IP Library Granted Patent US 9,637,420
Granted Patent B2
US 9,637,420 · App. 14/553,107 · Granted May 2, 2017

Increased longevity of the nitrogen content of soil through improved liquid delivery formulations of urease inhibitors and/or nitrification inhibitors designed for urea and manure based fertilizers

Inventors: Gary David McKnight (High Point, NC); Randall Linwood Rayborn (Burlington, NC); David Bruce Parker (Canyon, TX); Wei Xu (Sugarland, TX); Zehui Yang (Ningbo, CN); Raymond Patrick Perkins (Tierra Verde, FL); Andrew Michael Semple (Bradenton, FL)
C05G3/08C05C9/00C05D9/02C09K15/28C05F3/00Y02P20/145Y02P60/218
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Quick Facts
Patent No.
US 9,637,420
App. No.
14/553,107
Granted
May 2, 2017
Kind
B2
Abstract

Increasing longevity of the nitrogen content of soil through improved liquid delivery formulations of urease inhibitors and/or nitrification inhibitors designed to apply to fertilizers, especially urea and manure based fertilizers These delivery formulations provide an environmentally sound and inherently safe solvating system that improves the storage stability of the urease inhibitors by utilizing aprotic solvents, maintain the urease inhibitors and/or nitrification inhibitors in solution to storage temperatures of at least 10° C. and provides improved application to fertilizer of urease and/or nitrification inhibitors. These delivery formulations enable safe storage, transport and subsequent application or blending with urea based or manure based fertilizers that can be applied to soil in either a liquid or granular form to provide improved nitrogen retention in the soil for uptake for plant life.

Claims (66)

1. A composition comprising one or more nitrification inhibitors and one or more urease inhibitors in an organic liquid solvating system comprising a mixture of aprotic solvents

wherein a first aprotic solvent is dimethyl sulfoxide, dialkyl sulfoxide, diaryl sulfoxide, or an alkylaryl sulfoxide having the formula

R 1 —S(O)—R 2 ,

wherein R 1 is methyl, ethyl, n-propyl, phenyl or benzyl and R 2 is ethyl, n-propyl, phenyl or benzyl,

and a second aprotic solvent is one or more members selected from the group consisting of:

1) a C 1 -C 12 ester of

a) an alcohol or polyol from the family of C 1-10 alkynols and poly(C 1-10 alkylene) glycols,

b) an alkylene glycol selected from the group consisting of ethylene, propylene, and butylene glycol,

c) glycerin,

d) an alkylene glycol alkyl ether selected from the group consisting of dipropylene glycol methyl ether, tripropylene glycol methyl ether, and tripropylene glycol butyl ether

wherein the organic liquid solvating system meets the following criteria:

a. environmentally safe

b. has a flashpoint above 145° F.

c. inherently rated safe for contact with humans and animals

d. results in a composition comprising at least one of nitrification and urease inhibitors with a Chill Point <40° F.

2. The composition of claim 1 , wherein the nitrification inhibitor is one or more members selected from the group consisting of 1) dicyandiamide, 2) 2-chloro-6 trichloromethyl)pyridine, 3) 4-amino-1,2,4-6-triazole-HCl, 4) 2,4-diamino-6-trichloromethyltriazine, 5) thiourea, 6) 1-mercapto-1,2,4-triazole and 2-amino-4-chloro-6-methylpyrimidine, and 7) 3,4-dimethylpyrazole phosphate.

3. The composition of claim 1 , wherein one of the aprotic solvents in the mixture is dimethyl sulfoxide.

4. The composition of claim 3 , wherein dimethyl sulfoxide comprises between about 10 and 90% of the composition.

5. The composition of claim 1 wherein the one or more nitrification inhibitors comprises one or more members selected from the group consisting of 1) dicyandiamide, 2) 2-chloro-6 trichloromethyl)pyridine, 3) 4-amino-1,2,4-6-triazole-HCl, 4) 2,4-diamino-6-trichloromethyltriazine, 5) thiourea, 6) 1-mercapto-1,2,4-triazole and 2-amino-4-chloro-6-methylpyrimidine, and 7) 3,4 dimethylpyrazole phosphate;

in a formulation wherein nitrification inhibitor(s) is/are present in an amount that is between about 5-45% of a total formulation amount and the composition also contains a mixture of DMSO and one or more aprotic solvents in ratios that are between about 20/80 to 80/20.

