AR099120A1 - DERIVATIVES OF QUINOLINE AS INSECTICIDES AND ACARICIDES - Google Patents

DERIVATIVES OF QUINOLINE AS INSECTICIDES AND ACARICIDES

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Publication number
AR099120A1
AR099120A1 ARP150100125A ARP150100125A AR099120A1 AR 099120 A1 AR099120 A1 AR 099120A1 AR P150100125 A ARP150100125 A AR P150100125A AR P150100125 A ARP150100125 A AR P150100125A AR 099120 A1 AR099120 A1 AR 099120A1
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AR
Argentina
Prior art keywords
alkyl
alkoxy
halogen
cyano
nitro
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ARP150100125A
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Spanish (es)
Inventor
Prof Dr Jeschke Peter
Dr Voerste Arnd
Grgens Ulrich
Dr Heil Markus
Dr Maue Michael
Kevin Dr Heilmann Eike
Dr Ilg Kerstin
Dr Turberg Andreas
Original Assignee
Bayer Cropscience 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.)
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Publication date
Application filed by Bayer Cropscience Ag filed Critical Bayer Cropscience Ag
Publication of AR099120A1 publication Critical patent/AR099120A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La presente solicitud se refiere a compuestos, procedimiento para su preparación y su uso como insecticidas y acaricidas. Reivindicación 1: Compuestos de la formula general (1) en la que R¹ representa halógeno, nitro, ciano, representa alquilo C₁₋₆, cicloalquilo C₃₋₆, alcoxi C₁₋₆, alquiltio C₁₋₆, alquilsulfinilo C₁₋₆, alquilsulfonilo C₁₋₆, alquilcarbonilo C₁₋₆, alcoxicarbonilo C₁₋₆, alcoxiimino C₁₋₆-alquilo C₁₋₆ o alquilsulfoniloxi C₁₋₆ dado el caso mono- o polisustituidos con halógeno, o R¹ representa una cadena de carbono C₁₋₄ que dado el caso contiene 1 ó 2 heteroátomos, que está unida en dos posiciones de anillo adyacentes y forma un anillo alifático, aromático, heteroaromático o heterocíclico el cual, dado el caso está mono- o polisustituido con alquilo C₁₋₆ o con halógeno, siendo entonces n igual a 1 y siendo los heteroátomos seleccionados del grupo que se compone de N, S y O; n representa 1, 2, 3, 4 ó 5; R² representa hidrógeno, halógeno, ciano, hidroxi o representa alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆ o alcoxi C₁₋₆ dado el caso mono- o polisustituidos, de manera igual o diferente, habiéndose seleccionado los sustituyentes independientemente entre sí de flúor, cloro, bromo o yodo; R³ representa hidrógeno, representa alquilo C₁₋₄, alquenilo C₂₋₄, alquinilo C₃₋₄, alquilcarbonilo C₁₋₄ o alcoxicarbonilo C₁₋₄ dado el caso mono- o polisustituidos, de manera igual o diferente, habiéndose seleccionado los sustituyentes independientemente entre sí de ciano, halógeno, alquilo C₁₋₄ o alcoxi C₁₋₄; Q¹ representa C-R⁴ o N; Q² representa C-R⁴; Q³ representa C-R⁴; Q⁴ representa C-R⁴ o N; siendo que Q¹ representa C-R⁴, cuando Q⁴ representa N y Q⁴ representa C-R⁴, cuando Q¹ representa N; R⁴ representa hidrógeno, halógeno, nitro, ciano, alquilo C₁₋₄, haloalquilo C₁₋₄ o alcoxi C₁₋₄; R⁶ representa hidrógeno, halógeno, nitro, ciano, representa alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₆, alcoxi C₁₋₆, (alcoxi C₁₋₆)carbonilo, alquilamino C₁₋₆, formilo, (alquil-C₁₋₆)carbonilo, alcoxiimino C₁₋₆-alquilo C₁₋₆, dialquilamino C₁₋₆, (alquilamino C₁₋₆)carbonilo, (dialquilamino C₁₋₆)carbonilo, alquiltio C₁₋₆, alquilsulfinilo C₁₋₆, alquilsulfonilo C₁₋₆, alquilaminosulfonilo C₁₋₆ o alquilsulfonilamino C₁₋₆ dado el caso mono- o polisustituidos, de manera igual o diferente, habiéndose seleccionado los sustituyentes independientemente entre sí de halógeno, ciano, nitro, hidroxi, amino, alquilo C₁₋₆, alcoxi C₁₋₆, cicloalquilo C₃₋₆, haloalcoxi C₁₋₆ o alquiltio C₁₋₆; X representa haloalquilo C₁₋₆ que dado el caso puede estar mono- a trisustituido adicionalmente, habiéndose seleccionado los sustituyentes independientemente entre sí de hidroxi, ciano o alcoxi C₁₋₄; W representa O ó S; G representa un par de electrones libre o representa oxígeno; A representa un grupo químico bivalente, que está seleccionado de los grupos -C(=O)NR¹³-, -C(=S)NR¹³-, -C(=O)NR¹³-NR¹⁶-, -C(=O)NR¹³C(R¹⁴)(R¹⁵)C(=O)NR¹⁶-, C(R¹⁴)(R¹⁵)NR¹³-C(=O)-, -CH=N-N(R¹³)-C(=W)-N(R¹⁶)-, -N(R¹³)-N(R¹⁶)-C(=O)- en el que el punto de unión (izquierdo) mencionado en cada caso en primer lugar se enlaza en el anillo y el punto de unión (derecho) mencionado en cada caso en segundo lugar se enlaza con Y; R¹³, R¹⁶ independientemente entre sí representan hidrógeno, representan alquilo C₁₋₄, alcoxi C₁₋₄-alquilo C₁₋₄, cianoalquilo C₁₋₄, cicloalquilo C₃₋₆, alquilcarbonilo C₁₋₄, alcoxicarbonilo C₁₋₄ o alquenilo C₂₋₄; R¹⁴, R¹⁵ independientemente entre sí representan hidrógeno o representan alquilo C₁₋₄ o R¹⁴, R¹⁵ juntos forman un anillo alifático de 3 a 6 miembros; Y representa hidrógeno o representa alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₆ o cicloalquenilo C₃₋₆ dado el caso mono- o polisustituidos, de manera igual o diferente, habiéndose seleccionado los sustituyentes de halógeno, nitro, ciano, hidroxi, aminotiocarbonilo, aminocarbonilo, alquilaminocarbonilo C₁₋₄, alquilaminotiocarbonilo C₁₋₄, haloalquilaminocarbonilo C₁₋₄, di-(alquil-C₁₋₄)-aminocarbonilo, di-(alquil-C₁₋₄)-aminotiocarbonilo, hidroxicarbonilo, alquilo C₁₋₄, haloalquilo C₁₋₄, cicloalquilo C₃₋₆, alquil C₁₋₄-cicloalquilo C₃₋₄, alquenilo C₂₋₆, alquinilo C₂₋₆, alcoxi C₁₋₆, haloalcoxi C₁₋₆, alcoxicarbonilo C₁₋₆, alquilcarbonilo C₁₋₆, alcoxiimino C₁₋₄-alquilo C₁₋₄, alquiltio C₁₋₆, alquilsulfinilo C₁₋₆,alquilsulfonilo C₁₋₆ o de arilo o heteroarilo dado el caso mono- o polisustituidos, de manera igual o diferente, habiéndose seleccionado los sustituyentes de halógeno, nitro, ciano, hidroxi, alquilo C₁₋₄, haloalquilo C₁₋₄, alcoxi C₁₋₆ o haloalcoxi C₁₋₆, o Y representa heterociclilo, arilo, aril-alquilo C₁₋₄, hetarilo, oxo-heterociclilo