AR118243A1 - FUSED HETEROCYCLIC COMPOUNDS AND THEIR USE AS PEST CONTROL AGENTS - Google Patents

FUSED HETEROCYCLIC COMPOUNDS AND THEIR USE AS PEST CONTROL AGENTS

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Publication number
AR118243A1
AR118243A1 ARP200100591A ARP200100591A AR118243A1 AR 118243 A1 AR118243 A1 AR 118243A1 AR P200100591 A ARP200100591 A AR P200100591A AR P200100591 A ARP200100591 A AR P200100591A AR 118243 A1 AR118243 A1 AR 118243A1
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AR
Argentina
Prior art keywords
group
cycloalkyl
aryl
heterocyclyl
alkyl
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ARP200100591A
Other languages
Spanish (es)
Inventor
Kiran K C
Vishwanath Gade
Jagadish Pabba
Rohit Saxena
Jeevan Singh Verma
Sachin Baban Narute
Hardik Vinodbhai Mori
Vishalgiri G Goswami
Ramdas Balu Gadakh
Gagan Kukreja
Ravikumar Suryanarayana Saragur
Alexander G M Klausener
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Pi Industries Ltd
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Publication of AR118243A1 publication Critical patent/AR118243A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4196—1,2,4-Triazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline

Abstract

Compuestos heterocíclicos condensados y su uso como agentes de control de plagas, particularmente nematodos e insectos y para el control de parásitos en plantas y animales. Se provee además una composición que los comprende. Reivindicación 1: Un compuesto de la fórmula (1), en la que, A representa N o CR²; cuando A representa N, entonces no hay más de dos nitrógeno presentes en el anillo E simultáneamente; R² se selecciona a partir del grupo que consiste en hidrógeno, halógeno, C₁₋₆-alquilo, C₁₋₆-haloalquilo, C₂₋₆-haloalquenilo, C₃₋₈-cicloalquilo, OR⁴, NR⁵R⁶, S(O)₀₋₂R⁷, C(=O)R⁸, S(O)₀₋₁R⁹=NR¹⁰; en donde cada grupo puede estar opcionalmente sustituido con uno o más grupos de R²ᵃ; R²ᵃ se selecciona a partir del grupo que consiste en hidrógeno, halógeno, ciano, C₁₋₆-alquilo, C₂₋₆-alquenilo, C₂₋₆-alquinilo, C₁₋₆-haloalquilo, C₂₋₆-haloalquenilo, C₃₋₈-cicloalquilo, OR⁴, NR⁵R⁶, S(O)₀₋₂R⁷, C(=O)R⁸ y S(O)₀₋₁R⁹=NR¹⁰; X representa O ó S; R¹ se selecciona a partir del grupo que consiste en C₁₋₆-alquilo, C₂₋₆-alquenilo, C₂₋₆-alquinilo, C₁₋₆-haloalquilo, C₂₋₆-haloalquenilo, C₃₋₈-cicloalquilo y C₃₋₈-cicloalquilo-C₁₋₆-alquilo; R³ se selecciona a partir del grupo que consiste en halógeno, ciano, C₁₋₆-alquilo, C₂₋₆-alquenilo, C₂₋₆-alquinilo, C₁₋₆-haloalquilo, C₂₋₆-haloalquenilo, C₃₋₈-cicloalquilo, OR⁴, CR⁴=NR⁵, NR⁵R⁶, S(O)₀₋₂R⁷, C(=O)R⁸, S(O)₀₋₁R⁹=NR¹⁰, N=S(O)₀₋₁(R⁹)₂, Si(R’)₃, C₆₋₁₀-arilo, C₇₋₁₄-aralquilo y C₃₋₁₀-heterociclilo; en donde cada grupo alifático puede estar opcionalmente sustituido con uno o más grupos de R³ᵃ y el grupo arilo o heterociclilo puede