IP Library › Granted Patent US 12,384,769

Granted Patent B2

US 12,384,769 · App. 17/603,548 · Granted Aug 12, 2025

Heteroaryl-substituted aminoalkyl azole compounds as pesticides

Inventors: Andreas Turberg (Haan, DE); Iring Heisler (Duesseldorf, DE); Joachim Telser (Wuppertal, DE); Alexander Arlt (Cologne, DE); Peter Jeschke (Bergisch Gladbach, DE); Hans-Georg Schwarz (Dorsten, DE); Martin Fuesslein (Duesseldorf, DE); Yolanda Cancho Grande (Leverkusen, DE); Kerstin Ilg (Cologne, DE); Ulrich Ebbinghaus-Kintscher (Dortmund, DE); Peter Loesel (Leverkusen, DE); Marc Linka (Duesseldorf, DE); Arunas Jonas Damijonaitis (Leverkusen, DE); Ingo Limberg (Wuppertal, DE)

Assignee: Elanco Animal Health GmbH

C07D413/14 A01N43/653 A01N43/76 A01N43/78 A01N43/90 C07D403/14 C07D417/14 C07D471/04

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Quick Facts

Patent No.: US 12,384,769
App. No.: 17/603,548
Granted: Aug 12, 2025
Kind: B2

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Abstract

The present invention relates to novel heteroaryl-substituted aminoalkyl azole compounds of the general formula (I), in which the structural elements Y, Q 1 , Q 2 , R 1 , R 2 , R 3 and R 4 have the meaning given in the description, to formulations and compositions comprising such compounds and for their use in the control of animal pests including arthropods and insects in plant protection and to their use for control of ectoparasites on animals.

Claims (158)

1. A compound of formula (I)

wherein

Q 1 and Q 2 are independently CR 5 or N, provided at least one of Q 1 and Q 2 is N;

Y is a direct bond;

R 1 is hydrogen; C 1 -C 6 alkyl, C 3 -C 6 cycloalkylC 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, wherein C 1 -C 6 alkyl, 03-C 6 cycloalkylC 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl are optionally substituted;

or phenyl-C 1 -C 6 alkyl, wherein phenyl is optionally substituted with one to five substituents, each independently selected from the group consisting of halogen, hydroxy, —CN, —COOH, —CONH 2 , —CSNH 2 , —NO 2 , —Si(CH 3 ) 3 , —SF 5 , —NH 2 , and in each case optionally substituted C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl-C 1 -C 6 alkyl, C 1 -C 3 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl, C 1 -C 3 alkylsulfonyl, C 1 -C 3 haloalkylthio, C 1 -C 3 haloalkylsulfinyl, C 1 -C 3 haloalkylsulfonyl;

R 2 is a heteroaromatic bicyclic system containing 9-10 ring members including 1-4 heteroatoms selected from the group consisting of N, O, and S and optionally substituted with 0-4 substituents X, and 0-2 substituents Z and 0-1 substituents Z 1 ;

X is selected from the group consisting of hydrogen, halogen, hydroxy, —CN, —COOH, —CONH 2 , —NO 2 , —NH 2 , —SF 5 , and in each case optionally substituted C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 3 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 3 haloalkoxy, C 3 -C 6 cyloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl, C 1 -C 3 alkylsulfonyl, C 3 -C 6 cycloalkylthio, C 3 -C 6 cycloalkylsulfinyl, C 3 -C 6 cycloalkylsulfonyl, C 1 -C 3 haloalkylthio, C 1 -C 3 haloalkylsulfinyl, C 1 -C 3 haloalkylsulfonyl, phenylsulfanyl, phenylsulfinyl, phenylsulfonyl, heterocyclylsulfanyl, heterocyclylsulfinyl, heterocyclylsulfonyl, heteroarylsulfanyl, heteroarylsulfinyl, heteroarylsulfonyl, S—C 1 -C 6 alkylsulfinimidoyl, S—C 3 -C 6 cycloalkylsulfinimidoyl, S-phenylsulfinimidoyl, S—heterocyclylsulfinimidoyl, S-heteroarylsulfinimidoyl, S—C 1 -C 6 alkylsulfonimidoyl, S—C 3 -C 6 cycloalkylsulfonimidoyl, S-phenylsulfonimidoyl, S-heterocyclylsulfonimidoyl, S-heteroarylsulfonimidoyl, —NH(C 1 -C 4 alkyl), —N(C 1 -C 4 alkyl) 2 , —NHCO—C 1 -C 4 alkyl, NHCO—C 3 -C 6 cycloalkyl, —NHSO 2 (C 1 -C 4 alkyl), —N(C 1 -C 4 alkyl)CO—C 1 -C 4 alkyl, —N(C 1 -C 4 alkyl)CO—C 3 -C 6 cyclolkyl, —N(C 1 -C 4 alkyl)SO 2 C 1 -C 4 alkyl, —N(SO 2 C 1 -C 4 alkyl) 2 , —CO 2 C 1 -C 4 alkyl, —CONH(C 1 -C 4 alkyl), —CONH(C 3 -C 6 cycloalkyl), —CONH-phenyl, —CON(C 1 -C 4 alkyl) 2 , —CON(C 1 -C 4 alkyl)(C 3 -C 6 cycloalkyl), —CON(C 1 -C 4 alkyl)-phenyl, —SO 2 NH(C 1 -C 6 alkyl), —SO 2 N(C 1 -C 6 alkyl) 2 , —SO 2 N(C 1 -C 6 alkyl)(C 3 -C 6 cycloalkyl), —SO 2 NH(C 3 -C 6 cycloalkyl), —SO 2 N(C 3 -C 6 cycloalkyl) 2 , —SO 2 NH(heterocyclyl), —SO 2 N(C 1 -C 4 alkyl)(heterocyclyl), —SO 2 N(C 3 -C 6 cycloalkyl)(heterocyclyl), —C(═NOC 1 -C 4 alkyl)H, —C(═NOC 1 -C 4 alkyl)-C 1 -C 4 alkyl, tri(C 1 -C 4 alkyl)silyl;

and 3-6 membered heterocyclyl containing 1-2 heteroatoms selected from the group consisting of N, O, and S and optionally substituted with up to 4 substituents selected independently from the group consisting of fluorine, chlorine, bromine and C 1 -C 3 alkyl;

Z is selected from the group consisting of hydrogen, halogen, hydroxy, —CN, —COOH, —CONH 2 , —NO 2 , —NH 2 , —SF 5 , and in each case optionally substituted C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 3 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl, C 1 -C 3 alkylsulfonyl, C 3 -C 6 cycloalkylthio, C 3 -C 6 cycloalkylsulfinyl, C 3 -C 6 cycloalkylsulfonyl, phenylsulfanyl, phenylsulfinyl, phenylsulfonyl, C 1 -C 3 haloalkylthio, C 1 -C 3 haloalkylsulfinyl, C 1 -C 3 haloalkylsulfonyl, —NH(C 1 -C 4 alkyl), —N(C 1 -C 4 alkyl) 2 , —NHCO—C 1 -C 4 alkyl, NHCO—C 3 -C 6 cycloalkyl, —NHSO 2 (C 1 -C 4 alkyl), —N(C 1 -C 4 alkyl)CO—C 1 -C 4 alkyl, —N(C 1 -C 4 alkyl)CO—C 3 -C 6 cyclolkyl, —N(C 1 -C 4 alkyl)SO 2 C 1 -C 4 alkyl, —N(SO 2 C 1 -C 4 alkyl) 2 , —CO 2 C 1 -C 4 alkyl, —CONH(C 1 -C 4 alkyl), —CONH(C 3 -C 6 cycloalkyl), —CONH-phenyl, —CON(C 1 -C 4 alkyl) 2 , —CON(C 1 -C 4 alkyl)(C 3 -C 6 cycloalkyl), —CON(C 1 -C 4 alkyl)-phenyl, —C(═NOC 1 -C 4 alkyl)H, —C(═NOC 1 -C 4 alkyl)-C 1 -C 4 alkyl, tri(C 1 -C 4 alkyl)silyl;

