DK156511C - Optisk aktive, p-substituerede alfa-phenoxy-propionsyrederivater med anvendelse som herbicider - Google Patents
Optisk aktive, p-substituerede alfa-phenoxy-propionsyrederivater med anvendelse som herbicider Download PDFInfo
- Publication number
- DK156511C DK156511C DK579078AA DK579078A DK156511C DK 156511 C DK156511 C DK 156511C DK 579078A A DK579078A A DK 579078AA DK 579078 A DK579078 A DK 579078A DK 156511 C DK156511 C DK 156511C
- Authority
- DK
- Denmark
- Prior art keywords
- formula
- phenoxy
- alkyl
- group
- propionic acid
- Prior art date
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- SXERGJJQSKIUIC-UHFFFAOYSA-N 2-Phenoxypropionic acid Chemical class OC(=O)C(C)OC1=CC=CC=C1 SXERGJJQSKIUIC-UHFFFAOYSA-N 0.000 title claims description 5
- 239000004009 herbicide Substances 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 43
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000007529 inorganic bases Chemical class 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 125000000466 oxiranyl group Chemical group 0.000 claims description 2
- 230000000735 allogeneic effect Effects 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 230000008635 plant growth Effects 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 56
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 54
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- 229960001701 chloroform Drugs 0.000 description 28
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- -1 C 2 -C 4 alkyl Chemical class 0.000 description 21
- 239000002904 solvent Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000000460 chlorine Substances 0.000 description 18
- 230000000694 effects Effects 0.000 description 18
- 239000000203 mixture Substances 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 238000000034 method Methods 0.000 description 13
- 229910000027 potassium carbonate Inorganic materials 0.000 description 13
- 238000010992 reflux Methods 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 238000001816 cooling Methods 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 125000001309 chloro group Chemical group Cl* 0.000 description 9
- LZCLXQDLBQLTDK-BYPYZUCNSA-N ethyl (2S)-lactate Chemical compound CCOC(=O)[C@H](C)O LZCLXQDLBQLTDK-BYPYZUCNSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 241000209761 Avena Species 0.000 description 5
- 235000007319 Avena orientalis Nutrition 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- 241000196324 Embryophyta Species 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 5
- ALRGGAOHSITTLL-SECBINFHSA-N (2R)-2-[4-(2,4-dichlorophenoxy)phenoxy]propanoyl chloride Chemical compound ClC1=C(OC2=CC=C(O[C@@H](C(=O)Cl)C)C=C2)C=CC(=C1)Cl ALRGGAOHSITTLL-SECBINFHSA-N 0.000 description 4
- OOLBCHYXZDXLDS-SECBINFHSA-N (R)-diclofop Chemical compound C1=CC(O[C@H](C)C(O)=O)=CC=C1OC1=CC=C(Cl)C=C1Cl OOLBCHYXZDXLDS-SECBINFHSA-N 0.000 description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
- 235000007320 Avena fatua Nutrition 0.000 description 4
- 241000209764 Avena fatua Species 0.000 description 4
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 4
- 235000021536 Sugar beet Nutrition 0.000 description 4
- DHEPLMUINOAZLH-LLVKDONJSA-N ethyl (2R)-2-[4-(2,4-dichlorophenoxy)phenoxy]propanoate Chemical compound C1=CC(O[C@H](C)C(=O)OCC)=CC=C1OC1=CC=C(Cl)C=C1Cl DHEPLMUINOAZLH-LLVKDONJSA-N 0.000 description 4
- RGEUNBCMSKLYJC-GFCCVEGCSA-N ethyl (2r)-2-[4-(4-chlorophenoxy)phenoxy]propanoate Chemical compound C1=CC(O[C@H](C)C(=O)OCC)=CC=C1OC1=CC=C(Cl)C=C1 RGEUNBCMSKLYJC-GFCCVEGCSA-N 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 3
