SU1473707A3 - Способ получени сложных эфиров циклопропанкарбоновых кислот - Google Patents
Способ получени сложных эфиров циклопропанкарбоновых кислот Download PDFInfo
- Publication number
- SU1473707A3 SU1473707A3 SU813372847A SU3372847A SU1473707A3 SU 1473707 A3 SU1473707 A3 SU 1473707A3 SU 813372847 A SU813372847 A SU 813372847A SU 3372847 A SU3372847 A SU 3372847A SU 1473707 A3 SU1473707 A3 SU 1473707A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- group
- dimethyl
- radical
- acid
- cis
- Prior art date
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- 239000002253 acid Substances 0.000 title claims abstract description 53
- 150000002148 esters Chemical class 0.000 title claims abstract description 49
- 238000000034 method Methods 0.000 title claims description 10
- 150000007513 acids Chemical class 0.000 title claims description 7
- -1 cyclic alkyl radical Chemical class 0.000 claims abstract description 134
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 claims description 5
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 2
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 24
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- 125000004093 cyano group Chemical group *C#N 0.000 abstract description 2
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- 125000000524 functional group Chemical group 0.000 abstract 6
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- BQIKRTGTPBOIMK-UHFFFAOYSA-N [O]C[O] Chemical compound [O]C[O] BQIKRTGTPBOIMK-UHFFFAOYSA-N 0.000 abstract 1
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- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
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- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
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- 239000011203 carbon fibre reinforced carbon Substances 0.000 abstract 1
- JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 abstract 1
- 150000001942 cyclopropanes Chemical group 0.000 abstract 1
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- 125000001174 sulfone group Chemical group 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
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- 239000000243 solution Substances 0.000 description 51
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- 238000012360 testing method Methods 0.000 description 7
- HSIZPBYFVGZXMN-UHFFFAOYSA-N 1-(3-ethoxy-2-fluoro-3-oxoprop-1-enyl)cyclopropane-1-carboxylic acid Chemical compound CCOC(=O)C(F)=CC1(C(O)=O)CC1 HSIZPBYFVGZXMN-UHFFFAOYSA-N 0.000 description 6
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- LUFKUSVNPJDGLX-VOTSOKGWSA-N 1-[(E)-2-bromo-3-oxo-3-propoxyprop-1-enyl]cyclopropane-1-carboxylic acid Chemical compound Br/C(=C/C1(CC1)C(=O)O)/C(=O)OCCC LUFKUSVNPJDGLX-VOTSOKGWSA-N 0.000 description 4
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- 125000004122 cyclic group Chemical group 0.000 description 2
- YMGUBTXCNDTFJI-UHFFFAOYSA-M cyclopropanecarboxylate Chemical compound [O-]C(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-M 0.000 description 2
- 125000000950 dibromo group Chemical group Br* 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 235000013847 iso-butane Nutrition 0.000 description 2
