)dodecyl]quinazolin-4-amine Chemical compound CC1=CC=CC=C1OCCCCCCCCCCCCNC1=NC=NC2=CC=CC=C12 BLERWGGXWLMOBN-UHFFFAOYSA-N 0.000 description 1
- ASDDSAJFKAPZCT-UHFFFAOYSA-N n-[2-(2,3,6-trimethylphenoxy)ethyl]quinazolin-4-amine Chemical compound CC1=CC=C(C)C(OCCNC=2C3=CC=CC=C3N=CN=2)=C1C ASDDSAJFKAPZCT-UHFFFAOYSA-N 0.000 description 1
- GPSAFVBCFPMJML-UHFFFAOYSA-N n-[2-(2,4,5-trichlorophenoxy)ethyl]quinazolin-4-amine Chemical compound C1=C(Cl)C(Cl)=CC(Cl)=C1OCCNC1=NC=NC2=CC=CC=C12 GPSAFVBCFPMJML-UHFFFAOYSA-N 0.000 description 1
- JAZGFJQPLMKJTL-UHFFFAOYSA-N n-[2-(2,4,6-tribromophenoxy)ethyl]quinazolin-4-amine Chemical compound BrC1=CC(Br)=CC(Br)=C1OCCNC1=NC=NC2=CC=CC=C12 JAZGFJQPLMKJTL-UHFFFAOYSA-N 0.000 description 1
- QYFBWOQOVUYSSJ-UHFFFAOYSA-N n-[2-(2,4-dibromophenoxy)ethyl]quinazolin-4-amine Chemical compound BrC1=CC(Br)=CC=C1OCCNC1=NC=NC2=CC=CC=C12 QYFBWOQOVUYSSJ-UHFFFAOYSA-N 0.000 description 1
- LPXVWZZCSAUMBE-UHFFFAOYSA-N n-[2-(2,4-dichloro-6-methylphenoxy)ethyl]quinazolin-4-amine Chemical compound CC1=CC(Cl)=CC(Cl)=C1OCCNC1=NC=NC2=CC=CC=C12 LPXVWZZCSAUMBE-UHFFFAOYSA-N 0.000 description 1
- PGCXAAOZOBWVHJ-UHFFFAOYSA-N n-[2-(2,4-dichlorophenoxy)ethyl]quinazolin-4-amine Chemical compound ClC1=CC(Cl)=CC=C1OCCNC1=NC=NC2=CC=CC=C12 PGCXAAOZOBWVHJ-UHFFFAOYSA-N 0.000 description 1
- CAFDTMFAMUHGQH-UHFFFAOYSA-N n-[2-(2,4-dimethylphenoxy)ethyl]quinazolin-4-amine Chemical compound CC1=CC(C)=CC=C1OCCNC1=NC=NC2=CC=CC=C12 CAFDTMFAMUHGQH-UHFFFAOYSA-N 0.000 description 1
- SZDICOIWGVZBPL-UHFFFAOYSA-N n-[2-(2,5-dimethoxyphenoxy)ethyl]quinazolin-4-amine Chemical compound COC1=CC=C(OC)C(OCCNC=2C3=CC=CC=C3N=CN=2)=C1 SZDICOIWGVZBPL-UHFFFAOYSA-N 0.000 description 1
- NJURIEQRZJUJIH-UHFFFAOYSA-N n-[2-(2,6-dimethylphenoxy)ethyl]quinazolin-4-amine Chemical compound CC1=CC=CC(C)=C1OCCNC1=NC=NC2=CC=CC=C12 NJURIEQRZJUJIH-UHFFFAOYSA-N 0.000 description 1
- VOCOWOPEEMDQDG-UHFFFAOYSA-N n-[2-(2-bromophenoxy)ethyl]quinazolin-4-amine Chemical compound BrC1=CC=CC=C1OCCNC1=NC=NC2=CC=CC=C12 VOCOWOPEEMDQDG-UHFFFAOYSA-N 0.000 description 1
- IZAYFAKRMCIYAT-UHFFFAOYSA-N n-[2-(2-butan-2-ylphenoxy)ethyl]quinazolin-4-amine Chemical compound CCC(C)C1=CC=CC=C1OCCNC1=NC=NC2=CC=CC=C12 IZAYFAKRMCIYAT-UHFFFAOYSA-N 0.000 description 1
- VZNREXLFRVPIER-UHFFFAOYSA-N n-[2-(2-butoxyphenoxy)ethyl]quinazolin-4-amine Chemical compound CCCCOC1=CC=CC=C1OCCNC1=NC=NC2=CC=CC=C12 VZNREXLFRVPIER-UHFFFAOYSA-N 0.000 description 1