- XNBRPBFBBCFVEH-CQSZACIVSA-N 2-methylpropyl (2r)-2-[4-(4-chlorophenoxy)phenoxy]propanoate Chemical compound C1=CC(O[C@H](C)C(=O)OCC(C)C)=CC=C1OC1=CC=C(Cl)C=C1 XNBRPBFBBCFVEH-CQSZACIVSA-N 0.000 description 3
- 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 3
- 241001621841 Alopecurus myosuroides Species 0.000 description 3
- 235000016068 Berberis vulgaris Nutrition 0.000 description 3
- 241000335053 Beta vulgaris Species 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- BAWFPAQRZAGLPR-LLVKDONJSA-N ethyl (2R)-2-[4-(4-bromo-2-chlorophenoxy)phenoxy]propanoate Chemical compound C1=CC(O[C@H](C)C(=O)OCC)=CC=C1OC1=CC=C(Br)C=C1Cl BAWFPAQRZAGLPR-LLVKDONJSA-N 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- BSFAVVHPEZCASB-SNVBAGLBSA-N (2r)-2-[4-(4-chlorophenoxy)phenoxy]propanoic acid Chemical compound C1=CC(O[C@H](C)C(O)=O)=CC=C1OC1=CC=C(Cl)C=C1 BSFAVVHPEZCASB-SNVBAGLBSA-N 0.000 description 2
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 description 2
- BACHBFVBHLGWSL-SNVBAGLBSA-N (R)-diclofop-methyl Chemical compound C1=CC(O[C@H](C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-SNVBAGLBSA-N 0.000 description 2
- LVVQTPZQNHQLOM-UHFFFAOYSA-N 2,6-dichloro-1,3-benzoxazole Chemical compound C1=C(Cl)C=C2OC(Cl)=NC2=C1 LVVQTPZQNHQLOM-UHFFFAOYSA-N 0.000 description 2
- JJUNBBKSNIKPMW-ARLHGKGLSA-N 3-methoxybutyl (2R)-2-[4-(2,4-dichlorophenoxy)phenoxy]propanoate Chemical compound C1=CC(O[C@H](C)C(=O)OCCC(C)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl JJUNBBKSNIKPMW-ARLHGKGLSA-N 0.000 description 2
- FJFSSESWAFPCSU-UHFFFAOYSA-N 4-[4-(trifluoromethyl)phenoxy]phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(C(F)(F)F)C=C1 FJFSSESWAFPCSU-UHFFFAOYSA-N 0.000 description 2
- 241000743985 Alopecurus Species 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 231100000674 Phytotoxicity Toxicity 0.000 description 2
- 241000209504 Poaceae Species 0.000 description 2
- 241000209140 Triticum Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 150000001340 alkali metals Chemical group 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 2
- OZGWXXWBKDYPJV-GFCCVEGCSA-N ethyl (2R)-2-[4-[(2,4-dichlorophenyl)methyl]phenoxy]propanoate Chemical compound C1=CC(O[C@H](C)C(=O)OCC)=CC=C1CC1=CC=C(Cl)C=C1Cl OZGWXXWBKDYPJV-GFCCVEGCSA-N 0.000 description 2
- FEMOFHMHEFIHKN-GFCCVEGCSA-N ethyl (2r)-2-[4-[4-(trifluoromethyl)phenoxy]phenoxy]propanoate Chemical compound C1=CC(O[C@H](C)C(=O)OCC)=CC=C1OC1=CC=C(C(F)(F)F)C=C1 FEMOFHMHEFIHKN-GFCCVEGCSA-N 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- 229940035429 isobutyl alcohol Drugs 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- QIWVGZJFXBPJAR-LLVKDONJSA-N methyl (2R)-2-[4-[(2,4-dichlorophenyl)methyl]phenoxy]propanoate Chemical compound C1=CC(O[C@H](C)C(=O)OC)=CC=C1CC1=CC=C(Cl)C=C1Cl QIWVGZJFXBPJAR-LLVKDONJSA-N 0.000 description 2
- MDXGYOOITGBCBW-LLVKDONJSA-N methyl (2r)-2-[4-[4-(trifluoromethyl)phenoxy]phenoxy]propanoate Chemical compound C1=CC(O[C@H](C)C(=O)OC)=CC=C1OC1=CC=C(C(F)(F)F)C=C1 MDXGYOOITGBCBW-LLVKDONJSA-N 0.000 description 2
- LPEKGGXMPWTOCB-VKHMYHEASA-N methyl (S)-lactate Chemical compound COC(=O)[C@H](C)O LPEKGGXMPWTOCB-VKHMYHEASA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- YGTHVYSXHIVTOV-SECBINFHSA-N (2R)-2-[4-(4-bromo-2-chlorophenoxy)phenoxy]propanoic acid Chemical compound C1=CC(O[C@H](C)C(O)=O)=CC=C1OC1=CC=C(Br)C=C1Cl YGTHVYSXHIVTOV-SECBINFHSA-N 0.000 description 1
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 1
- XLHUBROMZOAQMV-UHFFFAOYSA-N 1,4-benzosemiquinone Chemical group [O]C1=CC=C(O)C=C1 XLHUBROMZOAQMV-UHFFFAOYSA-N 0.000 description 1
- TZGFQIXRVUHDLE-UHFFFAOYSA-N 1-chloro-2-nitro-4-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CC=C1Cl TZGFQIXRVUHDLE-UHFFFAOYSA-N 0.000 description 1
