DD256449A5 - Pyrazolo(3,4-b)pyridinderivate enthaltende mittel mit herbizider wirkung - Google Patents

Pyrazolo(3,4-b)pyridinderivate enthaltende mittel mit herbizider wirkung Download PDF

Info

Publication number: DD256449A5
Authority: DD; German Democratic Republic
Prior art keywords: radical; alkyl; alkoxy; hydrogen atom; substituted
Prior art date: 1986-05-16

Application number

DD87302780A

Other languages

German (de)

English (en)

Inventor

Erhard Nordhoff

Wilfried Franke

Friedrich Arndt

Clemens Koetter

Original Assignee

��@��k��

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.)

1986-05-16

Filing date

1987-05-14

Publication date

1988-05-11

1987-05-14 Application filed by ��@��k�� filed Critical ��@��k��

1988-05-11 Publication of DD256449A5 publication Critical patent/DD256449A5/de

Links

230000002363 herbicidal effect Effects 0.000 title abstract description 9
150000005230 pyrazolo[3,4-b]pyridines Chemical class 0.000 title description 4
239000000203 mixture Substances 0.000 claims abstract description 11
-1 C 3 -C 6 -cycloalkyl radical Chemical class 0.000 claims description 63
150000001875 compounds Chemical class 0.000 claims description 58
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 45
229910052736 halogen Inorganic materials 0.000 claims description 25
229910052799 carbon Inorganic materials 0.000 claims description 23
150000002367 halogens Chemical group 0.000 claims description 20
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
229910052760 oxygen Inorganic materials 0.000 claims description 16
239000001301 oxygen Substances 0.000 claims description 16
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
150000001768 cations Chemical class 0.000 claims description 14
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 9
239000002253 acid Substances 0.000 claims description 9
125000005843 halogen group Chemical group 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 9
125000004093 cyano group Chemical group *C#N 0.000 claims description 8
150000003254 radicals Chemical class 0.000 claims description 8
125000004434 sulfur atom Chemical group 0.000 claims description 8
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 7
229910052783 alkali metal Inorganic materials 0.000 claims description 5
150000001340 alkali metals Chemical class 0.000 claims description 5
150000003867 organic ammonium compounds Chemical class 0.000 claims description 5
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
125000002541 furyl group Chemical group 0.000 claims description 4
125000004430 oxygen atom Chemical group O* 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
KKFDJZZADQONDE-UHFFFAOYSA-N (hydridonitrato)hydroxidocarbon(.) Chemical compound O[C]=N KKFDJZZADQONDE-UHFFFAOYSA-N 0.000 claims description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 2
150000001204 N-oxides Chemical class 0.000 claims description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 claims description 2
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
150000001342 alkaline earth metals Chemical class 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000003282 alkyl amino group Chemical group 0.000 claims description 2
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
150000001721 carbon Chemical group 0.000 claims description 2
229910052802 copper Inorganic materials 0.000 claims description 2
239000010949 copper Substances 0.000 claims description 2
JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 claims description 2
125000005059 halophenyl group Chemical group 0.000 claims description 2
229910052742 iron Inorganic materials 0.000 claims description 2
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 2
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
125000006501 nitrophenyl group Chemical group 0.000 claims description 2
230000003287 optical effect Effects 0.000 claims description 2
125000000951 phenoxy group Chemical class [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
ZBZJXHCVGLJWFG-UHFFFAOYSA-N trichloromethyl(.) Chemical compound Cl[C](Cl)Cl ZBZJXHCVGLJWFG-UHFFFAOYSA-N 0.000 claims description 2
239000011701 zinc Substances 0.000 claims description 2
229910052725 zinc Inorganic materials 0.000 claims description 2
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 4
125000004970 halomethyl group Chemical group 0.000 claims 2
SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 claims 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims 1
125000000000 cycloalkoxy group Chemical group 0.000 claims 1
239000003795 chemical substances by application Substances 0.000 abstract description 13
239000000969 carrier Substances 0.000 abstract description 4
150000003222 pyridines Chemical class 0.000 abstract 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 71
229910052739 hydrogen Inorganic materials 0.000 description 32
241000196324 Embryophyta Species 0.000 description 31
238000000034 method Methods 0.000 description 25
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
238000006243 chemical reaction Methods 0.000 description 20
229910052757 nitrogen Inorganic materials 0.000 description 20
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 16
239000002904 solvent Substances 0.000 description 16
239000007858 starting material Substances 0.000 description 15
238000002360 preparation method Methods 0.000 description 14
239000004480 active ingredient Substances 0.000 description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
239000000047 product Substances 0.000 description 12
238000004458 analytical method Methods 0.000 description 11
239000000460 chlorine Substances 0.000 description 11
230000000694 effects Effects 0.000 description 11
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
235000010469 Glycine max Nutrition 0.000 description 9
239000001257 hydrogen Substances 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical class O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
230000006378 damage Effects 0.000 description 7
239000000243 solution Substances 0.000 description 7
244000068988 Glycine max Species 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000002585 base Substances 0.000 description 6
230000005764 inhibitory process Effects 0.000 description 6
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
230000008635 plant growth Effects 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
238000000354 decomposition reaction Methods 0.000 description 5
