AR111303A1 - REPLACED PIRROLIDINONES AND ITS SALTS AND THEIR USE AS HERBICIDE ACTIVE INGREDIENTS - Google Patents

REPLACED PIRROLIDINONES AND ITS SALTS AND THEIR USE AS HERBICIDE ACTIVE INGREDIENTS

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AR111303A1
AR111303A1 ARP180100756A ARP180100756A AR111303A1 AR 111303 A1 AR111303 A1 AR 111303A1 AR P180100756 A ARP180100756 A AR P180100756A AR P180100756 A ARP180100756 A AR P180100756A AR 111303 A1 AR111303 A1 AR 111303A1
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Argentina
Prior art keywords
alkyl
cycloalkyl
alkoxy
aryl
alkynyl
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ARP180100756A
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Spanish (es)
Inventor
Lehr Stefan Dr
Gatzweiler Elmar Dr
Rosinger Christopher Hugh Dr
Dietrich Hansjrg Dr
Dller Uwe Dr
Helmke Hendrik Dr
Mller Thomas Dr
Schmutzler Dirk Dr
Machettira Anu Bheemaiah Dr
Mleod Michael Charles Dr
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Bayer Ag
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Publication of AR111303A1 publication Critical patent/AR111303A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pyrrole Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Pirrolidinonas sustituidas y sus sales y su uso como ingredientes activos herbicidas, en particular para controlar malezas y/o malas hierbas en cultivos de plantas útiles y/o como reguladores del crecimiento de las plantas para influir en el crecimiento de cultivos de plantas útiles. Reivindicación 1: Pirrolidinonas sustituidas de la fórmula (1) o sus sales, en las que Q es un arilo opcionalmente sustituido, heteroarilo, C₃₋₁₀-cicloalquilo o C₃₋₁₀-cicloalquenilo, donde cada anillo o cada sistema de anillos opcionalmente puede estar sustituido con hasta 5 sustituyentes del grupo R⁶; o es un anillo heterocíclico de 5 - 7 miembros opcionalmente sustituido; o es un sistema de anillos bicíclico de 8 - 10 miembros opcionalmente sustituido, en el que cada anillo o cada sistema de anillos está compuesto por átomos de carbono y 1 - 5 heteroátomos, que contienen independientemente hasta 2 átomos de O, hasta 2 átomos de S y hasta 5 átomos de N, donde se pueden seleccionar hasta tres átomos de anillo de carbono independientemente de los grupos C(=O) y C(=S) y los átomos de anillo de azufre además se pueden seleccionar de los grupos S, S(=O), S(=O)₂, S(=NR¹) y S(=NR¹)(=O); donde cada anillo o cada sistema de anillos opcionalmente puede estar sustituido con hasta 5 sustituyentes del grupo R⁶, o Q es