DE3121704C2 - 2-Benzyl-3-isoxazolidinone, Verfahren zu deren Herstellung und deren Verwendung als Herbizide - Google Patents
2-Benzyl-3-isoxazolidinone, Verfahren zu deren Herstellung und deren Verwendung als HerbizideInfo
- Publication number
- DE3121704C2 DE3121704C2 DE3121704A DE3121704A DE3121704C2 DE 3121704 C2 DE3121704 C2 DE 3121704C2 DE 3121704 A DE3121704 A DE 3121704A DE 3121704 A DE3121704 A DE 3121704A DE 3121704 C2 DE3121704 C2 DE 3121704C2
- Authority
- DE
- Germany
- Prior art keywords
- isoxazolidinone
- methyl
- dimethyl
- chlorophenyl
- chlorine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000004009 herbicide Substances 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 9
- KLGTXQOZQXTQPQ-UHFFFAOYSA-N 2-benzyl-1,2-oxazolidin-3-one Chemical class O=C1CCON1CC1=CC=CC=C1 KLGTXQOZQXTQPQ-UHFFFAOYSA-N 0.000 title claims description 3
- 238000000034 method Methods 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 27
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- -1 4,5-methylenedioxy group Chemical group 0.000 claims description 11
- QXDOFVVNXBGLKK-UHFFFAOYSA-N 3-Isoxazolidinone Chemical compound OC1=NOCC1 QXDOFVVNXBGLKK-UHFFFAOYSA-N 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
- 244000068988 Glycine max Species 0.000 claims description 7
- 235000010469 Glycine max Nutrition 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- WYJKNTLYOUZFMS-UHFFFAOYSA-N 5-chloro-2-[(2-chlorophenyl)methyl]-4,4-dimethyl-1,2-oxazolidin-3-one Chemical compound O=C1C(C)(C)C(Cl)ON1CC1=CC=CC=C1Cl WYJKNTLYOUZFMS-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- KIEDNEWSYUYDSN-UHFFFAOYSA-N clomazone Chemical compound O=C1C(C)(C)CON1CC1=CC=CC=C1Cl KIEDNEWSYUYDSN-UHFFFAOYSA-N 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- PAZGRYNWUMJGHF-UHFFFAOYSA-N 2-(2-bromophenyl)-4,4,5-trimethyl-1,2-oxazolidin-3-one Chemical compound O=C1C(C)(C)C(C)ON1C1=CC=CC=C1Br PAZGRYNWUMJGHF-UHFFFAOYSA-N 0.000 claims description 3
- LXUIBQMTNGIQHW-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-methoxy-4,4,5-trimethyl-1,2-oxazolidin-3-one Chemical compound ClC1=C(C=CC=C1)N1OC(C(C1=O)(C)C)(OC)C LXUIBQMTNGIQHW-UHFFFAOYSA-N 0.000 claims description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- FHUKASKVKWSLCY-UHFFFAOYSA-N bixlozone Chemical compound O=C1C(C)(C)CON1CC1=CC=C(Cl)C=C1Cl FHUKASKVKWSLCY-UHFFFAOYSA-N 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- OFQBGLQJBQYYIW-UHFFFAOYSA-N 2-(2-chloro-4-fluorophenyl)-4,4,5-trimethyl-1,2-oxazolidin-3-one Chemical compound ClC1=C(C=CC(=C1)F)N1OC(C(C1=O)(C)C)C OFQBGLQJBQYYIW-UHFFFAOYSA-N 0.000 claims 1
- VFPYIMPZCODFIC-UHFFFAOYSA-N 2-(2-chloro-5-fluorophenyl)-4,4,5-trimethyl-1,2-oxazolidin-3-one Chemical compound ClC1=C(C=C(C=C1)F)N1OC(C(C1=O)(C)C)C VFPYIMPZCODFIC-UHFFFAOYSA-N 0.000 claims 1
- OBQWAFYBKSLODH-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-ethoxy-4,4,5-trimethyl-1,2-oxazolidin-3-one Chemical compound ClC1=C(C=CC=C1)N1OC(C(C1=O)(C)C)(OCC)C OBQWAFYBKSLODH-UHFFFAOYSA-N 0.000 claims 1
- DTCQPZUCKPPDLR-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-hydroxy-4,4,5-trimethyl-1,2-oxazolidin-3-one Chemical compound ClC1=C(C=CC=C1)N1OC(C(C1=O)(C)C)(O)C DTCQPZUCKPPDLR-UHFFFAOYSA-N 0.000 claims 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 125000004494 ethyl ester group Chemical group 0.000 claims 1
