DD154973A5 - Verfahren zur herstellung von cyclopropancarbonsaeureester-derivate - Google Patents
Verfahren zur herstellung von cyclopropancarbonsaeureester-derivate Download PDFInfo
- Publication number
- DD154973A5 DD154973A5 DD80225458A DD22545880A DD154973A5 DD 154973 A5 DD154973 A5 DD 154973A5 DD 80225458 A DD80225458 A DD 80225458A DD 22545880 A DD22545880 A DD 22545880A DD 154973 A5 DD154973 A5 DD 154973A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- isomers
- mixture
- lrcisr
- solution
- lscisr
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 31
- 230000008569 process Effects 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 239000002253 acid Substances 0.000 title description 3
- 150000002148 esters Chemical class 0.000 title 1
- 239000000203 mixture Substances 0.000 claims abstract description 53
- 150000001875 compounds Chemical class 0.000 claims abstract description 34
- 239000007787 solid Substances 0.000 claims abstract description 16
- 239000002904 solvent Substances 0.000 claims abstract description 14
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000000460 chlorine Substances 0.000 claims abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
- 239000000243 solution Substances 0.000 claims description 31
- 239000002585 base Substances 0.000 claims description 23
- -1 cyclopropanecarboxylic ester Chemical class 0.000 claims description 16
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- 238000002844 melting Methods 0.000 claims description 4
- 230000008018 melting Effects 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- BWYMTLSWYSEZCV-UHFFFAOYSA-N cyano 3-(2,2-dichloroethenyl)-2,2-dimethyl-1-[(3-phenoxyphenyl)methyl]cyclopropane-1-carboxylate Chemical compound CC1(C)C(C=C(Cl)Cl)C1(C(=O)OC#N)CC1=CC=CC(OC=2C=CC=CC=2)=C1 BWYMTLSWYSEZCV-UHFFFAOYSA-N 0.000 claims description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims 1
- 150000008041 alkali metal carbonates Chemical class 0.000 claims 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
- 230000007704 transition Effects 0.000 claims 1
- 230000000361 pesticidal effect Effects 0.000 abstract description 12
- 230000002363 herbicidal effect Effects 0.000 abstract description 2
- VFVUEHVSWANYJR-UHFFFAOYSA-N carbonic acid;cyclopropane Chemical class C1CC1.OC(O)=O VFVUEHVSWANYJR-UHFFFAOYSA-N 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
- 239000000047 product Substances 0.000 description 23
- 239000003208 petroleum Substances 0.000 description 17
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 11
- 238000002425 crystallisation Methods 0.000 description 10
- 230000008025 crystallization Effects 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000011141 high resolution liquid chromatography Methods 0.000 description 8
- 239000013078 crystal Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000002270 dispersing agent Substances 0.000 description 6
- 230000006340 racemization Effects 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000003158 alcohol group Chemical group 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 150000007942 carboxylates Chemical class 0.000 description 3
- 229920001429 chelating resin Polymers 0.000 description 3
- 239000004495 emulsifiable concentrate Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 239000004546 suspension concentrate Substances 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- PVVYCQYMEZFWPS-UHFFFAOYSA-N 3-(2,2-dibromoethenyl)-2,2-dimethyl-1-[(3-phenoxyphenyl)methyl]cyclopropane-1-carbonitrile Chemical compound C(#N)C1(C(C1C=C(Br)Br)(C)C)CC1=CC(=CC=C1)OC1=CC=CC=C1 PVVYCQYMEZFWPS-UHFFFAOYSA-N 0.000 description 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 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 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 1
- 102000014150 Interferons Human genes 0.000 description 1
- 108010050904 Interferons Proteins 0.000 description 1
- 241000899717 Itaya Species 0.000 description 1
- 241000212342 Sium Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000005263 alkylenediamine group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000002528 anti-freeze Effects 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 238000011914 asymmetric synthesis Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000005667 attractant Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical class [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical group OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 235000015872 dietary supplement Nutrition 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 229940047124 interferons Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000006259 organic additive Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000003016 pheromone Substances 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-O tert-butylammonium Chemical compound CC(C)(C)[NH3+] YBRBMKDOPFTVDT-UHFFFAOYSA-O 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- 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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7940856 | 1979-11-27 | ||
| GB7940857 | 1979-11-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD154973A5 true DD154973A5 (de) | 1982-05-05 |
Family
ID=26273687
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD80225458A DD154973A5 (de) | 1979-11-27 | 1980-11-25 | Verfahren zur herstellung von cyclopropancarbonsaeureester-derivate |
Country Status (25)
| Country | Link |
|---|---|
| AU (1) | AU6467780A (cs) |
| BG (1) | BG42352A3 (cs) |
| BR (1) | BR8007688A (cs) |
| CA (1) | CA1150301A (cs) |
| CH (1) | CH646837A5 (cs) |
| CS (1) | CS219296B2 (cs) |
| DD (1) | DD154973A5 (cs) |
| DE (1) | DE3044391A1 (cs) |
| DK (1) | DK501880A (cs) |
| ES (1) | ES8201940A1 (cs) |
| FR (1) | FR2470117A1 (cs) |
| GB (1) | GB2064528B (cs) |
| IE (1) | IE50479B1 (cs) |
| IL (1) | IL61557A0 (cs) |
| IN (1) | IN155143B (cs) |
| IT (1) | IT1134448B (cs) |
| MX (1) | MX6132E (cs) |
| NL (1) | NL8006398A (cs) |
| NZ (1) | NZ195637A (cs) |
| OA (1) | OA06708A (cs) |
| PL (1) | PL129811B1 (cs) |
| RO (1) | RO80004A (cs) |
| SE (1) | SE453079B (cs) |
| SU (1) | SU1068036A3 (cs) |
| YU (1) | YU41954B (cs) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1162560A (en) * | 1980-04-23 | 1984-02-21 | Ronald F. Mason | Process for preparing cyclopropane carboxylic acid ester derivatives |
| EP0106469B1 (en) * | 1982-10-11 | 1987-01-14 | Imperial Chemical Industries Plc | Insecticidal product and preparation thereof |
| GB2128607A (en) * | 1982-10-18 | 1984-05-02 | Ici Plc | An enantiomeric pair of cyhalothrin isomers and process for preparation thereof |
| GB8418331D0 (en) * | 1984-07-18 | 1984-08-22 | Ici Plc | Insecticidal ester |
| CA1275108A (en) * | 1985-01-16 | 1990-10-09 | Laszlo Pap | Insecticidal composition comprising more than one active ingredients |
| DE3522629A1 (de) * | 1985-06-25 | 1987-01-08 | Bayer Ag | Verfahren zur herstellung bestimmter enantiomerenpaare von permethrinsaeure-(alpha)-cyano-3-phenoxy-4-fluor-benzyl -ester |
| CA1314559C (en) * | 1987-06-15 | 1993-03-16 | John Winfrid Ager | Conversion of pyrethroid isomers to more active species |
| US4997970A (en) * | 1987-06-15 | 1991-03-05 | Fmc Corporation | Conversion of pyrethroid isomers to move active species |
| BR9004617A (pt) * | 1989-01-17 | 1991-07-30 | Chinoin Gyogyszer Es Vegyeszet | Processo para a preparacao de isomeros de cipermetrina |
