2-(het)aryl-substituted fused bicyclic heterocycle derivatives as pesticides

Patent metadata

Field	Value
Publication number	US-10654845-B2
Application number	US-201615547871-A
Country	US
Kind code	B2
Filing date	Feb 2, 2016
Priority date	Feb 5, 2015
Publication date	May 19, 2020
Grant date	May 19, 2020

Abstract

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

in which the R 1 , R 2a , R 2b , R 3 , A 1 , A 2 , A 4 and n have the meanings given above, to their use as acaricides and/or insecticides for controlling animal pests and to processes and intermediates for their preparation.

First claim

The invention claimed is:

1. A compound of formula (I)

wherein
A 1 represents nitrogen,
A 2 represents N—R 5 ,
A 4 represents C—H,
R 1 represents methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or tert-butyl,
R 2a represents hydrogen,
R 2b represents a group selected from
—C(═O)—R 8 (Q1), where R 8 represents methoxy or ethoxy,
—C(═O)—NR 11 R 12 (Q3), where R 11 represents hydrogen or methyl and R 12 represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl or cyclopropyl,
—C(═S)—NR 11 R 12 (Q4), where R 11 represents hydrogen or methyl and R 12 represents methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl or cyclopropyl,
—S(O) m —R 13 (Q5), where m represents 0, 1 or 2 and R 13 represents methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, phenyl or benzyl,
—S═O(═NH)—R 13 (Q6), where R 13 represents methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or tert-butyl,
—S(═N—CN)—R 13 (Q8), where R 13 represents methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or tert-butyl,
—S(O) 2 —NR 11 R 12 (Q9), where R 11 represents hydrogen, methyl, ethyl, n-propyl, isopropyl or cyclopropyl and R 12 represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl or cyclopropyl,
—NR 11 R 12 (Q10), where R 11 represents hydrogen, methyl, ethyl, n-propyl, isopropyl or cyclopropyl and R 12 represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl or cyclopropyl,
—NR 11 —NR 11 R 12 (Q11), where R 11 represents hydrogen, methyl, ethyl, n-propyl, isopropyl, cyclopropyl or COmethyl (acetyl) and R 12 represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl or COmethyl (acetyl),
—NR 11 —C(═O)—R 8 (Q12), where R 11 represents hydrogen or methyl and R 8 represents methyl, ethyl, n-propyl, isopropyl (where R 8 represents methyl, ethyl, n-propyl, or isopropyl only if R 11 does not represent hydrogen), trifluoromethyl, CHF 2 , CF 2 CF 3 , CF 2 CHF 2 , CH 2 OCH 3 , CH 2 SCH 3 , CH 2 OC 2 H 5 , CH 2 SOCH 3 , CH 2 SO 2 CH 3 , CH(CH 3 )CH 2 SCH 3 , CH(CH 3 )CH 2 SOCH 3 , CH(CH 3 )CH 2 SO 2 CH 3 , C 2 H 4 OC 2 H 5 , C 2 H 4 S C 2 H 5 , C 2 H 4 OC 2 H 5 , C 2 H 4 SOC 2 H 5 , C 2 H 4 SO 2 C 2 H 5 , CH(CH 3 )CH 2 SC 2 H 5 , CH(CH 3 )CH 2 SOC 2 H 5 , CH(CH 3 )CH 2 SO 2 C 2 H 5 , cyclopropyl, cyclopropylmethyl (—CH 2 -cyclopropyl), phenyl, benzyl,

NR 11 —C(═S)—R 8 (Q13), where R 8 represents methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl or cyclopropyl and R 11 represents hydrogen, methyl, ethyl, n-propyl, isopropyl or cyclopropyl,
—NR 11 —S(O) 2 —R 13 (Q14), where R 11 represents hydrogen, methyl, ethyl, n-propyl, isopropyl, methylsulphonyl or cyclopropyl and R 13 represents methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl or trifluoromethyl, and
—O—R 13 (Q17), where R 13 represents trifluoromethyl-1H-pyrazol-5-yl

with the proviso that if R 2b represents Q5, Q6, Q8 or Q9, then n represents 2,

R 3 represents fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl or pentafluoroethyl,
R 5 represents methyl, ethyl or isopropyl, and
n is 0, 1 or 2.

