AR115966A1 - PHENYLAMIDINE COMPOUNDS AND THEIR USES - Google Patents

PHENYLAMIDINE COMPOUNDS AND THEIR USES

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Publication number
AR115966A1
AR115966A1 ARP190102331A ARP190102331A AR115966A1 AR 115966 A1 AR115966 A1 AR 115966A1 AR P190102331 A ARP190102331 A AR P190102331A AR P190102331 A ARP190102331 A AR P190102331A AR 115966 A1 AR115966 A1 AR 115966A1
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Argentina
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group
alkyl
substituted
optionally including
ring
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ARP190102331A
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Spanish (es)
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Alexander G M Klausener
Hagalavadi M Venkatesha
Ruchi Garg
Sachin Nagnath Gumme
Santosh Shridhar Autkar
Shalaka Manikrao Mapari
Mohammed Abrar Abdul Gaffar Shaikh
Maruti Naik
Vishal A Mahajan
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Pi Industries Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
    • C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
    • C07C257/12—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having carbon atoms of amidino groups bound to hydrogen atoms
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/52—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing groups, e.g. carboxylic acid amidines
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

La presente describe compuestos de fenilamida de la fórmula (1), en la que, Cy, R¹, R², R³, R⁴, R⁵, R⁶,R⁷, R⁸, R⁹, R¹⁰ y m tienen los mismos significados que se definen en la descripción. La presente describe además un proceso para la preparación de compuestos de la fórmula (1). Además, la presente describe el uso de compuestos de la fórmula (1) y/o sus composiciones para proteger cultivos agrícolas y/u hortícolas contra microorganismos fitopatógenos no deseados. Reivindicación 1: Un compuesto la fórmula (1) en la que; R¹ se selecciona del grupo que consiste en hidrógeno, ciano, C₁₋₁₂-alquilo, C₂₋₁₂-alquenilo, C₂₋₁₂-alquinilo, C₁₋₁₂-haloalquilo, C₂₋₁₂-haloalquenilo, C₂₋₁₂-haloalquinilo, SR’’, OR’’, C₃₋₈-cicloalquilo, C₄₋₈-cicloalquenil y C₄₋₈-cicloalquinil; en el que uno o más átomos de carbono en dichos sistemas de anillo pueden reemplazarse por heteroátomos seleccionados del grupo que consiste en N, O, S y que opcionalmente incluyen 1 a 3 miembros del anillo seleccionados del grupo que consiste en C(=O), C(=S), S(O)ₘ y Si(R’)₂; R² y R³ se seleccionan independientemente del grupo que consiste en hidrógeno, ciano, C₁₋₁₂-alquilo, C₂₋₁₂-alquenilo, C₂₋₁₂-alquinilo, C₁₋₁₂-haloalquilo, C₂₋₁₂-haloalquenilo, C₂₋₁₂-haloalquinilo, C₃₋₈-cicloalquilo, C₄₋₈-cicloalquenil, C₄₋₈-cicloalquinil, S(O)ₙR’’, OR’’ y (C=O)-R’’; en el que uno o más átomos de carbono en dichos sistemas de anillo pueden reemplazarse por heteroátomos seleccionados del grupo que consiste en N, O, S y opcionalmente que incluyen 1 a 3 miembros del anillo seleccionados del grupo que consiste en C(=O), C(=S), S(O)ₘ y Si(R’)₂; R¹ y R², R² y R³ o R¹ y R³ junto con los átomos a los que están unidos o junto con los otros átomos seleccionados del grupo que consiste en C, N, O, S y que opcionalmente incluye de 1 a 3 miembros del anillo seleccionados del grupo que consiste en C(=O), C(=S), y S(O)ₘ o