CH626318A5 - - Google Patents
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- Publication number
- CH626318A5 CH626318A5 CH286777A CH286777A CH626318A5 CH 626318 A5 CH626318 A5 CH 626318A5 CH 286777 A CH286777 A CH 286777A CH 286777 A CH286777 A CH 286777A CH 626318 A5 CH626318 A5 CH 626318A5
- Authority
- CH
- Switzerland
- Prior art keywords
- torr
- formula
- och3
- phenoxy
- alkyl
- Prior art date
Links
- 239000000460 chlorine Substances 0.000 description 39
- 241000196324 Embryophyta Species 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 240000007594 Oryza sativa Species 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- -1 benzyloxy, phenoxy Chemical group 0.000 description 9
- 239000012954 diazonium Substances 0.000 description 9
- 235000007164 Oryza sativa Nutrition 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 125000005843 halogen group Chemical group 0.000 description 8
- 235000009566 rice Nutrition 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 7
- 125000004093 cyano group Chemical group *C#N 0.000 description 7
- 150000001989 diazonium salts Chemical class 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- 241001233957 eudicotyledons Species 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 244000155504 Rotala indica Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 230000002363 herbicidal effect Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 150000002828 nitro derivatives Chemical class 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- BNJMRELGMDUDDB-UHFFFAOYSA-N $l^{1}-sulfanylbenzene Chemical compound [S]C1=CC=CC=C1 BNJMRELGMDUDDB-UHFFFAOYSA-N 0.000 description 2
- HBUCPZGYBSEEHF-UHFFFAOYSA-N 3-phenoxyphenol Chemical class OC1=CC=CC(OC=2C=CC=CC=2)=C1 HBUCPZGYBSEEHF-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 244000108484 Cyperus difformis Species 0.000 description 2
- 244000058871 Echinochloa crus-galli Species 0.000 description 2
- 241000209510 Liliopsida Species 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- QUIMTLZDMCNYGY-UHFFFAOYSA-N 2,4-dichloro-1-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1Cl QUIMTLZDMCNYGY-UHFFFAOYSA-N 0.000 description 1
- 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 1
- KDTZBYPBMTXCSO-UHFFFAOYSA-N 2-phenoxyphenol Chemical class OC1=CC=CC=C1OC1=CC=CC=C1 KDTZBYPBMTXCSO-UHFFFAOYSA-N 0.000 description 1
- ABEUJUYEUCCZQF-UHFFFAOYSA-N 4-chloro-2-methoxy-1-nitrobenzene Chemical compound COC1=CC(Cl)=CC=C1[N+]([O-])=O ABEUJUYEUCCZQF-UHFFFAOYSA-N 0.000 description 1
- 241000219144 Abutilon Species 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- 235000006463 Brassica alba Nutrition 0.000 description 1
- 244000140786 Brassica hirta Species 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
- 101100387923 Caenorhabditis elegans dos-1 gene Proteins 0.000 description 1
- 241000251730 Chondrichthyes Species 0.000 description 1
- 235000007516 Chrysanthemum Nutrition 0.000 description 1
- 240000005250 Chrysanthemum indicum Species 0.000 description 1
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
- 240000005702 Galium aparine Species 0.000 description 1
- 235000014820 Galium aparine Nutrition 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 241000207890 Ipomoea purpurea Species 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 235000011999 Panicum crusgalli Nutrition 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 244000275012 Sesbania cannabina Species 0.000 description 1
- 240000006410 Sida spinosa Species 0.000 description 1
