IP Library Granted Patent US 10,941,157
Granted Patent B2
US 10,941,157 · App. 16/030,722 · Granted Mar 9, 2021

Pesticidal compositions and uses thereof

Inventors: Jennifer Lynn Bennett (Chesterfield, MO); Karen C. Fitzsimmons (Defiance, MO); Shomir Ghosh (Brookline, MA); Jeremy Robert Greenwood (Brooklyn, NY); William P. Haakenson, Jr. (St. Louis, MO); Geraldine C. Harriman (Charlestown, RI); Silvana Marcel Leit De Moradei (Burlington, MA); Barry J. Shortt (New Melle, MO); Urszula J. Slomczynska (Ballwin, MO); Jeffrey Michael Stein (Wildwood, MO)
Assignee: Gilead Apollo, LLC
C07D495/04A01N43/90
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Quick Facts
Patent No.
US 10,941,157
App. No.
16/030,722
Granted
Mar 9, 2021
Kind
B2
Abstract

Provided herein are compounds that exhibit activity as fungicides and are useful, for example, in methods for the control of fungal pathogens in plants and can be applied to said plants in a variety of ways.

Claims (26)

1. A method of controlling an agricultural fungal pathogen, the method comprising administering to a plant, a seed or soil a composition comprising a compound selected from the group consisting of:

(R)-ethyl-1-(2-(2-cyanoethoxy)-2-(5-fluoro-2-methoxyphenyl)ethyl)-3-(1-(isopropylamino)-2-methyl-1-oxopropan-2-yl)-5-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-6-carboxylate;

(R)-ethyl-1-(2-(5-fluoro-2-methoxyphenyl)-2-(2-hydroxyethoxy)ethyl)-3-(1-(isopropylamino)-2-methyl-1-oxopropan-2-yl)-5-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-6-carboxylate;

(R)-2-(1-(2-(2-cyanoethoxy)-2-(2-methoxyphenyl)ethyl)-5-methyl-2,4-dioxo-6-(1H-pyrazol-1-yl)-1,4-dihydrothieno[2,3-d]pyrimidin-3(2H)-yl)-N-isopropyl-2-methylpropanamide;

(R)-2-(1-(2-(2-cyanoethoxy)-2-(2-methoxyphenyl)ethyl)-5-methyl-2,4-dioxo-6-(2H-1,2,3-triazol-2-yl)-1,4-dihydrothieno[2,3-d]pyrimidin-3(2H)-yl)-N-isopropyl-2-methylpropanamide;

(R)-2-(1-(2-(2-cyano-2-methylpropoxy)-2-(5-fluoro-2-methoxyphenyl)ethyl)-5-methyl-2,4-dioxo-6-(2H-1,2,3-triazol-2-yl)-1,4-dihydrothieno [2,3-d]pyrimidin-3 (2H)-yl)-N-isopropyl-2-methylpropanamide;

(R)-ethyl-1-(2-(2-cyanoethoxy)-2-(5-fluoro-2-methoxyphenyl)ethyl)-3-((R)-1-(isopropylamino)-1-oxopropan-2-yl)-5-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-6-carboxylate;

(R)-ethyl-1-(2-(2-cyanoethoxy)-2-(5-fluoro-2-methoxyphenyl)ethyl)-3-(1-(ethylamino)-2-methyl-1-oxopropan-2-yl)-5-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-6-carboxylate;

(R)-ethyl-1-(2-(2-cyanoethoxy)-2-(2-methoxyphenyl)ethyl)-3-(1-(isopropylamino)-2-methyl-1-oxopropan-2-yl)-5-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-6-carboxylate; and

(R)-ethyl-1-(2-(2-cyanoethoxy)-2-(2-methoxyphenyl)ethyl)-3-(1-(ethylamino)-2-methyl-1-oxopropan-2-yl)-5-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-6-carboxylate;

or a salt thereof.

2. The method of claim 1 , wherein the composition further comprises a surfactant.

3. The method of claim 1 , wherein the composition further comprises a co-solvent.

4. The method of claim 1 , wherein the composition further comprises a biological control agent, microbial extract, natural product, plant growth activator plant defense agent, or a mixture thereof.

5. The method of claim 1 , wherein the composition further comprises an additional pesticide, wherein the additional pesticide is a fungicide, an insecticide, a herbicide, or a mixture thereof.

6. The method of claim 1 , wherein the composition further comprises an additional pesticide, wherein the additional pesticide is fluoxastrobin, fluxapyroxad, ipconazole, mefenoxam, metalaxyl, penflufen, prothioconazole, pyraclostrobin, trifloxystrobin, abamectin, clothianidin, imidacloprid, thiamethoxam, or a mixture thereof.

7. The method of claim 1 , wherein the composition further comprises tioxazafen.

8. The method of 1 , wherein the method comprises administering the composition to a seed.

9. A treated seed prepared according to the method of claim 1 .

10. The method of claim 1 , wherein the method comprises exogenously administering the composition to a plant.

11. The method of claim 10 , wherein the composition is applied to foliage of the plant.

12. The method of claim 10 , wherein the method comprises applying the composition to soil surrounding a root zone of the plant.

13. The method of claim 10 , wherein the composition is applied directly to a base of the plant or to soil immediately adjacent to the plant.

14. The method of claim 1 , wherein the agricultural fungal pathogen is selected from Ascomycetes, Deuteromycetes, Oomycetes, and Basidiomycetes.

15. The method of claim 1 , wherein the agricultural fungal pathogen is Blumeria graminis, Microsphaera spp., Podosphaera spp., Uncinula necator, Fusarium graminearum, Fusarium moniliforme, Fusarium virguliforme, Botrtyis cinerea, Sclerotinia sclerotiorum, Alternaria alternata, Alternaria solani, Collectotrichum graminicola, Cercospora spp., Septoria (Zymoseptoria) tritici, Rhizoctonia solani, Puccinia spp., Puccinia triticina, Phakopsora pachyrhizi, Diplodia maydis, Phytophthora capsici, Pythium spp., or Pythium ultimum.

16. The method of claim 1 , wherein the composition further comprises a biological control agent, wherein the biological control agent is Bacillus firmus.

Assignments (16)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 16, 2019
From: HARRIMAN, GERALDINE C.
To: NIMBUS DISCOVERY, INC.
Reel/Frame 049771/0278 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 12, 2019
From: STEIN, JEFFREY M.
To: MONSANTO COMPANY
Reel/Frame 049743/0291 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 12, 2019
From: SHORTT, BARRY J.
To: MONSANTO COMPANY
Reel/Frame 049743/0330 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 12, 2019
From: HAAKENSON, WILLIAM P., JR.
To: MONSANTO COMPANY
Reel/Frame 049743/0439 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 12, 2019
From: BENNETT, JENNIFER L.
To: MONSANTO COMPANY
Reel/Frame 049743/0504 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 12, 2019
From: FITZSIMMONS, KAREN C.
To: MONSANTO COMPANY
Reel/Frame 049743/0706 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 12, 2019
From: LEIT DE MORADEI, SILVANA MARCEL
To: NIMBUS APOLLO, INC.
Reel/Frame 049743/0843 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 12, 2019
From: NIMBUS DISCOVERY, INC.
To: NIMBUS APOLLO, INC.
Reel/Frame 049743/0857 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 12, 2019
From: SLOMCZYNSKA, URSZULA J.
To: MONSANTO COMPANY
Reel/Frame 049743/0189 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 12, 2019
From: GHOSH, SHOMIR
To: NIMBUS APOLLO, INC.
Reel/Frame 049743/0906 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 12, 2019
From: GREENWOOD, JEREMY ROBERT
To: SCHRÖDINGER, INC.
Reel/Frame 049744/0367 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 12, 2019
From: SCHRÖDINGER, INC.
To: SCHRÖDINGER, L.L.C.
Reel/Frame 049744/0432 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 12, 2019
From: SCHRÖDINGER, L.L.C.
To: NIMBUS DISCOVERY, INC.
Reel/Frame 049744/0520 →
CHANGE OF NAME Recorded Jul 12, 2019
From: GILEAD APOLLO, INC.
To: GILEAD APOLLO, LLC
Reel/Frame 049746/0072 →
CHANGE OF NAME Recorded Jul 12, 2019
From: NIMBUS APOLLO, INC.
To: GILEAD APOLLO, INC.
Reel/Frame 049746/0129 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 12, 2019
From: MONSANTO COMPANY
To: NIMBUS APOLLO, INC.
Reel/Frame 049743/0879 →
Continuity (3)
Continuation 15359531 · Nov 22, 2016
Provisional Application 62259935 · Nov 25, 2015
Related Publication 20190040078A1 · Feb 7, 2019