- WVJGVIWYHAOWJT-UHFFFAOYSA-N n-[2-(2-butylphenoxy)ethyl]quinazolin-4-amine Chemical compound CCCCC1=CC=CC=C1OCCNC1=NC=NC2=CC=CC=C12 WVJGVIWYHAOWJT-UHFFFAOYSA-N 0.000 description 1
- MTZCRQGYZZMYMP-UHFFFAOYSA-N n-[2-(2-chloro-4-methoxyphenoxy)ethyl]quinazolin-4-amine Chemical compound ClC1=CC(OC)=CC=C1OCCNC1=NC=NC2=CC=CC=C12 MTZCRQGYZZMYMP-UHFFFAOYSA-N 0.000 description 1
- UPTHYAKQHIHMJA-UHFFFAOYSA-N n-[2-(2-chlorophenoxy)-2-methylpropyl]quinazolin-4-amine Chemical compound N=1C=NC2=CC=CC=C2C=1NCC(C)(C)OC1=CC=CC=C1Cl UPTHYAKQHIHMJA-UHFFFAOYSA-N 0.000 description 1
- OKDMYKGANLSZGG-UHFFFAOYSA-N n-[2-(2-chlorophenoxy)ethyl]quinazolin-4-amine Chemical compound ClC1=CC=CC=C1OCCNC1=NC=NC2=CC=CC=C12 OKDMYKGANLSZGG-UHFFFAOYSA-N 0.000 description 1
- LBRFYSXFBCDIKP-UHFFFAOYSA-N n-[2-(2-chlorophenoxy)propyl]quinazolin-4-amine Chemical compound N=1C=NC2=CC=CC=C2C=1NCC(C)OC1=CC=CC=C1Cl LBRFYSXFBCDIKP-UHFFFAOYSA-N 0.000 description 1
- VPQLOHATNBCYCY-UHFFFAOYSA-N n-[2-(2-ethoxyphenoxy)ethyl]quinazolin-4-amine Chemical compound CCOC1=CC=CC=C1OCCNC1=NC=NC2=CC=CC=C12 VPQLOHATNBCYCY-UHFFFAOYSA-N 0.000 description 1
- SMZFPJHMPISOBX-UHFFFAOYSA-N n-[2-(2-fluorophenoxy)ethyl]quinazolin-4-amine Chemical compound FC1=CC=CC=C1OCCNC1=NC=NC2=CC=CC=C12 SMZFPJHMPISOBX-UHFFFAOYSA-N 0.000 description 1
- ARKRUXQLBJMOOV-UHFFFAOYSA-N n-[2-(2-iodophenoxy)ethyl]quinazolin-4-amine Chemical compound IC1=CC=CC=C1OCCNC1=NC=NC2=CC=CC=C12 ARKRUXQLBJMOOV-UHFFFAOYSA-N 0.000 description 1
- SAJZRPZNIZAINS-UHFFFAOYSA-N n-[2-(2-methoxy-4-methylphenoxy)ethyl]quinazolin-4-amine Chemical compound COC1=CC(C)=CC=C1OCCNC1=NC=NC2=CC=CC=C12 SAJZRPZNIZAINS-UHFFFAOYSA-N 0.000 description 1
- NXAAXOKKKBBBCI-UHFFFAOYSA-N n-[2-(2-methoxyphenoxy)-2-methylpropyl]quinazolin-4-amine Chemical compound COC1=CC=CC=C1OC(C)(C)CNC1=NC=NC2=CC=CC=C12 NXAAXOKKKBBBCI-UHFFFAOYSA-N 0.000 description 1
- UXKXTJKFXPMMQP-UHFFFAOYSA-N n-[2-(2-methoxyphenoxy)ethyl]quinazolin-4-amine Chemical compound COC1=CC=CC=C1OCCNC1=NC=NC2=CC=CC=C12 UXKXTJKFXPMMQP-UHFFFAOYSA-N 0.000 description 1
- ZKTNOCIFYNQVPH-UHFFFAOYSA-N n-[2-(2-methylphenoxy)ethyl]quinazolin-4-amine Chemical compound CC1=CC=CC=C1OCCNC1=NC=NC2=CC=CC=C12 ZKTNOCIFYNQVPH-UHFFFAOYSA-N 0.000 description 1
- CCXOJLMHTGQFRH-UHFFFAOYSA-N n-[2-(2-methylphenoxy)propyl]quinazolin-4-amine Chemical compound N=1C=NC2=CC=CC=C2C=1NCC(C)OC1=CC=CC=C1C CCXOJLMHTGQFRH-UHFFFAOYSA-N 0.000 description 1
- BHZMXJXAQMRSHN-UHFFFAOYSA-N n-[2-(2-methylphenyl)sulfanylethyl]quinazolin-4-amine Chemical compound CC1=CC=CC=C1SCCNC1=NC=NC2=CC=CC=C12 BHZMXJXAQMRSHN-UHFFFAOYSA-N 0.000 description 1
- ZIQZIANJXIGQMA-UHFFFAOYSA-N n-[2-(2-propylphenoxy)ethyl]quinazolin-4-amine Chemical compound CCCC1=CC=CC=C1OCCNC1=NC=NC2=CC=CC=C12 ZIQZIANJXIGQMA-UHFFFAOYSA-N 0.000 description 1
- GOVYNTILGXUFTH-UHFFFAOYSA-N n-[2-(2-tert-butylphenoxy)ethyl]quinazolin-4-amine Chemical compound CC(C)(C)C1=CC=CC=C1OCCNC1=NC=NC2=CC=CC=C12 GOVYNTILGXUFTH-UHFFFAOYSA-N 0.000 description 1
- PKKNBIRXJYKRKK-UHFFFAOYSA-N n-[2-(3,5-dimethylphenoxy)ethyl]quinazolin-4-amine Chemical compound CC1=CC(C)=CC(OCCNC=2C3=CC=CC=C3N=CN=2)=C1 PKKNBIRXJYKRKK-UHFFFAOYSA-N 0.000 description 1
- URDUQBTYGOKMTL-UHFFFAOYSA-N n-[2-(3-chloro-2-methylphenoxy)ethyl]quinazolin-4-amine Chemical compound CC1=C(Cl)C=CC=C1OCCNC1=NC=NC2=CC=CC=C12 URDUQBTYGOKMTL-UHFFFAOYSA-N 0.000 description 1
- QCXIKFZVSUSMNM-UHFFFAOYSA-N n-[2-(3-chlorophenoxy)-2-methylpropyl]quinazolin-4-amine Chemical compound N=1C=NC2=CC=CC=C2C=1NCC(C)(C)OC1=CC=CC(Cl)=C1 QCXIKFZVSUSMNM-UHFFFAOYSA-N 0.000 description 1
- VPDJADSXEVFDFK-UHFFFAOYSA-N n-[2-(3-chlorophenoxy)ethyl]quinazolin-4-amine Chemical compound ClC1=CC=CC(OCCNC=2C3=CC=CC=C3N=CN=2)=C1 VPDJADSXEVFDFK-UHFFFAOYSA-N 0.000 description 1
- AEQLYFGTTJUTCN-UHFFFAOYSA-N n-[2-(3-chlorophenoxy)propyl]quinazolin-4-amine Chemical compound N=1C=NC2=CC=CC=C2C=1NCC(C)OC1=CC=CC(Cl)=C1 AEQLYFGTTJUTCN-UHFFFAOYSA-N 0.000 description 1
- NIVWALJLPDPBKD-UHFFFAOYSA-N n-[2-(3-methylphenoxy)propyl]quinazolin-4-amine Chemical compound N=1C=NC2=CC=CC=C2C=1NCC(C)OC1=CC=CC(C)=C1 NIVWALJLPDPBKD-UHFFFAOYSA-N 0.000 description 1
- QBGGXFBUNRQGLF-UHFFFAOYSA-N n-[2-(3-methylphenyl)sulfanylethyl]quinazolin-4-amine Chemical compound CC1=CC=CC(SCCNC=2C3=CC=CC=C3N=CN=2)=C1 QBGGXFBUNRQGLF-UHFFFAOYSA-N 0.000 description 1
- RONONIGPGYCPQA-UHFFFAOYSA-N n-[2-(4-bromo-3,5-dimethylphenoxy)ethyl]quinazolin-4-amine Chemical compound CC1=C(Br)C(C)=CC(OCCNC=2C3=CC=CC=C3N=CN=2)=C1 RONONIGPGYCPQA-UHFFFAOYSA-N 0.000 description 1
- URVOCKMXAQDKAA-UHFFFAOYSA-N n-[2-(4-bromophenoxy)ethyl]quinazolin-4-amine Chemical compound C1=CC(Br)=CC=C1OCCNC1=NC=NC2=CC=CC=C12 URVOCKMXAQDKAA-UHFFFAOYSA-N 0.000 description 1
