DD151930A5 - Verfahren zur herstellung optisch aktiver cyclopropancarbonsaeurederivate - Google Patents

Verfahren zur herstellung optisch aktiver cyclopropancarbonsaeurederivate Download PDF

Info

Publication number: DD151930A5
Authority: DD; German Democratic Republic
Prior art keywords: formula; optically active; acid; methyl; hydrogen
Prior art date: 1978-12-15

Application number

DD79217653A

Other languages

German (de)

English (en)

Inventor

John G Dingwall

Hans Greuter

Pierre Martin

Peter Ackermann

Laurenz Gsell

Original Assignee

Ciba Geigy Ag

Priority date (The priority date 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 date listed.)

1978-12-15

Filing date

1979-12-13

Publication date

1981-11-11

1979-12-13 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1981-11-11 Publication of DD151930A5 publication Critical patent/DD151930A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 29
SHQSVMDWKBRBGB-UHFFFAOYSA-N cyclobutanone Chemical compound O=C1CCC1 SHQSVMDWKBRBGB-UHFFFAOYSA-N 0.000 claims abstract description 40
239000000203 mixture Substances 0.000 claims abstract description 35
238000006243 chemical reaction Methods 0.000 claims abstract description 27
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 18
YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims abstract description 15
238000002360 preparation method Methods 0.000 claims abstract description 15
238000000354 decomposition reaction Methods 0.000 claims abstract description 12
150000003460 sulfonic acids Chemical class 0.000 claims abstract description 9
230000031709 bromination Effects 0.000 claims abstract description 4
238000005893 bromination reaction Methods 0.000 claims abstract description 4
-1 phenoxy, 4-methylphenoxy, 4-chlorophenoxy, 4-fluorophenoxy Chemical group 0.000 claims description 50
125000004432 carbon atom Chemical group C* 0.000 claims description 36
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 33
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 31
125000000217 alkyl group Chemical group 0.000 claims description 28
239000000460 chlorine Substances 0.000 claims description 27
229910052801 chlorine Inorganic materials 0.000 claims description 25
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
229910052739 hydrogen Inorganic materials 0.000 claims description 22
239000001257 hydrogen Substances 0.000 claims description 22
150000003839 salts Chemical class 0.000 claims description 22
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 21
229910052794 bromium Chemical group 0.000 claims description 21
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 18
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 16
125000001309 chloro group Chemical group Cl* 0.000 claims description 14
229910052757 nitrogen Inorganic materials 0.000 claims description 13
239000003960 organic solvent Substances 0.000 claims description 13
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
239000002904 solvent Substances 0.000 claims description 12
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 6
125000001188 haloalkyl group Chemical group 0.000 claims description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 5
125000002947 alkylene group Chemical group 0.000 claims description 5
238000000926 separation method Methods 0.000 claims description 5
KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 claims description 4
KWGRBVOPPLSCSI-PSASIEDQSA-N (1s,2r)-2-(methylamino)-1-phenylpropan-1-ol Chemical compound CN[C@H](C)[C@@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-PSASIEDQSA-N 0.000 claims description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
150000003254 radicals Chemical class 0.000 claims description 4
RQEUFEKYXDPUSK-SSDOTTSWSA-N (1R)-1-phenylethanamine Chemical compound C[C@@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-SSDOTTSWSA-N 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
125000001246 bromo group Chemical group Br* 0.000 claims description 3
125000004093 cyano group Chemical group *C#N 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
238000001640 fractional crystallisation Methods 0.000 claims description 3
229910052740 iodine Inorganic materials 0.000 claims description 3
125000006501 nitrophenyl group Chemical group 0.000 claims description 3
239000011593 sulfur Substances 0.000 claims description 3
229910052717 sulfur Inorganic materials 0.000 claims description 3
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
150000002009 diols Chemical class 0.000 claims description 2
125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 2
239000012433 hydrogen halide Substances 0.000 claims description 2
229910000039 hydrogen halide Inorganic materials 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
229910052727 yttrium Inorganic materials 0.000 claims description 2
150000002431 hydrogen Chemical group 0.000 claims 4
BTANRVKWQNVYAZ-SCSAIBSYSA-N (2R)-butan-2-ol Chemical compound CC[C@@H](C)O BTANRVKWQNVYAZ-SCSAIBSYSA-N 0.000 claims 1
DTWQXQRQHDSUED-UHFFFAOYSA-N 1-(dimethylamino)propane-1,3-diol Chemical compound CN(C)C(O)CCO DTWQXQRQHDSUED-UHFFFAOYSA-N 0.000 claims 1
AOJJSUZBOXZQNB-VTZDEGQISA-N 4'-epidoxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-VTZDEGQISA-N 0.000 claims 1
LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims 1
BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 claims 1
