CA1339688C - 3,4,5,6,-tetrahydrophtalimides substitue-net leurs intermediares - Google Patents

3,4,5,6,-tetrahydrophtalimides substitue-net leurs intermediares

Info

Publication number: CA1339688C
Authority: CA; Canada
Prior art keywords: alkyl; hydrogen; acid; tetrahydrophthalimide; formula
Prior art date: 1986-02-07
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 - Fee Related

Application number

CA000616913A

Other languages

English (en)

Inventor

Peter Plath

Karl Eicken

Norbert Goetz

Jochen Wild

Norbert Meyer

Bruno Wuerzer

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BASF SE

Original Assignee

BASF SE

Priority date (The priority date 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 date listed.)

1986-02-07

Filing date

1994-09-01

Publication date

1998-02-24

1986-02-07 Priority claimed from DE19863603789 external-priority patent/DE3603789A1/de

1994-09-01 Application filed by BASF SE filed Critical BASF SE

1994-09-01 Priority to CA000616913A priority Critical patent/CA1339688C/fr

1998-02-24 Application granted granted Critical

1998-02-24 Publication of CA1339688C publication Critical patent/CA1339688C/fr

2007-02-02 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

239000000543 intermediate Substances 0.000 title abstract description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 74
150000001875 compounds Chemical class 0.000 claims abstract description 30
125000003903 2-propenyl group Chemical class [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 11
229910052801 chlorine Inorganic materials 0.000 claims abstract description 7
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 6
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims abstract description 6
125000006701 (C1-C7) alkyl group Chemical group 0.000 claims abstract description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 4
125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 4
229910052731 fluorine Inorganic materials 0.000 claims abstract description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 6
239000000460 chlorine Substances 0.000 claims description 123
229910052739 hydrogen Inorganic materials 0.000 claims description 27
239000001257 hydrogen Substances 0.000 claims description 25
238000000034 method Methods 0.000 claims description 24
125000001309 chloro group Chemical group Cl* 0.000 claims description 19
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 18
125000001246 bromo group Chemical group Br* 0.000 claims description 12
150000001448 anilines Chemical class 0.000 claims description 10
238000006243 chemical reaction Methods 0.000 claims description 9
239000003795 chemical substances by application Substances 0.000 claims description 8
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 7
150000005181 nitrobenzenes Chemical class 0.000 claims description 7
125000004093 cyano group Chemical group *C#N 0.000 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
150000002828 nitro derivatives Chemical class 0.000 claims description 5
IHTLKLSRRSWIGD-DAFODLJHSA-N 2-chloro-5-nitrocinnamic acid Chemical compound OC(=O)\C=C\C1=CC([N+]([O-])=O)=CC=C1Cl IHTLKLSRRSWIGD-DAFODLJHSA-N 0.000 claims description 3
CMWKITSNTDAEDT-UHFFFAOYSA-N 2-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC=C1C=O CMWKITSNTDAEDT-UHFFFAOYSA-N 0.000 claims description 2
OZORIZOKZULOBT-UHFFFAOYSA-N 3-(5-amino-2-chlorophenyl)prop-2-enoic acid Chemical compound NC1=CC=C(Cl)C(C=CC(O)=O)=C1 OZORIZOKZULOBT-UHFFFAOYSA-N 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
229910052727 yttrium Inorganic materials 0.000 claims description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
239000003638 chemical reducing agent Substances 0.000 claims 2
238000004519 manufacturing process Methods 0.000 claims 2
125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 1
BLGILVBHNUDJSB-UHFFFAOYSA-N 2-nitro-2-phenylacetaldehyde Chemical compound [O-][N+](=O)C(C=O)C1=CC=CC=C1 BLGILVBHNUDJSB-UHFFFAOYSA-N 0.000 claims 1
YPAKZCPHSZUMCR-UHFFFAOYSA-N benzene;nitrobenzene Chemical class C1=CC=CC=C1.[O-][N+](=O)C1=CC=CC=C1 YPAKZCPHSZUMCR-UHFFFAOYSA-N 0.000 claims 1
238000005984 hydrogenation reaction Methods 0.000 claims 1
239000007858 starting material Substances 0.000 claims 1
238000002360 preparation method Methods 0.000 abstract description 14
239000004009 herbicide Substances 0.000 abstract description 10
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 36
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
239000000047 product Substances 0.000 description 31
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
-1 N-substituted 3,4,5,6-tetrahydrophthalimides Chemical class 0.000 description 28
239000004480 active ingredient Substances 0.000 description 28
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
239000000203 mixture Substances 0.000 description 24
239000003921 oil Substances 0.000 description 24
239000000243 solution Substances 0.000 description 23
239000002253 acid Substances 0.000 description 21
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
238000002844 melting Methods 0.000 description 17
230000008018 melting Effects 0.000 description 17
229960000583 acetic acid Drugs 0.000 description 15
241000196324 Embryophyta Species 0.000 description 13
239000007787 solid Substances 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
229940073584 methylene chloride Drugs 0.000 description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
239000012362 glacial acetic acid Substances 0.000 description 9
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
229910052943 magnesium sulfate Inorganic materials 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
AFJWMGOTLUUGHF-UHFFFAOYSA-N 4,5,6,7-tetrahydroisoindole-1,3-dione Chemical group C1CCCC2=C1C(=O)NC2=O AFJWMGOTLUUGHF-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
239000012074 organic phase Substances 0.000 description 6
239000000725 suspension Substances 0.000 description 6
VFVHWCKUHAEDMY-UHFFFAOYSA-N 2-chloro-5-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(Cl)C(C=O)=C1 VFVHWCKUHAEDMY-UHFFFAOYSA-N 0.000 description 5
OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 5
239000006185 dispersion Substances 0.000 description 5
239000000839 emulsion Substances 0.000 description 5
238000001914 filtration Methods 0.000 description 5
150000002431 hydrogen Chemical class 0.000 description 5
239000002904 solvent Substances 0.000 description 5
238000012360 testing method Methods 0.000 description 5
238000011282 treatment Methods 0.000 description 5
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 4
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
244000068988 Glycine max Species 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
238000001816 cooling Methods 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
150000002170 ethers Chemical class 0.000 description 4
239000008187 granular material Substances 0.000 description 4
235000012054 meals Nutrition 0.000 description 4
239000006072 paste Substances 0.000 description 4
239000012071 phase Substances 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 3
240000005979 Hordeum vulgare Species 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
235000010582 Pisum sativum Nutrition 0.000 description 3
240000004713 Pisum sativum Species 0.000 description 3
241001506137 Rapa Species 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
240000006394 Sorghum bicolor Species 0.000 description 3
235000002017 Zea mays subsp mays Nutrition 0.000 description 3
238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
238000010410 dusting Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
230000002363 herbicidal effect Effects 0.000 description 3
125000000896 monocarboxylic acid group Chemical group 0.000 description 3
230000000802 nitrating effect Effects 0.000 description 3
229920000151 polyglycol Polymers 0.000 description 3
239000010695 polyglycol Substances 0.000 description 3
239000000843 powder Substances 0.000 description 3
FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
241000894007 species Species 0.000 description 3
238000003756 stirring Methods 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
229940086542 triethylamine Drugs 0.000 description 3
239000008096 xylene Substances 0.000 description 3
IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
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 2
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 2
SPAMRUYRVYMHPV-UHFFFAOYSA-N 3a,4,5,7a-tetrahydroisoindole-1,3-dione Chemical class C1=CCCC2C(=O)NC(=O)C21 SPAMRUYRVYMHPV-UHFFFAOYSA-N 0.000 description 2
HMMBJOWWRLZEMI-UHFFFAOYSA-N 4,5,6,7-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1CCCC2=C1C(=O)OC2=O HMMBJOWWRLZEMI-UHFFFAOYSA-N 0.000 description 2
244000105624 Arachis hypogaea Species 0.000 description 2
244000075850 Avena orientalis Species 0.000 description 2
235000021537 Beetroot Nutrition 0.000 description 2
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241000335053 Beta vulgaris Species 0.000 description 2
240000002791 Brassica napus Species 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
240000007154 Coffea arabica Species 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
235000014820 Galium aparine Nutrition 0.000 description 2
240000005702 Galium aparine Species 0.000 description 2
235000010469 Glycine max Nutrition 0.000 description 2
244000299507 Gossypium hirsutum Species 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
240000004658 Medicago sativa Species 0.000 description 2
235000004357 Mentha x piperita Nutrition 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
235000007195 Pennisetum typhoides Nutrition 0.000 description 2
235000010617 Phaseolus lunatus Nutrition 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
235000002594 Solanum nigrum Nutrition 0.000 description 2
235000011684 Sorghum saccharatum Nutrition 0.000 description 2
235000021536 Sugar beet Nutrition 0.000 description 2
235000015724 Trifolium pratense Nutrition 0.000 description 2
244000098338 Triticum aestivum Species 0.000 description 2
240000005592 Veronica officinalis Species 0.000 description 2
240000008042 Zea mays Species 0.000 description 2
238000001720 action spectrum Methods 0.000 description 2
150000008055 alkyl aryl sulfonates Chemical group 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
235000013877 carbamide Nutrition 0.000 description 2
239000000969 carrier Substances 0.000 description 2
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235000013339 cereals Nutrition 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
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238000001704 evaporation Methods 0.000 description 2
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239000005457 ice water Substances 0.000 description 2
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125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 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
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
239000011707 mineral Substances 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
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YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
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UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
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QFUSCYRJMXLNRB-UHFFFAOYSA-N 2,6-dinitroaniline Chemical class NC1=C([N+]([O-])=O)C=CC=C1[N+]([O-])=O QFUSCYRJMXLNRB-UHFFFAOYSA-N 0.000 description 1
PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
NDOPHXWIAZIXPR-UHFFFAOYSA-N 2-bromobenzaldehyde Chemical compound BrC1=CC=CC=C1C=O NDOPHXWIAZIXPR-UHFFFAOYSA-N 0.000 description 1
MLIREBYILWEBDM-UHFFFAOYSA-M 2-cyanoacetate Chemical compound [O-]C(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-M 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
REEXLQXWNOSJKO-UHFFFAOYSA-N 2h-1$l^{4},2,3-benzothiadiazine 1-oxide Chemical class C1=CC=C2S(=O)NN=CC2=C1 REEXLQXWNOSJKO-UHFFFAOYSA-N 0.000 description 1
YGRWDGMIJOLYCX-UHFFFAOYSA-N 3-(2-chloro-5-nitrophenyl)prop-2-enal Chemical compound [O-][N+](=O)C1=CC=C(Cl)C(C=CC=O)=C1 YGRWDGMIJOLYCX-UHFFFAOYSA-N 0.000 description 1
ZETIVVHRRQLWFW-UHFFFAOYSA-N 3-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC(C=O)=C1 ZETIVVHRRQLWFW-UHFFFAOYSA-N 0.000 description 1
241000191291 Abies alba Species 0.000 description 1
240000006995 Abutilon theophrasti Species 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
244000291564 Allium cepa Species 0.000 description 1
235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
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240000001592 Amaranthus caudatus Species 0.000 description 1
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Indole Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

CA000616913A 1986-02-07 1994-09-01 3,4,5,6,-tetrahydrophtalimides substitue-net leurs intermediares Expired - Fee Related CA1339688C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000616913A CA1339688C (fr)	1986-02-07	1994-09-01	3,4,5,6,-tetrahydrophtalimides substitue-net leurs intermediares

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
DEP3603789.3		1986-02-07
DE19863603789 DE3603789A1 (de)	1986-02-07	1986-02-07	N-substituierte 3,4,5,6-tetrahydrophthalimide
CA000528764A CA1337657C (fr)	1986-02-07	1987-02-02	3,4,5,6-tetrahydrophtalamides substitues en n et leurs intermediaires
CA000616913A CA1339688C (fr)	1986-02-07	1994-09-01	3,4,5,6,-tetrahydrophtalimides substitue-net leurs intermediares

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000528764A Division CA1337657C (fr)	1986-02-07	1987-02-02	3,4,5,6-tetrahydrophtalamides substitues en n et leurs intermediaires

Publications (1)

Publication Number	Publication Date
CA1339688C true CA1339688C (fr)	1998-02-24

Family

ID=25671225

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000616913A Expired - Fee Related CA1339688C (fr)	1986-02-07	1994-09-01	3,4,5,6,-tetrahydrophtalimides substitue-net leurs intermediares