- SPXOTSHWBDUUMT-UHFFFAOYSA-N 138-42-1 Chemical compound OS(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1 SPXOTSHWBDUUMT-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- OVZHLDGIWDPRAL-UHFFFAOYSA-N 2-[4-(2,4-dichlorophenoxy)phenoxy]-n,n-diethylpropanamide Chemical compound C1=CC(OC(C)C(=O)N(CC)CC)=CC=C1OC1=CC=C(Cl)C=C1Cl OVZHLDGIWDPRAL-UHFFFAOYSA-N 0.000 description 1
- 150000005749 2-halopyridines Chemical class 0.000 description 1
- JSGVZVOGOQILFM-UHFFFAOYSA-N 3-methoxy-1-butanol Chemical compound COC(C)CCO JSGVZVOGOQILFM-UHFFFAOYSA-N 0.000 description 1
- NWFAJOGQUGZVOS-UHFFFAOYSA-N 4-(3,5-dichloropyridin-2-yl)oxyphenol Chemical compound C1=CC(O)=CC=C1OC1=NC=C(Cl)C=C1Cl NWFAJOGQUGZVOS-UHFFFAOYSA-N 0.000 description 1
- AJIHBUNFLVGSRK-UHFFFAOYSA-N 4-(4-bromo-2-chlorophenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(Br)C=C1Cl AJIHBUNFLVGSRK-UHFFFAOYSA-N 0.000 description 1
- XQMRZWSYBUCVAX-UHFFFAOYSA-N 4-(4-chlorophenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(Cl)C=C1 XQMRZWSYBUCVAX-UHFFFAOYSA-N 0.000 description 1
- NPNHACUAJQMTLH-UHFFFAOYSA-N 4-[(2,4-dichlorophenyl)methyl]phenol Chemical compound C1=CC(O)=CC=C1CC1=CC=C(Cl)C=C1Cl NPNHACUAJQMTLH-UHFFFAOYSA-N 0.000 description 1
- JALNRUNPNYFRJM-UHFFFAOYSA-N 4-[(5-chloro-1,3-benzoxazol-2-yl)oxy]phenol Chemical compound C1=CC(O)=CC=C1OC1=NC2=CC(Cl)=CC=C2O1 JALNRUNPNYFRJM-UHFFFAOYSA-N 0.000 description 1
- RGECUFYJLMZQOI-UHFFFAOYSA-N 4-[(6-chloro-1,3-benzothiazol-2-yl)oxy]phenol Chemical compound C1=CC(O)=CC=C1OC1=NC2=CC=C(Cl)C=C2S1 RGECUFYJLMZQOI-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 244000152970 Digitaria sanguinalis Species 0.000 description 1
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 1
- 244000058871 Echinochloa crus-galli Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 101000653759 Homo sapiens Sphingosine 1-phosphate receptor 5 Proteins 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical group CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 235000011999 Panicum crusgalli Nutrition 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 235000008515 Setaria glauca Nutrition 0.000 description 1
- 244000010062 Setaria pumila Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical group [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 244000062793 Sorghum vulgare Species 0.000 description 1
- 102100029802 Sphingosine 1-phosphate receptor 5 Human genes 0.000 description 1
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical group OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 229940125810 compound 20 Drugs 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
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- HVCNNTAUBZIYCG-LLVKDONJSA-N ethyl (2r)-2-[4-[(6-chloro-1,3-benzothiazol-2-yl)oxy]phenoxy]propanoate Chemical compound C1=CC(O[C@H](C)C(=O)OCC)=CC=C1OC1=NC2=CC=C(Cl)C=C2S1 HVCNNTAUBZIYCG-LLVKDONJSA-N 0.000 description 1
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- WIQBLACSWFFUKI-SNVBAGLBSA-N methyl (2R)-2-[4-[2-nitro-4-(trifluoromethyl)phenoxy]phenoxy]propanoate Chemical compound C1=CC(O[C@H](C)C(=O)OC)=CC=C1OC1=CC=C(C(F)(F)F)C=C1[N+]([O-])=O WIQBLACSWFFUKI-SNVBAGLBSA-N 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 1
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- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 230000001473 noxious effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 150000004707 phenolate Chemical class 0.000 description 1
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- 239000002798 polar solvent Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 1
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- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 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
