Macrocyclic picolinamides as fungicides

Patent metadata

Field	Value
Publication number	US-2016007601-A1
Application number	US-201514793311-A
Country	US
Kind code	A1
Filing date	Jul 7, 2015
Priority date	Jul 8, 2014
Publication date	Jan 14, 2016
Grant date	—

Abstract

This disclosure relates to macrocyclic picolinamides of Formula I and their use as fungicides.

First claim

What is claimed is:

1 . A compound of Formula I

wherein:
X is hydrogen or C(O)R 3 ;
Y is hydrogen, C(O)R 3 , or Q;
Q is

R 1 and R 2 are independently selected from the group consisting of alkyl, alkenyl, and aryl, each optionally substituted with 0, 1 or multiple R 6 ;
R 3 is alkoxy or benzyloxy, each optionally substituted with 0, 1, or multiple R 6 ;
R 4 is hydrogen, —C(O)R 5 , or —CH 2 OC(O)R 5 ;
R 5 is alkyl, alkoxy, or aryl, each optionally substituted with 0, 1, or multiple R 6 ;
R 6 is hydrogen, alkyl, aryl, halo, acyloxy, alkenyl, alkoxy, heteroaryl, heterocyclyl, or thioalkyl, each optionally substituted with 0, 1, or multiple R 7 ; and
R 7 is hydrogen, alkyl, haloalkyl, alkoxy, haloalkoxy, aryl, or halo.

2 . The compound according to claim 1 , wherein X and Y are hydrogen.

3 . The compound according to claim 1 , wherein X is C(O)R 3 and Y is hydrogen.

4 . The compound according to claim 1 , wherein X is hydrogen and Y is Q.

5 . The compound according to claim 4 , wherein R 4 is hydrogen.

6 . The compound according to claim 4 , wherein R 4 is —C(O)R 5 or —CH 2 OC(O)R 5 .

7 . The compound according to claim 6 , wherein R 5 is alkyl or alkoxy, each optionally substituted with 0, 1, or multiple R 6 .

8 . The compound according to claim 7 , wherein R 5 is chosen from —CH 3 , —CH(CH 3 ) 2 , —CH 2 OCH 2 CH 3 , or —CH 2 CH 2 OCH 3 .

9 . A composition for the control of a fungal pathogen including at least one of the compounds of claim 1 and at least one additional compound selected from the group consisting of: a phytologically acceptable carrier material, a second fungicide, an insecticide, a nematocides, a miticide, an arthropodicide, a bactericide.

10 . The composition for the control of a fungal pathogen according to claim 9 , wherein the at least one additional compound is at least one phytologically acceptable carrier material.

11 . The compositions according to claim 9 , wherein the fungal pathogen is at least one pathogen selected from the group consisting of: Leaf Blotch of Wheat ( Mycosphaerella graminicola ; anamorph: Septoria tritici ), Wheat Brown Rust ( Puccinia triticina ), Stripe Rust ( Puccinia striiformis ), Scab of Apple ( Venturia inaequalis ), Blister Smut of Maize ( Ustilago maydis ), Powdery Mildew of Grapevine ( Uncinula necator ), Barley Scald ( Rhynchosporium secalis ), Blast of Rice ( Magnaporthe grisea ), Rust of Soybean ( Phakopsora pachyrhizi ), Glume Blotch of Wheat ( Leptosphaeria nodorum ), Powdery Mildew of Wheat ( Blumeria graminis f. sp. tritici ), Powdery Mildew of Barley ( Blumeria graminis f. sp. hordei ), Powdery Mildew of Cucurbits ( Erysiphe cichoracearum ), Anthracnose of Cucurbits ( Glomerella lagenarium ), Leaf Spot of Beet ( Cercospora beticola ), Early Blight of Tomato ( Alternaria solani ), and Net Blotch of Barley ( Pyrenophora teres ).

12 . The composition according to claim 11 wherein the fungal pathogen is at least one of the pathogens selected from the group consisting of: Leaf Blotch of Wheat ( Septoria tritici ), Wheat Brown Rust ( Puccinia triticina ), and Rust of Soybean ( Phakopsora pachyrhizi ).

13 . The compositions according to claim 10 wherein the fungal pathogen is at least one pathogen selected from the group consisting of: Leaf Blotch of Wheat ( Mycosphaerella graminicola ; anamorph: Septoria tritici ), Wheat Brown Rust ( Puccinia triticina ), Stripe Rust ( Puccinia striiformis ), Scab of Apple ( Venturia inaequalis ), Blister Smut of Maize ( Ustilago maydis ), Powdery Mildew of Grapevine ( Uncinula necator ), Barley Scald ( Rhynchosporium secalis ), Blast of Rice ( Magnaporthe grisea ), Rust of Soybean ( Phakopsora pachyrhizi ), Glume Blotch of Wheat ( Leptosphaeria nodorum ), Powdery Mildew of Wheat ( Blumeria graminis f. sp. tritici ), Powdery Mildew of Barley ( Blumeria graminis f. sp. hordei ), Powdery Mildew of Cucurbits ( Erysiphe cichoracearum ), Anthracnose of Cucurbits ( Glomerella lagenarium ), Leaf Spot of Beet ( Cercospora beticola ), Early Blight of Tomato ( Alternaria solani ), and Net Blotch of Barley ( Pyrenophora teres ).

14 . The composition according to claim 13 wherein the fungal pathogen is at least one of the pathogens selected from the group consisting of: Leaf Blotch of Wheat ( Septoria tritici ), Wheat Brown Rust ( Puccinia triticina ), and Rust of Soybean ( Phakopsora pachyrhizi ).

15 . A method for the control and/or prevention of fungal attack on a plant, the method including the step of:
applying a fungicidally effective amount of at least one of the compounds of Formula I to at least one portion of a plant, an area adjacent to the plant, a portion of soil adapted to support growth of the plant, a root of the plant, and foliage of the plant.

16 . The method according to claim 15 wherein the applying step further includes applying at least additional compound selected from the group consisting of: a phytologically acceptable carrier material, a second fungicide, an insecticide, a nematocides, a miticide, an arthropodicide, and a bactericide

17 . The method according to claim 16 , wherein the additional compound is at least one phytologically acceptable carrier material.

18 . The method according to claim 16 , wherein the additional compound is at least a one of the following; a second fungicide, an insecticide, a nematocides, a miticide, an arthropodicide, and a bactericide.

19 . The method according to claim 15 , wherein the compounds of Formula 1 includes X equal to H, and Y equal to Q.

20 . The method according to claim 19 wherein the applying step further includes applying at least additional compound selected from the group consisting of: a phytologically acceptable carrier material, a second fungicide, an insecticide, a nematocides, a miticide, an arthropodicide, and a bactericide.

Assignees

• Dow Agrosciences Llc

Inventors

• Boebel Timothy A
• Lu Yu
• Meyer Kevin G
• Yao Chenglin
• Daeuble John F
• Bravo-Altamirano Karla
• Nugent Benjamin M

Classifications

• A01N47/18

  containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring · CPC title

• C07D321/00

  Heterocyclic compounds containing rings having two oxygen atoms as the only ring hetero atoms, not provided for by groups C07D317/00 - C07D319/00 · CPC title

• A01N43/40 Primary

  six-membered rings · CPC title

• C07D405/12

  linked by a chain containing hetero atoms as chain links · CPC title

• A01N43/24

  with two or more hetero atoms · CPC title