Triazolinthione derivatives

Patent metadata

Field	Value
Publication number	US-9550752-B2
Application number	US-201414783207-A
Country	US
Kind code	B2
Filing date	Apr 9, 2014
Priority date	Apr 12, 2013
Publication date	Jan 24, 2017
Grant date	Jan 24, 2017

Abstract

The present invention relates to novel triazolinthione 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. Triazole derivative of formula (I)

wherein
R 1 represents substituted or non-substituted C 1 -C 8 -alkyl; substituted or non-substituted C 2 -C 8 -alkenyl; substituted or non-substituted C 2 -C 8 -alkynyl; substituted or non-substituted C 3 -C 7 -cycloalkyl; substituted or non-substituted C 4 -C 8 -cycloalkylalkyl; substituted or non-substituted C 3 -C 7 -cycloalkenyl; substituted or non-substituted arylalkyl; substituted or non-substituted arylalkenyl; substituted or non-substituted arylalkynyl, substituted or non-substituted phenoxyalkyl; substituted or non-substituted phenylcycloalkyl; substituted or non-substituted hetaryl; substituted hetarylalkyl; substituted or non-substituted heterocycloalkyl; substituted or non-substituted heterocycloalkyl-C 1 -C 8 -alkyl;
R 2 represents H, C 1 -C 8 -alkyl, —Si(R 3a )(R 3b )(R 3c ), —P(O)(OH) 2 , —CH 2 —O—P(O)(OH) 2 , substituted or non-substituted —C(O)—C 1 -C 8 -alkyl or substituted, non-substituted —C(O)—C 3 -C 7 -cycloalkyl, substituted or non-substituted —C(O)NH—C 1 -C 8 -alkyl; substituted or non-substituted —C(O)N-di-C 1 -C 8 -alkyl; substituted or non-substituted —C(O)O—C 1 -C 8 -alkyl;
R 3a , R 3b , R 3c independent from each other represent a substituted or non-substituted C 1 -C 8 -alkyl; and
X represents a substituted or non-substituted unsaturated 5- or 6-membered heterocycle containing 1 or 2 nitrogen atom(s) as heteroatom(s) or a benzannulated derivative thereof;
and/or a salt and/or N-oxide thereof.

2. Triazole derivative of formula (I) and/or a salt and/or N-oxide thereof according to claim 1 , wherein
R 1 represents substituted or non-substituted C 1 -C 8 -alkyl; substituted or non-substituted C 2 -C 8 -alkenyl; substituted or non-substituted C 2 -C 8 -alkynyl; substituted or non-substituted C 3 -C 7 -cycloalkyl; substituted or non-substituted C 4 -C 8 -cycloalkylalkyl; substituted or non-substituted C 3 -C 7 -cycloalkenyl; substituted or non-substituted arylalkyl; substituted or non-substituted arylalkenyl; substituted or non-substituted arylalkynyl, substituted or non-substituted phenoxyalkyl; substituted or non-substituted phenylcycloalkyl; substituted or non-substituted hetaryl; substituted hetarylalkyl; substituted or non-substituted heterocycloalkyl; substituted or non-substituted heterocycloalkyl-C 1 -C 8 -alkyl;
R 2 represents H, C 1 -C 8 -alkyl, —Si(R 3a )(R 3b )(R 3c ), —P(O)(OH) 2 , —CH 2 —O—P(O)(OH) 2 , substituted or non-substituted —C(O)—C 1 -C 8 -alkyl or substituted, non-substituted —C(O)—C 3 -C 7 -cycloalkyl, substituted or non-substituted —C(O)NH—C 1 -C 8 -alkyl; substituted or non-substituted —C(O)N-di-C 1 -C 8 -alkyl; substituted or non-substituted —C(O)O—C 1 -C 8 -alkyl;
R 3a , R 3b , R 3c independent from each other represent a substituted or non-substituted C 1 -C 8 -alkyl; and
X represents a substituted or non-substituted unsaturated 5- or 6 membered heterocycle containing 1 or 2 nitrogen atom(s) as heteroatom(s) or a benzannulated derivative thereof, with the provisio that X does not represent 2-pyridinyl.

3. Triazole derivative of formula (I) and/or a salt and/or N-oxide thereof according to claim 1 , wherein
R 1 represents substituted or non-substituted C 1 -C 8 -alkyl; substituted or non-substituted C 3 -C 7 -cycloalkyl;
R 2 represents H, C 1 -C 8 -alkyl, substituted or non-substituted —C(O)—C 1 -C 8 -alkyl; and
X represents a substituted or non-substituted 3-pyridinyl, 4-pyridinyl, 4-pyrimidinyl, 5-pyrimidinyl, pyrazin-2-yl, pyridazin-3-yl, pyridazin-4-yl, quinoline-2-yl or quinoline-3-yl.

4. Method for controlling one or more harmful microorganisms, comprising applying a compound of formula (I) and/or a salt and/or N-oxide thereof according to claim 1 , to the one or more harmful microorganisms and/or a habitat thereof.

5. Method for controlling phytopathogenic harmful fungi, comprising applying a compound of formula (I) and/or a salt and/or N-oxide thereof according to claim 1 to the phytopathogenic harmful fungi and/or a habitat thereof.

6. Composition for controlling one or more harmful microorganisms, optionally for controlling phytopathogenic harmful fungi, comprising a content of at least one compound of formula(I) and/or a salt and/or N-oxide thereof according to claim 1 , in addition to one or more extenders and/or surfactants.

7. Composition according to claim 6 comprising at least one further active ingredient selected from the group of the insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides, fertilizers, safeners and semiochemicals.

8. A compound of formula (I) and/or a salt and/or N-oxide thereof according to claim 1 , capable of being used for control of harmful microorganisms, optionally for controlling phytopathogenic harmful fungi.

9. Process for producing a composition for controlling one or more harmful microorganisms, optionally for controlling phytopathogenically harmful fungi, comprising mixing a compound of formula (I) and/or a salt and/or N-oxide thereof according to claim 1 , with one or more extenders and/or surfactants.

10. A compound of formula (I) and/or a salt and/or N-oxide thereof according to claim 1 , capable of being used for treatment of one or more transgenic plants.

11. A compound of formula (I) and/or a salt and/or N-oxide thereof according to claim 1 , capable of being used for treatment of seed and/or of seed of one or more transgenic plants.

12. Triazole derivative of formula (I) and/or a salt and/or N-oxide thereof according to claim 1 , wherein
R 1 represents 1-chlorocyclopropyl,
R 2 represents hydrogen, and
X represents 3-chloropyridin-4-yl.

Assignees

• Bayer Cropscience Ag

Inventors

• Hoffmann Sebastian
• Sudau Alexander
• Dahmen Peter
• Wachendorff-Neumann Ulrike
• Bernier David
• Lachaise Helene
• Brunet Stephane
• Vidal Jacky
• Genix Pierre
• Coqueron Pierre-Yves
• Geist Julie
• Vors Jean-Pierre
• Kennel Philippe
• Miller Ricarda

Classifications

• C07D213/42

  having hetero atoms attached to the substituent nitrogen atom (nitro radicals C07D213/26) · CPC title

• A01N43/653

  1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles · CPC title

• C07D403/06

  linked by a carbon chain containing only aliphatic carbon atoms · CPC title

• C07D401/06 Primary

  linked by a carbon chain containing only aliphatic carbon atoms · CPC title

• C07D401/14

  containing three or more hetero rings · CPC title