Si(R’)₂ pueden formar un anillo no aromático de tres a siete miembros, que por su parte puede estar sustituido por uno o más grupos seleccionados del grupo que consiste en X, CN, R’, OR’, SR’, N(R’)₂ y Si(R’)₃; cada grupo de R¹, R² y R³ pueden estar opcionalmente sustituidos por uno o más grupos seleccionados del grupo que consiste en X, CN, R’, OR’, SR’, N(R’)₂, Si(R’)₃, COOR’ y CON(R’)₂; R⁴ y R⁵ se seleccionan independientemente del grupo que consiste en X, ciano, C₁₋₁₂-alquilo, C₂₋₁₂-alquenilo, C₂₋₁₂-alquinilo, C₁₋₁₂-haloalquilo, C₂₋₁₂-haloalquenilo, C₂₋₁₂-haloalquinilo, N(R’’)₂, OR’’, S(O)ₙR’’, SCN, SF₅, Si(R’)₃, (C=O)-R’’, CR’=NR’’, C₃₋₈-cicloalquilo, C₄₋₈-cicloalquenil, y C₃₋₅-heterociclilo, en el que uno o más átomos de carbono en dichos sistemas de anillo pueden reemplazarse por heteroátomos seleccionados del grupo que consiste en N, O, S y que opcionalmente incluyen 1 a 3 miembros del anillo seleccionados del grupo que consiste en C(=O), C(=S), S(O)ₘ y Si(R’)₂; R⁶ y R⁷ se seleccionan independientemente del grupo que consiste en hidrógeno, X, ciano, C₁₋₁₂-alquilo, C₂₋₁₂-alquenilo, C₂₋₁₂-alquinilo, C₁₋₁₂-haloalquilo, C₂₋₁₂-haloalquenilo, C₂₋₁₂-haloalquinilo, (NR’’)₂, OR’’, S(O)ₙR’’, SCN, Si(R’)₃, (C=O)-R’’, CR’=NR’’, C₃₋₈-cicloalquilo, C₄₋₈-cicloalquenil y C₄₋₈-cicloalquinil; en el que uno o más átomos de carbono en dichos sistemas de anillo pueden reemplazarse por heteroátomos seleccionados del grupo que consiste en N, O, S y que opcionalmente incluyen 1 a 3 miembros del anillo seleccionados del grupo que consiste en C(=O), C(=S), S(O)ₘ y Si(R’₂); o R⁴ y R⁶ o R⁵ y R⁷ junto con el átomo al que están unidos o junto con otros átomos seleccionados del grupo que consiste en C, N, O, S y que opcionalmente incluyen 1 a 3 miembros del anillo seleccionados del grupo que consiste en C(=O), C(=S), S(O)ₘ y Si(R’)₂ pueden formar un anillo de tres a seis miembros, que por su parte puede estar sustituido por uno o más grupos seleccionados del grupo que consiste en X, CN, R’, OR’, SR’, N(R’)₂, Si(R’)₃, COOR’ y CON(R’)₂; R⁸ se selecciona del grupo que consiste en hidrógeno, ciano, C₁₋₁₂-alquilo, C₂₋₁₂-alquenilo, C₂₋₁₂-alquinilo, C₁₋₁₂-haloalquilo, C₂₋₁₂-haloalquenilo, C₂₋₁₂-haloalquinilo, S(O)ₙR’’, SiR’₃, NR’R’’, (C=O)-R’’, CR’=NR’’, C₃₋₈-cicloalquilo, C₄₋₈-cicloalquenil, C₄₋₈-cicloalquinil y C₇₋₁₉-aralquil; en el que uno o más átomos de carbono en dichos sistemas de anillo pueden reemplazarse por heteroátomos seleccionados del grupo que consiste en N, O, y S(O)ₙ; y todos los grupos mencionados anteriormente pueden estar sustituidos por uno o más grupos seleccionados del grupo que consiste X, CN, R’, OR’, SR’, NR’₂, SiR’₃, COOR’ y CONR’₂; R⁹ y R¹⁰ se seleccionan independientemente del grupo que consiste en hidrógeno, X, ciano, C₁₋₁₂-alquilo, C₂₋₁₂-alquenilo, C₂₋₁₂-alquinilo, C₁₋₁₂-haloalquilo, C₂₋₁₂-haloalquenilo, C₂₋₁₂-haloalquinilo, (NR’’)₂, OR’, S(O)ₙR’’, SCN, Si(R’)₃, (C=O)-R’’, CR’=NR’’, C₃₋₈-cicloalquilo, C₄₋₈-cicloalquenil y C₄₋₈-cicloalquinil; en el que uno o más átomos de carbono en dichos sistemas de anillo pueden reemplazarse por heteroátomos seleccionados del grupo que consiste en N, O, S y que opcionalmente incluyen 1 a 3 miembros del anillo seleccionados del grupo que consiste en C(=O), C(=S), S(O)ₘ y Si(R’)₂; o R⁹ y R¹⁰ junto con el átomo al que están unidos o junto con otros átomos