C₂₋₁₀-alquenilo, C₂₋₁₀-alquinilo, C₂₋₁₀-haloalquenilo, C₂₋₁₀-haloalquinilo, C₃₋₁₀-halocicloalquenilo, C₁₋₁₀-alquilcarbonilo o C₁₋₁₀-alcoxi-C₁₋₁₀-alquilo, C₁₋₁₀-haloalcoxi-C₁₋₁₀-alquilo; Z representa al grupo de fórmula (2); Y es -C(R⁷)(R⁸)-, oxígeno o NR¹; W¹ y W² son independientemente oxígeno o azufre; R¹ es hidrógeno, amino, hidroxi, ciano, formil, C₁₋₈-alquilo, C₁₋₈-haloalquilo, C₁₋₈-cianoalquilo, C₁₋₈-hidroxialquilo, C₁₋₈-alcoxi-C₁₋₈-alquilo, arilo-C₁₋₈-alquilo, heteroarilo-C₁₋₈-alquilo, heterociclilo-C₁₋₈-alquilo, C₃₋₁₀-cicloalquilo, C₃₋₁₀-cicloalquilo-C₁₋₈-alquilo, C₃₋₈-halocicloalquilo, C₃₋₈-halocicloalquilo-C₁₋₈-alquilo, C₁₋₈-alquilcarbonilo, C₁₋₈-alcoxicarbonilo, C₂₋₈-alquenilo, C₂₋₈-alquinilo, tris-[C₁₋₈-alquil]silil-C₂₋₈-alquinilo, tris-[C₁₋₈-alquil]sililo; R² es hidrógeno, halógeno, hidroxi, C₁₋₈-alquilo, C₁₋₈-haloalquilo, C₁₋₈-hidroxialquilo, C₁₋₈-alcoxi-C₁₋₈-alquilo; R³ es hidrógeno, halógeno, hidroxi, C₁₋₈-alquilo, C₁₋₈-haloalquilo, C₁₋₈-hidroxialquilo, C₁₋₈-alcoxi, C₁₋₈-alcoxi-C₁₋₈-alquilo; R⁴ es C₃₋₁₀-cicloalquilo opcionalmente sustituido, C₃₋₁₀-halocicloalquilo, C₃₋₁₀-cianocicloalquilo, C₁₋₁₀-alquilo-C₃₋₁₀-cicloalquilo, C₁₋₁₀-alcoxi-C₃₋₁₀-cicloalquilo, C₁₋₁₀-haloalcoxi-C₃₋₁₀-cicloalquilo, C₁₋₁₀-alquiltio-C₃₋₁₀-cicloalquilo, arilo-C₃₋₁₀-cicloalquilo, heteroarilo-C₃₋₁₀-cicloalquilo, C₁₋₁₀-alcoxicarbonilo-C₃₋₁₀-cicloalquilo, hidroxicarbonil-C₃₋₁₀-cicloalquilo, C₃₋₁₀-cicloalquilo-C₃₋₁₀-cicloalquilo, C₃₋₁₀-cicloalcanonil, y en donde en el caso de que Q es = fenilo, el radical R⁴ no es ciclopentanilo; R⁵ es hidrógeno, hidroxi, amino, C₁₋₈-alquilo, C₁₋₈-haloalquilo, C₂₋₈-alquenilo, C₃₋₈-alquinilo, C₁₋₈-alcoxi-C₁₋₈-alquilo, C₁₋₈-haloalcoxi-C₁₋₈-alquilo, C₁₋₈-alquiltio-C₁₋₈-alquilo, C₁₋₈-alquilsulfinilo-C₁₋₈-alquilo, C₁₋₈-alquilsulfonilo-C₁₋₈-alquilo, C₁₋₈-alquilcarbonilo, C₁₋₈-haloalquilcarbonilo, C₃₋₈-cicloalquilcarbonilo, C₁₋₈-alcoxicarbonilo, C₂₋₈-haloalcoxicarbonilo, C₄₋₈-cicloalcoxicarbonilo, C₂₋₈-alquilaminocarbonilo, C₃₋₁₀-dialquilaminocarbonilo, C₃₋₁₀-cicloalquilaminocarbonilo, C₁₋₈-alcoxi, C₁₋₈-alquiltio, C₁₋₈-haloalquiltio, C₃₋₈-cicloalquiltio, C₁₋₈-alquilsulfinilo, C₁₋₈-haloalquilsulfinilo, C₃₋₈-cicloalquilsulfinilo, C₁₋₈-alquilsulfonilo, C₁₋₈-haloalquilsulfonilo, C₃₋₈-cicloalquilsulfonilo, C₁₋₈-alquilaminosulfonilo, C₂₋₈-dialquilaminosulfonilo o C₃₋₈-trialquilsililo; R⁶ es