AR115086A1 - Pirrolin-2-onas sustituidas con 2-bromo-6-alcoxifenilo y su uso como herbicidas - Google Patents
Pirrolin-2-onas sustituidas con 2-bromo-6-alcoxifenilo y su uso como herbicidasInfo
- Publication number
- AR115086A1 AR115086A1 ARP190101271A ARP190101271A AR115086A1 AR 115086 A1 AR115086 A1 AR 115086A1 AR P190101271 A ARP190101271 A AR P190101271A AR P190101271 A ARP190101271 A AR P190101271A AR 115086 A1 AR115086 A1 AR 115086A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- methylpyridine
- bromo
- dimethylpyridine
- haloalkyl
- Prior art date
Links
- 239000004009 herbicide Substances 0.000 title abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 5
- -1 aluminum ion Chemical class 0.000 abstract 4
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 abstract 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 abstract 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 abstract 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 2
- JYYNAJVZFGKDEQ-UHFFFAOYSA-N 2,4-Dimethylpyridine Chemical compound CC1=CC=NC(C)=C1 JYYNAJVZFGKDEQ-UHFFFAOYSA-N 0.000 abstract 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 abstract 2
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 abstract 2
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 abstract 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000005347 halocycloalkyl group Chemical group 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical class O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 abstract 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000004434 sulfur atom Chemical group 0.000 abstract 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 1
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 abstract 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 abstract 1
- GIWQSPITLQVMSG-UHFFFAOYSA-N 1,2-dimethylimidazole Chemical compound CC1=NC=CN1C GIWQSPITLQVMSG-UHFFFAOYSA-N 0.000 abstract 1
- NTSLROIKFLNUIJ-UHFFFAOYSA-N 5-Ethyl-2-methylpyridine Chemical compound CCC1=CC=C(C)N=C1 NTSLROIKFLNUIJ-UHFFFAOYSA-N 0.000 abstract 1
- KNCHDRLWPAKSII-UHFFFAOYSA-N 5-ethyl-2-methylpyridine Natural products CCC1=CC=NC(C)=C1 KNCHDRLWPAKSII-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-O Piperidinium(1+) Chemical compound C1CC[NH2+]CC1 NQRYJNQNLNOLGT-UHFFFAOYSA-O 0.000 abstract 1
- 241000209504 Poaceae Species 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 229910001413 alkali metal ion Inorganic materials 0.000 abstract 1
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 abstract 1
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 239000012973 diazabicyclooctane Substances 0.000 abstract 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-O morpholinium Chemical compound [H+].C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-O 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 abstract 1
- 229910001428 transition metal ion Inorganic materials 0.000 abstract 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 abstract 1
- NRZWQKGABZFFKE-UHFFFAOYSA-N trimethylsulfonium Chemical compound C[S+](C)C NRZWQKGABZFFKE-UHFFFAOYSA-N 0.000 abstract 1
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 abstract 1
- 244000045561 useful plants Species 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/54—Spiro-condensed
-
- 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/12—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings condensed with a carbocyclic ring
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