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
Classifications
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/31—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of functional groups containing oxygen only in singly bound form
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
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- 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
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- C07D213/62—Oxygen or sulfur atoms
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- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/26—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles 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 in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/12—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Pest Control & Pesticides (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Furan Compounds (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2758002 | 1977-12-24 | ||
| DE19772758002 DE2758002A1 (de) | 1976-09-10 | 1977-12-24 | Optisch aktive herbizide mittel |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK579078A DK579078A (da) | 1979-06-25 |
| DK156511B DK156511B (da) | 1989-09-04 |
| DK156511C true DK156511C (da) | 1995-05-22 |
Family
ID=37084864
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK579078AA DK156511C (da) | 1977-12-24 | 1978-12-22 | Optisk aktive, p-substituerede alfa-phenoxy-propionsyrederivater med anvendelse som herbicider |
Country Status (29)
| Country | Link |
|---|---|
| US (2) | US4531969A (cs) |
| EP (1) | EP0002800B2 (cs) |
| JP (2) | JPS54112828A (cs) |
| AT (1) | AT368357B (cs) |
| AU (1) | AU527127B2 (cs) |
| BE (1) | BE873844A (cs) |
| BG (1) | BG33581A3 (cs) |
| BR (1) | BR7808443A (cs) |
| CA (1) | CA1268475A (cs) |
| CH (1) | CH650493A5 (cs) |
| CS (1) | CS204959B2 (cs) |
| DD (1) | DD141403A5 (cs) |
| DE (1) | DE2861428D1 (cs) |
| DK (1) | DK156511C (cs) |
| ES (1) | ES476100A1 (cs) |
| FR (1) | FR2447366A1 (cs) |
| GB (1) | GB2042503A (cs) |
| GR (1) | GR65233B (cs) |
| HU (1) | HU182883B (cs) |
| IE (1) | IE47703B1 (cs) |
| IL (1) | IL56283A (cs) |
| MX (2) | MX5673E (cs) |
| NZ (1) | NZ189267A (cs) |
| OA (1) | OA06138A (cs) |
| PL (1) | PL122180B1 (cs) |
| PT (1) | PT68979A (cs) |
| RO (2) | RO75478B (cs) |
| SU (2) | SU1336939A3 (cs) |
| ZA (1) | ZA787210B (cs) |
Families Citing this family (61)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0107866B1 (en) * | 1977-08-12 | 1988-03-30 | Imperial Chemical Industries Plc | Trihalomethylpyridine compounds |
| US4200587A (en) * | 1977-11-28 | 1980-04-29 | Hoffmann-La Roche Inc. | 2-[P-(p-Substituted phenoxy)phenoxy]propionyl oximes |
| JPH0224818B2 (cs) * | 1978-02-15 | 1990-05-30 | Imuperiaru Chem Ind Plc | |
| DE2964580D1 (en) * | 1978-03-01 | 1983-03-03 | Ici Plc | Herbicidal pyridine compounds and herbicidal compositions containing them |
| BE879987A (nl) * | 1978-11-21 | 1980-05-13 | Shell Int Research | Fenoxyfenoxypropionzuurderivaten, werkwijze ter bereiding daarvan, herbicidepreparaten die deze direvaten bevatten en methode ter bestrijding van onkruid onder toepassing van genoemde derivaten |
| IT8048925A0 (it) * | 1979-06-22 | 1980-06-10 | Sandoz Ag | Esteri del tetraidro-2h-2-piranilmetanolo loro preparazione e loro impiego come erbicidi |
| NZ194196A (en) * | 1979-07-17 | 1983-07-15 | Ici Australia Ltd | -(quinoxalin-2-yl(oxy or thio) phen (oxy or ylthio)-alkanoic acid derivatives or precursors |
| ZA811357B (en) * | 1980-03-10 | 1982-03-31 | Hoffmann La Roche | Oxime esters |
| US4358612A (en) | 1981-01-02 | 1982-11-09 | Stauffer Chemical Company | Process for production of α-haloalkylamides |
