Pyrazole Compounds for Controlling Invertebrate Pests

• US 20110173726A1
• Filed: 09/23/2009
• Published: 07/14/2011
• Est. Priority Date: 09/24/2008
• Status: Active Grant

• Current Assignee: BASF SE
• Original Assignee: BASF SE
• Inventors: Groß, Steffen, Sörgel, Sebastian, Körber, Karsten, Dickhaut, Joachim, Deshmukh, Prashant, Culbertson, Deborah L., Oloumi-Sadeghi, Hassan, Anspaugh, Douglas D., Pohlman, Matthias, Von Deyn, Wolfgang, Kaiser, Florian, Le Vezouet, Ronan
• Granted Patent: US 8,853,125 B2
• Time in Patent Office: Days
• US Class Current: 800/298
• CPC Class Codes: A01N 43/90 having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
• CPC Class Codes: A61P 33/00 Antiparasitic agents
• CPC Class Codes: C07D 471/04 Ortho-condensed systems
• CPC Class Codes: C07D 487/04 Ortho-condensed systems
• CPC Class Codes: C07D 498/04 Ortho-condensed systems

Abstract

The present invention relates to a method for controlling invertebrate pests which method comprises treating the pests, their food supply, their habitat or their breeding ground or a plant, seed, soil, area, material or environment in which the pests are growing or may grow, or the materials, plants, seeds, soils, surfaces or spaces to be protected from pest attack or infestation with a pesticidally effective amount of a pyrazole compound of formulae I or II or a salt or an N-oxide thereof, wherein A is a pyrazole radical of the formulae A1 or A2, wherein # denotes the binding; D is a 5- or 6-membered heterocyclic radical fused to the pyrazole moiety; R^p1, R^p2 and R^px are H, halogen, CN, NO₂, C₁-C₁₀-alkyl, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, etc.; n is 0 to 4; or two radicals R^px bound to the same ring-member may form an oxo substituent, or two radicals R^px bound to adjacent ring-members may form a 3- to 7-membered fused cyclic radical; B is N or CR⁴, wherein R⁴ is H, halogen, CN, NO₂, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, etc.; X¹ is S, O or NR^1a, wherein R^1a is H, C₁-C₁₀-alkyl, etc.; X² is O^2a, NR^2bR^2c or S(O)_mR^2d, wherein m is 0, 1 or 2; R^2a is C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl, etc.; R^2b, R^2c are H, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl, etc.; R^2d is C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl, etc.; R¹ is H, CN, C₁-C₁₀-alkyl, C₁-C₁₀-haloalkyl, C₃-C₁₀-cycloalkyl, etc.; R², R³ and R⁵ are H, halogen, CN, NO₂, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, etc., to a method for protecting plant propagation material and/or the plants which grow threfrom, to plant propagation material comprising at least one compound of formulae I or II, to a method for treating or protecting and animal from infestation or infection by parasites, to novel pyrazole compounds of formulae I or II and agricultural composition containing those compounds.

Claims

1-41. -41. (canceled)

42. A method for controlling invertebrate pests comprising treating the pests, their food supply, their habitat or their breeding ground or a plant, seed, soil, area, material or environment in which the pests are growing or may grow, or the materials, plants, seeds, soils, surfaces or spaces to be protected from pest attack or infestation with a pesticidally effective amount of a pyrazole compound of formulae I or II or a salt or an N-oxide thereof:

43. The method of claim 42, wherein the pyrazole compound is a compound of the formula I.

44. The method of claim 43, wherein X¹ in formula I is oxygen.

45. The method of claim 43, wherein R¹ is hydrogen, CN, C₁-C₁₀-alkyl, C₁-C₁₀-haloalkyl, C₂-C₁₀-alkenyl, C₂-C₁₀-haloalkenyl, C₂-C₁₀-alkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkylene-CN, OR^a, C(Y)R^b, C(Y)OR^c or S(O)₂R^d.

46. The method of claim 45, wherein R¹ is hydrogen or C₁-C₃-alkyl.

47. The method of claim 42, wherein R² is hydrogen, halogen, CN, NO₂, methyl, difluoromethyl, trifluoromethyl, methoxy, difluoromethoxy or trifluoromethoxy.

