AR114247A1 - PYRIDINE CARBOXAMIDES - Google Patents

PYRIDINE CARBOXAMIDES

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Publication number
AR114247A1
AR114247A1 ARP190100284A ARP190100284A AR114247A1 AR 114247 A1 AR114247 A1 AR 114247A1 AR P190100284 A ARP190100284 A AR P190100284A AR P190100284 A ARP190100284 A AR P190100284A AR 114247 A1 AR114247 A1 AR 114247A1
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Argentina
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alkyl
alkoxy
halogen
halogenalkyl
cycloalkyl
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ARP190100284A
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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
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3

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

Abstract

Reivindicación 1: Uso de los compuestos caracterizados por la fórmula (1), en donde X es O, S, NH; R³ se selecciona, en cada caso, independientemente de hidrógeno, halógeno, OH, CN, COOH, CONH₂, NO₂, SH, NH₂, NH(C₁₋₄-alquilo), N(C₁₋₄-alquilo)₂, NH-SO₂-Rˣ, C₁₋₆-alquilo, C₂₋₆-alquenilo, C₂₋₆-alquinilo, C₁₋₆-alcoxi, C₃₋₆-cicloalquilo, heteroarilo y arilo de 5 ó 6 miembros; en donde el heteroarilo contiene 1, 2 ó 3 heteroátomos seleccionados de N, O y S; y en donde Rˣ es C₁₋₄-alquilo, C₁₋₄-halogenalquilo, arilo no sustituido o arilo que se sustituye con 1, 2, 3, 4 ó 5 sustituyentes Rˣ¹ seleccionados independientemente de C₁₋₄-alquilo, halógeno, OH, CN, C₁₋₄-halogenalquilo, C₁₋₄-alcoxi y C₁₋₄-halogenalcoxi; en donde las porciones acíclicas de R¹ son no sustituidas o sustituidas con grupos R¹ᵃ idénticos o diferentes, que se seleccionan independientemente entre sí, de: R¹ᵃ halógeno, OH, CN, COOH, CONH₂, C₁₋₆-alcoxi, C₃₋₆-cicloalquilo, C₃₋₆-halogencicloalquilo, C₁₋₄-halogenalcoxi, C₁₋₆-alquiltio, arilo y fenoxi, en donde el grupo arilo es no sustituido o tiene 1, 2, 3, 4 ó 5 sustituyentes R¹¹ᵃ seleccionados del grupo que consiste en halógeno, OH, C₁₋₄-alquilo, C₁₋₄-halogenalquilo, C₁₋₄-alcoxi y C₁₋₄-halogenalcoxi; en donde las porciones carbocíclicas, heteroarilo y arilo de R¹ son no sustituidas adicionalmente o tienen 1, 2, 3, 4, 5 o hasta la máxima cantidad de grupos R¹ᵇ idénticos o diferentes que se seleccionan, independientemente entre sí, de: R¹ᵇ halógeno, OH, CN, COOH, CONH₂, C₁₋₄-alquilo, C₁₋₄-alcoxi, C₁₋₄-halogenalquilo, C₃₋₆-cicloalquilo, C₃₋₆-halogencicloalquilo, C₁₋₄-halogenalcoxi y C₁₋₆-alquiltio; R² se selecciona, en cada caso, independientemente de halógeno, OH, CN, COOH, CONH₂, NO₂, SH, NH₂, NH(C₁₋₄-alquilo), N(C₁₋₄-alquilo)₂, NH(C₂₋₄-alquenilo), N(C₂₋₄-alquenilo)₂, NH(C₂₋₄-alquinilo), N(C₂₋₄-alquinilo)₂, NH(C₃₋₆-cicloalquilo), N(C₃₋₆-cicloalquilo)₂, N(C₁₋₄-alquil)(C₂₋₄-alquenilo), N(C₁₋₄-alquil)(C₂₋₄-alquinilo), N(C₁₋₄-alquil)(C₃₋₆-cicloalquilo), N(C₂₋₄-alquenil)(C₂₋₄-alquinilo), N(C₂₋₄-alquenil)(C₃₋₆-cicloalquilo), N(C₂₋₄-alquinil)(C₃₋₆-cicloalquilo), NH(C(=O)C₁₋₄-alquilo), N(C(=O)C₁₋₄-alquilo)₂, NH-SO₂-Rˣ, S(O)ₙ-C₁₋₆-alquilo, S(O)ₙ-arilo, C₁₋₆-cicloalquiltio, S(O)ₙ-C₂₋₆-alquenilo, S(O)ₙ-C₂₋₆-alquinilo, CH(=O), C(=O)C₁₋₆-alquilo, C(=O)C₂₋₆-alquenilo, C(=O)C₂₋₆-alquinilo, C(=O)C₃₋₆-cicloalquilo, C(=O)NH(C₁₋₆-alquilo), C(=O)N(C₁₋₆-alquilo)₂, C(=O)N(C₂₋₆-alquenilo)₂, C(=O)N(C₂₋₆-alquinilo)₂, C(=O)N(C₃₋₇-cicloalquilo)₂, CH(=S), C(=S)C₁₋₆-alquilo, C(=S)C₂₋₆-alquenilo, C(=S)C₂₋₆-alquinilo, C(=S)C₃₋₆-cicloalquilo, C(=S)O(C₂₋₆-alquenilo), C(=S)O(C₂₋₆-alquinilo), C(=S)O(C₃₋₇-cicloalquilo), C(=S)NH(C₁₋₆-alquilo), C(=S)NH(C₂₋₆-alquenilo), C(=S)NH(C₂₋₆-alquinilo), C(=S)NH(C₃₋₇-cicloalquilo), C(=S)N(C₁₋₆-alquilo)₂, C(=S)N(C₂₋₆-alquenilo)₂, C(=S)N(C₂₋₆-alquinilo)₂, C(=S)N(C₃₋₇-cicloalquilo)₂, C₁₋₆-alquilo, C₁₋₆-halogenalquilo, C₂₋₆-alquenilo, C₂₋₆-alquinilo, ORY, C₃₋₆-cicloalquilo, arilo