| DE3115152A1 (de) * | 1981-04-15 | 1982-12-02 | Hoechst Ag, 6000 Frankfurt | "heterocyclische phenylether und diese enthaltende herbizide mittel" |
| DK220582A (da) * | 1981-05-26 | 1982-11-27 | Hoffmann La Roche | Propionsyreamider |
| DE3319289A1 (de) * | 1983-05-27 | 1984-11-29 | Bayer Ag, 5090 Leverkusen | Optisch aktive phenoxypropionsaeure-ester |
| DK305884A (da) * | 1983-06-24 | 1984-12-25 | Yamanouchi Pharma Co Ltd | Phenoxyderivat, fremgangsmaade til fremstilling deraf og farmaceutisk praeparat indeholdende et saadant derivat |
| US4532328A (en) * | 1983-07-14 | 1985-07-30 | The Dow Chemical Company | Process for making optically active esters of phenoxyphenoxypropionic acids or pyridyloxyphenoxypropionic acids |
| AU587366B2 (en) * | 1983-07-27 | 1989-08-17 | Imperial Chemical Industries Plc | Process for producing optically active aryloxypropionic acids and derivatives thereof |
| US4550192A (en) * | 1983-09-01 | 1985-10-29 | The Dow Chemical Company | Fluorophenoxyphenoxypropionates and derivatives thereof |
| US4642338A (en) * | 1983-09-01 | 1987-02-10 | The Dow Chemical Company | Fluorophenoxyphenoxypropionates and derivatives thereof |
| DE3415069A1 (de) * | 1983-11-19 | 1985-05-30 | Hoechst Ag, 6230 Frankfurt | Herbizide mittel |
| DE3502266A1 (de) * | 1985-01-24 | 1986-08-07 | Bayer Ag, 5090 Leverkusen | Optisch aktive phenoxypropionsaeure-derivate |
| EP0191736B1 (de) * | 1985-02-14 | 1991-07-17 | Ciba-Geigy Ag | Verwendung von Chinolinderivaten zum Schützen von Kulturpflanzen |
| AU602485B2 (en) * | 1985-03-16 | 1990-10-18 | Wellcome Foundation Limited, The | Lipoxygenase and/or cyclooxygenase inhibitory compounds |
| GB8531839D0 (en) * | 1985-12-30 | 1986-02-05 | Wellcome Found | Aryl derivatives |
| JPS61249954A (ja) * | 1985-04-26 | 1986-11-07 | Aguro Kanesho Kk | プロピオン酸誘導体 |
| US4857101A (en) * | 1985-12-06 | 1989-08-15 | Rohm And Haas Company | Method of selectively controlling weeds in crops of cereals |
| US4790868A (en) * | 1986-03-17 | 1988-12-13 | Ppg Industries, Inc. | Herbicidally active substituted phenoxy or phenylthio benzoxazolone (or benzthiazolone) compounds |
| US4746351A (en) * | 1986-05-12 | 1988-05-24 | Ppg Industries, Inc. | Herbicidally active substituted phenoxy benzoxazole (or benzothiazole) |
| CH679396A5 (cs) * | 1986-06-12 | 1992-02-14 | Ciba Geigy Ag | |
| NZ224297A (en) * | 1987-04-20 | 1990-07-26 | Agro Kanesho Co Ltd | Phenoxypropionic acid ester derivatives and herbicidal compositions |
| US5207819A (en) * | 1987-04-20 | 1993-05-04 | Agro-Kanesho Co., Ltd | Phenoxypropionic acid ester derivatives |
| US4789744A (en) * | 1987-08-05 | 1988-12-06 | The Dow Chemical Company | Process for the resolution of enantiomeric aryloxyphenoxy propionates |
| US4786732A (en) * | 1987-08-05 | 1988-11-22 | The Dow Chemical Company | Resolution of enantiomers of 2-(4-aryloxyphenoxy) propionic acids by liquid chromatography with a chiral eluent |
| US4786731A (en) * | 1987-08-05 | 1988-11-22 | The Dow Chemical Company | Resolution of enantiomers of 2-(phenyl or phenoxy/propionic acids using optically active alkanolamines |
| US4935522A (en) * | 1988-03-21 | 1990-06-19 | Hoechst Celanese Corporation | Process for producing ethyl 2-[4'-(6"-chloro-2"-benzoxazolyloxy)phenoxy]propionate |
| US4897481A (en) * | 1988-05-31 | 1990-01-30 | The Dow Chemical Company | Process for the minimization of racemization in the preparation of optically active ((aryloxy)phenoxy)propionate herbicides |
| US4831147A (en) * | 1988-07-05 | 1989-05-16 | The Dow Chemical Company | Resolution of enantiomers of herbicidal 2-(4-aryloxyphenoxy) propionates by chiral two-phase extraction |
| US5012017A (en) * | 1988-08-18 | 1991-04-30 | Dowelanco | Phenoxyphenoxypropionates, intermediates thereof and methods of preparation |