hidrógeno, nitro, amino, ciano, tiocianato, isotiocianato, halógeno, C₁₋₈-alquilo, C₃₋₈-cicloalquilo, C₂₋₈-alquenilo, C₂₋₈-alquinilo, arilo, arilo-C₁₋₈-alquilo, arilo-C₂₋₈-alquenilo, arilo-C₂₋₈-alquinilo, arilo-C₁₋₈-alcoxi, heteroarilo, C₁₋₈-alcoxi-C₁₋₈-alquilo, C₁₋₈-hidroxialquilo, C₁₋₈-haloalquilo, C₃₋₈-halocicloalquilo, C₁₋₈-alcoxi, C₁₋₈-haloalcoxi, ariloxi, heteroariloxi, C₃₋₈-cicloalquiloxi, hidroxi, C₃₋₈-cicloalquilo-C₁₋₈-alcoxi, C₁₋₈-alcoxicarbonilo, hidroxicarbonilo, aminocarbonilo, C₁₋₈-alquilaminocarbonilo, C₃₋₈-cicloalquilaminocarbonilo, C₁₋₈-cianoalquilaminocarbonilo, C₂₋₈-alquenilaminocarbonilo, C₂₋₈-alquinilaminocarbonilo, C₁₋₈-alquilamino, C₁₋₈-alquiltio, C₁₋₈-haloalquiltio, hidrotio, C₁₋₈-bis-alquilamino, C₃₋₈-cicloalquilamino, C₁₋₈-alquilcarbonilamino, C₃₋₈-cicloalquilcarbonilamino, formilamino, C₁₋₈-haloalquilcarbonilamino, C₁₋₈-alcoxicarbonilamino, C₁₋₈-alquilaminocarbonilamino, C₁₋₈-dialquilaminocarbonilamino, C₁₋₈-alquilsulfonilamino, C₃₋₈-cicloalquilsulfonilamino, arilsulfonilamino, hetarilsulfonilamino, aminosulfonilo, C₁₋₈-aminohaloalquilsulfonilo, C₁₋₈-alquilaminosulfonilo, C₁₋₈-bisalquilaminosulfonilo, C₃₋₈-cicloalquilaminosulfonilo, C₁₋₈-haloalquilaminosulfonilo, arilaminosulfonilo, arilo-C₁₋₈-alquilaminosulfonilo, C₁₋₈-alquilsulfonilo, C₃₋₈-cicloalquilsulfonilo, arilsulfonilo, C₁₋₈-alquilsulfinilo, C₃₋₈-cicloalquilsulfinilo, arilsulfinilo, N,S-C₁₋₈-dialquilsulfonimidoil, S-C₁₋₈-alquilsulfonimidoil, C₁₋₈-alquilsulfonilaminocarbonilo, C₃₋₈-cicloalquilsulfonilaminocarbonilo, C₃₋₈-cicloalquilaminosulfonilo, arilo-C₁₋₈-alquilcarbonilamino, C₃₋₈-cicloalquilo-C₁₋₈-alquilcarbonilamino, heteroarilcarbonilamino, C₁₋₈-alcoxi-C₁₋₈-alquilcarbonilamino, C₁₋₈-hidroxialquilcarbonilamino, C₁₋₈-trialquilsililo; y R⁷ y R⁸ son independientemente hidrógeno, hidroxi, halógeno, C₁₋₈-alquilo, C₁₋₈-haloalquilo, C₂₋₈-alquenilo, C₂₋₈-alquinilo, C₁₋₈-alcoxi-C₁₋₈-alquilo, C₁₋₈-haloalcoxi-C₁₋₈-alquilo, C₁₋₈-alquiltio-C₁₋₈-alquilo, C₁₋₈-alquilsulfinilo-C₁₋₈-alquilo, C₁₋₈-alquilsulfonilo-C₁₋₈-alquilo, C₁₋₈-alquilcarbonilo, C₁₋₈-haloalquilcarbonilo, C₃₋₈-cicloalquilcarbonilo, C₁₋₈-alcoxicarbonilo, C₂₋₈-haloalcoxicarbonilo, C₃₋₈-cicloalcoxicarbonilo, C₁₋₈-alquilaminocarbonilo, C₁₋₁₀-dialquilaminocarbonilo, C₃₋₁₀-cicloalquilaminocarbonilo, C₁₋₈-alcoxi, C₁₋₈-alquiltio, C₁₋₈-haloalquiltio, C₃₋₈-cicloalquiltio.Substituted pyrrolidinones and their salts and their use as active herbicidal ingredients, in particular to control weeds and / or weeds in useful plant crops and / or as plant growth regulators to influence the growth of useful plant crops. Claim 1: Substituted pyrrolidinones of the formula (1) or salts thereof, wherein Q is an optionally substituted aryl, heteroaryl, C₃₋₁₀-cycloalkyl or C₃₋₁₀-cycloalkenyl, where each ring or each ring system may optionally be substituted with up to 5 substituents of the group R⁶; or is an optionally substituted 5-7 membered heterocyclic