Amides and thioamides as pesticides

• US 8,536,204 B2
• Filed: 10/12/2010
• Issued: 09/17/2013
• Est. Priority Date: 10/12/2009
• Status: Expired due to Fees

• Current Assignee: Bayer Intellectual Property GmbH (Bayer AG)
• Original Assignee: Bayer Cropscience AG (Bayer AG)
• Inventors: Bretschneider, Thomas, Voerste, Arnd, Grgens, Ulrich, Flein, Martin, Khler, Adeline
• Primary Examiner(s): Morris, Patricia L
• Application Number:
  US12/902,894
• Publication Number:
  US 20110118290A1
• Time in Patent Office: 1,071 Days
• Field of Search: 546/275.4, 546/276.1, 514/341
• US Class Current: 514/341
• CPC Class Codes: A61P 33/00 Antiparasitic agents
• CPC Class Codes: C07D 401/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 401/14 containing three or more hetero rings
• CPC Class Codes: C07D 407/14 containing three or more hetero rings
• CPC Class Codes: C07D 413/14 containing three or more hetero rings

Abstract

The present application relates to novel amides and thioamides, to processes for preparation thereof and to use thereof for controlling animal pests, in particular arthropods and especially insects.

Claims

1. A compound of the formula (I)

2. A composition, comprising at least one compound of the formula (I) according to claim 1 and one or more extenders, surfactants, and combinations thereof.

3. A method for controlling insects or arthropods, comprising contacting an effective amount of a compound of the formula (I) according to claim 1 with one or more insects or arthropods, their habitat, or combinations thereof.

4. The compound according to claim 1,

in which

G is CH, C-halogen, C-nitro, C-cyano, C—

C₁-C₄ alkyl, C—

C₁-C₄-haloalkyl, C—

C₃-C₆-cycloalkyl, C—

C₁-C₄-alkoxy, or C—

C₁-C₄-haloalkoxy,

R¹ is hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl, halogen, cyano, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, amino, C₁-C₄-alkylamino, di(C₁-C₄)-alkylamino or C₁-C₄-thioalkyl,

X is oxygen or sulphur,

R² is a radical selected from the group consisting of hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₂-C₃-alkenyl, C₁-C₂-alkoxy-C₁-C₂-alkyl, C₁-C₂-alkylcarbonyl, C₁-C₂-alkoxycarbonyl, and in each case optionally halogen-substituted cyclopropylcarbonyl, cyclopentylcarbonyl or cyclohexylcarbonyl,

R³ is a radical selected from the group consisting of hydrogen, C₁-C₄-alkyl, C₁-C₅-haloalkyl, cyano-C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, optionally halogen-substituted C₁-C₂-alkoxy-C₁-C₄-alkyl, optionally halogen-substituted bis(C₁-C₂-alkoxy)-C₁-C₄-alkyl, optionally halogen-substituted C₁-C₄-alkylthio-C₁-C₄-alkyl, optionally halogen-substituted C₁-C₄-alkylcarbonyl-C₁-C₄-alkyl, optionally halogen-substituted C₁-C₄-alkylsulphinyl-C₁-C₄-alkyl, optionally halogen-substituted C₁-C₄-alkylsulphonyl-C₁-C₄-alkyl, optionally halogen-substituted C₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl, C₁-C₄-alkoxycarbonylamino optionally C₁-C₄-alkyl-substituted on the nitrogen, C₂-C₄-alkynyloxy, C₂-C₄-alkynyloxycarbonyl, optionally halogen-, cyano-, C₁-C₄-alkyl-, C₁-C₄-haloalkyl-, C₁-C₄-alkoxy-, C₁-C₄-haloalkoxy-, C₁-C₄-alkoxycarbonyl-, or C₁-C₄-haloalkoxycarbonyl-substituted C₃-C₆-cycloalkyl, optionally halogen-, cyano-, C₁-C₄-alkyl-, C₁-C₄-haloalkyl-, C₁-C₄-alkoxy-, C₁-C₄-haloalkoxy-, C₁-C₄-alkoxycarbonyl-, or C₁-C₄-haloalkoxycarbonyl-substituted C₃-C₆-cycloalkylcarbonyl, optionally halogen-, cyano-, C₁-C₄-haloalkyl-, C₁-C₄-alkoxy-, C₁-C₄-haloalkoxy-, C₁-C₄-alkoxycarbonyl-, or C₁-C₄-haloalkoxycarbonyl-substituted C₃-C₆-cycloalkyl-C₄-C₄-alkyl, optionally halogen-, cyano-, C₁-C₄-alkyl-, C₁-C₄-haloalkyl-, C₁-C₄-alkoxy- or C₁-C₄-haloalkoxy-substituted aryl-C₁-C₄-alkyl, aryloxy-C₁-C₄-alkyl optionally halogen-substituted in the aryl moiety.

5. The compound according to claim 1,

in which

G is CH, C-halogen, C-cyano, C—

CH₃, C—

CF₃, C-cyclopropyl, C—

OCH₃, or C—

OCF₃,

R¹ is hydrogen, methyl, trifluoromethyl, cyclopropyl, halogen, cyano, methoxy, trifluoromethoxy, amino, methylamino, or dimethylamino,

X is oxygen or sulphur,

R² is a radical selected from the group consisting of hydrogen, methyl, ethyl, CH₂CF₃, CH₂CF₂CH₃, CH₂CHF₂, CH₂CF₂CHF₂, CH₂CH₂F, CH₂—

CHFCH₃, CH₂CF₂Br, CH₂CFCl₂, CH(CH₃)CH₂F, CH₂CCl₃, CH₂CClF₂, CH₂CH₂CH₂F, CH₂CH(CH₃)Cl, CHCF₃CH(CH₃)₂, CH(CF₃)₂, CH₂CH₂Cl, CHCF₃CH₂CH₂CH₃, CH₂CF₂CF₃, methoxy, ethoxy, vinyl, CH₂OCH₃, CH₂OCH₂CH₃, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, cyclopropylcarbonyl and fluorocyclopropylcarbonyl,

and

R³ is a radical selected from the group consisting of hydrogen, methyl, ethyl, CH₂CF₃, CH₂CH₂CF₃, CH₂CF₂CH₃, CH₂CHF₂, CH₂CF₂CHF₂, CH₂CH₂F, CH₂CHFCH₃, CH₂CF₂Br, CH₂CFCl₂, CH(CH₃)CH₂F, CH₂CCl₃, CH₂CClF₂, CH₂CH₂CH₂F, CH₂CH(CH₃)Cl, CHCF₃CH(CH₃)₂, CH(CF₃)₂, CH₂CH₂Cl, CHCF₃CH₂CH₂CH₃, CH₂CF₂CF₃, C(CH₃)₂CN, CH(CN)CH(CH₃)₂, CH₂CN, CH₂CH₂CN, vinyl, C(CH₃)₂CCH, CH₂CCCH₃, methoxy, ethoxy, CH₂CH(OCH₃)₂, CH₂CH(CH₃)(OCH₃), CH₂C(CH₃)₂(OCH₃), CH(CH₃)CH(OCH₃)₂, CH₂C(CH₃)(OCH₃)₂, C(CH₃)₂—

CH₂SCH₃, CH₂CH₂SCH₃, CHCH₃CH₂SCH₃, optionally halogen-substituted C₁-C₄-alkylcarbonyl-C₁-C₄-alkyl, CH₃SO₂CH₂C(CH₃)₂, CH₃SO₂CH₂CHCH₃, propargyloxy, cyclopropyl, cyanocyclopropyl, fluorocyclopropyl, trifluoromethylcyclopropyl, trifluoromethylcyclohexyl, methoxycarbonylcyclopropyl, fluorocyclopropylcarbonyl, cyclopropylmethyl, 1-cyclopropylethyl, cyclohexylmethyl, 1-cyano-1-cyclopropyleth-1-yl, optionally halogen-, cyano-, methyl-, ethyl-, methoxy- or ethoxy-substituted benzyl, methoxycarbonylethyl, methoxycarbonylamino, 4,6-dimethoxypyrimid-2-ylmethyl, 2-(2,5-dichlorophenoxy)ethyl and N-methyl-N-methoxycarbonyl-amino.