- NNTNUHUNFAYQAI-UHFFFAOYSA-N n-[2-(4-bromophenyl)sulfanylethyl]quinazolin-4-amine Chemical compound C1=CC(Br)=CC=C1SCCNC1=NC=NC2=CC=CC=C12 NNTNUHUNFAYQAI-UHFFFAOYSA-N 0.000 description 1
- KWIQEYOCQRTABO-UHFFFAOYSA-N n-[2-(4-chloro-2-methoxyphenoxy)ethyl]quinazolin-4-amine Chemical compound COC1=CC(Cl)=CC=C1OCCNC1=NC=NC2=CC=CC=C12 KWIQEYOCQRTABO-UHFFFAOYSA-N 0.000 description 1
- COFJYMKAPWAVOV-UHFFFAOYSA-N n-[2-(4-chloro-2-methylphenoxy)ethyl]quinazolin-4-amine Chemical compound CC1=CC(Cl)=CC=C1OCCNC1=NC=NC2=CC=CC=C12 COFJYMKAPWAVOV-UHFFFAOYSA-N 0.000 description 1
- UOAUMNJWEYCMBJ-UHFFFAOYSA-N n-[2-(4-chlorophenyl)sulfanylethyl]quinazolin-4-amine Chemical compound C1=CC(Cl)=CC=C1SCCNC1=NC=NC2=CC=CC=C12 UOAUMNJWEYCMBJ-UHFFFAOYSA-N 0.000 description 1
- NAJWCGKQSVRJPL-UHFFFAOYSA-N n-[2-(4-fluorophenoxy)ethyl]quinazolin-4-amine Chemical compound C1=CC(F)=CC=C1OCCNC1=NC=NC2=CC=CC=C12 NAJWCGKQSVRJPL-UHFFFAOYSA-N 0.000 description 1
- VUKBIUDZZDJPLB-UHFFFAOYSA-N n-[2-(4-methoxyphenoxy)ethyl]quinazolin-4-amine Chemical compound C1=CC(OC)=CC=C1OCCNC1=NC=NC2=CC=CC=C12 VUKBIUDZZDJPLB-UHFFFAOYSA-N 0.000 description 1
- XXNXCDCAUBJHHF-UHFFFAOYSA-N n-[2-(4-methylphenoxy)propyl]quinazolin-4-amine Chemical compound N=1C=NC2=CC=CC=C2C=1NCC(C)OC1=CC=C(C)C=C1 XXNXCDCAUBJHHF-UHFFFAOYSA-N 0.000 description 1
- GFPABGQTUVJCBN-UHFFFAOYSA-N n-[2-(4-methylphenyl)sulfanylethyl]quinazolin-4-amine Chemical compound C1=CC(C)=CC=C1SCCNC1=NC=NC2=CC=CC=C12 GFPABGQTUVJCBN-UHFFFAOYSA-N 0.000 description 1
- HEANPWMDZWYMMO-UHFFFAOYSA-N n-[2-(4-propan-2-yloxyphenoxy)ethyl]quinazolin-4-amine Chemical compound C1=CC(OC(C)C)=CC=C1OCCNC1=NC=NC2=CC=CC=C12 HEANPWMDZWYMMO-UHFFFAOYSA-N 0.000 description 1
- ZKUIUJVDEJVYMC-UHFFFAOYSA-N n-[2-(4-tert-butylphenoxy)ethyl]quinazolin-4-amine Chemical compound C1=CC(C(C)(C)C)=CC=C1OCCNC1=NC=NC2=CC=CC=C12 ZKUIUJVDEJVYMC-UHFFFAOYSA-N 0.000 description 1
- URUJFQLEYLDWSX-UHFFFAOYSA-N n-[2-[2-(trifluoromethyl)phenoxy]ethyl]quinazolin-4-amine Chemical compound FC(F)(F)C1=CC=CC=C1OCCNC1=NC=NC2=CC=CC=C12 URUJFQLEYLDWSX-UHFFFAOYSA-N 0.000 description 1
- NRJFQMOHWOMQTN-UHFFFAOYSA-N n-[2-[3-(trifluoromethyl)phenoxy]ethyl]quinazolin-4-amine Chemical compound FC(F)(F)C1=CC=CC(OCCNC=2C3=CC=CC=C3N=CN=2)=C1 NRJFQMOHWOMQTN-UHFFFAOYSA-N 0.000 description 1
- NNXKRNOVQLHYEQ-UHFFFAOYSA-N n-[2-[4-chloro-2-(trifluoromethyl)phenoxy]ethyl]quinazolin-4-amine Chemical compound FC(F)(F)C1=CC(Cl)=CC=C1OCCNC1=NC=NC2=CC=CC=C12 NNXKRNOVQLHYEQ-UHFFFAOYSA-N 0.000 description 1
