AR112068A1 - SUBSTITUTED OXADIAZOLES TO COMBAT PHYTOPATOGENIC FUNGI - Google Patents

SUBSTITUTED OXADIAZOLES TO COMBAT PHYTOPATOGENIC FUNGI

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AR112068A1
AR112068A1 ARP180101485A ARP180101485A AR112068A1 AR 112068 A1 AR112068 A1 AR 112068A1 AR P180101485 A ARP180101485 A AR P180101485A AR P180101485 A ARP180101485 A AR P180101485A AR 112068 A1 AR112068 A1 AR 112068A1
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Argentina
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alkyl
group
heterocycle
groups
substituted
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ARP180101485A
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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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

Oxadiazoles sustituidos útiles en la agricultura y al uso de estos para controlar hongos fitopatógenos; un método para combatir hongos fitopatógenos dañinos, en donde el proceso comprende tratar los hongos, las plantas, el suelo o las semillas que se desean proteger del ataque fúngico, con una cantidad eficaz de al menos un compuesto y composiciones agroquímicas que comprenden al menos un compuesto. 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; B es un grupo divalente -C(R³)₂-C(R⁴)₂- o -C(R³)=C(R⁴)-; W es O ó S; V es un enlace simple directo o un grupo divalente -NR²-; R² es hidrógeno, C₁₋₆-alquilo, 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, fenilo, formilo o N(R²ᵃ)₂; 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, C₃₋₈-cicloalquilo y C₁₋₆-alcoxi; y 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; 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 V 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 R², junto con el átomo de nitrógeno al que están unidos, forman un heterociclo monocíclico 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, ningún heteroátomo adicional o 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; o R¹ y uno de los dos grupos R²ᵃ, junto con el átomo de nitrógeno al que R²ᵃ está unido, y junto con el átomo de nitrógeno del grupo -NR²-, 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; 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; R³, R⁴ se seleccionan, independientemente entre sí, del grupo que consiste en hidrógeno, halógeno, ciano, C₁₋₄-alquilo, C₁₋₄-haloalquilo, C₁₋₄-alcoxi y C₁₋₄-haloalcoxi; o, si B es -C(R³)₂-C(R⁴)₂-, dos radicales R³ y/o dos radicales R⁴, que están unidos al mismo átomo de carbono, junto con dicho átomo de carbono, 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; o si B es -C(R³)₂-C(R⁴)₂-, un radical R³ y un radical R⁴, junto con los átomos de carbono a los que cada uno de ellos está unido, 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, que están representados por radicales R³ y R⁴, 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.Substituted oxadiazoles useful in agriculture and their use to control phytopathogenic fungi; a method for combating harmful phytopathogenic fungi, wherein the process comprises treating the fungi, plants, soil or seeds that are desired to be protected from fungal attack, with an effective amount of at least one compound and agrochemical compositions comprising at least one compound. Claim 1: Compounds characterized by formula (1), or N-oxides, or salts of those acceptable in agriculture wherein: A is phenyl or a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the aromatic heterocycle 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 the 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; B is a divalent group -C (R³) ₂-C (R⁴) ₂- or -C (R³) = C (R⁴) -; W is O or S; V is a direct single bond or a divalent group -NR²-; R² is hydrogen, C₁₋₆-alkyl, 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, phenyl, formyl or N (R²ᵃ) ₂; 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, C₃₋ ₈-cycloalkyl and C₁₋₆-alkoxy; and 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; 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 3- to 10-membered saturated, partially unsaturated or aromatic mono- or bicyclic heterocycle, wherein the ring member atoms of said mono- or bicyclic heterocycle include, in addition to carbon atoms, other 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 ring member atoms of the heterocyclic ring 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 aliphatic or cyclic groups mentioned above 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 formula (2), where 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 formula (3), where 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 wherein the Y and Z groups are attached to Cᵃ and Cᵇ bridgehead carbon atoms; 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 the group T is attached to a carbon atom in each of the groups Y and Z; and provided that, if R¹ is a tricyclic carbocycle of formula (3), where X is a direct single bond or a divalent group -CH₂-, the 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 group V 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 R², together with the nitrogen atom to which they are attached, form a 3- to 10-membered saturated or partially unsaturated monocyclic or bicyclic heterocycle, wherein the heterocycle includes, in addition to a nitrogen atom and one or more atoms of carbon, no additional heteroatoms, or 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; or R¹ and one of the two R²ᵃ groups, together with the nitrogen atom to which R²ᵃ is attached, and together with the nitrogen atom of the group -NR²-, form a saturated or partially unsaturated mono- or bicyclic heterocycle of 3 to 10 members, wherein the heterocycle includes, in addition to two nitrogen atoms and one or more carbon atoms, no other heteroatoms or 1, 2, or 3 additional heteroatoms independently selected from N, O, and S as ring member atoms; and wherein the heterocycle is unsubstituted or substituted with 1, 2, 3, 4 or up to the maximum possible number of identical or different R¹ᵃ groups; 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; R³, R⁴ are independently selected from the group consisting of hydrogen, halogen, cyano, C₁₋₄-alkyl, C₁₋₄-haloalkyl, C₁₋₄-alkoxy, and C₁₋₄-haloalkoxy; or, if B is -C (R³) ₂-C (R⁴) ₂-, two radicals R³ and / or two radicals R⁴, which are attached to the same carbon atom, together with said carbon atom, form a saturated carbocycle of 3 to 7 membered or a 3 to 6 membered saturated heterocycle; wherein the saturated heterocycle includes, in addition to 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 group RN; 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 member atoms of the carbon ring 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; or if B is -C (R³) ₂-C (R⁴) ₂-, a radical R³ and a radical R⁴, together with the carbon atoms to which each of them is attached, form a saturated carbocycle of 3 to 7 members or a saturated 3- to 6-membered heterocycle; wherein the saturated heterocycle includes, in addition to carbon atoms, 1, 2, or 3 selected heteroatoms, independently from the group consisting of N, O, and S as ring member atoms; and wherein said N ring member atom is substituted with the group RN; 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 member atoms of the carbon ring of the saturated carbocycle or saturated heterocycle, which are represented by radicals R³ and R⁴, are unsubstituted or substituted with a total amount of 1, 2, 3, 4 or up to the maximum amount possible of identical or different radicals selected from the group consisting of halogen, cyano, C₁₋₆-alkyl, C₁₋₆-alkoxy, and C₃₋₈-cycloalkyl.

ARP180101485A 2017-06-02 2018-06-01 SUBSTITUTED OXADIAZOLES TO COMBAT PHYTOPATOGENIC FUNGI AR112068A1 (en)

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