Composition comprising an alkyltrhiophosphoric triamide urease inhibitor

Abstract

The present invention relates to a composition comprising a urease inhibitor, in particular a alkylthiophosphoric triamide such as N-(n-butyl)thiophosphoric triamide (NBPT), useful for agricultural compositions, and more particularly fertilizer formulations and its manufacture. It also relates to the agricultural compositions which can be derived therefrom and their use.

Description

[0001] COMPOSITION COMPRISING AN ALKYLTRHIOPHOSPHORIC TRIAMIDE UREASE INHIBITOR

[0002] TECHNICAL FIELD

[0003] The present invention relates to a composition comprising a urease inhibitor, in particular a alkylthiophosphoric triamide such as N-(n-butyl)thiophosphoric triamide (NBPT), useful for agricultural compositions, and more particularly fertilizer formulations and its manufacture. It also relates to the agricultural compositions which can be derived therefrom and their use.

[0004] BACKGROUND ART

[0005] In the agrochemical industry, farmers use various fertilizers to impart macronutrients to plants either by application to the soil or application to plant leaves. Nitrogen, phosphorus, potassium, calcium, magnesium, and sulfur are macronutrients that must be supplied to the plants and soil manually by farmers. In many crops, the amount of nitrogen supplied is critical to the overall quality and growth of the crop. Nitrogen is typically supplied in the form of nitrogenous, i.e., nitrogen precursor-containing, fertilizer compounds, such as urea, ammonium nitrate, or ammonium phosphate fertilizer compounds. Due to the high water solubility of these salts, however, applied nitrogen may be lost due to run-off and leaching of the nitrogenous fertilizer compounds. Once applied, the nitrogenous fertilizer compounds are typically degraded, for example, by microorganisms present in the soil, to nitrogenous species such as NH , NO?', NO?' , and ammonia gas, that may be even more readily lost through evaporation, run-off, and leaching than the fertilizer compounds themselves. If degradation of the fertilizer compounds occurs at a rate that is faster than the nitrogenous degradation products can be used by the plants, then the nitrogen values in the degradation products are at increased risk of being lost.

[0006] Nitrification and / or urease inhibitors are of potential use in delaying degradation of fertilizer compounds and thereby reducing losses of nitrogenous degradation products that would otherwise occur in the absence of the inhibitors. The use of nitrification and / or urease inhibitors in combination with nitrogenous fertilizer compounds tends to increase the amount of time the nitrogen sources remain in the soil and available for absorption by the plants, which tends to increase the effectiveness of the fertilizers and positively impact crop yield and quality. Aqueous end use fertilizer solutions are typically prepared in the field by diluting commercially available concentrated fertilizer compositions with water. Commonly used concentrated fertilizer compositions include concentrated ammonium nitrate compositions, such as, for example, UAN 18, UAN 28, UAN 30 and UAN 32.

[0007] Urease inhibitors can be used with a fertilizer (i.e., incorporated into a urea-containing fertilizer, e.g., urea and urea ammonium nitrate (UAN)) to slow the conversion of urea to ammonia gas and thus slow the loss of ammonia to volatilization, thus making ammonium available to plants in the soil for longer periods of time. The hydrolysis of urea is facilitated by urease enzyme present in the soil. In many crops, the amount of nitrogen supplied is critical to the overall quality and growth of the crop. Nitrogen is supplied in either urea or ammonium forms. Due to the high water solubility of these salts, however, much of the nitrogen applied is lost to run-off and leaching. In ammonium-based products, if the nitrogen is not lost due to leaching or run-off, then ammonium can bind to soil particles and be made available for the plant. Conversion occurring near the surface of the soil, however, does not allow for binding and this ammonia is lost to the atmosphere. Urease inhibitors are used to protect a farmer’s investment in fertilizers by preventing the breakdown of urea by urease, the soil microbe responsible for converting urea to usable ammonia in the soil. This increases the amount of time the nitrogen remains in the soil and is available to the plant for absorption.

