# US 8,785,647 B2 · Pesticidal arylpyrrolidines

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- Number: US 8,785,647 B2
- Document ID: US8785647B2
- Status: Granted
- Kind: B2
- Application number: 13/829,353
- Filed: 2013-03-14
- Published: 2013-11-21
- Granted: 2014-07-22
- Earliest claimed: 2008-10-17
- Assignees: Bayer Intellectual Property GmbH
- Applicants: Bayer Intellectual Property GmbH
- Inventors: Ulrich Görgens; Jun Mihara; Tetsuya Murata; Daiei Yamazaki; Yasushi Yoneta; Koichi Araki; Norio Sasaki; Kei Domon; Mamoru Hatazawa; Eiichi Shimojo; Teruyuki Ichihara; Masashi Ataka; Katsuhiko Shibuya
- Web page: https://patentgrep.com/patent/US8785647B2

## CPC

- A01N 43/84: six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
- A01N 43/36: five-membered rings
- A01N 43/40: six-membered rings
- A01N 43/54: 1,3-Diazines; Hydrogenated 1,3-diazines
- A01N 43/56: 1,2-Diazoles; Hydrogenated 1,2-diazoles
- A01N 43/653: 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- A01N 43/713: having rings with four or more nitrogen atoms as the only ring hetero atoms
- A01N 43/76: 1,3-Oxazoles; Hydrogenated 1,3-oxazoles
- A01N 43/78: 1,3-Thiazoles; Hydrogenated 1,3-thiazoles
- A61P 7/00: Drugs for disorders of the blood or the extracellular fluid
- A61P 33/00: Antiparasitic agents
- A61P 33/02: Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A61P 33/10: Anthelmintics
- A61P 33/12: Schistosomicides
- A61P 33/14: Ectoparasiticides, e.g. scabicides
- C07D 207/08: with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
- C07D 207/09: Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- C07D 401/04: directly linked by a ring-member-to-ring-member bond
- C07D 401/12: linked by a chain containing hetero atoms as chain links
- C07D 401/14: containing three or more hetero rings
- C07D 403/04: directly linked by a ring-member-to-ring-member bond
- C07D 403/12: linked by a chain containing hetero atoms as chain links
- C07D 403/14: containing three or more hetero rings
- C07D 405/12: linked by a chain containing hetero atoms as chain links
- C07D 405/14: containing three or more hetero rings
- C07D 409/12: linked by a chain containing hetero atoms as chain links
- C07D 409/14: containing three or more hetero rings
- C07D 413/12: linked by a chain containing hetero atoms as chain links
- C07D 417/04: directly linked by a ring-member-to-ring-member bond
- C07D 417/14: containing three or more hetero rings
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The invention is directed to arylpyrrolidines compounds which exhibit excellent insecticidal efficacy and which may be used as in the agrochemical field or in the vield of veterinary medicine. The compounds are represented by formula (I): wherein the respective substituents are defined in the specification.

## Claims

### Claim 1

An arylpyrrolidine compound having the formula
or salts thereof,
wherein
A1 represents C—Y2-4 or nitrogen;
X1, X2-1, X2-2, X2-3 and X2-4 each independently represents hydrogen, halogen, nitro, cyano, hydroxy, mercapto, amino, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylsulfanyl, alkylsulfinyl, alkylsulfonyl, haloalkylsulfanyl, haloalkylsulfinyl, haloalkylsulfonyl, acylamino, alkoxycarbonylamino, haloalkoxycarbonylamino, alkoxyimino, haloalkoxyimino, alkylsulfonylamino, or pentafluorosulfur;
Y2-1, Y2-3, and Y2-4 each independently represents hydrogen, halogen, nitro, cyano, hydroxy, mercapto, amino, alkyl, haloalkyl, cycloalkyl, cyclohaloalkyl, alkenyl, alkynyl, alkoxy, haloalkoxy, alkylsulfanyl, alkylsulfinyl, alkylsulfonyl, haloalkylsulfanyl, haloalkylsulfinyl, haloalkylsulfonyl, alkylsulfonyloxy, haloalkylsulfonyloxy, alkylaminosulfonyl, haloalkylaminosulfonyl, dialkylaminosulfonyl, di(haloalkyl)aminosulfonyl, alkylamino, dialkylamino, acylamino, alkoxycarbonylamino, haloalkoxycarbonylamino, alkylsulfonylamino, haloalkylsulfonylamino, trialkylsilyl, alkoxyimino, haloalkoxyimino, alkoxyiminoalkyl, haloalkoxyiminoalkyl, alkylsulfinylimino, alkylsulfinyliminoalkyl, alkylsulfinyliminoalkylcarbonyl, alkylsulfoxyimino, alkylsulfoxyiminoalkyl, alkoxycarbonyl, alkylcarbonyl, aminocarbonyl, alkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminocarbonyl, or dialkylaminothiocarbonyl;
R3 and R4 each independently represents hydrogen, cyano, alkyl, alkenyl, alkynyl, cycloalkyl or alkoxycarbonyl;
R5-1 represents hydrogen, amino, hydroxy, cyano, alkyl, haloalkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, aminocarbonylalkyl, iminoalkyl, alkylcarbonyl, alkylcarbonylamino, alkylimino, aryl, aralkyl, a heterocycle, a heterocyclic ring substituted alkyl, R7—C(═O)—, or R7—C(═S)—;
R6-1 represents C3-6cycloalkyl(C1-4)alkylcarbonyl, C1-4-alkoxy(C1-4)alkylcarbonyl, C1-4alkyl-S(C1-4)alkylcarbonyl, C1-4alkyl-SO(C1-4)alkylcarbonyl, C1-4 alkyl-SO2(C1-4)alkylcarbonyl,
R7 represents phenyl or a saturated or unsaturated heterocyclic ring.

