DE2700270A1 - Imidazoisoindoldione und verfahren zu ihrer herstellung - Google Patents
Imidazoisoindoldione und verfahren zu ihrer herstellungInfo
- Publication number
- DE2700270A1 DE2700270A1 DE19772700270 DE2700270A DE2700270A1 DE 2700270 A1 DE2700270 A1 DE 2700270A1 DE 19772700270 DE19772700270 DE 19772700270 DE 2700270 A DE2700270 A DE 2700270A DE 2700270 A1 DE2700270 A1 DE 2700270A1
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- chj
- formula
- alkyl
- substituents
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 36
- GCFBDIVEVTXDJZ-UHFFFAOYSA-N pyrrolo[3,4-e]benzimidazole-2,4-dione Chemical compound O=C1C2=NC(=O)N=C2C2=CN=CC2=C1 GCFBDIVEVTXDJZ-UHFFFAOYSA-N 0.000 title claims description 22
- 238000004519 manufacturing process Methods 0.000 title description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 129
- 150000001875 compounds Chemical class 0.000 claims description 43
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 42
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 39
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 35
- 239000000203 mixture Substances 0.000 claims description 32
- 239000002904 solvent Substances 0.000 claims description 29
- 239000004480 active ingredient Substances 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 239000004009 herbicide Substances 0.000 claims description 14
- 239000000460 chlorine Chemical group 0.000 claims description 13
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 9
- 239000012312 sodium hydride Substances 0.000 claims description 9
- LAFRKWDMWGHGPG-UHFFFAOYSA-N 1,3-dioxoisoindole-2-carboxamide Chemical compound C1=CC=C2C(=O)N(C(=O)N)C(=O)C2=C1 LAFRKWDMWGHGPG-UHFFFAOYSA-N 0.000 claims description 8
- 239000003513 alkali Substances 0.000 claims description 8
- 150000004678 hydrides Chemical class 0.000 claims description 8
- 230000003287 optical effect Effects 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 238000007363 ring formation reaction Methods 0.000 claims description 7
- 239000008096 xylene Substances 0.000 claims description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 125000005059 halophenyl group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- 239000000908 ammonium hydroxide Substances 0.000 claims description 3
- 239000003456 ion exchange resin Substances 0.000 claims description 3
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 3
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 claims description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 2
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 2
- 239000011698 potassium fluoride Substances 0.000 claims description 2
- 235000003270 potassium fluoride Nutrition 0.000 claims description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 3
- 229910052801 chlorine Chemical group 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- 241000196324 Embryophyta Species 0.000 description 36
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 23
- 239000000047 product Substances 0.000 description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 16
- 239000000155 melt Substances 0.000 description 16
- 238000003756 stirring Methods 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
- 239000002585 base Substances 0.000 description 11
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 210000003298 dental enamel Anatomy 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000003921 oil Substances 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- GPYTYOMSQHBYTK-UHFFFAOYSA-N 2-azaniumyl-2,3-dimethylbutanoate Chemical compound CC(C)C(C)(N)C(O)=O GPYTYOMSQHBYTK-UHFFFAOYSA-N 0.000 description 7
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 7
- 230000002363 herbicidal effect Effects 0.000 description 7
- 238000002329 infrared spectrum Methods 0.000 description 7
- AZPJXONNBLOZFE-UHFFFAOYSA-N 2-[(3-methylphenyl)carbamoyl]benzoic acid Chemical compound CC1=CC=CC(NC(=O)C=2C(=CC=CC=2)C(O)=O)=C1 AZPJXONNBLOZFE-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000011835 investigation Methods 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- GVTLFGJNTIRUEG-ZHACJKMWSA-N (e)-n-(3-methoxyphenyl)-3-phenylprop-2-enamide Chemical compound COC1=CC=CC(NC(=O)\C=C\C=2C=CC=CC=2)=C1 GVTLFGJNTIRUEG-ZHACJKMWSA-N 0.000 description 5
- 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 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 125000005242 carbamoyl alkyl group Chemical group 0.000 description 5
- 230000012010 growth Effects 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- -1 isoindoline acetamide Chemical compound 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- OWLRLMNLEKSCMX-UHFFFAOYSA-N 1-(1,3-dioxoisoindol-2-yl)cyclohexane-1-carbonyl chloride Chemical compound O=C1C2=CC=CC=C2C(=O)N1C1(C(=O)Cl)CCCCC1 OWLRLMNLEKSCMX-UHFFFAOYSA-N 0.000 description 4
- XEUACMUIDVGNCY-UHFFFAOYSA-N 1-(1,3-dioxoisoindol-2-yl)cyclohexane-1-carboxylic acid Chemical compound O=C1C2=CC=CC=C2C(=O)N1C1(C(=O)O)CCCCC1 XEUACMUIDVGNCY-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- MGAZWNTXVAQXCQ-UHFFFAOYSA-N C(C)(=O)N.C1(C=2C(C(N1)=O)=CC=CC2)=O Chemical compound C(C)(=O)N.C1(C=2C(C(N1)=O)=CC=CC2)=O MGAZWNTXVAQXCQ-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 244000062793 Sorghum vulgare Species 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 125000005219 aminonitrile group Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 235000019713 millet Nutrition 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- WOXWUZCRWJWTRT-UHFFFAOYSA-N 1-amino-1-cyclohexanecarboxylic acid Chemical compound OC(=O)C1(N)CCCCC1 WOXWUZCRWJWTRT-UHFFFAOYSA-N 0.000 description 3
- 241001290610 Abildgaardia Species 0.000 description 3
- 240000006995 Abutilon theophrasti Species 0.000 description 3
- 240000001592 Amaranthus caudatus Species 0.000 description 3
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 3
- 241000217446 Calystegia sepium Species 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241001570521 Lonicera periclymenum Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 244000235659 Rubus idaeus Species 0.000 description 3
- 241000158147 Sator Species 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- KCUOMAWBYCUWMA-UHFFFAOYSA-N 2-[(2-cyano-3-methylbutan-2-yl)carbamoyl]benzoic acid Chemical compound CC(C)C(C)(C#N)NC(=O)C1=CC=CC=C1C(O)=O KCUOMAWBYCUWMA-UHFFFAOYSA-N 0.000 description 2
- KFAFXURIKULROI-UHFFFAOYSA-N 2-acetamido-2,3-dimethylbutanoic acid Chemical compound CC(C)C(C)(C(O)=O)NC(C)=O KFAFXURIKULROI-UHFFFAOYSA-N 0.000 description 2
- 241000270728 Alligator Species 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 244000075850 Avena orientalis Species 0.000 description 2
- 235000007319 Avena orientalis Nutrition 0.000 description 2
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
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- 244000064817 Sorghum halepense var. sudanense Species 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 229960000892 attapulgite Drugs 0.000 description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 2
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
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- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
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- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
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- 239000007921 spray Substances 0.000 description 2
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- TUPNSSNDXLGGBQ-UHFFFAOYSA-N 1,3-dioxoisoindole-2-carboxylic acid Chemical compound C1=CC=C2C(=O)N(C(=O)O)C(=O)C2=C1 TUPNSSNDXLGGBQ-UHFFFAOYSA-N 0.000 description 1
- HUMMCZRNZCKXHL-UHFFFAOYSA-N 1-aminocyclohexane-1-carbonitrile Chemical compound N#CC1(N)CCCCC1 HUMMCZRNZCKXHL-UHFFFAOYSA-N 0.000 description 1
- GQEXBJOPGJUKIL-UHFFFAOYSA-N 1-aminocyclohexane-1-carboxamide Chemical compound NC(=O)C1(N)CCCCC1 GQEXBJOPGJUKIL-UHFFFAOYSA-N 0.000 description 1
- UXQFYFKOUHGJQD-UHFFFAOYSA-N 2-(2,3-dimethylphenyl)propan-2-ylazanium;hydroxide Chemical compound [OH-].CC1=CC=CC(C(C)(C)[NH3+])=C1C UXQFYFKOUHGJQD-UHFFFAOYSA-N 0.000 description 1
- PAZAAUKLIHJNJP-UHFFFAOYSA-N 2-amino-2,3,3-trimethylbutanamide Chemical compound CC(C)(C)C(C)(N)C(N)=O PAZAAUKLIHJNJP-UHFFFAOYSA-N 0.000 description 1
- CAOHBROWLMCZRP-UHFFFAOYSA-N 2-amino-2,3-dimethylbutanenitrile Chemical compound CC(C)C(C)(N)C#N CAOHBROWLMCZRP-UHFFFAOYSA-N 0.000 description 1
- AUWOKGIWMDMIRQ-UHFFFAOYSA-N 2-amino-2-ethylbutanenitrile Chemical compound CCC(N)(CC)C#N AUWOKGIWMDMIRQ-UHFFFAOYSA-N 0.000 description 1
- GOCHUMXNGQDAOQ-UHFFFAOYSA-N 3h-pyrrolo[3,4-e]benzimidazole-6,8-dione Chemical class O=C1NC(=O)C2=C1C=CC1=C2NC=N1 GOCHUMXNGQDAOQ-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
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- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
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- 241000380130 Ehrharta erecta Species 0.000 description 1
- 241000508725 Elymus repens Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 244000207543 Euphorbia heterophylla Species 0.000 description 1
- RCZNYTXJVULKCR-UHFFFAOYSA-N I.I.I.I.I.I.I.I Chemical compound I.I.I.I.I.I.I.I RCZNYTXJVULKCR-UHFFFAOYSA-N 0.000 description 1
- 241000207890 Ipomoea purpurea Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
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- 235000000656 Rosa multiflora Nutrition 0.000 description 1
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- 235000003982 Rubus allegheniensis Nutrition 0.000 description 1
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- 241000533293 Sesbania emerus Species 0.000 description 1
- 240000003461 Setaria viridis Species 0.000 description 1
- 235000002248 Setaria viridis Nutrition 0.000 description 1
- 240000006410 Sida spinosa Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 240000002439 Sorghum halepense Species 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
- 235000021028 berry Nutrition 0.000 description 1
- 235000021029 blackberry Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000009194 climbing Effects 0.000 description 1
- ZBYYWKJVSFHYJL-UHFFFAOYSA-L cobalt(2+);diacetate;tetrahydrate Chemical compound O.O.O.O.[Co+2].CC([O-])=O.CC([O-])=O ZBYYWKJVSFHYJL-UHFFFAOYSA-L 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
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- 235000005822 corn Nutrition 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
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- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- 241001233957 eudicotyledons Species 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 208000006278 hypochromic anemia Diseases 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 230000001795 light effect Effects 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- DHEHLOBJCYUXDU-UHFFFAOYSA-N methyl 2-[(1-amino-2,3,3-trimethyl-1-oxobutan-2-yl)carbamoyl]benzoate Chemical compound COC(=O)C1=CC=CC=C1C(=O)NC(C)(C(N)=O)C(C)(C)C DHEHLOBJCYUXDU-UHFFFAOYSA-N 0.000 description 1
- GNBWUEAMCSHHMO-UHFFFAOYSA-N methyl 2-carbonochloridoylbenzoate Chemical compound COC(=O)C1=CC=CC=C1C(Cl)=O GNBWUEAMCSHHMO-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000005544 phthalimido group Chemical group 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- IZWPGJFSBABFGL-GMFCBQQYSA-M sodium;2-[methyl-[(z)-octadec-9-enoyl]amino]ethanesulfonate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC(=O)N(C)CCS([O-])(=O)=O IZWPGJFSBABFGL-GMFCBQQYSA-M 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 150000003738 xylenes Chemical class 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
- C12P41/006—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by reactions involving C-N bonds, e.g. nitriles, amides, hydantoins, carbamates, lactames, transamination reactions, or keto group formation from racemic mixtures
- C12P41/007—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by reactions involving C-N bonds, e.g. nitriles, amides, hydantoins, carbamates, lactames, transamination reactions, or keto group formation from racemic mixtures by reactions involving acyl derivatives of racemic amines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Agronomy & Crop Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biotechnology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Genetics & Genomics (AREA)
- Microbiology (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- Environmental Sciences (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ZA00780046A ZA7846B (en) | 1977-01-05 | 1978-01-05 | Method and apparatus for the gasification of solid fuel particularly coal |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/631,357 US4017510A (en) | 1975-11-12 | 1975-11-12 | Imidazoisoindolediones and the use thereof as herbicidal agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2700270A1 true DE2700270A1 (de) | 1978-07-13 |
Family
ID=24530858
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772700270 Withdrawn DE2700270A1 (de) | 1975-11-12 | 1977-01-05 | Imidazoisoindoldione und verfahren zu ihrer herstellung |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US4017510A (enExample) |
| JP (1) | JPS5390295A (enExample) |
| CA (1) | CA1082713A (enExample) |
| DE (1) | DE2700270A1 (enExample) |
| FR (1) | FR2377402A1 (enExample) |
| GB (1) | GB1566523A (enExample) |
| NL (1) | NL7700386A (enExample) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0150854A3 (en) * | 1984-02-02 | 1985-08-14 | Stamicarbon B.V. | Optically active substituted butyramide, and process for the optical separation of substitute butyramide |
| EP0127883A3 (en) * | 1983-06-02 | 1985-08-21 | American Cyanamid Company | (2-imidazolin-2-yl)thieno- and (furo 2,3-b) and (3,2-b) pyridines and intermediates for the preparation thereof, and use of said compounds as herbicidal agents |
| EP0153583A1 (de) * | 1984-02-03 | 1985-09-04 | Hoechst Aktiengesellschaft | Isoindole, Verfahren zu ihrer Herstellung und ihre Verwendung in der Landwirtschaft |
| US4741767A (en) * | 1984-11-16 | 1988-05-03 | Hoffmann-La Roche Inc. | 2H-Imidazo(1',2':1,2)pyrrolo(3,4-B)pyridine compounds, and their use as herbicidal agents |
| EP0298029A1 (de) * | 1987-07-01 | 1989-01-04 | Ciba-Geigy Ag | Substituierte Imidazolone mit herbizider Wirkung |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4608437A (en) * | 1977-08-08 | 1986-08-26 | American Cyanamid Company | Preparation of imidazolinyl benzoic acids |
| IL62794A0 (en) * | 1980-06-02 | 1981-07-31 | American Cyanamid Co | Substituted nicotinic acid esters and salts thereof and their use as herbicidal agents |
| US4518780A (en) * | 1982-05-25 | 1985-05-21 | American Cyanamid Company | Process for the preparation of 2-(5,5-disubstituted-4-oxo-2-imidazolin-2-yl)nicotinic acids and quinoline-3-carboxylic acids |
| DE3474815D1 (en) * | 1983-03-28 | 1988-12-01 | American Cyanamid Co | Novel process for the preparation of aminonitriles useful for the preparation of herbicides |
| US4650514A (en) * | 1983-06-02 | 1987-03-17 | American Cyanamid Company | (2-imidazolin-2-yl)thieno- and furo[2,3-b] and [3,2-b]pyridines and intermediates for the preparation thereof, and use of said compounds as herbicidal agents |
| EP0135711B1 (en) * | 1983-08-02 | 1989-08-09 | American Cyanamid Company | 5-thioxo-2-imidazolinyl benzoic acids, esters, salts and related compounds, and use thereof as herbicidal agents |
| US4911747A (en) * | 1983-08-02 | 1990-03-27 | American Cyanamid Co. | Herbicidal 3-thio-5H-imidazo[2,1-A]isoindole-3-(2H),5-diones |