YSVZGWAJIHWNQK-UHFFFAOYSA-N [3-(hydroxymethyl)-2-bicyclo[2.2.1]heptanyl]methanol Chemical compound C1CC2C(CO)C(CO)C1C2 YSVZGWAJIHWNQK-UHFFFAOYSA-N 0.000 claims 1
150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
KTHXBEHDVMTNOH-UHFFFAOYSA-N cyclobutanol Chemical class OC1CCC1 KTHXBEHDVMTNOH-UHFFFAOYSA-N 0.000 claims 1
229960002179 ephedrine Drugs 0.000 claims 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
210000002700 urine Anatomy 0.000 claims 1
239000002917 insecticide Substances 0.000 abstract description 4
239000000575 pesticide Substances 0.000 abstract description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 62
239000000243 solution Substances 0.000 description 36
239000002585 base Substances 0.000 description 33
150000001875 compounds Chemical class 0.000 description 30
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 25
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
239000002253 acid Substances 0.000 description 24
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
150000007513 acids Chemical class 0.000 description 13
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000000741 silica gel Substances 0.000 description 12
229910002027 silica gel Inorganic materials 0.000 description 12
239000003054 catalyst Substances 0.000 description 11
GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 11
238000001704 evaporation Methods 0.000 description 11
UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
230000008020 evaporation Effects 0.000 description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
230000006340 racemization Effects 0.000 description 8
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
125000001931 aliphatic group Chemical group 0.000 description 7
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
229910000147 aluminium phosphate Inorganic materials 0.000 description 6
150000001408 amides Chemical class 0.000 description 6
238000004587 chromatography analysis Methods 0.000 description 6
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
SMISKVVLRWGLGK-UHFFFAOYSA-N 2-chloro-3,3-dimethyl-4-(2,2,2-trichloroethyl)cyclobutan-1-one Chemical compound CC1(C)C(Cl)C(=O)C1CC(Cl)(Cl)Cl SMISKVVLRWGLGK-UHFFFAOYSA-N 0.000 description 5
229910052783 alkali metal Inorganic materials 0.000 description 5
150000001340 alkali metals Chemical class 0.000 description 5
239000012043 crude product Substances 0.000 description 5
QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 5
239000012071 phase Substances 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
238000003756 stirring Methods 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
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 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
238000001816 cooling Methods 0.000 description 4
GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 4
239000000284 extract Substances 0.000 description 4
230000000749 insecticidal effect Effects 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
239000007858 starting material Substances 0.000 description 4
ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 4
RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 3
SUTSHJDDLIPDFI-UHFFFAOYSA-N 2-chloro-3,3-dimethyl-4-(2,2,2-tribromoethyl)cyclobutan-1-one Chemical compound CC1(C)C(Cl)C(=O)C1CC(Br)(Br)Br SUTSHJDDLIPDFI-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
239000005977 Ethylene Substances 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
239000007983 Tris buffer Substances 0.000 description 3
235000011054 acetic acid Nutrition 0.000 description 3
229910052784 alkaline earth metal Inorganic materials 0.000 description 3
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000011575 calcium Substances 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
150000003950 cyclic amides Chemical class 0.000 description 3
150000004292 cyclic ethers Chemical class 0.000 description 3
239000003480 eluent Substances 0.000 description 3
238000000605 extraction Methods 0.000 description 3
XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
239000000155 melt Substances 0.000 description 3
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 3
125000001624 naphthyl group Chemical group 0.000 description 3
150000007530 organic bases Chemical class 0.000 description 3
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 3
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
239000000047 product Substances 0.000 description 3
239000002728 pyrethroid Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
239000000725 suspension Substances 0.000 description 3
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 3
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 description 2
AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 2
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
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 2
JCBPETKZIGVZRE-UHFFFAOYSA-N 2-aminobutan-1-ol Chemical compound CCC(N)CO JCBPETKZIGVZRE-UHFFFAOYSA-N 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
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150000008045 alkali metal halides Chemical class 0.000 description 1
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TZIHFWKZFHZASV-UHFFFAOYSA-N anhydrous methyl formate Natural products COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 1
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239000008346 aqueous phase Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
