IP Library Granted Patent US 11,596,151
Granted Patent B2
US 11,596,151 · App. 16/219,466 · Granted Mar 7, 2023

Compositions for the protection of agrarian crops and use thereof

Inventors: Robbie Moss Haines (Evesham, GB); Charlie James Flood (Evesham, GB); Hong Zhang (Cary, NC); David Bird (Randolph, NJ); Laibin B. Yan (North Wales, PA); Frank J. Zawacki (Yardley, PA); Claudio Dacarro (Milan, IT); Elisa Galimberti (Lissone, IT); Ilenia Mazzali (Novara, IT)
A01N43/56A01N25/04A01N25/30A01N43/653
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Quick Facts
Patent No.
US 11,596,151
App. No.
16/219,466
Granted
Mar 7, 2023
Kind
B2
Abstract

An emulsifiable concentrate may include: an aminoindane amide having the structure of formula (I); and an amide having the structure of formula (II); wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 11 , R 12 , R 13 , and n are as defined herein, as well as to formulations containing the same, and to methods of their preparation and use for treatment and protection of agricultural crops.

Claims (52)

1. An emulsifiable concentrate comprising:

a) an aminoindane amide having the structure of formula (I):

wherein

R 1 , R 2 , R 4 and R 6 are each methyl;

R 3 is H;

R 5 is H or methyl;

R 7 is methyl, difluoromethyl or trifluoromethyl;

R 8 is F; and

n is 1 to 3; and

b) an amide having the structure of formula (II):

wherein

R 11 is C 5-19 alkyl;

R 12 is C 1-4 alkyl; and

R 13 is C 1-4 alkyl.

2. The emulsifiable concentrate of claim 1 , wherein the aminoindane amide having the structure of formula (I) is

3. The emulsifiable concentrate of claim 1 , wherein R12 and R13 are each methyl.

4. The emulsifiable concentrate of claim 1 , wherein R11 is C7-11 alkyl.

5. The emulsifiable concentrate of claim 1 , wherein the amide having the structure of formula (II) is

6. The emulsifiable concentrate of claim 1 , comprising a mixture of at least two amides having the structure of formula (II).

7. The emulsifiable concentrate of claim 6 , wherein the mixture of at least two amides having the structure of formula (II) comprises:

at ratio of 0.1:99.9 wt % to 99.9:0.1 wt %.

8. The emulsifiable concentrate of claim 1 , wherein the aminoindane amide having the structure of formula (I) is fluindapyr; and the amide having the structure of formula (II) is N,N-dimethyldecanamide, N,N-dimethyloctanamide, or a mixture thereof.

9. The emulsifiable concentrate of claim 1 , further comprising an azole compound having fungicidal or insecticidal activity.

10. The emulsifiable concentrate of claim 9 , wherein the azole compound is cyproconazole, difenoconazole, epoxyconazole, flutriafol, penconazole, prochloraz, prothioconazole, tebuconazole, or tetraconazole.

11. The emulsifiable concentrate of claim 9 , wherein the azole compound is prothioconazole.

12. The emulsifiable concentrate of claim 9 , wherein the aminoindane amide having the structure of formula (I) is fluindapyr; the amide having the structure of formula (II) is N,N-dimethyldecanamide, N,N-dimethyloctanamide, or a mixture thereof; and the azole compound is prothioconazole.

13. The emulsifiable concentrate of claim 1 , wherein the aminoindane amide having the structure of formula (I) is present from about 1 wt % to about 20 wt %.

14. The emulsifiable concentrate of claim 1 , wherein the aminoindane amide having the structure of formula (I) is present from about 10 wt % to about 18 wt %.

15. The emulsifiable concentrate of claim 1 , wherein the aminoindane amide having the structure of formula (I) is present at about 14 wt %.

16. The emulsifiable concentrate of claim 13 , wherein the aminoindane amide having the structure of formula (I) is fluindapyr.

