Halogen-substituted compounds

Patent metadata

Field	Value
Publication number	US-9936699-B2
Application number	US-201515501733-A
Country	US
Kind code	B2
Filing date	Aug 5, 2015
Priority date	Aug 8, 2014
Publication date	Apr 10, 2018
Grant date	Apr 10, 2018

Abstract

The invention relates inter alia to halogen-substituted compounds of the general formula (I) in which the substituents A 1 , R 1 -R 3 and Z 1 -Z 3 have the meanings given in the description. Also described are processes for preparing the compounds of the formula (I) and possible intermediates for the preparation of these compounds. The compounds according to the invention are particularly suitable for controlling insects, arachnids and nematodes in agriculture and ectoparasites in veterinary medicine.

First claim

The invention claimed is:

1. A compound of formula (I),

in which
Z 1 represents perhalogenated (C 1 -C 2 )-alkyl;
Z 2 represents —S(O) 0-2 —(C 1 -C 2 )-alkyl or —S(O) 0-2 —(C 1 -C 2 )-halogenalkyl;
Z 3 represents (C 1 -C 2 )-alkyl;
R 1 represents hydrogen (H) or (C 1 -C 2 )-alkyl;
R 2 represents H or cyano (CN);
R 3 represents CH 3 or chlorine (Cl); and
A 1 represents CH or nitrogen (N)
with the proviso that the two compounds characterized by the following combinations are excluded:

Z 1
Z 2
Z 3
R 1
A 1
R 3
R 2

—CF 3
—S(O)—CH 3
—CH 3
—H
C—H
—Cl
—CN

—CF 2 CF 3
—S—CH 3
—CH 3
—H
C—H
—Cl
—CN.

2. A compound according to claim 1 , wherein A 1 is CH.

3. A compound according to claim 1 , wherein A 1 is CH and R 3 is Cl.

4. A compound according to claim 1 , wherein
Z 1 is CF 3 or C 2 F 5 ;
Z 2 is —S—CH 3 —S—C 2 H 5 , —S—CF 3 , —S—CH 2 —CF 3 , —SO—CH 3 , SO 2 —CH 3 , —SO—C 2 H 5 or —SO 2 —C 2 H 5 ; and
Z 3 is CH 3 .

5. A compound according to claim 1 , wherein
Z 1 is CF 3 or C 2 F 5 ;
Z 2 is —S—CH 2 CF 3 , —SO—CH 2 CF 3 , or SO 2 —CH 2 CF 3 ; and
Z 3 is CH 3 .

6. A compound according to claim 1 , wherein R 1 is H.

7. A compound according to claim 1 , wherein A 1 is N.

8. A compound according to claim 1 , wherein R 3 is Cl.

9. A method for controlling one or more insects, arachnids, and/or nematodes comprising applying a compound of formula (I) according to claim 1 to the one or more insects, arachnids and/or nematodes.

10. A pharmaceutical composition comprising at least one compound according to claim 1 .

11. A medicament for the treatment of parasites in an animal comprising a compound according to claim 1 .

12. A method for preparing a pharmaceutical composition for controlling parasites on one or more animals comprising combining a compound according to claim 1 with auxiliaries or further active compounds.

13. A compound selected from the group consisting of

14. A method for controlling one or more pests, comprising applying a compound according to claim 1 to the pests and/or a habitat thereof.

15. A method for protecting a propagation material of one or more plants comprising applying a compound according to claim 1 to the propagation material of one or more plants or its habitat.

16. A method for protecting one or more plants and/or plant parts, comprising applying a compound according to claim 1 to the one or more plants and/or plant parts, their surroundings, habitat, or storage space.

17. A method for controlling parasites in livestock, breeding, zoo, laboratory, experimental, or domestic animal comprising administering a compound according to claim 1 to the animal.

18. A compound according to claim 1 , wherein
Z 1 is CF 3 or C 2 F 5 ;
Z 2 is —S—CH 3 —S—C 2 H 5 , —SO—CH 3 , SO 2 —CH 3 , or —SO—C 2 H 5 ;
Z 3 is CH 3 ;
A 1 is CH or N;
R 1 is H;
R 2 is CN or H; and
R 3 is Cl or CH 3 .

Assignees

• Bayer Cropscience Ag

Inventors

• Maue Michael
• Harschneck Tobias
• Hahn Julia Johanna
• Bretschneider Thomas
• Decor Anne
• Fischer Reiner
• Hallenbach Werner
• Schwarz Hans-Georg
• Velten Robert
• Böhnke Niels
• Malsam Olga
• Görgens Ulrich
• Horstmann Sebastian
• Raming Klaus
• Köbberling Johannes
• Hübsch Walter

Classifications

• A61P33/00

  Antiparasitic agents · CPC title

• A01N43/56 Primary

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

• C07D231/16

  Halogen atoms or nitro radicals · CPC title

• C07D231/38

  Nitrogen atoms (nitro radicals C07D231/16) · CPC title

• C07D231/18

  One oxygen or sulfur atom · CPC title