Use of macrocyclic picolinamides as fungicides

Patent metadata

Field	Value
Publication number	US-9439422-B2
Application number	US-201414500628-A
Country	US
Kind code	B2
Filing date	Sep 29, 2014
Priority date	Oct 1, 2013
Publication date	Sep 13, 2016
Grant date	Sep 13, 2016

Abstract

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

First claim

What is claimed is:

1. A method for the control and/or the prevention of fungal growth comprising the steps of:
applying a fungicidally effective amount of at least one compound of Formula I

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

R 1 is chosen from H, alkyl, alkenyl, aryl, —Si(R 6 ) 3 , or —C(O)R 6 , each optionally substituted with 0, 1 or multiple R 5 ;
R 2 is chosen from H, alkyl, aryl, heteroaryl, or arylalkyl, each optionally substituted with 0, 1 or multiple R 5 ;
R 3 is chosen from alkoxy, or benzyloxy, each optionally substituted with 0, 1, or multiple R 5 ;
R 4 is chosen from H, —C(O)R 7 , or —CH 2 OC(O)R 7 ;
R 5 is chosen from H, alkyl, alkenyl, halo, haloalkyl, alkoxy, aryl, heteroaryl, heterocyclyl, or —C(O)R 6 ;
R 6 is chosen from alkyl, alkenyl, haloalkyl, alkoxy, aryl or heteroaryl; and
R 7 is chosen from alkyl or alkoxy, each optionally substituted with 0, 1, or multiple R 6 ;
with the proviso that R 2 is not unsubstituted phenyl or unsubstituted cyclohexyl;
to at least one selected from the group consisting of: a fungi, an animal, an inert surface, a plant, an area adjacent to a plant, soil adapted to support growth of a plant, and a seed adapted to produce a plant.

2. The method according to claim 1 , wherein X and Y are independently chosen from H or C(O)R 3 .

3. The method according to claim 2 , wherein R 1 is chosen from H, alkyl, alkenyl, aryl, —Si(R 6 ) 3 , or —C(O)R 6 , each optionally substituted with 0, 1 or multiple R 5 .

4. The method according to claim 3 , wherein R 2 is chosen from H, alkyl, aryl, heteroaryl, or arylalkyl, each optionally substituted with 0, 1 or multiple R 5 .

5. The method according to claim 1 , wherein X is H and Y is Q.

6. The method according to claim 5 , wherein R 1 is chosen from H, alkyl, alkenyl, aryl, —Si(R 6 ) 3 , or —C(O)R 6 , each optionally substituted with 0, 1 or multiple R 5 .

7. The method according to claim 6 , wherein R 2 is chosen from H, alkyl, aryl, heteroaryl, or arylalkyl, each optionally substituted with 0, 1 or multiple R 5 .

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

9. The method according to claim 8 , wherein R 7 is alkyl or alkoxy, each optionally substituted with 0, 1, or multiple R 6 .

10. The method according to claim 1 , wherein:
at least one compound of said Formula I is applied in combination with a phytologically acceptable carrier material.

11. The method according to claim 10 , wherein:
the compound of Formula I is admixed with a phytologically acceptable carrier material.

12. The method according to claim 1 , wherein:
the compound of Formula I is applied in combination with at least one agriculturally active ingredient selected from the group consisting of: fungicides, insecticides, nematocides, miticides, arthropodicides, bactericides and combinations thereof.

13. The method according to claim 12 , wherein:
the compound of Formula I is admixed with at least one agriculturally active ingredient selected from the group consisting of: fungicides, insecticides, nematocides, miticides, arthropodicides, bactericides and combinations thereof.

14. The method according to claim 1 , wherein the compound of Formula I is suitable for the control of at least one fungal pathogen selected from the group consisting of: Mycosphaerella graminicola ; anamorph: Septoria tritici, Puccinia triticina, Puccinia striiformis, Venturia inaequalis, Ustilago maydis, Uncinula necator, Rhynchosporium secalis, Magnaporthe grisea, Pseudoperonospora cubensis, Phakopsora pachyrhizi, Leptosphaeria nodorum, Blumeria graminis f. sp. tritici, Blumeria graminis f. sp. hordei, Erysiphe cichoracearum, Glomerella lagenarium, Cercospora beticola, Alternaria solani , and Pyrenophora teres.

15. The method according to claim 1 , wherein the compound of Formula I is suitable for the control of a fungal pathogen comprising Septoria tritici, Puccinia triticina , and Phakopsora pachyrhizi.

16. The method according to claim 12 , wherein the compound of Formula I is suitable for the control of at least one fungal pathogen selected from the group consisting of Mycosphaerella graminicola ; anamorph: Septoria tritici, Puccinia triticina, Puccinia striiformis, Venturia inaequalis, Ustilago maydis, Uncinula necator, Rhynchosporium secalis, Magnaporthe grisea, Pseudoperonospora cubensis, Phakopsora pachyrhizi, Leptosphaeria nodorum, Blumeria graminis f. sp. tritici, Blumeria graminis f. sp. hordei, Erysiphe cichoracearum, Glomerella lagenarium, Cercospora beticola, Alternaria solani , and Pyrenophora teres.

17. The method according to claim 13 , wherein the compound of Formula I is suitable for the control of at least one fungal pathogen selected from the group consisting of Mycosphaerella graminicola ; anamorph: Septoria tritici, Puccinia triticina, Puccinia striiformis, Venturia inaequalis, Ustilago maydis, Uncinula necator, Rhynchosporium secalis, Magnaporthe grisea, Pseudoperonospora cubensis, Phakopsora pachyrhizi, Leptosphaeria nodorum, Blumeria graminis f. sp. tritici, Blumeria graminis f. sp. hordei, Erysiphe cichoracearum, Glomerella lagenarium, Cercospora beticola, Alternaria solani , and Pyrenophora teres.

18. The method according to claim 12 , wherein the compound of Formula I is suitable for the control of a fungal pathogen comprising Septoria tritici, Puccinia triticina , and Phakopsora pachyrhizi.

19. The method according to claim 13 , wherein the compound of Formula I is suitable for the control of a fungal pathogen comprising Septoria tritici, Puccinia triticina , and Phakopsora pachyrhizi.

20. The method according to claim 1 , wherein the compound of Formula I is applied to a root of the plant or foliage of the plant.

Assignees

• Dow Agrosciences Llc

Inventors

• Martin Timothy P
• Meyer Kevin G
• Nugent Benjamin
• Yao Chenglin
• Owen W John
• Wilson Anne M
• O'Callaghan Ian
• Wilmot Jeremy
• Delorbe Johnathan E
• Dent Iii William

Classifications

• A01N43/40

  six-membered rings · CPC title

• A01N43/24 Primary

  with two or more hetero atoms · CPC title

• C07D405/12

  linked by a chain containing hetero atoms as chain links · 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

• A01N47/18

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