HU184193B - Process for preparing /s/-alpha-cyano-3-phenoxy-benzyl-alcohol ester with insecticide activity formed with d-2-isopropyl-2-/4-chloro-phenyl/-acetic acid - Google Patents
Process for preparing /s/-alpha-cyano-3-phenoxy-benzyl-alcohol ester with insecticide activity formed with d-2-isopropyl-2-/4-chloro-phenyl/-acetic acid Download PDFInfo
- Publication number
- HU184193B HU184193B HU79RO1009A HURO001009A HU184193B HU 184193 B HU184193 B HU 184193B HU 79RO1009 A HU79RO1009 A HU 79RO1009A HU RO001009 A HURO001009 A HU RO001009A HU 184193 B HU184193 B HU 184193B
- Authority
- HU
- Hungary
- Prior art keywords
- isopropyl
- alpha
- cyano
- chlorophenyl
- acetic acid
- Prior art date
Links
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 title claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title description 5
- 238000004519 manufacturing process Methods 0.000 title description 3
- 239000002917 insecticide Substances 0.000 title description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 54
- 238000002360 preparation method Methods 0.000 claims description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 14
- GXUQMKBQDGPMKZ-CQSZACIVSA-N (2s)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrile Chemical compound N#C[C@@H](O)C1=CC=CC(OC=2C=CC=CC=2)=C1 GXUQMKBQDGPMKZ-CQSZACIVSA-N 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 238000002425 crystallisation Methods 0.000 claims description 6
- 230000008025 crystallization Effects 0.000 claims description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
- GXUQMKBQDGPMKZ-UHFFFAOYSA-N 2-hydroxy-2-(3-phenoxyphenyl)acetonitrile Chemical compound N#CC(O)C1=CC=CC(OC=2C=CC=CC=2)=C1 GXUQMKBQDGPMKZ-UHFFFAOYSA-N 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 239000003208 petroleum Substances 0.000 claims description 3
- VTJMSIIXXKNIDJ-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-methylbutyric acid Chemical compound CC(C)C(C(O)=O)C1=CC=C(Cl)C=C1 VTJMSIIXXKNIDJ-UHFFFAOYSA-N 0.000 claims description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 2
- 239000000908 ammonium hydroxide Substances 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims 1
- 238000011081 inoculation Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
- -1 phenoxybenzyl alcohol ester Chemical class 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 13
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 9
- 230000000749 insecticidal effect Effects 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 150000001721 carbon Chemical group 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000003828 vacuum filtration Methods 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 125000002560 nitrile group Chemical group 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 241000238631 Hexapoda Species 0.000 description 3
- 238000002983 circular dichroism Methods 0.000 description 3
- 238000010908 decantation Methods 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 241000255925 Diptera Species 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 125000003158 alcohol group Chemical group 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 229960005235 piperonyl butoxide Drugs 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000002211 ultraviolet spectrum Methods 0.000 description 2
- RQEUFEKYXDPUSK-SSDOTTSWSA-N (1R)-1-phenylethanamine Chemical class C[C@@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-SSDOTTSWSA-N 0.000 description 1
