AR120663A1 - HERBICIDE COMPOUNDS - Google Patents

HERBICIDE COMPOUNDS

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Publication number
AR120663A1
AR120663A1 ARP200103365A ARP200103365A AR120663A1 AR 120663 A1 AR120663 A1 AR 120663A1 AR P200103365 A ARP200103365 A AR P200103365A AR P200103365 A ARP200103365 A AR P200103365A AR 120663 A1 AR120663 A1 AR 120663A1
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Argentina
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phenyl
group
alkyl
substituents
optionally substituted
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ARP200103365A
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Spanish (es)
Inventor
James Nicholas Scutt
Nigel James Willetts
Joseph Andrew Tate
Rosemary Anna Croft
Andrea Mgranaghan
Sunil Chakave
Vanitha Acharya
Mangala Phadte
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Syngenta Crop Protection Ag
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Publication of AR120663A1 publication Critical patent/AR120663A1/en

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    • 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
    • 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
    • A01N43/74—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 1,3
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
    • 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
    • A01N43/74—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 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems

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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)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pyridine Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Compuestos de fórmula (1) donde los sustituyentes son como se definen en la reivindicación 1, útiles como pesticidas, especialmente como herbicidas. Reivindicación 1: Uso de un compuesto de fórmula (1) o una especie zwitteriónica o sal agronómicamente aceptable de este, como herbicida: donde R¹ se selecciona del grupo que consiste en hidrógeno, halógeno, alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₆, haloalquilo C₁₋₆, -OR⁷, -OR¹⁵ᵃ, -N(R⁶)S(O)₂R¹⁵, -N(R⁶)C(O)R¹⁵, -N(R⁶)C(O)OR¹⁵, -N(R⁶)C(O)NR¹⁶R¹⁷, -N(R⁶)CHO, -N(R⁷ᵃ)₂ y -S(O)ʳR¹⁵; R² se selecciona del grupo que consiste en hidrógeno, halógeno, alquilo C₁₋₆ y haloalquilo C₁₋₆; y donde, cuando R¹ se selecciona del grupo que consiste en -OR⁷, -OR¹⁵ᵃ, -N(R⁶)S(O)₂R¹⁵, -N(R⁶)C(O)R¹⁵, -N(R⁶)C(O)OR¹⁵, -N(R⁶)C(O)NR¹⁶R¹⁷, -N(R⁶)CHO, -N(R⁷ᵃ)₂ y -S(O)ʳR¹⁵, R² se selecciona del grupo que consiste en hidrógeno y alquilo C₁₋₆; o R¹ y R², junto con el átomo de carbono al que están unidos, forman un anillo de cicloalquilo C₃₋₆ o un heterociclilo de 3 a 6 miembros, que comprende 1 ó 2 heteroátomos seleccionados individualmente entre N y O; y Q es (CR¹ᵃR²ᵇ)ₘ; m es 0, 1, 2 ó 3; cada uno de R¹ᵃ y R²ᵇ se seleccionan independientemente a partir del grupo que consiste en hidrógeno, halógeno, alquilo C₁₋₆, haloalquilo C₁₋₆, -OH, -OR⁷, -OR¹⁵ᵃ, -NH₂, -NHR⁷, -NHR¹⁵ᵃ, -N(R⁶)CHO, -NR⁷ᵇR⁷ᶜ y -S(O)ʳR¹⁵; o cada R¹ᵃ y R²ᵇ, junto con el átomo de carbono al que están unidos, forman un anillo de cicloalquilo C₃₋₆ o un heterociclilo de 3 a 6 miembros, que comprende 1 ó 2 heteroátomos seleccionados individualmente entre N y O; y R³, R³ᵃ, R⁴ y R⁵ se seleccionan independientemente del grupo que consiste en hidrógeno, halógeno, ciano, nitro, -S(O)ʳR¹⁵, alquilo C₁₋₆, fluoroalquilo C₁₋₆, fluoroalcoxi C₁₋₆, alcoxi C₁₋₆, cicloalquilo C₃₋₆ y -N(R⁶)₂; cada R⁶ se selecciona independientemente entre hidrógeno y alquilo C₁₋₆; cada R⁷ se selecciona independientemente del grupo que consiste en alquilo C₁₋₆, -S(O)₂R¹⁵, -C(O)R¹⁵, -C(O)OR¹⁵ y -C(O)NR¹⁶R¹⁷; cada R⁷ᵃ se selecciona independientemente del grupo que consiste en -S(O)₂R¹⁵, -C(O)R¹⁵, -C(O)OR¹⁵ -C(O)NR¹⁶R¹⁷ y -C(O)NR⁶R¹⁵ᵃ; R⁷ᵇ y R⁷ᶜ se seleccionan independientemente del grupo que consiste en alquilo C₁₋₆, -S(O)₂R¹⁵, -C(O)R¹⁵, -C(O)OR¹⁵, -C(O)NR¹⁶R¹⁷ y fenilo, y donde dicho fenilo está opcionalmente sustituido por 1, 2 ó 3 sustituyentes R⁹, que pueden ser iguales o diferentes; o R⁷ᵇ y R⁷ᶜ, junto con el átomo de nitrógeno al que están unidos, forman un anillo de heterociclilo de 4 a 6 miembros que comprende opcionalmente un heteroátomo adicional seleccionado individualmente entre N, O y S; y A es una estructura bicíclica condensada de fórmula general (2); en la que: (i) el anillo A¹ tiene 6 elementos y el anillo A² tiene 5 elementos; (ii) A incluye al menos un heteroátomo seleccionado de N, O y S, siendo el resto átomos de carbono; (iii) al menos uno del anillo A¹ y el anillo A² es aromático, o A en su conjunto es aromático; (iv) A puede estar unido al resto del compuesto de fórmula (1) en cualquier posición disponible del anillo A² siempre que sea un átomo de carbono; (v) uno de los átomos de carbono es opcionalmente un carbonilo; (vi) A está opcionalmente sustituido en cualquier posición disponible en uno cualquier o en ambos del anillo A¹ o el anillo A² con p sustituyentes R⁸, que pueden ser iguales o diferentes; y (vii) p es 0 a 6; cuando A está sustituido en uno o más átomos de carbono por R⁸, entonces cada R⁸ se selecciona independientemente del grupo que consiste en halógeno, nitro, ciano, -NH₂, -NHR⁷, -N(R⁷)₂, -OH, -OR⁷, -S(O)ʳR¹⁵, -NR⁶S(O)₂R¹⁵, -C(O)OR¹⁰, -C(O)R¹⁵, -C(O)NR¹⁶R¹⁷, -S(O)₂NR¹⁶R¹⁷, alquilo C₁₋₆, haloalquilo C₁₋₆, cicloalquilo C₃₋₆, halocicloalquilo C₃₋₆, cicloalcoxi C₃₋₆, alquenilo C₂₋₆, haloalquenilo C₂₋₆, alquinilo C₂₋₆, alcoxi C₁₋₃alquil C₁₋₃-, hidroxi-alquil C₁₋₆-, alcoxi C₁₋₃-alcoxi C₁₋₃-, haloalcoxi C₁₋₆, haloalcoxi C₁₋₃-alquil C₁₋₃-, alquenil C₃₋₆oxi, alquinil C₃₋₆oxi, N-cicloalquil C₃₋₆amino, -C(R⁶)=NOR⁶, fenilo, un heterociclilo de 3 a 6 miembros, que comprende 1 ó 2 heteroátomos individualmente seleccionados de N y O, y un heteroarilo de 5 ó 6 miembros, que comprende 1, 2, 3 ó 4 heteroátomos, individualmente seleccionados de N, O y S, y donde dichos restos fenilo, heterociclilo o heteroarilo están opcionalmente sustituidos por 1, 2 ó 3 sustituyentes, que pueden ser idénticos o diferentes, seleccionados de R⁹; y cuando A está sustituido en uno o más