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150000007514 bases Chemical class 0.000 description 1
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235000019445 benzyl alcohol Nutrition 0.000 description 1
150000003938 benzyl alcohols Chemical class 0.000 description 1
CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
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BLGXFZZNTVWLAY-UHFFFAOYSA-N beta-Yohimbin Natural products C1=CC=C2C(CCN3CC4CCC(O)C(C4CC33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
WRMFBHHNOHZECA-UHFFFAOYSA-N butan-2-olate Chemical compound CCC(C)[O-] WRMFBHHNOHZECA-UHFFFAOYSA-N 0.000 description 1
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229910052791 calcium Inorganic materials 0.000 description 1
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150000004649 carbonic acid derivatives Chemical class 0.000 description 1
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239000003795 chemical substances by application Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
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125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
KMPWYEUPVWOPIM-UHFFFAOYSA-N cinchonidine Natural products C1=CC=C2C(C(C3N4CCC(C(C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-UHFFFAOYSA-N 0.000 description 1
KMPWYEUPVWOPIM-QAMTZSDWSA-N cinchonine Chemical compound C1=CC=C2C([C@@H]([C@@H]3[N@]4CC[C@H]([C@H](C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-QAMTZSDWSA-N 0.000 description 1
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125000000753 cycloalkyl group Chemical group 0.000 description 1
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150000004985 diamines Chemical class 0.000 description 1
150000001991 dicarboxylic acids Chemical class 0.000 description 1
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239000012259 ether extract Substances 0.000 description 1
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230000003287 optical effect Effects 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
238000005949 ozonolysis reaction Methods 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
229960003975 potassium Drugs 0.000 description 1
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239000002244 precipitate Substances 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
150000003139 primary aliphatic amines Chemical class 0.000 description 1
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235000019260 propionic acid Nutrition 0.000 description 1
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239000012429 reaction media Substances 0.000 description 1
LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
150000005619 secondary aliphatic amines Chemical class 0.000 description 1
150000003336 secondary aromatic amines Chemical class 0.000 description 1
229910052711 selenium Inorganic materials 0.000 description 1
229910001961 silver nitrate Inorganic materials 0.000 description 1
101150114085 soc-2 gene Proteins 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
229940001593 sodium carbonate Drugs 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000011775 sodium fluoride Substances 0.000 description 1
235000013024 sodium fluoride Nutrition 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
241000894007 species Species 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
150000003455 sulfinic acids Chemical class 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
QOISWWBTZMFUEL-NSHDSACASA-N tert-butyl (2s)-2-amino-3-phenylpropanoate Chemical compound CC(C)(C)OC(=O)[C@@H](N)CC1=CC=CC=C1 QOISWWBTZMFUEL-NSHDSACASA-N 0.000 description 1
150000003510 tertiary aliphatic amines Chemical class 0.000 description 1
150000003513 tertiary aromatic amines Chemical class 0.000 description 1
NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 1
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238000004809 thin layer chromatography Methods 0.000 description 1
ZPHGMBGIFODUMF-UHFFFAOYSA-N thiophen-2-ylmethanol Chemical compound OCC1=CC=CS1 ZPHGMBGIFODUMF-UHFFFAOYSA-N 0.000 description 1
LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 1
150000004992 toluidines Chemical class 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
KLBOFRLEHJAXIU-UHFFFAOYSA-N tributylazanium;chloride Chemical compound Cl.CCCCN(CCCC)CCCC KLBOFRLEHJAXIU-UHFFFAOYSA-N 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
125000006000 trichloroethyl group Chemical group 0.000 description 1
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125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
SZEMGTQCPRNXEG-UHFFFAOYSA-M trimethyl(octadecyl)azanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C SZEMGTQCPRNXEG-UHFFFAOYSA-M 0.000 description 1
GNMJFQWRASXXMS-UHFFFAOYSA-M trimethyl(phenyl)azanium;bromide Chemical compound [Br-].C[N+](C)(C)C1=CC=CC=C1 GNMJFQWRASXXMS-UHFFFAOYSA-M 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
BLGXFZZNTVWLAY-SCYLSFHTSA-N yohimbine Chemical compound C1=CC=C2C(CCN3C[C@@H]4CC[C@H](O)[C@@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-SCYLSFHTSA-N 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/54—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of compounds containing doubly bound oxygen atoms, e.g. esters
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Detergent Compositions (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Furan Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

