DD280097A5 - Verfahren zur herstellung neuer cyclopropancarbonsaeureester - Google Patents
Verfahren zur herstellung neuer cyclopropancarbonsaeureester Download PDFInfo
- Publication number
- DD280097A5 DD280097A5 DD88312674A DD31267488A DD280097A5 DD 280097 A5 DD280097 A5 DD 280097A5 DD 88312674 A DD88312674 A DD 88312674A DD 31267488 A DD31267488 A DD 31267488A DD 280097 A5 DD280097 A5 DD 280097A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- alpha
- dimethyl
- radical
- formula
- propenyl
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 35
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- 238000004519 manufacturing process Methods 0.000 title description 4
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- 125000003118 aryl group Chemical group 0.000 claims abstract description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 20
- 239000000460 chlorine Substances 0.000 claims abstract description 10
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000011737 fluorine Substances 0.000 claims abstract description 4
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- -1 substituted alkyl radical Chemical class 0.000 claims description 144
- 238000000034 method Methods 0.000 claims description 57
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- 230000008569 process Effects 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 31
- 238000002360 preparation method Methods 0.000 claims description 27
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- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims description 20
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- 125000005843 halogen group Chemical group 0.000 claims description 10
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- QQHOVRKETYPQHY-UHFFFAOYSA-N 2-(hydroxymethyl)-4,5,6,7-tetrahydroisoindole-1,3-dione Chemical compound O=C1N(CO)C(=O)C2=C1CCCC2 QQHOVRKETYPQHY-UHFFFAOYSA-N 0.000 claims description 4
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- 230000009471 action Effects 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- VJFUPGQZSXIULQ-XIGJTORUSA-N pyrethrin II Chemical class 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 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- VTJMSIIXXKNIDJ-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-methylbutyric acid Chemical class CC(C)C(C(O)=O)C1=CC=C(Cl)C=C1 VTJMSIIXXKNIDJ-UHFFFAOYSA-N 0.000 claims description 2
- MDIQXIJPQWLFSD-UHFFFAOYSA-N 3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical class CC1(C)C(C=C(Br)Br)C1C(O)=O MDIQXIJPQWLFSD-UHFFFAOYSA-N 0.000 claims description 2
- LLMLSUSAKZVFOA-UHFFFAOYSA-N 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid Chemical class CC1(C)C(C=C(Cl)Cl)C1C(O)=O LLMLSUSAKZVFOA-UHFFFAOYSA-N 0.000 claims description 2
- GJRLRWILVCEVKI-UHFFFAOYSA-N 3-[2-fluoro-3-[(2-methylpropan-2-yl)oxy]-3-oxoprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC(C)(C)OC(=O)C(F)=CC1C(C(O)=O)C1(C)C GJRLRWILVCEVKI-UHFFFAOYSA-N 0.000 claims description 2
- 235000007516 Chrysanthemum Nutrition 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- UIWNHGWOYRFCSF-KTERXBQFSA-N (1r,3r)-3-[(e)-3-methoxy-2-methyl-3-oxoprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound COC(=O)C(\C)=C\[C@@H]1[C@@H](C(O)=O)C1(C)C UIWNHGWOYRFCSF-KTERXBQFSA-N 0.000 claims 1
- 244000189548 Chrysanthemum x morifolium Species 0.000 claims 1
- UIWNHGWOYRFCSF-UHFFFAOYSA-N Pyrethric acid Natural products COC(=O)C(C)=CC1C(C(O)=O)C1(C)C UIWNHGWOYRFCSF-UHFFFAOYSA-N 0.000 claims 1
- 241000607479 Yersinia pestis Species 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 29
- 239000001257 hydrogen Substances 0.000 abstract description 29
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 14
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 3
- 230000000361 pesticidal effect Effects 0.000 abstract description 3
- 238000006243 chemical reaction Methods 0.000 description 70
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 65
- KXGVEGMKQFWNSR-LLQZFEROSA-N deoxycholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 KXGVEGMKQFWNSR-LLQZFEROSA-N 0.000 description 58
- 239000000047 product Substances 0.000 description 58
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
- OKKJLVBELUTLKV-UHFFFAOYSA-N methyl alcohol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 49
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
