Microbiocidal heterobicyclic derivatives

Patent metadata

Field	Value
Publication number	US-10906897-B2
Application number	US-201615751976-A
Country	US
Kind code	B2
Filing date	Aug 8, 2016
Priority date	Aug 12, 2015
Publication date	Feb 2, 2021
Grant date	Feb 2, 2021

Abstract

Compounds of the formula (I) wherein Q 1 , Q 2 , Y—X, R 1 , R 2 , R 3 , R 4 , R b , R c , R d , R 5 , R 6 , R 7 , Ra, m 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
Q 1 is a carbon atom and Q 2 is a nitrogen atom;
Y—X represents:

R 1 and R 2 are each independently selected from hydrogen, cyano, C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 2 -C 6 alkenyl and 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 and C 1 -C 6 alkylthio;
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 and 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 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, C═NOR d , or C═C(R b )(R c ); where R b and R c 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, C 1 -C 6 alkoxy and C 1 -C 6 alkylthio, 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 and C 1 -C 6 alkylthio, and where R d is selected from hydrogen, C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 3 -C 6 alkenyl and C 3 -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 and C 1 -C 6 alkylthio;
each R 5 independently represents halogen, hydroxyl, mercapto, nitro, cyano, formyl, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 7 cycloalkyl, C 1 -C 6 alkoxy, C 3 -C 6 alkenyloxy, C 3 -C 6 alkynyloxy, C 1 -C 6 alkylthio, —C(═NOR a )C 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyl, aryl or phenoxy, in which the alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, and aryl groups may be optionally substituted with 1 to 5 substituents independently selected from halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, cyano and C 1 -C 6 alkylthio; n is 0, 1, 2, 3 or 4;
R 6 is hydrogen, halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy or hydroxyl;
each R 7 independently represents hydroxyl, mercapto, cyano, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkenyl, C 3 -C 6 haloalkynyl, C 1 -C 6 alkylthio, C 1 -C 6 haloalkoxy, C 1 -C 6 haloalkylthio, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylcarbonyl, C 3 -C 7 cycloalkyl, C 1 -C 6 alkoxy, C 3 -C 6 alkenyloxy or C 3 -C 6 alkynyloxy; m is 0, 1, 2, 3 or 4; and
R a is 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. The compound according to claim 1 wherein R 1 and R 2 are each independently selected from hydrogen, 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.

3. The 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 and C 3 -C 7 cycloalkyl, in which the alkyl, alkoxy 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 3 and R 4 together with the carbon atom to which they are attached represent C═O, C═NOR d , or C═C(R b )(R c ), where R b and R c 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, C 1 -C 6 alkoxy and C 1 -C 6 alkylthio, 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 and C 1 -C 6 alkylthio, and where R d is selected from hydrogen, C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 3 -C 6 alkenyl and C 3 -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 and C 1 -C 6 alkylthio.

4. The compound according to claim 1 wherein each R 5 independently represents halogen, cyano, C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 1 -C 6 alkoxy, C 3 -C 6 alkenyloxy, C 3 -C 6 alkynyloxy, C 1 -C 6 alkylthio, —C(═NOR a )C 1 -C 6 alkyl, phenyl or phenoxy in which the alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, and phenyl groups may be optionally substituted with 1 to 5 substituents independently selected from halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, cyano and C 1 -C 6 alkylthio;
n is 0, 1, 2, 3 or 4.

5. The compound according to claim 1 wherein R 6 is hydrogen, halogen, or C 1 -C 2 alkyl.

6. The compound according to claim 1 wherein each R 7 independently represents cyano, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkenyl, C 3 -C 6 haloalkynyl, C 1 -C 6 alkylthio, C 1 -C 6 haloalkoxy, C 1 -C 6 haloalkylthio, C 3 -C 7 cycloalkyl, C 1 -C 6 alkoxy, C 3 -C 6 alkenyloxy or C 3 -C 6 alkynyloxy; m is 0, 1, 2, 3 or 4.

7. The compound according to claim 1 wherein:
R 1 and R 2 are each independently a hydrogen or C 1 -C 4 alkyl group, 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 3 and R 4 are each independently selected from hydrogen, halogen, C 1 -C 4 alkyl and C 3 -C 4 cycloalkyl, in which the alkyl and cycloalkyl groups may be optionally substituted with 1 to 3 substituents independently selected from halogen, C 1 -C 3 alkoxy and C 1 -C 3 alkylthio; or
R 3 and R 4 together with the carbon atom to which they are attached represent C═O or C═NOR d , where R d is selected from hydrogen, C 1 -C 4 alkyl and C 3 -C 5 cycloalkyl, in which the alkyl and cycloalkyl groups may be optionally substituted with 1 to 3 substituents independently selected from halogen, C 1 -C 3 alkoxy and C 1 -C 3 alkylthio;
each R 5 independently represents halogen, cyano, C 1 -C 4 alkyl, C 3 -C 4 cycloalkyl, C 1 -C 3 alkoxy, C 3 -C 6 alkenyloxy, C 3 -C 6 alkynyloxy, phenyl, in which the alkyl, cycloalkyl, alkoxy, alkenyloxy, alkynyloxy, and phenyl groups may be optionally substituted with 1 to 3 substituents independently selected from halogen, C 1 -C 3 alkyl and C 1 -C 3 alkoxy;
n is 0, 1 or 2;
R 6 is hydrogen, fluoro, chloro, or methyl;
each R 7 independently represents cyano, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 3 alkynyl, C 1 -C 4 alkylthio or C 3 -C 4 cycloalkyl; and
m is 0, 1 or 2; or
a salt or N-oxide thereof.

8. The compound according to claim 1 wherein:
R 1 and R 2 are each independently a C 1 -C 3 alkyl;
R 3 and R 4 are each independently selected from hydrogen, halogen and C 1 -C 4 alkyl; or
R 3 and R 4 together with the carbon atom to which they are attached represent C═O;
each R 5 independently represents halogen, cyano, C 1 -C 3 alkyl, C 3 -C 3 cycloal

Assignees

• Syngenta Participations Ag

Inventors

• Quaranta Laura
• Trah Stephan
• Weiss Matthias
• Bou Hamdan Farhan

Classifications

• C07D471/04 Primary

  Ortho-condensed systems · CPC title

• C07D217/24 Primary

  Oxygen atoms · CPC title

• A01N43/52

  condensed with carbocyclic rings, e.g. benzimidazoles · CPC title

• A01N43/42 Primary

  condensed with carbocyclic rings · CPC title

• A01N43/56

  1,2-Diazoles; Hydrogenated 1,2-diazoles · CPC title