Triazole derivatives

Patent metadata

Field	Value
Publication number	US-9668481-B2
Application number	US-201414782801-A
Country	US
Kind code	B2
Filing date	Apr 9, 2014
Priority date	Apr 12, 2013
Publication date	Jun 6, 2017
Grant date	Jun 6, 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 substituted or non-substituted C 1 -C 8 -alkyl; substituted or non-substituted C 4 -C 8 -cycloalkylalkyl; substituted or non-substituted C 2 -C 8 -alkenyl; substituted or non-substituted C 2 -C 8 -alkynyl;
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; substituted or 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 6-membered heterocycle containing 1 or 2 nitrogen atom(s) as heteroatom(s) or a benzannulated derivative thereof; and/or 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 substituted or non-substituted C 1 -C 8 -alkyl; substituted or non-substituted C 4 -C 8 -cycloalkylalkyl; substituted or non-substituted C 2 -C 8 -alkenyl; substituted or non-substituted C 2 -C 8 -alkynyl;
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; substituted or 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 6 membered heterocycle containing 1 or 2 nitrogen atom(s) as heteroatom(s) or a benzannulated derivative thereof, with the proviso 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 substituted or non-substituted C 1 -C 8 -alkyl;
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 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. 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.

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. The composition according to claim 6 for control of phytopathogenic harmful fungi.

9. Process for producing a composition for controlling one or more harmful microorganisms, comprising mixing a compound of formula (I) according to claim 1 with one or more extenders and/or surfactants.

10. The method of claim 4 comprising treatment of one or more transgenic plants.

11. Seed treated with the 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 3-pyridinyl or 4-pyridinyl or a benzannulated derivative thereof;
and
R 1 represents 2-methyl-butan-2-yl, 3-methyl-pentan-3-yl or 2,3-dimethyl-butan-2-yl; and/or a 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 substituted or non-substituted C 2 -C 8 -alkyl; substituted or non-substituted C 4 -C 8 -cycloalkylalkyl; substituted or non-substituted C 2 -C 8 -alkenyl; substituted or non-substituted C 2 -C 8 -alkynyl; and/or a salt and/or N-oxide thereof.

14. 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;
R 1 represents substituted or non-substituted C 1 -C 8 -alkyl; substituted or non-substituted C 4 -C 8 -cycloalkylalkyl; substituted or non-substituted C 2 -C 8 -alkenyl; substituted or non-substituted C 2 -C 8 -alkynyl;
and
A represents chlorine, bromine, iodine, O—SO 2 — C 1 -C 8 -alkyl or O—SO 2 -aryl; and/or a salt and/or N-oxide thereof.

Assignees

• Bayer Cropscience Ag

Inventors

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

Classifications

• C07D403/06

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

• A01N43/653 Primary

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

• A01N47/02

  the carbon atom having no bond to a nitrogen atom · CPC title

• C07D213/61

  Halogen atoms or nitro radicals · CPC title

• C07D213/50

  Ketonic radicals · CPC title