NO763934L - - Google Patents
Info
- Publication number
- NO763934L NO763934L NO763934A NO763934A NO763934L NO 763934 L NO763934 L NO 763934L NO 763934 A NO763934 A NO 763934A NO 763934 A NO763934 A NO 763934A NO 763934 L NO763934 L NO 763934L
- Authority
- NO
- Norway
- Prior art keywords
- group
- lower alkyl
- hydrogen atom
- phenyl
- carboxylate
- Prior art date
Links
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- USPVNSDVCUTNJN-UHFFFAOYSA-N ethenyl cyclopropanecarboxylate Chemical compound C=COC(=O)C1CC1 USPVNSDVCUTNJN-UHFFFAOYSA-N 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000003435 aroyl group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 125000003368 amide group Chemical group 0.000 claims 2
- 125000002560 nitrile group Chemical group 0.000 claims 2
- YMGUBTXCNDTFJI-UHFFFAOYSA-M cyclopropanecarboxylate Chemical compound [O-]C(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-M 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 238000006798 ring closing metathesis reaction Methods 0.000 claims 1
- 239000002917 insecticide Substances 0.000 description 7
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 6
- 239000002728 pyrethroid Substances 0.000 description 6
- VQXSOUPNOZTNAI-UHFFFAOYSA-N Pyrethrin I Natural products CC(=CC1CC1C(=O)OC2CC(=O)C(=C2C)CC=C/C=C)C VQXSOUPNOZTNAI-UHFFFAOYSA-N 0.000 description 5
- -1 dimethyl-vinyl group Chemical group 0.000 description 5
- ROVGZAWFACYCSP-VUMXUWRFSA-N pyrethrin I Chemical compound 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 ROVGZAWFACYCSP-VUMXUWRFSA-N 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000002367 halogens Chemical group 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 description 2
- LTNDZDRYUXNFCU-NEWSRXKRSA-N Cinerin II Natural products CC=CCC1=C(C)[C@H](CC1=O)OC(=O)[C@@H]2[C@@H](C=C(C)OC(=O)C)C2(C)C LTNDZDRYUXNFCU-NEWSRXKRSA-N 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 241001608567 Phaedon cochleariae Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 241000250966 Tanacetum cinerariifolium Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000003158 alcohol group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 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
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000001589 carboacyl group Chemical group 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- SHCRDCOTRILILT-WOBDGSLYSA-N cinerin II Chemical compound 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(=O)C1 SHCRDCOTRILILT-WOBDGSLYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical group OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- ORVPAYHEPQBFFC-UHFFFAOYSA-N ethyl 3-ethenyl-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CCOC(=O)C1C(C=C)C1(C)C ORVPAYHEPQBFFC-UHFFFAOYSA-N 0.000 description 2
- WLLVIDYONYJCTH-UHFFFAOYSA-N ethyl 6-bromo-2,3,3-trimethylhex-4-enoate Chemical compound CCOC(=O)C(C)C(C)(C)C=CCBr WLLVIDYONYJCTH-UHFFFAOYSA-N 0.000 description 2
- NNVHQXPXPLWGML-UHFFFAOYSA-N ethyl 6-bromo-3,3-dimethylhex-4-enoate Chemical compound CCOC(=O)CC(C)(C)C=CCBr NNVHQXPXPLWGML-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- WKNSDDMJXANVMK-XIGJTORUSA-N jasmolin II Chemical compound C1C(=O)C(C\C=C/CC)=C(C)[C@H]1OC(=O)[C@H]1C(C)(C)[C@@H]1\C=C(/C)C(=O)OC WKNSDDMJXANVMK-XIGJTORUSA-N 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 229930014626 natural product Natural products 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 2
- 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 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 241000723353 Chrysanthemum Species 0.000 description 1
- 235000007516 Chrysanthemum Nutrition 0.000 description 1
- FMTFEIJHMMQUJI-UHFFFAOYSA-N Cinerin I Natural products C1C(=O)C(CC=CC)=C(C)C1OC(=O)C1C(C)(C)C1C=C(C)C FMTFEIJHMMQUJI-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- NZKIRHFOLVYKFT-UHFFFAOYSA-N Jasmolin I Natural products C1C(=O)C(CC=CCC)=C(C)C1OC(=O)C1C(C)(C)C1C=C(C)C NZKIRHFOLVYKFT-UHFFFAOYSA-N 0.000 description 1
- 206010058667 Oral toxicity Diseases 0.000 description 1
- 235000017372 Piretro di Dalmazia Nutrition 0.000 description 1
