DD255730A5 - Verfahren zur herstellung von neuen aryloxy-phenoxyacyl-malonsaeureester-derivaten - Google Patents
Verfahren zur herstellung von neuen aryloxy-phenoxyacyl-malonsaeureester-derivaten Download PDFInfo
- Publication number
- DD255730A5 DD255730A5 DD86301114A DD30111486A DD255730A5 DD 255730 A5 DD255730 A5 DD 255730A5 DD 86301114 A DD86301114 A DD 86301114A DD 30111486 A DD30111486 A DD 30111486A DD 255730 A5 DD255730 A5 DD 255730A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- general formula
- phenoxy
- halogen
- compound
- malonate
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 35
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 14
- 150000002367 halogens Chemical class 0.000 claims abstract description 14
- -1 5-trifluoromethyl-2-pyridyloxy Chemical group 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 3
- 150000002431 hydrogen Chemical class 0.000 claims abstract 6
- 239000000460 chlorine Substances 0.000 claims description 10
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 150000002736 metal compounds Chemical class 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 150000002366 halogen compounds Chemical class 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 230000002363 herbicidal effect Effects 0.000 abstract description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 239000011541 reaction mixture Substances 0.000 description 14
- 239000000203 mixture Substances 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- 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 3
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 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
- ALRGGAOHSITTLL-UHFFFAOYSA-N 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoyl chloride Chemical compound C1=CC(OC(C)C(Cl)=O)=CC=C1OC1=CC=C(Cl)C=C1Cl ALRGGAOHSITTLL-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical class [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 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
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- VAIZTNZGPYBOGF-UHFFFAOYSA-N butyl 2-(4-{[5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoate Chemical group C1=CC(OC(C)C(=O)OCCCC)=CC=C1OC1=CC=C(C(F)(F)F)C=N1 VAIZTNZGPYBOGF-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- FMPJHEINDXIEHS-UHFFFAOYSA-N (2-phenoxyphenyl) hydrogen carbonate Chemical class OC(=O)OC1=CC=CC=C1OC1=CC=CC=C1 FMPJHEINDXIEHS-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
- HBAKZIQTSJVVNU-UHFFFAOYSA-N 2-[4-(4-cyanophenoxy)phenoxy]propanoyl chloride Chemical compound C1=CC(OC(C)C(Cl)=O)=CC=C1OC1=CC=C(C#N)C=C1 HBAKZIQTSJVVNU-UHFFFAOYSA-N 0.000 description 1
- VFERGEXMZIIIBD-UHFFFAOYSA-N 2-[4-[4-(trifluoromethyl)phenoxy]phenoxy]propanoyl bromide Chemical compound C1=CC(OC(C)C(Br)=O)=CC=C1OC1=CC=C(C(F)(F)F)C=C1 VFERGEXMZIIIBD-UHFFFAOYSA-N 0.000 description 1
- GBNPVXZNWBWNEN-UHFFFAOYSA-N 2-chloro-4-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=NC(Cl)=C1 GBNPVXZNWBWNEN-UHFFFAOYSA-N 0.000 description 1
- CHZCERSEMVWNHL-UHFFFAOYSA-N 2-hydroxybenzonitrile Chemical compound OC1=CC=CC=C1C#N CHZCERSEMVWNHL-UHFFFAOYSA-N 0.000 description 1
- DPRSKCAGYLXDCY-UHFFFAOYSA-N 4-(2,4-dichlorophenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(Cl)C=C1Cl DPRSKCAGYLXDCY-UHFFFAOYSA-N 0.000 description 1
- IMZBBUOCARAPNW-UHFFFAOYSA-N 4-[4-(2,4-dichlorophenoxy)phenoxy]pent-2-enoyl chloride Chemical compound C1=CC(OC(C)C=CC(Cl)=O)=CC=C1OC1=CC=C(Cl)C=C1Cl IMZBBUOCARAPNW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 235000017896 Digitaria Nutrition 0.000 description 1
- 241001303487 Digitaria <clam> Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000209082 Lolium Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 240000004713 Pisum sativum Species 0.000 description 1
- 235000010582 Pisum sativum Nutrition 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 235000005775 Setaria Nutrition 0.000 description 1
