HUP0301001A2 - Eljárás optikailag tiszta piretroid típusú inszekticid hatóanyagok és intermedierjeik előállítására - Google Patents
Eljárás optikailag tiszta piretroid típusú inszekticid hatóanyagok és intermedierjeik előállításáraInfo
- Publication number
- HUP0301001A2 HUP0301001A2 HU0301001A HUP0301001A HUP0301001A2 HU P0301001 A2 HUP0301001 A2 HU P0301001A2 HU 0301001 A HU0301001 A HU 0301001A HU P0301001 A HUP0301001 A HU P0301001A HU P0301001 A2 HUP0301001 A2 HU P0301001A2
- Authority
- HU
- Hungary
- Prior art keywords
- enantiomers
- general formula
- enantiomer
- formula
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 2
- 239000002917 insecticide Substances 0.000 title 1
- 239000000543 intermediate Substances 0.000 title 1
- 239000002728 pyrethroid Substances 0.000 title 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 abstract 9
- 150000001875 compounds Chemical class 0.000 abstract 6
- 239000000203 mixture Substances 0.000 abstract 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 4
- 229910052801 chlorine Inorganic materials 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 2
- 125000001188 haloalkyl group Chemical group 0.000 abstract 2
- 230000000749 insecticidal effect Effects 0.000 abstract 2
- SPVZAYWHHVLPBN-AVCLAYCWSA-N (1s,3s)-3-[(z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)[C@H](\C=C(/Cl)C(F)(F)F)[C@@H]1C(O)=O SPVZAYWHHVLPBN-AVCLAYCWSA-N 0.000 abstract 1
- 230000000895 acaricidal effect Effects 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 238000005903 acid hydrolysis reaction Methods 0.000 abstract 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 238000005660 chlorination reaction Methods 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 230000001069 nematicidal effect Effects 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
-
- 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
- C07C61/15—Saturated compounds containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/14—Preparation of carboxylic acid esters from carboxylic acid halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
Abstract
A találmány tárgya (I) általános képletű vegyületek - a képletben Yklór- vagy brómatomot jelent, Z klóratomot, brómatomot vagy halogén-alkil-csoportot jelent, és E inszekticid aktivitású észterképzőcsoportot jelent - tiszta enantiomerjeinek vagy az egyik enantiomerbendús enantiomer-elegyeinek előállítására, melynek során (a) egy (III)általános képletű vegyület - a képletben Y és Z jelentése a fenti -egyik enantiomerjét vagy az egyik enantiomerben dús enantiomerelegyét;(b) az (a) lépésben kapott terméket klórozással egy (II) általánosképletű vegyület - a képletben Y és Z jelentése a fenti - egyikenantiomerjévé vagy az egyik enantiomerben dús enantiomer elegyévéalakítják; és (c) a (b) lépésben kapott terméket észterezéssel egy (I)általános képletű vegyület egyik enantiomerjévé vagy az egyikenantiomerben dús enantiomerelegyévé alakítják. A találmány továbbitárgya eljárás (VIIa) és (VIIb) általános képletű vegyületekelőállítására - a képletekben X kilépő atomot vagy csoportot jelent, Yés Y' egymástól függetlenül klór- vagy brómatomot jelent, és Zklóratomot, brómatomot vagy halogén-alkil-csoportot képvisel - olymódon, hogy a) egy (VII) általános képletű vegyületet - a képletben X,Y, Y' és Z jelentése a fenti - oldószer jelenlétében egy optikailaglényegében tiszta királis