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 1
- 244000061457 Solanum nigrum Species 0.000 description 1
- 235000002594 Solanum nigrum Nutrition 0.000 description 1
- 240000006394 Sorghum bicolor Species 0.000 description 1
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 241001148683 Zostera marina Species 0.000 description 1
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 1
- LYVWMIHLNQLWAC-UHFFFAOYSA-N [Cl].[Cu] Chemical compound [Cl].[Cu] LYVWMIHLNQLWAC-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 125000003302 alkenyloxy group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- ACEONLNNWKIPTM-UHFFFAOYSA-N methyl 2-bromopropanoate Chemical compound COC(=O)C(C)Br ACEONLNNWKIPTM-UHFFFAOYSA-N 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- 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
- 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
- A01N39/04—Aryloxy-acetic acids; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Polyurethanes Or Polyureas (AREA)
- Paints Or Removers (AREA)
Priority Applications (31)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH286777A CH626318A5 (es) | 1977-03-08 | 1977-03-08 | |
| FR7806325A FR2383165A1 (fr) | 1977-03-08 | 1978-03-06 | Nouveaux derives d'acides phenoxy-a-phenoxy-alcanecarboxyliques, leur preparation et leur application comme herbicides |
| DD78203989A DD135347A5 (de) | 1977-03-08 | 1978-03-06 | Herbizides mittel |
| CA298,224A CA1108167A (en) | 1977-03-08 | 1978-03-06 | HERBICIDALLY ACTIVE PHENOXY-.alpha.-PHENOXY- ALKANECARBOXYLIC ACID DERIVATIVES |
| DE19782809541 DE2809541A1 (de) | 1977-03-08 | 1978-03-06 | Neue herbizid wirksame phenoxy- alpha-phenoxy-alkancarbonsaeurederivate |
| GB9008/78A GB1600071A (en) | 1977-03-08 | 1978-03-07 | Herbicidally active phenoxy-a-phenoxyalkanecarboxylic acid derivatives |
| ZA00781342A ZA781342B (en) | 1977-03-08 | 1978-03-07 | Novel herbicidally active phenoxy-a-phenoxy-alkanecarboxylic acid derivatives |
| CS143478A CS204020B2 (cs) | 1977-03-08 | 1978-03-07 | Herbicidní prostředek a způsob výroby účinné složky |
| BR7801399A BR7801399A (pt) | 1977-03-08 | 1978-03-07 | Derivados de acido fenoxi-fenoxialcanocarboxilico,processo para sua preparacao,composicao herbicida e sua aplicacao |
| SU782587604A SU1075943A3 (ru) | 1977-03-08 | 1978-03-07 | Способ борьбы с нежелательной растительностью |
| NL7802487A NL7802487A (nl) | 1977-03-08 | 1978-03-07 | Fenoxy-alfa-fenoxy-alkaancarbonzuurderivaten, werkwijze voor het bereiden ervan alsmede de toepassing ervan als herbicide. |
| AU33909/78A AU523611B2 (en) | 1977-03-08 | 1978-03-07 | Herbicidally active phenoxy-phenoxy-alkane carboxylic acid derivatives |
| BE185719A BE864632A (fr) | 1977-03-08 | 1978-03-07 | Nouveaux derives d'acides phenoxy-alpha-phenoxy-alcanecarboxyliques, leur preparation et leur application comme herbicides |
| GB20736/80A GB1600072A (en) | 1977-03-08 | 1978-03-07 | Herbicidally active phenoxy-a-phenoxyalkanecarboxylic acid derivatives |
| HU78CI1817A HU180702B (en) | 1977-03-08 | 1978-03-07 | Herbicide compositions containing phenoxy-alpha-phenoxy-alkane-carboxylic acid derivatives,and process for producing the active agents |
| GB22531/80A GB1600074A (en) | 1977-03-08 | 1978-03-07 | Herbicidally active phenoxy-a-phenoxyalkanecarboxylic acid derivatives |
| AT162578A AT360267B (de) | 1977-03-08 | 1978-03-07 | Herbizides mittel |
| IL54218A IL54218A (en) | 1977-03-08 | 1978-03-07 | Alpha-(6-substituted-3-phenoxyphenoxy)alkanoic acid derivatives,their production and herbicidal compositions containing them |
