KR840008645A - 2,2-디메틸-3-(2-할로게노-비닐)-사이클로프로판 카복실산에스테르의 제조방법 - Google Patents
2,2-디메틸-3-(2-할로게노-비닐)-사이클로프로판 카복실산에스테르의 제조방법 Download PDFInfo
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- KR840008645A KR840008645A KR1019840001828A KR840001828A KR840008645A KR 840008645 A KR840008645 A KR 840008645A KR 1019840001828 A KR1019840001828 A KR 1019840001828A KR 840001828 A KR840001828 A KR 840001828A KR 840008645 A KR840008645 A KR 840008645A
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- 229920002554 vinyl polymer Polymers 0.000 title claims 5
- 238000000034 method Methods 0.000 title claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 23
- 125000004432 carbon atom Chemical group C* 0.000 claims 15
- 125000001188 haloalkyl group Chemical group 0.000 claims 14
- -1 2-pyridinyl Chemical group 0.000 claims 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 12
- 229910052801 chlorine Inorganic materials 0.000 claims 12
- 239000000460 chlorine Substances 0.000 claims 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 11
- 229910052794 bromium Inorganic materials 0.000 claims 11
- 229910052731 fluorine Inorganic materials 0.000 claims 10
- 239000011737 fluorine Substances 0.000 claims 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 9
- 150000001875 compounds Chemical class 0.000 claims 7
- 125000005843 halogen group Chemical group 0.000 claims 7
- 125000003107 substituted aryl group Chemical group 0.000 claims 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 239000001301 oxygen Substances 0.000 claims 6
- 229910052717 sulfur Chemical group 0.000 claims 6
- 239000011593 sulfur Chemical group 0.000 claims 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 claims 1
- RNDVGJZUHCKENF-UHFFFAOYSA-N 5-hexen-2-one Chemical compound CC(=O)CCC=C RNDVGJZUHCKENF-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 229910001413 alkali metal ion Inorganic materials 0.000 claims 1
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 claims 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 claims 1
- 230000002140 halogenating effect Effects 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 239000002728 pyrethroid Substances 0.000 claims 1
- 229910052709 silver Inorganic materials 0.000 claims 1
- 239000004332 silver Substances 0.000 claims 1
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims 1
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- 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
- C07C69/743—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 acids with a three-membered ring and with unsaturation outside the ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/16—Unsaturated compounds
- C07C61/40—Unsaturated compounds containing halogen
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- 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
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
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- C07C47/24—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing halogen
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/227—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing halogen
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Abstract
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Claims (6)
- 일반식(Ⅱ)의 2,2-디메틸-3-(2-할로게노-비닐)-사이클로프로판 카복실산 또는 이의 반응성 유도체를, 적절하게는 산수용체 존재하에, 적절하게는 촉매존재하에 및 적절하게는 희석제 존재하에 일반식(Ⅲ)의 알코올 또는 이의 반응성 유도체와 반응시킴을 특징으로 하여, 일반식(Ⅰ)의 2,2-디메틸-3-(2-할로게노-비닐)-사이클로프로판 카복실산 에스테르를 제조하는 방법.상기식에서 R1및 R2는 동일 또는 상이하며, 알킬 또는 할로게노알킬이고, R3는 알킬 또는 그룹-(CH2)nR4이며, n은 0 또는 1이고 R4는 할로게노 알킬, 임의로 치환된 아릴 또는 그룹-XR5이며, X는 산소 또는 황이고, R5는 알킬, 할로게노알킬, 임의로 치환된 아릴 또는 임의로 치환된 아르알킬이며, Hal은 불소, 또는 브롬이고, R는 피레트로이드의 경우에 사용될 수 있는 알코올기이는.