o hetaril-alquilo C₁₋₄ dado el caso sustituidos, habiéndose seleccionado los sustituyentes de halógeno, nitro, ciano, hidroxi, alquilo C₁₋₄, haloalquilo C₁₋₄, alcoxi C₁₋₆, o haloalcoxi C₁₋₆, alquiltio C₁₋₆, alquilsulfinilo C₁₋₆ o alquilsulfonilo C₁₋₆; así como sales y N-óxidos de compuestos de la fórmula (1). Reivindicación 10: Ácidos quinolincarboxílicos de la fórmula (2) en la que R⁴ᵃ, R⁴ᵇ, R⁴ᶜ y R⁴ᵈ independientemente entre sí tienen el significado descrito para R⁴ en la reivindicación 4 y R⁶ tiene el significado indicado en la reivindicación 4.The present application refers to compounds, process for their preparation and their use as insecticides and acaricides. Claim 1: Compounds of the general formula (1) wherein R¹ represents halogen, nitro, cyano, represents C₁₋₆ alkyl, C₃₋₆ cycloalkyl, C₁₋₆ alkoxy, C₁₋₆ alkylthio, C₁₋₆ alkylsulfinyl, C₁ alkylsulfonyl ₋₆, C₁₋₆ alkylcarbonyl, C₁₋₆ alkoxycarbonyl, C₁₋₆ alkoxyimino-C₁₋₆ alkyl or Cils-alkylsulfonyloxy, where appropriate mono- or polysubstituted with halogen, or R¹ represents a C₁₋₄ carbon chain given the case contains 1 or 2 heteroatoms, which is attached in two adjacent ring positions and forms an aliphatic, aromatic, heteroaromatic or heterocyclic ring which, if necessary, is mono- or polysubstituted with C₁₋₆ alkyl or halogen, then being n equal to 1 and the heteroatoms being selected from the group consisting of N, S and O; n represents 1, 2, 3, 4 or 5; R² represents hydrogen, halogen, cyano, hydroxy or represents C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl or C₁₋₆ alkoxy, if the case is mono- or polysubstituted, in the same or different manner, the substituents having been independently selected from yes of fluorine, chlorine, bromine or iodine; R³ represents hydrogen, represents C₁₋₄ alkyl, C₂₋₄ alkenyl, C₃₋₄ alkynyl, C₁₋₄ alkylcarbonyl or C₁₋₄ alkoxycarbonyl, if the case is mono- or polysubstituted, in the same or different manner, the substituents having been independently selected from each other cyano, halogen, C₁₋₄ alkyl or C₁₋₄ alkoxy; Q¹ represents C-R⁴ or N; Q² represents C-R⁴; Q³ represents C-R⁴; Q⁴ represents C-R⁴ or N; being that Q¹ represents C-R⁴, when Q⁴ represents N and Q⁴ represents C-R⁴, when Q¹ represents N; R⁴ represents hydrogen, halogen, nitro, cyano, C₁₋₄ alkyl, C₁₋₄ haloalkyl or C₁₋₄ alkoxy; R⁶ represents hydrogen, halogen, nitro, cyano, represents C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl, C₃₋₆ cycloalkyl, C₁₋₆ alkoxy, (C₁₋₆ alkoxy) carbonyl, C₁₋₆ alkylamino, formyl , (C-alkyl) carbonyl, C₁₋₆ alkoxyimino-C₁₋₆ alkyl, Cquila dialkylamino, (C₁₋₆ alkylamino) carbonyl, (C₁₋₆ dialkylamino) carbonyl, C₁₋₆ alkylthio, C₁₋₆ alkylsulfinyl , C₁₋₆ alkylsulfonyl, C₁₋₆ alkylaminosulfonyl or C₁₋₆ alkylsulfonylamino, in the same or different manner, the substituents having been independently selected from each other from halogen, cyano, nitro, hydroxy, amino, C₁₋ alkyl ₆, C₁₋₆ alkoxy, C₃₋₆ cycloalkyl, C₁₋₆ haloalkoxy or C₁₋₆ alkylthio; X represents C₁₋₆ haloalkyl which, if necessary, may be additionally mono-substituted, the substituents having been independently selected from each other of hydroxy, cyano or C₁₋₄ alkoxy; W represents O or S; G represents a free electron pair or represents oxygen; A represents a bivalent chemical group, which is selected from the groups -C (= O) NR¹³-, -C (= S) NR¹³-, -C (= O) NR¹³-NR¹⁶-, -C (= O) NR¹³C ( R¹⁴) (R¹⁵) C (= O) NR¹⁶-, C (R¹⁴) (R¹⁵) NR¹³-C (= O) -, -CH = NN (R¹³) -C (= W) -N (R¹⁶) -, - N (R¹³) -N (R¹⁶) -C (= O) - where the junction point (left) mentioned in each case is first linked to the ring and the junction point (right) mentioned in each case secondly it is linked with Y; R¹³, R¹⁶ independently represent each other hydrogen, represent C₁₋₄ alkyl, C₁₋₄ alkoxy-C₁₋₄ alkyl, Ciano cyanoalkyl, C₃₋₆ cycloalkyl, C₁₋₄ alkylcarbonyl, C₁₋₄ alkoxycarbonyl or C₂₋₄ alkenyl; R¹⁴, R¹⁵ independently of each other represent hydrogen or represent C₁₋₄ or R¹⁴ alkyl, R¹⁵ together form a 3- to 6-membered aliphatic ring; Y represents hydrogen or represents C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl, C₃₋₆ cycloalkyl or C₃₋₆ cycloalkenyl, in the same or different case, in the same or different manner, the halogen substituents having been selected, nitro, cyano, hydroxy, aminothiocarbonyl, aminocarbonyl, C₁₋₄ alkylaminocarbonyl, C₁₋₄ alkylaminothiocarbonyl, C₁₋₄ haloalkylaminocarbonyl, di- (C--alkyl) -aminocarbonyl, di- (C-alkyl) -amino-thiocarbonyl, hydroxycarbonyl , C₁₋₄ alkyl, C₁₋₄ haloalkyl, C₃₋₆ cycloalkyl, C₁₋₄ alkyl-C₃₋₄ cycloalkyl, C₂₋₆ alkenyl, C₁₋₆ alkynyl, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, C₁₋₆ alkoxycarbonyl , C₁₋₆ alkylcarbonyl, C₁₋₄ alkoxyimino-C₁₋₄ alkyl, Cilt alkylthio, C₁₋₆ alkylsulfinyl, C₁₋₆ alkylsulfonyl or aryl or heteroaryl, where appropriate mono- or polysubstituted, equally or differently nte, the halogen, nitro, cyano, hydroxy, C₁₋₄ alkyl, C halo haloalkyl, C₁₋₆ alkoxy or C₁₋₆ haloalkoxy substituents having been selected, and Y represents heterocyclyl, aryl, aryl-C₁₋₄ alkyl, heteroaryl , substituted oxo-heterocyclyl or C-alkyl, where the halogen, nitro, cyano, hydroxy, C₁₋₄ alkyl, C₁₋₄ haloalkyl, C₁₋₆ alkoxy, or C₁₋₆ haloalkoxy substituents have been selected, C₁₋₆ alkylthio, C₁₋₆ alkylsulfinyl or C₁₋₆ alkylsulfonyl; as well as salts and N-oxides of compounds of the formula (1). Claim 10: Quinolinecarboxylic acids of the formula (2) in which R⁴ᵃ, R⁴ᵇ, R⁴ᶜ and R⁴ᵈ independently of one another have the meaning described for R⁴ in claim 4 and R⁶ has the meaning indicated in claim 4.

ARP150100125A 2014-01-20 2015-01-16 DERIVATIVES OF QUINOLINE AS INSECTICIDES AND ACARICIDES AR099120A1 (en)

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WO2015107133A1 (en) 2015-07-23
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