DK168599B1 - Herbicidt aktive dihydroimidazopyrrolopyridiner, en fremgangsmåde til deres fremstilling og en fremgangsmåde til bekæmpelse af uønskede en- og tokimbladede plantearter samt en herbicid sammensætning - Google Patents

Herbicidt aktive dihydroimidazopyrrolopyridiner, en fremgangsmåde til deres fremstilling og en fremgangsmåde til bekæmpelse af uønskede en- og tokimbladede plantearter samt en herbicid sammensætning Download PDF

Info

Publication number: DK168599B1
Authority: DK; Denmark
Prior art keywords: ooo; oooooo; alkyl; hydrogen; halogen
Prior art date: 1983-08-02

Application number

DK373884A

Other languages

Danish (da)

English (en)

Other versions

DK373884A (da

DK373884D0 (da

Inventor

Marinus Los

Original Assignee

American Cyanamid Co

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.)

1983-08-02

Filing date

1984-08-01

Publication date

1994-05-02

1984-08-01 Application filed by American Cyanamid Co filed Critical American Cyanamid Co

1984-08-01 Publication of DK373884D0 publication Critical patent/DK373884D0/da

1985-02-03 Publication of DK373884A publication Critical patent/DK373884A/da

1994-05-02 Application granted granted Critical

1994-05-02 Publication of DK168599B1 publication Critical patent/DK168599B1/da

Links

239000000203 mixture Substances 0.000 title claims description 94
238000000034 method Methods 0.000 title claims description 49
230000002363 herbicidal effect Effects 0.000 title claims description 25
241000196324 Embryophyta Species 0.000 title claims description 23
238000002360 preparation method Methods 0.000 title claims description 14
230000008569 process Effects 0.000 title claims description 9
150000001875 compounds Chemical class 0.000 claims description 136
229910052739 hydrogen Inorganic materials 0.000 claims description 53
239000001257 hydrogen Substances 0.000 claims description 50
239000007787 solid Substances 0.000 claims description 47
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 45
-1 alkoxyphenyl hydrogen Chemical compound 0.000 claims description 45
150000002431 hydrogen Chemical class 0.000 claims description 36
125000000217 alkyl group Chemical group 0.000 claims description 33
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
229910052736 halogen Inorganic materials 0.000 claims description 28
150000002367 halogens Chemical group 0.000 claims description 27
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 25
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
125000005843 halogen group Chemical group 0.000 claims description 15
125000003545 alkoxy group Chemical group 0.000 claims description 14
239000004009 herbicide Substances 0.000 claims description 12
229910052717 sulfur Chemical group 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 11
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 10
229910052760 oxygen Inorganic materials 0.000 claims description 10
125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 9
230000003287 optical effect Effects 0.000 claims description 9
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
125000003302 alkenyloxy group Chemical group 0.000 claims description 7
125000003282 alkyl amino group Chemical group 0.000 claims description 7
125000004414 alkyl thio group Chemical group 0.000 claims description 7
125000005133 alkynyloxy group Chemical group 0.000 claims description 7
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
229910052799 carbon Inorganic materials 0.000 claims description 7
239000007788 liquid Substances 0.000 claims description 7
239000001301 oxygen Substances 0.000 claims description 7
239000002689 soil Substances 0.000 claims description 7
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
239000011593 sulfur Chemical group 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
125000005037 alkyl phenyl group Chemical group 0.000 claims description 4
125000000068 chlorophenyl group Chemical group 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
230000001902 propagating effect Effects 0.000 claims description 4
125000003944 tolyl group Chemical group 0.000 claims description 4
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 3
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
