5-substituted imidazole derivatives

Patent metadata

Field	Value
Publication number	US-10568326-B2
Application number	US-201816190285-A
Country	US
Kind code	B2
Filing date	Nov 14, 2018
Priority date	Apr 2, 2015
Publication date	Feb 25, 2020
Grant date	Feb 25, 2020

Abstract

The present invention relates to novel 5-substituted imidazolylmethyl 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 and as plant growth regulators.

First claim

The invention claimed is:

1. A compound of formula (XVII)

wherein
R 1 represents hydrogen, in each case optionally branched C 1 -C 8 -alkyl, C 1 -C 8 -haloalkyl, C 2 -C 7 -alkenyl, C 2 -C 7 -haloalkenyl, C 2 -C 8 -alkynyl, C 2 -C 8 -haloalkynyl, 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 -alkylthio- or C 1 -C 4 -haloalkylthio-substituted C 3 -C 7 -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 -alkylthio- or C 1 -C 4 -haloalkylthio-substituted bicycloalkyl, 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 -alkylthio- or C 1 -C 4 -haloalkylthio-substituted C 3 -C 8 -cycloalkylalkyl; 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 -alkylthio- or C 1 -C 4 -haloalkylthio-substituted C 3 -C 7 -halocycloalkyl-C 1 -C 4 -alkyl; 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 -alkylthio- or C 1 -C 4 -haloalkylthio-substituted C 3 -C 7 -halocycloalkyl-C 1 -C 4 -haloalkyl; 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 -alkylthio- or C 1 -C 4 -haloalkylthio-substituted C 3 -C 7 -cycloalkyl-C 1 -C 4 -haloalkyl; 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 -alkylthio- or C 1 -C 4 -haloalkylthio-substituted C 3 -C 7 -cycloalkyl-C 3 -C 7 -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 -alkylthio- or C 1 -C 4 -haloalkylthio-substituted C 3 -C 7 -cycloalkenyl, 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 -alkylthio- or C 1 -C 4 -haloalkylthio-substituted tri(C 1 -C 8 -alkyl)silyl-C 1 -C 4 -alkyl; 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 -alkylthio- or C 1 -C 4 -haloalkylthio-substituted tri(C 1 -C 8 -alkyl)silyl-C 3 -C 7 -cycloalkyl;
and
R 3 represents halogen; hydroxyl; cyano; isocyano; amino; sulfanyl; pentafluoro-λ 6 -sulfanyl; carboxaldehyde; C 1 -C 8 -alkyl; C 1 -C 8 -haloalkyl; C 1 -C 8 -cyanoalkyl; C 1 -C 8 -alkyloxy; C 1 -C 8 -halogenalkyloxy; tri(C 1 -C 8 -alkyl)silyl; tri(C 1 -C 8 -alkyl)silyl-C 1 -C 8 -alkyl; C 3 -C 7 -cycloalkyl; C 3 -C 7 -halogencycloalkyl; C 3 -C 7 -cycloalkenyl; C 3 -C 7 -halogencycloalkenyl; C 4 -C 10 -cycloalkylalkyl; C 4 -C 10 -halocycloalkylalkyl; C 6 -C 12 -cycloalkylcycloalkyl; C 1 -C 8 -alkyl-C 3 -C 7 -cycloalkyl; C 1 -C 8 -alkoxy-C 3 -C 7 -cycloalkyl; tri(C 1 -C 8 -alkyl)silyl-C 3 -C 7 -cycloalkyl; C 2 -C 8 -alkenyl; C 2 -C 8 -alkynyl; C 2 -C 8 -alkenyloxy; C 2 -C 8 -halogenalkenyloxy; C 3 -C 8 -alkynyloxy; C 3 -C 8 -halogenoalkynyloxy; C 1 -C 8 -alkylamino; C 1 -C 8 -halogenalkylamino; C 1 -C 8 -cyanoalkoxy; C 4 -C 8 -cycloalkylalkoxy; C 3 -C 6 -cycloalkoxy; C 1 -C 8 -alkylsulfanyl; C 1 -C 8 -halogenoalkylsulfanyl; C 1 -C 8 -alkylcarbonyl; C 1 -C 8 -halogenoalkylcarbonyl; arylcarbonyl; aryl-C 1 -C 6 -alkylcarbonyl; C 3 -C 8 -cycloalkylcarbonyl; C 3 -C 8 -halogenocycloalkylcarbonyl; C 1 -C 8 -alkylcarbamoyl; di-C 1 -C 8 -alkylcarbamoyl; N—C 1 -C 8 -alkyloxycarbamoyl; C 1 -C 8 -alkoxycarbamoyl; N—C 1 -C 8 -alkyl-C 1 -C 8 -alkoxycarbamoyl; aminothiocarbonyl; C 2 -C 8 -alkoxycarbonyl; C 1 -C 8 -halogenoalkoxycarbonyl; C 3 -C 8 -cycloalkoxycarbonyl; C 2 -C 8 -alkoxyalkylcarbonyl; C 2 -C 8 -halogenoalkoxyalkylcarbonyl; C 3 -C 10 -cycloalkoxyalkylcarbonyl; C 1 -C 8 -alkylaminocarbonyl; di-C 1 -C 8 -alkylaminocarbonyl; C 3 -C 8 -cycloalkylaminocarbonyl; C 1 -C 8 -alkylcarbonyloxy; C 1 -C 8 -halogenoalkylcarbonyloxy; C 3 -C 8 -cycloalkylcarbonyloxy; C 1 -C 8 -alkylcarbonylamino; C 1 -C 8 -halogenoalkylcarbonylamino; C 1 -C 8 -alkylaminocarbonyloxy; di-C 1 -C 8 -alkylaminocarbonyloxy; C 1 -C 8 -alkyloxycarbonyloxy; C 1 -C 8 -alkylsulfinyl; C 1 -C 8 -halogenoalkylsulfinyl; C 1 -C 8 -alkylsulfonyl; C 1 -C 8 -halogenoalkylsulfonyl; C 1 -C 8 -alkylsulfonyloxy; C 1 -C 8 -halogenoalkylsulfonyloxy; C 1 -C 8 -alkylaminosulfamoyl; di-C 1 -C 8 -alkylaminosulfamoyl; (C 1 -C 8 -alkoxyimino)-C 1 -C 8 -alkyl; (C 3 -C 7 -cycloalkoxyimino)-C 1 -C 8 -alkyl; hydroxyimino-C 1 -C 8 -alkyl; (C 1 -C 8 -alkoxyimino)-C 3 -C 7 -cycloalkyl; hydroxyimino-C 3 -C 7 -cycloalkyl; (C 1 -C 8 -alkylimino)-oxy; (C 1 -C 8 -alkylimino)-oxy-C 1 -C 8 -alkyl; (C 3 -C 7 -cycloalkylimino)-oxy-C 1 -C 8 -alkyl; (C 1 -C 6 -alkylimino)-oxy-C 3 -C 7 -cycloalkyl; (C 1 -C 8 -alkenyloxyimino)-C 1 -C 8 -alkyl; (C 1 -C 8 -alkynyloxyimino)-C 1 -C 8 -alkyl; (benzyloxyimino)-C 1 -C 8 -alkyl; C 1 -C 8 -alkoxyalkyl; C 1 -C 8 -alkylthioalkyl; C 1 -C 8 -alkoxyalkoxyalkyl; C 1 -C 8 -halogenoalkoxyalkyl; benzyl; 5-membered heteroaryl; 6-membered heteroaryl; benzyloxy; phenyloxy; benzylsulfanyl; benzylamino; phenylsulfanyl; or phenylamino; wherein the benzyl, 5-membered heteroaryl, 6-membered heteroaryl, benzyloxy or phenyloxy may be optionally substituted by one or more group(s) selected from halogen; hydroxyl; cyano; isocyano; amino; sulfanyl; pentafluoro-λ 6 -sulfanyl; carboxaldehyde, hydroxycarbonyl, C 1 -C 8 -alkyl; C 1 -C 8 -haloalkyl; C 1 -C 8 -cyanoalkyl; C 1 -C 8 -alkyloxy; C 1 -C 8 -halogenalkyloxy; tri(C 1 -C 8 -alkyl)silyl; tri(C 1 -C 8 -alkyl)silyl-C 1 -C 8 -alkyl; C 3 -C 7 -cycloalkyl; C 3 -C 7 -halogencycloalkyl; C 3 -C 7 -cycloalkenyl; C 3 -C 7 -halogencycloalkenyl; C 4 -C 10 -cycloalkylalkyl; C 4 -C 10 -halocycloalkylalkyl; C 6 -C 12 -cycloalkylcycloalkyl; C 1 -C 8 -alkyl-C 3 -C 7 -cycloalkyl; C 1 -C 8 -alkoxy-C 3 -C 7 -cycloalkyl; tri(C 1 -C 8 -alkyl)silyl-C 3 -C 7 -cycloalkyl; C 2 -C 8 -alkenyl; C 2 -C 8 -alkynyl; C 2 -C 8 -alkenyloxy; C 2 -C 8 -halogenalkenyloxy; C 3 -C 8 -alkynyloxy; C 3 -C 8 -halogenoalkynyloxy; C 1 -C 8 -alkylamino; C 1 -C 8 -halogenalkylamino; C 1 -C 8 -cyanoalkoxy; C 4 -C 8 -cycloalkylalkoxy; C 3 -C 6 -cycloalkoxy; C 1 -C 8 -alkylsulfanyl; C 1 -C 8 -halogenoalkylsulfanyl; C 1 -C 8 -alkylcarbonyl; C 1 -C 8 -halogenoalkylcarbonyl; arylcarbonyl; aryl-C 1 -C 6 -alkylcarbonyl; C 3 -C 8 -cycloalkylcarbonyl; C 3 -C 8 -halogenocycloalkylcarbonyl; C 1 -C 8 -alkylcarbamoyl; di-C 1 -C 8 -alkylcarbamoyl; N—C 1 -C 8 -alkyloxycarbamoyl; C 1 -C 8 -alkoxycarbamoyl; N—C 1 -C 8 -alkyl-C 1 -C 8 -alkoxycarbamoyl; aminothiocarbonyl; C 1 -C 8 -alkoxycarbonyl; C 1 -C 8 -halogenoalkoxycarbonyl; C 3 -C 8 -cycloalkoxycarbonyl; C 2 -C 8 -alkoxyalkylcarbonyl; C 2 -C 8 -halogenoalkoxyalkylcarbonyl; C 3 -C 10 -
R 1 represents in each case optionally branched C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 2 -C 5 -alkenyl, C 2 -C 5 -haloalkenyl, or optionally halogen-, cyano-, C 1 -C 4 -alkyl-, C 1 -C 4 -haloalkyl-, C 1 -C 4 -haloalkoxy-, C 1 -C 4 -alkoxy-, C 1 -C 4 -alkylthio- or C 1 -C 4 -haloalkylthio-substituted C 3 -C 6 -cycloalkyl.

