BE1030915A1 - Anilino derivatives as plant growth promoters - Google Patents

Description

Anilino derivatives as plant growth promoters

Description

The present invention relates to plant growth promoters, a method for promoting the growth of a plant, a mixture for promoting the growth of a plant, a fertilizer mixture, a process for their production and a method for fertilizing the soil.

The use of nitrogen and phosphorus in the form of fertilizers is necessary to meet the food demand of a growing population. Fertilization must be site-specific to ensure optimal crop production with minimal environmental pollution.

Root hairs are important for the absorption of nutrients and water by plants.

Induction of root hairs and root hair elongation results in a larger total root and root hair surface area and therefore in greater nutrient uptake, especially phosphorus, but also nitrogen, iron and other nutrients, and water, and leads to better tolerance to nutrient starvation or drought stress or can improve plant growth and yield. Likewise, root hairs provide increased tolerance to salt stress and osmotic stress. They are important in stress responses, not only by increasing the recording surface, but also as a biosensor. Root hairs are also important for anchoring and penetration into the soil. In this way they ensure better growth in strong (compact) soils. Root hairs improve root-soil contact and provide the site of symbiotic interactions with soil-dwelling microorganisms. The latter include arbuscular mycorrhiza and ectomycorrhiza. These fungi can create an extensive network in the soil to capture and transport nutrients and water to the plants, but also help in the search for water or nutrients, indicating the direction in which the roots should grow. Root hairs are also directly involved in the formation of root nodules in legumes to form a symbiosis with nitrogen-fixing bacteria, thus improving nitrogen nutrition.

In addition, root hairs prevent harmful microorganisms from entering the plant. Root hair cells also secrete acids (e.g. malic and citric acids), which dissolve minerals in the soil to release nutrients. For example, these acids make phosphate available to the plant from phosphorus-containing sources in the soil, such as rock phosphate or mineralized phosphate. As a result, a greater number of root hairs or a larger root surface area generally improves the fitness and growth efficiency of the plant. These roles and benefits are demonstrated or discussed in numerous peer-reviewed articles, including Vissenberg et al., 2020, J Exp Bot. , 71(8):2412-2427; Wang et al., 2020,

Plant Physiol., 184(1):176-193; Zou et al., 2019, Pak. J. Bot, 51(2); Kwasniewski et al., 2016,

JExp Bot., 67(4):1079-94; Haling et al., 2013, J Exp Bot. , 64(12):3711-3721; Wang et al, 2008,

J Plant Res, 121:87-96; Grierson and Schiefelbein, 2002, Arabidopsis Book. , 1:e0060.

The aim of this invention is to provide compounds as fertilizer additives that can act as plant growth promoters by increasing the total root hair surface area of plants. Preferably, the compounds reduce/soothe hunger or

2 BE2022/5772 drought stress of plants and/or they increase the efficiency of the use of nutrients (fertilizers) and/or they improve the absorption of nutrients or water by plants.

The objectives are achieved by using a compound with the general formula (I)

R1 R2

Dx (I) with the following definitions:

X heteroatom, selected from the group consisting of nitrogen, oxygen and sulfur, wherein X is preferably nitrogen;

R1; R2 is independently hydrogen, C1-3 hydrocarbon residue, preferably a C1-10, more preferably a C1-5 hydrocarbon residue, more preferably a C1-3 hydrocarbon residue, which may contain one to three halogen atoms and/or one to seven heteroatoms , selected from the group consisting of nitrogen, oxygen and sulfur, preferably R1 or R2 has a keto group, more preferably the keto group is on C2 of R1 or R2;

R3 independently hydrogen, halogen, heteroatom functional group, C17 hydrocarbon residue, C1; -hydrocarbon residue, preferably one

Cs -hydrocarbon residue, which may contain one or two halogen atoms and/or one to three heteroatoms, selected from the group consisting of nitrogen, oxygen and sulphur, preferably oxygen, it being also possible that R1 and R3 are covalently linked to form a heterocyclic ring with 5 to 8 members, which may contain 1 or 2 halogen atoms and/or 1 to 3 other heteroatoms in addition to the heteroatoms N already part of the heterocyclic ring, wherein R3 is preferably a methoxy group n 0; 1; 2; 3; 4 or 5, where n is preferably 0 or 1; as a growth promoter for plants.

3 BE2022/5772

According to this invention it has been found that compounds of the above general formula (I) can be successfully used as plant growth promoters or root hair inducers or a combination thereof. They induce root hairs and root hair elongation and improve the nutrient use efficiency and water uptake of plants. They reduce/mitigate the nutrient hunger or drought stress of plants.

A preferred option is to use the compound of the general formula (I)

R1 R2 x Pt >) (I)

With the following definitions:

X heteroatom, selected from the group consisting of nitrogen and oxygen, wherein X is preferably nitrogen;

R1; R2 if X is nitrogen, R1 and R2 are independently hydrogen or one

C 1 - hydrocarbon residue, preferably a C 1 hydrocarbon residue, which may contain one to seven heteroatoms selected from the group consisting of nitrogen, oxygen and sulphur, preferably R 1 or R 2 has a keto group and/or an amino group, more preferably R1 is a C2 hydrocarbon with a carboxamide group on C2 of R1 and R2 is hydrogen;

R1 when

R3 independently hydrogen, halogen, heteroatom functional group, C12 hydrocarbon residue, preferably a C1; -hydrocarbon residue, more preferably a C,; -hydrocarbon residue, which may contain one or two halogen atoms and/or one to three heteroatoms, selected from the group consisting of nitrogen, oxygen and sulfur, preferably oxygen, it is also possible that R1 and R3 are covalently linked to form a heterocyclic ring

4 BE2022/5772 with 5 to 8 members, which may contain 1 or 2 halogen atoms and/or 1 to 3 other heteroatoms in addition to the heteroatoms N that are already part of the heterocyclic ring, wherein R3 is preferably a hydrogen, a methyl group or a methoxy group is;

N0; 1; 2; 3; 4 or 5, where n is preferably 0 or 1; as a plant growth promoter, in which the plant growth promoter improves - root hair development, - Phosphate use efficiency/uptake - plant nutrient use efficiency, - nutrient uptake by plants, - nutrient availability, - water uptake by plants, - food and water supply by plants , - drought resistance, - root penetration into the soil, - anchorage in the soil, - useful symbiotic interactions of plants, - protection against harmful micro-organisms, and/or - plant growth or yield; and/or to alleviate and/or reduce nutrient starvation, drought, salt and/or osmotic stress in plants.

Preferably the compound of formula (I) is one of the following compounds:

NH, in 5

NE HO Me

Od D

HC Gr Hé ì a “, 1 >

HO 2

DQC :

0 Et, Mer,

HC H,C

The T Ch > in HN AA

Ses nan 3 D

CO € © CE ©

N ne ; we (0 ° Das ii ch. un ;

No { ; r 1 9 ee

CH; o DN '5 =

Hi Ch; ;

N.CH,

Es De L ‚

OE A

CH;

MOL u

H.C 2 c A

Ng me CH, Y NM o ww“ Se

G

Nn

D

HC t,

HG Os 205 D

Thu D {} TD Hs fe. CHa N

ST { ; ' and, 1 ©.

HO

CH, hey, HO, © HR 70 ' Ÿ

DesNaH 2.7; > 5 Particular preference is given to the compound of formula (II)

6 BE2022/5772

Ve

A

[> (N)

Preferably the pH value of the substrate or soil is between 4.5 and 7.5, preferably between 5 and 7, and even more preferably between 5.5 and 6.5.

The use of the compounds of formula (|) or formula (II) is preferably aimed at improving - root hair development, - efficiency of nutrient use of plants, - absorption of nutrients by plants, - availability of nutrients, - water absorption of plants , - food and water supply by plants, - drought resistance, - root penetration into the soil, - anchorage in the soil, - useful symbiotic interactions of plants, - protection against harmful microorganisms, - plant growth or yield or for illumination and/ or reducing food hunger, drought, salt and/or osmotic stress in plants.

The object is further achieved by a method for promoting the growth of a plant, whereby a compound as described above is added to the growing medium or soil in which the plant is grown.

The invention further relates to a mixture containing at least one compound of general formula (I) as defined above, and at least one additional agrochemical agent, preferably selected from the group consisting of - at least one inorganic and/or organic and /or organomineral fertilizer - at least one nitrification inhibitor, preferably selected from the group consisting of 2-(3,4-dimethyl-pyrazol-1-yl)-succinic acid (DMPSA), 3,4-dimethylpyrazole (DMP), 3, 4-dimethylpyrazole phosphate (DMPP), dicyandiamide (DCD), 1H-1,2,4-triazole, 3-methylpyrazole (3-MP), 2-chloro-6-(trichloromethyl)-pyridine, 5-ethoxy-3-trichloromethyl -1,2,4-thiadiazole, 2-amino-4-chloro-6-methyl-pyrimidine, 2-mercapto-benzothiazole, 2-sulfanilamidothiazole, thiourea, sodium azide, potassium azide, 1-

7 BE2022/5772 hydroxypyrazole, 2-methylpyrazole-1-carboxamide, 4-amino-1,2,4-triazole, 3-mercapto-1,2,4-triazole, 2,4-diamino-6-trichloromethyl-5- triazine, carbon bisulfide, ammonium thiosulfate, sodium trithiocarbonate, 2,3-dihydro-2,2-dimethyl-7-benzofuranol methyl carbamate and N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-alanine methyl ester, - at least one urease inhibitor , preferably selected from N-n-butylthiophosphorus triamide (NBTPT or NBPT) and/or N-n-propylthiophosphorus triamide (NPTPT or NPPT), - at least one common agrochemical additive, preferably selected from the group consisting of aqueous and/or organic solvents, pH- regulators, surfactants, wetting agents, spreading agents, adhesion promoters, carriers, fillers, viscosity regulators, emulsifiers, dispersants, sequestering agents, anti-caking agents, coalescing agents, rheology modifiers, anti-foaming agents, photoprotectors, antifreezes, (additional or further) biostimulators, pesticides/plant protection products, biocides, (additional or further) plant growth regulators, protectants, penetrants, anti-caking agents, mineral and/or vegetable oils and/or waxes, dyes and drift control agents, and mixtures thereof.

The invention further relates to a mixture of fertilizers containing:

A. an inorganic and/or organic and/or organic-mineral fertilizer and

B. 10 to 10000 percent by weight, based on the fertilizer, of a compound of the general formula (|) as defined above.

The invention further relates to a process for the manufacture of the fertilizer mixture described above by introducing the compound of the general formula (|) into the fertilizer and/or applying the compound of the general formula (I) to the surface of the fertilizer to bring.

The invention further relates to a method for fertilizing agricultural or horticultural land, including house and garden, in which a fertilizer mixture containing compounds A and B

A. an inorganic and/or organic and/or organic-mineral fertilizer and

B. an effective amount, preferably 10 to 10,000 percent by weight, more preferably 100 to 3,000 percent by weight, based on the fertilizer, of a compound of the general formula (|) as described above, or compounds A and B separately, but within is applied to or in the soil for a period of 0 to 5 hours, preferably 0 to 1 hour, preferably approximately simultaneously, using any application technique.

The term "independent" means that the meaning for each residue can be chosen independently of the meaning for another member or the binding position of said residues. For example, Rt and R3 can be the same or different.

The compounds of the present invention can be combined with a nitrification inhibitor and/or a urease inhibitor.

8 BE2022/5772

Furthermore, especially if the fertilizer contains urea, the compound can also be used together with or in combination with a urease inhibitor, preferably selected from N-n-butylthiophosphorus triamide (NBTPT or NBPT) and/or N-n-propylthiophosphorus triamide (NPTPT or

NPPT).

The compounds of the present invention can also be combined with a nitrification inhibitor and a urease inhibitor, especially in the case of fertilizers containing ammonium and urea and a phosphorus source.

When the compound of the present invention is combined with a nitrification inhibitor, the weight ratio between the compound of the present invention and the nitrification inhibitor is preferably 0.01 to 100:1, preferably 0.1 to 10:1.

When the compound of the present invention is combined with a urease inhibitor, the weight ratio between the compound of the present invention and the urease inhibitor is preferably between 0.01 and 100:1, preferably between 0.1 and 10:1.

If the nitrification inhibitor is combined with N-n-butylthiophosphorus triamide (NBTPT) and/or N-n-propylthiophosphorus triamide (NPTPT), the weight ratio between nitrification inhibitor(s) and urease inhibitor is preferably between 0.1 and 10: 1, preferably between 0.5 and 8:1, and preferably between 1 and 6:1.

Furthermore, the compounds of the present invention can be combined with an inorganic and/or organic and/or organic-mineral fertilizer, in particular a fertilizer containing a phosphorus source.

Furthermore, it is possible to combine the compounds of the present invention with at least one common agrochemical (auxiliary) agent.

Therefore, the present invention defines a mixture of the compounds of general formula (I) as defined above, with - at least one fertilizer, or - at least one nitrification inhibitor, preferably selected from the group consisting of 2-(3,4-dimethyl -pyrazol-1-yl)-succinic acid (DMPSA), 3,4-dimethylpyrazole (DMP), 3,4-dimethylpyrazole phosphate (DMPP) dicyandiamide (DCD), 1H-1,2,4-triazole, 3-methylpyrazole (3 -MP), 2-chloro-6-(trichloromethyl)-pyridine, 5-ethoxy-3-trichloromethyl-1,2,4-thiadiazole, 2-amino-4-chloro-6-methyl-pyrimidine, 2-mercapto- benzothiazole, 2-sulfanilamidothiazole, thiourea, sodium azide, potassium azide, 1-hydroxypyrazole, 2-methylpyrazole-1-carboxamide, 4-amino-1,2,4-triazole, 3-mercapto-1,2,4-triazole, 2, 4-diamino-6-trichloromethyl-5-triazine, carbon bisulfide, ammonium thiosulfate, sodium trithiocarbonate, 2,3-dihydro-2,2-dimethyl-7-benzofuranol methyl carbamate and N-(2,6-dimethylphenyl)-N-(methoxyacetyl! )-alanine methyl ester, or - at least one urease inhibitor, preferably selected from N-n-butylthiophosphorus triamide

9 BE2022/5772 (NBTPT) and/or N-n-propylthiophosphorus triamide (NPTPT), or - at least one common agrochemical additive, preferably selected from the group consisting of aqueous and/or organic solvents, pH regulators, surfactants, wetting agents, spreading agents, adhesion promoters, carriers, fillers, viscosity regulators, emulsifiers, dispersants, sequestering agents, anti-caking agents, coalescing agents, rheology modifiers, anti-foaming agents, photo protectors, antifreezes, (additional or further) biostimulators, pesticides/plant protection agents, biocides, (additional or further) plant growth regulators, protectants, penetration agents , anti-caking agents, mineral and/or vegetable oils and/or waxes, dyes and drift control agents, or mixtures thereof.

The term "additional or further" describes biostimulants and/or plant growth regulators other than the compounds of general formula (I).

The compounds of the invention are preferably used in combination with a fertilizer, preferably a phosphorus source or an (ammonium) nitrogen-containing fertilizer, for example a solid or liquid inorganic, organic and/or organomineral fertilizer, or manure. The compound is used, for example, on solid fertilizers, or is used in liquid organic, inorganic or organomineral fertilizers or manure.

The compounds of general formula (|) are usually known per se and can be synthesized by standard techniques. Some of them are commercially available and can be obtained from ENAMINE Ltd, UkrOrgSynthesis Ltd., or Vitas-M Laboratory,

Ltd. or from Merck Millipore, Burlington, MA, USA, or Merck KGaA.

The compounds of the invention are plant additives that can alleviate starvation or drought symptoms in plants and promote the growth of plants experiencing starvation or drought problems.

They can significantly improve overall plant growth, especially in low nutrient or drought conditions.

An advantage is that the compound of the present invention is useful for reducing the need for fertilizers for growing plants.

The term "plant" includes any monocotyledonous or dicotyledonous plant, such as a plant of the family Fabaceae or Brassicaceae, in particular Medicago sativa (Alfalfa).

In another embodiment, the plant is grown under nutrient-limiting conditions. "Low nutrient conditions" here means conditions with few nutrients, i.e. with a content of

10 BE2022/5772 nutrients that are not optimal for the growth of the specific plant.

The mixture of this invention provides a vegetable additive composition consisting of: a compound of formula (I) as defined above and a formulation aid such as a carrier, a solvent or a surfactant.

"Plant additive composition" means any type of soil additive, soil improver, fertilizer or soil improver, which can of course be used to amend a soil, but also in hydroponics.

More specifically, this vegetable additive composition is a composition for promoting plant growth and/or for alleviating nutrient hunger or drought symptoms.

The vegetable additive composition of the present invention is not normally intended for use as a herbicide, in particular as a defoliant, desiccant, weed killer, germination inhibitor or herbicide.

The composition of the vegetable additive may be a liquid or solid (usually granulated or powdered) composition, such as dusting powders, gels, wettable powders, water-dispersible granules, water-dispersible tablets, effervescent tablets, emulsifiable concentrates, micro-emulsifiable concentrates, oil-based in-water emulsions, liquefied oil, aqueous dispersions, oil dispersions, suspension emulsions, capsule suspensions, emulsifiable granules, soluble liquids, water-soluble concentrates (with water or a water-miscible organic solvent as carrier), or impregnated polymer films.

In a particular embodiment, the plant additive composition further contains at least

A primary nutrient from the group nitrogen and potassium, and/or at least one secondary nutrient from the group calcium, magnesium, sodium and sulphur, and/or at least one micronutrient from the group boron, cobalt, copper, iron, manganese, molybdenum and zinc.

Preferably, this vegetable additive composition contains a compound of formula (|) as defined above and at least one or the two primary nutrients as defined above.

Preferably, this vegetable additive composition contains a compound of formula (I) as defined above and at least one or the two primary nutrients and the four secondary nutrients as defined above.

Preferably, this vegetable additive composition contains a compound of formula (I) as defined above, nitrogen, potassium, calcium, magnesium, sodium, sulphur, boron, cobalt, copper, iron, manganese, molybdenum and zinc.

11 BE2022/5772

A liquid vegetable additive composition preferably contains a solvent such as a polar, water-soluble solvent, a micelle or a surfactant.

The present invention provides a method of promoting the growth of a plant, consisting of adding to the growing medium or soil on which that plant is grown, a compound of formula (|) as defined above, or a composition of plant additives which consists of a compound of formula (I) as defined above and a formulation aid as defined above.

The method of this invention is not intended to promote the growth of a plant by inhibiting the growth of another plant (e.g. a weed).

The growing medium includes a liquid, semi-solid or solid medium suitable for supporting the growth of a plant. For example, it can be a mineral nutrient solution or an inert material such as heydite, clay granules, perlite, vermiculite or rock wool. The growing medium preferably contains the nutrients needed to support the growth of the plant.

The present invention provides the use of a compound of formula (I) as defined above for the preparation of a vegetable additive composition as defined above useful for promoting the growth of a plant.

One or more compounds of formula (I) can be used as plant growth promoters in the fertilizer discussed below. Furthermore, mixtures of one or more compounds of general formula (I) can be used. This is evident from the expression formula (|).

The plant growth promoters of the present invention are expected to have favorable toxicological properties, have a low vapor pressure and are well absorbed into the soil. As a result, the plant growth promoter is not significantly emitted into the atmosphere by sublimation or easily leached by water.

This primarily creates economic benefits, such as high profitability given the longer-lasting effect of the plant growth promoters, and environmental benefits, such as a reduction in the burden on the air (climate gas reduction) and on surface and groundwater.

The plant growth promoters can be applied to soils or substrates that are fertilized with an inorganic, organic or organic-mineral fertilizer. Usually they are used in a fertilizer mixture containing such fertilizer and the compound of general formula (|). Usually, the compound of general formula (I) is used in an amount of 10 to 10000 ppm by weight, preferably 100 to 10000 ppm by weight, based on the fertilizer without water. The application rate is based on the dry fertilizer.

The plant growth promoters of the present invention can be in substance, in

12 BE2022/5772 solution, dispersion or emulsion can be used. Therefore, the invention also relates to a solution, dispersion or emulsion containing the compound of general formula (I) of this invention, preferably in an amount of 0.1 to 50 wt%, more preferably 0.5 to 30 wt% %, preferably 1 to 20 wt%.

Preferably, according to this invention, fertilizers are used to form a fertilizer mixture containing compounds A and B.

A. an inorganic and/or organic and/or organic-mineral fertilizer and

B. 10 to 10000% by weight, preferably 100 to 10000% by weight, based on the fertilizer, of the compound of general formula (I) as defined above.

The water fraction in compound A and in the fertilizer mixture is often not more than 1.5 wt%, preferably not more than 1.0 wt%, preferably not more than 0.5 wt%, and preferably not more than 0. 3 wt%. Compounds A and B preferably constitute at least 95 wt% and preferably at least 98 wt% of the fertilizer mixture.

The nitrogen content of component A (without water) is often at least 12 wt%, preferably at least 20 wt%, and preferably at least 22 wt%. The nitrogen content can be, for example, 25 to 29 wt%, in particular 26 to 28 wt%. The nitrogen content can be divided between fast-acting nitrate nitrogen and slow-acting ammonium nitrogen.

The inorganic fertilizers are preferably ammonium and/or urea-containing fertilizers, preferably ammonium-containing fertilizers that may also contain urea.

Urea-containing fertilizers are further described in WO 2016/207210.

Fertilizers usually provide, in different proportions: -three important macronutrients: -Nitrogen (N): leaf growth -Phosphorus (P): Development of roots, flowers, seeds, fruits; -Potassium (K): Strong stem growth, movement of water in plants, promoting flowering and fruiting; three secondary macronutrients: calcium (Ca), magnesium (Mg) and sulfur (S); -micronutrients: copper (Cu), iron (Fe), manganese (Mn), molybdenum (Mo), zinc (Zn), boron (B). Of incidental interest are silicon (Si), cobalt (Co) and vanadium (V).

The fertilizers used in accordance with the present invention may be of natural or synthetic origin and are applied to soil or plant tissue to provide one or more plant nutrients essential for plant growth. The fertilizers used in accordance with this invention must provide at least nitrogen as a nutrient. Other nutrients include K and P.

Multinutrient fertilizers/complex fertilizers provide two or more nutrients.

13 BE2022/5772

Inorganic fertilizers exclude carbonaceous materials, except urea.

Organic fertilizers usually come from plants or animals.

Organomineral fertilizers (a combination of inorganic and organic fertilizers) can also be used.

The most important straight nitrogen fertilizer is ammonia or its solutions. Ammonium nitrate is also widely used. Urea is another popular nitrogen source, with the advantage of being solid and non-explosive. Another nitrogen-based fertilizer is calcium ammonium nitrate.

The most important straight phosphate fertilizers are the superphosphates. "Single superphosphate" (SSP) consists of 14-18% P, O, , again in the form of Ca(H, PO, ), but also of phosphogypsum (CaSO, - 2H, O). Triple superphosphate (TSP) typically consists of 44-48% P, Os and not gypsum. A mixture of single superphosphate and triple superphosphate is called double superphosphate. More than 90% of a typical superphosphate fertilizer is soluble in water.

Diammonium phosphate (DAP) quickly became the commodity most commonly used by growers today, and it has the highest concentration of phosphate and nitrogen at 18 N- 46P, Os -0K, O

Monoammonium phosphate (MAP) is essentially the same as DAP, but has a lower nitrogen concentration of 11 N - 52 P, O, -0 K, O. It is completely soluble in water and has a granular material; it mixes well and often serves as an ingredient in bulk fertilizers.

Granulated triple superphosphate (GTSP) is very similar to the superphosphate fertilizer containing 46%

P,O5, which supplies calcium and sulfur to plants. GTSP is formed by reaction of phosphate rock with phosphoric acid.

Superphosphoric acid is an acid used to make a concentrated or liquid fertilizer.

Phosphoric acid is used in granulation plants where ammonia is added to phosphoric acid to produce the ammonized phosphate fertilizer.

Phosphate fertilizers are obtained by extraction from phosphate rock, which contains two important phosphorus-containing minerals, namely fluorapatite Ca, (PO, ), F (CFA) and hydroxyapatite Ca, (PO, ), OH. These minerals are converted into water-soluble phosphate salts by treatment with sulfuric acid (H, SO, ) or phosphoric acid (Hs PO, ).

In the nitrophosphate process or Odda process, phosphate rock with a phostor content of up to 20% (P) is dissolved with nitric acid (HNO; ) to obtain a mixture of phosphoric acid (H, PO, ) and calcium nitrate (Ca(NO, ), ). This mixture can be added with a potassium fertilizer

14 BE2022/5772 combined into a compound fertilizer with the three macronutrients N, P and K in easily soluble form.

The most important straight potassium fertilizer is potassium chloride (MOP).

Binary (NP, PK) fertilizers can also be used:

Important two-component fertilizers supply both nitrogen and phosphorus to the plants.

These are called NP fertilizers. The most important NP fertilizers are monoammonium phosphate (MAP) and diammonium phosphate (DAP). The active substance in MAP is

NH, H, PO, . The active substance in DAP is (NH, ), HPO, . About 85% of fertilizers

MAP and DAP are soluble in water.

NPK fertilizers are three-component fertilizers that provide nitrogen, phosphorus and potassium.

NPK fertilizers can be produced by mixing the above-mentioned straight fertilizers in bulk or per granule, such as in Nitrophoska®. In some cases, chemical reactions can occur between the two or more components.

NPK fertilizers are at least three-component fertilizers that supply nitrogen, phosphorus and potassium. NPK fertilizers can be produced by mixing the above-mentioned straight fertilizers in bulk or in each granule, such as in Nitrophoska®. In some cases, chemical reactions can occur between the two or more components.

For example, monoammonium and diammonium phosphates, which provide plants with both N and P, are produced by neutralization of phosphoric acid (from phosphate rock) and ammonia:

NH; + Hs PO, — (NH, )H, PO, 2 NH; + Hs PO, — (NH, ), HPO,

In addition to the main components, such as N, P and K, micronutrients (trace elements) may be present in the fertilizers. The most important micronutrients are molybdenum, zinc, boron and copper. These elements are generally supplied as water-soluble salts.

Preferred fertilizers contain ammonium or urea. Examples of preferred ammonium fertilizers are NPK fertilizers, calcium ammonium nitrate, ammonium sulfate nitrate, ammonium sulfate and ammonium phosphate.

Other preferred ingredients of the fertilizer compositions include trace elements, other minerals, normalizers and binders.

Organic fertilizers are fertilizers of organic or biological origin, i.e. fertilizers derived from living or previously living materials, such as animals, plants or algae. Fertilizers of organic origin include animal waste, vegetable waste, for example from food processing or agriculture, compost and treated sewage sludge (biosolids). Animal sources can be manure, but also products from it

15 BE2022/5772 slaughter of animals, such as blood meal, bone meal, feather meal, hides, hooves and horns.

Soil improvers such as peat or coir, bark and sawdust can also be used.

Fertilizers may include without limitation ammonium sulfate, ammonium nitrate, ammonium sulfate nitrate, ammonium chloride, ammonium bisulfate, ammonium polysulfide, ammonium thiosulfate, aqueous ammonia, ammonium polyphosphate, aluminum sulfate, calcium nitrate, calcium ammonium nitrate, calcium sulfate, calcitic limestone, calcium oxide, hampene (iron chelate), dolomitic limestone, hydrated lime, calcium carbonate, diammonium phosphate, monoammonium phosphate, potassium nitrate, potassium bicarbonate, monopotassium phosphate, magnesium nitrate, magnesium sulfate, potassium sulfate, potassium chloride, sodium nitrates, magnesia limestone, magnesia, disodium dihydromolybdate, cobalt chloride hexahydrate, nickel chloride hexahydrate, indolebutyric acid, L-tryptophan, urea, urea formaldehydes, urea ammonium nitrate, sulfuric acid d urea, polymeric urea, isobutylidene diurea, K, SO, -2MgS0,, kainite, sylvinite, Kieserite, Epsom salts, elemental sulfur, marl, ground oyster shells, fish meal, oil cakes, fish manure, blood meal, rock phosphate, superphosphates, slag, bone meal, wood ash, biochar, algae, algae extract, struvite, manure, bat guano, peat moss, compost, green sand, cottonseed meal, feather meal, crab meal, fish emulsion or a combination thereof. The micronutrient fertilizer may consist of boric acid, borate, boron frit, copper sulphate, copper frit, copper chelate, sodium tetraborate decahydrate, iron sulphate, iron oxide, iron ammonium sulphate, iron frit, iron chelate manganese sulphate, manganese oxide, manganese chelate, manganese chloride, manganese frit, sodium molybdate, molybdic acid, zinc sulphate, zinc oxide, zinc carbonate, zinc frit, zinc phosphate, zinc chelate or a combination thereof. In a special embodiment, this fertilizer or fertilizer composition does not contain insoluble selenium, selenium mineral, soluble selenium or salts thereof.

