LOW TEMPERATURE STABLE HIGH CONCENTRATION FORMULATIONS OF NITRAPYRIN

Abstract

The present disclosure relates to a high concentration nitrapyrin liquid formulation with improved stability against crystallization and/or freezing under exposure to low temperatures of 0 C. or below, and methods to make and use such a formulation.

Claims

1. A formulation, comprising: i) nitrapyrin in an amount ranging from about 30% to about 50% by weight; ii) a glycol, a glycol derivative, and/or an alkylene glycol alkyl ether in an amount ranging from about 10% to about 50% by weight; and/or iii) N-methyl-2-pyrrolidinone (NMP) in an amount ranging from about 20% to about 70% by weight; wherein each component is present in amount by weight of the total formulation.

2. The formulation of claim 1, further comprising a urease inhibitor.

3. The formulation of claim 1, further comprising an excipient.

4. The formulation of claim 1, further comprising a dye.

5. The formulation of claim 1, wherein said glycol or glycol derivative or alkylene glycol alkyl ether is diethylene glycol or dipropylene glycol.

6. The formulation of claim 1, wherein said glycol or glycol derivative or alkylene glycol alkyl ether is an alkylene glycol alkyl ether selected from diethylene glycol monoethyl ether, diethylene glycol monopropyl ether, diethylene glycol monopentyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monoisobutyl ether, diethylene glycol monohexyl ether, triethylene glycol monomethyl ether, triethylene glycol monopropyl ether, triethylene glycol monobutyl ether, triethylene glycol monopentyl ether, triethylene glycol monoisopropyl ether, triethylene glycol monoisobutyl ether, triethylene glycol monohexyl ether, tetraethylene glycol monomethyl ether, tetraethylene glycol monoethyl ether, tetraethylene glycol monopropyl ether, tetraethylene glycol monobutyl ether, tetraethylene glycol monopentyl ether, tetraethylene glycol monoisopropyl ether, tetraethylene glycol monoisobutyl ether, tetraethylene glycol monohexyl ether, dipropylene glycol monoethyl ether, dipropylene glycol monopropyl ether, dipropylene glycol monobutyl ether, dipropylene glycol monopentyl ether, dipropylene glycol monoisopropyl ether, dipropylene glycol monoisobutyl ether, dipropylene glycol monohexyl ether, tripropylene glycol monoethyl ether, tripropylene glycol monopropyl ether, tripropylene glycol monobutyl ether, tripropylene glycol monopentyl ether, tripropylene glycol monoisopropyl ether, tripropylene glycol monoisobutyl ether, tripropylene glycol monohexyl ether, and combinations thereof.

7. The formulation of claim 1, wherein said alkylene glycol alkyl ether is a mixture of triethylene glycol monobutyl ether, tetraethylene glycol monobutyl ether, and diethylene glycol monobutyl ether.

8. The formulation of claim 7, wherein said mixture of triethylene glycol monobutyl ether, tetraethylene glycol monobutyl ether, and diethylene glycol monobutyl ether alkylene glycol alkyl ether contains 70-80% triethylene glycol monobutyl ether, 15-25% tetraethylene glycol monobutyl ether, and less than 5% diethylene glycol monobutyl ether.

9. The formulation of claim 2, wherein the urease inhibitor is N-(n-butyl) thiophosphoric triamide (NBPT).

10. The formulation of claim 1, wherein the formulation is stable at 0 C.

11. The formulation of claim 10, wherein the formulation is stable for at least 2 weeks.

12. The formulation of claim 10, wherein less than about 5% of the total solution is frozen and/or wherein less than about 5% of total solids crystallize out from solution.

13. The formulation of claim 1, wherein nitrapyrin is present in an amount of about 30% by weight and NMP is present in an amount of about 70% by weight.

14. The formulation of claim 1, wherein nitrapyrin is present in an amount of about 30% by weight; a glycol, a glycol derivative and/or alkylene glycol alkyl ether is present in an amount of about 47% by weight; and NMP is present in an amount of about 23% by weight.

