BG62253B1 - Халогенирани естери, метод за получаването им и приложениетоим като междинни съединения за получаване на инсектициди - Google Patents

Халогенирани естери, метод за получаването им и приложениетоим като междинни съединения за получаване на инсектициди Download PDF

Info

Publication number: BG62253B1
Authority: BG; Bulgaria
Prior art keywords: compound; formula; preparation; alkali metal; base
Prior art date: 1994-11-25

Application number

BG101606A

Other languages

Bulgarian (bg)

English (en)

Other versions

BG101606A (en

Inventor

Martin C. Bowden

Original Assignee

Zeneca Limited

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.)

1994-11-25

Filing date

1997-06-11

Publication date

1999-06-30

1994-11-25 Priority claimed from GB9423800A external-priority patent/GB9423800D0/en

1995-07-18 Priority claimed from GBGB9514652.8A external-priority patent/GB9514652D0/en

1997-06-11 Application filed by Zeneca Limited filed Critical Zeneca Limited

1998-03-31 Publication of BG101606A publication Critical patent/BG101606A/xx

1999-06-30 Publication of BG62253B1 publication Critical patent/BG62253B1/bg

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 37
238000000034 method Methods 0.000 title claims abstract description 23
238000002360 preparation method Methods 0.000 title claims abstract description 19
239000002917 insecticide Substances 0.000 title claims description 5
238000004519 manufacturing process Methods 0.000 title claims description 4
150000002148 esters Chemical class 0.000 title description 4
125000000217 alkyl group Chemical group 0.000 claims abstract description 8
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
239000001257 hydrogen Substances 0.000 claims abstract description 4
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
239000002585 base Substances 0.000 claims description 18
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 12
-1 alkali metal alkoxide Chemical class 0.000 claims description 12
229910052783 alkali metal Inorganic materials 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 claims description 6
239000000460 chlorine Substances 0.000 claims description 6
125000001309 chloro group Chemical group Cl* 0.000 claims description 6
229910000042 hydrogen bromide Inorganic materials 0.000 claims description 6
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 5
239000011953 free-radical catalyst Substances 0.000 claims description 5
239000012442 inert solvent Substances 0.000 claims description 5
229910052708 sodium Inorganic materials 0.000 claims description 5
239000011734 sodium Substances 0.000 claims description 5
ZXQYGBMAQZUVMI-RDDWSQKMSA-N (1S)-cis-(alphaR)-cyhalothrin Chemical compound CC1(C)[C@H](\C=C(/Cl)C(F)(F)F)[C@@H]1C(=O)O[C@@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-RDDWSQKMSA-N 0.000 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
229910052794 bromium Chemical group 0.000 claims description 4
239000005910 lambda-Cyhalothrin Substances 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 4
150000001451 organic peroxides Chemical group 0.000 claims description 3
ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical group [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 claims description 3
229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 2
150000008041 alkali metal carbonates Chemical group 0.000 claims description 2
230000018044 dehydration Effects 0.000 claims description 2
238000006297 dehydration reaction Methods 0.000 claims description 2
239000000543 intermediate Substances 0.000 abstract description 3
230000000749 insecticidal effect Effects 0.000 abstract description 2
125000004429 atom Chemical group 0.000 abstract 1
125000001246 bromo group Chemical group Br* 0.000 abstract 1
125000001559 cyclopropyl group Chemical class [H]C1([H])C([H])([H])C1([H])* 0.000 abstract 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
239000000203 mixture Substances 0.000 description 16
MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 11
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
239000002904 solvent Substances 0.000 description 6
238000001704 evaporation Methods 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
238000004821 distillation Methods 0.000 description 4
239000000284 extract Substances 0.000 description 4
YMSWZMRJZFMZEV-UHFFFAOYSA-N methyl 6,6-dichloro-7,7,7-trifluoro-3,3-dimethylhept-4-enoate Chemical compound COC(=O)CC(C)(C)C=CC(Cl)(Cl)C(F)(F)F YMSWZMRJZFMZEV-UHFFFAOYSA-N 0.000 description 4
239000008096 xylene Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