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 239000003444 phase transfer catalyst Substances 0.000 claims 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical class CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 claims 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 20
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- 239000007788 liquid Substances 0.000 description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 13
- 241000196324 Embryophyta Species 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 238000000862 absorption spectrum Methods 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 235000019198 oils Nutrition 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 230000002363 herbicidal effect Effects 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- UUXRXRHXOZHHJV-UHFFFAOYSA-N 4,4-dimethyl-1,2-oxazolidin-3-one Chemical compound CC1(C)CONC1=O UUXRXRHXOZHHJV-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 238000004809 thin layer chromatography Methods 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 244000062793 Sorghum vulgare Species 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 241000894007 species Species 0.000 description 4
- LOBXXWMXAMOBAH-UHFFFAOYSA-N 3-chloro-n-hydroxy-2,2-dimethylpropanamide Chemical compound ClCC(C)(C)C(=O)NO LOBXXWMXAMOBAH-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 244000025254 Cannabis sativa Species 0.000 description 3
- 235000010617 Phaseolus lunatus Nutrition 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000004495 emulsifiable concentrate Substances 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 235000019713 millet Nutrition 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- PZUMUPHOBDVNNI-UHFFFAOYSA-N 2-[(2-chloro-4-fluorophenyl)methyl]-4,4-dimethyl-1,2-oxazolidin-3-one Chemical compound O=C1C(C)(C)CON1CC1=CC=C(F)C=C1Cl PZUMUPHOBDVNNI-UHFFFAOYSA-N 0.000 description 2
- ASGSCGAJFYIXOJ-UHFFFAOYSA-N 2-[(2-chlorophenyl)methyl]-5-ethoxy-4,4-dimethyl-1,2-oxazolidin-3-one Chemical compound O=C1C(C)(C)C(OCC)ON1CC1=CC=CC=C1Cl ASGSCGAJFYIXOJ-UHFFFAOYSA-N 0.000 description 2
- 244000105624 Arachis hypogaea Species 0.000 description 2
- 235000010777 Arachis hypogaea Nutrition 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 244000024671 Brassica kaber Species 0.000 description 2
- 235000014750 Brassica kaber Nutrition 0.000 description 2
- 244000045232 Canavalia ensiformis Species 0.000 description 2
- 244000299507 Gossypium hirsutum Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- 231100000674 Phytotoxicity Toxicity 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000009331 sowing Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- PAHVTLRWCQYFEB-UHFFFAOYSA-N 1,2-oxazolidine-3,5-dione Chemical class O=C1CC(=O)ON1 PAHVTLRWCQYFEB-UHFFFAOYSA-N 0.000 description 1
- IIDGYIYCPTWTST-UHFFFAOYSA-N 1,3-oxazolidine-2,4,5-trione Chemical class O=C1NC(=O)C(=O)O1 IIDGYIYCPTWTST-UHFFFAOYSA-N 0.000 description 1
- KZEVSDGEBAJOTK-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[5-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CC=1OC(=NN=1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O KZEVSDGEBAJOTK-UHFFFAOYSA-N 0.000 description 1
- PHDKMRIKFBWJGE-UHFFFAOYSA-N 1-(bromomethyl)-2,4,5-trichlorobenzene Chemical compound ClC1=CC(Cl)=C(CBr)C=C1Cl PHDKMRIKFBWJGE-UHFFFAOYSA-N 0.000 description 1
- GAUUDQVOPUKGJD-UHFFFAOYSA-N 1-(bromomethyl)-2-chloro-4-fluorobenzene Chemical compound FC1=CC=C(CBr)C(Cl)=C1 GAUUDQVOPUKGJD-UHFFFAOYSA-N 0.000 description 1
- CJNMJQCIRKZNRZ-UHFFFAOYSA-N 2,2-dichloro-2-[2-[(2-chlorophenyl)methyl]-4,4-dimethyl-3-oxo-1,2-oxazolidin-5-yl]acetic acid Chemical compound O=C1C(C)(C)C(C(Cl)(Cl)C(O)=O)ON1CC1=CC=CC=C1Cl CJNMJQCIRKZNRZ-UHFFFAOYSA-N 0.000 description 1
- AUVLFQDKJFSFIX-UHFFFAOYSA-N 2-(bromomethyl)-1-chloro-4-fluorobenzene Chemical compound FC1=CC=C(Cl)C(CBr)=C1 AUVLFQDKJFSFIX-UHFFFAOYSA-N 0.000 description 1
- ZTMOLOVAQWCURR-UHFFFAOYSA-N 2-[(2,5-dichlorophenyl)methyl]-4,4-dimethyl-1,2-oxazolidin-3-one Chemical compound O=C1C(C)(C)CON1CC1=CC(Cl)=CC=C1Cl ZTMOLOVAQWCURR-UHFFFAOYSA-N 0.000 description 1
- XPXZSOWIHDVVDU-UHFFFAOYSA-N 2-[(2-bromo-4-fluorophenyl)methyl]-4,4-dimethyl-1,2-oxazolidin-3-one Chemical compound O=C1C(C)(C)CON1CC1=CC=C(F)C=C1Br XPXZSOWIHDVVDU-UHFFFAOYSA-N 0.000 description 1
- JUTPLQFUKBJMHB-UHFFFAOYSA-N 2-[(2-bromo-5-fluorophenyl)methyl]-4,4-dimethyl-1,2-oxazolidin-3-one Chemical compound O=C1C(C)(C)CON1CC1=CC(F)=CC=C1Br JUTPLQFUKBJMHB-UHFFFAOYSA-N 0.000 description 1
- ICOVTZYCOSUCFP-UHFFFAOYSA-N 2-[(2-bromophenyl)methyl]-4,4-dimethyl-5-prop-2-ynoxy-1,2-oxazolidin-3-one Chemical compound O=C1C(C)(C)C(OCC#C)ON1CC1=CC=CC=C1Br ICOVTZYCOSUCFP-UHFFFAOYSA-N 0.000 description 1
- VUGAGFDYOGGZQW-UHFFFAOYSA-N 2-[(2-bromophenyl)methyl]-5-chloro-4,4-dimethyl-1,2-oxazolidin-3-one Chemical compound O=C1C(C)(C)C(Cl)ON1CC1=CC=CC=C1Br VUGAGFDYOGGZQW-UHFFFAOYSA-N 0.000 description 1
- XRQDYLGWKVMPCH-UHFFFAOYSA-N 2-[(2-chloro-4-methoxyphenyl)methyl]-4,4-dimethyl-1,2-oxazolidin-3-one Chemical compound ClC1=CC(OC)=CC=C1CN1C(=O)C(C)(C)CO1 XRQDYLGWKVMPCH-UHFFFAOYSA-N 0.000 description 1
- LIGJLLLFKITYIY-UHFFFAOYSA-N 2-[(2-chloro-5-fluorophenyl)methyl]-4,4-dimethyl-1,2-oxazolidin-3-one Chemical compound O=C1C(C)(C)CON1CC1=CC(F)=CC=C1Cl LIGJLLLFKITYIY-UHFFFAOYSA-N 0.000 description 1
- LGEFDLILYZYQOK-UHFFFAOYSA-N 2-[(2-chloro-5-methoxyphenyl)methyl]-4,4-dimethyl-1,2-oxazolidin-3-one Chemical compound COC1=CC=C(Cl)C(CN2C(C(C)(C)CO2)=O)=C1 LGEFDLILYZYQOK-UHFFFAOYSA-N 0.000 description 1
- JCKPCQSOTQJDGL-UHFFFAOYSA-N 2-[(2-chlorophenyl)methyl]-4,4-dimethyl-3-(3-oxo-1,2-oxazolidin-5-yl)cyclohexa-1,5-diene-1-carboxylic acid Chemical compound CC1(C=CC(=C(C1C2CC(=O)NO2)CC3=CC=CC=C3Cl)C(=O)O)C JCKPCQSOTQJDGL-UHFFFAOYSA-N 0.000 description 1
- VERVUZUDYQFYOR-UHFFFAOYSA-N 2-[(2-chlorophenyl)methyl]-4,4-dimethyl-5-prop-2-enoxy-1,2-oxazolidin-3-one Chemical compound O=C1C(C)(C)C(OCC=C)ON1CC1=CC=CC=C1Cl VERVUZUDYQFYOR-UHFFFAOYSA-N 0.000 description 1
- PZTGAWAHLAIXEW-UHFFFAOYSA-N 2-[(2-chlorophenyl)methyl]-4,4-dimethyl-5-prop-2-ynoxy-1,2-oxazolidin-3-one Chemical compound O=C1C(C)(C)C(OCC#C)ON1CC1=CC=CC=C1Cl PZTGAWAHLAIXEW-UHFFFAOYSA-N 0.000 description 1
- FJFRVNKWPLREDS-UHFFFAOYSA-N 2-[(2-chlorophenyl)methyl]-4,4-dimethyl-5-propan-2-yloxy-1,2-oxazolidin-3-one Chemical compound O=C1C(C)(C)C(OC(C)C)ON1CC1=CC=CC=C1Cl FJFRVNKWPLREDS-UHFFFAOYSA-N 0.000 description 1
- WMKOKZDCJOJNEL-UHFFFAOYSA-N 2-[(2-chlorophenyl)methyl]-4,4-dimethyl-5-propoxy-1,2-oxazolidin-3-one Chemical compound O=C1C(C)(C)C(OCCC)ON1CC1=CC=CC=C1Cl WMKOKZDCJOJNEL-UHFFFAOYSA-N 0.000 description 1
- GEVBORUWQBRUDU-UHFFFAOYSA-N 2-[(2-chlorophenyl)methyl]-5-(cyclopropylmethoxy)-4,4-dimethyl-1,2-oxazolidin-3-one Chemical compound O1N(CC=2C(=CC=CC=2)Cl)C(=O)C(C)(C)C1OCC1CC1 GEVBORUWQBRUDU-UHFFFAOYSA-N 0.000 description 1
- MDZOMCCXUBFSBT-UHFFFAOYSA-N 2-[(2-chlorophenyl)methyl]-5-hydroxy-4,4-dimethyl-1,2-oxazolidin-3-one Chemical compound O=C1C(C)(C)C(O)ON1CC1=CC=CC=C1Cl MDZOMCCXUBFSBT-UHFFFAOYSA-N 0.000 description 1
- FETSJLMCIHGQTG-UHFFFAOYSA-N 2-[(4-bromo-2-chlorophenyl)methyl]-4,4-dimethyl-1,2-oxazolidin-3-one Chemical compound O=C1C(C)(C)CON1CC1=CC=C(Br)C=C1Cl FETSJLMCIHGQTG-UHFFFAOYSA-N 0.000 description 1
- XGDMEFVNGXHSHG-UHFFFAOYSA-N 2-[(6-chloro-1,3-benzodioxol-5-yl)methyl]-4,4-dimethyl-1,2-oxazolidin-3-one Chemical compound O=C1C(C)(C)CON1CC(C(=C1)Cl)=CC2=C1OCO2 XGDMEFVNGXHSHG-UHFFFAOYSA-N 0.000 description 1
- IUKZXWNMRJSQCA-UHFFFAOYSA-N 2-[2-[(2-chlorophenyl)methyl]-4,4-dimethyl-3-oxo-1,2-oxazolidin-5-yl]acetic acid Chemical compound O=C1C(C)(C)C(CC(O)=O)ON1CC1=CC=CC=C1Cl IUKZXWNMRJSQCA-UHFFFAOYSA-N 0.000 description 1
- VWVRASTUFJRTHW-UHFFFAOYSA-N 2-[3-(azetidin-3-yloxy)-4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound O=C(CN1C=C(C(OC2CNC2)=N1)C1=CN=C(NC2CC3=C(C2)C=CC=C3)N=C1)N1CCC2=C(C1)N=NN2 VWVRASTUFJRTHW-UHFFFAOYSA-N 0.000 description 1
- JVKRKMWZYMKVTQ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C=NN(C=1)CC(=O)NC1=CC2=C(NC(O2)=O)C=C1 JVKRKMWZYMKVTQ-UHFFFAOYSA-N 0.000 description 1
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 1
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- MQZNDDUMJVSIMH-UHFFFAOYSA-N 3-chloro-2,2-dimethylpropanoyl chloride Chemical compound ClCC(C)(C)C(Cl)=O MQZNDDUMJVSIMH-UHFFFAOYSA-N 0.000 description 1
- SDQDJSJXPJPIBQ-UHFFFAOYSA-N 3-chloro-4-[(4,4-dimethyl-3-oxo-1,2-oxazolidin-2-yl)methyl]benzonitrile Chemical compound O=C1C(C)(C)CON1CC1=CC=C(C#N)C=C1Cl SDQDJSJXPJPIBQ-UHFFFAOYSA-N 0.000 description 1
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- QBWUTXXJFOIVME-UHFFFAOYSA-N 4h-1,2-oxazol-5-one Chemical class O=C1CC=NO1 QBWUTXXJFOIVME-UHFFFAOYSA-N 0.000 description 1
- IMSRJPMLEXEDMH-UHFFFAOYSA-N 5-anilino-2-[(2-chlorophenyl)methyl]-4,4-dimethyl-1,2-oxazolidin-3-one Chemical compound O1N(CC=2C(=CC=CC=2)Cl)C(=O)C(C)(C)C1NC1=CC=CC=C1 IMSRJPMLEXEDMH-UHFFFAOYSA-N 0.000 description 1
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- BZROFCXBUSLVPV-UHFFFAOYSA-N 5-butoxy-2-[(2-chlorophenyl)methyl]-4,4-dimethyl-1,2-oxazolidin-3-one Chemical compound O=C1C(C)(C)C(OCCCC)ON1CC1=CC=CC=C1Cl BZROFCXBUSLVPV-UHFFFAOYSA-N 0.000 description 1
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- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical group O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
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- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
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- 239000011248 coating agent Substances 0.000 description 1
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- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
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- IWAQNEOYEXNXMC-UHFFFAOYSA-N n-[(2-bromophenyl)methyl]-3-chloro-n-hydroxy-2,2-dimethylpropanamide Chemical compound ClCC(C)(C)C(=O)N(O)CC1=CC=CC=C1Br IWAQNEOYEXNXMC-UHFFFAOYSA-N 0.000 description 1
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- 229910052757 nitrogen Inorganic materials 0.000 description 1
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- 238000004806 packaging method and process Methods 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229920000056 polyoxyethylene ether Polymers 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
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- 239000002244 precipitate Substances 0.000 description 1
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- 239000000725 suspension Substances 0.000 description 1
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- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
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Classifications
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- A01N37/28—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the group; Thio analogues thereof
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- C07C239/00—Compounds containing nitrogen-to-halogen bonds; Hydroxylamino compounds or ethers or esters thereof
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- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
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- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
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- A01N43/30—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3 with two oxygen atoms in positions 1,3, condensed with a carbocyclic ring
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
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- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
- A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
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- A—HUMAN NECESSITIES
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- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
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- 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
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/363—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/04—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-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
- C07D309/08—Heterocyclic compounds containing six-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 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
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0892—Compounds with a Si-O-N linkage
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Pest Control & Pesticides (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
ber.: C 60,13; H 5,89; N 5,84;
gef.: C 60,01; H 5,60; N 6,09.