15. The formulation of claim 1, wherein nitrapyrin is present in an amount of about 50% by weight; a glycol, a glycol derivative and/or alkylene glycol alkyl ether is present in an amount of about 14.2% by weight; NMP is present in an amount of about 28.5% by weight; a urease inhibitor is present in an amount of about 7.1% by weight; and a dye is present in an amount of about 0.2% by weight.

16. The formulation of claim 1, further comprising a surfactant selected from octylphenol polyether alcohol, sulfosuccinate, naphthalene sulfonate, sulfated ester, phosphate ester, sulfated alcohol, alkyl benzene sulfonate, polycarboxylate, naphthalene sulfonate condensate, phenol sulfonic acid condensate, lignosulfonate, methyl oleyl taurate, polyvinyl alcohol, polysorbates, or any combination thereof.

17. A method of making a nitrapyrin formulation, the method comprising: mixing nitrapyin; at least one of the following: a glycol, a glycol derivative or alkylene glycol alkyl ether; and NMP to form a composition according to claim 1.

18. A method of making an incorporated urea-containing fertilizer, the method comprising: mixing the nitrapyrin formulation according to claim 1 into a molten urea-containing fertilizer.

19. A method of fertilizing soil, the method comprising: contacting soil with a formulation according to claim 1.

20. The method of claim 19, wherein the formulation is sprayed onto the soil.

Description

EXAMPLES

Example 1: Concentrated Nitrapyrin Solution

General Preparation Method:

[0035] A 66.08 wt. percent stock solution of nitrapyrin in NMP was formulated. This solution was made by taking crystalline nitrapyrin and grinding it to a homogeneous coarse powder with a mortar and pestle. Then the appropriate amount of ground nitrapyrin corresponding to 66.08 wt. percent of the final solution was added to 33.92 wt. percent NMP in a glass vessel. A stir bar was then added and the solution stirred at room temperature (22 C.) on a stir plate until the nitrapyrin was fully dissolved into the solution. This typically took 3-4 hours depending on stir plate rpm. Aliquots were then taken of the previously mentioned stock solution and formulated into the appropriate formulations via further dilution with the appropriate solvents (additional NMP, glycol/glycol derivatives, and/or alkylene glycol alkyl ethers). The final formulations were placed into a glass vessel. A stir bar was then inserted and the solutions were stirred at room temperature for 10 minutes to ensure a homogenous mixture.

Example 2: Formulation of Nitrapyrin (30.00%), FLOMIN F660 (46.67%) and NMP (23.33%) Solution

[0036] According to example 1, 66.08 wt. percent nitrapyrin in NMP stock solution was formulated. In a glass vessel, a stir bar and 45.40 g of 66.08 wt. percent nitrapyrin in NMP stock solution were added and placed on stir plate. To which, was added 7.93 g additional NMP followed by 46.67 g FLOMIN F660. The stir plate was turned on and the formulation stirred at room temperature (22 C.) for 10 minutes to ensure homogeneity.

Example 3: Stability Experiments

[0037] Formulations in the following table were prepared according to Examples 1 and 2 using appropriate amounts of nitrapyrin stock solution and the remaining components.