125000005036 alkoxyphenyl group Chemical group 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
239000012038 nucleophile Substances 0.000 claims description 3
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
231100000252 nontoxic Toxicity 0.000 claims description 2
230000003000 nontoxic effect Effects 0.000 claims description 2
210000000056 organ Anatomy 0.000 claims description 2
125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 2
150000001721 carbon Chemical group 0.000 claims 2
ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 claims 1
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims 1
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
239000003085 diluting agent Substances 0.000 claims 1
125000001188 haloalkyl group Chemical group 0.000 claims 1
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 claims 1
229910000103 lithium hydride Inorganic materials 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 94
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 78
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 74
239000000460 chlorine Substances 0.000 description 73
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 72
239000000243 solution Substances 0.000 description 64
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 61
238000006243 chemical reaction Methods 0.000 description 57
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 56
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 54
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
229910001868 water Inorganic materials 0.000 description 43
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 38
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
DTAFLBZLAZYRDX-UHFFFAOYSA-N OOOOOO Chemical compound OOOOOO DTAFLBZLAZYRDX-UHFFFAOYSA-N 0.000 description 33
RTYZCUMXOXNVSI-UHFFFAOYSA-N OOOOOOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOOOOOO RTYZCUMXOXNVSI-UHFFFAOYSA-N 0.000 description 32
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
239000011541 reaction mixture Substances 0.000 description 30
239000002904 solvent Substances 0.000 description 28
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
239000002253 acid Substances 0.000 description 24
239000000047 product Substances 0.000 description 24
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical class OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 23
238000010992 reflux Methods 0.000 description 20
PWTOMWQKTVMNMM-UHFFFAOYSA-N OOOOOOOOOOOOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOOOOOOOOOOOO PWTOMWQKTVMNMM-UHFFFAOYSA-N 0.000 description 19
150000002148 esters Chemical class 0.000 description 18
238000003756 stirring Methods 0.000 description 18
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 17
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 17
235000001968 nicotinic acid Nutrition 0.000 description 17
238000012360 testing method Methods 0.000 description 17
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
240000008042 Zea mays Species 0.000 description 15
RSPISYXLHRIGJD-UHFFFAOYSA-N OOOO Chemical compound OOOO RSPISYXLHRIGJD-UHFFFAOYSA-N 0.000 description 14
235000002017 Zea mays subsp mays Nutrition 0.000 description 14
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 14
229910000041 hydrogen chloride Inorganic materials 0.000 description 14
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 12
239000011664 nicotinic acid Substances 0.000 description 12
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 12
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 11
101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 11
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 11
238000002425 crystallisation Methods 0.000 description 11
230000008025 crystallization Effects 0.000 description 11
GJAWHXHKYYXBSV-UHFFFAOYSA-N quinolinic acid Chemical class OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 description 11
239000007858 starting material Substances 0.000 description 11
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 10
235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 10
239000002585 base Substances 0.000 description 10
238000001914 filtration Methods 0.000 description 10
235000009973 maize Nutrition 0.000 description 10
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 10