48. The method of claim 42, wherein R³ is hydrogen, halogen, CN, NO₂, methyl, difluoromethyl, trifluoromethyl, methoxy, difluoromethoxy or trifluoromethoxy.

49. The method of claim 42, wherein R⁵ is hydrogen, halogen, CN, NO₂, methyl, difluoromethyl, trifluoromethyl, methoxy, difluoromethoxy or trifluoromethoxy.

50. The method of claim 42, wherein B is CR⁴.

51. The method of claim 50, wherein R⁴ is hydrogen, methyl, difluoromethyl, trifluoromethyl, methoxy, difluoromethoxy or trifluoromethoxy.

52. The method of claim 50, wherein at least three of the radicals R², R³, R⁴ or R⁵ are hydrogen.

53. The method of claim 52, wherein the radicals R², R³, R⁴ and R⁵ are hydrogen.

54. The method of claim 42, wherein B is N.

55. The method of claim 54, wherein at least two of the radicals R², R³ or R⁵ are hydrogen.

56. The method of claim 55, wherein the radicals R², R³ and R⁵ are hydrogen.

57. The method of claim 42, wherein R^px is selected from the group consisting of halogen, CN, C₁-C₄-alkyl and C₂-C₁₀-alkenyl, wherein the 2 last mentioned radicals may be unsubstituted, may be partially or fully halogenated or may carry 1, 2 or 3 identical or different substituents selected from the group consisting of C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₃-C₆-cycloalkyl, hetaryl, phenyl and phenoxy, wherein the last three mentioned radicals may be unsubstituted or may carry 1, 2, 3, 4 or 5 radicals selected from the group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylsulfonyl and C₁-C₄-haloalkylsulfonyl, or wherein R^px is further selected from C₃-C₆-cycloalkyl, hetaryl and phenyl, wherein the three last mentioned radicals may be unsubstituted or may carry 1, 2, 3, 4 or 5 identical or different substituents selected from the group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylsulfonyl and C₁-C₄-haloalkylsulfonyl.

58. The method of claim 57, wherein R^px is selected from the group consisting of halogen, CN, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl and phenyl, wherein phenyl may be unsubstituted or may carry 1, 2, 3, 4 or 5 radicals selected from the group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy.

59. The method of claim 58, wherein R^px is selected from the group consisting of halogen, CN, C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl and C₃-C₆-halocycloalkyl.

60. The method of claim 42, wherein n is 0, 1 or 2.

61. The method of claim 60, wherein n is 0.

62. The method of claim 42, wherein the cyclic radical D is selected from the group consisting of fused pyridine, dihydropyridine, tetrahydropyridine, pyrazine, dihydropyrazine, tetrahydropyrazine, pyrimidine, dihydropyrimidine, tetrahydropyrimidine, pyridazine, dihydropyridazine and tetrahydropyridazine.

63. The method of claim 62, wherein the cyclic radical D together with the pyrazole forms a radical derived from pyrazolo[1,5-a]pyrazine, 4,5-dihydropyrazolo[1,5-a]pyrazine, 6,7-dihydropyrazolo[1,5-a]pyrazine, 4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine, pyrazolo[1,5-c]pyrimidine, 4,5-dihydropyrazolo[1,5-c]pyrimidine, 6,7-dihydropyrazolo[1,5-c]pyrimidine, 4,5,6,7-tetrahydropyrazolo[1,5-c]pyrimidine, pyrazolo[1,5-b]pyridazine, 4,5-dihydropyrazolo[1,5-b]pyridazine, 6,7-dihydropyrazolo[1,5-b]pyridazine or pyrazolo[1,5-b]tetrahydropyridazine.

64. The method of claim 42, wherein A is a radical A1.

65. The method of claim 64, wherein R^p1 is selected from the group consisting of hydrogen, halogen, CN, NO₂, C₁-C₄-alkyl and C₂-C₁₀-alkenyl, wherein the 2 last mentioned radicals may be unsubstituted, may be partially or fully halogenated or may carry 1, 2 or 3 identical or different substituents selected from the group consisting of C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₃-C₆-cycloalkyl, hetaryl, phenyl and phenoxy, wherein the last three mentioned radicals may be unsubstituted or may carry 1, 2, 3, 4 or 5 radicals selected from the group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylsulfonyl and C₁-C₄-haloalkylsulfonyl, or wherein R^p1 is further selected from the group consisting of C₃-C₆-cycloalkyl, hetaryl and phenyl, wherein the three last mentioned radicals may be unsubstituted or may carry 1, 2, 3, 4 or 5 identical or different substituents selected from the group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylsulfonyl and C₁-C₄-haloalkylsulfonyl.

66. The method of claim 65, wherein R^p1 is selected from the group consisting of hydrogen, halogen, CN, NO₂, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl and phenyl, wherein phenyl may be unsubstituted or may carry 1, 2, 3, 4 or 5 radicals selected from the group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy.

67. The method of claim 66, wherein R^p1 is selected from the group consisting of hydrogen, halogen, CN, NO₂, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl and C₃-C₆-halocycloalkyl.

68. The method of claim 67, wherein R^p1 is hydrogen.

69. The method of claim 42, wherein A is a radical A2.

70. The method of claim 69, wherein R^p2 is selected from the group consisting of hydrogen, halogen, CN, NO₂, C₁-C₄-alkyl and C₂-C₁₀-alkenyl, wherein the 2 last mentioned radicals may be unsubstituted, may be partially or fully halogenated or may carry 1, 2 or 3 identical or different substituents selected from the group consisting of C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₃-C₆-cycloalkyl, hetaryl, phenyl and phenoxy, wherein the last three mentioned radicals may be unsubstituted or may carry 1, 2, 3, 4 or 5 radicals selected from the group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylsulfonyl and C₁-C₄-haloalkylsulfonyl, or wherein R^p2 is further selected from the group consisting of C₃-C₆-cycloalkyl, hetaryl and phenyl, wherein the three last mentioned radicals may be unsubstituted or may carry 1, 2, 3, 4 or 5 identical or different substituents selected from the group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylsulfonyl and C₁-C₄-haloalkylsulfonyl.

71. The method of claim 70, wherein R^p2 is selected from the group consisting of hydrogen, halogen, CN, NO₂, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl and phenyl, wherein phenyl may be unsubstituted or may carry 1, 2, 3, 4 or 5 radicals selected from the group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy.

72. The method of claim 71, wherein R^p2 is selected from the group consisting of hydrogen, halogen, CN, NO₂, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl and C₃-C₆-halocycloalkyl.

73. The method of claim 72, wherein R^p2 is hydrogen.

74. The method of claim 42, wherein the invertebrate pests are arthropod pests and/or nematodes.

75. The method of claim 74, wherein the invertebrate pests are insects.

76. The method of claim 75, wherein the invertebrate pests are insects of the order Homoptera.

77. The method of claim 42, wherein the invertebrate pests are acaridae.

78. A method for protecting plant propagation material and/or the plants which grow therefrom, comprising treating the plant propagation material with a pesticidally effective amount of a compound of the formulae I or II or an agriculturally acceptable salt or an N-oxide thereof:

79. A plant propagation material treated with at least one compound of formulae I or II, and/or an agriculturally acceptable salt or an N-oxide thereof:

a pyrazole compound of formulae I or II or a salt or an N-oxide thereof;

80. A method for treating or protecting an animal from infestation or infection by parasites which comprises bringing the animal in contact with a parasiticidally effective amount of a compound of the formulae I or II or a veterinarily acceptable salt or an N-oxide thereof

a pyrazole compound of formulae I or II or a salt or an N-oxide thereof:

81. A pyrazole compound of formulae I or II or a salt or an N-oxide thereof:

82. An agricultural composition containing at least one compound of formulae I or II as defined in claim 81, and/or an agriculturally acceptable salt or N-oxide thereof and at least one liquid or solid carrier.