Heterocyclic compounds as pesticides

• US 8,686,004 B2
• Filed: 06/28/2011
• Issued: 04/01/2014
• Est. Priority Date: 06/28/2010
• Status: Expired due to Fees

• Current Assignee: Bayer Intellectual Property GmbH (Bayer AG)
• Original Assignee: Bayer Cropscience AG (Bayer AG)
• Inventors: Bretschneider, Thomas, Fischer, Reiner, Flein, Martin, Jeschke, Peter, Khler, Adeline, Kluth, Joachim, Mhlthau, Friedrich August, Sato, Yoshitaka, Voerste, Arnd, Shimojo, Eiichi
• Primary Examiner(s): RAO, DEEPAK R
• Application Number:
  US13/171,030
• Publication Number:
  US 20120165345A1
• Time in Patent Office: 1,008 Days
• Field of Search: 546/193, 546/256, 546/268.7, 546/269.7, 546/270.4, 514/318, 514/333, 514/341, 514/342
• US Class Current: 514/318
• CPC Class Codes: A01N 43/40 six-membered rings
• CPC Class Codes: A01N 43/54 1,3-Diazines; Hydrogenated 1,3-diazines
• CPC Class Codes: A01N 43/56 1,2-Diazoles; Hydrogenated 1,2-diazoles
• CPC Class Codes: A01N 43/58 1,2-Diazines; Hydrogenated 1,2-diazines
• CPC Class Codes: A01N 43/78 1,3-Thiazoles; Hydrogenated 1,3-thiazoles
• CPC Class Codes: A01N 43/82 five-membered rings with three ring hetero atoms
• CPC Class Codes: A61P 33/00 Antiparasitic agents
• CPC Class Codes: A61P 33/14 Ectoparasiticides, e.g. scabicides
• CPC Class Codes: C07D 401/14 containing three or more hetero rings
• CPC Class Codes: C07D 417/14 containing three or more hetero rings

Abstract

The present application relates to novel heterocyclic compounds, to the use thereof for controlling animal pests, which include arthropods and especially insects, and to processes for preparing the novel compounds.

Claims

1. A compound of the formula (I)

3. The compound according to claim 1, or a salt or N-oxide thereof,

in which

A¹ and A² are each independently hydrogen, halogen, cyano, nitro, C₁-C₆-alkyl, C₃-C₆-cycloalkyl or C₁-C₆-alkoxy,

R¹ is hydrogen, halogen, cyano, C₁-C₆-alkyl, C₁-C₆-alkoxy or C₁-C₆-haloalkyl,

R² is in each case hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, cyano-C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₂-C₆-alkenyl, C₂-C₆-alkynyl, or C₁-C₆-alkoxy-C₁-C₆-alkyl, in each case optionally halogen-substituted C₁-C₆-alkylcarbonyl or C₁-C₆-alkylsulphonyl, optionally halogen-substituted C₁-C₆-alkoxycarbonyl, in each case optionally halogen-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₆-haloalkyl- or cyano-substituted C₃-C₆-cycloalkylcarbonyl, or a mono or divalent metal ion, or an optionally C₁-C₆-alkyl- or aryl-C₁-C₆-alkyl-substituted ammonium ion,

R⁷ is in each case optionally halogen-, C₁-C₆-alkoxy-, C₁-C₆-haloalkoxy-, C₁-C₆-alkylthio-, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulphinyl-, C₁-C₆-haloalkylsulphinyl-, C₁-C₆-alkylsulphonyl- or C₁-C₆-haloalkylsulphonyl-substituted C₁-C₆-alkyl, C₂-C₆-alkenyl or C₂-C₆-alkynyl, in each case optionally halogen-, C₁-C₆-alkyl-, C₁-C₆-haloalkyl-, C₁-C₆-alkoxy- or C₁-C₆-haloalkoxy-substituted C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₆-alkyl or C₃-C₆-cycloalkenyl, in which the rings may contain at least one heteroatom selected from the group consisting of sulphur, oxygen (where oxygen atoms must not be immediately adjacent) and nitrogen, or is in each case a radical

4. The compound according to claim 1, or a salt or N-oxide thereof, in which

A¹ is hydrogen, halogen or cyano,

A² is hydrogen,

R¹ is hydrogen or C₁-C₄-alkyl,

X is oxygen,

n is 2,

R² is in each case hydrogen, C₁-C₄-alkyl, C₂-C₄-alkynyl, cyano-C₁-C₄alkyl or C₁-C₄-alkoxy-C₁-C₄-alkyl, optionally halogen-substituted C₁-C₄-alkylcarbonyl or C₁-C₄-alkylsulphonyl, in each case optionally halogen-substituted C₁-C₄-alkoxycarbonyl, optionally halogen-, C₁-C₄-alkyl-, C₁-C₄-haloalkyl- or cyano-substituted C₃-C₆-cycloalkylcarbonyl, or a mono- or divalent metal ion or an optionally C₁-C₄-alkyl- or aryl-C₁-C₄-alkyl-substituted ammonium ion,

R⁵ is in each case optionally halogen-, C₁-C₄-alkoxy-, C₁-C₄-haloalkoxy-, C₁-C₄-haloalkylthio-, C₁-C₄-alkylsulphinyl-, C₁-C₄-haloalkylsulphinyl-, C₁-C₄-alkylsulphonyl- or C₁-C₄-haloalkylsulphonyl-substituted C₁-C₄-alkyl, C₂-C₄-alkenyl or C₂-C₄-alkynyl, in each case optionally halogen-, C₁-C₄-alkyl-, C₁-C₄-haloalkyl-, C₁-C₄-alkoxy-, or C₁-C₄-haloalkoxy-substituted C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl or C₃-C₄-cycloalkenyl, in which the rings may contain at least one heteroatom selected from the group consisting of sulphur, oxygen (where oxygen atoms must not be immediately adjacent) and nitrogen, or

is in each case a radical

5. The compound according to claim 1, or a salt or N-oxide thereof,

in which

A¹ is hydrogen, fluorine or chlorine,

A² is hydrogen,

R¹ is hydrogen or methyl,

X is oxygen,

is 2,

R² is hydrogen, methyl, ethyl, CH₂OCH₃, CH₂OCH₂CH₃, COCH₃, COCH₂CH₃, CH₂CN, propynyl, cyclopropyl, Na⁺, K⁺ or ⁺N(CH₃)₄,

R⁵ is methyl, ethyl, i-propyl, CF₃, CHF₂, CH₂F, CH₂CF₃, cyclopropyl, dimethylammo, diethylamino, phenyl or benzyl, and

R⁷ is methyl, ethyl, i-propyl, CF₃, CHF₂, CH₂F, CH₂CF₃, cyclopropyl, dimethylamino, diethylamino, phenyl and benzyl.

6. The compound according to claim 1, or a salt or N-oxide thereof,

in which

A¹ is hydrogen, fluorine or chlorine,

A² is hydrogen,

R¹ is hydrogen or methyl, and

G³ and G⁴ form a bicycle group

8. A compound according to claim 1 which is:

9. A composition comprising at least one compound of the formula (I) or a salt or N-oxide thereof according to claims 1 or 2, and a carrier.

10. A method for controlling pests, comprising allowing at least one compound of formula (I) or a salt or N-oxide thereof according to claim 1 or 2, to act on the pests and/or their habitat.

11. A method for controlling pests, comprising allowing a composition according to claim 9, to act on the pests and/or their habitat.

2. A compound of formula (IA)

7. The compound according to claim 2, or a salt or N-oxide thereof,

in which

G¹ is C—

F,

R¹ is hydrogen, and

G⁴ is the radical (E),