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AR111850A1 - SUBSTITUTED TRIFLUOROMETILOXADIAZOLS TO FIGHT FITOPATHOGEN FUNGI - Google Patents

SUBSTITUTED TRIFLUOROMETILOXADIAZOLS TO FIGHT FITOPATHOGEN FUNGI

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AR111850A1
AR111850A1 ARP180101171A ARP180101171A AR111850A1 AR 111850 A1 AR111850 A1 AR 111850A1 AR P180101171 A ARP180101171 A AR P180101171A AR P180101171 A ARP180101171 A AR P180101171A AR 111850 A1 AR111850 A1 AR 111850A1
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Argentina
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alkyl
group
groups
alkoxy
heterocycle
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ARP180101171A
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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
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
    • 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
    • A01N43/82—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 five-membered rings with three ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

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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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Reivindicación 1: Compuestos caracterizados por la fórmula (1), o los N-óxidos, o las sales de aquellos aceptables en la agricultura, en donde: A es fenilo o un heterociclo aromático de 5 ó 6 miembros, en donde los átomos miembros del anillo del heterociclo aromático incluyen, además de los átomos de carbono, 1, 2, 3 ó 4 heteroátomos seleccionados de N, O y S como átomos miembros del anillo; y en donde el anillo de fenilo o el heterociclo aromático es no sustituido o sustituido con 1, 2, 3 ó 4 grupos RA idénticos o diferentes; en donde RA es halógeno, ciano, C₁₋₆-alquilo, C₁₋₆-haloalquilo, C₁₋₆-alcoxi o C₁₋₆-haloalcoxi; W es -NR²-(C=O)-#, -NR²-(C=S)-#, -NR²-S(=O)ₚ-#, -(C=O)-NR²-#, -(C=S)-NR²-#, -S(=O)ₚ-NR²-#, -NR²-(C=O)-NR⁵-#, -NR⁵-(C=O)-NR²-#, -NR²-(C=S)-NR⁵-#, -NR⁵-(C=S)-NR²-#, -NR²-S(=O)ₚ-NR⁵-#, -O-(C=O)-NR²-#, -O-(C=S)-NR²-#, -NR²-(C=O)-O-# o -NR²-(C=S)-O-#, en donde # indica la posición, que está unida a R¹; p es 0, 1 ó 2; R² es -N(R²ᵃ)₂; en donde R²ᵃ se selecciona independientemente del grupo que consiste en hidrógeno, OH, C₁₋₆-alquilo, C₂₋₆-alquenilo, C₂₋₆-alquinilo, C₃₋₈-cicloalquilo, C₃₋₈-cicloalquenilo, C₁₋₆-alcoxi, C₁₋₄-alcoxi-C₁₋₄-alquilo y C₁₋₆-alquiltio; y en donde cualquiera de los grupos alifáticos o cíclicos es no sustituido o sustituido con 1, 2, 3 o hasta la máxima cantidad posible de radicales idénticos o diferentes seleccionados del grupo que consiste en halógeno, hidroxi, oxo, ciano, C₁₋₆-alquilo, C₁₋₆-alcoxi y C₃₋₈-cicloalquilo; R⁵ es hidrógeno, C₁₋₆-alquilo, C₁₋₆-alcoxi, C₂₋₆-alquenilo, C₂₋₆-alquinilo, C₁₋₆-alcoxi, C₃₋₈-cicloalquilo, C₃₋₈-cicloalquenilo, C₃₋₈-cicloalquil-C₁₋₆-alquilo, fenil-C₁₋₄-alquilo o fenilo; y en donde cualquiera de los grupos alifáticos o cíclicos es no sustituido o sustituido