AR089885A1 - PIRIMIDINE FUNGICIDE COMPOUNDS - Google Patents

PIRIMIDINE FUNGICIDE COMPOUNDS

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Publication number
AR089885A1
AR089885A1 ARP130100329A AR089885A1 AR 089885 A1 AR089885 A1 AR 089885A1 AR P130100329 A ARP130100329 A AR P130100329A AR 089885 A1 AR089885 A1 AR 089885A1
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Argentina
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alkyl
alkoxy
haloalkoxy
haloalkyl
halogen
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Spanish (es)
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Basf Se
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Publication of AR089885A1 publication Critical patent/AR089885A1/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

Reivindicación 1: Compuestos de fórmula (1) en donde Rᵃ⁶ es A-B-D, en donde A es un enlace directo, B es un grupo divalente -C(=O)-, y D es alcoxi C₁₋₄; Rᵃ², Rᵃ⁵ independientemente uno de otro son hidrógeno, 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 independientemente uno de otro son 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 independientemente uno de otro son 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-, cicloalcoxi C₃₋₈, cicloalquil C₃₋₈-alquilo-C₁₋₄, NRARB, C(=O)R, C(=NOR)R, C(=NH)-O-R o bencilo, en donde el resto fenilo de bencilo está no sustituido o transporta 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 están unidos al mismo átomos de carbono forman juntos 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 del miembro del anillo del heterociclo antes mencionado incluyen además de los átomos de carbono 1, 2, 3 ó 4 heteroátomos seleccionados del grupo de N, O y S, y en donde el ciclo antes mencionado está no sustituido o transporta 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 pueden ser reemplazados por uno o dos grupos C(=O) o C(=S) respectivamente; X es un grupo divalente seleccionado de -CR³R⁴-, -C(=O)-, -C(=S)-, -C(=NRD) y -C(=NORD)-, en donde R³, R⁴ independientemente uno de otro son hidrógeno, halógeno, CN, alquilo C₁₋₄, haloalquilo C₁₋₄, hidroxialquilo 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-, cicloalquil C₃₋₈-alquilo C₁₋₄, cicloalquiloxi C₃₋₈, NRARB, C(=O)R, C(NOR)R, C(=NH)-O-R o bencilo, en donde el resto fenilo del bencilo está no sustituido o transporta 1, 2, 3, 4, ó 5 sustituyentes seleccionados del grupo que consiste de CN, halógeno, alquilo C₁₋₄, haloalquilo C₁₋₄, alcoxi C₁₋₄, haloalcoxi C₁₋₄, (alcoxi C₁₋₄)carbonilo y di(alquilo C₁₋₄)aminocarbonilo, o dos radicales R³ y R⁴ que están unidos 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 del miembro del anillo del heterociclo antes mencionado incluyen además de los átomos de carbono 1, 2, 3 ó 4 heteroátomos seleccionados del grupo de N, O y S, y en donde el ciclo antes mencionado está no sustituido o transporta 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 pueden ser reemplazados por uno o dos grupos C(=O) o C(=S) respectivamente; y RD es hidrógeno o alquilo C₁₋₄-; n indica el número 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, siendo 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 del miembro 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 está no sustituido o transporta 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-, haloalquilsulfinilo 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-, cicloalquilo C₃₋₈-alquilo C₁₋₄-, fenilo, fenilalquilo C₁₋₄-, fenoxi, fenoxi-alquilo C₁₋₄ o un heteroarilo de 5 ó 6 miembros, en donde los átomos del miembro 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 están no sustituidos o transportan 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 están unidos a los átomos del miembro del anillo adyacente del grupo Het forman junto con dichos átomos del miembro del anillo un carbociclo o heterociclo fusionado de 5, 6, ó 7 miembros saturado, parcialmente insaturado o aromático, donde los átomos del miembro del anillo del heterociclo fusionado incluyen además de los 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 está no sustituido o trasporta 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 sus N-óxidos y sus sales aceptables para uso agrícola.Claim 1: Compounds of formula (1) wherein Rᵃ⁶ is A-B-D, wherein A is a direct bond, B is a divalent group -C (= O) -, and D is C₁₋₄ alkoxy; Rᵃ², Rᵃ⁵ independently of each other are hydrogen, CN, NO₂, OH, SH, C₁₋₄ alkyl, C₁₋₄ haloalkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkoxy, C₁₋₄ alkylthio, C₁₋₄ haloalkylthio, C₁ alkylsulfinyl ₋₄, C₁₋₄ haloalkylsulfinyl, C₁₋₄ alkylsulfonyl, C₁₋₄ haloalkylsulfonyl, C₁₋₄ alkoxy-C₁₋₄ alkoxy, C₂₋₄-alkoxy-C₂₋₄- alkenyl, C₂₋₄ alkynyl, haloalkenyl C₂₋₄-, C₂₋₄- haloalkynyl, C₃₋₈ cycloalkyl, C₃₋₈ cycloalkyloxy, C₃₋₈ cycloalkyl-C alquilo alkyl, NRARB, C (= O) R, C (= NOR) R or C (= NH) -OR; RA, RB independently of each other are 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 di (C₁₋₄-) alkyl; 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 independently of each other are hydrogen, halogen, OH, CN, 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, C₂₋₄ haloalkenyl, C₂₋₄ alkynyl, C₂₋₄ haloalkynyl, C₃₋₈ cycloalkyl, C₃₋₈ cycloalkoxy, C₃₋₈-C-alkylcycloalkyl, NRARB, C (= O) R, C (= NOR) R, C (= NH) -OR or benzyl, wherein the phenyl benzyl moiety is unsubstituted or transports 1, 2, 3, 4, or 5 substituents selected from the group consisting of 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 attached to the same carbon atoms together with said carbon atom a saturated or partially unsaturated carbocycle of 3, 4, 5, 6 or 7-members or a saturated heterocycle C or partially unsaturated 3, 4, 5, 6 or 7-membered, wherein the atoms of the heterocycle ring member mentioned above also include carbon atoms 1, 2, 3 or 4 heteroatoms selected from the group of N, O and S, and wherein the above-mentioned cycle is unsubstituted or transports 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; X is a divalent group selected from -CR³R⁴-, -C (= O) -, -C (= S) -, -C (= NRD) and -C (= NORD) -, where R³, R⁴ independently one of other are hydrogen, halogen, CN, C₁₋₄ alkyl, C₁₋₄ haloalkyl, C₁₋₄ hydroxyalkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkoxy, C₁₋₄ alkoxy-C₁₋₄ alkyl, C₁₋₄ haloalkoxy-C alquilo alkyl ₋₄, C₂₋₄ alkenyl, C₂₋₄ haloalkenyl, C₂₋₄ alkynyl, C₂₋₄ haloalkynyl, C₃₋₈- cycloalkyl, C₃₋₈ cycloalkyl-C₁₋₄ alkyl, C₃₋₈ cycloalkyloxy, NRARB, C (= O ) R, C (NOR) R, C (= NH) -OR or benzyl, wherein the phenyl moiety of the benzyl is unsubstituted or carries 1, 2, 3, 4, or 5 substituents selected from the group consisting of 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 R³ and R⁴ radicals that are attached thereto carbon atom form together with said carbon atom 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 atoms of the ring member of the Heterocycle mentioned above also includes carbon atoms 1, 2, 3 or 4 heteroatoms selected from the group of N, O and S, and wherein the above-mentioned cycle is unsubstituted or transports 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; and RD is hydrogen or C₁₋₄- alkyl; n indicates the number 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, haloalkynyl C₂₋₄-, NRARB, C (= NOR) R or C (= NH) -OR, it being possible for n = 2, 3, or 4 that Rᵇ be identical or different; Het is a 5- or 6-membered heteroaryl, wherein the atoms of the heteroaryl ring member 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 transports 1, 2, 3 or 4 identical or different Rᶜ groups: Rᶜ is halogen, CN, NO₂, C₁₋₆- alkyl, C₁₋₆- haloalkyl, C₁₋₆- alkoxy, C₁₋₆- haloalkoxy, alkylthio C₁₋₆-, haloalkylthio C₁₋₆-, alkylsulfinyl C₁₋₆-, haloalkylsulfinyl C₁₋₆-, alkylsulfonyl C₁₋₆-, haloalkylsulfinyl C₁₋₆-, alkoxy C₁₋₆-alkyl C₁₋₄-, haloalkoxy C₁₋₆ -C₁₋₄- alkyl, C₂₋₆- alkenyl, C₂₋₆- alkynyl, NRARB, C (= O) R, C (= NOR) R, C (= NH) -OR, C₃₋₈- cycloalkyl, cycloalkyl C₃₋₈-C₁₋₄- alkyl, phenyl, C₁₋₄- phenylalkyl, phenoxy, phenoxy-C₁₋₄ alkyl or a 5- or 6-membered heteroaryl, wherein the atoms of the het ring member eroaryl also include 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 carry 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 which are attached to the atoms of the adjacent ring member of the Het group together with said atoms of the ring member a fused carbocycle or heterocycle of 5, 6, or 7 members saturated, partially unsaturated or aromatic, where the atoms of the fused heterocycle ring member 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 transports 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 its N-oxides and salts acceptable for agricultural use.

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