y heteroarilo de 5 ó 6 miembros; en donde el heteroarilo contiene 1, 2 ó 3 heteroátomos seleccionados de N, O y S; en donde Rˣ es como se definió anteriormente; RY es C₁₋₆-alquilo, C₁₋₆-halogenalquilo, C₂₋₆-alquenilo, C₂₋₆-halogenalquenilo, C₂₋₆-alquinilo, C₂₋₆-halogenalquinilo, C₃₋₆-cicloalquilo, C₃₋₆-halogencicloalquilo, fenilo y fenil-C₁₋₆-alquilo; en donde los grupos fenilo son no sustituidos o tienen 1, 2, 3, 4 ó 5 sustituyentes seleccionados del grupo que consiste en CN, halógeno, OH, C₁₋₄-alquilo, C₁₋₄-halogenalquilo, C₁₋₄-alcoxi y C₁₋₄-halogenalcoxi; en donde las porciones acíclicas de R² son no-sustituidas o sustituidas con grupos R²ᵃ, que se seleccionan, independientemente entre sí, de: R²ᵃ halógeno, OH, CN, COOH, CONH₂, C₁₋₆-alcoxi, C₃₋₆-cicloalquilo, C₃₋₆-halogencicloalquilo, C₁₋₄-halogenalcoxi, C₁₋₆-alquiltio y fenoxi, en donde el grupo fenilo es no sustituido o sustituido con sustituyentes R⁹¹ᵃ seleccionados del grupo que consiste en halógeno, OH, C₁₋₄-alquilo, C₁₋₄-halogenalquilo, C₁₋₄-alcoxi y C₁₋₄-halogenalcoxi; en donde las porciones carbocíclicas, heteroarilo y arilo de R² son no sustituidas o sustituidas con grupos R²ᵇ que se seleccionan, independientemente entre sí, de: R²ᵇ halógeno, OH, CN, COOH, CONH₂, C₁₋₄-alquilo, C₁₋₄-alcoxi, C₁₋₄-halogenalquilo, C₃₋₆-cicloalquilo, C₃₋₆-halogencicloalquilo, C₁₋₄-halogenalcoxi y C₁₋₆-alquiltio; y en donde n es como se definió anteriormente; R³ se selecciona, en cada caso, independientemente de los sustituyentes como se definen para R², en donde los sustituyentes posibles para R³ son R³ᵃ y R³ᵇ, respectivamente, que corresponden a R²ᵃ y R²ᵇ, respectivamente; R⁴ se selecciona, en cada caso, independientemente de hidrógeno, halógeno, OH, CN, COOH, CONH₂, NO₂, SH, NH₂, NH(C₁₋₄-alquilo), N(C₁₋₄-alquilo)₂, NH-SO₂-Rˣ, C₁₋₆-alquilo, C₂₋₆-alquenilo, C₂₋₆-alquinilo, C₁₋₆-alcoxi, C₃₋₆-cicloalquilo, heteroarilo y arilo de 5 ó 6 miembros; en donde el heteroarilo contiene 1, 2 ó 3 heteroátomos seleccionados de N, O y S; y en donde Rˣ es como se definió anteriormente, en donde las porciones alifáticas de R⁴ son no sustituidas o sustituidas con grupos R⁴ᵃ idénticos o diferentes que se seleccionan, independientemente entre sí, de: R⁴ᵃ halógeno, OH, CN, COOH, CONH₂, C₁₋₆-alcoxi, C₃₋₆-cicloalquilo, C₃₋₆-halogencicloalquilo, C₁₋₄-halogenalcoxi, C₁₋₆-alquiltio, arilo y fenoxi, en donde el grupo arilo es no sustituido o tiene 1, 2, 3, 4 ó 5 sustituyentes R⁴¹ᵃ seleccionados del grupo que consiste en halógeno, OH, C₁₋₄-alquilo, C₁₋₄-halogenalquilo, C₁₋₄-alcoxi y C₁₋₄-halogenalcoxi; en donde las porciones cicloalquilo, heteroarilo y arilo de R⁴ son no sustituidas adicionalmente o tienen 1, 2, 3, 4, 5 o hasta la máxima cantidad de grupos R⁴ᵇ idénticos o diferentes que se seleccionan, independientemente entre sí, de: R⁴ᵇ halógeno, OH, CN, COOH, CONH₂, C₁₋₄-alquilo, C₁₋₄-alcoxi, C₁₋₄-halogenalquilo, C₃₋₆-cicloalquilo, C₃₋₆-halogencicloalquilo, C₁₋₄-halogenalcoxi y C₁₋₆-alquiltio; R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰ y R¹¹ se seleccionan independientemente de H, halógeno, OH, CN, NO₂, COOH, CONH₂, SH, C₁₋₆-alquiltio, NH₂, NH(C₁₋₄-alquilo), N(C₁₋₄-alquilo)₂, NH-SO₂-Rˣ, C₁₋₆-alquilo, C₁₋₆-halogenalquilo, C₂₋₆-alquenilo, C₂₋₆-halogenalquenilo, C₂₋₆-alquinilo, C₂₋₆-halogenalquinilo, C₁₋₆-alcoxi, C₁₋₆-halogenalcoxi, C₂₋₆-alqueniloxi, C₂₋₆-alquiniloxi, CH(=O), C(=O)C₁₋₆-alquilo, C(=O)O(C₁₋₆-alquilo), C(=O)NH(C₁₋₆-alquilo), C(=O)N(C₁₋₆-alquilo)₂, CR’=NOR’’, un