estar opcionalmente sustituido con uno o más grupos de R³ᵇ; R³ᵃ se selecciona a partir del grupo que consiste en hidrógeno, halógeno, ciano, C₃₋₈-cicloalquilo, OR⁴, CR⁴=NR⁵, NR⁵R⁶, S(O)₀₋₂R⁷, C(=O)R⁸, S(O)₀₋₁R⁹=NR¹⁰, N=S(O)₀₋₁(R⁹)₂, Si(R’)₃, C₆₋₁₀-arilo, C₇₋₁₄-aralquilo y C₃₋₁₀-heterociclilo; R³ᵇ se selecciona a partir del grupo que consiste en hidrógeno, halógeno, ciano, C₁₋₆-alquilo, C₂₋₆-alquenilo, C₂₋₆-alquinilo, C₁₋₆-haloalquilo, C₂₋₆-haloalquenilo, C₃₋₈-cicloalquilo, OR⁴, C(R’)₂-NR⁵R⁶, C(R’)₂-OR⁴, CR⁴=NR⁵, NR⁵R⁶, S(O)₀₋₂R⁷, C(=O)R⁸, S(O)₀₋₁R⁹=NR¹⁰, N=S(O)₀₋₁(R⁹)₂, Si(R’)₃, C₆₋₁₀-arilo, C₇₋₁₄-aralquilo y C₃₋₁₀-heterociclilo; o dos R³ᵃ o dos R³ᵇ sustituyentes 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)₀₋₂ y Si(R’)₂, pueden formar un anillo de 3 a 7 miembros, que por su parte puede ser sustituido por uno o más grupos de R¹¹; R¹¹ se selecciona a partir del grupo que consiste en hidrógeno, halógeno, ciano, C₁₋₆-alquilo, C₂₋₆-alquenilo, C₂₋₆-alquinilo, C₁₋₆-haloalquilo, C₂₋₆-haloalquenilo, C₃₋₈-cicloalquilo, OR⁴, NR⁵R⁶, S(O)₀₋₂R⁷, S(O)₀₋₁R⁹=NR¹⁰, N=S(O)₀₋₁(R⁹)₂, Si(R’)₃, C₆₋₁₀-arilo, C₇₋₁₄-aralquilo y C₃₋₁₀-heterociclilo; R⁴ se selecciona a partir del grupo que consiste en hidrógeno, C₁₋₆-alquilo, C₂₋₆-alquenilo, C₂₋₆-alquinilo, C₁₋₆-haloalquilo, C₂₋₆-haloalquenilo, C₃₋₈-cicloalquilo, S(O)₂R⁷, Si(R’)₃, C₆₋₁₀-arilo, C₇₋₁₄-aralquilo y C₃₋₁₀-heterociclilo; en el que cada grupo alifático puede estar opcionalmente sustituido con R⁴ᵃ y el grupo arilo o heterociclilo puede estar opcionalmente sustituido con uno o más grupos de R⁴ᵇ; R⁴ᵃ se selecciona a partir del grupo que consiste en hidrógeno, halógeno, ciano, C₃₋₈-cicloalquilo, OR’, NR’R’’, S(O)₀₋₂R’, C(=O)R’, Si(R’)₃, C₆₋₁₀-arilo, C₇₋₁₄-aralquilo y C₃₋₁₀-heterociclilo; R⁴ᵇ se selecciona a partir del grupo que consiste en hidrógeno, halógeno, ciano, C₁₋₆-alquilo, C₂₋₆-alquenilo, C₂₋₆-alquinilo, C₁₋₆-haloalquilo, C₂₋₆-haloalquenilo, C₃₋₈-cicloalquilo, OR’, NR’R’’, S(O)₀₋₂R’, C(=O)R’, Si(R’)₃, C₆₋₁₀-arilo, C₇₋₁₄-aralquilo y C₃₋₁₀-heterociclilo; R⁵ se selecciona a partir del grupo que consiste en hidrógeno, C₁₋₆-alquilo, C₂₋₆-alquenilo, C₂₋₆-alquinilo, C₁₋₆-haloalquilo, C₂₋₆-haloalquenilo, C₃₋₈-cicloalquilo, OR⁴, S(O)₀₋₂R⁷, C(=O)R⁸, Si(R’)₃, C₆₋₁₀-arilo, C₇₋₁₄-aralquilo y C₃₋₁₀-heterociclilo; en el que cada grupo alifático puede estar opcionalmente sustituido con R⁵ᵃ y el grupo arilo o heterociclilo puede estar opcionalmente sustituido con uno o más grupos de R⁵ᵇ; R⁵ᵃ se selecciona a partir del grupo que consiste en hidrógeno, halógeno, ciano, C₃₋₈-cicloalquilo, OR’, NR’R’’, S(O)₀₋₂R’, C(=O)R’, Si(R’)₃, C₆₋₁₀-arilo, C₇₋₁₄-aralquilo y C₃₋₁₀-heterociclilo; R⁵ᵇ se selecciona a partir del grupo que consiste en hidrógeno, halógeno, ciano, C₁₋₆-alquilo, C₂₋₆-alquenilo, C₂₋₆-alquinilo, C₁₋₆-haloalquilo, C₂₋₆-haloalquenilo, C₃₋₈-cicloalquilo, OR’, NR’R’’, S(O)₀₋₂R’, Si(R’)₃, C(=O)R’, C₆₋₁₀-arilo, C₇₋₁₄-aralquilo