seleccionados del grupo que consiste en C, N, O, S y que opcionalmente incluyen 1 a 3 miembros del anillo seleccionados del grupo que consiste en C(=O), C(=S), S(O)ₘ o Si(R’)₂ pueden formar un anillo de tres a seis miembros, que por su parte puede estar sustituido por uno o más grupos seleccionados del grupo que consiste en X, CN, R’, OR’, SR’, N(R’)₂, Si(R’)₃, COOR’ y CON(R’)₂; Cy se selecciona del grupo que consiste en un grupo carbociclilo C₃₋₁₈, fusionado o no fusionado, o heterociclilo C₃₋₁₈, que opcionalmente puede estar sustituido con uno o más grupos de R¹¹; R¹¹ se selecciona del grupo que consiste en hidrógeno, X, ciano, nitro, C₁₋₁₂-alquilo, C₂₋₁₂-alquenilo, C₂₋₁₂-alquinilo, C₁₋₁₂-haloalquilo, C₂₋₁₂-haloalquenilo, C₂₋₁₂-haloalquinilo, C₃₋₈-cicloalquilo, C₄₋₈-cicloalquenil, C₄₋₈-cicloalquinil, C₇₋₁₉-aralquil, C₅₋₁₂-bicicloalquil, C₅₋₁₂-bicicloalquenil, C₆₋₁₀-arilo, C₃₋₆-heterociclilo, SCN, SF₅, N(R’’)₂, OR’, S(O)ₙR’’, Si(R’)₃, (C=O)-R’’, C₁₋₈-alquilo-S(O)ₙR’’, C₁₋₈-alquilo-C(=O)-R’’, CR’=NR’’, S(O)ₙC₆₋₁₈-arilo y S(O)ₙC₇₋₁₉-aralquil, en el que uno o más átomos de carbono en dicho el sistema de anillo puede ser reemplazado por heteroátomos seleccionados del grupo que consiste en N, O, S y que opcionalmente incluye de 1 a 3 miembros del anillo seleccionados del grupo que consiste en C(=O), C(=S), S(O)ₘ y Si(R’)₂; o R¹¹ se selecciona del grupo que consiste en grupo de fórmulas (2), en el que la línea ondulada representa uniones del átomo o grupo; R⁹ᵃ y R¹⁰ᵃ se seleccionan independientemente del grupo que consiste en hidrógeno, X, ciano, C₁₋₁₂-alquilo, C₂₋₁₂-alquenilo, C₂₋₁₂-alquinilo, C₁₋₁₂-haloalquilo, C₂₋₁₂-haloalquenilo, C₂₋₁₂-haloalquinilo, (NR’’)₂, OR’, S(O)ₙR’’, (C=O)-R’’, C₃₋₈-cicloalquilo, C₄₋₈-cicloalquenilo y C₄₋₈-cicloalquinil; en el que uno o más átomos de carbono en dichos sistemas de anillo pueden reemplazarse por heteroátomos seleccionados del grupo que consiste en N, O, S y que opcionalmente incluyen 1 a 3 miembros del anillo seleccionados del grupo que consiste en C(=O), C(=S), S(O)ₘ y Si(R’)₂; o R⁹ᵃ y R¹⁰ᵃ junto con el átomo al que están unidos o junto con otros átomos seleccionados del grupo que consiste en C, N, O, S y que opcionalmente incluyen 1 a 3 miembros del anillo seleccionados del grupo que consiste en C(=O), C(=S), S(O)ₘ o Si(R’)₂ pueden formar un anillo de tres a seis miembros, que por su parte puede estar sustituido por uno o más grupos seleccionados del grupo que consiste en X, CN, R’, OR’, SR’, N(R’)₂, Si(R’)₃, COOR’ y CON(R’)₂; o R⁹ᵃ y R¹⁰ᵃ junto con el átomo al que están unidos pueden formar un grupo de =O ó =S; R¹² se selecciona independientemente del grupo que consiste en C₁₋₁₂-alquilo, C₂₋₁₂-alquenilo, C₂₋₁₂-alquinilo, C₁₋₁₂-haloalquilo, C₂₋₁₂-haloalquenilo, C₂₋₁₂-haloalquinilo, (C=O)-R’’, C₃₋₈-cicloalquilo, C₄₋₈-cicloalquenilo, C₇₋₁₉-aralquil, C₅₋₁₂-bicicloalquil y C₃₋₁₈-carbociclo fusionado o no fusionado sustituido con uno o más grupos de R¹⁴; en el que uno o más átomos de carbono en los sistemas de anillo mencionados pueden reemplazarse por heteroátomos seleccionados del grupo que consiste en N, O, S y que opcionalmente incluyen 1 a 3 miembros del anillo seleccionados del grupo que consiste en C(=O), C(=S), S(O)ₘ o Si(R’)₂; R¹³ se selecciona del grupo que consiste en