IP Library Granted Patent US 8,536,204
Granted Patent B2
US 8,536,204 · App. 12/902,894 · Granted Sep 17, 2013

Amides and thioamides as pesticides

Inventors: Thomas Bretschneider (Lohmar, DE); Arnd Voerste (Köln, DE); Martin Füβlein (Düsseldorf, DE); Adeline Köhler (Wuppertal, DE); Ulrich Görgens (Ratingen, DE)
Assignee: Bayer CropScience AG
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Quick Facts
Patent No.
US 8,536,204
App. No.
12/902,894
Granted
Sep 17, 2013
Kind
B2
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 (27)

1. A compound of the formula (I)

in which

G is CH, C-halogen, C-nitro, C-cyano, C—C 1 -C 6 -haloalkyl, C—C 3 -C 6 -cycloalkyl, C—C 1 -C 6 -alkoxy, or C—C 1 -C 6 -haloalkoxy,

R 1 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, halogen, cyano, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, amino, C 1 -C 6 -alkylamino, di(C 1 -C 6 )-alkylamino or C 1 -C 6 -thioalkyl,

X is oxygen or sulphur,

R 2 is a radical selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 2 -C 4 -alkenyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, optionally halogen-substituted C 1 -C 4 -alkylcarbonyl, optionally halogen-substituted C 1 -C 4 -alkoxycarbonyl and optionally halogen-substituted C 3 -C 6 -cycloalkylcarbonyl,

and

R 3 is a radical selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, cyano-C 1 -C 6 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 2 -C 4 -haloalkynyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, optionally halogen-substituted C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, optionally halogen-substituted bis(C 1 -C 6 -alkoxy)-C 1 -C 6 -alkyl, optionally halogen-substituted C 1 -C 6 -alkylthio-C 1 -C 6 -alkyl, optionally halogen-substituted C 1 -C 4 -alkylcarbonyl-C 1 -C 6 -alkyl, optionally halogen-substituted C 1 -C 6 -alkylsulphinyl-C 1 -C 6 -alkyl, optionally halogen-substituted C 1 -C 6 -alkyl sulphonyl-C 1 -C 6 -alkyl, optionally halogen-substituted C 1 -C 6 -alkoxycarbonyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonylamino optionally C 1 -C 6 -alkyl-substituted on the nitrogen, C 2 -C 4 -alkynyloxy, C 2 -C 4 -alkynyloxycarbonyl, optionally halogen-, cyano-, C 1 -C 6 -alkyl-, C 1 -C 6 -haloalkyl-, C 1 -C 6 -alkoxy-, C 1 -C 6 -haloalkoxy-, C 1 -C 6 -alkoxycarbonyl-, or C 1 -C 6 -haloalkoxycarbonyl-substituted C 3 -C 6 -cycloalkyl, optionally halogen-, cyano-, C 1 -C 6 -alkyl-, C 1 -C 6 -haloalkyl-, C 1 -C 6 -alkoxy-, C 1 -C 6 -haloalkoxy-, C 1 -C 6 -alkoxycarbonyl-, or C 1 -C 6 -haloalkoxycarbonyl-substituted C 3 -C 6 -cycloalkylcarbonyl, optionally halogen-, cyano-, C 1 -C 6 -alkyl-, C 1 -C 6 -haloalkyl-, C 1 -C 6 -alkoxy-, C 1 -C 6 -haloalkoxy-, C 1 -C 6 -alkoxycarbonyl-, or C 1 -C 6 -haloalkoxycarbonyl-substituted C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, optionally halogen-, cyano-, C 1 -C 6 -alkyl-, C 1 -C 6 -alkoxy- or C 1 -C 6 -haloalkoxy-substituted aryl-C 1 -C 6 -alkyl, optionally in the aryl moiety, halogen-substituted aryloxy-C 1 -C 6 -alkyl, and NR 4 R 5 in which R 4 and R 5 are each independently a radical selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl and C 1 -C 6 -alkoxycarbonyl,

and

a salt and a N-oxide of the 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—C 1 -C 4 alkyl, C—C 1 -C 4 -haloalkyl, C—C 3 -C 6 -cycloalkyl, C—C 1 -C 4 -alkoxy, or C—C 1 -C 4 -haloalkoxy,

R 1 is hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, halogen, cyano, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, amino, C 1 -C 4 -alkylamino, di(C 1 -C 4 )-alkylamino or C 1 -C 4 -thioalkyl,

X is oxygen or sulphur,

R 2 is a radical selected from the group consisting of hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 2 -C 3 -alkenyl, C 1 -C 2 -alkoxy-C 1 -C 2 -alkyl, C 1 -C 2 -alkylcarbonyl, C 1 -C 2 -alkoxycarbonyl, and in each case optionally halogen-substituted cyclopropylcarbonyl, cyclopentylcarbonyl or cyclohexylcarbonyl,

R 3 is a radical selected from the group consisting of hydrogen, C 1 -C 4 -alkyl, C 1 -C 5 -haloalkyl, cyano-C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 2 -C 4 -haloalkynyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, optionally halogen-substituted C 1 -C 2 -alkoxy-C 1 -C 4 -alkyl, optionally halogen-substituted bis(C 1 -C 2 -alkoxy)-C 1 -C 4 -alkyl, optionally halogen-substituted C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, optionally halogen-substituted C 1 -C 4 -alkylcarbonyl-C 1 -C 4 -alkyl, optionally halogen-substituted C 1 -C 4 -alkylsulphinyl-C 1 -C 4 -alkyl, optionally halogen-substituted C 1 -C 4 -alkylsulphonyl-C 1 -C 4 -alkyl, optionally halogen-substituted C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonylamino optionally C 1 -C 4 -alkyl-substituted on the nitrogen, C 2 -C 4 -alkynyloxy, C 2 -C 4 -alkynyloxycarbonyl, optionally halogen-, cyano-, C 1 -C 4 -alkyl-, C 1 -C 4 -haloalkyl-, C 1 -C 4 -alkoxy-, C 1 -C 4 -haloalkoxy-, C 1 -C 4 -alkoxycarbonyl-, or C 1 -C 4 -haloalkoxycarbonyl-substituted C 3 -C 6 -cycloalkyl, optionally halogen-, cyano-, C 1 -C 4 -alkyl-, C 1 -C 4 -haloalkyl-, C 1 -C 4 -alkoxy-, C 1 -C 4 -haloalkoxy-, C 1 -C 4 -alkoxycarbonyl-, or C 1 -C 4 -haloalkoxycarbonyl-substituted C 3 -C 6 -cycloalkylcarbonyl, optionally halogen-, cyano-, C 1 -C 4 -haloalkyl-, C 1 -C 4 -alkoxy-, C 1 -C 4 -haloalkoxy-, C 1 -C 4 -alkoxycarbonyl-, or C 1 -C 4 -haloalkoxycarbonyl-substituted C 3 -C 6 -cycloalkyl-C 4 -C 4 -alkyl, optionally halogen-, cyano-, C 1 -C 4 -alkyl-, C 1 -C 4 -haloalkyl-, C 1 -C 4 -alkoxy- or C 1 -C 4 -haloalkoxy-substituted aryl-C 1 -C 4 -alkyl, aryloxy-C 1 -C 4 -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—CH 3 , C—CF 3 , C-cyclopropyl, C—OCH 3 , or C—OCF 3 ,

R 1 is hydrogen, methyl, trifluoromethyl, cyclopropyl, halogen, cyano, methoxy, trifluoromethoxy, amino, methylamino, or dimethylamino,

X is oxygen or sulphur,

R 2 is a radical selected from the group consisting of hydrogen, methyl, ethyl, CH 2 CF 3 , CH 2 CF 2 CH 3 , CH 2 CHF 2 , CH 2 CF 2 CHF 2 , CH 2 CH 2 F, CH 2 —CHFCH 3 , CH 2 CF 2 Br, CH 2 CFCl 2 , CH(CH 3 )CH 2 F, CH 2 CCl 3 , CH 2 CClF 2 , CH 2 CH 2 CH 2 F, CH 2 CH(CH 3 )Cl, CHCF 3 CH(CH 3 ) 2 , CH(CF 3 ) 2 , CH 2 CH 2 Cl, CHCF 3 CH 2 CH 2 CH 3 , CH 2 CF 2 CF 3 , methoxy, ethoxy, vinyl, CH 2 OCH 3 , CH 2 OCH 2 CH 3 , methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, cyclopropylcarbonyl and fluorocyclopropylcarbonyl,

and

R 3 is a radical selected from the group consisting of hydrogen, methyl, ethyl, CH 2 CF 3 , CH 2 CH 2 CF 3 , CH 2 CF 2 CH 3 , CH 2 CHF 2 , CH 2 CF 2 CHF 2 , CH 2 CH 2 F, CH 2 CHFCH 3 , CH 2 CF 2 Br, CH 2 CFCl 2 , CH(CH 3 )CH 2 F, CH 2 CCl 3 , CH 2 CClF 2 , CH 2 CH 2 CH 2 F, CH 2 CH(CH 3 )Cl, CHCF 3 CH(CH 3 ) 2 , CH(CF 3 ) 2 , CH 2 CH 2 Cl, CHCF 3 CH 2 CH 2 CH 3 , CH 2 CF 2 CF 3 , C(CH 3 ) 2 CN, CH(CN)CH(CH 3 ) 2 , CH 2 CN, CH 2 CH 2 CN, vinyl, C(CH 3 ) 2 CCH, CH 2 CCCH 3 , methoxy, ethoxy, CH 2 CH(OCH 3 ) 2 , CH 2 CH(CH 3 )(OCH 3 ), CH 2 C(CH 3 ) 2 (OCH 3 ), CH(CH 3 )CH(OCH 3 ) 2 , CH 2 C(CH 3 )(OCH 3 ) 2 , C(CH 3 ) 2 —CH 2 SCH 3 , CH 2 CH 2 SCH 3 , CHCH 3 CH 2 SCH 3 , optionally halogen-substituted C 1 -C 4 -alkylcarbonyl-C 1 -C 4 -alkyl, CH 3 SO 2 CH 2 C(CH 3 ) 2 , CH 3 SO 2 CH 2 CHCH 3 , 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.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 23, 2015
From: BAYER CROPSCIENCE AG
To: BAYER INTELLECTUAL PROPERTY GMBH
Reel/Frame 035009/0531 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 7, 2011
From: BRETSCHNEIDER, THOMAS; VOERSTE, ARND; FUSSLEIN, MARTIN; KOHLER, ADELINE; GORGENS, ULRICH
To: BAYER CROPSCIENCE AG
Reel/Frame 025601/0810 →
Priority Claims (1)
EP 09172736 · Oct 12, 2009 · regional
Continuity (2)
Provisional Application 61251042 · Oct 13, 2009
Related Publication 20110118290A1 · May 19, 2011