aminnal reagáltatva diasztereoizomer sópártképeznek, b) az egyedi enantiomerek diasztereoizomer sóit elválasztjákegymástól, és c) az egyedi enantiomerek diasztereoizomer sóiból savasvagy lúgos hidrolízissel külön-külön felszabadítják a (VIIa) és (VIIb)általános képletű vegyületeket. A találmány tárgya továbbáinszekticid, akaricid vagy nematicid készítmény, ami a Z-(1 RS)-cisz-3-(2klór-3,3,3-trifluor-prop-1-enil)-2,2-dimetil-ciklopropán-karbonsav-2,3,5,6-tetrafluor-4-metil-benzil-észter (+)-enantiomerjéttartalmazza hatásos mennyiségben. Ó
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0017617.2A GB0017617D0 (en) | 2000-07-18 | 2000-07-18 | Chemical process |
| PCT/GB2001/003180 WO2002006202A1 (en) | 2000-07-18 | 2001-07-16 | Process for the preparation of enantiomerically pure pyrethroid insecticides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUP0301001A2 true HUP0301001A2 (hu) | 2003-08-28 |
| HUP0301001A3 HUP0301001A3 (en) | 2004-06-28 |
Family
ID=9895882
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU0301001A HUP0301001A3 (en) | 2000-07-18 | 2001-07-16 | Process for the preparation of enantiomerically pure pyrethroid insecticides and their intermediates and use thereof |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US6875885B2 (hu) |
| EP (1) | EP1303474B1 (hu) |
| JP (1) | JP5047441B2 (hu) |
| KR (1) | KR100839558B1 (hu) |
| CN (1) | CN1277796C (hu) |
| AT (1) | ATE483677T1 (hu) |
| AU (1) | AU2001270829A1 (hu) |
| BR (1) | BRPI0112528B1 (hu) |
| CA (1) | CA2413472C (hu) |
| DE (1) | DE60143200D1 (hu) |
| ES (1) | ES2352883T3 (hu) |
| GB (1) | GB0017617D0 (hu) |
| HU (1) | HUP0301001A3 (hu) |
| IL (1) | IL153521A0 (hu) |
| WO (1) | WO2002006202A1 (hu) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0304132D0 (en) * | 2003-02-24 | 2003-03-26 | Syngenta Ltd | Chemical process |
| EP2083632A2 (en) * | 2006-11-21 | 2009-08-05 | Mitam Ltd. | Formulations of entomopathogenic fungi for insect control |
| KR101014604B1 (ko) * | 2008-07-25 | 2011-02-16 | 미광창호주식회사 | 비상시 개방이 용이한 자동문 |
| CN101838195B (zh) * | 2009-03-17 | 2014-08-13 | 天士力制药集团股份有限公司 | 光学纯的β-3,4-二羟基苯基乳酸的化学拆分制备法 |
| TWI508962B (zh) | 2009-04-22 | 2015-11-21 | Du Pont | 氮雜環醯胺之固體形態 |
| BR102013021210B1 (pt) | 2013-01-25 | 2015-12-01 | Fundação Universidade Fed De São Carlos | processo de obtenção de nanopartículas biopoliméricas contendo óleo e extratos de azadirachta indica a. juss (neem), nanopartículas biopoliméricas e micropartículas em pó |
| WO2015021991A1 (en) | 2013-08-16 | 2015-02-19 | Cheminova A/S | Combination of 2-methylbiphenyl-3-ylmethyl (z)-(1r)-cis-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylate with at least one insecticide, acaricide, nematicide and/or fungicide. |
| AR097518A1 (es) * | 2013-09-02 | 2016-03-23 | Cheminova As | Combinación de (z)-(1r)-cis-3-(2-cloro-3,3,3-trifluoro-1-propenil)-2,2-dimetilciclopropanocarboxilato de 2,3,5,6-tetrafluoro-4-metilbencilo con al menos un insecticida, acaricida, nematicida y/o fungicida |
| GB2519787B (en) * | 2013-10-30 | 2018-08-29 | Rotam Agrochem Int Co Ltd | Process for the preparation of herbicidal carboxylic acid salts |
| AU2020311625A1 (en) * | 2019-07-10 | 2022-03-03 | Gharda Chemicals Limited | A process for isolating S-isomer crystals of Indoxacarb |
