Heterocycle derivatives as pesticides

Patent metadata

Field	Value
Publication number	US-11655258-B2
Application number	US-201816640656-A
Country	US
Kind code	B2
Filing date	Aug 17, 2018
Priority date	Aug 22, 2017
Publication date	May 23, 2023
Grant date	May 23, 2023

Abstract

The present invention relates to novel fused bicyclic heterocycle derivatives of formula (I)

in which Aa, Ab, Ac, Ad and Q have the meanings mentioned above,

agrochemical formulations containing the compounds of formula (I) and their use as acaricides and/or insecticides for controlling animal pests, particularly arthropods and especially insects and arachnids.

First claim

The invention claimed is:

1. A compound of formula (I)

in which
Aa represents nitrogen or C(R 1 ),
Ab represents nitrogen or C(R 2 ),
Ac represents nitrogen or C(R 3 ),
Ad represents nitrogen or C(R 4 ),
where at most one of the groups Aa, Ab, Ac and Ad represents nitrogen,
R 1 , R 2 , R 3 , R 4 each independently of one another represent hydrogen, halogen, cyano, SF 5 , (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-haloalkoxy, (C 3 -C 6 )-cycloalkyl, (C 1 -C 4 )-cyanoalkyl, cyano-(C 3 -C 6 )-cycloalkyl, (C 1 -C 4 )-alkylthio, (C 1 -C 4 )-haloalkylthio, (C 1 -C 4 )-alkylsulfinyl, (C 1 -C 4 )-haloalkylsulfinyl, (C 1 -C 4 )-alkyl sulfonyl or (C 1 -C 4 )-haloalkylsulfonyl,
where at most two of the radicals R 1 , R 2 , R 3 and R 4 represent a radical other than hydrogen,
Q represents a heteroaromatic 8-, 9- or 10-membered fused bicyclic ring system selected from the group consisting of Q1, Q4, Q5, Q7, Q8 and Q9,

Ae represents nitrogen, C(R 6 ) or C(R 7 ),
Af represents nitrogen, C(R 6 ) or C(R 7 ),
Ag represents nitrogen, C(R 6 ) or C(R 7 ),
Ah represents nitrogen, C(R 6 ) or C(R 7 ),
where at most one of the groups Ae, Af, Ag and Ah represents nitrogen,
R 5 represents (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl or (C 3 -C 6 )-cycloalkyl,
R 6 represents hydrogen,
R 7 represents hydrogen, halogen, cyano, SF 5 , (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-haloalkoxy, (C 1 -C 4 )-alkoxy, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-halocycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 4 )-alkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-alkyl-(C 3 -C 6 )-cycloalkyl, (C 1 -C 4 )-haloalkyl-(C 3 -C 6 )-cycloalkyl, (C 1 -C 4 )-cyanoalkyl, cyano-(C 3 -C 6 )-cycloalkyl or
R 7 represents a group selected from —C(═O)—R 21 , —C(═S)—R 21 , —C(═O)—OR 21 , —C(═O)—NR 20 R 21 , —C(═S)—NR 20 R 21 , —CH(═N—OR 23 ), —CH(═N—NR 23 R 24 ), —OR 21 , —OC(═O)—NR 20 R 21 , —NR 20 R 21 , —N(R 20 )—NR 21 R 22 , —N(R 20 )—C(═O)—R 21 , —N(R 20 )—C(═S)—R 21 , —N(R 20 )—C(═O)—OR 21 , —N(R 20 )—C(═S)—OR 21 , —N(R 20 )—C(═O)—NR 21 R 22 , —N(R 20 )—C(═S)—NR 21 R 22 or —S(═O) m R 21 , where
R 20 , R 21 , R 22 each independently of one another represent hydrogen or represent (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkoxy, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-halocycloalkyl or (C 3 -C 6 )-cycloalkyl, each of which is optionally mono- or polysubstituted by identical or different substituents, where the substituents independently of one another may be selected from halogen, cyano, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 3 -C 6 )-cycloalkyl, (C 1 -C 4 )-alkoxy or (C 1 -C 4 )-haloalkoxy,
R 23 , R 24 each independently of one another represent hydrogen, (C 1 -C 4 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-halocycloalkyl, (C 1 -C 4 )-haloalkyl, (C 2 -C 6 )-haloalkenyl or (C 2 -C 6 )-haloalkynyl and
m represents 0, 1 or 2 and
n represents 0, 1 or 2.