- VSDHCDVLFFKWJB-UHFFFAOYSA-N n-[2-methyl-2-(2-methylphenoxy)propyl]quinazolin-4-amine Chemical compound CC1=CC=CC=C1OC(C)(C)CNC1=NC=NC2=CC=CC=C12 VSDHCDVLFFKWJB-UHFFFAOYSA-N 0.000 description 1
- OCHLQRRIMDYHFY-UHFFFAOYSA-N n-[2-methyl-2-(3-methylphenoxy)propyl]quinazolin-4-amine Chemical compound CC1=CC=CC(OC(C)(C)CNC=2C3=CC=CC=C3N=CN=2)=C1 OCHLQRRIMDYHFY-UHFFFAOYSA-N 0.000 description 1
- CJLXVDYUXDNPGC-UHFFFAOYSA-N n-[2-methyl-2-(4-methylphenoxy)propyl]quinazolin-4-amine Chemical compound C1=CC(C)=CC=C1OC(C)(C)CNC1=NC=NC2=CC=CC=C12 CJLXVDYUXDNPGC-UHFFFAOYSA-N 0.000 description 1
- FUDJHOPWOFYFSV-UHFFFAOYSA-N n-[3-(2,5-dimethylphenoxy)propyl]quinazolin-4-amine Chemical compound CC1=CC=C(C)C(OCCCNC=2C3=CC=CC=C3N=CN=2)=C1 FUDJHOPWOFYFSV-UHFFFAOYSA-N 0.000 description 1
- NZTNVYKAPCAZLA-UHFFFAOYSA-N n-[3-(2-chloro-4-methoxyphenoxy)propyl]quinazolin-4-amine Chemical compound ClC1=CC(OC)=CC=C1OCCCNC1=NC=NC2=CC=CC=C12 NZTNVYKAPCAZLA-UHFFFAOYSA-N 0.000 description 1
- BACIVTRRPMEBCG-UHFFFAOYSA-N n-[3-(2-chlorophenoxy)propyl]quinazolin-4-amine Chemical compound ClC1=CC=CC=C1OCCCNC1=NC=NC2=CC=CC=C12 BACIVTRRPMEBCG-UHFFFAOYSA-N 0.000 description 1
- JBDXTKCCDVLMDT-UHFFFAOYSA-N n-[3-(2-methoxyphenoxy)propyl]quinazolin-4-amine Chemical compound COC1=CC=CC=C1OCCCNC1=NC=NC2=CC=CC=C12 JBDXTKCCDVLMDT-UHFFFAOYSA-N 0.000 description 1
- UQHNYEVOMOAHQD-UHFFFAOYSA-N n-[3-(2-methylphenoxy)propyl]quinazolin-4-amine Chemical compound CC1=CC=CC=C1OCCCNC1=NC=NC2=CC=CC=C12 UQHNYEVOMOAHQD-UHFFFAOYSA-N 0.000 description 1
- ZONXLAWWIYRZOO-UHFFFAOYSA-N n-[3-(2-methylphenyl)sulfanylpropyl]quinazolin-4-amine Chemical compound CC1=CC=CC=C1SCCCNC1=NC=NC2=CC=CC=C12 ZONXLAWWIYRZOO-UHFFFAOYSA-N 0.000 description 1
- KUEVHRBZTOLMDM-UHFFFAOYSA-N n-[3-(3,5-dimethylphenoxy)propyl]quinazolin-4-amine Chemical compound CC1=CC(C)=CC(OCCCNC=2C3=CC=CC=C3N=CN=2)=C1 KUEVHRBZTOLMDM-UHFFFAOYSA-N 0.000 description 1
- UQEUIMQBCSLAGS-UHFFFAOYSA-N n-[3-(3-chlorophenoxy)propyl]quinazolin-4-amine Chemical compound ClC1=CC=CC(OCCCNC=2C3=CC=CC=C3N=CN=2)=C1 UQEUIMQBCSLAGS-UHFFFAOYSA-N 0.000 description 1
- VRKRIPFXGNXICL-UHFFFAOYSA-N n-[3-(3-methylphenoxy)propyl]quinazolin-4-amine Chemical compound CC1=CC=CC(OCCCNC=2C3=CC=CC=C3N=CN=2)=C1 VRKRIPFXGNXICL-UHFFFAOYSA-N 0.000 description 1
