AR089882A1 - PIRIMIDINE FUNGICIDE COMPOUNDS - Google Patents

PIRIMIDINE FUNGICIDE COMPOUNDS

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Publication number
AR089882A1
AR089882A1 ARP130100326A AR089882A1 AR 089882 A1 AR089882 A1 AR 089882A1 AR P130100326 A ARP130100326 A AR P130100326A AR 089882 A1 AR089882 A1 AR 089882A1
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AR
Argentina
Prior art keywords
alkyl
alkoxy
haloalkoxy
haloalkyl
alkynyl
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Spanish (es)
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Basf Se
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Publication of AR089882A1 publication Critical patent/AR089882A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom

Abstract

Compuestos I fungicidas de pirimidina, su uso y los métodos para combatir hongos fitopatogénicos. Asimismo, procesos para preparar compuestos de la fórmula (1) e intermediarios. Reivindicación 1: Compuestos de la fórmula (1) en donde: Rᵃ⁵ es metoxi o halometoxi; Rᵃ², Rᵃ⁶ son, independientemente entre sí, hidrógeno, halógeno, CN, NO₂, OH, SH, alquilo C₁₋₄, haloalquilo C₁₋₄, alcoxi C₁₋₄, haloalcoxi C₁₋₄, alquiltio C₁₋₄, haloalquiltio C₁₋₄, alquilsulfinilo C₁₋₄, haloalquilsulfinilo C₁₋₄, alquilsulfonilo C₁₋₄, haloalquilsulfonilo C₁₋₄, alcoxi C₁₋₄-alquilo C₁₋₄, alcoxi C₁₋₄-alcoxi C₁₋₄, alquenilo C₂₋₄, alquinilo C₂₋₄, haloalquenilo C₂₋₄, haloalquinilo C₂₋₄, cicloalquilo C₃₋₈, cicloalquiloxi C₃₋₈, cicloalquil C₃₋₈-alquilo C₁₋₄, NRARB, C(=O)R, C(=NOR)R o C(=NH)-O-R; RA, RB son, independientemente entre sí, hidrógeno, alquilo C₁₋₄, alquenilo C₂₋₄, alquinilo C₂₋₄, fenilo, bencilo, cicloalquilo C₃₋₈, cicloalquenilo C₃₋₈ o C(=O)-R; R es hidrógeno, OH, NH₂, alquilo C₁₋₄, haloalquilo C₁₋₄, alquenilo C₂₋₄, alquinilo C₂₋₄, alcoxi C₁₋₄, haloalcoxi C₁₋₄, alquilamino C₁₋₄ o di(alquil C₁₋₄)amino; R es hidrógeno, alquilo C₁₋₄, haloalquilo C₁₋₄, alquenilo C₂₋₄, alquinilo C₂₋₄ o alcoxi C₁₋₄-alquilo C₁₋₄, R es hidrógeno o alquilo C₁₋₄; R es hidrógeno, alquilo C₁₋₄, haloalquilo C₁₋₄, alcoxi C₁₋₄, haloalcoxi C₁₋₄, alcoxi C₁₋₄-alquilo C₁₋₄, haloalcoxi C₁₋₄-alquilo C₁₋₄, alquenilo C₂₋₄, haloalquenilo C₂₋₄, alquinilo C₂₋₄, haloalquinilo C₂₋₄, CN, CH₂CN, NRARB o CH₂-O-C(=O)R; R¹, R² son, independientemente entre sí, hidrógeno, halógeno, OH, CN, alquilo C₁₋₄, haloalquilo C₁₋₄, alcoxi C₁₋₄, haloalcoxi C₁₋₄, alcoxi C₁₋₄-alquilo C₁₋₄, haloalcoxi C₁₋₄-alquilo C₁₋₄, alquenilo C₂₋₄, haloalquenilo C₂₋₄, alquinilo C₂₋₄, haloalquinilo C₂₋₄, cicloalquilo C₃₋₈, cicloalquiloxi C₃₋₈, cicloalquil C₃₋₈-alquilo C₁₋₄, NRARB, C(=O)R, C(=NOR)R, C(=NH)-O-R o bencilo, en donde la porción fenilo de bencilo es no sustituida o tiene 1, 2, 3, 4 ó 5 