239000012267 brine Substances 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000007788 liquid Substances 0.000 description 3
POSHLXMCOVQXJC-UHFFFAOYSA-N methyl 3,3-dimethyl-5-oxopentanoate Chemical compound COC(=O)CC(C)(C)CC=O POSHLXMCOVQXJC-UHFFFAOYSA-N 0.000 description 3
RAHJLGGRLBRALU-UHFFFAOYSA-N methyl 6,6-dichloro-7,7,7-trifluoro-5-hydroxy-3,3-dimethylheptanoate Chemical compound COC(=O)CC(C)(C)CC(O)C(Cl)(Cl)C(F)(F)F RAHJLGGRLBRALU-UHFFFAOYSA-N 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
239000003921 oil Substances 0.000 description 3
239000003880 polar aprotic solvent Substances 0.000 description 3
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
HWWYDZCSSYKIAD-UHFFFAOYSA-N 3,5-dimethylpyridine Chemical compound CC1=CN=CC(C)=C1 HWWYDZCSSYKIAD-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
239000004342 Benzoyl peroxide Substances 0.000 description 2
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
238000004566 IR spectroscopy Methods 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
238000010533 azeotropic distillation Methods 0.000 description 2
235000019400 benzoyl peroxide Nutrition 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
ANNHJHCLRBLWBB-UHFFFAOYSA-N ethyl 3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CCOC(=O)C1C(C=C(Cl)C(F)(F)F)C1(C)C ANNHJHCLRBLWBB-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
239000007789 gas Substances 0.000 description 2
RJBYQZLKYNWVPE-UHFFFAOYSA-N methyl 5-bromo-3,3-dimethylpentanoate Chemical compound COC(=O)CC(C)(C)CCBr RJBYQZLKYNWVPE-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
239000012258 stirred mixture Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
238000005406 washing Methods 0.000 description 2
SPVZAYWHHVLPBN-NJGYIYPDSA-N (1r,3r)-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)[C@@H](C=C(Cl)C(F)(F)F)[C@H]1C(O)=O SPVZAYWHHVLPBN-NJGYIYPDSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
PRKQVKDSMLBJBJ-UHFFFAOYSA-N ammonium carbonate Chemical class N.N.OC(O)=O PRKQVKDSMLBJBJ-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229950005499 carbon tetrachloride Drugs 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
ZXQYGBMAQZUVMI-UNOMPAQXSA-N cyhalothrin Chemical compound CC1(C)C(\C=C(/Cl)C(F)(F)F)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-UNOMPAQXSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
JBNOXTPQXVDODI-UHFFFAOYSA-N ethyl 6,6-dichloro-7,7,7-trifluoro-3,3-dimethylhept-4-enoate Chemical compound CCOC(=O)CC(C)(C)C=CC(Cl)(Cl)C(F)(F)F JBNOXTPQXVDODI-UHFFFAOYSA-N 0.000 description 1
BEAGBOJVYQJNAS-UHFFFAOYSA-N ethyl 6-bromo-6-chloro-7,7,7-trifluoro-5-hydroxy-3,3-dimethylheptanoate Chemical compound CCOC(=O)CC(C)(C)CC(O)C(Cl)(Br)C(F)(F)F BEAGBOJVYQJNAS-UHFFFAOYSA-N 0.000 description 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N ethylene glycol dimethyl ether Natural products COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
239000011521 glass Substances 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
IPCWFHVHMBOKPA-UHFFFAOYSA-N methyl 3,3-dimethylpentanoate Chemical compound CCC(C)(C)CC(=O)OC IPCWFHVHMBOKPA-UHFFFAOYSA-N 0.000 description 1
ZRLLIXSRKOMDAU-UHFFFAOYSA-N methyl 3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound COC(=O)C1C(C=C(Cl)C(F)(F)F)C1(C)C ZRLLIXSRKOMDAU-UHFFFAOYSA-N 0.000 description 1
LUFYYMAELPSZRE-UHFFFAOYSA-N methyl 4,6-dichloro-7,7,7-trifluoro-3,3-dimethylhept-5-enoate Chemical compound COC(=O)CC(C)(C)C(Cl)C=C(Cl)C(F)(F)F LUFYYMAELPSZRE-UHFFFAOYSA-N 0.000 description 1
MEXKFCWMWJZDMF-UHFFFAOYSA-N n,n-dibutylacetamide Chemical compound CCCCN(C(C)=O)CCCC MEXKFCWMWJZDMF-UHFFFAOYSA-N 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
WQKGAJDYBZOFSR-UHFFFAOYSA-N potassium;propan-2-olate Chemical compound [K+].CC(C)[O-] WQKGAJDYBZOFSR-UHFFFAOYSA-N 0.000 description 1
238000010926 purge Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
WBQTXTBONIWRGK-UHFFFAOYSA-N sodium;propan-2-olate Chemical compound [Na+].CC(C)[O-] WBQTXTBONIWRGK-UHFFFAOYSA-N 0.000 description 1
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
239000012485 toluene extract Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/675—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids of saturated hydroxy-carboxylic acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/62—Halogen-containing esters
- C07C69/65—Halogen-containing esters of unsaturated acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C69/743—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring of acids with a three-membered ring and with unsaturation outside the ring