con 1, 2, 3 o hasta la máxima cantidad posible de radicales idénticos o diferentes seleccionados del grupo que consiste en halógeno, ciano, C₁₋₆-alquilo y C₁₋₆-alcoxi; R¹ es C₁₋₆-alquilo, C₃₋₈-cicloalquilo, C₃₋₈-cicloalquenilo, C₂₋₆-alquenilo, C₂₋₆-alquinilo, C₁₋₆-alcoxiimino-C₁₋₄-alquilo, C₂₋₆-alqueniloxiimino-C₁₋₄-alquilo, C₂₋₆-alquiniloxiimino-C₁₋₄-alquilo, fenil-C₁₋₄-alquilo, fenil-C₁₋₄-alquenilo, fenil-C₁₋₄-alquinilo, heteroaril-C₁₋₄-alquilo, fenilo, naftilo o un heterociclo mono- o bicíclico saturado, parcialmente insaturado o aromático de 3 a 10 miembros, en donde los átomos miembros del anillo de dicho heterociclo mono- o bicíclico incluyen, además de los átomos de carbono, otros 1, 2, 3 ó 4 heteroátomos seleccionados de N, O y S como átomos miembros del anillo; y en donde el grupo heteroarilo en el grupo heteroaril-C₁₋₄-alquilo es un heterociclo aromático de 5 ó 6 miembros, en donde los átomos miembros del anillo del anillo heterocíclico incluyen, además de los átomos de carbono, 1, 2, 3 ó 4 heteroátomos seleccionados de N, O y S como átomos miembros del anillo; y en donde cualquiera de los grupos alifáticos o cíclicos mencionados anteriormente es no sustituido o sustituido con 1, 2, 3 o hasta la máxima cantidad posible de grupos R¹ᵃ idénticos o diferentes; o R¹ es un carbociclo bicíclico de la fórmula (2) en donde Cᵃ y Cᵇ son átomos de carbono cabeza de puente; X es un enlace simple directo o un grupo divalente seleccionado del grupo que consiste en -CH₂-, -CH₂-CH₂-, -(CH₂)₃-, -(CH₂)₄-, -CH=CH-, -CH₂-CH=CH-, -CH=CH-CH₂- y -CH=CH-CH=CH-; Y y Z independientemente entre sí, son un grupo divalente seleccionado del grupo que consiste en -CH₂-, -CH₂-CH₂-, -(CH₂)₃-, -(CH₂)₄-, -CH=CH-, -CH₂-CH=CH-, CH=CH-CH₂- y -CH=CH-CH=CH-; o R¹ es un carbociclo tricíclico de la fórmula (3) en donde Cᵃ y Cᵇ son átomos de carbono cabeza de puente; X es un enlace simple directo o un grupo divalente seleccionado del grupo que consiste en CH₂-, -CH₂-CH₂-, -(CH₂)₃-, -(CH₂)₄-, -CH=CH-, -CH₂-CH=CH-, -CH=CH-CH₂- y -CH=CH-CH=CH-; Y y Z, independientemente entre sí, son un grupo divalente seleccionado del grupo que consiste en -CH₂-, -CH₂-CH₂-, -(CH₂)₃-, -(CH₂)₄-, -CH=CH-, -CH₂-CH=CH-, -CH=CH-CH₂- y -CH=CH-CH=CH-; y en donde los grupos Y y Z están unidos a átomos de carbono cabeza de puente Cᵃ y Cᵇ; T es un grupo divalente seleccionado del grupo que consiste en -CH₂-, -CH₂-CH₂-, -(CH₂)₃-, -(CH₂)₄-, -CH=CH-, -CH₂-CH=CH-, -CH=CH-CH₂- y -CH=CH-CH=CH-; y en donde el grupo T se une a un átomo de carbono en cada uno de los grupos Y y Z; y siempre que, si R¹ es un carbociclo tricíclico de la fórmula (3), en donde X es un enlace simple directo o un grupo divalente -CH₂-, los grupos T y Z, independientemente entre sí, son un grupo divalente seleccionado del grupo que consiste en -CH₂-CH₂-, -(CH₂)₃-, -(CH₂)₄-, -CH=CH-, -CH₂-CH=CH-, -CH=CH-CH₂- y -CH=CH-CH=CH-; y en donde los grupos de fórmula (2) ó (3) están conectados al grupo W a través de uno de los átomos de carbono del anillo; y en donde los grupos de fórmula (2) ó (3) son no sustituidos o sustituidos con 1, 2, 3, 4 o hasta la máxima cantidad posible de radicales seleccionados del grupo que consiste en oxo, hidroxi, halógeno, C₁₋₃-alquilo, C₁₋₃-haloalquilo, C₃₋₆-cicloalquilo, vinilideno y diclorovinilideno; o R¹ y uno de los dos grupos R²ᵃ, junto con el átomo de nitrógeno al que R²ᵃ está unido, y junto con grupos interyacentes, que se ubican entre dicho átomo de nitrógeno y el grupo R¹, forman un heterociclo mono- o bicíclico saturado o parcialmente insaturado de 3 a 10 miembros, en donde el heterociclo incluye, además de dos átomos de nitrógeno y uno o más átomos de carbono, ningún otro heteroátomo o 1, 2 ó 3 heteroátomos adicionales seleccionados independientemente de N, O y S como átomos miembros del anillo; y en donde el heterociclo es no sustituido o sustituido con 1, 2, 3, 4 o hasta la máxima cantidad posible de grupos R¹ᵃ idénticos o diferentes; o R¹ y R⁵, junto con el átomo de nitrógeno al que están unidos y junto con los grupos interyacentes, de haberlos, que se ubican entre dicho átomo de nitrógeno y el grupo R¹, forman un heterociclo mono- o bicíclico saturado o parcialmente insaturado de 3 a 10 miembros, en donde el heterociclo incluye, además de un átomo de nitrógeno y uno o más átomos de carbono, 1, 2 ó 3 heteroátomos seleccionados independientemente de N, O y S como átomos miembros del anillo; y en donde uno o dos grupos CH₂ del heterociclo se pueden reemplazar por uno o dos grupos seleccionados independientemente del grupo que consiste en C(=O)- y -C(=S)-; y en donde el heterociclo es no sustituido o sustituido con 1, 2, 3, 4 o hasta la máxima cantidad posible de radicales idénticos o diferentes seleccionados del grupo que consiste en halógeno, ciano, C₁₋₆-alquilo, C₁₋₆-haloalquilo, C₁₋₆-alcoxi y C₁₋₆-haloalcoxi; R¹ᵃ es halógeno, oxo, ciano, NO₂, OH, SH, NH₂, C₁₋₆-alquilo, C₁₋₆-haloalquilo, C₁₋₆-alcoxi, C₁₋₆-haloalcoxi, C₁₋₆-alquiltio, C₁₋₆-haloalquiltio, C₃₋₈-cicloalquilo, -NHSO₂-C₁₋₄-alquilo, (C=O)-C₁₋₄-alquilo, C(=O)-C₁₋₄-alcoxi, C₁₋₆-alquilsulfonilo, hidroxi-C₁₋₄-alquilo, C(=O)-NH₂, C(=O)-NH(C₁₋₄-alquilo), C₁₋₄-alquiltio-C₁₋₄-alquilo, amino-C₁₋₄-alquilo, C₁₋₄-alquilamino-C₁₋₄-alquilo, di-C₁₋₄-alquilamino-C₁₋₄-alquilo, aminocarbonil-C₁₋₄-alquilo o C₁₋₄-alcoxi-C₁₋₄-alquilo; m es 0 ó 1; R³, R⁴ se seleccionan, independientemente entre sí, del grupo que consiste en hidrógeno, halógeno, ciano, C₁₋₄-alquilo, C₁₋₄-alquenilo, C₁₋₄-alquinilo, C₁₋₄-haloalquilo y C₁₋₄-alcoxi; o R³ y R⁴, junto con el átomo de carbono al que están unidos, forman un carbociclo saturado de 3 a 7 miembros o un heterociclo saturado de 3 a 6 miembros; en donde el heterociclo saturado incluye, además de los átomos de carbono, 1, 2 ó 3 heteroátomos seleccionados independientemente del grupo que consiste en N, O y S como átomos miembros del anillo; y en donde dicho átomo miembro del anillo de N se sustituye con el grupo RN; en donde RN es hidrógeno, C₁₋₆-alquilo o halógeno; y en donde el