[0008] A typical urease inhibitor, alkyl thiophosphoric triamide (for example, N-(n-butyl)- thiophosphoric triamide or otherwise “NBPT”), however, faces drawbacks in its use as NBPT is extremely difficult to handle. NBPT is a sticky, waxy, heat and water sensitive material, which cannot be used in its solid form, as it is used at low concentrations making it difficult to evenly distribute on urea prills (i.e., large granules) and in soil. In order to evenly distribute the NBPT onto the urea, the NBPT should be dispersed into a carrier prior to being sprayed onto the urea. It is known (see for example US10173935) that the use of a solvent system containing the NBPT in a liquid solvent system is capable of distributing the NBPT into granular urea (e.g., urea prills) and into liquid fertilizers containing urea. By introducing the NBPT to liquid fertilizers containing urea (for example, urea-ammonium nitrate solutions or UAN) in a solvent system, the NBPT is capable of being better dispersed in the liquid fertilizer.

[0009] There is a very limited number of solvents available that can solubilize high amounts of NBPT. It has been already reported to use dimethylsulfoxide (DMSO) in order to solubilize N-(n- butyl)-thiophosphoric triamide (NBPT), see for example US10597338. DMSO however, has some drawbacks notably in terms of stability of the solutions obtained and the capability of carrying high loads of urease inhibitor over the whole applicable temperature range. US10487019 proposes phosphoric or thiophosphoric triamide compositions having a concentration range of 35 to 50 wt.% and comprising 5-30 wt% of specific glycol or glycol derivative and 20-50 wt. % of an amide solvent wherein the preferred solvent is n-methylpyrrolidone, which is highly toxic. Thus, the present invention discloses an advantageous composition comprising high loadings of urease inhibitor, which is stable over storage over a large range of temperature, while having a favorable and / or ecological profile and desirable characteristics in terms of low volatility, biodegradability.

[0010] Another problem associated with the use of NBPT is its degradation at higher temperature typically above 45°C. Often times temperature in agricultural fields (e.g. com fields, wheat fields etc..) reach in excess of 35°C and sometimes up to 45°C or higher. For example, at 45°C, NBPT formulated in different solvents changes color in days from colorless to a darker green / brown, followed by sludge / precipitate formation. This it is also desirable to have solvent systems containing urease inhibitor that are stabilized at high temperatures.

[0011] WO2017 / 144698 discloses a method for the manufacture of a liquid composition essentially consisting of an organic solvent of the type glycol and a urease inhibitor of the type phosphoric triamide. The compositions are only able to maintain a low urease inhibitor load and they appear to crystallize at < -10°C and do not appear to present a storage stability at that temperature.

[0012] BRIEF DESCRIPTION

[0013] The present invention makes available new compositions comprising urease inhibitor having improved properties, notably in terms of stability, coloration, odor, toxicity and handling. Further the loading of urease inhibitor can be increased compared to standard formulation.

[0014] A first embodiment of the present invention relates to a composition comprising: i. an alkylthiophosphoric triamide, ii. dimethylsulfoxide (DMSO), and iii. at least one diol selected from the group consisting of 1,3 -propanediol and 1,5 pentanediol.

[0015] Preferably, this first embodiment relates to a composition comprising: i. an alkylthiophosphoric triamide, ii. dimethylsulfoxide (DMSO), and iii. 1,3-propanediol.

[0016] In another embodiment, the present invention relates to an agricultural composition comprising a nitrogenous fertilizer and a composition composition comprising: i. an alkylthiophosphoric triamide, ii. DMSO, and iii. at least one diol selected from the group consisting of 1,3-propanediol and 1,5 pentanediol.

[0017] Preferably, the present invention relates to an agricultural composition comprising a nitrogenous fertilizer and a composition composition comprising: i. an alkylthiophosphoric triamide, ii. DMSO, and iii. 1,3-propanediol.

[0018] In another aspect, the present invention relates to methods for fertilizing target plants, said methods comprising applying an aqueous end use fertilizer composition that comprises (a) one or more nitrogenous fertilizer compounds, (b) a composition comprising i. an alkylthiophosphoric triamide, ii. DMSO, and iii. at least one diol selected from the group consisting of 1,3-propanediol and 1,5 pentanediol.

