Heteroaryl-triazole and heteroaryl-tetrazole compounds as pesticides

Patent metadata

Field	Value
Publication number	US-11528907-B2
Application number	US-201917049722-A
Country	US
Kind code	B2
Filing date	Apr 18, 2019
Priority date	Apr 25, 2018
Publication date	Dec 20, 2022
Grant date	Dec 20, 2022

Abstract

The present invention relates to novel heteroaryl-triazole and heteroaryl-tetrazole compounds of the general formula (I), in which the structural elements Y, Q 1 , Q 2 , R 1 , R 2 , R 3 , R 4 and R 5 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.

First claim

The invention claimed is:

1. A compound of formula (I),

in which
X is O or S;
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 or CH 2 ;
R 1 is hydrogen; C 1 -C 6 alkyl optionally substituted with one substituent selected from —CN, —CONH 2 , —COOH, —NO 2 and —Si(CH 3 ) 3 ; 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 4 cycloalkyl-C 1 -C 2 alkyl- wherein the C 3 -C 4 cycloalkyl is optionally substituted with one or two halogen atoms; oxetan-3-yl-CH 2 - or benzyl optionally substituted with halogen atoms or C 1 -C 3 haloalkyl;
R 2 is phenyl, pyridine, pyrimidine, pyrazine or pyridazine, wherein the phenyl, pyridine, pyrimidine, pyrazine or pyridazine is optionally substituted with one to three substituents, provided the substituent(s) are not on either carbon adjacent to the carbon bonded to the C═X-group, each independently selected from the group consisting of C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 haloalkylthio, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, halogen, —NO 2 , —SF 5 , —CN, —CONH 2 , —COOH and —C(S)NH 2 ;
R 3 is C 1 -C 3 alkyl or C 1 -C 3 haloalkyl;
R 4 is pyridine, pyrimidine, pyrazine or pyridazine, wherein the pyridine, pyrimidine, pyrazine or pyridazine is substituted with two to three substituents independently selected from the group consisting of
halogen, hydroxy, —CN, —COOH, —CONH 2 , —CSNH 2 , —NO 2 , —NH 2 , C 1 -C 6 alkyl, optionally substituted C 3 -C 6 cycloalkyl, C 1 -C 3 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 3 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 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, —N(C 1 -C 4 alkyl)CO—C 1 -C 4 alkyl, —CO 2 C 1 -C 4 alkyl, —CONH(C 1 -C 4 alkyl), —CON(C 1 -C 4 alkyl) 2 , —C(═NOC 1 -C 4 alkyl)H, —C(═NOC 1 -C 4 alkyl)-C 1 -C 4 alkyl;
and phenyl and 5- to 6-membered heteroaryl, wherein the phenyl or 5- to 6-membered heteroaryl is optionally substituted with one to two substituents, each independently selected from the group consisting of halogen, —CN, C 1 -C 6 alkyl, C 1 -C 3 haloalkyl and C 1 -C 4 alkoxy;
or

R 4 is pyridine, pyrimidine, pyrazine or pyridazine, wherein the pyridine, pyrimidine, pyrazine or pyridazine is substituted with a total of one to three substituent(s), provided at least one and up to three substituent(s) are independently selected from group A consisting of
—CN, —COOH, —CONH 2 , —CSNH 2 , —NO 2 , —NH 2 , C 5 -C 6 cycloalkyl, substituted C 3 -C 4 cycloalkyl, C 1 -C 4 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 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 1 -C 4 haloalkyl, —NHCO—C 1 -C 4 cyanoalkyl, —NHCO—C 3 -C 6 cycloalkyl, wherein the cycloalkyl is optionally substituted with one to three substituents selected from the group consisting of cyano, halogen, C 1 -C 3 alkyl and C 2 -C 4 haloalkenyl; —NHCO—C 1 -C 4 alkyl-C 3 -C 6 cycloalkyl, —NHCO-phenyl, wherein the phenyl is optionally substituted with one to two substituents selected from the group consisting of halogen, CN, C 1 -C 6 alkyl and C 1 -C 3 haloalkyl; —N(SO 2 C 1 -C 3 alkyl) 2 , —NH(SO 2 C 1 -C 3 alkyl), —N(C 1 -C 4 alkyl)CO—C 1 -C 4 alkyl, —NHSO 2 C 1 -C 4 haloalkyl, —NHCS—C 1 -C 4 alkyl, —NHCS—C 3 -C 5 cycloalkyl, —NHCS—C 1 -C 4 alkyl-C 3 -C 5 cycloalkyl, —CO 2 C 1 -C 4 alkyl, —CONH(C 1 -C 5 alkyl), wherein the alkyl is optionally substituted with one to three substituents selected from the group consisting of cyano and halogen; —CON(C 1 -C 4 alkyl) 2 , —CONH—C 3 -C 5 cycloalkyl, wherein the cycloalkyl is optionally substituted with one to three substituents selected from the group consisting of cyano and halogen; —CON(C 1 -C 5 alkyl)(C 3 -C 5 cycloalkyl), CONH-phenyl, wherein the phenyl is optionally substituted with one to three substituents selected from the group consisting of cyano and halogen; —CONHSO 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 phenyl and 5- to 6-membered heteroaryl, wherein the phenyl or 5- to 6-membered heteroaryl is optionally substituted with one to two substituents, each independently selected from the group consisting of halogen, —CN, C 1 -C 6 alkyl, C 1 -C 3 haloalkyl and C 1 -C 4 alkoxy;

