JPH0258259B2 - - Google Patents
Info
- Publication number
- JPH0258259B2 JPH0258259B2 JP14200382A JP14200382A JPH0258259B2 JP H0258259 B2 JPH0258259 B2 JP H0258259B2 JP 14200382 A JP14200382 A JP 14200382A JP 14200382 A JP14200382 A JP 14200382A JP H0258259 B2 JPH0258259 B2 JP H0258259B2
- Authority
- JP
- Japan
- Prior art keywords
- ethyl
- phenoxy
- methyl
- halogen
- fluorophenoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims description 61
- 239000000203 mixture Substances 0.000 claims description 51
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 40
- 239000001257 hydrogen Substances 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 229910052736 halogen Inorganic materials 0.000 claims description 31
- 150000002367 halogens Chemical class 0.000 claims description 30
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 25
- 241000607479 Yersinia pestis Species 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 23
- KWBIXTIBYFUAGV-UHFFFAOYSA-M n-ethylcarbamate Chemical compound CCNC([O-])=O KWBIXTIBYFUAGV-UHFFFAOYSA-M 0.000 claims description 21
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 19
- 150000002431 hydrogen Chemical class 0.000 claims description 19
- 229910052717 sulfur Inorganic materials 0.000 claims description 19
- 239000011593 sulfur Chemical group 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 14
- -1 that is Chemical class 0.000 claims description 14
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 238000009472 formulation Methods 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- DWZFDQHAHAZMGP-UHFFFAOYSA-N 2-(2-fluoro-4-phenoxyphenoxy)ethyl n-ethylcarbamate Chemical compound C1=C(F)C(OCCOC(=O)NCC)=CC=C1OC1=CC=CC=C1 DWZFDQHAHAZMGP-UHFFFAOYSA-N 0.000 claims description 3
- QWJRSGHXDBATOX-UHFFFAOYSA-N o-[2-[4-(3-bromophenoxy)phenoxy]ethyl] n-ethylcarbamothioate Chemical compound C1=CC(OCCOC(=S)NCC)=CC=C1OC1=CC=CC(Br)=C1 QWJRSGHXDBATOX-UHFFFAOYSA-N 0.000 claims description 3
- CAACPWQCDSMMLA-UHFFFAOYSA-N o-[2-[4-(4-fluorophenoxy)phenoxy]ethyl] n-ethylcarbamothioate Chemical compound C1=CC(OCCOC(=S)NCC)=CC=C1OC1=CC=C(F)C=C1 CAACPWQCDSMMLA-UHFFFAOYSA-N 0.000 claims description 3
- PLYSJWVYPFIUOP-UHFFFAOYSA-N 2-(3-fluoro-4-phenoxyphenoxy)ethyl n-ethylcarbamate Chemical compound FC1=CC(OCCOC(=O)NCC)=CC=C1OC1=CC=CC=C1 PLYSJWVYPFIUOP-UHFFFAOYSA-N 0.000 claims description 2
- ZHFSEDMGYKEFNW-UHFFFAOYSA-N 2-(5-methyl-2-phenoxyphenoxy)ethyl n-ethylcarbamate Chemical compound CCNC(=O)OCCOC1=CC(C)=CC=C1OC1=CC=CC=C1 ZHFSEDMGYKEFNW-UHFFFAOYSA-N 0.000 claims description 2
- SFSWSVHUCMJAMU-UHFFFAOYSA-N 2-[4-(3-fluorophenoxy)phenoxy]ethyl n-ethylcarbamate Chemical compound C1=CC(OCCOC(=O)NCC)=CC=C1OC1=CC=CC(F)=C1 SFSWSVHUCMJAMU-UHFFFAOYSA-N 0.000 claims description 2
- DTHXKOSZKGBMPD-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)sulfanylphenoxy]ethyl n-ethylcarbamate Chemical compound C1=CC(OCCOC(=O)NCC)=CC=C1SC1=CC=C(Cl)C=C1 DTHXKOSZKGBMPD-UHFFFAOYSA-N 0.000 claims description 2