- VMORCWYWLVLMDG-YZGWKJHDSA-N Pyrethrin-II Natural products CC(=O)OC(=C[C@@H]1[C@H](C(=O)O[C@H]2CC(=O)C(=C2C)CC=CC=C)C1(C)C)C VMORCWYWLVLMDG-YZGWKJHDSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- ROVGZAWFACYCSP-MQBLHHJJSA-N [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 Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(C\C=C/C=C)C(=O)C1 ROVGZAWFACYCSP-MQBLHHJJSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- FMTFEIJHMMQUJI-DFKXKMKHSA-N cinerin I Chemical compound C1C(=O)C(C\C=C/C)=C(C)[C@H]1OC(=O)[C@H]1C(C)(C)[C@@H]1C=C(C)C FMTFEIJHMMQUJI-DFKXKMKHSA-N 0.000 description 1
- 150000001942 cyclopropanes Chemical class 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- XXCGAENPCKWVAA-UHFFFAOYSA-N ethyl 3-ethenyl-1,2,2-trimethylcyclopropane-1-carboxylate Chemical compound CCOC(=O)C1(C)C(C=C)C1(C)C XXCGAENPCKWVAA-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- NZKIRHFOLVYKFT-VUMXUWRFSA-N jasmolin I Chemical compound C1C(=O)C(C\C=C/CC)=C(C)[C@H]1OC(=O)[C@H]1C(C)(C)[C@@H]1C=C(C)C NZKIRHFOLVYKFT-VUMXUWRFSA-N 0.000 description 1
- WKNSDDMJXANVMK-UHFFFAOYSA-N jasmolin II Natural products C1C(=O)C(CC=CCC)=C(C)C1OC(=O)C1C(C)(C)C1C=C(C)C(=O)OC WKNSDDMJXANVMK-UHFFFAOYSA-N 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 231100000418 oral toxicity Toxicity 0.000 description 1
- 238000005949 ozonolysis reaction Methods 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- VJFUPGQZSXIULQ-XIGJTORUSA-N pyrethrin II Chemical compound 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 VJFUPGQZSXIULQ-XIGJTORUSA-N 0.000 description 1
- 229940015367 pyrethrum Drugs 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 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)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO763934A NO763934L (enrdf_load_html_response) | 1974-09-10 | 1976-11-18 |
Applications Claiming Priority (20)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10352174A JPS5141316A (en) | 1974-09-10 | 1974-09-10 | Ganmaa harokarubonsanesuterunoseizohoho |
| JP10352074A JPS5545062B2 (enrdf_load_html_response) | 1974-09-10 | 1974-09-10 | |
| JP10997674A JPS5139624A (en) | 1974-09-26 | 1974-09-26 | Ganmaa fuhowa epushiron harokarubonsanesuteru no seizoho |
| JP10997574A JPS5545063B2 (enrdf_load_html_response) | 1974-09-26 | 1974-09-26 | |
| JP13663174A JPS5165734A (ja) | 1974-11-30 | 1974-11-30 | Shikuropuropankarubonsanesuteruo seizosuru hoho |
| JP13663274A JPS5165710A (en) | 1974-11-30 | 1974-11-30 | Ganma fuhowakarubonsanesuteruno seizohoho |
| JP13702674A JPS5165735A (ja) | 1974-12-02 | 1974-12-02 | Shikuropuropankarubonsanesuteruo seizosuru hoho |
| JP13775274A JPS5165714A (en) | 1974-12-03 | 1974-12-03 | Ganma fuhowa ipushiron harokarubonsanesuteruo seizosuru hoho |
| JP50006429A JPS5182216A (en) | 1975-01-16 | 1975-01-16 | Ganma harokarubonsanesuteruno seizoho |
| JP50008673A JPS5817735B2 (ja) | 1975-01-22 | 1975-01-22 | ガンマ − フホウワカルボンサンエステルノセイホウ |
| JP1238975A JPS5821901B2 (ja) | 1975-01-31 | 1975-01-31 | ２−（２，２−ジクロルビニル）−３，３−ジメチルシクロプロパンカルボン酸エステルの製造方法 |
| JP50019918A JPS5198213A (en) | 1975-02-19 | 1975-02-19 | arufua chikan ganma harokarubonsanesuteruno seizohoho |
| JP1991775A JPS5821902B2 (ja) | 1975-02-19 | 1975-02-19 | アルフア− チカンシクロプロパンカルボンサンエステルノ セイゾウホウホウ |
| JP50021857A JPS5198248A (enrdf_load_html_response) | 1975-02-24 | 1975-02-24 | |
| JP50028606A JPS5817451B2 (ja) | 1975-03-11 | 1975-03-11 | γ↓−クロル↓−δ↓−不飽和カルボン酸エステルの製法 |
| JP50028607A JPS5822463B2 (ja) | 1975-03-11 | 1975-03-11 | チカンビニルキオユウスル シクロプロパンカルボンサンユウドウタイノセイホウ |
| JP6659375A JPS5828263B2 (ja) | 1975-06-04 | 1975-06-04 | ３ ３− ジメチル −２−（２ ２− ジハロビニル ） シクロプロパンカルボンサンエステルノ セイゾウホウホウ |
| JP50066592A JPS5819661B2 (ja) | 1975-06-04 | 1975-06-04 | ガンマ− − ハロ−カルボンサンエステルノ セイゾウホウホウ |
| NO75753085A NO147792C (no) | 1974-09-10 | 1975-09-09 | Fremgangsmaate for fremstilling av estere av dihalogen-vinylcyklopropankarboksylsyrer |
| NO763934A NO763934L (enrdf_load_html_response) | 1974-09-10 | 1976-11-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO763934L true NO763934L (enrdf_load_html_response) | 1976-03-11 |
Family
ID=27586372
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO763934A NO763934L (enrdf_load_html_response) | 1974-09-10 | 1976-11-18 |
Country Status (1)
| Country | Link |
|---|---|
| NO (1) | NO763934L (enrdf_load_html_response) |
-
1976
- 1976-11-18 NO NO763934A patent/NO763934L/no unknown
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