# US 10,501,425 B2 · Microbiocidal oxadiazole derivatives

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- Number: US 10,501,425 B2
- Document ID: US10501425B2
- Status: Granted
- Kind: B2
- Application number: 15/765,089
- Filed: 2016-09-29
- Published: 2018-09-20
- Granted: 2019-12-10
- Earliest claimed: 2015-10-02
- Assignees: Syngenta Participations AG
- Applicants: Syngenta Participations AG
- Inventors: Daniel Stierli; Thomas James Hoffman; Renaud Beaudegnies; Martin Pouliot
- Web page: https://patentgrep.com/patent/US10501425B2

## CPC

- C07D 271/06: 1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
- A01N 43/82: five-membered rings with three ring hetero atoms
- A01N 47/12: containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
- A01N 47/28: Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< (isoureas, isothioureas A01N47/42)
- A01N 47/32: containing >N—CO—N< or >N—CS—N< groups directly attached to a cycloaliphatic ring
- A61P 31/02: Local antiseptics
- A61P 31/04: Antibacterial agents
- C07D 413/04: directly linked by a ring-member-to-ring-member bond
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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

## Abstract

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

## Claims

### Claim 1

A compound of formula (I):
wherein
n is 1 or 2;
A1 represents N or CR1, wherein R1 is hydrogen, halogen, methyl, ethyl, trifluoromethyl, methoxy, ethoxy or difluoromethoxy;
A2 represents N or CR2, wherein R2 is hydrogen, halogen, methyl, ethyl, trifluoromethyl, methoxy, ethoxy or difluoromethoxy;
A3 represents N or CR3, wherein R3 is hydrogen or halogen;
A4 represents N or CR4, wherein R4 is hydrogen or halogen; and
wherein no more than two of A1 to A4 are N;
R5 and R6 are independently selected from hydrogen, C1-4alkyl, halogen, cyano, trifluoromethyl and difluoromethyl;
R7 is hydrogen;
R8 represents —C(O)R9, wherein R9 is hydrogen, C1-6alkyl, C2-6alkenyl, C2-6alkynyl, cyanoC1-6alkyl, C1-6haloalkyl, C2-6haloalkenyl, hydroxyC1-6alkyl, hydroxyC1-6haloalkyl, C1-4alkoxyC1-6alkyl, C1-4haloalkoxyC1-6alkyl, C1-4alkoxyC1-4alkoxyC1-6alkyl, C2-6alkynyloxyC1-6alkyl, aminoC1-6alkyl, N—C1-4alkylaminoC1-6alkyl, N,N-diC1-4alkylaminoC1-6alkyl, C1-6alkylcarbonylC1-6alkyl, C1-6alkylcarbonylC2-6alkenyl, C1-6alkoxycarbonylC1-6alkyl, C1-6alkylcarbonyloxyC1-6alkyl, N—C1-4alkylcarbonylaminoC1-6alkyl, N—C1-4alkylaminocarbonylC1-6alkyl, N,N-diC1-4alkylaminocarbonylC1-6alkyl, C1-6alkylsulfanylC1-6alkyl, C1-6alkylsulfonylC1-6alkyl or C1-6alkylsulfonylaminoC1-6alkyl; or
R8 represents —C(O)OR10, wherein R10 is hydrogen, C1-8alkyl, C3-6alkenyl, C3-6alkynyl, cyanoC1-6alkyl, C1-6haloalkyl, C3-6haloalkenyl, hydroxyC1-6alkyl, C1-4alkoxyC1-6alkyl, C1-4haloalkoxyC1-6alkyl, C1-4alkoxyC1-4alkoxyC1-6alkyl, C2-6alkynyloxyC1-6alkyl, aminoC1-6alkyl, N—C1-4alkylaminoC1-6alkyl, N,N-diC1-4alkylaminoC1-6alkyl, C1-6alkylcarbonylC1-6alkyl, C1-6alkylcarbonylC2-6alkenyl, C1-6alkoxycarbonylC1-6alkyl, C1-6alkylcarbonyloxyC1-6alkyl, N—C1-4alkylaminocarbonylC1-6alkyl, N,N-diC1-4alkylaminocarbonylC1-6alkyl, C1-4alkylsulfanylC1-6alkyl, C1-6alkylsulfonylC1-6alkyl or C1-6alkylsulfonylaminoC1-6alkyl; or
R8 represents —C(O)NR11R12, wherein R11 is hydrogen, cyano, C1-7alkyl, C2-6alkenyl, C2-6alkynyl, cyanoC1-8alkyl, C1-6haloalkyl, C2-6haloalkenyl, hydroxyC1-6alkyl, C1-4alkoxyC1-6alkyl, C1-4haloalkoxyC1-6alkyl, C1-4alkoxyC1-4alkoxyC1-6alkyl, C2-6alkynyloxyC1-6alkyl, aminoC1-6alkyl, N—C1-4alkylaminoC1-6alkyl, N,N-diC1-4alkylaminoC1-6alkyl, C1-6alkylcarbonylC1-6alkyl, C1-6alkylcarbonylC2-6alkenyl, C1-6alkoxycarbonylC1-6alkyl, C1-6alkylcarbonyloxyC1-6alkyl, N—C1-4alkylaminocarbonylC1-6alkyl, N,N-diC1-4alkylaminocarbonylC1-6alkyl, C1-4alkylsulfanylC1-6alkyl, C1-6alkylsulfonylC1-6alkyl or C1-6alkylsulfonylaminoC1-6alkyl;
R12 is hydrogen, C1-4alkyl, C1-4alkoxy, C1-4alkoxyC1-6alkyl, C3-6alkenoxy or C3-6alkynoxy; or
R11 and R12 together with the nitrogen atom they share form a 4-, 5- or 6-membered cycle optionally containing a heteroatom moiety comprising O, S or NR13;
R13 is hydrogen, methyl, methoxy, formyl or acyl; or
a salt or an N-oxide thereof;
with the proviso that the compound of Formula (I) is not:
tert-butyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]carbamate.

### Claim 2 (depends on 1)

The compound according to claim 1, wherein:
A1 is N or CR1 wherein R1 represents hydrogen, halogen, methyl or trifluoromethyl;
A2 is N or C—H;
A3 is N or CR3 wherein R3 represents hydrogen or halogen; and
A4 is C—H.

### Claim 3 (depends on 1)

The compound according to claim 1, wherein n is 1, and R5 and R6 are independently selected from hydrogen and methyl.

### Claim 4 (depends on 1)

The compound according to claim 1, wherein n is 2, and R5 and R6 are independently selected from hydrogen and fluoro.

### Claim 5 (depends on 1)

The compound according to claim 1, wherein:
R8 is —C(O)R9, wherein R9 is hydrogen, C1-6alkyl, C2-6alkenyl, C2-6alkynyl, cyanoC1-6alkyl, C1-6haloalkyl, C2-6haloalkenyl, hydroxyC1-6alkyl, hydroxyC1-6haloalkyl, C1-4alkoxyC1-6alkyl, C1-4haloalkoxyC1-6alkyl, C1-4alkoxyC1-4alkoxyC1-6alkyl, C2-4alkynyloxyC1-6alkyl, aminoC1-6alkyl, N—C1-4alkylaminoC1-6alkyl, C1-2alkylcarbonylC1-4alkyl or N—C1-2alkylcarbonylaminoC1-2alkyl; or
R8 is —C(O)OR10, wherein R′° is hydrogen, C1-8alkyl, C3-6alkenyl, C3-6alkynyl, cyanoC1-6alkyl, C1-6haloalkyl, C3-6haloalkenyl, hydroxyC1-6alkyl, C1-4alkoxyC1-6alkyl, C1-4haloalkoxyC1-6alkyl, C1-4alkoxyC1-4alkoxyC1-6alkyl or aminoC1-6alkyl; or
R8 represents —C(O)NR11R12, wherein R11 is hydrogen, cyano, C1-6alkyl, C2-6alkenyl, C2-6alkynyl, cyanoC1-8alkyl, C1-6haloalkyl, C2-6haloalkenyl, hydroxyC1-6alkyl, C1-4alkoxyC1-6alkyl, aminoC1-6alkyl or C1-4alkylsulfanylC1-6alkyl; and
R12 is hydrogen, C1-4alkyl or C1-4alkoxy.

### Claim 6 (depends on 1)

The compound according to claim 1, wherein R9 is C1-6alkyl, C3-6alkenyl, C3-6alkynyl, cyanoC1-4alkyl, C1-6haloalkyl, hydroxyC1-4alkyl, hydroxyC1-4haloalkyl, C1-2alkoxyC1-4alkyl, C1-2haloalkoxyC1-4alkyl, C1-2alkylcarbonylC1-4alkyl or N—C1-2alkylcarbonylaminoC1-2alkyl.

### Claim 7 (depends on 1)

The compound according to claim 1, wherein R9 is C1-6alkyl, C3-4alkenyl, C3-6alkynyl, C1-4fluoroalkyl, C1-4chloroalkyl, C1-2alkoxyC1-4alkyl or C1-2fluoroalkoxyC1-4alkyl.

### Claim 8 (depends on 1)

The compound according to claim 1, wherein R10 is C1-8alkyl, C3-4alkenyl, C3-4alkynyl, C1-4haloalkyl or C1-2alkoxyC1-4alkyl.

### Claim 9 (depends on 1)

The compound according to claim 1, wherein R11 is hydrogen, cyano, C1-6alkyl, C2-4alkenyl, C2-4alkynyl, cyanoC1-4alkyl, C1-4haloalkyl, C2-4haloalkenyl, hydroxyC1-4alkyl, C1-4alkoxyC1-4alkyl, aminoC1-4alkyl or C1-4alkylsulfanylC1-4alkyl.

### Claim 10 (depends on 1)

The compound according to claim 1, wherein R11 is hydrogen, C1-6alkyl or C1-4alkoxyC1-6alkyl.

### Claim 11 (depends on 1)

The compound according to claim 1, wherein R12 is hydrogen, methyl, ethyl, methoxy or ethoxy.

### Claim 12 (depends on 1)

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

### Claim 13 (depends on 12)

The composition according to claim 12, further comprising at least one additional active ingredient and/or an agrochemically-acceptable diluent or carrier.

### Claim 14 (depends on 1)

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

### Claim 15 (depends on 1)

A compound according to claim 1, said compound being selected from: