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EP-4739673-A1 - TRIAZOLE COMPOUNDS FOR THE CONTROL OF INVERTEBRATE PESTS

EP4739673A1EP 4739673 A1EP4739673 A1EP 4739673A1EP-4739673-A1

Abstract

The invention relates to compounds of formula (I) wherein the variables have the meanings as defined in the specification, to compositions comprising them, to active compound combinations comprising them, and to their use for protecting growing plants and animals from attack or infestation by invertebrate pests, furthermore, to seed comprising such compounds.

Inventors

  • Pedroni, Julia

Assignees

  • BASF SE

Dates

Publication Date
20260513
Application Date
20240627

Claims (18)

  1. 1. Compounds of formula I wherein R 1 is H, OH, NR 12 R 13 , Ci-Ce-alkyl, Ci-Ce-haloalkyl, Cs-Ce-cycloalkyl, Cs-Ce-halocycloalkyl, Ci-Cs-alkoxy, Ci-C4-alkyl-C3-C6-cycloalkyl, Ci-C^alkyl-Ca-Ce-halocycloalkyl, C 3 -C6-alkenyl, C 3 -C6-alkynyl, which groups are unsubstituted, or partially or fully substituted with R 11 ; or C(=N-R 11 )R 12 , C(O)R 11a ; R 11 is halogen, CN, NO 2 , NR 12 R 13 , C(O)NH 2 , C(S)NH 2 , C(O)OH, OR 14 , Si(CH 3 ) 3 ; Ci-C 6 -alkyl; Ci-C 6 - haloalkyl; C 2 -C6-alkenyl; C 2 -C6-haloalkenyl; C 2 -C6-alkynyl; C 2 -C6-haloalkynyl; C 3 -C4-cycloalkyl- Ci-C 2 -alkyl, which ring is unsubstituted or substituted with 1 or 2 halogen; 3- to 6-membered heterocyclyl, 5- or 6-membered hetaryl, or phenyl, which rings are unsubstituted or substituted with halogen, Ci-C 3 -haloalkyl, and/or CN; R 11a is NR 12 R 13 , C(O)NH 2 , C(S)NH 2 , C(O)OH, OR 14 , Si(CH 3 ) 3 ; Ci-C 6 -haloalkyl; C 2 -C 6 -alkenyl; C 2 -C 6 - haloalkenyl; C 2 -C6-alkynyl; C 2 -C6-haloalkynyl; C 3 -C4-cycloalkyl-Ci-C 2 -alkyl, which ring is unsubstituted or substituted with 1 or 2 halogen; 3- to 6-membered heterocyclyl, which rings are unsubstituted or substituted with halogen, Ci-C 3 -haloalkyl, and/or CN; R 12 , R 13 are independently from each other H, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci- C4-haloalkyl, C 3 -C6-cycloalkyl, C(O)-Ci-C4-alkyl, C(O)-Ci-C4-haloalkyl, C(O)-C 3 -C4-cycloalkyl, C(O)-C 3 -C 4 -halocycloalkyl, C(O)NH-Ci-C 4 -alkyl, C(O)NH-Ci-C 4 -haloalkyl, C(O)N(Ci-C 4 -alkyl)- Ci-C4-alkyl, C(O)N(Ci-C4-haloalkyl)-Ci-C4-alkyl, C(O)N(Ci-C4-haloalkyl)-Ci-C4-haloalkyl, C(O)NH-Ci-C 4 -alkoxy, C(O)NH-Ci-C 4 -haloalkoxy, C(O)NH-Ci-C4-alkoxy-Ci-C 4 -alkyl, C(O)NH- Ci-C4-alkoxy-Ci-C4-haloalkyl; C(O)NH-phenyl, C(O)NH-3-6-membered heterocyclyl or 5- or 6- membered hetaryl, C(O)NH-Ci-C4-alkyl-phenyl, C(O)NH-Ci-C4-alkyl-3-6-membered heterocyclyl or 5- or 6-membered hetaryl which rings are unsubstituted or substituted with halogen, C1-C3- haloalkyl, and/or CN; S(O) m -Ci-C4-haloalkyl, S(O) m -C 3 -C4-cycloalkyl, S(O) m -C 3 -C4-halocycloal- kyl; 3- to 6-membered heterocyclyl, 5- or 6-membered hetaryl, or phenyl, which rings are unsubstituted or substituted with halogen, Ci-C 3 -haloalkyl, and/or CN; or R 12 and R 13 together with the nitrogen atom to which they are bound, form a 3-, 4-, 5-, 6-, or 7-mem- bered saturated, partially or fully unsaturated heterocycle, which heterocycle may additionally contain 1 or 2 heteroatoms or heteroatom-containing groups selected from N, 0, S(0) m , and optionally one or two groups C(O) as ring members, and which heterocycle is unsubstituted or substituted with one or more R 3a ; or R 12 and R 13 together with the nitrogen atom to which they are bound, form a sulfoximino group =S(O)R 12a R 12b ; wherein R 12a , R 12b are independently Ci-Cs-alkyl, or together with the sulfur atom to which they are bound, form a 3-, 4-, 5-, 6-, or 7-membered saturated, partially or fully unsaturated heterocycle; m is O, 1 , or 2; each R 3a is independently selected from halogen, CN, NO2, OH, Ci-C4-alkyl, Ci-C haloalkyl, C1- C4-alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy, C3-C4-cycloalkyl, C3-C4-halocycloalkyl, S(O) m -Ci-C4- alkyl, S(O) m -Ci-C4-haloalkyl, S(O) m -C3-C4-cycloalkyl, S(O) m -C3-C4-halocycloalkyl, C(O)NR 12 R 13 , C(O)OR 141 , C(O)R 151 , C(=N-OR 141 )C3-C 6 -cycloalkyl, C(=N-OR 141 )NR 121 R 131 ; R 2 is H, CN, Ci-Cs-alkyl, Ci-Cs-haloalkyl, or C2-C3-alkynyl; each R 3 is independently selected from halogen, CN, NO2; Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-Ce-haloalkyl, Ci-Ce-halocycloalkyl, Ci-Ce-alkenyl, Ci-Ce-alkynyl, Cs-Ce-cycloalkyl-Ci-Ce-alkyl, Ci-Ce-alkyl-Cs-Ce-cy- cloalkyl which are unsubstituted or substituted with R 3a ; OR 14 , NR 121 R 131 , C(O)NR 121 R 122 , C(O)OR 14 , C(O)R 15 , S(O) m -R 15 , C(=N-OR 14 )NR 121 R 131 , or C(=N-OR 14 )C 3 -C 6 -cycloalkyl wherein the ring is unsubstituted or substituted with R 3a ; R 121 , R 131 are independently from each other H, or a group R 122 or R 132 ; R 122 , R 132 are independently from each other Ci-C4-alkyl, Ci-C4-al koxy , Ci -C4-haloalkoxy, C1-C4- haloalkyl, Cs-Ce-cycloalkyl, Ci-C4-alkyl-C3-C6-cycloalkyl, C(O)-Ci-C4-alkyl, C(O)-Ci-C4-haloalkyl, C(O)-C3-C4-cycloalkyl, C(O)-C3-C4-halocycloalkyl, C(O)NH-Ci-C4-alkyl, C(O)NH-Ci-C4-haloal- kyl, C(O)N(Ci-C 4 -alkyl)-Ci-C 4 -alkyl, C(O)N(Ci-C 4 -haloalkyl)-Ci-C 4 -alkyl, C(O)N(Ci-C 4 -haloalkyl)- Ci-C4-haloalkyl, C(O)NH-Ci-C4-alkoxy, C(O)NH-Ci-C4-haloalkoxy, C(O)NH-Ci-C4-alkoxy-Ci-C4- alkyl, C(O)NH-Ci-C4-alkoxy-Ci-C4-haloalkyl; C(O)NH-phenyl, C(O)NH-3-6-membered heterocy- clyl or 5- or 6-membered hetaryl, C(O)NH-Ci-C4-alkyl-phenyl, C(O)NH-Ci-C4-alkyl-3-6-mem- bered heterocyclyl or 5- or 6-membered hetaryl which rings are unsubstituted or substituted with halogen, Ci-Cs-haloalkyl, and/or CN; S(O) m -Ci-C4-haloalkyl, S(O) m -C3-C4-cycloalkyl, S(O) m -C3- C4-halocycloalkyl; 3- to 6-membered heterocyclyl, 5- or 6-membered hetaryl, or phenyl, which rings are unsubstituted or substituted with halogen, Ci-Cs-haloalkyl, and/or CN; or R 122 and R 132 , together with the nitrogen atom to which they are bound, form a 3-, 4-, 5-, 6- or 7-mem- bered saturated, partially unsaturated or fully unsaturated heterocycle, which heterocycle may additionally contain 1 or 2 heteroatoms or heteroatom-containing groups selected from N, 0, S(O) m , and C(O) as ring members, and which heterocycle is unsubstituted or substituted with one or more substituents R 3a ; or R 122 and R 132 , together with the nitrogen atom to which they are bound, form a sulfoximino group =S(O)R 12a R 12b ; R 14 is H, Ci-C4-alkyl, Ci-C^haloalkyl, Cs-Ce-cycloalkyl, Cs-Ce-halocycloalkyl, C3-C4-cycloalkyl-Ci-C2- alkyl, C3-C4-halocycloalkyl-Ci-C2-alkyl, C(O)-Ci-C4-alkyl, C(O)-Ci-C4-haloalkyl, C(O)-C3-C4-cy- cloalkyl, C(O)-C3-C4-halocycloalkyl, or phenyl which is unsubstituted or partially or fully substituted with R 3a ; R 141 is H, Ci-C4-alkyl, Ci-C4-haloalkyl, Cs-Ce-cycloalkyl, Cs-Ce-halocycloalkyl, C3-C4-cycloalkyl-Ci-C2- alkyl, C3-C4-halocycloalkyl-Ci-C2-alkyl, C(O)-Ci-C4-alkyl, C(O)-Ci-C4-haloalkyl, C(O)-C3-C4-cy- cloalkyl, C(O)-C3-C4-halocycloalkyl, or phenyl which is unsubstituted or substituted with halogen, Ci-Cs-haloalkyl, and/or CN; R 15 is H, Ci-C4-alkyl, or Ci-C4-haloalkyl, Cs-Ce-cycloalkyl, Cs-Ce-halocycloalkyl, which carbon chains are unsubstituted or partially or fully substituted with R 11 ; or 3- to 6-membered heterocyclyl, 5- or 6-membered hetaryl, or phenyl, which rings are unsubstituted or substituted with R 3a ; R 151 is H, Ci-C4-alkyl, or Ci-C4-haloalkyl, Cs-Ce-cycloalkyl, Cs-Ce-halocycloalkyl, which carbon chains are unsubstituted or partially or fully substituted with R 11 ; or 3- to 6-membered heterocyclyl, 5- or 6-membered hetaryl, or phenyl, which rings are unsubstituted or substituted with halogen, Ci-Cs-haloalkyl, and/or CN; n Is O, 1 , 2, or 3; R 4 is Cs-Ce-cycloalkyl partially or fully substituted with R 40 , or Cs-Ce-cycloalkeny I unsubstituted or partially or fully substituted with R 40 ; R 40 independently from one another are selected from halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, OR 15 , OC(O)OR 15 , OC(O)R 15 , OC(O)NR 12 R 13 , S(O) m -R 15 , C(O)OR 15 , C(O)R 15 , C(O)NHR 121 , C(O)NR 121 R 131 , C(O)NR 15 NR 12 R 13 , C(=NOR 14 )R 15 , C(=NOR 14 )NR 12 R 13 , NR 15 C(O)OR 15 , NR 15 NR 12 R 13 , 3- or 4-membered heterocycle unsubstituted or substituted with R 3 , 5- or 6-mem- bered heteroaryl or phenyl unsubstituted or substituted with R 3 ; provided that R 4 is not unsubstituted cyclopropyl, if Q is N, and R 5 and R 6 are both H; R 5 , R 6 are independently H, or as defined for R 3 ; X, Q are independently N, CH, or CR 3b ; R 3b is as defined for R 3 ; and the N-oxides, stereoisomers, and agriculturally or veterinarily acceptable salts thereof.
  2. 2. Compounds of formula I according to claim 1 , wherein R 1 is H or CH2-CC3H5.
  3. 3. Compounds of formula I according to claim 1 or 2, wherein R 2 is CH3.
  4. 4. Compounds of formula I according to any of claim 1 to 3, wherein R 3 is halogen, CN, Ci-C4-haloalkyl, C1-C4- haloalkoxy, C3-C4-cycloalkyl unsubstituted or substituted with one or more CN or halogen, C3-C4-halocycloal- kyl, S(O)m-Ci-C4-alkyl, S(O) m -Ci-C4-haloalkyl, S(O) m -C3-C4-cycloalkyl, S(O) m -C3-C4-halocycloalkyl, S(O) m - (substituted phenyl), C(=N-OR 14 )NR 121 R 131 , C(=N-OR 14 )C3-C6-cycloalkyl wherein the ring is unsubstituted or substituted with R 3a .
  5. 5. Compounds of formula I according to any of claim 1 to 4, wherein n is 2 and R 3 is in positions 3 and 5.
  6. 6. Compounds of formula I according to any one of claims 1 to 6, wherein at least one R 3 is selected from C(=N- OR 14 )NR 121 R 131 and C(=N-OR 14 )C3-C6-cycloalkyl wherein the ring is unsubstituted or substituted with R 3a .
  7. 7. Compounds of formula I according to any one of claims 1 to 6, wherein X is CH.
  8. 8. Compounds of formula I according to any one of claims 1 to 7, wherein R 4 is Ca-Ce-cycloal ky I partially or fully substituted with R 40 .
  9. 9. Compounds of formula I according to any one of claims 1 to 7, wherein R 4 is Ca-Ce-cycloal keny I unsubstituted or partially or fully substituted with R 40 .
  10. 10. Compounds of formula I according to any one of claims 1 to 9, which correspond to formula I. A
  11. Compounds of formula I according to any one of claims 1 to 9, which correspond to formula I . B
  12. 12. Compounds of formula I according to any one of the preceding claims, which consist mainly of the isomer I.S.
  13. 13. An agricultural or veterinary composition comprising at least one compound according to any one of claims 1 to 12 and/or at least one agriculturally or veterinarily acceptable salt thereof, and at least one inert liquid and/or solid agriculturally or veterinarily acceptable carrier.
  14. 14. An agricultural composition for combating animal pests comprising at least one compound as defined in any of claims 1 to 12 and at least one inert liquid and/or solid acceptable carrier and, if desired, at least one surfactant.
  15. 15. A method for combating or controlling invertebrate pests, which method comprises contacting said pest or its food supply, habitat or breeding grounds with a pesticidal ly effective amount of at least one compound as defined in any one of claims 1 to 12.
  16. 16. A method for protecting growing plants from attack or infestation by invertebrate pests, which method comprises contacting a plant, or soil or water in which the plant is growing, with a pesticidally effective amount of at least one compound as defined in any of claims 1 to 12.
  17. 17. Seed comprising a compound as defined in any of claims 1 to 12, or the enantiomers, diastereomers or salts thereof, in an amount of from 0.1 g to 10 kg per 100 kg of seed.
  18. 18. A method for treating or protecting an animal from infestation or infection by invertebrate pests which comprises bringing the animal in contact with a pesticidally effective amount of at least one compound of the formula I as defined in any of claims 1 to 12, a stereoisomer thereof and/or at least one veterinarily acceptable salt thereof.