2. The compound of formula (I) according to claim 1 , wherein
Aa represents nitrogen or C(R 1 ),
Ab represents nitrogen or C(R 2 ),
Ac represents nitrogen or C(R 3 ),
Ad represents nitrogen or C(R 4 ),
where at most one of the groups Aa, Ab, Ac and Ad represents nitrogen,
R 1 , R 2 , R 3 , R 4 independently of one another represent hydrogen, halogen, cyano, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-haloalkoxy, (C 3 -C 6 )-cycloalkyl, (C 1 -C 4 )-cyanoalkyl, cyano-(C 3 -C 6 )-cycloalkyl, (C 1 -C 4 )-haloalkylthio, (C 1 -C 4 )-haloalkylsulfinyl or (C 1 -C 4 )-haloalkylsulfonyl,
where at most one of the radicals R 1 , R 2 , R 3 and R 4 represents a radical other than hydrogen,
Q represents a heteroaromatic 8-, 9- or 10-membered fused bicyclic ring system from the group consisting of Q1, Q4, Q5, Q7, Q8 and Q9,

Ae represents nitrogen, C(R 6 ) or C(R 7 ),
Af represents nitrogen, C(R 6 ) or C(R 7 ),
Ag represents nitrogen, C(R 6 ) or C(R 7 ),
Ah represents nitrogen, C(R 6 ) or C(R 7 ),
where at most one of the groups Ae, Af, Ag and Ah represents nitrogen,
R 5 represents (C 1 -C 4 )-alkyl or (C 3 -C 4 )-cycloalkyl,
R 6 represents hydrogen,
R 7 optionally represents hydrogen, halogen, cyano, SF 5 , (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-haloalkoxy, (C 1 -C 4 )-alkoxy, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-halocycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 4 )-alkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-alkyl-(C 3 -C 6 )-cycloalkyl, (C 1 -C 4 )-haloalkyl-(C 3 -C 6 )-cycloalkyl, (C 1 -C 4 )-cyanoalkyl, cyano-(C 3 -C 6 )-cycloalkyl or
R 7 represents a group selected from —C(═O)—R 21 , —C(═S)—R 21 , C(═O)—OR 21 , —C(═O)—NR 20 R 21 , —OR 21 , —NR 20 R 21 , —N(R 20 )—C(═O)—R 21 , —S(═O) m —R 21 or —N(R 20 )—C(═S)—R 21 , where
R 20 , R 21 , R 22 each independently of one another represent hydrogen or represent (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkoxy, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-halocycloalkyl or (C 3 -C 6 )-cycloalkyl, each of which is optionally mono- or polysubstituted by identical or different substituents, where the substituents independently of one another may be selected from halogen, cyano, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 3 -C 6 )-cycloalkyl, (C 1 -C 4 )-alkoxy or (C 1 -C 4 )-haloalkoxy, and
m represents 2 and
n optionally represents 0, 1 or 2.

3. The compound of formula (I) according to claim 1 , wherein
Aa represents nitrogen or CH,
Ab represents nitrogen or C(R 2 ),
Ac represents nitrogen or C(R 3 ),
Ad represents CH,
where at most one of the groups Aa, Ab and Ac represents nitrogen,
R 2 , R 3 independently of one another represent hydrogen or (C 1 -C 6 )-haloalkyl,
Q represents a heteroaromatic 8-, 9- or 10-membered fused bicyclic ring system from the group consisting of Q1, Q7, Q8 or Q9,

where
Ae represents CH,
Af represents CH,
Ag represents CH,
Ah represents CH,
R 5 represents (C 1 -C 4 )-alkyl,
R 6 represents hydrogen,
R 7 represents hydrogen, halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 3 -C 6 )-cycloalkyl or —N(R 20 )—C(═O)—R 21 , —C(═O)OR 21 , —S(═O) m —R 21 or (C 1 -C 4 )-haloalkoxy,
where R 20 represents hydrogen,
R 21 represents (C 3 -C 6 )-cycloalkyl, (C 1 -C 4 )-alkyl or (C 1 -C 4 )-alkoxy,
m represents 2 and
n represents 2.

4. The compound of formula (I) according to claim 3 , wherein R 7 in the case that Q=Q1, represents 3-halogen, 3-(C 1 -C 4 )-haloalkyl, 3-(C 3 -C 6 )-cycloalkyl, 3-(C 1 -C 4 )-haloalkoxy, 3-S(═O) m —R 21 , —C(═O)—OR 21 or 3-N(R 20 )—C(═O)—R 21 ,
where R 20 represents hydrogen,
R 21 represents (C 3 -C 6 )-cycloalkyl, (C 1 -C 4 )-alkoxy or (C 1 -C 4 )-alkyl
and m represents 2,
or in the case that Q=Q7, Q8 or Q9, represents hydrogen.

5. The compound of formula (I) according to claim 1 , wherein
Aa represents nitrogen or CH,
Ab represents nitrogen or C(R 2 ),
Ac r

Assignees

• Bayer Ag

Inventors

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

Classifications

• C07D471/04 Primary

  Ortho-condensed systems · CPC title

• A01N43/653

  1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles · CPC title

• C07D487/04

  Ortho-condensed systems · CPC title

• C07D519/00 Primary

  Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00 · CPC title

• A01N25/06

  Aerosols · CPC title