TABLE-US-00001 0 C. 15 C. Entry Formulation stability stability 10 C. stability 1 30% Nitrapyrin, 15.4% NMP, Crystallized out immediately at Room temp. 54.6% PG 2 30% Nitrapyrin, 15.4% NMP, Crystallized out immediately at Room temp. 54.6% ethylene glycol 3 30% Nitrapyrin, 15.4% NMP, Liquid at 30 50 days 3 days 54.6% FLOMIN F660 days 4 30% Nitrapyrin, 15.4% NMP, <1 day <1 day 54.6% diethylene glycol 5 30% Nitrapyrin, 15.4% NMP, <1 day <1 day 54.6% dipropylene glycol 6 30% Nitrapyrin, 70% NMP Liquid >30 Liquid >400 Liquid >400 days days days 7 30% Nitrapyrin, 23.33% NMP, <1 day <1 day 46.67% PG 8 30% Nitrapyrin, 35% NMP, 35% t = 17 days 3 days PG 9 30% Nitrapyrin, 46.67% NMP, Liquid >21 5 days 3 days 23.33% PG days 10 30% Nitrapyrin, 23.33% NMP, Liquid >30 Liquid >400 Liquid >400 46.67% FLOMIN F660 days days days 11 30% Nitrapyrin, 35% NMP, 35% Liquid >30 Liquid >400 Liquid >400 FLOMIN F660 days days days 12 30% Nitrapyrin, 46.67% NMP, Liquid >30 Liquid >400 Liquid >400 23.33% FLOMIN F660 days days days 13 30% Nitrapyrin, 23.33% NMP, 3 days 3 days 46.67% diethylene glycol 14 30% Nitrapyrin, 35% NMP, 35% Liquid >21 27 days 3 days diethylene glycol days 15 30% Nitrapyrin, 46.67% NMP, Liquid >21 Liquid >400 Liquid >391 23.33% diethylene glycol days days days 16 30% Nitrapyrin, 23.33% NMP, Crystallized out immediately at Room temp. 46.67% ethylene glycol 17 30% Nitrapyrin, 35% NMP, 35% 1 day 1 day ethylene glycol 18 30% Nitrapyrin, 46.67% NMP, Liquid >21 1 day 3 days 23.33% ethylene glycol days 19 30% Nitrapyrin, 23.33% NMP, Liquid >21 1 day 3 days 46.67% Dipropylene glycol days 20 30% Nitrapyrin, 35% NMP, 2 days 2 days 35% Dipropylene glycol 21 30% Nitrapyrin, 46.67% NMP, Liquid >17 Liquid >400 Liquid >387 23.33% Dipropylene glycol days days days 22 60% Nitrapyrin, 30.8% NMP, <1 day 9.2% FLOMIN F660 23 50% Nitrapyrin, 20% NMP, 30% <1 day FLOMIN F660 24 50% Nitrapyrin, 50% NMP Liquid >17 2 days 15 days days 25 45% Nitrapyrin, 45% NMP, Liquid >17 2 days 15 days 10% FLOMIN F660 days 26 45% Nitrapyrin, 30% NMP, Liquid >17 Liquid >385 Liquid >351 25% FLOMIN F660 days days days 27 40% Nitrapyrin, 40% NMP, Liquid >17 Liquid >385 Liquid >351 20% FLOMIN F660 days days days 28 35% Nitrapyrin, 55% NMP, Liquid >17 Liquid >385 Liquid >351 10% FLOMIN F660 days days days 29 35% Nitrapyrin, 30% NMP, Liquid >17 Liquid >385 Liquid >351 35% FLOMIN F660 days days days 30 30% Nitrapyrin, 46.67% NMP, Liquid >357 Liquid >328 23.33% FLOMIN F660 days days 31 45% Nitrapyrin, 30% NMP, 1 day 2 days 25% FLOMIN F660 32 45% Nitrapyrin, 30% NMP, 1 day 1 day 25% FLOMIN F660 33 50% Nitrapyrin, 50% NMP 1 day 1 day 34 45% Nitrapyrin, 45% NMP, 2 days 7 days 10% FLOMIN F660 35 30% Nitrapyrin, 20% NMP, 16 days 16 days 50% FLOMIN F660 36 35% Nitrapyrin, 30% NMP, Liquid >357 Liquid >328 35% FLOMIN F660 days days 37 30% Nitrapyrin, 70% NMP Liquid >357 Liquid >328 days days 38 35% Nitrapyrin, 55% NMP, Liquid >357 Liquid >328 10% FLOMIN F660 days days 39 40% Nitrapyrin, 40% NMP, Liquid >357 Liquid >328 20% FLOMIN F660 days days 40 50% Nitrapyrin, 20% NMP, <1 day 30% FLOMIN F660

[0038] Formulations according to the table above were tested for their stability at 0 C., 10 C., and 15 C. to determine if they would freeze or if any solid would precipitate from the solution at 0 C. or below after being stored at 0 C. or below for at least 14 days.

[0039] A formulation (Examples 1-40) in a sealed jar was placed into a freezer that is set to the desired temperature (0 C., 10 C., and 15 C.). The time when the sample is first placed into the freezing temperature is set to time zero. Samples are monitored daily for solidification by slowly tilting each container to observe for fluidity. Freezing time is based on the time at which a particular formulation appeared to be solidified. Formulations that appear to be solidified are removed to ambient temperature and allowed to thaw. Some samples that are frozen may re-solubilize when the temperature is brought to ambient conditions. Other samples that are frozen may remain as solid after elevating the temperature to ambient. The samples are kept at 0 C., 10 C., and 15 C. for at least 14 days.

Results

[0040] Formulations 6, 10-12, 15, 21, 26-30, and 36-39 remained as a homogeneous solution after at least 357 days at 15 C. The stability test demonstrates that the formulations of entries 6, 10-12, 15, 21, 26-30, and 36-39 can maintain a homogeneous solution for at least 357 days at 15 C. The stability test also shows that the formulations of entries 3 and 14, which each comprise 30% nitrapyrin by weight can maintain a homogeneous solution for at least 27 days at 15 C. Also, the stability test indicates that the formulations of entries 24 and 25, which each comprise 50% and 45% nitrapyrin by weight, respectively, can maintain a homogeneous solution for at least 15 days at 15 C.

Example 4: Concentrated Nitrapyrin and NBPT Formulation

[0041]

TABLE-US-00002 Glycol Ethers AGROTAIN NBPT Propylene (FLOMIN NMP Ultra Green Nitrapyrin (% Glycol F660) (% Blend Dye Entry (% w/w) w/w) (% w/w) (% w/w) w/w) (% w/w) 41 50.00 7.14 11.13 3.10 28.47 0.16 42 50.00 7.14 4.17 1.17 37.36 0.16 43 33.31 4.79 16.11 4.48 41.21 0.10 44 33.31 4.79 2.82 0.78 58.20 0.10

[0042] Formulations 41-44, according to the table above, each include nitrapyrin and, a urease inhibitor, NBPT, in a mixture of solvents, PG, glycol ethers (such as FLOMIN F660) and NMP. These formulations also contained a dye, such as AGROTAIN Ultra Green Blend Dye. These liquid formulations contain a high concentration nitrapyrin, ranging from about 33.3% by wt. to about 50.0% by wt.

[0043] Embodiments of the present disclosure further relate to any one or more of the following paragraphs:

Embodiment 1

[0044] A formulation, comprising: i) nitrapyrin in an amount ranging from about 30% to about 50% by weight; ii) a glycol, a glycol derivative, and/or an alkylene glycol alkyl ether in an amount ranging from about 10% to about 50% by weight; and/or iii) N-methyl-2-pyrrolidinone (NMP) in an amount ranging from about 20% to about 70% by weight; wherein each component is present in amount by weight of the total formulation.

Embodiment 2

[0045] The formulation of Embodiment 1, further comprising a urease inhibitor.

Embodiment 3

[0046] The formulation of any one of Embodiments 1 or 2, further comprising an excipient.

Embodiment 4

[0047] The formulation of any one of Embodiments 1 to 3, further comprising a dye.

Embodiment 5

[0048] A formulation, comprising: i) nitrapyrin in an amount ranging from about 30% to about 50% by weight; ii) a urease inhibitor in an amount ranging from about 1% to about 10% by weight; iii) a glycol, a glycol derivative, and/or an alkylene glycol alkyl ether in an amount ranging from about 3% to about 50% by weight; and/or iv) N-methyl-2-pyrrolidinone (NMP) in an amount ranging from about 20% to about 70% by weight; wherein each component is present in amount by weight of the total formulation.

Embodiment 6

[0049] The formulation of Embodiment 5, further comprising an excipient.

Embodiment 7

[0050] The formulation of any one of Embodiments 5 or 6, further comprising a dye.

Embodiment 8

[0051] The formulation of any one of Embodiments 1 or 5, wherein said glycol or glycol derivative or alkylene glycol alkyl ether is diethylene glycol.

Embodiment 9

[0052] The formulation of any one of Embodiments 1 or 5, wherein said glycol or glycol derivative or alkylene glycol alkyl ether is dipropylene glycol.

Embodiment 10

[0053] The formulation of any one of Embodiments 1 or 5, wherein said glycol or glycol derivative or alkylene glycol alkyl ether is an alkylene glycol alkyl ether selected from diethylene glycol monoethyl ether, diethylene glycol monopropyl ether, diethylene glycol monopentyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monoisobutyl ether, diethylene glycol monohexyl ether, triethylene glycol monomethyl ether, triethylene glycol monopropyl ether, triethylene glycol monobutyl ether, triethylene glycol monopentyl ether, triethylene glycol monoisopropyl ether, triethylene glycol monoisobutyl ether, triethylene glycol monohexyl ether, tetraethylene glycol monomethyl ether, tetraethylene glycol monoethyl ether, tetraethylene glycol monopropyl ether, tetraethylene glycol monobutyl ether, tetraethylene glycol monopentyl ether, tetraethylene glycol monoisopropyl ether, tetraethylene glycol monoisobutyl ether, tetraethylene glycol monohexyl ether, dipropylene glycol monoethyl ether, dipropylene glycol monopropyl ether, dipropylene glycol monobutyl ether, dipropylene glycol monopentyl ether, dipropylene glycol monoisopropyl ether, dipropylene glycol monoisobutyl ether, dipropylene glycol monohexyl ether, tripropylene glycol monoethyl ether, tripropylene glycol monopropyl ether, tripropylene glycol monobutyl ether, tripropylene glycol monopentyl ether, tripropylene glycol monoisopropyl ether, tripropylene glycol monoisobutyl ether, tripropylene glycol monohexyl ether, and combinations thereof.

Embodiment 11

[0054] The formulation of any one of Embodiments 1 or 5, wherein said alkylene glycol alkyl ether is a mixture of triethylene glycol monobutyl ether, tetraethylene glycol monobutyl ether, and diethylene glycol monobutyl ether.

Embodiment 12

[0055] The formulation of Embodiment 11, wherein said mixture of triethylene glycol monobutyl ether, tetraethylene glycol monobutyl ether, and diethylene glycol monobutyl ether alkylene glycol alkyl ether contains 70-80% triethylene glycol monobutyl ether, 15-25% tetraethylene glycol monobutyl ether, and less than 5% diethylene glycol monobutyl ether.

Embodiment 13

[0056] The formulation of any one of Embodiments 2 or 5, wherein the urease inhibitor is N-(n-butyl) thiophosphoric triamide (NBPT).

Embodiment 14

[0057] The formulation of any one of Embodiments 1 or 5, wherein the formulation is stable at 0 C.

Embodiment 15

[0058] The formulation of Embodiment 14, wherein the formulation is stable for 2 weeks.

Embodiment 16

[0059] The formulation of Embodiment 14, wherein the formulation is stable for about 1 month.

Embodiment 17

[0060] The formulation of Embodiment 14, wherein the formulation is stable for about 6 months.

Embodiment 18

[0061] The formulation of Embodiment 14, wherein the formulation is stable for about 1 year.

Embodiment 19

[0062] The formulation of Embodiment 14, wherein the formulation is stable for about 1.5 years.

Embodiment 20

[0063] The formulation of any one of Embodiment 14 to 19, wherein less than about 5% of the total solution is frozen.

Embodiment 21

[0064] The formulation of any one of Embodiment 14 to 19, wherein less than about 5% of total solids crystallize out from solution.

Embodiment 22

[0065] The formulation of any one of Embodiments 1 or 5, wherein the formulation is stable at 10 C.

Embodiment 23

[0066] The formulation of Embodiment 22, wherein the formulation is stable for 2 weeks.

Embodiment 24

[0067] The formulation of Embodiment 22, wherein the formulation is stable for about 1 month.

Embodiment 25

[0068] The formulation of Embodiment 22, wherein the formulation is stable for about 6 months.

Embodiment 26

[0069] The formulation of Embodiment 22, wherein the formulation is stable for about 1 year.

Embodiment 27

[0070] The formulation of Embodiment 22, wherein the formulation is stable for about 1.5 years.

Embodiment 28

[0071] The formulation of any one of Embodiments 22 to 27, wherein less than about 5% of the total solution is frozen.

Embodiment 29

[0072] The formulation of any one of Embodiments 22 to 27, wherein less than about 5% of total solids crystallize out from solution.

Embodiment 30

[0073] The formulation of any one of Embodiments 1 or 5, wherein the formulation is stable at 15 C.

Embodiment 31

[0074] The formulation of Embodiment 30, wherein the formulation is stable for 2 weeks.

Embodiment 32

[0075] The formulation of Embodiment 30, wherein the formulation is stable for about 1 month.

Embodiment 33

[0076] The formulation of Embodiment 30, wherein the formulation is stable for about 6 months.

Embodiment 34

[0077] The formulation of Embodiment 30, wherein the formulation is stable for about 1 year.

Embodiment 35

[0078] The formulation of Embodiment 30, wherein the formulation is stable for about 1.5 years.

Embodiment 36

[0079] The formulation of any one of Embodiments 30 to 35, wherein less than about 5% of the total solution is frozen.

Embodiment 37

[0080] The formulation of any one of Embodiment 30 to 35, wherein less than about 5% of total solids crystallize out from solution.

Embodiment 38

[0081] The formulation of Embodiment 1, wherein nitrapyrin is present in an amount of about 30% by weight and NMP is present in an amount of about 70% by weight.

Embodiment 39

[0082] The formulation of Embodiment 1, wherein nitrapyrin is present in an amount of about 30% by weight; a glycol, a glycol derivative and/or alkylene glycol alkyl ether is present in an amount of about 47% by weight; and NMP is present in an amount of about 23% by weight.

Embodiment 40

[0083] The formulation of Embodiment 36, wherein nitrapyrin is present in an amount of 30.00% by weight; a glycol, a glycol derivative and alkylene glycol alkyl ether is present in an amount of 46.67% by weight; and/or NMP is present in an amount of 23.33% by weight.

Embodiment 41

[0084] The formulation of Embodiment 1, wherein nitrapyrin is present in an amount of about 30% by weight; a glycol, a glycol derivative and/or alkylene glycol alkyl ether is present in an amount of about 35% by weight; and NMP is present in an amount of about 35% by weight.

Embodiment 42

[0085] The formulation of Embodiment 1, wherein nitrapyrin is present in an amount of about 30% by weight; a glycol, a glycol derivative and/or alkylene glycol alkyl ether is present in an amount of about 23% by weight; and NMP is present in an amount of about 47% by weight.

Embodiment 43

[0086] The formulation of Embodiment 39, wherein nitrapyrin is present in an amount of 30.00% by weight; a glycol, a glycol derivative and/or alkylene glycol alkyl ether is present in an amount of 23.33% by weight; and NMP is present in an amount of 46.67% by weight.

Embodiment 44

[0087] The formulation of Embodiment 1, wherein nitrapyrin is present in an amount of about 35% by weight; a glycol, a glycol derivative and/or alkylene glycol alkyl ether is present in an amount of about 10% by weight; and NMP is present in an amount of about 55% by weight.

Embodiment 45

[0088] The formulation of Embodiment 1, wherein nitrapyrin is present in an amount of about 35% by weight; a glycol, a glycol derivative and/or alkylene glycol alkyl ether is present in an amount of about 35% by weight; and NMP is present in an amount of about 30% by weight.

Embodiment 46

[0089] The formulation of Embodiment 1, wherein nitrapyrin is present in an amount of about 40% by weight; a glycol, a glycol derivative and/or alkylene glycol alkyl ether is present in an amount of about 20% by weight; and NMP is present in an amount of about 40% by weight.

Embodiment 47

[0090] The formulation of Embodiment 1, wherein nitrapyrin is present in an amount of about 45% by weight; a glycol, a glycol derivative and/or alkylene glycol alkyl ether is present in an amount of about 25% by weight; and NMP is present in an amount of about 30% by weight.

Embodiment 48

[0091] The formulation of Embodiment 1, wherein nitrapyrin is present in an amount of about 50% by weight, and NMP is present in an amount of about 50% by weight.

Embodiment 49

[0092] The formulation of Embodiment 1, wherein nitrapyrin is present in an amount of about 30% by weight and NMP is present in an amount of about 70% by weight.

Embodiment 50

[0093] The formulation of Embodiment 7, wherein nitrapyrin is present in an amount of about 50% by weight; a glycol, a glycol derivative and/or alkylene glycol alkyl ether is present in an amount of about 14.2% by weight; NMP is present in an amount of about 28.5% by weight; a urease inhibitor is present in an amount of about 7.1% by weight; and a dye is present in an amount of about 0.2% by weight.

Embodiment 51

[0094] The formulation of Embodiment 7, wherein nitrapyrin is present in an amount of about 50% by weight; a glycol, a glycol derivative and/or alkylene glycol alkyl ether is present in an amount of about 5.3% by weight; NMP is present in an amount of about 37.4% by weight; a urease inhibitor is present in an amount of about 7.1% by weight; and a dye is present in an amount of about 0.2% by weight.

Embodiment 52

[0095] The formulation of Embodiment 7, wherein nitrapyrin is present in an amount of about 33.3% by weight; a glycol, a glycol derivative and/or alkylene glycol alkyl ether is present in an amount of about 20.6% by weight; NMP is present in an amount of about 41.2% by weight; a urease inhibitor is present in an amount of about 4.8% by weight; and a dye is present in an amount of about 0.1% by weight.

Embodiment 53

[0096] The formulation of Embodiment 7, wherein nitrapyrin is present in an amount of about 33.3% by weight; a glycol, a glycol derivative and/or alkylene glycol alkyl ether is present in an amount of about 3.6% by weight; NMP is present in an amount of about 58.2% by weight; a urease inhibitor is present in an amount of about 4.8% by weight; and a dye is present in an amount of about 0.1% by weight.

Embodiment 54

[0097] The formulation of any one of the proceeding Embodiments, wherein the formulation comprises a surfactant selected from octylphenol polyether alcohol, sulfosuccinate, naphthalene sulfonate, sulfated ester, phosphate ester, sulfated alcohol, alkyl benzene sulfonate, polycarboxylate, naphthalene sulfonate condensate, phenol sulfonic acid condensate, lignosulfonate, methyl oleyl taurate, polyvinyl alcohol, polysorbates, or any combination thereof.

Embodiment 55

[0098] A method of making a nitrapyrin formulation according to any one of the preceding Embodiment, the method comprising: mixing nitrapyin; at least one of a glycol, a glycol derivative or alkylene glycol alkyl ether; and NMP.

Embodiment 56

[0099] A method of making an incorporated urea-containing fertilizer, the method comprising mixing the formulation according to any one of Embodiments 1 to 54 into a molten urea-containing fertilizer.

Embodiment 57

[0100] A method of fertilizing soil, the method comprising: contacting soil with a formulation according to any one of Embodiment 1 to 45.

Embodiment 58

[0101] The method of Embodiment 57, wherein the formulation is sprayed onto the soil.

Embodiment 59

[0102] The method of Embodiment 57, wherein the formulation of Embodiment 1 is added to the irrigation water of the soil.