| IT20972/78A IT1093509B (it) | 1977-03-08 | 1978-03-07 | Derivati di acidi fenossi und fenossi,alcan,carbossilici attivi come erbicidi e procedimento per la loro preparazione |
| AT0009280A AT367390B (de) | 1977-03-08 | 1978-03-07 | Verfahren zur herstellung neuer alfa-(3-phenoxyphenoxy)-alkancarbons[urederivate |
| ES467627A ES467627A1 (es) | 1977-03-08 | 1978-03-07 | Procedimiento para la preparacion de derivados de acido 3- fenoxi-alfa-fenoxi-alcancarboxilico |
| GB22530/80A GB1600073A (en) | 1977-03-08 | 1978-03-07 | Herbicidally active phenoxy-a-pehnoxyalkanecarboxylic acid derivatives |
| JP2647978A JPS53112821A (en) | 1977-03-08 | 1978-03-08 | 33phenoxyyalphaaphenoxyyalkanee carboxylate derivative process for preparing same herbicide and method of defoliating or dryyuping culture plant |
| PH20860A PH15239A (en) | 1977-03-08 | 1978-03-08 | Novel herbicidally active phenoxy-alpha-phenoxy alkanecarboxylic acid derivatives |
| TR19997A TR19997A (tr) | 1977-03-08 | 1978-03-08 | Herbisid olarak mueessir yeni fenokai-fenoksi-alkan-karboksili asid tuerevleri |
| US06/083,905 US4304936A (en) | 1977-03-08 | 1979-10-11 | Herbicidal 3-(trifluro-methyl-halophenoxy)-α-phenoxyalkanecarboxylic acid amides |
| CS798710A CS204022B2 (cs) | 1977-03-08 | 1979-12-12 | Herbicidní prostředek a způsob výroby účinné látky |
| CS798709A CS204021B2 (cs) | 1977-03-08 | 1979-12-12 | Herbicidní prostředek a způsob výroby účinné složky |
| CA342,422A CA1127347A (en) | 1977-03-08 | 1979-12-20 | Process for producing thermosetting binders for cathodically depositable electrodeposition paints |
| US06/263,650 US4394327A (en) | 1977-03-08 | 1981-05-14 | Herbicidally active phenoxy-α-phenoxy-alkanecarboxylic acid derivatives |
| US06/297,299 US4417918A (en) | 1977-03-08 | 1981-08-28 | Herbicidal α-[3-(2-halo-4-trifluoromethylphenoxy)-6-halophenoxy]propionic acid thio esters and acids |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH286777A CH626318A5 (es) | 1977-03-08 | 1977-03-08 | |
| CH818277 | 1977-07-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH626318A5 true CH626318A5 (es) | 1981-11-13 |
Family
ID=25691594
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH286777A CH626318A5 (es) | 1977-03-08 | 1977-03-08 |
Country Status (19)
| Country | Link |
|---|---|
| US (3) | US4304936A (es) |
| JP (1) | JPS53112821A (es) |
| AT (2) | AT360267B (es) |
| AU (1) | AU523611B2 (es) |
| BE (1) | BE864632A (es) |
| BR (1) | BR7801399A (es) |
| CA (2) | CA1108167A (es) |
| CH (1) | CH626318A5 (es) |
| DD (1) | DD135347A5 (es) |
| DE (1) | DE2809541A1 (es) |
| ES (1) | ES467627A1 (es) |
| FR (1) | FR2383165A1 (es) |
| GB (4) | GB1600074A (es) |
| HU (1) | HU180702B (es) |
| IL (1) | IL54218A (es) |
| IT (1) | IT1093509B (es) |
| NL (1) | NL7802487A (es) |
| PH (1) | PH15239A (es) |
| TR (1) | TR19997A (es) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4059435A (en) * | 1976-08-31 | 1977-11-22 | Rohm And Haas Company | Herbicidal 4-trifluoromethyl-3-cyanoalkoxy-4-nitro diphenyl ethers |
| LU78554A1 (de) * | 1977-11-21 | 1979-06-13 | Ciba Geigy Ag | Verfahren zur herstellung neuer 3-hydroxydiphenylaether |
| DE2805982A1 (de) * | 1978-02-13 | 1979-08-16 | Bayer Ag | Phenoxyessigsaeure-derivate, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| DE2805981A1 (de) * | 1978-02-13 | 1979-08-16 | Bayer Ag | Phenoxypropionsaeure-derivate, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| DE2906237A1 (de) * | 1979-02-17 | 1980-08-28 | Bayer Ag | Phenoxycarbonsaeureamide, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| EP0018324A1 (de) * | 1979-04-12 | 1980-10-29 | Ciba-Geigy Ag | Herbizid wirksame substituierte Diphenylätherderivate, Verfahren zu ihrer Herstellung sowie herbizide Mittel und deren Verwendung |
