# US 10,499,642 B2 · Isoxazoline-substituted benzamides and analogues as insecticides

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- Number: US 10,499,642 B2
- Document ID: US10499642B2
- Status: Granted
- Kind: B2
- Application number: 15/762,498
- Filed: 2016-09-22
- Published: 2018-09-27
- Granted: 2019-12-10
- Earliest claimed: 2015-09-23
- Assignees: Syngenta Participations AG
- Applicants: Syngenta Participations AG
- Inventors: Anthony Cornelius O'Sullivan; Myriem El Qacemi; Jérôme Yves Cassayre; Thomas Pitterna; André Stoller
- Web page: https://patentgrep.com/patent/US10499642B2

## CPC

- A01N 43/80: five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
- A61P 33/10: Anthelmintics
- A61P 33/14: Ectoparasiticides, e.g. scabicides
- C07D 261/04: having one double bond between ring members or between a ring member and a non-ring member
- C07D 413/12: linked by a chain containing hetero atoms as chain links
- C07D 413/14: 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

Compounds of formula (I) wherein the substituents are as defined in claim 1, and the agrochemically acceptable salts salts, stereoisomers, enantiomers, tautomers and N-oxides of those compounds, and their uses as insecticides.

## Claims

### Claim 1

A compound of formula (I),
wherein
A1, A2, A3 and A4 are, independently of one another, C—H, C—R5 or N;
R1 is hydrogen, formyl, C1-C8alkyl, C1-C8alkylcarbonyl-, C1-C8alkoxy, C1-C8alkoxy-C1-C8alkyl or C1-C8alkoxycarbonyl, phenyl-C1-C8alkoxycarbonyl, phenyl-C1-C4alkyl, or phenyl-C1-C4alkyl wherein the phenyl moiety is substituted by one to three R7;
R2 is hydrogen, halogen, cyano, —NH(R8), —N(R8)(R9), —OR10, —SR10, —S(O)R10, —S(O)2R10, CORM, COOR10, C1-C8alkyl or C1-C8alkyl substituted by one to three R6a, C1-C8haloalkyl or C1-C8haloalkyl substituted by one to three R6a, C3-C8cycloalkyl or C3-C8cycloalkyl substituted by one to three R6b, C3-C8cycloalkyl where one carbon atom is replaced by O, S, S(O) or SO2, or C3-C8cycloalkyl-C1-C8alkyl, C3-C8cycloalkyl-C1-C8alkyl where one carbon atom in the cycloalkyl group is replaced by O, S, S(O) or SO2, or C3-C8cycloalkyl-C1-C8haloalkyl, C2-C8alkenyl or C2-C8alkenyl substituted by one to three R6a, C2-C8haloalkenyl or C2-C8haloalkenyl substituted by one to three R6a, C2-C8alkynyl, C2-C8haloalkynyl, phenyl, phenyl substituted by one to three R7, phenyl-C1-C4alkyl, phenyl-C1-C4alkyl wherein the phenyl moiety is substituted by one to three R7, 5-6 membered heteroaryl, 5-6 membered heteroaryl substituted by one to three R7, or 5-6 membered heteroaryl-C1-C4alkyl or 5-6 membered heteroaryl-C1-C4alkyl wherein the heteroaryl moiety is substituted by one to three R7;
R3 is C1-C8haloalkyl;
R4 is phenyl or phenyl substituted by one to three R6b or pyridine or pyridine substituted by one to three R6b;
each R5 is independently halogen, cyano, nitro, C1-C8alkyl, C3-C8cycloalkyl, C1-C8haloalkyl, C2-C8alkenyl, C2-C8haloalkenyl, C2-C8alkynyl, C2-C8haloalkynyl, C1-C8alkoxy, C1-C8haloalkoxy, or C1-C8alkoxycarbonyl-, or two R5 on adjacent carbon atoms together form a —CH═CH—CH═CH— bridge or a —N═CH—CH═CH— bridge;
each R6a is independently halogen, cyano, nitro, amino, hydroxy, oxo, C1-C8alkylamino, hydroxyimino, C1-C8alkyloxyimino, di-C1-C8alkylamino, C1-C8alkoxy, acetyloxy, formyloxy, C1-C8halo alkoxy, C1-C4alkylthio or tri-(C1-C4alkyl)silyl;