BMIJPENHOIPIPI-UHFFFAOYSA-N 2H-pyrazolo[3,4-b]pyridine-3,4-dicarboxylic acid Chemical class N1N=C(C2=C1N=CC=C2C(=O)O)C(=O)O BMIJPENHOIPIPI-UHFFFAOYSA-N 0.000 description 4
241000219144 Abutilon Species 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
235000011331 Brassica Nutrition 0.000 description 4
240000004658 Medicago sativa Species 0.000 description 4
235000010624 Medicago sativa Nutrition 0.000 description 4
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
238000009835 boiling Methods 0.000 description 4
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 4
150000004682 monohydrates Chemical class 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
239000000725 suspension Substances 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical class C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
NQDNEJQKMFVZER-UHFFFAOYSA-N 1-methyl-6-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)pyrazolo[3,4-b]pyridine-5-carboxylic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C(C(=C1)C(O)=O)=NC2=C1C=NN2C NQDNEJQKMFVZER-UHFFFAOYSA-N 0.000 description 3
239000005995 Aluminium silicate Substances 0.000 description 3
241000220243 Brassica sp. Species 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
244000058871 Echinochloa crus-galli Species 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
235000011999 Panicum crusgalli Nutrition 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
235000012480 Solanum sp Nutrition 0.000 description 3
241000209140 Triticum Species 0.000 description 3
235000021307 Triticum Nutrition 0.000 description 3
150000008065 acid anhydrides Chemical class 0.000 description 3
239000013543 active substance Substances 0.000 description 3
125000004414 alkyl thio group Chemical group 0.000 description 3
235000012211 aluminium silicate Nutrition 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
159000000007 calcium salts Chemical class 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000012954 diazonium Substances 0.000 description 3
150000001989 diazonium salts Chemical class 0.000 description 3
239000011737 fluorine Substances 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
230000012010 growth Effects 0.000 description 3
230000009036 growth inhibition Effects 0.000 description 3
239000004009 herbicide Substances 0.000 description 3
150000003840 hydrochlorides Chemical class 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
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 3
239000007788 liquid Substances 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000003921 oil Substances 0.000 description 3
235000019198 oils Nutrition 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
GJAWHXHKYYXBSV-UHFFFAOYSA-N quinolinic acid Chemical class OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 description 3
239000007787 solid Substances 0.000 description 3
NDKUWHHTBIIHGL-UHFFFAOYSA-N 1-methyl-pyrazolo[5,4-b]pyridine-5,6-dicarboxylic acid anhydride Chemical compound N1=C2N(C)N=CC2=CC2=C1C(=O)OC2=O NDKUWHHTBIIHGL-UHFFFAOYSA-N 0.000 description 2
FPJANZSAEGDDAS-UHFFFAOYSA-N 1-methylpyrazolo[3,4-b]pyridine-5,6-dicarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)N=C2N(C)N=CC2=C1 FPJANZSAEGDDAS-UHFFFAOYSA-N 0.000 description 2
CABMTIJINOIHOD-UHFFFAOYSA-N 2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]quinoline-3-carboxylic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC2=CC=CC=C2C=C1C(O)=O CABMTIJINOIHOD-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
244000075850 Avena orientalis Species 0.000 description 2
GGLOWSKDVXIRTL-UHFFFAOYSA-N C(C)OC(=O)C1=NNC=2N=CC=C(C21)C(=O)OCC Chemical compound C(C)OC(=O)C1=NNC=2N=CC=C(C21)C(=O)OCC GGLOWSKDVXIRTL-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
244000108484 Cyperus difformis Species 0.000 description 2
244000285774 Cyperus esculentus Species 0.000 description 2
235000005853 Cyperus esculentus Nutrition 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
235000012827 Digitaria sp Nutrition 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
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
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
244000042664 Matricaria chamomilla Species 0.000 description 2
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241000219823 Medicago Species 0.000 description 2
235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
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OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
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241000207763 Solanum Species 0.000 description 2
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239000003638 chemical reducing agent Substances 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
JDXYSCUOABNLIR-UHFFFAOYSA-N diethyl 2-oxobutanedioate Chemical compound CCOC(=O)CC(=O)C(=O)OCC JDXYSCUOABNLIR-UHFFFAOYSA-N 0.000 description 2
229940071094 diethyl oxalacetate Drugs 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
150000007857 hydrazones Chemical class 0.000 description 2
239000005457 ice water Substances 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
239000011630 iodine Substances 0.000 description 2
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
229920005610 lignin Polymers 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
239000011707 mineral Substances 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
238000002156 mixing Methods 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
230000001105 regulatory effect Effects 0.000 description 2
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
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239000012279 sodium borohydride Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
239000002689 soil Substances 0.000 description 2
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 2
150000003461 sulfonyl halides Chemical class 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 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 1
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KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical class O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 description 1
LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 description 1
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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
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Classifications