- NFLCYIMHLSOSCM-UHFFFAOYSA-N n-[3-(3-methylphenyl)sulfanylpropyl]quinazolin-4-amine Chemical compound CC1=CC=CC(SCCCNC=2C3=CC=CC=C3N=CN=2)=C1 NFLCYIMHLSOSCM-UHFFFAOYSA-N 0.000 description 1
- UZCZDQWOKWFECD-UHFFFAOYSA-N n-[3-(4-chloro-2-methylphenoxy)propyl]quinazolin-4-amine Chemical compound CC1=CC(Cl)=CC=C1OCCCNC1=NC=NC2=CC=CC=C12 UZCZDQWOKWFECD-UHFFFAOYSA-N 0.000 description 1
- IEKAUXINAPJACZ-UHFFFAOYSA-N n-[3-(4-chloro-3-methylphenoxy)propyl]quinazolin-4-amine Chemical compound C1=C(Cl)C(C)=CC(OCCCNC=2C3=CC=CC=C3N=CN=2)=C1 IEKAUXINAPJACZ-UHFFFAOYSA-N 0.000 description 1
- QHIVOIUHXPLEON-UHFFFAOYSA-N n-[3-(4-chlorophenoxy)propyl]quinazolin-4-amine Chemical compound C1=CC(Cl)=CC=C1OCCCNC1=NC=NC2=CC=CC=C12 QHIVOIUHXPLEON-UHFFFAOYSA-N 0.000 description 1
- GOVRNHVGFONILY-UHFFFAOYSA-N n-[3-(4-methoxyphenoxy)propyl]quinazolin-4-amine Chemical compound C1=CC(OC)=CC=C1OCCCNC1=NC=NC2=CC=CC=C12 GOVRNHVGFONILY-UHFFFAOYSA-N 0.000 description 1
- IJSBFNCFNKFCLA-UHFFFAOYSA-N n-[3-(4-methylphenoxy)propyl]quinazolin-4-amine Chemical compound C1=CC(C)=CC=C1OCCCNC1=NC=NC2=CC=CC=C12 IJSBFNCFNKFCLA-UHFFFAOYSA-N 0.000 description 1
- AUBGOYGUQFSOLT-UHFFFAOYSA-N n-[4-(2-chlorophenoxy)butyl]-6-methylquinazolin-4-amine Chemical compound C12=CC(C)=CC=C2N=CN=C1NCCCCOC1=CC=CC=C1Cl AUBGOYGUQFSOLT-UHFFFAOYSA-N 0.000 description 1
- GGJQISHWUPLOGL-UHFFFAOYSA-N n-[4-(2-chlorophenoxy)butyl]quinazolin-4-amine Chemical compound ClC1=CC=CC=C1OCCCCNC1=NC=NC2=CC=CC=C12 GGJQISHWUPLOGL-UHFFFAOYSA-N 0.000 description 1
- AZKOHGVXSIFCGQ-UHFFFAOYSA-N n-[4-(2-methoxyphenoxy)butyl]quinazolin-4-amine Chemical compound COC1=CC=CC=C1OCCCCNC1=NC=NC2=CC=CC=C12 AZKOHGVXSIFCGQ-UHFFFAOYSA-N 0.000 description 1
- LVFXLHNLDLJCEQ-UHFFFAOYSA-N n-[4-(2-methylphenoxy)butyl]quinazolin-4-amine Chemical compound CC1=CC=CC=C1OCCCCNC1=NC=NC2=CC=CC=C12 LVFXLHNLDLJCEQ-UHFFFAOYSA-N 0.000 description 1
- URVOXMOQESPQSD-UHFFFAOYSA-N n-[4-(3-methylphenoxy)butyl]quinazolin-4-amine Chemical compound CC1=CC=CC(OCCCCNC=2C3=CC=CC=C3N=CN=2)=C1 URVOXMOQESPQSD-UHFFFAOYSA-N 0.000 description 1
- PGUWULNIFCSBND-UHFFFAOYSA-N n-[4-(4-methylphenoxy)butyl]quinazolin-4-amine Chemical compound C1=CC(C)=CC=C1OCCCCNC1=NC=NC2=CC=CC=C12 PGUWULNIFCSBND-UHFFFAOYSA-N 0.000 description 1
- RVDTXENDAOZYDT-UHFFFAOYSA-N n-[5-(2-chlorophenoxy)pentyl]quinazolin-4-amine Chemical compound ClC1=CC=CC=C1OCCCCCNC1=NC=NC2=CC=CC=C12 RVDTXENDAOZYDT-UHFFFAOYSA-N 0.000 description 1