| DE3902372A1 (de) * | 1989-01-27 | 1990-08-02 | Hoechst Ag | Verfahren zur herstellung von d((pfeil hoch)+(pfeil hoch))-2-(4-acetylphenoxy)- propionsaeureestern |
| EP0383613A3 (en) * | 1989-02-16 | 1991-04-03 | Tosoh Corporation | Optically active lactate, derivatives thereof and processes of producing same |
| US5258521A (en) * | 1989-07-26 | 1993-11-02 | Tosoh Corporation | Process of producing optically active propionic acid ester derivatives |
| DE59010829D1 (de) * | 1989-10-18 | 1998-07-16 | Hoechst Schering Agrevo Gmbh | Herbizide wirkstoffkombinationen |
| US5811374A (en) * | 1991-02-07 | 1998-09-22 | Bayer Aktiengesellschaft | 3-aryl-pyrrolidine-2,4-dione derivatives |
| DE4126999A1 (de) * | 1991-08-16 | 1993-02-18 | Basf Ag | Herbizide mittel, enthaltend 3-aminobenzo(b)thiophene als antidots |
| ATE161389T1 (de) * | 1991-09-14 | 1998-01-15 | Hoechst Schering Agrevo Gmbh | Selektive herbizide mittel in form konzentrierter mikroemulsionen |
| DE4131585A1 (de) * | 1991-09-23 | 1993-03-25 | Bayer Ag | (alpha)-(5-dichlorphenoxy-naphthalin-l-yl-oxy) -propionsaeure-derivate |
| DE69314718T2 (de) * | 1992-07-21 | 1998-02-26 | Ciba Geigy Ag | Oxamidsäure-Derivate als hypocholesterämische Mittel |
| JPH06179646A (ja) * | 1992-12-15 | 1994-06-28 | Tokuyama Soda Co Ltd | シアノケトン誘導体 |
| US5756425A (en) * | 1996-09-09 | 1998-05-26 | Ash; David | Fluazifop-butyl formulation and process for the selective control of Bermuda and other grasses in Bentgrass and St. Augustinegrass turf |
| US6600048B2 (en) | 1998-07-25 | 2003-07-29 | Dongbu Hannong Chemical Co., Ltd. | Herbicidal phenoxypropionic acid N-alkyl-N-2-fluorophenyl amide compounds |
| TW561153B (en) | 1998-07-25 | 2003-11-11 | Dongbu Hannong Chemical Co Ltd | Herbicidal phenoxypropionic acid N-alkyl-N-2-fluoro-phenyl amide compounds |
| ATE250855T1 (de) * | 1999-08-03 | 2003-10-15 | Dongbu Hannong Chemical Co Ltd | Hochselektive herbizide phenoxypropionsäure- alkoxycarbonylanilide und verfahren zu ihrer herstellung |
| KR100419853B1 (ko) * | 2000-05-04 | 2004-02-25 | 동부한농화학 주식회사 | 제초활성을 가지는 광활성 (r)-페녹시프로피온산-n-메틸-n-2-플루오로페닐아미드 화합물 |
| KR100552133B1 (ko) * | 2002-06-26 | 2006-02-14 | 한국화학연구원 | 광학활성 (r)-아릴옥시 프로피온산 에스터 유도체의제조방법 |
| EP2052607A1 (de) | 2007-10-24 | 2009-04-29 | Bayer CropScience AG | Herbizid-Kombination |
| DE102008037622A1 (de) | 2008-08-14 | 2010-02-25 | Bayer Cropscience Ag | Herbizid-Kombination mit Dimethoxytriazinyl-substituierten Difluormethansulfonylaniliden |
| CN101372481B (zh) * | 2008-08-19 | 2012-03-14 | 江苏中意化学有限公司 | 6-氯-2-(对羟基)-苯氧基-苯并噁唑的合成方法 |
| US8186436B2 (en) * | 2009-09-10 | 2012-05-29 | Warren Carlos | Thermal insulating packer fluid |
| CN102351808B (zh) * | 2011-09-06 | 2013-07-03 | 江苏中旗作物保护股份有限公司 | 一种新的精恶唑禾草灵的合成方法 |
| WO2015131019A1 (en) * | 2014-02-28 | 2015-09-03 | The Texas A&M University System | Compositions and methods for inhibition of mycobacteria |
| EP3222143A1 (en) | 2016-03-24 | 2017-09-27 | Bayer CropScience Aktiengesellschaft | Use of certain herbicide combinations based on iodosulfuron in teff plants |
| CN106699649B (zh) * | 2016-12-15 | 2019-10-08 | 三峡大学 | 2-(六元芳氧基苯氧基)烷酸衍生物及其应用 |
| CN118546105A (zh) * | 2023-02-24 | 2024-08-27 | 沈阳中化农药化工研发有限公司 | 一种芳氧苯氧丙酸酯类化合物及应用 |
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| DE2546251A1 (de) * | 1974-10-17 | 1976-04-29 | Ishihara Mining & Chemical Co | Alpha- eckige klammer auf 4-(5- mono-substituiert- oder 3,5-disubstituiert-pyridyl-2-oxy)phenoxy eckige klammer zu alkancarbonsaeuren und ihre derivate |
| DE2623558A1 (de) * | 1976-05-26 | 1977-12-15 | Hoechst Ag | Phenoxi-phenoxipropionsaeure-derivate |
