AR119790A1 - ISOXAZOLINE COMPOUNDS AND THEIR USE AS PEST CONTROL AGENTS - Google Patents

ISOXAZOLINE COMPOUNDS AND THEIR USE AS PEST CONTROL AGENTS

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Publication number
AR119790A1
AR119790A1 ARP200102338A ARP200102338A AR119790A1 AR 119790 A1 AR119790 A1 AR 119790A1 AR P200102338 A ARP200102338 A AR P200102338A AR P200102338 A ARP200102338 A AR P200102338A AR 119790 A1 AR119790 A1 AR 119790A1
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Argentina
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group
alkyl
cycloalkyl
haloalkyl
alkenyl
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ARP200102338A
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Spanish (es)
Inventor
Yogesh Dhage
Jagadish Pabba
Rohit Saxena
Ganesh Dhage
Vikas Kumar
Vishwanath Gade
- Saragur Ravikumar Suryanarayana Geetanjly
Alexander G M Klausener
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Pi Industries Ltd
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Publication of AR119790A1 publication Critical patent/AR119790A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/04—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • 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
    • A01N43/80—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 one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2

Abstract

Reivindicación 1: Un compuesto de la fórmula (1), en el que, R¹ se selecciona a partir del grupo que consiste en C₁₋₆-alquilo, C₁₋₆-haloalquil, C₃₋₆-cicloalquil y C₃₋₆-halocicloalquil; R²ᵃ, R²ᵇ y R²ᶜ se seleccionan independientemente a partir del grupo que consiste en hidrógeno, X, ciano, C₁₋₆-alquilo, C₂₋₆-alquenilo, C₂₋₆-alquinilo, C₁₋₆-haloalquil, C₂₋₆-haloalquenil y C₃₋₈-cicloalquil; A se selecciona a partir del grupo que consiste en fenil y un grupo C₅₋₆-heterociclilo, que puede estar opcionalmente sustituido con uno o más grupos de R³; R³ se selecciona a partir del grupo que consiste en hidrógeno, X, ciano, SCN, nitro, C₁₋₆-alquilo, C₂₋₆-alquenilo, C₂₋₆-alquinilo, C₁₋₆-haloalquil, C₂₋₆-haloalquenil, C₂₋₆-haloalquinil, C₃₋₈-cicloalquil, C₄₋₈-cicloalquenil, C₄₋₈-cicloalquinil, SF₅, N(R’’)₂, OR⁴, S(=O)ₙR’’, C(=O)-R’’, C₁₋₈-alquilo-S(O)ₙR’’, C₁₋₈-alquilo-C(=O)-R’’ y CR’=NR’’; T representa -N=S(O)₀₋₁R⁷-, -(CR⁵R⁶)ₚN=S(O)₀₋₁R⁷-, -C(O)N=S(O)₀₋₁R⁷-, -C(O)(CR⁵R⁶)ₚN=S(O)₀₋₁R⁷- y -C(O)NR⁹S(O)-; en el que, el LHS del fragmento T está unido a A y el RHS del fragmento T está unido a Z; R⁴ se selecciona a partir del grupo que consiste en hidrógeno, C₁₋₆-alquilo, C₂₋₆-alquenilo, C₂₋₆-alquinilo, C₁₋₆-haloalquil, C₂₋₆-haloalquenil, C₃₋₈-cicloalquil, C₆₋₁₀-arilo, y C₃₋₈-heterociclilo; R⁵ y R⁶ se seleccionan independientemente a partir del grupo que consiste en hidrógeno, X, ciano, C₁₋₆-alquilo, C₂₋₆-alquenilo, C₁₋₆-haloalquil, OR⁴, C₃₋₈-cicloalquil; en el que uno o más átomos de carbono en el sistema de anillos cíclico pueden estar sustituido por heteroátomos seleccionados a partir del grupo que consiste en N, O, S y que opcionalmente incluye de 1 a 3 miembros del anillo seleccionados a partir del grupo que consiste en C(=O), C(=S), S(O)ₘ y Si(R’)₂; o R⁵ y R⁶ junto con el átomo al que están unidos o junto con otros átomos seleccionados a