6. The composition of claim 1 , further comprising one or more members selected from the group consisting of protic solvents present in the amount of 0.5-15%, surfactants, buffers, fragrance/odor masking agents, colorants, micro-nutrients, dispersed nitrification inhibitors, dispersed urease inhibitor(s), crystallization inhibitors and flow modifiers.

7. The composition of claim 1 , wherein the one or more nitrification inhibitors comprises one or more members selected from the group consisting of 1) dicyandiamide, 2) 2-chloro-6 trichloromethyl)pyridine, 3) 4-amino-1,2,4-6-triazole-HCl, 4) 2,4-diamino-6-trichloromethyltriazine, 5) thiourea, 6) 1-Mercapto-1,2,4-triazole and 2-amino-4-chloro-6-methylpyrimidine, and 7) 3,4 dimethylpyrazole phosphate

in a formulation wherein nitrification inhibitor(s) is/are present in an amount that is between about 5-45% of a total formulation amount and the formulation also comprises N-(n-butyl) thiophosphoric triamide in an amount that is between about 5-45% of the total formulation amount.

8. The composition of claim 4 , wherein the composition is substantially free of water.

9. A fertilizer granule additive or a liquid fertilizer additive, which comprises one or more nitrification inhibitors and one or more urease inhibitors in an organic liquid solvating system comprising a mixture of aprotic solvents

wherein a first aprotic solvent is dimethyl sulfoxide, dialkyl sulfoxide, diaryl sulfoxide, or an alkylaryl sulfoxide having the formula

R 1 —S(O)—R 2 ,

wherein R 1 is methyl, ethyl, n-propyl, phenyl or benzyl and R 2 is ethyl, n-propyl, phenyl or benzyl,

and a second aprotic solvent is one or more members selected from the group consisting of

1) a C 1 -C 12 ester of

a) an alcohol or polyol from the family of C 1-10 alkynols and poly(C 1-10 alkylene) glycols,

b) an alkylene glycol selected from the group consisting of ethylene, propylene, and butylene glycol,

c) glycerin,

d) an alkylene glycol alkyl ether selected from the group consisting of dipropylene glycol methyl ether, tripropylene glycol methyl ether, and tripropylene glycol butyl ether;

wherein the organo liquid solvating system meets the following criteria:

a. Environmentally safe

b. Have flashpoint above 145 F

c. Inherently rated safe for contact with humans and animals

d. That result in a composition comprising of nitrification and urease inhibitor with a Chill Point <40 F.

10. The fertilizer granule additive or the liquid fertilizer additive of claim 9 , wherein the one or more nitrification inhibitors is selected from the group consisting of 1) dicyandiamide, 2) 2-chloro-6 trichloromethyl)pyridine, 3) 4-amino-1,2,4-6-triazole-HCl, 4) 2,4-diamino-6-trichloromethyltriazine, 5) thiourea, 6) 1-mercapto-1,2,4-triazole and 2-amino-4-chloro-6-methylpyrimidine, and 7) 3,4 dimethylpyrazole phosphate.

11. The fertilizer granule additive or the liquid fertilizer additive of claim 9 , further comprising one or more urease inhibitors selected from the group consisting of phosphoric triamides, thiophosphoric triamides and alkylated thiophosphoric triamides, wherein the alkylated thiophosphoric triamides has one or more alkyl groups that independently contain between 1 and 6 carbon atoms.

12. The fertilizer granule additive or the liquid fertilizer additive of claim 11 , wherein the one or more nitrification inhibitors comprises 1) dicyandiamide, 2) 2-chloro-6 trichloromethyl)pyridine, 3) 4-amino-1,2,4-6-triazole-HCl, 4) 2,4-diamino-6-trichloromethyltriazine, 5) thiourea, 6) 1-mercapto-1,2,4-triazole and 2-Amino-4-chloro-6-methylpyrimidine, or 7) 3,4 dimethylpyrazole phosphate;

and the one or more urease inhibitors comprises phosphoramides.

13. A method of making a composition to be added to a fertilizer comprising:

heating a mixture comprising one or more nitrification inhibitors in an organic liquid solvating system comprising a mixture of aprotic solvents

wherein a first aprotic solvent is dimethyl sulfoxide, dialkyl sulfoxide, diaryl sulfoxide, or an alkylaryl sulfoxide having the formula

R 1 —S(O)—R 2 ,

wherein R 1 is methyl, ethyl, n-propyl, phenyl or benzyl and R 2 is ethyl, n-propyl, phenyl or benzyl,

and a second aprotic solvent is one or more members selected from the group consisting of:

1) a C 1 -C 12 ester of

a) an alcohol or polyol from the family of C 1-10 alkynols and poly(C 1-10 alkylene) glycols,

b) an alkylene glycol selected from the group consisting of ethylene, propylene, and butylene glycol,

c) glycerin,

d) an alkylene glycol alkyl ethers selected from the group consisting of Dipropylene glycol methyl ether, Tripropylene glycol methyl ether, and Tripropylene glycol butyl ether,

wherein the organo liquid solvating system meets the following criteria:

a. Environmentally safe

b. Have flashpoints above 145 F

c. Inherently rated safe for contact with humans and animals

e. That result in a composition comprising of nitrification and urease inhibitor with a chill point <40 F

cooling the mixture to a temperature that optionally allows an addition of one or more of

protic solvents present in the amount of 0.5-15%, surfactants, buffers, fragrance/odor masking agents, colorants, micro-nutrients, dispersed nitrification inhibitors, dispersed urease inhibitor(s), crystallization inhibitors and flow modifiers.

14. The method of claim 13 , further comprising adding the composition to a fertilizer granule or liquid.

15. The method of claim 13 , wherein the one or more nitrification inhibitors is one or more members selected from the group consisting of 1) dicyandiamide, 2) 2-chloro-6 trichloromethyl)pyridine, 3) 4-amino-1,2,4-6-triazole-HCl, 4) 2,4-diamino-6-trichloromethyltriazine, 5) thiourea, 6) 1-mercapto-1,2,4-triazole and 2-amino-4-chloro-6-methylpyrimidine, and 7) 3,4 dimethylpyrazole phosphate.

16. The method of claim 13 , further comprising one or more urease inhibitors selected from the group consisting of phosphoric triamides, thiophosphoric triamides and alkylated thiophosphoric triamides, wherein the alkylated thiophosphoric triamides have one or more alkyl groups that independently contain between 1 and 6 carbon atoms.

17. The method of claim 16 , wherein the one or more nitrification inhibitors is one or more members selected from the group consisting of 1) dicyandiamide, 2) 2-chloro-6 trichloromethyl)pyridine, 3) 4-amino-1,2,4-6-triazole-HCl, 4) 2,4-diamino-6-trichloromethyltriazine, 5) thiourea, 6) 1-mercapto-1,2,4-triazole and 2-amino-4-chloro-6-methylpyrimidine, and 7) 3,4 dimethylpyrazole phosphate and the one or more urease inhibitors comprises phosphoramides.

18. The method of claim 13 , wherein the composition is substantially free of water.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 6, 2022
From: WORLD SOURCE ENTERPRISES LLC
To: SOILGENIC TECHNOLOGIES, LLC
Reel/Frame 060592/0249 →
CORRECTIVE ASSIGNMENT TO CORRECT THE THE APPLICATION NUMBER PREVIOUSLY RECORDED AT REEL: 039056 FRAME: 0887. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded May 11, 2017
From: ECO WORLD RESEARCH AND DEVELOPMENT GROUP LLC
To: WORLDSOURCE ENTERPRISES, LLC
Reel/Frame 042380/0078 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 30, 2016
From: ECO WORLD RESEARCH AND DEVELOPMENT GROUP LLC
To: WORLDSOURCE ENTERPRISES, LLC
Reel/Frame 039056/0887 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 30, 2015
From: MCKNIGHT, GARY DAVID, MR; RAYBORN, RANDALL LINWOOD, MR; PARKER, DAVID BRUCE, MR; XU, WEI, MR; YANG, ZEHUI, MR; PERKINS, RAYMOND PATRICK, MR; SEMPLE, ANDREW MICHAEL, MR
To: ECO WORLD RESEARCH AND DEVELOPMENT GROUP, LLC
Reel/Frame 036927/0655 →
Continuity (2)
Provisional Application 61909129 · Nov 26, 2013
Related Publication 20150143860A1 · May 28, 2015