WO2015001391A1

WO2015001391A1 - Compositions with improved urease-inhibiting effect comprising (thio)phosphoric acid triamide and further compounds

Info

Publication number: WO2015001391A1
Application number: PCT/IB2013/055484
Authority: WO
Inventors: Karl-Heinrich Schneider; Claudia Klodwig; Gregor Pasda; Alexander Wissemeier; Daniella LOHE; Achim Reddig; Christian Carlos MIYAGAWA; Wolfram Zerulla; Steffen Tschirschwitz; Ralf-Thomas Rahn; Ansgar Gereon Altenhoff; Stephan Hüffer
Original assignee: Basf Se; Basf (China) Company Limited
Priority date: 2013-07-04
Filing date: 2013-07-04
Publication date: 2015-01-08
Also published as: UY35645A; AR097136A1

Abstract

An composition comprising: (A)a mixture comprising at least one(thio)phosphoric acid triamide according to the general formula (I): R¹R²N–P(X)(NH₂)₂, wherein X is oxygen or sulfur; R¹ is a C₁ to C₂₀ alkyl, C₃ to C₂₀ cycloalkyl, C₆ to C₂₀ aryl, or dialkylaminocarbonyl group; R² is H, or R¹ and R² together with the nitrogen atom linking them define a 5-or 6-membered saturated or unsaturated heterocyclic radical, which optionally comprises or 2 further heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, and (C) at least one amine selected from the group consisting of (C1) a polymeric polyamine, and (C2) an amine containing not more than one amino group and at least three alkoxy- or hydroxy-substituted C₂ to C₁₂ alkyl groups R²¹, wherein at least one of the groups R²¹ is different to the other groups R²¹, and (C3) an amine containing not more than one amino group and at least two alkoxy- or hydroxy-substituted C₂ to C₁₂ alkyl groups R²², wherein at least one of the groups R²² bears the alkoxy or hydroxy substituent at a secondary or tertiary carbon atom and wherein at least one of the groups R²² is different to the other group(s) R²², and (C4) an amine containing at least one saturated or unsaturated C₈ to C₄₀ alkyl group R²³, and (C5) a saturated or unsaturated heterocyclic amine which contains at least one oxygen atom as ring atom and which does not contain a further alkoxy group.

Description

Compositions with improved urease-inhibiting effect comprising (thio)phosphoric acid triamide and further compounds

Description

Field of the Invention

This invention essentially relates to compositions with improved urease-inhibiting effect comprising (thio)phosphoric acid triamide and further compounds and the use of such compositions as additive or coating material for nitrogen-containing fertilizers.

Description of the Prior Art

Worldwide, the predominant and further-increasing amount of the nitrogen used for fertilizing is employed in the form of urea or urea-containing fertilizers. Urea itself, however, is a form of nitrogen which is absorbed very little if at all, being hydrolyzed relatively rapidly by the enzyme urease, which is present ubiquitously in the soil, to form ammonia and carbon dioxide. In this process, in certain circumstances, gaseous ammonia is emitted to the atmosphere, and is then no longer available in the soil for the plants, thereby lowering the efficiency of fertilization.

It is known that the degree of utilization of the nitrogen when using urea-containing fertilizers can be improved by spreading urea-containing fertilizers together with substances which are able to inhibit or decrease the enzymatic cleavage of urea (for a general review, see Kiss, S. Simihaian, M. (2002) Improving Efficiency of Urea Fertilizers by Inhibition of Soil Urease Activity, ISBN 1 -4020-0493-1 , Kluwer Academic Publishers, Dordrecht, The Netherlands). Among the most potent known urease inhibitors are N-alkylthiophosphoric acid triamides and N- alkylphosphoric acid triamides, which are described in EP 0 119 487, for example.

Additionally, mixtures of N-alkylthiophosphoric acid triamides such as N-(n-butyl)thiophosphoric acid triamide (NBPT) and N-(n-propyl)thiophosphoric acid triamide (NPPT) can be used. The mixtures and their preparation are described in US 2010/218575 A1 , for example.

These urease inhibitors are described in U.S. Pat. No. 4,530,714, for example. In order for this class of compound to be able to act as a urease inhibitor, there must first be a conversion to the corresponding oxo form. That form reacts subsequently with the urease, causing its inhibition.

It is advisable to apply the urease inhibitors together with the urea onto or into the soil, since this ensures that the inhibitor comes into contact, together with the fertilizer, with the soil. The urease inhibitor may be incorporated in the urea by, for example, dissolving it into the melt prior to urea granulation or prilling. A process of this kind is described in U.S. Pat. No. 5,352,265, for example. A further option is to apply the urease inhibitor to the urea granules or prills, in the form of a solution, for example. Corresponding processes for application, and suitable solvents, are described in US 2010/218575 A1 , for example. Other suitable additives, for example amines selected from me- thyldiethanolamine, tetrahydroxypropylethylenediamine, trimethylaminoethylethanolamine, N,N,N',N'-tetramethyl-1 ,6-hexanediamine, N,N',N"-tris(dimethylaminopropyl)hexahydrotriazine, and 2,2'-dimorpholinyldiethyl ether, are described in US 201 1/0154874 A1.

The storage life of the urease inhibitor is limited. The higher the temperature, the shorter the storage life. If, for example, urea is stored under tropical conditions, a major part of the urease inhibitor has undergone decomposition, generally, after about four weeks of storage. If the ure- ase inhibitor is introduced into the urea melt, the decomposition is less. For the commercialization of the urea stabilized with the urease inhibitor, however, it is often vital to apply the urease inhibitor to urea and to store the treated fertilizer until the time of its spreading to the soil.

Objects of the invention

One of the objects of the present invention was to provide a composition containing (thio)phosphoric acid triamide which

(i) enhances the stability of the (thio)phosphoric acid triamide(s), and/or

(ii) has a relatively long storage life, particularly before being applied to or coated on nitrogen-containing fertilizers, and/or

(iii) enhances the stability of the (thio)phosphoric acid triamide particularly when applied to or coated on nitrogen-containing fertilizers such as urea, and/or

(iv) protects the (thio)phosphoric acid triamide applied to or coated on nitrogen- containing fertilizers such as urea from decomposition or loss, and/or

(v) is toxicologically unobjectionable, and/or

(vi) does not adversely affect the urease-inhibiting effect and/or activity of the (thio)phosphoric acid triamide, and/or

(vii) can be easily and safely packaged, transported and shipped, even in large quantities,

(viii) can be easily and safely handled and applied for soil treatment, even in large quantities. ary of the invention Accordingly, a composition (Q1 ) was found which comprises:

(A) a mixture comprising at least one (thio)phosphoric acid triamide according to the general formula (I)

R R²N-P(X)(NH₂)₂ ,

wherein

X is oxygen or sulfur;

R¹ is a Ci to C20 alkyl, C3 to C20 cycloalkyl, Ce to C20 aryl, or dialkylaminocarbonyl group;

R² is H, or R¹ and R² together with the nitrogen atom linking them define a 5- or 6-membered saturated or unsaturated heterocyclic radical, which optionally comprises 1 or 2 further heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur,

and

(B) an aromatic alcohol according to the general formula (II) .

R -C(R¹²)(R¹³)-OH ,

in an amount of more than 10 wt.% (wt.% stands for "percent by weight") based on the total weight of the composition (Q1 ),

wherein

R¹¹ is aryl or alkylaryl;

R¹² is H or alkyl;

R¹³ is H or alkyl. Accordingly, a further composition (Q2) was found which comprises:

R R²N-P(X)(NH₂)₂ ,

wherein

X is oxygen or sulfur;

R² is H, or

R¹ and R² together with the nitrogen atom linking them define a 5- or 6-membered satu- rated or unsaturated heterocyclic radical, which optionally comprises 1 or 2 further heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur,

and

(C) at least one amine selected from the group consisting of

(C1 ) a polymeric polyamine, and

(C2) an amine containing not more than one amino group and at least three alkoxy- or hydroxy-substituted C2 to C12 alkyl groups R²¹ , wherein at least one of the groups R²¹ is different to the other groups R²¹ , and

(C3) an amine containing not more than one amino group and at least two alkoxy- or hy- droxy-substituted C2 to C12 alkyl groups R²², wherein at least one of the groups R²² bears the alkoxy or hydroxy substituent at a secondary or tertiary carbon atom and wherein at least one of the groups R²² is different to the other group(s) R²², and

(C4) an amine containing at least one saturated or unsaturated Ce to C40 alkyl group R²³, and

(C5) a saturated or unsaturated heterocyclic amine which contains at least one oxygen atom as ring atom and which does not contain a further alkoxy group.

Accordingly, yet a further composition (Q3) was found which comprises: (A) a mixture comprising at least one (thio)phosphoric acid triamide according to the general formula (I)

R R²N-P(X)(NH₂)₂ ,

wherein

X is oxygen or sulfur;

R² is H , or

R¹ and R² together with the nitrogen atom linking them define a 5- or 6-membered saturated or unsaturated heterocyclic radical, which optionally comprises 1 or 2 further heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur,

and

(D) at least one amide according to the general formula (III)

R³¹CO-N R³²R³³

wherein

R³¹CO is an acyl radical having 1 to 22 carbon atoms,

R³² is hydrogen or alkyl, and

R³³ is hydrogen or alkyl, or

R³² and R³³ together with the nitrogen atom linking them define a 5- or 6-membered saturated or unsaturated heterocyclic radical, which optionally comprises 1 or 2 further heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur. In addition, a process for treating the soil comprising applying the compositions of the invention into the soil in-furrow and/or as side dress and/or as broadcast was found.

Moreover, the use of the compositions of the invention as additive or coating material for nitrogen-containing fertilizers has been found.

Preferred embodiments are explained in the claims and the specification. It is understood that combinations of preferred embodiments are within the scope of the present invention.

The term "at least one" is to be understood as 1 , 2, 3 or more. A mixture comprising at least one amine refers for example to a mixture comprising 1 , 2, 3 or more amines.

The term "soil" is to be understood as a natural body comprised of living (e.g. microorganisms (such as bacteria and fungi), animals and plants) and non-living matter (e.g. minerals and organic matter (e.g. organic compounds in varying degrees of decomposition), liquid, and gases) that occurs on the land surface, and is characterized by soil horizons that are distinguishable from the initial material as a result of various physical, chemical, biological, and anthropogenic processes. From an agricultural point of view, soils are predominantly regarded as the anchor and primary nutrient base for plants (plant habitat). The term "fertilizer" is to be understood as chemical compounds applied to promote plant and fruit growth. Fertilizers are typically applied either through the soil (for uptake by plant roots) or by foliar feeding (for uptake through leaves). The term "fertilizer" can be subdivided into two major categories: a) organic fertilizers (composed of decayed plant/animal matter) and b) inor- ganic fertilizers (composed of chemicals and minerals). Organic fertilizers include manure, slurry, worm castings, peat, seaweed, sewage, and guano. Green manure crops are also regularly grown to add nutrients (especially nitrogen) to the soil. Manufactured organic fertilizers include compost, blood meal, bone meal and seaweed extracts. Further examples are enzymatically digested proteins, fish meal, and feather meal. The decomposing crop residue from prior years is another source of fertility. In addition, naturally occurring minerals such as mine rock phosphate, sulfate of potash and limestone are also considered inorganic fertilizers. Inorganic fertilizers are usually manufactured through chemical processes (such as the Haber-Bosch process), also using naturally occurring deposits, while chemically altering them (e.g. concentrated triple superphosphate). Naturally occurring inorganic fertilizers include Chilean sodium nitrate, mine rock phosphate, and limestone.

"Manure" is organic matter used as organic fertilizer in agriculture. Depending on its structure, manure can be divided into liquid manure, semi-liquid manure, stable or solid manure and straw manure. Depending on its origin, manure can be divided into manure derived from animals or plants. Common forms of animal manure include feces, urine, farm slurry (liquid manure) or farmyard manure (FYM) whereas FYM also contains a certain amount of plant material (typically straw), which may have been used as bedding for animals. Animals from which manure can be used comprise horses, cattle, pigs, sheep, chickens, turkeys, rabbits, and guano from seabirds and bats. The application rates of animal manure when used as fertilizer highly depends on the origin (type of animals). Plant manures may derive from any kind of plant whereas the plant may also be grown explicitly for the purpose of plowing them in (e.g. leguminous plants), thus improving the structure and fertility of the soil. Furthermore, plant matter used as manure may include the contents of the rumens of slaughtered ruminants, spent hops (left over from brewing beer) or seaweed.

The compositions of the invention are referred to as the compositions (Q1 ), (Q2), and (Q3) in the following. The composition (Q1) comprises (A) and (B) - latter in an amount of more than 10wt.% based on the total weight of (Q1) - and optionally further components as described below. The composition (Q2) comprises (A) and (C) and optionally further components as de- scribed below. The composition (Q3) comprises (A) and (D) and optionally further components as described below.

According to the invention, the compositions (Q1), (Q2), and (Q3) comprises - as one of their essential components -

R ²N-P(X)(NH₂)₂ , wherein

X is oxygen or sulfur;

R² is H, or

R¹ and R² together with the nitrogen atom linking them define a 5- or 6-membered saturated or unsaturated heterocyclic radical, which optionally comprises 1 or 2 further heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur.

X in the general formula (I) of (A) is preferably sulfur.

R¹ in the general formula (I) of (A) is preferably Ci-C2o-alkyl, more preferably Ci-Cio-alkyl, most preferably C2-C7 alkyl, for example C3-C4 alkyl.