partir del grupo que consiste en C, N, O, S y que opcionalmente incluye de 1 a 3 miembros del anillo seleccionados a partir 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 a partir del grupo que consiste en X, CN, R’, OR’, SR’, N(R’)₂, Si(R’)₃, COOR’, y CON(R’)₂; R⁷ y Z se seleccionan independientemente a partir del grupo que consiste en C₁₋₆-alquilo, C₁₋₆-cianoalquil, C₂₋₆-alquenilo, C₂₋₆-alquinilo, C₁₋₆-haloalquil, C₂₋₆-haloalquenil, C₂₋₆-haloalquinil, C(=O)-R’’, C₁₋₈-alquilo-C(=O)-R’’, C(=O)-N(R’R’’), C₁₋₈-alquilo-C(=O)-N(R’R’’), C₂₋₈-alquenilo-C(=O)-N(R’R’’), C₃₋₈-cicloalquil, C₄₋₈-cicloalquenil, C₄₋₈-cicloalquinil, C₆₋₁₀-arilo, C₇₋₁₅-aralquil, C₅₋₁₂-alquilo bicíclico, C₇₋₁₂-alquenilo bicíclico, fusionado o no fusionado o C₃₋₁₈-carbociclo bicíclico; en el que uno o más átomos de carbono en el sistema de anillos cíclico pueden estar sustituidos por heteroátomos seleccionados a partir del grupo que consiste en N, O, S y que opcionalmente incluye de 1 a 3 miembros del anillo seleccionados a partir del grupo que consiste en C(=O), C(=S), S(O)ₘ y Si(R’)₂; en el que cada grupo de R⁷ o Z está opcionalmente sustituido con uno o más grupos de R⁸; R⁸ se selecciona a partir del grupo que consiste en hidrógeno, X, ciano, SCN, nitro, C₁₋₆-alquilo, C₂₋₆-alquenilo, C₂₋₆-alquinilo, C₁₋₆-haloalquil, C₂₋₆-haloalquenil, C₂₋₆-haloalquinil, SF₅, OR⁴, N(R’’)₂, Si(R’)₃, (C=O)-R’’, S(O)ₙR’’, C₁₋₈-alquilo-S(O)ₙR’’, C₁₋₈-alquilo-(C=O)-R’’, CR’=NR’’, C₃₋₈-cicloalquil, C₄₋₈-cicloalquenil; en el que uno o más átomos de carbono en el sistema de anillo cíclico pueden estar sustituidos por heteroátomos seleccionados a partir del grupo que consiste en N, O, S y que opcionalmente incluye de 1 a 3 miembros del anillo seleccionados a partir del grupo que consiste en C(=O), C(=S), S(O)ₘ y Si(R’)₂; R⁹ se selecciona a partir del grupo que consiste en hidrógeno, C₁₋₁₂-alquilo, C₂₋₁₂-alquenilo, C₂₋₁₂-alquinilo, C₁₋₁₂-haloalquil, C₂₋₁₂-haloalquenil, C₂₋₁₂-haloalquinil, C₃₋₈-cicloalquil, Si(R’)₃, OR⁴, C(=O)-R’’; R⁵ o R⁶ y R⁷, R⁷ y R³, R⁸ y Z o R⁷ y Z junto con el átomo al que están unidos o junto con otros átomos seleccionados a partir del grupo que consiste en C, N, O, S y que opcionalmente incluye de 1 a 3 miembros del anillo seleccionados a partir 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 a partir del grupo que consiste en X, CN, R’, OR’, SR’, N(R’)₂, Si(R’)₃, COOR’, y CON(R’)₂; cada grupo de R¹, R²ᵃ, R²ᵇ, R²ᶜ, R³, R⁴, R⁵, R⁶, R⁷, R⁸ y R⁹ puede estar opcionalmente sustituido por uno o más grupos seleccionados a partir 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’ representa hidrógeno, C₁₋₆-alquilo o C₃₋₈-ciclalquil; en el que los grupos alquilo y cicloalquil pueden estar opcionalmente sustituidos por uno o más X; R’’ representa hidrógeno, C₁₋₆-alquilo, C₁₋₆-haloalquil, C₃₋₈-cicloalquil, N(R’)₂, OR’ y C₆₋₁₀-arilo; en el que uno o más átomos de carbono en el sistema de anillos cíclico pueden estar sustituidos por heteroátomos seleccionados a partir del grupo que consiste en N, O, S y que opcionalmente incluye de 1 a 3 miembros del anillo seleccionados a partir del grupo que consiste en C(=O), C(=S), S(O)ₘ y Si(R’)₂ y cada grupo de R’’ puede estar opcionalmente sustituido por uno o más grupos seleccionados