| DE2531643B2 (de) * | 1974-07-17 | 1978-07-13 | Ishihara Sangyo Kaisha, Ltd. Osaka (Japan) | a-[4- (4- Trifluormethylphenoxy) -phenoxy] -propionsäurederivate und diese enthaltende Unkrautvertilgungsmittel |
| DK346079A (da) * | 1977-12-23 | 1979-08-17 | Ici Ltd | Herbicidt pyridinderivat |
| DK156830B (da) * | 1977-07-22 | 1989-10-09 | Dow Chemical Co | Trifluormethylpyridyl(oxy/thio)phenoxypropionsyreforbindelser til anvendelse i herbicider, herbicidt middel, samt fremgangsmaade til bekaempelse af uoensket plantevaekst |
| DK157296B (da) * | 1977-08-12 | 1989-12-04 | Ici Ltd | 2-chlor-pyridinforbindelser til brug som udgangsmateriale ved fremstilling af herbicide pyridinforbindelser |
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| CA683033A (en) * | 1964-03-24 | Frommer Werner | OPTICALLY-ACTIVE .alpha.-ALKYL-SUBSTITUTED PHENOXYACETIC ACIDS AND PROCESSES FOR PRODUCING THE SAME | |
| CH2246A (de) * | 1890-05-18 | 1890-09-15 | J Pontius | Petroleumbehälter mit Schutzvorrichtung |
| US2668104A (en) * | 1951-08-23 | 1954-02-02 | Dow Chemical Co | Plant growth regulant compositions comprising chloroaryloxyacetic acids and esters thereof |
| DE2223894C3 (de) * | 1972-05-17 | 1981-07-23 | Hoechst Ag, 6000 Frankfurt | Herbizide Mittel auf Basis von Phenoxycarbonsäurederivaten |
| IL45894A0 (en) * | 1973-10-25 | 1974-12-31 | Ciba Geigy Ag | New aryl alkyl ethers,their preparation and their use in pest control |
| DE2417487C2 (de) * | 1974-04-10 | 1983-01-20 | Hoechst Ag, 6000 Frankfurt | Benzyl-phenoxyalkancarbonsäuren, deren Derivate und Verfahren zu ihrer Herstellung |
| DE2433067B2 (de) * | 1974-07-10 | 1977-11-24 | a- [4-(4" Trifluormethylphenoxy)-phenoxy] -propionsäuren und deren Derivate, Verfahren zu ihrer Herstellung und diese enthaltende herbizide Mittel Hoechst AG, 6000 Frankfurt | Alpha- eckige klammer auf 4-(4' trifluormethylphenoxy)-phenoxy eckige klammer zu -propionsaeuren und deren derivate, verfahren zu ihrer herstellung und diese enthaltende herbizide mittel |
| US4106925A (en) * | 1975-11-20 | 1978-08-15 | Ishihara Sangyo Kaisha Ltd. | Novel herbicidally active, nuclear-substituted phenoxy-phenoxy-alkanecarboxylic acid derivatives and use thereof for controlling grass-like weeds |
| JPS5283640A (en) * | 1976-01-01 | 1977-07-12 | Hoechst Ag | Benzyllphenoxyalkane carboxylate and derivatives thereof |
| DE2601548C2 (de) * | 1976-01-16 | 1984-01-26 | Hoechst Ag, 6230 Frankfurt | 2-[4-(2'-Chlor-4'-bromphenoxy)-phenoxy]-propionsäure und Derivate sowie diese enthaltende herbizide Mittel |
| JPS52131539A (en) * | 1976-04-13 | 1977-11-04 | Ishihara Sangyo Kaisha Ltd | Phenoxyphenoxypropionic acid derivatives and herbicides |
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| DE2617804C2 (de) * | 1976-04-23 | 1985-01-24 | Hoechst Ag, 6230 Frankfurt | 2-(4-Phenoxy phenoxy)-propionsäurederivate und ihre Verwendung als Herbizide |
| DE2640730C2 (de) * | 1976-09-10 | 1983-08-25 | Hoechst Ag, 6230 Frankfurt | Benzoxazolyloxy- und Benzothiazolyloxy-phenoxy-Verbindungen und diese enthaltende herbizide Mittel |
| IT1091580B (it) * | 1977-01-31 | 1985-07-06 | Hoffmann La Roche | Esteri di acidi fenossi-alcan-carbossilici sostituiti |
| US4090866A (en) * | 1977-03-14 | 1978-05-23 | O. M. Scott & Sons Company | Process for the selective control of tall fescue in turf |
| US4200587A (en) * | 1977-11-28 | 1980-04-29 | Hoffmann-La Roche Inc. | 2-[P-(p-Substituted phenoxy)phenoxy]propionyl oximes |
| DE2964580D1 (en) * | 1978-03-01 | 1983-03-03 | Ici Plc | Herbicidal pyridine compounds and herbicidal compositions containing them |
| DE2963229D1 (en) * | 1978-06-29 | 1982-08-19 | Ciba Geigy Ag | Herbicidal, optically active r(+)-dichloropyridyloxy-alpha-phenoxy-propionic acid-propargylesters, process for their preparation and their use in herbicidal compositions |