átomo miembro del anillo de S es no sustituido o sustituido con 1 ó 2 radicales oxo; y en donde uno o dos grupos CH₂ del carbociclo saturado o del heterociclo saturado se pueden reemplazar con uno o dos grupos seleccionados independientemente de -C(=O)- y -C(=S)-; y en donde los átomos miembros del anillo de carbono del carbociclo saturado o del heterociclo saturado son no sustituidos o sustituidos con una cantidad total de 1, 2, 3, 4 o hasta la máxima cantidad posible de radicales idénticos o diferentes seleccionados del grupo que consiste en halógeno, ciano, C₁₋₆-alquilo, C₁₋₆-alcoxi y C₃₋₈-cicloalquilo; con la excepción de los compuestos de la fórmula (1), en donde m es 0, y W es -(C=O)-NR²-#.Claim 1: Compounds characterized by the formula (1), or the N-oxides, or salts of those acceptable in agriculture, wherein: A is phenyl or an aromatic heterocycle of 5 or 6 members, wherein the atoms atoms of the aromatic heterocycle ring include, in addition to carbon atoms, 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein the phenyl ring or aromatic heterocycle is unsubstituted or substituted with 1, 2, 3 or 4 identical or different RA groups; wherein RA is halogen, cyano, C₁₋₆-alkyl, C₁₋₆-haloalkyl, C₁₋₆-alkoxy or C₁₋₆-haloalkoxy; W is -NR²- (C = O) - #, -NR²- (C = S) - #, -NR²-S (= O) ₚ- #, - (C = O) -NR²- #, - (C = S) -NR²- #, -S (= O) ₚ-NR²- #, -NR²- (C = O) -NR⁵- #, -NR⁵- (C = O) -NR²- #, -NR²- ( C = S) -NR⁵- #, -NR⁵- (C = S) -NR²- #, -NR²-S (= O) ₚ-NR⁵- #, -O- (C = O) -NR²- #, - O- (C = S) -NR²- #, -NR²- (C = O) -O- # or -NR²- (C = S) -O- #, where # indicates the position, which is attached to R¹ ; p is 0, 1 or 2; R² is -N (R²ᵃ) ₂; wherein R²ᵃ is independently selected from the group consisting of hydrogen, OH, C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkynyl, C₃₋₈-cycloalkyl, C₃₋₈-cycloalkenyl, C₁₋₆-alkoxy , C₁₋₄-alkoxy-C₁₋₄-alkyl and C₁₋₆-alkylthio; and wherein any of the aliphatic or cyclic groups is unsubstituted or substituted with 1, 2, 3 or up to the maximum possible amount of identical or different radicals selected from the group consisting of halogen, hydroxy, oxo, cyano, C₁₋₆- alkyl, C₁₋₆-alkoxy and C₃₋₈-cycloalkyl; R⁵ is hydrogen, C₁₋₆-alkyl, C₁₋₆-alkoxy, C₂₋₆-alkenyl, C₂₋₆-alkynyl, C₁₋₆-alkoxy, C₃₋₈-cycloalkyl, C₃₋₈-cycloalkenyl, C₃₋₈- cycloalkyl-C₁₋₆-alkyl, phenyl-C₁₋₄-alkyl or phenyl; and wherein any of the aliphatic or cyclic groups is unsubstituted or substituted with 1, 2, 3 or up to the maximum possible amount of identical or different radicals selected from the group consisting of halogen, cyano, C₁₋₆-alkyl and C₁₋ ₆-alkoxy; R¹ is C₁₋₆-alkyl, C₃₋₈-cycloalkyl, C₃₋₈-cycloalkenyl, C₂₋₆-alkenyl, C₂₋₆-alkynyl, C₁₋₆-alkoxyimino-C₁₋₄-alkyl, C₂₋₆-alkenyloxyimino- C₁₋₄-alkyl, C₂₋₆-alkynyloxyimino-C₁₋₄-alkyl, phenyl-C₁₋₄-alkyl, phenyl-C₁₋₄-alkenyl, phenyl-C₁₋₄-alkynyl, heteroaryl-C₁₋₄-alkyl, phenyl, naphthyl or a saturated mono- or bicyclic heterocycle, partially unsaturated or aromatic of 3 to 10 members, wherein the ring