Use of substituted dihydrooxindolylsulfonamides, or the salts thereof, for increasing the stress tolerance of plants

Patent metadata

Field	Value
Publication number	US-10065926-B2
Application number	US-201415025104-A
Country	US
Kind code	B2
Filing date	Oct 2, 2014
Priority date	Oct 4, 2013
Publication date	Sep 4, 2018
Grant date	Sep 4, 2018

Abstract

The invention relates to the use of substituted dihydrooxindolylsulfonamides or salts thereof of the formula (I)

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, and/or for increasing plant yield.

First claim

The invention claimed is:

1. A method for treating a plant to increase the plants resistance to an abiotic stress factor, comprising applying to the plant or an area where the plant grows, or to a seed of the plant, or to part of the plant, a nontoxic amount, effective for increasing the resistance of the plant to an abiotic stress factor of one or more compounds of formulae (Ia) to (Iz) or (Iab), or salt thereof

in which
R 1 represents hydrogen, (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 1 -C 6 )-haloalkyl, (C 3 -C 6 )-halocycloalkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-haloalkenyl, (C 1 -C 5 )-alkoxy-(C 1 -C 5 )-haloalkyl, (C 2 -C 5 )-alkynyl, aryl, aryl-(C 1 -C 5 )-alkyl, heteroaryl, heteroaryl-(C 1 -C 5 )-alkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 5 )-alkyl, (C 2 -C 5 )-haloalkynyl, heterocyclyl, heterocyclyl-(C 1 -C 5 )-alkyl, (C 1 -C 5 )-alkoxy-(C 1 -C 5 )-alkyl, (C 1 -C 5 )-alkylcarbonyl-(C 1 -C 5 )-alkyl, hydroxycarbonyl-(C 1 -C 5 )-alkyl, (C 1 -C 5 )-alkoxycarbonyl-(C 1 -C 5 )-alkyl, (C 2 -C 5 )-alkenyloxycarbonyl-(C 1 -C 5 )-alkyl, (C 2 -C 5 )-alkynyloxycarbonyl-(C 1 -C 5 )-alkyl, aryl-(C 1 -C 5 )-alkoxycarbonyl-(C 1 -C 5 )-alkyl, (C 3 -C 6 )-cycloalkoxycarbonyl-(C 1 -C 5 )-alkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 5 )-alkoxycarbonyl-(C 1 -C 5 )-alkyl, aminocarbonyl-(C 1 -C 5 )-alkyl, (C 1 -C 5 )-alkylaminocarbonyl-(C 1 -C 5 )-alkyl, (C 3 -C 6 )-cycloalkylaminocarbonyl-(C 1 -C 5 )-alkyl, aryl-(C 1 -C 5 )-alkylaminocarbonyl-(C 1 -C 5 )-alkyl, heteroaryl-(C 1 -C 5 )-alkylaminocarbonyl-(C 1 -C 5 )-alkyl, (C 1 -C 5 )-alkoxy-(C 1 -C 5 )-alkoxy-(C 1 -C 5 )-alkyl, (C 1 -C 5 )-alkylcarbonyl, (C 1 -C 5 )-haloalkylcarbonyl, (C 3 -C 6 )-cycloalkylcarbonyl, (C 1 -C 5 )-alkoxycarbonyl, aryl-(C 1 -C 5 )-alkoxycarbonyl, arylcarbonyl, heteroarylcarbonyl, heterocyclylcarbonyl, aryl-(C 1 -C 6 )-alkylcarbonyl, (C 1 -C 6 )-alkylaminocarbonyl, (C 3 -C 6 )-cycloalkylaminocarbonyl, arylaminocarbonyl, aryl-(C 1 -C 6 )-alkylaminocarbonyl, heteroarylaminocarbonyl, heterocyclylaminocarbonyl, heteroaryl-(C 1 -C 6 )-alkylaminocarbonyl, heterocyclyl-(C 1 -C 6 )-alkylaminocarbonyl, (C 1 -C 6 )-alkylsulfonyl, (C 3 -C 6 )-cycloalkylsulfonyl, arylsulfonyl, aryl-(C 1 -C 6 )-alkylsulfonyl, heteroarylsulfonyl, heterocyclylsulfonyl, cyano-(C 1 -C 5 )-alkyl, bis-[(C 1 -C 5 )-alkyl]amino, (C 3 -C 6 )-cycloalkyl[(C 1 -C 5 )-alkyl]amino,
R 2 , R 3 , R 4 independently of one another represent hydrogen, halogen, (C 1 -C 5 )-alkoxy, (C 1 -C 5 )-alkyl, (C 1 -C 5 )-haloalkyl, (C 1 -C 5 )-haloalkoxy, (C 1 -C 5 )-alkylthio, (C 1 -C 5 )-haloalkylthio, aryl, aryl-(C 1 -C 5 )-alkyl, heteroaryl, heteroaryl-(C 1 -C 5 )-alkyl, heterocyclyl, heterocyclyl-(C 1 -C 5 )-alkyl, (C 3 -C 6 )-cycloalkyl, nitro, amino, hydroxy, (C 1 -C 5 )-alkylamino, bis-[(C 1 -C 5 )-alkyl]amino, hydrothio, (C 1 -C 5 )-alkylcarbonylamino, (C 3 -C 6 )-cycloalkylcarbonylamino, arylcarbonylamino, heteroarylcarbonylamino, heterocyclylcarbonylamino, formyl, hydroxyiminomethyl, (C 1 -C 5 )-alkoxyiminomethyl, (C 3 -C 6 )-cycloalkoxyiminomethyl, aryloxyiminomethyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 5 )-alkoxyiminomethyl, thiocyanato, isothiocyanato, aryloxy, heteroaryloxy, (C 3 -C 6 )-cycloalkoxy, (C 3 -C 6 )-cycloalkyl-(C 1 -C 5 )-alkoxy, aryl-(C 1 -C 5 )-alkoxy, (C 2 -C 5 )-alkynyl, (C 2 -C 5 )-alkenyl, aryl-(C 1 -C 5 )-alkynyl, tris-[(C 1 -C 5 )-alkyl]silyl-(C 2 -C 5 )-alkynyl, bis-[(C 1 -C 5 )-alkyl](aryl)silyl-(C 2 -C 5 )-alkynyl, bis-aryl[(C 1 -C 5 )-alkyl]silyl-(C 2 -C 5 )-alkynyl, (C 3 -C 6 )-cycloalkyl-(C 2 -C 5 )-alkynyl, aryl-(C 2 -C 5 )-alkenyl, heteroaryl-(C 2 -C 5 )-alkenyl, (C 3 -C 6 )-cycloalkyl-(C 2 -C 5 )-alkenyl, (C 2 -C 5 )-haloalkynyl, (C 2 -C 5 )-haloalkenyl, (C 4 -C 5 )-cycloalkenyl, (C 1 -C 5 )-alkoxy-(C 1 -C 5 )-alkoxy-(C 1 -C 5 )-alkyl, (C 1 -C 5 )-alkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, (C 1 -C 5 )-alkylsulfonylamino, arylsulfonylamino, aryl-(C 1 -C 5 )-alkylsulfonylamino, heteroarylsulfonylamino, heteroaryl-(C 1 -C 5 )-alkylsulfonylamino, bis-[(C 1 -C 5 )-alkyl]aminosulfonyl,
R 5 represents amino, (C 1 -C 5 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 5 )-alkyl, (C 1 -C 5 )-haloalkyl, (C 3 -C 6 )-halocycloalkyl, (C 4 -C 6 )-cycloalkenyl, aryl, heteroaryl, heterocyclyl, aryl-(C 1 -C 5 )-alkyl, heteroaryl-(C 1 -C 5 )-alkyl, heterocyclyl-(C 1 -C 5 )-alkyl, (C 1 -C 5 )-alkoxycarbonyl-(C 1 -C 5 )-alkyl, aryl-(C 1 -C 5 )-alkoxycarbonyl-(C 1 -C 5 )-alkyl, (C 3 -C 6 )-cycloalkoxycarbonyl-(C 1 -C 5 )-alkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 5 )-alkoxycarbonyl-(C 1 -C 5 )-alkyl, heteroaryl-(C 1 -C 5 )-alkoxycarbonyl-(C 1 -C 5 )-alkyl, aminocarbonyl-(C 1 -C 5 )-alkyl, (C 1 -C 5 )-alkylaminocarbonyl-(C 1 -C 5 )-alkyl, (C 3 -C 6 )-cycloalkylaminocarbonyl-(C 1 -C 5 )-alkyl, aryl-(C 1 -C 5 )-alkylaminocarbonyl-(C 1 -C 5 )-alkyl, (C 1 -C 5 )-alkylamino, arylamino, (C 3 -C 6 )-cycloalkylamino, aryl-(C 1 -C 5 )-alkylamino, heteroaryl-(C 1 -C 5 )-alkylamino, heteroarylamino, heterocyclylamino, aryloxy-(C 1 -C 5 )-alkyl, (C 1 -C 5 )-alkoxy-(C 1 -C 5 )-alkyl, heteroaryloxy-(C 1 -C 5 )-alkyl, (C 2 -C 5 )-alkenyl, (C 2 -C 5 )-alkynyl, (C 2 -C 5 )-alkenylamino, (C 2 -C 5 )-alkynylamino, bis-[(C 1 -C 5 )-alkyl]amino, aryloxy, (C 3 -C 6 )-cycloalkyl-(C 2 -C 5 )-alkyl, bis-[(C 1 -C 5 )-alkyl]amino, aryl-(C 2 -C 5 )-alkenyl, heteroaryl-(C 2 -C 5 )-alkenyl, heterocyclyl-(C 2 -C 5 )-alkenyl,
R 6 represents hydrogen, (C 1 -C 5 )-alkyl, (C 3 -C 6 )-cycloalkyl, cyano-(C 1 -C 5 )-alkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 5 )-alkyl, (C 1 -C 5 )-alkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, (C 3 -C 6 )-cycloalkylsulfonyl, heterocyclylsulfonyl, aryl-(C 1 -C 5 )-alkylsulfonyl, (C 1 -C 5 )-alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, (C 3 -C 6 )-cycloalkylcarbonyl, heterocyclylcarbonyl, (C 1 -C 5 )-alkoxycarbonyl, aryl-(C 1 -C 5 )-alkoxycarbonyl, (C 1 -C 5 )-haloalkylcarbonyl, (C 2 -C 5 )-alkenyl, (C 2 -C 5 )-alkynyl, (C 1 -C 5 )-haloalkyl, halo-(C 2 -C 5 )-alkynyl, halo-(C 2 -C 5 )-alkenyl, (C 1 -C 5 )-alkoxy-(C 1 -C 5 )-alkyl and
W represents oxygen or sulfur.