carbociclo o heterociclo saturado o parcialmente insaturado de 3, 4, 5, 6, 7, 8, 9 ó 10 miembros, un arilo o heteroarilo de 5 ó 6 miembros; en donde, en cada caso, 1 ó 2 grupos CH₂ del carbo- y heterociclo se pueden reemplazar por un grupo independientemente seleccionado de C(=O) y C(=S), y en donde el heterociclo y heteroarilo contienen independientemente 1, 2, 3 ó 4 heteroátomos seleccionados de N, O y S; y en donde R’ y R’’ se seleccionan independientemente de H, C₁₋₄-alquilo, C₂₋₆-alquenilo, C₂₋₆-alquinilo, carbo- y heterociclo saturado o parcialmente insaturado de 3, 4, 5, 6, 7, 8, 9 ó 10 miembros, arilo o heteroarilo de 5 ó 6 miembros; en donde el heterociclo o heteroarilo contiene 1, 2 ó 3 heteroátomos seleccionados de N, O y S, y en donde R’ y R’’ son independientemente no sustituidos o sustituidos con R’’’ que se selecciona independientemente de halógeno, OH, CN, NO₂, SH, NH₂, NH(C₁₋₄-alquilo), N(C₁₋₄-alquilo)₂, NH-SO₂-Rˣ, C₁₋₆-alquilo, C₁₋₆-halogenalquilo, C₂₋₆-alquenilo, C₂₋₆-halogenalquenilo, C₂₋₆-alquinilo, C₂₋₆-halogenalquinilo, C₁₋₆-alcoxi, C₁₋₆-halogenalcoxi, C₃₋₆-cicloalquilo, C₃₋₆-halogencicloalquilo y fenilo; en donde Rˣ es como se definió anteriormente; en donde las porciones acíclicas de R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰ y R¹¹ son independientemente no sustituidas adicionalmente o tienen 1, 2, 3 o hasta la máxima cantidad posible de grupos R⁵ᵃ, R⁶ᵃ, R⁷ᵃ, R⁸ᵃ, R⁹ᵃ, R¹⁰ᵃ y R¹¹ᵃ idénticos o diferentes que se seleccionan, independientemente entre sí, de: halógeno, OH, CN, NO₂, SH, NH₂, NH(C₁₋₄-alquilo), N(C₁₋₄-alquilo)₂, NH(C(=O)C₁₋₄-alquilo), N(C(=O)C₁₋₄-alquilo)₂, NH-SO₂-Rˣ, C₁₋₆-alcoxi, C₁₋₄-halogenalcoxi, C₃₋₆-cicloalquilo, C₃₋₆-halogencicloalquilo, C₁₋₆-alquiltio, C₁₋₆-halogenalquiltio, S(O)ₙ-C₁₋₆-alquilo, S(O)ₙ-arilo, CH(=O), C(=O)C₁₋₆-alquilo, C(=O)O(C₁₋₆-alquilo), C(=O)NH(C₁₋₆-alquilo), C(=O)N(C₁₋₆-alquilo)₂, CR’=NOR’’, un carbo- o heterociclo saturado o parcialmente insaturado de 3, 4, 5, 6, 7, 8, 9 ó 10 miembros, un fenoxi, arilo o heteroarilo de 5, 6 ó 10 miembros, en donde, en cada caso, 1 ó 2 grupos CH₂ del carbo- y heterociclo se pueden reemplazar por un grupo independientemente seleccionado de C(=O) y C(=S), y en donde el heterociclo y el heteroarilo contienen independientemente 1, 2, 3 ó 4 heteroátomos seleccionados de N, O y S; en donde los grupos carbo-, heterocíclicos, heteroarilo y fenilo son independientemente no sustituidos o tienen 1, 2, 3, 4 ó 5 sustituyentes seleccionados del grupo que consiste en halógeno, OH, CN, NO₂, SH, NH₂, NH(C₁₋₄-alquilo), N(C₁₋₄-alquilo)₂, NH(C(=O)C₁₋₄-alquilo), N(C(=O)C₁₋₄-alquilo)₂, NH-SO₂-Rˣ, C₁₋₆-alquiltio, C₁₋₄-alquilo, C₁₋₄-halogenalquilo, C₁₋₄-alcoxi, C₁₋₄-halogenalcoxi y S(O)ₙ-C₁₋₆-alquilo; y en donde Rˣ, R’ y R’’ son como se definió anteriormente; n es 0, 1, 2; y en donde las porciones carbo-, heterocíclicas, heteroarilo y arilo de R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰ y R¹¹ son independientemente no sustituidas o sustituidas con grupos idénticos o diferentes R⁵ᵇ, R⁶ᵇ, R⁷ᵇ, R⁸ᵇ, R⁹ᵇ, R¹⁰ᵇ y R¹¹ᵇ, que se seleccionan, independientemente entre sí, de: halógeno, OH, CN, NO₂, SH, NH₂, NH(C₁₋₄-alquilo), N(C₁₋₄-alquilo)₂, NH(C(=O)C₁₋₄-alquilo), N(C(=O)C₁₋₄-alquilo)₂, NH-SO₂-Rˣ, C₁₋₄-alquilo, C₁₋₄-alcoxi, C₁₋₄-halogenalquilo, C₃₋₆-cicloalquilo, C₃₋₆-halogencicloalquilo, C₁₋₄-halogenalcoxi, C₁₋₆-alquiltio, C₁₋₆-halogenalquiltio, S(O)ₙ-C₁₋₆-alquilo, C₁₋₄-alcoxi-C₁₋₄-alquilo, fenilo y fenoxi, en donde los grupos fenilo son no sustituidos o tienen 1, 2, 3, 4 ó 5 sustituyentes seleccionados del grupo que consiste en