átomos de N por uno o más R⁸, entonces cada R⁸ se selecciona independientemente del grupo que consiste en -OR⁷, -S(O)ʳR¹², alquilo C₁₋₆, haloalquilo C₁₋₆, cicloalquilo C₃₋₆, halocicloalquilo C₃₋₆, cicloalcoxi C₃₋₆, alquenilo C₂₋₆, haloalquenilo C₂₋₆, alquinilo C₂₋₆, alcoxi C₁₋₃alquilo C₁₋₃, hidroxialquilo C₂₋₆, haloalcoxi C₁₋₆, haloalcoxi C₁₋₃alquilo C₁₋₃, alcoxi C₁₋₆carbonilo, alqueniloxi C₃₋₆, alquiniloxi C₃₋₆, alquil C₁₋₆carbonilo, alquil C₁₋₆aminocarbonilo, dialquil-C₁₋₆aminocarbonilo, fenilo y heteroarilo, donde el resto heteroarilo es un anillo aromático monocíclico de 5 ó 6 miembros que comprende 1, 2, 3 ó 4 heteroátomos individualmente seleccionados entre N, O y S, y donde cualquiera de dichos restos fenilo o heteroarilo están opcionalmente sustituidos por 1, 2 ó 3 sustituyentes, que pueden ser iguales o diferentes, seleccionados de R⁹; cada R⁹ se selecciona independientemente del grupo que consiste en halógeno, ciano, -OH, -N(R⁶)₂, alquilo C₁₋₄, alcoxi C₁₋₄, haloalquilo C₁₋₄ y haloalcoxi C₁₋₄; X se selecciona a partir del grupo que consiste en cicloalquilo C₃₋₆, fenilo, un heteroarilo de 5 ó 6 miembros, que comprende 1, 2, 3 ó 4 heteroátomos seleccionados individualmente entre N, O y S, y un heterociclilo de 4 a 6 miembros, que comprende 1, 2 ó 3 heteroátomos seleccionados individualmente entre N, O y S, y donde dichos restos cicloalquilo, fenilo, heteroarilo o heterociclilo están sustituidos opcionalmente por 1 ó 2 sustituyentes, que pueden ser idénticos o diferentes, seleccionados de R⁹, y donde los restos CR¹R², Q y Z mencionados anteriormente se pueden unir a cualquier posición de dichos restos cicloalquilo, fenilo, heteroarilo o heterociclilo; n es 0 ó 1; Z se selecciona a partir del grupo que consiste en -C(O)OR¹⁰, -CH₂OH, -CHO, -C(O)NHOR¹¹, -C(O)NHCN, -OC(O)NHOR¹¹, -OC(O)NHCN, -NR⁶C(O)NHOR¹¹, -NR⁶C(O)NHCN, -C(O)NHS(O)₂R¹², -OC(O)NHS(O)₂R¹², -NR⁶C(O)NHS(O)₂R¹², -S(O)₂OR¹⁰, -OS(O)₂OR¹⁰, -NR⁶S(O)₂OR¹⁰, -NR⁶S(O)OR¹⁰, -NHS(O)₂R¹⁴, -S(O)OR¹⁰, -OS(O)OR¹⁰, -S(O)₂NHCN, -S(O)₂NHC(O)R¹⁸, -S(O)₂NHS(O)₂R¹², -OS(O)₂NHCN, -OS(O)₂NHS(O)₂R¹², -OS(O)₂NHC(O)R¹⁸, -NR⁶S(O)₂NHCN, -NR⁶S(O)₂NHC(O)R¹⁸, -N(OH)C(O)R¹⁵, -ONHC(O)R¹⁵, -NR⁶S(O)₂NHS(O)₂R¹², -P(O)(R¹³)(OR¹⁰), -P(O)H(OR¹⁰), -OP(O)(R¹³)(OR¹⁰), -NR⁶P(O)(R¹³)(OR¹⁰) y tetrazol; R¹⁰ se selecciona del grupo que consiste en hidrógeno, alquilo C₁₋₆, fenilo y bencilo, y donde dichos fenilo o bencilo están opcionalmente sustituidos por 1, 2 ó 3 sustituyentes R⁹, que pueden ser iguales o diferentes; R¹¹ se selecciona del grupo que consiste en hidrógeno, alquilo C₁₋₆ y fenilo, y donde dicho fenilo está opcionalmente sustituido por 1, 2 ó 3 sustituyentes R⁹, que pueden ser iguales o diferentes; R¹² se selecciona del grupo que consiste en alquilo C₁₋₆, haloalquilo C₁₋₆, alcoxi C₁₋₆, -OH, -N(R⁶)₂ y fenilo, y donde dicho fenilo está opcionalmente sustituido por 1, 2 ó 3 sustituyentes R⁹, que pueden ser iguales o diferentes; R¹³ se selecciona del grupo que consiste en -OH, alquilo C₁₋₆, alcoxi C₁₋₆ y fenilo; R¹⁴ es haloalquilo C₁₋₆; R¹⁵ se selecciona del grupo que consiste en alquilo C₁₋₆ y fenilo, y