| BE879987A (nl) * | 1978-11-21 | 1980-05-13 | Shell Int Research | Fenoxyfenoxypropionzuurderivaten, werkwijze ter bereiding daarvan, herbicidepreparaten die deze direvaten bevatten en methode ter bestrijding van onkruid onder toepassing van genoemde derivaten |
-
1978
- 1978-01-25 CH CH829/78A patent/CH650493A5/de not_active IP Right Cessation
- 1978-12-15 MX MX787608U patent/MX5673E/es unknown
- 1978-12-18 ES ES476100A patent/ES476100A1/es not_active Expired
- 1978-12-19 BG BG041786A patent/BG33581A3/xx unknown
- 1978-12-20 US US05/971,427 patent/US4531969A/en not_active Expired - Lifetime
- 1978-12-20 EP EP78101792A patent/EP0002800B2/de not_active Expired - Lifetime
- 1978-12-20 DE DE7878101792T patent/DE2861428D1/de not_active Expired
- 1978-12-21 NZ NZ189267A patent/NZ189267A/xx unknown
- 1978-12-21 IE IE2547/78A patent/IE47703B1/en unknown
- 1978-12-21 ZA ZA00787210A patent/ZA787210B/xx unknown
- 1978-12-22 DK DK579078AA patent/DK156511C/da not_active IP Right Cessation
- 1978-12-22 AU AU42849/78A patent/AU527127B2/en not_active Expired
- 1978-12-22 CS CS788850A patent/CS204959B2/cs unknown
- 1978-12-22 CA CA000318525A patent/CA1268475A/en not_active Expired - Lifetime
- 1978-12-22 RO RO96022A patent/RO75478B/ro unknown
- 1978-12-22 IL IL56283A patent/IL56283A/xx unknown
- 1978-12-22 OA OA56694A patent/OA06138A/xx unknown
- 1978-12-22 RO RO7899034A patent/RO79065A/ro unknown
- 1978-12-22 BR BR7808443A patent/BR7808443A/pt unknown
- 1978-12-22 PT PT68979A patent/PT68979A/pt unknown
- 1978-12-22 AT AT0921278A patent/AT368357B/de not_active IP Right Cessation
- 1978-12-22 GR GR57976A patent/GR65233B/el unknown
- 1978-12-22 HU HU78HO2126A patent/HU182883B/hu unknown
- 1978-12-22 DD DD78210128A patent/DD141403A5/de not_active IP Right Cessation
- 1978-12-22 SU SU782700051A patent/SU1336939A3/ru active
- 1978-12-23 PL PL1978212111A patent/PL122180B1/pl unknown
- 1978-12-23 JP JP15817978A patent/JPS54112828A/ja active Pending
-
1979
- 1979-01-22 GB GB7902307A patent/GB2042503A/en not_active Withdrawn
- 1979-01-23 FR FR7901604A patent/FR2447366A1/fr active Granted
- 1979-01-31 BE BE193191A patent/BE873844A/xx not_active IP Right Cessation
-
1981
- 1981-01-20 SU SU813233698A patent/SU1075969A3/ru active
-
1983
- 1983-03-25 MX MX667383A patent/MX6673A/es unknown
-
1987
- 1987-10-07 JP JP62251741A patent/JPS63211250A/ja active Pending
-
1995
- 1995-06-06 US US08/465,889 patent/US5712226A/en not_active Expired - Lifetime
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2531643B2 (de) * | 1974-07-17 | 1978-07-13 | Ishihara Sangyo Kaisha, Ltd. Osaka (Japan) | a-[4- (4- Trifluormethylphenoxy) -phenoxy] -propionsäurederivate und diese enthaltende Unkrautvertilgungsmittel |
| DE2546251A1 (de) * | 1974-10-17 | 1976-04-29 | Ishihara Mining & Chemical Co | Alpha- eckige klammer auf 4-(5- mono-substituiert- oder 3,5-disubstituiert-pyridyl-2-oxy)phenoxy eckige klammer zu alkancarbonsaeuren und ihre derivate |
| DE2623558A1 (de) * | 1976-05-26 | 1977-12-15 | Hoechst Ag | Phenoxi-phenoxipropionsaeure-derivate |
| DK156830B (da) * | 1977-07-22 | 1989-10-09 | Dow Chemical Co | Trifluormethylpyridyl(oxy/thio)phenoxypropionsyreforbindelser til anvendelse i herbicider, herbicidt middel, samt fremgangsmaade til bekaempelse af uoensket plantevaekst |
| DK157296B (da) * | 1977-08-12 | 1989-12-04 | Ici Ltd | 2-chlor-pyridinforbindelser til brug som udgangsmateriale ved fremstilling af herbicide pyridinforbindelser |
| DK346079A (da) * | 1977-12-23 | 1979-08-17 | Ici Ltd | Herbicidt pyridinderivat |
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| Date | Code | Title | Description |
|---|---|---|---|
| PUP | Patent expired |