- 제1항에 있어서, R1및 R2는 동일 또는 상이하며, 탄소수 1 내지 6의 알킬, 또는 알킬부 위에 1 내지 4개의 탄소원자를 함유하고 1 내지 5개의 동일 또는 상이한 할로겐원자(예:불소, 염소 및/또는 브롬)를 함유하는 할로게노 알킬이고, R3는 탄소수 1내지 12의 알팀 또는 그룹-(CH2)nR4이며, n는 0 또는 1이고, R4는 알킬부 위에 1 내지 4개의 탄소원자를 함유하고 1 내지 5의 동일 또는 상이한 할로겐원자를 함유하는 할로게노알킬, 탄소수 6 내지 10의 임의로 치환된 아릴(예:나프틸 또는 페닐, 바람직하게는 페닐), 또는 그룹-XR5이며, X는 산소 또는 황이고, R5는 탄소수 1 내지 6의 알킬, 1 내지 4개의 탄소원자 및 1내지 5개의 동일 또는 상이한 할로겐 원자를 함유하는 할로게노알킬, 또는 탄소수 6 내지 10의 아릴, 및 아릴부위에 6 내지 10개의 탄소원자를 함유하고 알킬부위에 1 또는 2개의 탄소원자를 함유하는 아르알킬[아릴 또는 아르알킬은 각각 1 내지 4개의 탄소원자를 함유하는 알킬, 알콕시 및 알킬티오, 각각 1내지 4개의 탄소원자및 1 내지 5개의 동일 또는 상이한 할로겐 원자를 함유하는 할로게노알킬, 할로게노알콕시 및 할로게노알킬티오, 및/또는 할로겐(예: 불소, 염서 및/또는 브롬)에 의해 임의 치환됨이고, Hal은 불소, 염소 또는 브롬이며, R은 기-CHR6R7이고, R6은 수소, 시아노 또는 탄소수 2 내지 4의 임의로 치환된 알케닐 또는 알키닐이며, R7은 페닐 또는 2-피리디닐(이들은 각각 할로겐 및/또는 할로겐, 알킬 또는 할로게노 알킬에 의해 치환되는 페녹시에 의해 치환됨)인 일반식(Ⅰ)의 화합물을 제조하는 방법.
- 제1항에 있어서, R1및 R2는 동일 또는 상이하며, 탄소수 1 내지 4의 알킬, 또는 알킬부위에 1 내지 2개의 탄소원자를 함유하고 1내지 3개의 동일 또는 상이한 할로겐 원자(예:불소 및/또는 염소)를 함유하는 할로게노 알킬이며, R3는 탄소수 1 내지 6의 알킬 또는 그룹-(CH2)nR4이고, n는 0 또는 1이며, R4는 알킬부위에 1 내지 4개의 탄소원자를 함유하며 1 내지 5개의 동일 또는 상이한 할로겐원자를 함유하는 할로게노알킬, 임의로 치환된 페닐 또는 그룹-XR5이고, X는 산소 또는 황이며, R5는 탄소수 1 내지 4의 알킬 1 내지 4개의 탄소원자 및 1내지 5개의 동일 또는 상이한 할로겐원자를 함유하는 할로게노알킬, 또는 페닐 또는 알킬부위에 1 또는 2개의 탄소원자를 함유하는 페닐알킬(페닐 또는 페닐알킬은 불소, 염소, 메틸, 3급-부틸,메톡시,메틸티오,트리플루오로메틸 및/또는 트리플루오로메톡시에 의해 임의치환된다)이고, Hal은 염소 또는 브롬이며, R는 기-CHR6R7이고, R6는 수소 또는 시아노이며, R7은 3-페녹시, 4-페닐플루오로-3-페녹시-페닐, 3-(4-플루오로-페녹시)-페닐, 4-플루오로-3-(4-플루오르-페녹시)-페닐, 펜타플루오로-페닐, 또는 6-페녹시-2-피리딜인 일반식(Ⅰ)의 화합물을 제조하는 방법.
- 제1항에 있어서, R1및R2는 동일 또는 상이하며, 메틸, 에틸, 클로로메틸, 클로로에틸, 플루오로메틸 또는 플루오로 에틸이며, R3는 메틸, 에틸, n-프로필, i-프로필, n-부틸, n-펜틸, n-헥실 또는 그룹-(CH2)nR4이고, n는 0 또는 1이며, R4는 클로로메틸, 플루오로메틸, 페닐(페닐은 불소, 염소, 브롬, 메틸메톡시, 트리플루오로메틸, 또는 트리플루오로메톡시에 의해 임의 치환된다),또는 그룹 R5이고, X는 산소 또는 황이며, XR5는 메틸, 에틸, 트리플루오로메틸, 트리클로로메틸, 또는 페닐 또는 벤질(페닐 또는 벤질은 불소, 염소, 브롬, 메틸, 메톡시, 트리플루오로메틸 및/또는 트리플루오로메톡시에 의해 임의 치환된다)이고, Hal은 염소이며,R은-CHR6R7이고, R6은 수소 또는 시아노이며, R7은 3-페녹시-페닐, 4-플루오로-3-페녹시-페닐 또는 펜타플루오로페닐인 일반식(Ⅰ)의 화합물을 제조하는 방법.
- 일반식(Ⅵ)의 비닐-알데히드를 할로겐화수소산 존재하에 일반식(Ⅶ)의 메틸-부탄-3-은과 반응시키고, 생성된 일반식(Ⅷ)의 4,4-디메틸-3-할로게노-1-헥센-5-온을 할로겐화시키고, 수득된 일반식(Ⅸ)의 화합물을 일반식(Ⅹ)의 염기와 반응시키며, 적절하게는 생성된 산, 에스테르 또는 염으로부터 산 할라이드를 제조함을 특징으로 하여, 일반식(Ⅱb)의 2,2-디메틸-3-(2-할로게노-비닐) 사이클로프로판-카복실산 및 이의 유도체를 제조하는 방법.상기식에서 R1및 R2는 동일 또는 상이하며 알킬 또는 할로게노알킬이고 R3는 알킬 또는 그룹-(CH2)nR4이며, n는 0 또는 1이고, R⁴는 할로게노알킬, 임의로 치환된 아릴, 또는 그룹-XR5이며, X는 산소 또는 황이고 R5는 알킬, 할로게노알킬, 임의로 치환된 아릴 또는 임의로 치환된 아르알킬이며, Hal은 불소, 염소, 또는 브롬이고, Hal1및 Hal2각각은 염소 또는 브롬이며, W는 OH, 할로겐 또는 C1-C4-알콕시이고 M은 1당량의 알카리금속 또는 알카리토금속 이온이며, Z는 수소 또는 C1-C4-일킬이다.
- 일반식(Ⅵ)의 비닐 알데히드를 할로겐화수소산 존재하에 일반식(Ⅶ)의 메틸부타논과 반응시킴을 특징으로 하여 일반식(Ⅷ)의 화합물을 제조하는 방법.상기식에서 R1및 R2는 동일 또는 상이하며 알킬 또는 할로게노알킬이고 R3는 알킬 또는 그룹-(CH2)nR4이며, n는 0 또는 1이고, R4는 할로게노알킬, 임의로 치환된 아릴, 또는 그룹-XR5이며, X는 산소 또는 황이고, R5는 알킬, 할로게노알킬, 임의로 치환된 아릴 또는 임의로 치환된 아르알킬이며, Hal은 불소, 염소 또는 브롬이고, Hal1은 염소 또는 브롬이다.※ 참고사항 : 최초출원내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3312543A DE3312543A1 (de) | 1983-04-07 | 1983-04-07 | 2,2-dimethyl-3-(2-halogen-vinyl)-cyclopropancarbonsaeureester, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel |
| DEP3312543.0 | 1983-04-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR840008645A true KR840008645A (ko) | 1984-12-17 |
Family
ID=6195695
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019840001828A KR840008645A (ko) | 1983-04-07 | 1984-04-07 | 2,2-디메틸-3-(2-할로게노-비닐)-사이클로프로판 카복실산에스테르의 제조방법 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4582856A (ko) |
| EP (1) | EP0121847B1 (ko) |
| JP (1) | JPS59196837A (ko) |
| KR (1) | KR840008645A (ko) |
| AT (1) | ATE24895T1 (ko) |
| DE (2) | DE3312543A1 (ko) |
| DK (1) | DK182584A (ko) |
| HU (1) | HU195184B (ko) |
| IL (1) | IL71438A (ko) |
| ZA (1) | ZA842575B (ko) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1269994A (en) * | 1985-04-05 | 1990-06-05 | Noritada Matsuo | Method for producing cyclopropanecarboxylic acid derivatives |
| NZ221534A (en) * | 1986-08-27 | 1990-10-26 | Montedison Spa | Derivatives of 2,2-dimethyl-cyclopropane carboxylic acid; insecticides and acaricides |
| FR2628103B1 (fr) * | 1988-03-03 | 1991-06-14 | Roussel Uclaf | Nouveaux esters pyrethrinoides portant un noyau indanyle, leur procede de preparation et leur application comme pesticides |
| US5238957A (en) * | 1988-07-07 | 1993-08-24 | Presidenza Del Consiglio Dei Ministri-Uffico Del Ministro Per Il Coordinamento Delle Iniziative Per La Ricerca Scientifica E Tecnologica | Esters of 2,2-dimethyl-cyclopropane-carboxylic acid |
| DE3900275A1 (de) * | 1989-01-07 | 1990-07-12 | Basf Ag | Substituierte cyclopropancarbonsaeurepropargylester, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von schaedlingen |
| CA2166450C (en) * | 1995-01-20 | 2008-03-25 | Ronald Salovey | Chemically crosslinked ultrahigh molecular weight polyethylene for artificial human joints |
| JP2000514481A (ja) * | 1996-07-09 | 2000-10-31 | ザ オーソピーディック ホスピタル | 放射線及び熱処理を用いた低摩耗ポリエチレンの架橋 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4183942A (en) * | 1976-08-27 | 1980-01-15 | Fmc Corporation | Insecticidal (β-phenyl-β-substituted-vinyl)cyclopropanecarboxylates |
| US4200644A (en) * | 1978-01-26 | 1980-04-29 | Fmc Corporation | Arylthiovinylcyclopropanecarboxylate insecticides |
| DE2842541A1 (de) * | 1978-09-29 | 1980-05-22 | Bayer Ag | Fluoralkenylsubstituierte cyclopropancarbonsaeureester und ihre verwendung als insektizide |
| DE2939913A1 (de) * | 1979-10-02 | 1981-04-30 | Bayer Ag, 5090 Leverkusen | 3-(2,3-dichlor-3,3-difluor-prop-1-en-1-yl)-2,2-dimethyl-cyclopropancarbonsaeure-fluor-benzylester, verfahren zu ihrer herstellung sowie ihre verwendung in schaedlingsbekaempfungsmitteln |
| DE3361336D1 (en) * | 1982-05-05 | 1986-01-09 | Bayer Ag | Process for the preparation of 3-vinyl-substituted 2,2-dimethyl-cyclopropane-1-carboxylic acids or their esters, and intermediate products therefor |
-
1983
- 1983-04-07 DE DE3312543A patent/DE3312543A1/de not_active Withdrawn
-
1984
- 1984-03-20 US US06/591,661 patent/US4582856A/en not_active Expired - Fee Related
- 1984-03-26 AT AT84103291T patent/ATE24895T1/de not_active IP Right Cessation
- 1984-03-26 EP EP84103291A patent/EP0121847B1/de not_active Expired
- 1984-03-26 DE DE8484103291T patent/DE3462033D1/de not_active Expired
- 1984-04-04 IL IL71438A patent/IL71438A/xx unknown
- 1984-04-05 ZA ZA842575A patent/ZA842575B/xx unknown
- 1984-04-06 HU HU841366A patent/HU195184B/hu not_active IP Right Cessation
- 1984-04-06 DK DK182584A patent/DK182584A/da not_active Application Discontinuation
- 1984-04-06 JP JP59067816A patent/JPS59196837A/ja active Pending
- 1984-04-07 KR KR1019840001828A patent/KR840008645A/ko not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0121847A2 (de) | 1984-10-17 |
| DK182584A (da) | 1984-10-08 |
| IL71438A0 (en) | 1984-07-31 |
| DK182584D0 (da) | 1984-04-06 |
| DE3462033D1 (en) | 1987-02-19 |
| EP0121847B1 (de) | 1987-01-14 |
| IL71438A (en) | 1987-09-16 |
| HUT34325A (en) | 1985-03-28 |
| ATE24895T1 (de) | 1987-01-15 |
| DE3312543A1 (de) | 1984-10-11 |
| US4582856A (en) | 1986-04-15 |
| ZA842575B (en) | 1984-11-28 |
| HU195184B (en) | 1988-04-28 |
| EP0121847A3 (en) | 1985-01-30 |
| JPS59196837A (ja) | 1984-11-08 |
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