Heterocycle derivatives as pesticides

Patent metadata

Field	Value
Publication number	US-RE50663-E
Application number	US-201818101865-A
Country	US
Kind code	E1
Filing date	Sep 28, 2018
Priority date	Oct 4, 2017
Publication date	Nov 18, 2025
Grant date	Nov 18, 2025

Abstract

The invention relates to novel compounds of the formula (I)

in which Aa, Ab, R 1 , R 2 , R 3 , R 4 , R 5 and n have the meanings mentioned above,
to the use thereof as acaricides and/or insecticides for controlling animal pests and to methods and intermediates for the preparation thereof.

First claim

The invention claimed is:

1 . Compound of formula (I)

in which
Aa represents N (nitrogen) or ═C(H)—,
Ab represents N (nitrogen) or ═C(H)—,
R 1 represents (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 8 )-cycloalkyl, halo-(C 3 -C 8 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkyl-(C 3 -C 8 )-cycloalkyl, (C 1 -C 6 )-haloalkyl-(C 3 -C 8 )-cycloalkyl, (C 3 -C 8 )-cycloalkyl-(C 3 -C 8 )-cycloalkyl, spiro-(C 3 -C 8 )-cycloalkyl-(C 3 -C 8 )-cycloalkyl, (C 4 -C 12 )-bicycloalkyl, (C 1 -C 6 )-cyanoalkyl, (C 1 -C 6 )-hydroxyalkyl, (C 1 -C 6 )-alkoxycarbonyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl, (C 2 -C 6 )-cyanoalkenyl, (C 3 -C 6 )-cycloalkyl-(C 2 -C 6 )-alkenyl, (C 2 -C 6 )-cyanoalkynyl, (C 3 -C 6 )-cycloalkyl-(C 2 -C 6 )-alkynyl, (C 1 -C 6 )-haloalkoxy-(C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyloxy-(C 1 -C 6 )-alkyl, (C 2 -C 6 )-haloalkenyloxy-(C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkynyloxy-(C 1 -C 4 )-alkyl, (C 2 -C 6 )-haloalkynyloxy-(C 1 -C 6 )-alkyl, amino, (C 1 -C 6 )-alkylthio-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkylsulfinyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkylsulfonyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkylthio-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkylsulfinyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkylsulfonyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkylthio-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkylsulfinyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkylsulfonyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkylcarbonyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkylcarbonyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxycarbonyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkoxycarbonyl-(C 1 -C 6 )-alkyl, tri-(C 1 -C 6 )-alkylsilyl, aminosulfonyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkylaminosulfonyl-(C 1 -C 6 )-alkyl or di-(C 1 -C 6 )-alkylaminosulfonyl-(C 1 -C 6 )-alkyl,
R 2 , R 3 independently of one another represent hydrogen, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-haloalkyl-(C 3 -C 8 )-cycloalkyl, spiro-(C 3 -C 8 )-cycloalkyl-(C 3 -C 8 )-cycloalkyl, (C 4 -C 12 )-bicycloalkyl, (C 3 -C 8 )-cycloalkyl-(C 2 -C 6 )-alkenyl, (C 3 -C 8 )-cycloalkyl-(C 2 -C 6 )-alkynyl, cyano-(C 3 -C 6 )-cycloalkyl, (C 2 -C 6 )-alkenyloxy-(C 1 -C 6 )-alkyl, (C 2 -C 6 )-haloalkenyloxy-(C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkynyloxy-(C 1 -C 4 )-alkyl, (C 2 -C 6 )-haloalkynyloxy-(C 1 -C 6 )-alkyl,
—C(═O)—R 11 , —c(═S)—R 11 , —C(═O)—OR 12 , —C(═S)—OR 13 , —C(═O)—NR 15 R 16 , —C(═S)—NR 13 R 14 ,
—OR 17 , —OC(═O)—R 12 , —OC(═S)—R 13 , —OC(═O)—OR 13 , —OC(═S)—OR 13 , —OC(═O)—NR 18 R 19 , —OC(═S)—NR 13 R 14 , —O—NR 13 R 14 , —OS(═O)m-R 12 , —OS(═O)m-NR 18 R 19 ,
—N(R 13 )—OR 14 , —NR 15 R 16 , —N(H)—NR 13 R 14 , —N(H)—C(═O)—R 19 , —N(H)—C(═S)—R 14 , —N(H)—C(═O)—OR 19 , —N(H)—C(═S)—OR 14 , —N(H)—C(═O)—NR 18 R 19 , —N(H)—C(═S)—NR 18 R 19 , —N(H)—S(═O) p —R 12 ,
—N(H)—S(═O) p —OR 14 , —N(H)—S(═O) p —NR 18 R 19 ,
—S(═O)—R 17 , —S(═O) 2 —R 17 , —S—C(═O)—R 12 , —S—C(═O)—OR 13 , —S—C(═O)—NR 13 R 14 , —S(═O) m —NR 18 R 19 or
—S(═O) m —OR 13 ,
where one of the radicals R 2 or R 3 has to represent a substituent other than hydrogen,