- KGANAERDZBAECK-UHFFFAOYSA-N (3-phenoxyphenyl)methanol Chemical compound OCC1=CC=CC(OC=2C=CC=CC=2)=C1 KGANAERDZBAECK-UHFFFAOYSA-N 0.000 description 1
- XNRCGJVOJYKMSA-UHFFFAOYSA-N 5-[bis[2-(2-butoxyethoxy)ethoxy]methyl]-1,3-benzodioxole Chemical compound CCCCOCCOCCOC(OCCOCCOCCCC)C1=CC=C2OCOC2=C1 XNRCGJVOJYKMSA-UHFFFAOYSA-N 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- 241000255777 Lepidoptera Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- HFCMQKFXCMZZMZ-UHFFFAOYSA-N bicyclo[3.1.0]hexan-2-one Chemical compound O=C1CCC2CC12 HFCMQKFXCMZZMZ-UHFFFAOYSA-N 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- WJYHCYBNUJVCEH-UHFFFAOYSA-N cyclohexane;ethoxyethane Chemical compound CCOCC.C1CCCCC1 WJYHCYBNUJVCEH-UHFFFAOYSA-N 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000006345 epimerization reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000002316 fumigant Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
- A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/64—Acyl halides
- C07C57/76—Acyl halides containing halogen outside the carbonyl halide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7802622A FR2416219A1 (fr) | 1978-01-31 | 1978-01-31 | Esters d'acide acetique substitue optiquement actif et d'alcool benzylique substitue racemique ou optiquement actif, doues de proprietes insecticides, leur procede de preparation et les compositions les renfermant |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU184193B true HU184193B (en) | 1984-07-30 |
Family
ID=9204008
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU79RO1009A HU184193B (en) | 1978-01-31 | 1979-01-26 | Process for preparing /s/-alpha-cyano-3-phenoxy-benzyl-alcohol ester with insecticide activity formed with d-2-isopropyl-2-/4-chloro-phenyl/-acetic acid |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS54109945A (enExample) |
| AU (1) | AU4375579A (enExample) |
| BE (1) | BE873798A (enExample) |
| BR (1) | BR7900515A (enExample) |
| CA (1) | CA1204122A (enExample) |
| CH (1) | CH637371A5 (enExample) |
| DE (1) | DE2902478A1 (enExample) |
| DK (1) | DK20679A (enExample) |
| FR (1) | FR2416219A1 (enExample) |
| GB (1) | GB2014137B (enExample) |
| HU (1) | HU184193B (enExample) |
| IL (1) | IL56522A0 (enExample) |
| IT (1) | IT1116506B (enExample) |
| OA (1) | OA06149A (enExample) |
| PL (1) | PL213093A1 (enExample) |
| RO (2) | RO81958A (enExample) |
| SE (1) | SE7900150L (enExample) |
| ZA (1) | ZA79342B (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55104249A (en) | 1979-02-05 | 1980-08-09 | Sumitomo Chem Co Ltd | Optically active carboxylic ester its preparation, and insecticide, and acaricide comprising it |
| FR2472570A1 (fr) * | 1979-07-31 | 1981-07-03 | Roussel Uclaf | Procede de preparation du (1,5) 6,6-dimethyl 4-hydroxy 3-oxa bicylo(3.1.0.)hexan-2-one et de ses ethers en position 4, sous toutes leurs formes stereoisomeres |
| JPS56133253A (en) * | 1980-03-24 | 1981-10-19 | Sumitomo Chem Co Ltd | Optical isomer of cyanohydrin ester, its production and insecticide and acaricide containing the same as effective ingredient |
| JPS56167654A (en) * | 1980-05-28 | 1981-12-23 | Sumitomo Chem Co Ltd | Method for obtaining stereoisomeric mixture of more highly active phenylacetic ester derivative |
| DE3167334D1 (en) * | 1980-10-20 | 1985-01-03 | Sumitomo Chemical Co | Preparation of insecticidal optically active isovalerate esters |