- 239000002904 solvent Substances 0.000 description 38
- 235000019441 ethanol Nutrition 0.000 description 36
- 239000012442 inert solvent Substances 0.000 description 35
- 239000000243 solution Substances 0.000 description 33
- 150000002170 ethers Chemical class 0.000 description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 239000002585 base Substances 0.000 description 27
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 26
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 26
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 25
- 229910052736 halogen Inorganic materials 0.000 description 25
- 125000004093 cyano group Chemical group *C#N 0.000 description 22
- 230000002829 reductive effect Effects 0.000 description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
- 150000002367 halogens Chemical class 0.000 description 21
- 125000003710 aryl alkyl group Chemical group 0.000 description 20
- 230000009467 reduction Effects 0.000 description 19
- 238000006722 reduction reaction Methods 0.000 description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 18
- 241000238631 Hexapoda Species 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- 125000003545 alkoxy group Chemical group 0.000 description 17
- 150000008282 halocarbons Chemical class 0.000 description 17
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- 125000000524 functional group Chemical group 0.000 description 16
- 229930195733 hydrocarbon Natural products 0.000 description 16
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- 150000003839 salts Chemical class 0.000 description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- 150000002431 hydrogen Chemical class 0.000 description 14
- 230000007062 hydrolysis Effects 0.000 description 14
- 238000006460 hydrolysis reaction Methods 0.000 description 14
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 13
- 125000003282 alkyl amino group Chemical group 0.000 description 13
- 125000004663 dialkyl amino group Chemical group 0.000 description 13
- 125000001072 heteroaryl group Chemical group 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
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- 150000001340 alkali metals Chemical class 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 229910052783 alkali metal Inorganic materials 0.000 description 11
- 150000001735 carboxylic acids Chemical class 0.000 description 11
- FDDYTYUUDGHIAU-UHFFFAOYSA-N 8-chloro-n,n-dipropyl-1,2,3,4-tetrahydronaphthalen-2-amine Chemical compound C1=CC(Cl)=C2CC(N(CCC)CCC)CCC2=C1 FDDYTYUUDGHIAU-UHFFFAOYSA-N 0.000 description 10
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 10
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- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 10
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- 235000015424 sodium Nutrition 0.000 description 10
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
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- 150000008064 anhydrides Chemical class 0.000 description 8
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- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 6
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- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
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- 239000011541 reaction mixture Substances 0.000 description 6
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- SODWJACROGQSMM-UHFFFAOYSA-N 5,6,7,8-tetrahydronaphthalen-1-amine Chemical class C1CCCC2=C1C=CC=C2N SODWJACROGQSMM-UHFFFAOYSA-N 0.000 description 5
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- NDCJIWUGZHTHAE-UHFFFAOYSA-N n-(5,6,7,8-tetrahydronaphthalen-1-yl)formamide Chemical class C1CCCC2=C1C=CC=C2NC=O NDCJIWUGZHTHAE-UHFFFAOYSA-N 0.000 description 5
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- 125000004104 aryloxy group Chemical group 0.000 description 4
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 229910052987 metal hydride Inorganic materials 0.000 description 4
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- 231100000252 nontoxic Toxicity 0.000 description 4
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
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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
- C07C69/743—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L22/00—Testing or measuring during manufacture or treatment; Reliability measurements, i.e. testing of parts without further processing to modify the parts as such; Structural arrangements therefor
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L27/00—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Power Engineering (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Health & Medical Sciences (AREA)
- Computer Hardware Design (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Manufacturing & Machinery (AREA)
- Physics & Mathematics (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8701458A FR2610624B1 (fr) | 1987-02-06 | 1987-02-06 | Nouveaux esters d'acides cyclopropanecarboxyliques apparentes a l'acide pyrethrique, leur procede de preparation et leur application a la lutte contre les parasites |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD280097A5 true DD280097A5 (de) | 1990-06-27 |
Family
ID=9347652
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD88312674A DD280097A5 (de) | 1987-02-06 | 1988-02-04 | Verfahren zur herstellung neuer cyclopropancarbonsaeureester |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4939172A (xx) |
| EP (1) | EP0281439B1 (xx) |
| JP (1) | JPH0729989B2 (xx) |
| KR (1) | KR960005514B1 (xx) |
| AT (1) | ATE64368T1 (xx) |
| AU (1) | AU601808B2 (xx) |
| BR (1) | BR8800473A (xx) |
| CA (1) | CA1325013C (xx) |
| DD (1) | DD280097A5 (xx) |
| DE (1) | DE3863202D1 (xx) |
| DK (1) | DK58288A (xx) |
| EG (1) | EG18663A (xx) |
| ES (1) | ES2022993B3 (xx) |
| FR (1) | FR2610624B1 (xx) |
| GR (1) | GR3002415T3 (xx) |
| HU (1) | HU204668B (xx) |
| IL (1) | IL85315A (xx) |
| MX (1) | MX10309A (xx) |
| NZ (1) | NZ223411A (xx) |
| OA (1) | OA08806A (xx) |
| PT (1) | PT86708B (xx) |
| SU (1) | SU1746881A3 (xx) |
| ZA (1) | ZA88822B (xx) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2208509B (en) * | 1987-08-06 | 1990-11-21 | Ici Plc | Insecticidal cyclopropane carboxylic acid esters and intermediates therefor |
| GB8902324D0 (en) * | 1989-02-02 | 1989-03-22 | Ici Plc | Insecticidal compounds |
| FR2678609B1 (fr) * | 1991-07-04 | 1994-08-26 | Roussel Uclaf | Nouveaux esters pyrethrinouides de l'alcool 4-amino 2,3,5,6-tetrafluorophenyl methylique, leur procede de preparation et leur application comme pesticides. |
| FR2687666A1 (fr) * | 1992-02-21 | 1993-08-27 | Roussel Uclaf | Nouveaux esters pyrethrinouiques, derives de l'alcool 6-(trifluoromethyl) benzylique, leur procede de preparation et leur application comme pesticides. |
| FR2693191B1 (fr) * | 1992-07-01 | 1994-08-26 | Roussel Uclaf | Nouvel ester de l'acide [1R[1alpha,3beta(Z)]] 2,2-diméthyl 3-(2-fluoro 3-méthoxy 3-oxo propényl) cyclopropane carboxylique, son procédé de préparation et son application comme pesticide. |
| FR2708600B1 (fr) * | 1993-08-05 | 1995-09-15 | Roussel Uclaf | Nouveaux dérivés de l'alcool 6-trifluorométhyl benzylique, leur procédé de préparation et leur application comme pesticides. |
| JP3376395B2 (ja) * | 1995-02-07 | 2003-02-10 | 大日本除虫菊株式会社 | 新規カルボン酸エステル誘導体、及び殺虫、防虫剤組成物 |
| US6358883B1 (en) * | 1998-11-16 | 2002-03-19 | American Cyanamid Company | Pesticidal and parasiticidal use of 1-aryl-1-(substituted thio, sulfinyl and sulfonyl)-2-nitroethane compounds |
| JP3991812B2 (ja) * | 2001-12-11 | 2007-10-17 | 住友化学株式会社 | エステル化合物およびその用途 |
| JP2004143151A (ja) * | 2002-10-02 | 2004-05-20 | Dainippon Jochugiku Co Ltd | ハエ取り線香 |
| ZA200409433B (en) * | 2003-11-26 | 2005-07-14 | Sumitomo Chemical Co | Process for the preparation of carboxylic acid esters. |
| JP4488765B2 (ja) * | 2004-02-26 | 2010-06-23 | 大日本除蟲菊株式会社 | エアゾール殺虫剤 |
| CA2603818A1 (en) * | 2005-04-29 | 2006-11-09 | Wyeth | Process for preparing 3,3-disubstituted oxindoles and thio-oxindoles |
| JP5076623B2 (ja) * | 2006-05-11 | 2012-11-21 | 住友化学株式会社 | エステル化合物及びその有害生物防除用途 |
| US20090143465A1 (en) * | 2006-05-11 | 2009-06-04 | Sumitomo Chemical Company, Limited | Ester compound and its use in pest control |
| CN108084054B (zh) * | 2017-11-21 | 2020-08-07 | 成都大学 | 一种多取代手性烯基环丙烷化合物及其晶体和其制备方法与用途 |
| CN108178716B (zh) * | 2017-11-21 | 2021-06-01 | 成都大学 | 一种具有多取代基的手性环丙烷化合物及其合成方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4370346A (en) * | 1979-12-21 | 1983-01-25 | Imperial Chemical Industries Plc | Halogenated esters |
| DE3065914D1 (en) * | 1979-12-21 | 1984-01-19 | Ici Plc | Substituted benzyl esters of cyclopropane carboxylic acids and their preparation, compositions containing them and methods of combating insect pests therewith, and substituted benzyl alcohols |
| US4459305A (en) * | 1980-04-10 | 1984-07-10 | Dainippon Sochugiku Kabushiki Kaisha | Cyclopropanecarboxylic acid ester derivatives, a method of manufacturing them, and their uses |
| OA06786A (fr) * | 1980-04-16 | 1982-12-31 | Roussel Uclaf | Nouveaux dérivés de l'acide cyclopropane, leur préparation, leur application à la lutte contre les parasites des végétaux et des animaux, les compositions les renfermant et les nouveaux intermediaires obtenus. |
| FR2482955A1 (fr) * | 1980-05-23 | 1981-11-27 | Roussel Uclaf | Nouveaux derives de l'acide cyclopropane carboxylique, leur procede de preparation et leur application a la lutte contre les parasites |
| FR2486073A1 (fr) * | 1980-07-02 | 1982-01-08 | Roussel Uclaf | Nouveaux derives de l'acide cyclopropane carboxylique, leur procede de preparation, et leur application a la lutte contre les parasites |
| AU543390B2 (en) * | 1980-07-18 | 1985-04-18 | Commonwealth Scientific And Industrial Research Organisation | Pentafluorobenzyl esters of pyrethroid type insecticides |
| FR2491060A1 (fr) * | 1980-10-01 | 1982-04-02 | Roussel Uclaf | Esters d'acides cyclopropanes carboxyliques apparentes a l'acide pyrethrique, leur procede de preparation et leur application a la lutte contre les parasites |
| US4489093A (en) * | 1980-10-01 | 1984-12-18 | Roussel Uclaf | Insecticidal esters |
| GB8505819D0 (en) * | 1985-03-06 | 1985-04-11 | Ici Plc | Fluorobenzyl esters |
| GB8522656D0 (en) * | 1985-09-13 | 1985-10-16 | Ici Plc | Fluoro alcohols |
| GB8629806D0 (en) * | 1986-12-12 | 1987-01-21 | Ici Plc | Fluorobenzyl esters |
-
1987
- 1987-02-06 FR FR8701458A patent/FR2610624B1/fr not_active Expired
-
1988
- 1988-02-02 ES ES88400240T patent/ES2022993B3/es not_active Expired - Lifetime
- 1988-02-02 DE DE8888400240T patent/DE3863202D1/de not_active Expired - Lifetime
- 1988-02-02 EP EP88400240A patent/EP0281439B1/fr not_active Expired - Lifetime
- 1988-02-02 AT AT88400240T patent/ATE64368T1/de not_active IP Right Cessation
- 1988-02-03 JP JP63022155A patent/JPH0729989B2/ja not_active Expired - Lifetime
- 1988-02-03 MX MX1030988A patent/MX10309A/es unknown
- 1988-02-04 SU SU884355520A patent/SU1746881A3/ru active
- 1988-02-04 NZ NZ223411A patent/NZ223411A/xx unknown
- 1988-02-04 IL IL85315A patent/IL85315A/xx not_active IP Right Cessation
- 1988-02-04 DD DD88312674A patent/DD280097A5/de not_active IP Right Cessation
- 1988-02-04 EG EG59/88A patent/EG18663A/xx active
- 1988-02-05 PT PT86708A patent/PT86708B/pt not_active IP Right Cessation
- 1988-02-05 AU AU11344/88A patent/AU601808B2/en not_active Ceased
- 1988-02-05 OA OA59277A patent/OA08806A/xx unknown
- 1988-02-05 CA CA000558326A patent/CA1325013C/fr not_active Expired - Fee Related
- 1988-02-05 HU HU88545A patent/HU204668B/hu unknown
- 1988-02-05 ZA ZA88822A patent/ZA88822B/xx unknown
- 1988-02-05 DK DK058288A patent/DK58288A/da not_active Application Discontinuation
- 1988-02-05 BR BR8800473A patent/BR8800473A/pt not_active IP Right Cessation
- 1988-02-06 KR KR1019880001160A patent/KR960005514B1/ko not_active IP Right Cessation
- 1988-02-08 US US07/153,157 patent/US4939172A/en not_active Expired - Lifetime
-
1991
- 1991-08-02 GR GR90401169T patent/GR3002415T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US4939172A (en) | 1990-07-03 |
| SU1746881A3 (ru) | 1992-07-07 |
| EP0281439A1 (fr) | 1988-09-07 |
| DK58288D0 (da) | 1988-02-05 |
| JPH0729989B2 (ja) | 1995-04-05 |
| FR2610624B1 (fr) | 1989-06-09 |
| ZA88822B (en) | 1989-04-26 |
| BR8800473A (pt) | 1988-09-20 |
| PT86708B (pt) | 1992-04-30 |
| HUT47211A (en) | 1989-02-28 |
| KR880009901A (ko) | 1988-10-05 |
| AU1134488A (en) | 1988-08-11 |
| CA1325013C (fr) | 1993-12-07 |
| DK58288A (da) | 1988-08-07 |
| ES2022993B3 (es) | 1991-12-16 |
| DE3863202D1 (de) | 1991-07-18 |
| AU601808B2 (en) | 1990-09-20 |
| NZ223411A (en) | 1990-02-26 |
| FR2610624A1 (fr) | 1988-08-12 |
| PT86708A (pt) | 1988-03-01 |
| MX10309A (es) | 1993-11-01 |
| KR960005514B1 (ko) | 1996-04-25 |
| ATE64368T1 (de) | 1991-06-15 |
| JPS63201146A (ja) | 1988-08-19 |
| GR3002415T3 (en) | 1992-12-30 |
| EG18663A (fr) | 1993-10-30 |
| EP0281439B1 (fr) | 1991-06-12 |
| HU204668B (en) | 1992-02-28 |
| IL85315A0 (en) | 1988-07-31 |
| OA08806A (fr) | 1989-03-31 |
| IL85315A (en) | 1992-07-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ENJ | Ceased due to non-payment of renewal fee |