AR118247A1 - COMBINATION OF ACTIVE COMPOUNDS - Google Patents

COMBINATION OF ACTIVE COMPOUNDS

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Publication number
AR118247A1
AR118247A1 ARP200100595A ARP200100595A AR118247A1 AR 118247 A1 AR118247 A1 AR 118247A1 AR P200100595 A ARP200100595 A AR P200100595A AR P200100595 A ARP200100595 A AR P200100595A AR 118247 A1 AR118247 A1 AR 118247A1
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Argentina
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alkyl
halogen atoms
different
same
aryl
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ARP200100595A
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Spanish (es)
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Ruth Meissner
Sbastien Naud
Andreas Grtz
Jrmy Dufour
Philippe Desbordes
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Bayer Ag
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/498—Pyrazines or piperazines ortho- and peri-condensed with carbocyclic ring systems, e.g. quinoxaline, phenazine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/10—Antimycotics

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pest Control & Pesticides (AREA)
  • Communicable Diseases (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Agronomy & Crop Science (AREA)
  • Oncology (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Reivindicación 1: La combinación de compuesto activo, caracterizado por que comprende (A) un compuesto de fórmula [1] en donde A es un anillo heterociclilo bicíclico fusionado, parcialmente saturado o insaturado de 8, 9, 10 u 11 miembros que comprende 1 átomo de nitrógeno y de 0 a 4 más heteroátomos seleccionados independientemente del grupo que consiste en N, O y S; B es un anillo heterociclilo parcialmente saturado o insaturado de 5 miembros que comprende 1, 2, 3 ó 4 heteroátomos seleccionados independientemente del grupo que consiste en N, O y S; Q es C; Z se selecciona del grupo que consiste en átomo de hidrógeno, átomo de halógeno, hidroxilo, alquilo C₁₋₈, alquenilo C₂₋₈, alquinilo C₂₋₈, halógenoalquinilo C₂₋₈ que comprende hasta 9 átomos de halógeno que pueden ser iguales o diferentes, alcoxi C₁₋₈, halógenoalquilo C₁₋₈ que comprende hasta 9 átomos de halógeno que pueden ser iguales o diferentes, halógenoalquenilo C₂₋₈ que comprende hasta 9 átomos de halógeno que pueden ser iguales o diferentes, halógenoalcoxi C₁₋₈ que comprende hasta 9 átomos de halógeno que pueden ser iguales o diferentes, cicloalquilo C₃₋₇, cicloalquenilo C₄₋₇, arilo, heterociclilo, formilo, alquilocarbonilo C₁₋₈, (hidroxiimino)-alquilo C₁₋₈, (alcoxiimino C₁₋₈)-alquilo C₁₋₈, carboxilo, alcoxicarbonilo C₁₋₈, alquilcarbamoílo C₁₋₈, dialquilcarbamoílo C₁₋₈, alquilamino C₁₋₈, dialquilamino C₁₋₈, sulfanilo, alquilsulfanilo C₁₋₈, alquilsulfinilo C₁₋₈, alquilsulfonilo C₁₋₈, trialquilsililo C₁₋₆, ciano y nitro, en donde dicho cicloalquilo C₃₋₇, cicloalquenilo C₄₋₇, arilo y heterociclilo pueden sustituirse con uno o más sustituyentes Zᵃ que pueden ser iguales o diferentes; m es 0, 1, 2, 3 ó 4; n es 0, 1, 2, 3 