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
239000000741 silica gel Substances 0.000 description 10
229910002027 silica gel Inorganic materials 0.000 description 10
235000010469 Glycine max Nutrition 0.000 description 9
244000068988 Glycine max Species 0.000 description 9
125000005336 allyloxy group Chemical group 0.000 description 9
229910052794 bromium Inorganic materials 0.000 description 9
239000000284 extract Substances 0.000 description 9
239000000463 material Substances 0.000 description 9
229910052757 nitrogen Inorganic materials 0.000 description 9
239000001632 sodium acetate Substances 0.000 description 9
235000017281 sodium acetate Nutrition 0.000 description 9
YCPQUHCGFDFLSI-UHFFFAOYSA-N 2-amino-2,3-dimethylbutanamide Chemical compound CC(C)C(C)(N)C(N)=O YCPQUHCGFDFLSI-UHFFFAOYSA-N 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
240000005979 Hordeum vulgare Species 0.000 description 8
235000007340 Hordeum vulgare Nutrition 0.000 description 8
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
239000012298 atmosphere Substances 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 8
QQVDYSUDFZZPSU-UHFFFAOYSA-M chloromethylidene(dimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)=CCl QQVDYSUDFZZPSU-UHFFFAOYSA-M 0.000 description 8
238000001816 cooling Methods 0.000 description 8
229910052740 iodine Inorganic materials 0.000 description 8
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 8
229910052753 mercury Inorganic materials 0.000 description 8
150000003839 salts Chemical class 0.000 description 8
239000008096 xylene Substances 0.000 description 8
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
239000002244 precipitate Substances 0.000 description 7
150000003222 pyridines Chemical class 0.000 description 7
230000009467 reduction Effects 0.000 description 7
238000006722 reduction reaction Methods 0.000 description 7
239000012279 sodium borohydride Substances 0.000 description 7
239000000725 suspension Substances 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 6
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
AZRRZGIBBLWSSQ-UHFFFAOYSA-N 4-ethyl-7-phenyl-3,5-diazabicyclo[2.2.2]octane-2,6-dione Chemical compound N1C(=O)C2C(=O)NC1(CC)CC2C1=CC=CC=C1 AZRRZGIBBLWSSQ-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
244000025254 Cannabis sativa Species 0.000 description 6
UIQWBVPFHHQZHH-UHFFFAOYSA-N OOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOO UIQWBVPFHHQZHH-UHFFFAOYSA-N 0.000 description 6
CQGRLHBOVUGVEA-UHFFFAOYSA-N OOOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOOO CQGRLHBOVUGVEA-UHFFFAOYSA-N 0.000 description 6
240000007594 Oryza sativa Species 0.000 description 6
235000007164 Oryza sativa Nutrition 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
239000007795 chemical reaction product Substances 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
239000008187 granular material Substances 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
239000000543 intermediate Substances 0.000 description 6
239000012044 organic layer Substances 0.000 description 6
229910000033 sodium borohydride Inorganic materials 0.000 description 6
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
238000003786 synthesis reaction Methods 0.000 description 6
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 5
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 5
241000219144 Abutilon Species 0.000 description 5
244000299507 Gossypium hirsutum Species 0.000 description 5
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
KUGRPPRAQNPSQD-UHFFFAOYSA-N OOOOO Chemical compound OOOOO KUGRPPRAQNPSQD-UHFFFAOYSA-N 0.000 description 5
FYKAKDPHDGCKTF-UHFFFAOYSA-N OOOOOOOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOOOOOOO FYKAKDPHDGCKTF-UHFFFAOYSA-N 0.000 description 5
150000001299 aldehydes Chemical class 0.000 description 5
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 5
239000012043 crude product Substances 0.000 description 5
238000005520 cutting process Methods 0.000 description 5
VHILMKFSCRWWIJ-UHFFFAOYSA-N dimethyl acetylenedicarboxylate Chemical compound COC(=O)C#CC(=O)OC VHILMKFSCRWWIJ-UHFFFAOYSA-N 0.000 description 5
