5-halogenopyrazole indanyl carboxamides

Patent metadata

Field	Value
Publication number	US-9682937-B2
Application number	US-201615162041-A
Country	US
Kind code	B2
Filing date	May 23, 2016
Priority date	May 9, 2012
Publication date	Jun 20, 2017
Grant date	Jun 20, 2017

Abstract

The present invention relates to novel 1-methyl-3-dihalogenomethyl-5-halogenopyrazole(thio)indanyl 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. Compound according to formula (III-a),

in which
Q represents hydrogen;
X represents halogen, cyclopropyl, or methyl;
m represents 0 or 1;
R 1 , R 2 , R 3 , R 4 , R 5 and R 6 independently of one another represent hydrogen, methyl, ethyl, isopropyl, isobutyl, tert butyl, dimethylpropyl, benzyl, or cyclopentyl,
provided that not all of R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are hydrogen at the same time, and
provided that R 1 , R 5 and R 6 do not represent methyl at the same time when R 2 , R 3 and R 4 represent hydrogen at the same time;
R 3 and R 4 can form together with the carbon to which they are attached a cyclopentyl;
R 5 and R 6 can form together with the carbon to which they are attached an unsubstituted cyclopropyl or an cyclopropyl substituted by chlorine or a group ═N—O—R c , where R c represents methyl ethyl, propyl or butyl.

2. Compound according to formula (III-b),

in which X represents halogen, cyclopropyl, or methyl;
m represents 0 or 1;
R 1 , R 2 , R 3 , R 4 , R 5 and R 6 independently of one another represent hydrogen, methyl, ethyl, isopropyl, isobutyl, tert butyl, dimethylpropyl, benzyl, or cyclopentyl,
provided that not all of R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are hydrogen at the same time, and
provided that R 1 , R 5 and R 6 do not represent methyl at the same time when R 2 , R 3 and R 4 represent hydrogen at the same time;
R 3 and R 4 can form together with the carbon to which they are attached a cyclohexyl;
R 5 and R 6 can form together with the carbon to which they are attached an unsubstituted cyclobutyl or a cyclobutyl substituted by chlorine or a group ═N—O—R c , where R c represents methyl ethyl, propyl or butyl.

3. A compound according to claim 1 , wherein m is zero.

4. A compound according to claim 1 , wherein m is one.

5. A compound according to claim 1 , wherein R3 and R4 form together with the carbon to which they are attached a cyclopentyl.

6. A compound according to claim 1 , wherein R5 and R6 form together with the carbon to which they are attached an unsubstituted cyclopropyl or an cyclopropyl substituted by chlorine or a group ═N—O—Rc, where Rc represents methyl ethyl, propyl or butyl.

7. A compound according to claim 4 , wherein X represents halogen.

8. A compound according to claim 4 , wherein X represents cyclopropyl.

9. A compound according to claim 4 , wherein X represents methyl.

10. A compound according to claim 1 , provided that not more than four of R1, R2, R3, R4, R5 and R6 are hydrogen at the same time.

11. A compound according to claim 2 , wherein m is zero.

12. A compound according to claim 2 , wherein m is one.

13. A compound according to claim 2 , wherein R3 and R4 form together with the carbon to which they are attached a cyclopentyl.

14. A compound according to claim 2 , wherein R5 and R6 form together with the carbon to which they are attached an unsubstituted cyclopropyl or an cyclopropyl substituted by chlorine or a group ═N—O—Rc, where Rc represents methyl ethyl, propyl or butyl.

15. A compound according to claim 12 , wherein X represents halogen.

16. A compound according to claim 12 , wherein X represents cyclopropyl.

17. A compound according to claim 12 , wherein X represents methyl.

18. A compound according to claim 2 , provided that not more than four of R1, R2, R3, R4, R5 and R6 are hydrogen at the same time.

Assignees

• Bayer Cropscience Ag

Inventors

• Coqueron Pierre-Yves
• Maechling Simon
• Es-Sayed Mazen
• Wasnaire Pierre
• Wachendorff-Neumann Ulrike
• Bernier David
• Carles Lionel
• Dubost Christophe
• Vors Jean-Pierre
• Brunet Stephane
• Lachaise Helene
• Genix Pierre

Classifications

• C07D231/16

  Halogen atoms or nitro radicals · CPC title

• C07D413/12

  linked by a chain containing hetero atoms as chain links · CPC title

• A01N43/56

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

• C07C251/50

  having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals · CPC title

• C07D231/14 Primary

  with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms · CPC title