- 241000232088 Setaria <nematode> Species 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 241001148683 Zostera marina Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001341 alkaline earth metal compounds Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 244000038559 crop plants Species 0.000 description 1
- MMSZLARHVLHGJD-UHFFFAOYSA-N diethyl 2-(2-chloropropanoyl)propanedioate Chemical compound CCOC(=O)C(C(=O)C(C)Cl)C(=O)OCC MMSZLARHVLHGJD-UHFFFAOYSA-N 0.000 description 1
- ZBCHXTIIHPNFFT-UHFFFAOYSA-N diethyl 2-[2-(4-fluorophenoxy)propanoyl]propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)C(=O)C(C)OC1=CC=C(F)C=C1 ZBCHXTIIHPNFFT-UHFFFAOYSA-N 0.000 description 1
- PKGJQNBBCCYSMO-UHFFFAOYSA-N diethyl 2-[2-(4-hydroxyphenoxy)propanoyl]propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)C(=O)C(C)OC1=CC=C(O)C=C1 PKGJQNBBCCYSMO-UHFFFAOYSA-N 0.000 description 1
- WARDJMHXGIWJMM-UHFFFAOYSA-N diethyl 2-[2-[4-(2,4-dichlorophenoxy)phenoxy]propanoyl]propanedioate Chemical compound C1=CC(OC(C)C(=O)C(C(=O)OCC)C(=O)OCC)=CC=C1OC1=CC=C(Cl)C=C1Cl WARDJMHXGIWJMM-UHFFFAOYSA-N 0.000 description 1
- NKFHAVTYARLOPM-UHFFFAOYSA-N diethyl 2-[2-[4-(4-cyanophenoxy)phenoxy]propanoyl]propanedioate Chemical compound C1=CC(OC(C)C(=O)C(C(=O)OCC)C(=O)OCC)=CC=C1OC1=CC=C(C#N)C=C1 NKFHAVTYARLOPM-UHFFFAOYSA-N 0.000 description 1
- KJLZHIZXTLZNQD-UHFFFAOYSA-N diethyl 2-[4-[4-[4-(trifluoromethyl)phenoxy]phenoxy]pent-2-enoyl]propanedioate Chemical compound C1=CC(OC(C)C=CC(=O)C(C(=O)OCC)C(=O)OCC)=CC=C1OC1=CC=C(C(F)(F)F)C=C1 KJLZHIZXTLZNQD-UHFFFAOYSA-N 0.000 description 1
- MFJUJDJVNXTBBF-UHFFFAOYSA-N diethyl propanedioate;magnesium Chemical compound [Mg].CCOC(=O)CC(=O)OCC MFJUJDJVNXTBBF-UHFFFAOYSA-N 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002680 magnesium Chemical class 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 150000002690 malonic acid derivatives Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- BACHBFVBHLGWSL-UHFFFAOYSA-N methyl 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoate Chemical compound C1=CC(OC(C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- WZDGUCWCNAJOOS-UHFFFAOYSA-M sodium;4-(2,4-dichlorophenoxy)phenolate Chemical compound [Na+].C1=CC([O-])=CC=C1OC1=CC=C(Cl)C=C1Cl WZDGUCWCNAJOOS-UHFFFAOYSA-M 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 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
- C07D213/643—2-Phenoxypyridines; Derivatives thereof
-
- 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
- A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
- A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- 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
- C07C69/716—Esters of keto-carboxylic acids or aldehydo-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
- C07C69/66—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
- C07C69/73—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 unsaturated acids
- C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU853798A HU196885B (en) | 1985-10-01 | 1985-10-01 | Herbicides containing as active substance aryloxiphenoxi-acyl-malonic acid esthers and process for production of the active substances |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD255730A5 true DD255730A5 (de) | 1988-04-13 |
Family
ID=10965553
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD86301114A DD255730A5 (de) | 1985-10-01 | 1986-09-25 | Verfahren zur herstellung von neuen aryloxy-phenoxyacyl-malonsaeureester-derivaten |
| DD86294690A DD249841A5 (de) | 1985-10-01 | 1986-09-25 | Herbizide aryloxy-phenoxy-acyl-malonsaeureester-derivate |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD86294690A DD249841A5 (de) | 1985-10-01 | 1986-09-25 | Herbizide aryloxy-phenoxy-acyl-malonsaeureester-derivate |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US4765825A (cs) |
| AU (1) | AU588911B2 (cs) |
| BE (1) | BE905535A (cs) |
| CA (1) | CA1233468A (cs) |
| CH (1) | CH676596A5 (cs) |
| CS (1) | CS274720B2 (cs) |
| DD (2) | DD255730A5 (cs) |
| DE (1) | DE3632433A1 (cs) |
| FR (1) | FR2587999B1 (cs) |
| GB (1) | GB2181134B (cs) |
| HU (1) | HU196885B (cs) |
| IL (1) | IL79975A (cs) |
| NL (1) | NL8602483A (cs) |
| SE (1) | SE8604149L (cs) |
| SU (1) | SU1584737A3 (cs) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU196885B (en) * | 1985-10-01 | 1989-02-28 | Mta Koezponti Kemiai Kutato In | Herbicides containing as active substance aryloxiphenoxi-acyl-malonic acid esthers and process for production of the active substances |
| JP2000321600A (ja) * | 1999-05-13 | 2000-11-24 | Internatl Business Mach Corp <Ibm> | 液晶表示装置及びこれの製造方法 |
| PL375364A1 (en) * | 2002-07-12 | 2005-11-28 | Bayer Cropscience Gmbh | Liquid adjuvants |
| DE10231615A1 (de) * | 2002-07-12 | 2004-02-05 | Bayer Cropscience Gmbh | Feste Adjuvantien |
| CN108752269A (zh) * | 2018-07-06 | 2018-11-06 | 浙江工业大学 | 一种含手性碳的芳氧苯氧丙酰胺类化合物及其制备方法和应用 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR8005226A (pt) * | 1979-08-23 | 1981-03-04 | Du Pont | Composto herbicida, composicao e processo para o controle de vegetacao indesejavel, composicao e processo para o controle de er vas gramineas em plantas de folhas grandes e processo para preparar um composto herbicida |
| JPS5646842A (en) * | 1979-09-27 | 1981-04-28 | Kanesho Kk | Novel herbicide and its preparation |
| US4522647A (en) * | 1982-07-30 | 1985-06-11 | Zoecon Corporation | Substituted phenoxyalkanediones and their herbicidal method of use |
| ZA848416B (en) * | 1983-11-10 | 1986-06-25 | Dow Chemical Co | Fluorophenoxy compounds,herbicidal compositions and methods |
| HU196885B (en) * | 1985-10-01 | 1989-02-28 | Mta Koezponti Kemiai Kutato In | Herbicides containing as active substance aryloxiphenoxi-acyl-malonic acid esthers and process for production of the active substances |
-
1985
- 1985-10-01 HU HU853798A patent/HU196885B/hu not_active IP Right Cessation
-
1986
- 1986-09-08 IL IL79975A patent/IL79975A/xx unknown
- 1986-09-19 CH CH3683/86A patent/CH676596A5/de not_active IP Right Cessation
- 1986-09-23 CA CA000518815A patent/CA1233468A/en not_active Expired
- 1986-09-23 US US06/910,892 patent/US4765825A/en not_active Expired - Fee Related
- 1986-09-24 DE DE19863632433 patent/DE3632433A1/de not_active Withdrawn
- 1986-09-25 DD DD86301114A patent/DD255730A5/de not_active IP Right Cessation
- 1986-09-25 DD DD86294690A patent/DD249841A5/de not_active IP Right Cessation
- 1986-09-30 SU SU864028250A patent/SU1584737A3/ru active
- 1986-09-30 SE SE8604149A patent/SE8604149L/xx not_active Application Discontinuation
- 1986-09-30 AU AU63267/86A patent/AU588911B2/en not_active Ceased
- 1986-09-30 GB GB8623487A patent/GB2181134B/en not_active Expired
- 1986-09-30 FR FR868613598A patent/FR2587999B1/fr not_active Expired
- 1986-10-01 BE BE0/217242A patent/BE905535A/fr not_active IP Right Cessation
- 1986-10-01 NL NL8602483A patent/NL8602483A/nl not_active Application Discontinuation
- 1986-10-01 CS CS705986A patent/CS274720B2/cs unknown
-
1988
- 1988-08-12 US US07/231,883 patent/US4948420A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| IL79975A0 (en) | 1986-12-31 |
| NL8602483A (nl) | 1987-05-04 |
| GB2181134B (en) | 1989-09-13 |
| DE3632433A1 (de) | 1987-04-09 |
| DD249841A5 (de) | 1987-09-23 |
| AU588911B2 (en) | 1989-09-28 |
| GB2181134A (en) | 1987-04-15 |
| HU196885B (en) | 1989-02-28 |
| AU6326786A (en) | 1987-04-02 |
| US4765825A (en) | 1988-08-23 |
| CS274720B2 (en) | 1991-10-15 |
| SU1584737A3 (ru) | 1990-08-07 |
| CS705986A2 (en) | 1991-02-12 |
| BE905535A (fr) | 1987-02-02 |
| HUT41591A (en) | 1987-05-28 |
| IL79975A (en) | 1991-01-31 |
| SE8604149D0 (sv) | 1986-09-30 |
| FR2587999A1 (fr) | 1987-04-03 |
| SE8604149L (sv) | 1987-04-02 |
| CA1233468A (en) | 1988-03-01 |
| US4948420A (en) | 1990-08-14 |
| GB8623487D0 (en) | 1986-11-05 |
| FR2587999B1 (fr) | 1989-05-19 |
| CH676596A5 (cs) | 1991-02-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ENJ | Ceased due to non-payment of renewal fee |