YWDOHLFCHGYVJF-UHFFFAOYSA-N dimethyl thieno[3,2-b]pyridine-5,6-dicarboxylate Chemical compound N1=C(C(=O)OC)C(C(=O)OC)=CC2=C1C=CS2 YWDOHLFCHGYVJF-UHFFFAOYSA-N 0.000 description 5
230000000694 effects Effects 0.000 description 5
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 5
239000011777 magnesium Substances 0.000 description 5
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 5
235000009566 rice Nutrition 0.000 description 5
239000011734 sodium Substances 0.000 description 5
229910052720 vanadium Inorganic materials 0.000 description 5
WRFWAYDBNCOWRA-UHFFFAOYSA-N 3,4-dichloro-1-(6-iodo-4-oxo-2-thiophen-2-ylquinazolin-3-yl)pyrrole-2,5-dione Chemical compound O=C1C(Cl)=C(Cl)C(=O)N1N1C(=O)C2=CC(I)=CC=C2N=C1C1=CC=CS1 WRFWAYDBNCOWRA-UHFFFAOYSA-N 0.000 description 4
235000007320 Avena fatua Nutrition 0.000 description 4
235000016068 Berberis vulgaris Nutrition 0.000 description 4
241000335053 Beta vulgaris Species 0.000 description 4
241001049165 Caria Species 0.000 description 4
229920000742 Cotton Polymers 0.000 description 4
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
244000058871 Echinochloa crus-galli Species 0.000 description 4
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 4
238000005481 NMR spectroscopy Methods 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
241000005601 Trisetum Species 0.000 description 4
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
239000013543 active substance Substances 0.000 description 4
229910052783 alkali metal Inorganic materials 0.000 description 4
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
238000004440 column chromatography Methods 0.000 description 4
235000005822 corn Nutrition 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
LIYSYIKDUZFTJS-UHFFFAOYSA-N furo[3,2-b]pyridine-6-carboxylic acid Chemical class OC(=O)C1=CN=C2C=COC2=C1 LIYSYIKDUZFTJS-UHFFFAOYSA-N 0.000 description 4
YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 4
229910052500 inorganic mineral Inorganic materials 0.000 description 4
235000010755 mineral Nutrition 0.000 description 4
239000011707 mineral Substances 0.000 description 4
238000002156 mixing Methods 0.000 description 4
230000020477 pH reduction Effects 0.000 description 4
229910052700 potassium Inorganic materials 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
238000000746 purification Methods 0.000 description 4
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NBGMRMDAEWWFIR-UHFFFAOYSA-N imidazole-2-thione Chemical compound S=C1N=CC=N1 NBGMRMDAEWWFIR-UHFFFAOYSA-N 0.000 description 1
MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
229910003480 inorganic solid Inorganic materials 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
235000000396 iron Nutrition 0.000 description 1
ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 description 1
230000001795 light effect Effects 0.000 description 1
235000014666 liquid concentrate Nutrition 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
230000036244 malformation Effects 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
RDBBFJAPMNVENH-UHFFFAOYSA-N methyl 1h-pyrazolo[4,3-b]pyridine-5-carboxylate Chemical compound COC(=O)C1=CC=C2NN=CC2=N1 RDBBFJAPMNVENH-UHFFFAOYSA-N 0.000 description 1
FSTMRKLYWAJEGR-UHFFFAOYSA-N methyl 2-(4,5-dihydro-1h-imidazol-2-yl)furo[3,2-b]pyridine-6-carboxylate Chemical class O1C2=CC(C(=O)OC)=CN=C2C=C1C1=NCCN1 FSTMRKLYWAJEGR-UHFFFAOYSA-N 0.000 description 1
YGJJDFDGVZKGKZ-UHFFFAOYSA-N methyl 2-(4-methyl-5-oxo-4-propan-2-ylimidazol-1-yl)pyridine-3-carboxylate Chemical compound COC(=O)C1=CC=CN=C1N1C(=O)C(C)(C(C)C)N=C1 YGJJDFDGVZKGKZ-UHFFFAOYSA-N 0.000 description 1
RDKAWHKZHJUEAE-UHFFFAOYSA-N methyl 2-(acetyloxymethyl)-1-oxidopyridin-1-ium-3-carboxylate Chemical compound COC(=O)C1=CC=C[N+]([O-])=C1COC(C)=O RDKAWHKZHJUEAE-UHFFFAOYSA-N 0.000 description 1
QJIBXDDKGOFLCH-UHFFFAOYSA-N methyl 2-(diacetyloxymethyl)pyridine-3-carboxylate Chemical compound COC(=O)C1=CC=CN=C1C(OC(C)=O)OC(C)=O QJIBXDDKGOFLCH-UHFFFAOYSA-N 0.000 description 1
WKIMDXSTGOQVOQ-UHFFFAOYSA-N methyl 2-(hydroxymethyl)pyridine-3-carboxylate Chemical class COC(=O)C1=CC=CN=C1CO WKIMDXSTGOQVOQ-UHFFFAOYSA-N 0.000 description 1
OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