sustituyentes seleccionados del grupo que consiste en CN, halógeno, alquilo C₁₋₄, haloalquilo C₁₋₄, alcoxi C₁₋₄, haloalcoxi C₁₋₄, (alcoxi C₁₋₄)carbonilo y di(alquil C₁₋₄)aminocarbonilo, o dos radicales R¹ y R² que se unen al mismo átomo de carbono forman, junto con dicho átomo de carbono, 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 los átomos miembros del anillo del heterociclo antes mencionado incluyen, además de átomos de carbono, 1, 2, 3 ó 4 heteroátomos seleccionados del grupo de N, O y S, y en donde el ciclo antes mencionado es no sustituido o tiene 1, 2, 3 ó 4 sustituyentes seleccionados de halógeno, CN, OH, SH, alquilo C₁₋₄, alcoxi C₁₋₄ o alquiltio C₁₋₄; y uno o dos grupos CH₂ de los ciclos antes mencionados se pueden reemplazar por uno o dos grupos C(=O) o C(=S), respectivamente; n indica la cantidad de sustituyentes Rᵇ en el anillo fenilo, y n es 0, 1, 2, 3 ó 4; Rᵇ es halógeno, CN, NO₂, alquilo C₁₋₄, haloalquilo C₁₋₄, alcoxi C₁₋₄, haloalcoxi C₁₋₄, alquenilo C₂₋₄, haloalquenilo C₂₋₄, alquinilo C₂₋₄, haloalquinilo C₂₋₄, NRARB, C(=NOR)R o C(=NH)-O-R, en donde es posible para n = 2, 3 ó 4 que Rᵇ sean idénticos o diferentes; Het es un heteroarilo de 5 ó 6 miembros, en donde los átomos miembros del anillo del heteroarilo incluyen, además de átomos de carbono, 1, 2, 3 ó 4 heteroátomos seleccionados del grupo de N, O y S y en donde el heteroarilo es no sustituido o tiene 1, 2, 3 ó 4 grupos Rᶜ idénticos o diferentes: Rᶜ es halógeno, CN, NO₂, alquilo C₁₋₆, haloalquilo C₁₋₆, alcoxi C₁₋₆, haloalcoxi C₁₋₆, alquiltio C₁₋₆, haloalquiltio C₁₋₆, alquilsulfinilo C₁₋₆, haloalquilsulfinilo C₁₋₆, alquilsulfonilo C₁₋₆, haloalquilsulfonilo C₁₋₆, alcoxi C₁₋₆-alquilo C₁₋₄, haloalcoxi C₁₋₆-alquilo C₁₋₄, alquenilo C₂₋₆, alquinilo C₂₋₆, NRARB, C(=O)R, C(=NOR)R, C(=NH)-O-R, cicloalquilo C₃₋₈, cicloalquil C₃₋₈-alquilo C₁₋₄, fenilo, fenil-alquilo C₁₋₄, fenoxi, fenoxi-alquilo C₁₋₄ o un heteroarilo de 5 ó 6 miembros, en donde los átomos miembros del anillo del heteroarilo incluyen, además de átomos de carbono, 1, 2, 3 ó 4 heteroátomos seleccionados del grupo de N, O y S, y en donde los radicales cíclicos antes mencionados son no sustituidos o tienen 1, 2, 3 ó 4 sustituyentes Rᵈ idénticos o diferentes: Rᵈ es halógeno, CN, alquilo C₁₋₄, haloalquilo C₁₋₄, alcoxi C₁₋₄ o haloalcoxi C₁₋₄; o dos radicales Rᶜ que se unen a los átomos miembros del anillo adyacente del grupo Het forman, junto con dichos átomos miembros del anillo, un carbociclo o heterociclo fusionado, saturado, parcialmente insaturado o aromático de 5, 6 ó 7 miembros, en donde los átomos miembros del anillo del heterociclo fusionado incluyen, además de átomos de carbono, 1, 2, 3 ó 4 heteroátomos seleccionados del grupo de N, O y S, y en donde el carbociclo o heterociclo fusionado es no sustituido o tiene 1, 2, 3 ó 4 grupos radicales Rᵉ idénticos o diferentes: Rᵉ es halógeno, CN, alquilo C₁₋₄, haloalquilo C₁₋₄, alcoxi C₁₋₄ o haloalcoxi C₁₋₄; y los N-óxidos y las sales de estos aceptables en la agricultura.Pyrimidine fungicidal compounds I, their use and methods to combat phytopathogenic fungi. Also, processes for preparing compounds of the formula (1) and intermediates. Claim 1: Compounds of the formula (1) wherein: Rᵃ⁵ is methoxy or halomethoxy; Rᵃ², Rᵃ⁶ are, independently of each other, hydrogen, halogen, CN, NO₂, OH, SH, C₁₋₄ alkyl, C₁₋₄ haloalkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkoxy, C₁₋₄ alkylthio, C₁₋₄ haloalkylthio , C₁₋₄ alkylsulfinyl, C₁₋₄ haloalkylsulfinyl, C₁₋₄ alkylsulfonyl, C₁₋₄ haloalkylsulfonyl, C₁₋₄ alkoxyC₁₋₄ alkyl, C₁₋₄ alkoxyC₁₋₄ alkoxy, C₂₋₄ alkenyl, C₂₋₄ alkynyl , C₂₋₄ haloalkenyl, C₂₋₄ haloalkynyl, C₃₋₈ cycloalkyl, C₃₋₈ cycloalkyloxy, C₃₋₈ cycloalkyl, NRARB, C (= O) R, C (= NOR) R or C (= NH) -OR; RA, RB are, independently of one another, hydrogen, C₁₋₄ alkyl, C₂₋₄ alkenyl, C₂₋₄ alkynyl, phenyl, benzyl, C₃₋₈ cycloalkyl, C₃₋₈ or C (= O) -R cycloalkenyl; R is hydrogen, OH, NH₂, C₁₋₄ alkyl, C₁₋₄ haloalkyl, C₂₋₄ alkenyl, C₂₋₄ alkynyl, C₁₋₄ alkoxy, C₁₋₄ haloalkoxy, C₁₋₄ alkylamino or di (C₁₋₄ alkyl) Not me; R is hydrogen, C₁₋₄ alkyl, C₁₋₄ haloalkyl, C₂₋₄ alkenyl, C₂₋₄ alkynyl or C₁₋₄ alkoxy-C₁₋₄ alkyl, R is hydrogen or C₁₋₄ alkyl; R is hydrogen, C₁₋₄ alkyl, C₁₋₄ haloalkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkoxy, C₁₋₄ alkoxy-C₁₋₄ alkyl, C₁₋₄ haloalkoxy-C₁₋₄ alkyl, C₂₋₄ alkenyl, haloalkenyl C₂₋₄, C₂₋₄ alkynyl, C₂₋₄ haloalkynyl, CN, CH₂CN, NRARB or CH₂-OC (= O) R; R¹, R² are, independently of one another, hydrogen, halogen, OH, CN, C₁₋₄ alkyl, C₁₋₄ haloalkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkoxy, C₁₋₄ alkoxy-C₁₋₄ alkyl, C₁₋ haloalkoxy ₄-C₁₋₄ alkyl, C₂₋₄ alkenyl, C₂₋₄ haloalkenyl, C₂₋₄ alkynyl, C₂₋₄ haloalkynyl, C₃₋₈ cycloalkyl, C₃₋₈ cycloalkyloxy, C₃₋₈ cycloalkyl-C₁₋₄ alkyl, NRARB, C (= O) R, C (= NOR) R, C (= NH) -OR or benzyl, wherein the phenyl portion of benzyl is unsubstituted or has 1, 2, 3, 4 or 5 substituents selected from the group consisting in CN, halogen, C₁₋₄ alkyl, C₁₋₄ haloalkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkoxy, (C₁₋₄ alkoxy) carbonyl and di (C₁₋₄ alkyl) aminocarbonyl, or two radicals R¹ and R² which are together with the same carbon atom they form, together with said carbon atom, a saturated or partially unsaturated carbocycle of 3, 4, 5, 6 or 7 members or a saturated or partial heterocycle Highly unsaturated 3, 4, 5, 6 or 7 members, wherein the ring member atoms of