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

BG101606A 1994-11-25 1997-06-11 Халогенирани естери, метод за получаването им и приложениетоим като междинни съединения за получаване на инсектициди BG62253B1 (bg)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GB9423800A GB9423800D0 (en)	1994-11-25	1994-11-25	Halogenated esters useful as intemediates for insecticides
GBGB9514652.8A GB9514652D0 (en)	1995-07-18	1995-07-18	Halogenated esters useful as intermediates for insecticides
PCT/GB1995/002569 WO1996016925A1 (fr)	1994-11-25	1995-11-02	Esters halogenes utiles comme intermediaires pour des insecticides

Publications (2)

Publication Number	Publication Date
BG101606A BG101606A (en)	1998-03-31
BG62253B1 true BG62253B1 (bg)	1999-06-30

Family

ID=26306041

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BG101606A BG62253B1 (bg)	1994-11-25	1997-06-11	Халогенирани естери, метод за получаването им и приложениетоим като междинни съединения за получаване на инсектициди

Country Status (23)

Country	Link
US (2)	US5750769A (fr)
EP (1)	EP0793637B1 (fr)
JP (2)	JP3839051B2 (fr)
KR (1)	KR100374689B1 (fr)
CN (1)	CN1071306C (fr)
AT (1)	ATE172710T1 (fr)
AU (1)	AU702551B2 (fr)
BG (1)	BG62253B1 (fr)
BR (1)	BR9509752A (fr)
CA (1)	CA2201363A1 (fr)
CZ (1)	CZ288016B6 (fr)
DE (1)	DE69505695T2 (fr)
DK (1)	DK0793637T3 (fr)
ES (1)	ES2122688T3 (fr)
FI (1)	FI119426B (fr)
HU (1)	HU215935B (fr)
IL (1)	IL115833A (fr)
MX (1)	MX9703663A (fr)
NZ (1)	NZ294889A (fr)
PL (1)	PL180666B1 (fr)
TW (1)	TW306913B (fr)
WO (1)	WO1996016925A1 (fr)
ZA (1)	ZA959721B (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US20090052498A1 (en) *	2007-08-24	2009-02-26	Asm America, Inc.	Thermocouple
US8262287B2 (en) *	2008-12-08	2012-09-11	Asm America, Inc.	Thermocouple
US9297705B2 (en) *	2009-05-06	2016-03-29	Asm America, Inc.	Smart temperature measuring device
EP2668190B1 (fr)	2011-01-26	2016-08-17	Nerviano Medical Sciences S.r.l.	Dérivés pyrrolo tricycliques, leur procédé de préparation et leur utilisation à titre d'inhibiteurs de kinases

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4113968A (en) *	1974-10-03	1978-09-12	Kuraray Co., Ltd.	Process for preparation of substituted cyclopropane carboxylic acids and esters thereof and intermediates of said acids and esters
US4183948A (en) *	1977-01-24	1980-01-15	Imperial Chemical Industries Limited	Halogenated esters
US4238505A (en) *	1978-01-20	1980-12-09	Fmc Corporation	Insecticidal biphenylmethyl perhaloalkylvinylcyclopropanecarboxylates
EP0304271A3 (fr) *	1987-08-20	1992-09-02	Smith Kline & French Laboratories Limited	Acides oméga-arylsulphonamidoalkanoiques pour le traitement de maladies par médiation du thromboxane
GR900100129A (el) *	1989-02-23	1991-06-28	Ici Australia Operations	Συν?έσεις και ενώσεις που απορροφούν το υπεριώδες φως.
GB9311142D0 (en) *	1993-05-28	1993-07-14	Zeneca Ltd	Preparation and use of halogenated alcohols

