HU180702B - Herbicide compositions containing phenoxy-alpha-phenoxy-alkane-carboxylic acid derivatives,and process for producing the active agents - Google Patents
Herbicide compositions containing phenoxy-alpha-phenoxy-alkane-carboxylic acid derivatives,and process for producing the active agents Download PDFInfo
- Publication number
- HU180702B HU180702B HU78CI1817A HUCI001817A HU180702B HU 180702 B HU180702 B HU 180702B HU 78CI1817 A HU78CI1817 A HU 78CI1817A HU CI001817 A HUCI001817 A HU CI001817A HU 180702 B HU180702 B HU 180702B
- Authority
- HU
- Hungary
- Prior art keywords
- phenoxy
- formula
- group
- hydrogen
- alkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 11
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 9
- 239000000203 mixture Substances 0.000 title claims description 54
- 239000004009 herbicide Substances 0.000 title claims description 6
- 239000013543 active substance Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 63
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 27
- 239000001257 hydrogen Substances 0.000 claims abstract description 26
- 239000002253 acid Substances 0.000 claims abstract description 15
- 125000005843 halogen group Chemical group 0.000 claims abstract description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 40
- 239000003921 oil Substances 0.000 claims description 36
- 239000004480 active ingredient Substances 0.000 claims description 35
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 34
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 22
- -1 alkali metal cation Chemical class 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 7
- 239000005995 Aluminium silicate Substances 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 235000012211 aluminium silicate Nutrition 0.000 claims description 6
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 claims description 6
- 229920000151 polyglycol Polymers 0.000 claims description 6
- 239000010695 polyglycol Substances 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 150000007530 organic bases Chemical class 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 claims description 2
- 206010029897 Obsessive thoughts Diseases 0.000 claims description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims description 2
- 150000007529 inorganic bases Chemical class 0.000 claims description 2
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 claims description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 3
- CDFPXALLOJLBDX-UHFFFAOYSA-N 2,3-dibutylnaphthalene-1-sulfonic acid;sodium Chemical compound [Na].C1=CC=C2C(S(O)(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 CDFPXALLOJLBDX-UHFFFAOYSA-N 0.000 claims 1
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims 1
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 claims 1
- DNEHKUCSURWDGO-UHFFFAOYSA-N aluminum sodium Chemical compound [Na].[Al] DNEHKUCSURWDGO-UHFFFAOYSA-N 0.000 claims 1
- HCWYXKWQOMTBKY-UHFFFAOYSA-N calcium;dodecyl benzenesulfonate Chemical compound [Ca].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 HCWYXKWQOMTBKY-UHFFFAOYSA-N 0.000 claims 1
- 239000012050 conventional carrier Substances 0.000 claims 1
- ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical group C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 0.000 claims 1
- 239000002270 dispersing agent Substances 0.000 claims 1
- 239000002516 radical scavenger Substances 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 abstract description 29
- 235000007164 Oryza sativa Nutrition 0.000 abstract description 11
- 235000009566 rice Nutrition 0.000 abstract description 11
- 229920000742 Cotton Polymers 0.000 abstract description 7
- 235000010469 Glycine max Nutrition 0.000 abstract description 6
- 244000068988 Glycine max Species 0.000 abstract description 5
- 240000008042 Zea mays Species 0.000 abstract description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 abstract description 3
- 235000013339 cereals Nutrition 0.000 abstract description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 abstract description 2
- 235000005822 corn Nutrition 0.000 abstract description 2
- 244000299507 Gossypium hirsutum Species 0.000 abstract 1
- 240000007594 Oryza sativa Species 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 203
