CH626320A5 - Process for the preparation of esters of cyclopropanecarboxylic acids and of optically active allethrolone, their use and insecticidal composition containing them - Google Patents
Process for the preparation of esters of cyclopropanecarboxylic acids and of optically active allethrolone, their use and insecticidal composition containing them Download PDFInfo
- Publication number
- CH626320A5 CH626320A5 CH1107077A CH1107077A CH626320A5 CH 626320 A5 CH626320 A5 CH 626320A5 CH 1107077 A CH1107077 A CH 1107077A CH 1107077 A CH1107077 A CH 1107077A CH 626320 A5 CH626320 A5 CH 626320A5
- Authority
- CH
- Switzerland
- Prior art keywords
- allethrolone
- dimethyl
- cyclopropane
- carboxylate
- mixture
- Prior art date
Links
- KZYVOZABVXLALY-UHFFFAOYSA-N 4-hydroxy-3-methyl-2-prop-2-enylcyclopent-2-en-1-one Chemical compound CC1=C(CC=C)C(=O)CC1O KZYVOZABVXLALY-UHFFFAOYSA-N 0.000 title claims description 115
- 239000000203 mixture Substances 0.000 title claims description 75
- 238000000034 method Methods 0.000 title claims description 49
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 title claims description 35
- 230000008569 process Effects 0.000 title claims description 26
- 150000002148 esters Chemical class 0.000 title claims description 17
- 238000002360 preparation method Methods 0.000 title claims description 12
- 230000000749 insecticidal effect Effects 0.000 title claims description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 138
- KZYVOZABVXLALY-QMMMGPOBSA-N (4s)-4-hydroxy-3-methyl-2-prop-2-enylcyclopent-2-en-1-one Chemical compound CC1=C(CC=C)C(=O)C[C@@H]1O KZYVOZABVXLALY-QMMMGPOBSA-N 0.000 claims description 67
- -1 alkyl radicals Chemical class 0.000 claims description 47
- 229950011148 cyclopropane Drugs 0.000 claims description 42
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims description 40
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 33
- 159000000000 sodium salts Chemical class 0.000 claims description 25
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 25
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 19
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- NSLLWJFTSBYHDX-UHFFFAOYSA-N 2-(2,2-difluoroethenyl)-1,1-dimethylcyclopropane Chemical compound CC1(C)CC1C=C(F)F NSLLWJFTSBYHDX-UHFFFAOYSA-N 0.000 claims description 15
- 239000003960 organic solvent Substances 0.000 claims description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 9
- IDVSZKGRCBMUQW-UHFFFAOYSA-N 2-(2,2-dichloroethenyl)-1,1-dimethylcyclopropane Chemical compound CC1(C)CC1C=C(Cl)Cl IDVSZKGRCBMUQW-UHFFFAOYSA-N 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
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- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 4
- 150000001721 carbon Chemical group 0.000 claims description 4
- 150000003254 radicals Chemical group 0.000 claims description 4
- 239000012429 reaction media Substances 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
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- 239000002917 insecticide Substances 0.000 claims description 3
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 3
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 150000001942 cyclopropanes Chemical class 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- 239000012074 organic phase Substances 0.000 description 20
- 239000000047 product Substances 0.000 description 20
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 239000002253 acid Substances 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 239000000284 extract Substances 0.000 description 16
- 239000000843 powder Substances 0.000 description 15
- 239000008346 aqueous phase Substances 0.000 description 14
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 14
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 238000002983 circular dichroism Methods 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- 238000010908 decantation Methods 0.000 description 11
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
- 238000003197 gene knockdown Methods 0.000 description 10
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 9
- 239000012141 concentrate Substances 0.000 description 9
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 9
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- 241000238631 Hexapoda Species 0.000 description 8
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- 230000005494 condensation Effects 0.000 description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 8
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- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
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- JKPDFYUIUGBVOW-UHFFFAOYSA-N 2,2-difluoroethenyl cyclopropanecarboxylate Chemical compound FC(F)=COC(=O)C1CC1 JKPDFYUIUGBVOW-UHFFFAOYSA-N 0.000 description 1
