JPS636539B2 - - Google Patents
Info
- Publication number
- JPS636539B2 JPS636539B2 JP54026837A JP2683779A JPS636539B2 JP S636539 B2 JPS636539 B2 JP S636539B2 JP 54026837 A JP54026837 A JP 54026837A JP 2683779 A JP2683779 A JP 2683779A JP S636539 B2 JPS636539 B2 JP S636539B2
- Authority
- JP
- Japan
- Prior art keywords
- active compound
- test
- solvent
- formula
- chlorine
- 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 100
- -1 pentafluorobenzyloxycarbonyl Chemical class 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- GXGJIOMUZAGVEH-UHFFFAOYSA-N Chamazulene Chemical group CCC1=CC=C(C)C2=CC=C(C)C2=C1 GXGJIOMUZAGVEH-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 239000003701 inert diluent Substances 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 3
- 150000001649 bromium compounds Chemical group 0.000 claims 1
- 239000003495 polar organic solvent Substances 0.000 claims 1
- 238000012360 testing method Methods 0.000 description 59
- 239000002904 solvent Substances 0.000 description 45
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- 238000002360 preparation method Methods 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
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- XDEPVFFKOVDUNO-UHFFFAOYSA-N pentafluorobenzyl bromide Chemical compound FC1=C(F)C(F)=C(CBr)C(F)=C1F XDEPVFFKOVDUNO-UHFFFAOYSA-N 0.000 description 4
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
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- 239000000969 carrier Substances 0.000 description 3
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 3
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
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- 239000007858 starting material Substances 0.000 description 3
- SJKVITNXHPKFTD-UHFFFAOYSA-N 3-(cyclobutylidenemethyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical class OC(=O)C1C(C)(C)C1C=C1CCC1 SJKVITNXHPKFTD-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
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- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
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- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
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- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
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- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
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- XLOPRKKSAJMMEW-UHFFFAOYSA-N chrysanthemic acid Chemical class CC(C)=CC1C(C(O)=O)C1(C)C XLOPRKKSAJMMEW-UHFFFAOYSA-N 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
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- 150000002148 esters Chemical class 0.000 description 2
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- ZFZXRNVTYVRULM-UHFFFAOYSA-N ethyl 3-formyl-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CCOC(=O)C1C(C=O)C1(C)C ZFZXRNVTYVRULM-UHFFFAOYSA-N 0.000 description 2
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- 159000000001 potassium salts Chemical class 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
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- ABDBJRNDNOSENP-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenyl)methyl 3-(cyclobutylidenemethyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound FC=1C(F)=C(F)C(F)=C(F)C=1COC(=O)C1C(C)(C)C1C=C1CCC1 ABDBJRNDNOSENP-UHFFFAOYSA-N 0.000 description 1
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- PGJYYCIOYBZTPU-UHFFFAOYSA-N 2,3,4,5,6-pentafluorobenzyl alcohol Chemical compound OCC1=C(F)C(F)=C(F)C(F)=C1F PGJYYCIOYBZTPU-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C69/753—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring of polycyclic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
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èš±è«æ±ã®ç¯å²ïŒèšèŒã®çµæç©ã
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782810634 DE2810634A1 (de) | 1978-03-11 | 1978-03-11 | Pentafluorbenzyloxycarbonylderivate, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS54128556A JPS54128556A (en) | 1979-10-05 |
| JPS636539B2 true JPS636539B2 (ja) | 1988-02-10 |
Family
ID=6034169