1995
- 1995-10-31 IL IL11583395A patent/IL115833A/en not_active IP Right Cessation
- 1995-11-02 DK DK95936009T patent/DK0793637T3/da active
- 1995-11-02 CZ CZ19971584A patent/CZ288016B6/cs not_active IP Right Cessation
- 1995-11-02 HU HU9701327A patent/HU215935B/hu not_active IP Right Cessation
- 1995-11-02 PL PL95320417A patent/PL180666B1/pl unknown
- 1995-11-02 KR KR1019970703318A patent/KR100374689B1/ko not_active Expired - Fee Related
- 1995-11-02 CN CN95196405A patent/CN1071306C/zh not_active Expired - Fee Related
- 1995-11-02 NZ NZ294889A patent/NZ294889A/xx unknown
- 1995-11-02 JP JP51839496A patent/JP3839051B2/ja not_active Expired - Fee Related
- 1995-11-02 AU AU38102/95A patent/AU702551B2/en not_active Ceased
- 1995-11-02 AT AT95936009T patent/ATE172710T1/de active
- 1995-11-02 EP EP95936009A patent/EP0793637B1/fr not_active Expired - Lifetime
- 1995-11-02 ES ES95936009T patent/ES2122688T3/es not_active Expired - Lifetime
- 1995-11-02 DE DE69505695T patent/DE69505695T2/de not_active Expired - Lifetime
- 1995-11-02 WO PCT/GB1995/002569 patent/WO1996016925A1/fr not_active Ceased
- 1995-11-02 BR BR9509752A patent/BR9509752A/pt not_active IP Right Cessation
- 1995-11-02 CA CA002201363A patent/CA2201363A1/fr not_active Abandoned
- 1995-11-02 MX MX9703663A patent/MX9703663A/es unknown
- 1995-11-03 TW TW084111633A patent/TW306913B/zh not_active IP Right Cessation
- 1995-11-08 US US08/554,648 patent/US5750769A/en not_active Expired - Lifetime
- 1995-11-15 ZA ZA959721A patent/ZA959721B/xx unknown
1997
- 1997-05-22 FI FI972189A patent/FI119426B/fi not_active IP Right Cessation
- 1997-06-11 BG BG101606A patent/BG62253B1/bg unknown
- 1997-09-22 US US08/934,835 patent/US5756835A/en not_active Expired - Lifetime
2004
- 2004-11-12 JP JP2004328441A patent/JP4044923B2/ja not_active Expired - Fee Related

Also Published As

Publication number	Publication date
EP0793637B1 (fr)	1998-10-28
ZA959721B (en)	1996-06-18
JP3839051B2 (ja)	2006-11-01
JP4044923B2 (ja)	2008-02-06
AU702551B2 (en)	1999-02-25
WO1996016925A1 (fr)	1996-06-06
NZ294889A (en)	1999-07-29
DK0793637T3 (da)	1999-07-12
DE69505695D1 (de)	1998-12-03
ES2122688T3 (es)	1998-12-16
FI119426B (fi)	2008-11-14
MX9703663A (es)	1997-08-30
JPH10509971A (ja)	1998-09-29
FI972189A0 (fi)	1997-05-22
US5756835A (en)	1998-05-26
EP0793637A1 (fr)	1997-09-10
CN1071306C (zh)	2001-09-19
BG101606A (en)	1998-03-31
TW306913B (fr)	1997-06-01
CZ158497A3 (en)	1997-10-15
US5750769A (en)	1998-05-12
HU215935B (hu)	1999-03-29
KR970707070A (ko)	1997-12-01
CZ288016B6 (cs)	2001-04-11
HUT76750A (en)	1997-11-28
BR9509752A (pt)	1998-06-16
DE69505695T2 (de)	1999-03-18
PL180666B1 (pl)	2001-03-30
ATE172710T1 (de)	1998-11-15
PL320417A1 (en)	1997-09-29
AU3810295A (en)	1996-06-19
FI972189L (fi)	1997-05-22
IL115833A0 (en)	1996-01-19
CN1166824A (zh)	1997-12-03
CA2201363A1 (fr)	1996-06-06
KR100374689B1 (ko)	2003-05-17
IL115833A (en)	1998-10-27
JP2005041886A (ja)	2005-02-17

Publication	Publication Date	Title
BG62253B1 (bg)	1999-06-30	Халогенирани естери, метод за получаването им и приложениетоим като междинни съединения за получаване на инсектициди
RU2144528C1 (ru)	2000-01-20	Галогенированный сложный эфир, способ его получения и способ получения алкилового эфира 3-(2-хлор-3,3,3-трифторпроп-1-ен-1-ил)-2,2-диметилциклопропанкарбоновой кислоты
MXPA97003663A (en)	1997-08-01	Halogenated eteres useful as intermediaries for insecticide
US4258202A (en)	1981-03-24	Cyclopropanecarboxylic acids and esters
KR100239232B1 (ko)	2000-01-15	할로겐화된 알콜의 제조방법
USH49H (en)	1986-04-01	Process for producing 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylates
GB2295389A (en)	1996-05-29	Halogenated acyclic carboxylic acid intermediates
US4299776A (en)	1981-11-10	Preparation of esters
US5723649A (en)	1998-03-03	Preparation of cyclopropane esters
RU2120936C1 (ru)	1998-10-27	Способ получения сложных эфиров циклопропана из 3-метилбут-2-ен-1-аля