| US5128497A (en) * | 1990-01-03 | 1992-07-07 | Fmc Corporation | Conversion of pyrethroid isomers to more active species |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4152410A (en) * | 1975-09-03 | 1979-05-01 | Eisai Co., Ltd. | Diagnosis reagent for neoplasm and method for diagnosis of neoplasm |
| FR2375161A1 (fr) * | 1976-04-23 | 1978-07-21 | Roussel Uclaf | Procede de transformation d'un ester d'acide chiral d'alcool secondaire a-cyane optiquement actif de structure (r) en ester d'acide chiral d'alcool secondaire a-cyane de structure (s) |
| FR2348901A1 (fr) * | 1976-04-23 | 1977-11-18 | Roussel Uclaf | Procede de transformation d'un ester d'acide chiral d'alcool secondaire alpha-cyane optiquement actif en ester d'acide chiral d'alcool secondaire alpha-cyane racemique |
| US4261921A (en) * | 1979-06-06 | 1981-04-14 | Fmc Corporation | Process for preparation of a crystalline insecticidal pyrethroid enantiomer pair |
-
1980
- 1980-10-10 CA CA000362132A patent/CA1150301A/en not_active Expired
- 1980-11-21 OA OA57259A patent/OA06708A/xx unknown
- 1980-11-23 SU SU803007801A patent/SU1068036A3/ru active
- 1980-11-24 NL NL8006398A patent/NL8006398A/nl not_active Application Discontinuation
- 1980-11-25 SE SE8008254A patent/SE453079B/sv not_active IP Right Cessation
- 1980-11-25 ES ES497098A patent/ES8201940A1/es not_active Expired
- 1980-11-25 IN IN836/DEL/80A patent/IN155143B/en unknown
- 1980-11-25 DE DE19803044391 patent/DE3044391A1/de not_active Withdrawn
- 1980-11-25 DD DD80225458A patent/DD154973A5/de unknown
- 1980-11-25 YU YU2988/80A patent/YU41954B/xx unknown
- 1980-11-25 GB GB8037693A patent/GB2064528B/en not_active Expired
- 1980-11-25 PL PL1980228060A patent/PL129811B1/pl unknown
- 1980-11-25 IL IL61557A patent/IL61557A0/xx unknown
- 1980-11-25 FR FR8024980A patent/FR2470117A1/fr active Pending
- 1980-11-25 IT IT26215/80A patent/IT1134448B/it active
- 1980-11-25 NZ NZ195637A patent/NZ195637A/xx unknown
- 1980-11-25 BG BG049773A patent/BG42352A3/xx unknown
- 1980-11-25 RO RO80102679A patent/RO80004A/ro unknown
- 1980-11-25 BR BR8007688A patent/BR8007688A/pt not_active IP Right Cessation
- 1980-11-25 AU AU64677/80A patent/AU6467780A/en not_active Abandoned
- 1980-11-25 CH CH871980A patent/CH646837A5/de not_active IP Right Cessation
- 1980-11-25 CS CS808146A patent/CS219296B2/cs unknown
- 1980-11-25 IE IE2442/80A patent/IE50479B1/en not_active IP Right Cessation
- 1980-11-25 MX MX809176U patent/MX6132E/es unknown
- 1980-11-25 DK DK501880A patent/DK501880A/da not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| BG42352A3 (en) | 1987-11-14 |
| GB2064528B (en) | 1983-10-19 |
| DK501880A (da) | 1981-05-28 |
| OA06708A (fr) | 1982-05-30 |
| YU298880A (en) | 1984-02-29 |
| FR2470117A1 (fr) | 1981-05-29 |
| IN155143B (cs) | 1985-01-05 |
| RO80004A (ro) | 1982-10-11 |
| CA1150301A (en) | 1983-07-19 |
| AU6467780A (en) | 1981-06-04 |
| CH646837A5 (de) | 1984-12-28 |
| SU1068036A3 (ru) | 1984-01-15 |
| YU41954B (en) | 1988-02-29 |
| CS219296B2 (en) | 1983-03-25 |
| BR8007688A (pt) | 1981-06-09 |
| SE453079B (sv) | 1988-01-11 |
| IT8026215A0 (it) | 1980-11-25 |
| ES497098A0 (es) | 1982-01-01 |
| IT1134448B (it) | 1986-08-13 |
| PL129811B1 (en) | 1984-06-30 |
| ES8201940A1 (es) | 1982-01-01 |
| DE3044391A1 (de) | 1981-08-27 |
| IL61557A0 (en) | 1980-12-31 |
| MX6132E (es) | 1984-11-22 |
| PL228060A1 (cs) | 1981-07-24 |
| IE802442L (en) | 1981-05-27 |
| SE8008254L (sv) | 1981-05-28 |
| IE50479B1 (en) | 1986-04-30 |
| NZ195637A (en) | 1983-09-30 |
| NL8006398A (nl) | 1981-07-01 |
| GB2064528A (en) | 1981-06-17 |
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