Examples of alkyl groups are methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert- butyl, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, 2-methylpentyl, heptyl, octyl, 2-ethylhexyl, isooctyl, nonyl, isononyl, decyl and isodecyl. Examples of cycloalkyl groups are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cyclooctyl, examples of aryl groups are phenyl or naph- thyl. Examples of heterocyclic radicals R1 R2N- are piperazinyl, morpholinyl, pyrrolyl, pyrazolyl, triazolyl, oxazolyl, thiazolyl or imidazolyl groups.

According to one embodiment, (A) comprises N-n-butylthiophosphoric acid triamide (NBPT) and/or N-n-propylthiophosphoric acid triamide (NPPT), preferably NBPT and NPPT.

According to another embodiment, (A) comprises at least two different (thio)phosphoric acid triamides having structures of the general formula (I) and wherein said at least two different (thio)phosphoric acid triamides differ in at least one of radicals R¹ or R², and preferably, one of said at least two different (thio)phosphoric acid triamides is N-n-butylthiophosphoric acid tri- amide (NBPT), and more preferably, the other of said at least two different (thio)phosphoric acid triamides is selected from the group consisting of N-cyclohexyl-, N-pentyl-, N-isobutyl- and N-n- propylphosphoric acid triamide and -thiophosphoric acid triamide. Especially preferred are mixtures (A) which comprise NBPT in amounts of from 40 to 95 wt.%, most preferably from 60 to 85% wt.%, particularly preferably from 72 to 80 wt.%, in each case based on the total weight of (A).

Generally, the mixture (A) can be contained in varying amounts in the composition (Q1 ), (Q2), or (Q3). Preferably, the amount of (A) is not more than 85 wt.% (wt.% stands for "percent by weight"), more preferably not more than 60 wt.%, most preferably not more than 45 wt.%, most particularly preferably not more than 35 wt.%, particularly not more than 30 wt.%, for example not more than 27 wt.%, based on the total weight of the composition (Q1 ), (Q2), or (Q3). Preferably, the amount of (A) is at least 1 wt.%, more preferably at least 4 wt.%, most preferably at least 10 wt.%, most particularly preferably at least 15 wt.%, particularly at least 20 wt.%, for example at least 23 wt.%, based on the total weight of the composition (Q1 ), (Q2), or (Q3).

According to the invention, the composition (Q1) comprises - as one of its essential compo- nents -

(B) an aromatic alcohol according to the general formula (II)

R -C(R¹²)(R¹³)-OH ,

in an amount of more than 10 wt.% based on the total weight of the composition (Q1 ), wherein

R¹¹ is aryl or alkylaryl;

R¹² is H or alkyl;

R¹³ is H or alkyl.

The compositions (Q2) and (Q3) can further optionally comprise

(B) an aromatic alcohol according to the general formula (II)

R -C(R¹²)(R¹³)-OH ,

wherein

R¹¹ is aryl or alkylaryl;

R¹² is H or alkyl;

R¹³ is H or alkyl.

The aromatic alcohol (B) is preferably used as solvent in the composition (Q1 ). If present, the aromatic alcohol (B) is preferably used as solvent in the compositions (Q2), or (Q3). According to one embodiment, R¹² in the general formula (I I) of (B) is C1-C40 alkyl, preferably Ci to C20 alkyl, more preferably Ci to C10 alkyl, most preferably Ci to C₅ alkyl. According to another embodiment, R¹³ in the general formula (I I) of (B) is C1-C40 alkyl, preferably Ci to C20 alkyl, more preferably Ci to C10 alkyl, most preferably Ci to C₅ alkyl. According to another embodiment, R¹² in the general formula (I I) of (B) is H. According to another embodiment, R¹³ in the general formula (I I) of (B) is H. According to another embodiment, R¹³ in the general formula (I I) of (B) is H.

According to one embodiment, R¹¹ in the general formula (I I) of (B) is aryl. According to another embodiment, R¹¹ in the general formula (I I) of (B) is phenyl, naphthyl, pyridyl, or pyrrolyl, pyra- zolyl, triazolyl, oxazolyl, thiazolyl or imidazolyl. According to another embodiment, R¹¹ in the general formula (I I) of (B) is phenyl.

According to one embodiment, (B) is benzyl alcohol.

Generally, the aromatic alcohol (B) can be contained in any amounts greater than 10 wt.% in the composition (Q1 ) based on the total weight of the composition (Q1 ). Preferably, the amount of (B) is not more than 99 wt.% (wt.% stands for "percent by weight"), more preferably not more than 93 wt.%, most preferably not more than 87 wt.%, most particularly preferably not more than 80 wt.%, particularly not more than 75 wt.%, for example not more than 70 wt.%, based on the total weight of the composition (Q1). Preferably, the amount of (B) is at least 13 wt.%, more preferably at least 20 wt.%, most preferably at least 35 wt.%, most particularly preferably at least 45 wt.%, particularly at least 55 wt.%, for example at least 60 wt.%, based on the total weight of the composition (Q1 ).

According to another embodiment, the amount of (B) is preferably not more than 78 wt.%, more preferably not more than 67 wt.%, most preferably not more than 61 wt.%, most particularly preferably not more than 56 wt.%, particularly not more than 53 wt.%, for example not more than 50 wt.%, based on the total weight of the composition (Q1). Preferably, the amount of (B) is at least 16 wt.%, more preferably at least 21 wt.%, most preferably at least 26 wt.%, most particularly preferably at least 30 wt.%, particularly at least 37 wt.%, for example at least 40 wt.%, based on the total weight of the composition (Q1).

If present, the aromatic alcohol (B) can generally be contained in varying amounts in the composition (Q2) or (Q3). If present, the amount of (B) is preferably not more than 95 wt.% (wt.% stands for "percent by weight"), more preferably not more than 80 wt.%, most preferably not more than 70 wt.%, most particularly preferably not more than 60 wt.%, particularly not more than 55 wt.%, for example not more than 50 wt.%, based on the total weight of the composition (Q2) or (Q3). If present, the amount of (B) is preferably at least 6 wt.%, more preferably at least 13 wt.%, most preferably at least 21 wt.%, most particularly preferably at least 30 wt.%, particularly at least 35 wt.%, for example at least 40 wt.%, based on the total weight of the composition (Q2), or (Q3).

According to the invention, the composition (Q2) comprises - as one of its essential components - and the compositions (Q1 ) and (Q3) can further comprise - as one of its optional components -

(C) at least one amine selected from the group consisting of

(C1 ) a polymeric polyamine, and

(C2) an amine containing not more than one amino group and at least three alkoxy- or hydroxy-substituted C2 to C12 alkyl groups R²¹ , wherein at least one of the groups R²¹ is different to the other groups R²¹, and

(C3) an amine containing not more than one amino group and at least two alkoxy- or hydroxy-substituted C2 to C12 alkyl groups R²², wherein at least one of the groups R²² bears the alkoxy or hydroxy substituent at a secondary or tertiary carbon atom and wherein at least one of the groups R²² is different to the other group(s) R²², and

(C5) a saturated or unsaturated heterocyclic amine which contains at least one oxygen atom as ring atom and which does not contain a further alkoxy group. Generally, the amine(s) (C) can be contained in varying amounts in the composition (Q2). Preferably, the amount of (C) is not more than 90 wt.% (wt.% stands for "percent by weight"), more preferably not more than 65 wt.%, most preferably not more than 48 wt.%, most particularly preferably not more than 37 wt.%, particularly not more than 30 wt.%, for example not more than 24 wt.%, based on the total weight of the composition (Q2). Preferably, the amount of (C) is at least 1 wt.%, more preferably at least 3 wt.%, most preferably at least 6 wt.%, most particularly preferably at least 9 wt.%, particularly at least 14 wt.%, for example at least 18 wt.%, based on the total weight of the composition (Q2). If present, the amine(s) (C) can generally be contained in varying amounts in the composition (Q1 ) or (Q3). If present, the amount of (C) is preferably not more than 90 wt.% (wt.% stands for "percent by weight"), more preferably not more than 65 wt.%, most preferably not more than 48 wt.%, most particularly preferably not more than 37 wt.%, particularly not more than 30 wt.%, for example not more than 24 wt.%, based on the total weight of the composition (Q1 ) or (Q3). If present, the amount of (C) is preferably at least 1 wt.%, more preferably at least 3 wt.%, most preferably at least 6 wt.%, most particularly preferably at least 9 wt.%, particularly at least 14 wt.%, for example at least 18 wt.%, based on the total weight of the composition (Q1 ) or (Q3).

According to one embodiment, (C) is

(C1 ) a polymeric polyamine.

Generally, (C1 ) can be any polymeric polyamine, and is preferably a polyalkyleneimine or poly- vinylamine, more preferably a polyalkyleneimine, most preferably a polyethyleneimine, polypro- pyleneimine, or polybutyleneimine, particularly a polyethyleneimine.

According to one embodiment, (C1 ) is preferably any polymeric polyamine comprising ethylene- imine (— CH2CH2NH— ) as monomeric units, including homopolymers and any copolymers of ethyleneimine, and is preferably a homopolymer of ethyleneimine. Copolymers can be alternating, periodic, statistical or block copolymers.

Generally, (C1 ) can be of any polymer structure, for example a linear polymer, a ring polymer, a cross-linked polymer, a branched polymer, a star polymer, a comb polymer, a brush polymer, a dendronized polymer, or a dendrimer etc. According to one embodiment, (C1 ) is an essentially linear polymer, and is preferably a linear polymer.

Polyethyleneimines which may be used are polyethyleneimine homopolymers which may be present in uncrosslinked or crosslinked form. The polyethyleneimine homopolymers can be prepared by known processes, as described, for example, in Rompps (Chemie Lexikon, 8th edition, 1992, pages 3532-3533), or in Ullmanns Enzyklopadie der Technischen Chemie, 4th edition, 1974, vol. 8, pages 212-213. and the literature stated there. They have a molecular weight in the range from about 200 to 1 000 000 g/mol. Corresponding commercial products are for example available under the name Lupasol® from BASF SE. According to one embodiment of the invention, the polyethyleneimine (C1) is preferably a poly- ethylenimine having a degree of branching in the range of from 0.1 to 0.95 (also referred to as "highly branched polyethyleneimine"), and more preferably a polyethylenimine having a degree of branching in the range of from 0.25 to 0.90, more preferably a polyethylenimine having a de- gree of branching in the range of from 0.30 to 0.80, und most preferably a polyethylenimine having a degree of branching in the range of 0.50 to 0.80.

Highly branched polyethyleneimines are characterized by its high degree of branching, which can be determined for example via ¹³C-NM spectroscopy, preferably in D2O, and is defined as follows:

Degree of branching = D +T/D+T+L

D (dendritic) equals the percentage of tertiary amino groups, L (linear) equals the percentage of secondary amino groups, and T (terminal) equals the percentage of primary amino groups. Generally, the polymeric polyamine (C1 ) can have different weight average molecular weights. The weight average molecular weight of (C1) is preferably at least 200, more preferably at least 400, most preferably at least 550, particularly at least 650, for example at least 750. The weight average molecular weight of (C1) is preferably not more than 10,000, more preferably not more than 4,000, most preferably not more than 1 ,900, particularly not more than 1 ,500, for example not more than 1 ,350. The weight average molecular weight can be determined by standard gel permeation chromatography (GPC) known to the person skilled in the art.

According to another embodiment, (C) is

(C2) an amine containing not more than one amino group and at least three alkoxy- or hy- droxy-substituted C2 to C12 alkyl groups R²¹, wherein at least one of the groups R²¹ is different to the other groups R²¹.

A number of groups R²¹ within (C2) is at least 3, preferably 3 to 5, more preferably 3 to 4, and most preferably 3.

The number of carbon atoms in each group R²¹ within (C2) is 2 to 12, preferably 2 to 9, more preferably 2 to 7, most preferably 2 to 5, particularly preferably 2 to 4, particularly 2 to 3, for example 3, wherein said number of carbon atoms does not include carbon atoms in any alkoxy groups or any other substituents of R²¹.

The groups R²¹ within (C2) are alkoxy- or hydroxy-substituted, preferably hydroxy-substituted.

For one amine (C2), among the at least three groups R²¹, at least one of the groups R²¹ is different to the other groups R²¹, preferably one of the groups R²¹ is different to the other groups R² . Preferably at least one of the groups R²¹, more preferably at least two of the groups R²¹, most preferably at least three of the groups R²¹, particularly all groups R²¹ is or are covalently bound to the amino group of the amine (C2). According to another preferred embodiment, (C2)

- is an amine containing not more than one amino group and at least three hydroxy-substituted C∑ to Ce - or preferably C2 to C₅ - alkyl groups R²¹, wherein at least one of the groups R²¹ is different to the other groups R²¹,

- is preferably an amine containing not more than one amino group and at least three hydroxy- substituted C2 to C3 alkyl groups R²¹, wherein at least one of the groups R²¹ is different to the other groups R²¹,

- is more preferably an amine containing not more than one amino group and three hydroxy- substituted C2 to C3 alkyl groups R²¹ which are covalently bound to the amino group, wherein one of the groups R²¹ is different to the other groups R²¹, and

- is for example an amine selected from the group consisting of Bis(hydroxyethyl)- isopropanolamine (DEIPA), and 1 ,1 '-((2-Hydroxyethyl)imino)dipropan-2-ol.

According to another preferred embodiment, (C2) is an amine N(R²¹)3 wherein

R²¹ is a an alkoxy- or hydroxy-substituted - preferably a hydroxyl-substituted - C2 to C12 - pref- erably a C2 to C7, more preferably a C2 to C3 - alkyl group and wherein one of the groups R²¹ is different to the other group R²¹.