2. The method as claimed in claim 1 , wherein the abiotic stress conditions are one or more conditions selected from the group consisting of aridity, cold stress, heat stress, drought stress, osmotic stress, waterlogging, elevated soil salinity, elevated exposure to minerals, ozone conditions, strong light conditions, limited availability of nitrogen nutrients and limited availability of phosphorus nutrients.

3. The method as claimed in claim 1 , wherein said applying comprises spraying the one or more compounds in combination with one or more active compounds selected from the group consisting of insecticides, attractants, acaricides, fungicides, nematicides, herbicides, growth regulators, safeners, and substances which affect plant maturity and bactericides.

4. The method as claimed in claim 1 , wherein said applying comprises spraying plants and parts of plants with the one or more compounds in combination with fertilizers.

5. The method of claim 1 , wherein the compound is applied to a genetically modified cultivars, the seed thereof, or to cultivated areas on which these cultivars grow.

6. The method of claim 1 , comprising increasing stress tolerance in plants selected from the group of useful plants, ornamental plants, turfgrasses and trees, comprising applying-the one or more compounds to an area where a corresponding effect is desired, comprising application to the plants, the seed thereof or to the area on whic

Assignees

• Bayer Cropscience Ag

Inventors

• Frackenpohl Jens
• Bojack Guido
• Helmke Hendrik
• Lehr Stefan
• Mueller Thomas
• Willms Lothar
• Dittgen Jan
• Schmutzler Dirk
• Bickers Udo
• Strek Harry
• Baltz Rachel

Classifications

• A01N47/16

  the nitrogen atom being part of a heterocyclic ring · CPC title

• C07D209/34

  in position 2 · CPC title

• C07D471/10

  Spiro-condensed systems · CPC title

• C07D491/107

  with only one oxygen atom as ring hetero atom in the oxygen-containing ring · CPC title

• A01N43/90

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