[0019] Preferably, the present invention relates to methods for fertilizing target plants, said methods comprising applying an aqueous end use fertilizer composition that comprises (a) one or more nitrogenous fertilizer compounds, (b) a composition comprising i. an alkylthiophosphoric triamide, ii. DMSO, and iii. 1,3-propanediol.

[0020] DETAILLED DESCRIPTION

[0021] Throughout the description, the expression “alkyl” means a saturated straight chain, branched chain or cyclic hydrocarbon radical, including but not limited to methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, t-butyl, pentyl, -hexyl and cyclohexyl.

[0022] As used herein, the term "aryl" means a monovalent unsaturated hydrocarbon radical containing one or more six-membered carbon rings in which the unsaturation may be represented by three conjugated double bonds, which may be substituted one or more of carbons of the ring with hydroxy, alkyl, alkenyl, halo, haloalkyl, or amino, including but not limited to, phenoxy, phenyl, methylphenyl, dimethylphenyl, trimethylphenyl, chlorophenyl, trichloromethylphenyl, aminophenyl, and tri styrylphenyl.

[0023] As used herein, the term "alkylene" means a divalent saturated straight or branched chain hydrocarbon radical, such as for example, methylene, dimethylene, trimethylene.

[0024] As used herein, the term "alkoxyl" means an oxy radical that is substituted with an alkyl group, such as for example, methoxyl, ethoxyl, propoxyl, isopropoxyl, or butoxyl, which may optionally be further substituted on one or more of the carbon atoms of the radical.

[0025] As used herein, the term "alkoxyalkyl" means an alkyl radical that is substituted with one or more alkoxy substituents, more typically a (Ci-C22)alkyloxy-(Ci-Ce)alkyl radical, such as methoxymethyl, and ethoxybutyl.

[0026] As used herein, the term "alkenyl" means an unsaturated straight or branched hydrocarbon radical, more typically an unsaturated straight, branched, (which, in one particular embodiment, is C1-C75) hydrocarbon radical, that contains one or more carbon-carbon double bonds, such as, for example, ethenyl, n-propenyl, iso-propenyl.

[0027] As used herein, the term "arylalkyl" means an alkyl group substituted with one or more aryl groups, more typically a (Ci-Cis)alkyl substituted with one or more (Ce-Ci4)aryl substituents, such as, for example, phenylmethyl, phenylethyl, and triphenylmethyl.

[0028] As used herein, the term "aryloxy" means an oxy radical substituted with an aryl group, such as, for example, phenyloxy, methylphenyloxy, isopropylmethylphenyloxy.

[0029] As used herein, the terminology "(Cr-C3)" in reference to an organic group, wherein r and s are each integers, indicates that the group may contain from r carbon atoms to s carbon atoms per group.

[0030] Throughout the description, the expression “comprises” includes the meaning of “consists of’.

[0031] A first embodiment of the present invention relates to a composition comprising: i. at least one urease inhibitor, ii. dimethylsulfoxide (DMSO), and iii. at least one diol selected from the group consisting of 1,3 -propanediol and 1,5 pentanediol, preferably 1,3 -propanediol. According to the present invention, the composition may further comprise at least one quaternary ammonium compound, in particular at least one salt of a quaternary ammonium compound. The quaternary ammonium compound may be selected from tetraalkyl ammonium compounds, preferably wherein the at least one of the alkyl radical comprises at least one hydroxyl group or is selected from the group consisting of methyl, ethyl, n-propyl, iso-propyl, n-butyl, secbutyl, t-butyl, pentyl, -hexyl and cyclohexyl. Non-limiting examples of quaternary ammonium compounds include chloline derivatives and tributylmethylammonium chloride (CAS 56375-79- 2). Choline derivatives include chlorine as such, a salt thereof and any chemically modified forms thereof. In particular chlorine derivative may be a choline salt, such as choline halide, in particular choline chloride. In a preferred embodiment, the composition of the present invention further comprises choline chloride.

[0032] Accordingly, according to a specific embodiment, the present invention relates to a composition comprising: i. at least one urease inhibitor, ii. dimethylsulfoxide (DMSO), iii. at least one diol selected from the group consisting of 1,3 -propanediol and 1,5 pentanediol, preferably 1,3-propanediol, and iv. optionally at least one quaternary ammonium compound as defined herein.