According to another preferred embodiment, (C2) is an amine N(R²¹)3 wherein

R²¹ is a an alkoxy- or hydroxy-substituted - preferably a hydroxyl-substituted - C2 to C12 - pref- erably a C2 to C7, more preferably a C2 to C3 - alkyl group and wherein one of the groups R²¹ is different to the other group R²¹ and wherein at least one of the groups R²¹ bears the alkoxy or hydroxy substituent at a secondary or tertiary carbon atom.

According to another embodiment, (C) is

(C3) an amine containing not more than one amino group and at least two alkoxy- or hydroxy- substituted C2 to C12 alkyl groups R²², wherein at least one of the groups R²² bears the alkoxy or hydroxy substituent at a secondary or tertiary carbon atom and wherein at least one of the groups R²² is different to the other group(s) R²². A number of groups R²² within (C3) is at least 2, preferably 2 to 5, more preferably 2 to 4, and most preferably 2 to 3, for example 2.

The number of carbon atoms in each group R²² within (C3) is 2 to 12, preferably 2 to 9, more preferably 2 to 7, most preferably 2 to 5, particularly preferably 2 to 4, particularly 2 to 3, for ex- ample 3, wherein said number of carbon atoms does not include carbon atoms in any alkoxy groups or any other substituents of R²².

The groups R²² within (C3) are alkoxy- or hydroxy-substituted, preferably hydroxy-substituted. For one amine (C3), among the at least two groups R²², at least one of the groups R²² is different to the other group(s) R²², preferably one of the groups R²² is different to the other group(s) R²². Preferably at least one of the groups R²², more preferably at least two of the groups R²², most preferably all groups R²² is or are covalently bound to the amino group of the amine (C3).

Preferably at least one of the groups R²², more preferably one of the groups R²² bears the alkoxy or hydroxy substituent at a secondary or tertiary carbon atom, particularly at a secondary carbon atom.

According to another preferred embodiment, (C3)

- is an amine containing not more than one amino group and at least two hydroxy-substituted C∑ to C7 alkyl groups R²², wherein at least one of the groups R²² bears the hydroxy substitu- ent at a secondary or tertiary carbon atom and wherein at least one of the groups R²² is different to the other group(s) R²²,

- is more preferably an amine containing not more than one amino group and at least two hydroxy-substituted C2 to C4 alkyl groups R²², wherein at least one of the groups R²² bears the hydroxy substituent at a secondary carbon atom and wherein at least one of the groups R²² is different to the other group(s) R²²,

- is most preferably an amine containing not more than one amino group and two hydroxy- substituted C2 to C3 alkyl groups R²² which are covalently bound to the amino group of the amine (C3), wherein at least one of the groups R²² bears the hydroxy substituent at a secondary carbon atom and wherein one of the groups R²² is different to the other group R²², - is for example an amine selected from the group consisting of 1-((2-hydroxyethyl)amino)- propan-2-ol, and N-Methyl-N-hydroxyethyl-isopropanolamine.

According to another preferred embodiment, (C3) is an amine R²⁴N(R²²)2 wherein

R²⁴ is H or a Ci to C12- preferably a Ci to C₇, more preferably a Ci to C3 - alkyl group and R²² is an alkoxy- or hydroxy-substituted - preferably a hydroxyl-substituted - C2 to C12 - preferably a C2 to C₇, more preferably a C2 to C3 - alkyl group and wherein at least one of the groups R²² bears the hydroxy substituent at a secondary carbon atom and wherein one of the groups R²² is different to the other group R²². According to another embodiment, (C) is

(C4) an amine containing at least one saturated or unsaturated Ce to C40 alkyl group R²³.

The number of carbon atoms in each group R²³ within (C4) is 8 to 40, preferably 8 to 32, more preferably 8 to 24, most preferably 8 to 19, particularly preferably 8 to 16.

The group R²³ within (C4) is saturated or unsaturated, preferably unsaturated. According to another preferred embodiment, (C4) contains at least one alkoxy or hydroxy group, more preferably at least one alkoxy and at least one hydroxy groups, most preferably at least two alkoxy and at least one hydroxyl group, particularly at least four alkoxy and at least one hy- droxyl group.

For example, (C4) is an amine selected from the group consisting of: ethoxylated (2) cocoalkyl- amine, ethoxylated (5) cocoalkylamine, ethoxylated (15) cocoalkylamine, ethoxylated (2) oleylamine, lauryl-dimethylamine, oleyl-dimethylamine, and 2-propylheptylamine ethoxylate (5 EO), 2-propylheptylamine ethoxylate (10 EO), and 2-propylheptylamine ethoxylate (20 EO).

According to another embodiment, (C) is

(C5) a saturated or unsaturated heterocyclic amine which contains at least one oxygen atom as ring atom and which does not contain a further alkoxy group. The term "heterocyclic amine" stands for a heterocyclic compound in which at least one ring atom of the heterocyclic ring is a nitrogen atom.

The heterocyclic amine (C5) is saturated or unsaturated, preferably saturated. The heterocyclic amine (C5) contains preferably a 5-, 6- or 7-membered heterocyclic ring, more preferably a 5- or 6-membered ring, most preferably a 6-membered ring.

The heterocyclic amine (C5) contains at least one, more preferably 1 to 3, most preferably 1 to 2, particularly one oxygen atom(s) as ring atom(s) of the heterocyclic ring.

The heterocyclic amine (C5) is preferably a morpholine or morpholine derivative, more preferably N-alkyl morpholine, most preferably N-methyl, N-ethyl, N-propyl, or N-butyl morpholine, for example N-methyl morpholine. According to the invention, the composition (Q3) comprises - as one of its essential components - and the compositions (Q1 ) and (Q2) can further comprise - as one of its optional components -

(D) at least one amide according to the general formula (III)

3¹CO-NR^{32 33}

wherein

R³ CO is an acyl radical having 1 to 22 carbon atoms;

_R32 is H or alkyl, and

R33 is H or alkyl, or

R³² and R³³ together with the nitrogen atom linking them define a 5- or 6-membered saturated or unsaturated heterocyclic radical, which optionally comprises 1 or 2 further heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur. Generally, the amide(s) (D) can be contained in varying amounts in the composition (Q3). Preferably, the amount of (D) is not more than 90 wt.% (wt.% stands for "percent by weight"), more preferably not more than 65 wt.%, most preferably not more than 45 wt.%, most particularly preferably not more than 30 wt.%, particularly not more than 22 wt.%, for example not more than 16 wt.%, based on the total weight of the composition (Q3). Preferably, the amount of (D) is at least 1 wt.%, more preferably at least 3 wt.%, most preferably at least 6 wt.%, most particularly preferably at least 9 wt.%, particularly at least 12 wt.%, for example at least 15 wt.%, based on the total weight of the composition (Q3). If present, the amide (D) can generally be contained in varying amounts in the composition (Q1 ) or (Q2). If present, the amount of (D) is preferably not more than 90 wt.% (wt.% stands for "percent by weight"), more preferably not more than 65 wt.%, most preferably not more than 45 wt.%, most particularly preferably not more than 30 wt.%, particularly not more than 22 wt.%, for example not more than 16 wt.%, based on the total weight of the composition (Q1 ) or (Q2). If present, the amount of (D) is preferably at least 1 wt.%, more preferably at least 3 wt.%, most preferably at least 6 wt.%, most particularly preferably at least 9 wt.%, particularly at least 12 wt.%, for example at least 15 wt.%, based on the total weight of the composition (Q1 ) or (Q2).

In the general formula (III) of (D) ³² is H or alkyl, preferably H or Ci to C40 alkyl, more prefera- bly H or Ci to C20 alkyl, most preferably H or Ci to C10 alkyl, particularly preferably H or Ci to C4 alkyl, most particularly preferably Ci to C₄ alkyl, particularly Ci to C₂ alkyl, for example methyl.

In the general formula (III) of (D) R³³ is H or alkyl, preferably H or Ci to C40 alkyl, more preferably H or Ci to C20 alkyl, most preferably H or Ci to C10 alkyl, particularly preferably H or Ci to C₄ alkyl, most particularly preferably Ci to C₄ alkyl, particularly Ci to C₂ alkyl, for example methyl.

According to one preferred embodiment, in the general formula (III) of (D) R³² is H or Ci to C₄ alkyl, and R³³ is H or Ci to C₄ alkyl, more preferably, R³² is Ci to C₄ alkyl, and R³³ is Ci to C₄ alkyl, most preferably, R³² is Ci to C2 alkyl, and R³³ is Ci to C2 alkyl.

According to one preferred embodiment (D1 PE), in the general formula (III) of (D) R³¹CO is a hydroxysubstituted acyl radical having 1 to 22 carbon atoms, and more preferably, R³¹CO is a hydroxysubstituted acyl radical having 1 to 22 carbon atoms, and R³² is alkyl, and R³³ is alkyl, and most preferably, R³¹CO is a hydroxysubstituted acyl radical having 1 to 7 carbon atoms, and R³² is Ci to C₄ alkyl, and R³³ is Ci to C₄ alkyl.

According to another preferred embodiment, the amide (D) is a Ν,Ν-dialkyl amide based on lactic acid, citric acid, tartaric acid, ricinoleic acid, 12-hydroxy stearic acid, or their mixtures, preferably a Ν,Ν-dialkyl amide based on lactic acid, citric acid, tartaric acid, or their mixtures, most preferably a Ν,Ν-dimethyl amide based on lactic acid, citric acid, tartaric acid, particularly a lactic acid N,N-dimethylamide. According to another preferred embodiment (D2PE), in the general formula (III) of (D) R³ CO is an acyl radical having 6 to 12 carbon atoms, more preferably, R³¹CO is an acyl radical having 8 to 10 carbon atoms. According to another preferred embodiment, in the general formula (III) of (D) R³¹CO does not contain a hydroxy group, and more preferably, R³¹CO does not contain a hydroxy group and is an acyl radical having 6 to 12 carbon atoms, and most preferably, R³¹CO does not contain a hydroxy group and is an acyl radical having 8 to 10 carbon atoms. For example, the amide (D) is selected from the group consisting of Ν ,Ν-dimethyloctanamide, N,N-dimethylnonanamide, and N,N-dimethyldecanamide.

According to another preferred embodiment (D3PE), in the general formula (III) of (D) R³¹CO is an acyl radical having 1 to 3 carbon atoms, more preferably, R³¹CO is an acyl radical having 1 to 2 carbon atoms.

According to another preferred embodiment, in the general formula (II I) of (D) R³² and R³³ together with the nitrogen atom linking them define a 5- or 6-membered saturated or unsaturated heterocyclic radical which optionally comprises 1 or 2 further heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, and more preferably, R³² and R³³ together with the nitrogen atom linking them define a 6-membered saturated or unsaturated heterocyclic radical which optionally comprises one further heteroatom selected from the group consisting of nitrogen, oxygen, and sulfur, most preferably R³² and R³³ together with the nitrogen atom linking them define a 6-membered saturated heterocyclic radical which comprises one further oxygen heteroatom, particularly R³² and R³³ together with the nitrogen atom linking them define a mor- pholinyl radical. For example, the amide (D) is N-acetylmorpholine or N-formylmorpholine.

According to another preferred embodiment (D4PE), in the general formula (I II) of (D) R³² and R³³ together with the nitrogen atom linking them define a 5-membered saturated or unsaturated heterocyclic radical which optionally comprises 1 or 2 further heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, and more preferably, R³² and R³³ together with the nitrogen atom linking them define a 5-membered saturated heterocyclic radical which optionally comprises one further nitrogen heteroatoms, most preferably R³² and R³³ together with the nitrogen atom linking them define a 5-membered saturated heterocyclic radical which comprises one further nitrogen heteroatom which is covalently bound to the carbon atom of the car- bonyl group of R³¹CO, particularly R³² and R³³ together with the nitrogen atom linking them define a imidazolidinonyl radical. For example, the amide (D) is 1 ,3-Dimethyl-2-imidazolidinone (also referred to as dimethylethylenurea).

According to another preferred embodiment (D5PE), in the general formula (III) of (D) R³² is an acyloxy substituted alkyl group, more preferably, R³¹CO is an acyl radical having 1 to 4 carbon atoms, and R³² is an acyloxy substituted alkyl group, most preferably, R³¹CO is an acyl radical having 1 to 4 carbon atoms, R³² is an acyloxy substituted alkyl group and R³³ is Ci to C4 alkyl. For example, the amide (D) is N-[2-(acetyloxy)ethyl]-N-methyl acetamide. The composition (Q1), (Q2), or (Q3) can further optionally comprise

(E) an alcohol comprising at least two hydroxy groups which are not dissociable in the aqueous medium. The alcohol (E) is different from the components (A), (B), (C) and (D). "Not dissociable" means that the pK_a value (logarithmic measure of the acid dissociation constant) for the reaction alcohol (D)→ deprotonated alcohol (D) + H⁺ of the hydroxy group in the neutral aqueous phase is more than 9.9, more preferably more than 1 1 , most preferably more than 12, particularly preferably more than 13, for example more than 14 as measured in de-ionized water at 25°C and atmospheric pressure. For example, propane- 1 ,2-diol (alpha-propylene glycol) has a pK_a value of 14.9 as measured in de-ionized water at 25°C and atmospheric pressure.

If present, the alcohol (E) is preferably used as solvent in the compositions (Q1 ), (Q2), or (Q3). Preferably, the alcohol (E) is a diol, triol, tetraol, pentaol, hexaol, heptaol, octaol, nonaol, decaol, or a polyol. More preferably, (E) is a diol, triol, tetraol, pentaol, or hexaol. Most preferably, (E) is a diol. Particularly most preferably, (E) is ethanediol (ethylene glycol), propanediol (propylene glycol), or butanediol (butylene glycol). Particularly, (E) is propanediol (propylene glycol). For example, (E) is propane-1 ,2-diol (alpha-propylene glycol).

The alcohol (E) is preferably an alcohol having 2 to 50 carbon atoms, more preferably an alcohol having 2 to 20 carbon atoms, most preferably an alcohol having 2 to 1 1 carbon atoms, particularly preferably an alcohol having 2 to 7 carbon atoms, in particular an alcohol having 2 to 4 carbon atoms, for example an alcohol having 3 carbon atoms.

If present, the alcohol (E) can be contained in varying amounts in the composition (Q1), (Q2), or (Q3). If present, the amount of (E) is preferably not more than 99 wt.% (wt.% stands for "percent by weight"), more preferably not more than 93 wt.%, most preferably not more than 87 wt.%, most particularly preferably not more than 80 wt.%, particularly not more than 75 wt.%, for ex- ample not more than 70 wt.%, based on the total weight of the composition (Q1), (Q2), or (Q3). If present, the amount of (E) is at least 13 wt.%, more preferably at least 20 wt.%, most preferably at least 35 wt.%, most particularly preferably at least 45 wt.%, particularly at least 55 wt.%, for example at least 60 wt.%, based on the total weight of the composition (Q1 ), (Q2), or (Q3). According to another embodiment, the amount of (E) is preferably not more than 78 wt.%, more preferably not more than 67 wt.%, most preferably not more than 61 wt.%, most particularly preferably not more than 56 wt.%, particularly not more than 53 wt.%, for example not more than 50 wt.%, based on the total weight of the composition (Q1), (Q2), or (Q3). Preferably, the amount of (E) is at least 16 wt.%, more preferably at least 21 wt.%, most preferably at least 26 wt.%, most particularly preferably at least 30 wt.%, particularly at least 37 wt.%, for example at least 40 wt.%, based on the total weight of the composition (Q1 ), (Q2), or (Q3).

The composition (Q1), (Q2), or (Q3) can further optionally comprise (F) a nitrogen-containing fertilizer. The nitrogen-containing fertilizer (F) is different from the components (A), (B), (C) and (D).

The nitrogen-containing fertilizer (F) preferably comprises manure, ammonium sulfate, ammoni- um nitrate, ammonium chloride, cyanamide, dicyandiamide (DCD), calcium nitrate, or urea- containing fertilizer (F1 ), more preferably comprises urea-containing fertilizer (F1 ), most preferably comprises urea, for example is urea.

The urea-containing fertilizer (F1 ) is defined as a fertilizer comprising at least one component selected from the group consisting of urea, urea ammonium nitrate (UAN), isobutylidene diurea (IBDU), crotonylidene diurea (CDU) and urea formaldehyde (UF), urea-acetaldehyde, and urea- glyoxal condensates.

In customary commercial fertilizer quality, the urea has a purity of at least 90%, and may for example be in crystalline, granulated, compacted, prilled or ground form.

If present, the fertilizer (F) can be contained in varying amounts in the composition (Q1 ), (Q2), or (Q3). If present, the amount of (F) is preferably not more than 99.99 wt.% (wt.% stands for "percent by weight"), more preferably not more than 99.9 wt.%, most preferably not more than 99.5 wt.%), most particularly preferably not more than 99 wt.%o , particularly not more than 98 wt.%, for example not more than 97 wt.%, based on the total weight of the composition (Q1 ), (Q2), or (Q3). If present, the amount of (F) is preferably at least 96 wt.%, more preferably at least 93 wt.%, most preferably at least 90 wt.%, most particularly preferably at least 82 wt.%, particularly at least 70 wt.%, for example at least 50 wt.%, based on the total weight of the com- position (Q1), (Q2), or (Q3).

The properties of the composition (Q1), (Q2), or (Q3) - such as stability, storage life, or stability when applied to or coated on nitrogen-containing fertilizers (F) such as urea - may depend on the pH of the corresponding composition. In general, the composition (Q1 ), (Q2), or (Q3) can have any pH value. The pH value of the composition (Q1 ), (Q2), or (Q3) is preferably not more than 14, more preferably not more than 13, most preferably not more than 12, particularly preferably not more than 1 1.6, particularly most preferably not more than 11 .3, particularly not more than 11 , for example not more than 10.7. The pH value of the composition (Q1 ), (Q2), or (Q3) is preferably at least 6, more preferably at least 7, most preferably at least 7.5, particularly prefer- ably at least 8.0, particularly most preferably at least 8.2, particularly at least 8.5, for example at least 8.7. The pH value of the composition (Q1 ), (Q2), or (Q3) is preferably in the range of from 6 to 14, more preferably from 7 to 13, most preferably from 7.5 to 12, particularly preferably from 8 to 1 1.6, particularly most preferably from 8.2 to 11 .3, particularly from 8.5 to 1 1 , for example from 8.7 to 10.7.

The composition (Q1 ), (Q2), or (Q3) can further optionally contain at least one pH adjusting agent (G). The pH adjusting agent (G) is different from the components (A), (B), (C) and (D). In general, the pH adjusting agent (G) is a compound which is added to the composition (Q1 ), (Q2), or (Q3) to have its pH value adjusted to the required value. Preferably, the composition (Q1 ), (Q2), or (Q3) contains at least one pH adjusting agent (G). Preferred pH adjusting agents are inorganic acids, carboxylic acids, amine bases, alkali hydroxides, ammonium hydroxides, including tetraalkylammonium hydroxides. Particularly, the pH adjusting agent (G) is nitric acid, sulfuric acid, ammonia, sodium hydroxide, or potassium hydroxide. For example, the pH adjusting agent (G) is potassium hydroxide.

If present, the pH adjusting agent (G) can be contained in varying amounts in the composition (Q1 ), (Q2), or (Q3). If present, the amount of (G) is preferably not more than 10 wt.%, more preferably not more than 2 wt.%, most preferably not more than 0.5 wt.%, particularly not more than 0.1 wt.%, for example not more than 0.05 wt.%, based on the total weight of the corresponding composition (Q1 ), (Q2), or (Q3). If present, the amount of (G) is preferably at least 0.0005 wt.%, more preferably at least 0.005 wt.%, most preferably at least 0.025 wt.%, particularly at least 0.1 wt.%, for example at least 0.4 wt.%, based on the total weight of the corre- sponding composition (Q1 ), (Q2), or (Q3).

The composition (Q1), (Q2), or (Q3) can further optionally contain the compound (K) selected from the group consisting of (K1) an amine selected from the group consisting of methyldiethanolamine, tetrahydroxypro- pylethylenediamine, trimethylaminoethylethanolamine, N,N,N',N'-tetramethyl-1 ,6- hexanediamine, N,N',N"-tris(dimethylaminopropyl)hexahydrotriazine, and 2,2'- dimorpholinyldiethyl ether,

(K2) an amine containing not more than one amino group and at least three alkoxy- or hydroxy- substituted C2 to C12 alkyl groups R⁴¹, wherein all groups R⁴¹ within said amine are identical, and

(K3) an amine containing not more than one amino group and at least two alkoxy- or hydroxy- substituted C2 to C12 alkyl groups R⁴², wherein at least one of the groups R⁴² bears the alkoxy or hydroxy substituent at a secondary or tertiary carbon atom and wherein all groups R⁴² with said amine are identical.

(K2) or (K3) are preferably triethanolamine, tripropanolamine, diisopropanolamine, triisopro- panolamine, diethanolamine, methyldiethanolamine, or methyldipropanolamine. If present, the compound (K) can generally be contained in varying amounts in the composition (Q1 ), (Q2), or (Q3). If present, the amount of (K) is preferably not more than 40 wt.% (wt.% stands for "percent by weight"), more preferably not more than 30 wt.%, most preferably not more than 25 wt.%, most particularly preferably not more than 20 wt.%, particularly not more than 18 wt.%, for example not more than 15 wt.%, based on the total weight of the composition (Q1 ), (Q2), or (Q3).). If present, the amount of (K) is preferably at least 1 wt.%, more preferably at least 3 wt.%, most preferably at least 5 wt.%, most particularly preferably at least 8 wt.%, particularly at least 1 1 wt.%, for example at least 14 wt.%, based on the total weight of the composition (Q1), (Q2), or (Q3). The composition (Q1), (Q2), or (Q3) can further optionally contain components (H) which are selected from the group consisting of auxiliaries, solvents, solid carriers, surfactants, adjuvants, thickeners, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers, binders, preservatives, antioxidants, and odorants. The component (H) is different from the components (A), (B), (C) and (D).

Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders.

Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions of medium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, paraffin, tetrahydronaphthalene, al- kylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, cyclohexanol; glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g. lactates, carbonates, fatty acid esters, gamma- butyrolactone; fatty acids; phosphonates; amines; amides, e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof. Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, e.g. cellulose, starch; fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.

Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emusifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon's, Vol.1 : Emulsifiers & De- tergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).

Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof. Examples of sulfonates are alkylarylsulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates. Suitable nonionic surfactants are alkoxylates, N-subsituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents. Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide. Examples of N-subsititued fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerol esters or monoglycerides. Examples of sugar- based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or al- kylpolyglucosides. Examples of polymeric surfactants are home- or copolymers of vinylpyrroli- done, vinylalcohols, or vinylacetate.

Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkylbetains and imidazolines. Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines or pol- yethyleneamines.

Suitable adjuvants are compounds, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of the compound I on the target. Examples are surfactants, mineral or vegetable oils, and other auxilaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.

Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethylcellulose), anorganic clays (organically modified or unmodified), polycarboxylates, and silicates. Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones.

Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin. Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.

Suitable colorants (e.g. in red, blue, or green) are pigments of low water solubility and water- soluble dyes. Examples are

- inorganic colorants, such as iron oxide, titan oxide, iron hexacyanoferrate,

- metal-complex dyes such as chromium-complex dyes, for example Orasol Yellow 141 ,

- organic colorants such as alizarin-, azo- and phthalocyanine colorants.

Preferred colorants are metal-complex dyes, more preferably chromium-complex dyes, for example Orasol Yellow 141. Suitable tackifiers or binders are polyvinylpyrrolidones, polyvinylacetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.

Suitable preservatives include e.g. sodium benzoate, benzoic acid, sorbic acid, and derivatives thereof.

Suitable antioxidants include sulfites, ascorbic acid, tocopherol, tocopherol acetate, tocotrienol, melatonin, carotene, beta-carotene, ubiquinol, and derivatives thereof. Tocophercol acetate is preferred as antioxidant. Suitable odorants include perfume materials which are for example mentioned in US 7 182 537, including allo-ocimene, Allyl cyclohexanepropionate, Allyl heptanoate, trans-Anethole, Benzyl butyrate, Camphene, Cadinene, Carvacrol, cis-3-Hexenyl tiglate, Citronellol, Citronellyl acetate, Citronellyl nitrile, Citronellyl propionate, Cyclohexylethyl acetate, Decyl Aldehyde (Capralde- hyde), Dihydromyrcenol, Dihydromyrcenyl acetate, 3,7-Dimethyl-1-octanol, Diphenyloxide, Fen- chyl Acetate (1 ,3,3-Trimethyl-2-norbornanyl acetate), Geranyl acetate, Geranyl formate, Gera- nyl nitrile, cis-3-Hexenyl isobutyrate, Hexyl Neopentanoate, Hexyl tiglate, alpha-lonone, Ethyl Vanillin L80, Isoeugenol, Methyl cinnamate, Methyl dihydrojasmonate, Methyl beta-naphthyl ketone, Phenoxy ethyl isobutyrate, Vanillin L28, Isobornyl acetate, Isobutyl benzoate, Isononyl acetate, Isononyl alcohol (3,5,5-Trimethyl-1-hexanol), Isopulegyl acetate, Lauraldehyde, d- Limonene, Linalyl acetate, (-)-L-Menthyl acetate, Methyl Chavicol (Estragole), Methyl n-nonyl acetaldehyde, methyl octyl acetaldehyde, beta-Myrcene, Neryl acetate, Nonyl acetate, Non- aldehyde, p-Cymene, alpha-Pinene, beta-Pinene, alpha-Terpinene, gamma-Terpinene, alpha- Terpinyl acetate, Tetrahydrolinalool, Tetrahydromyrcenol, 2-Undecenal, Verdox (o-t- Butylcyclohexyl acetate), Vertenex (4-tert,Butylcyclohexyl acetate). Citronellyl nitrile is preferred as odorant.

According to one embodiment, individual components of the compositions (Q1), (Q2), or (Q3) such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropriate.

If present, the component (H) can be contained in varying amounts in the composition (Q1 ), (Q2), or (Q3). If present, the amount of (H) is preferably not more than 10 wt.%, more preferably not more than 4 wt.%, most preferably not more than 2 wt.%, particularly not more than 1 wt.%, for example not more than 0.5 wt.%, based on the total weight of the corresponding composition (Q1 ), (Q2), or (Q3). If present, the amount of (H) is preferably at least 0.0005 wt.%, more preferably at least 0.005 wt.%, most preferably at least 0.025 wt.%, particularly at least 0.1 wt.%, for example at least 0.4 wt.%, based on the total weight of the corresponding composition (Q1 ), (Q2), or (Q3). With respect to the composition (Q1), (Q2), or (Q3), the weight ratio of the mixture (A) to the aromatic alcohol (B) - in case of (Q2) or (Q3) only as far as (B) is present - is preferably between 50:1 and 1 :50, more preferably between 10:1 and 1 :10, most preferably between 5:1 and 1 :5, particularly preferably between 3:1 and 1 :3, particularly most preferably between 2:1 and 1 :2, particularly between 1 :1 and 1 :2, for example between 1 :1.5 to 1 :1.8.

