# US 9,040,708 B2 · Pesticidal compounds

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- Number: US 9,040,708 B2
- Document ID: US9040708B2
- Status: Granted
- Kind: B2
- Application number: 14/354,170
- Filed: 2012-10-31
- Published: 2014-10-02
- Granted: 2015-05-26
- Earliest claimed: 2011-11-04
- Assignees: Syngenta Limited; Syngenta Participations AG
- Applicants: Syngenta Participants AG
- Inventors: Thomas Pitterna; Olivier Loiseleur; Paul Anthony Worthington; Anthony Cornelius O'Sullivan; Torsten Luksch; Vladimir Bobosik
- Web page: https://patentgrep.com/patent/US9040708B2

## CPC

- A01N 43/40: six-membered rings
- A01N 43/54: 1,3-Diazines; Hydrogenated 1,3-diazines
- A01N 43/58: 1,2-Diazines; Hydrogenated 1,2-diazines
- A01N 43/60: 1,4-Diazines; Hydrogenated 1,4-diazines
- A61P 33/00: Antiparasitic agents
- A61P 33/10: Anthelmintics
- A61P 33/14: Ectoparasiticides, e.g. scabicides
- C07D 213/40: Acylated substituent nitrogen atom
- C07D 213/61: Halogen atoms or nitro radicals
- C07D 213/71: to which a second hetero atom is attached
- C07D 213/81: Amides; Imides
- C07D 213/82: in position 3
- C07D 213/85: in position 3
- C07D 213/89: with hetero atoms directly attached to the ring nitrogen atom
- C07D 401/12: linked by a chain containing hetero atoms as chain links
- 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

A compound of formula (I) wherein R1 to R4 are, for example, each hydrogen, R5 is pyridyl, which has two or more substituents selected, for example, from halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, and cyano; R6 is, for example, hydrogen; R7 is, for example, hydrogen, cyano, hydroxyl, formyl, C1-C4-alkyl, C1-C4-alkoxy, C2-C4-alkenyl, or C2-C4-alkynyl; and A1 to A5 are, independently selected, from, for example, N, and C—H; and its use as a pesticidal agent.

## Claims

### Claim 1

A compound of the formula (I) wherein
wherein
R1 is hydrogen;
R2 is hydrogen;
R3 is hydrogen;
R4 is hydrogen;
R5 is pyridyl, which has two or more substituents selected independently from each other from halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylsulfanyl, C1-C4-haloalkylsulfanyl, C1-C4-alkylsulfinyl, C1-C4-haloalkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-haloalkylsulfonyl, C3-C6-cycloalkyl, which cycloalkyl is unsubstituted or substituted by one or more substituents Rx;
R6 is hydrogen or C1-C4-alkyl;
R7 is hydrogen, cyano, hydroxyl, formyl, C1-C4-alkyl, C1-C4-alkoxy, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-cyanoalkyl, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl, benzyl, C3-C6-cycloalkylcarbonyl or C3-C6-cycloalkoxycarbonyl;
A1 is N, C—H or C—X;
A2 is N, C—H or C—X;
A3 is N, C—H or C—X;
A4 is N, C—H or C—X;
A5 is N, C—H or C—X;
X is a halogen, OH, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
Rx, independently of each other, is selected from halogen, C1-C4-alkyl, and C1-C4-haloalkyl;
with the proviso that at most three of A1 to A5 are N;
as well as its acceptable salts, enantiomers, diastereomers, tautomers, and N-oxides.

### Claim 2 (depends on 1)

A compound according to claim 1, wherein
R1, R2, R3 and R4 are each hydrogen;
R5 is pyridyl, which has two or more substituents selected independently from each other from halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C3-C6-cycloalkyl, which cycloalkyl is unsubstituted or substituted by one or more substituents Rx;
R6 is hydrogen or C1-C4-alkyl;
R7 is hydrogen, C1-C4-alkylcarbonyl or C1-C4-alkoxycarbonyl;
A1, A2, A3, A4 and A5 are, independently of each other, N, C—H or C—X;
X, independently of each other, is a halogen, cyano or C1-C4-haloalkyl; and
Rx, independently of each other, is selected from halogen and C1-C4-haloalkyl.

### Claim 3 (depends on 1)

The compound according to claim 1, wherein the pyridyl in R5 has two substituents.

### Claim 4 (depends on 1)

The compound according to claim 1 wherein the pyridyl in R5 has as one of its substituents a C3-C6-cycloalkyl, which cycloalkyl is unsubstituted or substituted by one or more substituents Rx; wherein Rx, independently of each other, is selected from halogen and C1-C4-haloalkyl.

### Claim 5 (depends on 1)

A compound of the formula (I) defined in claim 1, wherein
R1, R2, R3 and R4 are each hydrogen;
R5 is pyridyl, which has two or more substituents selected independently from each other from halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C3-C6-cycloalkyl, which cycloalkyl is unsubstituted or substituted by one or more substituents Rx;
R6 is hydrogen or C1-C4-alkyl;
R7 is hydrogen, C1-C4-alkylcarbonyl or C1-C4-alkoxycarbonyl;
A1, A2, A3, A4 and A5 are, independently of each other, N, C—H or C—X;
X, independently of each other, is a C1-C4-alkylsulfanyl, C1-C4-haloalkylsulfanyl, C1-C4-alkylsulfinyl, C1-C4-haloalkylsulfinyl, C1-C4-alkylsulfonyl, or C1-C4-haloalkylsulfonyl; and
Rx, independently of each other, is selected from halogen and C1-C4-haloalkyl.