y C₃₋₁₀-heterociclilo; R⁶ se selecciona a partir del grupo que consiste en hidrógeno, C₁₋₆-alquilo, C₂₋₆-alquenilo, C₂₋₆-alquinilo, C₁₋₆-haloalquilo, C₂₋₆-haloalquenilo, C₁₋₆-cicloalquilo y C(=O)R⁸; R⁷ se selecciona a partir del grupo que consiste en C₁₋₆-alquilo, C₂₋₆-alquenilo, C₂₋₆-alquinilo, C₁₋₆-haloalquilo, C₂₋₆-haloalquenilo, C₃₋₈-cicloalquilo, NR⁵R⁶, C₆₋₁₀-arilo, C₇₋₁₄-aralquilo y C₃₋₁₀-heterociclilo; en donde cada grupo alifático puede estar opcionalmente sustituido con uno o más grupos de R⁷ᵃ y el grupo arilo o heterociclilo puede estar opcionalmente sustituido con uno o más grupos de R⁷ᵇ; R⁷ᵃ se selecciona a partir del grupo que consiste en hidrógeno, halógeno, ciano, C₃₋₈-cicloalquilo, OR’, NR’R’’, S(O)₀₋₂R’, C(=O)R’, C₆₋₁₀-arilo, C₇₋₁₄-aralquilo y C₃₋₁₀-heterociclilo; R⁷ᵇ se selecciona a partir del grupo que consiste en hidrógeno, halógeno, ciano, C₁₋₆-alquilo, C₂₋₆-alquenilo, C₂₋₆-alquinilo, C₁₋₆-haloalquilo, C₂₋₆-haloalquenilo, C₃₋₈-cicloalquilo, OR’, NR’R’’, S(O)₀₋₂R’, C(=O)R’, C₆₋₁₀-arilo, C₇₋₁₄-aralquilo y C₃₋₁₀-heterociclilo; R⁸ se selecciona a partir del grupo que consiste en hidrógeno, C₁₋₆-alquilo, C₂₋₆-alquenilo, C₂₋₆-alquinilo, C₁₋₆-haloalquilo, C₂₋₆-haloalquenilo, C₃₋₈-cicloalquilo, OR⁴, NR⁵R⁶, N=S(O)₀₋₁(R⁹)₂, C₆₋₁₀-arilo, C₇₋₁₄-aralquilo y C₃₋₁₀-heterociclilo; en donde cada grupo alifático puede estar opcionalmente sustituido con uno o más grupos de R⁸ᵃ y el grupo arilo o heterociclilo puede estar opcionalmente sustituido con uno o más grupos de R⁸ᵇ; R⁸ᵃ se selecciona a partir del grupo que consiste en hidrógeno, halógeno, ciano, C₃₋₈-cicloalquilo, OR’, NR’R’’, S(O)₀₋₂R’, C(=O)R’, C₆₋₁₀-arilo, C₇₋₁₄-aralquilo y C₃₋₁₀-heterociclilo; R⁸ᵇ se selecciona a partir del grupo que consiste en hidrógeno, halógeno, ciano, C₁₋₆-alquilo, C₂₋₆-alquenilo, C₂₋₆-alquinilo, C₁₋₆-haloalquilo, C₂₋₆-haloalquenilo, C₃₋₈-cicloalquilo, OR’, NR’R’’, S(O)₀₋₂R’, C(=O)R’, C₆₋₁₀-arilo, C₇₋₁₄-aralquilo y C₃₋₁₀-heterociclilo; R⁹ se selecciona a partir del grupo que consiste en C₁₋₆-alquilo, C₂₋₆-alquenilo, C₂₋₆-alquinilo, C₁₋₆-haloalquilo, C₂₋₆-haloalquenilo, C₃₋₈-cicloalquilo y C(=O)R⁸; R¹⁰ se selecciona a partir del grupo que consiste en hidrógeno, ciano, C₁₋₆-alquilo, C₂₋₆-alquenilo, C₂₋₆-alquinilo, C₁₋₆-haloalquilo, C₂₋₆-haloalquenilo, C₃₋₈-cicloalquilo, Si(R’)₃, S(O)₀₋₂R⁷ y C(=O)R⁸; R’ se selecciona a partir del grupo que consiste en hidrógeno, halógeno, ciano, C₁₋₆-alquilo, C₂₋₆-alquenilo, C₂₋₆-alquinilo, C₃₋₈-cicloalquilo, OR’’, N(R’’)₂, S(O)₀₋₂R’’, C(=O)R’’, C(=O)OR’’, y C(=O)N(R’’)₂R⁸; R’’ se selecciona a partir del grupo que consiste en hidrógeno, C₁₋₆-alquilo, C₂₋₆-alquenilo y C₂₋₆-alquinilo y C₃₋₈-cicloalquilo; en el que cada uno puede estar opcionalmente sustituido