| DE3100387A1 (de) * | 1981-01-09 | 1982-09-02 | Basf Ag, 6700 Ludwigshafen | Substituierte diphenylether, diese enthaltende herbizide und ihre anwendung als herbizide |
| US4419123A (en) * | 1981-10-19 | 1983-12-06 | Rohm And Haas Company | Herbicidal 4-trifluoromethyl-3'-carbon-substituted-4'-substituted diphenyl ethers |
| US4509970A (en) * | 1981-12-17 | 1985-04-09 | Zoecon Corporation | Substituted phenylphosphinyloxy- and phosphinylthio-iminocarboxylates useful for the control of weeds |
| US4402729A (en) * | 1982-05-07 | 1983-09-06 | Velsicol Chemical Corporation | Heterocyclic amides of phenoxyphenoxyalkanoic acids |
| GB2121174B (en) * | 1982-05-20 | 1986-01-08 | Robert James Redding | Measurement of distance using ultrasound |
| CA1249993A (en) * | 1983-10-18 | 1989-02-14 | Paul Winternitz | Aryloxyphenoxy(acyloxy)alkyloximes, -carbamates and-phosphonates |
| US4600432A (en) * | 1984-07-25 | 1986-07-15 | Agro-Kanesho Co., Ltd. | Propionic acid derivatives and herbicides employing them |
| FR2598146B1 (fr) * | 1986-04-30 | 1989-01-20 | Rech Ind | Nouveau procede de preparation de fibrates. |
| ES2045018T3 (es) * | 1987-08-05 | 1994-01-16 | Dowelanco | Acidos fluorofenoxifenoxialcanoicos y sus derivados de caracter herbicida. |
| DE3926055A1 (de) * | 1989-08-07 | 1991-02-14 | Basf Ag | Verwendung von diphenyletherderivaten zur desikkation und abszission von pflanzenorganen |
| EP0533925A1 (en) * | 1990-06-11 | 1993-03-31 | Teijin Limited | Optical isomer of r-form of diphenyl ether derivative and herbicide containing the same as active ingredient |
| DE4111619A1 (de) * | 1991-04-10 | 1992-10-15 | Bayer Ag | (alpha)-(5-aryloxy-naphthalin-1-yl-oxy)-carbonsaeure-derivate |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2412510A (en) * | 1944-06-02 | 1946-12-10 | American Chem Paint Co | Methods and compositions for killing weeds |
| GB1041982A (en) * | 1963-09-30 | 1966-09-07 | Boots Pure Drug Co Ltd | Herbicidal compounds and compositions |
| US3287106A (en) * | 1963-11-15 | 1966-11-22 | Monsanto Co | Method for inhibiting the growth of grass type weeds |
| US3268324A (en) * | 1965-10-11 | 1966-08-23 | Monsanto Co | Herbicidal composition and method employing oxa aliphatic acetamide |
| US3557209A (en) * | 1967-10-18 | 1971-01-19 | Velsicol Chemical Corp | Phenoxyacetamides |
| US3784635A (en) * | 1969-04-25 | 1974-01-08 | Mobil Oil Corp | Substituted phenoxybenzoic acids and esters thereof |
| DE2223894C3 (de) * | 1972-05-17 | 1981-07-23 | Hoechst Ag, 6000 Frankfurt | Herbizide Mittel auf Basis von Phenoxycarbonsäurederivaten |
| JPS5071826A (es) * | 1973-11-09 | 1975-06-14 | ||
| 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 |
| GB1563195A (en) * | 1975-08-20 | 1980-03-19 | Sori Soc Rech Ind | Derivating of phenoxy-alkylcarboxylic acids |
| US4070178A (en) * | 1975-09-03 | 1978-01-24 | Rohm And Haas Company | Herbicidal diphenyl ethers |
| JPS5934705B2 (ja) * | 1976-03-05 | 1984-08-24 | 石原産業株式会社 | フエノキシフエノキシアルカンニトリル誘導体及びそれらを含有する除草剤 |
| JPS5828262B2 (ja) * | 1976-03-17 | 1983-06-15 | 石原産業株式会社 | フエノキシフエノキシアルカンカルボン酸誘導体及びそれらを含有する除草剤 |
| JPS5814402B2 (ja) * | 1975-09-27 | 1983-03-18 | 石原産業株式会社 | ジヨソウザイ |
| NZ181994A (en) * | 1975-09-27 | 1978-09-20 | Ishihara Sangyo Kaisha | (2-chloro-4-trifluorom-ethylphenoxy)-phenoxy acids,esters,ethers,amides and nitriles and herbicidal compositions |