17. The emulsifiable concentrate of claim 9 , wherein the azole compound is present from about 1 wt % to about 20 wt %.

18. The emulsifiable concentrate of claim 9 , wherein the azole compound is present from about 10 wt % to about 18 wt %.

19. The emulsifiable concentrate of claim 9 , wherein the azole compound is present at about 14 wt %.

20. The emulsifiable concentrate of claim 17 , wherein the azole compound is prothioconazole.

21. The emulsifiable concentrate of claim 12 , wherein fluindapyr is present at about 14 wt % and prothioconazole is present at about 14 wt %.

22. The emulsifiable concentrate of claim 1 , wherein the aminoindane amide having the structure of formula (I) is present at a concentration of at least about 100 g/L.

23. The emulsifiable concentrate of claim 1 , wherein the aminoindane amide having the structure of formula (I) is present at a concentration of at least about 120 g/L.

24. The emulsifiable concentrate of claim 1 , wherein the aminoindane amide having the structure of formula (I) is present at a concentration of at least about 140 g/L.

25. The emulsifiable concentrate of claim 22 , wherein the aminoindane amide having the structure of formula (I) is fluindapyr.

26. The emulsifiable concentrate of claim 9 , wherein the azole compound is present at a concentration of at least 100 g/L.

27. The emulsifiable concentrate of claim 9 , wherein the azole compound is present at a concentration of at least 120 g/L.

28. The emulsifiable concentrate of claim 9 , wherein the azole compound is present at a concentration of at least 140 g/L.

29. The emulsifiable concentrate of claim 26 , wherein the azole compound is prothioconazole.

30. The emulsifiable concentrate of claim 12 , wherein fluindapyr is present at a concentration of at least about 140 g/L and prothioconazole is present at a concentration of at least about 140 g/L.

31. The emulsifiable concentrate of claim 1 , wherein the concentrate is a homogeneous solution.

32. A formulation comprising the emulsifiable concentrate of claim 1 emulsified in water.

33. The formulation of claim 32 , wherein the emulsifiable concentrate is emulsified in water with a dilution of at least 0.25% v/v.

34. The formulation of claim 32 , wherein the emulsifiable concentrate is emulsified in water with a dilution of at least 1.0% v/v.

35. The formulation of claim 32 , wherein the emulsifiable concentrate is emulsified in water with a dilution of at least 2.0% v/v.

36. The formulation of claim 32 , wherein the formulation is free from crystal formation by the aminoindane amide having the structure of formula (I).

37. A formulation comprising the emulsifiable concentrate of claim 9 emulsified in water.

38. The formulation of claim 37 wherein the formulation is free from crystal formation by the azole compound.

Assignments (8)
CHANGE OF ADDRESS Recorded Sep 14, 2025
From: FMC IP TECHNOLOGY GMBH
To: FMC IP TECHNOLOGY GMBH
Reel/Frame 072892/0066 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 6, 2024
From: FMC AGRO SINGAPORE PTE. LTD.
To: FMC IP TECHNOLOGY GMBH
Reel/Frame 067639/0738 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 29, 2023
From: FMC AGRICULTURAL PRODUCTS INTERNATIONAL AG
To: FMC AGRO SINGAPORE PTE. LTD.
Reel/Frame 062539/0825 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 30, 2022
From: STICHTING I-F PRODUCT COLLABORATION
To: FMC AGRICULTURAL PRODUCTS INTERNATIONAL AG
Reel/Frame 059436/0641 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 22, 2020
From: BIRD, DAVID; YAN, LAIBIN B.; ZAWACKI, FRANK J.; DACARRO, CLAUDIO; GALIMBERTI, ELISA; MAZZALI, ILENIA
To: STICHTING I-F PRODUCT COLLABORATION
Reel/Frame 053287/0788 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 31, 2020
From: ARYSTA LIFESCIENCE INC
To: ISAGRO S.P.A.
Reel/Frame 052274/0106 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 31, 2020
From: ISAGRO S.P.A.
To: STICHTING I-F PRODUCT COLLABORATION
Reel/Frame 052275/0079 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 18, 2020
From: HAINES, ROBBIE MOSS; FLOOD, CHARLIE JAMES; ZHANG, HONG
To: ARYSTA LIFESCIENCE INC.
Reel/Frame 052148/0801 →