US 12,187,705 B2
Heteroaryl-triazole and heteroaryl-tetrazole compounds as pesticides
Alexander Arlt, Cologne (DE); Werner Hallenbach, Nordhorn (DE); Hans-Georg Schwarz, Dorsten (DE); Martin Fuesslein, Duesseldorf (DE); Heinz-Juergen Wroblowsky, Langenfeld (DE); Marc Linka, Duesseldorf (DE); Sascha Eilmus, Leichlingen (DE); Kerstin Ilg, Cologne (DE); Ulrich Goergens, Ratingen (DE); Arunas Jonas Damijonaitis, Leverkusen (DE); Yolanda Cancho Grande, Leverkusen (DE); Ulrich Ebbinghaus-Kintscher, Dortmund (DE); Peter Jeschke, Bergisch Gladbach (DE); Weijie Ha, Tianjin (CN); Iring Heisler, Duesseldorf (DE); and Andreas Turberg, Haan (DE)
Assigned to BAYER AKTIENGESELLSCHAFT, Leverkusen (DE)
Appl. No. 17/046,365
Filed by Bayer Aktiengesellschaft, Leverkusen (DE)
PCT Filed Apr. 10, 2019, PCT No. PCT/EP2019/059089
§ 371(c)(1), (2) Date Oct. 9, 2020,
PCT Pub. No. WO2019/197468, PCT Pub. Date Oct. 17, 2019.
Claims priority of application No. 18167084 (EP), filed on Apr. 12, 2018; application No. PCT/CN2018/099141 (WO), filed on Aug. 7, 2018; and application No. 18209259 (EP), filed on Nov. 29, 2018.
Prior Publication US 2021/0147387 A1, May 20, 2021
Int. Cl. C07D 403/04 (2006.01); A01N 43/653 (2006.01); A01N 55/00 (2006.01)
CPC C07D 403/04 (2013.01) [A01N 43/653 (2013.01); A01N 55/00 (2013.01)] 10 Claims
 
1. A compound of formula (I)

OG Complex Work Unit Chemistry
wherein
X is O or S;
Q1 is N
Q2 is CR5
Y is a direct bond or CH2;
R1 is hydrogen, methyl, ethyl, 2-(trimethylsilyl) ethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 3,3,3-trifluoropropyl, or cyclopropyl-CH2—;
R2 3-chloro-5-(methylsulfonyl)phenyl, 3-methylsulfonyl-5-(trifluoromethyl)phenyl, 5-(methylsulfonyl) pyridin-3-yl, 3-(methylsulfonyl)phenyl, 3-(trifluoromethylsulfonyl)phenyl, 5-[(trifluoromethyl)sulfonyl]pyridin-3-yl, 3-chloro-5-[(cyclopropylamino)carbonyl]phenyl, 3-cyclopropyl-5-(trifluoromethyl)phenyl, 3-phenyl-5-(trifluoromethyl)phenyl, 3-(4-fluorophenyl)-5-(trifluoromethyl)phenyl, 3-fluoro-5-(trifluoromethylsulfonyl)phenyl, 3-chloro-5-(trifluoromethylsulfonyl)phenyl, 5-chloro-3-thienyl, 3,4,5-trichloro-2-thienyl, 2,5-dichloro-3-thienyl, 4,5-dichloro-2-thienyl, 1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl, 4-chloro-1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl, 5-methyl-1,2-oxazol-3-yl, 5-cyclopropyl-1,2-oxazol-3-yl, 3-chloro-1,2-oxazol-5-yl, 2-chloro-1,3-thiazol-5-yl, 1-methyl-1H-pyrazol-4-yl, 5-chloro-1-methyl-1H-pyrazol-4-yl, 3-chloro-5-cyclopropylsulfonylphenyl, 3-chloro-5-(4-fluorophenyl)sulfonylphenyl, 3-chloro-5-ethylsulfonylphenyl, 3-cyclopropyl-5-fluorophenyl, 3-chloro-5-(isopropylthio)phenyl, 3-chloro-5-(1H-pyrazol-1-yl)phenyl, 3-chloro-5-(1H-1,2,4-triazol-1-yl)phenyl, 3-fluoro-5-cyclopropylphenyl, 3-chloro-5-cyclopropylphenyl, 3-chloro-5-isopropylsulfonylphenyl, 1-(4-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl, 3-cyclopropyl-5-(trifluoromethoxy)phenyl, 4-(trifluoromethylsulfonyl)phenyl, 3-chloro-5-[1-(methoxyimino) ethyl]phenyl, 3-(tert-butylthio)-5-chlorophenyl, 1-(4-fluorophenyl)-1H-pyrazol-4-yl, 1-(4-fluorophenyl)-5-(trifluoromethyl)-1H-pyrazol-3-yl, 5-[4-(trifluoromethoxy)phenyl]pyridin-3-yl, 3-chloro-5-methylsulfanylphenyl, 3-chloro-5-methylsulfinylphenyl, 3-benzamido-5-chlorophenyl, 3-(tert-butylsulfonyl)-5-chlorophenyl, 5-[4-(trifluoromethyl)phenyl]-pyridin-3-yl, 5-[4-(trifluoromethoxy)phenyl]-pyridin-3-yl, 5-(4-chlorophenyl) pyridin-3-yl, 5-(4-fluorophenyl)pyridin-3-yl, 3-chloro-5-[(phenylsulfonyl)amino]phenyl, 3-acetamido-5-chlorophenyl, 3-chloro-5-[(cyclopropylcarbonyl)amino]phenyl, 3-chloro-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl, 3-chloro-5-[(2,2,2-trifluoroethyl)sulfonyl]phenyl, 3-chloro-5-[3-(trifluoromethyl)-1H-pyrazol-1-yl]phenyl, 3,5-bis(methylsulfonyl)phenyl, pyrazolo[1,5-a]pyridin-2-yl, 7-(trifluoromethyl)pyrazolo[1,5-a]pyridin-2-yl, 6-chloropyrazolo[1,5-a]pyridin-2-yl, 3-[4′-(trifluoromethoxy)phenyl]-phenyl, 3-(4′-fluorophenyl)-5-(trifluoromethyl)phenyl or 3-chloro-5-(1-cyanocyclopropyl)phenyl;
R3a, R3b are independently hydrogen, methyl or methoxymethyl wherein R3a and R3b are not both hydrogen;
or
R3a and R3b form together with the carbon to which they are connected a cyclopropane ring;
R4 is pyridin-2-yl, pyrimidin-2-yl, pyrimidin-4-yl, 5-fluoropyrimidin-2-yl, 5-chloropyrimidin-2-yl, 5-cyanopyrimidin-2-yl, 5-(trifluoromethyl)pyrimidin-2-yl, 5-methylpyrimidin-2-yl, 5-fluoropyridin-2-yl, 5-chloropyridin-2-yl, 2-chloropyridin-4-yl, 5-cyanopyridin-2-yl, 4-cyano-pyridin-2-yl, 6-cyano-pyridin-2-yl, 5-methoxy-pyridin-2-yl, 5-(trifluoromethyl)-pyridin-2-yl, 5-(difluoromethoxy)pyridin-2-yl, 5-(trifluoromethylthio)pyridin-2-yl, 5-nitropyridin-2-yl, 5-aminopyridin-2-yl, 3,5-difluoropyridin-2-yl, 5-chloro-3-fluoropyridin-2-yl, pyridin-2-yl-5-carboxylic acid, methyl pyridin-2-yl-5-carboxylate, N-methyl-pyridin-2-yl-5-carboxamide, N-cyclopropyl-pyridin-2-yl-5-carboxamide, N-cyclopropyl-N-methyl-pyridin-2-yl-5-carboxamide, N-(1-cyanocyclopropyl)-pyridin-2-yl-5-carboxamide, N-(2,2-difluoroethyl)-pyridin-2-yl-5-carboxamide, N-(2,2,2-trifluoroethyl)-pyridin-2-yl-5-carboxamide, N-methylsulfonyl-pyridin-2-yl-5-carboxamide, N-(4-fluorophenyl)-pyridin-2-yl-5-carboxamide, 5-acetamidopyridin-2-yl, 5-(trifluoroacetamido)-pyridin-2-yl, 5-(2-cyanoacetylamino)-pyridin-2-yl, 5-[(cyclopropylcarbonyl)amino]pyridin-2-yl, 5-[(1-cyanocyclopropylcarbonyl)amino]-pyridin-2-yl, 5-(methanesulfonamido)-pyridin-2-yl, 5-(trifluoromethylsulfonamido)-pyridin-2-yl, 5-[(4-fluorobenzoyl)amino]pyridine-2-yl pyrazin-2-yl, 2-cyano-pyrazin-5-yl, or 1,3-thiazol-2-yl;
R5 is hydrogen, methyl or trifluoromethyl.