R 4 represents (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-cyanoalkyl, (C 1 -C 6 )-hydroxyalkyl, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkoxy-(C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkenyloxy-(C 1 -C 6 )-alkyl, (C 2 -C 6 )-haloalkenyloxy-(C 1 -C 6 )-alkyl, (C 2 -C 6 )-haloalkenyl, (C 2 -C 6 )-cyanoalkenyl, (C 2 -C 6 )-alkynyl, (C 2 -C 6 )-alkynyloxy-(C 1 -C 6 )-alkyl, (C 2 -C 6 )-haloalkynyloxy-(C 1 -C 6 )-alkyl, (C 2 -C 6 )-haloalkynyl, (C 2 -C 6 )-cyanoalkynyl, (C 3 —C 8 )-cycloalkyl, (C 3 -C 8 )-cycloalkyl-(C 3 -C 8 )-cycloalkyl, (C 1 -C 6 )-alkyl-(C 3 -C 8 )-cycloalkyl, halo-(C 3 -C 8 )-cycloalkyl, (C 1 -C 6 )-alkylthio-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkylthio-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkylsulfinyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkylsulfinyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkylsulfonyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkylsulfonyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkylthio-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkylsulfinyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkylsulfonyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkylcarbonyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkylcarbonyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxycarbonyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkoxycarbonyl-(C 1 -C 6 )-alkyl, aminocarbonyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkylamino-(C 1 -C 6 )-alkyl, di-(C 1 -C 6 )-alkylamino-(C 1 -C 6 )-alkyl, tri-(C 1 -C 6 )-alkylsilyl or (C 3 -C 8 )-cycloalkylamino-(C 1 -C 6 )-alkyl,
R 5 represents hydrogen, halogen, cyano, hydroxycarbonyl, SCN, SF 5 , (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 1 -C 6 )-alkoxy, (C 1 -C 6 )-haloalkoxy, (C 3 -C 8 )-cycloalkyl, halo-(C 3 -C 8 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkyl-(C 3 -C 8 )-cycloalkyl, (C 1 -C 6 )-haloalkyl-(C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 3 -C 6 )-cycloalkyl, spiro-(C 3 -C 6 )-cycloalkyl-(C 3 -C 6 )-cycloalkyl, (C 4 -C 12 )-bicycloalkyl, (C 1 -C 6 )-cyanoalkyl, cyano-(C 3 -C 6 )-cycloalkyl, (C 1 -C 6 )-alkylthio, (C 1 -C 6 )-haloalkylthio, (C 1 -C 6 )-alkylsulfinyl, (C 1 -C 6 )-haloalkylsulfinyl, (C 1 -C 6 )-alkylsulfonyl, (C 1 -C 6 )-haloalkylsulfonyl, (C 1 -C 6 )-alkylsulfonyloxy, aminosulfonyl, (C 1 -C 6 )-alkylaminosulfonyl or di-(C 1 -C 6 )-alkylaminosulfonyl,
R 11 represents (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-haloalkenyl, (C 2 -C 6 )-alkynyl, (C 2 -C 6 )-haloalkynyl, (C 3 -C 8 )-cycloalkyl, halo-(C 3 -C 8 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkyl-(C 3 -C 8 )-cycloalkyl, (C 1 -C 6 )-haloalkyl-(C 3 -C 8 )-cycloalkyl, (C 3 -C 8 )-cycloalkyl-(C 3 -C 8 )-cycloalkyl, spiro-(C 3 -C 8 )-cycloalkyl-(C 3 -C 8 )-cycloalkyl, (C 4 -C 12 )-bicycloalkyl, (C 1 -C 6 )-cyanoalkyl, cyano-(C 3 -C 6 )-cycloalkyl, (C 1 -C 6 )-hydroxyalkyl, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxycarbonyl-(C 1 -C 6 )-alkyl, (C 2 -C 6 )-cyanoalkenyl, (C 3 -C 6 )-cycloalkyl-(C 2 -C 6 )-alkenyl, (C 2 -C 6 )-cyanoalkynyl, (C 3 -C 6 )-cycloalkyl-(C 2 -C 6 )-alkynyl, (C 1 -C 6 )-haloalkoxy-(C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyloxy-(C 1 -C 6 )-alkyl, (C 2 -C 6 )-haloalkenyloxy-(C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkynyloxy-(C 1 -C 4 )-alkyl, (C 2 -C 6 )-haloalkynyloxy-(C 1 —C 6 )-alkyl, (C 1 -C 6 )-alkylthio-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkylsulfinyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkylsulfonyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkylcarbonyl, (C 1 -C 6 )-alkylcarbonyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkylcarbonyl, hydroxycarbonyl, (C 1 -C 6 )-alkoxycarbonyl, (C 1 -C 6 )-haloalkoxycarbonyl, aminocarbonyl, (C 1 -C 6 )-alkylaminocarbonyl, di-(C 1 -C 6 )-alkylaminocarbonyl, (C 3 -C 5 )-cycloalkylaminocarbonyl, tri-(C 1 -C 6 )-alkylsilyl, a phenyl ring or a 3- to 6-membered aromatic, partially saturated or saturated heterocycle, where the phenyl ring or heterocycle may in each case optionally be mono- or polysubstituted by identical or different substituents and where the substituents independently of one another may be selected from the group consisting of halogen, cyano, nitro, hydroxy, hydroxycarbonyl, amino, (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 1 -C 6 )-alkoxy, (C 1 -C 6 )-haloalkoxy, (C 3 -C 5 )-cycloalkyl, halo-(C 3 -C 5 )-cycloalkyl, (C 1 -C 6 )-alkylthio, (C 1 -C 6 )-haloalkylthio, (C 1 -C 6 )-alkylsulfinyl, (C 1 -C 6 )-haloalkylsulfinyl, (C 1 -C 6 )-alkyl

Assignees

• Bayer Ag

Inventors

• Hager Dominik
• Fischer Ruediger
• Hoffmeister Laura
• Kausch-Busies Nina
• Mosrin Marc
• Wilcke David
• Willot Matthieu
• Ilg Kerstin
• Eilmus Sascha
• Goergens Ulrich
• Turberg Andreas

Classifications

• A01N43/90

  having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system · CPC title

• A01N25/06

  Aerosols · CPC title

• C07D487/04

  Ortho-condensed systems · CPC title

• A01P7/04

  Insecticides · CPC title

• A01P7/02

  Acaricides · CPC title