The treated (inorganic, organic or organic-mineral) fertilizers according to the invention are preferably in powder form, prill form or in granular form.

In addition to the compound of the general formula (I), formulations consisting of the compound and agronomic excipients can be used to incorporate the plant growth promoters into the fertilizer. Agronomic additives include solvents, dispersants, pH regulators, fillers, stability improvers and surfactants.

The plant growth promoters can be included in the fertilizer mixture by mixing them or the formulation containing them with a solid or liquid fertilizer or fertilizer formulation. Preferably, the fertilizer mixture is in solid form and the plant growth promoter is applied to the surface of the (inorganic, organic or organominal) fertilizer.

In a process for the manufacture of the fertilizer mixture of the present invention, the plant growth promoters or the formulation containing them may be incorporated into the fertilizer (inorganic, organic or organic-mineral) and/or applied to the

16 BE2022/5772 surface of the fertilizer.

Fertilizer granules are impregnated or coated with the plant growth promoters, for example by spraying them with a formulation such as a solution or a dispersion of the plant growth promoters and then drying. The method is known from, for example

DE-A-41 28 828. Sealing the impregnated granules with, for example, a paraffin wax, which is an additional proposal in the latter document, is possible, but generally not necessary.

Granulating aids that can be used for the preparation of solid fertilizer compositions can be lime, gypsum, silica or kaolinite.

An alternative is the addition of the nitrification inhibitor during the actual production of the fertilizer or, for example, in the liquid manure.

As a rule, growth promoters are applied to the soil in quantities that are effective for the desired effect.

Release of the plant growth promoters in liquid fertilizer formulas can be effected, for example, by fertigation with or without water surplus as described in DE-C-102 30 593.

The fertilizer mixture may contain at least one nitrification inhibitor. This at least one further nitrification inhibitor preferably inhibits ammonia-oxidizing bacteria (AOB) and is preferably selected from the group consisting of 2-(3,4-dimethyl-pyrazol-1-yl)-succinic acid, 3,4-dimethylpyrazole (DMP) , 3,4-dimethylpyrazole phosphate (DMPP), dicyandiamide (DCD), 1H-1,2,4-triazole, 3-methylpyrazole (3-MP), 2-chloro-6-(trichloromethyl)-pyridine, 5-ethoxy- 3-trichloromethyl-1,2,4-thiadiazole, 2-amino-4-chloro-6-methyl-pyrimidine, 2-mercapto-benzothiazole, 2-sulfanilamidothiazole, thiourea, sodium azide, potassium azide, 1-hydroxypyrazole, 2-methylpyrazole- 1-carboxamide, 4-amino-1,2,4-triazole, 3-mercapto-1,2,4-triazole, 2.,4-diamino-6-trichloromethyl-5-triazine, carbon bisulfide, ammonium thiosulfate, sodium triocarbonate, 2 ,3-dihydro-2,2-dimethyl-7-benzofuranol methyl carbamate and N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-alanine methyl ester. Nitrification inhibitors that inhibit ammonia-oxidizing archaea (AOA) can also be used together with the compound of general formula (|).

When the nitrification inhibitor is used, the weight ratio between the compound of general formula (|) and the nitrification inhibitor is preferably 0.01 to 100:1, more preferably 0.1 to 10:1.

Furthermore, the fertilizer mixture may contain at least one urease inhibitor, which is preferably selected from N-n-butylthiophosphorus triamide (NBTPT) and/or N-n-propylthiophosphorus triamide (NPTPT). A urease inhibitor is usually added when the fertilizer contains urea. Urea nitrogen is released as ammonium through the action of urease, and the ammonium can undergo nitrification. Therefore, it may be advantageous to combine a urease inhibitor with the nitrification inhibitor.

17 BE2022/5772

When the compound of general formula (I) of the present invention is combined with N-n-butylthiophosphorus triamide (NBTPT) and/or N-n-propylthiophosphorus triamide (NPTPT), the weight ratio between plant growth promoter(s) and urease inhibitor is preferably 0.01 to 100: 1, more preferably 0.1 to 10:1.

It is known that thiophosphorus triamides are converted relatively easily to the corresponding phosphorus triamides and thiophosphorus diamides, as well as to other metabolites.

Since moisture generally cannot be completely excluded, thiophosphorus triamide and the corresponding phosphorus triamide are often present in a mixture with each other. In this specification, the term "(thio)phosphorus-containing triamide" therefore denotes not only the pure thiophosphorus-containing triamides and phosphorus-containing triamides, but also mixtures thereof.

According to this invention, mixtures of N-(n-butyl)thiophosphorus triamide and N-(n-)propylthiophosphorus triamide can also be used, as described in EP-A-1 820 788.

The fertilizer mixtures may contain other ingredients such as coatings, for example of inorganic or organic polyacids, which are described in US 6,139,596.

Furthermore, coatings of powders, prills and granules can be formed from inorganic material, such as sulfur or mineral-based coatings, or with an organic polymer.

The respective coatings are described in WO 2013/121384 on page 23, line 37 to page 24, line 16.

As mentioned, the agrochemical formulations containing the compounds of formula (I) are used in "effective amounts". This means that they are used in an amount that can achieve the desired effect, namely a (synergistic) improvement in the health or growth of a plant, but which does not cause phytotoxic symptoms on the treated plant.

For use according to the present invention, the agrochemical formulations containing the compounds of formula (|) can be converted into the usual formulations, for example solutions, emulsions, suspensions, dusts, powders, pastes and granules. The form of use depends on the specific intended purpose; in any case, it must ensure a fine and even distribution of the agrochemical formulations containing the compounds of formula (I) of this invention. The formulations are prepared in a manner known to those skilled in the art.

The agrochemical formulations may also contain excipients that are common in agrochemical formulations. The excipients used depend on the specific application form and the active substance. Examples of suitable excipients are solvents, solid carriers, dispersants or emulsifiers (such as further solubility enhancers, protective colloids, surfactants and adhesion agents), organic and inorganic thickeners, bactericides, antifreezes, antifoaming agents, possibly dyes and tackifiers or binders

18 BE2022/5772 (for example for seed treatment formulations).

Suitable solvents are water, organic solvents such as mineral oil fractions with a medium to high boiling point, such as kerosene or diesel oil, also coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or derivatives thereof, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, glycols, ketones such as cyclohexanone and gamma-butyrolactone, dimethylamides of fatty acids, fatty acids and fatty acid esters and highly polar solvents, for example amines such as N-methylpyrrolidone.

Solid carriers are mineral earths such as silicates, silica gels, talc, kaolin, lime, chalk, coal, loess, clay, dolomite, diatomaceous earth, calcium sulphate, magnesium sulphate, magnesium oxide, ground plastics, fertilizers such as ammonium sulphate, ammonium phosphate, ammonium nitrate, urea, and products from vegetable origin, such as grain flour, tree bark flour, wood flour and nutshell flour, cellulose powders and other solid carriers.

Suitable surfactants (auxiliary agents, wetting agents, tackifiers, dispersants or emulsifiers) are alkali metal, alkaline earth metal and ammonium salts of aromatic sulfonic acids, such as lignin sulfonic acid, phenol sulfonic acid, naphthalene sulfonic acid, dibutyl naphthalene sulfonic acid and fatty acids, alkyl sulfonates, alkyl aryl sulfonates, alkyl sulfates, lau ryl ether sulphates, fatty alcohol sulphates , and sulfated hexa-, hepta- and octadecanolates, sulfated fatty alcohol glycol ethers, also condensates of naphthalene or naphthalene sulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenyl ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkyl phenyl polyglycol ethers, tributyl phenyl polyglyc ol ethers, tristearylphenyl polyglycol ethers, alkylaryl polyether alcohols, alcohol and fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin sulphite waste liquor and proteins, denatured proteins, polysaccharides (e.g. methylcellulose), hydrophobically modified starch, polyvinyl alcohols, polycarboxylates, polyalkoxylates, polyvinylamines, polyvinylpyrrolidone and their copolymers. Examples of thickeners (i.e. compounds that impart modified fluidity to formulations, i.e. high viscosity in static conditions and low viscosity under agitation) are polysaccharides and organic and inorganic clays such as xanthan gum.

A biostimulant is any substance or microorganism, in the form in which it is applied to plants, seeds or the root environment, with the aim of stimulating natural processes of plants that increase nutrient use efficiency and/or tolerance to abiotic stress. regardless of the nutrient content, or any combination of such substances and/or micro-organisms intended for this use.

A plant biostimulant is any microorganism or substance based on natural resources, in the form in which it is applied to plants, seeds or soil and any

19 BE2022/5772 other substrate with the aim of stimulating the natural processes of plants to improve their efficiency in using nutrients and/or their resistance to stress, regardless of the nutrient content, or any combination of such substances and/or micro-organisms intended for this use.

A "pesticide" is something that prevents, destroys or controls a harmful organism ("pest") or disease, or protects plants or plant products during production, storage and transportation.

The term includes: herbicides, fungicides, insecticides, acaricides, nematicides, molluscicides, rodenticides, growth regulators, repellents, rodenticides and biocides, as well as crop protection products.

Plant protection products (GBPs) are "pesticides" that protect crops or desired or target plants. They are mainly used in the agricultural sector, but also in forestry, horticulture, in recreational areas and in private gardens.

They contain at least one active substance and have one of the following functions: - protect plants or plant products against pests/diseases, before or after harvest; -influence the life processes of plants (such as substances that affect their growth, with the exception of nutrients); -preservation of plant products; -destroy or prevent the growth of unwanted plants or plant parts.

They may also contain other ingredients, including safeners and synergists.

An active substance is any chemical substance, plant extract, pheromone or microorganism (including viruses) that is active against "pests" or on plants, parts of plants or plant products.