2. The compound of formula (I) according to claim 1
wherein
A 1 represents nitrogen,
A 2 represents N—R 5 ,
A 4 represents C—H,
R 1 represents ethyl,
R 2a represents hydrogen,
R 2b represents a group selected from
Q1, where R 8 represents methoxy,
Q3, where R 11 represents hydrogen and R 12 represents hydrogen, methyl, ethyl or cyclopropyl,
Q4, where R 11 represents hydrogen and R 12 represents methyl, ethyl or cyclopropyl,
Q5, where m represents 0, 1 or 2 and R 13 represents methyl, ethyl, isopropyl, phenyl or benzyl,
Q6, where R 13 represents ethyl,
Q8, where R 13 represents methyl,
Q9, where R 11 represents hydrogen or methyl and R 12 represents methyl, ethyl or isopropyl,
Q10, where R 11 represents hydrogen or methyl and R 12 represents hydrogen, methyl or ethyl,
Q11, where R 11 represents hydrogen, methyl or COmethyl (acetyl) and R 12 represents hydrogen, methyl or COmethyl (acetyl),
Q12, where R 11 represents hydrogen or methyl and R 8 represents methyl (only if R 11 does not represent hydrogen), trifluoromethyl, CHF 2 , CF 2 CF 3 , CF 2 CHF 2 , CH 2 OCH 3 , CH 2 SCH 3 , CH 2 OC 2 H 5 , CH 2 SOCH 3 , CH 2 SO 2 CH 3 , CH(CH 3 )CH 2 SCH 3 , CH(CH 3 )CH 2 SOCH 3 , CH(CH 3 )CH 2 SO 2 CH 3 , cyclopropyl, cyclopropylmethyl (—CH 2 -cyclopropyl), phenyl, benzyl,

Q13, where R 8 represents methyl and R 11 represents hydrogen,
Q14, where R 11 represents hydrogen or methylsulphonyl and R 13 represents methyl, ethyl or trifluoromethyl, and
Q17, where R 13 represents trifluoromethyl-1H-pyrazol-5-yl

with the proviso that if R 2b represents Q5, Q6, Q8 or Q9, then n represents 2,

R 3 represents trifluoromethyl or pentafluoroethyl,
R 5 represents methyl, and
n is 0, 1 or 2.

3. The compound of formula (I) according to claim 1
wherein
A 1 represents nitrogen,
A 2 represents N—R 5 ,
A 4 represents C—H,
R 1 represents methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or tert-butyl,
R 2a represents hydrogen,
R 2b represents a group selected from the group consisting of

R 3 represents fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl or pentafluoroethyl,
R 5 represents methyl, ethyl or isopropyl, and
n represents 0 or 2, with the proviso that if R 2b represents Q5a-j, Q6a, Q8a, or Q9a-d, then n represents 2.

4. The compound of formula (I) according to claim 1
wherein
A 1 represents nitrogen,
A 2 represents N—R 5 ,
A 4 represents C—H,
R 1 represents ethyl,
R 2a represents hydrogen,
R 3 represents trifluoromethyl or pentafluoroethyl,
R 5 represents methyl,
n represents 0 or 2, and
R 2b is selected from the group consisting of

with the proviso that if R 2b represents Q5a-j, Q6a, Q8a or Q9a-d, then n represents 2.

5. The compound of formula (I) according to claim 1 wherein R 1 , R 2a , R 2b , R 3 , A 1 , A 2 , A 4 and n have the meanings given in the table:

Assignees

• Bayer Cropscience Ag

Inventors

• Fischer Ruediger
• Wilcke David
• Ilg Kerstin
• Portz Daniela
• Goergens Ulrich
• Eilmus Sascha
• Malsam Olga
• Turberg Andreas
• Horstmann Sebastian

Classifications

• A01N47/40

  the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides · CPC title

• A01N43/90

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

• C07D471/04 Primary

  Ortho-condensed systems · CPC title

• A61P33/14

  Ectoparasiticides, e.g. scabicides · CPC title

• A01N25/30

  characterised by the surfactants · CPC title