Macrocyclic picolinamides compounds with fungicidal activity

Patent metadata

Field	Value
Publication number	US-9629365-B2
Application number	US-201414500708-A
Country	US
Kind code	B2
Filing date	Sep 29, 2014
Priority date	Oct 1, 2013
Publication date	Apr 25, 2017
Grant date	Apr 25, 2017

Abstract

The invention relates to compounds of macrocyclic picolinamides of Formula I suitable to control or prevent growth of fungi.

First claim

What is claimed is:

1. A compound of Formula I

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

R 1 is chosen from H, alkyl, —CH 2 —CH═CH 2 , phenyl, or —C(O)R 6 , each optionally substituted with 0, 1 or multiple R 6 ;
R 2 is chosen from CH 2 R 8 , phenyl, alkyl, or —CH═CH 2 , each optionally substituted with 0, 1, or multiple R 6 ,
R 3 is chosen from alkyl, benzyl, 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 alkyl, or halo;
R 6 is chosen from alkyl, halo, haloalkyl, OCH 3 ,
—O—CH 2 -cyclopropyl, phenyl, 2-furanyl, —S—CH 3 , or —C(O)R 5 ;
R 7 is chosen from alkyl, —CH 2 —CH 2 —O—CH 3 , or —CH 2 —O—CH 2 —CH 3 , each optionally substituted with 0, 1, or multiple R 6 ; and
R 8 is chosen from H, alkyl, or phenyl, each optionally substituted with 0, 1, or multiple R 6 ;
wherein alkyl refers to a substituent selected from the group consisting of:
methyl, ethyl, propyl, butyl, isopropyl, isobutyl, tertiary butyl, branched or unbranched pentyl, branched or unbranched hexyl, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl, and
wherein haloalkyl refers to an alkyl which is substituted with one or more of Cl, F, I, or Br, or a combination thereof.

2. The compound according to claim 1 , wherein R 1 is chosen from H, alkyl, phenyl, or —C(O)R 6 , each optionally substituted with 0, 1 or multiple R 6 .

3. The compound according to claim 2 , wherein R 2 is chosen from CH 2 R 8 , phenyl, or alkyl, each optionally substituted with 0, 1, or multiple R 6 .

4. The compound according to claim 3 , wherein R 8 is chosen from H, alkyl, or phenyl, each optionally substituted with 0, 1, or multiple R 6 .

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

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

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

8. A formulation for the control of a fungal pathogen, comprising:
at least one of the compounds of claim 1 ; and
a phytologically acceptable carrier material.

9. The formulation according to claim 8 , wherein the formulation is suitable for treating plants.

10. A compound of Formula I,

wherein:
X is H;
Y is

R 1 is alkyl;
R 2 is alkyl optionally substituted with 0, 1, or multiple R 6 ;
R 4 is —CH 2 OC(O)R 7 ;
R 5 is alkyl or halo;
R 6 is alkyl or phenyl; and
R 7 is alkyl;
wherein alkyl refers to a substituent selected from the group consisting of: methyl, ethyl, propyl, butyl, isopropyl, isobutyl, tertiary butyl, branched or unbranched pentyl, branched or unbranched hexyl, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

11. The compound of claim 10 , wherein the compound is

12. A formulation for the control of a fungal pathogen, comprising:
at least one of the compounds of claim 10 ; and
a phytologically acceptable carrier material.

13. The formulation according to claim 12 , wherein the formulation is suitable for treating plants.

14. A formulation for the control of a fungal pathogen, comprising:
the compound of claim 11 ; and
a phytologically acceptable carrier material.

15. The formulation according to claim 14 , wherein the formulation is suitable for treating plants.

Assignees

• Dow Agrosciences Llc

Inventors

• Li Fangzheng
• Meyer Kevin G
• Renga James M
• Yao Chenglin
• Wilmot Jeremy
• Herrick Jessica
• Bravo-Altamirano Karla
• Boebel Timothy A

Classifications

• C07F7/1804

  Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896) · CPC title

• C07D313/00 Primary

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

• A01N43/04

  with one hetero atom · CPC title

• A01N43/08

  with oxygen as the ring hetero atom · CPC title

• A01N43/90

  having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system · CPC title