con halógeno; cada grupo de R¹ a R¹¹, R²ᵃ, R²ᵇ, R³ᵃ, R³ᵇ, R⁴ᵃ, R⁴ᵇ, R⁵ᵃ, R⁵ᵇ, R⁷ᵃ, R⁷ᵇ, R⁸ᵃ y R⁸ᵇ puede ser opcionalmente sustituido por uno o más grupos seleccionados a partir del grupo que consiste en X, CN, R’, OR’, SR’, N(R’)₂, COOR’ y CON(R’)₂; “m” es un número entero que varía de 0 a 2; “n” es un número entero que varía de 0 a 2; o sales agrícolamente aceptables, isómeros / isómeros estructurales, estereoisómeros, diastereoisómeros, enantiómeros, tautómeros, polimorfos, complejos metálicos o N-óxidos de los mismos, con la condición de que los siguientes compuestos estén excluidos de la definición del compuesto de la fórmula (1): 2-(3-(etilsulfonilo)piridina-2-ilo)-7-(trifluorometilo)-[1,2,4]triazolo[4,3-a]piridina-3(2H)-ona, 2-(5-ciclopropilo-3-(etilsulfonilo)piridina-2-ilo)-7-(trifluorometilo)-[1,2,4]triazolo[4,3-a]piridina-3(2H)-ona, 2-(3-(etilsulfonilo)-5-(trifluorometilo)piridina-2-ilo)-7-(trifluorometilo)-[1,2,4]triazolo[4,3-a]piridina-3(2H)-ona, 2-(3-(etilsulfonilo)-5-(trifluorometilo)piridina-2-ilo)-6-(trifluorometilo)-[1,2,4]triazolo[4,3-a]piridina-3(2H)-ona, 2-(5-ciclopropilo-3-(etilsulfonilo)piridina-2-ilo)-6-(trifluorometilo)-[1,2,4]triazolo[4,3-a]piridina-3(2H)-ona, 2-(3-(etilsulfonilo)piridina-2-ilo)-6-(trifluorometilo)-[1,2,4]triazolo[4,3-a]piridina-3(2H)-ona, 2-(5-bromo-3-(etilsulfonilo)piridina-2-ilo)-6-(trifluorometilo)-[1,2,4]triazolo[4,3-a]pirazina-3(2H)-ona, 2-(5-ciclopropilo-3-(etilsulfonilo)piridina-2-ilo)-6-(trifluorometilo)-[1,2,4]triazolo[4,3-a]pirazina-3(2H)-ona, 2-(3-(etilsulfonilo)-5-(trifluorometilo)piridina-2-ilo)-6-(trifluorometilo)-[1,2,4]triazolo[4,3-a]pirazina3(2H)-ona, 2-(3-(etilsulfonilo)-5-(4-fluorofenilo)piridina-2-ilo)-6-(trifluorometilo)-[1,2,4]triazolo[4,3-a]pirazina-3(2H)-ona, 2-(5-(etilsulfonilo)-6’-fluoro-[3,3’-bipiridina]-6-ilo)-6-(trifluorometilo)-[1,2,4]triazolo[4,3-a]pirazina-3(2H)-ona, 4-(5-(etilsulfonilo)-6-(3-oxo-6-(trifluorometilo)-[1,2,4]triazolo[4,3-a]pirazina-2(3H)-ilo)piridina-3-ilo)benzonitrilo, 2-(3-(etilsulfonilo)-5-metilpiridina-2-ilo)-6-(trifluorometilo)-[1,2,4]triazolo[4,3-a]piridina-3(2H)-ona y terc-butilo (5-(etilsulfonilo)-6-(3-oxo-6-(trifluorometilo)-[1,2,4]triazolo[4,3-a]pirazina-2(3H)-ilo)piridina-3-ilo)carbamato.Condensed heterocyclic compounds and their use as pest control agents, particularly nematodes and insects, and for the control of parasites in plants and animals. A composition comprising them is further provided. Claim 1: A compound of the formula (1), in which A represents N or CR²; when A represents N, then no more than two nitrogens are present in ring E simultaneously; R² is selected from the group consisting of hydrogen, halogen, C₁₋₆-alkyl, C₁₋₆-haloalkyl, C₂₋₆-haloalkenyl, C₃₋₈-cycloalkyl, OR⁴, NR⁵R⁶, S(O)₀₋₂R⁷, C(=O)R⁸, S(O)₀₋₁R⁹=NR¹⁰; wherein each group may be optionally