- YZAGLAUUZVJLBG-UHFFFAOYSA-N n-[5-(2-methoxyphenoxy)pentyl]quinazolin-4-amine Chemical compound COC1=CC=CC=C1OCCCCCNC1=NC=NC2=CC=CC=C12 YZAGLAUUZVJLBG-UHFFFAOYSA-N 0.000 description 1
- KTLYCVIXIJSMHX-UHFFFAOYSA-N n-[5-(2-methylphenoxy)pentyl]quinazolin-4-amine Chemical compound CC1=CC=CC=C1OCCCCCNC1=NC=NC2=CC=CC=C12 KTLYCVIXIJSMHX-UHFFFAOYSA-N 0.000 description 1
- SCOYUJHMOPGWPN-UHFFFAOYSA-N n-[5-(3-methylphenoxy)pentyl]quinazolin-4-amine Chemical compound CC1=CC=CC(OCCCCCNC=2C3=CC=CC=C3N=CN=2)=C1 SCOYUJHMOPGWPN-UHFFFAOYSA-N 0.000 description 1
- RXDQHHWXSSPBIP-UHFFFAOYSA-N n-[5-(4-methylphenoxy)pentyl]quinazolin-4-amine Chemical compound C1=CC(C)=CC=C1OCCCCCNC1=NC=NC2=CC=CC=C12 RXDQHHWXSSPBIP-UHFFFAOYSA-N 0.000 description 1
- HYKQWTCUUCVCHM-UHFFFAOYSA-N n-[6-(2-methylphenoxy)hexyl]quinazolin-4-amine Chemical compound CC1=CC=CC=C1OCCCCCCNC1=NC=NC2=CC=CC=C12 HYKQWTCUUCVCHM-UHFFFAOYSA-N 0.000 description 1
- XFYRIFTTWFUSTR-UHFFFAOYSA-N n-[8-(2-methylphenoxy)octyl]quinazolin-4-amine Chemical compound CC1=CC=CC=C1OCCCCCCCCNC1=NC=NC2=CC=CC=C12 XFYRIFTTWFUSTR-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- DHUSVDMQIGWDLT-UHFFFAOYSA-N n-ethylquinazolin-2-amine Chemical compound C1=CC=CC2=NC(NCC)=NC=C21 DHUSVDMQIGWDLT-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000012053 oil suspension Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000003151 ovacidal effect Effects 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229940116315 oxalic acid Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000006069 physical mixture Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 229960004319 trichloroacetic acid Drugs 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15123578A JPS5576803A (en) | 1978-12-06 | 1978-12-06 | Agent for controlling noxious life |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15123578A JPS5576803A (en) | 1978-12-06 | 1978-12-06 | Agent for controlling noxious life |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5576803A JPS5576803A (en) | 1980-06-10 |
| JPS626547B2 true JPS626547B2 (pt) | 1987-02-12 |
Family
ID=15514195
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15123578A Granted JPS5576803A (en) | 1978-12-06 | 1978-12-06 | Agent for controlling noxious life |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5576803A (pt) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6267A (ja) * | 1985-03-14 | 1987-01-06 | Sankyo Co Ltd | フエノキシアルキルアミン誘導体、その製法および殺虫殺ダニ剤 |
