AR115088A1 - SPIROCICLOHEXYLPIRROLIN-2-ONAS AND ITS USE AS HERBICIDES - Google Patents
SPIROCICLOHEXYLPIRROLIN-2-ONAS AND ITS USE AS HERBICIDESInfo
- Publication number
- AR115088A1 AR115088A1 ARP190101273A ARP190101273A AR115088A1 AR 115088 A1 AR115088 A1 AR 115088A1 AR P190101273 A ARP190101273 A AR P190101273A AR P190101273 A ARP190101273 A AR P190101273A AR 115088 A1 AR115088 A1 AR 115088A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- methylpyridine
- ethyl
- independently
- cation
- Prior art date
Links
- 239000004009 herbicide Substances 0.000 title 1
- 125000004178 (C1-C4) alkyl group Chemical group 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
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- 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
- -1 cyano, hydroxy Chemical group 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 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
- 229920006395 saturated elastomer Polymers 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
- 125000004765 (C1-C4) haloalkyl 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
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 abstract 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 abstract 1
- FTTATHOUSOIFOQ-UHFFFAOYSA-N 1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine Chemical compound C1NCCN2CCCC21 FTTATHOUSOIFOQ-UHFFFAOYSA-N 0.000 abstract 1
- GIWQSPITLQVMSG-UHFFFAOYSA-N 1,2-dimethylimidazole Chemical compound CC1=NC=CN1C GIWQSPITLQVMSG-UHFFFAOYSA-N 0.000 abstract 1
- WOKQGMYCUGJNIJ-UHFFFAOYSA-M 1,3-dimethylimidazol-1-ium;methyl sulfate Chemical compound COS([O-])(=O)=O.CN1C=C[N+](C)=C1 WOKQGMYCUGJNIJ-UHFFFAOYSA-M 0.000 abstract 1
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2,5-dimethylpyridine Chemical compound CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-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 group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [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
- 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
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 abstract 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 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 Chemical group 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 Chemical group 0.000 abstract 1
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 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
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 125000004969 haloethyl group Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- 230000002363 herbicidal effect Effects 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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 class 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
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 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
- 229910052723 transition metal Inorganic materials 0.000 abstract 1
- 150000003624 transition metals Chemical class 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
- A01N43/34—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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
Abstract
Se proveen compuestos derivados de espirociclohexilpirrolin-2-onas o sus sales agroquímicamente aceptables que poseen actividad herbicida y su uso para el combate de malezas y pastos dañinos en cultivos de plantas útiles. Reivindicación 1: Espirociclohexilpirrolin-2-onas de la fórmula general (1) o una de sus sales agroquímicamente aceptables, en donde los restos presentan el siguiente significado R¹ es etilo o haloetilo; R² es alquilo C₁₋₆ o haloalquilo C₁₋₆; 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 R³ es alquilo C₁₋₄ o alcoxi C₁₋₃-alquilo C₁₋₄; R⁴ es alquilo C₁₋₄; R⁵ es alquilo C₁₋₄, un fenilo no sustituido o un fenilo mono- o polisustituido con halógeno, alquilo C₁₋₄, haloalquilo C₁₋₄, alcoxi C₁₋₄, haloalcoxi C₁₋₄, nitro o ciano; R⁶, R⁶’ son, de modo independiente entre sí, metoxi o etoxi; R⁷, R⁸ 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, un catión de magnesio-halógeno o un ión amonio, en donde opcionalmente uno, dos, tres o los cuatro átomos de hidrógeno están reemplazados por restos iguales o diferentes de los grupos alquilo C₁₋₁₀ o cicloalquilo C₃₋₇, que pueden estar independientemente entre sí, mono- o polisustituidos con flúor, cloro, bromo, ciano, hidroxi o pueden estar interrumpidos por uno o varios átomos de oxígeno o azufre, un ión amonio cíclico secundario o alifático terciario o heteroalifático, por ejemplo, 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), un catión amonio heteroaromático, por ejemplo, piridina, 2-metilpiridina, 3-metilpiridina, 4-metilpiridina, 2,4-dimetilpiridina, 2,5-di-metilpiridina, 2,6-dimetilpiridina, 5-etil-2-metilpiridina, colidina, pirrol, imidazol, quinolina, quinoxalina, 1,2-dimetilimidazol, metilsulfato de 1,3-dimetilimidazolio en cada caso protonado o también representa un ión trimetilsulfonio.Compounds derived from spirocyclohexylpyrrolin-2-ones or their agrochemically acceptable salts are provided which possess herbicidal activity and their use for the control of harmful weeds and grasses in crops of useful plants. Claim 1: Spirocyclohexylpyrrolin-2-ones of the general formula (1) or one of its agrochemically acceptable salts, wherein the residues have the following meaning: R¹ is ethyl or haloethyl; R² is C₁₋₆ alkyl or C₁₋₆ haloalkyl; G is hydrogen, a cleavable group L or a cation E, where L is one of the moieties from the group of formulas (2), where R³ is C₁₋₄ alkyl or C₁₋₃ alkoxy-C₁₋₄ alkyl; R⁴ is C₁₋₄ alkyl; R⁵ is C₁₋₄ alkyl, an unsubstituted phenyl, or a phenyl mono- or polysubstituted with halogen, C alqu alkyl, C₁₋₄ haloalkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkoxy, nitro or cyano; R⁶, R⁶ 'are, independently of one another, methoxy or ethoxy; R⁷, R⁸ are, independently of each other, methyl, ethyl, phenyl or together they form a saturated 5, 6 or 7 membered ring or together they form a saturated 5, 6 or 7 membered heterocycle with an oxygen or sulfur atom ; E is an alkali metal ion, an ionic equivalent of an alkaline earth metal, an ionic equivalent of aluminum, an ionic equivalent of a transition metal, a magnesium-halogen cation, or an ammonium ion, where optionally one, two, three or the four hydrogen atoms are replaced by the same or different residues from the C₁₋₁₀ alkyl or C₃₋₇ cycloalkyl groups, which can be independently of each other, mono- or polysubstituted with fluorine, chlorine, bromine, cyano, hydroxy or they can be interrupted by one or more oxygen or sulfur atoms, a cyclic secondary or tertiary aliphatic or heteroaliphatic ammonium ion, for example morpholinium, thiomorpholinium, piperidinium, pyrrolidino or in each case 1,4-diazabicyclo [1.1.2] protonated octane (DABCO ) or 1,5-diazabicyclo [4.3.0] undec-7-ene (DBU), a heteroaromatic ammonium cation, for example pyridine, 2-methylpyridine, 3-methylpyridine, 4-methylpyridine, 2,4-dimethylpyridine, 2 , 5-di-methylpyridine, 2,6-dimethylpyridine, 5-ethyl-2-methyl pyridine, collidine, pyrrole, imidazole, quinoline, quinoxaline, 1,2-dimethylimidazole, 1,3-dimethylimidazolium methylsulfate in each case protonated or also represents a trimethylsulfonium ion.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP18172346 | 2018-05-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR115088A1 true AR115088A1 (en) | 2020-11-25 |
Family
ID=62167231
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP190101273A AR115088A1 (en) | 2018-05-15 | 2019-05-13 | SPIROCICLOHEXYLPIRROLIN-2-ONAS AND ITS USE AS HERBICIDES |
Country Status (2)
| Country | Link |
|---|---|
| AR (1) | AR115088A1 (en) |
| WO (1) | WO2019219584A1 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2021209486A1 (en) | 2020-04-15 | 2021-10-21 | Bayer Aktiengesellschaft | Specifically substituted pyrroline-2-ones and their use as herbicides |
| BR112022022128A2 (en) | 2020-05-27 | 2022-12-13 | Bayer Ag | SPECIFICALLY SUBSTITUTED PIRROLIN-2-ONES AND THEIR USE AS HERBICIDES |
| WO2022253700A1 (en) | 2021-06-01 | 2022-12-08 | Bayer Aktiengesellschaft | Specifically substituted pyrroline-2-ones and their use as herbicides |
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-
2019
- 2019-05-13 AR ARP190101273A patent/AR115088A1/en not_active Application Discontinuation
- 2019-05-13 WO PCT/EP2019/062168 patent/WO2019219584A1/en active Application Filing
Also Published As
| Publication number | Publication date |
|---|---|
| WO2019219584A1 (en) | 2019-11-21 |
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