DE2902478A1 - Mit insektiziden eigenschaften ausgestattete ester von optisch aktiver substituierter essigsaeure mit racemischem oder optisch aktivem substituierten benzylalkohol, deren herstellungsverfahren und die sie enthaltenden insektiziden zusammensetzungen - Google Patents
Mit insektiziden eigenschaften ausgestattete ester von optisch aktiver substituierter essigsaeure mit racemischem oder optisch aktivem substituierten benzylalkohol, deren herstellungsverfahren und die sie enthaltenden insektiziden zusammensetzungenInfo
- Publication number
- DE2902478A1 DE2902478A1 DE19792902478 DE2902478A DE2902478A1 DE 2902478 A1 DE2902478 A1 DE 2902478A1 DE 19792902478 DE19792902478 DE 19792902478 DE 2902478 A DE2902478 A DE 2902478A DE 2902478 A1 DE2902478 A1 DE 2902478A1
- Authority
- DE
- Germany
- Prior art keywords
- isopropyl
- cyano
- benzyl alcohol
- phenoxy
- acid
- 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.)
- Withdrawn
Links
- 150000002148 esters Chemical class 0.000 title claims description 70
- 230000000749 insecticidal effect Effects 0.000 title claims description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical class CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title description 10
- 238000004519 manufacturing process Methods 0.000 title description 8
- 239000002917 insecticide Substances 0.000 title description 2
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical class O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 title description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 90
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 54
- 239000000203 mixture Substances 0.000 claims description 43
- 239000002253 acid Substances 0.000 claims description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 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 19
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 14
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 10
- 150000007513 acids Chemical class 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical group N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 6
- 238000002425 crystallisation Methods 0.000 claims description 6
- 230000008025 crystallization Effects 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 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 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 150000001805 chlorine compounds Chemical class 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 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 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims 2
- 150000001298 alcohols Chemical class 0.000 claims 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 229960003424 phenylacetic acid Drugs 0.000 claims 1
- 239000003279 phenylacetic acid Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 229910052739 hydrogen Inorganic materials 0.000 description 16
- 239000001257 hydrogen Substances 0.000 description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- WVDDGKGOMKODPV-UHFFFAOYSA-N hydroxymethyl benzene Natural products OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 238000004821 distillation Methods 0.000 description 8
- 238000003756 stirring Methods 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 6
- HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical compound C[CH]C HNUALPPJLMYHDK-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
- 239000003999 initiator Substances 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 238000002983 circular dichroism Methods 0.000 description 5
- 125000002560 nitrile group Chemical group 0.000 description 5
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 235000011054 acetic acid Nutrition 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- -1 des Ester Chemical class 0.000 description 4
- 230000032050 esterification Effects 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- 241000255925 Diptera Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical class CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 description 2
- 125000003158 alcohol group Chemical group 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229960005235 piperonyl butoxide Drugs 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000002211 ultraviolet spectrum Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- OPLCSTZDXXUYDU-UHFFFAOYSA-N 2,4-dimethyl-6-tert-butylphenol Chemical compound CC1=CC(C)=C(O)C(C(C)(C)C)=C1 OPLCSTZDXXUYDU-UHFFFAOYSA-N 0.000 description 1
- TXILIAXAWMMBHD-UHFFFAOYSA-N 2-(4-chlorophenyl)pentanoic acid Chemical compound CCCC(C(O)=O)C1=CC=C(Cl)C=C1 TXILIAXAWMMBHD-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- QKSGIGXOKHZCQZ-UHFFFAOYSA-N 2-chloro-2-phenylacetic acid Chemical compound OC(=O)C(Cl)C1=CC=CC=C1 QKSGIGXOKHZCQZ-UHFFFAOYSA-N 0.000 description 1
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-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
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- CLJIBHYYSDHPOU-UHFFFAOYSA-N C1=CC2CC1C1C2C(=O)N(CC(CC)CCCCC)C1=O Chemical compound C1=CC2CC1C1C2C(=O)N(CC(CC)CCCCC)C1=O CLJIBHYYSDHPOU-UHFFFAOYSA-N 0.000 description 1
- 241000218645 Cedrus Species 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000255777 Lepidoptera Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 240000004460 Tanacetum coccineum Species 0.000 description 1
- ROVGZAWFACYCSP-MQBLHHJJSA-N [2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(C\C=C/C=C)C(=O)C1 ROVGZAWFACYCSP-MQBLHHJJSA-N 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
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical group CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229960001506 brilliant green Drugs 0.000 description 1
- HXCILVUBKWANLN-UHFFFAOYSA-N brilliant green cation Chemical compound C1=CC(N(CC)CC)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](CC)CC)C=C1 HXCILVUBKWANLN-UHFFFAOYSA-N 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000010828 elution Methods 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
- 238000001914 filtration Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 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
- 150000002596 lactones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 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
- 238000000746 purification Methods 0.000 description 1
- 229940015367 pyrethrum Drugs 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000008096 xylene 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 |
|---|---|
| DE2902478A1 true DE2902478A1 (de) | 1979-08-02 |
Family
ID=9204008
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19792902478 Withdrawn DE2902478A1 (de) | 1978-01-31 | 1979-01-23 | Mit insektiziden eigenschaften ausgestattete ester von optisch aktiver substituierter essigsaeure mit racemischem oder optisch aktivem substituierten benzylalkohol, deren herstellungsverfahren und die sie enthaltenden insektiziden zusammensetzungen |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS54109945A (en, 2012) |
| AU (1) | AU4375579A (en, 2012) |
| BE (1) | BE873798A (en, 2012) |
| BR (1) | BR7900515A (en, 2012) |
| CA (1) | CA1204122A (en, 2012) |
| CH (1) | CH637371A5 (en, 2012) |
| DE (1) | DE2902478A1 (en, 2012) |
| DK (1) | DK20679A (en, 2012) |
| FR (1) | FR2416219A1 (en, 2012) |
| GB (1) | GB2014137B (en, 2012) |
| HU (1) | HU184193B (en, 2012) |
| IL (1) | IL56522A0 (en, 2012) |
| IT (1) | IT1116506B (en, 2012) |
| OA (1) | OA06149A (en, 2012) |
| PL (1) | PL213093A1 (en, 2012) |
| RO (2) | RO79169A (en, 2012) |
| SE (1) | SE7900150L (en, 2012) |
| ZA (1) | ZA79342B (en, 2012) |
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 |
| JPS57169453A (en) * | 1981-04-13 | 1982-10-19 | Sumitomo Chem Co Ltd | Preparation of optically active carboxylic ester |
| US4422978A (en) * | 1980-10-20 | 1983-12-27 | Sumitomo Chemical Company, Limited | Method for preparing optically active carboxylic acid esters |
| 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 |
| AU2004321853B2 (en) * | 2004-07-20 | 2011-03-17 | 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 RO7996387A patent/RO79169A/ro unknown
- 1979-01-25 RO RO79106660A patent/RO81958A/ro unknown
- 1979-01-26 HU HU79RO1009A patent/HU184193B/hu not_active IP Right Cessation
- 1979-01-26 ZA ZA79342A patent/ZA79342B/xx unknown
- 1979-01-29 IT IT47811/79A patent/IT1116506B/it active
- 1979-01-29 IL IL56522A patent/IL56522A0/xx unknown
- 1979-01-29 BR BR7900515A patent/BR7900515A/pt unknown
- 1979-01-30 AU AU43755/79A patent/AU4375579A/en not_active Abandoned