the other one to two optional substituent(s) are each independently selected from group B consisting of
halogen, hydroxy, —CN, —COOH, —CONH 2 , —NO 2 , —NH 2 , 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 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 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, —N(C 1 -C 4 alkyl)CO—C 1 -C 4 alkyl, —CO 2 C 1 -C 4 alkyl, —CONH(C 1 -C 4 alkyl), —CON(C 1 -C 4 alkyl) 2 , —C(═NOC 1 -C 4 alkyl)H, —C(═NOC 1 -C 4 alkyl)-C 1 -C 4 alkyl;
and phenyl and 5- to 6-membered heteroaryl, wherein the phenyl or 5- to 6-membered heteroaryl is optionally substituted with one to two substituents, each independently selected from the group consisting of halogen, —CN, C 1 -C 6 alkyl, C 1 -C 3 haloalkyl and C 1 -C 4 alkoxy;
or

R 4 is a 5-membered heteroaryl optionally substituted with one to three substituents independently selected from the group consisting of
halogen, hydroxy, —CN, —COOH, —CONH 2 , —CSNH 2 , —NO 2 , —NH 2 , 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 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 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, —N(C 1 -C 4 alkyl)CO—C 1 -C 4 alkyl, —CO 2 C 1 -C 4 alkyl, —CONH(C 1 -C 4 alkyl), —CON(C 1 -C 4 alkyl) 2 , —C(═NOC 1 -C 4 alkyl)H, —C(═NOC 1 -C 4 alkyl)-C 1 -C 4 alkyl;
and phenyl and 5- to 6-membered heteroaryl, wherein the phenyl or 5- to 6-membered heteroaryl is optionally substituted with one to two substituents, each independently selected from the group consisting of halogen, —CN, C 1 -C 6 alkyl, C 1 -C 3 haloalkyl and C 1 -C 4 alkoxy;

or

R 4 is a heterocyclic ring which is selected from the group consisting of 4- to 10-membered saturated or partially unsaturated heterocyclyl, 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), hydroxy, —CN, —COOH, —CONH 2 , —CSNH 2 , —NO 2 , —SF 5 , —NH 2 , 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 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 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, —N(C 1 -C 4 alkyl)CO—C 1 -C 4 alkyl, —CO 2 C 1 -C 4 alkyl, —CONH(C 1 -C 4 alkyl), —CON(C 1 -C 4 alkyl) 2 , —C(═NOC 1 -C 4 alkyl)H, —C(═NOC 1 -C 4 alkyl)-C 1 -C 4 alkyl;
and phenyl and 5- to 6-membered he

Assignees

• Bayer Ag

Inventors

• Arlt Alexander
• Hallenbach Werner
• Schwarz Hans-Georg
• Fuesslein Martin
• Wroblowsky Heinz-Juergen
• Buscato Arsequell Estella
• Linka Marc
• Ilg Kerstin
• Damijonaitis Arunas Jonas
• Ebbinghaus-Kintscher Ulrich
• Goergens Ulrich
• Cancho Grande Yolanda
• Jeschke Peter
• Telser Joachim
• Heisler Iring
• Turberg Andreas

Classifications

• C07D401/04 Primary

  directly linked by a ring-member-to-ring-member bond · CPC title

• C07D403/04 Primary

  directly linked by a ring-member-to-ring-member bond · CPC title

• A61P33/00

  Antiparasitic agents · CPC title

• C07D417/04

  directly linked by a ring-member-to-ring-member bond · CPC title

• C07D409/04

  directly linked by a ring-member-to-ring-member bond · CPC title