GB1446304A - 3-substituted cyclopropane carboxylic acids and derivatives thereof - Google Patents
3-substituted cyclopropane carboxylic acids and derivatives thereofInfo
- Publication number
- GB1446304A GB1446304A GB2201075A GB2201075A GB1446304A GB 1446304 A GB1446304 A GB 1446304A GB 2201075 A GB2201075 A GB 2201075A GB 2201075 A GB2201075 A GB 2201075A GB 1446304 A GB1446304 A GB 1446304A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- hydrogen
- alkyl
- halogen
- substituted
- 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
- -1 3-substituted cyclopropane carboxylic acids Chemical class 0.000 title abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 5
- 239000001257 hydrogen Substances 0.000 abstract 5
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 229910052736 halogen Inorganic materials 0.000 abstract 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- 150000002431 hydrogen Chemical class 0.000 abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- 125000005907 alkyl ester group Chemical group 0.000 abstract 1
- 150000001728 carbonyl compounds Chemical class 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 abstract 1
- 229910001392 phosphorus oxide Inorganic materials 0.000 abstract 1
- VSAISIQCTGDGPU-UHFFFAOYSA-N tetraphosphorus hexaoxide Chemical compound O1P(O2)OP3OP1OP2O3 VSAISIQCTGDGPU-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/535—Organo-phosphoranes
- C07F9/5352—Phosphoranes containing the structure P=C-
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1446304 3 - Substituted cyclopropane carboxylic acid derivatives NATIONAL RESEARCH DEVELOPMENT CORP 15 Aug 1973 [25 May 1972 30 June 1972 21 Dec 1972 24 May 1973] 22010/75 22011/75 22012/75 and 22013/75 Divided out of 1413491 Heading C2C The invention comprises compounds having the general formula wherein R<SP>1</SP> is hydrogen or methyl; R<SP>2</SP> is hydrogen, halogen or alkyl; R<SP>3</SP> is hydrogen, halogen, alkyl or carboalkoxy; at least one of R<SP>2</SP> and R<SP>3</SP> representing a halogeno group and E is halogen or OE<SP>1</SP> where E<SP>1</SP> is hydrogen, a cation or alkyl; with the proviso that when R<SP>1</SP> is hydrogen and the compound is racemic, R<SP>2</SP> and R<SP>3</SP> are not both chlorine. They may be prepared by reacting a phosphorane of formula with a carbonyl compound of the formula wherein Z<SP>4</SP> is an organic residue which forms a stable triorgano phosphorus oxide and E<SP>2</SP> is alkyl, and if desired, converting the resulting alkyl ester into the corresponding free acid or acid halide. The phcsphorane of Formula X may be prepared by reacting a substituted methylhalide of the formula R<SP>3</SP>(R<SP>2</SP>)CH-halogen with a triorgano phosphine of formula P(Z<SP>4</SP>) 3 and if necessary treating the resulting quaternary phosphonium halide with a base to bring about dehydrohalogenation.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2201075A GB1446304A (en) | 1972-05-25 | 1972-05-25 | 3-substituted cyclopropane carboxylic acids and derivatives thereof |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2201075A GB1446304A (en) | 1972-05-25 | 1972-05-25 | 3-substituted cyclopropane carboxylic acids and derivatives thereof |
| GB2201175 | 1972-06-30 | ||
| GB2201275 | 1972-12-21 | ||
| GB2201375 | 1973-05-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1446304A true GB1446304A (en) | 1976-08-18 |
Family
ID=27448547
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2201075A Expired GB1446304A (en) | 1972-05-25 | 1972-05-25 | 3-substituted cyclopropane carboxylic acids and derivatives thereof |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1446304A (en) |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2362817A1 (en) * | 1976-08-26 | 1978-03-24 | Bayer Ag | CYCLOPROPANE-CARBOXYLIC ACIDS AND THEIR PREPARATION PROCESS |
| EP0003060A1 (en) | 1978-01-10 | 1979-07-25 | Bayer Ag | Process for the separation of stereoisomers of substituted vinylcyclopropanecarboxylic acids |
| US4296241A (en) * | 1979-07-21 | 1981-10-20 | Bayer Aktiengesellschaft | Preparation of 3-(2,2-dichlorovinyl)-2,2-dimethyl-cyclopropane-1-carboxylic acid derivatives |
| US4299967A (en) | 1978-12-15 | 1981-11-10 | Ciba-Geigy Corporation | Process for producing optically active 2-(2,2-dihalogenovinyl)-cyclopropane-1-carboxylic acids substituted in the 3-position, and derivatives thereof, as well as novel 4-(2,2,2-trihalogenoethyl)-cyclobutane-1-sulfonic acid salts |
| JPS6023343A (en) * | 1980-10-01 | 1985-02-05 | ルセル−ユクラフ | Esters of cyclopropanecarboxylic acids related with pyrethric acids and manufacture |
| US4954651A (en) * | 1988-05-02 | 1990-09-04 | Sumitomo Chemical Company, Limited | Process for preparing trans-2,2-dimethyl-3-(2,2-dihalovinyl)-cyclopropane carboxylic acid halide |
