IP Library › Granted Patent US 9,066,945
Granted Patent B2
US 9,066,945 · App. 13/995,958 · Granted Jun 30, 2015

Ectoparasiticidal active substance combinations

Inventors: Andreas Turberg (Haan, DE); Ulrich Görgens (Ratingen, DE); Hans-Georg Schwarz (Dorsten, DE); Stefan Werner (Berlin, DE)
Assignee: Bayer Intellectual Property GmbH
A61K31/497A01N43/60C07D401/14C07D403/04C07D403/14C07D405/14A61K45/06
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Quick Facts
Patent No.
US 9,066,945
App. No.
13/995,958
Granted
Jun 30, 2015
Kind
B2
Abstract

The present application relates to active compound combinations of pyrazin-2-ylpyrazoles (component A) with at least one further ectoparasiticide or synergists (component B), and to products comprising such active compound combinations. These active compound combinations are suitable for controlling animal pests in the field of veterinary medicine.

Claims (76)

1. A veterinary pharmaceutical combination comprising, as component A, a compound of the general formula (I)

in which

X represents phenyl, 2-pyridyl or 3-pyridyl, each of which is substituted by one or more substituents selected from the group consisting of halogen, alkyl, haloalkyl, alkoxy, alkoxyalkyl, alkoxyalkoxy, cycloalkyl, alkenyloxy, alkynyloxy, benzyloxy, cycloalkylalkoxy, haloalkoxy, haloalkoxyalkyl, alkylsulphanyl, haloalkylsulphanyl, alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyl, haloalkylsulphonyl, cyano, nitro, alkylcarbonyl, alkoxycarbonyl, alkoxycarbonylalkyl, carboxyl, carboxamide, dialkylcarboxamide, trialkylsilyl, amino, alkylamino, dialkyl-amino, alkylsulphonylamino, dialkylsulphonylamino, formyl, —CH═NO—H, —CH═NO-alkyl, —CH═NO-halolkyl, —C(CH 3 )═NO—H, —C(CH 3 )═NO-alkyl, —C(CH 3 )═NO-haloalkyl; and phenyl, 2-pyridyl and 3-pyridyl which are optionally substituted by one or more halogen atoms, cyano, nitro, alkyl, alkoxy or haloalkyl, where vicinal alkyl, haloalkyl, alkoxy and/or haloalkoxy groups at the phenyl substituent, 2-pyridyl substituent or 3-pyridyl substituent together with the carbon atoms to which they are attached may form a five- to six-membered cyclic system which contains 0 to oxygen or nitrogen atoms, where two oxygen atoms are not directly attached to one another, and whose alkyl moiety may optionally be substituted by one or more halogen atoms and/or further alkyl radicals,

R 1 represents alkyl which is optionally monosubstituted or independently polysubstituted by alkoxy, haloalkoxy, alkylsulphanyl, haloalkylsulphanyl, alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyl, haloalkylsulphonyl, alkylcarbonyl, alkoxycarbonyl, hydroxyl and/or cycloalkyl; alkenyl which is optionally monosubstituted or independently polysubstituted by halogen, alkoxy, haloalkoxy, alkylsulphanyl, haloalkylsulphanyl, alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyl, haloalkylsulphonyl, alkylcarbonyl, alkoxycarbonyl and/or cycloalkyl; cycloalkyl which is optionally monosubstituted or independently polysubstituted by alkyl, haloalkyl and/or halogen; haloalkyl which is optionally monosubstituted or independently polysubstituted by alkoxy, alkylsulphanyl, haloalkylsulphanyl, alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyl, haloalkylsulphonyl and/or phenyl which is optionally monosubstituted or independently polysubstituted by halogen, alkyl, haloalkyl and/or alkoxy; phenyl which is optionally monosubstituted or independently polysubstituted by halogen, alkyl, haloalkyl and/or alkoxy; benzyl which is optionally monosubstituted or independently polysubstituted by halogen, alkyl, haloalkyl and/or alkoxy; cyano, formyl, alkylcarbonyl, —CH═NO—H, —CH═NO-alkyl, —CH═NO-haloalkyl, —C(CH 3 )═NO—H, —C(CH 3 )═NO-alkyl or —C(CH 3 )═NO-haloalkyl,

R 2 represents optionally substituted amino, where amino may be monosubstituted or independently disubstituted by alkyl, haloalkyl, alkoxyalkyl, alkylsulphanylalkyl, alkylsulphinylalkyl, alkylsulphonylalkyl, alkylcarbonyl, cycloalkyl, cycloalkylalkyl, alkenyl, where the radicals listed above are optionally substituted by halogen, cyano, alkoxy, alkoxycarbonyl and phenyl, where the phenyl ring is optionally mono- or polysubstituted by one or more substituents independently of one another selected from the group consisting of halogen, alkyl, haloalkyl and alkoxy; alkynyl, alkoxycarbonyl, alkenyloxycarbonyl, alkinyloxycarbonyl, alkoxycarbonylalkyl, alkoxycarbonylcarbonyl, heterocyclyl, heteroaryl, heterocyclylalkyl or heteroarylalkyl, where the heterocyclic or heteroaromatic ring may optionally be mono- or polysubstituted by one or more substituents independently of one another selected from the group consisting of halogen, alkyl, haloalkyl and alkoxy; benzyl or phenylcarbonyl, where the phenyl ring in benzyl and phenylcarbonyl is optionally mono- or polysubstituted by one or more substituents independently of one another selected from the group consisting of halogen, alkyl, haloalkyl and alkoxy, and

R 3 , R 4 independently of one another represent hydrogen, halogen, alkyl, cycloalkyl, haloalkyl, cyano, hydroxyl, formyl, alkylcarbonyl, —CH═NO—H, —CH═NO-alkyl, —CH═NO-halo-alkyl, —C(CH 3 )═NO—H, —C(CH 3 )═NO-alkyl, —C(CH 3 )═NO-haloalkyl, nitro, hydroxyl, SH, alkoxy, alkylsulphanyl, haloalkylsulphanyl, alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyl or haloalkylsulphonyl,

R 5 represents halogen, alkyl, haloalkyl, hydroxyl, alkoxy, alkoxyalkyl, alkoxyalkoxy, cycloalkyl, alkenyloxy, alkynyloxy, benzyloxy, cycloalkylalkoxy, haloalkoxy, haloalkoxyalkyl, —SH, alkyl-sulphanyl, haloalkylsulphanyl, alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyl, haloalkylsulphonyl, cyano, nitro, alkylcarbonyl, alkoxycarbonyl, alkoxycarbonylalkyl, carboxyl, carboxamide, dialkylcarboxamide, trialkylsilyl, amino, alkylamino, dialkylamino, alkylsulphonylamino, dialkylsulphonylamino, formyl, —CH═NO—H, —CH═NO-alkyl, —CH═NO-haloalkyl, —C(CH 3 )═NO—H, —C(CH 3 )═NO-alkyl, —C(CH 3 )═NO-haloalkyl, heteroaryl, where the heteroaromatic ring may optionally be mono- or polysubstituted by one or more substituents independently of one another selected from the group consisting of halogen, alkyl, haloalkyl and alkoxy,

or N-oxides or salts thereof,

and, as component B, an active compound selected from the group consisting of: (I-1) acetylcholinesterase (AChE) inhibitors; (I-2) GABA-gated chloride channel antagonists; (I-3) sodium channel modulators/voltage-dependent sodium channel blockers; (I-4) nicotinergic acetylcholine receptor agonists; (I-5) allosteric acetylcholine receptor modulators (agonists); (I-6) chloride channel activators; (I-7) juvenile hormone analogues; (I-8) mite growth inhibitors; (I-9) Slo-1 and latrophilin receptor agonists; (I-10) oxidative phosphorylation inhibitors, ATP disruptors; (I-12) nicotinergic acetylcholine receptor antagonists; (I-13) chitin biosynthesis inhibitors, type 0; (I-14) chitin biosynthesis inhibitors, type 1; (I-15) moulting disruptors; (I-16) ecdysone agonists/disruptors; (I-17) octopaminergic agonists; (I-18) complex-III electron transport inhibitors; (I-19) complex-I electron transport inhibitors; (I-20) voltage-dependent sodium channel blockers; (I-21) inhibitors of acetyl-CoA carboxylase; (I-22) complex-II electron transport inhibitors; (I-23) ryanodine receptor effectors; (I-24) active compounds selected from benzoximate, chinomethionat, cyflumetofen, pyridalyl, sulfoxaflor, and penigequinolone A; and (I-25) synergists MGK264 and piperonyl butoxide (PBO).

2. The combination according to claim 1 , comprising, as component B, an active compound selected from the group consisting of: (I-2) GABA-gated chloride channel antagonists; (I-3) sodium channel modulators/voltage-dependent sodium channel blockers; (I-4) nicotinergic acetylcholine receptor agonists; (I-5) allosteric acetylcholine receptor modulators (agonists); (I-6) chloride channel activators; (I-17) octopaminergic agonists; and (I-25) synergists MGK264 and piperonyl butoxide (PBO).

3. The combination according to claim 1 , comprising, as component A, a compound selected from the group consisting of:

A-1

4-(7-chloro-1,3-benzodioxol-5-yl)-1-(3-ethoxypyrazin-2-yl)-3-

(trifluoromethyl)-1H-pyrazole-5-amine

A-2

4-(7-chloro-1,3-benzodioxol-5-yl)-1-(3-methoxypyrazin-2-yl)-3-

(trifluoromethyl)-1H-pyrazole-5-amine

A-3

4-(7-chloro-1,3-benzodioxol-5-yl)-1-(3-methoxypyrazin-2-yl)-

3-methyl-1H-pyrazole-5-amine

A-4

4-(7-chloro-1,3-benzodioxol-5-yl)-1-(3-ethoxypyrazin-2-yl)-

3-ethyl-1H-pyrazole-5-amine

A-5

4-(7-chloro-1,3-benzodioxol-5-yl)-1-(3-methoxypyrazin-2-yl)-

3-ethyl-1H-pyrazole-5-amine

A-6

4-(7-chloro-1,3-benzodioxol-5-yl)-1-(3-methoxypyrazin-2-yl)-

3-isopropyl-1H-pyrazole-5-amine

A-7

4-(7-chloro-1,3-benzodioxol-5-yl)-1-(3-methoxypyrazin-2-yl)-

3-cyclopropyl-1H-pyrazole-5-amine

A-8

4-(7-bromo-1,3-benzodioxol-5-yl)-1-(3-ethoxypyrazin-2-yl)-

3-(trifluoromethyl)-1H-pyrazole-5-amine

A-9

4-(7-bromo-1,3-benzodioxol-5-yl)-1-(3-methoxypyrazin-2-yl)-

3-(trifluoromethyl)-1H-pyrazole-5-amine

A-10

4-(7-bromo-1,3-benzodioxol-5-yl)-1-(3-ethoxypyrazin-2-yl)-

3-ethyl-1H-pyrazole-5-amine

A-11

4-(7-bromo-1,3-benzodioxol-5-yl)-1-(3-methoxypyrazin-2-yl)-

3-ethyl-1H-pyrazole-5-amine

A-12

1-(3-ethoxypyrazin-2-yl)-3-(triluoromethyl)-4-[7-

(trifluoromethyl)-1,3-benzodioxol-5-yl]-1H-pyrazole-5-amine

A-13

1-(3-methoxypyrazin-2-yl)-3-(triluoromethyl)-4-[7-

(trifluoromethyl)-1,3-benzodioxol-5-yl]-1H-pyrazole-5-amine

A-14

4-(3,5-dichloro-4-methoxyphenyl)-1-(3-ethoxypyrazin-2-yl)-3-

(trifluoromethyl)-1H-pyrazole-5-amine; and

A-15

4-[3,5-dichloro-4-(dimethylamino)phenyl]-1-(3-ethoxypyrazin-

2-yl)-3-(trifluoromethyl)-1H-pyrazole-5-amine.

4. The combination according to claim 1 , comprising, as component B, a compound selected from the group consisting of: endosulphan (alpha-), lindane; fipronil, pyriprole; A1443; allethrin, bioallethrin, permethrin, phenothrin, resmethrin, tetramethrin; cyfluthrin (beta-), cyhalothrin (lambda-), cypermethrin (alpha-, zeta-), deltamethrin, fenvalerate, flucythrinate, flumethrin, fluvalinate (tau-); etofenprox, silafluofen; chlothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid; spinosad, spinetoram; doramectin, eprinomectin, ivermectin, milbemycin oxime, moxidectin, selamectin; amitraz, cymiazole, demiditraz; piperonyl butoxide, and MGK264.

5. The combination according to claim 1 , wherein A is 4-(3,5-Dichloro-4-methoxyphenyl)-1-(3-ethoxypyrazin-2-yl)-3-(trifluoromethyl)-1H-pyrazole-5-amine.

6. The combination according to claim 1 , wherein A is 4-[3,5-Dichloro-4-(dimethylamino)phenyl]-1-(3-ethoxypyrazin-2-yl)-3-(trifluoromethyl)-1H-pyrazole-5-amine.

7. A method for controlling ectoparasites comprising administering to an animal in need thereof an effective amount of a combination according to claim 1 .

8. The method according to claim 7 , wherein components A and B of the combination are administered simultaneously.

9. The combination according to claim 1 , wherein A is 4-(7-chloro-1,3-benzodioxol-5-yl)-1-(3-ethoxypyrazin-2-yl)-3-(trifluoromethyl)-1H-pyrazole-5-amine, and B is selected from the group consisting of: endosulphan (alpha-), lindane; fipronil, pyriprole; A1443; allethrin, bioallethrin, permethrin, phenothrin, resmethrin, tetramethrin; cyfluthrin (beta-), cyhalothrin (lambda-), cypermethrin (alpha-, zeta-), deltamethrin, fenvalerate, flucythrinate, flumethrin, fluvalinate (tau-); etofenprox, silafluofen; chlothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid; spinosad, spinetoram; doramectin, eprinomectin, ivermectin, milbemycin oxime, moxidectin, selamectin; amitraz, cymiazole, demiditraz; piperonyl butoxide, and MGK264.

10. The combination according to claim 1 , wherein A is 4-(7-chloro-1,3-benzodioxol-5-yl)-1-(3-methoxypyrazin-2-yl)-3-(trifluoromethyl)-1H-pyrazole-5-amine, and B is selected from the group consisting of: endosulphan (alpha-), lindane; fipronil, pyriprole; A1443; allethrin, bioallethrin, permethrin, phenothrin, resmethrin, tetramethrin; cyfluthrin (beta-), cyhalothrin (lambda-), cypermethrin (alpha-, zeta-), deltamethrin, fenvalerate, flucythrinate, flumethrin, fluvalinate (tau-); etofenprox, silafluofen; chlothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid; spinosad, spinetoram; doramectin, eprinomectin, ivermectin, milbemycin oxime, moxidectin, selamectin; amitraz, cymiazole, demiditraz; piperonyl butoxide, and MGK264.

11. The combination according to claim 1 , wherein A is 4-(7-chloro-1,3-benzodioxol-5-yl)-1-(3-methoxypyrazin-2-yl)-3-methyl-1H-pyrazole-5-amine, and B is selected from the group consisting of: endosulphan (alpha-), lindane; fipronil, pyriprole; A1443; allethrin, bioallethrin, permethrin, phenothrin, resmethrin, tetramethrin; cyfluthrin (beta-), cyhalothrin (lambda-), cypermethrin (alpha-, zeta-), deltamethrin, fenvalerate, flucythrinate, flumethrin, fluvalinate (tau-); etofenprox, silafluofen; chlothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid; spinosad, spinetoram; doramectin, eprinomectin, ivermectin, milbemycin oxime, moxidectin, selamectin; amitraz, cymiazole, demiditraz; piperonyl butoxide, and MGK264.

12. The combination according to claim 1 , wherein A is 4-(7-chloro-1,3-benzodioxol-5-yl)-1-(3-ethoxypyrazin-2-yl)-3-ethyl-1H-pyrazole-5-amine, and B is selected from the group consisting of: endosulphan (alpha-), lindane; fipronil, pyriprole; A1443; allethrin, bioallethrin, permethrin, phenothrin, resmethrin, tetramethrin; cyfluthrin (beta-), cyhalothrin (lambda-), cypermethrin (alpha-, zeta-), deltamethrin, fenvalerate, flucythrinate, flumethrin, fluvalinate (tau-); etofenprox, silafluofen; chlothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid; spinosad, spinetoram; doramectin, eprinomectin, ivermectin, milbemycin oxime, moxidectin, selamectin; amitraz, cymiazole, demiditraz; piperonyl butoxide, and MGK264.

13. The combination according to claim 1 , wherein A is 4-(7-chloro-1,3-benzodioxol-5-yl)-1-(3-methoxypyrazin-2-yl)-3-ethyl-1H-pyrazole-5-amine, and B is selected from the group consisting of: endosulphan (alpha-), lindane; fipronil, pyriprole; A1443; allethrin, bioallethrin, permethrin, phenothrin, resmethrin, tetramethrin; cyfluthrin (beta-), cyhalothrin (lambda-), cypermethrin (alpha-, zeta-), deltamethrin, fenvalerate, flucythrinate, flumethrin, fluvalinate (tau-); etofenprox, silafluofen; chlothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid; spinosad, spinetoram; doramectin, eprinomectin, ivermectin, milbemycin oxime, moxidectin, selamectin; amitraz, cymiazole, demiditraz; piperonyl butoxide, and MGK264.

14. The combination according to claim 1 , wherein A is 4-(7-chloro-1,3-benzodioxol-5-yl)-1-(3-methoxypyrazin-2-yl)-3-isopropyl-1H-pyrazole-5-amine, and B is selected from the group consisting of: endosulphan (alpha-), lindane; fipronil, pyriprole; A1443; allethrin, bioallethrin, permethrin, phenothrin, resmethrin, tetramethrin; cyfluthrin (beta-), cyhalothrin (lambda-), cypermethrin (alpha-, zeta-), deltamethrin, fenvalerate, flucythrinate, flumethrin, fluvalinate (tau-); etofenprox, silafluofen; chlothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid; spinosad, spinetoram; doramectin, eprinomectin, ivermectin, milbemycin oxime, moxidectin, selamectin; amitraz, cymiazole, demiditraz; piperonyl butoxide, and MGK264.

15. The combination according to claim 1 , wherein A is 4-(7-chloro-1,3-benzodioxol-5-yl)-1-(3-methoxypyrazin-2-yl)-3-cyclopropyl-1H-pyrazole-5-amine, and B is selected from the group consisting of: endosulphan (alpha-), lindane; fipronil, pyriprole; A1443; allethrin, bioallethrin, permethrin, phenothrin, resmethrin, tetramethrin; cyfluthrin (beta-), cyhalothrin (lambda-), cypermethrin (alpha-, zeta-), deltamethrin, fenvalerate, flucythrinate, flumethrin, fluvalinate (tau-); etofenprox, silafluofen; chlothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid; spinosad, spinetoram; doramectin, eprinomectin, ivermectin, milbemycin oxime, moxidectin, selamectin; amitraz, cymiazole, demiditraz; piperonyl butoxide, and MGK264.

16. The combination according to claim 1 , wherein A is 4-(7-bromo-1,3-benzodioxol-5-yl)-1-(3-ethoxypyrazin-2-yl)-3-(trifluoromethyl)-1H-pyrazole-5-amine, and B is selected from the group consisting of: endosulphan (alpha-), lindane; fipronil, pyriprole; A1443; allethrin, bioallethrin, permethrin, phenothrin, resmethrin, tetramethrin; cyfluthrin (beta-), cyhalothrin (lambda-), cypermethrin (alpha-, zeta-), deltamethrin, fenvalerate, flucythrinate, flumethrin, fluvalinate (tau-); etofenprox, silafluofen; chlothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid; spinosad, spinetoram; doramectin, eprinomectin, ivermectin, milbemycin oxime, moxidectin, selamectin; amitraz, cymiazole, demiditraz; piperonyl butoxide, and MGK264.

17. The combination according to claim 1 , wherein A is 4-(7-bromo-1,3-benzodioxol-5-yl)-1-(3-methoxypyrazin-2-yl)-3-(trifluoromethyl)-1H-pyrazole-5-amine, and B is selected from the group consisting of: endosulphan (alpha-), lindane; fipronil, pyriprole; A1443; allethrin, bioallethrin, permethrin, phenothrin, resmethrin, tetramethrin; cyfluthrin (beta-), cyhalothrin (lambda-), cypermethrin (alpha-, zeta-), deltamethrin, fenvalerate, flucythrinate, flumethrin, fluvalinate (tau-); etofenprox, silafluofen; chlothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid; spinosad, spinetoram; doramectin, eprinomectin, ivermectin, milbemycin oxime, moxidectin, selamectin; amitraz, cymiazole, demiditraz; piperonyl butoxide, and MGK264.

18. The combination according to claim 1 , wherein A is 4-(7-bromo-1,3-benzodioxol-5-yl)-1-(3-ethoxypyrazin-2-yl)-3-ethyl-1H-pyrazole-5-amine, and B is selected from the group consisting of: endosulphan (alpha-), lindane; fipronil, pyriprole; A1443; allethrin, bioallethrin, permethrin, phenothrin, resmethrin, tetramethrin; cyfluthrin (beta-), cyhalothrin (lambda-), cypermethrin (alpha-, zeta-), deltamethrin, fenvalerate, flucythrinate, flumethrin, fluvalinate (tau-); etofenprox, silafluofen; chlothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid; spinosad, spinetoram; doramectin, eprinomectin, ivermectin, milbemycin oxime, moxidectin, selamectin; amitraz, cymiazole, demiditraz; piperonyl butoxide, and MGK264.

19. The combination according to claim 1 , wherein A is 4-(7-bromo-1,3-benzodioxol-5-yl)-1-(3-methoxypyrazin-2-yl)-3-ethyl-1H-pyrazole-5-amine, and B is selected from the group consisting of: endosulphan (alpha-), lindane; fipronil, pyriprole; A1443; allethrin, bioallethrin, permethrin, phenothrin, resmethrin, tetramethrin; cyfluthrin (beta-), cyhalothrin (lambda-), cypermethrin (alpha-, zeta-), deltamethrin, fenvalerate, flucythrinate, flumethrin, fluvalinate (tau-); etofenprox, silafluofen; chlothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid; spinosad, spinetoram; doramectin, eprinomectin, ivermectin, milbemycin oxime, moxidectin, selamectin; amitraz, cymiazole, demiditraz; piperonyl butoxide, and MGK264.

20. The combination according to claim 1 , wherein A is 1-(3-ethoxypyrazin-2-yl)-3-(triluoromethyl)-4-[7-(trifluoromethyl)-1,3-benzodioxol-5-yl]-1H-pyrazole-5-amine, and B is selected from the group consisting of: endosulphan (alpha-), lindane; fipronil, pyriprole; A1443; allethrin, bioallethrin, permethrin, phenothrin, resmethrin, tetramethrin; cyfluthrin (beta-), cyhalothrin (lambda-), cypermethrin (alpha-, zeta-), deltamethrin, fenvalerate, flucythrinate, flumethrin, fluvalinate (tau-); etofenprox, silafluofen; chlothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid; spinosad, spinetoram; doramectin, eprinomectin, ivermectin, milbemycin oxime, moxidectin, selamectin; amitraz, cymiazole, demiditraz; piperonyl butoxide, and MGK264.

21. The combination according to claim 1 , wherein A is 1-(3-methoxypyrazin-2-yl)-3-(triluoromethyl)-4-[7-(trifluoromethyl)-1,3-benzodioxol-5-yl]-1H-pyrazole-5-amine, and B is selected from the group consisting of: endosulphan (alpha-), lindane; fipronil, pyriprole; A1443; allethrin, bioallethrin, permethrin, phenothrin, resmethrin, tetramethrin; cyfluthrin (beta-), cyhalothrin (lambda-), cypermethrin (alpha-, zeta-), deltamethrin, fenvalerate, flucythrinate, flumethrin, fluvalinate (tau-); etofenprox, silafluofen; chlothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid; spinosad, spinetoram; doramectin, eprinomectin, ivermectin, milbemycin oxime, moxidectin, selamectin; amitraz, cymiazole, demiditraz; piperonyl butoxide, and MGK264.

22. The combination according to claim 1 , wherein A is 4-(3,5-dichloro-4-methoxyphenyl)-1-(3-ethoxypyrazin-2-yl)-3-(trifluoromethyl)-1H-pyrazole-5-amine; and, and B is selected from the group consisting of: endosulphan (alpha-), lindane; fipronil, pyriprole; A1443; allethrin, bioallethrin, permethrin, phenothrin, resmethrin, tetramethrin; cyfluthrin (beta-), cyhalothrin (lambda-), cypermethrin (alpha-, zeta-), deltamethrin, fenvalerate, flucythrinate, flumethrin, fluvalinate (tau-); etofenprox, silafluofen; chlothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid; spinosad, spinetoram; doramectin, eprinomectin, ivermectin, milbemycin oxime, moxidectin, selamectin; amitraz, cymiazole, demiditraz; piperonyl butoxide, and MGK264.

23. The combination according to claim 1 , wherein A is 4-[3,5-dichloro-4-(dimethylamino)phenyl]-1-(3-ethoxypyrazin-2-yl)-3-(trifluoromethyl)-1H-pyrazole-5-amine, and B is selected from the group consisting of: endosulphan (alpha-), lindane; fipronil, pyriprole; A1443; allethrin, bioallethrin, permethrin, phenothrin, resmethrin, tetramethrin; cyfluthrin (beta-), cyhalothrin (lambda-), cypermethrin (alpha-, zeta-), deltamethrin, fenvalerate, flucythrinate, flumethrin, fluvalinate (tau-); etofenprox, silafluofen; chlothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid; spinosad, spinetoram; doramectin, eprinomectin, ivermectin, milbemycin oxime, moxidectin, selamectin; amitraz, cymiazole, demiditraz; piperonyl butoxide, and MGK264.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 19, 2014
From: TURBERG, ANDREAS, DR.; GORGENS, ULRICH; SCHWARZ, HANS-GEORG, DR.; WERNER, STEFAN, DR.
To: BAYER INTELLECTUAL PROPERTY GMBH
Reel/Frame 032472/0535 →
Priority Claims (1)
DE 10 2010 063 691 · Dec 21, 2010 · national
Continuity (1)
Related Publication 20140179623A1 · Jun 26, 2014