donde dicho fenilo está opcionalmente sustituido por 1, 2 ó 3 sustituyentes R⁹, que pueden ser iguales o diferentes; R¹⁵ᵃ es fenilo, donde dicho fenilo está opcionalmente sustituido por 1, 2 ó 3 sustituyentes R⁹, que pueden ser iguales o diferentes; R¹⁶ y R¹⁷ se seleccionan independientemente del grupo que consiste en hidrógeno y alquilo C₁₋₆; o R¹⁶ y R¹⁷, en conjunto con el átomo de nitrógeno al que estos están unidos, forman un anillo de heterociclilo de 4 a 6 elementos que comprende opcionalmente un heteroátomo adicional seleccionado individualmente de N, O y S; y R¹⁸ se selecciona del grupo que consiste en hidrógeno, alquilo C₁₋₆, haloalquilo C₁₋₆, alcoxi C₁₋₆, -N(R⁶)₂ y fenilo, y donde dicho fenilo está opcionalmente sustituido por 1, 2 ó 3 sustituyentes R⁹, que pueden ser iguales o diferentes; y r es 0, 1 ó 2; con la condición de que el compuesto de fórmula (1) no sea 2-[4-(1-metil-[1,2,4]triazolo[1,5-a]piridin-1-ium-2-il)piridin-1-ium-1-il]acetato de etilo de fórmula (3) o 2-[4-([1,2,4]triazolo[1,5-a]piridin-2-il)piridin-1-ium-1-il]acetato de etilo de fórmula (4).Compounds of formula (1) where the substituents are as defined in claim 1, useful as pesticides, especially as herbicides. Claim 1: Use of a compound of formula (1) or a zwitterionic species or agronomically acceptable salt thereof, as a herbicide: wherein R¹ is selected from the group consisting of hydrogen, halogen, C₁₋₆ alkyl, C₂₋₆ alkenyl, alkynyl C₂₋₆, C₃₋₆ cycloalkyl, C₁₋₆ haloalkyl, -OR⁷, -OR¹⁵ᵃ, -N(R⁶)S(O)₂R¹⁵, -N(R⁶)C(O)R¹⁵, -N(R⁶)C(O )OR¹⁵, -N(R⁶)C(O)NR¹⁶R¹⁷, -N(R⁶)CHO, -N(R⁷ᵃ)₂ and -S(O)ʳR¹⁵; R² is selected from the group consisting of hydrogen, halogen, C₁₋₆ alkyl, and C₁₋₆ haloalkyl; and where, when R¹ is selected from the group consisting of -OR⁷, -OR¹⁵ᵃ, -N(R⁶)S(O)₂R¹⁵, -N(R⁶)C(O)R¹⁵, -N(R⁶)C(O)OR¹⁵ , -N(R⁶)C(O)NR¹⁶R¹⁷, -N(R⁶)CHO, -N(R⁷ᵃ)₂ and -S(O)ʳR¹⁵, R² is selected from the group consisting of hydrogen and C₁₋₆ alkyl; or R¹ and R², together with the carbon atom to which they are attached, form a 3- to 6-membered C₃₋₆ cycloalkyl or heterocyclyl ring, comprising 1 or 2 heteroatoms individually selected from N and O; and Q is (CR¹ᵃR²ᵇ)ₘ; m is 0, 1, 2 or 3; R¹ᵃ and R²ᵇ are each independently selected from the group consisting of hydrogen, halogen, C₁₋₆ alkyl, C₁₋₆ haloalkyl, -OH, -OR⁷, -OR¹⁵ᵃ, -NH₂, -NHR⁷, -NHR¹⁵ᵃ, -N (R⁶)CHO, -NR⁷ᵇR⁷ᶜ and -S(O)ʳR¹⁵; or each R¹ᵃ and R²ᵇ, together with the carbon atom to which they are attached, form a 3- to 6-membered C₃₋₆ cycloalkyl or heterocyclyl ring, comprising 1 or 2 heteroatoms individually selected from N and O; and R³, R³ᵃ, R⁴ and R⁵ are independently selected from the group consisting of hydrogen, halogen, cyano, nitro, -S(O)ʳR¹⁵, C₁₋₆ alkyl, C₁₋₆ fluoroalkyl, C₁₋₆ fluoroalkoxy, C₁₋₆ alkoxy , C₃₋₆ cycloalkyl and -N(R⁶)₂; each R⁶ is independently selected from hydrogen and C₁₋₆ alkyl; each R⁷ is independently selected from the group consisting of C₁₋₆ alkyl, -S(O)₂R¹⁵, -C(O)R¹⁵, -C(O)OR¹⁵, and -C(O)NR¹⁶R¹⁷; each R⁷ᵃ is independently selected from the group consisting of -S(O)₂R¹⁵, -C(O)R¹⁵, -C(O)OR¹⁵ -C(O)NR¹⁶R¹⁷ and -C(O)NR⁶R¹⁵ᵃ; R⁷ᵇ and R⁷ᶜ are independently selected from the group consisting of C₁₋₆ alkyl, -S(O)₂R¹⁵, -C(O)R¹⁵, -C(O)OR¹⁵, -C(O)NR¹⁶R¹⁷ and phenyl, and wherein said phenyl is optionally substituted by 1, 2 or 3 R⁹ substituents, which may be the same or different; or R⁷ᵇ and R⁷ᶜ, together with the nitrogen atom to which they are attached, form a 4 to 6 membered heterocyclyl ring optionally comprising an additional heteroatom individually selected from N, O and S; and A is a fused bicyclic structure of general formula (2); in which: (i) ring A¹ has 6 elements and ring A² has 5 elements; (ii) A includes at least one heteroatom selected from N, O and S, the remainder being carbon atoms; (iii) at least one of ring A¹ and ring A² is aromatic, or A as a whole is aromatic; (iv) A may be attached to the rest of the compound of formula (1) at any available position on the A² ring as long as it is a carbon atom; (v) one of the carbon atoms is optionally a carbonyl; (vi) A is optionally substituted at any available position on either or both of ring A¹ or ring A² with p substituents R⁸, which may be the same or different; and (vii) p is 0 to 6; when A is substituted on one or more carbon atoms by R⁸, then each R⁸ is independently selected from the group consisting of halogen, nitro, cyano, -NH₂, -NHR⁷, -N(R⁷)₂, -OH, -OR⁷, -S(O)ʳR¹⁵, -NR⁶S(O)₂R¹⁵, -C(O)OR¹⁰, -C(O)R¹⁵, -C(O)NR¹⁶R¹⁷, -S(O)₂NR¹⁶R¹⁷, C₁₋₆ alkyl, C₁₋ haloalkyl ₆, C₃₋₆-cycloalkyl, C₃₋₆-halocycloalkyl, C₃₋₆-cycloalkoxy, C₂₋₆-alkenyl, C₂₋₆-haloalkenyl, C₂₋₆-alkynyl, C₁₋₆-alkoxy, C₁₋₁-alkyl-,₋-C₁-alkoxy, C₁₋₃-C₁₋₃-alkoxy-, C₁₋₆-haloalkoxy, C₁₋₃-haloalkoxy-C₁₋₃-alkyl-, C₃₋₆alkenyloxy, C₃₋₆alkynyloxy, N-C₃₋₆cycloalkylamino, -C(R⁶)= , phenyl, a 3 to 6 membered heterocyclyl, comprising 1 or 2 heteroatoms individually selected from N and O, and a 5 or 6 membered heteroaryl, comprising 1, 2, 3 or 4 heteroatoms, individually selected from N, O and S, and where said phenyl, heterocyclyl or heteroaryl moieties are optionally substituted by 1, 2 or 3 substituents, which may be identical or different s, selected from R⁹; and when A is substituted on one or more N atoms by one or more R⁸, then each R⁸ is independently selected from the group consisting of -OR⁷, -S(O)ʳR¹², C₁₋₆ alkyl, C₁₋₆ haloalkyl, cycloalkyl C₃₋₆, Halocicloalquilo C₃₋₆, Cycloalxi C₃₋₆, Alquenilo C₂₋₆, Haloalquenilo C₂₋₆, Alquinil ₃C₁₋₃alkyl, C₁₋₆alkoxycarbonyl, C₃₋₆alkenyloxy, C₃₋₆alkynyloxy, C₁₋₆alkylcarbonyl, C₁₋₆alkylaminocarbonyl, dialkyl-C₁₋₆aminocarbonyl, phenyl and heteroaryl, wherein the monocyclic aromatic ring moiety is 5 or 6 members comprising 1, 2, 3 or 4 heteroatoms individually selected from N, O and S, and where any of said phenyl or heteroaryl moieties are optionally substituted by 1, 2 or 3 substituents, which may be the same or different, selected from R⁹; each R⁹ is independently selected from the group consisting of halogen, cyano, -OH, -N(R⁶)₂, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkyl, and C₁₋₄ haloalkoxy; X is selected from the group consisting of C₃₋₆ cycloalkyl, phenyl, a 5 or 6 membered heteroaryl, comprising 1, 2, 3 or 4 heteroatoms individually selected from N, O and S, and a 4 to 6 membered heterocyclyl. 