DK169105B1 - 2,3-Dihydro-3-oxo-5H-imidazo[2',1':4,3]imidazo[1,5-a]-pyridin-carboxylsyre(ester)-indre salte og -ylider, fremgangsmåde til deres fremstilling og en fremgangsmåde til bekæmpelse af en- og tokimbladede, et- og flerårige planter samt vandplanter - Google Patents
2,3-Dihydro-3-oxo-5H-imidazo[2',1':4,3]imidazo[1,5-a]-pyridin-carboxylsyre(ester)-indre salte og -ylider, fremgangsmåde til deres fremstilling og en fremgangsmåde til bekæmpelse af en- og tokimbladede, et- og flerårige planter samt vandplanter Download PDFInfo
- Publication number
- DK169105B1 DK169105B1 DK038387A DK38387A DK169105B1 DK 169105 B1 DK169105 B1 DK 169105B1 DK 038387 A DK038387 A DK 038387A DK 38387 A DK38387 A DK 38387A DK 169105 B1 DK169105 B1 DK 169105B1
- Authority
- DK
- Denmark
- Prior art keywords
- imidazo
- oxo
- alkyl
- dihydro
- compound according
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 150000003839 salts Chemical class 0.000 title claims abstract description 11
- 150000002148 esters Chemical class 0.000 title claims description 10
- -1 2,3-Dihydro-3-oxo-5H-imidazo [2 ', 1': 4,3] imidazo [1,5-a] -pyridine carboxylic acid Chemical compound 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 46
- 230000002363 herbicidal effect Effects 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 239000004009 herbicide Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 239000002689 soil Substances 0.000 claims description 7
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- CVDQDFLRMFSFLU-UHFFFAOYSA-N 3-(4,5-dihydro-1h-imidazol-2-yl)pyridine-2-carboxylic acid Chemical compound OC(=O)C1=NC=CC=C1C1=NCCN1 CVDQDFLRMFSFLU-UHFFFAOYSA-N 0.000 claims description 2
- CGDAWEVRGAIHJH-UHFFFAOYSA-N 3-carbamoylpyridine-2-carboxylic acid Chemical compound NC(=O)C1=CC=CN=C1C(O)=O CGDAWEVRGAIHJH-UHFFFAOYSA-N 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims description 2
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 claims 1
- 230000001850 reproductive effect Effects 0.000 claims 1
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- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
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- 240000003461 Setaria viridis Species 0.000 description 2
- 235000002248 Setaria viridis Nutrition 0.000 description 2
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- 244000067505 Xanthium strumarium Species 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
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- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
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- 125000005843 halogen group Chemical group 0.000 description 2
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- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
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- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 description 1
- POWQZFXZDXTXIO-UHFFFAOYSA-N imidazo[1,5-a]pyridine-1-carboxylic acid Chemical compound C1=CC=CC2=C(C(=O)O)N=CN21 POWQZFXZDXTXIO-UHFFFAOYSA-N 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
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- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- HLSYPCGUANRZJM-UHFFFAOYSA-N methyl 2-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)pyridine-3-carboxylate Chemical compound COC(=O)C1=CC=CN=C1C1=NC(C)(C(C)C)C(=O)N1 HLSYPCGUANRZJM-UHFFFAOYSA-N 0.000 description 1
- JLFYGDWQXDWRPX-UHFFFAOYSA-N methyl 2-[(1-amino-2,3-dimethyl-1-oxobutan-2-yl)carbamoyl]pyridine-3-carboxylate Chemical compound COC(=O)C1=CC=CN=C1C(=O)NC(C)(C(C)C)C(N)=O JLFYGDWQXDWRPX-UHFFFAOYSA-N 0.000 description 1
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- IYNMDWMQHSMDDE-MHXJNQAMSA-N perindopril erbumine Chemical compound CC(C)(C)N.C1CCC[C@@H]2N(C(=O)[C@H](C)N[C@@H](CCC)C(=O)OCC)[C@H](C(O)=O)C[C@@H]21 IYNMDWMQHSMDDE-MHXJNQAMSA-N 0.000 description 1
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- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical class C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
- RAYMXZBXQCGRGX-UHFFFAOYSA-N quinoline-5-carboxylic acid Chemical class C1=CC=C2C(C(=O)O)=CC=CC2=N1 RAYMXZBXQCGRGX-UHFFFAOYSA-N 0.000 description 1
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- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/14—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
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Health & Medical Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Fertilizers (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/822,098 US4698092A (en) | 1986-01-24 | 1986-01-24 | 5H-imidazo[2',1':4,3]imidazo-[1,5a]pyridin-6-ium salts and their use as herbicidal agents |
| US82209886 | 1986-01-24 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK38387D0 DK38387D0 (da) | 1987-01-23 |
| DK38387A DK38387A (da) | 1987-07-25 |
