AR117990A1 - HERBICIDE COMPOUNDS - Google Patents
HERBICIDE COMPOUNDSInfo
- Publication number
- AR117990A1 AR117990A1 ARP200100287A ARP200100287A AR117990A1 AR 117990 A1 AR117990 A1 AR 117990A1 AR P200100287 A ARP200100287 A AR P200100287A AR P200100287 A ARP200100287 A AR P200100287A AR 117990 A1 AR117990 A1 AR 117990A1
- Authority
- AR
- Argentina
- Prior art keywords
- phenyl
- group
- alkyl
- substituents
- hydrogen
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 3
- 239000004009 herbicide Substances 0.000 title abstract 2
- 230000002363 herbicidal effect Effects 0.000 title 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 22
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 17
- 125000001424 substituent group Chemical group 0.000 abstract 11
- 229910052739 hydrogen Inorganic materials 0.000 abstract 10
- 239000001257 hydrogen Substances 0.000 abstract 10
- 125000000623 heterocyclic group Chemical group 0.000 abstract 9
- 125000005842 heteroatom Chemical group 0.000 abstract 8
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 abstract 7
- 150000002431 hydrogen Chemical group 0.000 abstract 7
- 229910052736 halogen Inorganic materials 0.000 abstract 6
- 150000002367 halogens Chemical group 0.000 abstract 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 5
- 229910052760 oxygen Inorganic materials 0.000 abstract 5
- 229910052717 sulfur Inorganic materials 0.000 abstract 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 4
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 3
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 3
- 125000001072 heteroaryl group Chemical group 0.000 abstract 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 2
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 abstract 2
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 abstract 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 abstract 2
- -1 C3− cycloalkoxy 6 Chemical group 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 abstract 1
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 abstract 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 abstract 1
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 abstract 1
- 125000003302 alkenyloxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000005133 alkynyloxy group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000006310 cycloalkyl amino group Chemical group 0.000 abstract 1
- 125000004428 fluoroalkoxy group Chemical group 0.000 abstract 1
- 125000000262 haloalkenyl group Chemical group 0.000 abstract 1
- 125000004438 haloalkoxy group Chemical group 0.000 abstract 1
- 125000005347 halocycloalkyl group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000000575 pesticide Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 150000003536 tetrazoles Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/707—1,2,3- or 1,2,4-triazines; Hydrogenated 1,2,3- or 1,2,4-triazines
-
- 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
- A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Agronomy & Crop Science (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine 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: Un compuesto de fórmula (1) o una especie zwitteriónica o sal agronómicamente aceptable de este, donde A¹, A², A³, A⁴ y A⁵ se seleccionan cada uno independientemente del grupo constituido por C-H, C-R⁸ y N; y de 2 a 4 de entre A¹, A², A³, A⁴ y A⁵ son N; y el anillo que comprende A¹, A², A³, A⁴ y A⁵ es aromático; R¹ se selecciona del grupo constituido por 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 constituido por hidrógeno, halógeno, alquilo C₁₋₆ y haloalquilo C₁₋₆; y donde, cuando R¹ se selecciona del grupo constituido por -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 constituido por 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 R¹ᵃ y R²ᵇ se selecciona independientemente del grupo constituido por 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 constituido por 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 constituido por alquilo C₁₋₆, -S(O)₂R¹⁵, -C(O)R¹⁵, -C(O)OR¹⁵ y -C(O)NR¹⁶R¹⁷; cada R⁷ᵃ se selecciona independientemente del grupo constituido por -S(O)₂R¹⁵, -C(O)R¹⁵, -C(O)OR¹⁵, -C(O)NR¹⁶R¹⁷ y -C(O)NR⁶R¹⁵ᵃ; R⁷ᵇ y R⁷ᶜ se seleccionan independientemente del grupo constituido por alquilo C₁₋₆, -S(O)₂R¹⁵, -C(O)R¹⁵, -C(O)OR¹⁵, -C(O)NR¹⁶R¹⁷ y fenilo, y donde dicho fenilo está opcionalmente sustituido con 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 cada R⁸ se selecciona independientemente del grupo constituido por 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 C₁₋₃)(alquil C₁₋₃)-, hidroxi(alquil C₁₋₆)-, (alcoxi C₁₋₃)(alcoxi C₁₋₃)-, haloalcoxi C₁₋₆, (haloalcoxi C₁₋₃)(alquil C₁₋₃)-, alqueniloxi C₃₋₆, alquiniloxi C₃₋₆, N-(cicloalquilamino C₃₋₆), -C(R⁶)=NOR⁶, fenilo, un heterociclilo de 3 a 6 miembros, que comprende 1 ó 2 heteroátomos seleccionados individualmente entre N y O, y un heteroarilo de 5 ó 6 miembros, que comprende 1, 2, 3 ó 4 heteroátomos seleccionados individualmente entre N, O y S, y donde dichos fenilo, heterociclilo o heteroarilo están opcionalmente sustituidos con 1, 2 ó 3 sustituyentes R⁹, que pueden ser iguales o diferentes; cada R⁹ se selecciona independientemente del grupo constituido por halógeno, ciano, -OH, -N(R⁶)₂, alquilo C₁₋₄, alcoxi C₁₋₄, haloalquilo C₁₋₄ y haloalcoxi C₁₋₄; X se selecciona del grupo constituido por 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 opcionalmente sustituidos con 1 ó 2 sustituyentes R⁹, y donde los restos CR¹R², Q y Z mencionados anteriormente pueden estar unidos a cualquier posición de dichos restos de cicloalquilo, fenilo, heteroarilo o heterociclilo; n es 0 ó 1; Z se selecciona del grupo constituido por -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 constituido por hidrógeno, alquilo C₁₋₆, fenilo y bencilo, y donde dichos fenilo o bencilo están opcionalmente sustituidos con 1, 2 ó 3 sustituyentes R⁹, que pueden ser iguales o diferentes; siempre que, cuando A¹, A³ y A⁵ sean todos N, A² y A⁴ sean C-H, n sea 0, m sea 0 y Z sea -C(O)OR¹⁰, entonces R¹⁰ se selecciona del grupo constituido por alquilo C₃₋₆, fenilo y bencilo, y donde dichos fenilo o bencilo están opcionalmente sustituidos con 1, 2 ó 3 sustituyentes R⁹, que pueden ser iguales o diferentes; R¹¹ se selecciona del grupo constituido por hidrógeno, alquilo C₁₋₆ y fenilo, y donde dicho fenilo está opcionalmente sustituido con 1, 2 ó 3 sustituyentes R⁹, que pueden ser iguales o diferentes; R¹² se selecciona del grupo constituido por alquilo C₁₋₆, haloalquilo C₁₋₆, alcoxi C₁₋₆, -OH, -N(R⁶)₂ y fenilo, y donde dicho fenilo está opcionalmente sustituido con 1, 2 ó 3 sustituyentes R⁹, que pueden ser iguales o diferentes; R¹³ se selecciona del grupo constituido por -OH, alquilo C₁₋₆, alcoxi C₁₋₆ y fenilo; R¹⁴ es haloalquilo C₁₋₆; R¹⁵ se selecciona del grupo constituido por alquilo C₁₋₆ y fenilo, y donde dicho fenilo está opcionalmente sustituido con 1, 2 ó 3 sustituyentes R⁹, que pueden ser iguales o diferentes; R¹⁵ᵃ es fenilo, donde dicho fenilo está opcionalmente sustituido con 1, 2 ó 3 sustituyentes R⁹, que pueden ser iguales o diferentes; R¹⁶ y R¹⁷ se seleccionan independientemente del grupo constituido por hidrógeno y alquilo C₁₋₆; o R¹⁶ y R¹⁷, 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 R¹⁸ se selecciona del grupo constituido por hidrógeno, alquilo C₁₋₆, haloalquilo C₁₋₆, alcoxi C₁₋₆, -N(R⁶)₂ y fenilo, y donde dicho fenilo está opcionalmente sustituido con 1, 2 ó 3 sustituyentes R⁹, que pueden ser iguales o diferentes; y r es 0, 1 ó 2.Compounds of formula (1) where the substituents are as defined in claim 1, useful as pesticides, especially herbicides. Claim 1: A compound of formula (1) or a zwitterionic species or agronomically acceptable salt thereof, wherein A¹, A², A³, A⁴ and A⁵ are each independently selected from the group consisting of C-H, C-R⁸ and N; and from 2 to 4 of A¹, A², A³, A⁴ and A⁵ are N; and the ring comprising A¹, A², A³, A⁴ and A⁵ is aromatic; R¹ is selected from the group consisting of hydrogen, halogen, C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl, 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 C₃₋₆ cycloalkyl ring or a 3- to 6-membered heterocyclyl, comprising 1 or 2 heteroatoms individually selected from N and O; and Q is (CR¹ᵃR²ᵇ) ₘ; m is 0, 1, 2, or 3; each R¹ᵃ and R²ᵇ is 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 C₃₋₆ cycloalkyl or 3- to 6-membered 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 and -N (R⁶) cycloalkyl; 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 where said phenyl is optionally substituted with 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 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, C₁₋₆ haloalkyl, C₃₋₆ cycloalkyl, C₃₋₆ halocycloalkyl, C₃₋ cycloalkoxy ₆, C₂₋₆ alkenyl, C₂₋₆ haloalkenyl, C₂₋₆ alkynyl, (C₁₋₃ alkoxy) (C₁₋₃ alkyl) -, hydroxy (C₁₋₆ alkyl) -, (C₁₋₃ alkoxy) (C₁₋ alkoxy ₃) -, C₁₋₆ haloalkoxy, (C₁₋₃ haloalkoxy) (C₁₋₃ alkyl) -, C₃₋₆ alkenyloxy, C₃₋₆ alkynyloxy, N- (C₃₋₆ cycloalkylamino), -C (R⁶) = NOR⁶, 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 are optionally substituted with 1, 2 or 3 R⁹ substituents, which may be the same or different; 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, 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 with 1 or 2 R⁹ substituents, and where 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 are optionally substituted with 1, 2 or 3 R⁹ substituents, which may be the same or different; provided that when A¹, A³ and A⁵ are all N, A² and A⁴ are CH, n is 0, m is 0 and Z is -C (O) OR¹⁰, then R¹⁰ is selected from the group consisting of C₃₋₆ alkyl, phenyl and benzyl, and where said phenyl or benzyl are optionally substituted with 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 with 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 with 1, 2 or 3 R⁹ substituents, that they 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 with 1, 2 or 3 R⁹ substituents, which may be the same or different; R¹⁵ᵃ is phenyl, where said phenyl is optionally substituted with 1, 2 or 3 substituents R⁹, 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 with 1, 2 or 3 R⁹ substituents, that they can be the same or different; and r is 0, 1, or 2.
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| CA2005658A1 (en) | 1988-12-19 | 1990-06-19 | Eliahu Zlotkin | Insecticidal toxins, genes encoding these toxins, antibodies binding to them and transgenic plant cells and plants expressing these toxins |
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