ring; or is an optionally substituted 8-10-membered bicyclic ring system, in which each ring or each ring system is composed of carbon atoms and 1-5 heteroatoms, which independently contain up to 2 O atoms, up to 2 atoms of S and up to 5 N atoms, where up to three carbon ring atoms can be selected independently of the C (= O) and C (= S) groups and the sulfur ring atoms can also be selected from the S groups, S (= O), S (= O) ₂, S (= NR¹) and S (= NR¹) (= O); where each ring or each ring system may optionally be substituted with up to 5 substituents of the group R⁶, or Q is C₂₋₁₀-alkenyl, C₂₋₁₀-alkynyl, C₂₋₁₀-haloalkenyl, C₂₋₁₀-haloalkynyl, C₃₋₁₀ -halocycloalkenyl, C₁₋₁₀-alkylcarbonyl or C₁₋₁₀-alkoxy-C₁₋₁₀-alkyl, C₁₋₁₀-haloalkoxy-C₁₋₁₀-alkyl; Z represents the group of formula (2); Y is -C (R⁷) (R⁸) -, oxygen or NR¹; W¹ and W² are independently oxygen or sulfur; R¹ is hydrogen, amino, hydroxy, cyano, formyl, C₁₋₈-alkyl, C₁₋₈-haloalkyl, C₁₋₈-cyanoalkyl, C₁₋₈-hydroxyalkyl, C₁₋₈-alkoxy-C₁₋₈-alkyl, aryl- C₁₋₈-alkyl, heteroaryl-C₁₋₈-alkyl, heterocyclyl-C₁₋₈-alkyl, C₃₋₁₀-cycloalkyl, C₃₋₁₀-cycloalkyl-C₁₋₈-alkyl, C₃₋₈-halocycloalkyl, C₃₋₈- halocycloalkyl-C₁₋₈-alkyl, C₁₋₈-alkylcarbonyl, C₁₋₈-alkoxycarbonyl, C₂₋₈-alkenyl, C₂₋₈-alkynyl, tris- [C₁₋₈-alkyl] silyl-C₂₋₈-alkynyl, tris - [C₁₋₈-alkyl] silyl; R² is hydrogen, halogen, hydroxy, C₁₋₈-alkyl, C₁₋₈-haloalkyl, C₁₋₈-hydroxyalkyl, C₁₋₈-alkoxy-C₁₋₈-alkyl; R³ is hydrogen, halogen, hydroxy, C₁₋₈-alkyl, C₁₋₈-haloalkyl, C₁₋₈-hydroxyalkyl, C₁₋₈-alkoxy, C₁₋₈-alkoxy-C₁₋₈-alkyl; R⁴ is optionally substituted C₃₋₁₀-cycloalkyl, C₃₋₁₀-halocycloalkyl, C₃₋₁₀-cyanocycloalkyl, C₁₋₁₀-alkyl-C alquilo-cycloalkyl, C₁₋₁₀-alkoxy-C₃₋₁₀-cycloalkyl, C₁₋₁₀- haloalkoxy-C₃₋₁₀-cycloalkyl, C₁₋₁₀-alkylthio-C₃₋₁₀-cycloalkyl, aryl-C₃₋₁₀-cycloalkyl, heteroaryl-C₃₋₁₀-cycloalkyl, C₁₋₁₀-alkoxycarbonyl-C₃₋₁₀-cycloalkyl, hydroxycarbonyl- C₃₋₁₀-cycloalkyl, C₃₋₁₀-cycloalkyl-C₃₋₁₀-cycloalkyl, C₃₋₁₀-cycloalcanonyl, and where in the case that Q is = phenyl, the radical R⁴ is not cyclopentanyl; R⁵ is hydrogen, hydroxy, amino, C₁₋₈-alkyl, C₁₋₈-haloalkyl, C₂₋₈-alkenyl, C₃₋₈-alkynyl, C₁₋₈-alkoxy-C₁₋₈-alkyl, C₁₋₈-haloalkoxy- C₁₋₈-alkyl, C₁₋₈-alkylthio-C₁₋₈-alkyl, C₁₋₈-alkylsulfinyl-C₁₋₈-alkyl, C₁₋₈-alkylsulfonyl-C₁₋₈-alkyl, C₁₋₈-alkylcarbonyl, C₁₋ ₈-haloalkylcarbonyl, C₃₋₈-cycloalkylcarbonyl, C₁₋₈-alkoxycarbonyl, C₂₋₈-haloalkoxycarbonyl, C₄₋₈-cycloalkoxycarbonyl, C₂₋₈-alkylaminocarbonyl, C₃₋₁₀-dialkylaminocarbonyl, C₃₋₁₀-cycloalkylaminocarbonyl, C₁₋₈- alkoxy, C₁₋₈-alkylthio, C₁₋₈-haloalkylthio, C₃₋₈-cycloalkylthio, C₁₋₈-alkylsulfinyl, C₁₋₈-haloalkylsulfinyl, C₃₋₈-cycloalkylsulfinyl, C₁₋₈-alkylsulfonyl, C₁₋₈-haloalkylsulfonyl, C₃₋₈-cycloalkylsulfonyl, C₁₋₈-alkylaminosulfonyl, C₂₋₈-dialkylaminosulfonyl