[0033] In the present invention, the at least one urease inhibitor may be selected from the group consisting of alkylthiophosphoric triamide. Non-limiting examples of alkylthiophosphoric triamide urease inhibitors comprise any one of n-butyl thiophosphoric triamide (NBPT), n-propyl thiophosphoric triamide and cyclohexyl thiophosphoric triamide.

[0034] N-(n-butyl)-thiophosphoric triamide (“NBPT”) is particularly preferred as urease inhibitor.

[0035] The purity of the urease inhibitor, in particular the alkylthiophosphoric triamide and more particularly the NBPT used in the compositions according to the invention is generally at least of 90% by weight, preferably at least of 95% by weight, more preferably at least of 97% by weight, and still more preferably at least of 98% by weight.

[0036] In general, the at least one urease inhibitor may be present in an amount higher than about 35 wt%, preferably higher than about 40 wt%, more preferably higher than about 45 wt% and still more preferably higher than about 50 wt%. In general, the at least one urease inhibitor may be present in an amount lower than about 75 wt%, preferably lower than about 65 wt%, more preferably lower than about 60 wt% and still more preferably lower than about 55wt%.

[0037] The composition of the present invention comprises at least one diol selected from the group consisting of 1,3 -propanediol (CAS 504-63-2) and 1,5 pentanediol (CAS 111-29-5).

[0038] In general, the at least one diol selected from the group consisting of 1,3 -propanediol and 1,5 pentanediol may be present in an amount comprised between about 10 wt% and about 35 wt%, preferably comprised between about 12 wt% and about 30 wt%. According to a particular embodiment, the at least one diol is 1,3-propanediol. In such embodiment wherein the at least one diol is 1,3-propanediol, the 1,3-propanediol may be present in an amount comprised between about 10 wt% and about 35 wt%, preferably 15 about wt% and 30 about wt%, more preferably between about 20 wt% and about 30 wt%, for example about 21 wt%, about 22 wt%, about 23 wt%, about 24 wt%, about 25 wt%, about 26 wt%, about 27 wt%, about 28 wt%, about 29 wt%. According to another embodiment, the at least one diol is 1,5 -pentanediol. In such embodiment wherein the at least one diol is 1,5-pentanediol, the 1,5-pentanediol may be present in an amount comprised between about 10 wt% and about 35 wt%, preferably about 12 wt% and 20 wt%.

[0039] According to the present invention, the at least one quaternary ammonium compound, preferably choline chloride may be present in an amount comprised between 0wt% and 10 wt%, preferably comprised between about 1 wt% and about 8 wt%, for example about 4 wt%, about 5 wt%, about 6 wt%, about 7 wt%.

[0040] In general, the at least one diol selected from the group consisting of 1,3-propanediol and 1,5 pentanediol and at least one quaternary ammonium compound, preferably choline chloride may be present in a total amount comprised between about 10 wt% and about 40 wt%, preferably comprised between about 12wt% and about 35wt%, for example about about 16wt% or about about 30wt%. According to a preferred embodiment, 1,3-propanediol and at least one quaternary ammonium compound, preferably choline chloride may be present in a total amount comprised between about 10 wt% and about 40 wt%, preferably comprised between about 12wt% and about 35wt%, for example about 16wt% or about 30wt%.

[0041] In general, the DMSO may be present in an amount from about 10 wt% to about 40 wt%, preferably from about 20 wt% to about 35 wt%. According to a preferred embodiment, the DMSO is present in an amount superior or equal to 28.5 wt. %, preferably from 28.5 wt. % to 40 wt. %, more preferably from 28.5 wt. % to 35 wt. %.

[0042] According to a particular embodiment, the invention relates to a composition comprising: i. NBPT, ii. dimethylsulfoxide (DMSO), and iii. 1,3-propanediol and optionally chlorine chloride.

[0043] According to another particular embodiment, the invention relates to a composition comprising: i. NBPT, ii. dimethylsulfoxide (DMSO), and iii. 1,5-pentanediol and chlorine chloride.

[0044] According to the present invention, the composition may further comprise an odor masking agent. Suitable odor masking agents include but are not limited to methyl acetate, ethyl acetate, cyclohexyl acetate, benzyl acetate, isoamyl acetate, geranyl acetate, hexyl acetate, octyl acetate, phenylethyl acetate, methyl butyrate, ethyl butyrate, 2-methylbutyl butyrate, isoamyl butyrate, methyl formate, methyl propionate, pentyl butyrate, 2-methylbutyl 2 -methylbutyrate, ethyl methylphenylglycidate, dimethyl phthalate, or diethyl malonate. Suitable odor masking agents include but are not limited to: citral, citronellol, camphor, cedrene, carvone, dipentene, eucalyptol, geraniol, a-ionone, linalool, limonene, menthol, myrcene, neral, nerolidol, a-pinene, P-pinene, a- phellandrene, P-phellandrene, terpineol, a-terpinene, P-terpinene, or thujone. Suitable odor masking agents include but are not limited to: acetaldehyde, anisic aldehyde, benzaldehyde, butyraldehyde, cinnamaldehyde, capraldehyde, cuminaldehyde, decanal, hexanal, hexyl cinnamaldehyde, isomenthone, isovaleraldehyde, menthone, propionaldehyde or valeraldehyde. Suitable odor masking agents include but are not limited to: benzyl alcohol, cis-3-hexen-l-ol, furaneol, 1 -hexanol, phenyl ethyl alcohol; 4-allylanisole, anisole, anethole, eugenol, y-decalactone, y-nonalactone, thymol dihydrojasmone, vanillin, mint, oil Japanese cherry or lactones. In one embodiment, the odor masking agent is chosen from at least one of isoamyl butyrate, 4- allylanisole, Limonene, Terpineol , terpenes, 4-(2,6,6-Trimethyl-2-cyclohexenyl)-3-buten-2-one, Benzaldehyde, Diethyl Malonate, Cyclohexyl acetate, Anisole, a-Ionone, mint, oil Japanese cherry and rose ketones. In one embodiment, the odor-masking agent is isoamyl butyrate. In some embodiments, an amount of from 1 wt% to 3 wt% of the odor masking agent (for example, isoamyl butyrate) is added to the liquid formulations of the present invention.

[0045] According to the present invention, the composition may further comprise at least one nitrification inhibitor, preferably selected from the group consisting of N-2,5-dichlorophenyl succinamic acid, dicyandiamide (DCD), zinc-ethylene-bis-dithiocarbamate, 2,4,6-triehloroaniline, pentachlorophenol, thio-urea, ammonium thiosulphate (ATS) or 3,4-dimethypyrazole phosphate (DMPP), most preferably the nitrification inhibitor is dicyandiamide.

[0046] In certain aspects, the composition according to the invention may comprise a dye. Suitable dyes are commercially available, one example is Oracet ® Blue 780 F or Sensient Blue LF. It has been found that the compositions according to the invention are compatible with dyes used in agricultural compositions. If a dye is used, its content is generally equal to or lower than 1% wt., preferably equal to or lower than 0.5% wt. relative to the total weight of the composition. If a dye is used, its content is generally sufficient to impart the desired coloration, for example equal to or more than 0.1% wt. relative to the total weight of the composition.

[0047] Without wishing to be bound by any theory, it is believed that the use of at least one diol according to the present invention, notably of 1,3-propandiol, improves the stability of the urease inhibitor. Advantageously said combination further improves color stability and avoids unwanted smell, odor and or toxic gases (H2S, DMS or DMDS), known to occur over storage of NBPT with DMSO.

[0048] Further, the combination of at least one diol, notably of 1,3 -propanediol, and at least one quaternary ammonium compound significantly improves stability of the urease inhibitor, especially at high concentration (by weight) of urease inhibitor at low and at high temperature compared to control. Advantageously said combination further improves color stability and avoids unwanted smell, odor and or toxic gases (H2S, DMS or DMDS), known to occur over storage of NBPT with DMSO.

[0049] Advantageously, the compositions of the present invention remains flowable after storage at -5°C for 9 weeks.

[0050] Advantageously, the compositions of the present invention are substantially not discolored upon heating at temperature up to 54°C for 2 weeks. Advantageously, the compositions of the present invention do not precipitate upon heating at temperature up to 54°C for 2 weeks.

[0051] The invention also relates to an agricultural composition comprising a composition according to the present invention and a nitrogenous fertilizer. Non-limiting examples of nitrogenous fertilizer include urea, ammonium nitrate or ammonium phosphate fertilizers. Particular nitrogenous fertilizer compositions which can be included in the agricultural composition according to the invention include concentrated ammonium nitrate compositions, such as UAN 18, UAN 28, UAN 30 or UAN 32.

[0052] A particular embodiment of the agricultural composition according to the invention concerns an end-use composition. In one embodiment, the end use composition is a solid end use composition comprising a solid nitrogenous fertilizer and the composition of the present invention. The end-use composition may be in solid state, for example in particulate or granular form or as a pellet, which comprises the agricultural composition according to the invention. More particularly, the end-use composition may comprise a core of nitrogenous fertilizer, as described above and a coating comprising the composition according to the invention. In another embodiment, the end use composition is a liquid end use composition comprising a solid nitrogenous fertilizer and the composition of the present invention. In that case, it generally comprises or consists of a mixture or blend of a composition of the invention and of a liquid fertilizer, which can be in particular a concentrated ammonium nitrate composition as cited above. In that aspect, the amount of composition according to the invention may generally be from about 0.05 wt. % to about 0.50 wt. % relative to the total weight of the end-use composition.

[0053] The invention further relates to a method of making a solid or liquid en use composition comprising contacting one or more nitrogenous fertilizer compounds with a composition of the present invention.

[0054] In another aspect, described herein are methods of making an aqueous end-use fertilizer composition comprising contacting one or more nitrogenous fertilizer compounds with an agricultural composition according to the invention and an aqueous medium, preferably water.

[0055] In another aspect, described herein are methods for fertilizing target plants, wherein the end-use composition according to the invention is applied to target plants or to an environment for the target plants. The end-use composition, in particular in its liquid state, can be used diluted with any appropriate solvent, such as water. The invention also concerns a process for manufacturing the composition according to the invention or the agricultural composition according to the invention which comprises mixing a urease inhibitor, in particular an alkylthiophosphoric triamide type, DMSO, at least one diol selected from the group consisting of 1,3 -propanediol and 1,5-pentanediol, notably 1,3- propanedidol, and optionally at least one quaternary ammonium compound. According to a preferred embodiment, the at least one diol, notably 1,3 -propanediol, is mixed with the at least one quaternary ammonium compound to form a homogeneous phase, then DMSO is added followed by addition of the at least one urease inhibitor. If appropriate, the process according to the invention comprises adding further functional additives such as for example one or more stabilizers and / or a dye and / or an odor masking agent.

[0056] Preferably, in the process according to the invention the mixing forms a homogeneous liquid phase. This is advantageous in terms of processing and storage of the composition while maintaining an adequate physical and chemical stability of the composition.

[0057] In another aspect, the present invention relates to the use of a diol selected from the group consisting of 1,3 -propanediol and 1,5-pentanediol, notably 1,3 -propanediol, and optionally chlorine chloride for stabilizing a composition comprising a urease inhibitor and DMSO wherein the urease inhibitor is preferably an alkylthiophosphoric triamide, more preferably NBPT.

[0058] Should the disclosure of any patents, patent applications, and publications which are incorporated herein by reference conflict with the description of the present application to the extent that it may render a term unclear, the present description shall take precedence.

[0059] The examples hereafter are intended to further illustrate the invention without however limiting its scope.

[0060] EXAMPLES

[0061] Examples 1 to 23

[0062] Compositions according to the present invention and comparative examples were prepared by mixing a diol with choline chloride if required. This composition is stirred until dissolution of the choline chloride. Then DMSO is added and mixed until homogeneous clear mixture is observed. NBPT is then added and stirring is continued until homogenous clear liquid is obtained. Dye and / or masking agent are added according to the Table 1. Table 1 polyethyleneimine having a weight-average molecular weight equal to 600 g.mol'1 * 1,3-propanediol, ** Propylene glycol (CAS 57-55-6), *** 1,5-pentanediol, **** Tiethylene glycol

[0063] The stability of the compositions was analyzed: - After storage for 9 weeks at -5°C (1), or at 0°C (2).

[0064] After heating for 2 weeks at 54°C.

[0065] The results of stability are shown in Table 2. Table 2

[0066] The degradation of the NBPT is the formulation of example 3, 6, 10, 21 and 22 was also analysed through the formation of an odorous degradation product: dimethylsulfide (DMS). The formation of the DMS was measured after a period of 2 or 4 weeks at varying high temperature. The Results are shown in Table 3.

[0067] Table 3 The results show that the formulations according to the present invention improves stability and avoids unwanted smell, odor by preventing the formation of DMS.

Claims

CLAIMS1. A composition comprising: i. at least one urease inhibitor, ii. dimethylsulfoxide (DMSO), and iii. at least one compound selected from the group consisting of 1,3 -propanediol and 1,5 pentanediol.

2. The composition according to any of the preceding claims further comprising a quaternary ammonium compound, preferably choline chloride.

3. The composition according to claim 1 wherein the urease inhibitor is an alkylthiophosphoric triamide, preferably n-(n-butyl)-thiophosphoric triamide (NBPT).

4. The composition according to any of the preceding claims comprising: i. NBPT, ii. dimethylsulfoxide (DMSO), and iii. 1,3-propanediol and optionally chlorine chloride.

5. The composition according to any of the preceding claims comprising: i. NBPT, ii. dimethylsulfoxide (DMSO), and iii. 1,5-pentanediol and chlorine chloride.

6. The composition according to any of the preceding claims further comprising an odor masking agent.

7. The composition according to any of the preceding claims wherein the at least one urease inhibitor is present in an amount higher than about 35 wt%, preferably higher than about 40 wt%, more preferably higher than about 45 wt% and still more preferably higher than about 50 wt%.

8. The composition according to any of the preceding claims wherein the at least one urease inhibitor is present in an amount lower than about 75 wt%, preferably lower than about 65%, more preferably lower than about 60wt% and still more preferably lower than about 55wt%.

9. The composition according to any of the preceding claims wherein the at least one compound selected from the group consisting of 1,3-propanediol and 1,5 pentanediol is present in an amount comprised between about 10 wt% and 35 about wt%, preferably comprised between about 12 wt% and about 30wt%.

10. The composition according to any of the preceding claims wherein the quaternary ammonium compound, preferably choline chloride is present in an amount comprised between 0 wt% and about 10 wt%, preferably comprised between about 1 wt% and about 8 wt%.

11. The composition according to any of the preceding claims wherein the at least one compound selected from the group consisting of 1,3-propanediol and 1,5 pentanediol and the quaternary ammonium compound, preferably choline chloride are present in a total amount comprised between about 10 wt% and about 40 wt%, preferably comprised between about 12wt% and about 35 wt%, for example about about 16 wt% or about 30wt%.

12. The composition according to any of the preceding claims further comprising a nitrification inhibitor.

13. An agricultural composition comprising: a. a nitrogenous fertilizer, and b. a composition as defined in claims 1 to 12.

14. A method of making a solid or concentrated liquid fertilizer composition comprising contacting one or more nitrogenous fertilizer compounds with a composition as defined in claims 1 to 12.

15. A liquid end-use composition comprising a liquid nitrogenous fertilizer and the composition according to anyone of claims 1 to 12.

16. A solid end-use composition comprising a solid nitrogenous fertilizer and the composition according to anyone of claims 1 to 12, preferably comprising a core of nitrogenous fertilizer and a coating comprising the composition according to anyone of claims 1 to 12.

17. A method for fertilizing target plants, wherein the end-use composition according to claim 15 or 16 is applied to target plants or to an environment for the target plants.

18. Use of a diol selected from the group consisting of 1,3-propanediol and 1,5-pentanediol and optionally chlorine chloride for stabilizing a composition comprising a urease inhibitor and DMSO wherein the urease inhibitor is preferably an alkylthiophosphoric triamide, more preferably NBPT.

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