AR094157A1 - TRIAZOLS AND REPLACED IMIDAZOLS AND THEIR USE AS FUNGICIDES - Google Patents

TRIAZOLS AND REPLACED IMIDAZOLS AND THEIR USE AS FUNGICIDES

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Publication number
AR094157A1
AR094157A1 ARP130104882A ARP130104882A AR094157A1 AR 094157 A1 AR094157 A1 AR 094157A1 AR P130104882 A ARP130104882 A AR P130104882A AR P130104882 A ARP130104882 A AR P130104882A AR 094157 A1 AR094157 A1 AR 094157A1
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Argentina
Prior art keywords
alkyl
cycloalkyl
alkoxy
halogen
independently selected
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ARP130104882A
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Spanish (es)
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Basf Se
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Abstract

Compuestos de triazol e imidazol sustituidos de la fórmula (1), a sus N-óxidos y sales, a su preparación y a intermediarios para prepararlos. También el uso de estos compuestos para combatir hongos dañinos, a semillas recubiertas con al menos uno de dichos compuestos y también a composiciones que comprenden al menos uno de dichos compuestos. Reivindicación 1: Compuestos de la fórmula (1) en donde: R es O ó CH₂; Q es O ó CH₂; en donde R o Q son O; A es CH o N; D es H, halógeno o SRD; en donde RD es hidrógeno, alquilo C₁₋₆, haloalquilo C₁₋₆, alquenilo C₂₋₆, haloalquenilo C₂₋₆, alquinilo C₂₋₆, haloalquinilo C₂₋₆ o CN; R³ se selecciona independientemente de halógeno, CN, NO₂, OH, SH, alquilo C₁₋₆, alcoxi C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₈, cicloalquiloxi C₃₋₈, NH₂, NH(alquilo C₁₋₄), N(alquilo C₁₋₄)₂, NH(cicloalquilo C₃₋₆), N(cicloalquilo C₃₋₆)₂, S(O)ₚ(alquilo C₁₋₄), C(=O)(alquilo C₁₋₄), C(=O)(OH), C(=O)(O-alquilo C₁₋₄), C(=O)(NH(alquilo C₁₋₄)), C(=O)(N(alquilo C₁₋₄)₂), C(=O)(NH(cicloalquilo C₃₋₆)) y C(=O)-(N(cicloalquilo C₃₋₆)₂; en donde cada uno de R³ es no sustituido o sustituido adicionalmente con 1, 2, 3 ó 4 R³ᵃ; en donde R³ᵃ se selecciona independientemente de halógeno, CN, NO₂, OH, alquilo C₁₋₄, haloalquilo C₁₋₄, cicloalquilo C₃₋₈, halocicloalquilo C₃₋₈, alcoxi C₁₋₄ y halógeno-alcoxi C₁₋₄; n es 0, 1, 2, 3 ó 4; Y es un enlace directo o un grupo divalente seleccionado del grupo que consiste en -O-, -S-, -SO-, -SO₂-, -NH-, -N(alquil C₁₋₄)-, CR¹⁵R⁸-, -CR⁹R¹⁰-CR¹¹R¹²-, -CR¹³=CR¹⁴ y -CºC-; en donde R⁸, R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵ se seleccionan independientemente de hidrógeno, halógeno, CN, nitro, OH, alquilo C₁₋₄, halógeno-alquilo C₁₋₄, alcoxi C₁₋₄ y halógeno-alcoxi C₁₋₄; Z es un heteroarilo de 5 ó 6 miembros, en donde el heteroarilo contiene 1, 2, 3 ó 4 heteroátomos seleccionados del grupo que consiste en O, N, y S, o fenilo, en donde el heteroarilo o fenilo es no sustituido (m = 0) o sustituido con (R⁴)ₘ, en donde m es 0, 1, 2, 3, 4 ó 5; R⁴ se selecciona independientemente de halógeno, CN, NO₂, OH, SH, alquilo C₁₋₆, alcoxi C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₈, cicloalquiloxi C₃₋₈, NH₂, NH(alquilo C₁₋₄, N(alquilo C₁₋₄)₂, NH(cicloalquilo C₃₋₆), N(cicloalquilo C₃₋₆)₂, S(O)ₚ(alquilo C₁₋₄), C(=O)(alquilo C₁₋₄, C₍₌O₎₍OH₎, C₍₌O₎₍O₋ₐₗqᵘⁱₗₒ C₁₋₄), C(=O)(NH(alquilo C₁₋₄)), C(=O)(N(alquilo C₁₋₄)₂), C(=O)(NH(cicloalquilo C₃₋₆)) y C(=O)-(N(cicloalquilo C₃₋₆)₂; en donde cada uno de R⁴ es no sustituido o sustituido adicionalmente con 1, 2, 3 ó 4 R⁴ᵃ; en donde R⁴ᵃ se selecciona independientemente de halógeno, CN, NO₂, OH, alquilo C₁₋₄, haloalquilo C₁₋₄, cicloalquilo C₃₋₈, halocicloalquilo C₃₋₈, alcoxi C₁₋₄ y haloalcoxi C₁₋₄; p es 0, 1 ó 2; x es 0, 1, 2, 3 ó 4; R⁵ es H, halógeno, CN, NO₂, OH, SH, alquilo C₁₋₆, alcoxi C₁₋₆, alquil C₁₋₆tio, alquil C₁₋₆sulfinilo, alquil C₁₋₆sulfonilo, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₈, cicloalquiloxi C₃₋₈, cicloalquil C₃₋₈-alquilo C₁₋₄, NH₂, NH(alquilo C₁₋₄), N(alquilo C₁₋₄)₂, NH(cicloalquilo C₃₋₆), N(cicloalquilo C₃₋₆)₂, C(=O)-alquilo C₁₋₄, C₍₌O₎OH, C₍₌O₎₋O₋ₐₗqᵘⁱₗₒ C₁₋₄, C₍₌O₎₋NH₍ₐₗqᵘⁱₗₒ C₁₋₄), C(=O)-N(alquilo C₁₋₄)₂, C(=O)-NH(cicloalquilo C₃₋₆, C₍₌O₎₋N₍ᶜⁱᶜₗₒₐₗqᵘⁱₗₒ C₃₋₆)₂, fenilo, heteroarilo, fenil-alquilo C₁₋₄ y heteroaril-alquilo C₁₋₄, en donde el radical heteroarilo en los últimos grupos mencionados tienen 5 ó 6 miembros; y en donde las porciones alifáticas, alicíclicas y aromáticas de R⁵ son no sustituidas o sustituidas con 1, 2, 3, 4 o hasta la mayor cantidad posible de sustituyentes R⁵ᵃ; en donde R⁵ᵃ se selecciona independientemente de halógeno, CN, NO₂, OH, SH, NH₂, alquilo C₁₋₆, haloalquilo C₁₋₆, cicloalquilo C₃₋₈, halocicloalquilo C₃₋₈, alcoxi C₁₋₆, haloalcoxi C₁₋₆, alquil C₁₋₆tio, haloalquil C₁₋₆tio y alcoxi C₁₋₄-alquilo C₁₋₄; R⁶ es H o se selecciona de los sustituyentes definidos para R⁵, en donde las porciones alifáticas, alicíclicas y aromáticas de R⁶ son no sustituidas o sustituidas con 1, 2, 3, 4 o hasta la mayor cantidad posibles de R⁶ᵃ, en donde R⁶ᵃ se define como R⁵ᵃ; o R⁵ y R⁶, junto con el átomo de carbono al que están unidos, forman un carbociclo saturado o parcialmente insaturado de 3, 4, 5, 6 ó 7 miembros, o un heterociclo saturado o parcialmente insaturado de 3, 4, 5, 6 ó 7 miembros, en donde el heterociclo contiene 1, 2, 3 ó 4 heteroátomos seleccionados de N, O y S, y en donde el carbociclo o heterociclo son no sustituidos o tienen 1, 2, 3 ó 4 sustituyentes seleccionados independientemente de halógeno, CN, NO₂, OH, SH, NH₂, alquilo C₁₋₆, haloalquilo C₁₋₆, alcoxi C₁₋₆, haloalcoxi C₁₋₆, alquil C₁₋₆tio, haloalquil C₁₋₆tio, alcoxi C₁₋₄-alquilo C₁₋₄, fenilo y fenoxi; y en donde uno o dos grupos CH₂ del carbociclo o heterociclo se pueden reemplazar por un grupo seleccionado independientemente de C(=O) y C(=S); o R⁵ y R⁶, junto con el átomo de carbono al que están unidos (denominado C*), forman un grupo (C*=CR⁵⁵R⁶⁶), en donde R⁵⁵, R⁶⁶ se seleccionan independientemente del grupo que consiste en hidrógeno, halógeno, CN, NO₂, OH, SH, NH₂, alquilo C₁₋₆, haloalquilo C₁₋₆, alcoxi C₁₋₆, haloalcoxi C₁₋₆, alquil C₁₋₆tio, haloalquil C₁₋₆tio y alcoxi C₁₋₄-alquilo C₁₋₄; R⁷ se selecciona independientemente de alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₈, en donde cada R⁷ es no sustituido o sustituido adicionalmente con 1, 2, 3 ó 4 R⁷ᵃ; en donde R⁷ᵃ se selecciona independientemente de halógeno, OH y alcoxi C₁₋₆; o dos sustituyentes R⁷: R⁷¹ y R⁷², junto con los átomos de carbono a los que están unidos, forman un carbociclo o heterociclo saturado de 3, 4, 5, 6 ó 7 miembros, en donde el heterociclo