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- 150000007530 organic bases Chemical class 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 238000003307 slaughter Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000012747 synergistic agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH44181A CH626868A5 (en) | 1977-09-09 | 1981-01-23 | Esters of optically active allethrolone and cyclopropanecarboxylic acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7627288A FR2364199A1 (fr) | 1976-09-10 | 1976-09-10 | Procede de preparation d'esters d'acide cyclopropane carboxyliques d'allethrolone optiquement active au depart d'allethrolone de configuration antipodale |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH626320A5 true CH626320A5 (en) | 1981-11-13 |
Family
ID=9177574
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1107077A CH626320A5 (en) | 1976-09-10 | 1977-09-09 | Process for the preparation of esters of cyclopropanecarboxylic acids and of optically active allethrolone, their use and insecticidal composition containing them |
Country Status (23)
| Country | Link |
|---|---|
| JP (1) | JPS5334756A (en]) |
| AU (1) | AU512196B2 (en]) |
| BE (1) | BE858555A (en]) |
| BR (1) | BR7706029A (en]) |
| CH (1) | CH626320A5 (en]) |
| DE (1) | DE2740701C2 (en]) |
| DK (1) | DK158655C (en]) |
| EG (1) | EG13016A (en]) |
| ES (1) | ES462242A1 (en]) |
| FR (1) | FR2364199A1 (en]) |
| GB (1) | GB1583600A (en]) |
| GR (1) | GR71905B (en]) |
| HU (1) | HU177736B (en]) |
| IE (1) | IE45486B1 (en]) |
| IL (1) | IL52785A (en]) |
| IT (1) | IT1091136B (en]) |
| LU (1) | LU78102A1 (en]) |
| NL (1) | NL188690C (en]) |
| PH (1) | PH21134A (en]) |
| PT (1) | PT67015B (en]) |
| SE (1) | SE437152B (en]) |
| SU (2) | SU1178310A3 (en]) |
| ZA (1) | ZA775153B (en]) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2247140A5 (en]) * | 1973-10-06 | 1975-05-02 | Bosch Gmbh Robert | |
| JPS6328731U (en]) * | 1986-08-08 | 1988-02-25 | ||
| JPS6443126U (en]) * | 1987-09-10 | 1989-03-15 | ||
| JP5892105B2 (ja) | 2013-04-12 | 2016-03-23 | 株式会社デンソー | Ａ／ｆセンサ素子及びその製造方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EG14503A (en) * | 1973-04-21 | 1983-12-31 | Sumitomo Chemical Co | Novel insecticidal composition |
| JPS533384B2 (en]) * | 1974-01-25 | 1978-02-06 |
-
1976
- 1976-09-10 FR FR7627288A patent/FR2364199A1/fr active Granted
-
1977
- 1977-08-01 SE SE7708768A patent/SE437152B/xx not_active IP Right Cessation
- 1977-08-22 IL IL52785A patent/IL52785A/xx unknown
- 1977-08-25 ZA ZA00775153A patent/ZA775153B/xx unknown
- 1977-08-26 PH PH20168A patent/PH21134A/en unknown
- 1977-09-07 EG EG515/77A patent/EG13016A/xx active
- 1977-09-08 GR GR54321A patent/GR71905B/el unknown
- 1977-09-08 HU HU77RO940A patent/HU177736B/hu not_active IP Right Cessation
- 1977-09-08 PT PT67015A patent/PT67015B/pt unknown
- 1977-09-09 AU AU28694/77A patent/AU512196B2/en not_active Expired
- 1977-09-09 BE BE180787A patent/BE858555A/xx not_active IP Right Cessation
- 1977-09-09 IT IT50957/77A patent/IT1091136B/it active
- 1977-09-09 NL NLAANVRAGE7709966,A patent/NL188690C/xx not_active IP Right Cessation
- 1977-09-09 CH CH1107077A patent/CH626320A5/fr not_active IP Right Cessation
- 1977-09-09 ES ES462242A patent/ES462242A1/es not_active Expired
- 1977-09-09 DK DK401677A patent/DK158655C/da not_active IP Right Cessation
- 1977-09-09 LU LU78102A patent/LU78102A1/xx unknown
- 1977-09-09 JP JP10800477A patent/JPS5334756A/ja active Granted
- 1977-09-09 GB GB37781/77A patent/GB1583600A/en not_active Expired
- 1977-09-09 DE DE2740701A patent/DE2740701C2/de not_active Expired
- 1977-09-09 BR BR7706029A patent/BR7706029A/pt unknown
- 1977-09-09 IE IE1869/77A patent/IE45486B1/en unknown
-
1978
- 1978-06-30 SU SU782631494A patent/SU1178310A3/ru active
-
1987
- 1987-10-27 SU SU874203530A patent/SU1713436A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| BR7706029A (pt) | 1978-06-06 |
| DE2740701A1 (de) | 1978-03-16 |
| PT67015A (fr) | 1977-10-01 |
| DK158655C (da) | 1991-01-14 |
| ZA775153B (en) | 1978-09-27 |
| GB1583600A (en) | 1981-01-28 |
| SE7708768L (sv) | 1978-03-11 |
| IE45486B1 (en) | 1982-09-08 |
| SU1178310A3 (ru) | 1985-09-07 |
| NL7709966A (nl) | 1978-03-14 |
| IL52785A (en) | 1982-11-30 |
| FR2364199A1 (fr) | 1978-04-07 |
| JPS6238345B2 (en]) | 1987-08-17 |
| JPS5334756A (en) | 1978-03-31 |
| DE2740701C2 (de) | 1987-03-26 |
| IT1091136B (it) | 1985-06-26 |
| EG13016A (en) | 1980-07-31 |
| SE437152B (sv) | 1985-02-11 |
| HU177736B (en) | 1981-12-28 |
| NL188690C (nl) | 1992-09-01 |
| IL52785A0 (en) | 1977-10-31 |
| DK158655B (da) | 1990-07-02 |
| AU2869477A (en) | 1979-03-15 |
| NL188690B (nl) | 1992-04-01 |
| BE858555A (fr) | 1978-03-09 |
| LU78102A1 (en]) | 1978-06-01 |
| FR2364199B1 (en]) | 1979-10-12 |
| GR71905B (en]) | 1983-08-11 |
| DK401677A (da) | 1978-03-11 |
| PH21134A (en) | 1987-07-27 |
| SU1713436A3 (ru) | 1992-02-15 |
| AU512196B2 (en) | 1980-09-25 |
| ES462242A1 (es) | 1978-06-01 |
| IE45486L (en) | 1978-03-10 |
| PT67015B (fr) | 1979-09-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |