DK158262B - Mellemprodukter til fremstilling af herbicide tetrahydrophthalimidforbindelser - Google Patents
Mellemprodukter til fremstilling af herbicide tetrahydrophthalimidforbindelser Download PDFInfo
- Publication number
- DK158262B DK158262B DK237988A DK237988A DK158262B DK 158262 B DK158262 B DK 158262B DK 237988 A DK237988 A DK 237988A DK 237988 A DK237988 A DK 237988A DK 158262 B DK158262 B DK 158262B
- Authority
- DK
- Denmark
- Prior art keywords
- compounds
- tetrahydrophthalimide
- preparation
- fluoro
- herbicide
- Prior art date
Links
- SPAMRUYRVYMHPV-UHFFFAOYSA-N 3a,4,5,7a-tetrahydroisoindole-1,3-dione Chemical class C1=CCCC2C(=O)NC(=O)C21 SPAMRUYRVYMHPV-UHFFFAOYSA-N 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 9
- 239000000543 intermediate Substances 0.000 title description 6
- 230000002363 herbicidal effect Effects 0.000 title description 5
- 239000004009 herbicide Substances 0.000 title description 3
- 239000000460 chlorine Substances 0.000 claims description 17
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Chemical group 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 150000001875 compounds Chemical class 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- -1 methylcelosolve Chemical compound 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- CIFFBTOJCKSRJY-UHFFFAOYSA-N 3α,4,7,7α-tetrahydro-1h-isoindole-1,3(2h)-dione Chemical compound C1C=CCC2C(=O)NC(=O)C21 CIFFBTOJCKSRJY-UHFFFAOYSA-N 0.000 description 3
- WRULFQRXGSSDPQ-UHFFFAOYSA-N 4-chloro-2-fluoro-5-nitroaniline Chemical compound NC1=CC([N+]([O-])=O)=C(Cl)C=C1F WRULFQRXGSSDPQ-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 244000068988 Glycine max Species 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 240000008042 Zea mays Species 0.000 description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- HPUXLXZOXYXHMD-UHFFFAOYSA-N 2-(4-bromo-2-fluoro-5-nitrophenyl)-4,5,6,7-tetrahydroisoindole-1,3-dione Chemical compound C1=C(Br)C([N+](=O)[O-])=CC(N2C(C3=C(CCCC3)C2=O)=O)=C1F HPUXLXZOXYXHMD-UHFFFAOYSA-N 0.000 description 2
- PLTMBXHQMSOBIJ-UHFFFAOYSA-N 2-(4-chloro-2-fluoro-5-nitrophenyl)-4,5,6,7-tetrahydroisoindole-1,3-dione Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC(N2C(C3=C(CCCC3)C2=O)=O)=C1F PLTMBXHQMSOBIJ-UHFFFAOYSA-N 0.000 description 2
- PDNZCDDWSKYNTE-UHFFFAOYSA-N 4-bromo-2-fluoro-5-nitroaniline Chemical compound NC1=CC([N+]([O-])=O)=C(Br)C=C1F PDNZCDDWSKYNTE-UHFFFAOYSA-N 0.000 description 2
- GZRMNMGWNKSANY-UHFFFAOYSA-N 4-bromo-2-fluoroaniline Chemical compound NC1=CC=C(Br)C=C1F GZRMNMGWNKSANY-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 244000020551 Helianthus annuus Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 235000002594 Solanum nigrum Nutrition 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000003978 alpha-halocarboxylic acids Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- SWZLSCLJPOHBAC-UHFFFAOYSA-N 2-(5-amino-4-chloro-2-fluorophenyl)-4,5,6,7-tetrahydroisoindole-1,3-dione Chemical compound C1=C(Cl)C(N)=CC(N2C(C3=C(CCCC3)C2=O)=O)=C1F SWZLSCLJPOHBAC-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- CSFDTBRRIBJILD-UHFFFAOYSA-N 4-chloro-2-fluoroaniline Chemical compound NC1=CC=C(Cl)C=C1F CSFDTBRRIBJILD-UHFFFAOYSA-N 0.000 description 1
- 241000219144 Abutilon Species 0.000 description 1
- 240000002245 Acer pensylvanicum Species 0.000 description 1
- 235000006760 Acer pensylvanicum Nutrition 0.000 description 1
- 244000237956 Amaranthus retroflexus Species 0.000 description 1
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 1
- 244000036975 Ambrosia artemisiifolia Species 0.000 description 1
- 235000003133 Ambrosia artemisiifolia Nutrition 0.000 description 1
- 235000000509 Chenopodium ambrosioides Nutrition 0.000 description 1
- 244000098897 Chenopodium botrys Species 0.000 description 1
- 235000005490 Chenopodium botrys Nutrition 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000207894 Convolvulus arvensis Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 240000008853 Datura stramonium Species 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 244000058871 Echinochloa crus-galli Species 0.000 description 1
- 244000283628 Elatine triandra Species 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- 235000003222 Helianthus annuus Nutrition 0.000 description 1
- 235000015184 Helianthus annuus ssp. lenticularis Nutrition 0.000 description 1
- 235000021506 Ipomoea Nutrition 0.000 description 1
- 241000207783 Ipomoea Species 0.000 description 1
- 240000004428 Lindernia procumbens Species 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 235000003990 Monochoria hastata Nutrition 0.000 description 1
- 240000000178 Monochoria vaginalis Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 235000011999 Panicum crusgalli Nutrition 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 241000227425 Pieris rapae crucivora Species 0.000 description 1
- 244000234609 Portulaca oleracea Species 0.000 description 1
- 235000001855 Portulaca oleracea Nutrition 0.000 description 1
- 244000155504 Rotala indica Species 0.000 description 1
- 241001408202 Sagittaria pygmaea Species 0.000 description 1
- 241000124033 Salix Species 0.000 description 1
- 241000533293 Sesbania emerus Species 0.000 description 1
- 240000006410 Sida spinosa Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 244000061457 Solanum nigrum Species 0.000 description 1
- 240000002307 Solanum ptychanthum Species 0.000 description 1
- 244000067505 Xanthium strumarium Species 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- VJGNLOIQCWLBJR-UHFFFAOYSA-M benzyl(tributyl)azanium;chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CC1=CC=CC=C1 VJGNLOIQCWLBJR-UHFFFAOYSA-M 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000008429 bread Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- OCVVXESRCSKPQB-UHFFFAOYSA-N ethyl 2-[[6-bromo-3-(1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)-4-fluorocyclohexa-2,4-dien-1-ylidene]amino]acetate Chemical compound FC1=CC(Br)C(=NCC(=O)OCC)C=C1N1C(=O)C(CCCC2)=C2C1=O OCVVXESRCSKPQB-UHFFFAOYSA-N 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical compound [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000009304 pastoral farming Methods 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 235000011845 white flour Nutrition 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- 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
- A01N37/00—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
- 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
-
- 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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Indole Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
DK 158262 B
i
Den foreliggende opfindelse angår tetrahydrophthalimidforbindelser med den almene formel o
hvor X er chlor eller brom, og Q er amino eller nitro. Sådanne forbindelser er anvendelige som mellemprodukter ved fremstilling af te-5 trahydrophthalimidslutforbindelser med den almene formel I
0
R1-Z-C-CH-Y/ (I
! o R2 hvor R^ er hydrogen, g-alkyl, ^-cycloalkyl, g-alkyl-C^ γ cycloalkyl, ^-cycloalkyl-C^ g-alkyl, g-alkoxy-C^ g-alkyl, g-alkenyl, C,. g-cycloalkenyl, C,. g-cycloalkeny1- g-alkyl, phenyl, cyano-C^ g-alkyl, C^ g-alkynyl, g-alkylidenamino, g-alkylthio-10 Cl g-alkyl, benzyl, halogen-g-alkyl såsom chlor-C^ g-alkyl og brom-C^ g-alkyl, eller ^-cycloalkylidenamino, R2 er hydrogen, g-alkyl eller g-alkoxy, X er chlor eller brom, Y er imino, og Z er oxygen eller svovl.
Forbindelser med den almene formel I er beskrevet i dansk patentan-15 søgning nr. 5734/82 (fremlagt som dansk fremlæggelsesskrift nr.
154.703), hvoraf nærværende ansøgning er afdelt.
Tetrahydrophthalimidslutforbindelserne med den almene formel I er fordelagtige ved, at de udviser en kraftig herbicid virkning mod et bredt spektrum af ukrudtsplanter ved behandling på bladene eller i 20 jorden i pløjede marker. Det er fordelagtigt, at visse af dem ikke forårsager nogen væsentlig phytotoxicitet hos landbrugsmæssige afgrøder (fx majs, sojabønne og bomuld). Deres herbicide virkning er
DK 158262B
2 særlig bemærkelsesværdig ved bladbehandling efter opløbning hos bredbladede ukrudtsplanter såsom Portulaca oleracea (almindelig portulak) , Chenopodixm album (almindelig hvidmelet gåsefod), Amaranthus -retroflexus, Sesbania exaltata, Abutilon tbeophrasti, Sida spinosa, 5 Ipomoea hederacea, Ipomoea purpurea (høj ipomoea), Convolvulus arvensis (agersnerle), Datura stramonium (pigæble), Solanum nigrum (sort natskygge), Xanthium pensylvanicum (brødfrø), Helianthus annus (vild solsikke) eller Ambrosia artemisifolia (almindelig ambrosie) i korneller sojabønnemarker, eftersom de ikke frembyder nogen toxisk virk-10 ning over for majs eller sojabønner. På samme måde udviser de også god herbicid virkning mod græsagtige ukrudtsplanter såsom Echinoch-loa crus-galli (hanespore), bredbladede ukrudtsplanter såsom Linder-nia procumbens, Rotala indica og Elatine triandra (bækarve) og paddy-marks ukrudtsplanter såsom Cyperns serotinus, Monochoria vaginalis og 15 Sagittaria pygmaea (pilblad) i paddy-rismarker uden at forårsage nogen signifikant skade på risplanter. Forbindelserne kan derfor anvendes som herbicider, der kan påføres både paddy-marker såvel som pløjemarkearealer. De er også nyttige som herbicider, der kan anvendes i haver, græsningsarealer, græsplæner, skove og ikke- landbrugs-20 mæssige arealer.
Forbindelser ifølge opfindelsen, hvor Q er amino, kan fremstilles ved, at forbindelsen, hvor Q er nitro, behandles med 2,0-10 ækvivalenter jern i nærværelse af en syre i et opløsningsmiddel (fx eddikesyre, vand, methanol, ethanol, tetrahydrofuran) ved en temperatur på 25 20-100°C.
Fremstilling af forbindelser ifølge opfindelsen, hvor Q er nitro, kan opsummeres i følgende reaktionsskema: X_c5-NH2 -* Χ-(Ι^ΝΗ2 -» o2w 0/ Π
O
V VI
hvor X er som ovenfor defineret.
DK 158262 8 3
Halogenanilinen med den almene formel V behandles med 1,0-1,5 ækvivalenter koncentreret salpetersyre i koncentreret svovlsyre ved en temperatur på 10 til -10°C, hvilket giver nitroanilinen med den almene formel VI, som derefter omsættes med 3,4,5,6-tetrahydrophthalanhydrid 5 i et opløsningsmiddel (fx toluen, xylen, eddikesyre, propionsyre, vand, dioxan) ved en temperatur på 0-200°C, hvorved fås forbindelsen ifølge opfindelsen, hvor Q er nitro.
Den således fremkomne forbindelse, hvor Q er nitro, kan underkastes normal oparbejdning eller, hvis det er nødvendigt, oprensning ved 10 chromatografi eller omkrystallisering.
Ved anvendelse af forbindelser ifølge opfindelsen til fremstilling af de herbicidt virksomme tetrahydrophthalimidforbindelser med den almene formel I omsættes en forbindelse ifølge opfindelsen, hvor Q er amino, med en a-halogencarboxylsyreester med den almene formel III
0
II
15 A-CH-C-Z-Rj m R2 hvor A er chlor eller brom, og Rj_, R£ og Z hver er som ovenfor defineret, i et opløsningsmiddel i nærværelse eller fraværelse af et de-hydrohalogeneringsmiddel, sædvanligvis ved en temperatur på 0-200°C i 1-240 timer. Mængderne af a-halogencarboxylsyreesteren med den al-20 mene formel III og dehydrohalogeneringsmidlet kan være henholdsvis 1,0-10 ækvivalenter og 0,5-1,5 ækvivalenter i forhold til HY-phenyl-tetrahydrophthalimidet med den almene formel II. Hvis det ønskes, kan der anvendes en faseoverføringskatalysator såsom tetrabutylammonium-bromid eller benzyltributylammoniumchlorid.
25 Som opløsningsmiddel kan anvendes et aliphatisk carbonhydrid (fx hexan, heptan, ligroin eller petroleumsether), et aromatisk carbonhydrid (fx benzen, toluen, xylen), et halogeneret carbonhydrid (fx chloroform, carbontetrachlorid, dichlorethan, chlorbenzen, dichlor-benzen), en ether (fx diethylether, diisopropylether, dioxan, tetra-30 hydrofuran, diethylenglycoldimethylether), enketon (fx acetone, me-
DK 158262 B
4 thylethylketon, methylisobutylketon, isophoron, cyclohexanon), en alkohol (fx methanol, ethanol, isopropanol, tert.butanol, octanol, cyclohexanol, methylcelosolve, diethylenglycol, glycerol), et nitril (fx acetonitril, isobutyronitril), et syreamid (fx formamid, N,N-5 dimethylformamid, acetamid), en svovlforbindelse (fx dimethylsul-foxid, sulfolan), vand etc. Opløsningsmidlerne kan anvendes alene eller kombineret med hinanden.
Eksempler på dehydrohalogeneringsmidlet er en organisk base (fx pyri-din, triethylamin, Ν,Ν-diethylanilin), en uorganisk base (fx natrium-10 hydroxid, kaliumhydroxid, natriumcarbonat, kaliumcarbonat, natrium-hydrid), et alkalimetalalkoxid (fx natriummethoxid, natriumethoxid) etc.
Fremstilling af forbindelser ifølge opfindelsen og udgangsstoffer derfor samt anvendelse deraf ved fremstilling af herbicidt virksomme 15 slutforbindelser er illustreret i følgende eksempler.
EKSEMPEL 1
Fremstilling af mellemproduktforbindelse, hvor X er Cl, og Q er NH2
En opløsning af N-(4-chlor-2-fluor-5-nitrophenyl)-3,4,5,6-tetrahydro-phthalimid (16,2 g) i eddikesyre (200 ml) blev dråbevis sat til en 20 suspension af jernpulver (14 g) i en 5%'s vandig eddikesyreopløsning (30 ml) ved 90-100°C, og der blev tilbagesvalet i 1 time. Efter at have fået lov at afkøle blev den resulterende blanding tilsat chloroform, hvorefter den blev filtreret. Den organiske fase blev skilt fra filtratet, vasket med en mættet natriumhydrogencarbonatopløsning, 25 tørret og koncentreret. Remanensen blev omkrystalliseret af en blanding af ether og petroleumsether, hvilket gav 7,5 g N-(3-amino-4-chlor-6-fluorphenyl)-3,4,5,6-tetrahydrophthalimid. Smeltepunkt 144,5-146,5°C.
EKSEMPEL 2
DK 158262B
5
Fremstilling af mellemproduktforbindelse, hvor X er Br, og Q er NH2 På samme måde som i eksempel 1, men under anvendelse af N-(4- brom-2-fluor-5-nitrophenyl)-3,4,5,6-tetrahydrophthalimid i stedet for N-(4-5 chlor-2-fluor-5-nitrophenyl)-3,4,5,6-tetrahydrophthalimid, fremstil ledes N-(3-amino-4-brom-6-fluorphenyl)-3,4,5,'6-tetrahydrophthalimid. Smeltepunkt 163-164,5°C.
EKSEMPEL 3
Fremstilling af mellemproduktforbindelse, hvor X er Cl, og Q er NO2 10 4-Chlor-2-fluor-5-nitroanilin (19 g) og 3,4,5,6-tetrahydrophthalan-hydrid (15,2 g) blev opløst i eddikesyre (50 ml) og tilbagesvalet i 6 timer. Efter at have fået lov at køle af blev den resulterende blanding hældt ud i vand og ekstraheret med toluen. Toluenfasen blev vasket med vand, en vandig natriumhydrogencarbonatopløsning og der-15 efter med vand, tørret og koncentreret. Remanensen blev omkrystalliseret af ethanol, hvilket gav 20 g N-(4-chlor-2-fluor-5-nitrophenyl)-3,4,5,6-tetrahydrophthalimid. Smeltepunkt 157-157,5°C.
EKSEMPEL 4
Fremstilling af mellemproduktforbindelse, hvor X er Br, og Q er NO2 20 På samme måde som i eksempel 3, men under anvendelse af 4-brom-2- fluor-5-nitroanilin i stedet for 4-chlor-2-fluor-5-nitroanilin, fremstilledes N-(4-brom-2-fluor-5-nitrophenyl)-3,4,5,6-tetrahydrophthalimid. Smeltepunkt 155-156eC.
DK 158262 B
6 EKSEMPEL 5
De i eksemplerne 3 og 4 som udgangsforbindelser anvendte forbindelser blev fremstillet på følgende måde:
En opløsning af 4-brom-2-fluoranilin (58,6 g) i koncentreret svovl -5 syre (100 ml) blev dråbevis tilsat en blanding af koncentreret salpetersyre (25,3 g) og koncentreret svovlsyre (15 ml) ved en temperatur på 0 til- 10°C, Den resulterende blanding blev omrørt ved 0-5°G i 1 time, hældt ud i isvand og ekstraheret med toluen. Toluenfasen blev vasket med vand og en vandig natriumhydrogencarbonatopløsning og der-10 efter koncentreret. Remanensen blev oprenset ved silicagelchromato-grafi, hvilket gav 16,4 g 4-brom-2-fluor-5-nitroanilin. Smeltepunkt 90-92°C.
EKSEMPEL 6 2-(3-Amino-4-brom-6-fluorphenyl)-4,5,6,7-tetrahydro-2H-isoindol-1,3-15 dion (0,85 g) blev opløst i 1,4-dioxan (5 ml), og der blev tilsat ethylbromacetat (3,3 g). Den resulterende blanding blev tilbagesvalet i 6 timer. Der blev tilsat triethylamin (0,2 g), og blandingen blev tilbagesvalet i 1 time. Efter at have fået lov at afkøle blev blandingen tilsat vand og toluen, og derefter ekstraheret med toluen. To-20 luenfasen blev tørret og koncentreret. Remanensen blev oprenset ved silicagelsøjlechromatografi, hvilket gav 1,0 g 2-(4-brom-2-fluor-5-ethoxycarbonylmethyliminophenyl)-4,5,6,7-tetrahydro-2H-isoindol-1,3-dion (forbindelse nr. 89). n^»® 1,5281.
Eksempler på herbicidt virksomme tetrahydrophthalimidslutforbinde1-25 ser, som er fremstillet ved samme fremgangsmåde som vist ovenfor, er vist i tabel 1.
Tabel 1
O
j x^S\jO
r.-z-c-ch-y' 1 I o R2 5
DK 158262B
7
Tabel 1
Forbin- Fysisk delse X Y Z Rj^ R2 konstant A Cl -NH- O -CH2CH3 H ng8 1,5519 B Cl -NH- O -CHCH2CH3 H ng4>5 1,5445 CH3 CH2CH3 10 C Cl -NH- O -CH H njj5 1,5401 x ch2ch3 D Cl -NH- O H Glasagtig E Cl -NH- O -CH2—Q H nfj5 1,5466 F Cl -NH- O -CH2CHC12 H Glasagtig
15 Smp. °C
G Cl -NH- O -CH2CHCH2C1 H 119-120
Cl ,H Cl -NH- O -CH2CH2OCH2CH2CH3 Η nβ5 1,5364 I Cl -NH- O -CH2CH2CN H nj5 1,5541 20 J Cl -NH- S -CH2CH2CH2CH2CH3 H nj4 1,5621 K Cl -NH- O -CH3 -CH3 Glasagtig L Br -NH- O -CH2CH3 H n$6 1,5281
Smp. °C
M Br -NH- O -CH2CH2OCH3 H 106-107 25 N Br -NH- O -CH3 -CH3 ng4>5 1,5661 O Br -NH- O -<^J -OCH3 ng4>5 1,5596 På samme måde som ovenfor, men under anvendelse af 4-chlor- 2-fluora-nilin i stedet for 4-brom-2-fluoranilin, ^fremstilledes 4-chlor- 2-30 fluor-5-nitroanilin. Smeltepunkt 83-84,5°C.
Claims (1)
- DK 158262 B 8 Tetrahydrophthalimidforbindelser med den almene formel 0 hvor X er chlor eller brom, og Q er amino eller nitro.
Applications Claiming Priority (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21239681 | 1981-12-25 | ||
| JP56212396A JPS58110566A (ja) | 1981-12-25 | 1981-12-25 | ２−フエニル−４，５，６，７−テトラヒドロ−２ｈ−イソインド−ル誘導体、その製造法およびそれを有効成分とする除草剤 |
| JP1384582A JPS58131969A (ja) | 1982-01-29 | 1982-01-29 | ２−フェニル−４，５，６，７−テトラヒドロ−２ｈ−イソインド−ル誘導体、その製造法およびそれを有効成分とする除草剤 |
| JP1384582 | 1982-01-29 | ||
| JP1785882 | 1982-02-05 | ||
| JP1785882A JPS58135864A (ja) | 1982-02-05 | 1982-02-05 | ２−フェニル−４，５，６，７−テトラヒドロ−２ｈ−イソインド−ル誘導体、その製造法およびそれを有効成分とする除草剤 |
| JP4694082 | 1982-03-23 | ||
| JP4694082A JPS58162574A (ja) | 1982-03-23 | 1982-03-23 | ２−フエニル−４，５，６，７−テトラヒドロ−２ｈ−イソインド−ル誘導体、その製造法およびそれを有効成分とする除草剤 |
| JP7630682 | 1982-05-06 | ||
| JP7630682A JPS58192868A (ja) | 1982-05-06 | 1982-05-06 | ２−フェニル−４，５，６，７−テトラヒドロ−２ｈ−イソインド−ル誘導体、その製造法およびそれを有効成分とする除草剤 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| DK237988A DK237988A (da) | 1988-05-02 |
| DK237988D0 DK237988D0 (da) | 1988-05-02 |
| DK158262B true DK158262B (da) | 1990-04-23 |
| DK158262C DK158262C (da) | 1990-10-08 |
Family
ID=27519566
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK573482A DK154703C (da) | 1981-12-25 | 1982-12-23 | Tetrahydrophthalimidforbindelser, herbicide praeparater indeholdende disse samt anvendelse deraf ved bekaempelse af ukrudt |
| DK237988A DK158262C (da) | 1981-12-25 | 1988-05-02 | Mellemprodukter til fremstilling af herbicide tetrahydrophthalimidforbindelser |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK573482A DK154703C (da) | 1981-12-25 | 1982-12-23 | Tetrahydrophthalimidforbindelser, herbicide praeparater indeholdende disse samt anvendelse deraf ved bekaempelse af ukrudt |
Country Status (14)
| Country | Link |
|---|---|
| US (5) | US4670046A (da) |
| EP (2) | EP0172306B1 (da) |
| AU (1) | AU557324B2 (da) |
| BG (2) | BG41995A3 (da) |
| BR (1) | BR8207478A (da) |
| CA (1) | CA1181407A (da) |
| CZ (1) | CZ279697B6 (da) |
| DE (1) | DE3273387D1 (da) |
| DK (2) | DK154703C (da) |
| HU (1) | HU188525B (da) |
| MY (2) | MY101267A (da) |
| PL (1) | PL134968B1 (da) |
| SK (1) | SK954482A3 (da) |
| UA (1) | UA7085A1 (da) |
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| US3808230A (en) * | 1960-01-21 | 1974-04-30 | Delmar Chem | 2-oxy-4-phthaloylamido-5-halobenzoate compounds |
| US3235605A (en) * | 1963-03-01 | 1966-02-15 | Ethyl Corp | Preparation of thiophenylethers |
| US3465001A (en) * | 1966-03-31 | 1969-09-02 | Merck & Co Inc | Maleimido aryloxy alkanoic acids,alkyl esters and amides thereof |
| US3654302A (en) * | 1970-01-30 | 1972-04-04 | Herbert Schwartz | Tetrahydrophthalanils |
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| US3878224A (en) * | 1970-12-23 | 1975-04-15 | Mitsubishi Chem Ind | N-substituted-{66 {40 -tetrahydrophthalimides |
| DE2223894C3 (de) * | 1972-05-17 | 1981-07-23 | Hoechst Ag, 6000 Frankfurt | Herbizide Mittel auf Basis von Phenoxycarbonsäurederivaten |
| US4001272A (en) * | 1974-09-03 | 1977-01-04 | E. I. Du Pont De Nemours And Company | Herbicidal 2-fluoro-4-halo-phenyl-4,5,6,7-tetrahydro-2h-isoindole-1,3-diones |
| US4032326A (en) * | 1974-12-24 | 1977-06-28 | E. I. Du Pont De Nemours And Company | Herbicidal 2-substituted aryl-4,5,6,7-tetrahydro-2h-isoindole-1,3-diones |
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| EP0000351A1 (de) * | 1977-07-07 | 1979-01-24 | Ciba-Geigy Ag | Phenoxy-phenylthio-alkancarbonsäurederivate, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und als Pflanzenwachstumsregulierungsmittel |
| GB2005668B (en) * | 1977-09-14 | 1982-05-26 | Shell Int Research | Herbicides |
| US4124375A (en) * | 1977-10-12 | 1978-11-07 | Monsanto Company | Substituted phthalimides for regulating the growth of plants |
| FR2433013A1 (fr) * | 1978-08-07 | 1980-03-07 | Rhone Poulenc Agrochimie | Procede de fabrication de l'acide trichloro-2,4,5 phenoxyacetique dont la mise en oeuvre ne necessite pas l'utilisation du trichloro-2,4,5 phenol |
| JPS55130954A (en) * | 1979-03-29 | 1980-10-11 | Sumitomo Chem Co Ltd | Phenylthioacetic acid ester derivative, its preparation, and herbicide containing said compound as effective component |
| US4292070A (en) * | 1979-04-13 | 1981-09-29 | Mitsubishi Chemical Industries, Ltd. | N-Substituted tetrahydrophthalimide and herbicidal composition |
| JPS5724355A (en) * | 1980-07-21 | 1982-02-08 | Mitsui Toatsu Chem Inc | Novel diphenyl ether type compound |
| US4420327A (en) * | 1980-10-07 | 1983-12-13 | Mitsubishi Chemical Industries Ltd. | Tetrahydrophthalimides and herbicidal composition |
| EP0049508A1 (en) * | 1980-10-07 | 1982-04-14 | Mitsubishi Kasei Corporation | N-(3-Substituted oxyphenyl) tetrahydrophthalimides and herbicidal composition |
| AU550845B2 (en) * | 1981-03-30 | 1986-04-10 | Sumitomo Chemical Company, Limited | Tetrahydrophthalimides and their starting compounds |
| US4431822A (en) * | 1981-03-30 | 1984-02-14 | Sumitomo Chemical Company, Limited | Tetrahydrophthalimides, and their production and use |
| DE3123157A1 (de) * | 1981-06-11 | 1983-01-05 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von s-aryl-thioglycolsaeuren |
| US4439229A (en) * | 1981-06-29 | 1984-03-27 | Rohm And Haas Company | Substituted phthalimides herbicides |
| US4484941A (en) * | 1981-09-01 | 1984-11-27 | Sumitomo Chemical Company, Limited | Tetrahydrophthalimides, and their production and use as herbicides |
| US4484940A (en) * | 1981-09-01 | 1984-11-27 | Sumitomo Chemical Company, Limited | Tetrahydrophthalimides, and their production and use as herbicides |
| EP0077938A3 (en) * | 1981-10-23 | 1983-08-24 | Mitsubishi Kasei Corporation | N-(3-substituted aminophenyl) tetrahydrophthalimides and herbicidal composition |
| AU557324B2 (en) * | 1981-12-25 | 1986-12-18 | Sumitomo Chemical Company, Limited | Tetrahydro phthalimide compounds |
| DE3377646D1 (en) * | 1982-05-26 | 1988-09-15 | Sumitomo Chemical Co | Tetrahydrophthalimides, and their production and use |
| JPS59101405A (ja) * | 1982-12-02 | 1984-06-12 | Sumitomo Chem Co Ltd | 除草組成物 |
| JPS59212472A (ja) * | 1983-05-16 | 1984-12-01 | Sumitomo Chem Co Ltd | ４，５，６，７−テトラヒドロ−２ｈ−イソインド−ル−１，３−ジオン誘導体、その製造法およびそれを有効成分とする除草剤 |
| JPS6054362A (ja) * | 1983-08-31 | 1985-03-28 | Sumitomo Chem Co Ltd | テトラヒドロフタルイミド誘導体，その製造法およびそれを有効成分とする除草剤 |
| US4563535A (en) * | 1983-09-19 | 1986-01-07 | Sumitomo Chemical Co., Ltd. | Process for producing tetrahydrophthalimides |
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-
1982
- 1982-12-01 AU AU91035/82A patent/AU557324B2/en not_active Ceased
- 1982-12-06 CA CA000417107A patent/CA1181407A/en not_active Expired
- 1982-12-20 DE DE8282111841T patent/DE3273387D1/de not_active Expired
- 1982-12-20 EP EP85103131A patent/EP0172306B1/en not_active Expired
- 1982-12-20 EP EP82111841A patent/EP0083055B1/en not_active Expired
- 1982-12-22 HU HU824131A patent/HU188525B/hu not_active IP Right Cessation
- 1982-12-22 SK SK9544-82A patent/SK954482A3/sk unknown
- 1982-12-22 CZ CS829544A patent/CZ279697B6/cs not_active IP Right Cessation
- 1982-12-23 PL PL1982239711A patent/PL134968B1/pl unknown
- 1982-12-23 BR BR8207478A patent/BR8207478A/pt not_active IP Right Cessation
- 1982-12-23 DK DK573482A patent/DK154703C/da not_active IP Right Cessation
- 1982-12-24 BG BG059040A patent/BG41995A3/xx unknown
- 1982-12-24 UA UA3525700A patent/UA7085A1/uk unknown
-
1983
- 1983-03-09 US US06/473,755 patent/US4670046A/en not_active Expired - Lifetime
-
1986
- 1986-07-21 US US06/887,970 patent/US4770695A/en not_active Expired - Lifetime
- 1986-12-17 US US06/942,703 patent/US4938795A/en not_active Expired - Lifetime
-
1987
- 1987-07-14 MY MYPI87000999A patent/MY101267A/en unknown
- 1987-09-30 US US07/102,617 patent/US4881970A/en not_active Expired - Fee Related
- 1987-09-30 US US07/102,615 patent/US4826533A/en not_active Expired - Fee Related
-
1988
- 1988-05-02 DK DK237988A patent/DK158262C/da not_active IP Right Cessation
- 1988-12-30 MY MY90/88A patent/MY8800090A/xx unknown
-
1994
- 1994-02-24 BG BG098553A patent/BG61119B2/bg unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BG41995A3 (en) | 1987-09-15 |
| EP0083055B1 (en) | 1986-09-17 |
| DK237988A (da) | 1988-05-02 |
| DE3273387D1 (en) | 1986-10-23 |
| MY8800090A (en) | 1988-12-31 |
| EP0172306A1 (en) | 1986-02-26 |
| EP0083055A2 (en) | 1983-07-06 |
| US4670046A (en) | 1987-06-02 |
| PL239711A1 (en) | 1984-02-27 |
| CZ954482A3 (en) | 1995-01-18 |
| DK154703B (da) | 1988-12-12 |
| SK278417B6 (en) | 1997-04-09 |
| EP0172306B1 (en) | 1988-09-07 |
| UA7085A1 (uk) | 1995-06-30 |
| DK158262C (da) | 1990-10-08 |
| US4770695A (en) | 1988-09-13 |
| SK954482A3 (en) | 1997-04-09 |
| PL134968B1 (en) | 1985-09-30 |
| US4826533A (en) | 1989-05-02 |
| DK154703C (da) | 1989-06-19 |
| AU557324B2 (en) | 1986-12-18 |
| BR8207478A (pt) | 1983-10-18 |
| US4881970A (en) | 1989-11-21 |
| CZ279697B6 (cs) | 1995-06-14 |
| DK573482A (da) | 1983-06-26 |
| EP0083055A3 (en) | 1983-09-07 |
| CA1181407A (en) | 1985-01-22 |
| AU9103582A (en) | 1983-06-30 |
| DK237988D0 (da) | 1988-05-02 |
| MY101267A (en) | 1991-08-17 |
| BG61119B2 (bg) | 1996-11-29 |
| HU188525B (en) | 1986-04-28 |
| US4938795A (en) | 1990-07-03 |
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Legal Events
| Date | Code | Title | Description |
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| PBP | Patent lapsed |