DEUNNRRXGAUDMY-UHFFFAOYSA-N methyl 5-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)furo[3,2-b]pyridine-6-carboxylate Chemical compound COC(=O)C1=CC=2OC=CC=2N=C1C1=NC(C)(C(C)C)C(=O)N1 DEUNNRRXGAUDMY-UHFFFAOYSA-N 0.000 description 1
BZQPCCRDCIHBKX-UHFFFAOYSA-N methyl 5-(4-methyl-5-oxo-4-propan-2-ylimidazolidin-2-yl)furo[3,2-b]pyridine-6-carboxylate Chemical compound COC(=O)C1=CC=2OC=CC=2N=C1C1NC(=O)C(C)(C(C)C)N1 BZQPCCRDCIHBKX-UHFFFAOYSA-N 0.000 description 1
AYBNKSIMDHSACH-UHFFFAOYSA-N methyl 6-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)thieno[2,3-b]pyridine-5-carboxylate Chemical compound COC(=O)C1=CC=2C=CSC=2N=C1C1=NC(C)(C(C)C)C(=O)N1 AYBNKSIMDHSACH-UHFFFAOYSA-N 0.000 description 1
ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
MVVJMHXGMCIHNE-UHFFFAOYSA-N n-(2-formylthiophen-3-yl)acetamide Chemical compound CC(=O)NC=1C=CSC=1C=O MVVJMHXGMCIHNE-UHFFFAOYSA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
PVNIIMVLHYAWGP-UHFFFAOYSA-M nicotinate Chemical compound [O-]C(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-M 0.000 description 1
229960002715 nicotine Drugs 0.000 description 1
SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
229960003512 nicotinic acid Drugs 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
UYDLBVPAAFVANX-UHFFFAOYSA-N octylphenoxy polyethoxyethanol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(OCCOCCOCCOCCO)C=C1 UYDLBVPAAFVANX-UHFFFAOYSA-N 0.000 description 1
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
230000037361 pathway Effects 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
239000012071 phase Substances 0.000 description 1
RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 1
238000004382 potting Methods 0.000 description 1
230000002265 prevention Effects 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
YWMLAVTVQMSPBB-UHFFFAOYSA-N propan-2-yl n-thiophen-3-ylcarbamate Chemical compound CC(C)OC(=O)NC=1C=CSC=1 YWMLAVTVQMSPBB-UHFFFAOYSA-N 0.000 description 1
AUBWNDVGMWLNSU-UHFFFAOYSA-N propan-2-yl thiophene-3-carboxylate Chemical compound CC(C)OC(=O)C=1C=CSC=1 AUBWNDVGMWLNSU-UHFFFAOYSA-N 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
LOAUVZALPPNFOQ-UHFFFAOYSA-M quinaldate Chemical compound C1=CC=CC2=NC(C(=O)[O-])=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-M 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
239000004576 sand Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000002002 slurry Substances 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
239000012265 solid product Substances 0.000 description 1
238000009331 sowing Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006277 sulfonation reaction Methods 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
235000013616 tea Nutrition 0.000 description 1
FBWNMEQMRUMQSO-UHFFFAOYSA-N tergitol NP-9 Chemical compound CCCCCCCCCC1=CC=C(OCCOCCOCCOCCOCCOCCOCCOCCOCCO)C=C1 FBWNMEQMRUMQSO-UHFFFAOYSA-N 0.000 description 1
IRFHMTUHTBSEBK-QGZVFWFLSA-N tert-butyl n-[(2s)-2-(2,5-difluorophenyl)-3-quinolin-3-ylpropyl]carbamate Chemical compound C1([C@H](CC=2C=C3C=CC=CC3=NC=2)CNC(=O)OC(C)(C)C)=CC(F)=CC=C1F IRFHMTUHTBSEBK-QGZVFWFLSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
KKYDMQCDYWKQTJ-UHFFFAOYSA-N thieno[2,3-b]pyridine-2,3-dicarboxylic acid Chemical class C1=CC=C2C(C(O)=O)=C(C(=O)O)SC2=N1 KKYDMQCDYWKQTJ-UHFFFAOYSA-N 0.000 description 1
SVLWTDXNOASIRL-UHFFFAOYSA-N thieno[3,2-b]pyridine-2,3-dicarboxylic acid Chemical class C1=CN=C2C(C(O)=O)=C(C(=O)O)SC2=C1 SVLWTDXNOASIRL-UHFFFAOYSA-N 0.000 description 1
WEYMRIJRWNCSFV-UHFFFAOYSA-N thieno[3,2-b]pyridine-6-carboxylic acid Chemical group OC(=O)C1=CN=C2C=CSC2=C1 WEYMRIJRWNCSFV-UHFFFAOYSA-N 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
GLQWRXYOTXRDNH-UHFFFAOYSA-N thiophen-2-amine Chemical class NC1=CC=CS1 GLQWRXYOTXRDNH-UHFFFAOYSA-N 0.000 description 1
125000000464 thioxo group Chemical group S=* 0.000 description 1
244000045561 useful plants Species 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/14—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Wood Science & Technology (AREA)
Environmental Sciences (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Agronomy & Crop Science (AREA)
Zoology (AREA)
Pest Control & Pesticides (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Pyridine Compounds (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

