JPH0533221B2 - - Google Patents
Info
- Publication number
- JPH0533221B2 JPH0533221B2 JP59138237A JP13823784A JPH0533221B2 JP H0533221 B2 JPH0533221 B2 JP H0533221B2 JP 59138237 A JP59138237 A JP 59138237A JP 13823784 A JP13823784 A JP 13823784A JP H0533221 B2 JPH0533221 B2 JP H0533221B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- benzyl chloride
- atom
- carbon atoms
- compound
- 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 - Lifetime
Links
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 239000000642 acaricide Substances 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- 125000004434 sulfur atom Chemical group 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 125000005108 alkenylthio group Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 4
- 125000005109 alkynylthio group Chemical group 0.000 claims description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 3
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 description 33
- 150000001875 compounds Chemical class 0.000 description 31
- -1 3,4-methylenedioxy groups Chemical group 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 15
- 230000000895 acaricidal effect Effects 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 9
- 229940073608 benzyl chloride Drugs 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 241001454295 Tetranychidae Species 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000004927 clay Substances 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- LDZYRENCLPUXAX-UHFFFAOYSA-N 2-methyl-1h-benzimidazole Chemical compound C1=CC=C2NC(C)=NC2=C1 LDZYRENCLPUXAX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000005995 Aluminium silicate Substances 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 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
- 235000012211 aluminium silicate Nutrition 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 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 3
- 239000003350 kerosene Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229910052814 silicon oxide Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- POYLDOYOMVDCPG-UHFFFAOYSA-N 1-(chloromethyl)-4-(4-ethoxyphenoxy)benzene Chemical compound C1=CC(OCC)=CC=C1OC1=CC=C(CCl)C=C1 POYLDOYOMVDCPG-UHFFFAOYSA-N 0.000 description 2
- ANGJJOILHZZNIU-UHFFFAOYSA-N 1-(chloromethyl)-4-(4-propoxyphenoxy)benzene Chemical compound C1=CC(OCCC)=CC=C1OC1=CC=C(CCl)C=C1 ANGJJOILHZZNIU-UHFFFAOYSA-N 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
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- HPEUJPJOZXNMSJ-UHFFFAOYSA-N Methyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC HPEUJPJOZXNMSJ-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
- 229910019142 PO4 Inorganic materials 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-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
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- 150000001556 benzimidazoles Chemical class 0.000 description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
- RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
