Use of macrocyclic picolinamides as fungicides

Patent metadata

Field	Value
Publication number	US-9247741-B2
Application number	US-201414577940-A
Country	US
Kind code	B2
Filing date	Dec 19, 2014
Priority date	Dec 26, 2013
Publication date	Feb 2, 2016
Grant date	Feb 2, 2016

Abstract

The invention relates to macrocyclic picolinamides of Formula I and their use as fungicides.

First claim

What is claimed is:

1. A composition for the control of a fungal pathogen including at least one 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 is hydrogen, alkyl, alkenyl, aryl, alkoxy, or acyl, each optionally substituted with 0, 1 or multiple R 6 ;
R 2 is hydrogen, alkyl, acyl, aryl, alkenyl, or —Si(R 5 ) 3 , 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, acyl, halo, alkenyl, alkoxy, heteroaryl, heterocyclyl,or thioalkyl, each optionally substituted with 0, 1, or multiple R 7 ; and
R 7 is hydrogen, alkyl, aryl, or halo.

2. The composition according to claim 1 , wherein X is hydrogen and Y is Q.

3. The composition according to claim 2 , wherein R 4 is hydrogen.

4. The composition according to claim 3 , wherein R 1 is chosen from alkyl and aryl, each optionally substituted with 0, 1 or multiple R 6 .

5. The composition according to claim 3 , wherein R 2 is chosen from alkyl, aryl, and acyl, each optionally substituted with 0, 1 or multiple R 6 .

6. The composition according to claim 3 , wherein R 1 is chosen from alkyl and aryl, each optionally substituted with 0, 1 or multiple R 6 , and
R 2 is chosen from alkyl, aryl, and acyl, each optionally substituted with 0, 1 or multiple R 6 .

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

8. The composition according to claim 7 , wherein R 5 is chosen from alkyl and alkoxy, each optionally substituted with 0, 1, or multiple R 6 .

9. The composition according to claim 8 , wherein R 1 is chosen from alkyl and aryl, each optionally substituted with 0, 1 or multiple R 6 .

10. The composition according to claim 8 , wherein R 2 is chosen from alkyl, aryl, and acyl, each optionally substituted with 0, 1 or multiple R 6 .

11. The composition according to claim 8 , wherein R 1 is chosen from alkyl and aryl, each optionally substituted with 0, 1 or multiple R 6 , and
R 2 is chosen from alkyl, aryl, and acyl, each optionally substituted with 0, 1 or multiple R 6 .

12. The composition according to claim 11 , wherein R 5 is chosen from —CH 3 and —CH 2 OCH 2 CH 3 .

13. The composition according to claim 6 , further comprising a phytologically acceptable carrier material.

14. The composition according to claim 11 , further comprising a phytologically acceptable carrier material.

15. The composition according to claim 12 , further comprising a phytologically acceptable carrier material.

16. The composition according to claim 6 , further comprising another pesticide selected from the group consisting of fungicides, insecticides, nematocides, miticides, arthropodicides, bactericides and combinations thereof.

17. The composition according to claim 11 , further comprising another pesticide selected from the group consisting of fungicides, insecticides, nematocides, miticides, arthropodicides, bactericides and combinations thereof.

18. The composition according to claim 12 , further comprising another pesticide selected from the group consisting of fungicides, insecticides, nematocides, miticides, arthropodicides, bactericides and combinations thereof.

19. The composition according to claim 2 wherein the fungal pathogen is 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 ).

20. The composition according to claim 6 wherein the fungal pathogen is selected from the group consisting of: Leaf Blotch of Wheat ( Septoria tritici ), Wheat Brown Rust ( Puccinia triticina ), and Rust of Soybean ( Phakopsora pachyrhizi ).

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

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

23. A method for the control and prevention of fungal attack on a plant, the method including the step of: applying a fungicidally effective amount of the composition according to claim 6 to at least one of the plant, an area adjacent to the plant, soil adapted to support growth of the plant, a root of the plant, and foliage of the plant.

24. A method for the control and prevention of fungal attack on a plant, the method including the step of: applying a fungicidally effective amount of the composition according to claim 11 to at least one of the plant, an area adjacent to the plant, soil adapted to support growth of the plant, a root of the plant, and foliage of the plant.

25. A method for the control and prevention of fungal attack on a plant, the method including the step of: applying a fungicidally effective amount of the composition according to claim 12 to at least one of the plant, an area adjacent to the plant, soil adapted to support growth of the plant, a root of the plant, and foliage of the plant.

26. A method for the control and prevention of fungal attack on a plant, the method including the step of: applying a fungicidally effective amount of the composition according to claim 15 to at least one of the plant, an area adjacent to the plant, soil adapted to support growth of the plant, a root of the plant, and foliage of the plant.

27. A method for the control and prevention of fungal attack on a plant, the method including the step of: applying a fungicidally effective amount of the composition according to claim 18 to at least one of the plant, an area adjacent to the plant, soil adapted to support growth of the plant, a root of the plant, and foliage of the plant.

Assignees

• Dow Agrosciences Llc

Inventors

• Delorbe Jonathan E
• Dekorver Kyle A
• Meyer Kevin G
• Yao Chenglin
• Wilmot Jeremy
• O'Callaghan Ian
• Heemstra Ronald J
• Dent Iii William H
• Lalonde Rebecca Lyn K C

Classifications

• C07D405/12

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

• C07D313/00

  Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom · CPC title

• A01N25/00

  Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application {, e.g. seed treatment or sequential application}; Substances for reducing the noxious effect of the active ingredients to organisms other than pests · CPC title

• A01N53/00

  Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof · CPC title

• A01N43/22 Primary

  rings with more than six members · CPC title