DK373884A 1983-08-02 1984-08-01 Herbicidt aktive dihydroimidazopyrrolopyridiner, en fremgangsmåde til deres fremstilling og en fremgangsmåde til bekæmpelse af uønskede en- og tokimbladede plantearter samt en herbicid sammensætning DK168599B1 (da)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US51960383A	1983-08-02	1983-08-02
US51960383		1983-08-02

Publications (3)

Publication Number	Publication Date
DK373884D0 DK373884D0 (da)	1984-08-01
DK373884A DK373884A (da)	1985-02-03
DK168599B1 true DK168599B1 (da)	1994-05-02

Family

ID=24069013

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
DK373884A DK168599B1 (da)	1983-08-02	1984-08-01	Herbicidt aktive dihydroimidazopyrrolopyridiner, en fremgangsmåde til deres fremstilling og en fremgangsmåde til bekæmpelse af uønskede en- og tokimbladede plantearter samt en herbicid sammensætning
DK232790A DK170703B1 (da)	1983-08-02	1990-09-26	Imidazopyrrolopyridiner

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
DK232790A DK170703B1 (da)	1983-08-02	1990-09-26	Imidazopyrrolopyridiner

Country Status (15)

Country	Link
EP (2)	EP0133309B1 (de)
JP (2)	JPH0670054B2 (de)
KR (1)	KR900004996B1 (de)
AR (1)	AR241812A1 (de)
AT (2)	ATE80631T1 (de)
AU (1)	AU570256B2 (de)
BR (1)	BR8403838A (de)
CA (1)	CA1337349C (de)
DE (2)	DE3485928T2 (de)
DK (2)	DK168599B1 (de)
ES (1)	ES8604221A1 (de)
HU (2)	HU196999B (de)
IL (1)	IL72601A (de)
YU (2)	YU45904B (de)
ZA (1)	ZA845959B (de)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NZ208327A (en) *	1983-06-02	1988-04-29	American Cyanamid Co	(2-imidazolin-2-yl)-thieno- and furo-(2,3-b) and (2,3-b)pyridine derivatives and herbicidal compositions
EP0133310B1 (de) *	1983-08-02	1988-09-14	American Cyanamid Company	Imidazolinone und Imidazolidinthione, Verfahren zu deren Herstellung und Verwendung dieser Verbindungen als Herbizide
EP0133311A3 (de) *	1983-08-02	1987-12-23	American Cyanamid Company	Substituierte Imidazolinylbenzoesäuren, Ester und Salze sowie ihre Verwendung als Herbizide
EP0166907A3 (de) *	1984-06-04	1988-09-14	American Cyanamid Company	Herbizide 2-(2-Imidazolin-2-yl)-fluoralkoxy-, -alkenyloxy- und -alkinyloxypyridine und -chinoline
DE3520390A1 (de) *	1984-07-07	1986-02-06	Bayer Ag, 5090 Leverkusen	Imidazo-pyrrolo-pyridin-derivate
EP0183993A3 (de) *	1984-11-16	1987-12-09	F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft	2H-Imidazo[1',2':1,2]pyrrolo[3,4-b]pyridine und deren Verwendung als Unkrautbekämpfungsmittel
EP0195745B1 (de) *	1985-03-12	1990-09-12	Ciba-Geigy Ag	Heterocyclisch kondensierte Pyridin-Verbindungen als Herbizide
US4851029A (en) *	1985-08-23	1989-07-25	Ciba-Geigy Corporation	Thiazolylalkyl esters of α-imidazolinonenicotinic acids and herbicidal methods of use
DE3534948A1 (de) *	1985-10-01	1987-04-09	Bayer Ag	Fungizide und wachstumsregulatorische mittel
ES2046167T3 (es) *	1985-12-13	1994-02-01	American Cyanamid Company	Procedimiento para la preparacion de composiciones herbicidas de (2-imidazolin-2-il)-heteropiridina condensadas.
DK41387A (da) *	1986-02-21	1987-08-22	Hoffmann La Roche	Glyphosatholdigt ukrudtsbekaempelsesmiddel
GB2174395A (en) *	1986-05-09	1986-11-05	American Cyanimid Co	Herbicidal 2-(2-imidazolin-2-yl)pyridine derivatives
DE3751524T2 (de) *	1986-07-28	1996-06-13	American Cyanamid Co	5(und/oder6) Substituierte 2-(2-Imidazolin-2-yl)nicotinsäuren, Ester und Salze, verwendbar als herbizide Mittel und Zwischenverbindungen für die Herstellung dieser Nikotinsäuren, Ester und Salze.
ES2052769T3 (es) *	1987-07-01	1994-07-16	Ciba Geigy Ag	Procedimiento para la obtencion de imidazolonas sustituidas con actividad herbicida.
EP0322616A3 (de) *	1987-12-31	1989-10-18	American Cyanamid Company	5- und/oder 6-substituierte 2(-imidazolinyl-2)-nicotinsäure, Ester und Salze, nützlich als Herbizide, und Zwischenverbindungen zur Herstellung von diesen Nicotinsäuren, Estern und Salzen
KR100893453B1 (ko) *	2002-09-24	2009-04-17	두산인프라코어 주식회사	축관통 냉각구조를 갖는 고속 회전 테이블
CN100415738C (zh) *	2004-12-21	2008-09-03	浙江工业大学	一种含吡唑双杂环化合物、制备方法及其应用