halógeno, OH, C₁₋₄-alquilo, C₁₋₄-halogenalquilo, C₁₋₄-alcoxi y C₁₋₄-halogenalcoxi; n es 0, 1, 2; R⁶, R⁷ junto con el átomo de carbono al que están unidos forman un carbociclo o heterociclo saturado o parcialmente insaturado de 3, 4, 5, 6, 7, 8, 9 ó 10 miembros; en donde el heterociclo contiene 1, 2, 3 ó 4 heteroátomos seleccionados de N, O y S, en donde N puede tener un sustituyente RN seleccionado de C₁₋₄-alquilo, C₁₋₄-halogenalquilo y SO₂Ph, en donde Ph es fenilo no sustituido o fenilo que se sustituye con 1, 2 ó 3 sustituyentes seleccionados de CN, C₁₋₄-alquilo, halógeno, C₁₋₄-halogenalquilo, C₁₋₄-alcoxi y C₁₋₄-halogenalcoxi; y en donde S puede ser en forma de su óxido SO o SO₂, y en donde el carbociclo o heterociclo es no sustituido o tiene 1, 2, 3 ó 4 sustituyentes R⁶⁷ independientemente seleccionados de halógeno, OH, CN, NO₂, SH, NH₂, C₁₋₆-alquilo, C₁₋₆-halogenalquilo, C₁₋₆-alcoxi, C₁₋₆-halogenalcoxi, C₁₋₆-alquiltio, C₁₋₆-halogenalquiltio, C₁₋₄-alcoxi-C₁₋₄-alquilo, fenilo y fenoxi, en donde los grupos fenilo son no sustituidos o sustituidos con sustituyentes R⁶⁷ᵃ seleccionados del grupo que consiste en CN, halógeno, OH, C₁₋₄-alquilo, C₁₋₄-halogenalquilo, C₁₋₄-alcoxi y C₁₋₄-halogenalcoxi; y en donde, en cada caso, 1 ó 2 grupos CH₂ del carbo- o heterociclo se pueden reemplazar por un grupo independientemente seleccionado de C(=O) y C(=S); o R⁶, R⁷ junto con el átomo de carbono al que están unidos forman un grupo =N-OR, en donde R se selecciona independientemente de H, C₁₋₄-alquilo, C₂₋₆-alquenilo, C₂₋₆-alquinilo, carbo- y heterociclo saturado o parcialmente insaturado de 3, 4, 5, 6, 7, 8, 9 ó 10 miembros, arilo o heteroarilo de 5 ó 6 miembros; en donde el heterociclo o heteroarilo contiene 1, 2 ó 3 heteroátomos seleccionados de N, O y S, y en donde R es no sustituido o sustituido con halógeno, OH, CN, NO₂, SH, NH₂, NH(C₁₋₄-alquilo), N(C₁₋₄-alquilo)₂, NH-SO₂-Rˣ, C₁₋₆-alquilo, C₁₋₆-halogenalquilo, C₂₋₆-alquenilo, C₂₋₆-halogenalquenilo, C₂₋₆-alquinilo, C₂₋₆-halogenalquinilo, C₁₋₆-alcoxi, C₁₋₆-halogenalcoxi, C₃₋₆-cicloalquilo, C₃₋₆-halogencicloalquilo y fenilo; R⁹, R¹⁰ junto con el átomo de carbono al que están unidos forman un carbociclo o heterociclo saturado o parcialmente insaturado de 3, 4, 5, 6, 7, 8, 9 ó 10 miembros; en donde el heterociclo contiene 1, 2, 3 ó 4 heteroátomos seleccionados de N, O y S, en donde N puede tener un sustituyente RN seleccionado de C₁₋₄-alquilo, C₁₋₄-halogenalquilo y SO₂Ph, en donde Ph es fenilo no sustituido o fenilo que se sustituye con 1, 2 ó 3 sustituyentes seleccionados de CN, C₁₋₄-alquilo, halógeno, C₁₋₄-halogenalquilo, C₁₋₄-alcoxi y C₁₋₄-halogenalcoxi; y en donde S puede ser en forma de su óxido SO o SO₂, y en donde el carbociclo o heterociclo es no sustituido o tiene 1, 2, 3 ó 4 sustituyentes R⁹¹⁰ independientemente seleccionados de halógeno, OH, CN, NO₂, SH, NH₂, C₁₋₆-alquilo, C₁₋₆-halogenalquilo, C₁₋₆-alcoxi, C₁₋₆-halogenalcoxi, C₁₋₆-alquiltio, C₁₋₆-halogenalquiltio, C₁₋₄-alcoxi-C₁₋₄-alquilo, fenilo y fenoxi, en donde los grupos fenilo son no sustituidos o sustituidos con sustituyentes R⁹¹⁰ᵃ seleccionados del grupo que consiste en -CN, halógeno, OH, C₁₋₄-alquilo, C₁₋₄-halogenalquilo, C₁₋₄-alcoxi y C₁₋₄-halogenalcoxi; y en donde, en cada caso, 1 ó 2 grupos CH₂ del carbo- o heterociclo se pueden reemplazar por un grupo independientemente seleccionado de C(=O) y C(=S); o R⁹, R¹⁰ junto con el átomo de carbono al que están unidos forman un grupo =N-OR, en donde R se selecciona independientemente de H, C₁₋₄-alquilo, C₂₋₆-alquenilo, C₂₋₆-alquinilo, carbo- y heterociclo saturado o parcialmente insaturado de 3, 4, 5, 6, 7, 8, 9 ó 10 miembros, arilo o heteroarilo de 5 ó 6 miembros; en donde el heterociclo o heteroarilo contiene 1, 2 ó 3 heteroátomos seleccionados de N, O y S, y en donde R es no sustituido o sustituido con halógeno, OH, CN, NO₂, SH, NH₂, NH(C₁₋₄-alquilo), N(C₁₋₄-alquilo)₂, NH-SO₂-Rˣ, C₁₋₆-alquilo, C₁₋₆-halogenalquilo, C₂₋₆-alquenilo, C₂₋₆-halogenalquenilo, C₂₋₆-alquinilo, C₂₋₆-halogenalquinilo, C₁₋₆-alcoxi, C₁₋₆-halogenalcoxi, C₃₋₆-cicloalquilo, C₃₋₆-halogencicloalquilo y fenilo; y los N-óxidos y las sales de aquellos aceptables en la agricultura como fungicidas.Claim 1: Use of the compounds characterized by formula (1), wherein X is O, S, NH; R³ is selected, in each case, independently from hydrogen, halogen, OH, CN, COOH, CONH₂, NO₂, SH, NH₂, NH (C₁₋₄-alkyl), N (C₁₋₄-alkyl) ₂, NH-SO₂ -Rˣ, C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkynyl, C₁₋₆-alkoxy, C₃₋₆-cycloalkyl, heteroaryl, and 5- or 6-membered aryl; wherein the heteroaryl contains 1, 2, or 3 heteroatoms selected from N, O, and S; and wherein Rˣ is C₁₋₄-alkyl, C₁₋₄-halogenalkyl, unsubstituted aryl, or aryl which is substituted with 1, 2, 3, 4, or 5 Rˣ¹ substituents independently selected from C₁₋₄-alkyl, halogen, OH, CN, C₁₋₄-halogenalkyl, C₁₋₄-alkoxy and C₁₋₄-halogenalkoxy; wherein the acyclic portions of R¹ are unsubstituted or substituted with identical or different R¹ᵃ groups, independently selected from each other, from: R¹ᵃ halogen, OH, CN, COOH, CONH₂, C₁₋₆-alkoxy, C₃₋₆-cycloalkyl , C₃₋₆-halogenocycloalkyl, C₁₋₄-halogenalkoxy, C₁₋₆-alkylthio, aryl, and phenoxy, wherein the aryl group is unsubstituted or has 1, 2, 3, 4, or 5 R¹¹ᵃ substituents selected from the group consisting of halogen, OH, C₁₋₄-alkyl, C₁₋₄-halogenalkyl, C₁₋₄-alkoxy and C₁₋₄-halogenalkoxy; wherein the carbocyclic, heteroaryl, and aryl portions of R¹ are further unsubstituted or have 1, 2, 3, 4, 5 or up to the maximum amount of identical or different R¹ᵇ groups that are independently selected from: R¹ᵇ halogen, OH, CN, COOH, CONH₂, C₁₋₄-alkyl, C₁₋₄-alkoxy, C₁₋₄-halogenalkyl, C₃₋₆-cycloalkyl, C₃₋₆-halogencycloalkyl, C₁₋₄-halogenalkoxy and C₁₋₆-alkylthio; R² is selected, at each occurrence, independently from halogen, OH, CN, COOH, CONH₂, NO₂, SH, NH₂, NH (C₁₋₄-alkyl), N (C₁₋₄-alkyl) ₂, NH (C₂₋₄ -alkenyl), N (C₂₋₄-alkenyl) ₂, NH (C₂₋₄-alkynyl), N (C₂₋₄-alkynyl) ₂, NH (C₃₋₆-cycloalkyl), N (C₃₋₆-cycloalkyl) ₂, N (C₁₋₄-alkyl) (C₂₋₄-alkenyl), N (C₁₋₄-alkyl) (C₂₋₄-alkynyl), N (C₁₋₄-alkyl) (C₃₋₆-cycloalkyl), N (C₂₋₄-alkenyl) (C₂₋₄-alkynyl), N (C₂₋₄-alkenyl) (C₃₋₆-cycloalkyl), N (C₂₋₄-alkynyl) (C₃₋₆-cycloalkyl), NH ( C (= O) C₁₋₄-alkyl), N (C (= O) C₁₋₄-alkyl) ₂, NH-SO₂-Rˣ, S (O) ₙ-C₁₋₆-alkyl, S (O) ₙ -aryl, C₁₋₆-cycloalkylthio, S (O) ₙ-C₂₋₆-alkenyl, S (O) ₙ-C₂₋₆-alkynyl, CH (= O), C (= O) C₁₋₆-alkyl, C (= O) C₂₋₆-alkenyl, C (= O) C₂₋₆-alkynyl, C (= O) C₃₋₆-cycloalkyl, C (= O) NH (C₁₋₆-alkyl), C (= O) N (C₁₋₆-alkyl) ₂, C (= O) N (C₂₋₆-alkenyl) ₂, C (= O) N (C₂₋₆-alkynyl) ₂, C (= O) N (C₃ ₋₇-cycloalkyl) ₂, CH (= S), C (= S) C₁₋₆-alkyl, C (= S) C₂₋₆-alkenyl, C (= S) C₂₋₆-alkynyl, C (= S ) C₃₋₆-cycloalkyl, C (= S) O (C₂₋₆-alkenyl), C (= S) O (C₂₋₆-alkynyl), C (= S) O (C₃₋₇-cycloal chyl), C (= S) NH (C₁₋₆-alkyl), C (= S) NH (C₂₋₆-alkenyl), C (= S) NH (C₂₋₆-alkynyl), C (= S) NH (C₃₋₇-cycloalkyl), C (= S) N (C₁₋₆-alkyl) ₂, C (= S) N (C₂₋₆-alkenyl) ₂, C (= S) N (C₂₋₆- alkynyl) ₂, C (= S) N (C₃₋₇-cycloalkyl) ₂, C₁₋₆-alkyl, C₁₋₆-halogenalkyl, C₂₋₆-alkenyl, C₂₋₆-alkynyl, ORY, C₃₋₆-cycloalkyl 5- or 6-membered aryl and heteroaryl; wherein the heteroaryl contains 1, 2, or 3 heteroatoms selected from N, O, and S; where Rˣ is as defined above; RY is C₁₋₆-alkyl, C₁₋₆-halogenalkyl, C₂₋₆-alkenyl, C₂₋₆-halogenalkenyl, C₂₋₆-alkynyl, C₂₋₆-halogenalkynyl, C₃₋₆-cycloalkyl, C₃₋₆-halogencycloalkyl, phenyl and phenyl-C₁₋₆-alkyl; wherein the phenyl groups are unsubstituted or have 1, 2, 3, 4, or 5 substituents selected from the group consisting of CN, halogen, OH, C₁₋₄-alkyl, C₁₋₄-halogenalkyl, C₁₋₄-alkoxy, and C₁₋₄-halogenalkoxy; wherein the acyclic portions of R² are unsubstituted or substituted with R²ᵃ groups, which are independently selected from: R²ᵃ halogen, OH, CN, COOH, CONH₂, C₁₋₆-alkoxy, C₃₋₆-cycloalkyl, C₃₋₆-halogenocycloalkyl, C₁₋₄-halogenalkoxy, C₁₋₆-alkylthio, and phenoxy, wherein the phenyl group is unsubstituted or substituted with R⁹¹ᵃ substituents selected from the group consisting of halogen, OH, C₁₋₄-alkyl, C₁ ₋₄-halogenalkyl, C₁₋₄-alkoxy and C₁₋₄-halogenalkoxy; wherein the carbocyclic, heteroaryl, and aryl portions of R² are unsubstituted or substituted with R²ᵇ groups that are independently selected from: R²ᵇ halogen, OH, CN, COOH, CONH₂, C₁₋₄-alkyl, C₁₋₄- alkoxy, C₁₋₄-halogenalkyl, C₃₋₆-cycloalkyl, C₃₋₆-halogenocycloalkyl, C₁₋₄-halogenalkoxy and C₁₋₆-alkylthio; and where n is as defined above; R³ is selected, at each occurrence, independently of the substituents as defined for R², wherein the possible substituents for R³ are R³ᵃ and R³ᵇ, respectively, corresponding to R²ᵃ and R²ᵇ, respectively; R⁴ is selected, in each case, independently from hydrogen, halogen, OH, CN, COOH, CONH₂, NO₂, SH, NH₂, NH (C₁₋₄-alkyl), N (C₁₋₄-alkyl) ₂, NH-SO₂ -Rˣ, C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkynyl, C₁₋₆-alkoxy, C₃₋₆-cycloalkyl, heteroaryl, and 5- or 6-membered aryl; wherein the heteroaryl contains 1, 2, or 3 heteroatoms selected from N, O, and S; and wherein Rˣ is as defined above, where the aliphatic portions of R⁴ are unsubstituted or substituted with identical or different R⁴ᵃ groups that are independently selected from: R⁴ᵃ halogen, OH, CN, COOH, CONH₂, C₁ ₋₆-alkoxy, C₃₋₆-cycloalkyl, C₃₋₆-halogenocycloalkyl, C₁₋₄-halogenalkoxy, C₁₋₆-alkylthio, aryl and phenoxy, where the aryl group is unsubstituted or has 1, 2, 3, 4 or 5 R⁴¹ᵃ substituents selected from the group consisting of halogen, OH, C₁₋₄-alkyl, C₁₋₄-halogenalkyl, C₁₋₄-alkoxy, and C₁₋₄-halogenalkoxy; wherein the cycloalkyl, heteroaryl and aryl portions of R⁴ are additionally unsubstituted or have 1, 2, 3, 4, 5 or up to the maximum number of identical or different R⁴ᵇ groups that are independently selected from: R⁴ᵇ halogen, OH, CN, COOH, CONH₂, C₁₋₄-alkyl, C₁₋₄-alkoxy, C₁₋₄-halogenalkyl, C₃₋₆-cycloalkyl, C₃₋₆-halogencycloalkyl, C₁₋₄-halogenalkoxy and C₁₋₆-alkylthio; R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, and R¹¹ are independently selected from H, halogen, OH, CN, NO₂, COOH, CONH₂, SH, C₁₋₆-alkylthio, NH₂, NH (C₁₋₄-alkyl), N (C₁₋₄-alkyl) ₂, NH-SO₂-Rˣ, C₁₋₆-alkyl, C₁₋₆-halogenalkyl, C₂₋₆-alkenyl, C₂₋₆-halogenalkenyl, C₂₋₆-alkynyl, C₂₋₆- halogenalkynyl, C₁₋₆-alkoxy, C₁₋₆-halogenalkoxy, C₂₋₆-alkenyloxy, C₂₋₆-alkynyloxy, CH (= O), C (= O) C₁₋₆-alkyl, C (= O) O ( C₁₋₆-alkyl), C (= O) NH (C₁₋₆-alkyl), C (= O) N (C₁₋₆-alkyl) ₂, CR '= NOR' ', a partially or saturated carbocycle or heterocycle 3, 4, 5, 6, 7, 8, 9 or 10 membered unsaturated, a 5 or 6 membered aryl or heteroaryl; wherein, in each case, 1 or 2 CH₂ groups of the carbo- and heterocycle can be replaced by a group independently selected from C (= O) and C (= S), and wherein the heterocycle and heteroaryl independently contain 1, 2 , 3 or 4 heteroatoms selected from N, O and S; and wherein R 'and R' 'are independently selected from H, C₁₋₄-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkynyl, carbo- and saturated or partially unsaturated heterocycle of 3, 4, 5, 6, 7, 8, 9 or 10 membered, 5 or 6 membered aryl or heteroaryl; wherein the heterocycle or heteroaryl contains 1, 2, or 3 heteroatoms selected from N, O, and S, and wherein R 'and R' 'are independently unsubstituted or substituted with R' '' which is independently selected from halogen, OH, CN, NO₂, SH, NH₂, NH (C₁₋₄-alkyl), N (C₁₋₄-alkyl) ₂, NH-SO₂-Rˣ, C₁₋₆-alkyl, C₁₋₆-halogenalkyl, C₂₋₆-alkenyl , C₂₋₆-halogenalkenyl, C₂₋₆-alkynyl, C₂₋₆-halogenalkynyl, C₁₋₆-alkoxy, C₁₋₆-halogenalkoxy, C₃₋₆-cycloalkyl, C₃₋₆-halogenocycloalkyl and phenyl; where Rˣ is as defined above; where the acyclic portions of R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰ and R¹¹ are independently additionally unsubstituted or have 1, 2, 3 or up to the maximum possible number of groups R grupos, R⁶ᵃ, R⁷ᵃ, R⁸ᵃ, R⁹ᵃ, R¹⁰ᵃ and R¹¹ᵃ identical or different which are independently selected from: halogen, OH, CN, NO₂, SH, NH₂, NH (C₁₋₄-alkyl), N (C₁₋₄-alkyl) ₂, NH (C ( = O) C₁₋₄-alkyl), N (C (= O) C₁₋₄-alkyl) ₂, NH-SO₂-Rˣ, C₁₋₆-alkoxy, C₁₋₄-halogenalkoxy, C₃₋₆-cycloalkyl, C₃ ₋₆-halogenocycloalkyl, C₁₋₆-alkylthio, C₁₋₆-halogenalkylthio, S (O) ₙ-C₁₋₆-alkyl, S (O) ₙ-aryl, CH (= O), C (= O) C₁₋ ₆-alkyl, C (= O) O (C₁₋₆-alkyl), C (= O) NH (C₁₋₆-alkyl), C (= O) N (C₁₋₆-alkyl) ₂, CR '= NOR '', a 3, 4, 5, 6, 7, 8, 9 or 10 membered saturated or partially unsaturated carbo- or heterocycle, a 5, 6 or 10 membered phenoxy, aryl or heteroaryl, wherein, in each In this case, 1 or 2 CH₂ groups of the carbo- and heterocycle can be replaced by a group independently selected from C (= O) and C (= S), and wherein the heterocyclic o and the heteroaryl independently contain 1, 2, 3, or 4 heteroatoms selected from N, O, and S; wherein the carbo-, heterocyclic, heteroaryl and phenyl groups are independently unsubstituted or have 1, 2, 3, 4 or 5 substituents selected from the group consisting of halogen, OH, CN, NO₂, SH, NH₂, NH (C₁₋ ₄-alkyl), N (C₁₋₄-alkyl) ₂, NH (C (= O) C₁₋₄-alkyl), N (C (= O) C₁₋₄-alkyl) ₂, NH-SO₂-Rˣ, C₁₋₆-alkylthio, C₁₋₄-alkyl, C₁₋₄-halogenalkyl, C₁₋₄-alkoxy, C₁₋₄-halogenalkoxy and S (O) ₙ-C₁₋₆-alkyl; and where Rˣ, R 'and R' 'are as defined above; n is 0, 1, 2; and wherein the carbo-, heterocyclic, heteroaryl and aryl portions of R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, and R¹¹ are independently unsubstituted or substituted with identical or different groups R⁵ᵇ, R⁶ᵇ, R⁷ᵇ, R⁸ᵇ, R⁹ᵇ, R¹⁰ᵇ, and R¹¹ᵇ, which are independently selected from: halogen, OH, CN, NO₂, SH, NH₂, NH (C₁₋₄-alkyl), N (C₁₋₄-alkyl) ₂, NH (C (= O) C₁₋₄-alkyl), N (C (= O) C₁₋₄-alkyl) ₂, NH-SO₂-Rˣ, C₁₋₄-alkyl, C₁₋₄-alkoxy, C₁₋₄-halogenalkyl, C₃₋₆- cycloalkyl, C₃₋₆-halogenocycloalkyl, C₁₋₄-halogenalkoxy, C₁₋₆-alkylthio, C₁₋₆-halogenalkylthio, S (O) ₙ-C₁₋₆-alkyl, C₁₋₄-alkoxy-C₁₋₄-alkyl, phenyl and phenoxy, wherein the phenyl groups are unsubstituted or have 1, 2, 3, 4, or 5 substituents selected from the group consisting of halogen, OH, C₁₋₄-alkyl, C₁₋₄-halogenalkyl, C₁₋₄- alkoxy and C₁₋₄-halogenalkoxy; n is 0, 1, 2; R⁶, R⁷ together with the carbon atom to which they are attached form a 3, 4, 5, 6, 7, 8, 9 or 10 membered carbocycle or saturated or partially unsaturated heterocycle; wherein the heterocycle contains 1, 2, 3, or 4 heteroatoms selected from N, O, and S, where N may have an RN substituent selected from C₁₋₄-alkyl, C₁₋₄-halogenalkyl, and SO₂Ph, where Ph is phenyl unsubstituted or phenyl which is substituted with 1, 2 or 3 substituents selected from CN, C₁₋₄-alkyl, halogen, C₁₋₄-halogenalkyl, C₁₋₄-alkoxy, and