IP Library Granted Patent US 9,233,951
Granted Patent B2
US 9,233,951 · App. 13/183,709 · Granted Jan 12, 2016

Heterocyclic compounds as pesticides

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 9,233,951
App. No.
13/183,709
Granted
Jan 12, 2016
Kind
B2
Abstract

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

Claims (45)

1. A compound of the formula (I)

in which

G 1 is N or C-A 1 ,

A 1 is hydrogen, halogen, cyano, nitro, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 3 -haloalkyl or C 1 -C 6 -alkoxy,

A 2 is hydrogen, halogen, cyano, nitro, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl or C 1 -C 6 -alkoxy,

Q is

R 1 is hydrogen, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, halogen, cyano, C 1 -C 3 -haloalkyl, hydroxyl or C 1 -C 6 -alkoxy,

G 2 is C(=X)NR 3 R 4 ,

X is oxygen or sulphur,

R 3 is hydrogen, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -haloalkyl, cyano-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, optionally halogen-substituted C 1 -C 6 -alkylcarbonyl, optionally halogen-substituted C 1 -C 6 -alkoxycarbonyl, C 3 -C 6 -cycloalkylcarbonyl which is optionally substituted by halogen, C 1 -C 6 -alkyl, optionally halogen-substituted C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkyl or cyano; or a cation,

R 4 is cyano, C 1 -C 6 -alkyl which is optionally substituted by halogen, cyano, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -haloalkylsulphinyl, C 1 -C 6 -alkylsulphonyl or C 1 -C 6 haloalkylsulphonyl; C 2 -C 6 -alkenyl which is optionally substituted by halogen, cyano, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -haloalkylsulphinyl, C 1 -C 6 -alkylsulphonyl or C 1 -C 6 -haloalkylsulphonyl; C 2 -C 6 -alkynyl which is optionally substituted by halogen, cyano, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -haloalkylsulphinyl, C 1 -C 6 -alkylsulphonyl or C 1 -C 6 -haloalkylsulphonyl; C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, optionally halogen-substituted bis(C 1 -C6-alkoxy)-C 1 -C 6 -alkyl, optionally halogen-substituted bis(C 1 -C 6 -alkylthio)-C 1 -C 6 -alkyl, optionally halogen-substituted C 1 -C 6 -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 -alkylsulphonyl-C 1 -C 6 -alkyl, optionally halogen-substituted C 1 -C 6 -alkoxycarbonyl-C 1 -C 6 -alkyl, C 2 -C 4 -alkynyloxy, optionally halogen-substituted C 3 -C 6 -cycloalkylcarbonyl, optionally halogen-substituted C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl which is optionally substituted by halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy or C 1 -C 6 -haloalkoxy, wherein the cycloalkyl ring may contain one to three heteroatoms selected from the group consisting of sulphur, oxygen where oxygen atoms must not be immediately adjacent and nitrogen; C 3 -C 6 -cycloalkenyl which is optionally substituted by halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy or C 1 -C 6 -haloalkoxy, wherein the cycloalkenyl ring may contain one to three heteroatoms selected from the group consisting of sulphur, oxygen where oxygen atoms must not be immediately adjacent and nitrogen; aryl which is optionally substituted by halogen, cyano, nitro, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 C 6 -alkylsulphinyl, C 1 -C 6 -haloalkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 6 -haloalkylsulphonyl, amino, C 1 -C 6 -alkylamino, di(C 1 -C 6 -alkyl)amino, C 1 -C 6 -alkylcarbonylamino, C 1 -C 6 -alkoxycarbonylamino, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -haloalkoxy-C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl or aminocarbonyl; heteroaryl which is optionally substituted by halogen, cyano, nitro, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -haloalkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 6 -haloalkylsulphonyl, amino, C 1 -C 6 -alkylamino, di(C 1 -C 6 -alkyl)amino, C 1 -C 6 -alkylcarbonylamino, C 1 -C 6 -alkoxycarbonylamino, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -haloalkoxy-C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonyl or C 1 -C 6 -alkoxycarbonyl; heterocyclyl-C 1 -C 6 -alkyl which is optionally substituted by halogen, cyano, nitro, C 1 -C 6 alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -haloalkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 6 -haloalkylsulphonyl, amino, C 1 -C 6 -alkylamino, di(C 1 -C 6 -alkyl)amino, C 1 -C 6 -alkylcarbonylamino, C 1 -C 6 -alkoxycarbonylamino, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -haloalkoxy-C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl or aminocarbonyl; aryl-C 1 -C 6 -alkyl which is optionally substituted by halogen, cyano, nitro, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -haloalkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 6 -haloalkylsulphonyl, amino, C 1 -C 6 -alkylamino, di(C 1 -C 6 -alkyl)amino, C 1 -C 6 -alkylcarbonylamino, C 1 -C 6 -alkoxycarbonylamino, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -haloalkoxy-C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl or aminocarbonyl; heteroaryl-C 1 -C 6 -alkyl which is optionally substituted by halogen, cyano, nitro, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -haloalkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 6 -haloalkylsulphonyl, amino, C 1 -C 6 -alkylamino, di(C 1 -C 6 -alkyl)amino, C 1 -C 6 -alkylcarbonylamino, C 1 -C 6 -alkoxycarbonylamino, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -haloalkoxy-C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonyl or C 1 -C 6 -alkoxycarbonyl; or NR 5 R 6 in which R 5 and R 6 are each independently a radical from the group 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, C 1 -C 6 -alkoxylcarbonyl, hetaryl and heterocyclyl, or R 5 and R 6 together with the nitrogen atom to which they are bonded form an optionally halogen-substituted heterocycle, or

R 3 and R 4 may also, together with the nitrogen atom to which they are bonded, form a 3- to 7- membered ring which is optionally substituted by C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy or halogen, wherein said 3- to 7- membered ring optionally contains one or two heteroatoms selected from the group of oxygen, nitrogen and sulphur, where oxygen atoms must not be immediately adjacent.

2. The compound of formula (I) according to claim 1 , in which

G 1 is N or C-A 1 ;

A 1 is hydrogen, halogen, cyano, nitro, C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 3 -haloalkyl or C 1 -C 4 -alkoxy,

A 2 is hydrogen, halogen, cyano, nitro, C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl or C 1 -C 4 -alkoxy,

Q is

R 1 is hydrogen, C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, halogen, cyano, C 1 -C 3 -haloalkyl, hydroxyl or C 1 -C 4 -alkoxy,

G 2 is C(=X)NR 3 R 4 ,

X is oxygen or sulphur,

R 3 is hydrogen, C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -haloalkyl, cyano-C 1 -C 4 -alkyl, 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, C 3 -C 6 -cycloalkylcarbonyl which is optionally substituted by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl and cyano; or a cation,

R 4 is cyano, C 1 -C 4 -alkyl which is optionally substituted by halogen, cyano, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -haloalkylsulphinyl, C 1 -C 4 -alkylsulphonyl or C 1 -C 4 -haloalkylsulphonyl; C 2 -C 4 -alkenyl which is optionally substituted by halogen, cyano, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -haloalkylsulphinyl, C 1 -C 4 -alkylsulphonyl or C 1 -C 4 -haloalkylsulphonyl; C 2 -C 4 -alkynyl which is optionally substituted by halogen, cyano, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -haloalkylsulphinyl, C 1 -C 4 -alkylsulphonyl or C 1 -C 4 -haloalkylsulphonyl; C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, optionally halogen-substituted bis(C 1 -C 4 -alkoxy)-C 1 -C 4 -alkyl, optionally halogen-substituted bis(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 2 -C 4 -alkynyloxy, optionally halogen-substituted C 3 -C 6 -cycloalkylcarbonyl, optionally halogen-substituted C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl which is optionally substituted with halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy, wherein the cycloalkyl ring may contain one to three heteroatoms selected from the group consisting of sulphur, oxygen where oxygen atoms must not be immediately adjacent and nitrogen; C 3 -C 6 -cycloalkenyl which is optionally substituted with halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy, wherein the cycloalkenyl ring may contain one to three heteroatoms selected from the group consisting of sulphur, oxygen where oxygen atoms must not be immediately adjacent and nitrogen; aryl which is optionally substituted by halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -haloalkylsulphinyl, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -haloalkylsulphonyl, amino, C 1 -C 4 -alkylamino, di(C 1 -C 4 -alkyl)amino, C 1 -C 4 -alkylcarbonylamino, C 1 -C 4 -alkoxycarbonylamino, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -haloalkoxy-C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl or aminocarbonyl; heteroaryl which is optionally substituted by halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -haloalkylsulphinyl, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -haloalkylsulphonyl, amino, C 1 -C 4 -alkylamino, di(C 1 -C 4 -alkyl)amino, C 1 -C 4 -alkylcarbonylamino, C 1 -C 4 -alkoxycarbonylamino, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -haloalkoxy-C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkylcarbonyl or C 1 -C 4 -alkoxycarbonyl; heterocyclyl-C 1 -C 4 -alkyl which is optionally substituted by halogen, cyano, nitro, C 1 -C 4 -alkyl-, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -haloalkylsulphinyl, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -haloalkylsulphonyl, amino, C 1 -C 4 -alkylamino, di(C 1 -C 4 -alkyl)amino, C 1 -C 4 -alkylcarbonylamino, C 1 -C 4 -alkoxycarbonylamino, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -haloalkoxy-C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl or aminocarbonyl; aryl-C 1 -C 4 -alkyl which is optionally substituted by halogen, cyano, nitro, C 1 -C 4 -alkyl-, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -haloalkylsulphinyl, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -haloalkylsulphonyl, amino, C 1 -C 4 -alkylamino, di(C 1 -C 4 -alkyl)amino, C 1 -C 4 -alkylcarbonylamino, C 1 -C 4 -alkoxycarbonylamino, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -haloalkoxy-C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl or aminocarbonyl; heteroaryl-C 1 -C 4 -alkyl which is optionally substituted by halogen, cyano, nitro, C 1 -C 4 -alkyl-,C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -haloalkylsulphinyl, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -haloalkylsulphonyl, amino, C 1 -C 4 -alkylamino, di(C 1 -C 4 -alkyl)amino, C 1 -C 4 -alkylcarbonylamino, C 1 -C 4 -alkoxycarbonylamino, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -haloalkoxy-C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkylcarbonyl or C 1 -C 4 -alkoxycarbonyl; or NR 5 R 6 in which R 5 and R 6 are each independently a radical from the group of hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxylcarbonyl, hetaryl and heterocyclyl, or R 5 and R 6 together with the nitrogen atom to which they are bonded form an optionally halogen-substituted heterocycle, or

R 3 and R 4 may also, together with the nitrogen atom to which they are bonded, form a 3-to 7-membered ring which is optionally substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or halogen; wherein the 3-to 7-membered ring optionally contains one or two heteroatoms selected from the group of oxygen, nitrogen and sulphur, where oxygen atoms must not be immediately adjacent.

3. The compound of formula (I) according to claim 1 , in which

G 1 is C-A 1 ,

A 1 is hydrogen,

A 2 is hydrogen,

Q is

R 1 is hydrogen or C 1 -C 4 -alkyl,

G 2 is C(=X)NR 3 R 4 ,

X is oxygen,

R 3 is hydrogen or C 1 -C 4 -alkyl,

R 4 is C 1 -C 4 -alkyl which is optionally substituted by halogen, cyano or C 1 -C 4 -alkylthio; C 2 -C 4 -alkenyl which is optionally substituted by halogen, cyano or C 1 -C 4 -alkylthio; C 2 -C 4 -alkynyl which is optionally substituted by halogen, cyano or C 1 -C 4 -alkylthio; optionally halogen-substituted C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl and optionally C 1 -C 4 -haloalkyl-substituted heteroaryl-C 1 -C 4 -alkyl, or

R 3 and R 4 may also, together with the nitrogen atom to which they are bonded, form a 3-to 7-membered ring which does not contain any further heteroatoms.

4. The compound of formula (I) according to claim 1 having the formula:

5. The compound of claim 1 , wherein said cation is a mono- or divalent metal ion or a quaternary ammonium group optionally substituted with C 1 -C 4 -alkyl or aryl-C 1 -C 4 -alkyl substituents.

6. The compound of claim 2 , wherein said cation is a mono- or divalent metal ion or a quaternary ammonium group optionally substituted with C 1 -C 4 -alkyl or aryl-C 1 -C 4 -alkyl substituents.

7. The compound of claim 1 wherein R 4 is C 1 -C 6 alkyl substituted by halogen, cyano, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -haloalkylsulphinyl, C 1 -C 6 -alkylsulphonyl or C 1 -C 6 -haloalkylsulphonyl.

8. The compound of claim 1 , wherein R 3 and R 4 are C 1 -C 6 -alkyl.

9. The compound of claim 1 , wherein R 4 is C 1 -C 6 -alkyl substituted by halogen.

10. The compound of claim 1 , wherein R 4 is C 1 -C 6 -alkyl substituted by cyano.

11. The compound of claim 1 , wherein R 3 and R 4 together with the nitrogen atom to which they are bonded form a 3-to 7-membered ring.

12. The compound of claim 1 , wherein R 4 is C 2 -C 6 -alkenyl substituted by halogen.

13. The compound of claim 1 selected from the group consisting of

14. The compound of claim 1 , wherein R 3 is a cation.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 27, 2015
From: BAYER CROPSCIENCE AG
To: BAYER INTELLECTUAL PROPERTY GMBH
Reel/Frame 035051/0545 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 5, 2012
From: MUHLTHAU, FRIEDRICH AUGUST; BRETSCHNEIDER, THOMAS; FISCHER, REINER; FUSSLEIN, MARTIN; HEIL, MARKUS; HENSE, ACHIM; KLUTH, JOACHIM; KOHLER, ADELINE; FRANKEN, EVA-MARIA; MALSAM, OLGA; VOERSTE, ARND; JESCHKE, PETER; BECKER, ANGELA; LOSEL, PETER; SATO, YOSHITAKA
To: BAYER CROPSCIENCE AG
Reel/Frame 027481/0208 →