- 1979-01-30 GB GB7903132A patent/GB2014137B/en not_active Expired
- 1979-01-30 CA CA000320523A patent/CA1204122A/fr not_active Expired
- 1979-01-30 PL PL21309379A patent/PL213093A1/xx unknown
- 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 |
|---|---|
| RO79169A (ro) | 1982-06-25 |
| ZA79342B (en) | 1980-01-30 |
| GB2014137A (en) | 1979-08-22 |
| OA06149A (fr) | 1981-06-30 |
| AU4375579A (en) | 1979-08-09 |
| FR2416219A1 (fr) | 1979-08-31 |
| RO81958B (ro) | 1983-05-30 |
| IT1116506B (it) | 1986-02-10 |
| SE7900150L (sv) | 1979-08-01 |
| DK20679A (da) | 1979-08-01 |
| FR2416219B1 (en, 2012) | 1982-10-22 |
| GB2014137B (en) | 1982-08-18 |
| IL56522A0 (en) | 1979-03-12 |
| RO81958A (ro) | 1983-06-01 |
| IT7947811A0 (it) | 1979-01-29 |
| BR7900515A (pt) | 1979-08-21 |
| PL213093A1 (en, 2012) | 1979-11-05 |
| JPS54109945A (en) | 1979-08-29 |
| HU184193B (en) | 1984-07-30 |
| CA1204122A (fr) | 1986-05-06 |
| BE873798A (fr) | 1979-07-30 |
| CH637371A5 (fr) | 1983-07-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2742546A1 (de) | Neue ester von cyclopropancarbonsaeuren mit einem polyhalogenierten substituenten, verfahren zu deren herstellung und pestizide zusammensetzungen | |
| DE2902478A1 (de) | Mit insektiziden eigenschaften ausgestattete ester von optisch aktiver substituierter essigsaeure mit racemischem oder optisch aktivem substituierten benzylalkohol, deren herstellungsverfahren und die sie enthaltenden insektiziden zusammensetzungen | |
| DE2902466A1 (de) | Optisch aktiver substituierter benzylalkohol und dessen herstellungsverfahren | |
| DE3329186A1 (de) | Chromonalkaloid, verfahren zu seiner isolierung aus dysoxylum binectariferum, und seine verwendung als arzneimittel | |
| DE69319296T2 (de) | Verfahren zur Reinigung von roher Clavulansäure | |
| DE2406628A1 (de) | Alkylester von partricin, verfahren zu ihrer herstellung und diese ester enthaltende pharmazeutische mittel | |
| DE69412598T2 (de) | Formylierungsverfahren für aromatische aldehyde | |
| DE2903268A1 (de) | Neue ester von cyclopropancarbonsaeuren mit einem polyhalogenierten substituenten, verfahren zu deren herstellung und pestizide zusammensetzungen | |
| DE2502504C3 (de) | Phenothiazinderivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zusammensetzungen | |
| DE69227803T2 (de) | Pyrethroide Ester des 1,3,4,5,6,7-Hexahydro-1,3-dioxol 2H-isoindol-2-yl Methylalkohols, Verfahren zu ihrer Herstellung und ihre Anwendung als Pestizide | |
| DE69210639T2 (de) | 3-(3,3,3-Trifluor-2-Chlorpropenyl)-2,2-Dimethylcyclopropancarbonsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung als Pestitzide | |
| DE2740701C2 (de) | Verfahren zur Herstellung von Cyclopropancarbonsäureestern des optisch aktiven Allethrolons | |
| DE1695763B2 (de) | Cyclopropancarbonsäureester | |
| DE3207009A1 (de) | Ester heterocyclischer sich von thiazol oder thiadiazol ableitender alkohole, deren herstellungsverfahren und die sie enthaltenden pestiziden zusammensetzungen | |
| DE2624177A1 (de) | Verfahren zur herstellung von m-benzoylhydratropsaeure | |
| DE2316705B2 (de) | 9-Acyl-3' '-thiomethoxymethyl-SF-837-Macrolid-Antibiotika, Verfahren zur Herstellung derselben sowie diese enthaltende pharmazeutische MIttel | |
| DE1620200C3 (de) | 7-Oxo-desacetamido-colchicinderivate, ein Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel. Ausscheidung aus: 1235322 | |
| DE3879018T2 (de) | Pyrethrinoid-derivate, die ein n-heteroring enthalten, verfahren und zwischenprodukte zu deren herstellung, deren anwendung als pestizide, und diese enthaltende zusammenstellungen. | |
| CH637401A5 (de) | Acylderivate der 2-(3-(2-chloraethyl)-3-nitrosoureido)-2-desoxy-d-glucopyranose. | |
| DE4436619C2 (de) | Nematizide Mittel gegen Kiefernholz-Nematoden | |
| DE1445626A1 (de) | Verfahren zur Gewinnung von Alkaloiden | |
| DE1298981B (de) | D-threo-1-Phenyl-2-amino-1, 3-propandiolderivate und Verfahren zu ihrer Herstellung | |
| DE1593964C3 (de) | Triacetyl-Spiramycin I und Verfahren zu seiner Herstellung | |
| DE2335759C2 (de) | Disteroidyläther, Verfahren zur Herstellung derselben und diese enthaltende pharmazeutische Präparate | |
| DE69909960T2 (de) | Cyclopropylestern von Alfa-Tocopherol, Vitamin E Derivate und Verfahren zu deren Herstellung |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |