# US 11,026,427 B2 · Microbiocidal oxadiazole derivatives

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- Number: US 11,026,427 B2
- Document ID: US11026427B2
- Status: Granted
- Kind: B2
- Application number: 16/312,113
- Filed: 2017-06-19
- Published: 2019-07-25
- Granted: 2021-06-08
- Earliest claimed: 2016-06-21
- Assignees: Syngenta Participations AG
- Applicants: Syngenta Participations AG
- Inventors: Thomas James Hoffman; Daniel Stierli; Martin Pouliot
- Web page: https://patentgrep.com/patent/US11026427B2

## CPC

- A01N 43/82: five-membered rings with three ring hetero atoms
- C07D 271/06: 1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
- C07D 413/10: linked by a carbon chain containing aromatic rings
- C07D 417/10: linked by a carbon chain containing aromatic 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
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Compounds of the Formula (I), wherein the substituents are as defined in claim 1, useful as pesticides, especially as fungicides.

## Claims

### Claim 1

A compound of formula (I):
wherein
A1 represents N or CR1, wherein R1 is hydrogen, halogen, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy or difluoromethoxy;
A2 represents N or CR2, wherein R2 is hydrogen, halogen, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy or difluoromethoxy;
A3 represents N or CR3, wherein R3 is hydrogen or fluoro;
A4 represents N or CR4, wherein R4 is hydrogen or fluoro; and
wherein no more than two of A1 to A4 are N;
L1 represents —C(O)—;
R5 represents cyano, cyanoC1-6alkyl, C1-3alkoxyC1-4alkyl, C1-2fluoroalkoxyC1-4alkyl, C3-6alkenyl, C3-6alkynyl, C3-8cycloalkyl or C3-8cycloalkylC1-2alkyl wherein the cycloalkyl moiety is optionally partially unsaturated, phenyl, phenylC1-2alkyl, heteroaryl bonded to L1 through a carbon atom or heteroarylC1-2alkyl, wherein the heteroaryl moiety is a 5- or 6-membered monocyclic aromatic ring which comprises 1, 2, 3 or 4 heteroatoms individually selected from N, O and S, heterocyclyl bonded to L1 through a carbon atom or heterocyclylC1-2alkyl, wherein the heterocyclyl moiety is a 4- to 6-membered non-aromatic ring which comprises 1, 2 or 3 heteroatoms individually selected from N, O and S, and wherein C3-8cycloalkyl, phenyl, heteroaryl and heterocyclyl are optionally substituted by 1, 2 or 3 substituents, which may be the same or different, selected from R7, and wherein when R5 represents C3-8cycloalkyl, C3-8cycloalkylC1-2alkyl, heterocyclyl or heterocyclylC1-2alkyl, the C3-8cycloalkyl or heterocyclyl moiety is optionally substituted by 1 or 2 oxo groups;
R7 represents cyano, halogen, hydroxy, C1-4alkyl, C1-2haloalkyl, C1-4alkoxy, C1-2haloalkoxy, C1-4alkylcarbonyl, C1-4alkoxycarbonyl, aminocarbonyl, C1-4alkylaminocarbonyl or diC1-4alkylaminocarbonyl;
or
a salt or an N-oxide thereof.

### Claim 2

A compound of formula (I):
wherein
A1 represents N or CR1, wherein R1 is hydrogen, halogen, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy or difluoromethoxy;
A2 represents N or CR2, wherein R2 is hydrogen, halogen, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy or difluoromethoxy;
A3 represents Nor CR3, wherein R3 is hydrogen or fluoro;
A4 represents N or CR4, wherein R4 is hydrogen or fluoro; and
wherein no more than two of A1 to A4 are N;
L1 represents —C(OH)(R6)—;
R5 represents cyano, C1-6haloalkyl, cyanoC1-6alkyl, C1-3alkoxyC1-4alkyl, C1-2fluoroalkoxyC1-4alkyl, C3-6alkenyl, C3-6alkynyl, C3-8cycloalkyl or C3-8cycloalkylC1-2alkyl wherein the cycloalkyl moiety is optionally partially unsaturated, phenyl, phenylC1-2alkyl, heteroaryl bonded to L1 through a carbon atom or heteroarylC1-2alkyl, wherein the heteroaryl moiety is a 5- or 6-membered monocyclic aromatic ring which comprises 1, 2, 3 or 4 heteroatoms individually selected from N, O and S, heterocyclyl bonded to L1 through a carbon atom or heterocyclylC1-2alkyl, wherein the heterocyclyl moiety is a 4- to 6-membered non-aromatic ring which comprises 1, 2 or 3 heteroatoms individually selected from N, O and S, and wherein C3-8cycloalkyl, phenyl, heteroaryl and heterocyclyl are optionally substituted by 1, 2 or 3 substituents, which may be the same or different, selected from R7, and wherein when R5 represents C3-8cycloalkyl, C3-8cycloalkylC1-2alkyl, heterocyclyl or heterocyclylC1-2alkyl, the C3-8cycloalkyl or heterocyclyl moiety is optionally substituted by 1 or 2 oxo groups;
R6 represents hydrogen, C1-6alkyl, C3-6alkenyl, C3-6alkynyl or C1-2haloalkyl;
R7 represents cyano, halogen, hydroxy, C1-4alkyl, C1-2haloalkyl, C1-4alkoxy, C1-2haloalkoxy, C1-4alkylcarbonyl, C1-4alkoxycarbonyl, aminocarbonyl, C1-4alkylaminocarbonyl or diC1-4alkylaminocarbonyl;
or
a salt or an N-oxide thereof.

### Claim 3 (depends on 1, 2)

The compound according to claim 1 or claim 2, wherein A1, A2, A3, and A4 are C—H.

### Claim 4 (depends on 1, 2)

The compound according to claim 1 or claim 2, wherein R5 is C3-4alkenyl, C3-4alkynyl or C3-6cycloalkyl wherein the cycloalkyl moiety is optionally partially unsaturated, phenyl or heteroaryl bonded to L1 through a carbon atom wherein the heteroaryl moiety is a 5- or 6-membered monocyclic aromatic ring which comprises 1 or 2 heteroatoms individually selected from N, O and S and wherein C3-6cycloalkyl, phenyl, and heteroaryl are optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R7, and wherein when R5 represents C3-6cycloalkyl, the C3-6cycloalkyl moiety is optionally substituted by 1 or 2 oxo groups.

### Claim 5 (depends on 1, 2)

The compound according to claim 1 or claim 2, wherein R5 is:
(i) C3-4alkenyl or C3-4alkynyl; or
(ii) cyclopropyl, phenyl, pyridyl, pyrimidinyl, pyrazolyl, thiazolyl, thienyl or isoxazolyl optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R7.

### Claim 6 (depends on 1, 2)

The compound according to claim 1 or claim 2, wherein R5 is:
(i) C3-4alkenyl or C3-4alkynyl; or
(ii) cyclopropyl, phenyl, 2-pyridyl, 3-pyridyl, pyrimidin-2-yl, pyrazol-4-yl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, thien-2-yl or isoxazol-5-yl optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R7.

### Claim 7 (depends on 1, 2)

The compound according to claim 1 or claim 2, wherein R7 is independently selected from cyano, halogen, hydroxy, C1-4alkyl, C1-2haloalkyl, C1-4alkoxy, C1-2haloalkoxy and C-4alkoxycarbonyl.

### Claim 8 (depends on 1, 2)

The compound according to claim 1 or claim 2, wherein R7 is independently selected from fluoro, methyl, ethyl, methoxy and trifluoromethoxy.

### Claim 9 (depends on 1, 2)

An agrochemical composition comprising a fungicidally effective amount of a compound of formula (I) according to claim 1 or claim 2.

### Claim 10 (depends on 9)

The composition according to claim 9, further comprising at least one additional active ingredient and/or an agrochemically-acceptable diluent or carrier.

### Claim 11 (depends on 1, 2)

A method of controlling infestation of useful plants by phytopathogenic microorganisms, wherein a fungicidally effective amount of a compound of formula (I) according to claim 1 or claim 2, or a composition comprising this compound as active ingredient, is applied to the plants, to parts thereof or the locus thereof.

### Claim 12 (depends on 1)

The compound according to claim 1, said compound being selected from the group consisting of:

### Claim 13 (depends on 2)

The compound according to claim 2, said compound being selected from the group consisting of: