# US 2016/0355518 A1 · Microbiocidal heterobicyclic derivatives

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 2016/0355518 A1
- Document ID: US20160355518A1
- Status: Published application
- Kind: A1
- Application number: 15/116,635
- Filed: 2015-02-06
- Published: 2016-12-08
- Earliest claimed: 2014-02-07
- Assignees: Syngenta Participations AG; Syngenta (China) Investement Co., Ltd.
- Applicants: Syngenta Participations AG; Syngenta (China) Investment Co., Ltd.
- Inventors: Farhan BOU HAMDAN; Laura QUARANTA; Stephan TRAH; Clemens LAMBERTH; Long LU; Qiang LU
- Web page: https://patentgrep.com/patent/US20160355518A1

## CPC

- C07D 487/04: Ortho-condensed systems
- A01N 43/90: having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
- A61P 31/00: Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- C07D 519/00: Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- 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 Y—X, R1, R2, R3, R4, R5, R6, R7, R8, A1, A2, A3, Ra and n are as defined in claim 1. Furthermore, the present invention relates to agrochemical compositions which comprise compounds of formula (I), to preparation of these compositions, and to the use of the compounds or compositions in agriculture or horticulture for combating, preventing or controlling infestation of plants, harvested food crops, seeds or non-living materials by phytopathogenic microorganisms, in particular fungi.

## Claims

### Claim 1

A compound of formula I:
wherein
each of A1, A2, and A3 independently represents a nitrogen atom or CR7;
Y—X represents a radical selected from G1, G2, G3 and G4:
R1 and R2 are each independently selected from hydrogen, halogen, cyano, C1-C6 alkyl, C3-C7 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, in which the alkyl, cycloalkyl, alkenyl and alkynyl groups may be optionally substituted with 1 to 3 substituents independently selected from halogen, C1-C6 alkoxy, C1-C6 alkylthio and phenoxy; or
R1 and R2 together with the carbon atom to which they are attached represent a C3-C10 cycloalkyl group (which may be optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, C1-C6 alkyl, C1-C6 alkoxy and phenoxy);
R3 and R4 are each independently selected from hydrogen, halogen, hydroxyl, C1-C6 alkyl, C1-C6 alkoxy, C3-C7 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, in which the alkyl, alkoxy, cycloalkyl, alkenyl and alkynyl groups may be optionally substituted with 1 to 3 substituents independently selected from halogen, C1-C6 alkoxy, C1-C6 alkylthio and phenoxy; or
R3 and R4 together with the carbon atom to which they are attached represent C═O, C═CH2 or C3-C10 cycloalkyl (which may be optionally substituted with 1 to 3 substituents independently selected from the group consisting of a halogen, C1-C6 alkyl, C1-C6 alkoxy and phenoxy);
R5 is hydrogen, halogen, C1-C6 alkyl, C1-C6 alkoxy or hydroxyl;
R6 is hydrogen, halogen, C1-C6 alkyl, C1-C6 alkoxy or hydroxyl;
each R7 independently represents hydrogen, cyano, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C3-C7 cycloalkyl, C2-C6 alkynyl, or hydroxyl;
each R8 independently represents hydroxyl, halogen, cyano, amino, C1-C6 alkyl, C2-C6 alkenyl, C3-C7 cycloalkyl, C2-C6 alkenyloxy, C3-C6 alkynyloxy, C1-C6 alkylthio, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylcarbonyl, NH(C1-C6 alkyl), N(C1-C6 alkyl)2, CO2H, CO2(C1-C6 alkyl), C(O)N(C1-C6 alkyl)2, C(O)NH(C1-C6 alkyl), C(O)NH2, NH(C1-C6 alkylcarbonyl), N(C1-C6 alkylcarbonyl)2, aryl, heteroraryl, aryloxy or heteroraryloxy, in which the alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy groups may be optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, C1-C6 alkoxy, hydroxyl, C1-C6 alkylthio, C1-C6 alkoxycarbonyl and phenoxy, and the aryl or heteroaryl groups may be optionally substituted with 1 to 5 substituents independently selected from the group consisting of halogen, C1-C6 alkyl (which itself may be optionally substituted with 1 to 3 halogen atoms), C1-C6 alkoxy, amino (which itself may be substituted with 1 or 2 groups independently selected from C1-C6 alkyl, C1-C6 alkylcarbonyl), nitro, cyano, hydroxyl, mercapto and C1-C6 alkylthio; n is 0, 1, 2, 3 or 4;
Ra is hydrogen, C1-C6 alkylcarbonyl or C1-C6 alkyl, which may be optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, C1-C6 alkoxy, C1-C6 alkylthio and phenoxy; or a salt or N-oxide thereof.

### Claim 2 (depends on 1)

A compound according to claim 1 wherein one or more of A1, A2, and A3 represents CR7.

### Claim 3 (depends on 1)

A compound according to claim 1 wherein each R7 independently represents hydrogen, halogen, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkynyl, or hydroxyl.

### Claim 4 (depends on 1)

A compound according to claim 1, wherein Y—X is G1, G2 or G4.

### Claim 5 (depends on 1)

A compound according to claim 1, wherein R1 and R2 are each independently selected from hydrogen, cyano, C1-C6 alkyl, C3-C7 cycloalkyl, in which the alkyl and cycloalkyl groups may be optionally substituted with 1 to 3 substituents independently selected from halogen, C1-C6 alkoxy, and C1-C6 alkylthio; or R1 and R2 together with the carbon atom to which they are attached represent a C3-C6 cycloalkyl group.

### Claim 6 (depends on 1)

A compound according to claim 1, wherein R3 and R4 are each independently selected from hydrogen, halogen, hydroxyl, C1-C6 alkyl, C1-C6 alkoxy, in which the alkyl and alkoxy groups may be optionally substituted with 1 to 3 substituents independently selected from halogen, C1-C6 alkoxy, and C1-C6 alkylthio; or R3 and R4 together with the carbon atom to which they are attached represent C═O, or C3-C7 cycloalkyl, which may be optionally substituted with 1 to 3 substituents independently selected from halogen.

### Claim 7 (depends on 1)

A compound according to claim 1, wherein R5 is hydrogen, halogen, or C1-C6 alkyl.

### Claim 8 (depends on 1)

A compound according to claim 1, wherein R6 is hydrogen, halogen, or C1-C6 alkyl.

### Claim 9 (depends on 1)

A compound according to claim 1, wherein each R8 independently represents hydroxyl, halogen, cyano, amino, C1-C6 alkyl, C2-C6 alkenyl, C3-C7 cycloalkyl, C2-C6 alkenyloxy, C3-C6 alkynyloxy, C1-C6 alkylthio, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylcarbonyl, phenyl, heteroraryl (wherein heteroaryl is pyridyl, thiophenyl, thiazolyl, imidazolyl, or oxazolyl), phenoxy or heteroraryloxy (wherein heteroaryl is pyridyl, thiophenyl, thiazolyl, imidazolyl, or oxazolyl), in which the alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy groups may be optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, C1-C6 alkoxy, hydroxyl, and the phenyl, phenoxy and heteroaryl groups may be optionally substituted with 1 to 5 substituents independently selected from the group consisting of halogen, C1-C6 alkyl (which itself may be optionally substituted with 1 to 3 halogen atoms), or C1-C6 alkoxy; n is 0, 1, 2, or 3.

### Claim 10 (depends on 1)

A compound according to claim 1, wherein Ra is hydrogen or C1-C6 alkyl when Y—X is G2.

### Claim 11 (depends on 1)

A compound according to claim 1 wherein two or more of A1, A2, and A3 represent CR7; each R7 independently represents hydrogen, halogen, C1-C6 alkyl, or hydroxyl; Y—X is G1; R1 and R2 are each independently selected from C1-C6 alkyl, in which the alkyl group may be optionally substituted with 1 to 3 substituents independently selected from halogen, and C1-C6 alkoxy; or R1 and R2 together with the carbon atom to which they are attached represent a C3-C6 cycloalkyl group; R3 and R4 are each independently selected from hydrogen, halogen, C1-C6 alkyl; or R3 and R4 together with the carbon atom to which they are attached represent C═O, or cyclopropyl; R5 is hydrogen, or halogen; R6 is hydrogen, or C1-C6 alkyl; each R8 independently represents halogen, C1-C6 alkyl, C1-C6 alkoxy, phenyl, heteroraryl (wherein heteroaryl is pyridyl, thiophenyl or thiazolyl), phenoxy or heteroraryloxy (wherein heteroaryl is pyridyl, thiophenyl or thiazolyl), in which the alkyl and alkoxy groups may be optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, and the phenyl, phenoxy and heteroaryl groups may be optionally substituted with 1 or 2 substituents independently selected from the group consisting of halogen, or C1-C3 alkyl (which itself may be optionally substituted with 1 to 3 halogen atoms); n is 0, 1, or 2; and Ra is hydrogen, or C1-C2 alkyl; or a salt or N-oxide thereof.

### Claim 12 (depends on 1)

A method of combating, preventing or controlling phytopathogenic diseases which comprises applying to a phytopathogen, to the locus of a phytopathogen, or to a plant susceptible to attack by a phytopathogen, or to propagation material thereof, a fungicidally effective amount of a compound of formula (I) as defined in claim 1 or a composition comprising a fungicidally effective amount of said compound.

### Claim 13 (depends on 1)

A composition comprising a fungicidally effective amount of a compound of formula
(I) as defined in claim 1.

### Claim 14 (depends on 13)

A composition according to claim 13, wherein the composition further comprises at least one additional active ingredient and/or a diluent.