ó 4; p es 0, 1, 2, 3, 4 ó 5; L es CR¹R² o NR³ en donde R¹ y R² se seleccionan independientemente del grupo que consiste en átomo de hidrógeno, átomo de halógeno, alcoxi C₁₋₈ y alquilo C₁₋₈; R³ se selecciona del grupo que consiste en átomo de hidrógeno, alquilo C₁₋₈, halógenoalquilo C₁₋₈ que comprende hasta 9 átomos de halógeno que pueden ser iguales o diferentes, alquenilo C₂₋₈, halógenoalquenilo C₂₋₈ que comprende hasta 9 átomos de halógeno que pueden ser iguales o diferentes, alquinilo C₃₋₈, halógenoalquinilo C₃₋₈ que comprende hasta 9 átomos de halógeno que pueden ser iguales o diferentes, cicloalquilo C₃₋₇, halógenocicloalquilo C₃₋₇ que comprende hasta 9 átomos de halógeno que pueden ser iguales o diferentes, cicloalquil C₃₋₇-alquilo C₁₋₈, alquilcarbonilo C₁₋₈, halógenoalquilcarbonilo C₁₋₈ que comprende hasta 9 átomos de halógeno que pueden ser iguales o diferentes, alcoxicarbonilo C₁₋₈, halógenoalcoxicarbonilo C₁₋₈ que comprende hasta 9 átomos de halógeno que pueden ser iguales o diferentes, alquilsulfonilo C₁₋₈, halógenoalquilsulfonilo C₁₋₈ que comprende hasta 9 átomos de halógeno que pueden ser iguales o diferentes, aril-alquilo C₁₋₈ y fenilsulfonilo, en donde dicho cicloalquilo C₃₋₇, cicloalquil C₃₋₇-alquilo C₁₋₈, aril-alquilo C₁₋₈ y fenilsulfonilo pueden sustituirse con uno o más sustituyentes R³ᵃ que pueden ser iguales o diferentes; W se selecciona independientemente del grupo que consiste en átomo de halógeno, hidroxilo, alquilo C₁₋₈, halógenoalquiloC₁₋₈ que comprende hasta 9 átomos de halógeno que pueden ser iguales o diferentes, alcoxi C₁₋₈, halógenoalcoxi C₁₋₈ que comprende hasta 9 átomos de halógeno que pueden ser iguales o diferentes, hidroxialquilo C₁₋₈, alcoxi C₁₋₈-alquilo C₁₋₈, alquenilo C₂₋₈, halógenoalquenilo C₂₋₈ que comprende hasta 9 átomos de halógeno que pueden ser iguales o diferentes, alquinilo C₂₋₈, halógenoalquinilo C₂₋₈ que comprende hasta 9 átomos de halógeno que pueden ser iguales o diferentes, cicloalquilo C₃₋₇, cicloalquenilo C₄₋₈, arilo, arilalquilo C₁₋₈, heterociclilo, heterociclil-alquilo C₁₋₈, ariloxi, heteroariloxi, arilsulfanilo, arilsulfinilo, arilsulfonilo, heteroarilsulfanilo, heteroarilsulfinilo, heteroarilsulfonilo, arilamino, heteroarilamino, ariloxialquilo C₁₋₈, heteroariloxi-alquilo C₁₋₈, arilsulfanil-alquilo C₁₋₈, arilsulfinil-alquilo C₁₋₈, arilsulfonil-alquilo C₁₋₈, heteroarilsulfanilalquilo C₁₋₈, heteroarilsulfinil-alquilo C₁₋₈, heteroarilsulfonil-alquilo C₁₋₈, arilamino-alquilo C₁₋₈, heteroarilamino-alquilo C₁₋₈, aril-alcoxi C₁₋₈, heteroaril-alcoxi C₁₋₈, aril-alquilsulfanilo C₁₋₈, aril-alquilsulfinilo C₁₋₈, aril-alquilsulfonilo C₁₋₈, heteroaril-alquilsulfanilo C₁₋₈, heteroaril-alquilsulfinilo C₁₋₈, heteroaril-alquilsulfonilo C₁₋₈, arilalquilamino C₁₋₈, heteroaril-alquilamino C₁₋₈, formilo, alquilocarbonilo C₁₋₈, (hidroxiimino)-alquilo C₁₋₈, (alcoxiimino C₁₋₈)-alquilo C₁₋₈, carboxilo, alcoxicarbonilo C₁₋₈, carbamoílo, alquilcarbamoílo C₁₋₈, dialquilcarbamoílo C₁₋₈, amino, alquilamino C₁₋₈, dialquilamino C₁₋₈, sulfanilo, alquilsulfanilo C₁₋₈, alquilsulfinilo C₁₋₈, alquilsulfonilo C₁₋₈, trialquilsililo C₁₋₆, tri(alquil C₁₋₈)sililoxi, tri(alquil C₁₋₈)sililoxialquilo C₁₋₈, ciano y nitro, donde dicho cicloalquilo C₃₋₇, cicloalquenilo C₄₋₈, heterociclilo, arilo y las porciones arilo, heterociclilo y heteroarilo de los grupos aril-alquilo C₁₋₈, heterociclil-alquilo C₁₋₈, ariloxi, heteroariloxi, arilsulfanilo, arilsulfinilo, arilsulfonilo, heteroarilsulfanilo, heteroarilsulfinilo, heteroarilsulfonilo, arilamino, heteroarilamino, ariloxi-alquilo C₁₋₈, heteroariloxi-alquilo C₁₋₈, arilsulfanil-alquilo C₁₋₈, arilsulfinil-alquilo C₁₋₈, arilsulfonil-alquilo C₁₋₈, heteroarilsulfanil-alquilo C₁₋₈, heteroarilsulfinil-alquilo C₁₋₈, heteroarilsulfonil-alquilo C₁₋₈, arilaminoalquilo C₁₋₈, heteroarilamino-alquilo C₁₋₈, aril-alcoxi C₁₋₈, heteroarilalcoxi C₁₋₈, aril-alquilsulfanilo C₁₋₈, aril-alquilsulfinilo C₁₋₈, arilalquilsulfonilo C₁₋₈, heteroaril-alquilsulfanilo C₁₋₈, heteroarilalquilsulfinilo C₁₋₈, heteroaril-alquilsulfonilo C₁₋₈, aril-alquilamino C₁₋₈, heteroaril-alquilamino C₁₋₈pueden sustituirse con uno o más sustituyentes Wᵃ que pueden ser iguales o diferentes; X se selecciona independientemente del grupo que consiste en átomo de halógeno, hidroxilo, alquilo C₁₋₈, halógenoalquilo C₁₋₈ que comprende hasta 9 átomos de halógeno que pueden ser iguales o diferentes, alcoxi C₁₋₈, halógenoalcoxi C₁₋₈ que comprende hasta 9 átomos de halógeno que pueden ser iguales o diferentes, alquenilo C₂₋₈, halógenoalquenilo C₂₋₈ que comprende hasta 9 átomos de halógeno que pueden ser iguales o diferentes, alquinilo C₂₋₈, halógenoalquinilo C₂₋₈ que comprende hasta 9 átomos de halógeno que pueden ser iguales o diferentes, cicloalquilo C₃₋₇, cicloalquenilo C₄₋₇, arilo, heterociclilo, formilo, alquilcarbonilo C₁₋₈, (hidroxiimino)-alquilo C₁₋₈, (alcoxiimino C₁₋₈)-alquilo C₁₋₈, carboxilo, alcoxicarbonilo C₁₋₈, carbamoílo, alquilcarbamoílo C₁₋₈, dialquilcarbamoílo C₁₋₈, amino, alquilamino C₁₋₈, dialquilamino C₁₋₈, sulfanilo, alquilsulfanilo C₁₋₈, alquilsulfinilo C₁₋₈, alquilsulfonilo C₁₋₈, trialquilsililo C₁₋₆, ciano, nitro e hidroxialquilo C₁₋₈, donde dicho cicloalquilo C₃₋₇, cicloalquenilo C₄₋₇, arilo y heterociclilo pueden sustituirse con uno o más sustituyentes Xᵃ que pueden ser iguales o diferentes; Y se selecciona independientemente del grupo que consiste en átomo de halógeno, hidroxilo, alquilo C₁₋₈, halógenoalquilo C₁₋₈ que comprende hasta 9 átomos de halógeno que pueden ser iguales o diferentes, alcoxi C₁₋₈, halógenoalcoxi C₁₋₈ que comprende hasta 9 átomos de halógeno que pueden ser iguales o diferentes, alquenilo C₂₋₈, halógenoalquenilo C₂₋₈ que comprende hasta 9 átomos de halógeno que pueden ser iguales o diferentes, alquinilo C₂₋₈, halógenoalquinilo C₂₋₈ que comprende hasta 9 átomos de halógeno que pueden ser iguales o diferentes, cicloalquilo C₃₋₇, cicloalquenilo C₄₋₇, arilo, heterociclilo, formilo, alquilcarbonilo C₁₋₈, (hidroxiimino)-alquilo C₁₋₈, (alcoxiimino C₁₋₈)-alquilo C₁₋₈, carboxilo, alcoxicarbonilo C₁₋₈, carbamoílo, alquilcarbamoílo C₁₋₈, dialquilcarbamoílo C₁₋₈, amino, alquilamino C₁₋₈, dialquilamino C₁₋₈, sulfanilo, alquilsulfanilo C₁₋₈, alquilsulfinilo C₁₋₈, alquilsulfonilo C₁₋₈, trialquilsililo C₁₋₆, ciano y nitro, donde dicho cicloalquilo C₃₋₇, cicloalquenilo C₄₋₇, arilo y heterociclilo pueden sustituirse con uno o más sustituyentes Yᵃ que pueden ser iguales o diferentes; Zᵃ, R³ᵃ, Wᵃ, Xᵃ e Yᵃ se seleccionan independientemente del grupo que consiste en átomo de halógeno, nitro, hidroxilo, ciano, carboxilo, amino, sulfanilo, pentafluoro-l⁶-sulfanilo, formilo, carbamoílo, carbamato, alquilo C₁₋₈, cicloalquilo C₃₋₇, halógenoalquilo C₁₋₈ que tiene de 1 a 5 átomos de halógeno, halógenocicloalquilo C₃₋₈ que tiene de 1 a 5 átomos de halógeno, alquenilo C₂₋₈, alquinilo C₂₋₈, alquilamino C₁₋₈, dialquilamino C₁₋₈, alcoxi C₁₋₈, halógenoalcoxi C₁₋₈ que tiene de 1 a 5 átomos de halógeno, alquilsulfanilo C₁₋₈, halógenoalquilsulfanilo C₁₋₈ que tiene de 1 a 5 átomos de halógeno, alquilcarbonilo C₁₋₈, halógenoalquilcarbonilo C₁₋₈ que tiene de 1 a 5 átomos de halógeno, alquilcarbamoílo C₁₋₈, dialquilcarbamoílo C₁₋₈, alcoxicarbonilo C₁₋₈, halógenoalcoxicarbonilo C₁₋₈ que tiene de 1 a 5 átomos de halógeno, alquilcarboniloxi C₁₋₈, halógenoalquilcarboniloxi C₁₋₈ que tiene de 1 a 5 átomos de halógeno, alquilcarbonilamino C₁₋₈, halógenoalquilcarbonilamino C₁₋₈ que tiene de 1 a 5 átomos de halógeno, alquilsulfanilo C₁₋₈, halógenoalquilsulfanilo C₁₋₈ que tiene de 1 a 5 átomos de halógeno, alquilsulfinilo C₁₋₈, halógenoalquilsulfinilo C₁₋₈ que tiene de 1 a 5 átomos de halógeno, alquilsulfonilo C₁₋₈ y halógenoalquilsulfonilo C₁₋₈ que tiene de 1 a 5 átomos de halógeno, o una sal o N-óxido de este, y (B) o un compuesto activo adicional seleccionado de los siguientes grupos (1) inhibidores de la síntesis de ergosterol, (2) inhibidores de la cadena respiratoria en el complejo I o II, (3) inhibidores de la cadena respiratoria en el complejo III, (4) inhibidores de la mitosis y de la división celular, (5) compuestos capaces de tener una acción multisitio, (6) compuestos capaces de inducir una defensa del huésped, (7) inhibidores de la biosíntesis de aminoácidos y/o proteínas, (8) inhibidores de la producción de ATP, (9) inhibidores de la síntesis de la pared celular, (10) inhibidores de la síntesis de lípidos y de la membrana, (11) inhibidores de la biosíntesis de melanina, (12) inhibidores de la síntesis de ácidos nucleicos, (13) inhibidores de la transducción de señal, (14) compuestos capaces de actuar como desacopladores, (15) otros fungicidas, en donde los compuestos (A) y (B) están presentes en una relación en peso A:B de 5000:1 a 1:5000. Reivindicación 4: La combinación del compuesto activo de acuerdo con la reivindicación 1, caracterizado por que el compuesto de la fórmula [1] es un compuesto de la fórmula [2] en donde W¹ es etilo o propilo; W⁴ es un átomo de hidrógeno; X átomo de hidrógeno, flúor o cloro; L es NH o CR¹R² en donde ambos R¹ y R² son átomos de hidrógeno; Q¹ es N o CH; Y² e Y³ son átomos de hidrógeno; Y⁴ es flúor; Y⁵ es flúor; Z es metilo; o una sal o N-óxido de estos. Reivindicación 12: La combinación de compuestos activos de acuerdo con cualquiera de las reivindicaciones 1 a 10, caracterizado por que el otro compuesto activo es seleccionado del grupo que consiste en (1,002) difenoconazol, (1,018) protioconazol, (1,020) espiroxamina, (1,021) tebuconazol, (1,081) mefentrifluconazol, (1,083) 2-[6-(4-bromofenoxi)-2-(trifluorometil)-3-piridil]-1-(1,2,4-triazol-1-il)propan-2-ol, (2,002) bixafen, (2,005) fluopiram, (2,038) N-(5-cloro-2-isopropilbencilo)-N-ciclopropil-3-(difluorometil)-5-fluoro-1-metil-1H-pirazol-4-carboxamida, (3,003) azoxistrobina, (3,016) picoxistrobina, (3,017) piraclostrobina, (3,020) trifloxistrobina, (3,030) (1S)-2,2-bis(4-fluorofenil)-1-metiletil N-{[3-(acetiloxi)-4-metoxi-2-piridil]carbonil}-L-alaninato, (5,010) ditianon, (5,018) propineb, (6,002) isotianil, (7,005) pirmetanil, (15,012) fosetil-aluminio y (15,066) (N’-[2-cloro-4-(2-fluorofenoxi)-5-metilfenil]-N-etil-N-metilimidoformamida). Reivindicación 13: La combinación de compuestos activos de acuerdo con cualquiera de las reivindicaciones 1 a 12 para uso en controlar microorganismos dañinos en protección de cultivos y en la protección de materiales. Reivindicación 14: La combinación de compuestos activos de acuerdo con cualquiera de las reivindicaciones 1 a 12 para uso en el tratamiento de una planta transgénica o para el tratamiento de semillas.Claim 1: The combination of active compound, characterized in that it comprises (A) a compound of formula [1] wherein A is a fused, partially saturated or unsaturated bicyclic heterocyclyl ring of 8, 9, 10 or 11 members comprising 1 atom from nitrogen and from 0 to 4 more heteroatoms independently selected from the group consisting of N, O and S; B is a 5-membered partially saturated or unsaturated heterocyclyl ring comprising 1, 2, 3 or 4 heteroatoms independently selected from the group consisting of N, O and S; Q is C; Z is selected from the group consisting of hydrogen atom, halogen atom, hydroxyl, C₁₋₈ alkyl, C₂₋₈ alkenyl, C₂₋₈ alkynyl, C₂₋₈ halogenoalkynyl comprising up to 9 halogen atoms which may be the same or different , C₁₋₈ alkoxy, C₁₋₈ halogenoalkyl comprising up to 9 halogen atoms which may be the same or different, C₂₋₈ halogenoalkenyl comprising up to 9 identical or different halogen atoms, C₁₋₈ halogenoalkoxy comprising up to 9 halogen atoms which may be the same or different, C₃₋₇-cycloalkyl, C₄₋₇-cycloalkenyl, aryl, heterocyclyl, formyl, C₁₋₈-alkylcarbonyl, (hydroxyimino)-C₁₋₈-alkyl, (C₁₋₈-alkoxyimino)-C₁₋-alkyl ₈, carboxyl, alcoxicarbonyl c₁₋₈, alkarbamoílo c₁₋₈, dialquarbamoílo c₁₋₈, alquine , cyano and nitro, wherein said C₃₋₇ cycloalkyl, C₄₋₇ cycloalkenyl, aryl and heterocyclyl may be substituted with one or more substituents Zᵃ which may be the same or different; m is 0, 1, 2, 3 or 4; n is 0, 1, 2, 3 or 4; p is 0, 1, 2, 3, 4 or 5; L is CR¹R² or NR³ wherein R¹ and R² are independently selected from the group consisting of hydrogen atom, halogen atom, C₁₋₈ alkoxy, and C₁₋₈ alkyl; R³ is selected from the group consisting of hydrogen atom, C₁₋₈ alkyl, C₁₋₈ halogenoalkyl comprising up to 9 halogen atoms which may be