JPS625938A - ２−（置換フエニル）−イソ吉草酸エステル - Google Patents
２−（置換フエニル）−イソ吉草酸エステルInfo
- Publication number
- JPS625938A JPS625938A JP28731285A JP28731285A JPS625938A JP S625938 A JPS625938 A JP S625938A JP 28731285 A JP28731285 A JP 28731285A JP 28731285 A JP28731285 A JP 28731285A JP S625938 A JPS625938 A JP S625938A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- isovalerate
- butynyl
- 2och
- ethoxyphenyl
- 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.)
- Granted
Links
- 150000002148 esters Chemical class 0.000 title abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title abstract description 3
- -1 carboxylic acid halide Chemical class 0.000 claims abstract description 14
- 125000005843 halogen group Chemical group 0.000 claims abstract description 8
- 239000002917 insecticide Substances 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 239000000126 substance Substances 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 22
- 239000002904 solvent Substances 0.000 abstract description 8
- YHYQPGONTMWSMP-UHFFFAOYSA-N 2-(4-ethoxyphenyl)-3-methylbutanoic acid Chemical compound CCOC1=CC=C(C(C(C)C)C(O)=O)C=C1 YHYQPGONTMWSMP-UHFFFAOYSA-N 0.000 abstract description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 3
- 239000002253 acid Substances 0.000 abstract description 3
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- 238000002360 preparation method Methods 0.000 abstract description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- LJXPWUAAAAXJBX-UHFFFAOYSA-N 2-methylallyl radical Chemical compound [CH2]C(C)=C LJXPWUAAAAXJBX-UHFFFAOYSA-N 0.000 abstract 1
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000003921 oil Substances 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- 230000000749 insecticidal effect Effects 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- ZCVAOQKBXKSDMS-AQYZNVCMSA-N (+)-trans-allethrin Chemical class CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(CC=C)C(=O)C1 ZCVAOQKBXKSDMS-AQYZNVCMSA-N 0.000 description 3
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 3
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241000238631 Hexapoda Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- VXSIXFKKSNGRRO-MXOVTSAMSA-N [(1s)-2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate;[(1s)-2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-3-[(e)-3-methoxy-2-methyl-3-oxoprop-1-enyl Chemical class CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1.CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VXSIXFKKSNGRRO-MXOVTSAMSA-N 0.000 description 3
- HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 description 3
- 229940070846 pyrethrins Drugs 0.000 description 3
- 239000002728 pyrethroid Substances 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- FMTFEIJHMMQUJI-NJAFHUGGSA-N 102130-98-3 Natural products CC=CCC1=C(C)[C@H](CC1=O)OC(=O)[C@@H]1[C@@H](C=C(C)C)C1(C)C FMTFEIJHMMQUJI-NJAFHUGGSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000257159 Musca domestica Species 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-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
- 241000607479 Yersinia pestis Species 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 229940024113 allethrin Drugs 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 1
- PKUXHMIREKJBJQ-UHFFFAOYSA-N 2-(3-bromo-4-ethoxyphenyl)-3-methylbutanoyl chloride Chemical compound CCOC1=CC=C(C(C(C)C)C(Cl)=O)C=C1Br PKUXHMIREKJBJQ-UHFFFAOYSA-N 0.000 description 1
- VIBRWYNSLBFAAO-UHFFFAOYSA-N 2-(4-ethoxy-3-fluorophenyl)-3-methylbutanoic acid Chemical compound CCOC1=CC=C(C(C(C)C)C(O)=O)C=C1F VIBRWYNSLBFAAO-UHFFFAOYSA-N 0.000 description 1