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 238000009472 formulation Methods 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 241000209094 Oryza Species 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 239000000839 emulsion Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000012141 concentrate Substances 0.000 description 9
- 241000219146 Gossypium Species 0.000 description 7
- 239000012954 diazonium Substances 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000001768 cations Chemical class 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 150000001989 diazonium salts Chemical class 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
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- 244000058871 Echinochloa crus-galli Species 0.000 description 4
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- 235000011999 Panicum crusgalli Nutrition 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 240000009132 Sagittaria sagittifolia Species 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
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- 241000533293 Sesbania emerus Species 0.000 description 3
- 240000006410 Sida spinosa Species 0.000 description 3
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 3
- 241000209140 Triticum Species 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 239000002585 base Substances 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
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
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- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 3
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- XXSPGBOGLXKMDU-UHFFFAOYSA-N 2-bromo-2-methylpropanoic acid Chemical compound CC(C)(Br)C(O)=O XXSPGBOGLXKMDU-UHFFFAOYSA-N 0.000 description 2
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- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
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- 229910052802 copper Inorganic materials 0.000 description 1
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
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- 238000006193 diazotization reaction Methods 0.000 description 1
- NVYQDQZEMGUESH-UHFFFAOYSA-N dimethylsilyloxy(dimethyl)silane Chemical compound C[SiH](C)O[SiH](C)C NVYQDQZEMGUESH-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
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- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- KTRGHLZBDIJZLQ-UHFFFAOYSA-N elatine Natural products CCN1CC2(CCC(OC)C34C2C(OC)C5(OCOC56CC(OC)C7CC3(O)C6C7OC)C14)OC(=O)c8ccccc8N9C(=O)CC(C)C9=O KTRGHLZBDIJZLQ-UHFFFAOYSA-N 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
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- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 1
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- 230000002140 halogenating effect Effects 0.000 description 1
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- 238000010438 heat treatment Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
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- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
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- LSNDXPAVCFTYEF-UHFFFAOYSA-N methyl 2-(2-chlorophenoxy)-3-[2-cyano-4-(trifluoromethyl)phenoxy]propanoate Chemical compound C=1C=CC=C(Cl)C=1OC(C(=O)OC)COC1=CC=C(C(F)(F)F)C=C1C#N LSNDXPAVCFTYEF-UHFFFAOYSA-N 0.000 description 1
- BTJRWOICZAYTEK-UHFFFAOYSA-N methyl 2-(2-cyanophenoxy)-3-(2,4-dichlorophenoxy)propanoate Chemical compound C=1C=CC=C(C#N)C=1OC(C(=O)OC)COC1=CC=C(Cl)C=C1Cl BTJRWOICZAYTEK-UHFFFAOYSA-N 0.000 description 1
- ACEONLNNWKIPTM-UHFFFAOYSA-N methyl 2-bromopropanoate Chemical compound COC(=O)C(C)Br ACEONLNNWKIPTM-UHFFFAOYSA-N 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 238000002156 mixing Methods 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
- KRKPYFLIYNGWTE-UHFFFAOYSA-N n,o-dimethylhydroxylamine Chemical compound CNOC KRKPYFLIYNGWTE-UHFFFAOYSA-N 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 230000008635 plant growth Effects 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
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000000429 sodium aluminium silicate Substances 0.000 description 1
- 235000012217 sodium aluminium silicate Nutrition 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