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4041045A (en) *	1975-11-12	1977-08-09	American Cyanamid Company	Dihydroimidaz oisoindolediones and the use thereof as herbicidal agents
US4017510A (en) *	1975-11-12	1977-04-12	American Cyanamid Company	Imidazoisoindolediones and the use thereof as herbicidal agents
GB1547660A (en) *	1976-12-23	1979-06-27	American Cyanamid Co	Substituted dihydroimidazoisoindoles and their use as herbicides
US4188487A (en) *	1977-08-08	1980-02-12	American Cyanamid Company	Imidazolinyl benzoic acids, esters and salts and their use as herbicidal agents
IL62794A0 (en) *	1980-06-02	1981-07-31	American Cyanamid Co	Substituted nicotinic acid esters and salts thereof and their use as herbicidal agents
IN153523B (de) *	1980-06-02	1984-07-21	American Cyanamid Co
JPS5724369A (en) *	1980-07-19	1982-02-08	Tokyo Kinzoku Kogyo Kk	Pyrimidine derivative and its preparation
EP0133311A3 (de) *	1983-08-02	1987-12-23	American Cyanamid Company	Substituierte Imidazolinylbenzoesäuren, Ester und Salze sowie ihre Verwendung als Herbizide

1984
- 1984-02-08 AR AR84297446A patent/AR241812A1/es active
- 1984-07-27 EP EP84108921A patent/EP0133309B1/de not_active Expired
- 1984-07-27 AT AT88101870T patent/ATE80631T1/de not_active IP Right Cessation
- 1984-07-27 AT AT84108921T patent/ATE48134T1/de not_active IP Right Cessation
- 1984-07-27 EP EP88101870A patent/EP0277661B1/de not_active Expired - Lifetime
- 1984-07-27 DE DE8888101870T patent/DE3485928T2/de not_active Expired - Fee Related
- 1984-07-27 DE DE8484108921T patent/DE3480541D1/de not_active Expired
- 1984-07-31 CA CA000460059A patent/CA1337349C/en not_active Expired - Fee Related
- 1984-08-01 DK DK373884A patent/DK168599B1/da not_active IP Right Cessation
- 1984-08-01 ZA ZA845959A patent/ZA845959B/xx unknown
- 1984-08-01 AU AU31392/84A patent/AU570256B2/en not_active Ceased
- 1984-08-01 YU YU135784A patent/YU45904B/sh unknown
- 1984-08-01 BR BR8403838A patent/BR8403838A/pt not_active IP Right Cessation
- 1984-08-01 KR KR1019840004596A patent/KR900004996B1/ko not_active Expired
- 1984-08-01 ES ES534790A patent/ES8604221A1/es not_active Expired
- 1984-08-02 JP JP59161663A patent/JPH0670054B2/ja not_active Expired - Lifetime
- 1984-08-02 HU HU842946A patent/HU196999B/hu not_active IP Right Cessation
- 1984-08-02 HU HU885805A patent/HU199472B/hu not_active IP Right Cessation
- 1984-08-06 IL IL72601A patent/IL72601A/xx not_active IP Right Cessation
1986
- 1986-11-19 YU YU197986A patent/YU45805B/sh unknown
1990
- 1990-09-26 DK DK232790A patent/DK170703B1/da not_active IP Right Cessation
1993
- 1993-05-24 JP JP5144277A patent/JPH0714933B2/ja not_active Expired - Lifetime

Also Published As

Publication number	Publication date
DE3485928T2 (de)	1993-03-25
AR241812A1 (es)	1992-12-30
JPH0670054B2 (ja)	1994-09-07
DK232790A (da)	1990-09-26
JPH06116264A (ja)	1994-04-26
ZA845959B (en)	1985-03-27
JPS6069083A (ja)	1985-04-19
DE3485928D1 (de)	1992-10-22
DK373884A (da)	1985-02-03
BR8403838A (pt)	1985-07-09
YU135784A (en)	1987-02-28
DE3480541D1 (en)	1989-12-28
EP0277661B1 (de)	1992-09-16
HU196999B (en)	1989-02-28
DK373884D0 (da)	1984-08-01
KR850001755A (ko)	1985-04-01
AU3139284A (en)	1985-02-07
EP0133309B1 (de)	1989-11-23
ATE48134T1 (de)	1989-12-15
AU570256B2 (en)	1988-03-10
IL72601A (en)	1990-04-29
YU197986A (en)	1988-04-30
HU199472B (en)	1990-02-28
CA1337349C (en)	1995-10-17
EP0277661A1 (de)	1988-08-10
DK170703B1 (da)	1995-12-11
HUT36679A (en)	1985-10-28
ATE80631T1 (de)	1992-10-15
KR900004996B1 (ko)	1990-07-16
YU45805B (sh)	1992-07-20
EP0133309A1 (de)	1985-02-20
ES8604221A1 (es)	1986-02-01
DK232790D0 (da)	1990-09-26
YU45904B (sh)	1992-09-07
IL72601A0 (en)	1984-11-30
JPH0714933B2 (ja)	1995-02-22
ES534790A0 (es)	1986-02-01

