Microbiocidal heterobicyclic derivatives

Patent metadata

Field	Value
Publication number	US-10273221-B2
Application number	US-201615561788-A
Country	US
Kind code	B2
Filing date	Mar 21, 2016
Priority date	Mar 27, 2015
Publication date	Apr 30, 2019
Grant date	Apr 30, 2019

Abstract

Compounds of the formula (I) wherein the substituents 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
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; 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 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 a , C═C(R b )(R c ) 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 C 1 -C 6 alkylthio); or
R 2 and R 3 together with the carbon atoms to which they are attached represent a C 5 -C 10 cycloalkyl (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 C 1 -C 6 alkylthio, and, additionally, a ring carbon unit may be replaced by an oxygen or sulphur atom);
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, heteroraryl, aryloxy or heteroraryloxy, in which the alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, aryl and heteroaryl 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 or C 1 -C 6 alkoxy;
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; or
Two adjacent R 7 substitutents together with the carbon atoms to which they are attached represent a C 5 -C 7 cycloalkyl (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 C 1 -C 6 alkylthio, and, additionally, a ring carbon unit may be replaced by an oxygen or sulphur atom);
R a 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;
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; or a salt or N-oxide thereof.

2. A compound according to claim 1 wherein R 1 and R 2 are each independently selected from hydrogen, C 1 -C 6 alkyl and 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 (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 C 1 -C 6 alkylthio); or
R 2 and R 3 together with the carbon atoms to which they are attached represent a C 5 -C 7 cycloalkyl (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 C 1 -C 6 alkylthio, and, additionally, a ring carbon unit may be replaced by an oxygen or sulphur atom).

3. 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 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 a , C═C(R b )(R c ) or C 3 -C 6 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 C 1 -C 6 alkylthio); or
R 2 and R 3 together with the carbon atoms to which they are attached represent a C 5 -C 7 cycloalkyl (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 C 1 -C 6 alkylthio, and, additionally, a ring carbon unit may be replaced by an oxygen or sulphur atom).

4. A compound according to claim 1 wherein each R 5 independently represents halogen, cyano, 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, 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, alkenyloxy, alkynyloxy, phenyl and heteroaryl 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. A compound according to claim 1 wherein R 6 is hydrogen, halogen or C 1 -C 6 alkyl.

6. A 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; or Two adjacent R 7 substituents together with the carbon atoms to which they are attached represent a C 5 -C 7 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 C 1 -C 6 alkylthio,

Assignees

• Syngenta Participations Ag

Inventors

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

Classifications

• C07D417/14

  containing three or more hetero rings · CPC title

• A01N43/52 Primary

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

• C07D401/04 Primary

  directly linked by a ring-member-to-ring-member bond · CPC title

• A01N43/54

  1,3-Diazines; Hydrogenated 1,3-diazines · CPC title

• A01N43/78

  1,3-Thiazoles; Hydrogenated 1,3-thiazoles · CPC title