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N sec-butylidene Natural products CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- IIHPVYJPDKJYOU-UHFFFAOYSA-N triphenylcarbethoxymethylenephosphorane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OCC)C1=CC=CC=C1 IIHPVYJPDKJYOU-UHFFFAOYSA-N 0.000 description 2
- WSGNMYKZEWLHAH-PBFHFMIUSA-N (1R,3R)-3-[(E)-2-chloro-3-methoxy-3-oxoprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1([C@@H]([C@@H]1\C=C(/C(=O)OC)\Cl)C(=O)O)C WSGNMYKZEWLHAH-PBFHFMIUSA-N 0.000 description 1
- GNACAIQZXUOEEU-MMIQFEHNSA-N (1r,3r)-3-[(e)-3-ethoxy-2-fluoro-3-oxoprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CCOC(=O)C(\F)=C/[C@H]1[C@@H](C(O)=O)C1(C)C GNACAIQZXUOEEU-MMIQFEHNSA-N 0.000 description 1
- PTQGFDXPHNRDCV-UHNVWZDZSA-N (1r,3r)-3-formyl-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)[C@H](C=O)[C@H]1C(O)=O PTQGFDXPHNRDCV-UHNVWZDZSA-N 0.000 description 1
- KGANAERDZBAECK-UHFFFAOYSA-N (3-phenoxyphenyl)methanol Chemical compound OCC1=CC=CC(OC=2C=CC=CC=2)=C1 KGANAERDZBAECK-UHFFFAOYSA-N 0.000 description 1
- KZYVOZABVXLALY-QMMMGPOBSA-N (4s)-4-hydroxy-3-methyl-2-prop-2-enylcyclopent-2-en-1-one Chemical compound CC1=C(CC=C)C(=O)C[C@@H]1O KZYVOZABVXLALY-QMMMGPOBSA-N 0.000 description 1
- JKPUYKJKKHNPBX-UHFFFAOYSA-N 1-(3-ethoxy-3-oxoprop-1-enyl)cyclopropane-1-carboxylic acid Chemical compound CCOC(=O)C=CC1(C(O)=O)CC1 JKPUYKJKKHNPBX-UHFFFAOYSA-N 0.000 description 1
- ZMHJKFCIOXAOOK-UHFFFAOYSA-N 1-[2-fluoro-3-[(2-methylpropan-2-yl)oxy]-3-oxoprop-1-enyl]cyclopropane-1-carboxylic acid Chemical compound CC(C)(C)OC(=O)C(F)=CC1(C(O)=O)CC1 ZMHJKFCIOXAOOK-UHFFFAOYSA-N 0.000 description 1
- XVVDJXADJFNWAZ-UHFFFAOYSA-N 2-diethoxyphosphoryl-2-fluoroacetic acid Chemical compound CCOP(=O)(OCC)C(F)C(O)=O XVVDJXADJFNWAZ-UHFFFAOYSA-N 0.000 description 1
- FUSGVCNDISKHSY-UHFFFAOYSA-N 2-fluoro-3-oxobutanedioic acid Chemical compound OC(=O)C(F)C(=O)C(O)=O FUSGVCNDISKHSY-UHFFFAOYSA-N 0.000 description 1
- GXUQMKBQDGPMKZ-UHFFFAOYSA-N 2-hydroxy-2-(3-phenoxyphenyl)acetonitrile Chemical class N#CC(O)C1=CC=CC(OC=2C=CC=CC=2)=C1 GXUQMKBQDGPMKZ-UHFFFAOYSA-N 0.000 description 1
- IBUQEIIFTPFARK-UHFFFAOYSA-N 3-phenoxybenzonitrile Chemical compound N#CC1=CC=CC(OC=2C=CC=CC=2)=C1 IBUQEIIFTPFARK-UHFFFAOYSA-N 0.000 description 1
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 241001674044 Blattodea Species 0.000 description 1
- RPDIXANSCBKQAQ-UHFFFAOYSA-N C(CC)OC(=O)C1C(C1)(C(=O)O)C=C Chemical compound C(CC)OC(=O)C1C(C1)(C(=O)O)C=C RPDIXANSCBKQAQ-UHFFFAOYSA-N 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- 241001301805 Epilachna Species 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical class NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
- RQJDPOCDSLKVSG-WAYWQWQTSA-N O=C(/C(=C/C1(CC1)C(=O)O)/Cl)OCC Chemical compound O=C(/C(=C/C1(CC1)C(=O)O)/Cl)OCC RQJDPOCDSLKVSG-WAYWQWQTSA-N 0.000 description 1
- DVXDSMVRPKTCFN-VOTSOKGWSA-N O=C(\C(=C/C1(CC1)C(=O)O)\Cl)OCCC Chemical compound O=C(\C(=C/C1(CC1)C(=O)O)\Cl)OCCC DVXDSMVRPKTCFN-VOTSOKGWSA-N 0.000 description 1
- 241000488581 Panonychus citri Species 0.000 description 1
