Macrocyclic picolinamides as fungicides

Patent metadata

Field	Value
Publication number	US-9681664-B2
Application number	US-201314142183-A
Country	US
Kind code	B2
Filing date	Dec 27, 2013
Priority date	Dec 31, 2012
Publication date	Jun 20, 2017
Grant date	Jun 20, 2017

Abstract

The disclosure relates to macrocyclic picolinamides of Formula (I) and to the use of these compounds as fungicides.

First claim

What is claimed:

1. A compound of Formula I:

wherein:
X is H;
Y is Q;
Q is

R 1 is H, alkyl, alkenyl, aryl, —C(O)R 4 , each substituted with 0, 1 or multiple R 4 ;
R 2 is alkyl, alkenyl, aryl —C(O)R 4 , each substituted with 0, 1 or multiple R 4 ;
R 3 is H, —C(O)R 6 or —CH 2 OC(O)R 6 ;
R 4 is alkyl, alkenyl, halo, haloalkyl, alkoxy, or aryl;
R 5 is alkyl, alkoxy, benzyl, benzyloxy, each substituted with 0, 1, or multiple R 7 , wherein each R 7 may be substituted with 0, 1, or multiple R 4 ;
R 6 is alkyl or alkoxy, each substituted with 0, 1, or multiple R 4 ; and
R 7 is alkyl, alkenyl, halo, haloalkyl, alkoxy, aryl, —Si(R 4 ) 3 , —C(O)R 4 , —S(O) n R 4 , each substituted with 0, 1, or multiple R 4 .

2. The compound according to claim 1 wherein R 1 is chosen from H, alkyl, alkenyl, aryl, or —C(O)R 4 , each substituted with 0, 1, or multiple R 4 , and
wherein R 2 is chosen from alkyl, alkenyl, aryl, or —C(O)R 4 , each substituted with 0, 1, or multiple R 4 .

3. The compound according to claim 1 wherein R 1 and R 2 are independently alkyl, alkenyl, aryl, or —C(O)R 4 , each substituted with 0, 1, or multiple R 4 .

4. A method for the treatment of plant disease, comprising the steps of:
applying a fungicidally effective amount of at least one of the compounds of claim 1 to at least one surface selected from the group consisting of: at least one surface of a plant, an area adjacent to a plant, soil in contact with a plant, soil adjacent to a plant, seeds, and equipment for use in agriculture.

5. The method of claim 4 , wherein the fungicidally effective amount of the compound of Formula I is applied to a surface in the range of about 0.01 g/m 2 to about 0.45 g/m 2 of the compound of Formula I.

6. The compound of claim 1 , wherein the compound is:

7. A method for the treatment of plant disease, comprising the steps of:
applying a fungicidally effective amount the compound of claim 6 to at least one surface selected from the group consisting of: at least one surface of a plant, an area adjacent to a plant, soil in contact with a plant, soil adjacent to a plant, seeds, and equipment for use in agriculture.

8. The method of claim 7 , wherein the fungicidally effective amount of the compound of Formula I is applied to a surface in the range of about 0.01 g/m 2 to about 0.45 g/m 2 of the compound of Formula I.

9. A compound of Formula I:

wherein:
X is H;
Y is Q;
Q is

R 1 is alkyl, alkenyl, aryl, —C(O)R 4 , each substituted with 0, 1 or multiple R 4 ;
R 2 is H, alkyl, alkenyl, aryl —C(O)R 4 , each substituted with 0, 1 or multiple R 4 ;
R 3 is H, —C(O)R 6 or —CH 2 OC(O)R 6 ;
R 4 is alkyl, alkenyl, halo, haloalkyl, alkoxy, or aryl;
R 5 is alkyl, alkoxy, benzyl, benzyloxy, each substituted with 0, 1, or multiple R 7 , wherein each R 7 may be substituted with 0, 1, or multiple R 4 ;
R 6 is alkyl or alkoxy, each substituted with 0, 1, or multiple R 4 ; and
R 7 is alkyl, alkenyl, halo, haloalkyl, alkoxy, aryl, —Si(R 4 ) 3 , —C(O)R 4 , —S(O) n R 4 , each substituted with 0, 1, or multiple R 4 .

10. The compound according to claim 9 wherein R 1 is chosen from alkyl, alkenyl, aryl, or —C(O)R 4 , each substituted with 0, 1, or multiple R 4 , and wherein R 2 is chosen from H, alkyl, alkenyl, aryl, or —C(O)R 4 , each substituted with 0, 1, or multiple R 4 .

11. A method for the treatment of plant disease, comprising the steps of:
applying a fungicidally effective amount of at least one of the compounds of claim 9 to at least one surface selected from the group consisting of: at least one surface of a plant, an area adjacent to a plant, soil in contact with a plant, soil adjacent to a plant, seeds, and equipment for use in agriculture.

12. The method of claim 11 , wherein the fungicidally effective amount of the compound of Formula I is applied to a surface in the range of about 0.01 g/m 2 to about 0.45 g/m 2 of the compound of Formula I.

Assignees

• Dow Agrosciences Llc

Inventors

• Lalonde Rebecca
• Meyer Kevin G
• Li Fangzheng
• Wilmot Jeremy
• Bravo-Altamirano Karla
• Yao Chenglin
• O'Callaghan Iain
• Herrick Jessica
• Dekorver Kyle
• Lu Yu

Classifications

• A01N43/40

  six-membered rings · CPC title

• C07D405/12

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

• A01N53/00 Primary

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

• A01N43/22

  rings with more than six members · CPC title