### Claim 6 (depends on 5)

The compound according to claim 5 wherein X is, independently of each other, a C1-C2-alkylsulfanyl, C1-C2-haloalkylsulfanyl, C1-C2-alkylsulfinyl, C1-C2-haloalkylsulfinyl, C1-C2-alkylsulfonyl, or C1-C2-haloalkylsulfonyl.

### Claim 7 (depends on 1)

The compound according to claim 1, wherein the substituents on the pyridyl at R5 are selected, independently from each other, from halogen, cyano, C1-C2-alkyl, C1-C2-haloalkyl or C3-C4-cycloalkyl, which cycloalkyl is unsubstituted or substituted by one or more substituents Rx, wherein Rx is, independently selected, from halogen, C1-C4-alkyl, and C1-C4-haloalkyl.

### Claim 8 (depends on 1)

The compound according to claim 1, wherein there is one substituent Rx on cycloalkyl, which is selected from halogen, C1-C2-alkyl, and C1-C2-haloalkyl, such as chlorine, fluorine, methyl, and trifluoromethyl.

### Claim 9 (depends on 1)

The compound according to claim 1, wherein the two or more substituents on the pyridyl at R5 are independently selected from a halogen, such as chlorine, fluorine and bromine.

### Claim 10 (depends on 1)

The compound according to claim 1, wherein R5, which is pyridyl, has two substituents selected, independently from each other, from halogen, and C1-C2-haloalkyl.

### Claim 11 (depends on 1)

The compound according to claim 1 wherein R5 is 2-pyridyl having two substituents at positions 3 and 5.

### Claim 12 (depends on 1)

The compound according to claim 1 wherein R5 is 3-pyridyl having two substituents at positions 2 and 6.

### Claim 13 (depends on 1)

The compound according to claim 1 wherein R5 is 4-pyridyl having two substituents at positions 3 and 5 or positions 2 and 3.

### Claim 14 (depends on 1)

The compound according to claim 1, wherein R1, R2, R3 and R4 are each hydrogen; R5 is pyrid-2-yl or pyrid-3-yl, which has two substituents selected independently from each other from halogen, cyano, C1-C4-haloalkyl, and C3-C6-cycloalkyl, which cycloalkyl is optionally substituted by one Rx; R6 is hydrogen or methyl; R7 is hydrogen; A1, A2, A3, A4 and A5 are, independently of each other, N, C—H or C—X, where X is a halogen, C1-C4-alkyl or C1-C4-haloalkyl; with the proviso that one of A1 to A5 are N; and Rx is selected from halogen, C1-C4-alkyl, and C1-C4-haloalkyl.

### Claim 15 (depends on 1)

The compound according to claim 1, wherein R1 to R4 are each hydrogen; R5 is pyrid-2-yl substituted in 3- and 5-position, independently of each other, by C3-C4-cycloalkyl, which cycloalkyl is optionally substituted by one Rx, C1-C2-haloalkyl, halogen or cyano; R6 and R7 are each hydrogen; A1 is C—CF3, A2 to A4 is CH and A5 is CH or N; and Rx is selected from halogen, C1-C4-alkyl, and C1-C4-haloalkyl.

### Claim 16 (depends on 1)

The compound according to claim 1, wherein R1 to R4 are each hydrogen; R5 is pyrid-3-yl substituted in 2- and 6-position, independently of each other, by C3-C4-cycloalkyl, which cycloalkyl is optionally substituted by one Rx, C1-C2-haloalkyl, halogen or cyano; R6 and R7 are each hydrogen; A1 is C—CF3, A2 to A4 are each CH and A5 is CH or N; and Rx is selected from halogen, C1-C4-alkyl, and C1-C4-haloalkyl.

### Claim 17 (depends on 15)

The compound according to claim 15, wherein the R5 is pyrid-2-yl substituted in 3- and 5-position, independently of each other, by a C3-C4-cycloalkyl, which cycloalkyl is optionally substituted by one Rx, and a substituent selected from C1-C2-haloalkyl, halogen or cyano; and Rx is selected from halogen, C1-C4-alkyl, and C1-C4-haloalkyl.

### Claim 18 (depends on 1)

A composition comprising a compound defined in claim 1 and a agronomically carrier and optionally one or more customary formulation auxiliaries.

### Claim 19 (depends on 13)

The composition according to claim 13 further comprising one or more other biologically active compounds.

### Claim 20 (depends on 1)

The compound according to claim 1 wherein R6 is hydrogen or C1-C2-alkyl.

### Claim 21 (depends on 1)

The compound according to claim 1 wherein R7 is selected from hydrogen, hydroxyl, and C1-C4-alkoxy.

### Claim 22 (depends on 1)

The compound according to claim 1 wherein A1 is CX, A2 to A5 are each CH and R5 is 2-pyridyl.

### Claim 23 (depends on 1)

The compound according to claim 1 wherein A1 to A5 is independently selected from C—H and C—X.

### Claim 24 (depends on 1)

The compound according to claim 1 wherein A2 to A5 are CH and A1 is C—CF3.