Z 1 is hydrogen, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 3 haloalkyl, or C 1 -C 4 alkoxy, wherein C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 3 haloalkyl, or C 1 -C 4 alkoxy are optionally substituted;

R 3 is hydrogen or optionally substituted C 1 -C 6 alkyl;

R 4 is pyridine, pyrimidine, pyrazine, pyridazine or 5-membered heteroaryl wherein the pyridine, pyrimidine, pyrazine, pyridazine or 5-membered heteroaryl is optionally substituted with one to three substituents selected from the group consisting of

halogen, hydroxy, —CN, —COOH, —CO 2 —C 1 -C 6 alkyl, —SO 2 NH 2 , —CONH 2 , —CSNH 2 , —NO 2 , —NH 2 , —SF 5 ;

and in each case optionally substituted C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 haloalkyl, C 3 -C 6 halocycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylthio, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 haloalkylsulfonyl, C 3 -C 6 cycloalkylsulfanyl, C 3 -C 6 cycloalkylsulfinyl, C 3 -C 6 cycloalkylsulfonyl, C 2 -C 4 alkenylsulfanyl, C 2 -C 4 alkenylsulfinyl, C 2 -C 4 alkenylsulfonyl, C 2 -C 4 alkinylsulfanyl, C 2 -C 4 alkinylsulfinyl, C 2 -C 4 alkinylsulfonyl, phenylsulfanyl, phenylsulfinyl, phenylsulfonyl, S—C 1 -C 6 alkylsulfinimidoyl, S—C 3 -C 6 cycloalkylsulfinimidoyl, S—C 2 -C 6 alkenylsulfinimidoyl, S—C 2 -C 6 alkinylsulfinimidoyl, S-phenylsulfinimidoyl, S—C 1 -C 6 alkylsulfonimidoyl, S—C 3 -C 6 cycloalkylsulfonimidoyl, S—C 2 -C 6 alkenylsulfonimidoyl, S—C 2 -C 6 alkinylsulfonimidoyl, S-phenylsulfonimidoyl, —NH(C 1 -C 6 alkyl), —N(C 1 -C 6 alkyl) 2 , —NHCO—C 1 -C 6 alkyl, —N(C 1 -C 6 alkyl)CO—C 1 -C 6 alkyl, —N(C 3 -C 6 cycloalkyl)CO—C 1 -C 6 alkyl, —NHCO—C 3 -C 6 cycloalkyl, —N(C 1 -C 6 alkyl)CO—(C 3 -C 6 cycloalkyl), —N(C 3 -C 6 cycloalkyl)CO—(C 3 -C 6 cycloalkyl), —N(C 1 -C 6 alkyl)CO-phenyl, —N(C 3 -C 6 cycloalkyl)CO-phenyl, —NHCO-phenyl, —N(CO—C 1 -C 6 alkyl) 2 , —N(CO—C 3 -C 6 cyclo-alkyl) 2 , —N(CO-phenyl) 2 , —N(CO—C 3 -C 6 cycloalkyl)(CO—C 1 -C 6 alkyl), —N(CO—C 3 -C 6 cycloalkyl)(CO-phenyl), —N(CO—C 1 -C 6 alkyl)(CO-phenyl), —CONH(C 1 -C 6 alkyl), —CON(C 1 -C 6 alkyl) 2 , —CONH(C 3 -C 6 cycloalkyl), —CON(C 1 -C 6 alkyl)(C 3 -C 6 cycloalkyl), —CONH(C 3 -C 6 cycloalkylalkyl), CON(C 1 -C 6 alkyl)(C 3 -C 6 cycloalkylalkyl), —CON(C 3 -C 6 cycloalkyl) 2 , —CONH—SO 2 —C 1 -C 6 alkyl, —CONH—SO 2 -phenyl, —CONH—SO 2 —(C 3 -C 6 cycloalkyl), —CON(C 1 -C 6 alkyl)-SO 2 —C 1 -C 6 alkyl, —CON(C 1 -C 6 alkyl)-SO 2 -phenyl, —CON(C 1 -C 6 alkyl)-SO 2 —(C 3 -C 6 cycloalkyl), —CONH— phenyl, —CON(C 1 -C 6 alkyl)phenyl, —CON(C 3 -C 6 cycloalkyl)phenyl, —N(SO 2 C 1 -C 6 alkyl) 2 , —N(SO 2 C 1 -C 6 haloalkyl) 2 , —N(SO 2 C 3 -C 6 cycloalkyl) 2 , —N(SO 2 C 1 -C 6 alkyl)SO 2 -phenyl, —N(SO 2 C 3 -C 6 cycloalkyl)SO 2 -phenyl, —NHSO 2 —C 1 -C 6 alkyl, —NHSO 2 —C 1 -C 6 haloalkyl, —N(C 1 -C 6 alkyl)SO 2 —C 1 -C 6 alkyl, —N(C 3 -C 6 cycloalkyl)SO 2 —C 1 -C 6 alkyl, —NHSO 2 -phenyl, —N(C 1 -C 6 alkyl)SO 2 -phenyl, —N(C 3 -C 6 cycloalkyl)SO 2 -phenyl, —NHSO 2 C 3 -C 6 cycloalkyl, —N(C 1 -C 6 alkyl)SO 2 —(C 3 -C 6 cycloalkyl), —N(C 3 -C 6 cycloalkyl)SO 2 —(C 3 -C 6 cycloalkyl), —SO 2 NH(C 1 -C 6 alkyl), —SO 2 N(C 1 -C 6 alkyl) 2 , —SO 2 N(C 1 -C 6 alkyl)(C 3 -C 6 cycloalkyl), —SO 2 NH(C 3 -C 6 cycloalkyl), —SO 2 N(C 3 -C 6 cycloalkyl) 2 , —SO 2 NH(phenyl), —SO 2 N(C 1 -C 6 alkyl)(phenyl), —SO 2 N(C 1 -C 4 cycloalkyl)(phenyl), —C(═NOC 1 -C 6 alkyl)H and —C(═NOC 1 -C 6 alkyl)-C 1 -C 6 alkyl;

or one of the substituents may optionally be selected from the following substructures S1-S24, in which the bond to the pyridine, pyrimidine, pyrazine, pyridazine or 5-membered heteroaryl is marked with a # and Z 4 is CO or SO 2 and Y 4 is independently selected from CO or SO 2 :

R 41 is a heterocyclic ring which is selected from the group consisting of 3- to 10-membered saturated or partially unsaturated heterocyclyl, 5-membered heteroaryl, 6-membered heteroaryl, 9-membered heteroaryl and 10-membered heteroaryl, each of which is optionally substituted by one to three substituents independently selected from the group consisting of halogen, ═O (oxo), ═S (thiono), hydroxy, —CN, —COOH, —SO 2 NH 2 , —CONH 2 , —CSNH 2 , —NO 2 , —SF 5 , —NH 2 ;