- NKGOVPXIMSSPLG-UHFFFAOYSA-N 2-[4-(4-fluorophenoxy)phenoxy]ethyl n,n-dimethylcarbamate Chemical compound C1=CC(OCCOC(=O)N(C)C)=CC=C1OC1=CC=C(F)C=C1 NKGOVPXIMSSPLG-UHFFFAOYSA-N 0.000 claims description 2
- RLAARHGKYTVYLJ-UHFFFAOYSA-N 2-[4-(4-fluorophenoxy)phenoxy]ethyl n-methylcarbamate Chemical compound C1=CC(OCCOC(=O)NC)=CC=C1OC1=CC=C(F)C=C1 RLAARHGKYTVYLJ-UHFFFAOYSA-N 0.000 claims description 2
- PZCLCCQYVGLWGR-UHFFFAOYSA-N 2-[4-(4-fluorophenoxy)phenoxy]ethyl n-propan-2-ylcarbamate Chemical compound C1=CC(OCCOC(=O)NC(C)C)=CC=C1OC1=CC=C(F)C=C1 PZCLCCQYVGLWGR-UHFFFAOYSA-N 0.000 claims description 2
- MJADPUXZHICPJZ-UHFFFAOYSA-N o-[2-[4-(3-chlorophenoxy)phenoxy]ethyl] n-ethylcarbamothioate Chemical compound C1=CC(OCCOC(=S)NCC)=CC=C1OC1=CC=CC(Cl)=C1 MJADPUXZHICPJZ-UHFFFAOYSA-N 0.000 claims description 2
- JNBBAJZBBIFRCG-UHFFFAOYSA-N o-[2-[4-(3-fluorophenoxy)phenoxy]ethyl] n-ethylcarbamothioate Chemical compound C1=CC(OCCOC(=S)NCC)=CC=C1OC1=CC=CC(F)=C1 JNBBAJZBBIFRCG-UHFFFAOYSA-N 0.000 claims description 2
- BRUZHVOFQJZKAP-UHFFFAOYSA-N o-[2-[4-(3-methylphenoxy)phenoxy]ethyl] n-ethylcarbamothioate Chemical compound C1=CC(OCCOC(=S)NCC)=CC=C1OC1=CC=CC(C)=C1 BRUZHVOFQJZKAP-UHFFFAOYSA-N 0.000 claims description 2
- FCJUGAVEBNOLHJ-UHFFFAOYSA-N 1-[4-(3-fluorophenoxy)phenoxy]propan-2-yl n-methylcarbamate Chemical compound C1=CC(OCC(C)OC(=O)NC)=CC=C1OC1=CC=CC(F)=C1 FCJUGAVEBNOLHJ-UHFFFAOYSA-N 0.000 claims 2
- LCUOWFBUWBGUPV-UHFFFAOYSA-N 2-(4-benzoylphenoxy)ethyl n-ethylcarbamate Chemical compound C1=CC(OCCOC(=O)NCC)=CC=C1C(=O)C1=CC=CC=C1 LCUOWFBUWBGUPV-UHFFFAOYSA-N 0.000 claims 1
- WUONCXFBWWPCTF-UHFFFAOYSA-N 2-(4-benzylphenoxy)ethyl n-ethylcarbamate Chemical compound C1=CC(OCCOC(=O)NCC)=CC=C1CC1=CC=CC=C1 WUONCXFBWWPCTF-UHFFFAOYSA-N 0.000 claims 1
- WLPNGJQKCWDUTR-UHFFFAOYSA-N 2-(4-phenylsulfanylphenoxy)ethyl n-ethylcarbamate Chemical compound C1=CC(OCCOC(=O)NCC)=CC=C1SC1=CC=CC=C1 WLPNGJQKCWDUTR-UHFFFAOYSA-N 0.000 claims 1
- OBSBMPKUBTWDRL-UHFFFAOYSA-N 2-[4-(3,5-dichlorophenoxy)phenoxy]ethyl n-ethylcarbamate Chemical compound C1=CC(OCCOC(=O)NCC)=CC=C1OC1=CC(Cl)=CC(Cl)=C1 OBSBMPKUBTWDRL-UHFFFAOYSA-N 0.000 claims 1
- ZGLJNYCLSVGTAH-UHFFFAOYSA-N 2-[4-(3,5-dimethylphenoxy)phenoxy]ethyl n-ethylcarbamate Chemical compound C1=CC(OCCOC(=O)NCC)=CC=C1OC1=CC(C)=CC(C)=C1 ZGLJNYCLSVGTAH-UHFFFAOYSA-N 0.000 claims 1
- LEJCOZMUAJXRCQ-UHFFFAOYSA-N 2-[4-(3-chloro-4-fluorophenoxy)phenoxy]ethyl n-ethylcarbamate Chemical compound C1=CC(OCCOC(=O)NCC)=CC=C1OC1=CC=C(F)C(Cl)=C1 LEJCOZMUAJXRCQ-UHFFFAOYSA-N 0.000 claims 1
- ZHONHYJCMIVZGC-UHFFFAOYSA-N 2-[4-(3-chloro-5-fluorophenoxy)phenoxy]ethyl n-ethylcarbamate Chemical compound C1=CC(OCCOC(=O)NCC)=CC=C1OC1=CC(F)=CC(Cl)=C1 ZHONHYJCMIVZGC-UHFFFAOYSA-N 0.000 claims 1
- ONBDCDRQWCACII-UHFFFAOYSA-N 2-[4-(3-chlorophenoxy)phenoxy]ethyl n-ethylcarbamate Chemical compound C1=CC(OCCOC(=O)NCC)=CC=C1OC1=CC=CC(Cl)=C1 ONBDCDRQWCACII-UHFFFAOYSA-N 0.000 claims 1
- CRGFKXUCLPEXOS-UHFFFAOYSA-N 2-[4-(3-methylphenoxy)phenoxy]ethyl n-ethylcarbamate Chemical compound C1=CC(OCCOC(=O)NCC)=CC=C1OC1=CC=CC(C)=C1 CRGFKXUCLPEXOS-UHFFFAOYSA-N 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- 239000000243 solution Substances 0.000 description 28