| JPS57169453A (en) * | 1981-04-13 | 1982-10-19 | Sumitomo Chem Co Ltd | Preparation of optically active carboxylic ester |
| JPS5793948A (en) * | 1980-12-02 | 1982-06-11 | Sumitomo Chem Co Ltd | Preparation of stereoisomer mixture of higher active phenylacetic ester derivative |
| EP0312124A3 (en) * | 1982-11-22 | 1989-09-13 | E.I. Du Pont De Nemours And Company | Process for the preparation of optically-active cyanomethyl esters |
| EP0291626A3 (en) | 1982-11-22 | 1989-05-31 | E.I. Du Pont De Nemours And Company | Process for the preparation of optically-active cyanomethyl esters |
| JPH0684332B2 (ja) * | 1985-06-20 | 1994-10-26 | 住友化学工業株式会社 | ａ−イソプロピル−ｐ−クロルフエニル酢酸の光学分割法 |
| EP1583732A1 (en) * | 2003-01-03 | 2005-10-12 | Council of Scientific and Industrial Research | Process for preparing (+)-2-(4-chlorophenyl)-3-methyl butanoic acid |
| WO2006010994A1 (en) * | 2004-07-20 | 2006-02-02 | Council Of Scientific And Industrial Research | Process for preparing (s)-alpha-cyano-3-phenoxybenzyl-(s)-2-(4-chlorophenyl)-isovalerate |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1559799A (en) * | 1975-11-12 | 1980-01-30 | Shell Int Research | Process for preparing substituted benzylesters |
| CA1122224A (en) * | 1976-03-01 | 1982-04-20 | Roger A. Sheldon | Preparation of pesticidal benzyl esters |
-
1978
- 1978-01-31 FR FR7802622A patent/FR2416219A1/fr active Granted
-
1979
- 1979-01-08 SE SE7900150A patent/SE7900150L/xx not_active Application Discontinuation
- 1979-01-13 OA OA56708A patent/OA06149A/xx unknown
- 1979-01-18 DK DK20679A patent/DK20679A/da not_active Application Discontinuation
- 1979-01-23 DE DE19792902478 patent/DE2902478A1/de not_active Withdrawn
- 1979-01-25 RO RO79106660A patent/RO81958A/ro unknown
- 1979-01-25 RO RO7996387A patent/RO79169A/ro unknown
- 1979-01-26 ZA ZA79342A patent/ZA79342B/xx unknown
- 1979-01-26 HU HU79RO1009A patent/HU184193B/hu not_active IP Right Cessation
- 1979-01-29 IT IT47811/79A patent/IT1116506B/it active
- 1979-01-29 BR BR7900515A patent/BR7900515A/pt unknown
- 1979-01-29 IL IL56522A patent/IL56522A0/xx unknown
- 1979-01-30 GB GB7903132A patent/GB2014137B/en not_active Expired
- 1979-01-30 PL PL21309379A patent/PL213093A1/xx unknown
- 1979-01-30 CA CA000320523A patent/CA1204122A/fr not_active Expired
- 1979-01-30 AU AU43755/79A patent/AU4375579A/en not_active Abandoned
- 1979-01-30 BE BE0/193149A patent/BE873798A/xx not_active IP Right Cessation
- 1979-01-31 CH CH93879A patent/CH637371A5/fr not_active IP Right Cessation
- 1979-01-31 JP JP927579A patent/JPS54109945A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| PL213093A1 (enExample) | 1979-11-05 |
| RO81958B (ro) | 1983-05-30 |
| CH637371A5 (fr) | 1983-07-29 |
| FR2416219A1 (fr) | 1979-08-31 |
| IL56522A0 (en) | 1979-03-12 |
| AU4375579A (en) | 1979-08-09 |
| BE873798A (fr) | 1979-07-30 |
| BR7900515A (pt) | 1979-08-21 |
| IT7947811A0 (it) | 1979-01-29 |
| CA1204122A (fr) | 1986-05-06 |
| RO81958A (ro) | 1983-06-01 |
| RO79169A (ro) | 1982-06-25 |
| SE7900150L (sv) | 1979-08-01 |
| DK20679A (da) | 1979-08-01 |
| GB2014137A (en) | 1979-08-22 |
| GB2014137B (en) | 1982-08-18 |
| DE2902478A1 (de) | 1979-08-02 |
| IT1116506B (it) | 1986-02-10 |
| FR2416219B1 (enExample) | 1982-10-22 |
| ZA79342B (en) | 1980-01-30 |
| JPS54109945A (en) | 1979-08-29 |
| OA06149A (fr) | 1981-06-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |