Nitrogen-containing heterocyclic compounds for plant disease control

Patent metadata

Field	Value
Publication number	US-9776993-B2
Application number	US-201615335832-A
Country	US
Kind code	B2
Filing date	Oct 27, 2016
Priority date	Sep 28, 2012
Publication date	Oct 3, 2017
Grant date	Oct 3, 2017

Abstract

The present invention relates to novel isoxazoline carboxamide derivatives, to processes for preparing these compounds, to compositions comprising these compounds, and to the use thereof as biologically active compounds, especially for control of harmful microorganisms in crop protection and in the protection of materials.

First claim

The invention claimed is:

1. Quinoline-isoxazoline-5-carboxylic acid and/or acid ester and/or quinoline-isoxazoline-5-thiocarboxylic acid and/or acid ester of formula (II)

in which
R c represents hydrogen, substituted or non-substituted C 1 -C 8 -alkyl; C 1 -C 8 -haloalkyl; substituted or non-substituted C 2 -C 8 -alkenyl; C 2 -C 8 -haloalkenyl; substituted or non-substituted C 2 -C 8 -alkynyl; C 2 -C 8 -haloalkynyl; substituted or non-substituted aryl; or substituted or non-substituted 5, 6 or 7 membered unsaturated heterocycle ring with 1 to 3 heteroatoms;
R 1 and R 2 independently of one another represent hydrogen; substituted or non-substituted C 1 -C 8 -alkyl; C 1 -C 8 -haloalkyl; substituted or non-substituted C 2 -C 8 -alkenyl; C 2 -C 8 -haloalkenyl; substituted or non-substituted C 2 -C 8 -alkynyl; C 2 -C 8 -haloalkynyl; cyano; isonitrile; nitro; halogen; substituted or non-substituted C 1 -C 8 -alkoxy; C 1 -C 8 -haloalkoxy; substituted or non-substituted C 2 -C 8 -alkenyloxy; C 2 -C 8 -haloalkenyloxy, substituted or non-substituted C 2 -C 8 -alkynyloxy; C 1 -C 8 -haloalkynyloxy; substituted or non-substituted C 3 -C 7 -cycloalkyl; substituted or non-substituted C 1 -C 8 -alkylsulfanyl; substituted or non-substituted C 1 -C 8 -alkylsulfonyl; substituted or non-substituted C 1 -C 8 -alkylsulfinyl; amino; substituted or non-substituted C 1 -C 8 -alkylamino; substituted or non-substituted di-C 1 -C 8 -alkylamino; substituted or non-substituted C 1 -C 8 -alkoxycarbonyl; substituted or non-substituted C 1 -C 8 -alkylcarbamoyl; substituted or non-substituted di-C 1 -C 8 -alkylcarbamoyl; or substituted or non-substituted N—C 1 -C 8 -alkyl-C 1 -C 8 -alkoxy-carbamoyl; or
R 1 and R 2 can form together with the carbon atom to which they are attached a substituted or non-substituted C 3 -C 7 -cycloalkyl; or C 3 -C 7 -halocycloalkyl;
R 3 represents hydrogen; substituted or non-substituted C 1 -C 8 -alkyl; C 1 -C 8 -haloalkyl; substituted or non-substituted C 2 -C 8 -alkenyl; C 2 -C 8 -haloalkenyl; substituted or non-substituted C 2 -C 8 -alkynyl; C 2 -C 8 -haloalkynyl; cyano; isonitrile; nitro; halogen; substituted or non-substituted C 1 -C 8 -alkoxy; C 1 -C 8 -haloalkoxy; substituted or non-substituted C 2 -C 8 -alkenyloxy; C 2 -C 8 -haloalkenyloxy, substituted or non-substituted C 2 -C 8 -alkynyloxy; C 1 -C 8 -haloalkynyloxy; substituted or non-substituted C 3 -C 7 -cycloalkyl; substituted or non-substituted C 1 -C 8 -alkylsulfanyl; substituted or non-substituted C 1 -C 8 -alkylsulfonyl; substituted or non-substituted C 1 -C 8 -alkylsulfinyl; amino; substituted or non-substituted C 1 -C 8 -alkylamino; substituted or non-substituted di-C 1 -C 8 -alkylamino; substituted or non-substituted tri(C 1 -C 8 )alkylsilyl-C 1 -C 8 -alkyl; substituted or non-substituted tri(C 1 -C 8 )alkylsilyl-C 2 -C 8 -alkenyl; substituted or non-substituted tri(C 1 -C 8 )alkylsilyl-C 2 -C 8 -alkynyl; substituted or non-substituted C 1 -C 8 -alkoxycarbonyl; substituted or non-substituted C 1 -C 8 -alkylcarbamoyl; substituted or non-substituted di-C 1 -C 8 -alkylcarbamoyl; or substituted or non-substituted N—C 1 -C 8 -alkyl-C 1 -C 8 -alkoxy-carbamoyl; substituted or non-substituted aryl; or substituted or non-substituted 5, 6 or 7 membered heterocycle ring with 1 to 3 heteroatoms; or
R 3 together with R 1 or R 2 together with the carbon atoms to which they are attached can form a substituted or non-substituted C 3 -C 7 cycloalkyl; C 3 -C 7 -halocycloalkyl; or a substituted or non-substituted saturated 5, 6 or 7 membered heterocycle;
Y represents an oxygen or sulfur atom;
Q 1 , Q 2 , Q 3 , Q 4 , Q 5 and Q 6 independently of one another represent hydrogen; halogen; nitro; cyano; isonitrile; hydroxyl; amino; sulfanyl; pentafluoro-λ 6 -sulfanyl; formyl; formyloxy; formylamino; substituted or non-substituted (hydroxyimino)-C 1 -C 8 -alkyl; substituted or non-substituted (C 1 -C 8 -alkoxyimino)-C 1 -C 8 -alkyl; substituted or non-substituted (C 2 -C 8 -alkenyloxyimino)-C 1 -C 8 -alkyl; substituted or non-substituted (C 2 -C 8 -alkynyloxyimino)-C 1 -C 8 -alkyl; substituted or non-substituted (benzyloxyimino)-C 1 -C 8 -alkyl; carboxy; carbamoyl; N-hydroxycarbamoyl; carbamate; substituted or non-substituted C 1 -C 8 -alkyl; C 1 -C 8 -haloalkyl; substituted or non-substituted C 2 -C 8 -alkenyl; C 2 -C 8 -haloalkenyl; substituted or non-substituted C 2 -C 8 -alkynyl; C 2 -C 8 -haloalkynyl; substituted or non-substituted C 1 -C 8 -alkoxy; C 1 -C 8 -haloalkoxy; substituted or non-substituted C 1 -C 8 -alkylsulfanyl; C 1 -C 8 -haloalkylsulfanyl; substituted or non-substituted C 1 -C 8 -alkylsulfinyl; C 1 -C 8 -haloalkylsulfinyl; substituted or non-substituted C 1 -C 8 -alkylsulfonyl; C 1 -C 8 -haloalkylsulfonyl; substituted or non-substituted C 1 -C 8 -alkylamino; substituted or non-substituted di-C 1 -C 8 -alkylamino; substituted or non-substituted C 2 -C 8 -alkenyloxy; C 2 -C 8 -haloalkenyloxy; substituted or non-substituted C 3 -C 8 -alkynyloxy; C 2 -C 8 -haloalkynyloxy; substituted or non-substituted C 3 -C 7 -cycloalkyl; C 3 -C 7 -halocycloalkyl; substituted or non-substituted (C 3 -C 7 -cycloalkyl)-C 1 -C 8 -alkyl; substituted or non-substituted C 4 -C 7 -cycloalkenyl; C 4 -C 7 -halocycloalkenyl; substituted or non-substituted (C 3 -C 7 -cycloalkyl)-C 2 -C 8 -alkenyl; substituted or non-substituted (C 3 -C 7 -cycloalkyl)-C 2 -C 8 -alkynyl; substituted or non-substituted tri(C 1 -C 8 )alkylsilyl; substituted or non-substituted tri(C 1 -C 8 )alkylsilyl-C 1 -C 8 -alkyl; substituted or non-substituted tri(C 1 -C 8 )alkylsilyl-C 2 -C 8 -alkenyl; substituted or non-substituted tri(C 1 -C 8 )alkylsilyl-C 2 -C 8 -alkynyl; substituted or non-substituted C 1 -C 8 -alkylcarbonyl; C 1 -C 8 -haloalkylcarbonyl; substituted or non-substituted C 1 -C 8 -alkylcarbonyloxy; C 1 -C 8 -haloalkylcarbonyloxy; substituted or non-substituted C 1 -C 8 -alkylcarbonylamino; C 1 -C 8 -haloalkylcarbonylamino; substituted or non-substituted C 1 -C 8 -alkoxycarbonyl; C 1 -C 8 -haloalkoxycarbonyl; substituted or non-substituted C 1 -C 8 -alkyloxycarbonyloxy; C 1 -C 8 -haloalkoxycarbonyloxy; substituted or non-substituted C 1 -C 8 -alkylcarbamoyl; substituted or non-substituted di-C 1 -C 8 -alkylcarbamoyl; substituted or non-substituted C 1 -C 8 -alkylaminocarbonyloxy; substituted or non-substituted di-C 1 -C 8 -alkylaminocarbonyloxy; substituted or non-substituted N—(C 1 -C 8 -alkyl)hydroxy carbamoyl; substituted or non-substituted C 1 -C 8 -alkoxycarbamoyl; substituted or non-substituted N—(C 1 -C 8 -alkyl)-C 1 -C 8 -alkoxycarbamoyl; aryl which is optionally substituted by up to 6 identical or different groups R a ; C 1 -C 8 -arylalkyl which is optionally substituted by up to 6 identical or different groups R a ; C 2 -C 8 -arylalkenyl which is optionally substituted by up to 6 identical or different groups R a ; C 2 -C 8 -arylalkynyl which is optionally substituted by up to 6 identical or different groups R a ; aryloxy which is optionally substituted by up to 6 identical or different groups R a ; arylsulfanyl which is optionally substituted by up to 6 identical or different groups R a ; arylamino which is optionally substituted by up to 6 identical or different groups R a ; C 1 -C 8 -arylalkyloxy which is optionally substituted by up to 6 identical or different groups R a ; C 1 -C 8 -arylalkylsulfanyl which is optionally substituted by up to 6 identical or different groups R a ; C 1 -C 8 -arylalkylamino which is optionally substituted by up to 6 identical or different groups R a ; 5, 6 or 7 membered heterocycle with 1 to 3 heteroatoms which is optionally substituted by up to 4 identical or different groups R a ;
R a independently of one another represent halogen; cyano; nitro; substituted or non-substituted C

Assignees

• Bayer Cropscience Ag

Inventors

• Willms Lothar
• Schmitt Monika H
• Frenzel Thomas
• Haaf Klaus Bernhard
• Haeuser-Hahn Isolde
• Heinemann Ines
• Gatzweiler Elmar
• Rosinger Christopher Hugh
• Kehne Heinz
• Dittgen Jan
• Feucht Dieter
• Hills Martin
• Schmidt Jan Peter
• Es-Sayed Mazen
• Rinolfi Philipe
• Brunet Stephane
• Grosjean-Cournoyer Marie-Claire
• Lachaise Helene
• Vidal Jacky
• Coqueron Pierre-Yves
• Tuch Arounarith

Classifications

• A01N43/84

  six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4 · CPC title

• C07D413/04 Primary

  directly linked by a ring-member-to-ring-member bond · CPC title

• A01N55/00

  Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur (containing organo-phosphorus compounds A01N57/00) · CPC title

• A01N43/82

  five-membered rings with three ring hetero atoms · CPC title

• C07D498/04

  Ortho-condensed systems · CPC title