member atoms of said mono- or bicyclic heterocycle include, in addition to the carbon atoms, another 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein the heteroaryl group in the heteroaryl-C₁₋₄-alkyl group is a 5- or 6-membered aromatic heterocycle, wherein the heterocyclic ring ring member atoms include, in addition to the carbon atoms, 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein any of the aforementioned aliphatic or cyclic groups is unsubstituted or substituted with 1, 2, 3 or up to the maximum possible amount of identical or different R¹ᵃ groups; or R¹ is a bicyclic carbocycle of the formula (2) wherein Cᵃ and Cᵇ are bridgehead carbon atoms; X is a direct single bond or a divalent group selected from the group consisting of -CH₂-, -CH₂-CH₂-, - (CH₂) ₃-, - (CH₂) ₄-, -CH = CH-, -CH₂-CH = CH-, -CH = CH-CH₂- and -CH = CH-CH = CH-; Y and Z independently of each other, are a divalent group selected from the group consisting of -CH₂-, -CH₂-CH₂-, - (CH₂) ₃-, - (CH₂) ₄-, -CH = CH-, -CH₂- CH = CH-, CH = CH-CH₂- and -CH = CH-CH = CH-; or R¹ is a tricyclic carbocycle of the formula (3) wherein Cᵃ and Cᵇ are bridgehead carbon atoms; X is a direct single bond or a divalent group selected from the group consisting of CH₂-, -CH₂-CH₂-, - (CH₂) ₃-, - (CH₂) ₄-, -CH = CH-, -CH₂-CH = CH-, -CH = CH-CH₂- and -CH = CH-CH = CH-; Y and Z, independently of each other, are a divalent group selected from the group consisting of -CH₂-, -CH₂-CH₂-, - (CH₂) ₃-, - (CH₂) ₄-, -CH = CH-, -CH₂ -CH = CH-, -CH = CH-CH₂- and -CH = CH-CH = CH-; and where the groups Y and Z are attached to bridgehead carbon atoms Cᵃ and Cᵇ; T is a divalent group selected from the group consisting of -CH₂-, -CH₂-CH₂-, - (CH₂) ₃-, - (CH₂) ₄-, -CH = CH-, -CH₂-CH = CH-, - CH = CH-CH₂- and -CH = CH-CH = CH-; and wherein group T binds to a carbon atom in each of groups Y and Z; and provided that, if R¹ is a tricyclic carbocycle of the formula (3), where X is a direct single bond or a divalent group -CH₂-, groups T and Z, independently of each other, are a divalent group selected from the group consisting of -CH₂-CH₂-, - (CH₂) ₃-, - (CH₂) ₄-, -CH = CH-, -CH₂-CH = CH-, -CH = CH-CH₂- and -CH = CH- CH = CH-; and wherein the groups of formula (2) or (3) are connected to the group W through one of the ring carbon atoms; and wherein the groups of formula (2) or (3) are unsubstituted or substituted with 1, 2, 3, 4 or up to the maximum possible amount of radicals selected from the group consisting of oxo, hydroxy, halogen, C₁₋₃ -alkyl, C₁₋₃-haloalkyl, C₃₋₆-cycloalkyl, vinylidene and dichlorovinylidene; or R¹ and one of the two R²ᵃ groups, together with the nitrogen atom to which R²ᵃ is attached, and together with interjacent groups, which are located between said nitrogen atom and the R¹ group, form a saturated mono- or bicyclic heterocycle or partially unsaturated 3 to 10 members, wherein the heterocycle includes, in addition to two nitrogen atoms and one or more carbon atoms, no other heteroatom or 1, 2 or 3 additional heteroatoms independently selected from N, O and S as member atoms From the ring; and wherein the heterocycle is unsubstituted or substituted with 1, 2, 3, 4 or up to the maximum possible amount of identical or different R¹ᵃ groups; or R¹ and R⁵, together with the nitrogen atom to which they are attached and together with the interjacent groups, if any, which are located between said nitrogen atom and the group R¹, form a saturated or partially unsaturated mono- or bicyclic heterocycle of 3 to 10 members, wherein the heterocycle includes, in addition to a nitrogen atom and one or more carbon atoms, 1, 2 or 3 heteroatoms independently selected from N, O and S as ring member atoms; and wherein one or two CH₂ groups of the heterocycle can be replaced by one or two groups independently selected from the group consisting of C (= O) - and -C (= S) -; and wherein the heterocycle is unsubstituted or substituted with 1, 2, 3, 4 or up to the maximum possible amount of identical or different radicals selected from the group consisting of halogen, cyano, C₁₋₆-alkyl, C₁₋₆-haloalkyl , C₁₋₆-alkoxy and C₁₋₆-haloalkoxy; R¹ᵃ is halogen, oxo, cyano, NO₂, OH, SH, NH₂, C₁₋₆-alkyl, C₁₋₆-haloalkyl, C₁₋₆-alkoxy, C₁₋₆-haloalkoxy, C₁₋₆-alkylthio, C₁₋₆- haloalkylthio, C₃₋₈-cycloalkyl, -NHSO₂-C₁₋₄-alkyl, (C = O) -C₁₋₄-alkyl, C (= O) -C₁₋₄-alkoxy, C₁₋₆-alkylsulfonyl, hydroxy-C₁ ₋₄-alkyl, C (= O) -NH₂, C (= O) -NH (C₁₋₄-alkyl), C₁₋₄-alkylthio-C₁₋₄-alkyl, amino-C₁₋₄-alkyl, C₁₋ ₄-alkylamino-C₁₋₄-alkyl, di-C₁₋₄-alkylamino-C₁₋₄-alkyl, aminocarbonyl-C₁₋₄-alkyl or C₁₋₄-alkoxy-C₁₋₄-alkyl; m is 0 or 1; R³, R⁴ are independently selected from the group consisting of hydrogen, halogen, cyano, C₁₋₄-alkyl, C₁₋₄-alkenyl, C₁₋₄-alkynyl, C₁₋₄-haloalkyl and C₁₋₄-alkoxy ; or R³ and R⁴, together with the carbon atom to which they are attached, form a saturated carbocycle of 3 to 7 members or a saturated heterocycle of 3 to 6 members; wherein the saturated heterocycle includes, in addition to the carbon atoms, 1, 2 or 3 heteroatoms independently selected from the group consisting of N, O and S as ring member atoms; and wherein said N ring member atom is substituted with the RN group; wherein RN is hydrogen, C₁₋₆-alkyl or halogen; and wherein the S ring member atom is unsubstituted or substituted with 1 or 2 oxo radicals; and wherein one or two CH₂ groups of the saturated carbocycle or saturated heterocycle can be replaced with one or two groups independently selected from -C (= O) - and -C (= S) -; and wherein the carbon ring member atoms of the saturated carbocycle or saturated heterocycle are unsubstituted or substituted with a total amount of 1, 2, 3, 4 or up to the maximum possible amount of identical or different radicals selected from the group consisting in halogen, cyano, C₁₋₆-alkyl, C₁₋₆-alkoxy and C₃₋₈-cycloalkyl; with the exception of the compounds of the formula (1), where m is 0, and W is - (C = O) -NR²- #.

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