Legal Events

Date	Code	Title	Description
1994-05-02	B1	Patent granted (law 1993)
2000-04-10	PBP	Patent lapsed

Publication	Publication Date	Title
FI76082C (fi)	1988-09-09	2-(2-imidazolin-2-yl)pyridiner och -kinoliner, foerfarande foer deras framstaellning och deras anvaendning som herbicider.
US6444617B1 (en)	2002-09-03	Fused-heterocycle dicarboxylic acid diamide derivatives or salts thereof, herbicide and usage thereof
DK170703B1 (da)	1995-12-11	Imidazopyrrolopyridiner
EP0770076A1 (de)	1997-05-02	Benzokondensierte fünfgliedrig heterocyclische carboxamidderivate als 5ht2b/2c -rezeptorantagonisten
EP0254951B1 (de)	1995-09-20	5(und/oder6) Substituierte 2-(2-Imidazolin-2-yl)nicotinsäuren, Ester und Salze, verwendbar als herbizide Mittel und Zwischenverbindungen für die Herstellung dieser Nikotinsäuren, Ester und Salze
US4701208A (en)	1987-10-20	Dihydroimidazopyrrolopyridine, quinoline, thieno- and furo[2,3-b]pyridine, dihydrothieno- and furo[2,3-b]-pyridine, thieno- and furo[3,2-b]pyridine and dihydrothieno- and furo[3,2-b]pyridine herbicides and method for preparation thereof
EP0227932B1 (de)	1993-01-13	Neue kondensierte Pyridinverbindungen, Zwischenverbindungen für die Herstellung und ihre Verwendung als herbizide Wirkstoffe
BG60497B2 (bg)	1995-05-31	Семикарбазони и тиосемикарбазони
RU2058313C1 (ru)	1996-04-20	Производные (2-имидазолин-2-ил)-тиено или фуро(3,2-в) пиридин карбоновой кислоты, гербицидная композиция, ингредиенты для их получения
CA1256439A (en)	1989-06-27	Imidazolidinones, and imidazolidine-thiones, process and intermediates for the preparation thereof, and use of said compounds as herbicidal agents
US4752323A (en)	1988-06-21	(2-imidazolin-2-yl)thieno- and furo[2,3-b] and [3,2-b]pyridines and use of said compounds as herbicidal agents
US4650514A (en)	1987-03-17	(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
CA1339315C (en)	1997-08-19	5h-imidazopyrrolopyridine, quinoline, thieno- and furopyridine, dihydrothieno- and furopyridine 2-5-diones
NO163056B (no)	1989-12-18	Analogifremgangsmaate for fremstilling av terapeutisk aktive pyrazolo (3,4-d) - pyridin-3-on-derivater.
NO301012B1 (no)	1997-09-01	Fremgangsmåte for fremstilling av benzo£b\|naftyridiner
CA1272728A (en)	1990-08-14	Substituted thieno-and furoimidazopyrrolspyridinedione compounds having herbicidal activity
JPS62123185A (ja)	1987-06-04	２−（２−イミダゾリン−２−イル）−ピリジン−３−カルボン酸誘導体、その製法及びこれを含有する除草剤
US4920226A (en)	1990-04-24	Intermediates for the preparation of (2-imidazolin-2-yl)thieno- and furo(2,3-b) and (3,2-b) pyridines
KR900006860B1 (ko)	1990-09-22	신규(2-이미다졸린-2-일) 융합 헤테로피리딘 화합물
SI8411356A8 (sl)	1995-12-31	Postopek za pridobivanje imidazolidinonov in imidazolidintionov