Use of substituted isoquinolinones, isoquinolindiones, isoquinolintriones and dihydroisoquinolinones or in each case salts thereof as active agents against abiotic stress in plants

Patent metadata

Field	Value
Publication number	US-9173395-B2
Application number	US-201214130640-A
Country	US
Kind code	B2
Filing date	Jul 2, 2012
Priority date	Jul 4, 2011
Publication date	Nov 3, 2015
Grant date	Nov 3, 2015

Abstract

Use of substituted isoquinolinones, isoquinolinediones, isoquinolinetriones and dihydroisoquinolinones of the general formula (I) or their respective salts

where the radicals in the general formula (I) correspond to the definitions given in the description,
for enhancing stress tolerance in plants to abiotic stress, for strengthening plant growth and/or for increasing plant yield, and selected processes for preparing the compounds mentioned above.

First claim

The invention claimed is:

1. A substituted isoquinolinone of formula (I) and/or a respective salt thereof

capable of being used for increasing tolerance to abiotic stress in a plant, where
Q represents

where the arrow represents a bond to the group N—R 5 ,

W represents oxygen or sulphur,
R 1 , R 2 , and R 3 independently of one another represent hydrogen, nitro, amino, hydroxyl, cyano, alkyl, cycloalkyl, alkenyl, alkynyl, optionally halogen-, alkyl-, alkoxy-, or haloalkyl-substituted phenyl, arylalkyl, heteroaryl, cycloalkylalkyl, haloalkyl, alkoxyalkyl, alkoxy, haloalkoxy, cycloalkyloxy, arylalkoxy, alkoxycarbonyl, alkylthio, haloalkylthio, aryloxy, or aminoalkyl,
R 4 represents hydrogen, nitro, amino, hydroxyl, cyano, alkyl, cycloalkyl, alkenyl, alkynyl, arylalkyl, cycloalkylalkyl, haloalkyl, alkoxyalkyl, alkoxy, haloalkoxy, cycloalkyloxy, arylalkoxy, alkoxycarbonyl, alkylthio, haloalkylthio, heterocyclyl-N-alkoxy, aryloxy, or aminoalkyl,
R 5 represents hydrogen, hydroxyl, alkyl, cycloalkyl, halogen, haloalkyl, alkoxyalkyl, alkynyl, alkenyl, cycloalkylalkyl, cyanoalkyl, arylalkyl, heteroarylalkyl, aryl, alkylcarbonyl, cycloalkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, alkylsulphonyl, arylsulphonyl, or a negative charge,
R 6 represents hydrogen, hydroxyl, halogen, amino, alkyl, cycloalkyl, alkylcarbonyl, arylcarbonyl, alkylaminocarbonyl, bisalkylaminocarbonyl, cycloalkylaminocarbonyl, arylaminocarbonyl, cyanoalkylaminocarbonyl, hydroxycarbonyl, alkoxycarbonyl, cycloalkyloxycarbonyl, cycloalkylalkoxycarbonyl, haloalkoxycarbonyl, arylaminocarbonylamino, alkylaminocarbonylamino, heteroarylaminocarbonylamino, alkoxy, alkylcarbonyloxy, arylcarbonyloxy, haloalkyl, alkoxyalkyl, alkynyl, alkenyl, aryl, heteroaryl, heterocyclyl, alkylamino, bisalkylamino, cycloalkylamino, or arylalkylamino, and
R 7 represents hydrogen, halogen, amino, alkyl, haloalkyl, cycloalkyl, alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, cycloalkylcarbonyl, alkoxycarbonyl, hydroxycarbonyl, cycloalkylalkoxycarbonyl, alkylcarbonyloxy, arylaminocarbonyl, alkylaminocarbonyl, bisalkylaminocarbonyl, cycloalkylaminocarbonyl, cyanoalkylaminocarbonyl, alkylamino, arylamino, cycloalkylamino, or bisalkylamino.

2. A substituted isoquinolinone of formula (I) and/or a respective salt thereof, according to claim 1 , where, in formula (I),
Q represents