| WO2021144812A1 (en) * | 2020-01-17 | 2021-07-22 | Srf Limited | Process for preparation of cyclopropane carboxylic acids and intermediates thereof |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ180822A (en) * | 1975-05-16 | 1979-03-16 | Ici Ltd | Preparation of 2-(2,2-dihalovinyl)-3,3-dimethylcyolopropane carboxylates intermediates |
| JPS52125121A (en) * | 1976-04-08 | 1977-10-20 | Kuraray Co Ltd | Carboxylic acids having halogen atoms at gamma- and epsilon-positions and method of preparing the same |
| IN150399B (hu) * | 1978-01-20 | 1982-09-25 | Fmc Corp | |
| US4166064A (en) * | 1978-02-13 | 1979-08-28 | Fmc Corporation | Process for preparing high cis 3-(2,2,2-trichloroethyl)-2,2-dimethylcyclopropane-1-carboxylates |
| US4333950A (en) * | 1979-05-24 | 1982-06-08 | Fmc Corporation | (+)-4-Substituted-2-indanol insecticidal ester derivatives |
| US4335252A (en) * | 1979-05-24 | 1982-06-15 | Fmc Corporation | Insecticidal pyrethroid enantiomer pair |
| DE3064018D1 (en) * | 1979-07-13 | 1983-08-11 | Ici Plc | Process for the preparation of cyclopropane carboxylic acid esters |
| EP0031199B1 (en) * | 1979-12-21 | 1983-12-14 | Imperial Chemical Industries 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 |
| US4429149A (en) * | 1980-12-31 | 1984-01-31 | Fmc Corporation | 4-Phenyl-2-indanyl esters of 1R,cis-3-(2-halo-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylic acid |
-
2000
- 2000-07-18 GB GBGB0017617.2A patent/GB0017617D0/en not_active Ceased
-
2001
- 2001-07-16 US US10/332,884 patent/US6875885B2/en not_active Expired - Fee Related
- 2001-07-16 DE DE60143200T patent/DE60143200D1/de not_active Expired - Lifetime
- 2001-07-16 KR KR1020037000695A patent/KR100839558B1/ko not_active IP Right Cessation
- 2001-07-16 BR BRPI0112528-1A patent/BRPI0112528B1/pt not_active IP Right Cessation
- 2001-07-16 HU HU0301001A patent/HUP0301001A3/hu unknown
- 2001-07-16 WO PCT/GB2001/003180 patent/WO2002006202A1/en active Application Filing
- 2001-07-16 ES ES01949710T patent/ES2352883T3/es not_active Expired - Lifetime
- 2001-07-16 AT AT01949710T patent/ATE483677T1/de not_active IP Right Cessation
- 2001-07-16 JP JP2002512109A patent/JP5047441B2/ja not_active Expired - Fee Related
- 2001-07-16 IL IL15352101A patent/IL153521A0/xx not_active IP Right Cessation
- 2001-07-16 CN CNB01812982XA patent/CN1277796C/zh not_active Expired - Fee Related
- 2001-07-16 AU AU2001270829A patent/AU2001270829A1/en not_active Abandoned
- 2001-07-16 EP EP01949710A patent/EP1303474B1/en not_active Expired - Lifetime
- 2001-07-16 CA CA2413472A patent/CA2413472C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US6875885B2 (en) | 2005-04-05 |
| CA2413472C (en) | 2011-04-19 |
| DE60143200D1 (de) | 2010-11-18 |
| AU2001270829A1 (en) | 2002-01-30 |
| CN1277796C (zh) | 2006-10-04 |
| US20030199709A1 (en) | 2003-10-23 |
| KR20030017639A (ko) | 2003-03-03 |
| IL153521A0 (en) | 2003-07-06 |
| JP5047441B2 (ja) | 2012-10-10 |
| ATE483677T1 (de) | 2010-10-15 |
| BRPI0112528B1 (pt) | 2015-09-01 |
| WO2002006202A1 (en) | 2002-01-24 |
| ES2352883T3 (es) | 2011-02-23 |
| JP2004504290A (ja) | 2004-02-12 |
| KR100839558B1 (ko) | 2008-06-19 |
| HUP0301001A3 (en) | 2004-06-28 |
| CA2413472A1 (en) | 2002-01-24 |
| GB0017617D0 (en) | 2000-09-06 |
| CN1443153A (zh) | 2003-09-17 |
| EP1303474A1 (en) | 2003-04-23 |
| BR0112528A (pt) | 2003-07-01 |
| EP1303474B1 (en) | 2010-10-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FD9A | Lapse of provisional protection due to non-payment of fees |