| AR241812A1 (es) * | 1983-08-02 | 1992-12-30 | American Cyanamit Company | Nuevas hidroimidazo pirrolopirinas, o vinolinas, tieno-y furo¡2,3b¿ piridinas dihidrotieno-y furo ¡2,3b¿ piridinas, tieno-y furo ¡3,2b¿ piridinas tautomeros de las mismas. |
| GB2172886A (en) * | 1985-03-26 | 1986-10-01 | Shell Int Research | Imidazoisoindole dione herbicides |
| CA1309096C (en) | 1985-08-13 | 1992-10-20 | Sumitomo Chemical Co., Ltd. | Butenoic acid derivatives, and their production and use |
| EP0261705A1 (en) * | 1986-08-25 | 1988-03-30 | Shell Internationale Researchmaatschappij B.V. | Herbicidal imidazolinyl benzoic acids and derivatives |
| FR2681067B1 (fr) | 1991-09-10 | 1993-12-17 | Elf Sanofi | Derives heterocycliques n-substitues, leur preparation, les compositions pharmaceutiques en contenant. |
| US5108485A (en) * | 1990-08-31 | 1992-04-28 | American Cyanamid Company | Herbicidal 2-(2-imidazolin-2-yl)-benzazoles |
| CA2274527A1 (en) * | 1997-01-16 | 1998-07-23 | Hampshire Chemical Corp. | Preparation of .alpha.-amino carboxylic acid amides |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3409425A (en) * | 1966-01-24 | 1968-11-05 | Du Pont | 2-substituted pyrazoloisoindolones as herbicides |
| US3555042A (en) * | 1968-10-04 | 1971-01-12 | American Home Prod | 2,3,5,9b-tetrahydro-1h-imidazo(2,1-a) isoindol-5-ols |
| ZA718536B (en) * | 1971-01-11 | 1972-09-27 | Wyeth John & Brother Ltd | Heterocyclic compounds |
| US3849436A (en) * | 1972-10-04 | 1974-11-19 | Du Pont | Cyclization of 2-(3-aryl-5-pyrazolyl)benzoic acids,esters and amides to 2-arylpyrazolo(5,1-a)isoindol-8-ones |
-
1975
- 1975-11-12 US US05/631,357 patent/US4017510A/en not_active Expired - Lifetime
-
1976
- 1976-10-18 US US05/733,635 patent/US4062671A/en not_active Expired - Lifetime
- 1976-12-21 CA CA268,327A patent/CA1082713A/en not_active Expired
-
1977
- 1977-01-05 DE DE19772700270 patent/DE2700270A1/de not_active Withdrawn
- 1977-01-11 GB GB1035/77A patent/GB1566523A/en not_active Expired
- 1977-01-12 FR FR7700770A patent/FR2377402A1/fr active Granted
- 1977-01-14 JP JP350577A patent/JPS5390295A/ja active Pending
- 1977-01-14 NL NL7700386A patent/NL7700386A/xx not_active Application Discontinuation
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0127883A3 (en) * | 1983-06-02 | 1985-08-21 | American Cyanamid Company | (2-imidazolin-2-yl)thieno- and (furo 2,3-b) and (3,2-b) pyridines and intermediates for the preparation thereof, and use of said compounds as herbicidal agents |
| EP0150854A3 (en) * | 1984-02-02 | 1985-08-14 | Stamicarbon B.V. | Optically active substituted butyramide, and process for the optical separation of substitute butyramide |
| JPS60188355A (ja) * | 1984-02-02 | 1985-09-25 | デーエスエム ナムローゼ フェンノートシャップ | Ｄ−２−アミノ−２，３−ジメチルブチルアミドおよびｄ−２−アミノ−２，３−ジメチルブチルアミドおよび／またはｌ−２−アミノ−２，３−ジメチル酪酸の製法 |
| US4812403A (en) * | 1984-02-02 | 1989-03-14 | Stamicarbon B.V. | Optically active substituted butyramide, and process for the optical separation of substituted butyramide |
| EP0153583A1 (de) * | 1984-02-03 | 1985-09-04 | Hoechst Aktiengesellschaft | Isoindole, Verfahren zu ihrer Herstellung und ihre Verwendung in der Landwirtschaft |
| US4741767A (en) * | 1984-11-16 | 1988-05-03 | Hoffmann-La Roche Inc. | 2H-Imidazo(1',2':1,2)pyrrolo(3,4-B)pyridine compounds, and their use as herbicidal agents |
| EP0298029A1 (de) * | 1987-07-01 | 1989-01-04 | Ciba-Geigy Ag | Substituierte Imidazolone mit herbizider Wirkung |
| US4895588A (en) * | 1987-07-01 | 1990-01-23 | Ciba-Geigy Corporation | Substituted imidazolones having herbicidal activity |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2377402A1 (fr) | 1978-08-11 |
| GB1566523A (en) | 1980-04-30 |
| US4017510A (en) | 1977-04-12 |
| CA1082713A (en) | 1980-07-29 |
| NL7700386A (nl) | 1978-07-18 |
| US4062671A (en) | 1977-12-13 |
| JPS5390295A (en) | 1978-08-08 |
| FR2377402B1 (enExample) | 1980-10-10 |
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