The most common use of pesticides is in the form of crop protection products (GBPs).

The term "pesticide" is often used interchangeably with "plant protection product", but pesticide is a broader term that also includes non-plant/crop applications, for example biocides.

Biocides can be added, such as herbicides, bactericides, molluscicides, algicides, phytotoxic agents, fungicides and mixtures thereof.

Bactericides can be added to preserve and stabilize the formulation.

Examples of suitable bactericides are those based on dichlorophene and benzyl alcohol hemi formal (Proxel® from ICI or Acticide® RS from Thor Chemie and Kathon® MK from Rohm &

Haas) and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones (Acticide® M BS from Thor Chemie). Examples of suitable antifreezes are:

20 BE2022/5772 ethylene glycol, propylene glycol, urea and glycerin. Examples of anti-foaming agents are silicone emulsions (such as Silikon” SRE, Wacker, Germany or Rhodorsil°,

Rhodia, France), long chain alcohols, fatty acids, salts of fatty acids, organofluorine compounds and agrochemical formulations containing the compounds of formula (I) thereof.

Suitable dyes are pigments with low water solubility and solvent-soluble, for example water-soluble, dyes.

Examples of adhesion promoting substances, such as tackifiers or binders, are polyvinylpyrrolidones, polyvinyl acetates, polyvinyl alcohols and cellulose ethers (Tylose',

Shin Etsu, Japan).

Granules, for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active substances to solid carriers. Examples of solid carriers are mineral earths such as silica, silicates, talc, kaolin, attaclay, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulphate, magnesium sulphate, magnesium oxide, ground plastics, fertilizers, such as ammonium sulphate, ammonium phosphate, ammonium nitrate, urea, and products of vegetable origin, such as grain flour, tree bark flour, wood flour and nutshell flour, cellulose powders and other solid carriers.

Anti-caking agents such as oils and/or waxes can be added.

The agrochemical formulations generally contain between 0.01 and 95%, preferably between 0.1 and 90%, preferably between 0.5 and 90%, by weight of active substances. The compounds of the agrochemical formulations containing the compounds of formula (|) are used in a purity of 90% to 100%, preferably from 95% to 100% (according to their NMR spectrum).

The compounds of the agrochemical formulations containing the compounds of formula (I) can be used as such or in the form of their agricultural compositions, for example in the form of directly sprayable solutions, powders, suspensions, dispersions, emulsions, oil dispersions, pastes, dustable products, spreading agents or granules, by means of spraying, atomizing, pollinating, spreading, brushing, immersing or pouring. The forms of application depend entirely on the intended purposes; in any case, the aim is to ensure the best possible distribution of the compounds present in the agrochemical formulas containing the compounds of formula (|).

Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (sprayable powders, oil dispersions) by adding water. To prepare emulsions, pastes or oil dispersions, the substances, as such or dissolved in an oil or solvent, can be homogenized in water using a wetting agent, tackifier, dispersant or emulsifier. Another option is the preparation of

21 BE2022/5772 concentrates consisting of an active substance, a wetting agent, tackifier, dispersant or emulsifier and possibly a solvent or oil, and such concentrates are suitable for dilution with water.

The concentrations of the active substances in the ready-to-use preparations can be varied within relatively wide margins. In general they amount to 0.0001 to 10%, preferably 0.001 to 1% by weight of the agrochemical formulations containing the compounds of formula (|).

The agrochemical formulations containing the compounds of formula (I) can also be successfully used in the ultra-low-volume process (ULV), where it is possible to use compositions containing more than 95% by weight of active substance, or even Apply the active substance without additives.

Different types of oils, wetting agents, additives, herbicides, fungicides, other pesticides or bactericides can be added to the active substances, possibly only just before use (tank mixture). These agents can be mixed with the compounds of the agrochemical formulations containing the compounds of formula (|) in a weight ratio of 1:100 to 100:1, preferably 1:10 to 10:1.

Compositions of this invention may also contain fertilizers (such as ammonium nitrate, urea, potassium carbonate and superphosphate), phytotoxic substances and plant growth regulators (plant growth mixes) and protectants. These can be used consecutively or in combination with the compositions described above, or may be added just before use (tank mix). For example, the plant(s) may be sprayed with a composition of this invention before or after treatment with the fertilizers.

In the agrochemical formulations containing the compounds of formula (|), the weight ratio of the compounds generally depends on the properties of the compounds of the agrochemical formulations containing the compounds of formula (I).

The compounds of the agrochemical formulations containing the compounds of formula (I) can be used separately or in whole or part mixture with each other to prepare the composition according to the invention. They can also be packaged and further used as a combination composition such as a kit of parts.

The user usually applies the composition according to the invention from a pre-dosing device, a backpack sprayer, a spray tank or a spray surface. The agrochemical composition is supplemented with water and/or buffer to the desired application concentration, whereby other additives can possibly be added, and thus the ready-to-use spray liquid or the agrochemical composition according to the invention is obtained. Usually 50 to 500 liters of the ready-to-use spray liquid are applied per hectare of useful agricultural area, preferably 50 to 400 liters.

22 BE2022/5772

In one embodiment, the absolute amount of the active substances represented by formula (I) is used in a range between 1 mg/liter and 100 mg/liter, in particular in a range between 1 mg/l and 20 mg/liter. l, in particular in a range between 1mg/l and 25 mg/l, in particular in a range between 2 mg/l and 200 mg/l, in particular between 2 mg/l and 100 mg/l, in particular in particular between 2 mg/l and 50 mg/l, in particular between 2 mg/l and 25 mg/l, in particular between 4 mg/l and 40 mg/l, in particular between 4 mg/l and 20 mg/l, in particular between 4 mg/l and 16 mg/l, in particular between 4 mg/l and 12 mg/l.

In one embodiment, the individual compounds of the agrochemical formulations containing the compounds of formula (|) may be mixed in a spray tank by the user as a composition (or formulation) such as parts of a kit or parts of the inventive mixture and may optionally further additives are added (tank mix). "Agrochemical", as used herein, means any active substance that can be used in the agrochemical industry (including agriculture, horticulture, floriculture and home and garden uses, but also products intended for uses other than crops such as public health/pest control uses, uses to control unwanted insects and rodents, domestic uses, such as household fungicides and insecticides and products to protect plants or parts of plants, crops, bulbs, tubers, fruits (e.g. e.g. against harmful organisms, diseases or pests); to control, preferably promote or increase the growth of plants and/or to improve the yield of plants, crops or the harvested plant parts (e.g. the fruits, flowers , seeds, etc.).

An "agrochemical composition", as used herein, is a composition for agrochemical use, as defined herein, containing at least one active substance of a compound of formula (I), optionally with one or more additives that ensure optimal dispersion, dusting, promote deposition, wetting of the leaf, distribution, retention and/or absorption of agrochemical substances. Such additives are, for example, diluents, solvents, auxiliary agents, surfactants, wetting agents, spreading agents, oils, adhesives, viscosity regulators (such as thickeners, penetrants), pH-adhesives. regulators (such as buffering agents, acidifying agents), anti-caking agents, antifreeze agents, photo protectants, anti-foaming agents, biocides and/or drift control agents.

A "carrier", as used herein, means any solid, semi-solid or liquid carrier in or on which an active substance can be suitably incorporated, contained, immobilized, adsorbed, absorbed, bonded, encapsulated, embedded, adhered or compounded. Non-limiting examples of such carriers are nanocapsules, microcapsules, nanospheres, microspheres, nanoparticles, microparticles, liposomes, vesicles, spheres, a gel, weak ionic resin particles, liposomes, cochleate transporters, small beads, granules, nanotubes, bucky-balls, water drops that part

23 BE2022/5772 form a water-in-oil emulsion, oil droplets that form part of an oil-in-water emulsion, organic materials such as cork, wood or other plant-derived materials (e.g. in the form of seed pods , wood chips, pulp, balls, beads, sheets or any other suitable shape), paper or cardboard, inorganic materials such as talc, clay, microcrystalline cellulose, silica, alumina, silicates and zeolites, or even microbial cells (such as yeast cells) or suitable fractions or fragments thereof.

The terms "effective amount", "effective dose" and "effective amount" as used herein mean the amount required to achieve the desired result(s). More exemplary information on quantities, methods of application and suitable proportions is given below. The skilled person is well aware of the fact that such an amount can vary within a wide range and depends on various factors such as the cultivated plant treated and the climatic and soil conditions.

In this document the terms "assess", "measure", "assess", "monitor" and "determine" are used interchangeably; they include both quantitative and qualitative determinations.

It is clear that the agrochemical composition is stable both during storage and in use, meaning that the integrity of the agrochemical composition is maintained under storage and/or use conditions of the agrochemical composition, including elevated temperatures, freeze-thaw cycles, changes in pH or in ionic strength,

UV radiation, presence of harmful chemicals and the like. Preferably, the compounds of formula (|), (I) described herein remain stable in the agrochemical composition, meaning that the integrity and activity of the compounds are maintained under storage and/or use conditions of the agrochemical composition, including elevated temperatures , freeze-thaw cycles, changes in pH or ionic strength, UV radiation, presence of harmful chemicals and the like. Preferably, said compounds of formula (I), (I) remain stable in the agrochemical composition when the agrochemical composition is stored at ambient temperature for two years or when the agrochemical composition is stored at 54°C for two weeks. Preferably, the agrochemical composition of this invention retains at least about 70% activity, preferably at least 70% to 80% activity, preferably 80% to 90% activity or more. Examples of suitable carriers include alginates, gums, starch, cyclodextrins, celluloses, polyurea, polyurethane, polyester or clay.