Description

Triazole compounds for the control of invertebrate pests Description The invention relates to compounds of formula I wherein R1 is H, OH, NR12R13, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Cs-Ce-cycloalkyl, Cs-Ce-halocycloalkyl, Ci-Cs-alkoxy, C1-C4- alkyl-Cs-Ce-cycloalkyl, Ci-C^alkyl-Cs-Ce-halocycloalkyl, Cs-Ce-alkenyl, Cs-Ce-alkynyl, which groups are unsubstituted, or partially or fully substituted with R11; or C(=N-R11)R12, C(O)R11a; R11 is halogen, ON, NO2, NR12R13, C(O)NH2, C(S)NH2, C(O)OH, OR14, Si (CH3)3; Ci-C6-alkyl; Ci-C6-haloal- kyl; C2-C6-alkenyl; C2-C6-haloalkenyl; C2-C6-alkynyl; C2-C6-haloalkynyl; C3-C4-cycloalkyl-Ci-C2-alkyl, which ring is unsubstituted or substituted with 1 or 2 halogen; 3- to 6-membered heterocyclyl, 5- or 6- membered hetaryl, or phenyl, which rings are unsubstituted or substituted with halogen, Ci-C3-haloal- kyl, and/or ON; R11a is NR12R13, C(O)NH2, C(S)NH2, C(O)OH, OR14, Si(CH3)3; Ci-C6-haloalkyl; C2-C6-alkenyl; C2-C6-haloal- kenyl; C2-C6-alkynyl; C2-C6-haloalkynyl; C3-C4-cycloalkyl-Ci-C2-alkyl, which ring is unsubstituted or substituted with 1 or 2 halogen; 3- to 6-membered heterocyclyl, which rings are unsubstituted or substituted with halogen, Ci-Cs-haloalkyl, and/or ON; R12, R13 are independently from each other H, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-haloal- kyl, Ca-Ce-cycloalkyl, C(O)-Ci-C4-alkyl, C(O)-Ci-C4-haloalkyl, C(O)-C3-C4-cycloalkyl, C(O)-C3-C4-halo- cycloalkyl, C(O)NH-Ci-C4-alkyl, C(O)NH-Ci-C4-haloalkyl, C(O)N(Ci-C4-alkyl)-Ci-C4-alkyl, C(O)N(CI-C4- haloalkyl)-Ci-C4-alkyl, C(O)N(Ci-C4-haloalkyl)-Ci-C4-haloalkyl, C(O)NH-Ci-C4-alkoxy, C(O)NH-CI-C4- haloalkoxy, C(O)NH-Ci-C4-alkoxy-Ci-C4-alkyl, C(O)NH-Ci-C4-alkoxy-Ci-C4-haloalkyl; C(O)NH-phenyl, C(O)NH-3-6-membered heterocyclyl or 5- or 6-membered hetaryl, C(O)NH-Ci-C4-alkyl-phenyl, C(O)NH-Ci-C4-alkyl-3-6-membered heterocyclyl or 5- or 6-membered hetaryl which rings are unsubstituted or substituted with halogen, Ci-Cs-haloalkyl, and/or CN; S(O)m-Ci-C4-haloalkyl, S(O)m-C3-C4-cy- cloalkyl, S(O)m-C3-C4-halocycloalkyl; 3- to 6-membered heterocyclyl, 5- or 6-membered hetaryl, or phenyl, which rings are unsubstituted or substituted with halogen, Ci-Cs-haloalkyl, and/or CN; or R12 and R13 together with the nitrogen atom to which they are bound, form a 3-, 4-, 5-, 6-, or 7-membered saturated, partially or fully unsaturated heterocycle, which heterocycle may additionally contain 1 or 2 heteroatoms or heteroatom-containing groups selected from N, 0, S(0)m, and optionally one or two groups C(O) as ring members, and which heterocycle is unsubstituted or substituted with one or more R3a; R12 and R13 together with the nitrogen atom to which they are bound, form a sulfoximino group =S(O)R12aR12b; wherein R12a, R12b are independently Ci-Cs-alkyl, or together with the sulfur atom to which they are bound, form a 3-, 4-, 5-, 6-, or 7-membered saturated, partially or fully unsaturated heterocycle; m Is O, 1 , or 2; each R3a is independently selected from halogen, CN, NO2, OH, Ci-C4-alkyl, Ci-C haloalkyl, C1-C4- alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy, C3-C4-cycloalkyl, C3-C4-halocycloalkyl, S(O)m-Ci-C4-alkyl, S(O)m- Ci-C4-haloalkyl, S(O)m-C3-C4-cycloalkyl, S(O)m-C3-C4-halocycloalkyl, C(O)NR12R13, C(O)OR141, C(O)R151, C(=N-OR141)C3-C6-cycloalkyl, C(=N-OR141)NR121R131; R2 is H, CN, Ci-Cs-alkyl, Ci-Cs-haloalkyl, or C2-C3-alkynyl; each R3 is independently selected from halogen, CN, NO2; Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-Ce-haloalkyl, Ci-Ce- halocycloalkyl, Ci-Ce-alkenyl, Ci-Ce-alkynyl, Cs-Ce-cycloalkyl-Ci-Ce-alkyl, Ci-Ce-alkyl-Cs-Ce-cycloalkyl which are unsubstituted or substituted with R3a; OR14, NR121R131, C(O)NR121R122, C(O)OR14, C(O)R15, S(O)m-R15, C(=N-OR14)NR121R131, or C(=N-OR14)C3-C6-cycloalkyl wherein the ring is unsubstituted or substituted with R3a; R121, R131 are independently from each other H, or a group R122 or R132; R122, R132 are independently from each other Ci-C4-alkyl, Ci-C4-al koxy , Ci -C4-haloalkoxy, Ci-C4-haloalkyl, Cs-Ce-cycloalkyl, Ci-C4-alkyl-C3-C6-cycloalkyl, C(O)-Ci-C4-alkyl, C(O)-Ci-C4-haloalkyl, C(O)-C3-C4-cy- cloalkyl, C(O)-C3-C4-halocycloalkyl, C(O)NH-Ci-C4-alkyl, C(O)NH-Ci-C4-haloalkyl, C(O)N(Ci-C4-alkyl)- Ci-C4-alkyl, C(O)N(Ci-C4-haloalkyl)-Ci-C4-alkyl, C(O)N(Ci-C4-haloalkyl)-Ci-C4-haloalkyl, C(O)NH-Ci- C4-alkoxy, C(O)NH-Ci-C4-haloalkoxy, C(O)NH-Ci-C4-alkoxy-Ci-C4-alkyl, C(O)NH-Ci-C4-alkoxy-Ci-C4- haloalkyl; C(O)NH-phenyl, C(O)NH-3-6-membered heterocyclyl or 5- or 6-membered hetaryl, C(O)NH- Ci-C4-alkyl-phenyl, C(O)NH-Ci-C4-alkyl-3-6-membered heterocyclyl or 5- or 6-membered hetaryl which rings are unsubstituted or substituted with halogen, Ci-Cs-haloalkyl, and/or CN; S(O)m-Ci-C4-haloalkyl, S(O)m-C3-C4-cycloalkyl, S(O)m-C3-C4-halocycloalkyl; 3- to 6-membered heterocyclyl, 5- or 6-membered hetaryl, or phenyl, which rings are unsubstituted or substituted with halogen, Ci-Cs-haloalkyl, and/or CN; or R122 and R132, together with the nitrogen atom to which they are bound, form a 3-, 4-, 5-, 6- or 7-memb