With respect to the composition (Q1 ), (Q2), or (Q3), the weight ratio of the mixture (A) to the amine (C) - in case of (Q1 ) or (Q3) only as far as (C) is present - is preferably between 100:1 and 1 :20, more preferably between 40:1 and 1 :8, most preferably between 30:1 and 1 :6, particularly preferably between 20:1 and 1 :5, particularly most preferably between 10:1 and 1 :2, particularly between 5:1 and 1 :1.2, for example between 2:1 to 1 :1. With respect to the composition (Q1 ), (Q2), or (Q3), the weight ratio of the mixture (A) to the amide (D) - in case of (Q1 ) or (Q2) only as far as (D) is present - is preferably between 50:1 and 1 :50, more preferably between 10:1 and 1 :10, most preferably between 5:1 and 1 :5, particularly preferably between 3:1 and 1 :3, particularly most preferably between 2.5:1 and 1 :2, particularly between 2:1 and 1 :1 , for example between 1.8:1 to 1.2:1.

According to the invention, a process for treating the soil comprising applying the compositions (Q1 ), (Q2), or (Q3) into the soil in-furrow and/or as side-dress and/or as broadcast was found.

Preferably, said process comprises: applying the compositions (Q1 ), (Q2), or (Q3) by spraying it onto the soil. More preferably, said process are conducted in a way wherein the compositions (Q1 ), (Q2), or (Q3) are - either at the same time (i.e. simultaneously) or with a time difference (i.e. separately) - applied together with at least one nitrogen-containing fertilizer (F) into the soil in-furrow and/or as side-dress and/or as broadcast. According to the invention, the compositions (Q1 ), (Q2), or (Q3) can be used as additive or as coating material for nitrogen-containing fertilizers (F), particularly for urea-containing fertilizer (F1 ), for example for urea. According to one preferred embodiment, the compositions (Q1 ), (Q2), or (Q3) are used as coating material for nitrogen-containing fertilizers (F), particularly for urea-containing fertilizer (F1 ), for example for urea. The nitrogen-containing fertilizer (F) cam be in crystalline, granulated, compacted, prilled or ground form, and is preferably in granulated from.

The compositions (Q1 ), (Q2), or (Q3) can be applied to or on nitrogen-containing fertilizers (F) by either mixing the (Q1 ), (Q2), or (Q3), in either liquid or solid form, with the nitrogen-containing fertilizer (F), or incorporating them into (F) by granulation, compacting or prilling, by addition to a corresponding fertilizer mixture or to a mash or melt. Preferably, the compositions (Q1 ), (Q2), or (Q3) are applied to the surface of existing granules, compacts or prills of the nitrogen-containing fertilizer (F) - particularly of the urea-containing fertilizer (F1) - by means of spraying, powder application or impregnating, for example. This can also be done using further auxiliaries such as adhesive promoters or encasing materials. Examples of apparatuses suitable for performing such application include plates, drums, mixers or fluidized-bed apparatus, although application may also take place on conveyor belts or their discharge points or by means of pneumatic conveyors for solids. A concluding treatment with anticaking agents and/or antidust agents is like- wise possible. The compositions (Q1 ), (Q2), or (Q3) are used in the context of fertilization with nitrogen-containing fertilizer (F), particularly with urea-containing fertilizer (F1 ). Application takes place preferably to an agriculturally or horticulturally exploited plot.

In parallel with the improvement of the utilization of nitrogen in the urea-containing, mineral and organic fertilizers, the use of the compositions (Q1 ), (Q2), or (Q3) has the effect that there is an Increase - in some cases considerably - in the yields or production of biomass of crop plants.

The compositions (Q1), (Q2), or (Q3) may be added to organic fertilizers, such as liquid manure, for example, during the actual storage of such fertilizers, in order thus to prevent nitrogen nutri- ent losses, by virtue of decelerated conversion of the individual forms of nitrogen into gaseous nitrogen compounds, which are therefore volatile, and in order as a result, at the same time, to contribute to a lowering of the ammonia load in animal stables.

In this context it is immaterial whether the compositions (Q1 ), (Q2), (Q3) are incorporated, by melting, for example, into the nitrogen-containing fertilizer (F), or else are applied to the fertilizer surface or applied separately from the spreading of the fertilizer, in the form, for example, of a (suspension) concentrate, a solution or a formulation.

For the below examples and the below tables, the following abbreviations have been used:

% = percent by weight (wt. %)

ad100 = the percent by weight of this component is 100% minus the sum of the weight percentages (in percent by weight) of all other components comprised in the composition

BDA = Butyldiethanolamine

BZ = benzyl alcohol

(C)i = amine component (C)

(C)ii = additional amine component (C)

Coat. = coated on urea (all the data in the rows below the "coated row" are experimental data after the composition has been coated on urea)

colo. = colorant Orasol Yellow 141

cone. = concentration (e.g. amount) of NxPT in percent by weight based on the total weight of the urea fertilizer on which the composition was coated

Comp. = comparative example

DEI = Bis(hydroxyethyl)-isopropanolamine (DEI PA)

dev. = deviation, as an indicator for the stability after coated on urea, calculated as difference between the NxPT content in the heat stability test and the content in the cold stability test - both after coated on urea -, indicated as percent

DMI = 1 ,3-Dimethyl-2-imidazolidinone (Dimethylethylenurea)

DML = Dimethyllactamide

E15 = ethoxylated (5) cocoalkylamine

E25 = ethoxylated (15) cocoalkylamine

Ex# = Example no.

F.ex. = formulation example HBI = 1 -((2-hydroxyethyl)amino)propan-2-ol (Hydroxyethyl-bis-isopropanolamin)

Inv. = Example of the invention

LES = 2-propylheptylamine ethoxylate (10 EO)

LFG = polyethyleneimine with a weight average molecular weight of 800 g/mol as measured by GPC (dry substance, at pH 4.5)

LGA = polyethyleneimine with a weight average molecular weight of 1300 g/mol as measured by GPC (dry substance, at pH 4.5)

LL = technical mixture (with a 85.20% concentration of NxPT) containing 23.8% NPPT and 76.2% NBPT

LPN = N,N',N"-tris(dimethylaminopropyl)hexahydrotriazine

LT = technical mixture (with a 84.27% concentration of NxPT based on the total amount of the technical mixture) containing 23.7% NPPT and 76.3% NBPT, based on the total amount of NxPT within the technical mixture

HCM = Mixture of N,N-Dimethyloctanamide (50-65%) and N,N-Dimethyldecanamide (37 -50%) MDA = Methyldiethanolamine

MPA = n-Acetyl-morpholine

MPF = n-Formyl-morpholine

NB/c = Content (percent by weight) of NBPT in cold stability test (2 weeks at 5°C)

NP/c = Content (percent by weight) of NPPT in cold stability test (2 weeks at 5°C)

Nx/c = Content (Percent by weight) of NxPT in cold stability test (2 weeks at 5°C)

NB/h = Content (Percent by weight) of NBPT in heat stability test (2 weeks at 54°C)

NP/h = Content (Percent by weight) of NPPT in heat stability test (2 weeks at 54°C)

Nx/h = Content (Percent by weight) of NxPT in heat stability test (2 weeks at 54°C)

NB/a = Content (Percent by weight) of NBPT in cold stability test (2 weeks at 5°C) after coated on urea

NP/a = Content (Percent by weight) of NPPT in cold stability test (2 weeks at 5°C) after coated on urea

Nx/a = Content (Percent by weight) of NxPT in cold stability test (2 weeks at 5°C) after coated on urea

NB/b = Percent by weight of NBPT in heat stability test (4 weeks at 40°C and 50% air humidity) after coated on urea

NP/b = Percent by weight of NPPT in heat stability test (4 weeks at 40°C and 50% air humidity) after coated on urea

Nx/b = Percent by weight of NxPT in heat stability test (4 weeks at 40°C and 50% air humidity) after coated on urea

NxPT = Mixture (A) comprising NBPT and NPPT (the content of NxPT is the sum of the content of NBPT and NPPT)

NyPT = Mixture (A) comprising NBPT and/or NPPT

NMM = N-methyl-morpholine

NMP = N-methyl-pyrrolidinone

PEI = polyethyleneimine

PG = propylene glycol

pH = pH value measured at 2% concentration SEA = is N-[2-(acetyloxy)ethyl]-N-methyl acetamide

stabi. = storage stability of NxPT, calculated as difference between the NxPT content in the heat stability test and the content in the cold stability test, indicated as percent

TEA = triethanolamine

TPA = tocopherol acetate

vise. = viscosity in mPas

The following compositions as listed in Table 1 are preferred embodiments of the present invention.

For the preferred embodiments PE1 to PE161 , the following abbreviations are used in addition to the abbreviations listed above:

(C1 ) is a polymeric polyamine;

(C2) is an amine containing not more than one amino group and at least three alkoxy- or hydroxy-substituted C2 to C12 alkyl groups R²¹, wherein at least one of the groups R²¹ is different to the other groups R²¹;

(C3) is an amine containing not more than one amino group and at least two alkoxy- or hydroxy- substituted C2 to C12 alkyl groups R²², wherein at least one of the groups R²² bears the alkoxy or hydroxy substituent at a secondary or tertiary carbon atom and wherein at least one of the groups R²² is different to the other group(s) R²²;

(C4) is an amine containing at least one saturated or unsaturated Ce to C40 alkyl group R²³, and (C5) is a saturated or unsaturated heterocyclic amine which contains at least one oxygen atom as ring atom and which does not contain a further alkoxy group.

(D1 ) is an amide according to the general formula (III)

R³¹CO-NR³²R³³

wherein

R³¹CO is a hydroxysubstituted acyl radical having 1 to 22 carbon atoms;

R³² is H or Ci to C₄ alkyl, and

R³³ is H or Ci to C₄ alkyl.

(D2) is an amide according to the general formula (III)

R³ CO-NR³²R³³

wherein

R³¹CO is a is an acyl radical having 1 to 22 carbon atoms which do not contain a hydroxyl group;

R³² is H or Ci to C₄ alkyl, and

R³³ is H or Ci to C₄ alkyl.

(D3) is an amide according to the general formula (III)

R³¹CO-NR³²R³³

wherein

R³¹CO is an acyl radical having 1 to 22 carbon atoms;

R³² and R³³ together with the nitrogen atom linking them define a 6-membered saturated heterocyclic radical which comprises one further oxygen heteroatom. (D4) is an amide according to the general formula (III)

R³¹CO-NR³²R³³

wherein

R³¹CO is an acyl radical having 1 to 22 carbon atoms;

R³² and R³³ together with the nitrogen atom linking them define a 5-membered saturated heterocyclic radical which comprises one further nitrogen heteroa- tom.

(D5) is an amide according to the general formula (III

R³ CO-NR³²R³³

wherein

R³¹CO is an acyl radical having 1 to 22 carbon atoms;

R³² is an acyloxy substituted alkyl group, and

R³³ is H or alkyl.

Table 1

PE# (A) (B) (C)i (C)ii (D) (E) (K) (H)

1 NyPT >10%BZ

2 NyPT DMI

3 NyPT (D4)

4 NyPT HCM

5 NyPT (D2)

6 NyPT SEA

7 NyPT (D5)

8 NyPT DML

9 NyPT (D1)

10 NyPT MPA

1 1 NyPT MPF

12 NyPT (D3)

13 NyPT LES

14 NyPT (C4)

15 NyPT PEI

16 NyPT (C1 )

17 NyPT NMM

18 NyPT (C5)

19 NyPT LES SEA

20 NyPT (C4) (D5)

21 NyPT PEI SEA

22 NyPT (C1 ) (D5)

23 NyPT SEA TEA

24 NyPT (D5) (K2)

25 NyPT NMM SEA NyPT (C5) (D5)

NyPT LES DML

NyPT (C4) (D1)

NyPT PEI DML

NyPT (C1 ) (D1)

NyPT DML TEA

NyPT (D1) (K2)

NyPT LES PEI DML

NyPT (C4) (C1) (D1)

NyPT LES NMM DML

NyPT (C4) (C5) (D1)

NyPT LES HCM

NyPT (C4) (D2)

NyPT PEI HCM

NyPT (C1 ) (D2)

NyPT HCM TEA

NyPT (D2) (K2)

NyPT NMM HCM

NyPT (C5) (D2)

NyPT NMM DML

NyPT (C5) (D1)

NyPT LES DML TEA

NyPT (C4) (D1) (K2)

NyPT LES DML BDA

NyPT (C4) (D1) (K3)

NyPT LES DML MDA

NyPT (C4) (D1) (K3)

NyPT PEI LES

NyPT (C1 ) (C4)

NyPT LES PEI HCM

NyPT (C4) (C1) (D2)

NyPT >10%BZ PG

NyPT DMI PG

NyPT (D4) PG

NyPT HCM PG

NyPT (D2) PG

NyPT SEA PG

NyPT (D5) PG

NyPT DML PG

NyPT (D1) PG

NyPT MPA PG

NyPT MPF PG NyPT (D3) PG

NyPT LES PG

NyPT (C4) PG

NyPT PEI PG

NyPT (C1 ) PG

NyPT NMM PG

NyPT (C5) PG

NyPT LES SEA PG

NyPT (C4) (D5) PG

NyPT PEI SEA PG

NyPT (C1 ) (D5) PG

NyPT SEA PG TEA

NyPT (D5) PG (K2)