| DK169105B1 true DK169105B1 (da) | 1994-08-15 |
Family
ID=25235134
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK038387A DK169105B1 (da) | 1986-01-24 | 1987-01-23 | 2,3-Dihydro-3-oxo-5H-imidazo[2',1':4,3]imidazo[1,5-a]-pyridin-carboxylsyre(ester)-indre salte og -ylider, fremgangsmåde til deres fremstilling og en fremgangsmåde til bekæmpelse af en- og tokimbladede, et- og flerårige planter samt vandplanter |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4698092A (enExample) |
| EP (1) | EP0231800B1 (enExample) |
| JP (1) | JP2502561B2 (enExample) |
| KR (1) | KR900005517B1 (enExample) |
| AT (1) | ATE86996T1 (enExample) |
| AU (1) | AU586730B2 (enExample) |
| BR (1) | BR8700310A (enExample) |
| CA (1) | CA1329202C (enExample) |
| DE (1) | DE3784744T2 (enExample) |
| DK (1) | DK169105B1 (enExample) |
| ES (1) | ES2054624T3 (enExample) |
| FI (1) | FI84354C (enExample) |
| GR (1) | GR3007471T3 (enExample) |
| HU (1) | HU199417B (enExample) |
| IE (1) | IE59790B1 (enExample) |
| IL (1) | IL81330A (enExample) |
| YU (1) | YU45933B (enExample) |
| ZA (1) | ZA87518B (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060174366A1 (en) | 2002-07-09 | 2006-08-03 | Mariette Andersson | Use of ahas mutant genes as selection marker in potato transformation |
| EP2319872A1 (en) | 2009-11-04 | 2011-05-11 | BASF Plant Science GmbH | Amylopectin type starch with enhanced retrogradation stability |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4179277A (en) * | 1976-03-12 | 1979-12-18 | Bayer Aktiengesellschaft | 4,5-Dichloroimidazole-2-carboxylic acid derivatives |
| US4143142A (en) * | 1976-09-24 | 1979-03-06 | Adhikary Parimal K | Novel pyrido-imidazo-indoles, compositions and method therewith |
| US4207320A (en) * | 1978-08-28 | 1980-06-10 | Warner-Lambert Company | Amino-substituted imidazo[1,2-a:3,4-a']diquinolin-15-ium salts compositions and method of use |
| IL62794A0 (en) * | 1980-06-02 | 1981-07-31 | American Cyanamid Co | Substituted nicotinic acid esters and salts thereof and their use as herbicidal agents |
| HU183330B (en) * | 1981-02-13 | 1984-04-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing new of 2,4,8-triazaphenalenium-salts |
| EP0166907A3 (en) * | 1984-06-04 | 1988-09-14 | American Cyanamid Company | Herbicidal 2-(2-imidazolin-2-yl)-fluoroalkoxy-, alkenyloxy- and alkynyloxypyridines and quinolines |
-
1986
- 1986-01-24 US US06/822,098 patent/US4698092A/en not_active Expired - Lifetime
-
1987
- 1987-01-19 EP EP87100607A patent/EP0231800B1/en not_active Expired - Lifetime
- 1987-01-19 DE DE87100607T patent/DE3784744T2/de not_active Expired - Fee Related
- 1987-01-19 AT AT87100607T patent/ATE86996T1/de not_active IP Right Cessation
- 1987-01-19 ES ES87100607T patent/ES2054624T3/es not_active Expired - Lifetime
- 1987-01-20 IL IL81330A patent/IL81330A/xx not_active IP Right Cessation
- 1987-01-22 CA CA000527898A patent/CA1329202C/en not_active Expired - Fee Related
- 1987-01-23 YU YU8987A patent/YU45933B/sh unknown
- 1987-01-23 IE IE18187A patent/IE59790B1/en not_active IP Right Cessation
- 1987-01-23 FI FI870292A patent/FI84354C/fi not_active IP Right Cessation
- 1987-01-23 BR BR8700310A patent/BR8700310A/pt not_active IP Right Cessation
- 1987-01-23 HU HU87212A patent/HU199417B/hu unknown
- 1987-01-23 DK DK038387A patent/DK169105B1/da not_active IP Right Cessation
- 1987-01-23 ZA ZA87518A patent/ZA87518B/xx unknown
- 1987-01-23 AU AU67967/87A patent/AU586730B2/en not_active Ceased
- 1987-01-23 KR KR1019870000541A patent/KR900005517B1/ko not_active Expired
- 1987-01-24 JP JP62015017A patent/JP2502561B2/ja not_active Expired - Lifetime
-
1993
- 1993-03-26 GR GR910402239T patent/GR3007471T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IE59790B1 (en) | 1994-04-06 |
| JPS62228077A (ja) | 1987-10-06 |
| IE870181L (en) | 1987-07-24 |
| FI84354B (fi) | 1991-08-15 |
| FI870292A0 (fi) | 1987-01-23 |
| JP2502561B2 (ja) | 1996-05-29 |
| BR8700310A (pt) | 1987-12-08 |
| KR900005517B1 (ko) | 1990-07-30 |
| KR870007124A (ko) | 1987-08-17 |
| EP0231800A3 (en) | 1988-10-19 |
| ZA87518B (en) | 1987-09-30 |
| ATE86996T1 (de) | 1993-04-15 |
| IL81330A0 (en) | 1987-08-31 |
| FI84354C (fi) | 1991-11-25 |
| HU199417B (en) | 1990-02-28 |
| AU586730B2 (en) | 1989-07-20 |
| YU8987A (en) | 1988-08-31 |
| HUT44693A (en) | 1988-04-28 |
| EP0231800B1 (en) | 1993-03-17 |
| US4698092A (en) | 1987-10-06 |
| DK38387D0 (da) | 1987-01-23 |
| FI870292L (fi) | 1987-07-25 |
| EP0231800A2 (en) | 1987-08-12 |
| DK38387A (da) | 1987-07-25 |
| CA1329202C (en) | 1994-05-03 |
| GR3007471T3 (enExample) | 1993-07-30 |
| DE3784744T2 (de) | 1993-10-07 |
| AU6796787A (en) | 1987-07-30 |
| IL81330A (en) | 1991-01-31 |
| DE3784744D1 (de) | 1993-04-22 |
| ES2054624T3 (es) | 1994-08-16 |
| YU45933B (sh) | 1992-09-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B1 | Patent granted (law 1993) | ||
| PBP | Patent lapsed |