- A01N43/38—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic rings
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (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)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyrrole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Catching Or Destruction (AREA)
Abstract
Se proveen pirrolin-2-onas sustituidas con 2-bromo-6-alcoxifenilo como herbicidas y sus sales agroquímicamente aceptables y su uso para el combate de malezas y pastos dañinos en cultivos de plantas útiles. Reivindicación 1: Pirrolin-2-onas sustituidas con 2-bromo-6-alcoxifenilo de la fórmula general (1), y sus sales agroquímicamente tolerables, caracterizadas porque R¹ es alquilo C₁₋₆, haloalquilo C₂₋₆, cicloalquilo C₃₋₆, halocicloalquilo C₃₋₆ o alcoxi C₁₋₃-alquilo C₂₋₄; R² es alquilo C₁₋₄, haloalquilo C₁₋₄, cicloalquilo C₃₋₆ o halocicloalquilo C₃₋₆; R³ es metilo, halogenmetilo, dihalogenmetilo o trihalogenmetilo; G es hidrógeno, un grupo escindible L o un catión E, en donde L es uno de los restos del grupo de fórmulas (2), en donde R⁴ es alquilo C₁₋₄ o alcoxi C₁₋₃-alquilo C₂₋₄; R⁵ es alquilo C₁₋₄; R⁶ es alquilo C₁₋₄, un fenilo no sustituido o mono- o polisustituido con halógeno, alquilo C₁₋₄, haloalquilo C₁₋₄, alcoxi C₁₋₄, haloalcoxi C₁₋₄, nitro o ciano; R⁷, R⁷ son, de modo independiente entre sí, metoxi o etoxi; R⁸, R⁹ son, de modo independiente entre sí, metilo, etilo, fenilo o juntos forman un anillo saturado de 5, 6 ó 7 miembros o juntos forman un heterociclo saturado de 5, 6 ó 7 miembros con un átomo de oxígeno o de azufre; E es un ión de metal alcalino, un equivalente iónico de un metal alcalinotérreo, un equivalente iónico de aluminio, un equivalente iónico de un metal de transición o es un catión de magnesio-halógeno, es un ión amonio en el que opcionalmente uno, dos, tres o los cuatro pueden estar reemplazados por átomos de hidrógeno por restos iguales o diferentes de los grupos alquilo C₁₋₁₀ o cicloalquilo C₃₋₇, en donde pueden estar mono- o polisustituidos, independientemente entre sí, con flúor, cloro, bromo, ciano, hidroxi o pueden estar interrumpidos por uno o varios átomos de oxígeno o azufre, es un ión amonio cíclico secundario o alifático terciario o heteroalifático, por ejemplo, en cada caso, morfolinio, tiomorfolinio, piperidinio, pirrolidino o en cada caso 1,4-diazabiciclo[1.1.2]octano protonado (DABCO) o 1,5-diazabiciclo[4.3.0]undec-7-eno (DBU), es un catión amonio heteroaromático, por ejemplo, piridina, 2-metilpiridina, 3-metilpiridina, 4-metilpiridina, 2,4-dimetilpiridina, 2,5-dimetilpiridina, 2,6-dimetilpiridina, 5-etil-2-metilpiridina, colidina, pirrol, imidazol, quinolina, quinoxalina, 1,2-dimetilimidazol, 1,3-metilsulfato de dimetilimidazolio en cada caso protonados o también puede representar un ión trimetilsulfonio.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP18172341 | 2018-05-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR115086A1 true AR115086A1 (es) | 2020-11-25 |
Family
ID=62167228
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP190101271A AR115086A1 (es) | 2018-05-15 | 2019-05-13 | Pirrolin-2-onas sustituidas con 2-bromo-6-alcoxifenilo y su uso como herbicidas |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US20220106271A1 (es) |
| EP (1) | EP3793977A1 (es) |
| JP (1) | JP2021523904A (es) |
| KR (1) | KR20210008069A (es) |
| CN (1) | CN112334446A (es) |
| AR (1) | AR115086A1 (es) |
| AU (1) | AU2019269028A1 (es) |
| BR (1) | BR112020022808A2 (es) |
| CA (1) | CA3100089A1 (es) |
| EA (1) | EA202092643A1 (es) |
| WO (1) | WO2019219587A1 (es) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2021204884A1 (de) | 2020-04-09 | 2021-10-14 | Bayer Aktiengesellschaft | 3-(4-alkenyl-phenyl)-3-pyrrolin-2-one und deren verwendung als herbizide |
| WO2021209486A1 (de) | 2020-04-15 | 2021-10-21 | Bayer Aktiengesellschaft | Speziell substituierte pyrrolin-2-one und deren verwendung als herbizide |
| US20230180758A1 (en) * | 2020-05-27 | 2023-06-15 | Bayer Aktiengesellschaft | Substituted pyrroline-2-ones and their use as herbicides |
| WO2022253700A1 (de) | 2021-06-01 | 2022-12-08 | Bayer Aktiengesellschaft | Speziell substituierte pyrrolin-2-one und deren verwendung als herbizide |
| WO2023274869A1 (de) | 2021-06-29 | 2023-01-05 | Bayer Aktiengesellschaft | 3-(4-alkenyl-phenyl)-3-pyrrolin-2-one und deren verwendung als herbizide |
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| EP3095869B1 (en) | 2008-04-14 | 2019-06-19 | BASF Agricultural Solutions Seed US LLC | Mutated hydroxyphenylpyruvate dioxygenase, dna sequence and isolation of plants which are tolerant to hppd inhibitor herbicides |
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| JP5987007B2 (ja) * | 2011-03-01 | 2016-09-06 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | ２−アシルオキシピロリン−４−オン類 |
| WO2015032702A1 (en) | 2013-09-06 | 2015-03-12 | Syngenta Limited | Herbicidally active 2-halogen-4-alkynyl- phenyl-pyrazolidine-dione or pyrrolidine-dione derivatives |
| AU2014323070B2 (en) | 2013-09-20 | 2018-05-10 | Syngenta Limited | Herbicidally active 2-halogen-4-alkynyl-phenyl-pyrazolidine-dione or pyrrolidine-dione derivatives |
| BR112018007013B1 (pt) * | 2015-10-06 | 2021-12-28 | Bayer Cropscience Aktiengesellschaft | N-fenilpirrolidina-2,4-dionas substituídas por alquinila; composição herbicida; método para controlar o crescimento de plantas indesejáveis e o uso dos referidos compostos substituídos |
| WO2019228788A1 (de) * | 2018-05-29 | 2019-12-05 | Bayer Aktiengesellschaft | 2-brom-6-alkoxyphenyl-substituierte pyrrolin-2-one und deren verwendung als herbizide |
| US20220056040A1 (en) * | 2019-03-15 | 2022-02-24 | Bayer Aktiengesellschaft | Novel 3-(2-bromo-4-alkynyl-6-alkoxyphenyl)-3-pyrrolin-2-ones and their use as herbicides |
-
2019
- 2019-05-13 CA CA3100089A patent/CA3100089A1/en active Pending
- 2019-05-13 CN CN201980040072.XA patent/CN112334446A/zh active Pending
- 2019-05-13 EA EA202092643A patent/EA202092643A1/ru unknown
- 2019-05-13 KR KR1020207035575A patent/KR20210008069A/ko not_active Withdrawn
- 2019-05-13 WO PCT/EP2019/062174 patent/WO2019219587A1/de not_active Ceased
- 2019-05-13 AR ARP190101271A patent/AR115086A1/es not_active Application Discontinuation
- 2019-05-13 US US17/054,918 patent/US20220106271A1/en not_active Abandoned
- 2019-05-13 EP EP19722911.5A patent/EP3793977A1/de not_active Withdrawn
- 2019-05-13 BR BR112020022808-7A patent/BR112020022808A2/pt not_active Application Discontinuation
- 2019-05-13 AU AU2019269028A patent/AU2019269028A1/en not_active Abandoned
- 2019-05-13 JP JP2020563952A patent/JP2021523904A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| CA3100089A1 (en) | 2019-11-21 |
| BR112020022808A2 (pt) | 2021-02-02 |
| KR20210008069A (ko) | 2021-01-20 |
| EP3793977A1 (de) | 2021-03-24 |
| US20220106271A1 (en) | 2022-04-07 |
| CN112334446A (zh) | 2021-02-05 |
| WO2019219587A1 (de) | 2019-11-21 |
| EA202092643A1 (ru) | 2021-03-22 |
| AU2019269028A1 (en) | 2020-12-03 |
| JP2021523904A (ja) | 2021-09-09 |
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