| GT198900008A (es) * | 1988-01-29 | 1990-07-17 | Derivados de quinolina, quinazolina y cinolina. | |
| IL89029A (en) * | 1988-01-29 | 1993-01-31 | Lilly Co Eli | Fungicidal quinoline and cinnoline derivatives, compositions containing them, and fungicidal methods of using them |
| US5124333A (en) * | 1989-08-02 | 1992-06-23 | Ube Industries, Ltd. | Aminopyrimidine derivatives and harmful organisms preventive agent |
| JPWO2012096137A1 (ja) * | 2011-01-14 | 2014-06-09 | 株式会社エス・ディー・エス バイオテック | 農園芸用の有害生物防除剤としてのキナゾリン誘導体 |
| WO2012096115A1 (ja) * | 2011-01-14 | 2012-07-19 | 株式会社エス・ディー・エス バイオテック | 農園芸用の有害生物防除剤としての含フッ素キナゾリン誘導体 |
| BR112015018282B1 (pt) | 2013-02-01 | 2021-08-24 | Wellstat Therapeutics Corporation | Compostos de amina, composição compreendendo os referidos compostos e usos dos mesmos |
-
1978
- 1978-12-06 JP JP15123578A patent/JPS5576803A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5576803A (en) | 1980-06-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR930009443B1 (ko) | 페녹시알킬아미노 피리미딘 유도체의 제조방법 | |
| EP0186190B1 (en) | Benzimidazole derivatives, and their production and use | |
| EP0132606B1 (en) | Benzimidazole derivatives, and their production and use | |
| CZ167994A3 (en) | Novel phthalazine derivatives, process of their preparation and pesticidal agents based thereon | |
| JPH0533703B2 (pt) | ||
| EP0323757A2 (en) | Alkylaminopyrimidine derivative, process for producing the same, and insecticide, acaricide and fungicide containing the same as active ingredient | |
| JPS626547B2 (pt) | ||
| JPS626548B2 (pt) | ||
| JP2738010B2 (ja) | ピラゾール誘動体及び選択性除草剤 | |
| KR840001232B1 (ko) | 벤젠아민의 제조방법 | |
| JP2690816B2 (ja) | キノリニルオキサジアゾール除草剤 | |
| JPS63225364A (ja) | アラルキルアミノピリミジン誘導体、その製造法並びに該誘導体を有効成分とする殺虫剤、殺ダニ剤及び殺菌剤 | |
| JPH0424351B2 (pt) | ||
| JPH07116161B2 (ja) | ピリダジノン誘導体 | |
| JPH08245322A (ja) | 殺虫殺菌組成物 | |
| JPH0251549B2 (pt) | ||
| JPH0249297B2 (pt) | ||
| JPH0651685B2 (ja) | フェノキシアルキルアミン誘導体および殺虫殺ダニ剤 | |
| US4596801A (en) | 4H-3,1-benzoxazine derivatives, process for producing the same and agricultural or horticultural fungicide containing the same | |
| JPH0234944B2 (pt) | ||
| JPH0453841B2 (pt) | ||
| JPH0526781B2 (pt) | ||
| JPH045025B2 (pt) | ||
| JP2710672B2 (ja) | アミノピリミジン誘導体、その製造法及び殺虫・殺菌剤 | |
| JPS625428B2 (pt) |