The agrochemical composition can appear in any type of formulation; preferred formulations are powders, wettable powders, wettable granules, water dispersible granules, emulsions, emulsifiable concentrates, dusts, suspensions, suspension concentrates, suspension emulsions, capsule suspensions, aqueous dispersions, oil dispersions, aerosols, pastes, foams, slurries or flowable concentrates.

In yet another form, the invention provides the use of the agrochemical compositions of the invention to increase abiotic stress tolerance in

24 BE2022/5772 plants.

The agrochemical composition of the invention can be applied to a crop once, or it can be applied two or more times in succession with an interval between each two applications. The agrochemical composition according to the invention can be applied to the crop alone or mixed with other materials, preferably other agrochemical compositions; alternatively, the agrochemical composition of the invention can be applied separately to the crop with other materials, preferably other agrochemical compositions, applied at different times to the same crop.

In yet another embodiment, the invention provides a method for the manufacture of ("or production of" is an equivalent formulation) an agrochemical composition of the invention, comprising the formulation of a molecule of formula (|) as hereinbefore defined, together with at least one common agrochemical additive. Suitable production methods are known in the art and include, but are not limited to, high or low shear mixing, wet or dry milling, drip casting, encapsulation, emulsification, coating, encrusting, pilling, extrusion granulation, fluidized bed granulation, co-extrusion, spray drying, spray cooling, atomization, addition or condensation polymerization, interfacial polymerization, in situ polymerization, coacervation, spray encapsulation, cooling of molten dispersions, solvent evaporation, phase separation, solvent extraction, sol-gel polymerization, fluidized bed coating, pan coating, melting, passive or active absorption or adsorption.

The common agrochemical adjuvants are well known in the art and preferably include, but are not limited to, aqueous and/or organic solvents, pH adjusters (such as buffering agents, acidifying agents), surfactants, wetting agents, spreading agents, adhesion promoters (such as tackifiers, adhesives), carriers, fillers, viscosity regulators (such as thickeners), emulsifiers, dispersants, sequestering agents, anti-caking agents, coalescing agents, rheology modifiers, anti-foaming agents, photo protectants, antifreeze agents, additional or further biostimulants (including bacterial and/or fungal inoculants or micro-organisms in addition to non-microbial materials), biocides (preferably selected from herbicides, bactericides, phytotoxic agents, fungicides, pesticides/plant protection products and mixtures thereof), additional or further plant growth regulators, protectants, penetrants, anti-caking agents, mineral and/or vegetable oils and/or waxes, colorants and drift control agents or a suitable combination thereof.

If the compounds in formula (I) are considered biostimulators and/or plant growth regulators, the additional excipient may refer to additional or further biostimulators and/or plant growth regulators other than the compounds in formula (1).

The insecticide may consist of an organophosphate, a carbamate, a pyrethroid, a

25 BE2022/5772 acaricide, an alkyl phthalate, boric acid, a borate, a fluoride, sulphur, a haloaromatic substituted urea, a hydrocarbon ester, a biologically based insecticide or a combination thereof. The herbicide used to remove unwanted plants may consist of a chlorophenoxy compound, a nitrophenol compound, a nitrocresol compound, a dipyridyl compound, an acetamide, an aliphatic acid, an anilide, a benzamide, a benzoic acid, a benzoic acid derivative, an anisic acid, an anisic acid derivative, A Benzonitril, Benzothiadiazinondioxide, a thiocarbamate, a carbamate carbanilate, chlorine pyridinyl, a Cyclohexendi, a dinitroaminobenzendivaat, a fluorodinitolutinoninoninebinding , Oxadiazolinon, a phosphate, a phthalate, a picolinic acid connection, a triazine, a triazole, a uracil, a urea derivative, endothall, sodium chlorate or a combination thereof. The fungicide may consist of a substituted benzene, a thiocarbamate, an ethylene bis-dithiocarbamate, a thiophthalidamide, a copper compound, an organic mercury compound, an organotin compound, a cadmium compound, anilazine, benomyl, cyclohexamide, dodine, etridiazole, iprodione, metlax-yl, thiamimefon , triforine, or a combination thereof. The fungal inoculant may consist of a fungal inoculant of the family Glomeraceae, a fungal inoculant of the family Claroidoglomeraceae, a fungal inoculant of the family Acaulosporaceae, a fungal inoculant of the family

Sacculosprace-ae, a fungal inoculant of the family Entrophosporaceae, a fungal inoculant of the family Pacid-sproraceae, a fungal inoculant of the family

Diversisporaceae, a fungal inoculant of the family Paraglomeraceae, a fungal inoculant of the family Archaeosporaceae, a fungal inoculant of the family

Geosiphonaceae, a fungal inoculant of the family Ambisporacea, a fungal inoculant of the family Scutellosproaceae, a fungal inoculant of the family

Dentiscultataceae, a fungal inoculant of the family Racocetraceae, a fungal inoculant of the phylum Basidiomycota, a fungal inoculant of the phylum

Ascomycota, a fungal inoculant of the phylum Zygomycota, a fungal inoculant of the genus Glomus or a combination thereof. The bacterial inoculum may include a bacterial inoculum of the genus Rhizobium, a bacterial inoculum of the genus

Bradyrhizobium, a bacterial inoculum of the genus Mesorhizobium, a bacterial inoculum of the genus Azorhizobium, a bacterial inoculum of the genus Allorhizobium, bacterial inoculum of the genus Burkholderia, bacterial inoculum of the genus Sinorhizobium, bacterial inoculum of the genus Kluyvera, bacterial inoculant of the genus Azotobacter, bacterial inoculum of the genus

Pseudomonas, bacterial inoculant of the genus Azosprillium, bacterial inoculant of the genus Bacillus, bacterial inoculant of the genus Streptomyces, bacterial inoculant of the genus Paenibacillus, bacterial inoculant of the genus Paracoccus, bacterial inoculant of the genus £nterobacter, bacterial inoculant of the genus A/caligenes, bacterial inoculant of the genus Mycobacterium, bacterial inoculant of the genus

Trichoderma, bacterial inoculant of the genus G/ioc/adium, bacterial inoculant of the genus Æ/ebsie/la, or a combination thereof.

The mixture may additionally contain at least one micro-organism from the list consisting of Bacillus subtilis strain 713, Bacillus amyloliquefaciens MBI 600, Bacillus pumillus QST 2808,

Pseudomonas fluorescens, Bradyrhizobium japonicum, Trichoderma virus, Pseudomonas

26 BE2022/5772 putida, Trichoderma harzianum Fifai strain T22, Penicillium bilaï, Mesorhizobium,

Azospirillum, Azotobacter vinelandii and Clostridium pasteurianum, Glomus species.

The compounds of general formula (I) used according to the present invention can be used in combination with these excipients. The excipients used depend on the specific application form and the active substance and preferably include solvents, solid carriers, dispersants or emulsifiers, such as solvents, protective colloids, surfactants and adhesion agents. Furthermore, organic and inorganic thickeners, bactericides, antifreezes, antifoam agents, possibly dyes and tackifiers or binders can be used in combination with the nitrification inhibitors and in the fertilizer mixture. Suitable excipients are discussed in WO 2013/121384 on pages 25-26.

Other possible preferred ingredients include oils, humectants, adjuvants, biostimulants, herbicides, bactericides, other fungicides and/or pesticides. They are discussed, for example, in WO 2013/121384 on pages 28/29.

The fertilizer mixtures are preferably in solid form, including powders, prills and granules.

Furthermore, it is possible to apply the nitrification inhibitor in the form of a formulation, solution or dispersion separately or simultaneously with a fertilizer.

For the respective applications, reference can be made to US 6,139,596 and WO 2013/121384 as well as WO 2015/086823 and WO 2016/207210.

The invention also relates to a method for fertilizing agricultural or horticultural land, wherein a fertilizer mixture containing compounds A and B

A. an inorganic and/or organic and/or organic-mineral fertilizer and

B. 10 to 10000 % by weight, on the basis of the inorganic fertilizer, of a compound of general formula (|) as defined above, or compounds A and B separately, but within a period of 0 to 5 hours, preferably 0 to 1 hour , preferably approximately simultaneously, is applied to the bottom.

Parallel to the improvement of the use of phosphorus and possibly nitrogen in mineral, organic and organomineral fertilizers containing phosphorus and possibly ammonium or urea, the use of the plant growth promoters according to the present invention and of compositions containing them results in yield and crop biomass production increases, in some cases significantly.

The plants to be treated or rooted in soil according to the invention are preferably selected from the group consisting of agricultural, forestry, ornamental and horticultural plants, each in their natural or genetically modified form. Preferably, non-transgenic agricultural plants are treated.

27 BE2022/5772

Preferably, agricultural crops are selected from the group consisting of potatoes, sugar beets, wheat, barley, rye, oats, sorghum, rice, maize, cotton, rapeseed, oilseed rape, soybeans, peas, field beans, sunflowers, sugar cane; cucumbers, tomatoes, onions, leeks, lettuce, pumpkins; even more preferably, the plant is selected from the group consisting of wheat, barley, oats, rye, soybean, corn, rapeseed, cotton, sugar cane, rice and sorghum.

Preferably, the plant to be treated is selected from the group consisting of tomato, potato, wheat, barley, oats, rye, soy, maize, rapeseed, canola, sunflower, cotton, sugar cane, sugar beet, rice, sorghum, meadow grass and grassland.

In another preferred embodiment of the invention, the plant to be treated is selected from the group consisting of tomato, potato, wheat, barley, oats, rye, soy, corn, rapeseed, canola, sunflower, cotton, sugar cane, sugar beet, rice and sorghum.

In a particularly preferred embodiment of the invention, the plants to be treated are selected from the group consisting of tomato, wheat, barley, oats, rye, maize, rapeseed, rapeseed, sugar cane and rice.