NyPT NMM SEA PG

NyPT (C5) (D5) PG

NyPT LES DML PG

NyPT (C4) (D1) PG

NyPT PEI DML PG

NyPT (C1 ) (D1) PG

NyPT DML PG TEA

NyPT (D1) PG (K2)

NyPT LES PEI DML PG

NyPT (C4) (C1) (D1) PG

NyPT LES NMM DML PG

NyPT (C4) (C5) (D1) PG

NyPT LES HCM PG

NyPT (C4) (D2) PG

NyPT PEI HCM PG

NyPT (C1 ) (D2) PG

NyPT HCM PG TEA

NyPT (D2) PG (K2)

NyPT NMM HCM PG

NyPT (C5) (D2) PG

NyPT NMM DML PG

NyPT (C5) (D1) PG

NyPT LES DML PG TEA

NyPT (C4) (D1) PG (K2)

NyPT LES DML PG BDA

NyPT (C4) (D1) PG (K3)

NyPT LES DML PG MDA

NyPT (C4) (D1) PG (K3)

NyPT PEI LES PG NyPT (C1 ) (C4) PG

NyPT LES PEI HCM PG

NyPT (C4) (C1) (D2) PG

NyPT ≥10%BZ LPN

NyPT >10%BZ (K1 )

NyPT ≥10%BZ DMI

NyPT ≥10%BZ (D4)

NyPT ≥10%BZ HCM

NyPT ≥10%BZ (D2)

NyPT ≥10%BZ SEA

NyPT ≥10%BZ (D5)

NyPT ≥10%BZ DML

NyPT ≥10%BZ (D1)

NyPT ≥10%BZ MPA

NyPT ≥10%BZ MPF

NyPT >10%BZ (D3)

NyPT >10%BZ LES

NyPT ≥10%BZ (C4)

NyPT >10%BZ PEI

NyPT ≥10%BZ (C1 )

NyPT >10%BZ NMM

NyPT ≥10%BZ (C5)

NyPT >10%BZ LES SEA

NyPT ≥10%BZ (C4) (D5)

NyPT >10%BZ PEI SEA

NyPT ≥10%BZ (C1 ) (D5)

NyPT >10%BZ SEA TEA

NyPT ≥10%BZ (D5) (K2)

NyPT >10%BZ NMM SEA

NyPT ≥10%BZ (C5) (D5)

NyPT >10%BZ LES DML

NyPT ≥10%BZ (C4) (D1)

NyPT >10%BZ PEI DML

NyPT ≥10%BZ (C1 ) (D1)

NyPT >10%BZ DML TEA

NyPT >10%BZ (D1) (K2)

NyPT ≥10%BZ LES PEI DML

NyPT >10%BZ (C4) (C1) (D1)

NyPT ≥10%BZ LES NMM DML

NyPT >10%BZ (C4) (C5) (D1)

NyPT ≥10%BZ LES HCM 152 NyPT >10%BZ (C4) (D2)

153 NyPT ≥10%BZ PEI HCM

154 NyPT >10%BZ (C1 ) (D2)

155 NyPT ≥10%BZ HCM TEA

156 NyPT >10%BZ (D2) (K2)

157 NyPT ≥10%BZ NMM HCM

158 NyPT ≥10%BZ (C5) (D2)

159 NyPT ≥10%BZ NMM DML

160 NyPT ≥10%BZ (C5) (D1)

161 NyPT ≥10%BZ LES DML TEA

162 NyPT ≥10%BZ (C4) (D1) (K2)

163 NyPT ≥10%BZ LES DML BDA

164 NyPT ≥10%BZ (C4) (D1) (K3)

165 NyPT ≥10%BZ LES DML MDA

166 NyPT ≥10%BZ (C4) (D1) (K3)

167 NyPT >10%BZ PEI LES

168 NyPT ≥10%BZ (C1 ) (C4)

169 NyPT >10%BZ LES PEI HCM

147 NyPT ≥10%BZ (C4) (C1 ) (D2)

148 NyPT >10%BZ DEI

149 NyPT ≥10%BZ HBI

150 NyPT >10%BZ (C2)

151 NyPT ≥10%BZ E15

152 NyPT >10%BZ E25

153 NyPT ≥10%BZ (C4)

154 NyPT >10%BZ (C3)

155 NyPT DEI PG

156 NyPT HBI PG

157 NyPT (C2) PG

158 NyPT E15 PG

159 NyPT E25 PG

160 NyPT (C4) PG

161 NyPT (C3) PG

The advantages of the invention are that the enhancement of the stability of the (thio)phosphoric acid triamide(s) - particularly when applied to or coated on nitrogen-containing fertilizers such as urea - and a relatively long storage life - particularly before being applied to or coated on nitrogen-containing fertilizers - was achieved with the compositions (Q1 ), (Q2), (Q3). Moreover, the compositions (Q1 ), (Q2), (Q3) do not adversely affect the urease-inhibiting effect and/or activity of the (thio)phosphoric acid triamide. Last, but not least, the compositions (Q1 ), (Q2), (Q3) can be easily and safely packaged, transported and shipped, even in large quantities, and can be easily and safely handled and applied for soil treatment, even in large quantities

The examples which follow illustrate the invention without restricting it. Preparation of the formulations Preparation of the formulation

According to the ratios and components as specified in Table 2, all components were mixed, and the resulting mixture was stirred until complete dissolution of the solid and analyzed for the content of NBPT, NPPT, NxPT (by HPLC), viscosity, dissolution (2%) in water and pH.

For example, in case of Ex.# 310092, the technical mixture LT (25% pure NxPT) was mixed with 50.08% benzyl alcohole and 10% LFG,10% DML and 0.25% colo. The mixture was stirred until complete dissolution of the solid and analyzed for NxPT content (by HPLC), viscosity, dissolution (2%) in water and pH.

Formulation storage stability

The mixture of each example (e.g. Ex.#310092) was stored in closed bottles for 14 days at 54°C (referred to as heat stability test in the following) and then analyzed for the content of NxPT. The mixture of each example (e.g. Ex.#310092) was also stored in closed bottles for 14 days at 5°C (referred to as cold stability test in the following) and then analyzed for the content of NxPT. The storage stability in % was calculated as difference between the content in the heat stability test and the content in the cold stability test.

Coating of urea

Example 1 .1

500 g granulated urea was charged to a rotating drum (Type Hege 1 1) and 2g of the formulation of each example (e.g. Ex. #310092) was sprayed on the urea using a rotating disc. The homogeneous coated urea was discharged after 1 min and analyzed for the content of NBPT, NPPT, NxPT (by HPLC).

Stability on urea

The coated urea sample of 300 g was stored in a petri dish for 4 weeks at 50% humidity in a climate chamber. For analysis the sample was homogenized and analyzed for the content of NBPT, NPPT, NxPT (by HPLC)

The content of NxPT measured by HPLC measurement is always the sum of the both components NBPT and NBPT.

Viscosity was measured at the undiluted formulation with a cone-plate rheometer A 2000ex (TA Instruments) at shear rate of 100s^"1 and 20°C.

The pH value was measured at 2% concentration in CIPAC water D. All examples of the inventions are liquid, clear compositions which are either colourless or yellow.

Table 2: Examples of the compositions of the invention and of comparative compositions, and data on their viscosity, pH value, storage stability and stability after coated on urea Table 2 - part 1 of 1 1

Ex# 310007 310008 310010 310011 310012 310013 310014 310015

Inv. Inv. Inv. Inv. Inv. Inv. Inv. Inv.

29.67% 29.67% 29.67% 29.67% 29.67% 29.67% 29.67% 29.67%

(A) LT LT LT LT LT LT LT LT

PG ad100 ad 100 ad 100 ad100 ad 100 ad100 ad 100 ad100

BZ 20%

(C)i 20%LES

(C)ii

(D) 20% DM I 20%HCM 20%SEA 20%DML 20%MPA 20%MPF other

colo.

vise. 39 37 47 50 49 51 44 100 pH 8.2 8.1 8.4 7.5 8.1 8.2 8.2 9.6

NB/c 18.95% 19.20% 19.08% 18.81 % 18.89% 19.05% 18.68% 19.01 %

NP/c 5.82% 5.92% 5.85% 5.84% 5.75% 5.83% 5.72% 5.82%

Nx/c 24.77% 25.12% 24.93% 24.65% 24.64% 24.88% 24.40% 24.83%

NB/h 18.32% 18.86% 18.63% 18.57% 18.65% 18.68% 18.08% 18.51 %

NP/h 5.77% 5.92% 5.85% 5.91 % 5.81 % 5.84% 5.63% 5.77%

Nx/h 24.09% 24.78% 24.48% 24.48% 24.46% 24.52% 23.71 % 24.28% stabi. 97.25% 98.67% 98.20% 99.29% 99.27% 98.58% 97.14% 97.80%

Coat.

cone.

NB/a

NP/a

Nx/a

NB/b

NP/b

Nx/b

dev. Table 2 - part 2 of 11

Ex# 310016 310017 310021 310024 310025 310026 310027 310028

Inv. Inv. Inv. Inv. Inv. Inv. Inv. Inv.

29.67% 29.67% 29.67% 29.67% 29.67% 29.67% 29.67% 29.67%

(A) LT LT LT LT LT LT LT LT

PG ad100 ad 100 ad 100 ad100 ad 100 ad100 ad 100 ad100

BZ

(C)i 20%LFG 20%LGA 20%NMM 10%LES 10%LFG 10%LGA 10%TEA 10%NMM

(C)ii

(D) 10%SEA 10%SEA 10%SEA 10%SEA 10%SEA other

colo.

vise. 423 598 39 46 167 173 71 46 pH 10.7 10.6 9.4 9.3 10.3 10.2 9.2 9.1

NB/c 18.99% 19.06% 18.93% 18.85% 18.72% 18.71 % 18.84% 18.73%

NP/c 5.83% 5.86% 5.79% 5.97% 5.90% 5.92% 6.13% 6.04%

Nx/c 24.82% 24.92% 24.72% 24.82% 24.62% 24.63% 24.97% 24.77%

NB/h 18.50% 18.25% 18.80% 18.58% 18.59% 18.80% 18.27% 18.73%

NP/h 5.78% 5.70% 6.06% 5.89% 5.87% 5.94% 5.92% 5.96%

Nx/h 24.28% 23.95% 24.86% 24.47% 24.46% 24.74% 24.19% 24.69% stabi. 97.81 % 96.10% 100.54% 98.59% 99.36% 100.45% 96.88% 99.70%

Coat.

cone.

NB/a

NP/a

Nx/a

NB/b

NP/b

Nx/b

dev. Table 2 - part 3 of 11

Ex# 310029 310031 310032 310034 310035 310036 310037 310039

Inv. Inv. Inv. Inv. Inv. Inv. Inv. Inv.

29.67% 29.67% 29.67% 29.67% 29.67% 29.67% 29.67% 29.67%

(A) LT LT LT LT LT LT LT LT

PG ad100 ad 100 ad 100 ad100 ad 100 ad100 ad 100 ad100

BZ

(C)i 10%LES 10%LGA 10%TEA 10%LES 10%LES 10%LES 10%LES 10%LGA

(C)ii 10%LFG 10%LGA 10%NMM

(D) 10%DML 10%DML 10%DML 10%DML 10%DML 10%DML 10%HCM 10%HCM other

colo.

vise. 67 161 71 179 21 1 55 60 167 pH 9.4 10.4 9.3 10.5 10.4 9.4 9.4 10.4

NB/c 18.79% 19.06% 19.03% 18.51 % 18.71 % 18.98% 18.96% 18.84%

NP/c 5.80% 5.90% 5.88% 5.73% 5.76% 6.08% 5.88% 5.83%

Nx/c 24.59% 24.96% 24.91 % 24.24% 24.47% 25.06% 24.84% 24.67%

NB/h 18.87% 18.98% 18.71 % 18.62% 18.74% 18.98% 18.93% 18.79%

NP/h 5.83% 5.86% 5.80% 5.76% 5.79% 6.03% 5.87% 5.82%

Nx/h 24.70% 24.84% 24.51 % 24.38% 24.53% 25.01 % 24.80% 24.61 % stabi. 100.46% 99.52% 98.37% 100.60% 100.22% 99.80% 99.83% 99.73%

Coat.

cone.

NB/a

NP/a

Nx/a

NB/b

NP/b

Nx/b

dev. Table 2 - part 4 of 11

Ex# 310040 310041 310044 310045 310046 310047 310048 310049

Inv. Inv. Inv. Inv. Inv. Inv. Inv. Inv.

29.67% 29.67% 29.67% 29.67% 29.67% 29.67% 29.67% 29.67%

(A) LT LT LT LT LT LT LT LT

PG ad100 ad 100 ad100 ad100 ad 100 ad100 ad 100 ad100

BZ

(C)i 10%TEA 10%NMM 1 %LFG 3%LFG 10%LFG

(C)ii

(D) 10%HCM 10%HCM 20%HCM 20%SEA 20%DML 20%DML 20%DML 20%DML other

colo. 0.25% 0.25% 0.25% 0.25% 0.25% 0.25% vise. 72 46 53 53 51 58 71 144 pH 9.4 9.3 8.8 7.9 8.5 9.6 10.1 10.5

NB/c 18.83% 18.64% 18.48% 18.77% 18.70% 18.61 % 18.62% 18.62%

NP/c 5.78% 6.10% 5.79% 5.90% 5.80% 5.81 % 5.81 % 5.78%

Nx/c 24.61 % 24.74% 24.27% 24.67% 24.50% 24.42% 24.43% 24.40%

NB/h 18.54% 18.78% 18.50% 18.46% 18.67% 18.75% 18.67% 18.67%

NP/h 5.75% 5.95% 5.79% 5.82% 5.78% 5.83% 5.82% 5.80%

Nx/h 24.29% 24.73% 24.29% 24.28% 24.45% 24.58% 24.49% 24.47% stabi. 98.70% 100.00% 100.08% 98.43% 99.80% 100.65% 100.26% 100.30%

Coat.

cone. 0.10% 0.09% 0.10% 0.10% 0.10% 0.10%

NB/a 0.057% 0.060% 0.064% 0.063% 0.065% 0.067%

NP/a 0.017% 0.019% 0.020% 0.019% 0.020% 0.021 %

Nx/a 0.074% 0.079% 0.084% 0.082% 0.085% 0.088%

NB/b 0.004% 0.008% 0.010% 0.01 1 % 0.024% 0.054%

NP/b 0.002% 0.003% 0.004% 0.004% 0.008% 0.017%

Nx/b 0.006% 0.01 1 % 0.014% 0.015% 0.032% 0.071 % dev. -91 .89% -86.08% -83.33% -81.71 % -62.35% -19.32% Table 2 - part 5 of 11

Ex# 310050 310051 310052 310053 310059 310060 310061 310062

Inv. Inv. Inv. Inv. Inv. Inv. Inv. Inv.

29.67% 29.67% 29.67% 29.67% 29.67% 29.67% 29.67% 29.67%

(A) LT LT LT LT LT LT LT LT

PG ad100 ad 100 ad 100 ad100 50.33% 55.33% 50.33% 50.33%

BZ

(C)i 1 %NMM 3%NMM 10%NMM 20%NMM 10%LES 5%LES 5%NMM 5%TEA

(C)ii 5%LES 5%LES

10% 10% 10% 10%

(D) 20%DML 20%DML 20%DML 20%DML DML DML DML DML other

colo. 0.25% 0.25% 0.25% 0.25% 0.25% 0.25% 0.25% 0.25% vise. 55 51 48 43 73 66 62 76 pH 8.7 8.9 9.2 9.3 9.4 9.2 9.3 9.4

NB/c 19.13% 18.87% 18.59% 20.40% 19.00% 19.10% 19.05% 18.95%

NP/c 5.93% 5.88% 5.86% 6.42% 6.01 % 6.04% 6.04% 5.93%

Nx/c 25.06% 24.75% 24.45% 26.82% 25.01 % 25.14% 25.09% 24.88%

NB/h 19.05% 19.00% 19.26% 21.64% 19.17% 19.10% 19.30% 18.94%

NP/h 5.92% 5.88% 5.93% 6.90% 6.02% 5.99% 6.04% 5.93%

Nx/h 24.97% 24.88% 25.19% 28.54% 25.19% 25.09% 25.34% 24.87% stabi. 99.64% 100.53% 103.05% 106.40% 100.74% 99.81 % 101.02% 99.98%

Coat.

cone. 0.10% 0.10% 0.09% 0.10% 0.10% 0.09% 0.10% 0.10%

NB/a 0.067% 0.062% 0.061 % 0.048% 0.068% 0.065% 0.065% 0.066%

NP/a 0.021 % 0.019% 0.019% 0.015% 0.021 % 0.020% 0.020% 0.020%

Nx/a 0.088% 0.081 % 0.080% 0.063% 0.089% 0.085% 0.085% 0.086%

NB/b 0.011 % 0.009% 0.009% 0.010% 0.012% 0.01 1 % 0.008% 0.037%

NP/b 0.004% 0.003% 0.003% 0.003% 0.002% 0.002% 0.001 % 0.007%

Nx/b 0.015% 0.012% 0.012% 0.013% 0.014% 0.013% 0.009% 0.044% dev. -82.95% -85.19% -85.00% -79.37% -84.27% -84.71 % -89.41 % -48.84% Table 2 - part 6 of 11

Ex# 310063 310064 310065 310066 310077 310078 310079 310080

Inv. Inv. Inv. Inv. Inv. Inv. Inv. Inv.

29.67% 29.67% 29.67% 29.67% 29.67% 29.67% 29.67% 29.67%

(A) LT LT LT LT LT LT LT LT

PG 50.33% 50.33% 53.33% 48.33% 60.08% 55.08% 50.08% 60.08%

BZ

(C)i 5%LES 5%LES 2%LFG 2%LFG 10%LFG 15%LFG 20%LFG 8%LFG

(C)ii 5%LES 5%LES 2%LES

10% 10% 10% 10%

(D) DML DML DML DML

other 5%BDA 5%MDA

colo. 0.25% 0.25% 0.25% 0.25% 0.25% 0.25% 0.25% 0.25% vise. 69 71 83 72 175 286 486 153 pH 9.8 9.7 10,0 9.9 10.5 10.6 10.7 10.4

NB/c 18.86% 18.78% 18.84% 18.97% 19.12% 19.18% 19.15% 19.15%

NP/c 5.96% 5.93% 5.96% 6.03% 6.17% 6.19% 6.19% 6.22%

Nx/c 24.82% 24.71 % 24.80% 25.00% 25.29% 25.37% 25.34% 25.37%

NB/h 18.83% 18.93% 18.79% 19.16% 19.02% 19.13% 18.99% 18.98%

NP/h 5.92% 5.96% 5.91 % 6.01 % 6.07% 6.07% 6.06% 5.98%

Nx/h 24.75% 24.89% 24.70% 25.17% 25.09% 25.20% 25.05% 24.96% stabi. 99.70% 100.72% 99.61 % 100.66% 99.24% 99.33% 98.84% 98.38%

Coat.

0.08% 0.08% 0.08% 0.08% cone. 0.10% 0.10% 0.10% 0.10% Target Target Target Target

NB/a 0.063% 0.068% 0.068% 0.067% 0.056% 0.058% 0.058% 0.054%

NP/a 0.019% 0.021 % 0.021 % 0.021 % 0.018% 0.019% 0.019% 0.018%

Nx/a 0.082% 0.089% 0.089% 0.088% 0.074% 0.077% 0.077% 0.072%

NB/b 0.038% 0.040% 0.017% 0.017% 0.048% 0.053% 0.048% 0.041 %

NP/b 0.008% 0.008% 0.003% 0.003% 0.014% 0.016% 0.014% 0.011 %

Nx/b 0.046% 0.048% 0.020% 0.020% 0.062% 0.069% 0.062% 0.052% dev. -43.90% -46.07% -77.53% -77.27% -16.22% -10.39% -19.48% -27.78% Table 2 - part 7 of 11

Ex# 310081 310082 310083 310084 310086 310087 310073 310088

Inv. Inv. Inv. Inv. Inv. Inv. Inv. Inv.

29.67% 29.67% 29.67% 29.67% 29.67% 29.67% 29.67% 29.67%

(A) LT LT LT LT LT LT LT LT

PG 50.08% 50.08% 50.08% 50.08% 49.08% 47.08%

BZ 70.33% 60.08%

(C)i 10%LFG 10%LFG 8%LFG 8%LFG 8%LFG 8%LFG 10%LFG

(C)ii 2%LES 2%LES 2%LES 2%LES

(D) 10%DML 10%HCM 10%DML 10%HCM 10%DML 10%DML

other 1 %TPA 3%TPA

colo. 0.25% 0.25% 0.25% 0.25% 0.25% 0.25% 0.25% vise. 152 156 127 127 129 140 1 1 34 pH 10.5 10.5 10.4 10.4 10.4 10.4 8.5 10.6

NB/c 19.11 % 19.23% 19.45% 19.66% 19.22% 18.91 % 19.21 % 19.17%

NP/c 6.16% 6.23% 6.24% 6.33% 6.16% 6.07% 6.23% 6.19%

Nx/c 25.27% 25.46% 25.69% 25.99% 25.38% 24.98% 25.44% 25.36%

NB/h 19.03% 19.1 1 % 19.34% 19.26% 19.48% 19.57% 18.28% 19.00%

NP/h 5.96% 6.01 % 6.08% 6.06% 6.10% 5.97% 5.93% 6.13%

Nx/h 24.99% 25.12% 25.42% 25.32% 25.58% 25.54% 24.21 % 25.13% stabi. 98.90% 98.66% 98.94% 97.44% 100.78% 102.24% -4.85% -0.91 %

Coat.

0.08% 0.08% 0.08% 0.08% 0.08% 0.08% 0.08% cone. Target Target Target Target Target Target Target

NB/a 0.057% 0.055% 0.057% 0.053% 0.056% 0.057% 0.060%

NP/a 0.019% 0.018% 0.018% 0.017% 0.018% 0.019% 0.019%

Nx/a 0.076% 0.073% 0.075% 0.070% 0.074% 0.076% 0.079%

NB/b 0.040% 0.044% 0.042% 0.045% 0.040% 0.038% 0.049%

NP/b 0.011 % 0.012% 0.01 1 % 0.013% 0.01 1 % 0.010% 0.014%

Nx/b 0.051 % 0.056% 0.053% 0.058% 0.051 % 0.048% 0.063% dev. -32.9% -23.3% -29.3% -17.1 % -31.1 % -36.8% -20.25% Table 2 - part 8 of 11

Ex# 310089 310090 310091 310092 310093 310094 310095 310096

Inv. Inv. Inv. Inv. Inv. Inv. Inv. Inv.

29.67% 29.67% 29.67% 29.67% 29.67% 29.67% 29.67% 29.67%

(A) LT LT LT LT LT LT LT LT

PG

BZ 55.08% 50.08% 60.08% 50.08% 50.08% 50.08% 50.08% 55.08%

(C)i 15%LFG 20%LFG 8%LFG 10%LFG 10%LFG 8%LFG 8%LFG

(C)ii 2%LES 2%LES 2%LES

(D) 10%DML 10%HCM 10%DML 10%HCM other 15% LPN colo. 0.25% 0.25% 0.25% 0.25% 0.25% 0.25% 0.25% 0.25% vise. 70 121 32 42 40 34 34 35 pH 10.6 10.7 10.5 10.5 10.5 10.4 10.5 1 1.4

NB/c 19.33% 19.08% 19.25% 19.1 1 % 19.00% 19.12% 19.68% 17.77%

NP/c 6.23% 6.15% 6.20% 6.17% 6.16% 6.14% 6.33% 5.73%

Nx/c 25.56% 25.23% 25.45% 25.28% 25.16% 25.26% 26.01 % 23.50%

NB/h 18.95% 19.07% 19.02% 18.97% 18.86% 19.08% 19.34% 15.60%

NP/h 6.15% 6.18% 6.14% 6.07% 6.08% 6.14% 6.24% 4.92%

Nx/h 25.10% 25.25% 25.16% 25.04% 24.94% 25.22% 25.58% 20.52% stabi. -1.82% 0.09% -1.15% -0.97% -0.89% -0.15% -1 .65% -12.68%

Coat.

0.08% 0.08% 0.08% 0.08% 0.08% 0.08% 0.08% 0.08% cone. Target Target Target Target Target Target Target Target

NB/a 0.061 % 0.058% 0.061 % 0.057% 0.059% 0.062% 0.065% 0.059%

NP/a 0.019% 0.018% 0.019% 0.018% 0.018% 0.019% 0.020% 0.019%

Nx/a 0.080% 0.076% 0.080% 0.075% 0.077% 0.081 % 0.085% 0.078%

NB/b 0.052% 0.051 % 0.046% 0.049% 0.050% 0.051 % 0.048% 0.050%

NP/b 0.016% 0.016% 0.013% 0.014% 0.015% 0.015% 0.014% 0.015%

Nx/b 0.068% 0.067% 0.059% 0.063% 0.065% 0.066% 0.062% 0.065% dev. -15.00% -1 1.84% -26.25% -16.00% -15.58% -18.52% -27.06% -16.67% Table 2 - part 9 of 11

Ex# 310104 310105 310106 310108 310109 3101 10 3101 1 1

Inv. Inv. Inv. Inv. Inv. Inv. Inv.

29,67% 29,67% 25% 29.34% 29.34% 29.34% 29.34%

(A) LT LT NBPT LL LL LL LL

PG

BZ 50.08% 40.08% 54.75% 50.41 % 40.41 % 60.41 % 60.41 %

(C)i 20%LFG 30%LFG 20%LFG 20%LFG 30%LFG 10% DEI 10%HBI

(C)ii

(D)

other

colo. 0.25% 0.25% 0.25% 0.25% 0.25% 0.25% 0.25% vise. 132 345 94 1 15 314 18 18 pH 10.5 10.6 10.7 12.3 9.1 8.7 9.1

NB/c 18.56% 18.62% 25.17% 19.79% 19.72% 19.32% 19.78%

NP/c 5.82% 5.89% 0.00% 6.19% 6.19% 6.06% 6.12%

Nx/c 24.38% 24.51 % 25.17% 25.98% 25.91 % 25.38% 25.90%

NB/h 18.70% 19.01 % 25.59% 19.90% 19.90% 19.41 % 19.40%

NP/h 5.95% 5.94% 0.00% 6.21 % 6.18% 6.16% 5.88%

Nx/h 24.65% 24.95% 25.59% 26.1 1 % 26.08% 25.57% 25.28% stabi. 1.1 1 % 1.80% 1.67% 0.50% 0.66% 0.75% -2.39%

Coat.