### Claim 2 (depends on 1)

The arylpyrrolidine compound of claim 1, wherein
X1, X2-1, X2-2, X2-3 and X2-4 each independently represents hydrogen, halogen or haloalkyl;
Y2-1, Y2-3, and Y2-4 each independently represents hydrogen, halogen, alkyl, haloalkyl, alkoxy, cycloalkyl, haloalkoxy, alkylsulfonyl, or haloalkylsulfinyl;
R3, R4 each independently represents hydrogen or alkyl;
R5-1 represents hydrogen, alkyl, or haloalkyl; and
R6-1 represents C3-6cycloalkyl(C1-4)alkylcarbonyl, C1-4alkoxy(C1-4)alkylcarbonyl, C1-4alkyl-S(C1-4)alkylcarbonyl, C1-4alkyl-SO(C1-4)alkylcarbonyl, C1-4 alkyl-SO2(C1-4)alkylcarbonyl,

### Claim 3 (depends on 1)

The arylpyrrolidine compound of claim 1, wherein
X1, Y2-1, Y2-2, Y2-3 and X2-4 each independently represents hydrogen, halogen or C1-4-haloalkyl;
Y2-1, Y2-3, and Y2-4 each independently represents hydrogen, halogen, C1-4-alkyl, C1-4-alkoxy, C1-4-haloalkoxy, C3-6-cycloalkyl, C1-4-haloalkyl, C1-4alkylsulfanyl, or C1-4-haloalkylsulfanyl;
R3 or R4 independently of each other represents hydrogen;
R5-1 represents hydrogen, C1-4 alkyl or C1-4-haloalkyl; and
R6-1 is selected from the group consisting of

### Claim 4 (depends on 2)

The arylpyrrolidine compound of claim 2, wherein at least one of X1, X2-1, X2-2, X2-3 and X2-4 is hydrogen.

### Claim 5 (depends on 2)

The arylpyrrolidine compound of claim 2, wherein at least one of X1, X2-2, and X2-4 is hydrogen.

### Claim 6 (depends on 2)

The arylpyrrolidine compound of claim 2, wherein X1 and X2-4 are hydrogen, and X2-1, X2-2, and X2-3 each independently is selected from the group consisting of CF3, F, Cl, and Br.

### Claim 7

An arylpyrrolidine compound having the formula
or salts thereof,
wherein
X1, X2-1, X2-2, X2-3 and X2-4 each independently represents hydrogen, halogen, nitro, cyano, hydroxy, mercapto, amino, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylsulfanyl, alkylsulfinyl, alkylsulfonyl, haloalkylsulfanyl, haloalkylsulfinyl, haloalkylsulfonyl, acylamino, alkoxycarbonylamino, haloalkoxycarbonylamino, alkoxyimino, haloalkoxyimino, alkylsulfonylamino, or pentafluorosulfur;
Y2-3 and Y2-4 each independently represents hydrogen, halogen, nitro, cyano, hydroxy, mercapto, amino, alkyl, haloalkyl, cycloalkyl, cyclohaloalkyl, alkenyl, alkynyl, alkoxy, haloalkoxy, alkylsulfanyl, alkylsulfinyl, alkylsulfonyl, haloalkylsulfanyl, haloalkylsulfinyl, haloalkylsulfonyl, alkylsulfonyloxy, haloalkylsulfonyloxy, alkylaminosulfonyl, haloalkylaminosulfonyl, dialkylaminosulfonyl, di(haloalkyl)aminosulfonyl, alkylamino, dialkylamino, acylamino, alkoxycarbonylamino, haloalkoxycarbonylamino, alkylsulfonylamino, haloalkylsulfonylamino, trialkylsilyl, alkoxyimino, haloalkoxyimino, alkoxyiminoalkyl, haloalkoxyiminoalkyl, alkylsulfinylimino, alkylsulfinyliminoalkyl, alkylsulfinyliminoalkylcarbonyl, alkylsulfoxyimino, alkylsulfoxyiminoalkyl, alkoxycarbonyl, alkylcarbonyl, aminocarbonyl, alkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminocarbonyl, or dialkylaminothiocarbonyl;
R3 and R4 each independently represents hydrogen, cyano, alkyl, alkenyl, alkynyl, cycloalkyl or alkoxycarbonyl;
R5-1 represents hydrogen, amino, hydroxy, cyano, alkyl, haloalkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, aminocarbonylalkyl, iminoalkyl, alkylcarbonyl, alkylcarbonylamino, alkylimino, aryl, aralkyl, a heterocycle, a heterocyclic ring substituted alkyl, R7—C(═O)—, or R7—C(═S)—;
R6-1 represents C3-6cycloalkyl(C1-4)alkylcarbonyl, C1-4alkoxy(C1-4)alkylcarbonyl, C1-4alkyl-S(C1-4)alkylcarbonyl, C1-4alkyl-SO(C1-4alkylcarbonyl, C1-4 alkyl-SO2(C1-4)alkylcarbonyl,
R7 represents phenyl or a saturated or unsaturated heterocyclic ring.