- 244000013123 dwarf bean Species 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000002316 fumigant Substances 0.000 description 2
- 235000021331 green beans Nutrition 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000003915 liquefied petroleum gas Substances 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- SJJSGXXYPZDZDH-UHFFFAOYSA-N (4-benzylphenyl)methyl methanesulfonate Chemical compound C1=CC(COS(=O)(=O)C)=CC=C1CC1=CC=CC=C1 SJJSGXXYPZDZDH-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- HRLZUTTVBDGKBN-UHFFFAOYSA-N 1-(2-bromo-1,1,2,2-tetrafluoroethoxy)-4-[4-(chloromethyl)phenoxy]benzene Chemical compound C1=CC(OC(F)(F)C(F)(Br)F)=CC=C1OC1=CC=C(CCl)C=C1 HRLZUTTVBDGKBN-UHFFFAOYSA-N 0.000 description 1
- IKGOOQKSNWOHQN-UHFFFAOYSA-N 1-(benzenesulfinyl)-4-(bromomethyl)benzene Chemical compound C1=CC(CBr)=CC=C1S(=O)C1=CC=CC=C1 IKGOOQKSNWOHQN-UHFFFAOYSA-N 0.000 description 1
- GPDSSRCOXIJNTM-UHFFFAOYSA-N 1-(bromomethyl)-4-(2-chlorophenyl)sulfanylbenzene Chemical compound ClC1=CC=CC=C1SC1=CC=C(CBr)C=C1 GPDSSRCOXIJNTM-UHFFFAOYSA-N 0.000 description 1
- BFIMPPAIHJQTTO-UHFFFAOYSA-N 1-(bromomethyl)-4-(3-fluorophenoxy)benzene Chemical compound FC1=CC=CC(OC=2C=CC(CBr)=CC=2)=C1 BFIMPPAIHJQTTO-UHFFFAOYSA-N 0.000 description 1
- JUXBGEATOASJLB-UHFFFAOYSA-N 1-(bromomethyl)-4-(3-methylphenoxy)benzene Chemical compound CC1=CC=CC(OC=2C=CC(CBr)=CC=2)=C1 JUXBGEATOASJLB-UHFFFAOYSA-N 0.000 description 1
- DLFIRFWYAQKJAK-UHFFFAOYSA-N 1-(bromomethyl)-4-[3-(trifluoromethyl)phenoxy]benzene Chemical compound FC(F)(F)C1=CC=CC(OC=2C=CC(CBr)=CC=2)=C1 DLFIRFWYAQKJAK-UHFFFAOYSA-N 0.000 description 1
- CPIGBCFBFZSCQI-UHFFFAOYSA-N 1-(bromomethyl)-4-phenoxybenzene Chemical compound C1=CC(CBr)=CC=C1OC1=CC=CC=C1 CPIGBCFBFZSCQI-UHFFFAOYSA-N 0.000 description 1
- JTMJOWJQRWQXJI-UHFFFAOYSA-N 1-(chloromethyl)-4-(3-ethoxyphenoxy)benzene Chemical compound CCOC1=CC=CC(OC=2C=CC(CCl)=CC=2)=C1 JTMJOWJQRWQXJI-UHFFFAOYSA-N 0.000 description 1
- DPBOGMVCKXARPE-UHFFFAOYSA-N 1-(chloromethyl)-4-(3-ethylphenoxy)benzene Chemical compound CCC1=CC=CC(OC=2C=CC(CCl)=CC=2)=C1 DPBOGMVCKXARPE-UHFFFAOYSA-N 0.000 description 1
- NCOSIYYGKXIFHB-UHFFFAOYSA-N 1-(chloromethyl)-4-(3-ethylphenyl)sulfanylbenzene Chemical compound C(C)C=1C=C(SC2=CC=C(CCl)C=C2)C=CC1 NCOSIYYGKXIFHB-UHFFFAOYSA-N 0.000 description 1
- WYYVHLRTPNYFQJ-UHFFFAOYSA-N 1-(chloromethyl)-4-(3-ethynoxyphenoxy)benzene Chemical compound C1=CC(CCl)=CC=C1OC1=CC=CC(OC#C)=C1 WYYVHLRTPNYFQJ-UHFFFAOYSA-N 0.000 description 1
- LVRZIZWOEWFGPF-UHFFFAOYSA-N 1-(chloromethyl)-4-(3-hexoxyphenoxy)benzene Chemical compound CCCCCCOC1=CC=CC(OC=2C=CC(CCl)=CC=2)=C1 LVRZIZWOEWFGPF-UHFFFAOYSA-N 0.000 description 1
- LIWUVRGGCOAJPX-UHFFFAOYSA-N 1-(chloromethyl)-4-(3-methoxyphenoxy)benzene Chemical compound COC1=CC=CC(OC=2C=CC(CCl)=CC=2)=C1 LIWUVRGGCOAJPX-UHFFFAOYSA-N 0.000 description 1
- CWJLJPLQQLOYDR-UHFFFAOYSA-N 1-(chloromethyl)-4-(3-methylphenoxy)benzene Chemical compound CC1=CC=CC(OC=2C=CC(CCl)=CC=2)=C1 CWJLJPLQQLOYDR-UHFFFAOYSA-N 0.000 description 1
- WCJUJRZYMFAZBF-UHFFFAOYSA-N 1-(chloromethyl)-4-(3-methylphenyl)sulfanylbenzene Chemical compound CC=1C=C(SC2=CC=C(CCl)C=C2)C=CC1 WCJUJRZYMFAZBF-UHFFFAOYSA-N 0.000 description 1
- HIHGYUUHTSIGAV-UHFFFAOYSA-N 1-(chloromethyl)-4-(3-pentoxyphenoxy)benzene Chemical compound CCCCCOC1=CC=CC(OC=2C=CC(CCl)=CC=2)=C1 HIHGYUUHTSIGAV-UHFFFAOYSA-N 0.000 description 1
- DNFDCJMUPHNIPX-UHFFFAOYSA-N 1-(chloromethyl)-4-(3-propan-2-yloxyphenoxy)benzene Chemical compound CC(C)OC1=CC=CC(OC=2C=CC(CCl)=CC=2)=C1 DNFDCJMUPHNIPX-UHFFFAOYSA-N 0.000 description 1
- WJUCIJYXQMURDI-UHFFFAOYSA-N 1-(chloromethyl)-4-(3-propan-2-ylphenoxy)benzene Chemical compound CC(C)C1=CC=CC(OC=2C=CC(CCl)=CC=2)=C1 WJUCIJYXQMURDI-UHFFFAOYSA-N 0.000 description 1
- HCALCJUSGYDIFW-UHFFFAOYSA-N 1-(chloromethyl)-4-(3-propoxyphenoxy)benzene Chemical compound CCCOC1=CC=CC(OC=2C=CC(CCl)=CC=2)=C1 HCALCJUSGYDIFW-UHFFFAOYSA-N 0.000 description 1
- HWUSQLIGEMNQFB-UHFFFAOYSA-N 1-(chloromethyl)-4-(3-propylphenoxy)benzene Chemical compound CCCC1=CC=CC(OC=2C=CC(CCl)=CC=2)=C1 HWUSQLIGEMNQFB-UHFFFAOYSA-N 0.000 description 1
- NQAQTZJHSGPQGU-UHFFFAOYSA-N 1-(chloromethyl)-4-(3-propylphenyl)sulfanylbenzene Chemical compound C(CC)C=1C=C(SC2=CC=C(CCl)C=C2)C=CC=1 NQAQTZJHSGPQGU-UHFFFAOYSA-N 0.000 description 1
- BFZISLMOTCRNON-UHFFFAOYSA-N 1-(chloromethyl)-4-(4-ethenoxyphenoxy)benzene Chemical compound C1=CC(CCl)=CC=C1OC1=CC=C(OC=C)C=C1 BFZISLMOTCRNON-UHFFFAOYSA-N 0.000 description 1
- KIGHRBPRQUPVSN-UHFFFAOYSA-N 1-(chloromethyl)-4-(4-ethoxyphenyl)sulfanylbenzene Chemical compound C1=CC(OCC)=CC=C1SC1=CC=C(CCl)C=C1 KIGHRBPRQUPVSN-UHFFFAOYSA-N 0.000 description 1
- RIGFISSODGBGBA-UHFFFAOYSA-N 1-(chloromethyl)-4-(4-ethylphenoxy)benzene Chemical compound C1=CC(CC)=CC=C1OC1=CC=C(CCl)C=C1 RIGFISSODGBGBA-UHFFFAOYSA-N 0.000 description 1
- OZEHRVXTBBKYQZ-UHFFFAOYSA-N 1-(chloromethyl)-4-(4-ethylphenyl)sulfanylbenzene Chemical compound C(C)C1=CC=C(SC2=CC=C(CCl)C=C2)C=C1 OZEHRVXTBBKYQZ-UHFFFAOYSA-N 0.000 description 1
- ATJPWSWXNIBYIQ-UHFFFAOYSA-N 1-(chloromethyl)-4-(4-hexylphenoxy)benzene Chemical compound C1=CC(CCCCCC)=CC=C1OC1=CC=C(CCl)C=C1 ATJPWSWXNIBYIQ-UHFFFAOYSA-N 0.000 description 1
- LQNOPXANJOVLRI-UHFFFAOYSA-N 1-(chloromethyl)-4-(4-methoxyphenoxy)benzene Chemical compound C1=CC(OC)=CC=C1OC1=CC=C(CCl)C=C1 LQNOPXANJOVLRI-UHFFFAOYSA-N 0.000 description 1
- JQFMCGQUENUYRZ-UHFFFAOYSA-N 1-(chloromethyl)-4-(4-methylphenyl)sulfanylbenzene Chemical compound C1=CC(C)=CC=C1SC1=CC=C(CCl)C=C1 JQFMCGQUENUYRZ-UHFFFAOYSA-N 0.000 description 1
- SZJJSNZCNRHCAM-UHFFFAOYSA-N 1-(chloromethyl)-4-(4-methylsulfonylphenoxy)benzene Chemical compound C1=CC(S(=O)(=O)C)=CC=C1OC1=CC=C(CCl)C=C1 SZJJSNZCNRHCAM-UHFFFAOYSA-N 0.000 description 1
- UBPDLULODYBPTO-UHFFFAOYSA-N 1-(chloromethyl)-4-(4-pentan-2-ylphenoxy)benzene Chemical compound C1=CC(C(C)CCC)=CC=C1OC1=CC=C(CCl)C=C1 UBPDLULODYBPTO-UHFFFAOYSA-N 0.000 description 1
- AHCZRFUOALOAAC-UHFFFAOYSA-N 1-(chloromethyl)-4-(4-pentoxyphenoxy)benzene Chemical compound C1=CC(OCCCCC)=CC=C1OC1=CC=C(CCl)C=C1 AHCZRFUOALOAAC-UHFFFAOYSA-N 0.000 description 1
- LKQTXNUHTRZOEO-UHFFFAOYSA-N 1-(chloromethyl)-4-(4-pentylphenoxy)benzene Chemical compound C1=CC(CCCCC)=CC=C1OC1=CC=C(CCl)C=C1 LKQTXNUHTRZOEO-UHFFFAOYSA-N 0.000 description 1
- XDXGTQZLCYUMGC-UHFFFAOYSA-N 1-(chloromethyl)-4-(4-pentylphenyl)sulfanylbenzene Chemical compound C(CCCC)C1=CC=C(SC2=CC=C(CCl)C=C2)C=C1 XDXGTQZLCYUMGC-UHFFFAOYSA-N 0.000 description 1
- JKLZFRPYAVLSJT-UHFFFAOYSA-N 1-(chloromethyl)-4-(4-prop-2-ynoxyphenoxy)benzene Chemical compound C1=CC(CCl)=CC=C1OC1=CC=C(OCC#C)C=C1 JKLZFRPYAVLSJT-UHFFFAOYSA-N 0.000 description 1
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- 125000000232 haloalkynyl group Chemical group 0.000 description 1
- 125000005292 haloalkynyloxy group Chemical group 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000000077 insect repellent Substances 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
- QPPQHRDVPBTVEV-UHFFFAOYSA-N isopropyl dihydrogen phosphate Chemical compound CC(C)OP(O)(O)=O QPPQHRDVPBTVEV-UHFFFAOYSA-N 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000005905 mesyloxy group Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 1
- 229940073769 methyl oleate Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- XKZZEPBLQGHSOR-UHFFFAOYSA-N n-[4-(chloromethyl)phenyl]-3-ethoxyaniline Chemical compound CCOC1=CC=CC(NC=2C=CC(CCl)=CC=2)=C1 XKZZEPBLQGHSOR-UHFFFAOYSA-N 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000012053 oil suspension Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000010665 pine oil Substances 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59138237A JPS6117569A (ja) | 1984-07-03 | 1984-07-03 | ベンズイミダゾ−ル誘導体およびそれを有効成分とする殺ダニ剤 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59138237A JPS6117569A (ja) | 1984-07-03 | 1984-07-03 | ベンズイミダゾ−ル誘導体およびそれを有効成分とする殺ダニ剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6117569A JPS6117569A (ja) | 1986-01-25 |
| JPH0533221B2 true JPH0533221B2 (ru) | 1993-05-19 |
Family
ID=15217281
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59138237A Granted JPS6117569A (ja) | 1984-07-03 | 1984-07-03 | ベンズイミダゾ−ル誘導体およびそれを有効成分とする殺ダニ剤 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6117569A (ru) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103483266A (zh) * | 2013-08-23 | 2014-01-01 | 广东东硕科技有限公司 | 2-取代苯并咪唑类化合物的合成方法 |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1329614C (en) * | 1987-05-02 | 1994-05-17 | Rainer Buerstinghaus | N-substituted azoles |
| EP0461040A1 (fr) * | 1990-06-08 | 1991-12-11 | Roussel Uclaf | Dérivés de l'imidazole, leur procédé de préparation, les intermédiaires obtenus, leur application à titre de médicaments et les compositions pharmaceutiques les renfermant |
| TWI731317B (zh) | 2013-12-10 | 2021-06-21 | 美商健臻公司 | 原肌球蛋白相關之激酶（ｔｒｋ）抑制劑 |
| EP3233057A2 (en) | 2014-12-18 | 2017-10-25 | Genzyme Corporation | Pharmaceutical formulations of tropomyosin related kinase (trk) inhibitors |
-
1984
- 1984-07-03 JP JP59138237A patent/JPS6117569A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103483266A (zh) * | 2013-08-23 | 2014-01-01 | 广东东硕科技有限公司 | 2-取代苯并咪唑类化合物的合成方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6117569A (ja) | 1986-01-25 |
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