Macrocyclic picolinamides as fungicides

Patent metadata

Field	Value
Publication number	US-9700047-B2
Application number	US-201515036321-A
Country	US
Kind code	B2
Filing date	Apr 30, 2015
Priority date	May 6, 2014
Publication date	Jul 11, 2017
Grant date	Jul 11, 2017

Abstract

This disclosure 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 and R 2 are independently selected from the group consisting of hydrogen, alkyl, alkenyl, and aryl, each optionally substituted with 0, 1 or multiple R 6 ;
R 3 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, halo, acyloxy, 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. 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 or aryl, each optionally substituted with 0, 1 or multiple R 6 .

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

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

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

7. A compound according to claim 5 , wherein R 2 is chosen from alkyl or aryl, each optionally substituted with 0, 1 or multiple R 6 .

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

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

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

11. A compound according to claim 9 , wherein R 4 is hydrogen.

12. A compound according to claim 9 , wherein R 4 is —C(O)R 5 or —CH 2 OC(O)R 5 .

13. A compound according to claim 12 , wherein R 5 is chosen from alkyl or alkoxy, each optionally substituted with 0, 1, or multiple R 6 .

14. A compound according to claim 13 , wherein R 5 is chosen from —CH 3 , —CH(CH 3 ) 2 , —CH 2 OCH 2 CH 3 , or —CH 2 CH 2 OCH 3 .

15. A composition for the control of a fungal pathogen including at least one of the compounds of claim 1 and a phytologically acceptable carrier material.

16. A composition for the control of a fungal pathogen including mixtures of at least one of the compounds of claim 1 with other pesticides including fungicides, insecticides, nematocides, miticides, arthropodicides, bactericides, and combinations thereof.

17. The composition according to claim 16 , further comprising an azole fungicide selected from the group consisting of epoxiconazole, tebuconazole, fluquinconazole, flutriafol, metconazole, myclobutanil, cycproconazole, prothioconazole, and propiconazole.

18. The composition according to claim 16 , further comprising a strobilurin fungicide selected from the group consisting of trifloxystrobin, pyraclostrobin, orysastrobin, fluoxastrobin, and azoxystrobin.

19. The composition according to claim 16 , further comprising a succinate dehydrogenase inhibiting (SDHI) fungicide selected from the group consisting of fluxapyroxad, boscalid, penthiopyrad, benzovindiflupyr, bixafen, flupyram, and isopyrazam.

20. The compositions according to claim 15 wherein the fungal pathogen is one 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 ).

21. The composition according to claim 20 wherein the fungal pathogen is one of Leaf Blotch of Wheat ( Septoria tritici ), Wheat Brown Rust ( Puccinia triticina ), and Rust of Soybean ( Phakopsora pachyrhizi ).

22. 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 at least one of the compounds of claim 1 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.

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 at least one of the compositions 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.

Assignees

• Dow Agrosciences Llc

Inventors

• Lu Yu
• Boebel Timothy A
• Li Fangzheng
• Bravo-Altamirano Karla
• Daeuble Sr John F
• Yao Chenglin
• Meyer Kevin G

Classifications

• A01N43/22

  rings with more than six members · CPC title

• A01N43/40 Primary

  six-membered rings · CPC title

• A01N47/36

  containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues 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

• A01N47/24

  containing the groups [IMAGE cpc-sch-A01N-0944.gif], [IMAGE cpc-sch-A01N-0945.gif] or[IMAGE cpc-sch-A01N-0946.gif]; Thio analogues thereof · CPC title