| US6462225B2 (en) * | 2000-01-12 | 2002-10-08 | Sumitomo Chemical Company, Limited | Method for producing 2,2-dimethyl-3-(1-propenyl)cyclopropanecarboxylate ester |
| WO2012150205A1 (en) | 2011-05-04 | 2012-11-08 | Bayer Cropscience Ag | Novel substituted benzyl alcohol esters of cyclopropanecarboxylic acid as pesticides |
| WO2012150223A1 (en) | 2011-05-04 | 2012-11-08 | Bayer Cropscience Ag | Novel pyridine methyl esters of cyclopropane carboxylic acid as pest control agents |
| WO2012150206A2 (en) | 2011-05-04 | 2012-11-08 | Bayer Cropscience Ag | Novel cyclopropanoic acid ester derivatives as pest control agents |
| WO2012150207A1 (en) | 2011-05-04 | 2012-11-08 | Bayer Cropscience Ag | Use of cyclopropanecarboxylic acid ester derivatives for controlling insecticide-resistant insects |
| WO2012150221A2 (en) | 2011-05-04 | 2012-11-08 | Bayer Cropscience Ag | Novel halogenated benzyl alcohol esters of cyclopropane carboxylic acid as pest control agents |
| WO2012150208A1 (en) | 2011-05-04 | 2012-11-08 | Bayer Cropscience Ag | Use of substituted benzyl alcohol esters of cyclopropanecarboxylic acid for controlling insecticide-resistant insects |
-
1972
- 1972-05-25 GB GB2201075A patent/GB1446304A/en not_active Expired
Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2362817A1 (en) * | 1976-08-26 | 1978-03-24 | Bayer Ag | CYCLOPROPANE-CARBOXYLIC ACIDS AND THEIR PREPARATION PROCESS |
| EP0003060A1 (en) | 1978-01-10 | 1979-07-25 | Bayer Ag | Process for the separation of stereoisomers of substituted vinylcyclopropanecarboxylic acids |
| US4236026A (en) | 1978-01-10 | 1980-11-25 | Bayer Aktiengesellschaft | Separation of stereoisomeric vinylcyclopropanecarboxylic acids |
| US4299967A (en) | 1978-12-15 | 1981-11-10 | Ciba-Geigy Corporation | Process for producing optically active 2-(2,2-dihalogenovinyl)-cyclopropane-1-carboxylic acids substituted in the 3-position, and derivatives thereof, as well as novel 4-(2,2,2-trihalogenoethyl)-cyclobutane-1-sulfonic acid salts |
| US4296241A (en) * | 1979-07-21 | 1981-10-20 | Bayer Aktiengesellschaft | Preparation of 3-(2,2-dichlorovinyl)-2,2-dimethyl-cyclopropane-1-carboxylic acid derivatives |
| JPS6023343A (en) * | 1980-10-01 | 1985-02-05 | ルセル−ユクラフ | Esters of cyclopropanecarboxylic acids related with pyrethric acids and manufacture |
| JPH0643369B2 (en) | 1980-10-01 | 1994-06-08 | ルセル − ユクラフ | Cyclopropanecarboxylic acid esters related to pyrethric acid and processes for their preparation |
| US4954651A (en) * | 1988-05-02 | 1990-09-04 | Sumitomo Chemical Company, Limited | Process for preparing trans-2,2-dimethyl-3-(2,2-dihalovinyl)-cyclopropane carboxylic acid halide |
| US6462225B2 (en) * | 2000-01-12 | 2002-10-08 | Sumitomo Chemical Company, Limited | Method for producing 2,2-dimethyl-3-(1-propenyl)cyclopropanecarboxylate ester |
| AT500971A1 (en) * | 2000-01-12 | 2006-05-15 | Sumitomo Chemical Co | PROCESS FOR PREPARING 2,2-DIMETHYL-3- (1-PROPENYL) CYCLOPROPANCARBOXYLATESTER |
| AT500971B1 (en) * | 2000-01-12 | 2006-10-15 | Sumitomo Chemical Co | PROCESS FOR PREPARING 2,2-DIMETHYL-3- (1-PROPENYL) CYCLOPROPANCARBOXYLATESTER |
| WO2012150205A1 (en) | 2011-05-04 | 2012-11-08 | Bayer Cropscience Ag | Novel substituted benzyl alcohol esters of cyclopropanecarboxylic acid as pesticides |
| WO2012150223A1 (en) | 2011-05-04 | 2012-11-08 | Bayer Cropscience Ag | Novel pyridine methyl esters of cyclopropane carboxylic acid as pest control agents |
| WO2012150206A2 (en) | 2011-05-04 | 2012-11-08 | Bayer Cropscience Ag | Novel cyclopropanoic acid ester derivatives as pest control agents |
| WO2012150207A1 (en) | 2011-05-04 | 2012-11-08 | Bayer Cropscience Ag | Use of cyclopropanecarboxylic acid ester derivatives for controlling insecticide-resistant insects |
| WO2012150221A2 (en) | 2011-05-04 | 2012-11-08 | Bayer Cropscience Ag | Novel halogenated benzyl alcohol esters of cyclopropane carboxylic acid as pest control agents |
| WO2012150208A1 (en) | 2011-05-04 | 2012-11-08 | Bayer Cropscience Ag | Use of substituted benzyl alcohol esters of cyclopropanecarboxylic acid for controlling insecticide-resistant insects |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| 429A | Application made for amendment of specification (sect. 29/1949) | ||
| 429H | Application (made) for amendment of specification now open to opposition (sect. 29/1949) | ||
| 429D | Case decided by the comptroller ** specification amended (sect. 29/1949) | ||
| SPA | Amended specification published | ||
| 732 | Registration of transactions, instruments or events in the register (sect. 32/1977) | ||
| PE20 | Patent expired after termination of 20 years |
Effective date: 19930814 |