In one case the plant to be treated according to the method of the invention is an agricultural plant. "Agricultural crops" are plants some or all of which (e.g. seeds) are harvested or grown on a commercial scale or which serve as an important source of animal feed, food, fibers (e.g. cotton, linen), fuels (e.g. wood, bioethanol , biodiesel, biomass) or other chemical compounds. Preferred agricultural crops include cereals, e.g. wheat, rye, barley, triticale, oats, sorghum or rice, beets, e.g. sugar beets or fodder beets; fruits, such as pome, stone or soft fruits, e.g. apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, blackberries or gooseberries; legumes, such as lentils, peas, alfalfa or soybeans; oilseed plants, such as rapeseed, rapeseed, canola, linseed, mustard seed, olives, sunflowers, coconut, cocoa beans, castor seeds, oil palms, groundnuts or soybeans; cucurbitaceae, such as pumpkins, cucumbers or melons; fiber crops, such as cotton, flax, hemp or jute; citrus fruits, such as oranges, lemons, grapefruits or mandarins; vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, cucurbits or peppers; milky plants, such as avocados, cinnamon or camphor; energy and commodity plants, such as corn, soy, rapeseed, canola, sugar cane or oil palm; tobacco; nuts; coffee; tea; bananas; vines (table grapes and grape juice); hop; peat; natural rubber plants.

Pasture grass and grassland consist of grass or grass mixtures with, for example, blue grassland (Poa spp.), bent grass (Agrostis spp.), ryegrass (Lolium spp), fescue (Festuca spp, hybrids and cultivars), Zoysia grass (Zoysia spp.), Bermuda grass (Cynodon spp.), St.

Augustine grass, Bahia grass (Paspalum), Centaury grass (Eremachloa), Carpet grass (Axonopus), Buffalo grass and Corn grass. Pastures can also consist of mixtures of the aforementioned grasses, for example ryegrass, and Trifolium species, for example Trifolium pratensis and Trifolium repens, Medicago species such as Medicago sativa, Lotus species such as

Lotus corniculatus, and Melilotus species, for example Melilotus albus.

28 BE2022/5772

In one case the plant to be treated according to the method of the invention is a horticultural plant. "Horticultural crops" means plants normally used in horticulture - for example the cultivation of ornamental plants, herbs, vegetables and/or fruit. Examples of ornamental plants are turf, geranium, pelargonia, petunia, begonia and fuchsia. Examples for vegetables are potatoes, tomatoes, peppers, cucumbers, melons, watermelons, garlic, onions, carrots, cabbage, beans, peas and lettuce and preferably tomatoes, onions, peas and lettuce. Examples of fruits include apples, pears, cherries, strawberries, citrus fruits, peaches, apricots and blueberries. In horticulture, a substrate often replaces (part of) the soil.

In one case the plant to be treated according to the method of the invention is an ornamental plant. "Ornamental plants" are plants that are commonly used in the garden, for example in parks, gardens and on balconies. Examples include turf, geranium, pelargonia, petunia, begonia and fuchsia.

In one case the plant to be treated according to the method of the invention is a forestry plant. The term "forestry crop" should be understood as trees, more specifically trees used in reforestation or industrial plantations. Industrial plantations generally serve the commercial production of forest products, such as timber, pulp, paper, rubber trees, Christmas trees or young trees for gardening. Examples of forestry crops are coniferous trees, such as pine, in particular Pinus spec, spruce, eucalyptus, tropical trees, such as teak, rubber tree, oil palm, willow (Salix), in particular Salix spec, poplar (cottonwood), in particular Populus spec, beech, particularly Fagus spec, birch, oil palm and oak.

The following definitions apply:

The term "plant growth promoters" should be understood as compounds of formula (I) which improve the absorption of nutrients or water and/or the use of the plants treated therewith and/or can lead to better plant growth.

"Plants" means plants of economic importance and/or plants cultivated by humans. They are preferably selected from agricultural, forestry, ornamental and horticultural plants, each in their natural or genetically modified form. The term "plant" as used herein includes all parts of a plant, such as germinating seeds, emerging seedlings, herbaceous vegetation, as well as established woody plants, including all underground parts (such as the roots) and above-ground parts.

The term "soil" is to be understood as a natural body consisting of living (e.g. microorganisms (such as bacteria and fungi), animals and plants) and non-living matter (e.g. minerals and organic substances (e.g. organic compounds in varying degrees of decomposition), liquids and gases) that occurs on the land surface, and is characterized by soil horizons that can be distinguished from the soil as a result of various physical, chemical, biological and anthropogenic processes

29 BE2022/5772 original material.

The term "nitrification inhibitor" should be understood as any chemical that retards or retards the nitrification process that normally takes place in (fertilized) soil.

Nitrification inhibitors slow down the natural conversion of ammonium to nitrate and target microorganisms, preferably ammonia-oxidizing bacteria (AOB), preferably by inhibiting the activity of the bacteria, such as Nitrosomonas spp. and/or

Nitrosospira spp. They can also act on ammonia-oxidizing archaea (AOA). The nitrification inhibitor is usually combined with a fertilizer, preferably an (ammonium) nitrogen-containing fertilizer, for example a solid or liquid inorganic, organic and/or organomineral fertilizer, or manure.

The term "nitrification" should be understood as the biological oxidation of ammonia (NH; ) or ammonium (N H,* ) with oxygen to nitrite (NO, ), followed by the oxidation of these nitrites to nitrates (NO, ) by micro- organisms. In addition to nitrate (NO, ), nitrification also produces nitrous oxide. Nitrification is an important step in the nitrogen cycle in the soil.

The term "fertilizers" should be understood as (chemical) compounds applied to promote the growth of plants and fruits. Fertilizers are usually applied through the soil (for uptake by the plant roots) or through the foliage (for uptake through the leaves). The term "fertilizers" can be divided into two broad categories: a) organic fertilizers (composed of digested plant/animal material) and b) inorganic fertilizers (composed of chemicals and minerals). Organic fertilizers include manure, worm castings, peat, seaweed, sewage and guano. Manufactured organic fertilizers include compost, blood meal, bone meal and seaweed extracts. Other examples include enzymatically digested protein, fish meal and feather meal.

The decomposition of crop residues from previous years and manure are another source of fertility. In addition, naturally occurring minerals, such as mine phosphate, potassium sulphate and limestone, are also considered inorganic fertilizers.

Inorganic fertilizers are usually produced by chemical processes (such as the Haber-Bosch process), which also use naturally occurring deposits while chemically modifying them (e.g. concentrated triple superphosphate). Naturally occurring inorganic fertilizers include Chilean sodium nitrate, minestone phosphate and limestone. The third category is organomineral fertilizers, a combination of inorganic and organic fertilizers.

“Fertilizer containing urea" means synthetic fertilizers containing urea, with the exception of natural fertilizers containing urea (e.g. manure as an example of a natural fertilizer containing urea). Examples of fertilizers containing urea are urea ammonium nitrate (UAN), isobutylidene diurea (IBDU), crotonylidene diurea (CDU) and urea formaldehyde (UF). Urea is usually made in the form of granules or prills. Urea fertilizers can be manufactured by dropping the liquid urea from a prill tower and drying the product

30 BE2022/5772 can also be obtained as a liquid formulation, which can be used for foliar fertilization, for example on potatoes, wheat, vegetables and soybeans, and for liquid application in the field. It is usually mixed with ammonium nitrate to form VAN with 28% N.

The term "locus" (plant habitat) should be understood as any type of environment, soil, area or material where the plant grows or is intended to grow. According to the invention, soil is preferred.

The invention is further illustrated by the following examples, which show that the compounds of formula (|) are strong root hair inducers.

Brief description of the drawings

Figure 1 shows representative images of the effect of the tested compounds on root hair induction and elongation. The scale bar is 0.5 mm.

Examples

We report a group of substances that induce root hairs and root hair elongation. These compounds were found by testing a series of small molecules and screening them for their root hair-inducing potential.

I. Materials and methods

For root hair measurements, Arabidopsis thaliana Columbia-0 seedlings were grown on a modified Murashige and Skoog medium (modMS - 1.25 mM KH, PO, 20 mM NH,

NO, , 0.1 mM H, BO, , 3 mM CaCl, 0.1 µM CoCl, *6H, O0, 0.1 µM CuSO, *5H, O, 0.1 MM Na,

EDTA*2H, O, 0.1 mM FeSO, *7H, O, 1.5 mM MgSO, *7H, O0, 0.1 MM MnSO, *H, O0, 1 u M Na,

MoO, *4H, O, 5 u M KI, 19 mM KNO: , 0. 03 mM ZnSO O, 0.03 mM ZnSO, *7H, O, 0.1 g/L myo-inositol, 0.5% sucrose and 0 .5 g/L MES (pH 5.7)). Arabidopsis seeds were stratified for 2 days at 4°C before germination. Seedlings were germinated in climate-controlled growth chambers at 22 °C under continuous light (100 4 mol m 2 s 1). The tested compounds were dissolved in DMSO and had a final concentration of 10 µM (0.1% DMSO). DMSO (final concentration 0.1%) was added to the no-compound controls.

After 10 days, the roots were imaged with a stereomicroscope or a VHX-6000. The number and length of root hairs were determined 4 to 6 mm above the root meristem. Root hair length was measured using ImageJ software.

II. Results 1. ... Anilino derivatives induce root hairs

34 BE2022/5772

To identify new root hair inducing substances, the root hair inducing effect of a series of small molecules was assessed. It was found that a group of anilino-based molecules or variants thereof had a positive effect on the number and/or length of root hairs (Table 1/Figure 1). Multiple substitutions on the benzene ring enhance the effect (compare, for example, example 8 (

SR LH, DH, > =

Ô OO Ô sa ), 9 ( SF ) and 10 ( we ) - table 1/figure 1), while the presence of an alkyl or other hydrocarbon group on the heteroatom also enhances the effect (compare for example example 15 ( vs me opk and !5 Sc

MO, | {

MO D

), 16 ( ) and 17 ( ) - table 1/figure 1). A carboxamide group substituted on the heteroatom at position 2 of the hydrocarbon group (compare for example example 11 (OD) and 20 (ee, in) - Table 1/Figure 1) further enhances this effect to a large extent. A ring closure by two substitutions on the benzene ring (e.g. example 25 (

COP

O

) - table 1/figure 1) also has a positive effect. Finally, we have also found that the nitrogen of the anilino can be replaced by one

HO

RO

> other heteroatom (e.g. example 4 ( ) - Table 1).

Table 1: Anilino derivatives and structural variants with a positive effect on the length of the root hairs and/or the number of root hairs, expressed in the average total

32 BE2022/5772 length of the root hairs per mm root.

Total root hair length in % compared to the

DMSO control without

Example Growth regulator structure

NH, 1 155

HC

NH

2 346

HC

3 No

OS

3 713

HC

3 No

HO pu 4 193

HC

SAH

CH, 907

33 BE2022/5772

HC

3 NH

HC” 5 6 3 668

HC

Nm

CH, 7 1118

CH, si 469

C.H.

L,

Hey '746

CH;

L

Hc” ‘ 401 0 NH,

TC

11 3226

34 BE2022/5772 oO

I CH my 12 830 0 OH

TL

13 842 1”

Ca 14:799

NH,

HO { 179

HC

DSH

HO

16 325

H.C

CH, NH 0

O

17 659

35 BE2022/5772

HC

CH” SH 3

a

O

CH

18 5 1176

CH;

X

19 287 cn 3192

HO oO

LC

21 124

NH,

AA

O

Ho” Û 22 689

S

N

23 594

36 BE2022/5772 ï NH 24 1106 (OÙ 25 0 1351 (UT

D

26 1985

Table of the English expressions in the drawings

Example

Claims (10)

Conclusions 1. The use of a compound of the general formula (I) R1 R2 ax" >) © With the following definitions: When R1 or R2 is a keto group and/or an amino group, more preferably R1 is a C2 hydrocarbon with a carboxamide group on C2 of R1 and R2 is hydrogen; if X is oxygen, R1 is hydrogen or a C1 hydrocarbon residue, preferably a C , hydrocarbon residue, which may contain one to seven heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur; ,_; -hydrocarbon residue, which may contain one or two halogen atoms and/or one to three heteroatoms, selected from the group consisting of nitrogen, oxygen and sulfur, preferably oxygen, it is also possible that R1 and R3 are covalently linked to form a heterocyclic ring with 5 to 8 members, which may contain 1 or 2 halogen atoms and/or 1 to 3 other heteroatoms in addition to the heteroatoms N already part of the heterocyclic ring, wherein R3 is preferably a hydrogen, a methyl group or a methoxy group; n 0; 1; 2; 3; 4 or 5, where n is preferably 0 or 1; as a plant growth promoter, in which the plant growth promoter improves the following BE2022/5772 - root hair development, - Phosphate use efficiency/uptake - efficiency of the nutrient use of plants, - absorption of nutrients by plants, - availability of nutrients, - water absorption of plants, - food and water supply by plants, - drought resistance, - root penetration into the soil, - anchorage in the soil, - useful symbiotic interactions of plants, - protection against harmful micro-organisms, and/or - plant growth or yield; and/or to alleviate and/or reduce nutrient starvation, drought, salt and/or osmotic stress in plants. The use according to claim 1, wherein the compound of formula (|) is selected from one of the following compounds: 5 ie 5 HC CH, ' ie CL. N pe I La Od DA He oe HO ! N MO 2 Ô CO im On ei fist, te Ÿ > NH EN AA. sh. € ö es > BE2022/5772 HC CO ii OH Du ; Now Ch | ; fs N Oo. He, se CH, a His © a H CH, : Feu CH, PO 7 L } NN N CH: Ho, Le NH 3 o 7 © > NH H,C i DW Sen U CH YT NH oM Ses F D SN Sa HC © Ds 0 Saut > X NH T 14 > Ch N ehs N vr a, N 5 HOL CH HE, HOL 20 AN a The . t Ÿ “it Eu 05 ; The use according to any of the preceding claims, wherein the compound of formula (I) is a compound of formula (II): 5 | A (IN) BE2022/5772 The use according to any of the preceding claims, wherein the pH value of the substrate or soil is between 4.5 and 7.5, preferably between 5 and 7, and more preferably between 5.5 and 6.5 ; 5. A mixture containing at least one compound of general formula (|) as defined in any of the preceding claims, and at least one additional agrochemical agent, preferably selected from the group consisting of - at least one inorganic and/or organic and/or organomineral fertilizer, - at least one nitrification inhibitor, preferably selected from the group consisting of 2-(3,4-dimethyl-pyrazol-1-yl)-succinic acid (DMPSA), 3,4-dimethylpyrazole (DMP), 3,4-dimethylpyrazole phosphate (DMPP), dicyandiamide (DCD), 1H-1,2,4-triazole, 3-methylpyrazole (3-MP), 2-chloro-6-(trichloromethyl)-pyridine, 5-ethoxy-3 -trichloromethyl-1,2,4-thiadiazole, 2-amino-4-chloro-6-methyl-pyrimidine, 2-mercapto-benzothiazole, 2-sulfanilamidothiazole, thiourea, sodium azide, potassium azide, 1-hydroxypyrazole, 2-methylpyrazole-1 -carboxamide, 4-amino-1,2,4-triazole, 3-mercapto-1,2,4-triazole, 2,4-diamino-6-trichloromethyl-5-triazine, carbon bisulfide, ammonium thiosulfate, sodium trithiocarbonate, 2,3 -dihydro-2,2-dimethyl-7-benzofuranol methyl carbamate and N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-alanine methyl ester, - at least one urease inhibitor, preferably selected from N-n-butylthiophosphorus triamide (NBPT) and/or N-n-propylthiophosphorus triamide (NPPT), - at least one common agrochemical additive, preferably selected from the group consisting of aqueous and/or organic solvents, pH regulators, surfactants, wetting agents, spreading agents, adhesion promoters, carriers, fillers, viscosity regulators, emulsifiers, dispersants, sequestering agents, anti-caking agents, coalescing agents, rheology modifiers, anti-foaming agents, photoprotectors, antifreezes, biostimulators, pesticides, biocides, plant growth regulators, protective agents, penetrants, anti-caking agents, mineral and/or vegetable oils and/or waxes, dyes and drift control agents, and mixtures of them. 6. A mixture of fertilizers, consisting of A. an inorganic and/or organic and/or organic-mineral fertilizer and B. effective amount, preferably 10 to 10,000 percent by weight, based on the fertilizer, of a compound of the general formula (I) as defined in any of claims 1 to 3. 7. The fertilizer mixture of claim 5, wherein the fertilizer mixture is in solid form and the compound of the general formula (|) is incorporated into the fertilizer or applied to the surface of the fertilizer, preferably inorganic. BE2022/5772 8. The fertilizer mixture as referred to in any of claims 5 or 6, wherein the fertilizer mixture contains at least one additional agrochemical agent, preferably selected from the group consisting of - at least one nitrification inhibitor, preferably selected from the group consisting of 2- (3,4-dimethyl-pyrazol-1-yl)-succinic acid (DMPSA), 3,4-dimethylpyrazole (DMP), 3,4-dimethylpyrazol phosphate (DMPP), dicyandiamide (DCD), 1H-1,2,4- triazole, 3-methylpyrazole (3-MP), 2-chloro-6-(trichloromethyl)-pyridine, 5-ethoxy-3-trichloromethyl-1,2,4-thiadiazole, 2-amino-4-chloro-6-methyl -pyrimidine, 2-mercapto-benzothiazoo, 2-sulfanilamidothiazole, thiourea, sodium azide, potassium azide, 1-hydroxypyrazole, 2-methylpyrazole-1-carboxamide, 4-amino-1,2,4-triazole, 3-mercapto-1,2 ,4-triazole, 2,4-diamino-6-trichloromethyl-5-triazine, carbon bisulfide, ammonium thiosulfate, sodium trithiocarbonate, 2,3-dihydro-2,2-dimethyl-7-benzofuranol methyl carbamate and N-(2,6-dimethylphenyl )-N-(methoxyacety!)-alanine methyl ester, - at least one urease inhibitor, preferably selected from N-n-butylthiophosphorus triamide (NBPT) and/or N-n-propylthiophosphorus triamide (NPPT), - at least one common agrochemical additive, preferably selected from the group consisting of aqueous and/or organic solvents, pH adjusters, surfactants, wetting agents, spreading agents, adhesion promoters, carriers, fillers, viscosity regulators, emulsifiers, dispersants, sequestering agents, anti-caking agents, coalescing agents, rheology modifiers, anti-foaming agents, photo protectants, antifreeze agents, biostimulators, pesticides /vegetable production agents, biocides, plant growth regulators, protective agents, penetrants, anti-caking agents, mineral and/or vegetable oils and/or waxes, dyes and drift control agents, and mixtures thereof. 9. A process for the production of the fertilizer mixture claimed in any of claims 5 to 7 by introducing the compound of the general formula (|) into the fertilizer and/or the compound of the general formula (I) on the surface of the fertilizer. 10. A method of fertilizing agricultural or horticultural land using a fertilizer mixture containing compounds A and B A. an inorganic and/or organic and/or organic-mineral fertilizer and B. 10 to 10000 % by weight, on the basis of the fertiliser, of a compound of the general formula (|) as defined in any of statements 1 to 3, or compounds A and B separately, but within a period of 0 to 5 hour, preferably 0 to 1 hour, preferably approximately simultaneously, is applied to the soil.