AR121820A1 - NEW 3-(4-ALKENIL-PHENYL)-3-PYRROLIN-2-ONES AND THEIR USE AS HERBICIDES - Google Patents

NEW 3-(4-ALKENIL-PHENYL)-3-PYRROLIN-2-ONES AND THEIR USE AS HERBICIDES

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Publication number
AR121820A1
AR121820A1 ARP210100958A ARP210100958A AR121820A1 AR 121820 A1 AR121820 A1 AR 121820A1 AR P210100958 A ARP210100958 A AR P210100958A AR P210100958 A ARP210100958 A AR P210100958A AR 121820 A1 AR121820 A1 AR 121820A1
Authority
AR
Argentina
Prior art keywords
alkyl
alkoxy
halogen
cycloalkyl
hydrogen
Prior art date
Application number
ARP210100958A
Other languages
Spanish (es)
Inventor
Guido Bojack
Andreas Rembiak
Alfred Angermann
Hartmut Ahrens
Arsequell Estella Buscato
Lars Arve
Elisabeth Asmus
Christopher Hugh Rosinger
Elmar Gatzweiler
Original Assignee
Bayer Ag
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.)
Filing date
Publication date
Application filed by Bayer Ag filed Critical Bayer Ag
Publication of AR121820A1 publication Critical patent/AR121820A1/en

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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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/612—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety

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  • 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)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

La presente invención se refiere a nuevas 3-fenilpirrolin-2-onas de eficacia herbicida de acuerdo con la fórmula general (1) o sus sales agroquímicamente aceptables, así como a su uso para el combate de malezas y malas hierbas en cultivos de plantas útiles. Reivindicación 1: 3-fenilpirrolin-2-onas de la fórmula general (1) o una de sus sales agroquímicamente aceptables, en donde R¹ es alquilo (C₁₋₆), halogen-alquilo (C₁₋₆), alcoxi (C₁₋₆), halogen-alcoxi (C₁₋₆), alcoxi (C₁₋₄)-alquilo (C₁₋₄), halogen-alcoxi (C₁₋₄)-alquilo (C₁₋₄), alcoxi (C₁₋₆)-alcoxi (C₁₋₄), halogen-alcoxi (C₁₋₆)-alcoxi (C₂₋₄), cicloalquilo (C₃₋₆), alquenil (C₂₋₆)-oxi, halogen-alquenil (C₂₋₆)-oxi, alquinil (C₂₋₆)-oxi o ciano-alcoxi (C₁₋₆), R² es hidrógeno, alquilo (C₁₋₆), alcoxi (C₁₋₄)-alquilo (C₁₋₄), halogen-alquilo (C₁₋₆), cicloalquilo (C₃₋₆), cicloalquil (C₃₋₆)-alquilo (C₁₋₄), alquenilo (C₂₋₆), alquinilo (C₂₋₆), alcoxi (C₁₋₆) o halogen-alcoxi (C₁₋₆), X es alquilo (C₁₋₆), halogen-alquilo (C₁₋₆), cicloalquilo (C₃₋₆), alcoxi (C₁₋₆), halogen-alcoxi (C₁₋₆), bromo, cloro o fluoro, Y es alquilo (C₁₋₆), halogen-alquilo (C₁₋₆), cicloalquilo (C₃₋₆), alcoxi (C₁₋₆), halogen-alcoxi (C₁₋₆), R¹⁰ es hidrógeno, fluoro, alquilo (C₁₋₆) o halogen-alquilo (C₁₋₆), R¹¹ es fluoro, alquilo (C₁₋₆) o halogen-alquilo (C₁₋₆), R¹² es hidrógeno, fluoro, alquilo (C₁₋₆) o halogen-alquilo (C₁₋₆), G es hidrógeno, un grupo L escindible o un catión E, en donde L es uno de los siguientes radicales 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), halogen-alquilo (C₁₋₄), alcoxi (C₁₋₄), halogen-alcoxi (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, junto con el átomo de nitrógeno al que están unidos, forman un anillo saturado de 5, 6 ó 7 miembros, en donde un átomo de carbono del anillo puede estar opcionalmente reemplazado por 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 radicales iguales o diferentes de los grupos alquilo (C₁₋₁₀) o cicloalquilo (C₃₋₇), que pueden estar sustituidos, de modo independiente entre sí, una o varias veces con fluoro, cloro, bromo, ciano, hidroxi o que pueden estar interrumpidos por uno o varios átomos de oxígeno o azufre, es un ión amonio alifático o heteroalifático secundario o terciario cíclico, por ejemplo, morfolinio, tiomorfolinio, piperidinio, pirrolidinio o 1,4-diazabiciclo[1.1.2]octano (DABCO) o 1,5-diazabiciclo[4.3.0]undec-7-eno (DBU) en cada caso protonado, es un catión amonio heteroaromático, por ejemplo, en cada caso protonado 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, metilsulfato de 1,3-dimetilimidazolio o también representa un ión trimetilsulfonio.The present invention relates to new herbicidally effective 3-phenylpyrrolin-2-ones according to general formula (1) or their agrochemically acceptable salts, as well as their use for combating weeds and weeds in crops of useful plants. . Claim 1: 3-phenylpyrrolin-2-ones of the general formula (1) or one of its agrochemically acceptable salts, wherein R¹ is (C₁₋₆)alkyl, (C₁₋₆)halogen-alkyl, (C₁₋₆)alkoxy ), halogen-(C₁₋₆)alkoxy, (C₁₋₄)alkoxy-(C₁₋₄)alkyl, halogen-(C₁₋₄)alkoxy-(C₁₋₄)alkyl, (C₁₋₆)alkoxy-alkoxy ( (C₁₋₄), halogen-(C₁₋₆)alkoxy-(C₂₋₄)alkoxy, (C₃₋₆)cycloalkyl, (C₂₋₆)alkenyl-oxy, halogen-(C₂₋₆)alkenyl-oxy, alkynyl ( C₂₋₆)-oxy or cyano-(C₁₋₆)alkoxy, R² is hydrogen, (C₁₋₆)alkyl, (C₁₋₄)alkoxy-(C₁₋₄)alkyl, halogen-(C₁₋₆)alkyl, (C₃₋₆)-cycloalkyl, (C₃₋₆)-cycloalkyl-(C₁₋₄)-alkyl, (C₂₋₆-alkenyl), (C₂₋₆-alkynyl), (C₁₋₆-alkoxy) or (C₁₋₆-)alkoxy Y is (C₁₋₆)alkyl, halogen-(C₁₋₆)alkyl, (C₃₋₆)cycloalkyl, (C₁₋₆)alkoxy, (C₁₋₆)halogen-alkoxy, R¹⁰ is hydrogen, fluoro, (C₁₋₆)alkyl ) or halogen-alkyl (C₁₋₆), R¹¹ is fluoro, alkyl (C₁₋₆ ) or halogen-(C₁₋₆)-alkyl, R¹² is hydrogen, fluoro, (C₁₋₆)-alkyl, or halogen-(C₁₋₆)-alkyl, G is hydrogen, a cleavable group L, or a cation E, where L is one of the following radicals from the group of formulas (2), wherein R³ is (C₁₋₄)alkyl or (C₁₋₃)alkoxy-(C₁₋₄)alkyl, R⁴ is (C₁₋₄)alkyl, R⁵ is alkyl (C₁₋₄), an unsubstituted phenyl or a phenyl mono- or polysubstituted with halogen, (C₁₋₄)-alkyl, (C₁₋₄-halogen-alkyl), (C₁₋₄-alkoxy), (C₁₋₄-halogen-alkoxy ), nitro or cyano, R⁶, R⁶ are independently methoxy or ethoxy, R⁷, R⁸ are independently methyl, ethyl, phenyl or, together with the nitrogen atom to which they are attached , form a saturated 5-, 6-, or 7-membered ring, where a carbon atom in the ring may optionally be replaced by 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 ion, a magnesium-halogen cation or an ammonium ion, wherein optionally one, two, three or all four hydrogen atoms are replaced by the same or different radicals of (C₁₋₁₀) alkyl or (C₃₋₇) cycloalkyl groups , which may be substituted independently of one another one or more times by fluorine, chlorine, bromine, cyano, hydroxy or may be interrupted by one or more oxygen or sulfur atoms, is a secondary aliphatic or heteroaliphatic ammonium ion or cyclic tertiary, for example morpholinium, thiomorpholinium, piperidinium, pyrrolidinium or 1,4-diazabicyclo[1.1.2]octane (DABCO) or 1,5-diazabicyclo[4.3.0]undec-7-ene (DBU) in each case protonated, is a heteroaromatic ammonium cation, e.g., in each occurrence protonated pyridine, 2-methylpyridine, 3-methylpyridine, 4-methylpyridine, 2,4-dimethylpyridine, 2,5-dimethylpyridine, 2,6-dimethylpyridine, 5-ethyl -2-methylpyridine, collidine, pyrrole, imidazole, quinoline, quinoxaline, 1,2-dimethylimidazole, 1,3-dimethylsulfate limidazolium or also represents a trimethylsulfonium ion.

ARP210100958A 2020-04-09 2021-04-09 NEW 3-(4-ALKENIL-PHENYL)-3-PYRROLIN-2-ONES AND THEIR USE AS HERBICIDES AR121820A1 (en)

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WO2023274869A1 (en) * 2021-06-29 2023-01-05 Bayer Aktiengesellschaft 3-(4-alkenyl-phenyl)-3-pyrrolino-2-ones and their use as herbicides

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