DD79217653A 1978-12-15 1979-12-13 Verfahren zur herstellung optisch aktiver cyclopropancarbonsaeurederivate DD151930A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1278478		1978-12-15

Publications (1)

Publication Number	Publication Date
DD151930A5 true DD151930A5 (de)	1981-11-11

Family

ID=4386366

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD79217653A DD151930A5 (de)	1978-12-15	1979-12-13	Verfahren zur herstellung optisch aktiver cyclopropancarbonsaeurederivate

Country Status (19)

Country	Link
US (2)	US4299967A (fr)
EP (1)	EP0012722B1 (fr)
JP (1)	JPS5932455B2 (fr)
AT (1)	ATE468T1 (fr)
BR (1)	BR7908212A (fr)
CA (1)	CA1136636A (fr)
CS (1)	CS214680B2 (fr)
DD (1)	DD151930A5 (fr)
DE (1)	DE2961566D1 (fr)
DK (1)	DK160546C (fr)
ES (1)	ES8107145A1 (fr)
FI (1)	FI793891A7 (fr)
GR (1)	GR72730B (fr)
HU (1)	HU184619B (fr)
IL (1)	IL58963A (fr)
MX (1)	MX6292E (fr)
NO (2)	NO150957C (fr)
PL (1)	PL220431A2 (fr)
ZA (1)	ZA796855B (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2499071A1 (fr) *	1981-02-05	1982-08-06	Roussel Uclaf	Nouveaux derives de l'acide cyclopropane carboxylique substitue en 3 par une chaine vinylique, leur procede de preparation et leur application comme agents parfumants
EP0074856A3 (fr) *	1981-09-16	1984-02-01	Glaxo Group Limited	Résolution de bicyclohepténones racémiques
US4845272A (en) *	1987-07-10	1989-07-04	Kuraray Co., Ltd.	Process for the optical resolution of (±)-cis or (±)-trans-permethric acid
US5807482A (en) *	1997-10-31	1998-09-15	Uop Llc	Chiral stationary phase based on yohimbinic acid
KR19990084855A (ko) *	1998-05-12	1999-12-06	성재갑	시스-퍼메스린산의 광학적 분할방법
DE19960914A1 (de) *	1998-12-28	2000-06-29	Luk Getriebe Systeme Gmbh	Umschlingungsmittel
CN101296917A (zh) *	2005-10-24	2008-10-29	霍夫曼-拉罗奇有限公司	由法沃斯基重排制备环状缩酮化酮及该方法在制备葡糖激酶活化剂70中的应用