6 members, comprising 1, 2 or 3 heteroatoms individually selected from N, O and S, and where said cycloalkyl, phenyl, heteroaryl or heterocyclyl moieties are optionally substituted by 1 or 2 substituents, which may be identical or different, selected from R⁹ , and wherein the aforementioned CR¹R², Q and Z moieties can be attached to any position of said cycloalkyl, phenyl, heteroaryl or heterocyclyl moieties; n is 0 or 1; Z is selected from the group consisting of -C(O)OR¹⁰, -CH₂OH, -CHO, -C(O)NHOR¹¹, -C(O)NHCN, -OC(O)NHOR¹¹, -OC(O)NHCN , -NR⁶C(O)NHOR¹¹, -NR⁶C(O)NHCN, -C(O)NHS(O)₂R¹², -OC(O)NHS(O)₂R¹², -NR⁶C(O)NHS(O)₂R¹², -S (O)₂OR¹⁰, -OS(O)₂OR¹⁰, -NR⁶S(O)₂OR¹⁰, -NR⁶S(O)OR¹⁰, -NHS(O)₂R¹⁴, -S(O)OR¹⁰, -OS(O)OR¹⁰, -S( O)₂NHCN, -S(O)₂NHC(O)R¹⁸, -S(O)₂NHS(O)₂R¹², -OS(O)₂NHCN, -OS(O)₂NHS(O)₂R¹², -OS(O)₂NHC (O)R¹⁸, -NR⁶S(O)₂NHCN, -NR⁶S(O)₂NHC(O)R¹⁸, -N(OH)C(O)R¹⁵, -ONHC(O)R¹⁵, -NR⁶S(O)₂NHS(O) ₂R¹², -P(O)(R¹³)(OR¹⁰), -P(O)H(OR¹⁰), -OP(O)(R¹³)(OR¹⁰), -NR⁶P(O)(R¹³)(OR¹⁰), and tetrazole; R¹⁰ is selected from the group consisting of hydrogen, C₁₋₆ alkyl, phenyl and benzyl, and wherein said phenyl or benzyl is optionally substituted by 1, 2 or 3 R⁹ substituents, which may be the same or different; R¹¹ is selected from the group consisting of hydrogen, C₁₋₆ alkyl and phenyl, and wherein said phenyl is optionally substituted by 1, 2 or 3 R⁹ substituents, which may be the same or different; R¹² is selected from the group consisting of C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, -OH, -N(R⁶)₂ and phenyl, and wherein said phenyl is optionally substituted by 1, 2 or 3 R⁹ substituents , which can be the same or different; R¹³ is selected from the group consisting of -OH, C₁₋₆ alkyl, C₁₋₆ alkoxy, and phenyl; R¹⁴ is C₁₋₆ haloalkyl; R¹⁵ is selected from the group consisting of C₁₋₆ alkyl and phenyl, and wherein said phenyl is optionally substituted by 1, 2 or 3 R⁹ substituents, which may be the same or different; R¹⁵ᵃ is phenyl, wherein said phenyl is optionally substituted by 1, 2 or 3 R⁹ substituents, which may be the same or different; R¹⁶ and R¹⁷ are independently selected from the group consisting of hydrogen and C₁₋₆ alkyl; or R¹⁶ and R¹⁷, together with the nitrogen atom to which they are attached, form a 4 to 6 membered heterocyclyl ring optionally comprising an additional heteroatom individually selected from N, O and S; and R¹⁸ is selected from the group consisting of hydrogen, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, -N(R⁶)₂ and phenyl, and wherein said phenyl is optionally substituted by 1, 2 or 3 R⁹ substituents , which can be the same or different; and r is 0, 1 or 2; with the proviso that the compound of formula (1) is not 2-[4-(1-methyl-[1,2,4]triazolo[1,5-a]pyridin-1-ium-2-yl)pyridin Ethyl -1-ium-1-yl]acetate of formula (3) or 2-[4-([1,2,4]triazolo[1,5-a]pyridin-2-yl)pyridin-1-ium Ethyl -1-yl]acetate of formula (4).

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