the same or different, C₂₋₈ alkenyl, C₂₋₈ halogenoalkenyl comprising up to 9 halogen atoms halogen which may be the same or different, C₃₋₈ alkynyl, C₃₋₈ halogenoalkynyl comprising up to 9 halogen atoms which may be the same or different, C₃₋₇ cycloalkyl, C₃₋₇ halogenocycloalkyl comprising up to 9 halogen atoms which may be same or different, C₃₋₇-cycloalkyl-C₁₋₈-alkyl, C₁₋₈-alkylcarbonyl, C₁₋₈-halogenoalkylcarbonyl comprising up to 9 halogen atoms which may be the same or different, C₁₋₈-alkoxycarbonyl, C₁₋₈-halogenoalkoxycarbonyl comprising up to 9 halogen atoms that may be the same or different, C₁₋₈ alkylsulfonyl, C₁₋₈ halogenoalkylsulfonyl comprising up to 9 halogen atoms that may be the same or different, aryl-C₁₋₈ alkyl and phenylsulfonyl, wherein said or C₃₋₇-cycloalkyl, C₃₋₇-cycloalkyl-C₁₋₈-alkyl, aryl-C₁₋₈-alkyl and phenylsulfonyl may be substituted with one or more R³ᵃ substituents which may be the same or different; W is independently selected from the group consisting of halogen atom, hydroxyl, C₁₋₈ alkyl, halogenoC₁₋₈ alkyl comprising up to 9 halogen atoms which may be the same or different, C₁₋₈ alkoxy, C₁₋₈ halogenoalkoxy comprising up to 9 halogen atoms which may be the same or different, C₁₋₈ hydroxyalkyl, C₁₋₈ alkoxy-C₁₋₈ alkyl, C₂₋₈ alkenyl, C₂₋₈ halogenoalkenyl comprising up to 9 halogen atoms which may be the same or different, C₂ alkynyl ₋₈, C₂₋₈ halogenoalkynyl comprising up to 9 halogen atoms which may be the same or different, C₃₋₇ cycloalkyl, C₄₋₈ cycloalkenyl, aryl, arylC₁₋₈alkyl, heterocyclyl, heterocyclyl-C₁₋₈ alkyl, aryloxy, heteroaryloxy , arylsulfanyl, arylsulfinyl, arylsulfonyl, heteroarylsulfanyl, heteroarylsulfinyl, heteroarylsulfonyl, arylamino, heteroarylamino, aryloxy-C 1₋ alkyl, heteroaryloxy-C 1₋ alkyl, arylsulfanyl-C 1₋ alkyl, arylsulfinyl-C 1₋ alkyl, arylsulfonyl-C₁₈,₋ alkyl heteroar C₁₋₈-ylsulfanylalkyl, heteroarylsulfinyl-C₁₋₈-alkyl, heteroarylsulfonyl-C₁₋₈-alkyl, arylamino-C₁₋₈-alkyl, heteroarylamino-C₁₋₈-alkyl, aryl-C₁₋₈-alkoxy, heteroaryl-C₁₋₈-alkoxy, aryl-alkylsulfanyl C₁₋₈, aryl-C₁₋₈-alkylsulfinyl, aryl-C₁₋₈-alkylsulfonyl, heteroaryl-C₁₋₈-alkylsulfanyl, heteroaryl-C₁₋₈-alkylsulfinyl, heteroaryl-C₁₋₈-alkylsulfonyl, aryl-C₁₋₈-alkylsulfonyl, heteroaryl-C₁₋₋-alkylamino , formyl, C₁₋₈-alkylcarbonyl, (hydroxyimino)-C₁₋₈-alkyl, (C₁₋₈-alkoxyimino)-C₁₋₈-alkyl, carboxyl, C₁₋₈-alkoxycarbonyl, carbamoyl, C₁₋₈-alkylcarbamoyl, C₁₈-dialkylcarbamoyl, amino C₁₋₈-alkylamino, C₁₋₈-dialkylamino, sulfanyl, C₁₋₈-alkylsulfanyl, C₁₋₈-alkylsulfinyl, C₁₋₈-alkylsulfonyl, C₁₋₆-trialkylsilyl, tri(C₁₋₈-alkyl)silyloxy, tri(C₁₋₈-alkyl)siloxy-C₈alkyl ₋₈, cyano and nitro, where said C₃₋₇ cycloalkyl, C₄₋₈ cycloalkenyl, heterocyclyl, aryl, and the aryl, heterocyclyl, and heteroaryl portions of aryl-C₁₋₈ alkyl, heterocyclyl-alk C₁₋₈-yl, aryloxy, heteroaryloxy, arylsulfanyl, arylsulfinyl, arylsulfonyl, heteroarylsulfanyl, heteroarylsulfinyl, heteroarylsulfonyl, arylamino, heteroarylamino, aryloxy-C₁₋₈-alkyl, heteroaryloxy-C₁₋₈-alkyl, arylsulfanyl-C₁₋₈-alkyl, aryl₁-Crylsulfinyl-alkyl ₋₈, arylsulfonyl-C₁₋₈-alkyl, heteroarylsulfanyl-C₁₋₈-alkyl, heteroarylsulfinyl-C₁₋₈-alkyl, heteroarylsulfonyl-C₁₋₈-alkyl, arylamino-C₁₋₈-alkyl, heteroarylamino-C₁₋₈-alkyl, aryl-C₈-alkoxy,₋ C₁₋₈ heteroarylalkoxy, C₁₋₈ arylalkylsulfinyl, C₁₋₈ arylalkylsulfinyl, C₁₋₈ arylalkylsulfonyl, C₁₋₈ heteroarylalkylsulfanyl, C₁₋₈ heteroarylalkylsulfinyl, C₁₋₋heteroarylalkylsulfinyl, C₁₋₋alkylalkylsulfonyl, aryl₋₈, aryl heteroaryl-C₁₋₈alkylamino may be substituted with one or more substituents Wᵃ which may be the same or different; X is independently selected from the group consisting of halogen atom, hydroxyl, C₁₋₈ alkyl, C₁₋₈ halogenoalkyl comprising up to 9 halogen atoms which may be the same or different, C₁₋₈ alkoxy, C₁₋₈ halogenoalkoxy comprising up to 9 halogen atoms which may be the same or different, C₂₋₈ alkenyl, C₂₋₈ halogenoalkenyl comprising up to 9 halogen atoms which may be the same or different, C₂₋₈ alkynyl, C₂₋₈ halogenoalkynyl comprising up to 9 halogen atoms which may be the same or different, C₃₋₇-cycloalkyl, C₄₋₇-cycloalkenyl, aryl, heterocyclyl, formyl, C₁₋₈-alkylcarbonyl, (hydroxyimino)-C₁₋₈-alkyl, (C₁₋₈-alkoxyimino)-C₁₋₈-alkyl, carboxyl , alcoxicarbonyl c₁₋₈, carbamoílo, alkarbamoílo c₁₋₈, dialquilcarbamoílo c₁₋₈, amino, alqumina c₁₋₈, dialquilamin c₁₋₈, sulphanyl, alklim c₁₋₈, alkloc ₆, cyano, nitro and C₁₋₈ hydroxyalkyl, where said cycloalkyl or C₃₋₇, C₄₋₇ cycloalkenyl, aryl and heterocyclyl may be substituted with one or more substituents Xᵃ which may be the same or different; Y is independently selected from the group consisting of halogen atom, hydroxyl, C₁₋₈ alkyl, C₁₋₈ halogenoalkyl comprising up to 9 halogen atoms which may be the same or different, C₁₋₈ alkoxy, C₁₋₈ halogenoalkoxy comprising up to 9 halogen atoms which may be the same or different, C₂₋₈ alkenyl, C₂₋₈ halogenoalkenyl comprising up to 9 halogen atoms which may be the same or different, C₂₋₈ alkynyl, C₂₋₈ halogenoalkynyl comprising up to 9 halogen atoms which may be the same or different, C₃₋₇-cycloalkyl, C₄₋₇-cycloalkenyl, aryl, heterocyclyl, formyl, C₁₋₈-alkylcarbonyl, (hydroxyimino)-C₁₋₈-alkyl, (C₁₋₈-alkoxyimino)-C₁₋₈-alkyl, carboxyl , alcoxicarbonyl c₁₋₈, carbamoílo, alkarbamoílo c₁₋₈, dialquilcarbamoílo c₁₋₈, amino, alqumina c₁₋₈, dialquilamin c₁₋₈, sulphanyl, alklim c₁₋₈, alkloc ₆, cyano and nitro, where said C₃₋₇ cycloalkyl, cycloalkenyl or C₄₋₇, aryl and heterocyclyl may be substituted with one or more substituents Yᵃ which may be the same or different; Zᵃ, R³ᵃ, Wᵃ, Xᵃ and Yᵃ are independently selected from the group consisting of halogen atom, nitro, hydroxyl, cyano, carboxyl, amino, sulfanyl, pentafluoro-l⁶-sulfanyl, formyl, carbamoyl, carbamate, C₁₋₈ alkyl, C₃₋₇ cycloalkyl, C₁₋₈ halogenoalkyl having 1 to 5 halogen atoms, C₃₋₈ halogenocycloalkyl having 1 to 5 halogen atoms, C₂₋₈ alkenyl, C₂₋₈ alkynyl, C₁₋₈ alkylamino, C₁ dialkylamino ₋₈, C₁₋₈ alkoxy, C₁₋₈ halogenalkoxy having 1 to 5 halogen atoms, C₁₋₈ alkylsulfanyl, C₁₋₈ halogenoalkylsulfanyl having 1 to 5 halogen atoms, C₁₋₈ alkylcarbonyl, C₁₈₋ halogenoalkylcarbonyl having 1 to 5 halogen atoms, C₁₋₈ alkylcarbamoyl, C₁₋₈ dialkylcarbamoyl, C₁₋₈ alkoxycarbonyl, C₁₋₈ halogenoalkoxycarbonyl having 1 to 5 halogen atoms, C₁₋₈ alkylcarbonyloxy, C₈₋ halogenoalkylcarbonyloxy from 1 to 5 halogen atoms, C₁₋₈ alkylcarbonylamino, C₁₋₈ halogenoalkylcarbonylamino having from 1 to 5 halogen atoms, C₁₋₈ alkylsulfanyl, C₁₋₈ halogenoalkylsulfanyl having 1 to 5 halogen atoms, C₁₋₈ alkylsulfinyl, C₁₋₈ halogenoalkylsulfinyl having 1 to 5 halogen atoms, C₁₋₈ alkylsulfonyl, and ₂alkylsulfonyl ₋₈ having 1 to 5 halogen atoms, or a salt or N-oxide thereof, and (B) or an additional active compound selected from the following groups (1) ergosterol synthesis inhibitors, (2) inhibitors of the respiratory chain in complex I or II, (3) inhibitors of the respiratory chain in complex III, (4) inhibitors of mitosis and cell division, (5) compounds capable of having a multisite action, (6 ) compounds capable of inducing host defense, (7) inhibitors of amino acid and/or protein biosynthesis, (8) inhibitors of ATP production, (9) inhibitors of cell wall synthesis, (10) inhibitors of lipid and membrane synthesis, (11) inhibitors of mel biosynthesis anine, (12) nucleic acid synthesis inhibitors, (13) signal transduction inhibitors, (14) compounds capable of acting as uncouplers, (15) other fungicides, wherein compounds (A) and (B) they are present in a weight ratio A:B of 5000:1 to 1:5000. Claim 4: The active compound combination according to claim 1, characterized in that the compound of the formula [1] is a compound of the formula [2] wherein W¹ is ethyl or propyl; W⁴ is a hydrogen atom; X hydrogen, fluorine or chlorine atom; L is NH or CR¹R² where both R¹ and R² are hydrogen atoms; Q¹ is N or CH; Y² and Y³ are hydrogen atoms; Y⁴ is fluorine; Y⁵ is fluorine; Z is methyl; or a salt or N-oxide of these. Claim 12: The combination of active compounds according to any of claims 1 to 10, characterized in that the other active compound is selected from the group consisting of (1.002) difenoconazole, (1.018) prothioconazole, (1.020) spiroxamine, (1.021 ) tebuconazole, (1,081) mefentrifluconazole, (1,083) 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan- 2-ol, (2.002) bixafen, (2.005) fluopyram, (2.038) N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole -4-Carboxamide, (3.003) Azoxystrobin, (3.016) Picoxystrobin, (3.017) Pyraclostrobin, (3.020) Trifloxystrobin, (3.030) (1S)-2,2-bis(4-fluorophenyl)-1-methylethyl N-{[ 3-(acetyloxy)-4-methoxy-2-pyridyl]carbonyl}-L-alaninate, (5.010) dithianon, (5.018) propineb, (6.002) isotianyl, (7.005) pyrmethanil, (15.012) fosetyl-aluminum, and (15.066 ) (N-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methylimidoformamide). Claim 13: The combination of active compounds according to any of claims 1 to 12 for use in controlling harmful microorganisms in crop protection and in the protection of materials. Claim 14: The combination of active compounds according to any of claims 1 to 12 for use in the treatment of a transgenic plant or for the treatment of seeds.

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