2. The compound of formula (XVII) and/or a salt and/or N-oxide thereof according to claim 1 , wherein
R 1 represents in each case optionally branched C 1 -C 8 -alkyl, C 1 -C 8 -haloalkyl, C 2 -C 7 -alkenyl, C 2 -C 7 -haloalkenyl, or 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 -alkylthio- or C 1 -C 4 -haloalkylthio-substituted C 3 -C 7 -cycloalkyl.

3. The compound of formula (XVII) and/or a salt and/or N-oxide thereof according to claim 1 , wherein
aminothiocarbonyl; C 2 -C 5 -alkoxycarbonyl; C 1 -C 8 -halogenoalkoxycarbonyl; C 3 -C 8 -cycloalkoxycarbonyl; C 1 -C 8 -alkylcarbonyloxy; C 1 -C 8 -halogenoalkylcarbonyloxy; C 3

Assignees

• Bayer Cropscience Ag

Inventors

• Hoffmann Sebastian
• Helmke Hendrik
• Dahmen Peter
• Wachendorff-Neumann Ulrike
• Bernier David
• Miller Ricarda
• Coqueron Pierre-Yves
• Genix Pierre
• Wittrock Sven
• Vors Jean-Pierre
• Kennel Philippe
• Brunet Stephane
• Naud Sebastien
• Meissner Ruth

Classifications

• A01N43/50 Primary

  1,3-Diazoles; Hydrogenated 1,3-diazoles · CPC title

• C07D233/68

  Halogen atoms · CPC title

• C07D233/92

  attached in position 4 or 5 · CPC title

• C07D233/61

  with hydrocarbon radicals, substituted by nitrogen atoms not forming part of a nitro radical, attached to ring nitrogen atoms · CPC title

• C07D233/74

  with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to other ring members · CPC title