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AR111371A1 - OXADIAZOLS REPLACED TO FIGHT FITOPATHOGEN FUNGI - Google Patents

OXADIAZOLS REPLACED TO FIGHT FITOPATHOGEN FUNGI

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AR111371A1
AR111371A1 ARP180100894A ARP180100894A AR111371A1 AR 111371 A1 AR111371 A1 AR 111371A1 AR P180100894 A ARP180100894 A AR P180100894A AR P180100894 A ARP180100894 A AR P180100894A AR 111371 A1 AR111371 A1 AR 111371A1
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Argentina
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alkyl
group
groups
atoms
heterocycle
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ARP180100894A
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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
    • C07D413/04—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 directly linked by a ring-member-to-ring-member bond

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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)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

Trifluorometiloxadiazoles, o los N-óxidos, o las sales útiles en la agricultura de aquellos; y a los intermediarios útiles para su preparación; y al uso de los compuestos para controlar hongos fitopatógenos; a un método para combatir hongos fitopatógenos dañinos, en donde el proceso comprende tratar los hongos o las plantas, el suelo o las semillas que se desean proteger del ataque fúngico, con una cantidad eficaz de al menos un compuesto, o un N-óxido, o una sal de aquel aceptable en la agricultura; a composiciones agroquímicas que comprenden al menos un compuesto; y a composiciones agroquímicas que también comprenden semillas. 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 de los heterociclos aromáticos incluyen, además de 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 los heterociclos aromáticos son no sustituidos o sustituidos con 1 ó 2 grupos RA idénticos o diferentes; en donde RA es halógeno, ciano, C₁₋₆-alquilo, C₁₋₆-haloalquilo, C₁₋₆-alcoxi o C₁₋₆-haloalcoxi; V es -NR²-NR²-; L es -(C=O)-, -(C=S)- o -S(=O)ₚ-; p es 0, 1 ó 2; W es R¹, -NR⁵-R¹ o -NR²-NR⁵-R¹; R¹ es C₁₋₆-alquilo, C₃₋₈-cicloalquilo, C₃₋₈-cicloalquenilo, C₂₋₆-alquenilo, C₂₋₆-alquinilo, fenil-C₁₋₄-alquilo, heteroaril-C₁₋₄-alquilo, fenilo, naftilo o un heterociclo monocíclico o bicíclico saturado, parcialmente insaturado o aromático de 3 a 10 miembros, en donde los átomos miembros del anillo de dicho heterociclo monocíclico o bicíclico incluyen, además de átomos de carbono, 1, 2, 3 ó 4 heteroátomos seleccionados de N, O y S como átomos miembros del anillo, y en donde 1 ó 2 átomos miembros del anillo de carbono del heterociclo se pueden reemplazar por 1 ó 2 grupos seleccionados independientemente de -C(=O)- y -C(=S)-; y en donde el grupo heteroarilo en 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 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 antes mencionados son no sustituidos o sustituidos con 1, 2, 3 o hasta la máxima cantidad posible de grupos R¹ᵃ idénticos o diferentes; en donde- 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; 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 está unido 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 resto de los compuestos de la fórmula (1) a través de uno de los átomos de carbono del anillo; y en donde los grupos de fórmula (2) y (3), independientemente entre sí, 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; R², R⁵ independientemente entre sí, se seleccionan del grupo que consiste en 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, C(=O)-C₁₋₆-alquilo y C(=O)-C₁₋₆-alcoxi; 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; o R¹ y R⁵, 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, 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 de -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; 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 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. Reivindicación 9: Los compuestos intermediarios caracterizados por las fórmulas seleccionadas del grupo de fórmulas (4), en donde las variables L, W, R², R³ y R⁴ son como se definen en la reivindicación 1 para los compuestos de la fórmula (1).Trifluoromethyloxadiazoles, or N-oxides, or salts useful in the agriculture of those; and to intermediaries useful for their preparation; and the use of the compounds to control phytopathogenic fungi; to a method to combat harmful phytopathogenic fungi, where the process involves treating fungi or plants, soil or seeds that are to be protected from fungal attack, with an effective amount of at least one compound, or an N-oxide, or a salt of that acceptable in agriculture; to agrochemical compositions comprising at least one compound; and to agrochemical compositions that also comprise seeds. 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 ring of aromatic heterocycles 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 heterocycles are unsubstituted or substituted with 1 or 2 identical or different RA groups; wherein RA is halogen, cyano, C₁₋₆-alkyl, C₁₋₆-haloalkyl, C₁₋₆-alkoxy or C₁₋₆-haloalkoxy; V is -NR²-NR²-; L is - (C = O) -, - (C = S) - or -S (= O) ₚ-; p is 0, 1 or 2; W is R¹, -NR⁵-R¹ or -NR²-NR⁵-R¹; R¹ is C₁₋₆-alkyl, C₃₋₈-cycloalkyl, C₃₋₈-cycloalkenyl, C₂₋₆-alkenyl, C₂₋₆-alkynyl, phenyl-C₁₋₄-alkyl, heteroaryl-C₁₋₄-alkyl, phenyl, naphthyl or a saturated monocyclic or bicyclic heterocycle, partially unsaturated or aromatic of 3 to 10 members, wherein the ring member atoms of said monocyclic or bicyclic 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 1 or 2 carbon ring hetero atoms of the heterocycle can be replaced by 1 or 2 groups independently selected from -C (= O) - and -C (= S) -; and wherein the heteroaryl-C hetero-alkyl heteroaryl group is a 5 or 6 membered aromatic heterocycle, wherein the heterocyclic ring ring member atoms include, in addition to 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 are unsubstituted or substituted with 1, 2, 3 or up to the maximum possible number of identical or different R¹ᵃ groups; where- 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; 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 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 is attached 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 rest of the compounds of the formula (1) through one of the ring carbon atoms; and wherein the groups of formula (2) and (3), independently of each other, 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; R², R⁵ independently of each other, are selected from the group consisting of 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, C (= O) -C₁₋₆-alkyl and C (= O) -C₁₋₆-alkoxy; 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; or R¹ and R⁵, together with the nitrogen atom to which they are attached, form a saturated or partially unsaturated monocyclic or bicyclic heterocycle of 3 to 10 members, wherein the heterocycle includes, in addition to a nitrogen atom and one or more atoms of carbon, 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 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; 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 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. Claim 9: The intermediate compounds characterized by the formulas selected from the group of formulas (4), wherein the variables L, W, R², R³ and R⁴ are as defined in claim 1 for the compounds of the formula (1).

ARP180100894A 2017-04-11 2018-04-10 OXADIAZOLS REPLACED TO FIGHT FITOPATHOGEN FUNGI AR111371A1 (en)

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