a partir del grupo que consiste en X, R’, CN, OR’, SR’, N(R’)₂, Si(R’)₃, COOR’ y CON(R’)₂; R’’’ se selecciona a partir de los grupos que consisten en hidrógeno, R’’, CN, C₁₋₆-alquilo, C₁₋₆-haloalquil, C₂₋₆-alquenilo, C₂₋₆-alquinilo, C₃₋₈-cicloalquil, C₄₋₈-cicloalquenil, C₄₋₈-cicloalquinil, OR⁴, (C=O)-R’, COOR’, CON(R’)₂, C₆₋₁₀-arilo, C₇₋₁₅-aralquil y C₅₋₁₀-heterociclilo grupo; en el que uno o más átomos de carbono en el sistema de anillos cíclico pueden estar sustituidos por heteroátomos seleccionados a partir del grupo que consiste en N, O, S y que opcionalmente incluye de 1 a 3 miembros del anillo seleccionados a partir del grupo que consiste en C(=O), C(=S), S(O)ₘ y Si(R’)₂; y cada grupo de R’’’ puede ser sustituido por uno o más grupos seleccionados a partir del grupo que consiste en X, R’, CN, OR’, SR’, N(R’)₂, Si(R’)₃, COOR’, o CON(R’)₂; p representa números enteros 1 ó 2; q representa números enteros 0 ó 1; m y n representan números enteros 0, 1 ó 2; o sales, isómeros, estereoisómeros, diastereómeros, enantiómeros, tautómeros, complejos metálicos, polimorfos o N-óxidos de los mismos aceptables en agricultura.Claim 1: A compound of formula (1), wherein R¹ is selected from the group consisting of C₁₋₆-alkyl, C₁₋₆-haloalkyl, C₃₋₆-cycloalkyl, and C₃₋₆-halocycloalkyl; R²ᵃ, R²ᵇ and R²ᶜ are independently selected from the group consisting of hydrogen, X, cyano, C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkynyl, C₁₋₆-haloalkyl, C₂₋₆-haloalkenyl and C₃₋₈-cycloalkyl; A is selected from the group consisting of phenyl and a C₅₋₆-heterocyclyl group, which may be optionally substituted with one or more R³ groups; R³ is selected from the group consisting of hydrogen, X, cyano, SCN, nitro, C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkynyl, C₁₋₆-haloalkyl, C₂₋₆-haloalkenyl, C₂₋₆-haloalkynyl, C₃₋₈-cycloalkyl, C₄₋₈-cycloalkenyl, C₄₋₈-cycloalkynyl, SF₅, N(R'')₂, OR⁴, S(=O)ₙR'', C(=O) -R'', C₁₋₈-alkyl-S(O)ₙR'', C₁₋₈-alkyl-C(=O)-R'' and CR'=NR''; T represents -N=S(O)₀₋₁R⁷-, -(CR⁵R⁶)ₚN=S(O)₀₋₁R⁷-, -C(O)N=S(O)₀₋₁R⁷-, -C(O) (CR⁵R⁶)ₚN=S(O)₀₋₁R⁷- and -C(O)NR⁹S(O)-; wherein, the LHS of fragment T is bound to A and the RHS of fragment T is bound to Z; R⁴ is selected from the group consisting of hydrogen, C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkynyl, C₁₋₆-haloalkyl, C₂₋₆-haloalkenyl, C₃₋₈-cycloalkyl, C₆₋ ₁₀-aryl, and C₃₋₈-heterocyclyl; R⁵ and R⁶ are independently selected from the group consisting of hydrogen, X, cyano, C₁₋₆-alkyl, C₂₋₆-alkenyl, C₁₋₆-haloalkyl, OR⁴, C₃₋₈-cycloalkyl; wherein one or more carbon atoms in the cyclic ring system 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 consists of C(=O), C(=S), S(O)ₘ and Si(R')₂; or R⁵ and R⁶ 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 ring of three to seven members, which in turn can be substituted by one or more groups selected from from the group consisting of X, CN, R', OR', SR', N(R')₂, Si(R')₃, COOR', and CON(R')₂; R⁷ and Z are independently selected from the group consisting of C₁₋₆-alkyl, C₁₋₆-cyanoalkyl, C₂₋₆-alkenyl, C₂₋₆-alkynyl, C₁₋₆-haloalkyl, C₂₋₆-haloalkenyl, C₂ ₋₆-haloalkynyl, C(=O)-R'', C₁₋₈-alkyl-C(=O)-R'', C(=O)-N(R'R''), C₁₋₈- alkyl-C(=O)-N(R’R’’), C₂₋₈-alkenyl-C(=O)-N(R’R’’), C₃₋₈-cycloalkyl, C₄₋₈-cycloalkenyl, C₄₋₈-cycloalkynyl, C₆₋₁₀-aryl, C₇₋₁₅-aralkyl, C₅₋₁₂-bicyclic