hidrógeno, ciano, C₁₋₁₂-alquilo, C₂₋₁₂-alquenilo, C₂₋₁₂-alquinilo, C₁₋₁₂-haloalquilo, C₂₋₁₂-haloalquenilo, C₂₋₁₂-haloalquinilo, OR’, N(R’R’’), Si(R’)₃, (C=O)-R’’’, S(O)ₙR’’’, C₁₋₈-alquilo-S(O)ₙR’’’, C₁₋₈-alquilo-(C=O)-R’’’, S(O)ₙC₆₋₁₈-arilo, S(O)ₙC₇₋₁₉-aralquil, C₃₋₈-cicloalquilo y C₄₋₈-cicloalquenil; en el que uno o más átomos de carbono en dichos sistemas de anillo pueden reemplazarse por heteroátomos seleccionados del grupo que consiste en N, O, S y que opcionalmente incluyen 1 a 3 miembros del anillo seleccionados del grupo que consiste en C(=O), C(=S), S(O)ₘ o Si(R’)₂; o R¹² y R¹³ junto con el átomo al que están unidos o junto con otro átomos seleccionados del grupo que consiste en C, N, O, S y que opcionalmente incluyen de 1 a 3 miembros del anillo seleccionados del grupo que consiste en C(=O), C(=S), S(O)ₘ y Si(R’)₂ pueden formar un anillo de tres a siete miembros, que por su parte puede estar sustituido por uno o más grupos seleccionados del grupo que consiste en X, CN, R’, OR’, SR’, N(R’)₂, Si(R’)₃, COOR’ y CON(R’)₂; o R¹¹ y R¹² o R¹¹ y R¹³ junto con el átomo al que están unidos o junto con otros átomos seleccionados del grupo que consiste en C, N, O, S y que opcionalmente incluyen de 1 a 3 miembros del anillo seleccionados del grupo que consiste en C(=O), C(=S), S(O)ₘ y Si(R’)₂ pueden formar un anillo de tres a siete miembros, que por su parte puede estar sustituido por uno o más grupos seleccionados del grupo que consiste en X, CN, R’, OR’, SR’, N(R’)₂, Si(R’)₃, COOR’ y CON(R’)₂; R¹⁴ se selecciona del grupo que consiste en hidrógeno, X, ciano, C₁₋₁₂-alquilo, C₂₋₁₂-alquenilo, C₂₋₁₂-alquinilo, C₁₋₁₂-haloalquilo, C₂₋₁₂-haloalquenilo, C₂₋₁₂-haloalquinilo, N(R’’)₂, SCN, S(O)ₙR’’, Si(R’)₃, OR’, (C=O)-R’’, CR’=NR’’, C₃₋₈-cicloalquilo y C₄₋₈-cicloalquenil, en el que uno o más átomos de carbono en los sistemas de anillo mencionados pueden estar sustituidos por heteroátomos seleccionados del grupo que consiste en N, O, S y que opcionalmente incluyen de 1 a 3 miembros del anillo seleccionados del grupo que consiste en C(=O), C(=S), S(O)ₘ y Si(R’)₂; R⁸ y R¹¹ o dos R¹¹ junto con el átomo al que están unidos o junto con otros átomos seleccionados del grupo que consiste en C, N, O, S, y que opcionalmente incluyen de 1 a 3 miembros del anillo seleccionados del grupo que consiste en C(=O), C(=S), S(O)ₘ y Si(R’₂), pueden formar un anillo de tres a diez miembros, que por su parte puede estar sustituido por uno o por más grupos seleccionados del grupo que consiste en X, CN, R’, OR’, SR’, N(R’)₂, Si(R’)₃, COOR’ y CON(R’)₂; o R⁹ y R¹¹ o R¹⁰ y R¹¹ junto con el átomo al que están unidos o junto con otros átomos seleccionados del grupo que consiste en C, N, O, S, y que opcionalmente incluyen de 1 a 3 miembros del anillo seleccionados del grupo que consiste en C(=O), C(=S), S(O)ₘ y Si(R’)₂, pueden formar un anillo de tres a diez miembros, que por su parte puede estar sustituido por uno o más grupos seleccionados del grupo que consiste en X, CN, R’, OR’, SR’, N(R’)₂, Si(R’)₃, COOR’ y CON(R’)₂; cada grupo de R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹² y R¹³ puede ser opcionalmente sustituido por uno o más grupos seleccionados del grupo que consiste en X, CN, R’, OR’, SR’, N(R’R’’), Si(R’)₃, COOR’ y CON(R’R’’); X representa halógeno; R’ se selecciona del grupo que consiste en hidrógeno, C₁₋₁₂-alquilo y C₃₋₈-cicloalquilo; en el que los grupos alquilo y cicloalquilo pueden estar opcionalmente sustituidos con uno o más X; R’’ se selecciona del grupo que consiste en hidrógeno, C₁₋₁₂-alquilo, C₁₋₁₂-haloalquilo, N(R’)₂, OR’, C₃₋₈-cicloalquilo y C₆₋₁₈-arilo, donde cada grupo de R’’ opcionalmente puede ser sustituido por uno o más grupos seleccionados del grupo que consiste en X, CN, R’, OR’, SR’, N(R’)₂, Si(R’)₃, COOR’ y CON(R’)₂; y uno o más átomos de carbono en dichos sistemas de anillo pueden sustituirse por heteroátomos seleccionados del grupo que consiste en N, O, S, y que opcionalmente incluyen de 1 a 3 miembros del anillo seleccionados del grupo que consiste en C(=O), C(=S), S(O)ₘ y Si(R’)₂; R’’’ se selecciona de los grupos que consisten en hidrógeno, R’’’, ciano, C₁₋₁₂-alquilo, C₁₋₁₂-haloalquilo, C₂₋₁₂-alquenilo, C₂₋₁₂-alquinilo, OR’, (C=O)-R’, COOR’, CON(R’)₂, C₃₋₈-cicloalquilo, C₄₋₈-cicloalquenilo, C₄₋₈-cicloalquinil, C₆₋₁₈-arilo y C₇₋₁₉-aralquilo; en el que uno o más átomos de carbono en dichos sistemas de anillo pueden estar sustituidos por heteroátomos seleccionados del grupo que consiste en N, O, S y que opcionalmente incluyen de 1 a 3 miembros del anillo seleccionados del grupo que consiste en C(=O), C(=S), S(O)ₘ o Si(R’)₂; y cada uno de los grupos anteriores puede estar sustituido por uno o más grupos seleccionados del grupo que consiste en X, CN, R’, OR’, SR’, N(R’)₂, Si(R’)₃, COOR’ y CON(R’)₂; n representa un número entero 0, 1 ó 2; m representa un número entero 1 ó 2; o sales agrícolamente aceptables, isómeros / isómeros estructurales, estereoisómeros, diastereómeros, enantiómeros, tautómeros, complejos metálicos, polimorfos o N-óxidos de los mismos.This describes phenylamide compounds of the formula (1), in which Cy, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰ and m have the same meanings as defined in the description. This further describes a process for the preparation of compounds of formula (1). Furthermore, the present invention describes the use of compounds of formula (1) and/or their compositions to protect agricultural and/or horticultural crops against unwanted phytopathogenic microorganisms. Claim 1: A compound of formula (1) in which; R¹ is selected from the group consisting of hydrogen, cyano, C₁₋₁₂-alkyl, C₂₋₁₂-alkenyl, C₂₋₁₂-alkynyl, C₁₋₁₂-haloalkyl, C₂₋₁₂-haloalkenyl, C₂₋₁₂-haloalkynyl, SR , OR, C₃₋₈-cycloalkyl, C₄₋₈-cycloalkenyl, and C₄₋₈-cycloalkynyl; wherein one or more carbon atoms in said ring systems may be replaced by heteroatoms selected from the group consisting of N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=O) , C(=S), S(O)ₘ and Si(R)₂; R² and R³ are independently selected from the group consisting of hydrogen, cyano, C₁₋₁₂-alkyl, C₂₋₁₂-alkenyl, C₂₋₁₂-alkynyl, C₁₋₁₂-haloalkyl, C₂₋₁₂-haloalkenyl, C₂₋₁₂-haloalkynyl , C₃₋₈-cycloalkyl, C₄₋₈-cycloalkenyl, C₄₋₈-cycloalkynyl, S(O)ₙR, OR, and (C=O)-R; wherein one or more carbon atoms in said ring systems may be replaced by heteroatoms selected from the group consisting of N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=O) , C(=S), S(O)ₘ and Si(R)₂; R¹ and R², R² and R³ or R¹ and R³ together with the atoms to which they are attached or together with other atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=O), C(=S), and S(O)ₘ or Si(R)₂ may form a three to seven membered non-aromatic ring, which itself may be substituted by one or more groups selected