Piperidine pyrazoles as fungicides

Patent metadata

Field	Value
Publication number	US-10004232-B2
Application number	US-201214342606-A
Country	US
Kind code	B2
Filing date	Sep 11, 2012
Priority date	Sep 15, 2011
Publication date	Jun 26, 2018
Grant date	Jun 26, 2018

Abstract

The invention relates to heteroarylpiperidine and -piperazine derivatives of formula (I)

to agrochemically active salts thereof, to their use and also to methods and compositions for controlling phytopathogenic harmful fungi in and/or on plants or in and/or on seed of plants, to methods for producing such compositions and to treated seed, and also to the use thereof for controlling phytopathogenic harmful plants in agriculture, horticulture and forestry, in animal health, in materials protection and also in the household and hygiene sector. The present invention further relates to a method for producing heteroarylpiperidine and -piperazine derivatives.

First claim

The invention claimed is:

1. A compound of formula (I),

in which the definitions of radicals have the following meanings:
Y is oxygen,
R 2 is hydrogen,
Q is

where the bond identified by “x” is bonded directly to the thiazole and the bond identified by “y” is bonded directly to L 1 or R 1 ,
R 5 is hydrogen or methyl,
L 1 is a direct bond,
R 1 is selected from the group consisting of 4,5-dimethyl-2-(prop-2-yn-1-yloxy)phenyl, 2,6-difluoro-3-(prop-2-yn-1-yloxy)phenyl, 2,6-difluoro-4-(prop-2-yn-1-yloxy)phenyl, 3-(allyloxy)-2,6-difluorophenyl, 2,6-difluoro-4-[(methylsulphonyl)amino]phenyl, 6-{[(2Z)-3-chloroprop-2-en-1-yl]oxy}-2,3-difluorophenyl, 6-[(2-chloroprop-2-en-1-yl)oxy]-2,3-difluorophenyl, 2,3-difluoro-6-(prop-2-yn-1-yloxy)phenyl, 4-[(cyclopropylcarbonyl)oxy]-2,6-difluorophenyl, 3,5-difluoro-2-(prop-2-yn-1-yloxy)phenyl, 4-(allyloxy)-2,6-difluorophenyl, 3,6-difluoro-2-(prop-2-yn-1-yloxy)phenyl, 2,4-difluoro-6-(prop-2-yn-1-yloxy)phenyl, 2,6-difluoro-4-formylphenyl, 2-(cyclopropylmethoxy)-4,6-difluorophenyl, 2-[(cylcopropylcarbonyl)oxy]-4,6-difluorophenyl, 6-(allyloxy)-2,3-difluorophenyl, 2-(allyloxy)-4,6-dichlorophenyl, 2-[(2-chloroprop-2-en-1-yl)oxy]-4,6-difluorophenyl, 2-(allyloxy)-4,6-difluorophenyl, and 2,4-dichloro-6-(prop-2-yn-1-yloxy)phenyl,
and/or a salt, metal complex and/or N-oxide of a compound of formula (I).

2. A compound of formula (I) and/or a salt, metal complex and/or N-oxide thereof according to claim 1 , wherein R 5 is methyl.

3. A compound of formula (I) and/or a salt, metal complex and/or N-oxide thereof according to claim 1 , wherein
Y is oxygen;
R 2 is hydrogen;
Q is Q-3;
R 5 is hydrogen;
L 1 is a direct bond;
R 1 is 4,5-dimethyl-2-(prop-2-yn-1-yloxy)phenyl or
R 1 is 2,6-difluoro-3-(prop-2-yn-1-yloxy)phenyl or
R 1 is 2,6-difluoro-4-(prop-2-yn-1-yloxy)phenyl or
R 1 is 2,6-difluoro-4-[(methylsulphonyl)amino]phenyl or
R 1 is 3-(allyloxy)-2,6-difluorophenyl or
R 1 is 4-(allyloxy)-2,6-difluorophenyl.

4. A method for controlling phytopathogenic harmful fungi, comprising delivering a compound of formula (I) and/or a salt, metal complex and/or N oxide thereof according to claim 1 to the phytopathogenic harmful fungi and/or a habitat thereof.

5. A composition for controlling phytopathogenic harmful fungi, comprising at least one compound of formula (I) and/or a salt, metal complex and/or N oxide thereof according to claim 1 , and at least one extender and/or surfactant.

6. A compound and/or a salt, metal complex and/or N oxide of formula (I) according to claim 1 capable of being used for controlling phytopathogenic harmful fungi in agriculture, horticulture and forestry, in animal health, in materials protection and/or in a household and/or hygiene sector.

7. A method for producing a composition for controlling phytopathogenic harmful fungi, comprising mixing a compound of formula (I) and/or a salt, metal complex and/or N oxide according to claim 1 with at least one extender and/or surfactant.

8. The method according to claim 4 wherein the at least one compound and/or salt, metal complex and/or N oxide of formula (I) is applied to a transgenic plant.

9. The method according to claim 4 wherein the at least one compound and/or salt, metal complex and/or N oxide of formula (I) is applied to seed and/or seed of a transgenic plant.

10. A compound of formula (I) and/or a salt, metal complex and/or N-oxide thereof according to claim 1 , wherein
R 1 is selected from the group consisting of 4,5-dimethyl-2-(prop-2-yn-1-yloxy)phenyl, 2,6-difluoro-3-(prop-2-yn-1-yloxy)phenyl, 2,6-difluoro-4-(prop-2-yn-1-yloxy)phenyl, 3-(allyloxy)-2,6-difluorophenyl, 2,6-difluoro-4-[(methylsulphonyl)amino]phenyl, 6-[(2-chloroprop-2-en-1-yl)oxy]-2,3-difluorophenyl, 2,3-difluoro-6-(prop-2-yn-1-yloxy)phenyl, 2,4-difluoro-6-(prop-2-yn-1-yloxy)phenyl, 6-(allyloxy)-2,3-difluorophenyl, 2-(allyloxy)-4,6-dichlorophenyl, 2-[(2-chloroprop-2-en-1-yl)oxy]-4,6-difluorophenyl, 2-(allyloxy)-4,6-difluorophenyl and 2,4-dichloro-6-(prop-2-yn-1-yloxy)phenyl.

11. The method according to claim 4 wherein the at least one compound and/or salt, metal complex and/or N oxide of formula (I) is applied to a fruit or vegetable.

12. The compound of formula (I) and/or a salt, metal complex and/or N-oxide thereof according to claim 1 , wherein
Y is oxygen;
R 2 is hydrogen;
Q is Q-3;
R 5 is hydrogen;
L 1 is a direct bond; and
R 1 is 4-(allyloxy)-2,6-difluorophenyl.

13. A method for controlling phytopathogenic harmful fungi, comprising delivering a compound of formula (I) and/or a salt, metal complex and/or N oxide thereof according to claim 12 to the phytopathogenic harmful fungi and/or a habitat thereof.

14. A composition for controlling phytopathogenic harmful fungi, comprising at least one compound of formula (I) and/or a salt, metal complex and/or N oxide thereof according to claim 12 , and at least one extender and/or surfactant.

Assignees

• Hillebrand Stefan
• Tsuchiya Tomoki
• Hoffmann Sebastian
• Cristau Pierre
• Wasnaire Pierre
• Seitz Thomas
• Benting Juergen
• Wachendorff Neumann Ulrike
• Schmidt Peter Jan
• Bayer Ip Gmbh

Inventors

• Hillebrand Stefan
• Tsuchiya Tomoki
• Hoffmann Sebastian
• Cristau Pierre
• Wasnaire Pierre
• Seitz Thomas
• Benting Juergen
• Wachendorff-Neumann Ulrike
• Schmidt Peter Jan

Classifications

• C07D417/14 Primary

  containing three or more hetero rings · CPC title

• A01N43/78

  1,3-Thiazoles; Hydrogenated 1,3-thiazoles · CPC title

• A01N43/80 Primary

  five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2 · CPC title

• C07D231/12

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms · CPC title