Pyridyloxyalkyl carboxamides and use thereof as endoparasiticides and nematicides

Patent metadata

Field	Value
Publication number	US-9556121-B2
Application number	US-201314441554-A
Country	US
Kind code	B2
Filing date	Nov 8, 2013
Priority date	Nov 13, 2012
Publication date	Jan 31, 2017
Grant date	Jan 31, 2017

Abstract

The present application relates to novel pyridyloxyalkylcarboxamides of the formula (I)

and to their use as endoparasiticides against endoparasites in animals or humans, and to their use as nematicides for controlling phytopathogenic nematodes, and furthermore to endoparasiticides and nematicides comprising pyridyloxyalkylcarboxamides.

First claim

The invention claimed is:

1. A method for controlling endoparasites selected from the group consisting of helminths, nematodes, Pentastoma, and Acanthocephala in animals or humans comprising administering prophylactically and/or therapeutically to the animal
or human a compound to thereby control said endoparasite, wherein the compound is a compound of formula (I)

where
Q represents the structural elements below, where n for each Q is in each case as defined below:

Y represents hydrogen or represents optionally mono- or poly-M 2 -substituted (C 1 -C 10 )-alkyl, (C 2 -C 10 )-alkenyl, (C 2 -C 10 )-alkynyl, (C 1 -C 10 )-haloalkyl, (C 2 -C 10 )-haloalkenyl, (C 2 -C 10 )-haloalkynyl, (C 1 -C 10 )-alkoxy, (C 2 -C 10 )-alkenyloxy, (C 3 -C 10 )-alkynyloxy, (C 3 -C 14 )-cycloalkyl-(C 1 -C 10 )-alkyl or represents an optionally mono- or poly-M 2 -substituted 3- to 14-membered cyclic group;
W represents oxygen or sulphur;
L 2 represents —C(R 21 , R 22 )—;
L 3 represents —C(R 31 , R 32 )—;
M 1 , M 2 and M 3 each independently of one another represent hydrogen, halogen, cyano, nitro, OH, (C 1 -C 10 )-alkyl, (C 1 -C 10 )-haloalkoxy, (C 1 -C 10 )-alkoxy, (C 1 -C 10 )-haloalkoxy, (C 1 -C 10 )-alkylthio, (C 1 -C 10 )haloalkylthio, (C 1 -C 10 )-alkylsulphonyl, (C 1 -C 10 )-haloalkylsulphonyl, (C 1 -C 10 )-alkylsulphanyl, (C 1 -C 10 )-haloalkylsulphanyl or (3- to 14-membered cyclic group)-O—;
M 4 represents hydrogen, halogen, cyano, nitro, OH, (C 1 -C 10 )-alkyl, (C 1 -C 10 )-haloalkyl, (C 1 -C 10 )-alkoxy, (C 1 -C 10 )-haloalkoxy, (C 1 -C 10 )-alkylthio, (C 1 -C 10 )-haloalkylthio, (C 1 -C 10 )-alkylsulphonyl, (C 1 -C 10 )-haloalkylsulphonyl, (C 1 -C 10 )-alkylsulphanyl, (C 1 -C 10 )-haloalkylsulphanyl or (3- to 14-membered cyclic group)-O—;
k represents 1, 2 or 3;
R 21 , R 22 each independently of one another represent hydrogen, halogen or optionally mono- or poly-M 2 -substituted (C 1 -C 10 )-alkyl, (C 2 -C 10 )-alkenyl, (C 2 -C 10 )-alkynyl, (C 1 -C 10 )-haloalkyl, (C 2 -C 10 )-haloalkenyl, (C 2 -C 10 )-haloalkynyl, (C 1 -C 10 )-alkoxy, (C 1 -C 10 )-haloalkoxy, (C 2 -C 10 )-alkenyloxy, (C 3 -C 10 )-alkynyloxy, (C 3 -C 14 )-cycloalkyl-(C 1 -C 10 )-alkyl or represent an optionally mono- or poly-M 2 -substituted 3- to 14-membered cyclic group; or
R 21 , R 22 together represent an optionally mono- or poly-M 2 -substituted spiro-attached 3- to 14-membered carbo- or 3- to 10-membered heterocyclic group;
R 31 , R 32 each independently of one another represent hydrogen, halogen or optionally mono- or poly-M 2 -substituted (C 1 -C 10 )-alkyl, (C 2 -C 10 )-alkenyl, (C 2 -C 10 )-alkynyl, (C 1 -C 10 )-haloalkyl, (C 2 -C 10 )-haloalkenyl, (C 2 -C 10 )-haloalkynyl, (C 3 -C 14 )-cycloalkyl-(C 1 -C 10 )-alkyl or represent an optionally mono- or poly-M 2 -substituted 3- to 14-membered cyclic group;
R 31 , R 32 together represent an optionally mono- or poly-M 5 -substituted spiro-attached 3- to 14-membered carbo- or 3- to 10-membered heterocyclic group;
M 5 in each case independently of the others represents halogen, formyl, cyano, nitro, (C 1 -C 10 )-alkyl, (C 1 -C 10 )-haloalkyl, (C 2 -C 10 )-alkenyl, (C 2 -C 10 )-haloalkenyl, (C 2 -C 10 )-alkynyl, (C 2 -C 10 )-haloalkynyl, (C 1 -C 10 )-alkoxy, (C 1 -C 10 )-haloalkoxy, (C 2 -C 10 )-alkenyloxy, (C 2 -C 10 )-haloalkenyloxy, (C 3 -C 10 )-alkynyloxy, (C 3 -C 10 )-haloalkynyloxy, (C 1 -C 10 )-alkylthio, (C 1 -C 10 )-haloalkylthio, (C 2 -C 10 )-alkenylthio, (C 2 -C 10 )-haloalkenylthio, (C 3 -C 10 )-alkynylthio, (C 3 -C 10 )-haloalkynylthio, (C 1 -C 10 )-alkylsulphonyl, (C 1 -C 10 )-haloalkylsulphonyl, (C 2 -C 10 )-alkenylsulphonyl, (C 2 -C 10 )-haloalkenylsulphonyl, (C 3 -C 10 )-alkynylsulphonyl, (C 3 -C 10 )-haloalkynylsulphonyl, (C 1 -C 10 )-alkylsulphanyl, (C 1 -C 10 )-haloalkylsulphanyl, (C 2 -C 10 )-alkenylsulphanyl, (C 2 -C 10 )-haloalkenylsulphanyl, (C 3 -C 10 )-alkynylsulphanyl, (C 3 -C 10 )-haloalkynylsulphanyl, (C 1 -C 10 )-alkylcarbonyl, (C 1 -C 10 )-haloalkylcarbonyl, (C 2 -C 10 )-alkenylcarbonyl, (C 2 -C 10 )-haloalkenylcarbonyl, (C 2 -C 10 )-alkynylcarbonyl, (C 2 -C 10 )-haloalkynylcarbonyl, (C 1 -C 10 )-alkoxycarbonyl, (C 1 -C 10 )-haloalkoxycarbonyl, (C 2 -C 10 )-alkenyloxycarbonyl, (C 2 -C 10 )-haloalkenyloxycarbonyl, (C 3 -C 10 )-alkynyloxycarbonyl, (C 3 -C 10 )-haloalkynyloxycarbonyl, (C 1 -C 10 )-alkylcarbonyloxy, (C 1 -C 10 )-haloalkylcarbonyloxy, (C 2 -C 10 )-alkenylcarbonyloxy, (C 2 -C 10 )-haloalkenylcarbonyloxy, (C 2 -C 10 )-alkynylcarbonyloxy, (C 2 -C 10 )-haloalkynylcarbonyloxy, a 3- to 14-membered cyclic group;
and/or a salt, N-oxide and/or tautomeric form of a compound of the formula (I),
except for the compounds
N-[2-(pyridin-2-yloxy)ethyl]-4-(trifluoromethyl)nicotinamide:

and
4-(trifluoromethyl)-N-(2-{[5-(trifluoromethyl)pyridin-2-yl]oxy}ethyl)nicotinamide:

2. A method according to claim 1
where
Q represents the structural elements below, where n for each Q is in each case as defined below:

Y represents hydrogen or represents optionally mono- or poly-M 2 -substituted (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 1 -C 6 )-haloalkyl, (C 2 -C 6 )-haloalkenyl, (C 2 -C 6 )-haloalkynyl, (C 1 -C 6 )-alkoxy, (C 2 -C 6 )-alkenyloxy, (C 3 -C 6 )-alkynyloxy, (C 3 -C 10 )-cycloalkyl-(C 1 -C 6 )-alkyl or represents an optionally mono- or poly-M 2 -substituted 3- to 10-membered cyclic group;
W represents oxygen,
M 1 , M 2 and M 3 each independently of one another represent hydrogen, halogen, cyano, nitro, OH, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-haloalkoxy, (C 1 -C 6 )-alkylthio, (C 1 -C 6 )-haloalkylthio, (C 1 -C 6 )-alkylsulphonyl, (C 1 -C 6 )-haloalkylsulphonyl, (C 1 -C 6 )-alkylsulphanyl, (C 1 -C 6 )-haloalkylsulphanyl, (C 3 -C 14 )-cycloalkyl-O—, (C 3 -C 14 )-cycloalkenyl-O—, (C 6 -C 14 )-aryl-O—, halogenated (C 3 -C 14 )-cycloalkyl-O—, halogenated (C 3 -C 14 )-cycloalkenyl-O—, halogenated (C 6 -C 14 )-aryl-O—, where, if Q corresponds to Q 11 , M 3 is not (C 1 -C 4 )-haloalkyl in position 4 at the pyridyl;
M 4 represents hydrogen, halogen, cyano, nitro, OH, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-haloalkoxy, (C 1 -C 6 )-alkylthio, (C 1 -C 6 )-haloalkylthio, (C 1 -C 6 )-alkyl sulphonyl, (C 1 -C 6 )-haloalkylsulphonyl, (C 1 -C 6 )-alkylsulphanyl, (C 1 -C 6 )-haloalkylsulphanyl, (C 3 -C 14 )-cycloalkyl-O—, (C 3 -C 14 )-cycloalkenyl-O—, (C 6 -C 14 )-aryl-O—, halogenated (C 3 -C 14 )-cycloalkyl-O—, halogenated (C 3 -C 14 )-cycloalkenyl-O—, halogenated (C 6 -C 14 )-aryl-O—, where, if Q corresponds to Q 10 , M 4 is not (C 1 -C 4 )-haloalkyl;
k represents for 2;
R 21 , R 22 each independently of one another represent hydrogen, fluorine or optionally mono- or poly-M 2 -substituted (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 1 -C 6 )-haloalkyl, (C 2 -C 6 )-haloalkenyl, (C 2 -C 6 )-haloalkynyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-haloalkoxy, (C 2 -C 6 )-alkenyloxy, (C 3 -C 6 )-alkynyloxy, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl or represent an optionally mono- or poly-M 2 -substituted (C 3 -C 14 )-carbocyclic group; or

Assignees

• Bayer Cropscience Ag

Inventors

• Greul Joerg Nico
• Schwarz Hans-Georg
• Alig Bernd
• Becker Angela
• Portz Daniela
• Ilg Kerstin
• Goergens Ulrich
• Welz Claudia

Classifications

• C07D401/12

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

• C07D213/84

  Nitriles · CPC title

• C07D409/12

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

• A61P33/00

  Antiparasitic agents · CPC title

• A01N43/56

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