from the group consisting of X, CN, R, OR, SR, N(R)₂ and Si(R)₃; each group of R¹, R² and R³ may be optionally substituted by one or more groups selected from the group consisting of X, CN, R, OR, SR, N(R)₂, Si(R)₃, COOR and CON(R)₂; R⁴ and R⁵ are independently selected from the group consisting of X, cyano, C₁₋₁₂-alkyl, C₂₋₁₂-alkenyl, C₂₋₁₂-alkynyl, C₁₋₁₂-haloalkyl, C₂₋₁₂-haloalkenyl, C₂₋-haloalkynyl , N(R)₂, OR, S(O)ₙR, SCN, SF₅, Si(R)₃, (C=O)-R, CR=NR, C₃ ₋₈-cycloalkyl, C₄₋₈-cycloalkenyl, and C₃₋₅-heterocyclyl, wherein one or more carbon atoms in said ring systems may be replaced by heteroatoms selected from the group consisting of N, O, S and optionally they include 1 to 3 ring members selected from the group consisting of C(=O), C(=S), S(O)ₘ and Si(R)₂; R⁶ and R⁷ are independently selected from the group consisting of hydrogen, X, cyano, C₁₋₁₂-alkyl, C₂₋₁₂-alkenyl, C₂₋₁₂-alkynyl, C₁₋₁₂-haloalkyl, C₂₋₁₂-haloalkenyl, C₂₁₋ -haloalkynyl, (NR)₂, OR, S(O)ₙR, SCN, Si(R)₃, (C=O)-R, CR=NR, C₃₋ ₈-cycloalkyl, C₄₋₈-cycloalkenyl and C₄₋₈-cycloalkynyl; wherein one or more carbon atoms in said ring systems may be replaced by heteroatoms selected from the group consisting of N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=O) , C(=S), S(O)ₘ and Si(R₂); or R⁴ and R⁶ or R⁵ and R⁷ together with the atom to which they are attached or together with other atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=O), C(=S), S(O)ₘ and Si(R)₂ may form a three to six membered ring, which in turn may be substituted by one or more groups selected from the group consisting of X, CN, R, OR, SR, N(R)₂, Si(R)₃, COOR and CON(R)₂; R⁸ is selected from the group consisting of hydrogen, cyano, C₁₋₁₂-alkyl, C₂₋₁₂-alkenyl, C₂₋₁₂-alkynyl, C₁₋₁₂-haloalkyl, C₂₋₁₂-haloalkenyl, C₂₋₁₂-haloalkynyl, S( O)ₙR, SiR₃, NRR, (C=O)-R, CR=NR, C₃₋₈-cycloalkyl, C₄₋₈-cycloalkenyl, C₄₋₈-cycloalkynyl and C₇₋₁₉-aralkyl; wherein one or more carbon atoms in said ring systems may be replaced by heteroatoms selected from the group consisting of N, O, and S(O)ₙ; and all of the aforementioned groups may be substituted by one or more groups selected from the group consisting of X, CN, R, OR, SR, NR₂, SiR₃, COOR and CONR₂; R⁹ and R¹⁰ are independently selected from the group consisting of hydrogen, X, cyano, C₁₋₁₂-alkyl, C₂₋₁₂-alkenyl, C₂₋₁₂-alkynyl, C₁₋₁₂-haloalkyl, C₂₋₁₂-haloalkenyl, C₁₋₋ -haloalkynyl, (NR)₂, OR, S(O)ₙR, SCN, Si(R)₃, (C=O)-R, CR=NR, C₃₋₈ -cycloalkyl, C₄₋₈-cycloalkenyl and C₄₋₈-cycloalkynyl; wherein one or more carbon atoms in said ring systems may be replaced by heteroatoms selected from the group consisting of N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=O) , C(=S), S(O)ₘ and Si(R)₂; or R⁹ and R¹⁰ together with the atom to which they are attached or together with other atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=O ), C(=S), S(O)ₘ or Si(R)₂ may form a three to six membered ring, which in turn may be substituted by one or more groups selected from the group consisting of X, CN, R, OR, SR, N(R)₂, Si(R)₃, COOR and CON(R)₂; Cy is selected from the group consisting of a fused or unfused C₃₋₁₈ carbocyclyl or C₃₋₁₈ heterocyclyl group, which may optionally be substituted with one or more groups of R¹¹; R¹¹ is selected from the group consisting of