or C₃₋₈-tri alkylsilyl; R⁶ is hydrogen, nitro, amino, cyano, thiocyanate, isothiocyanate, halogen, C₁₋₈-alkyl, C₃₋₈-cycloalkyl, C₂₋₈-alkenyl, C₂₋₈-alkynyl, aryl, aryl-C₁₋₈-alkyl, aryl-C₂₋₈-alkenyl, aryl-C₂₋₈-alkynyl, aryl-C₁₋₈-alkoxy, heteroaryl, C₁₋₈-alkoxy-C₁₋₈-alkyl, C₁₋₈-hydroxyalkyl, C₁₋₈-haloalkyl, C₃₋₈-halocycloalkyl, C₁₋₈-alkoxy, C₁₋₈-haloalkoxy, aryloxy, heteroaryloxy, C₃₋₈-cycloalkyloxy, hydroxy, C₃₋₈-cycloalkyl-C₁₋₈-alkoxy, C₁₋₈-alkoxycarbonyl, hydroxycarbonyl, aminocarbonyl, C₁₋₈-alkylaminocarbonyl, C₃₋₈-cycloalkylaminocarbonyl, C₁₋₈-cyanoalkylaminocarbonyl, C₂₋₈-alkenylaminocarbonyl, C₂₋₈-alkylaminocarbonyl, C₁₋₈-alkylamino, C₁₋₈-alkylthio, C₁₋₈-haloalkylthio, hydrotium, C₁₋₈-bis-alkylamino, C₃₋₈-cycloalkylamino, C₁₋₈-alkylcarbonylamino, C₃₋₈-cycloalkylcarbonyl amino, formylamino, C₁₋₈-haloalkylcarbonylamino, C₁₋₈-alkoxycarbonylamino, C₁₋₈-alkylaminocarbonylamino, C₁₋₈-dialkylaminocarbonylamino, C₁₋₈-alkylsulfonylamino, C₃₋₈-cycloalkylsulfonylamino, arylsulfonylamino, hetarylsulfonylamino, aminosulfonyl, C₁₋₈- aminohaloalkylsulfonyl, C₁₋₈-alkylaminosulfonyl, C₁₋₈-bisalkylaminosulfonyl, C₃₋₈-cycloalkylaminosulfonyl, C₁₋₈-haloalkylaminosulfonyl, arylaminosulfonyl, aryl-C₁₋₈-alkylaminosulfonyl, C₁₋₈-alkylsulfonyl, C₃₋₈-cycloalkylsulfonyl, arylsulfonyl, arylsulfonyl, arylsulfonyl C₁₋₈-alkylsulfinyl, C₃₋₈-cycloalkylsulfinyl, arylsulfinyl, N, S-C₁₋₈-dialkylsulfonymidoyl, S-C₁₋₈-alkylsulfonimidoyl, C₁₋₈-alkylsulfonylaminocarbonyl, C₃₋₈-cycloalkylsulfonylaminocarbonyl, C₃₋₈-cycloalkylaminosulfonyl, aryl-C₁₋₈-alkylcarbonylamino, C₃₋₈-cycloalkyl-C₁₋₈-alkylcarbonylamino, heteroarylcarbonylamino, C ₋₈-alkoxy-C₁₋₈-alkylcarbonylamino, C₁₋₈-hidroxialquilcarbonilamino, C₁₋₈-trialkylsilyl; and R⁷ and R⁸ are independently hydrogen, hydroxy, halogen, C₁₋₈-alkyl, C₁₋₈-haloalkyl, C₂₋₈-alkenyl, C₂₋₈-alkynyl, C₁₋₈-alkoxy-C₁₋₈-alkyl, C₁₋ ₈-haloalkoxy-C₁₋₈-alkyl, C₁₋₈-alkylthio-C₁₋₈-alkyl, C₁₋₈-alkylsulfinyl-C₁₋₈-alkyl, C₁₋₈-alkylsulfonyl-C₁₋₈-alkyl, C₁₋₈- alkylcarbonyl, C₁₋₈-haloalkylcarbonyl, C₃₋₈-cycloalkylcarbonyl, C₁₋₈-alkoxycarbonyl, C₂₋₈-haloalkoxycarbonyl, C₃₋₈-cycloalkoxycarbonyl, C₁₋₈-alkylaminocarbonyl, C₁₋₁₀-dialkylaminocarbonyl, C₃₋₁₀-cycloalkylaminocarbonyl, C₁₋₈-alkoxy, C₁₋₈-alkylthio, C₁₋₈-haloalkylthio, C₃₋₈-cycloalkylthio.

ARP180100756A 2017-03-30 2018-03-28 REPLACED PIRROLIDINONES AND ITS SALTS AND THEIR USE AS HERBICIDE ACTIVE INGREDIENTS AR111303A1 (en)

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