the aforementioned heterocycle include, in addition to carbon atoms, 1, 2, 3 or 4 heteroatoms selected from the group of N, O and S , and wherein the aforementioned cycle is unsubstituted or has 1, 2, 3 or 4 substituents selected from halogen, CN, OH, SH, C₁₋₄ alkyl, C₁₋₄ alkoxy or C₁₋₄ alkylthio; and one or two CH₂ groups of the aforementioned cycles may be replaced by one or two groups C (= O) or C (= S), respectively; n indicates the amount of substituents Rᵇ in the phenyl ring, and n is 0, 1, 2, 3 or 4; Rᵇ is halogen, CN, NO₂, C₁₋₄ alkyl, C₁₋₄ haloalkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkoxy, C₂₋₄ alkenyl, C₂₋₄ haloalkenyl, C₂₋₄ alkynyl, C₂₋₄ haloalkynyl, NRARB, C (= NOR) R or C (= NH) -OR, where it is possible for n = 2, 3 or 4 that Rᵇ be identical or different; Het is a 5- or 6-membered heteroaryl, wherein the heteroaryl ring member atoms include, in addition to carbon atoms, 1, 2, 3 or 4 heteroatoms selected from the group of N, O and S and where the heteroaryl is unsubstituted or has 1, 2, 3 or 4 identical or different Rᶜ groups: Rᶜ is halogen, CN, NO₂, C alquilo alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, C₁₋₆ alkylthio, C₁₋₆ haloalkylthio, C₁₋₆ alkylsulfinyl, C₁₋₆ haloalkylsulfinyl, C₁₋₆ alkylsulfonyl, C₁₋₆ haloalkylsulfonyl, C₁₋₆ alkoxy-C₁₋₄ alkyl, C₁₋₆ haloalkoxy-C₁₋₄ alkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl, NRARB, C (= O) R, C (= NOR) R, C (= NH) -OR, C₃₋₈ cycloalkyl, C₃₋₈ cycloalkyl-C alquilo alkyl, phenyl, phenyl-C₁ alkyl ₋₄, phenoxy, phenoxy-C₁₋₄ alkyl or a 5- or 6-membered heteroaryl, wherein the heteroaryl ring member atoms include, in addition to carbon atoms, 1, 2, 3 or 4 heteroatoms selected from the group of N, O and S, and wherein the aforementioned cyclic radicals are unsubstituted or have 1, 2, 3 or 4 identical or different Rᵈ substituents: Rᵈ is halogen, CN, C₁₋₄ alkyl, C₁₋₄ haloalkyl, C₁₋₄ alkoxy or C₁₋₄ haloalkoxy; or two radicals Rᶜ that bind to the adjacent ring member atoms of the Het group form, together with said ring member atoms, a fused, saturated, partially unsaturated or aromatic carbocycle or heterocycle of 5, 6 or 7 members, wherein the Fused heterocycle ring member atoms include, in addition to carbon atoms, 1, 2, 3 or 4 heteroatoms selected from the group of N, O and S, and wherein the fused carbocycle or heterocycle is unsubstituted or has 1, 2, 3 or 4 identical or different Rᵉ radical groups: Rᵉ is halogen, CN, C₁₋₄ alkyl, C₁₋₄ haloalkyl, C₁₋₄ alkoxy or C₁₋₄ haloalkoxy; and the N-oxides and salts thereof acceptable in agriculture.

ARP130100326 2012-02-03 2013-02-01 PIRIMIDINE FUNGICIDE COMPOUNDS AR089882A1 (en)

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