hydrogen, X, cyano, nitro, C₁₋₁₂-alkyl, C₂₋₁₂-alkenyl, C₂₋₁₂-alkynyl, C₁₋₁₂-haloalkyl, C₂₋₁₂-haloalkenyl, C₂₋₁₂- haloalkynyl, C₃₋₈-cycloalkyl, C₄₋₈-cycloalkenyl, C₄₋₈-cycloalkynyl, C₇₋₁₉-aralkyl, C₅₋₁₂-bicycloalkyl, C₅₋₁₂-bicycloalkenyl, C₆₋₁₀-heterocyl, C₋₋-aryl, C₋₋₀-aryl, C₋₋₀-aryl, C₋₋₀-aryl, SCN, SF₅, N(R)₂, OR, S(O)ₙR, Si(R)₃, (C=O)-R, C₁₋₈-alkyl-S(O) ₙR, C₁₋₈-alkyl-C(=O)-R, CR=NR, S(O)ₙC₆₋₁₈-aryl, and S(O)ₙC₇₋₁₉-aralkyl, where one or more carbon atoms in said ring system may be replaced by heteroatoms selected from the group consisting of N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=O) , C(=S), S(O)ₘ and Si(R)₂; or R¹¹ is selected from the group consisting of the group of formulas (2), in which the wavy line represents bonds of the atom or group; R⁹ᵃ and R¹⁰ᵃ are independently selected from the group consisting of hydrogen, X, cyano, C₁₋₁₂-alkyl, C₂₋₁₂-alkenyl, C₂₋₁₂-alkynyl, C₁₋₁₂-haloalkyl, C₂₋₁₂-haloalkenyl, C₂₋₁₂-haloalkenyl, C₂₋₁₂-haloalkenyl, -haloalkynyl, (NR)₂, OR, S(O)ₙR, (C=O)-R, C₃₋₈-cycloalkyl, C₄₋₈-cycloalkenyl and C₄₋₈-cycloalkynyl; wherein one or more carbon atoms in said ring systems may be replaced by heteroatoms selected from the group consisting of N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=O) , C(=S), S(O)ₘ and Si(R)₂; or R⁹ᵃ and R¹⁰ᵃ together with the atom to which they are attached or together with other atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=O ), C(=S), S(O)ₘ or Si(R)₂ may form a three to six membered ring, which in turn may be substituted by one or more groups selected from the group consisting of X, CN, R, OR, SR, N(R)₂, Si(R)₃, COOR and CON(R)₂; o R⁹ᵃ and R¹⁰ᵃ together with the atom to which they are attached can form a =O or =S group; R¹² is independently selected from the group consisting of C₁₋₁₂-alkyl, C₂₋₁₂-alkenyl, C₂₋₁₂-alkynyl, C₁₋₁₂-haloalkyl, C₂₋₁₂-haloalkenyl, C₂₋₁₂-haloalkynyl, (C=O) -R, C₃₋₈-cycloalkyl, C₄₋₈-cycloalkenyl, C₇₋₁₉-aralkyl, C₅₋₁₂-bicycloalkyl and C₃₋₁₈-fused or unfused carbocycle substituted with one or more groups of R¹⁴; wherein one or more carbon atoms in said ring systems may be replaced by heteroatoms selected from the group consisting of N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=O ), C(=S), S(O)ₘ or Si(R)₂; R¹³ is selected from the group consisting of hydrogen, cyano, C₁₋₁₂-alkyl, C₂₋₁₂-alkenyl, C₂₋₁₂-alkynyl, C₁₋₁₂-haloalkyl, C₂₋₁₂-haloalkenyl, C₂₋₁₂-haloalkynyl, OR , N(RR), Si(R)₃, (C=O)-R, S(O)ₙR, C₁₋₈-alkyl-S(O)ₙR , C₁₋₈-alkyl-(C=O)-R, S(O)ₙC₆₋₁₈-aryl, S(O)ₙC₇₋₁₉-aralkyl, C₃₋₈-cycloalkyl and C₄₋₈-cycloalkenyl ; wherein one or more carbon atoms in said ring systems may be replaced by heteroatoms selected from the group consisting of N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=O) , C(=S), S(O)ₘ or Si(R)₂; or R¹² and R¹³ together with the atom to which they are attached or together with other atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(= O), C(=S), S(O)ₘ and Si(R)₂ may form a three to seven membered ring, which in turn may be substituted by one or more groups selected from the group consisting of X , CN, R, OR, SR, N(R)₂, Si(R)₃, COOR and CON(R)₂; o R¹¹ and R¹² o R¹¹ and R¹³ together with the atom to which they are attached or together with other atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group consisting of in C(=O), C(=S), S(O)ₘ and Si(R)₂ can form a three to seven membered ring, which in turn can be substituted by one or more groups selected from the group consisting of X, CN, R, OR, SR, N(R)₂, Si(R)₃, COOR, and CON(R)₂; R¹⁴ is selected from the group consisting of hydrogen, X, cyano, C₁₋₁₂-alkyl, C₂₋₁₂-alkenyl, C₂₋₁₂-alkynyl, C₁₋₁₂-haloalkyl, C₂₋₁₂-haloalkenyl, C₂₋₁₂-haloalkynyl, N(R)₂, SCN, S(O)ₙR, Si(R)₃, OR, (C=O)-R, CR=NR, C₃₋₈-cycloalkyl and C₄₋₈-cycloalkenyl, wherein one or more carbon atoms in said ring systems may be substituted by heteroatoms selected from the group consisting of N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=O), C(=S), S(O)ₘ and Si(R)₂; R⁸ and R¹¹ or two R¹¹ together with the atom to which they are attached or together with other atoms selected from the group consisting of C, N, O, S, and optionally including 1 to 3 ring members selected from the group consisting of C(=O), C(=S), S(O)ₘ and Si(R₂), can form a ring with three to ten members, which in turn can be substituted by one or more groups selected from group consisting of X, CN, R, OR, SR, N(R)₂, Si(R)₃, COOR, and CON(R)₂; o R⁹ and R¹¹ o R¹⁰ and R¹¹ together with the atom to which they are attached or together with other atoms selected from the group consisting of C, N, O, S, and optionally including 1 to 3 ring members selected from the group consisting of consisting of C(=O), C(=S), S(O)ₘ and Si(R)₂, can form a three to ten membered ring, which in turn may be substituted by one or more selected groups from the group consisting of X, CN, R, OR, SR, N(R)₂, Si(R)₃, COOR, and CON(R)₂; each group of R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹² and R¹³ may be optionally substituted by one or more groups selected from the group consisting of X, CN, R, OR, SR, N(RR), Si(R)₃, COOR and CON(RR); X represents halogen; R is selected from the group consisting of hydrogen, C₁₋₁₂-alkyl, and C₃₋₈-cycloalkyl; wherein the alkyl and cycloalkyl groups may be optionally substituted with one or more X; R is selected from the group consisting of hydrogen, C₁₋₁₂-alkyl, C₁₋₁₂-haloalkyl, N(R)₂, OR, C₃₋₈-cycloalkyl, and C₆₋₁₈-aryl, where each group of R may optionally be substituted by one or more groups selected from the group consisting of X, CN, R, OR, SR, N(R)₂, Si(R)₃, COOR and CON( R)₂; and one or more carbon atoms in said ring systems may be substituted by heteroatoms selected from the group consisting of N, O, S, and optionally including 1 to 3 ring members selected from the group consisting of C(=O) , C(=S), S(O)ₘ and Si(R)₂; R is selected from the groups consisting of hydrogen, R, cyano, C₁₋₁₂-alkyl, C₁₋₁₂-haloalkyl, C₂₋₁₂-alkenyl, C₂₋₁₂-alkynyl, OR, (C =O)-R, COOR, CON(R)₂, C₃₋₈-cycloalkyl, C₄₋₈-cycloalkenyl, C₄₋₈-cycloalkynyl, C₆₋₁₈-aryl, and C₇₋₁₉-aralkyl; wherein one or more carbon atoms in said ring systems may be substituted by heteroatoms selected from the group consisting of N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(= O), C(=S), S(O)ₘ or Si(R)₂; and each of the above groups may be substituted by one or more groups selected from the group consisting of X, CN, R, OR, SR, N(R)₂, Si(R)₃, COOR and CON(R)₂; n represents an integer 0, 1 or 2; m represents an integer 1 or 2; or agriculturally acceptable salts, isomers/structural isomers, stereoisomers, diastereomers, enantiomers, tautomers, metal complexes, polymorphs, or N-oxides thereof.

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