IP Library › Granted Patent US 10,654,845
Granted Patent B2
US 10,654,845 · App. 15/547,871 · Granted May 19, 2020

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

Inventors: Ruediger Fischer (Pulheim, DE); David Wilcke (Duesseldorf, DE); Kerstin Ilg (Cologne, DE); Daniela Portz (Vettweiss, DE); Ulrich Goergens (Ratingen, DE); Sascha Eilmus (Leichlingen, DE); Olga Malsam (Roesrath, DE); Andreas Turberg (Haan, DE); Sebastian Horstmann (Leverkusen, DE)
Assignee: BAYER CROPSCIENCE AKTIENGESELLSCHAFT
C07D471/04A01N43/90A01N47/40
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Quick Facts
Patent No.
US 10,654,845
App. No.
15/547,871
Granted
May 19, 2020
Kind
B2
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.

Claims (121)

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:

R 1

n

A 4

A 2

A 1

R 2a

R 3

R 2b

ethyl

2

CH

N-methyl

N

H

CF 3

ethyl

2

CH

N-methyl

N

H

CF 3

.

6. An agrochemical formulation comprising one or more compounds of formula (I) according to claim 1 and one or more extenders and/or surfactants.

7. The agrochemical formulation according to claim 6 , additionally comprising a further agrochemically active compound.

8. A method for controlling one or more animal pests, comprising allowing a compound of formula (I) according to claim 1 or an agrochemical formulation thereof to act on the animal pests and/or a habitat thereof.

9. A product comprising one or more compounds of formula (I) according to claim 1 or one or more agrochemical formulations thereof for controlling animal pests.

10. The compound of formula (I) according to claim 1 ,

wherein

R 2b represents

R 3 represents trifluoromethyl, and

n is 2.

11. The compound of formula (I) according to claim 1 ,

wherein

R 2b represents

R 3 represents trifluoromethyl, and

n is 2.

12. The compound of formula (I) according to claim 1 ,

wherein

R 2b represents

R 3 represents trifluoromethyl, and

n is 2.

13. The compound of formula (I) according to claim 1 ,

wherein

R 2b represents

R 3 represents trifluoromethyl, and

n is 2.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 20, 2018
From: FISCHER, RUEDIGER, DR.; WILCKE, DAVID, DR.; ILG, KERSTIN, DR.; PORTZ, DANIELA, DR.; GOERGENS, ULRICH; HORSTMANN, SEBASTIAN, DR.; EILMUS, SASCHA, DR.; MALSAM, OLGA, DR.; TURBERG, ANDREAS, DR.
To: BAYER CROPSCIENCE AKTIENGESELLSCHAFT
Reel/Frame 046151/0987 →
Priority Claims (2)
EP 15153948 · Feb 5, 2015 · regional
EP 15171696 · Jun 11, 2015 · regional
Continuity (1)
Related Publication 20180016273A1 · Jan 18, 2018
Cited By (2)
US 12,297,196 US 12,741,967