Triazole derivatives

Patent metadata

Field	Value
Publication number	US-9822099-B2
Application number	US-201414783216-A
Country	US
Kind code	B2
Filing date	Apr 9, 2014
Priority date	Apr 12, 2013
Publication date	Nov 21, 2017
Grant date	Nov 21, 2017

Abstract

The present invention relates to novel triazole 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 C 1 -C 8 -haloalkyl; C 2 -C 8 -halooalkenyl; C 2 -C 8 -haloalkynyl; C 3 -C 7 -halocycloalkyl-C 1 -C 4 -alkyl; C 3 -C 7 -halocycloalkyl-C 1 -C 4 -haloalkyl; C 3 -C 7 -cycloalkyl-C 1 -C 4 -haloalkyl; substituted or non-substituted C 3 -C 7 -cycloalkyl; 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; or 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; or 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 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 salt and/or N-oxide according to claim 1 , wherein
R 1 represents C 1 -C 8 -haloalkyl; C 2 -C 5 -halooalkenyl; C 2 -C 8 -haloalkynyl; C 3 -C 7 -halocycloalkyl-C 1 -C 4 -alkyl; C 3 -C 7 -halocycloalkyl-C 1 -C 4 -haloalkyl; C 3 -C 7 -cycloalkyl-C 1 -C 4 -haloalkyl; substituted or non-substituted C 3 -C 7 -cycloalkyl; 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; or 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 5 -alkyl; substituted or non-substituted —C(O)N-di-C 1 -C 8 -alkyl; or 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 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 salt and/or N-oxide according to claim 1 , wherein
R 1 represents C 1 -C 5 -haloalkyl or substituted or non-substituted C 3 -C 7 -cycloalkyl;
R 2 represents H, C 1 -C 8 -alkyl or 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 salt and/or N-oxide according to claim 1 , to the harmful microorganisms and/or a habitat thereof.

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

6. The method according to claim 5 , comprising treatment of one or more transgenic plants.

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

8. Composition according to claim 7 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.

9. The composition according to claim 7 , for control of phytopathogenic harmful fungi.

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

11. Seed treated with a compound of formula (I) and/or salt and/or N-oxide according to claim 1 .

12. Compound of formula (V)

wherein
X represents a substituted or non-substituted unsaturated 6-membered heterocycle containing 1 or 2 nitrogen atom(s) as heteroatom(s) or a benzannulated derivative thereof;
and
R 1 represents a substituted or non-substituted 1-halogencyclopropyl, 1-halogen-2-methylpropan-2-yl or 2-halogen-propan-2-yl;
and/or salt and/or N-oxide thereof.

13. Epoxide of formula (XII)

wherein
X represents a substituted or non-substituted unsaturated 6-membered heterocycle containing 1 or 2 nitrogen atom(s) as heteroatom(s) or a benzannulated derivative thereof;
and
R 1 represents C 1 -C 8 -haloalkyl; C 2 -C 5 -halooalkenyl; C 2 -C 8 -haloalkynyl; C 3 -C 7 -halocycloalkyl-C 1 -C 4 -alkyl; C 3 -C 7 -halocycloalkyl-C 1 -C 4 -haloalkyl; C 3 -C 7 -cycloalkyl-C 1 -C 4 -haloalkyl; substituted or non-substituted C 3 -C 7 -cycloalkyl; substituted or non-substituted C 3 -C 7 -cycloalkenyl; 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; or substituted or non-substituted heterocycloalkyl
and/or salt and/or N-oxide of the epoxide of formula (XII).

14. Compound of formula (V)

wherein
X represents a substituted or non-substituted 3-pyridinyl or 4-pyridinyl or a benzannulated derivative thereof;
and
R 1 represents a substituted or non-substituted 1-C 1 -C 8 -alkylcyclopropyl, 2-C 1 -C 8 -alkylcyclopropyl, C 1 -C 8 -haloalkyl, 1-C 1 -C 8 -alkylcyclohexyl, 1-arylcyclopropyl or 2-arylcyclopropyl;
and/or salt and/or N-oxide of the compound of formula (V).

15. Alcohol of formula (XV)

wherein
X represents a substituted or non-substituted unsaturated 6-membered heterocycle containing 1 or 2 nitrogen atom(s) as heteroatom(s) or a benzannulated derivative thereof,
and
R 1 represents

Assignees

• Bayer Cropscience Ag

Inventors

• Sudau Alexander
• Hoffmann Sebastian
• 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

• A01N43/653

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

• C07D215/14

  Radicals substituted by oxygen atoms · CPC title

• C07D403/06 Primary

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

• A01N43/647

  Triazoles; Hydrogenated triazoles · CPC title

• C07D405/06

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