alkyl, C₇₋₁₂-bicyclic, fused or unfused alkenyl or C₃₋₁₈-bicyclic carbocycle; wherein one or more carbon atoms in the cyclic ring system 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 consists of C(=O), C(=S), S(O)ₘ and Si(R')₂; wherein each group of R⁷ or Z is optionally substituted with one or more groups of R⁸; R⁸ is selected from the group consisting of hydrogen, X, cyano, SCN, nitro, C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkynyl, C₁₋₆-haloalkyl, C₂₋₆-haloalkenyl, C₂₋₆-haloalkynyl, SF₅, OR⁴, N(R'')₂, Si(R')₃, (C=O)-R'', S(O)ₙR'', C₁₋₈-alkyl-S (O)ₙR'', C₁₋₈-alkyl-(C=O)-R'', CR'=NR'', C₃₋₈-cycloalkyl, C₄₋₈-cycloalkenyl; wherein one or more carbon atoms in the cyclic ring system 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 consists of C(=O), C(=S), S(O)ₘ and Si(R')₂; R⁹ is selected from the group consisting of hydrogen, C₁₋₁₂-alkyl, C₂₋₁₂-alkenyl, C₂₋₁₂-alkynyl, C₁₋₁₂-haloalkyl, C₂₋₁₂-haloalkenyl, C₂₋₁₂-haloalkynyl, C₂₋₁₂-haloalkynyl, C₂₋₁₂-haloalkynyl, ₈-cycloalkyl, Si(R')₃, OR⁴, C(=O)-R''; R⁵ or R⁶ and R⁷, R⁷ and R³, R⁸ and Z or R⁷ and Z 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 from 1 to 3 ring members selected from the group consisting of C(=O), C(=S), S(O)ₘ and Si(R')₂ can form a three to seven membered ring, which by its part 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; each group of R¹, R²ᵃ, R²ᵇ, R²ᶜ, R³, R⁴, R⁵, R⁶, R⁷, R⁸ and R⁹ may be optionally substituted by one or more groups selected from the group consisting of X, CN, R'', OR '', SR'', N(R'R''), Si(R')₃,COOR', and CON(R'R''); X represents halogen; R' represents hydrogen, C₁₋₆-alkyl or C₃₋₈-cyclalkyl; wherein the alkyl and cycloalkyl groups may be optionally substituted by one or more X; R'' represents hydrogen, C₁₋₆-alkyl, C₁₋₆-haloalkyl, C₃₋₈-cycloalkyl, N(R')₂, OR' and C₆₋₁₀-aryl; wherein one or more carbon atoms in the cyclic ring system 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 consists of C(=O), C(=S), S(O)ₘ and Si(R')₂ and each group of R'' may be optionally substituted by one or more groups selected from the group consisting of X, R', CN, OR', SR', N(R')₂, Si(R')₃, COOR' and CON(R')₂; R''' is selected from the groups consisting of hydrogen, R'', CN, C₁₋₆-alkyl, C₁₋₆-haloalkyl, C₂₋₆-alkenyl, C₂₋₆-alkynyl, C₃₋₈- cycloalkyl, C₄₋₈-cycloalkenyl, C₄₋₈-cycloalkynyl, OR⁴, (C=O)-R', COOR', CON(R')₂, C₆₋₁₀-aryl, C₇₋₁₅-aralkyl, and C₅₋₁₀ -heterocyclyl group; wherein one or more carbon atoms in the cyclic ring system 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 consists of C(=O), C(=S), S(O)ₘ and Si(R')₂; and each group of R''' may be substituted by one or more groups selected from the group consisting of X, R', CN, OR', SR', N(R')₂, Si(R')₃ , COOR', or CON(R')₂; p represents integers 1 or 2; q represents integers 0 or 1; m and n represent integers 0, 1 or 2; or agriculturally acceptable salts, isomers, stereoisomers, diastereomers, enantiomers, tautomers, metal complexes, polymorphs or N-oxides thereof.

ARP200102338A 2019-08-29 2020-08-19 ISOXAZOLINE COMPOUNDS AND THEIR USE AS PEST CONTROL AGENTS AR119790A1 (en)

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