Country Status (1)

Country	Link
CA (1)	CA1339688C (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
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RU2473541C2 (ru) *	2007-04-23	2013-01-27	Байер Кропсайенс Аг	Инсектицидные арилпирролидины
US8980937B2 (en)	2007-04-23	2015-03-17	Bayer Cropscience Ag	Insecticidal aryl pyrrolidines
US9266830B2 (en)	2007-04-23	2016-02-23	Bayer Intellectual Property Gmbh	Pesticidal arylpyrrolidines

1994
- 1994-09-01 CA CA000616913A patent/CA1339688C/fr not_active Expired - Fee Related

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
RU2473541C2 (ru) *	2007-04-23	2013-01-27	Байер Кропсайенс Аг	Инсектицидные арилпирролидины
RU2473541C9 (ru) *	2007-04-23	2013-06-20	Байер Кропсайенс Аг	Инсектицидные арилпирролидины
US8980937B2 (en)	2007-04-23	2015-03-17	Bayer Cropscience Ag	Insecticidal aryl pyrrolidines
US9266830B2 (en)	2007-04-23	2016-02-23	Bayer Intellectual Property Gmbh	Pesticidal arylpyrrolidines

Legal Events

Date	Code	Title	Description
2009-02-24	MKLA	Lapsed

Publication	Publication Date	Title
CA1337657C (fr)	1995-11-28	3,4,5,6-tetrahydrophtalamides substitues en n et leurs intermediaires
US4424363A (en)	1984-01-03	Substituted 3-aminopyrazoles
CA1145748A (fr)	1983-05-03	Derives de 4h-3,1-benzoxazine
US4933001A (en)	1990-06-12	Phenylalkenylcarboxylic acids and their esters
CS227322B2 (en)	1984-04-16	Herbicide and method of preparing active substance thereof
US5744425A (en)	1998-04-28	Saccharin derivatives
CH630615A5 (fr)	1982-06-30	Derives d'imidazole a proprietes herbicides.
US4523946A (en)	1985-06-18	Substituted 4,5-dimethoxypyridazones and their use for controlling undesirable plant growth
CA1231954A (fr)	1988-01-26	3-phenyl-4-methoxycarbonylpyrazoles, et leur emploi pour la repression des vegetations indesirables
US4981971A (en)	1991-01-01	Certain aromatic or heterocyclic mercapto-alkylene-cyclohexene dione intermediates
US5013354A (en)	1991-05-07	3-phenylpropionic acid derivatives
US4844733A (en)	1989-07-04	Herbicidal N-aryltetrahydrophthalimide derivatives
US4566900A (en)	1986-01-28	Aniline derivatives and their use for controlling undesirable plant growth
US5237089A (en)	1993-08-17	Nitro or amino substituted phenylalkyl or phenylalkenyl carboxylic acid derivatives
DE3329017A1 (de)	1985-02-28	Cyclohexan-1,3-dionderivate, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung unerwuenschten pflanzenwuchses
US5009701A (en)	1991-04-23	5-(N-3,4,5,6-tetrahydrophthalimido)cinnamic acid derivatives
US5716906A (en)	1998-02-10	Saccharin derivatives
US5723415A (en)	1998-03-03	5-hydroxypyrazol-4-ylcarbonyl-substituted saccharin derivatives
US4844729A (en)	1989-07-04	Substituted N-phenylpyridazone derivatives
US5074904A (en)	1991-12-24	Naphthindazole-4,9-quinones and use thereof for controlling undesirable plant growth
CA1269987A (fr)	1990-06-05	Thiazolylamides, leur preparation, et leur emploi pour la repression de la vegetation indesirable
US4522646A (en)	1985-06-11	3,7-Dichloroquinoline derivatives and their use for controlling undesirable plant growth
US5356860A (en)	1994-10-18	Styrene derivatives useful as herbicides and defoliants
CA2197121A1 (fr)	1996-02-22	Derives de la saccharine
EP0834503B1 (fr)	2001-06-27	Tétrahydrophtalimides, leur préparation et utilisation