NB/a 0.058% 0.057% 0.077% 0.060% 0.059% 0.063% 0.065%

NP/a 0.019% 0.019% 0.000% 0.019% 0.019% 0.019% 0.020%

Nx/a 0.077% 0.076% 0.077% 0.079% 0.078% 0.082% 0.085%

NB/b

NP/b

Nx/b

dev. Table 2 - part 10 of 1 1

NMP (at least in amounts as applied in Ex# 310043) is toxicologically objectionable. Table 2 - part 1 1 of 1 1

Ex# 310120 310121 310122 310123 310022 310043 310085

Inv. Inv. Inv. Inv. Comp. Comp. Comp.

29.34% 29.34% 29.34% 29.34% 29.67% 29.67% 29.67%

(A) LL LL LL LL LT LT LT

PG 60.41 % 60.41 % 40.41 % 40.41 % ad100 ad 100 55.08%

BZ

(C)i 10%E15 10%E25 30%E15 30%E25

(C)ii

(D)

other 20%LPN 20%NMP 15%LPN colo. 0.25% 0.25% 0.25% 0.25% 0.25% 0.25% vise. 75 81 114 140 181 36 141 pH 9.1 9.3 9.3 9.3 1 1.2 8.5 1 1.3

NB/c 20.05% 19.70% 20.04% 19.70% 18.39% 18.68% 18.12%

NP/c 6.25% 6.14% 6.25% 6.13% 5.71 % 5.86% 5.83%

Nx/c 26.30% 25.84% 26.29% 25.83% 24.10% 24.54% 23.95%

NB/h 20.07% 19.77% 19.82% 19.39% 15.67% 18.52% 16.38%

NP/h 6.28% 6.18% 6.18% 6.09% 4.91 % 5.81 % 5.21 %

Nx/h 26.35% 25.95% 26.00% 25.48% 20.58% 24.33% 21.59% stabi. 0.19% 0.43% -1.10% -1.36% 85.41 % 99.16% 90.1 1 %

Coat.

0.08% 0.08% 0.08% 0.08% 0.08% cone. Target Target Target Target 0.10% Target

NB/a 0.063% 0.062% 0.062% 0.062% 0.064% 0.053%

NP/a 0.020% 0.019% 0.019% 0.019% 0.019% 0.016%

Nx/a 0.083% 0.081 % 0.081 % 0.081 % 0.083% 0.069%

NB/b 0.005% 0.039%

NP/b 0.002% 0.010%

Nx/b 0.007% 0.049% dev. -91.57% -29.0%

Claims

laims

1. An composition comprising:

R R²N-P(X)(NH₂)₂ ,

wherein

X is oxygen or sulfur;

R¹ is a Ci to C20 alkyl, C3 to C20 cycloalkyl, Ce to C20 aryl, or dialkylaminocar- bonyl group;

R² is H , or

and

(C) at least one amine selected from the group consisting of

(C1 ) a polymeric polyamine, and

(C2) an amine containing not more than one amino group and at least three alkoxy- or hydroxy-substituted C2 to Ci₂ alkyl groups R²¹ , wherein at least one of the groups R²¹ is different to the other groups R²¹ , and

(C4) an amine containing at least one saturated or unsaturated Cs to C40 alkyl group R²³, and

The composition according to claim 1 , wherein in the general formula (I) of (A) X is sulfur.

The composition according to claim 1 or 2, wherein in the general formula (I) of (A) R¹ is C1-C20 alkyl and R² is H .

The composition according to anyone of the claims 1 to 3, wherein the mixture (A) comprises N-n-butylthiophosphoric acid triamide (NBPT) and/or N-n-propylthiophosphoric acid triamide (NPPT).

5. The composition according to claim 1 , wherein the mixture (A) comprises at least two different (thio)phosphoric acid triamides having structures of the general formula (I) and wherein said at least two different (thio)phosphoric acid triamides differ in at least one of radicals ¹ or R².

6. The composition according to claim 6, wherein one of said at least two different

(thio)phosphoric acid triamides is N-n-butylthiophosphoric acid triamide.

7. The composition according to anyone of the claims 1 to 6, wherein (C) is

(C1 ) a polymeric polyamine.

8. The composition according to anyone of the claims 1 to 6, wherein (C) is (C1 ) which is a polyalkylene imine.

9. The composition according to anyone of the claims 1 to 6, wherein (C) is (C1 ) which is a polyethylene imine.

10. The composition according to anyone of the claims 1 to 6, wherein (C) is

(C2) an amine containing not more than one amino group and at least three alkoxy- or hydroxy-substituted C2 to C12 alkyl groups R²¹, wherein at least one of the groups R²¹ is different to the other groups R²¹.

1 1. The composition according to anyone of the claims 1 to 6, wherein (C) is

(C2) an amine containing not more than one amino group and at least three hydroxy- substituted C2 to C3 alkyl groups which are covalently bound to the amino group.

12. The composition according to anyone of the claims 1 to 6, wherein (C) is

(C2) an amine selected from the group consisting of Bis(hydroxyethyl)-isopropanolamine (DEIPA), and 1 ,1 '-((2-Hydroxyethyl)imino)dipropan-2-ol.

13. The composition according to anyone of the claims 1 to 6, wherein (C) is

(C3) an amine containing not more than one amino group and at least two alkoxy- or hydroxy-substituted C2 to C12 alkyl groups R²², wherein at least one of said alkyl groups bears the alkoxy or hydroxy substituent at a secondary or tertiary carbon atom and wherein at least one of the groups R²² is different to the other group(s) R²².

14. The composition according to anyone of the claims 1 to 6, wherein (C) is

(C3) an amine selected from the group consisting of 1-((2-hydroxyethyl)amino)propan-2- ol, and N-Methyl-N-hydroxyethyl-isopropanolamine.

15. The composition according to anyone of the claims 1 to 6, wherein (C) is

(C) an amine which is

16. The composition according to anyone of the claims 1 to 6, wherein (C) is

(C4) an amine containing at least one saturated or unsaturated Cs to C19 alkyl group ²³.

17. The composition according to anyone of the claims 1 to 6, wherein (C) is

(C4) an amine selected from the group consisting of ethoxylated (2) cocoalkylamine, ethoxylated (5) cocoalkylamine, ethoxylated (15) cocoalkylamine, ethoxylated (2) oleyla- mine, lauryl-dimethylamine, oleyl-dimethylamine, and 2-propylheptylamine ethoxylate (5 EO), 2-propylheptylamine ethoxylate (10 EO), and 2-propylheptylamine ethoxylate (20 EO).

18. The composition according to anyone of the claims 1 to 6, wherein (C) is

(C5) a saturated or unsaturated heterocyclic amine which contain at least one oxygen atom as ring atom and which do not contain a further alkoxy group.

19. The composition according to anyone of the claims 1 to 6, wherein (C) is

(C5) an amine which is N-methyl morpholine.

20. The composition according to claim 1 , wherein

the mixture (A) comprises N-n-butylthiophosphoric acid triamide (NBPT) and/or N-n- propylthiophosphoric acid triamide (NPPT) and

(C) is (C1 ) a polymeric polyamine which is polyethyleneimine.

21. The composition according to anyone of the claims 1 to 20, further comprising

(B) an aromatic alcohol according to the general formula (II)

wherein

R¹¹ is aryl or alkylaryl;

R¹² is H or alkyl;

R¹³ is H or alkyl.

22. The composition according to anyone of the claims 1 to 21 , further comprising (B), wherein in the general formula (II) of (B) R¹² and R¹³ is H.

23. The composition according to anyone of the claims 1 to 22, further comprising (B), wherein in the general formula (II) of (B) R¹¹ is aryl.

24. The composition according to anyone of the claims 1 to 23, further comprising (B), wherein in the general formula (II) of (B) R¹¹ is phenyl.

25. The composition according to anyone of the claims 1 to 24, further comprising (B), wherein (B) is benzyl alcohol.

26. The composition according to anyone of the claims 1 to 25, further comprising

(D) at least one amide according to the general formula (III)

3 CO-NR³²R³³

wherein

R³¹CO is an acyl radical having 1 to 22 carbon atoms;

R³² is H or alkyl, and

R³³ is H or alkyl, or

R³² and R³³ together with the nitrogen atom linking them define a 5- or 6-membered saturated or unsaturated heterocyclic radical, which optionally comprises 1 or 2 further heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur.

27. The composition according to anyone of the claims 1 to 26, wherein in the general formula (III) of (D) R³² is H or Ci to C₄ alkyl, and R³³ is H or Ci to C₄ alkyl.

28. The composition according to anyone of the claims 1 to 27, wherein in the general formula (III) of (D) R³¹CO is a hydroxysubstituted acyl radical having 1 to 22 carbon atoms.

29. The composition according to anyone of the claims 1 to 28, wherein (D) is a N,N-dialkyl amide based on lactic acid, citric acid, tartaric acid, ricinoleic acid, 12-hydroxy stearic acid, or their mixtures.

The composition according to anyone of the claims 1 to 29, wherein (D) is a lactic acid N,N-dimethylamide.

The composition according to anyone of the claims 1 to 27, wherein in the general formula of (D) R³¹CO does not contain a hydroxy group.

32. The composition according to anyone of the claims 1 to 27 and 31 , wherein in the general formula (III) of (D) R³¹CO is an acyl radical having 6 to 12 carbon atoms.

33. The composition according to anyone of the claims 1 to 27 and 31 to 32, wherein (D) is selected from the group consisting of Ν,Ν-dimethyloctanamide, N,N-dimethylnonanamide, and N,N-dimethyldecanamide.

34. The composition according to anyone of the claims 1 to 27 and 31 , wherein in the general formula (III) of (D) R³¹CO is an acyl radical having 1 to 3 carbon atoms.

35. The composition according to anyone of the claims 1 to 26, wherein in the general formula (III) of (D) R³² and R³³ together with the nitrogen atom linking them define a 5- or 6- membered saturated or unsaturated heterocyclic radical which optionally comprises 1 or 2 further heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur.

36. The composition according to anyone of the claims 1 to 26 and 35, wherein in the general formula (III) of (D) ³² and R³³ together with the nitrogen atom linking them define a 6- membered saturated heterocyclic radical which comprises one further oxygen heteroatom.

37. The composition according to anyone of the claims 1 to 26 and 35 to 36, wherein (D) is N- acetylmorpholine or N-formylmorpholine.

38. The composition according to anyone of the claims 1 to 26 and 35, wherein in the general formula (III) of (D) R³² and R³³ together with the nitrogen atom linking them define a 5- membered saturated heterocyclic radical which comprises one further nitrogen heteroatom.

39. The composition according to anyone of the claims 1 to 26, 35, and 38, wherein (D) is 1 ,3- dimethyl-2-imidazolidinone.

40. The composition according to anyone of the claims 1 to 27, wherein in the general formula (III) of (D) R³² is an acyloxy substituted alkyl group.

41. The composition according to anyone of the claims 1 to 27, wherein in the general formula (III) of (D) R³¹CO is an acyl radical having 1 to 4 carbon atoms, R³² is an acyloxy substituted alkyl group and R³³ is Ci to C4 alkyl.

42. The composition according to anyone of the claims 1 to 27, wherein (D) is N-[2- (acetyloxy)ethyl]-N-methyl acetamide.

43. The composition according to anyone of the claims 1 to 42, further comprising

(E) an alcohol comprising at least two hydroxy groups which are not dissociable in the aqueous medium.

44. The composition according to anyone of the claims 1 to 42, further comprising

(E) propane-1 ,2-diol (alpha-propylene glycol).

45. The composition according to anyone of the claims 1 to 44, further comprising a com- pound (K) selected from the group consisting of

(K1) an amine selected from the group consisting of methyldiethanolamine, tetrahydroxy- propylethylenediamine, trimethylaminoethylethanolamine, N,N,N',N'-tetramethyl-1 ,6- hexanediamine, N,N',N"-tris(dimethylaminopropyl)hexahydrotriazine, and 2,2'- dimorpholinyldiethyl ether, an amine containing not more than one amino group and at least three alkoxy- or hydroxy-substituted C2 to C12 alkyl groups R⁴¹, wherein all groups R⁴¹ within said amine are identical, and

an amine containing not more than one amino group and at least two alkoxy- or hydroxy-substituted C2 to C12 alkyl groups R⁴², wherein at least one of the groups R⁴² bears the alkoxy or hydroxy substituent at a secondary or tertiary carbon atom and wherein all groups R⁴² with said amine are identical.

46. The composition according to anyone of the claims 1 to 45, further comprising

(F) a nitrogen-containing fertilizer.

47. The composition according to anyone of the claims 1 to 45, further comprising

(F1 ) a urea-containing fertilizer comprising at least one component selected from the group consisting of urea, urea ammonium nitrate (UAN), isobutylidene diurea (IBDU), cro- tonylidene diurea (CDU) and urea formaldehyde (UF), urea-acetaldehyde, and urea- glyoxal condensates.

48. The composition according to anyone of the claims 1 to 45, further comprising

(F) a nitrogen-containing fertilizer which comprises urea.

49. Process for treating the soil comprising:

applying the composition according to anyone of the claims 1 to 48 into the soil in-furrow and/or as side-dress and/or as broadcast.

Process according to claim 49 comprising:

applying the composition by spraying it onto the

Process according to claim 49, wherein the composition is - either at the same time or with a time difference - applied together with at least one nitrogen-containing fertilizer ( into the soil in-furrow and/or as side-dress and/or as broadcast.

52. Use of the composition according to anyone of the claims 1 to 45 as additive or coating material for nitrogen-containing fertilizers (F).