and in each case optionally substituted —CO 2 —C 1 -C 6 alkyl, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl-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 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 3 -C 6 cycloalkylsulfanyl, C 3 -C 6 cycloalkylsulfinyl, C 3 -C 6 cycloalkylsulfonyl, C 1 -C 6 haloalkylthio, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 haloalkylsulfonyl, C 2 -C 4 alkenylsulfanyl, C 2 -C 4 alkenylsulfinyl, C 2 -C 4 alkenylsulfonyl, C 2 -C 4 alkinylsulfanyl, C 2 -C 4 alkinylsulfinyl, C 2 -C 4 alkinylsulfonyl, phenylsulfanyl, phenylsulfinyl, phenylsulfonyl, S—C 1 -C 6 alkylsulfinimidoyl, S—C 3 -C 6 cycloalkylsulfinimidoyl, S—C 2 -C 6 alkenylsulfinimidoyl, S—C 2 -C 6 alkinylsulfinimidoyl, S-phenylsulfinimidoyl, S—C 1 -C 6 alkylsulfonimidoyl, S—C 3 -C 6 cycloalkylsulfonimidoyl, S—C 2 -C 6 alkenylsulfonimidoyl, S—C 2 -C 6 alkinylsulfonimidoyl, S-phenylsulfonimidoyl, —NH(C 1 -C 6 alkyl), —N(C 1 -C 6 alkyl) 2 , —NHCO—C 1 -C 6 alkyl, —N(C 1 -C 6 alkyl)CO—C 1 -C 6 alkyl, —N(C 3 -C 6 cycloalkyl)CO—C 1 -C 6 alkyl, —NHCO—C 3 -C 6 cycloalkyl, —N(C 1 -C 6 alkyl)CO—(C 3 -C 6 cycloalkyl), —N(C 3 -C 6 cycloalkyl)CO—(C 3 -C 6 cycloalkyl), —N(C 1 -C 6 alkyl)CO-phenyl, —N(C 3 -C 6 cycloalkyl)CO-phenyl, —NHCO-phenyl, —N(CO—C 1 -C 6 alkyl) 2 , —N(CO—C 3 -C 6 cycloalkyl) 2 , —N(CO-phenyl) 2 , —N(CO—C 3 -C 6 cycloalkyl)(CO—C 1 -C 6 alkyl), —N(CO—C 3 -C 6 cycloalkyl)(CO-phenyl), —N(CO—C 1 -C 6 alkyl)(CO-phenyl), —CONH(C 1 -C 6 alkyl), —CON(C 1 -C 6 alkyl) 2 , —CONH(C 3 -C 6 cycloalkyl), —CON(C 1 -C 6 alkyl)(C 3 -C 6 cycloalkyl), —CON(C 3 -C 6 cycloalkyl) 2 , —CONH—SO 2 —C 1 -C 6 alkyl, —CONH—SO 2 -phenyl, —CONH—SO 2 —(C 3 -C 6 cycloalkyl), —CON(C 1 -C 6 alkyl)-SO 2 —C 1 -C 6 alkyl, —CON(C 1 -C 6 alkyl)-SO 2 -phenyl, —CON(C 1 -C 6 alkyl)-SO 2 —(C 3 -C 6 cycloalkyl), —CONH-phenyl, —CON(C 1 -C 6 alkyl)phenyl, —CON(C 3 -C 6 cycloalkyl)phenyl, —N(SO 2 C 1 -C 6 alkyl) 2 , —N(SO 2 C 1 -C 6 haloalkyl) 2 , —N(SO 2 C 3 -C 6 cycloalkyl) 2 , —N(SO 2 C 1 -C 6 alkyl)SO 2 -phenyl, —N(SO 2 C 3 -C 6 cycloalkyl)SO 2 -phenyl, —NHSO 2 —C 1 -C 6 alkyl, —NHSO 2 —C 1 -C 6 haloalkyl, —N(C 1 -C 6 alkyl)SO 2 —C 1 -C 6 alkyl, —N(C 3 -C 6 cycloalkyl)SO 2 —C 1 -C 6 alkyl, —NHSO 2 -phenyl, —N(C 1 -C 6 alkyl)SO 2 -phenyl, —N(C 3 -C 6 cycloalkyl)SO 2 -phenyl, —NHSO 2 —C 3 -C 6 cycloalkyl, —N(C 1 -C 6 alkyl)SO 2 —(C 3 -C 6 cycloalkyl), —N(C 3 -C 6 cycloalkyl)SO 2 —(C 3 -C 6 cycloalkyl), —SO 2 NH(C 1 -C 6 alkyl), —SO 2 N(C 1 -C 6 alkyl) 2 , —SO 2 N(C 1 -C 6 alkyl)(C 3 -C 6 cycloalkyl), —SO 2 NH(C 3 -C 6 cycloalkyl), —SO 2 N(C 3 -C 6 cycloalkyl) 2 , —SO 2 NH(phenyl), —SO 2 N(C 1 -C 6 alkyl)(phenyl), —SO 2 N(C 1 -C 4 cycloalkyl)(phenyl), —NHCS—C 1 -C 6 alkyl, —N(C 1 -C 6 alkyl)CS—C 1 -C 6 alkyl, —N(C 3 -C 6 cycloalkyl)CS—C 1 -C 6 alkyl, —NHCS—C 3 -C 6 cycloalkyl, —N(C 1 -C 6 alkyl)CS—(C 3 -C 6 cycloalkyl), —N(C 3 -C 6 cycloalkyl)CS—(C 3 -C 6 cycloalkyl), —N(C 1 -C 6 alkyl)CS-phenyl, —N(C 3 -C 6 cycloalkyl)CS-phenyl, —NHCS-phenyl, —CSNH(C 1 -C 6 alkyl), —CSN(C 1 -C 6 alkyl) 2 , —CSNH(C 3 -C 6 cycloalkyl), —CSN(C 1 -C 6 alkyl)(C 3 -C 6 cycloalkyl), —CSN(C 3 -C 6 cycloalkyl) 2 , —CSNH-phenyl, —CSN(C 1 -C 6 alkyl)phenyl, —CSN(C 3 -C 6 cycloalkyl)phenyl, —C(═NOC 1 -C 6 alkyl)H, —C(═NOC 1 -C 6 alkyl)-C 1 -C 6 alkyl, phenyl and 5- to 6-membered heteroaryl;

R 42 is hydrogen, hydroxy;

or in each case optionally substituted C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl-C 1 -C 6 alkyl, phenyl-C 1 -C 6 alkyl, naphthyl-C 1 -C 6 alkyl, C 1 -C 6 alkoxy-, C 1 -C 6 haloalkoxy;

or phenyl, wherein the phenyl is optionally substituted by one to three substituents independently selected from the group consisting of halogen, —CN, and in each case optionally substituted C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 3 -C 6 cycloalkylthio, C 3 -C 6 cycloalkylsulfinyl, C 3 -C 6 cycloalkylsulfonyl, C 1 -C 6 haloalkylthio, C 1 -C 6 haloalkylsulfinyl, and C 1 -C 6 haloalkylsulfonyl;

R 43 is in each case optionally substituted C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl-C 1 -C 6 alkyl, phenyl-C 1 -C 6 alkyl, naphthyl-C 1 -C 6 alkyl, C 1 -C 6 alkoxy-, C 1 -C 6 haloalkoxy;

R 44 is in each case optionally substituted C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl-C 1 -C 6 alkyl, phenyl-C 1 -C 6 alkyl, naphthyl-C 1 -C 6 alkyl;

R 45 is hydrogen or in each case optionally substituted C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl-C 1 -C 6 alkyl, phenyl-C 1 -C 6 alkyl, naphthyl-C 1 -C 6 alkyl;

R 41 and R 42 together with the nitrogen atom to which they are attached, represent a monocyclic or polycyclic optionally substituted 3- to 12-membered saturated or partially unsaturated heterocyclyl which may contain further heteroatoms;

R 5 is —NH 2 , hydrogen, halogen, —CN, or in each case optionally substituted C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 3 -C 4 cycloalkyl, C 3 -C 4 halocycloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, —CH—(C 1 -C 3 alkoxy) 2 , —CO 2 C 1 -C 4 alkyl, —CONH(C 1 -C 4 alkyl), —CON(C 1 -C 4 alkyl) 2 , —NHCO—C 1 -C 4 alkyl, —N(C 1 -C 4 alkyl)CO—C 1 -C 4 alkyl, —NHCO—C 3 -C 6 cycloalkyl, —N(C 1 -C 4 alkyl)CO—C 3 -C 6 cycloalkyl, —N(C 3 -C 6 cycloalkyl)CO—C 3 -C 6 cycloalkyl, —C(═NOC 1 -C 4 alkyl)H, or —C(═NOC 1 -C 4 alkyl)-C 1 -C 4 alkyl.

2. The compound of claim 1 , wherein,

Q 1 and Q 2 are independently CR 5 or N, provided at least one of Q 1 and Q 2 is N;

Y is a direct bond;

R 1 is hydrogen; C 1 -C 6 alkyl, C 3 -C 6 cycloalkylC 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, wherein C 1 -C 6 alkyl, C 3 -C 6 cycloalkylC 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl are optionally substituted;

R 2 is selected from one of the following bicyclic heterocycles T1-T70, wherein the bond to the N atom is marked with a #;

wherein

n is an integer from 0 to 4;

m is an integer from 0 to 2;

X is selected from the group consisting of hydrogen, halogen, hydroxy, —CN, —COOH, —CONH 2 , —NO 2 , —NH 2 , and in each case optionally substituted C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 3 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl, C 1 -C 3 alkylsulfonyl, C 3 -C 6 cycloalkylthio, C 3 -C 6 cycloalkylsulfinyl, C 3 -C 6 cycloalkylsulfonyl, C 1 -C 3 haloalkylthio, C 1 -C 3 haloalkylsulfinyl, C 1 -C 3 haloalkylsulfonyl, phenylsulfanyl, phenylsulfinyl, phenylsulfonyl, —NH(C 1 -C 4 alkyl), —N(C 1 -C 4 alkyl) 2 , —NHCO—C 1 -C 4 alkyl, NHCO—C 3 -C 6 cycloalkyl, —NHSO 2 (C 1 -C 4 alkyl), —N(C 1 -C 4 alkyl)CO—C 1 -C 4 alkyl, —N(C 1 -C 4 alkyl)CO—C 3 -C 6 cyclolkyl, —N(C 1 -C 4 alkyl)SO 2 C 1 -C 4 alkyl, —N(SO 2 C 1 -C 4 alkyl) 2 , —CO 2 C 1 -C 4 alkyl, —CONH(C 1 -C 4 alkyl), —CONH(C 3 -C 6 cycloalkyl), —CONH-phenyl, —CONHSO 2 (C 1 -C 4 alkyl), —CON(C 1 -C 4 alkyl) 2 , —CON(C 1 -C 4 alkyl)(C 3 -C 6 cycloalkyl), —CON(C 1 -C 4 alkyl)-phenyl, —CON(C 1 -C 4 alkyl)SO 2 (C 1 -C 4 alkyl), —C(═NOC 1 -C 4 alkyl)H, —C(═NOC 1 -C 4 alkyl)-C 1 -C 4 alkyl;

and 4-6 membered heterocyclyl containing 1-2 heteroatoms selected from the group consisting of N and O and optionally substituted with 1-2 substituents selected from the group consisting of methyl and ethyl;

Z is selected from the group consisting of hydrogen, halogen, hydroxy, —CN, —COOH, —CONH 2 , —NO 2 , —NH 2 , and in each case optionally substituted C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 3 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl, C 1 -C 3 alkylsulfonyl, C 3 -C 6 cycloalkylthio, C 3 -C 6 cycloalkylsulfinyl, C 3 -C 6 cycloalkylsulfonyl, C 1 -C 3 haloalkylthio, C 1 -C 3 haloalkylsulfinyl, C 1 -C 3 haloalkylsulfonyl, —NH(C 1 -C 4 alkyl), —N(C 1 -C 4 alkyl) 2 , —NHCO—C 1 -C 4 alkyl, NHCO—C 3 -C 6 cycloalkyl, —NHSO 2 (C 1 -C 4 alkyl), —N(C 1 -C 4 alkyl)CO—C 1 -C 4 alkyl, —N(C 1 -C 4 alkyl)CO—C 3 -C 6 cyclolkyl, —N(C 1 -C 4 alkyl)SO 2 C 1 -C 4 alkyl, —N(SO 2 C 1 -C 4 alkyl) 2 , —CO 2 C 1 -C 4 alkyl, —CONH(C 1 -C 4 alkyl), —CONH(C 3 -C 6 cycloalkyl), —CONH-phenyl, —CONHSO 2 (C 1 -C 4 alkyl), —CON(C 1 -C 4 alkyl) 2 , —CON(C 1 -C 4 alkyl)(C 3 -C 6 cycloalkyl), —CON(C 1 -C 4 alkyl)-phenyl, —CON(C 1 -C 4 alkyl)SO 2 (C 1 -C 4 alkyl), —C(═NOC 1 -C 4 alkyl)H, —C(═NOC 1 -C 4 alkyl)-C 1 -C 4 alkyl;

Z 1 is hydrogen, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, or C 2 -C 3 haloalkyl, wherein C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, or C 2 -C 3 haloalkyl are optionally substituted;

R 3 is hydrogen or optionally substituted C 1 -C 6 alkyl;

halogen, hydroxy, —CN, —COOH, —CONH 2 , —SO 2 NH 2 , —NO 2 , —NH 2 , —SF 5 , and in each case optionally substituted C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 3 haloalkyl, C 3 -C 6 halocycloalkyl, C 1 -C 4 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl, C 1 -C 3 alkylsulfonyl, C 3 -C 6 cycloalkylthio, C 3 -C 6 cycloalkylsulfinyl, C 3 -C 6 cycloalkylsulfonyl, C 1 -C 3 haloalkylthio, C 1 -C 3 haloalkylsulfinyl, C 1 -C 3 haloalkylsulfonyl, —NH(C 1 -C 4 alkyl), —N(C 1 -C 4 alkyl) 2 , —NHCO—C 1 -C 4 alkyl, NHCO—C 3 -C 6 cycloalkyl, —NHSO 2 (C 1 -C 4 alkyl), —N(C 1 -C 4 alkyl)CO—C 1 -C 4 alkyl, —N(C 1 -C 4 alkyl)CO—C 3 -C 6 cyclolkyl, —N(C 1 -C 4 alkyl)SO 2 C 1 -C 4 alkyl, —N(SO 2 C 1 -C 4 alkyl) 2 , —CO 2 C 1 -C 4 alkyl, —CONH(C 1 -C 4 alkyl), —CONH(C 3 -C 6 cycloalkyl), —CONH-phenyl, —CONHSO 2 (C 1 -C 4 alkyl), —CON(C 1 -C 4 alkyl) 2 , —CON(C 1 -C 4 alkyl)(C 3 -C 6 cycloalkyl), —CONH(C 3 -C 6 cycloalkylalkyl), —CON(C 1 -C 6 alkyl)(C 3 -C 6 cycloalkylalkyl), —CON(C 1 -C 4 alkyl)-phenyl, —CON(C 1 -C 4 alkyl)SO 2 (C 1 -C 4 alkyl), —C(═NOC 1 -C 4 alkyl)H, —C(═NOC 1 -C 4 alkyl)-C 1 -C 4 alkyl;

and 3-6 membered heterocyclyl containing 1-2 heteroatoms selected from the group consisting of N, O and S and optionally substituted with up to 4 substituents selected independently from the group consisting of fluorine, chlorine, bromine and C 1 -C 3 alkyl;

or one of the substituents may optionally be selected from the following substructures S1-S24, wherein the bond to the pyridine, pyrimidine, pyrazine, pyridazine or 5-membered heteroaryl is marked with a # and Z 4 is CO or SO 2 and Y 4 is independently selected from CO or SO 2 :

R 41 is a heterocyclic ring which is selected from the group consisting of 4- to 10-membered saturated or partially unsaturated heterocyclyl, 5-membered heteroaryl and 6-membered heteroaryl, each of which is optionally substituted by one to three substituents independently selected from the group consisting of

halogen, ═O (oxo), ═S (thiono), hydroxy, —CN, —COOH, —SO 2 NH 2 , —CONH 2 , —CSNH 2 , —NO 2 , —SF 5 , —NH 2 ;

and —CO 2 —C 1 -C 4 alkyl, C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl-C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 3 -C 6 cycloalkylsulfanyl, C 3 -C 6 cycloalkylsulfinyl, C 3 -C 6 cycloalkylsulfonyl, C 1 -C 4 haloalkylthio, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, —NH(C 1 -C 4 alkyl), —N(C 1 -C 4 alkyl) 2 , —NHCO—C 1 -C 4 alkyl, —N(C 1 -C 4 alkyl)CO—C 1 -C 4 alkyl, —N(C 3 -C 6 cycloalkyl)CO—C 1 -C 4 alkyl, —NHCO—C 3 -C 4 cycloalkyl, —N(C 1 -C 4 alkyl)CO—(C 3 -C 6 cycloalkyl), —N(C 3 -C 6 cycloalkyl)CO—(C 3 -C 6 cycloalkyl), —N(CO—C 1 -C 4 alkyl) 2 , —N(CO—C 3 -C 6 cycloalkyl) 2 , —N(CO—C 3 -C 6 cycloalkyl)(CO—C 1 -C 4 alkyl), —CONH(C 1 -C 4 alkyl), —CON(C 1 -C 4 alkyl) 2 , —CONH(C 3 -C 6 cycloalkyl), —CON(C 1 -C 4 alkyl)(C 3 -C 6 cycloalkyl), —CON(C 3 -C 6 cycloalkyl) 2 , —CONH—SO 2 —C 1 -C 4 alkyl, —CONH—SO 2 —(C 3 -C 6 cycloalkyl), —CON(C 1 -C 4 alkyl)-SO 2 —C 1 -C 4 alkyl, —CON(C 1 -C 4 alkyl)-SO 2 —(C 3 -C 6 cycloalkyl), —N(SO 2 C 1 -C 4 alkyl) 2 , —N(SO 2 C 1 -C 4 haloalkyl) 2 , —N(SO 2 C 3 -C 6 cycloalkyl) 2 , —NHSO 2 —C 1 -C 4 alkyl, —NHSO 2 —C 1 -C 4 haloalkyl, —N(C 1 -C 4 alkyl)SO 2 —C 1 -C 4 alkyl, —N(C 3 -C 6 cycloalkyl)SO 2 —C 1 -C 4 alkyl, —NHSO 2 —C 3 -C 6 cycloalkyl, —N(C 1 -C 4 alkyl)SO 2 —(C 3 -C 6 cycloalkyl), —N(C 3 -C 6 cycloalkyl)SO 2 —(C 3 -C 6 cycloalkyl), —SO 2 NH(C 1 -C 4 alkyl), —SO 2 N(C 1 -C 4 alkyl) 2 , —SO 2 N(C 1 -C 4 alkyl)(C 3 -C 6 cycloalkyl), —SO 2 NH(C 3 -C 6 cycloalkyl), —SO 2 N(C 3 -C 6 cycloalkyl) 2 , —C(═NOC 1 -C 4 alkyl)H, —C(═NOC 1 -C 4 alkyl)-C 1 -C 4 alkyl;

R 42 is hydrogen, hydroxy;

and C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl-C 1 -C 4 alkyl, phenyl-C 1 -C 4 alkyl, naphthyl-C 1 -C 4 alkyl, C 1 -C 4 alkoxy-, C 1 -C 4 haloalkoxy;

R 43 is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl-C 1 -C 4 alkyl, phenyl-C 1 -C 4 alkyl, naphthyl-C 1 -C 4 alkyl, C 1 -C 4 alkoxy-, C 1 -C 4 haloalkoxy;

R 44 is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl-C 1 -C 4 alkyl, phenyl-C 1 -C 4 alkyl, naphthyl-C 1 -C 4 alkyl;

R 45 is hydrogen and C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl-C 1 -C 4 alkyl, phenyl-C 1 -C 4 alkyl, naphthyl-C 1 -C 4 alkyl;

R 41 and R 42 together with the nitrogen atom to which they are attached, represent a monocyclic, spirocyclic or bridged polycyclic 4- to 12-membered saturated or partially unsaturated heterocyclyl which may contain up to two further heteroatoms selected from the group of oxygen, nitrogen and sulfur and which is optionally substituted with one to three substituents selected from the group consisting of

halogen, ═O (oxo), =S (thiono), hydroxy, —CN, —COOH, —SO 2 NH 2 , —CONH 2 , —CSNH 2 , —NO 2 , —SF 5 , and —NH 2 ;

and in each case optionally substituted —CO 2 —C 1 -C 4 alkyl, C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 3 -C 6 cycloalkylsulfanyl, C 3 -C 6 cycloalkylsulfinyl, C 3 -C 6 cycloalkylsulfonyl, C 1 -C 4 haloalkylthio, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, —NHSO 2 —C 1 -C 4 alkyl, —NHCO 2 —C 1 -C 4 alkyl, —OCONH—C 1 -C 4 alkyl, —NH(C 1 -C 4 alkyl), —N(C 1 -C 4 alkyl) 2 , —NHCO—C 1 -C 4 alkyl, —N(C 1 -C 4 alkyl)CO—C 1 -C 4 alkyl, —NHCO—C 1 -C 4 cycloalkyl, —N(C 1 -C 4 alkyl)CO—C 3 -C 6 cycloalkyl, —CO 2 C 1 -C 4 alkyl, —CONH(C 1 -C 4 alkyl), —CONH(C 3 -C 6 cycloalkyl), —CON(C 1 -C 4 alkyl) 2 , —SO 2 NH(C 1 -C 4 alkyl);

R 5 is hydrogen, halogen, CN, or in each case optionally substituted C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 3 -C 4 cycloalkyl, C 3 -C 4 halocycloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, —CH—(C 1 -C 3 alkoxy) 2 , —CO 2 C 1 -C 4 alkyl, —CONH(C 1 -C 4 alkyl), —CON(C 1 -C 4 alkyl) 2 , —NHCO—C 1 -C 4 alkyl, —N(C 1 -C 4 alkyl)CO—C 1 -C 4 alkyl, —C(═NOC 1 -C 4 alkyl)H, or —C(═NOC 1 -C 4 alkyl)-C 1 -C 4 alkyl.

3. The compound of claim 1 , wherein,

Q 1 is N;

Q 2 is CR 5 ;

Y is a direct bond;

R 1 is hydrogen; C 1 -C 6 alkyl, optionally substituted with a substituent selected from the group of —CN, methoxy, ethoxy, methylthio and methylsulfonyl; or C 1 -C 6 haloalkyl; C 3 -C 6 cycloalkylC 1 -C 6 alkyl; C 2 -C 6 alkenyl; C 2 -C 6 alkynyl; or C 2 -C 6 haloalkenyl;

R 2 is selected from one of the following bicyclic heterocycles T1-T21, T23-T30, T32-T39, T41, T42, T68-T70, wherein the bond to the N atom is marked with a #;

wherein

n is an integer from 0 to 4;

m is an integer from 0 to 2;

X is selected from the group consisting of hydrogen, halogen, hydroxy, —CN, —COOH, —CONH 2 , —NO 2 , —NH 2 , SF 5 and in each case optionally substituted C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 3 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl, C 1 -C 3 alkylsulfonyl, cycloalkylthio, cycloalkylsulfinyl, cycloalkylsulfonyl, C 1 -C 3 haloalkylthio, C 1 -C 3 haloalkylsulfinyl, C 1 -C 3 haloalkylsulfonyl, phenylsulfonyl, —NH(C 1 -C 4 alkyl), —N(C 1 -C 4 alkyl) 2 , —NHCO—C 1 -C 4 alkyl, NHCO—C 3 -C 6 cycloalkyl, —NHSO 2 (C 1 -C 4 alkyl), —N(C 1 -C 4 alkyl)CO—C 1 -C 4 alkyl, —N(C 1 -C 4 alkyl)CO—C 3 -C 6 cyclolkyl, —N(C 1 -C 4 alkyl)SO 2 C 1 -C 4 alkyl, —N(SO 2 C 1 -C 4 alkyl) 2 , —CO 2 C 1 -C 4 alkyl, —CONH(C 1 -C 4 alkyl), —CONH(C 3 -C 6 cycloalkyl), —CONH-phenyl, —CONHSO 2 (C 1 -C 4 alkyl), —CON(C 1 -C 4 alkyl) 2 , —CON(C 1 -C 4 alkyl)(C 3 -C 6 cycloalkyl), —CON(C 1 -C 4 alkyl)-phenyl, —CON(C 1 -C 4 alkyl)SO 2 (C 1 -C 4 alkyl), —C(═NOC 1 -C 4 alkyl)H, —C(═NOC 1 -C 4 alkyl)-C 1 -C 4 alkyl;

and 4-6 membered heterocyclyl containing 1-2 oxygen atoms and optionally substituted with 1-2 substituents selected from the group consisting of methyl and ethyl;

Z is selected from the group consisting of hydrogen, halogen, hydroxy, —CN, —COOH, —CONH 2 , —NO 2 , —NH 2 , and in each case optionally substituted C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 3 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl, C 1 -C 3 alkylsulfonyl, C 1 -C 3 haloalkylthio, C 1 -C 3 haloalkylsulfinyl, C 1 -C 3 haloalkylsulfonyl, —NH(C 1 -C 4 alkyl), —N(C 1 -C 4 alkyl) 2 , —NHCO—C 1 -C 4 alkyl, NHCO—C 3 -C 6 cycloalkyl, —NHSO 2 (C 1 -C 4 alkyl), —N(C 1 -C 4 alkyl)CO—C 1 -C 4 alkyl, —N(C 1 -C 4 alkyl)CO—C 3 -C 6 cyclolkyl, —N(C 1 -C 4 alkyl)SO 2 C 1 -C 4 alkyl, —N(SO 2 C 1 -C 4 alkyl) 2 , —CO 2 C 1 -C 4 alkyl, —CONH(C 1 -C 4 alkyl), —CONH(C 3 -C 6 cycloalkyl), —CONH-phenyl, —CONHSO 2 (C 1 -C 4 alkyl), —CON(C 1 -C 4 alkyl) 2 , —CON(C 1 -C 4 alkyl)(C 3 -C 6 cycloalkyl), —CON(C 1 -C 4 alkyl)-phenyl, —CON(C 1 -C 4 alkyl)SO 2 (C 1 -C 4 alkyl), —C(═NOC 1 -C 4 alkyl)H, —C(═NOC 1 -C 4 alkyl)-C 1 -C 4 alkyl;

Z 1 is selected from the group consisting of hydrogen and C 1 -C 6 alkyl;

R 3 is hydrogen or C 1 -C 6 alkyl;

R 4 is pyridine, pyrimidine, pyrazine, pyridazine or 5-membered heteroaryl, wherein the pyridine, pyrimidine, pyrazine, pyridazine or 5-membered heteroaryl is optionally substituted with one to three substituents selected from the group consisting of halogen, hydroxy, —CN, —COOH, —CONH 2 , —SO 2 NH 2 , —NO 2 , —NH 2 , —SF 5 , and in each case optionally substituted C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 3 haloalkyl, C 3 -C 6 halocycloalkyl, C 1 -C 4 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl, C 1 -C 3 alkylsulfonyl, C 1 -C 3 haloalkylthio, C 1 -C 3 haloalkylsulfinyl, C 1 -C 3 haloalkylsulfonyl, —NHCO—C 1 -C 4 alkyl, NHCO—C 3 -C 6 cycloalkyl, —NHSO 2 (C 1 -C 4 alkyl), —N(C 1 -C 4 alkyl)CO—C 1 -C 4 alkyl, —N(C 1 -C 4 alkyl)CO—C 3 -C 6 cyclolkyl, —N(C 1 -C 4 alkyl)SO 2 C 1 -C 4 alkyl, —N(SO 2 C 1 -C 4 alkyl) 2 , —CO 2 C 1 -C 4 alkyl, —CONH(C 1 -C 4 alkyl), —CONH(C 3 -C 6 cycloalkyl), —CONH-phenyl, —CONHSO 2 (C 1 -C 4 alkyl), —CON(C 1 -C 4 alkyl) 2 , —CON(C 1 -C 4 alkyl)(C 3 -C 6 cycloalkyl), —CONH(C 3 -C 6 cycloalkylalkyl), —CON(C 1 -C 6 alkyl)(C 3 -C 6 cycloalkylalkyl), —CON(C 1 -C 4 alkyl)-phenyl, —CON(C 1 -C 4 alkyl)SO 2 (C 1 -C 4 alkyl);

or one of the substituents may optionally be selected from the following substructures S1, S2, S3, S4, S5, S16 and S17, in which the bond to the pyridine, pyrimidine, pyrazine, pyridazine or 5-membered heteroaryl is marked with a # and Z 4 is CO:

R 41 is a heterocyclic ring which is selected from the group consisting of 4- to 8-membered saturated or partially unsaturated heterocyclyl, 5-membered heteroaryl and 6-membered heteroaryl, each of which is optionally substituted by one to two substituents independently selected from the group consisting of

halogen, ═O (oxo), ═S (thiono), hydroxy, —CN, —COOH, —SO 2 NH 2 , —CONH 2 , —CSNH 2 , —NO 2 , —SF 5 , —NH 2 ;

and —CO 2 —C 1 -C 3 alkyl, C 1 -C 3 alkyl, C 3 -C 4 cycloalkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl, C 1 -C 3 alkylsulfonyl, C 3 -C 4 cycloalkylsulfanyl, C 3 -C 4 cycloalkylsulfinyl, C 3 -C 4 cycloalkylsulfonyl, C 1 -C 3 haloalkylthio, C 1 -C 3 haloalkylsulfinyl, C 1 -C 3 haloalkylsulfonyl, —NH(C 1 -C 3 alkyl), —N(C 1 -C 3 alkyl) 2 , —NHCO—C 1 -C 3 alkyl, —N(C 1 -C 3 alkyl)CO—C 1 -C 3 alkyl, —N(C 3 -C 4 cycloalkyl)CO—C 1 -C 3 alkyl, —NHCO—C 3 -C 4 cycloalkyl, —N(C 1 -C 3 alkyl)CO—(C 3 -C 4 cycloalkyl), —N(C 3 -C 4 cycloalkyl)CO—(C 3 -C 4 cycloalkyl), —CONH(C 1 -C 3 alkyl), —CON(C 1 -C 3 alkyl) 2 , —CONH(C 3 -C 4 cycloalkyl), —CON(C 1 -C 3 alkyl)(C 3 -C 4 cycloalkyl), —CON(C 3 -C 4 cycloalkyl) 2 , —NHSO 2 —C 1 -C 3 alkyl, —NHSO 2 —C 1 -C 3 haloalkyl, —N(C 1 -C 3 alkyl)SO 2 —C 1 -C 3 alkyl, —N(C 3 -C 4 cycloalkyl)SO 2 —C 1 -C 3 alkyl, —NHSO 2 —C 3 -C 4 cycloalkyl, —N(C 1 -C 3 alkyl)SO 2 —(C 3 -C 4 cycloalkyl), —N(C 3 -C 4 cycloalkyl)SO 2 —(C 3 -C 4 cycloalkyl), —SO 2 NH(C 1 -C 3 alkyl), —SO 2 N(C 1 -C 3 alkyl) 2 , —SO 2 N(C 1 -C 3 alkyl)(C 3 -C 4 cycloalkyl), —SO 2 NH(C 3 -C 4 cycloalkyl), —SO 2 N(C 3 -C 4 cycloalkyl) 2 ;

R 42 is hydrogen, hydroxy;

and C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 3 -C 4 cycloalkyl, C 3 -C 4 cycloalkyl-C 1 -C 2 alkyl, phenyl-C 1 -C 2 alky, C 1 -C 3 alkoxy;

R 43 is C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 3 -C 4 cycloalkyl, C 3 -C 4 cycloalkyl-C 1 -C 2 alkyl, phenyl-C 1 -C 2 alkyl, C 1 -C 3 alkoxy;

R 44 is C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 3 -C 4 cycloalkyl, C 3 -C 4 cycloalkyl-C 1 -C 2 alkyl, phenyl-C 1 -C 2 alkyl;

R 45 is hydrogen and C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 3 -C 4 cycloalkyl, C 3 -C 4 cycloalkyl-C 1 -C 2 alkyl, phenyl-C 1 -C 2 alkyl;

R 41 and R 42 together with the nitrogen atom to which they are attached, represent a monocyclic, spirocyclic or bridged polycyclic 4- to 8-membered saturated heterocyclyl which may contain up to one further heteroatom selected from the group of oxygen, nitrogen and sulfur and which is optionally substituted with one to three substituents selected from the group consisting of halogen, ═O (oxo), =S (thiono), hydroxy, and —CN;

R 5 is hydrogen, halogen, CN, or in each case optionally substituted C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 3 -C 4 cycloalkyl, C 3 -C 4 halocycloalkyl, C 1 -C 3 alkoxy, or C 1 -C 3 haloalkoxy.

4. The compound of claim 1 , wherein,

Q 1 is N;

Q 2 is CR 5 ;

Y is a direct bond;

R 1 is hydrogen, methyl, ethyl, n-propyl, isopropyl, cyanomethyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methylthioethyl, methylsulfonylethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, cyclopropylmethyl, cyclobutylmethyl, 2-propen-1-yl, 3-methyl-but-2-en-1-yl, 3,3-difluoro-prop-2-en-1-yl, 3,3-dichloro-prop-2-en-1-yl or 2-propyn-1-yl;

R 2 is selected from one of the following bicyclic heterocycles T1, T2, T3, T7 or T8, wherein the bond to the N atom is marked with a #;

wherein

n is an integer from 0 to 2; and

m is an integer from 0 to 1; and

X is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, —CN, —NO 2 , —SF 5 , methyl, ethyl, isopropyl, tert-butyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, cyclopropyl, cyclobutyl, oxacyclobutyl, cyclopentyl, oxacyclopent-2-yl, methoxy, difluoromethoxy, trifluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl, ethylthio, ethylsulfinyl, ethylsulfonyl, difluoromethylthio, difluoromethylsulfinyl, difluoromethylsulfonyl, trifluoromethylthio, trifluoromethylsulfinyl, and trifluoromethylsulfonyl; cyclopropylthio, cyclopropylsulfinyl, cylopropylsulfonyl, phenylsulfanyl, phenylsulfinyl, phenylsulfonyl, and Z is selected from the group consisting of hydrogen, fluorine, chlorine, bromine; methyl, ethyl and cyclopropyl;

Z 1 is selected from the group consisting of hydrogen and methyl;

R 3 is hydrogen or methyl;

R 4 is thiazol, pyridine, pyrazine, pyridazine or pyrimidine, wherein the thiazol, pyridine, pyrazine, pyridazine or pyrimidine is optionally substituted with one to three substituents selected from the group consisting of fluorine, chlorine, bromine, iodine, —CN, —NO 2 , —CONH 2 , —SO 2 NH 2 , methyl, ethyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, cyclopropyl, methoxy, difluoromethoxy, trifluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl, difluoromethylthio, difluoromethylsulfinyl, difluoromethylsulfonyl, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl morpholinylcarbonyl, dimethylmorpholinylcarbonyl, piperidinylcarbonyl, pyrrolidinylcarbonyl, azetidinylcarbonyl, azepanylcarbonyl, oxazepanylcarbonyl, N-methylcarbamoyl, N-ethylcarbamoyl, N,N-dimethylcarbamoyl, N,N-diethylcarbamoyl, N-cyclopropylmethyl, N-methylcarbamoyl, morpholinylsulfonyl, dimethylmorpholinylsulfonyl, piperidinylsulfonyl, pyrrolidinylsulfonyl, azetidinylsulfonyl, azepanylsulfonyl, and oxazepanylsulfonyl; oxetanyl, tetrahydrofuranyl, pyranyl

R 5 is hydrogen, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, trifluoromethyl, methoxy, ethoxy, n-propoxy, isopropoxy or difluoromethyl.

5. The compound of claim 1 , wherein,

Q 1 is N;

Q 2 is CR 5 ;

Y is a direct bond;

R 1 is hydrogen;

R 2 is selected from one of the following bicyclic heterocycles T1,T2 and T7 wherein the bond to the N atom is marked with a #

wherein

n is an integer of 0-2; and

X is independently selected from the group consisting of hydrogen, chlorine, bromine, —CN, —SF 5 , trifluoromethyl, trifluormethoxy, difluormethoxy, methyl, isopropyl, tert-butyl, cyclopropyl, methylthio, ethylthio, cyclopropylthio and phenylsulfonyl;

R 3 is methyl;

R 4 is thiazol, pyridine, pyrazine, pyridazine or pyrimidine, wherein the thiazol, pyridine, pyrazine, pyridazine or pyrimidine is unsubstituted or is substituted with one substituent selected from the group consisting of fluorine, chlorine, bromine, —CN, —NH 2 , —CONH 2 , —SO 2 NH 2 , methyl, trifluoromethyl, methoxy, ethoxy, morpholin-4-ylcarbonyl, dimethylmorpholin-4-ylcarbonyl, pyrrolidine-1-ylcarbonyl, N-ethylcarbamoyl, N,N-diethylcarbamoyl, (N-cyclopropylmethyl,N-methyl)carbamoyl and oxetanyl or said thiazol, pyridine, pyrazine, pyridazine or pyrimidine optionally carries a second substituent selected from fluorine, chlorine and bromine;

R 5 is hydrogen, methyl, methoxy or cyclopropyl.

6. The compound of claim 1 , comprising a structure according to formula (I′)

7. The compound of claim 1 , comprising a structure according to formula (I″)

8. The compound of claim 1 , wherein Q 1 represents N or CR 5 and Q 2 represents N.

9. The compound of claim 1 , wherein Q 1 represents N and Q 2 represents CR 5 .

10. A formulation, comprising at least one compound of formula (I)

wherein,

Q 1 and Q 2 are independently CR 5 or N, provided at least one of Q 1 and Q 2 is N;

Y is a direct bond;

R 1 is hydrogen;

C 1 -C 6 alkyl, C 3 -C 6 cycloalkylC 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, wherein C 1 -C 6 alkyl, C 3 -C 6 cycloalkylC 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl are optionally substituted;

R 2 is a heteroaromatic bicyclic system containing 9-10 rind members including 1-4 heteroatoms selected from the group consisting of N, O, and S and optionally substituted with 0-4 substituents X, and 0-2 substituents Z and 0-1 substituents Z 1 ;

X is selected from the group consisting of hydrogen, halogen, hydroxy, —CN, —COOH, —CONH 2 , —NO 2 , —NH 2 , —SF 5 , and in each case optionally substituted C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 3 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 3 haloalkoxy, C 3 -C 6 cyloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl, C 1 -C 3 alkylsulfonyl, C 3 -C 6 cycloalkylthio, C 3 -C 6 cycloalkylsulfinyl, C 3 -C 6 cycloalkylsulfonyl, C 1 -C 3 haloalkylthio, C 1 -C 3 haloalkylsulfinyl, C 1 -C 3 haloalkylsulfonyl, phenylsulfanyl, phenylsulfinyl, phenylsulfonyl, heterocyclylsulfanyl, heterocyclylsulfinyl, heterocyclylsulfonyl, heteroarylsulfanyl, heteroarylsulfinyl, heteroarylsulfonyl, S—C 1 -C 6 alkylsulfinimidoyl, S—C 3 -C 6 cycloalkylsulfinimidoyl, S-phenylsulfinimidoyl, S-heterocyclylsulfinimidoyl, S-heteroarylsulfinimidoyl, S—C 1 -C 6 alkylsulfonimidoyl, S—C 3 -C 6 cycloalkylsulfonimidoyl, S-phenylsulfonimidoyl, S-heterocyclylsulfonimidoyl, S-heteroarylsulfonimidoyl, —NH(C 1 -C 4 alkyl), —N(C 1 -C 4 alkyl) 2 , —NHCO—C 1 -C 4 alkyl, NHCO—C 3 -C 6 cycloalkyl, —NHSO 2 (C 1 -C 4 alkyl), —N(C 1 -C 4 alkyl)CO—C 1 -C 4 alkyl, —N(C 1 -C 4 alkyl)CO—C 3 -C 6 cyclolkyl, —N(C 1 -C 4 alkyl)SO 2 C 1 -C 4 alkyl, —N(SO 2 C 1 -C 4 alkyl) 2 , —CO 2 C 1 -C 4 alkyl, —CONH(C 1 -C 4 alkyl), —CONH(C 3 -C 6 cycloalkyl), —CONH-phenyl, —CON(C 1 -C 4 alkyl) 2 , —CON(C 1 -C 4 alkyl)(C 3 -C 6 cycloalkyl), —CON(C 1 -C 4 alkyl)-phenyl, —SO 2 NH(C 1 -C 6 alkyl), —SO 2 N(C 1 -C 6 alkyl) 2 , —SO 2 N(C 1 -C 6 alkyl)(C 3 -C 6 cycloalkyl), —SO 2 NH(C 3 -C 6 cycloalkyl), —SO 2 N(C 3 -C 6 cycloalkyl) 2 , —SO 2 NH(heterocycyl), —SO 2 N(C 1 -C 4 alkyl)(heterocyclyl), —SO 2 N(C 3 -C 6 cycloalkyl)(heterocyclyl), —C(═NOC 1 -C 4 alkyl)H, —C(═NOC 1 -C 4 alkyl)-C 1 -C 4 alkyl, tri(C 1 -C 4 alkyl)silyl;

R 3 is hydrogen or optionally substituted C 1 -C 6 alkyl;

halogen, hydroxy, —CN, —COOH, —CO 2 —C 1 -C 6 alkyl, —SO 2 NH 2 , —CONH 2 , —CSNH 2 , —NO 2 , —NH 2 , —SF 5 ;

and in each case optionally substituted C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 haloalkyl, C 3 -C 6 halocycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylthio, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 haloalkylsulfonyl, C 3 -C 6 cycloalkylsulfanyl, C 3 -C 6 cycloalkylsulfinyl, C 3 -C 6 cycloalkylsulfonyl, C 2 -C 4 alkenylsulfanyl, C 2 -C 4 alkenylsulfinyl, C 2 -C 4 alkenylsulfonyl, C 2 -C 4 alkinylsulfanyl, C 2 -C 4 alkinylsulfinyl, C 2 -C 4 alkinylsulfonyl, phenylsulfanyl, phenylsulfinyl, phenylsulfonyl, S—C 1 -C 6 alkylsulfinimidoyl, S—C 3 -C 6 cycloalkylsulfinimidoyl, S—C 2 -C 6 alkenylsulfinimidoyl, S—C 2 -C 6 alkinylsulfinimidoyl, S-phenylsulfinimidoyl, S—C 1 -C 6 alkylsulfonimidoyl, S—C 3 -C 6 cycloalkylsulfonimidoyl, S—C 2 -C 6 alkenylsulfonimidoyl, S—C 2 -C 6 alkinylsulfonimidoyl, S-phenylsulfonimidoyl, —NH(C 1 -C 6 alkyl), —N(C 1 -C 6 alkyl) 2 , —NHCO—C 1 -C 6 alkyl, —N(C 1 -C 6 alkyl)CO—C 1 -C 6 alkyl, —N(C 3 -C 6 cycloalkyl)CO—C 1 -C 6 alkyl, —NHCO—C 3 -C 6 cycloalkyl, —N(C 1 -C 6 alkyl)CO—(C 3 -C 6 cycloalkyl), —N(C 3 -C 6 cycloalkyl)CO—(C 3 -C 6 cycloalkyl), —N(C 1 -C 6 alkyl)CO-phenyl, —N(C 3 -C 6 cycloalkyl)CO-phenyl, —NHCO-phenyl, —N(CO—C 1 -C 6 alkyl) 2 , —N(CO—C 3 -C 6 cyclo-alkyl) 2 , —N(CO-phenyl) 2 , —N(CO—C 3 -C 6 cycloalkyl)(CO—C 1 -C 6 alkyl), —N(CO—C 3 -C 6 cycloalkyl)(CO-phenyl), —N(CO—C 1 -C 6 alkyl)(CO-phenyl), —CONH(C 1 -C 6 alkyl), —CON(C 1 -C 6 alkyl) 2 , —CONH(C 3 -C 6 cycloalkyl), —CON(C 1 -C 6 alkyl)(C 3 -C 6 cycloalkyl), —CONH(C 3 -C 6 cycloalkylalkyl), CON(C 1 -C 6 alkyl)(C 3 -C 6 cycloalkylalkyl), —CON(C 3 -C 6 cycloalkyl) 2 , —CONH—SO 2 —C 1 -C 6 alkyl, —CONH—SO 2 -phenyl, —CONH—SO 2 —(C 3 -C 6 cycloalkyl), —CON(C 1 -C 6 alkyl)-SO 2 —C 1 -C 6 alkyl, —CON(C 1 -C 6 alkyl)-SO 2 -phenyl, —CON(C 1 -C 6 alkyl)-SO 2 —(C 3 -C 6 cycloalkyl), —CONH-phenyl, —CON(C 1 -C 6 alkyl)phenyl, —CON(C 3 -C 6 cycloalkyl)phenyl, —N(SO 2 C 1 -C 6 alkyl) 2 , —N(SO 2 C 1 -C 6 haloalkyl) 2 , —N(SO 2 C 3 -C 6 cycloalkyl) 2 , —N(SO 2 C 1 -C 6 alkyl)SO 2 -phenyl, —N(SO 2 C 3 -C 6 cycloalkyl)SO 2 -phenyl, —NHSO 2 —C 1 -C 6 alkyl, —NHSO 2 —C 1 -C 6 haloalkyl, —N(C 1 -C 6 alkyl)SO 2 —C 1 -C 6 alkyl, —N(C 3 -C 6 cycloalkyl)SO 2 —C 1 -C 6 alkyl, —NHSO 2 -phenyl, —N(C 1 -C 6 alkyl)SO 2 -phenyl, —N(C 3 -C 6 cycloalkyl)SO 2 -phenyl, —NHSO 2 —C 3 -C 6 cycloalkyl, —N(C 1 -C 6 alkyl)SO 2 —(C 3 -C 6 cycloalkyl), —N(C 3 -C 6 cycloalkyl)SO 2 —(C 3 -C 6 cycloalkyl), —SO 2 NH(C 1 -C 6 alkyl), —SO 2 N(C 1 -C 6 alkyl) 2 , —SO 2 N(C 1 -C 6 alkyl)(C 3 -C 6 cycloalkyl), —SO 2 NH(C 3 -C 6 cycloalkyl), —SO 2 N(C 3 -C 6 cycloalkyl) 2 , —SO 2 NH(phenyl), —SO 2 N(C 1 -C 6 alkyl)(phenyl), —SO 2 N(C 1 -C 4 cycloalkyl)(phenyl), —C(═NOC 1 -C 6 alkyl)H and —C(═NOC 1 -C 6 alkyl)-C 1 -C 6 alkyl;

halogen, ═O (oxo), ═S (thiono), hydroxy, —CN, —COOH, —SO 2 NH 2 , —CONH 2 , —CSNH 2 , —NO 2 , —SF 5 , —NH 2 ;

R 42 is hydrogen, hydroxy;

R 43 is in each case optionally substituted C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynl, C 2 -C 6 haloalkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl-C 1 -C 6 alkyl, phenyl-C 1 -C 6 alkyl, naphthyl-C 1 -C 6 alkyl, C 1 -C 6 alkoxy-, C 1 -C 6 haloalkoxy;

11. The formulation of claim 10 , wherein the compound of formula (I) is in a mixture with at least one further active compound.

12. A method for controlling a pest, comprising allowing a compound of formula (I) of claim 1 or a formulation thereof to act on the pest and/or a habitat thereof, wherein methods for treatment of an animal body by surgery or therapy and methods practised on an animal body are excluded.

13. A method for protecting seed and/or a germinating plant from a pest, comprising contacting said seed with a compound of formula (I) of claim 1 or with a formulation thereof.

14. Seed A seed obtained by a method of claim 13 .

15. The method of claim 12 , wherein the pest is an animal pest.

16. The method of claim 13 , wherein the pest is an animal pest.

Assignments (2)

CHANGE OF NAME Recorded Nov 4, 2024

From: BAYER ANIMAL HEALTH GMBH

To: ELANCO ANIMAL HEALTH GMBH

Reel/Frame 069300/0663 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 14, 2021

From: TURBERG, ANDREAS; HEISLER, IRING; TELSER, JOACHIM; ARLT, ALEXANDER; JESCHKE, PETER; SCHWARZ, HANS-GEORG; FUESSLEIN, MARTIN; CANCHO-GRANDE, YOLANDA; ILG, KERSTIN; EBBINGHAUS-KINTSCHER, ULRICH; LOESEL, PETER; LINKA, MARC; DAMIJONAITIS, ARUNAS JONAS; LIMBERG, INGO

To: BAYER ANIMAL HEALTH GMBH

Reel/Frame 057795/0177 →

Priority Claims (1)

EP 19169209 · Apr 15, 2019 · regional

Continuity (1)

Related Publication 20230046680A1 · Feb 16, 2023

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