where the arrow represents a bond to the group N—R 5 ,

W represents oxygen or sulphur,
R 1 , R 2 , and R 3 are each independently hydrogen, nitro, amino, hydroxyl, cyano, (C 1 -C 8 )-alkyl, (C 3 -C 8 )-cycloalkyl, (C 2 -C 8 )-alkenyl, (C 2 -C 8 )-alkynyl, optionally halogen-, (C 1 -C 8 )-alkyl-, (C 1 -C 8 )-alkoxy-, or (C 1 -C 7 )-haloalkyl-substituted phenyl, aryl-(C 1 -C 8 )-alkyl, heteroaryl, (C 3 -C 8 )-cycloalkyl-(C 1 -C 8 )-alkyl, (C 1 -C 8 )-haloalkyl, (C 1 -C 8 )-alkoxy-(C 1 -C 8 )-alkyl, (C 1 -C 8 )-alkoxy, (C 1 -C 8 )-haloalkoxy, (C 3 -C 8 )-cycloalkyloxy, aryl-(C 1 -C 8 )-alkoxy, (C 1 -C 8 )-alkoxycarbonyl, (C 1 -C 8 )-alkylthio, (C 1 -C 8 )-haloalkylthio, aryloxy, or amino-(C 1 -C 8 )-alkyl,
R 4 represents hydrogen, nitro, amino, hydroxyl, cyano, (C 1 -C 8 )-alkyl, (C 3 -C 8 )-cycloalkyl, (C 2 -C 8 )-alkenyl, (C 2 -C 8 )-alkynyl, aryl-(C 1 -C 8 )-alkyl, (C 3 -C 8 )-cycloalkyl-(C 1 -C 8 )-alkyl, (C 1 -C 8 )-haloalkyl, (C 1 -C 8 )-alkoxy-(C 1 -C 8 )-alkyl, (C 1 -C 8 )-alkoxy, (C 1 -C 8 )-haloalkoxy, (C 3 -C 8 )-cycloalkyloxy, aryl-(C 1 -C 8 )-alkoxy, (C 1 -C 8 )-alkoxycarbonyl, (C 1 -C 8 )-alkylthio, (C 1 -C 8 )-haloalkylthio, heterocyclyl-N-alkoxy, aryloxy, or amino-(C 1 -C 8 )-alkyl,
R 5 represents hydrogen, hydroxy, (C 1 -C 8 )-alkyl, (C 3 -C 8 )-cycloalkyl, halogen, (C 1 -C 8 )-haloalkyl, (C 1 -C 8 )-alkoxy-(C 1 -C 8 )-alkyl, (C 2 -C 8 )-alkynyl, (C 2 -C 8 )-alkenyl, (C 3 -C 8 )-cycloalkyl-(C 1 -C 8 )-alkyl, cyano-(C 1 -C 8 )-alkyl, aryl-(C 1 -C 8 )-alkyl, heteroaryl-(C 1 -C 8 )-alkyl, aryl, (C 1 -C 8 )-alkylcarbonyl, (C 3 -C 8 )-cycloalkylcarbonyl, (C 1 -C 8 )-haloalkylcarbonyl, (C 1 -C 8 )-alkoxycarbonyl, (C 1 -C 8 )-alkylsulphonyl, arylsulphonyl, or a negative charge,
R 6 represents hydrogen, hydroxy, nitro, halogen, amino, (C 1 -C 8 )-alkyl, (C 3 -C 8 )-cycloalkyl, (C 1 -C 8 )-alkylcarbonyl, arylcarbonyl, (C 1 -C 8 )-alkylaminocarbonyl, bis-(C 1 -C 8 )-alkylaminocarbonyl, (C 3 -C 8 )-cycloalkylaminocarbonyl, arylaminocarbonyl, cyano-(C 1 -C 8 )-alkylaminocarbonyl, (C 1 -C 8 )-alkoxycarbonylamino, hydroxycarbonyl, (C 1 -C 8 )-alkoxycarbonyl, (C 1 -C 8 )-cycloalkoxycarbonyl, (C 1 -C 8 )-cycloalkyl-(C 1 -C 8 )-alkoxycarbonyl, (C 1 -C 8 )-haloalkoxycarbonyl, arylaminocarbonylamino, (C 1 -C 8 )-alkylaminocarbonylamino, heteroarylaminocarbonylamino, (C 1 -C 8 )-alkoxy, (C 1 -C 8 )-alkylcarbonyloxy, arylcarbonyloxy, (C 1 -C 8 )-haloalkyl, (C 1 -C 8 )-alkoxy-(C 1 -C 8 )-alkyl, (C 2 -C 8 )-alkynyl, (C 2 -C 8 )-alkenyl, aryl, heteroaryl, (C 1 -C 8 )-alkylamino, bis-(C 1 -C 8 )-alkylamino, (C 3 -C 8 )-cycloalkylamino, or aryl-(C 1 -C 8 )-alkylamino, and
R 7 represents hydrogen, halogen, amino, (C 1 -C 8 )-alkyl, (C 1 -C 8 )-haloalkyl, (C 3 -C 8 )-cycloalkyl, (C 1 -C 8 )-alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, (C 3 -C 8 )-cycloalkylcarbonyl, (C 1 -C 8 )-alkoxycarbonyl, hydroxycarbonyl, (C 3 -C 8 )-cycloalkyl-(C 1 -C 8 )-alkoxycarbonyl, (C 1 -C 8 )-alkylcarbonyloxy, arylaminocarbonyl, (C 1 -C 8 )-alkylaminocarbonyl, bis-(C 1 -C 8 )-alkylaminocarbonyl, (C 3 -C 8 )-cycloalkylaminocarbonyl, cyano-(C 1 -C 8 )-alkylaminocarbonyl, (C 1 -C 8 )-alkylamino, arylamino, (C 3 -C 8 )-cycloalkylamino, or bis-(C 1 -C 8 )-alkylamino.

3. A substituted isoquinolinone of formula (I) and/or a respective salt thereof according to claim 1 , where, in formula (I),
Q represents

where the arrow represents a bond to the group N—R 5 ,

W represents oxygen or sulphur,
R 1 , R 2 , and R 3 are each independently hydrogen, nitro, amino, hydroxyl, cyano, (C 1 -C 7 )-alkyl, (C 3 -C 7 )-cycloalkyl, (C 2 -C 7 )-alkenyl, (C 2 -C 7 )-alkynyl, optionally halogen-, (C 1 -C 8 )-alkyl-, (C 1 -C 8 )-alkoxy-, or (C 1 -C 7 )-haloalkyl-substituted phenyl, aryl-(C 1 -C 7 )-alkyl, (C 3 -C 7 )-cycloalkyl-(C 1 -C 7 )-alkyl, (C 1 -C 7 )-haloalkyl, (C 1 -C 7 )-alkoxy-(C 1 -C 7 )-alkyl, (C 1 -C 7 )-alkoxy, (C 1 -C 7 )-haloalkoxy, (C 3 -C 7 )-cycloalkyloxy, aryl-(C 1 -C 7 )-alkoxy, (C 1 -C 7 )-alkoxycarbonyl, (C 1 -C 7 )-alkylthio, (C 1 -C 7 )-haloalkylthio, or amino-(C 1 -C 7 )-alkyl,
R 4 represents hydrogen, nitro, amino, hydroxyl, cyano, (C 1 -C 8 )-alkyl, (C 3 -C 8 )-cycloalkyl, (C 2 -C 8 )-alkenyl, (C 2 -C 8 )-alkynyl, aryl-(C 1 -C 8 )-alkyl, (C 3 -C 8 )-cycloalkyl-(C 1 -C 8 )-alkyl, (C 1 -C 8 )-haloalkyl, (C 1 -C 8 )-alkoxy-(C 1 -C 8 )-alkyl, (C 1 -C 8 )-alkoxy, (C 1 -C 8 )-haloalkoxy, (C 3 -C 8 )-cycloalkyloxy, aryl-(C 1 -C 8 )-alkoxy, (C 1 -C 8 )-alkoxycarbonyl, (C 1 -C 8 )-alkylthio, (C 1 -C 8 )-haloalkylthio, heterocyclyl-N-alkoxy, aryloxy, or amino-(C 1 -C 8 )-alkyl,
R 5 represents hydrogen, hydroxy, (C 1 -C 7 )-alkyl, (C 3 -C 7 )-cycloalkyl, halogen, (C 1 -C 7 )-haloalkyl, (C 1 -C 7 )-alkoxy-(C 1 -C 7 )-alkyl, (C 2 -C 7 )-alkynyl, (C 2 -C 7 )-alkenyl, (C 3 -C 7 )-cycloalkyl-(C 1 -C 7 )-alkyl, cyano-(C 1 -C 7 )-alkyl, aryl-(C 1 -C 7 )-alkyl, heteroaryl-(C 1 -C 7 )-alkyl, optionally substituted phenyl, (C 1 -C 7 )-alkylcarbonyl, (C 3 -C 7

Assignees

• Frackenpohl Jens
• Zeiss I Hans-Joachim
• Heinemann Ines
• Willms Lothar
• Mueller Thomas
• Busch Marco
• Von Koskull-Doering Pascal
• Rosinger Christopher Hugh
• Dittgen Jan
• Hills Martin Jeffrey
• Bayer Ip Gmbh

Inventors

• Frackenpohl Jens
• Zeiss I Hans-Joachim
• Heinemann Ines
• Willms Lothar
• Mueller Thomas
• Busch Marco
• Von Koskull-Doering Pascal
• Rosinger Christopher Hugh
• Dittgen Jan
• Hills Martin Jeffrey

Classifications

• A01N43/42 Primary

  condensed with carbocyclic rings · CPC title

• A01N43/90 Primary

  having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system · CPC title

• A01N43/38

  condensed with carbocyclic rings · CPC title