N-aliphatic and N,N-aliphatic phosphoric triamide urease inhibitors and urease inhibited urea based fertilizer compositions

• US 4,530,714 A
• Filed: 01/16/1984
• Issued: 07/23/1985
• Est. Priority Date: 03/16/1983
• Status: Expired due to Term

• Current Assignee: Alliedsignal Inc.
• Original Assignee: Allied Corp. (Honeywell International Inc.)
• Inventors: Hendrickson, Larry L., Swerdloff, Michael D., Rogic, Milorad M., Van Der Puy, Michael, Kolc, Jaroslav F.
• Primary Examiner(s): Lander, Ferris H.
• Application Number:
  US06/571,226
• Time in Patent Office: 554 Days
• Field of Search: 71/11, 71/27-30, 71/902
• US Class Current: 71/28
• CPC Class Codes: C05G 3/90 for affecting the nitrification of ammonium compounds or urea in the soil
• CPC Class Codes: C07F 9/224 Phosphorus triamides
• CPC Class Codes: C07F 9/26 containing P-halide groups
• CPC Class Codes: C07F 9/572 Five-membered rings
• CPC Class Codes: C07F 9/59 Hydrogenated pyridine rings
• CPC Class Codes: Y10S 71/902 Nitrification inhibition

Abstract

The invention relates to novel urease inhibited fertilizer compositions containing urea and a urease inhibiting amount of one or more phosphoric triamide compounds, and methods and composition for inhibiting the urease catalyzed hydrolysis of urea through use of such compounds.

Claims

1. A composition comprising an acceptable carrier and a urease inhibiting effective amount of one or more phosphoric triamide compounds of the formula:

##STR5## wherein;

X is oxygen or sulfur;

R₁ is alkyl, cycloalkenyl, alkenyl, alkynyl, aralkyl or cycloalkyl;

R₂ is R₁, hydrogen, or R₁ and R₂ together may form an alkylene or alkenylene chain which may optionally include one or more heteroatoms of oxygen, nitrogen, or sulfur completing a 3, 4, 5, 6, 7 or 8 membered ring structure; and

R₃, R₄, R₅ and R₆ are individually hydrogen or alkyl having from 1 to about 4 carbon atoms.

2. A composition according to claim 1 wherein said urease inhibiting amount is at least about 0.00001 weight percent based on the total weight of the composition.

3. A composition according to claim 2 wherein said amount is from about 0.00001 to about 98 weight percent.

4. A composition according to claim 3 wherein said amount is from about 0.0001 to about 50 weight percent.

5. A composition according to claim 4 wherein said amount is from about 0.001 to about 20 weight percent.

6. A composition according to claim 1 wherein X is oxygen.

7. A composition according to claim 1 wherein X is sulfur.

8. A composition according to claim 1 wherein R₁ is alkyl, aralkyl, alkenyl, cycloalkyl, or R₁ together with R₂ form an alkylene chain completing a 3, 4, 5 or 6 membered ring structure.

9. A composition according to claim 8 wherein R₁ is alkyl having from 1 to about 8 carbon atoms.

10. A composition according to claim 9 wherein R₁ is alkyl having from 1 to about 4 carbon atoms.

11. A composition according to claim 10 wherein R₁ is methyl or ethyl.

12. A composition according to claim 8 wherein R₁ is cycloalkyl.

13. A composition according to claim 1 wherein R₁ is cyclohexyl, cyclopropyl, cyclopentyl or cyclobutyl.

14. A composition according to claim 1 wherein R₁ is alkenyl.

15. A composition according to claim 1 wherein R₁ is alkenyl having from 2 to about 8 carbon atoms.

16. A composition according to claim 15 wherein R₁ is alkenyl having from about 2 to about 4 carbon atoms.

17. A composition according to claim 16 wherein R₁ is allyl.

18. A composition according to claim 8 wherein R₁ is aralkyl.

19. A composition according to claim 18 wherein R₁ is phenylalkyl wherein the aliphatic moiety includes from 1 to about 4 carbon atoms.

20. A composition according to claim 19 wherein R₁ is benzyl.

21. A composition according to claim 8 wherein R₁ and R₂ together form an alkylene chain completing a 3, 4, 5, or 6 membered ring structure.

22. A composition according to claim 21 wherein R₁ and R₂ together form an alkylene chain completing a 5 or 6 membered ring structure.

23. A composition according to claim 22 wherein R₁ and R₂ together form an alkylene chain completing a 6 membered ring structure.

24. A composition according to claim 1 wherein R₃, R₄, R₅ and R₆ are individudally hydrogen, methyl or ethyl.

25. A composition according to claim 13 wherein R₃, R₄, R₅ and R₆ are hydrogen.

26. A composition according to claim 1 wherein R₂ is hydrogen or R₁.

27. A composition according to claim 26 wherein R₂ is hydrogen, alkyl, cycloalkyl, alkenyl or aralkyl.

28. A composition according to claim 27 wherein R₂ is alkyl.

29. A composition according to claim 27 wherein R₂ is cyclohexyl.

30. A composition according to claim 27 wherein R₂ is hydrogen.

31. A composition according to claim 27 wherein R₂ is alkyl.

32. A composition according to claim 31 wherein R₂ is methyl, ethyl or propyl.

33. A composition according to claim 1 wherein:

X is oxygen or sulfur;

R₁ is alkyl, aralkyl, alkenyl or cycloalkyl;

R₂ is R₁ or hydrogen, or R₁ and R₂ together form an alkylene chain completing a 3, 4, 5, 6 or 7 membered ring structure; and

R₃, R₄, R₅ and R₆ are individually hydrogen, methyl or ethyl.

34. A composition acording to claim 33 wherein:

X is oxygen or sulfur;

R₁ is alkyl or alkenyl having from 1 to about 8 carbon atoms, phenylalkyl having from 7 to about 12 carbon atoms, cyclohexyl, cyclopentyl, cyclopropyl or cyclobutyl;

R₂ is hydrogen, alkyl or R₁ and R₂ together form an alkylene chain completing a 5 or 6 membered ring structure; and

R₃, R₄, R₅ and R₆ are hydrogen.

35. A composition according to claim 34 wherein X is oxygen.

36. A composition according to claim 34 wherein X is sulfur.

37. A composition according to claim 34 wherein R₂ is hydrogen.

38. A composition according to claim 34 wherein R₁ is alkyl.

39. A composition according to claim 1 wherein said one or more compounds are selected from the group consisting of N-isopropylphosphoric triamide, N,N-dimethylphosphoric triamide, N-benzyl-N-methylphosphoric triamide, N,N-diethylphosphoric triamide, N-allyphosphoric triamide, N-cyclohexylphosphoric triamide, N-(diaminophosphinyl)piperidine, N-ethylphosphoric triamide, N-(n-butyl)phosphoric triamide, N-(n-butyl)thiophosphoric triamide, N-(sec-butyl)phosphoric triamide, N-(n-octyl)phosphoric triamide, N-(n-dodecyl)phosphoric triamide, N,N-diethylthiophosphoric triamide, N-cyclohexyl-N-methylphosphoric triamide, N-benzyl-N-methylthiophosphoric triamide, N-cyclohexylthiophosphoric triamide, N-(n-hexyl)thiophosphoric triamide, N-(diaminothiophosphinyl)pyrrolidine, N-(sec-butyl)thiophosphoric triamide, N,N-diisopropylthiophosphoric triamide, N-(diaminothiophosphinyl)piperidine, and N,N-di-(n-butyl)thiophosphoric triamide.

50. A composition according to claim 1 wherein said carrier is a liquid.

51. A composition according to claim 50 wherein said liquid carrier is selected from the group consisting of water and organic liquids.

52. A composition according to claim 1 wherein said carrier is a finely divided inert solid.

40. A method of inhibiting the urease catalyzed hydrolysis of urea at a situs which comprises applying to said situs a urease inhibiting effective amount of one or more phosphoric triamide compounds of the formula:

##STR6## wherein;

X is sulfur or oxygen;

R₁ is alkyl, cycloalkenyl, alkenyl, alkynyl, aralkyl or cycloalkyl;

R₂ is hydrogen, R₁, or R₁ and R₂ together may form an alkylene or alkenylene chain which may optionally include one or more heteroatoms of oxygen, nitrogen or sulfur completing a 3, 4, 5, 6, 7 or 8 membered ring structure; and

R₃, R₄, R₅ and R₆ are individually hydrogen or alkyl having from 1 to about 4 carbon atoms.

41. A method according to claim 40 wherein said urease inhibiting effective amount of said one or more phosphoric triamide compounds is applied to said situs prior to, after or in conjunction with the application to said situs or urea, and/or one or more urea precursor compounds capable of forming urea in situ on application to said situs.

42. A method according to claim 41 wherein said situs is a plant growth medium.

43. A method according to claim 42 wherein said urease inhibiting effective amount of said phosphoric triamide compounds is applied to said medium prior to the application to said medium of urea and/or said one or more urea precursor compounds.

44. A method according to claim 41 wherein the amount of said one or more phosphoric triamide compounds applied to said plant growth medium is at least about 0.02 p.p.m.

45. A method according to claim 44 wherein said amount is from about 0.02 to about 5000 p.p.m.

46. A method according to claim 45 wherein said amount is from about 1 to about 1000 p.p.m.

47. A method according to claim 46 wherein said amount is from about 5 to about 100 p.p.m.

48. An improved fertilizer composition which comprises urea and/or one or more compounds capable of forming urea under the use conditions of said composition and a urease inhibiting effective amount of one or more phosphoric triamide compounds of the formula:

##STR7## wherein;

X is sulfur and oxygen;

R₁ is alkyl, cycloalkenyl, alkenyl, alkynyl, aralkyl or cycloalkyl;

R₂ is hydrogen, R₁, or R₁ and R₂ together may form an alkylene or alkenylene chain which may optionally include one or more heteroatoms of oxygen, nitrogen, or sulfur completing a 3, 4, 5, 6, 7 or 8 membered ring structure; and

R₃, R₄, R₅ and R₆ are individually hydrogen or alkyl having from 1 to about 4 carbon atoms.

49. A method of enhancing plant growth and crop yield which comprises applying the composition according to claim 48 to a plant growth medium within the root zone of said plant.