contiene 1, 2, 3 ó 4 átomos O; o es 0, 1, 2, 3 ó 4; y los N-óxidos y las sales de estos aceptables en la agricultura; siempre que si R es O y Q es CH₂, x no es 0.Substituted triazole and imidazole compounds of the formula (1), their N-oxides and salts, their preparation and intermediates to prepare them. Also the use of these compounds to combat harmful fungi, to seeds coated with at least one of said compounds and also to compositions comprising at least one of said compounds. Claim 1: Compounds of the formula (1) wherein: R is O or CH₂; Q is O or CH₂; where R or Q are O; A is CH or N; D is H, halogen or SRD; wherein RD is hydrogen, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₂₋₆ alkenyl, C₂₋₆ haloalkenyl, C₂₋₆ alkynyl, C₂₋₆ haloalkynyl or CN; R³ is independently selected from halogen, CN, NO₂, OH, SH, C₁₋₆ alkyl, C alco alkoxy, C₂₋₆ alkenyl, C₂₋₆ alkynyl, C₃₋₈ cycloalkyl, C₃₋₈ cycloalkyloxy, NH₂, NH (alkyl C₁₋₄), N (C₁₋₄ alkyl) ₂, NH (C₃₋₆ cycloalkyl), N (C₃₋₆ cycloalkyl) ₂, S (O) ₚ (C₁₋₄ alkyl), C (= O) (alkyl C₁₋₄), C (= O) (OH), C (= O) (O-C₁₋₄ alkyl), C (= O) (NH (C₁₋₄ alkyl)), C (= O) (N (C₁₋₄ alkyl) ₂), C (= O) (NH (C₃₋₆ cycloalkyl)) and C (= O) - (N (C₃₋₆ cycloalkyl) ₂, where each of R³ is unsubstituted or further substituted with 1, 2, 3 or 4 R³ᵃ, wherein R³ᵃ is independently selected from halogen, CN, NO₂, OH, C₁₋₄ alkyl, C halo haloalkyl, C₃₋₈ cycloalkyl, C₃₋₈ halocycloalkyl, C₁₋ alkoxy ₄ and halogen-C₁₋₄ alkoxy; n is 0, 1, 2, 3 or 4; Y is a direct bond or a divalent group selected from the group consisting of -O-, -S-, -SO-, -S O₂-, -NH-, -N (C₁₋₄ alkyl) -, CR¹⁵R⁸-, -CR⁹R¹⁰-CR¹¹R¹²-, -CR¹³ = CR¹⁴ and -CºC-; where R⁸, R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴ , R¹⁵ are independently selected from hydrogen, halogen, CN, nitro, OH, C₁₋₄ alkyl, halogen-C₁₋₄ alkyl, C₁₋₄ alkoxy and halogen-C₁₋₄ alkoxy; Z is a 5 or 6 membered heteroaryl, wherein the heteroaryl contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N, and S, or phenyl, wherein the heteroaryl or phenyl is unsubstituted (m = 0) or substituted with (R⁴) ₘ, where m is 0, 1, 2, 3, 4 or 5; R⁴ is independently selected from halogen, CN, NO₂, OH, SH, C₁₋₆ alkyl, C alco alkoxy, C₂₋₆ alkenyl, C₂₋₆ alkynyl, C₃₋₈ cycloalkyl, C₃₋₈ cycloalkyloxy, NH₂, NH (alkyl C₁₋₄, N (C₁₋₄ alkyl) ₂, NH (C₃₋₆ cycloalkyl), N (C₃₋₆ cycloalkyl) ₂, S (O) ₚ (C₁₋₄ alkyl), C (= O) (C₁ alkyl ₋₄, C₍₌O₎₍OH₎, C₍₌O₎₍O₋ₐₗqᵘⁱₗₒ C₁₋₄), C (= O) (NH (C₁₋₄ alkyl)), C (= O) (N (alkyl C₁₋₄) ₂), C (= O) (NH (C₃₋₆ cycloalkyl)) and C (= O) - (N (C₃₋₆ cycloalkyl) ₂, where each of R⁴ is unsubstituted or additionally substituted with 1, 2, 3 or 4 R⁴ᵃ, wherein R⁴ᵃ is independently selected from halogen, CN, NO₂, OH, C₁₋₄ alkyl, C₁₋₄ haloalkyl, C₃₋₈ cycloalkyl, C₃₋₈ halocycloalkyl, C₁₋₄ alkoxy and C₁₋₄ haloalkoxy; p is 0, 1 or 2; x is 0, 1, 2, 3 or 4; R⁵ is H, halogen, CN, NO₂, OH, SH, C₁₋ alkyl , C₁₋₆ alkoxy, C₁₋₆thio alkyl, C₁₋₆sulfinyl alkyl, C₁₋₆sulfonyl alkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl, C₃₋₈ cycloalkyl, C₃₋₈ cycloalkyloxy, C₃₋₈ cycloalkyl , NH₂, NH (C₁₋₄ alkyl), N (C₁₋₄ alkyl) ₂, NH (C₃₋₆ cycloalkyl), N (C₃₋₆ cycloalkyl) ₂, C (= O) -C₁₋₄ alkyl, C₍ ₌O₎OH, C₍₌O₎₋O₋ₐₗqᵘⁱₗₒ C₁₋₄, C₍₌O₎₋NH₍ₐₗqᵘⁱₗₒ C₁₋₄), C (= O) -N (C₁₋₄ alkyl) ₂, C (= O) -NH (C₃₋₆ cycloalkyl, C₍₌O₎₋N₍ᶜⁱᶜₗₒₐₗqᵘⁱₗₒ C₃₋₆) ₂, phenyl, heteroaryl, phenyl-C₁₋₄ alkyl and heteroaryl-C₁₋₄ alkyl, wherein the heteroaryl radical in the Last mentioned groups have 5 or 6 members; and wherein the aliphatic, alicyclic and aromatic portions of R⁵ are unsubstituted or substituted with 1, 2, 3, 4 or even as many R⁵ᵃ substituents as possible; wherein R⁵ᵃ is independently selected from halogen, CN, NO₂, OH, SH, NH₂, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₃₋₈ cycloalkyl, C₃₋₈ halocycloalkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, alkyl C₁₋₆thio, C₁₋₆thio haloalkyl and C₁₋₄-C₁₋₄ alkoxy; R⁶ is H or is selected from the substituents defined for R⁵, wherein the aliphatic, alicyclic and aromatic portions of R⁶ are unsubstituted or substituted with 1, 2, 3, 4 or as many R⁶ᵃ as possible, where R⁶ᵃ is define as R⁵ᵃ; or R⁵ and R⁶, together with the carbon atom to which they are attached, form a saturated or partially unsaturated carbocycle of 3, 4, 5, 6 or 7 members, or a saturated or partially unsaturated heterocycle of 3, 4, 5, 6 or 7 members, wherein the heterocycle contains 1, 2, 3 or 4 heteroatoms selected from N, O and S, and wherein the carbocycle or heterocycle are unsubstituted or have 1, 2, 3 or 4 substituents independently selected from halogen, CN, NO₂, OH, SH, NH₂, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, C₁₋₆thio alkyl, C₁₋₆thio haloalkyl, C₁₋₄ alkoxy-C₁₋₄ alkyl, phenyl and phenoxy; and wherein one or two CH₂ groups of the carbocycle or heterocycle can be replaced by a group selected independently of C (= O) and C (= S); or R⁵ and R⁶, together with the carbon atom to which they are attached (called C *), form a group (C * = CR⁵⁵R⁶⁶), where R⁵⁵, R⁶⁶ are independently selected from the group consisting of hydrogen, halogen, CN, NO₂, OH, SH, NH₂, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, C₁₋₆thio alkyl, C₁₋₆thio haloalkyl and C₁₋₄ alkoxy-C₁₋₄ alkyl; R⁷ is independently selected from C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl, C₃₋₈ cycloalkyl, wherein each R⁷ is unsubstituted or further substituted with 1, 2, 3 or 4 R⁷ᵃ; wherein R⁷ᵃ is independently selected from halogen, OH and C₁₋₆ alkoxy; or two substituents R⁷: R⁷¹ and R⁷², together with the carbon atoms to which they are attached, form a saturated carbocycle or heterocycle of 3, 4, 5, 6 or 7 members, wherein the heterocycle contains 1, 2, 3 or 4 atoms O; or is 0, 1, 2, 3 or 4; and the N-oxides and salts thereof acceptable in agriculture; provided that if R is O and Q is CH₂, x is not 0.

ARP130104882A 2012-12-19 2013-12-19 TRIAZOLS AND REPLACED IMIDAZOLS AND THEIR USE AS FUNGICIDES AR094157A1 (en)

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WO2015086462A1 (en) 2013-12-12 2015-06-18 Basf Se Substituted [1,2,4]triazole and imidazole compounds
US9815798B2 (en) 2014-03-26 2017-11-14 Basf Se Substituted [1,2,4]triazole and imidazole compounds as fungicides
CA2948208A1 (en) 2014-05-13 2015-11-19 Basf Se Substituted [1,2,4]triazole and imidazole compounds as fungicides
AR100743A1 (en) 2014-06-06 2016-10-26 Basf Se COMPOUNDS OF [1,2,4] SUBSTITUTED TRIAZOL

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