DK141934B - Fremgangsmåde til fremstilling af substituerede cyclopropancarboxylsyreestere eller substituerede phenyleddikesyreestere. - Google Patents
Fremgangsmåde til fremstilling af substituerede cyclopropancarboxylsyreestere eller substituerede phenyleddikesyreestere. Download PDFInfo
- Publication number
- DK141934B DK141934B DK417174AA DK417174A DK141934B DK 141934 B DK141934 B DK 141934B DK 417174A A DK417174A A DK 417174AA DK 417174 A DK417174 A DK 417174A DK 141934 B DK141934 B DK 141934B
- Authority
- DK
- Denmark
- Prior art keywords
- phenoxybenzyl
- acid esters
- carboxylic acid
- formula
- substituted
- Prior art date
Links
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 title description 10
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 title description 7
- 238000004519 manufacturing process Methods 0.000 title description 3
- -1 2,2-dichlorovinyl Chemical group 0.000 description 35
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
- 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
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 19
- 150000002148 esters Chemical class 0.000 description 16
- 239000000203 mixture Substances 0.000 description 13
- 150000003839 salts Chemical class 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- 238000000034 method Methods 0.000 description 12
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 12
- 230000008569 process Effects 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000006227 byproduct Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- UIOXYHBIXWFNKN-UHFFFAOYSA-M triethyl-[(3-phenoxyphenyl)methyl]azanium;bromide Chemical compound [Br-].CC[N+](CC)(CC)CC1=CC=CC(OC=2C=CC=CC=2)=C1 UIOXYHBIXWFNKN-UHFFFAOYSA-M 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 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 6
- 150000003863 ammonium salts Chemical class 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000010410 layer Substances 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 125000005270 trialkylamine group Chemical group 0.000 description 5
- XLOPRKKSAJMMEW-SFYZADRCSA-M (R,R)-chrysanthemate Chemical compound CC(C)=C[C@@H]1[C@@H](C([O-])=O)C1(C)C XLOPRKKSAJMMEW-SFYZADRCSA-M 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- LDFPTHJERYPPKM-UHFFFAOYSA-M triethyl-[(3-phenoxyphenyl)methyl]azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC(OC=2C=CC=CC=2)=C1 LDFPTHJERYPPKM-UHFFFAOYSA-M 0.000 description 4
- ZQSXAXKUCAUPCM-UHFFFAOYSA-N 1-methyl-2-[3-[3-(2-methylphenyl)phenoxy]phenyl]benzene Chemical compound CC1=CC=CC=C1C1=CC=CC(OC=2C=C(C=CC=2)C=2C(=CC=CC=2)C)=C1 ZQSXAXKUCAUPCM-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000238631 Hexapoda Species 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000001733 carboxylic acid esters Chemical class 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 3
- 239000000575 pesticide Substances 0.000 description 3
- 229960003424 phenylacetic acid Drugs 0.000 description 3
- 239000003279 phenylacetic acid Substances 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- QQLJBZFXGDHSRU-UHFFFAOYSA-N 2-amino-4-chloro-5-sulfamoylbenzoic acid Chemical compound NC1=CC(Cl)=C(S(N)(=O)=O)C=C1C(O)=O QQLJBZFXGDHSRU-UHFFFAOYSA-N 0.000 description 2
- OFJWFSNDPCAWDK-UHFFFAOYSA-N 2-phenylbutyric acid Chemical compound CCC(C(O)=O)C1=CC=CC=C1 OFJWFSNDPCAWDK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000258937 Hemiptera Species 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- 125000005210 alkyl ammonium group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
- 150000003939 benzylamines Chemical class 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- OWIFNISFRBVGIX-UHFFFAOYSA-N (3-phenoxyphenyl)methanamine Chemical class NCC1=CC=CC(OC=2C=CC=CC=2)=C1 OWIFNISFRBVGIX-UHFFFAOYSA-N 0.000 description 1
- HVDHFAXIGUAEBE-UHFFFAOYSA-N (3-phenoxyphenyl)methyl 2-phenylbutanoate Chemical compound C=1C=CC=CC=1C(CC)C(=O)OCC(C=1)=CC=CC=1OC1=CC=CC=C1 HVDHFAXIGUAEBE-UHFFFAOYSA-N 0.000 description 1
- XPHQNMNGUGOWGU-UHFFFAOYSA-N (3-phenoxyphenyl)methyl acetate Chemical compound CC(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 XPHQNMNGUGOWGU-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- UJUNUASMYSTBSK-UHFFFAOYSA-N 1-(bromomethyl)-3-phenoxybenzene Chemical compound BrCC1=CC=CC(OC=2C=CC=CC=2)=C1 UJUNUASMYSTBSK-UHFFFAOYSA-N 0.000 description 1
- QUYVTGFWFHQVRO-UHFFFAOYSA-N 1-(chloromethyl)-3-phenoxybenzene Chemical compound ClCC1=CC=CC(OC=2C=CC=CC=2)=C1 QUYVTGFWFHQVRO-UHFFFAOYSA-N 0.000 description 1
- XNICSRPFAIGZAB-UHFFFAOYSA-M 1-[(3-phenoxyphenyl)methyl]pyridin-1-ium;chloride Chemical compound [Cl-].C=1C=CC=C[N+]=1CC(C=1)=CC=CC=1OC1=CC=CC=C1 XNICSRPFAIGZAB-UHFFFAOYSA-M 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- SFHVXKNMCGSLAR-UHFFFAOYSA-N 2,2,3,3-tetramethylcyclopropanecarboxylic acid Chemical compound CC1(C)C(C(O)=O)C1(C)C SFHVXKNMCGSLAR-UHFFFAOYSA-N 0.000 description 1
- DDZLZVXPBSNDAH-UHFFFAOYSA-N 2,2,3-trimethylcyclopropane-1-carboxylic acid Chemical compound CC1C(C(O)=O)C1(C)C DDZLZVXPBSNDAH-UHFFFAOYSA-N 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- JRGAUAWPCLQHTF-UHFFFAOYSA-N 2-amino-5-sulfamoylbenzoic acid Chemical class NC1=CC=C(S(N)(=O)=O)C=C1C(O)=O JRGAUAWPCLQHTF-UHFFFAOYSA-N 0.000 description 1
- 125000006020 2-methyl-1-propenyl group Chemical group 0.000 description 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- 241000934067 Acarus Species 0.000 description 1
- 241000584629 Aosa Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- UJPMKVURQSCMOP-UHFFFAOYSA-N C(C)(=O)OC1=C(C=C(C=C1)C)CC.[Na] Chemical compound C(C)(=O)OC1=C(C=C(C=C1)C)CC.[Na] UJPMKVURQSCMOP-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- 241001327708 Coriaria sarmentosa Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000255777 Lepidoptera Species 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- 241000244206 Nematoda Species 0.000 description 1
- CCAZWUJBLXKBAY-ULZPOIKGSA-N Tutin Chemical compound C([C@]12[C@@H]3O[C@@H]3[C@@]3(O)[C@H]4C(=O)O[C@@H]([C@H]([C@]32C)O)[C@H]4C(=C)C)O1 CCAZWUJBLXKBAY-ULZPOIKGSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 229940022682 acetone Drugs 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001340 alkali metals Chemical group 0.000 description 1
- 125000005599 alkyl carboxylate group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000005349 anion exchange Methods 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 150000001942 cyclopropanes Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000214 effect on organisms Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 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
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- YKASHPSKFYVZRC-UHFFFAOYSA-M furan-2-ylmethyl(trimethyl)azanium;iodide Chemical compound [I-].C[N+](C)(C)CC1=CC=CO1 YKASHPSKFYVZRC-UHFFFAOYSA-M 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 231100001225 mammalian toxicity Toxicity 0.000 description 1
- 230000029052 metamorphosis Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000017448 oviposition Effects 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- BOTNYLSAWDQNEX-UHFFFAOYSA-N phenoxymethylbenzene Chemical compound C=1C=CC=CC=1COC1=CC=CC=C1 BOTNYLSAWDQNEX-UHFFFAOYSA-N 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- PDMSESXLYVIQNJ-UHFFFAOYSA-M sodium;2,2,3-trimethylcyclopropane-1-carboxylate Chemical compound [Na+].CC1C(C([O-])=O)C1(C)C PDMSESXLYVIQNJ-UHFFFAOYSA-M 0.000 description 1
- UPPSRHIRBDBHDA-UHFFFAOYSA-M sodium;3-ethenyl-2,2-dimethylcyclopropane-1-carboxylate Chemical compound [Na+].CC1(C)C(C=C)C1C([O-])=O UPPSRHIRBDBHDA-UHFFFAOYSA-M 0.000 description 1
- HQIZDGAMCWYBKS-UHFFFAOYSA-M sodium;cyclopropanecarboxylate Chemical compound [Na+].[O-]C(=O)C1CC1 HQIZDGAMCWYBKS-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical class CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Chemical group 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
- A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
- A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
- A01N43/30—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3 with two oxygen atoms in positions 1,3, condensed with a carbocyclic ring
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/10—Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic 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
- C07C69/612—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety
-
- 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
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK145576A DK145576A (da) | 1973-08-06 | 1976-03-30 | 3-phenoxybenxylmethylhalogenidaminsalt til anvendelse som mellemprodukt og fremgangsmade til fremstilling deraf |
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8867473A JPS5111106B2 (enrdf_load_stackoverflow) | 1973-08-06 | 1973-08-06 | |
| JP8867473 | 1973-08-06 | ||
| JP9498073 | 1973-08-23 | ||
| JP9498073A JPS5212697B2 (enrdf_load_stackoverflow) | 1973-08-23 | 1973-08-23 | |
| JP48097063A JPS5228790B2 (enrdf_load_stackoverflow) | 1973-08-28 | 1973-08-28 | |
| JP9706373 | 1973-08-28 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK417174A DK417174A (enrdf_load_stackoverflow) | 1975-04-01 |
| DK141934B true DK141934B (da) | 1980-07-21 |
| DK141934C DK141934C (enrdf_load_stackoverflow) | 1980-12-01 |
Family
ID=27305880
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK417174AA DK141934B (da) | 1973-08-06 | 1974-08-05 | Fremgangsmåde til fremstilling af substituerede cyclopropancarboxylsyreestere eller substituerede phenyleddikesyreestere. |
Country Status (10)
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL53946A0 (en) * | 1977-03-03 | 1978-04-30 | American Cyanamid Co | Phenoxybenzyl esters of benzodioxole acetic acids |
| US4277617A (en) * | 1977-10-27 | 1981-07-07 | Roussel Uclaf | Process for the preparation of esters |
| FR2496652A1 (fr) * | 1980-12-23 | 1982-06-25 | Roussel Uclaf | Nouveaux derives de l'acide cyclopropane carboxylique substitues en 3 par une chaine vinylique, leur procede de preparation et leur utilisation comme agents parfumants |
| CA1301642C (en) * | 1987-03-30 | 1992-05-26 | Howard Bernard Dawson | Chemical formulations |
| WO2022200364A1 (en) | 2021-03-25 | 2022-09-29 | Syngenta Crop Protection Ag | Insect, acarina and nematode pest control |
| CN117320551A (zh) | 2021-05-14 | 2023-12-29 | 先正达农作物保护股份公司 | 种子处理组合物 |
| US20240260577A1 (en) | 2021-05-14 | 2024-08-08 | Syngenta Crop Protection Ag | Insect, acarina and nematode pest control |
| WO2022268813A1 (en) | 2021-06-24 | 2022-12-29 | Syngenta Crop Protection Ag | Insect, acarina and nematode pest control |
| WO2022268815A1 (en) | 2021-06-24 | 2022-12-29 | Syngenta Crop Protection Ag | Insect, acarina and nematode pest control |
| WO2023105064A1 (en) | 2021-12-10 | 2023-06-15 | Syngenta Crop Protection Ag | Insect, acarina and nematode pest control |
| WO2023105065A1 (en) | 2021-12-10 | 2023-06-15 | Syngenta Crop Protection Ag | Insect, acarina and nematode pest control |
-
1974
- 1974-08-02 IT IT7452434A patent/IT1047139B/it active
- 1974-08-05 DK DK417174AA patent/DK141934B/da not_active IP Right Cessation
- 1974-08-05 AU AU72030/74A patent/AU462570B2/en not_active Expired
- 1974-08-06 GB GB3468474A patent/GB1453655A/en not_active Expired
- 1974-08-06 IL IL45417A patent/IL45417A/xx unknown
- 1974-08-06 BR BR6433/74A patent/BR7406433D0/pt unknown
- 1974-08-06 NL NLAANVRAGE7410547,A patent/NL169996C/xx not_active IP Right Cessation
- 1974-08-06 FR FR7427304A patent/FR2295009A1/fr active Granted
- 1974-08-06 DE DE2437882A patent/DE2437882C3/de not_active Expired
- 1974-08-06 CH CH1072974A patent/CH593232A5/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| BR7406433D0 (pt) | 1975-05-27 |
| CH593232A5 (enrdf_load_stackoverflow) | 1977-11-30 |
| FR2295009A1 (fr) | 1976-07-16 |
| FR2295009B1 (enrdf_load_stackoverflow) | 1977-10-14 |
| IT1047139B (it) | 1980-09-10 |
| DK417174A (enrdf_load_stackoverflow) | 1975-04-01 |
| NL7410547A (nl) | 1975-02-10 |
| AU7203074A (en) | 1975-06-26 |
| DK141934C (enrdf_load_stackoverflow) | 1980-12-01 |
| NL169996C (nl) | 1982-09-16 |
| DE2437882A1 (de) | 1975-04-24 |
| DE2437882C3 (de) | 1978-05-11 |
| AU462570B2 (en) | 1975-06-26 |
| GB1453655A (en) | 1976-10-27 |
| DE2437882B2 (de) | 1977-08-25 |
| IL45417A (en) | 1978-10-31 |
| IL45417A0 (en) | 1974-11-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUP | Patent expired |