substituted with one or more R²ᵃ groups; R²ᵃ is selected from the group consisting of hydrogen, halogen, cyano, C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkynyl, C₁₋₆-haloalkyl, C₂₋₆-haloalkenyl, C₃₋₈- cycloalkyl, OR⁴, NR⁵R⁶, S(O)₀₋₂R⁷, C(=O)R⁸, and S(O)₀₋₁R⁹=NR¹⁰; X represents O or S; R¹ is selected from the group consisting of C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkynyl, C₁₋₆-haloalkyl, C₂₋₆-haloalkenyl, C₃₋₈-cycloalkyl, and C₃₋₈- cycloalkyl-C₁₋₆-alkyl; R³ is selected from the group consisting of halogen, cyano, C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkynyl, C₁₋₆-haloalkyl, C₂₋₆-haloalkenyl, C₃₋₈-cycloalkyl, OR⁴, CR⁴=NR⁵, NR⁵R⁶, S(O)₀₋₂R⁷, C(=O)R⁸, S(O)₀₋₁R⁹=NR¹⁰, N=S(O)₀₋₁(R⁹)₂, Si(R ’)₃, C₆₋₁₀-aryl, C₇₋₁₄-aralkyl and C₃₋₁₀-heterocyclyl; wherein each aliphatic group may be optionally substituted with one or more R³ᵃ groups and the aryl or heterocyclyl group may be optionally substituted with one or more R³ᵇ groups; R³ᵃ is selected from the group consisting of hydrogen, halogen, cyano, C₃₋₈-cycloalkyl, OR⁴, CR⁴=NR⁵, NR⁵R⁶, S(O)₀₋₂R⁷, C(=O)R⁸, S(O)₀ ₋₁R⁹=NR¹⁰, N=S(O)₀₋₁(R⁹)₂, Si(R')₃, C₆₋₁₀-aryl, C₇₋₁₄-aralkyl, and C₃₋₁₀-heterocyclyl; R³ᵇ is selected from the group consisting of hydrogen, halogen, cyano, C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkynyl, C₁₋₆-haloalkyl, C₂₋₆-haloalkenyl, C₃₋₈- cycloalkyl, OR⁴, C(R')₂-NR⁵R⁶, C(R')₂-OR⁴, CR⁴=NR⁵, NR⁵R⁶, S(O)₀₋₂R⁷, C(=O)R⁸, S(O)₀₋₁R⁹ =NR¹⁰, N=S(O)₀₋₁(R⁹)₂, Si(R')₃, C₆₋₁₀-aryl, C₇₋₁₄-aralkyl, and C₃₋₁₀-heterocyclyl; or two R³ᵃ or two R³ᵇ substituents 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 group consisting of C(=O), C(=S), S(O)₀₋₂ and Si(R’)₂, can form a 3- to 7-membered ring, which in turn can be substituted by one or more groups of R¹¹; R¹¹ is selected from the group consisting of hydrogen, halogen, cyano, C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkynyl, C₁₋₆-haloalkyl, C₂₋₆-haloalkenyl, C₃₋₈- cycloalkyl, OR⁴, NR⁵R⁶, S(O)₀₋₂R⁷, S(O)₀₋₁R⁹=NR¹⁰, N=S(O)₀₋₁(R⁹)₂, Si(R’)₃, C₆₋₁₀-aryl , C₇₋₁₄-aralkyl and C₃₋₁₀-heterocyclyl; 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, S( O)₂R⁷, Si(R')₃, C₆₋₁₀-aryl, C₇₋₁₄-aralkyl and C₃₋₁₀-heterocyclyl; wherein each aliphatic group may be optionally substituted by R⁴ᵃ and the aryl or heterocyclyl group may be optionally substituted by one or more groups of R⁴ᵇ; R⁴ᵃ is selected from the group consisting of hydrogen, halogen, cyano, C₃₋₈-cycloalkyl, OR', NR'R'', S(O)₀₋₂R', C(=O)R', Si( R')₃, C₆₋₁₀-aryl, C₇₋₁₄-aralkyl and C₃₋₁₀-heterocyclyl; R⁴ᵇ is selected from the group consisting of hydrogen, halogen, cyano, C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkynyl, C₁₋₆-haloalkyl, C₂₋₆-haloalkenyl, C₃₋₈- cycloalkyl, OR', NR'R'', S(O)₀₋₂R', C(=O)R', Si(R')₃, C₆₋₁₀-aryl, C₇₋₁₄-aralkyl and C₃₋₁₀ -heterocyclyl; R⁵ 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, OR⁴, S(O)₀₋₂R⁷, C(=O)R⁸, Si(R')₃, C₆₋₁₀-aryl, C₇₋₁₄-aralkyl, and C₃₋₁₀-heterocyclyl; wherein each aliphatic group may be optionally substituted by R⁵ᵃ and the aryl or heterocyclyl group may be optionally substituted by one or more groups of R⁵ᵇ; R⁵ᵃ is selected from the group consisting of hydrogen, halogen, cyano, C₃₋₈-cycloalkyl, OR', NR'R'', S(O)₀₋₂R', C(=O)R', Si( R')₃, C₆₋₁₀-aryl, C₇₋₁₄-aralkyl and C₃₋₁₀-heterocyclyl; R⁵ᵇ is selected from the group consisting of hydrogen, halogen, cyano, C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkynyl, C₁₋₆-haloalkyl, C₂₋₆-haloalkenyl, C₃₋₈- cycloalkyl, OR', NR'R'', S(O)₀₋₂R', Si(R')₃, C(=O)R', C₆₋₁₀-aryl, C₇₋₁₄-aralkyl and C₃₋₁₀ -heterocyclyl; R⁶ is selected from the group consisting of hydrogen, C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkynyl, C₁₋₆-haloalkyl, C₂₋₆-haloalkenyl, C₁₋₆-cycloalkyl, and C( =O)R⁸; R⁷ is selected from the group consisting of C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkynyl, C₁₋₆-haloalkyl, C₂₋₆-haloalkenyl, C₃₋₈-cycloalkyl, NR⁵R⁶, C₆₋ ₁₀-aryl, C₇₋₁₄-aralkyl, and C₃₋₁₀-heterocyclyl; wherein each aliphatic group may be optionally substituted with one or more groups of R⁷ᵃ and the aryl or heterocyclyl group may be optionally substituted with one or more groups of R⁷ᵇ; R⁷ᵃ is selected from the group consisting of hydrogen, halogen, cyano, C₃₋₈-cycloalkyl, OR', NR'R'', S(O)₀₋₂R', C(=O)R', C₆₋ ₁₀-aryl, C₇₋₁₄-aralkyl, and C₃₋₁₀-heterocyclyl; R⁷ᵇ is selected from the group consisting of hydrogen, halogen, cyano, C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkynyl, C₁₋₆-haloalkyl, C₂₋₆-haloalkenyl, C₃₋₈- cycloalkyl, OR', NR'R'', S(O)₀₋₂R', C(=O)R', C₆₋₁₀-aryl, C₇₋₁₄-aralkyl, and C₃₋₁₀-heterocyclyl; R⁸ 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, OR⁴, NR⁵R⁶, N=S(O)₀₋₁(R⁹)₂, C₆₋₁₀-aryl, C₇₋₁₄-aralkyl, and C₃₋₁₀-heterocyclyl; wherein each aliphatic group may be optionally substituted with one or more groups of R⁸ᵃ and the aryl or heterocyclyl group may be optionally substituted with one or more groups of R⁸ᵇ; R⁸ᵃ is selected from the group consisting of hydrogen, halogen, cyano, C₃₋₈-cycloalkyl, OR', NR'R'', S(O)₀₋₂R', C(=O)R', C₆₋ ₁₀-aryl, C₇₋₁₄-aralkyl, and C₃₋₁₀-heterocyclyl; R⁸ᵇ is selected from the group consisting of hydrogen, halogen, cyano, C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkynyl, C₁₋₆-haloalkyl, C₂₋₆-haloalkenyl, C₃₋₈- cycloalkyl, OR', NR'R'', S(O)₀₋₂R', C(=O)R', C₆₋₁₀-aryl, C₇₋₁₄-aralkyl, and C₃₋₁₀-heterocyclyl; R⁹ is selected from the group consisting of C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkynyl, C₁₋₆-haloalkyl, C₂₋₆-haloalkenyl, C₃₋₈-cycloalkyl, and C(=O )R⁸; R¹⁰ is selected from the group consisting of