Microbiocidal heterobicyclic derivatives

Patent metadata

Field	Value
Publication number	US-9586969-B2
Application number	US-201515116635-A
Country	US
Kind code	B2
Filing date	Feb 6, 2015
Priority date	Feb 7, 2014
Publication date	Mar 7, 2017
Grant date	Mar 7, 2017

Abstract

Compounds of the formula I wherein Y—X, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , A 1 , A 2 , A 3 , 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.

First claim

The invention claimed is:

1. A compound of formula I:

wherein
each of A 1 , A 2 , and A 3 independently represents a nitrogen atom or CR 7 ;
Y—X represents a radical selected from G1, G2, G3 and G4:

R 1 and R 2 are each independently selected from hydrogen, halogen, cyano, C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, in which the alkyl, cycloalkyl, alkenyl and alkynyl groups may be optionally substituted with 1 to 3 substituents independently selected from halogen, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio and phenoxy; or
R 1 and R 2 together with the carbon atom to which they are attached represent a C 3 -C 10 cycloalkyl group (which may be optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy and phenoxy);
R 3 and R 4 are each independently selected from hydrogen, halogen, hydroxyl, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 3 -C 7 cycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, in which the alkyl, alkoxy, cycloalkyl, alkenyl and alkynyl groups may be optionally substituted with 1 to 3 substituents independently selected from halogen, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio and phenoxy; or
R 3 and R 4 together with the carbon atom to which they are attached represent C═O, C═CH 2 or C 3 -C 10 cycloalkyl (which may be optionally substituted with 1 to 3 substituents independently selected from the group consisting of a halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy and phenoxy);
R 5 is hydrogen, halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy or hydroxyl;
R 6 is hydrogen, halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy or hydroxyl;
each R 7 independently represents hydrogen, cyano, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 3 -C 7 cycloalkyl, C 2 -C 6 alkynyl, or hydroxyl;
each R 8 independently represents hydroxyl, halogen, cyano, amino, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 3 -C 7 cycloalkyl, C 2 -C 6 alkenyloxy, C 3 -C 6 alkynyloxy, C 1 -C 6 alkylthio, C 2 -C 6 alkynyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylcarbonyl, NH(C 1 -C 6 alkyl), N(C 1 -C 6 alkyl) 2 , CO 2 H, CO 2 (C 1 -C 6 alkyl), C(O)N(C 1 -C 6 alkyl) 2 , C(O)NH(C 1 -C 6 alkyl), C(O)NH 2 , NH(C 1 -C 6 alkylcarbonyl), N(C 1 -C 6 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, C 1 -C 6 alkoxy, hydroxyl, C 1 -C 6 alkylthio, C 1 -C 6 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, C 1 -C 6 alkyl (which itself may be optionally substituted with 1 to 3 halogen atoms), C 1 -C 6 alkoxy, amino (which itself may be substituted with 1 or 2 groups independently selected from C 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyl), nitro, cyano, hydroxyl, mercapto and C 1 -C 6 alkylthio; n is 0, 1, 2, 3 or 4;
R a is hydrogen, C 1 -C 6 alkylcarbonyl or C 1 -C 6 alkyl, which may be optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio and phenoxy; or a salt or N-oxide thereof.

2. A compound according to claim 1 wherein one or more of A 1 , A 2 , and A 3 represents CR 7 .

3. A compound according to claim 1 wherein each R 7 independently represents hydrogen, halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 2 -C 6 alkynyl, or hydroxyl.

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

5. A compound according to claim 1 , wherein R 1 and R 2 are each independently selected from hydrogen, cyano, C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, in which the alkyl and cycloalkyl groups may be optionally substituted with 1 to 3 substituents independently selected from halogen, C 1 -C 6 alkoxy, and C 1 -C 6 alkylthio; or R 1 and R 2 together with the carbon atom to which they are attached represent a C 3 -C 6 cycloalkyl group.

6. A compound according to claim 1 , wherein R 3 and R 4 are each independently selected from hydrogen, halogen, hydroxyl, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, in which the alkyl and alkoxy groups may be optionally substituted with 1 to 3 substituents independently selected from halogen, C 1 -C 6 alkoxy, and C 1 -C 6 alkylthio; or R 3 and R 4 together with the carbon atom to which they are attached represent C═O, or C 3 -C 7 cycloalkyl, which may be optionally substituted with 1 to 3 substituents independently selected from halogen.

7. A compound according to claim 1 , wherein R 5 is hydrogen, halogen, or C 1 -C 6 alkyl.

8. A compound according to claim 1 , wherein R 6 is hydrogen, halogen, or C 1 -C 6 alkyl.

9. A compound according to claim 1 , wherein each R 8 independently represents hydroxyl, halogen, cyano, amino, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 3 -C 7 cycloalkyl, C 2 -C 6 alkenyloxy, C 3 -C 6 alkynyloxy, C 1 -C 6 alkylthio, C 2 -C 6 alkynyl, C 1 -C 6 alkoxy, C 1 -C 6 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, C 1 -C 6 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, C 1 -C 6 alkyl (which itself may be optionally substituted with 1 to 3 halogen atoms), or C 1 -C 6 alkoxy; n is 0, 1, 2, or 3.

10. A compound according to claim 1 , wherein R a is hydrogen or C 1 -C 6 alkyl when Y—X is G2.

11. A compound according to claim 1 wherein two or more of A 1 , A 2 , and A 3 represent CR 7 ; each R 7 independently represents hydrogen, halogen, C 1 -C 6 alkyl, or hydroxyl; Y—X is G1; R 1 and R 2 are each independently selected from C 1 -C 6 alkyl, in which the alkyl group may be optionally substituted with 1 to 3 substituents independently selected from halogen, and C 1 -C 6 alkoxy; or R 1 and R 2 together with the carbon atom to which they are attached represent a C 3 -C 6 cycloalkyl group; R 3 and R 4 are each independently selected from hydrogen, halogen, C 1 -C 6 alkyl; or R 3 and R 4 together with the carbon atom to which they are attached represent C═O, or cyclopropyl; R 5 is hydrogen, or halogen; R 6 is hydrogen, or C 1 -C 6 alkyl; each R 8 independently represents halogen, C 1 -C 6 alkyl, C 1 -C 6 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 het

Assignees

• Syngenta Participations Ag
• Syngenta (China) Invest Co Ltd

Inventors

• Bou Hamdan Farhan
• Quaranta Laura
• Trah Stephan
• Lamberth Clemens
• Lu Long
• Lu Qiang

Classifications

• C07D519/00

  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 · CPC title

• A01N43/90

  having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system · CPC title

• A61P31/00

  Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics · CPC title

• C07D487/04 Primary

  Ortho-condensed systems · CPC title