5-halogenopyrazole biphenylcarboxamides

Patent metadata

Field	Value
Publication number	US-9765034-B2
Application number	US-201314399543-A
Country	US
Kind code	B2
Filing date	May 6, 2013
Priority date	May 9, 2012
Publication date	Sep 19, 2017
Grant date	Sep 19, 2017

Abstract

The present invention relates to novel 1-methyl-3-dihalogenomehtyl-5-halogenopyrazole(thio)biphenyl carboxamides, 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.

First claim

The invention claimed is:

1. A compound of formula (I)

in which
Hal 1 represents a chlorine or fluorine;
Hal 2 represents a chlorine or fluorine;
T represents an oxygen or sulfur atom;
A represents

where the bond marked by * is attached to the amide while the bond marked # is attached to (O) n ;
m represents 0, 1 or 2;
B represents

where the bond marked by * is attached to (O) n while the bond marked # is attached to the imidoyl substituent
s represents 0, 1 or 2;
n represents 0;
R a represents halogen; nitro, cyano, C 1 -C 16 -alkyl; C 1 -C 6 -haloalkyl having 1 to 9 identical or different halogen atoms; C 1 -C 6 -alkoxy; C 1 -C 6 -haloalkoxy having 1 to 9 identical or different halogen atoms; C 1 -C 6 -alkylsulfanyl; C 1 -C 6 -haloalkylsulfanyl having 1 to 9 identical or different halogen atoms; C 1 -C 6 -alkylsulfonyl; C 1 -C 6 -haloalkylsulfonyl having 1 to 9 identical or different halogen atoms; C 2 -C 12 -alkenyl; C 2 -C 12 -alkynyl; C 3 -C 7 -cycloalkyl; tri(C 1 -C 8 )alkylsilyl; tri(C 1 -C 8 )alkylsilyl-C 1 -C 8 -alkyl;
R b represents halogen; nitro, cyano, C 1 -C 16 -alkyl; C 1 -C 6 -haloalkyl having 1 to 9 identical or different halogen atoms; C 1 -C 6 -alkoxy; C 1 -C 6 -haloalkoxy having 1 to 9 identical or different halogen atoms; C 1 -C 6 -alkylsulfanyl; C 1 -C 6 -haloalkylsulfanyl having 1 to 9 identical or different halogen atoms; C 1 -C 6 -alkylsulfonyl; C 1 -C 6 -haloalkylsulfonyl having 1 to 9 identical or different halogen atoms; C 2 -C 12 -alkenyl; C 2 -C 12 -alkynyl; C 3 -C 7 -cycloalkyl; tri(C 1 -C 8 )alkylsilyl; tri(C 1 -C 8 )alkylsilyl-C 1 -C 8 -alkyl;
R 1 represents hydrogen; C 1 -C 16 -alkyl; C 3 -C 8 -cycloalkyl; C 1 -C 6 -haloalkyl having 1 to 9 identical or different halogen atoms; (C 3 -C 8 -cycloalkyl)-C 1 -C 8 -alkyl; (C 3 -C 8 -cycloalkyl)-C 3 -C 8 -cycloalkyl; C 2 -C 8 -alkenyl; C 2 -C 8 -alkynyl; C 2 -C 8 -alkenyl-C 1 -C 16 -alkyl; C 2 -C 8 -alkynyl-C 1 -C 16 -alkyl;
R 2 represents hydrogen; C 1 -C 16 -alkyl; C 3 -C 8 -cycloalkyl; C 1 -C 6 -haloalkyl having 1 to 9 identical or different halogen atoms; (C 3 -C 8 -cycloalkyl)-C 3 -C 8 -cycloalkyl;
R 1 and R 2 furthermore may be linked to form a 5 or 6-member heterocyclic ring;
provided that R 1 and R 2 do not represent simultaneously a methyl group, further provided that R 1 does not represent hydrogen when R 2 represents isopropyl or tert-butyl.

2. The compound of formula (I) according to claim 1 , wherein
Hal 1 represents a chlorine or fluorine;
Hal 2 represents a chlorine or fluorine;
T represents an oxygen atom;
R a represents fluorine, chlorine, methyl or trifluoromethyl;
m represents 0, 1 or 2;
R b represents halogen; nitro, cyano, C 1 -C 12 -alkyl; C 1 -C 4 -haloalkyl having 1 to 9 identical or different halogen atoms; C 1 -C 4 -alkoxy; C 1 -C 4 -haloalkoxy having 1 to 9 identical or different halogen atoms; C 3 -C 6 -cycloalkyl; tri(C 1 -C 4 )alkylsilyl; tri(C 1 -C 4 )alkylsilyl-C 1 -C 6 -alkyl;
s represents 0, 1 or 2;
n represents 0;
R 1 represents hydrogen; C 1 -C 12 -alkyl; C 1 -C 4 -haloalkyl having 1 to 9 identical or different halogen atoms; C 3 -C 6 -cycloalkyl;
R 2 represents hydrogen; C 1 -C 12 -alkyl; C 3 -C 6 -cycloalkyl; C 1 -C 4 -haloalkyl having 1 to 9 identical or different halogen atoms; (C 3 -C 6 -cycloalkyl)-C 3 -C 6 -cycloalkyl;
provided that R 1 and R 2 do not represent simultaneously a methyl group, further provided that R 1 does not represent hydrogen when R 2 represents isopropyl or tert-butyl.

3. The compound of formula (I) according to claim 1 , wherein Hal 1 is fluorine.

4. The compound of formula (I) according to claim 1 , wherein T is oxygen.

5. The compound of formula (I) according to claim 1 , wherein m is 0.

6. The compound of formula (I) according to claim 1 , wherein s is 0.

7. A composition for controlling phytopathogenic harmful fungi, comprising at least one compound of the formula (I) according to claim 1 , and one or more extenders and/or surfactants.

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

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

10. A method for controlling phytopathogenic harmful fungi, wherein compounds of the formula (I)

according to claim 1 are applied to the phytopathogenic harmful fungi and/or their habitat.

11. The method according to claim 10 , wherein seed is treated with the compound of the formula (I).

12. A method according to claim 10 , wherein one or more transgenic plants is treated with the compound of the formula (I).

13. A seed or seed of one or more transgenic plants treated with the compound of formula (I) according to claim 1 .

14. A compound of formula (I),

in which
A represents

where the bond marked by * is attached to the amide while the bond marked # is attached to (O) n ;
B represents

where the bond marked by * is attached to (O) n while the bond marked # is attached to the imidoyl substituent,

wherein
Hal 1 represents a fluorine;
Hal 2 represents a chlorine or fluorine;
T represents an oxygen atom;
R a represents fluorine, chlorine;
m represents 0 or 1;
R b represents methyl, fluorine, chlorine, trifluoromethyl;
s represents 0, 1 or 2;
n represents 0;
R 1 represents hydrogen; methyl, trifluoromethyl;
R 2 represents methyl, ethyl, propyl, i-propyl, propargyl, n-, iso-, sec-, tert-butynyl;
provided that R 1 and R 2 do not represent simultaneously a methyl group, further provided that R 1 does not represent hydrogen when R 2 represents isopropyl or tert-butyl.

15. The compound of formula (I) according to claim 14 , wherein R 1 is hydrogen or methyl.

16. A method for controlling phytopathogenic harmful fungi, wherein compounds of the formula (I) according to claim 14 are applied to the phytopathogenic harmful fungi and/or their habitat.

Assignees

• Bayer Cropscience Ag

Inventors

• Maechling Simon
• Dahmen Peter
• Wachendorff-Neumann Ulrike
• Bernier David
• Carles Lionel
• Dubost Christophe
• Vors Jean-Pierre
• Brunet Stephane
• Lachaise Helene

Classifications

• A01N43/56

  1,2-Diazoles; Hydrogenated 1,2-diazoles · CPC title

• C07D231/16 Primary

  Halogen atoms or nitro radicals · CPC title