hydrogen, cyano, C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkynyl, C₁₋₆-haloalkyl, C₂₋₆-haloalkenyl, C₃₋₈-cycloalkyl, Si(R')₃, S(O)₀₋₂R⁷ and C(=O)R⁸; R' is selected from the group consisting of hydrogen, halogen, cyano, C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkynyl, C₃₋₈-cycloalkyl, OR'', N(R'' )₂, S(O)₀₋₂R'', C(=O)R'', C(=O)OR'', and C(=O)N(R'')₂R⁸; R'' is selected from the group consisting of hydrogen, C₁₋₆-alkyl, C₂₋₆-alkenyl, and C₂₋₆-alkynyl, and C₃₋₈-cycloalkyl; wherein each may be optionally substituted with halogen; each group from R¹ to R¹¹, R²ᵃ, R²ᵇ, R³ᵃ, R³ᵇ, R⁴ᵃ, R⁴ᵇ, R⁵ᵃ, R⁵ᵇ, R⁷ᵃ, R⁷ᵇ, R⁸ᵃ and R⁸ᵇ may be optionally substituted by one or more groups selected from the group consisting of X, CN , R', OR', SR', N(R')₂, COOR' and CON(R')₂; "m" is an integer ranging from 0 to 2; "n" is an integer ranging from 0 to 2; or agriculturally acceptable salts, isomers/structural isomers, stereoisomers, diastereomers, enantiomers, tautomers, polymorphs, metal complexes, or N-oxides thereof, with the proviso that the following compounds are excluded from the definition of compound of formula (1 ): 2-(3-(ethylsulfonyl)pyridine-2-yl)-7-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine-3(2H)-one, 2-( 5-Cyclopropyl-3-(ethylsulfonyl)pyridine-2-yl)-7-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine-3(2H)-one, 2-(3 -(ethylsulfonyl)-5-(trifluoromethyl)pyridine-2-yl)-7-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine-3(2H)-one, 2-( 3-(ethylsulfonyl)-5-(trifluoromethyl)pyridine-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine-3(2H)-one, 2- (5-Cyclopropyl-3-(ethylsulfonyl)pyridine-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine-3(2H)-one, 2-( 3-(ethylsulfonyl)pyridine-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine-3(2H)-one, 2-(5-bromo-3 -(ethylsulfonyl)pyridine- 2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyrazine-3(2H)-one, 2-(5-cyclopropyl-3-(ethylsulfonyl)pyridine-2 -yl)-6-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyrazine-3(2H)-one, 2-(3-(ethylsulfonyl)-5-(trifluoromethyl)pyridine- 2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyrazine3(2H)-one, 2-(3-(ethylsulfonyl)-5-(4-fluorophenyl)pyridine -2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyrazine-3(2H)-one, 2-(5-(ethylsulfonyl)-6'-fluoro- [3,3'-bipyridine]-6-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyrazine-3(2H)-one, 4-(5-( ethylsulfonyl)-6-(3-oxo-6-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyrazine-2(3H)-yl)pyridine-3-yl)benzonitrile, 2- (3-(ethylsulfonyl)-5-methylpyridine-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine-3(2H)-one and tert-butyl ( 5-(ethylsulfonyl)-6-(3-oxo-6-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyrazine-2(3H)-yl)pyridine-3-yl)carbamate .

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