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- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000008096 xylene 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Paints Or Removers (AREA)
- Polyurethanes Or Polyureas (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH286777A CH626318A5 (en, 2012) | 1977-03-08 | 1977-03-08 | |
| CH818277 | 1977-07-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU180702B true HU180702B (en) | 1983-04-29 |
Family
ID=25691594
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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 |
Country Status (19)
| Country | Link |
|---|---|
| US (3) | US4304936A (en, 2012) |
| JP (1) | JPS53112821A (en, 2012) |
| AT (2) | AT367390B (en, 2012) |
| AU (1) | AU523611B2 (en, 2012) |
| BE (1) | BE864632A (en, 2012) |
| BR (1) | BR7801399A (en, 2012) |
| CA (2) | CA1108167A (en, 2012) |
| CH (1) | CH626318A5 (en, 2012) |
| DD (1) | DD135347A5 (en, 2012) |
| DE (1) | DE2809541A1 (en, 2012) |
| ES (1) | ES467627A1 (en, 2012) |
| FR (1) | FR2383165A1 (en, 2012) |
| GB (4) | GB1600073A (en, 2012) |
| HU (1) | HU180702B (en, 2012) |
| IL (1) | IL54218A (en, 2012) |
| IT (1) | IT1093509B (en, 2012) |
| NL (1) | NL7802487A (en, 2012) |
| PH (1) | PH15239A (en, 2012) |
| TR (1) | TR19997A (en, 2012) |
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 |
| US4419122A (en) * | 1981-10-19 | 1983-12-06 | Rohm And Haas Company | Herbicidal 4-trifluoromethyl-3'-oxygen-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 (en, 2012) * | 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 |
| 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 |
| 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 |
| JPS5814402B2 (ja) * | 1975-09-27 | 1983-03-18 | 石原産業株式会社 | ジヨソウザイ |
| 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 |
| 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 |
| DK189677A (da) * | 1976-05-07 | 1977-11-08 | Sumitomo Chemical Co | M-phenoxybenzamid-derivater |
| 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 CA CA298,224A patent/CA1108167A/en not_active Expired
- 1978-03-06 FR FR7806325A patent/FR2383165A1/fr active Granted
- 1978-03-06 DD DD78203989A patent/DD135347A5/xx unknown
- 1978-03-07 HU HU78CI1817A patent/HU180702B/hu unknown
- 1978-03-07 BE BE185719A patent/BE864632A/xx not_active IP Right Cessation
- 1978-03-07 BR BR7801399A patent/BR7801399A/pt unknown
- 1978-03-07 GB GB22530/80A patent/GB1600073A/en not_active Expired
- 1978-03-07 GB GB20736/80A patent/GB1600072A/en not_active Expired
- 1978-03-07 AT AT0009280A patent/AT367390B/de not_active IP Right Cessation
- 1978-03-07 AT AT162578A patent/AT360267B/de not_active IP Right Cessation
- 1978-03-07 GB GB9008/78A patent/GB1600071A/en not_active Expired
- 1978-03-07 NL NL7802487A patent/NL7802487A/xx not_active Application Discontinuation
- 1978-03-07 IL IL54218A patent/IL54218A/xx unknown
- 1978-03-07 GB GB22531/80A patent/GB1600074A/en not_active Expired
- 1978-03-07 AU AU33909/78A patent/AU523611B2/en not_active Expired
- 1978-03-07 IT IT20972/78A patent/IT1093509B/it active
- 1978-03-07 ES ES467627A patent/ES467627A1/es not_active Expired
- 1978-03-08 PH PH20860A patent/PH15239A/en unknown
- 1978-03-08 JP JP2647978A patent/JPS53112821A/ja active Pending
- 1978-03-08 TR TR19997A patent/TR19997A/xx 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 |
|---|---|
| GB1600074A (en) | 1981-10-14 |
| DE2809541A1 (de) | 1978-09-14 |
| FR2383165A1 (fr) | 1978-10-06 |
| TR19997A (tr) | 1980-07-01 |
| US4417918A (en) | 1983-11-29 |
| IT7820972A0 (it) | 1978-03-07 |
| GB1600072A (en) | 1981-10-14 |
| CA1108167A (en) | 1981-09-01 |
| IL54218A0 (en) | 1978-06-15 |
| US4304936A (en) | 1981-12-08 |
| FR2383165B1 (en, 2012) | 1980-06-06 |
| GB1600073A (en) | 1981-10-14 |
| BE864632A (fr) | 1978-09-07 |
| IT1093509B (it) | 1985-07-19 |
| GB1600071A (en) | 1981-10-14 |
| ATA162578A (de) | 1980-05-15 |
| CH626318A5 (en, 2012) | 1981-11-13 |
| AT360267B (de) | 1980-12-29 |
| PH15239A (en) | 1982-10-07 |
| US4394327A (en) | 1983-07-19 |
| BR7801399A (pt) | 1978-10-31 |
| ES467627A1 (es) | 1979-09-01 |
| CA1127347A (en) | 1982-07-06 |
| AU523611B2 (en) | 1982-08-05 |
| DD135347A5 (de) | 1979-05-02 |
| IL54218A (en) | 1983-12-30 |
| AU3390978A (en) | 1979-09-13 |
| NL7802487A (nl) | 1978-09-12 |
| JPS53112821A (en) | 1978-10-02 |
| AT367390B (de) | 1982-06-25 |
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