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2683779A Granted JPS54128556A (en) | 1978-03-11 | 1979-03-09 | Novel pentafluorobenzyloxycarbonyl derivative* its preparation and its use as insecticide and miticide |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4423066A (ja) |
| EP (1) | EP0004022B1 (ja) |
| JP (1) | JPS54128556A (ja) |
| AR (1) | AR223669A1 (ja) |
| AU (1) | AU521652B2 (ja) |
| BR (1) | BR7901463A (ja) |
| DE (2) | DE2810634A1 (ja) |
| DK (1) | DK161512C (ja) |
| IL (1) | IL56822A (ja) |
| ZA (1) | ZA791092B (ja) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2730515A1 (de) * | 1977-07-06 | 1979-01-18 | Bayer Ag | Substituierte phenoxybenzyloxycarbonylderivate, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide |
| GB2066810A (en) * | 1979-12-21 | 1981-07-15 | Ici Ltd | Fluorinated benzyl esters of cyclopropane carboxylic acids |
| DE3025218A1 (de) * | 1980-07-03 | 1982-02-11 | Bayer Ag, 5090 Leverkusen | 1-aryl-cyclopropan-1-carbonsaeureester, verfahren zu deren herstellung und deren verwendung in schaedlingsbekaempfungsmitteln |
| FR2494265A1 (fr) * | 1980-11-18 | 1982-05-21 | Roussel Uclaf | Nouveaux derives de l'acide cyclopropane carboxylique, leur procede de preparation et leur application a la preparation de compositions parfumantes |
| GB2094785B (en) * | 1981-01-21 | 1985-02-13 | Ici Plc | Halobenzyl esters |
| FR2539411B2 (fr) * | 1983-01-17 | 1986-04-25 | Roussel Uclaf | Nouveaux derives de l'acide cyclopropane carboxylique, leur procede de preparation, leur application a la lutte contre les parasites |
| FR2578250B1 (fr) * | 1985-03-01 | 1987-06-26 | Roussel Uclaf | Nouveaux esters derives de l'acide 2,2 dimethyl 3-ethenyl cyclopropane carboxylique, leur procede de preparation et leur application a la lutte contre les parasites |
| GB8626520D0 (en) * | 1986-11-06 | 1986-12-10 | Ici Plc | Halogenated esters |
| US8317845B2 (en) * | 2007-01-19 | 2012-11-27 | Alexa Medical, Llc | Screw and method of use |
| US7909882B2 (en) * | 2007-01-19 | 2011-03-22 | Albert Stinnette | Socket and prosthesis for joint replacement |
| PL2922401T3 (pl) * | 2012-11-23 | 2018-10-31 | Bayer Cropscience Ag | Zastosowanie zwiÄ zku zawierajÄ cego ugrupowanie polifluorobenzylowe przeciwko pluskwom odpornym na insektycydy |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3786052A (en) * | 1966-08-26 | 1974-01-15 | J Martel | Novel cyclopropanecarboxylic acids and esters |
| FR2271196A1 (en) | 1974-05-16 | 1975-12-12 | Aries Robert | Polychlorobenzyl chrysanthemate insecticides - especially 2,3,4,5,6-pentachlorobenzyl 3,3-dimethyl-2-isopropylidenemethyl-cyclopropane carboxylate |
| ZA775160B (en) * | 1976-08-27 | 1978-07-26 | Fmc Corp | Insecticidal styryl- and substituted-styrylcyclopropanecarboxylates |
| US4157397A (en) * | 1976-08-27 | 1979-06-05 | Fmc Corporation | Insecticidal (β-phenylvinyl)cyclopropanecarboxylates |
| US4160842A (en) * | 1976-08-27 | 1979-07-10 | Fmc Corporation | Insecticidal [β-(substituted-phenyl)vinyl]cyclopropanecarboxylates |
-
1978
- 1978-03-11 DE DE19782810634 patent/DE2810634A1/de not_active Withdrawn
-
1979
- 1979-02-21 US US06/013,660 patent/US4423066A/en not_active Expired - Lifetime
- 1979-02-26 EP EP79100577A patent/EP0004022B1/de not_active Expired
- 1979-02-26 DE DE7979100577T patent/DE2960797D1/de not_active Expired
- 1979-03-07 AU AU44893/79A patent/AU521652B2/en not_active Ceased
- 1979-03-08 IL IL56822A patent/IL56822A/xx unknown
- 1979-03-09 JP JP2683779A patent/JPS54128556A/ja active Granted
- 1979-03-09 AR AR275763A patent/AR223669A1/es active
- 1979-03-09 DK DK099779A patent/DK161512C/da not_active IP Right Cessation
- 1979-03-09 ZA ZA791092A patent/ZA791092B/xx unknown
- 1979-03-09 BR BR7901463A patent/BR7901463A/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA791092B (en) | 1980-05-28 |
| DK99779A (da) | 1979-09-12 |
| AU4489379A (en) | 1979-09-13 |
| DE2810634A1 (de) | 1979-09-20 |
| EP0004022B1 (de) | 1981-09-16 |
| DK161512C (da) | 1991-12-23 |
| IL56822A0 (en) | 1979-05-31 |
| US4423066A (en) | 1983-12-27 |
| EP0004022A1 (de) | 1979-09-19 |
| AU521652B2 (en) | 1982-04-22 |
| JPS54128556A (en) | 1979-10-05 |
| DE2960797D1 (en) | 1981-12-03 |
| AR223669A1 (es) | 1981-09-15 |
| IL56822A (en) | 1982-12-31 |
| DK161512B (da) | 1991-07-15 |
| BR7901463A (pt) | 1979-10-09 |
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