- DKKJLWHZHAEHQJ-UHFFFAOYSA-N 2-(4-ethoxy-3-fluorophenyl)-3-methylbutanoyl chloride Chemical compound CCOC1=CC=C(C(C(C)C)C(Cl)=O)C=C1F DKKJLWHZHAEHQJ-UHFFFAOYSA-N 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
- XLSOWZJLVSDNNL-UHFFFAOYSA-N 4-(4-chlorophenoxy)but-2-ynyl 2-(4-ethoxyphenyl)-3-methylbutanoate Chemical compound C1=CC(OCC)=CC=C1C(C(C)C)C(=O)OCC#CCOC1=CC=C(Cl)C=C1 XLSOWZJLVSDNNL-UHFFFAOYSA-N 0.000 description 1
- DZAYFSCAXTYXDZ-UHFFFAOYSA-N 4-methoxybut-2-ynyl 2-(4-ethoxyphenyl)-3-methylbutanoate Chemical compound CCOC1=CC=C(C(C(C)C)C(=O)OCC#CCOC)C=C1 DZAYFSCAXTYXDZ-UHFFFAOYSA-N 0.000 description 1
- VNQNBMHJMMDAGK-UHFFFAOYSA-N 4-prop-2-ynoxybut-2-ynyl 2-(3-bromo-4-ethoxyphenyl)-3-methylbutanoate Chemical compound CCOC1=CC=C(C(C(C)C)C(=O)OCC#CCOCC#C)C=C1Br VNQNBMHJMMDAGK-UHFFFAOYSA-N 0.000 description 1
- LDSDIPVWUWVMNL-UHFFFAOYSA-N 4-prop-2-ynoxybut-2-ynyl 2-(4-ethoxy-3-fluorophenyl)-3-methylbutanoate Chemical compound CCOC1=CC=C(C(C(C)C)C(=O)OCC#CCOCC#C)C=C1F LDSDIPVWUWVMNL-UHFFFAOYSA-N 0.000 description 1
- DSQRRDNQYCNBEK-UHFFFAOYSA-N 5-methylhex-5-en-2-ynyl 2-(4-ethoxyphenyl)-3-methylbutanoate Chemical compound CCOC1=CC=C(C(C(C)C)C(=O)OCC#CCC(C)=C)C=C1 DSQRRDNQYCNBEK-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 206010059866 Drug resistance Diseases 0.000 description 1
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N benzyl-alpha-carboxylic acid Natural products OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N beta-methyl-butyric acid Natural products CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- NEEDEQSZOUAJMU-UHFFFAOYSA-N but-2-yn-1-ol Chemical compound CC#CCO NEEDEQSZOUAJMU-UHFFFAOYSA-N 0.000 description 1
- YDQNYWDPQUFSDU-UHFFFAOYSA-N but-2-ynyl 2-(3,4-dichlorophenyl)-3-methylbutanoate Chemical compound CC#CCOC(=O)C(C(C)C)C1=CC=C(Cl)C(Cl)=C1 YDQNYWDPQUFSDU-UHFFFAOYSA-N 0.000 description 1
- IRQDJZWGYJCHPL-UHFFFAOYSA-N but-2-ynyl 2-(3-bromo-4-ethoxyphenyl)-3-methylbutanoate Chemical compound CCOC1=CC=C(C(C(C)C)C(=O)OCC#CC)C=C1Br IRQDJZWGYJCHPL-UHFFFAOYSA-N 0.000 description 1
- DYUUIZRAYBPXJG-UHFFFAOYSA-N but-2-ynyl 2-(3-chloro-4-ethoxyphenyl)-3-methylbutanoate Chemical compound CCOC1=CC=C(C(C(C)C)C(=O)OCC#CC)C=C1Cl DYUUIZRAYBPXJG-UHFFFAOYSA-N 0.000 description 1
- BNCXISZBBYUWNA-UHFFFAOYSA-N but-2-ynyl 2-(3-chloro-4-propan-2-yloxyphenyl)-3-methylbutanoate Chemical compound CC#CCOC(=O)C(C(C)C)C1=CC=C(OC(C)C)C(Cl)=C1 BNCXISZBBYUWNA-UHFFFAOYSA-N 0.000 description 1
- UYSGQLLXKSDXPI-UHFFFAOYSA-N but-2-ynyl 2-(3-fluoro-4-methoxyphenyl)-3-methylbutanoate Chemical compound COC1=CC=C(C(C(C)C)C(=O)OCC#CC)C=C1F UYSGQLLXKSDXPI-UHFFFAOYSA-N 0.000 description 1
- IZEIBJKYPDLUFB-UHFFFAOYSA-N but-2-ynyl 2-(4-ethoxy-3-fluorophenyl)-3-methylbutanoate Chemical compound CCOC1=CC=C(C(C(C)C)C(=O)OCC#CC)C=C1F IZEIBJKYPDLUFB-UHFFFAOYSA-N 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- JWHOQZUREKYPBY-UHFFFAOYSA-N rubonic acid Natural products CC1(C)CCC2(CCC3(C)C(=CCC4C5(C)CCC(=O)C(C)(C)C5CC(=O)C34C)C2C1)C(=O)O JWHOQZUREKYPBY-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/751,313 US4668815A (en) | 1984-07-06 | 1985-07-02 | Derivatives of phenylacetic ester, a process for producing the same and insecticidal compositions containing the same as an active ingredient |
| US751313 | 1985-07-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS625938A true JPS625938A (ja) | 1987-01-12 |
| JPH0347260B2 JPH0347260B2 (en, 2012) | 1991-07-18 |
Family
ID=25021449
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP28731285A Granted JPS625938A (ja) | 1985-07-02 | 1985-12-20 | ２−（置換フエニル）−イソ吉草酸エステル |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS625938A (en, 2012) |
-
1985
- 1985-12-20 JP JP28731285A patent/JPS625938A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0347260B2 (en, 2012) | 1991-07-18 |
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