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 239000013543 active substance Substances 0.000 description 26
- 238000002844 melting Methods 0.000 description 26
- 230000008018 melting Effects 0.000 description 26
- 238000012360 testing method Methods 0.000 description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 17
- 239000008187 granular material Substances 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 239000000843 powder Substances 0.000 description 11
- 230000000694 effects Effects 0.000 description 10
- 230000009467 reduction Effects 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 235000013312 flour Nutrition 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 239000000284 extract Substances 0.000 description 8
- 239000002689 soil Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000007921 spray Substances 0.000 description 8
- 239000004094 surface-active agent Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 239000012876 carrier material Substances 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- HBNYJWAFDZLWRS-UHFFFAOYSA-N ethyl isothiocyanate Chemical compound CCN=C=S HBNYJWAFDZLWRS-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- XMAMIKBFRLMFMQ-UHFFFAOYSA-N 2-[4-(4-fluorophenoxy)phenoxy]ethanol Chemical compound C1=CC(OCCO)=CC=C1OC1=CC=C(F)C=C1 XMAMIKBFRLMFMQ-UHFFFAOYSA-N 0.000 description 5
- 241000238876 Acari Species 0.000 description 5
- 241000258937 Hemiptera Species 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- 239000011230 binding agent Substances 0.000 description 5
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 5
- 239000002612 dispersion medium Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- 241001414828 Aonidiella aurantii Species 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 241000255925 Diptera Species 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- 241000238631 Hexapoda Species 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 241000255777 Lepidoptera Species 0.000 description 4
- 230000019552 anatomical structure morphogenesis Effects 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- DYFMKNCWHJHTRK-UHFFFAOYSA-N 1-[4-(3-fluorophenoxy)phenoxy]propan-2-ol Chemical compound C1=CC(OCC(O)C)=CC=C1OC1=CC=CC(F)=C1 DYFMKNCWHJHTRK-UHFFFAOYSA-N 0.000 description 3
- WRSFVCFKNUAXAV-UHFFFAOYSA-N 2-[4-(3-chlorophenoxy)phenoxy]ethanol Chemical compound C1=CC(OCCO)=CC=C1OC1=CC=CC(Cl)=C1 WRSFVCFKNUAXAV-UHFFFAOYSA-N 0.000 description 3
- GIZYMZPZBYIAQS-UHFFFAOYSA-N 2-[4-(3-fluorophenoxy)phenoxy]ethanol Chemical compound C1=CC(OCCO)=CC=C1OC1=CC=CC(F)=C1 GIZYMZPZBYIAQS-UHFFFAOYSA-N 0.000 description 3
- WEOZCKPNKHGSOI-UHFFFAOYSA-N 4-(3-fluorophenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=CC(F)=C1 WEOZCKPNKHGSOI-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241000175828 Adoxophyes orana Species 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 3
- 241000630736 Ephestia Species 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 241000257159 Musca domestica Species 0.000 description 3
- 241000244206 Nematoda Species 0.000 description 3
- 241000526145 Psylla Species 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- 244000061456 Solanum tuberosum Species 0.000 description 3
- 235000002595 Solanum tuberosum Nutrition 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 238000005661 deetherification reaction Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000004495 emulsifiable concentrate Substances 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 150000002540 isothiocyanates Chemical class 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000008262 pumice Substances 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- NCTBMVAIKUNJFJ-UHFFFAOYSA-N 1-methoxy-4-(3-methylphenoxy)benzene Chemical compound C1=CC(OC)=CC=C1OC1=CC=CC(C)=C1 NCTBMVAIKUNJFJ-UHFFFAOYSA-N 0.000 description 2
- QIQFUYGVTPUCLN-UHFFFAOYSA-N 2-(2-fluoro-4-phenoxyphenoxy)ethanol Chemical compound C1=C(F)C(OCCO)=CC=C1OC1=CC=CC=C1 QIQFUYGVTPUCLN-UHFFFAOYSA-N 0.000 description 2
- UXKPNKNKTLJGHP-UHFFFAOYSA-N 2-(3-fluoro-4-phenoxyphenoxy)ethanol Chemical compound FC1=CC(OCCO)=CC=C1OC1=CC=CC=C1 UXKPNKNKTLJGHP-UHFFFAOYSA-N 0.000 description 2
- ATEXKBDVRSSKTA-UHFFFAOYSA-N 2-(4-benzylphenoxy)ethanol Chemical compound C1=CC(OCCO)=CC=C1CC1=CC=CC=C1 ATEXKBDVRSSKTA-UHFFFAOYSA-N 0.000 description 2
- WITXHDIRHLWCQY-UHFFFAOYSA-N 2-(5-methyl-2-phenoxyphenoxy)ethanol Chemical compound OCCOC1=CC(C)=CC=C1OC1=CC=CC=C1 WITXHDIRHLWCQY-UHFFFAOYSA-N 0.000 description 2
- ZBQZUUKHYYYRDL-UHFFFAOYSA-N 2-[4-(3,5-dichlorophenoxy)phenoxy]ethanol Chemical compound C1=CC(OCCO)=CC=C1OC1=CC(Cl)=CC(Cl)=C1 ZBQZUUKHYYYRDL-UHFFFAOYSA-N 0.000 description 2
- WCHBMBBJGOIPEQ-UHFFFAOYSA-N 2-[4-(3,5-dimethylphenoxy)phenoxy]ethanol Chemical compound CC1=CC(C)=CC(OC=2C=CC(OCCO)=CC=2)=C1 WCHBMBBJGOIPEQ-UHFFFAOYSA-N 0.000 description 2
- SVYYGDNXZWRRCQ-UHFFFAOYSA-N 2-[4-(3-chloro-4-fluorophenoxy)phenoxy]ethanol Chemical compound C1=CC(OCCO)=CC=C1OC1=CC=C(F)C(Cl)=C1 SVYYGDNXZWRRCQ-UHFFFAOYSA-N 0.000 description 2
- XIVLJUIXEYRFGI-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)sulfanylphenoxy]ethanol Chemical compound C1=CC(OCCO)=CC=C1SC1=CC=C(Cl)C=C1 XIVLJUIXEYRFGI-UHFFFAOYSA-N 0.000 description 2
- UKXWEXICPBNEFO-UHFFFAOYSA-N 2-fluoro-4-phenoxyphenol Chemical compound C1=C(F)C(O)=CC=C1OC1=CC=CC=C1 UKXWEXICPBNEFO-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
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- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
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- 239000008280 blood Substances 0.000 description 1
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- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 1
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- NHADDZMCASKINP-HTRCEHHLSA-N decarboxydihydrocitrinin Natural products C1=C(O)C(C)=C2[C@H](C)[C@@H](C)OCC2=C1O NHADDZMCASKINP-HTRCEHHLSA-N 0.000 description 1
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- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
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- 239000003085 diluting agent Substances 0.000 description 1
- KWABLUYIOFEZOY-UHFFFAOYSA-N dioctyl butanedioate Chemical compound CCCCCCCCOC(=O)CCC(=O)OCCCCCCCC KWABLUYIOFEZOY-UHFFFAOYSA-N 0.000 description 1
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- 229910010272 inorganic material Inorganic materials 0.000 description 1
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- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 230000001418 larval effect Effects 0.000 description 1
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- 239000002609 medium Substances 0.000 description 1
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- 235000010981 methylcellulose Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
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- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
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- 239000002245 particle Substances 0.000 description 1
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- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
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- 239000002574 poison Substances 0.000 description 1
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- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229940080236 sodium cetyl sulfate Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- GGHPAKFFUZUEKL-UHFFFAOYSA-M sodium;hexadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCOS([O-])(=O)=O GGHPAKFFUZUEKL-UHFFFAOYSA-M 0.000 description 1
- NWZBFJYXRGSRGD-UHFFFAOYSA-M sodium;octadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCCCOS([O-])(=O)=O NWZBFJYXRGSRGD-UHFFFAOYSA-M 0.000 description 1
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- 238000003860 storage Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
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- 229910052623 talc Inorganic materials 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003559 thiocarbamic acid halides Chemical class 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- 150000005671 trienes Chemical class 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH530481 | 1981-08-17 | ||
| CH5304/81-2 | 1981-08-17 | ||
| CH4205/82-2 | 1982-07-09 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5839654A JPS5839654A (ja) | 1983-03-08 |
| JPH0258259B2 true JPH0258259B2 (enrdf_load_stackoverflow) | 1990-12-07 |
Family
ID=4291340
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14200382A Granted JPS5839654A (ja) | 1981-08-17 | 1982-08-16 | カルバミン酸エステル |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS5839654A (enrdf_load_stackoverflow) |
| GR (1) | GR76252B (enrdf_load_stackoverflow) |
| ZA (1) | ZA825794B (enrdf_load_stackoverflow) |
-
1982
- 1982-08-10 ZA ZA825794A patent/ZA825794B/xx unknown
- 1982-08-13 GR GR69035A patent/GR76252B/el unknown
- 1982-08-16 JP JP14200382A patent/JPS5839654A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5839654A (ja) | 1983-03-08 |
| ZA825794B (en) | 1983-06-29 |
| GR76252B (enrdf_load_stackoverflow) | 1984-08-04 |
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