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1446304A (en)	1972-05-25	1976-08-18	Nat Res Dev	3-substituted cyclopropane carboxylic acids and derivatives thereof
CA1051454A (fr) *	1975-05-21	1979-03-27	Marinus J. Van Den Brink	Methode de preparation de cyclobutanones
GB1571581A (en) *	1976-01-06	1980-07-16	Shell Int Research	Process for the preparation of 2-halocyclobutanones and cyclopropane carbolic acids derived therefrom
DE2654062A1 (de) *	1976-08-26	1978-03-23	Bayer Ag	Verfahren zur herstellung vinylsubstituierter cyclopropancarbonsaeuren
SE441179B (sv) *	1976-09-21	1985-09-16	Roussel Uclaf	Nya cyklopropankarboxylsyror med polyhalogenerad substituent, sett for framstellning derav samt anvendning derav i pesticidkompositioner
DE2813337A1 (de) *	1977-03-31	1978-10-05	Ciba Geigy Ag	Verfahren zur herstellung von 2-(2', 2',2'-trihalogenaethyl)-4-halogencyclobutan1-onen
EP0002206A1 (fr) *	1977-11-24	1979-06-13	Ciba-Geigy Ag	Chlorures d'acides butyriques halogénés, leur préparation et leur utilisation comme produits intermédiaires pour la préparation de pesticides
US4255351A (en) *	1978-03-14	1981-03-10	Ciba-Geigy Corporation	Sulfonic acid esters of 2,2,2-trichloroethylhydroxycyclobutanones

1979
- 1979-12-10 AT AT79810176T patent/ATE468T1/de not_active IP Right Cessation
- 1979-12-10 DE DE7979810176T patent/DE2961566D1/de not_active Expired
- 1979-12-10 EP EP79810176A patent/EP0012722B1/fr not_active Expired
- 1979-12-12 FI FI793891A patent/FI793891A7/fi not_active Application Discontinuation
- 1979-12-13 CA CA000341786A patent/CA1136636A/fr not_active Expired
- 1979-12-13 MX MX798548U patent/MX6292E/es unknown
- 1979-12-13 DD DD79217653A patent/DD151930A5/de unknown
- 1979-12-13 GR GR60745A patent/GR72730B/el unknown
- 1979-12-14 IL IL58963A patent/IL58963A/xx unknown
- 1979-12-14 JP JP54161703A patent/JPS5932455B2/ja not_active Expired
- 1979-12-14 HU HU79CI1998A patent/HU184619B/hu unknown
- 1979-12-14 CS CS798819A patent/CS214680B2/cs unknown
- 1979-12-14 PL PL22043179A patent/PL220431A2/xx unknown
- 1979-12-14 NO NO794102A patent/NO150957C/no unknown
- 1979-12-14 DK DK533579A patent/DK160546C/da not_active IP Right Cessation
- 1979-12-14 BR BR7908212A patent/BR7908212A/pt unknown
- 1979-12-15 ES ES487505A patent/ES8107145A1/es not_active Expired
- 1979-12-17 US US06/103,983 patent/US4299967A/en not_active Expired - Lifetime
- 1979-12-18 ZA ZA00796855A patent/ZA796855B/xx unknown
1980
- 1980-08-27 NO NO802540A patent/NO150240C/no unknown
- 1980-12-24 US US06/219,803 patent/US4335057A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
NO150240C (no)	1984-09-12
ES487505A0 (es)	1980-12-16
JPS5932455B2 (ja)	1984-08-09
DK160546B (da)	1991-03-25
NO802540L (no)	1980-06-17
ES8107145A1 (es)	1980-12-16
HU184619B (en)	1984-09-28
DK533579A (da)	1980-06-16
IL58963A (en)	1983-09-30
EP0012722B1 (fr)	1981-12-09
US4335057A (en)	1982-06-15
CA1136636A (fr)	1982-11-30
NO150240B (no)	1984-06-04
FI793891A7 (fi)	1981-01-01
PL220431A2 (fr)	1980-10-06
JPS5585541A (en)	1980-06-27
CS214680B2 (en)	1982-05-28
US4299967A (en)	1981-11-10
ZA796855B (en)	1980-12-31
NO794102L (no)	1980-06-17
BR7908212A (pt)	1980-08-26
IL58963A0 (en)	1980-03-31
DK160546C (da)	1991-09-30
NO150957C (no)	1985-01-16
ATE468T1 (de)	1981-12-15
NO150957B (no)	1984-10-08
MX6292E (es)	1985-03-18
EP0012722A1 (fr)	1980-06-25
DE2961566D1 (en)	1982-02-04
GR72730B (fr)	1983-12-01