- VONGZNXBKCOUHB-UHFFFAOYSA-N Phenylmethyl butanoate Chemical compound CCCC(=O)OCC1=CC=CC=C1 VONGZNXBKCOUHB-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- ZWZUFQPXYVYAFO-UHFFFAOYSA-N Tert-butyl (triphenylphosphoranylidene)acetate Chemical class C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OC(C)(C)C)C1=CC=CC=C1 ZWZUFQPXYVYAFO-UHFFFAOYSA-N 0.000 description 1
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- ONXFNBOZJKXCNC-ZJSXRUAMSA-N [(3aR,9bR)-9b-(4-fluorophenyl)sulfonyl-7-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2,3a,4,5-tetrahydro-1H-benzo[e]indol-3-yl]-(4-hydroxy-1,1-dioxothian-4-yl)methanone Chemical compound OC1(CCS(=O)(=O)CC1)C(=O)N1CC[C@@]2([C@H]1CCc1cc(ccc21)C(F)(C(F)(F)F)C(F)(F)F)S(=O)(=O)c1ccc(F)cc1 ONXFNBOZJKXCNC-ZJSXRUAMSA-N 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- YRRFBANPGRXQNJ-UHFFFAOYSA-M acetyl(trimethyl)azanium;bromide Chemical compound [Br-].CC(=O)[N+](C)(C)C YRRFBANPGRXQNJ-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- QKYLHOOIOJOCIQ-UHFFFAOYSA-N cyclopropyl hydrogen carbonate Chemical compound OC(=O)OC1CC1 QKYLHOOIOJOCIQ-UHFFFAOYSA-N 0.000 description 1
- 230000002498 deadly effect Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000002373 hemiacetals Chemical class 0.000 description 1
- MOTRZVVGCFFABN-UHFFFAOYSA-N hexane;2-propan-2-yloxypropane Chemical compound CCCCCC.CC(C)OC(C)C MOTRZVVGCFFABN-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000001418 larval effect Effects 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- MECSOFYXVOLEOU-UHFFFAOYSA-N methyl 2-[chloromethylidene(diphenyl)-$l^{5}-phosphanyl]benzoate Chemical compound COC(=O)C1=CC=CC=C1P(=CCl)(C=1C=CC=CC=1)C1=CC=CC=C1 MECSOFYXVOLEOU-UHFFFAOYSA-N 0.000 description 1
- XYDYWTJEGDZLTH-UHFFFAOYSA-N methylenetriphenylphosphorane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=C)C1=CC=CC=C1 XYDYWTJEGDZLTH-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- VJMRKWPMFQGIPI-UHFFFAOYSA-N n-(2-hydroxyethyl)-5-(hydroxymethyl)-3-methyl-1-[2-[[3-(trifluoromethyl)phenyl]methyl]-1-benzothiophen-7-yl]pyrazole-4-carboxamide Chemical compound OCC1=C(C(=O)NCCO)C(C)=NN1C1=CC=CC2=C1SC(CC=1C=C(C=CC=1)C(F)(F)F)=C2 VJMRKWPMFQGIPI-UHFFFAOYSA-N 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- UOVFBPWSENTGJJ-UHFFFAOYSA-N propyl 2-[chloromethylidene(diphenyl)-$l^{5}-phosphanyl]benzoate Chemical compound CCCOC(=O)C1=CC=CC=C1P(=CCl)(C=1C=CC=CC=1)C1=CC=CC=C1 UOVFBPWSENTGJJ-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- ISIMQTCWOTYBLH-UHFFFAOYSA-N tert-butyl 2-chloroprop-2-enoate Chemical compound CC(C)(C)OC(=O)C(Cl)=C ISIMQTCWOTYBLH-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 1
- 150000004685 tetrahydrates Chemical class 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
- C07D213/647—One oxygen atom attached in position 2 or 6 and having in the molecule an acyl radical containing a saturated three-membered ring, e.g. chrysanthemumic acid esters
-
- 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
- C07C69/747—Chrysanthemumic acid esters
-
- 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
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/105—Aliphatic or alicyclic compounds
