Macrocyclic picolinamide compounds with fungicidal activity

Patent metadata

Field	Value
Publication number	US-9549555-B2
Application number	US-201414577944-A
Country	US
Kind code	B2
Filing date	Dec 19, 2014
Priority date	Dec 26, 2013
Publication date	Jan 24, 2017
Grant date	Jan 24, 2017

Abstract

The invention 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 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, or thioalkyl, each optionally substituted with 0, 1, or multiple R 7 ; and
R 7 is hydrogen, alkyl, aryl, or halo;
wherein acyl refers to —C(═O)-cyclopropyl or —C(═O)—CH(CH 3 ) 2 .

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

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

4. A compound according to claim 2 , wherein R 2 is chosen from hydrogen, alkyl, aryl, and acyl, each optionally substituted with 0, 1 or multiple R 6 .

5. A compound according to claim 2 , 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 hydrogen, alkyl, aryl, and acyl, each optionally substituted with 0, 1 or multiple R 6 .

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

7. A compound according to claim 6 , wherein R 1 is chosen from alkyl and aryl, each optionally substituted with 0, 1 or multiple R 6 .

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

9. A compound according to claim 6 , 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 hydrogen, alkyl, aryl, and acyl, each optionally substituted with 0, 1 or multiple R 6 .

10. A compound according to claim 1 , wherein X is hydrogen and Y is Q.

11. A compound according to claim 10 , wherein R 4 is hydrogen.

12. A compound according to claim 11 , wherein R 1 is chosen from alkyl and aryl, each optionally substituted with 0, 1 or multiple R 6 .

13. A compound according to claim 11 , wherein R 2 is chosen from hydrogen, alkyl, aryl, and acyl, each optionally substituted with 0, 1 or multiple R 6 .

14. A compound according to claim 11 , 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 hydrogen, alkyl, aryl, and acyl, each optionally substituted with 0, 1 or multiple R 6 .

15. A compound according to claim 10 , wherein R 4 is —C(O)R 5 or —CH 2 OC(O)R 5 .

16. A compound according to claim 15 , wherein R 5 is chosen from alkyl and alkoxy, each optionally substituted with 0, 1, or multiple R 6 .

17. A compound according to claim 16 , wherein R 1 is chosen from alkyl and aryl, each optionally substituted with 0, 1 or multiple R 6 .

18. A compound according to claim 16 , wherein R 2 is chosen from hydrogen, alkyl, aryl, and acyl, each optionally substituted with 0, 1 or multiple R 6 .

19. A compound according to claim 16 , 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 hydrogen, alkyl, aryl, and acyl, each optionally substituted with 0, 1 or multiple R 6 .

20. A compound according to claim 19 , wherein R 5 is chosen from —CH 2 OCH 2 CH 3 and —CH 3 .

21. A compound according to claim 1 , wherein acyl refers to —C(═O)—CH(CH 3 ) 2 .

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

• C07D313/00

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

• C07D405/12

  linked by a chain containing hetero atoms as chain links · 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

• A01N47/18

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