### Claim 8 (depends on 7)

The arylpyrrolidine compound of claim 7, wherein
X1, X2-1, X2-2, X2-3 and X2-4 each independently represents hydrogen, halogen or haloalkyl;
Y2-3 and Y2-4 each independently represents hydrogen, halogen, alkyl, haloalkyl, alkoxy, cycloalkyl, haloalkoxy, alkylsulfonyl, or haloalkylsulfinyl;
R3 and R4 each independently represents hydrogen or alkyl;
R5-1 represents hydrogen, alkyl, or haloalkyl; and
R6-1 represents C3-6cycloalkyl(C1-4)alkylcarbonyl, C1-4alkoxy(C1-4)alkylcarbonyl, C1-4alkyl-S(C1-4)alkylcarbonyl, C1-4alkyl-SO(C1-4)alkylcarbonyl, C1-4 alkyl-SO2(C1-4)alkylcarbonyl,

### Claim 9 (depends on 7)

The arylpyrrolidine compound of claim 7, wherein
X1, X2-1, X2-2, X2-3 and X2-4 each independently represents hydrogen, halogen or C1-4-haloalkyl;
Y2-3 and Y2-4 each independently represents hydrogen, halogen, C1-4-alkyl, C1-4-alkoxy, C1-4-haloalkoxy, C3-6-cycloalkyl, C1-4-haloalkyl, C1-4-alkylsulfanyl, or C1-4-haloalkylsulfanyl;
R3 and R4 independently of each other represents hydrogen;
R5-1 represents hydrogen, C1-4 alkyl or C1-4haloalkyl; and
R6-1 is selected from the group consisting of

### Claim 10 (depends on 7)

The arylpyrrolidine compound of claim 7, wherein at least one of X1, X2-1, X2-2, X2-3 and A2-4 is hydrogen.

### Claim 11 (depends on 7)

The arylpyrrolidine compound of claim 7, wherein at least one of X1, X2-2, and X2-4 is hydrogen.

### Claim 12 (depends on 7)

The arylpyrrolidine compound of claim 7, wherein X1 and X2-4 are hydrogen, and X2-1, X2-2, and X2-3 each independently is selected from the group consisting of CF3, F, Cl, and Br.

### Claim 13 (depends on 1)

A composition comprising one or more compounds selected from the compounds according to claim 1 and one or more diluents, emulsifiers, or a combination thereof.

### Claim 14 (depends on 3)

A composition comprising one or more compounds selected from the compounds according to claim 3 and one or more diluents, emulsifiers, or a combination thereof.

### Claim 15 (depends on 7)

A composition comprising one or more compounds selected from the compounds according to claim 7 and one or more diluents, emulsifiers, or a combination thereof.

### Claim 16 (depends on 9)

A composition comprising one or more compounds selected from the compounds according to claim 9 and one or more diluents, emulsifiers, or a combination thereof.

### Claim 17 (depends on 13, 14)

A method for controlling plant damaging animal pests comprising applying the composition according to claim 13 or 14 to said pests, their habitat, or a combination thereof.

### Claim 18 (depends on 14, 17)

The method of claim 17, wherein the composition according to claim 14 is applied to said pests, their habitat, or a combination thereof.

### Claim 19 (depends on 15, 16)

A method for controlling parasites in or on an animal comprising administering the composition according to claim 15 or 16 to said animal.

### Claim 20 (depends on 16, 19)

The method of claim 19, wherein the composition according to claim 16 is applied to said animal.

### Claim 21 (depends on 13, 14)

A method for treating seeds of conventional or transgenic plants comprising administering the composition according to claim 13 or 14 to said seeds.

### Claim 22 (depends on 14, 21)

The method of claim 21, wherein the composition according to claim 14 is applied to said seeds.

### Claim 23 (depends on 1)

The arylpyrrolidine compound of claim 1, wherein the compound is

### Claim 24 (depends on 1)

The arylpyrrolidine compound of claim 1, wherein the compound is

### Claim 25 (depends on 1)

The arylpyrrolidine compound of claim 1, wherein the compound is

### Claim 26 (depends on 1)

The arylpyrrolidine compound of claim 1, wherein the compound is

### Claim 27 (depends on 23, 24, 25, 26)

A composition comprising any of the compounds according to any of claims 23-26 and one or more diluents, emulsifiers, or a combination thereof.