| 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 |
| GB1565972A (en) * | 1976-04-15 | 1980-04-23 | Sori Soc Rech Ind | M-substituted phenoxypropionic acid dervatives |
| US4173464A (en) * | 1976-05-07 | 1979-11-06 | Sumitomo Chemical Company, Limited | m-Phenoxybenzamide derivatives |
| DOP1977002612A (es) | 1976-07-09 | 1983-05-25 | Ciba Geigy Ag | Nuevos derivados de acido fenixi-fenoxi-alcancarboxilico sustituidos en el nucleo de accion herbicida y empleo de ellos para combatir las malas hierbas |
| DE2632581C2 (de) * | 1976-07-20 | 1982-07-15 | Hoechst Ag, 6000 Frankfurt | Substituierte Nitrodiphenylether, Verfahren zu ihrer Herstellung und diese enthaltende herbizide Mittel |
-
1977
- 1977-03-08 CH CH286777A patent/CH626318A5/de not_active IP Right Cessation
-
1978
- 1978-03-06 DE DE19782809541 patent/DE2809541A1/de not_active Withdrawn
- 1978-03-06 FR FR7806325A patent/FR2383165A1/fr active Granted
- 1978-03-06 CA CA298,224A patent/CA1108167A/en not_active Expired
- 1978-03-06 DD DD78203989A patent/DD135347A5/xx unknown
- 1978-03-07 GB GB22531/80A patent/GB1600074A/en not_active Expired
- 1978-03-07 IL IL54218A patent/IL54218A/xx unknown
- 1978-03-07 AU AU33909/78A patent/AU523611B2/en not_active Expired
- 1978-03-07 AT AT162578A patent/AT360267B/de not_active IP Right Cessation
- 1978-03-07 IT IT20972/78A patent/IT1093509B/it active
- 1978-03-07 GB GB9008/78A patent/GB1600071A/en not_active Expired
- 1978-03-07 HU HU78CI1817A patent/HU180702B/hu unknown
- 1978-03-07 NL NL7802487A patent/NL7802487A/xx not_active Application Discontinuation
- 1978-03-07 AT AT0009280A patent/AT367390B/de not_active IP Right Cessation
- 1978-03-07 GB GB22530/80A patent/GB1600073A/en not_active Expired
- 1978-03-07 BE BE185719A patent/BE864632A/xx not_active IP Right Cessation
- 1978-03-07 ES ES467627A patent/ES467627A1/es not_active Expired
- 1978-03-07 BR BR7801399A patent/BR7801399A/pt unknown
- 1978-03-07 GB GB20736/80A patent/GB1600072A/en not_active Expired
- 1978-03-08 JP JP2647978A patent/JPS53112821A/ja active Pending
- 1978-03-08 TR TR19997A patent/TR19997A/xx unknown
- 1978-03-08 PH PH20860A patent/PH15239A/en unknown
-
1979
- 1979-10-11 US US06/083,905 patent/US4304936A/en not_active Ceased
- 1979-12-20 CA CA342,422A patent/CA1127347A/en not_active Expired
-
1981
- 1981-05-14 US US06/263,650 patent/US4394327A/en not_active Expired - Fee Related
- 1981-08-28 US US06/297,299 patent/US4417918A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| TR19997A (tr) | 1980-07-01 |
| GB1600072A (en) | 1981-10-14 |
| IT1093509B (it) | 1985-07-19 |
| IL54218A0 (en) | 1978-06-15 |
| US4394327A (en) | 1983-07-19 |
| FR2383165B1 (es) | 1980-06-06 |
| NL7802487A (nl) | 1978-09-12 |
| DD135347A5 (de) | 1979-05-02 |
| GB1600073A (en) | 1981-10-14 |
| AT360267B (de) | 1980-12-29 |
| PH15239A (en) | 1982-10-07 |
| IT7820972A0 (it) | 1978-03-07 |
| JPS53112821A (en) | 1978-10-02 |
| AU523611B2 (en) | 1982-08-05 |
| CA1127347A (en) | 1982-07-06 |
| BE864632A (fr) | 1978-09-07 |
| US4304936A (en) | 1981-12-08 |
| GB1600074A (en) | 1981-10-14 |
| FR2383165A1 (fr) | 1978-10-06 |
| US4417918A (en) | 1983-11-29 |
| BR7801399A (pt) | 1978-10-31 |
| DE2809541A1 (de) | 1978-09-14 |
| ATA162578A (de) | 1980-05-15 |
| CA1108167A (en) | 1981-09-01 |
| AU3390978A (en) | 1979-09-13 |
| ES467627A1 (es) | 1979-09-01 |
| GB1600071A (en) | 1981-10-14 |
| IL54218A (en) | 1983-12-30 |
| AT367390B (de) | 1982-06-25 |
| HU180702B (en) | 1983-04-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |