US 12,384,769 B2
Heteroaryl-substituted aminoalkyl azole compounds as pesticides
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); and Ingo Limberg, Wuppertal (DE)
Assigned to Elanco Animal Health GmbH, Monheim am Rhein (DE)
Appl. No. 17/603,548
Filed by Elanco Animal Health GmbH, Monheim am Rhein (DE)
PCT Filed Apr. 8, 2020, PCT No. PCT/EP2020/060069
§ 371(c)(1), (2) Date Oct. 13, 2021,
PCT Pub. No. WO2020/212235, PCT Pub. Date Oct. 22, 2020.
Claims priority of application No. 19169209 (EP), filed on Apr. 15, 2019.
Prior Publication US 2023/0046680 A1, Feb. 16, 2023
Int. Cl. C07D 413/14 (2006.01); A01N 43/653 (2006.01); A01N 43/76 (2006.01); A01N 43/78 (2006.01); A01N 43/90 (2006.01); C07D 403/14 (2006.01); C07D 417/14 (2006.01); C07D 471/04 (2006.01)
CPC C07D 413/14 (2013.01) [A01N 43/653 (2013.01); A01N 43/76 (2013.01); A01N 43/78 (2013.01); A01N 43/90 (2013.01); C07D 403/14 (2013.01); C07D 417/14 (2013.01); C07D 471/04 (2013.01)] 16 Claims
 
1. A compound of formula (I)

OG Complex Work Unit Chemistry
wherein
Q1 and Q2 are independently CR5 or N, provided at least one of Q1 and Q2 is N;
Y is a direct bond;
R1 is hydrogen; C1-C6alkyl, C3-C6cycloalkylC1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, wherein C1-C6alkyl, 03-C6cycloalkylC1-C6alkyl, C2-C6alkenyl, C2-C6 alkynyl are optionally substituted;
or phenyl-C1-C6alkyl, wherein phenyl is optionally substituted with one to five substituents, each independently selected from the group consisting of halogen, hydroxy, —CN, —COOH, —CONH2, —CSNH2, —NO2, —Si(CH3)3, —SF5, —NH2, and in each case optionally substituted C1-C6alkyl, C3-C6cycloalkyl, C3-C6cycloalkyl-C1-C6alkyl, C1-C3haloalkyl, C1-C4alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, C1-C3haloalkylsulfinyl, C1-C3haloalkylsulfonyl;
R2 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 Z1;
X is selected from the group consisting of hydrogen, halogen, hydroxy, —CN, —COOH, —CONH2, —NO2, —NH2, —SF5, and in each case optionally substituted C1-C6alkyl, C3-C6cycloalkyl, C1-C3haloalkyl, C1-C4alkoxy, C1-C3haloalkoxy, C3-C6cyloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C3-C6cycloalkylthio, C3-C6cycloalkylsulfinyl, C3-C6cycloalkylsulfonyl, C1-C3haloalkylthio, C1-C3haloalkylsulfinyl, C1-C3haloalkylsulfonyl, phenylsulfanyl, phenylsulfinyl, phenylsulfonyl, heterocyclylsulfanyl, heterocyclylsulfinyl, heterocyclylsulfonyl, heteroarylsulfanyl, heteroarylsulfinyl, heteroarylsulfonyl, S—C1-C6alkylsulfinimidoyl, S—C3-C6cycloalkylsulfinimidoyl, S-phenylsulfinimidoyl, S—heterocyclylsulfinimidoyl, S-heteroarylsulfinimidoyl, S—C1-C6alkylsulfonimidoyl, S—C3-C6cycloalkylsulfonimidoyl, S-phenylsulfonimidoyl, S-heterocyclylsulfonimidoyl, S-heteroarylsulfonimidoyl, —NH(C1-C4alkyl), —N(C1-C4alkyl)2, —NHCO—C1-C4alkyl, NHCO—C3-C6cycloalkyl, —NHSO2(C1-C4alkyl), —N(C1-C4alkyl)CO—C1-C4alkyl, —N(C1-C4alkyl)CO—C3-C6cyclolkyl, —N(C1-C4alkyl)SO2C1-C4alkyl, —N(SO2C1-C4alkyl)2, —CO2C1-C4alkyl, —CONH(C1-C4alkyl), —CONH(C3-C6cycloalkyl), —CONH-phenyl, —CON(C1-C4alkyl)2, —CON(C1-C4alkyl)(C3-C6cycloalkyl), —CON(C1-C4alkyl)-phenyl, —SO2NH(C1-C6alkyl), —SO2N(C1-C6alkyl)2, —SO2N(C1-C6alkyl)(C3-C6cycloalkyl), —SO2NH(C3-C6cycloalkyl), —SO2N(C3-C6cycloalkyl)2, —SO2NH(heterocyclyl), —SO2N(C1-C4alkyl)(heterocyclyl), —SO2N(C3-C6cycloalkyl)(heterocyclyl), —C(═NOC1-C4alkyl)H, —C(═NOC1-C4alkyl)-C1-C4alkyl, tri(C1-C4alkyl)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 C1-C3 alkyl;
Z is selected from the group consisting of hydrogen, halogen, hydroxy, —CN, —COOH, —CONH2, —NO2, —NH2, —SF5, and in each case optionally substituted C1-C6alkyl, C3-C6cycloalkyl, C1-C3haloalkyl, C1-C4alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C3-C6cycloalkylthio, C3-C6cycloalkylsulfinyl, C3-C6cycloalkylsulfonyl, phenylsulfanyl, phenylsulfinyl, phenylsulfonyl, C1-C3haloalkylthio, C1-C3haloalkylsulfinyl, C1-C3haloalkylsulfonyl, —NH(C1-C4alkyl), —N(C1-C4alkyl)2, —NHCO—C1-C4alkyl, NHCO—C3-C6cycloalkyl, —NHSO2(C1-C4alkyl), —N(C1-C4alkyl)CO—C1-C4alkyl, —N(C1-C4alkyl)CO—C3-C6cyclolkyl, —N(C1-C4alkyl)SO2C1-C4alkyl, —N(SO2C1-C4alkyl)2, —CO2C1-C4alkyl, —CONH(C1-C4alkyl), —CONH(C3-C6cycloalkyl), —CONH-phenyl, —CON(C1-C4alkyl)2, —CON(C1-C4alkyl)(C3-C6cycloalkyl), —CON(C1-C4alkyl)-phenyl, —C(═NOC1-C4alkyl)H, —C(═NOC1-C4alkyl)-C1-C4alkyl, tri(C1-C4alkyl)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 C1-C3alkyl;
Z1 is hydrogen, C1-C6alkyl, C3-C6cycloalkyl, C2-C3haloalkyl, or C1-C4 alkoxy, wherein C1-C6alkyl, C3-C6cycloalkyl, C2-C3haloalkyl, or C1-C4alkoxy are optionally substituted;
R3 is hydrogen or optionally substituted C1-C6 alkyl;
R4 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, —CO2—C1-C6alkyl, —SO2NH2, —CONH2, —CSNH2, —NO2, —NH2, —SF5;
and in each case optionally substituted C1-C6alkyl, C3-C6cycloalkyl, C1-C6haloalkyl, C3-C6halocycloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkylthio, C1-C6alkylsulfinyl, C1-C6alkylsulfonyl, C1-C6haloalkylthio, C1-C6haloalkylsulfinyl, C1-C6haloalkylsulfonyl, C3-C6cycloalkylsulfanyl, C3-C6cycloalkylsulfinyl, C3-C6cycloalkylsulfonyl, C2-C4alkenylsulfanyl, C2-C4alkenylsulfinyl, C2-C4alkenylsulfonyl, C2-C4alkinylsulfanyl, C2-C4alkinylsulfinyl, C2-C4alkinylsulfonyl, phenylsulfanyl, phenylsulfinyl, phenylsulfonyl, S—C1-C6alkylsulfinimidoyl, S—C3-C6cycloalkylsulfinimidoyl, S—C2-C6alkenylsulfinimidoyl, S—C2-C6alkinylsulfinimidoyl, S-phenylsulfinimidoyl, S—C1-C6alkylsulfonimidoyl, S—C3-C6cycloalkylsulfonimidoyl, S—C2-C6alkenylsulfonimidoyl, S—C2-C6alkinylsulfonimidoyl, S-phenylsulfonimidoyl, —NH(C1-C6alkyl), —N(C1-C6alkyl)2, —NHCO—C1-C6alkyl, —N(C1-C6alkyl)CO—C1-C6alkyl, —N(C3-C6cycloalkyl)CO—C1-C6alkyl, —NHCO—C3-C6cycloalkyl, —N(C1-C6alkyl)CO—(C3-C6cycloalkyl), —N(C3-C6cycloalkyl)CO—(C3-C6cycloalkyl), —N(C1-C6alkyl)CO-phenyl, —N(C3-C6cycloalkyl)CO-phenyl, —NHCO-phenyl, —N(CO—C1-C6alkyl)2, —N(CO—C3-C6cyclo-alkyl)2, —N(CO-phenyl)2, —N(CO—C3-C6cycloalkyl)(CO—C1-C6alkyl), —N(CO—C3-C6cycloalkyl)(CO-phenyl), —N(CO—C1-C6alkyl)(CO-phenyl), —CONH(C1-C6alkyl), —CON(C1-C6alkyl)2, —CONH(C3-C6cycloalkyl), —CON(C1-C6alkyl)(C3-C6cycloalkyl), —CONH(C3-C6cycloalkylalkyl), CON(C1-C6alkyl)(C3-C6cycloalkylalkyl), —CON(C3-C6cycloalkyl)2, —CONH—SO2—C1-C6alkyl, —CONH—SO2-phenyl, —CONH—SO2—(C3-C6cycloalkyl), —CON(C1-C6alkyl)-SO2—C1-C6alkyl, —CON(C1-C6alkyl)-SO2-phenyl, —CON(C1-C6alkyl)-SO2—(C3-C6cycloalkyl), —CONH— phenyl, —CON(C1-C6alkyl)phenyl, —CON(C3-C6cycloalkyl)phenyl, —N(SO2C1-C6alkyl)2, —N(SO2C1-C6haloalkyl)2, —N(SO2C3-C6cycloalkyl)2, —N(SO2C1-C6alkyl)SO2-phenyl, —N(SO2C3-C6cycloalkyl)SO2-phenyl, —NHSO2—C1-C6alkyl, —NHSO2—C1-C6haloalkyl, —N(C1-C6alkyl)SO2—C1-C6alkyl, —N(C3-C6cycloalkyl)SO2—C1-C6alkyl, —NHSO2-phenyl, —N(C1-C6alkyl)SO2-phenyl, —N(C3-C6cycloalkyl)SO2-phenyl, —NHSO2C3-C6cycloalkyl, —N(C1-C6alkyl)SO2—(C3-C6cycloalkyl), —N(C3-C6cycloalkyl)SO2—(C3-C6cycloalkyl), —SO2NH(C1-C6alkyl), —SO2N(C1-C6alkyl)2, —SO2N(C1-C6alkyl)(C3-C6cycloalkyl), —SO2NH(C3-C6cycloalkyl), —SO2N(C3-C6cycloalkyl)2, —SO2NH(phenyl), —SO2N(C1-C6alkyl)(phenyl), —SO2N(C1-C4cycloalkyl)(phenyl), —C(═NOC1-C6alkyl)H and —C(═NOC1-C6alkyl)-C1-C6alkyl;
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 C1-C3alkyl,
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 Z4 is CO or SO2 and Y4 is independently selected from CO or SO2:

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry
R41 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, —SO2NH2, —CONH2, —CSNH2, —NO2, —SF5, —NH2;
and in each case optionally substituted —CO2—C1-C6alkyl, C1-C6alkyl, C3-C6cycloalkyl, C3-C6cycloalkyl-C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkylthio, C1-C6alkylsulfinyl, C1-C6alkylsulfonyl, C3-C6cycloalkylsulfanyl, C3-C6cycloalkylsulfinyl, C3-C6cycloalkylsulfonyl, C1-C6haloalkylthio, C1-C6haloalkylsulfinyl, C1-C6haloalkylsulfonyl, C2-C4alkenylsulfanyl, C2-C4alkenylsulfinyl, C2-C4alkenylsulfonyl, C2-C4alkinylsulfanyl, C2-C4alkinylsulfinyl, C2-C4alkinylsulfonyl, phenylsulfanyl, phenylsulfinyl, phenylsulfonyl, S—C1-C6alkylsulfinimidoyl, S—C3-C6cycloalkylsulfinimidoyl, S—C2-C6alkenylsulfinimidoyl, S—C2-C6alkinylsulfinimidoyl, S-phenylsulfinimidoyl, S—C1-C6alkylsulfonimidoyl, S—C3-C6cycloalkylsulfonimidoyl, S—C2-C6alkenylsulfonimidoyl, S—C2-C6alkinylsulfonimidoyl, S-phenylsulfonimidoyl, —NH(C1-C6alkyl), —N(C1-C6alkyl)2, —NHCO—C1-C6alkyl, —N(C1-C6alkyl)CO—C1-C6alkyl, —N(C3-C6cycloalkyl)CO—C1-C6alkyl, —NHCO—C3-C6cycloalkyl, —N(C1-C6alkyl)CO—(C3-C6cycloalkyl), —N(C3-C6cycloalkyl)CO—(C3-C6cycloalkyl), —N(C1-C6alkyl)CO-phenyl, —N(C3-C6cycloalkyl)CO-phenyl, —NHCO-phenyl, —N(CO—C1-C6alkyl)2, —N(CO—C3-C6cycloalkyl)2, —N(CO-phenyl)2, —N(CO—C3-C6cycloalkyl)(CO—C1-C6alkyl), —N(CO—C3-C6cycloalkyl)(CO-phenyl), —N(CO—C1-C6alkyl)(CO-phenyl), —CONH(C1-C6alkyl), —CON(C1-C6alkyl)2, —CONH(C3-C6cycloalkyl), —CON(C1-C6alkyl)(C3-C6cycloalkyl), —CON(C3-C6cycloalkyl)2, —CONH—SO2—C1-C6alkyl, —CONH—SO2-phenyl, —CONH—SO2—(C3-C6cycloalkyl), —CON(C1-C6alkyl)-SO2—C1-C6alkyl, —CON(C1-C6alkyl)-SO2-phenyl, —CON(C1-C6alkyl)-SO2—(C3-C6cycloalkyl), —CONH-phenyl, —CON(C1-C6alkyl)phenyl, —CON(C3-C6cycloalkyl)phenyl, —N(SO2C1-C6alkyl)2, —N(SO2C1-C6haloalkyl)2, —N(SO2C3-C6cycloalkyl)2, —N(SO2C1-C6alkyl)SO2-phenyl, —N(SO2C3-C6cycloalkyl)SO2-phenyl, —NHSO2—C1-C6alkyl, —NHSO2—C1-C6haloalkyl, —N(C1-C6alkyl)SO2—C1-C6alkyl, —N(C3-C6cycloalkyl)SO2—C1-C6alkyl, —NHSO2-phenyl, —N(C1-C6alkyl)SO2-phenyl, —N(C3-C6cycloalkyl)SO2-phenyl, —NHSO2—C3-C6cycloalkyl, —N(C1-C6alkyl)SO2—(C3-C6cycloalkyl), —N(C3-C6cycloalkyl)SO2—(C3-C6cycloalkyl), —SO2NH(C1-C6alkyl), —SO2N(C1-C6alkyl)2, —SO2N(C1-C6alkyl)(C3-C6cycloalkyl), —SO2NH(C3-C6cycloalkyl), —SO2N(C3-C6cycloalkyl)2, —SO2NH(phenyl), —SO2N(C1-C6alkyl)(phenyl), —SO2N(C1-C4cycloalkyl)(phenyl), —NHCS—C1-C6alkyl, —N(C1-C6alkyl)CS—C1-C6alkyl, —N(C3-C6cycloalkyl)CS—C1-C6alkyl, —NHCS—C3-C6cycloalkyl, —N(C1-C6alkyl)CS—(C3-C6cycloalkyl), —N(C3-C6cycloalkyl)CS—(C3-C6cycloalkyl), —N(C1-C6alkyl)CS-phenyl, —N(C3-C6cycloalkyl)CS-phenyl, —NHCS-phenyl, —CSNH(C1-C6alkyl), —CSN(C1-C6alkyl)2, —CSNH(C3-C6cycloalkyl), —CSN(C1-C6alkyl)(C3-C6cycloalkyl), —CSN(C3-C6cycloalkyl)2, —CSNH-phenyl, —CSN(C1-C6alkyl)phenyl, —CSN(C3-C6cycloalkyl)phenyl, —C(═NOC1-C6alkyl)H, —C(═NOC1-C6alkyl)-C1-C6alkyl, phenyl and 5- to 6-membered heteroaryl;
R42 is hydrogen, hydroxy;
or in each case optionally substituted C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, C3-C6cycloalkyl, C3-C6cycloalkyl-C1-C6alkyl, phenyl-C1-C6alkyl, naphthyl-C1-C6alkyl, C1-C6alkoxy-, C1-C6 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 C1-C6alkyl, C3-C6cycloalkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkylthio, C1-C6alkylsulfinyl, C1-C6alkylsulfonyl, C3-C6cycloalkylthio, C3-C6cycloalkylsulfinyl, C3-C6cycloalkylsulfonyl, C1-C6haloalkylthio, C1-C6haloalkylsulfinyl, and C1-C6 haloalkylsulfonyl;
R43 is in each case optionally substituted C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, C3-C6cycloalkyl, C3-C6cycloalkyl-C1-C6alkyl, phenyl-C1-C6alkyl, naphthyl-C1-C6alkyl, C1-C6alkoxy-, C1-C6 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 C1-C6alkyl, C3-C6cycloalkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkylthio, C1-C6alkylsulfinyl, C1-C6alkylsulfonyl, C3-C6cycloalkylthio, C3-C6cycloalkylsulfinyl, C3-C6cycloalkylsulfonyl, C1-C6haloalkylthio, C1-C6haloalkylsulfinyl, and C1-C6 haloalkylsulfonyl;
R44 is in each case optionally substituted C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, C3-C6cycloalkyl, C3-C6cycloalkyl-C1-C6alkyl, phenyl-C1-C6alkyl, naphthyl-C1-C6alkyl;
R45 is hydrogen or in each case optionally substituted C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, C3-C6cycloalkyl, C3-C6cycloalkyl-C1-C6alkyl, phenyl-C1-C6alkyl, naphthyl-C1-C6 alkyl;
or
R41 and R42 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;
R5 is —NH2, hydrogen, halogen, —CN, or in each case optionally substituted C1-C3alkyl, C1-C3haloalkyl, C3-C4cycloalkyl, C3-C4halocycloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, —CH—(C1-C3alkoxy)2, —CO2C1-C4alkyl, —CONH(C1-C4alkyl), —CON(C1-C4alkyl)2, —NHCO—C1-C4alkyl, —N(C1-C4alkyl)CO—C1-C4alkyl, —NHCO—C3-C6cycloalkyl, —N(C1-C4alkyl)CO—C3-C6cycloalkyl, —N(C3-C6cycloalkyl)CO—C3-C6cycloalkyl, —C(═NOC1-C4alkyl)H, or —C(═NOC1-C4alkyl)-C1-C4alkyl.