Publication	Publication Date	Title
EP0318425B1 (fr)	1992-03-18	Dérivés du 2,2-difluorocyclopropyléthane, procédé pour leur fabrication et leur utilisation comme agent de destruction de parasites
EP0341475A2 (fr)	1989-11-15	Stéréo-isomères de N-(R)-1-aryl-éthyl)-1-alkyl-2,2-dichlorocyclopropane carboxamide
CH638171A5 (de)	1983-09-15	Substituierte cyclopropancarbonsaeureester.
DE3941966A1 (de)	1991-06-20	Halogenierte olefine, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel
EP0003060B1 (fr)	1981-11-25	Procédé de séparation d'acides vinylcyclopropanecarboxyliques stéréoisomériques substitués
DE2500265A1 (de)	1976-07-08	Neue mikrobizide
EP0012722B1 (fr)	1981-12-09	Procédé de préparation d'acides 2-(2',2'-dihalogénovinyl)-cyclopropan-1-carboxyliques 3-substitués optiquement actifs et de leurs dérivés; sels d'acides 4-(2',2',2'-trihalogéno-éthyl)-cyclobutan-1-sulphoniques et leur préparation
DE2812169C2 (fr)	1991-10-17
DE3908901A1 (de)	1990-09-20	2-halogencycloprohylethanderivate, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel
CH646837A5 (de)	1984-12-28	Gemisch von 1rciss- und 1scisr-cyclopropancarbonsaeureester-derivaten mit pesticider wirkung.
DE2727326C2 (de)	1986-04-30	Verfahren zur Herstellung von Dimethylcyclopropancarbonsäure- oder Phenylessigsäurederivaten
DD158239A5 (de)	1983-01-05	Verfahren zur herstellung von cyclopropancarbonsaeureester-derivaten
DD150455A6 (de)	1981-09-02	Verfahren zur herstellung von phenylalkansaeure-m-phenoxy-benzylestern
DE2813337C2 (fr)	1989-03-02
DE2258985A1 (de)	1973-06-14	Verfahren zur herstellung von 2-(3benzoylphenyl)-propionsaeure und analogen produkten
EP0002207B1 (fr)	1981-09-02	Dichlorovinylcyclobutanones, leur procédé de préparation et leur utilisation comme intermédiaires dans la préparation de pesticides
EP0008732A2 (fr)	1980-03-19	Esters fluorés d'acides phénylacétiques, procédé de préparation, leur utilisation comme insecticides et acaricides; produits intermédiaires pour leur préparation
EP0046950B1 (fr)	1984-04-11	Isomères optiquement actifs d'esters (alpha-cyano-4-fluoro-3-phénoxy)benzyliques d'acide trans-3-(2-chloro-2-(4-chlorophényl)-vinyl)-2,2-diméthylcyclopropionique, procédé pour leur préparation et utilisation comme ectoparasiticides
EP0025542A2 (fr)	1981-03-25	Esters (+/-)-(alpha-cyano-3-phénoxy-4-fluoro-benzyliques) de l'acide (+/-)-trans-3-(E,Z-2-chloro-2-(4-chloro-phényl)-vinyl)-2,2-diméthyl-cyclopropane carboxylique, leurs isomères E- et Z-, procédé pour la préparation de ces composés, leur utilisation comme ectoparasiticides et leurs intermédiaires
DD149012A5 (de)	1981-06-24	Bodeninsektizide mittel
CH647750A5 (de)	1985-02-15	Zweiringige aromatische insektizide.
DE4123585C1 (en)	1992-11-05	Fluoroolefin for insecticide and nematocide - prepd. by reacting fluoroolefin intermediate with phosphonium salt in base, for high acaricidal activity
EP0302331A2 (fr)	1989-02-08	Esters de carbinols arylbisperfluoralkyles, procédé pour leur fabrication et pour les carbinols arylbisperfluoralkyles en question
EP0004316B1 (fr)	1981-09-23	Esters de l'acide cyclopropanecarboxylique, procédé de préparation et leur utilisation dans la lutte contre les parasites
DE2335347C3 (de)	1977-04-07	Substituierte Essigsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung als Pestizide