C₁₋₄-halogenalkoxy; and where S can be in the form of its oxide SO or SO₂, and where the carbocycle or heterocycle is unsubstituted or has 1, 2, 3 or 4 substituents R⁶⁷ independently selected from halogen, OH, CN, NO₂, SH, NH₂ , C₁₋₆-alkyl, C₁₋₆-halogenalkyl, C₁₋₆-alkoxy, C₁₋₆-halogenalkoxy, C₁₋₆-alkylthio, C₁₋₆-halogenalkylthio, C₁₋₄-alkoxy-C₁₋₄-alkyl, phenyl and phenoxy, wherein the phenyl groups are unsubstituted or substituted with R⁶⁷ᵃ substituents selected from the group consisting of CN, halogen, OH, C₁₋₄-alkyl, C₁₋₄-halogenalkyl, C₁₋₄-alkoxy, and C₁₋₄- halogenalkoxy; and wherein, in each case, 1 or 2 CH₂ groups of the carbo- or heterocycle can be replaced by a group independently selected from C (= O) and C (= S); or R⁶, R⁷ together with the carbon atom to which they are attached form a group = N-OR, where R is independently selected from H, C₁₋₄-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkynyl, carbo - and 3, 4, 5, 6, 7, 8, 9 or 10 membered saturated or partially unsaturated heterocycle, 5 or 6 membered aryl or heteroaryl; wherein the heterocycle or heteroaryl contains 1, 2, or 3 heteroatoms selected from N, O, and S, and wherein R is unsubstituted or substituted with halogen, OH, CN, NO₂, SH, NH₂, NH (C₁₋₄-alkyl ), N (C₁₋₄-alkyl) ₂, NH-SO₂-Rˣ, C₁₋₆-alkyl, C₁₋₆-halogenalkyl, C₂₋₆-alkenyl, C₂₋₆-halogenalkenyl, C₂₋₆-alkynyl, C₂₋ ₆-halogenalkynyl, C₁₋₆-alkoxy, C₁₋₆-halogenalkoxy, C₃₋₆-cycloalkyl, C₃₋₆-halogenocycloalkyl, and phenyl; R⁹, R¹⁰ together with the carbon atom to which they are attached form a 3, 4, 5, 6, 7, 8, 9 or 10 membered carbocycle or saturated or partially unsaturated heterocycle; wherein the heterocycle contains 1, 2, 3, or 4 heteroatoms selected from N, O, and S, where N may have an RN substituent selected from C₁₋₄-alkyl, C₁₋₄-halogenalkyl, and SO₂Ph, where Ph is phenyl unsubstituted or phenyl which is substituted with 1, 2 or 3 substituents selected from CN, C₁₋₄-alkyl, halogen, C₁₋₄-halogenalkyl, C₁₋₄-alkoxy, and C₁₋₄-halogenalkoxy; and where S can be in the form of its oxide SO or SO₂, and where the carbocycle or heterocycle is unsubstituted or has 1, 2, 3 or 4 substituents R⁹¹⁰ independently selected from halogen, OH, CN, NO₂, SH, NH₂ , C₁₋₆-alkyl, C₁₋₆-halogenalkyl, C₁₋₆-alkoxy, C₁₋₆-halogenalkoxy, C₁₋₆-alkylthio, C₁₋₆-halogenalkylthio, C₁₋₄-alkoxy-C₁₋₄-alkyl, phenyl and phenoxy, wherein the phenyl groups are unsubstituted or substituted with R⁹¹⁰ᵃ substituents selected from the group consisting of -CN, halogen, OH, C₁₋₄-alkyl, C₁₋₄-halogenalkyl, C₁₋₄-alkoxy, and C₁₋₄ -halogenalkoxy; and wherein, in each case, 1 or 2 CH₂ groups of the carbo- or heterocycle can be replaced by a group independently selected from C (= O) and C (= S); or R⁹, R¹⁰ together with the carbon atom to which they are attached form a group = N-OR, where R is independently selected from H, C₁₋₄-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkynyl, carbo - and 3, 4, 5, 6, 7, 8, 9 or 10 membered saturated or partially unsaturated heterocycle, 5 or 6 membered aryl or heteroaryl; wherein the heterocycle or heteroaryl contains 1, 2, or 3 heteroatoms selected from N, O, and S, and wherein R is unsubstituted or substituted with halogen, OH, CN, NO₂, SH, NH₂, NH (C₁₋₄-alkyl ), N (C₁₋₄-alkyl) ₂, NH-SO₂-Rˣ, C₁₋₆-alkyl, C₁₋₆-halogenalkyl, C₂₋₆-alkenyl, C₂₋₆-halogenalkenyl, C₂₋₆-alkynyl, C₂₋ ₆-halogenalkynyl, C₁₋₆-alkoxy, C₁₋₆-halogenalkoxy, C₃₋₆-cycloalkyl, C₃₋₆-halogenocycloalkyl, and phenyl; and N-oxides and salts of those agriculturally acceptable as fungicides.

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