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/111—Aromatic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
- A61K31/225—Polycarboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Food Science & Technology (AREA)
- Animal Husbandry (AREA)
- Emergency Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Indole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyrane Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Furan Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8021017A FR2491060A1 (fr) | 1980-10-01 | 1980-10-01 | Esters d'acides cyclopropanes carboxyliques apparentes a l'acide pyrethrique, leur procede de preparation et leur application a la lutte contre les parasites |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1473707A3 true SU1473707A3 (ru) | 1989-04-15 |
Family
ID=9246463
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU813372847A SU1473707A3 (ru) | 1980-10-01 | 1981-09-30 | Способ получени сложных эфиров циклопропанкарбоновых кислот |
Country Status (24)
| Country | Link |
|---|---|
| EP (1) | EP0050534B1 (enExample) |
| JP (2) | JPS57126447A (enExample) |
| KR (1) | KR880001829B1 (enExample) |
| AT (1) | ATE12490T1 (enExample) |
| AU (1) | AU548041B2 (enExample) |
| BR (1) | BR8106299A (enExample) |
| CA (2) | CA1242648A (enExample) |
| DD (2) | DD202422A5 (enExample) |
| DE (1) | DE3169688D1 (enExample) |
| DK (2) | DK164740C (enExample) |
| ES (1) | ES505887A0 (enExample) |
| FI (1) | FI78679C (enExample) |
| FR (2) | FR2491060A1 (enExample) |
| GR (1) | GR75021B (enExample) |
| HU (1) | HU195759B (enExample) |
| IE (1) | IE52212B1 (enExample) |
| IL (1) | IL63979A0 (enExample) |
| MA (1) | MA19293A1 (enExample) |
| NZ (1) | NZ198515A (enExample) |
| OA (1) | OA07538A (enExample) |
| PT (1) | PT73753B (enExample) |
| SU (1) | SU1473707A3 (enExample) |
| ZA (1) | ZA816768B (enExample) |
| ZW (1) | ZW24181A1 (enExample) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2536392A2 (fr) * | 1982-11-22 | 1984-05-25 | Roussel Uclaf | Nouveaux derives de l'acide cyclopropane carboxylique, leur procede de preparation et leur application a la lutte contre les parasites |
| FR2491060A1 (fr) * | 1980-10-01 | 1982-04-02 | Roussel Uclaf | Esters d'acides cyclopropanes carboxyliques apparentes a l'acide pyrethrique, leur procede de preparation et leur application a la lutte contre les parasites |
| FR2536389B2 (fr) * | 1982-11-22 | 1986-06-27 | Roussel Uclaf | Esters d'acides cyclopropane carboxyliques apparentes a l'acide pyretrique, leur procede de preparation et leur application a la lutte contre les parasites |
| FR2533416B1 (fr) * | 1982-09-29 | 1988-09-02 | Roussel Uclaf | Nouvelles compositions pesticides renfermant un photostabilisant |
| FR2534252A1 (fr) * | 1982-10-12 | 1984-04-13 | Roussel Uclaf | Nouveaux derives de l'acide cyclopropane carboxylique substitues en 3 par une chaine vinylique elle-meme substituee, leur procede de preparation et leur application comme pesticides |
| FR2535315A1 (fr) * | 1982-11-02 | 1984-05-04 | Roussel Uclaf | Nouveaux derives de l'acide cyclopropane carboxylique comportant un groupement alcoylthio carbonyle et un atome d'halogene, leur preparation, leur application a la lutte contre les parasites des vegetaux, des animaux et des locaux et les compositions les renfermant |
| FR2536748A1 (fr) * | 1982-11-25 | 1984-06-01 | Roussel Uclaf | Nouveaux esters derives d'acides 2,2-dimethyl cyclopropane carboxyliques et d'alcools biaryliques, leur procede de preparation et leur application a la lutte contre les parasites |
| FR2547817B2 (fr) * | 1982-12-15 | 1986-02-14 | Roussel Uclaf | Esters d'acides cyclopropane carboxyliques et d'alcools aliphatiques insatures, leur procede de preparation et les compositions pesticides les renfermant |
| FR2537973B1 (fr) * | 1982-12-15 | 1985-11-08 | Roussel Uclaf | Esters d'acides cyclopropane carboxyliques et d'alcools aliphatiques insatures, leur procede de preparation et les compositions pesticides les renfermant |
| FR2569189B1 (fr) * | 1984-08-14 | 1986-12-19 | Roussel Uclaf | Nouveaux derives du pyrrole, leur procede de preparation et leur application comme pesticides |
| FR2590259B1 (fr) * | 1985-11-20 | 1989-05-12 | Roussel Uclaf | Procede de preparation de derives fluores de l'acide phosphonique, et produits obtenus par la mise en oeuvre de ce procede |
| FR2608152B1 (fr) * | 1986-12-11 | 1989-03-31 | Roussel Uclaf | Le 2,2-dimethyl 3-formyl cyclopropane carboxylate de pentafluorophenylmethyle, son procede de preparation et son application a la synthese de produits pesticides |
| FR2610624B1 (fr) * | 1987-02-06 | 1989-06-09 | Roussel Uclaf | Nouveaux esters d'acides cyclopropanecarboxyliques apparentes a l'acide pyrethrique, leur procede de preparation et leur application a la lutte contre les parasites |
| FR2618432B1 (fr) * | 1987-07-20 | 1989-12-01 | Roussel Uclaf | Nouveaux derives pyrethrinoides comportant un heterocycle azote, leur procede de preparation et leurs applications comme pesticides |
| JP2570388B2 (ja) * | 1988-06-10 | 1997-01-08 | 住友化学工業株式会社 | カルボン酸エステルおよびその殺虫剤としての用途 |
| GB8902324D0 (en) * | 1989-02-02 | 1989-03-22 | Ici Plc | Insecticidal compounds |
| FR2687666A1 (fr) * | 1992-02-21 | 1993-08-27 | Roussel Uclaf | Nouveaux esters pyrethrinouiques, derives de l'alcool 6-(trifluoromethyl) benzylique, leur procede de preparation et leur application comme pesticides. |
| FR2693082B1 (fr) * | 1992-07-01 | 1994-08-26 | Roussel Uclaf | Nouvelles compositions insecticides renfermant comme principe actif un ester de l'acide 3-[(DELTAZ) 2-fluoro 3-oxo 3-méthoxy propényl] cyclopropane carboxylique. |
| FR2703044B1 (fr) * | 1993-03-25 | 1995-06-02 | Roussel Uclaf | Nouveau procédé d'isomérisation de doubles liaisons. |
| JP3694915B2 (ja) | 1994-06-17 | 2005-09-14 | 住友化学株式会社 | エステル化合物およびそれを有効成分とする有害生物防除剤 |
| US5852048A (en) * | 1995-03-01 | 1998-12-22 | Sumitomo Chemical Company, Limited | Ester compound and a pesticidal agent containing the same as an active ingredient |
| JP3286598B2 (ja) * | 1998-06-11 | 2002-05-27 | 富士写真フイルム株式会社 | シートの搬送装置 |
| JP4552456B2 (ja) * | 2004-02-27 | 2010-09-29 | 住友化学株式会社 | エステル化合物およびその用途 |
| JP5066843B2 (ja) * | 2006-06-15 | 2012-11-07 | 住友化学株式会社 | エステル化合物及びその有害生物防除用途 |
| CN106642346A (zh) * | 2016-12-28 | 2017-05-10 | 武汉海尔电器股份有限公司 | 空调器 |
Family Cites Families (5)
| 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 |
| DE2326077C2 (de) * | 1972-05-25 | 1985-12-12 | National Research Development Corp., London | Ungesättigte Cyclopropancarbonsäuren und deren Derivate, deren Herstellung und diese enthaltende Insektizide |
| OA06786A (fr) * | 1980-04-16 | 1982-12-31 | Roussel Uclaf | Nouveaux dérivés de l'acide cyclopropane, leur préparation, leur application à la lutte contre les parasites des végétaux et des animaux, les compositions les renfermant et les nouveaux intermediaires obtenus. |
| FR2482955A1 (fr) * | 1980-05-23 | 1981-11-27 | Roussel Uclaf | Nouveaux derives de l'acide cyclopropane carboxylique, leur procede de preparation et leur application a la lutte contre les parasites |
| FR2491060A1 (fr) * | 1980-10-01 | 1982-04-02 | Roussel Uclaf | Esters d'acides cyclopropanes carboxyliques apparentes a l'acide pyrethrique, leur procede de preparation et leur application a la lutte contre les parasites |
-
1980
- 1980-10-01 FR FR8021017A patent/FR2491060A1/fr active Granted
-
1981
- 1981-08-28 EP EP81401360A patent/EP0050534B1/fr not_active Expired
- 1981-08-28 AT AT81401360T patent/ATE12490T1/de active
- 1981-08-28 DE DE8181401360T patent/DE3169688D1/de not_active Expired
- 1981-09-29 ZW ZW241/81A patent/ZW24181A1/xx unknown
- 1981-09-29 GR GR66153A patent/GR75021B/el unknown
- 1981-09-30 CA CA000386984A patent/CA1242648A/fr not_active Expired
- 1981-09-30 HU HU812824A patent/HU195759B/hu not_active IP Right Cessation
- 1981-09-30 DD DD81233716A patent/DD202422A5/de not_active IP Right Cessation
- 1981-09-30 CA CA000386995A patent/CA1237135A/fr not_active Expired
- 1981-09-30 FI FI813042A patent/FI78679C/fi not_active IP Right Cessation
- 1981-09-30 IE IE2274/81A patent/IE52212B1/en not_active IP Right Cessation
- 1981-09-30 SU SU813372847A patent/SU1473707A3/ru active
- 1981-09-30 ZA ZA816768A patent/ZA816768B/xx unknown
- 1981-09-30 PT PT73753A patent/PT73753B/pt not_active IP Right Cessation
- 1981-09-30 MA MA19494A patent/MA19293A1/fr unknown
- 1981-09-30 ES ES505887A patent/ES505887A0/es active Granted
- 1981-09-30 DD DD81249256A patent/DD211473A5/de not_active IP Right Cessation
- 1981-09-30 NZ NZ198515A patent/NZ198515A/en unknown
- 1981-09-30 BR BR8106299A patent/BR8106299A/pt unknown
- 1981-09-30 DK DK432781A patent/DK164740C/da not_active IP Right Cessation
- 1981-10-01 AU AU75961/81A patent/AU548041B2/en not_active Ceased
- 1981-10-01 JP JP56154927A patent/JPS57126447A/ja active Granted
- 1981-10-01 IL IL63979A patent/IL63979A0/xx not_active IP Right Cessation
- 1981-10-02 KR KR1019810003710A patent/KR880001829B1/ko not_active Expired
-
1983
- 1983-09-22 OA OA58107A patent/OA07538A/xx unknown
-
1984
- 1984-02-24 FR FR8402831A patent/FR2560189B2/fr not_active Expired
- 1984-05-21 JP JP59100736A patent/JPH0643369B2/ja not_active Expired - Lifetime
-
1991
- 1991-01-29 DK DK015691A patent/DK164402C/da not_active IP Right Cessation
Non-Patent Citations (1)
| Title |
|---|
| Патент FR № 2240914, кл. С 07 С 69/74, опублик. 1975. Патент FR № 2185612, кл. С 07 С 69/74, опублик. 1974„ ь * |
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