each R6b is independently halogen, cyano, nitro, C1-C8alkyl, C1-C8haloalkyl, amino, C1-C8alkylamino, di-C1-C8alkylamino, hydroxyl, C1-C4alkylthio, C1-C8alkoxy or C1-C8haloalkoxy;
each R7 is independently halogen, cyano, nitro, C1-C8alkyl, C1-C8haloalkyl, C1-C8alkoxy, or C1-C8haloalkoxy;
R8 and R9 are independently hydrogen, cyano, C1-C8alkyl or C1-C8alkyl substituted by one to three R6a, C1-C8alkoxy, C1-C8haloalkoxy, C1-C8haloalkoxy substituted by one to three R6a, C1-C8alkoxy substituted by one to three R6a,C1-C8haloalkyl or C1-C8haloalkyl substituted by one to three R6a, C3-C8cycloalkyl or C3-C8cycloalkyl substituted by one to three R6b, C3-C8cycloalkyl where one carbon atom is replaced by O, S, S(O) or SO2, or C3-C8cycloalkyl-C1-C8alkyl, C3-C8cycloalkyl-C1-C8alkyl where one carbon atom in the cycloalkyl group is replaced by O, S, S(O) or SO2, or C3-C8cycloalkyl-C1-C8haloalkyl, C2-C8alkenyl or C2-C8alkenyl substituted by one to three R6a, C2-C8haloalkenyl or C2-C8haloalkenyl substituted by one to three R6a, C2-C8alkynyl, C2-C8haloalkynyl, phenyl, phenyl substituted by one to three R7, phenyl-C1-C4alkyl, phenyl-C1-C4alkyl wherein the phenyl moiety is substituted by one to three R7, 5-6 membered heteroaryl, 5-6 membered heteroaryl substituted by one to three R7, 5-6 membered heteroaryl-C1-C4alkyl or 5-6 membered heteroaryl-C1-C4alkyl wherein the heteroaryl moiety is substituted by one to three R7, or R8 and R9 together with the nitrogen atom can be linked through a C3-C8alkylene chain, a C3-C8alkylene chain substituted by one to three R6b or a C3-C8alkylene chain, where one carbon atom is replaced by O, S, S(O) or SO2; and
R10 is hydrogen, cyano, C1-C8alkyl or C1-C8alkyl substituted by one to three R6a, C1-C8haloalkyl or C1-C8haloalkyl substituted by one to three R6a, C3-C8cycloalkyl or C3-C8cycloalkyl substituted by one to three R6b, C3-C8cycloalkyl where one carbon atom is replaced by O, S, S(O) or SO2, or C3-C8cycloalkyl-C1-C8alkyl, C3-C8cycloalkyl-C1-C8alkyl where one carbon atom in the cycloalkyl group is replaced by O, S, S(O) or SO2, or C3-C8cycloalkyl-C1-C8haloalkyl, C2-C8alkenyl or C2-C8alkenyl substituted by one to three R6a, C2-C8haloalkenyl or C2-C8haloalkenyl substituted by one to three R6a, C2-C8alkynyl, C2-C8haloalkynyl, phenyl, phenyl substituted by one to three R7, phenyl-C1-C4alkyl, phenyl-C1-C4alkyl wherein the phenyl moiety is substituted by one to three R7, 5-6 membered heteroaryl, 5-6 membered heteroaryl substituted by one to three R7, or 5-6 membered heteroaryl-C1-C4alkyl or 5-6 membered heteroaryl-C1-C4alkyl wherein the heteroaryl moiety is substituted by one to three R7; or
an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer and N-oxide thereof.

### Claim 2 (depends on 1)

The compound of claim 1, wherein A1 is C—R5; A2 is C—H; A3 is C—H; and A4 is C—H, wherein R5 is halogen, cyano, nitro, C1-C8alkyl, C3-C8cycloalkyl, C1-C8haloalkyl, or C2-C8alkenyl.

### Claim 3 (depends on 1)

The compound of claim 1, wherein R2 is halogen, C1-C4alkyl, C3-C5cycloalkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, di-C1-C4alkylamino, C1-C4alkylthio, or C1-C4alkyloxycarbonyl.

### Claim 4 (depends on 1)

The compound of claim 1, wherein R1 is hydrogen, formyl, C1-C8alkyl, C1-C8alkylcarbonyl- or C1-C8alkoxycarbonyl-.

### Claim 5 (depends on 1)

The compound of claim 1, wherein R3 is C1-C4haloalkyl.

### Claim 6 (depends on 1)

The compound of claim 1, wherein
R4 is phenyl or phenyl substituted by one to three R6b; and
each R6b independently is halogen, cyano, nitro, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, or C1-C4haloalkoxy.

### Claim 7 (depends on 6)

The compound of claim 6, wherein R6b is bromo, chloro, fluoro, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxy, difluoromethoxy, or trifluoromethoxy.

### Claim 8 (depends on 1)

The compound of claim 1, wherein at least two of A1, A2, A3 and A4 is C—H.

### Claim 9 (depends on 1)

The compound of claim 1, wherein R2 is halogen, cyano, —NH(R8), —N(R8)(R9), —OR10, —SR10, —S(O)R10, —S(O)2R10, COR10, COOR10,C1-C8alkyl or C1-C8alkyl substituted by one to three R6a, C1-C8haloalkyl or C1-C8haloalkyl substituted by one to three R6a, C3-C8cycloalkyl or C3-C8cycloalkyl substituted by one to three R6b, C3-C8cycloalkyl where one carbon atom is replaced by O, S, S(O) or SO2, or C3-C8cycloalkyl-C1-C8alkyl, C3-C8cycloalkyl-C1-C8alkyl where one carbon atom in the cycloalkyl group is replaced by O, S, S(O) or SO2, or C3-C8cycloalkyl-C1-C8haloalkyl, C2-C8alkenyl or C2-C8alkenyl substituted by one to three R6a, C2-C8haloalkenyl or C2-C8haloalkenyl substituted by one to three R6a, C2-C8alkynyl, C2-C8haloalkynyl, phenyl, phenyl substituted by one to three R7, phenyl-C1-C4alkyl, phenyl-C1-C4alkyl wherein the phenyl moiety is substituted by one to three R7, 5-6 membered heteroaryl, 5-6 membered heteroaryl substituted by one to three R7, or 5-6 membered heteroaryl-C1-C4alkyl or 5-6 membered heteroaryl-C1-C4alkyl wherein the heteroaryl moiety is substituted by one to three R7.

### Claim 10 (depends on 1)

The compound of claim 1, wherein R2 is halogen, cyano, —NH(R8), —N(R8)(R9), —OR10, —SR10, —S(O)R10, —S(O)2R10, COR10, COOR10, C8haloalkyl or C1-C8haloalkyl substituted by one to three R6a, C3-C8cycloalkyl or C3-C8cycloalkyl substituted by one to three R6b, C3-C8cycloalkyl where one carbon atom is replaced by O, S, S(O) or SO2, or C3-C8cycloalkyl-C1-C8alkyl, C3-C8cycloalkyl-C1-C8alkyl where one carbon atom in the cycloalkyl group is replaced by O, S, S(O) or SO2, or C3-C8cycloalkyl-C1-C8haloalkyl, C2-C8alkenyl or C2-C8alkenyl substituted by one to three R6a, C2-C8haloalkenyl or C2-C8haloalkenyl substituted by one to three R6a, C2-C8alkynyl, C2-C8haloalkynyl, phenyl, phenyl substituted by one to three R7, phenyl-C1-C4alkyl, phenyl-C1-C4alkyl wherein the phenyl moiety is substituted by one to three R7, 5-6 membered heteroaryl, 5-6 membered heteroaryl substituted by one to three R7, or 5-6 membered heteroaryl-C1-C4alkyl or 5-6 membered heteroaryl-C1-C4alkyl wherein the heteroaryl moiety is substituted by one to three R7.

### Claim 11 (depends on 1)

The compound of claim 1, wherein R2 is —NH(R8), —N(R8)(R9), OR10, SR10, —S(O)R10, —S(O)2R10, COR10, COOR10, C8alkyl or C3-C8alkyl substituted by one to three R6a, C3-C8haloalkyl or C3-C8haloalkyl substituted by one to three R6a, C3-C8cycloalkyl or C3-C8cycloalkyl substituted by one to three R6b, C3-C8cycloalkyl where one carbon atom is replaced by O, S, S(O) or SO2, or C3-C8cycloalkyl-C1-C8alkyl, C3-C8cycloalkyl-C1-C8alkyl where one carbon atom in the cycloalkyl group is replaced by O, S, S(O) or SO2, or C3-C8cycloalkyl-C1-C8haloalkyl, C2-C8alkenyl or C2-C8alkenyl substituted by one to three R6a, C2-C8haloalkenyl or C2-C8haloalkenyl substituted by one to three R6a, C2-C8alkynyl, C2-C8haloalkynyl, phenyl, phenyl substituted by one to three R7, phenyl-C1-C4alkyl, phenyl-C1-C4alkyl wherein the phenyl moiety is substituted by one to three R7, 5-6 membered heteroaryl, 5-6 membered heteroaryl substituted by one to three R7, or 5-6 membered heteroaryl-C1-C4alkyl or 5-6 membered heteroaryl-C1-C4alkyl wherein the heteroaryl moiety is substituted by one to three R7.

### Claim 12 (depends on 1)

The compound of claim 1 represented by the compound of formula (Ib)
wherein
A1 is C—R5 and A2, A3 and A4 are C—H;
R1 is hydrogen, formyl, phenyl-C1-C4alkyl, phenyl-C1-C4alkyl wherein the phenyl moiety is substituted by one to three R7;
R2 is hydrogen, halogen, —NH(R8), —N(R8)(R9), —OR10, —SR10, —S(O)R10, —S(O)2R10, COR10, COOR10, C1-C8haloalkyl or C1-C8haloalkyl substituted by one to three Rha, or C3-C8cycloalkyl or C3-C8cycloalkyl substituted by one to three R6b;
R5 is independently halogen, C1-C8alkyl;
each R6a is independently hydroxy, oxo, hydroxyimino, C1-C8alkyloxyimino, C1-C8alkoxy, acetyloxy, formyloxy or tri-(C1-C4alkyl)silyl;
each R6b is halogen, C1-C8haloalkyl, or C1-C4alkylthio;
each R7 is independently halogen, C1-C8alkoxy, or C1-C8haloalkoxy;
R8 and R9 are independently hydrogen, C1-C8alkyl or C1-C8alkyl substituted by one to three R6a;
R10 is hydrogen, C1-C8alkyl or C1-C8alkyl substituted by one to three R6a, C1-C8haloalkyl or C1-C8haloalkyl substituted by one to three R6a, C3-C8cycloalkyl or C3-C8cycloalkyl substituted by one to three R6b, C3-C8cycloalkyl where one carbon atom is replaced by O, S, S(O) or SO2, or C3-C8cycloalkyl-C1-C8alkyl, C3-C8cycloalkyl-C1-C8alkyl where one carbon atom in the cycloalkyl group is replaced by O, S, S(O) or SO2, or C3-C8cycloalkyl-C1-C8haloalkyl, C2-C8alkenyl or C2-C8alkenyl substituted by one to three R6a, C2-C8haloalkenyl or C2-C8haloalkenyl substituted by one to three R6a, C2-C8alkynyl, C2-C8haloalkynyl, phenyl, phenyl substituted by one to three R7, phenyl-C1-C4alkyl, phenyl-C1-C4alkyl wherein the phenyl moiety is substituted by one to three R7, 5-6 membered heteroaryl, 5-6 membered heteroaryl substituted by one to three R7, 5-6 membered heteroaryl-C1-C4alkyl or 5-6 membered heteroaryl-C1-C4alkyl wherein the heteroaryl moiety is substituted by one to three R7.

### Claim 13 (depends on 1)

A pesticidal composition, which comprises at least one compound of formula (I) according to claim 1 or, where appropriate, a tautomer thereof, in each case in free form or in agrochemically utilizable salt form, as active ingredient.

### Claim 14 (depends on 13)

A method for controlling pests, which comprises applying a composition according to claim 13 to the pests or their environment with the exception of a method for treatment of the human or animal body by surgery or therapy and diagnostic methods practised on the human or animal body.

### Claim 15 (depends on 13)

A method for the protection of plant propagation material from the attack by pests, which comprises treating the propagation material or the site, where the propagation material is planted, with a composition according to claim 13.

### Claim 16 (depends on 13)

Plant propagation material treated with the pesticidal composition according to claim 13.