- 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
- C07D471/02—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 two hetero rings
- C07D471/04—Ortho-condensed systems
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

DD87302780A 1986-05-16 1987-05-14 Pyrazolo(3,4-b)pyridinderivate enthaltende mittel mit herbizider wirkung DD256449A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19863616849 DE3616849A1 (de)	1986-05-16	1986-05-16	Pyrazolo(3,4-b)pyridinderivate, verfahren und zwischenstufen zu ihrer herstellung und ihre verwendung als mittel mit herbizider wirkung

Publications (1)

Publication Number	Publication Date
DD256449A5 true DD256449A5 (de)	1988-05-11

Family

ID=6301174

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD87302780A DD256449A5 (de)	1986-05-16	1987-05-14	Pyrazolo(3,4-b)pyridinderivate enthaltende mittel mit herbizider wirkung

Country Status (15)

Country	Link
EP (1)	EP0245860A2 (fr)
JP (1)	JPS62277385A (fr)
KR (1)	KR870011133A (fr)
CN (1)	CN87103495A (fr)
AU (1)	AU7311087A (fr)
BR (1)	BR8702501A (fr)
DD (1)	DD256449A5 (fr)
DE (1)	DE3616849A1 (fr)
DK (1)	DK247787A (fr)
FI (1)	FI871980A7 (fr)
HU (1)	HUT44132A (fr)
IL (1)	IL82532A0 (fr)
PT (1)	PT84871B (fr)
TR (1)	TR24917A (fr)
ZA (1)	ZA873507B (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE202013105149U1 (de)	2013-11-14	2013-11-27	Igus Gmbh	Leitungsführung

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5252538A (en) *	1984-05-21	1993-10-12	American Cyanamid Company	(2-imidazolin-2-yl) fused heteropyridine compounds, intermediates for the preparation of and use of said compounds as herbicidal agents
US5565412A (en) *	1984-05-21	1996-10-15	American Cyanamid Co.	(2-imidazolin-2-yl) fused heteropyridine compounds, intermediates for the preparation of and use of said compounds as herbicidal agents
DE3929698A1 (de) *	1989-09-07	1991-03-14	Basf Ag	Triazolopyridinfarbstoffe sowie ein verfahren zum thermischen transfer von methinfarbstoffen
DE4212919C2 (de) *	1992-04-15	1998-04-16	Schering Ag	Anellierte Pyrazolylpyrazole, ihre Herstellung sowie Zwischenprodukte zu ihrer Herstellung und ihre Verwendung als Mittel mit herbizider Wirkung

1986
- 1986-05-16 DE DE19863616849 patent/DE3616849A1/de not_active Withdrawn
1987
- 1987-05-05 FI FI871980A patent/FI871980A7/fi not_active Application Discontinuation
- 1987-05-14 CN CN198787103495A patent/CN87103495A/zh active Pending
- 1987-05-14 EP EP87107010A patent/EP0245860A2/fr not_active Withdrawn
- 1987-05-14 DK DK247787A patent/DK247787A/da not_active Application Discontinuation
- 1987-05-14 IL IL82532A patent/IL82532A0/xx unknown
- 1987-05-14 DD DD87302780A patent/DD256449A5/de unknown
- 1987-05-15 HU HU872192A patent/HUT44132A/hu unknown
- 1987-05-15 ZA ZA873507A patent/ZA873507B/xx unknown
- 1987-05-15 BR BR8702501A patent/BR8702501A/pt unknown
- 1987-05-15 JP JP62117221A patent/JPS62277385A/ja active Pending
- 1987-05-15 AU AU73110/87A patent/AU7311087A/en not_active Abandoned
- 1987-05-15 TR TR87/0330A patent/TR24917A/xx unknown
- 1987-05-15 PT PT84871A patent/PT84871B/pt unknown
- 1987-05-16 KR KR870004848A patent/KR870011133A/ko not_active Withdrawn

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE202013105149U1 (de)	2013-11-14	2013-11-27	Igus Gmbh	Leitungsführung

Also Published As

Publication number	Publication date
EP0245860A2 (fr)	1987-11-19
ZA873507B (en)	1987-11-09
TR24917A (tr)	1992-07-21
FI871980A0 (fi)	1987-05-05
IL82532A0 (en)	1987-11-30
DE3616849A1 (de)	1987-11-19
JPS62277385A (ja)	1987-12-02
DK247787D0 (da)	1987-05-14
PT84871A (de)	1987-06-01
DK247787A (da)	1987-11-17
CN87103495A (zh)	1987-12-09
AU7311087A (en)	1987-11-19
HUT44132A (en)	1988-02-29
KR870011133A (ko)	1987-12-21
FI871980A7 (fi)	1987-11-17
BR8702501A (pt)	1988-02-23
PT84871B (de)	1989-07-10

Publication	Publication Date	Title
DE3722072A1 (de)	1989-01-12	6,7-dihydro-pyrazolo(1,5-a)(1,3,5) triazin-2-sulfonsaeureamide, verfahren zu ihrer herstellung und ihre verwendung als mittel mit herbizider und pflanzenwuchsregulierender wirkung
EP0303573B1 (fr)	1993-06-09	Pyrrolidinediones-2,5 et tétrahydro-4,5,6,7 isoindolediones-1,3
EP0216360A2 (fr)	1987-04-01	Dérivés d'imidazoline, leur procédé de préparation et agents avec activité herbicide les contenant
DE3825041A1 (de)	1990-02-15	Pyrido(3,2-e)(1,2,4)triazolo(1,5-a)pyrimidin- 2-sulfonsaeureamide, verfahren zu ihrer herstellung und ihre verwendung als mittel mit herbizider, pflanzenwachstumsregulierender und fungizider wirkung
EP0915873A1 (fr)	1999-05-19	Derives de pyrazolyle-pyrazol substitues, procede permettant de les preparer et utilisation comme agents a effet herbicide
EP0256396A1 (fr)	1988-02-24	Triazolo-pyrimidinesulfonamides-2
EP0272628B1 (fr)	1992-04-29	6,7-Dihydro-[1,2,4]triazolo[1,5-a][1,3,5]triazine-2-sulfonamides, procédé pour leur préparation et leur utilisation comme agents à activité herbizide et régulatrice de la croissance
DD256449A5 (de)	1988-05-11	Pyrazolo(3,4-b)pyridinderivate enthaltende mittel mit herbizider wirkung
DE3737748A1 (de)	1989-05-18	3-arylsulfonylamino-1h-1,2,4-triazole, verfahren zu ihrer herstellung und ihre verwendung als mittel mit herbizider und wachstumsregulierender wirkung
DE3712782A1 (de)	1988-11-03	Anellierte uracilderivate, verfahren zu ihrer herstellung und ihre verwendung als herbizide mittel
EP0183993A2 (fr)	1986-06-11	2H-Imidazo[1',2':1,2]pyrrolo[3,4-b]pyridines et leur utilisation comme agents contre les mauvaises herbes
DE3539386A1 (de)	1987-05-14	N-(s-triazolo(1,5-a)pyrimidin-2-yl)-2-alkoxy-benzolsulfonamide, verfahren zur herstellung dieser verbindungen sowie diese enthaltende mittel mit herbizider und pflanzenwachstumsregulierender wirkung
DE3601688A1 (de)	1987-07-23	Naphthyridin-derivate, verfahren zu ihrer herstellung und ihre verwendung als mittel mit herbizider wirkung
DE3545597A1 (de)	1987-07-02	Neue herbizid wirksame imidazolinone
DE3809390A1 (de)	1989-09-28	Perhydro-imidazopyridine und -pyrroloimidazole, verfahren zu ihrer herstellung und ihre verwendung als herbizide mittel
DE3810706A1 (de)	1989-10-05	Substituierte cumarinderivate, verfahren zu ihrer herstellung und ihre verwendung als mittel mit herbizider wirkung
DD285283A5 (de)	1990-12-12	Herbizide mittel
EP0170860A1 (fr)	1986-02-12	Dérivés d'imidazo-pyrrolo-pyridines
DD252114A5 (de)	1987-12-09	Herbizide mittel
DE3913757A1 (de)	1990-10-25	Substituierte imidazolin-2-yl-acrylsaeurederivate, verfahren und zwischenstufen zu ihrer herstellung und ihre verwendung als mittel mit herbizider wirkung
EP0173319A1 (fr)	1986-03-05	Arylsulfonylguanidines substituées
DE4015647A1 (de)	1991-11-14	Heterocyclisch substituierte 1,2,4-triazolo(4,3-a)pyridine, heterocyclisch substituierte n'-(2-pyridyl)-aldehydhydrazone als vorstufen, verfahren zur herstellung dieser verbindungen und ihre verwendung als mittel mit herbizider wirkung
DE4241658A1 (de)	1994-06-09	Substituierte 2-Thiobenzthiazole, Verfahren zu ihrer Herstellung und ihre Verwendung als herbizide Mittel
DE3627356A1 (de)	1988-02-18	6,7-methylendioxychinolin-derivate, verfahren und zwischenstufen zu ihrer herstellung und ihre verwendung als mittel mit herbizider wirkung
DE19535842A1 (de)	1997-03-20	Herbizide 3- bzw. 3,4-heterosubstituierte Pyrrolinone

DD256449A5 - Pyrazolo(3,4-b)pyridinderivate enthaltende mittel mit herbizider wirkung - Google Patents

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