ber.: C 50,72; H 4,97; N 4,93;
gef.: C 51,01; H 4,68; N 5,16.
ber.: C 52,55; H 4,78; N 5,14;
gef.: C 52,56; H 4,80; N 5,01.
ber.: C 52,57; H 4,78; N 5,11;
gef.: C 52,39; H 4,56; N 5,20.
ber.: C 57,89; H 5,98; N 5,19;
gef.: C 57,64; H 6,13; N 5,04.
ber.: C 55,93; H 5,08; N 5,44;
gef.: C 55,55; H 5,04; N 5,33.
ber.: C 55,93; H 5,08; N 5,44;
gef.: C 55,89; H 4,92; N 5,37.
ber.: C 46,70; H 3,92; N 4,54;
gef.: C 46,86; H 3,86; N 4,59.
ber.: C 59,26; H 6,39; N 4,94;
gef.: C 59,61; H 6,57; N 4,72.
ber.: C 65,35; H 5,79; N 8,47;
gef.: C 65,63; H 5,93; N 8,43.
ber.: C 57,47; H 5,84; N 5,38;
gef.: C 57,29; H 5,71; N 5,56.
Claims (14)
- (1) ein Hydroxylamin der allgemeinen Formel R′₄NHOH, in der R′₄ der Rest oder ein Wasserstoffatom ist, oder des entsprechenden Trimethylsilylethers R′₄NHOSi(CH₃)₃ in einem inerten Lösungsmittel in Gegenwart eines Säureakzeptors mit einem substituierten Propionylchlorid der allgemeinen Formel in der R die vorstehend genannte Definition hat und R₇ ein Chlor- oder Bromatom ist, oder den Methyl- oder Ethylester zum entsprechenden Propanamid der allgemeinen Formel umsetzt, und
- (2) die erhaltene Verbindung unter basischen Bedingungen umsetzt, wobei ein Isoxazolidinon der allgemeinen Formel erhalten wird, welches
- (3) wenn R′₄ ein Wasserstoffatom ist, unter basischen Bedingungen ein Alkalimetallsalz bildet, das mit einem substituierten Benzylhalogenid der allgemeinen Formel gegebenenfalls in Gegenwart eines Phasentransferkatalysators umgesetzt wird, wobei ein Isoxazolidinon der allgemeinen Formel erhalten wird, das
- (4) wenn R₅ ein Chlor- oder Bromatom ist, gewünschtenfalls mit einer Verbindung der allgemeinen Formel HOR₉ weiter umgesetzt wird.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US15535380A | 1980-06-02 | 1980-06-02 | |
US06/262,715 US4405357A (en) | 1980-06-02 | 1981-05-11 | Herbicidal 3-isoxazolidinones and hydroxamic acids |
Publications (2)
Publication Number | Publication Date |
---|---|
DE3121704A1 DE3121704A1 (de) | 1982-02-11 |
DE3121704C2 true DE3121704C2 (de) | 1994-11-17 |
Family
ID=26852253
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE3153419A Expired - Lifetime DE3153419C2 (de) | 1980-06-02 | 1981-06-01 | |
DE3121704A Expired - Lifetime DE3121704C2 (de) | 1980-06-02 | 1981-06-01 | 2-Benzyl-3-isoxazolidinone, Verfahren zu deren Herstellung und deren Verwendung als Herbizide |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE3153419A Expired - Lifetime DE3153419C2 (de) | 1980-06-02 | 1981-06-01 |
Country Status (22)
Country | Link |
---|---|
US (1) | US4405357A (de) |
JP (1) | JPS60155164A (de) |
KR (2) | KR890003288B1 (de) |
AR (1) | AR230982A1 (de) |
AU (2) | AU550450B2 (de) |
BR (1) | BR8103484A (de) |
CA (1) | CA1171863A (de) |
CH (1) | CH656612A5 (de) |
DE (2) | DE3153419C2 (de) |
DK (1) | DK161516C (de) |
DO (1) | DOP1981004128A (de) |
ES (3) | ES8305188A1 (de) |
FR (1) | FR2483406A1 (de) |
GB (1) | GB2080289B (de) |
HU (1) | HU198117B (de) |
IE (1) | IE51289B1 (de) |
IL (1) | IL63000A (de) |
IT (1) | IT1194802B (de) |
MX (1) | MX7035E (de) |
MY (1) | MY8700176A (de) |
NL (2) | NL189193C (de) |
PH (1) | PH17364A (de) |
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-
1981
- 1981-05-11 US US06/262,715 patent/US4405357A/en not_active Expired - Lifetime
- 1981-05-20 AU AU70886/81A patent/AU550450B2/en not_active Expired
- 1981-05-20 IE IE1126/81A patent/IE51289B1/en not_active IP Right Cessation
- 1981-05-22 PH PH25667A patent/PH17364A/en unknown
- 1981-05-29 CA CA000378684A patent/CA1171863A/en not_active Expired
- 1981-05-29 GB GB8116505A patent/GB2080289B/en not_active Expired
- 1981-05-29 CH CH3540/81A patent/CH656612A5/de not_active IP Right Cessation
- 1981-05-31 IL IL63000A patent/IL63000A/xx not_active IP Right Cessation
- 1981-06-01 DE DE3153419A patent/DE3153419C2/de not_active Expired - Lifetime
- 1981-06-01 DO DO1981004128A patent/DOP1981004128A/es unknown
- 1981-06-01 MX MX819469U patent/MX7035E/es unknown
- 1981-06-01 IT IT22077/81A patent/IT1194802B/it active
- 1981-06-01 HU HU815023A patent/HU198117B/hu unknown
- 1981-06-01 DE DE3121704A patent/DE3121704C2/de not_active Expired - Lifetime
- 1981-06-01 DK DK239181A patent/DK161516C/da active Protection Beyond IP Right Term
- 1981-06-02 FR FR8110938A patent/FR2483406A1/fr active Granted
- 1981-06-02 BR BR8103484-9A patent/BR8103484A/pt not_active IP Right Cessation
- 1981-06-02 NL NLAANVRAGE8102661,A patent/NL189193C/xx active Protection Beyond IP Right Term
-
1982
- 1982-06-16 ES ES513181A patent/ES8305188A1/es not_active Expired
- 1982-06-16 ES ES513183A patent/ES513183A0/es active Granted
- 1982-06-16 ES ES513182A patent/ES8305189A1/es not_active Expired
-
1983
- 1983-09-14 AR AR294200A patent/AR230982A1/es active
-
1984
- 1984-03-12 JP JP59045751A patent/JPS60155164A/ja active Granted
- 1984-10-30 KR KR1019840006756A patent/KR890003288B1/ko not_active IP Right Cessation
- 1984-10-30 KR KR1019840006755A patent/KR890003287B1/ko not_active IP Right Cessation
-
1986
- 1986-02-13 AU AU53632/86A patent/AU574262B2/en not_active Expired
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1987
- 1987-12-30 MY MY176/87A patent/MY8700176A/xx unknown
-
2001
- 2001-03-14 NL NL350002C patent/NL350002I1/nl unknown
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