Trialkylsulfonium chlorides as fungicides

Abstract

The present invention relates to trialkylsulfonium chlorides, to compositions comprising said trialkylsulfonium chlorides, to agricultural compositions comprising such compositions and trialkylsulfonium chlorides, respectively, to the use of said trialkylsulfonium chlorides and said compositions as pesticides, preferably as fungicides, and to methods of controlling or preventing pests and / or improving the health of plants with said trialkylsulfonium chlorides and compositions.

Description

[0001] Priority is claimed to European Patent Application No. 20 199 746.7, filed October 2, 2020, and European Patent Application No. 20 199 747.5, filed October 2, 2020.

[0002] The present invention relates to trialkylsulfonium chlorides, compositions comprising trialkylsulfonium chlorides, agricultural compositions comprising such compositions and trialkylsulfonium chlorides, respectively, to the use of trialkylsulfonium chlorides and compositions as pesticides, preferably as fungicides, and to methods of controlling or preventing pests and / or improving plant health with trialkylsulfonium chlorides and compositions. Preferably, the trialkylsulfonium chloride is octadecyldimethylsulfonium chloride.

[0003] Fungi are distributed worldwide. There are currently about 100,000 different species of fungi known. Fungi pose one of the biggest biological challenges to crop health and food safety. During infection of a plant by a pathogenic fungus, different stages are usually observed. The first stage of the interaction between a plant pathogenic fungus and its potential host plant is crucial for the colonization of the plant by the fungus. During the first stage of infection, spores attach to the plant surface, germinate, and the fungus penetrates the plant. This can happen at existing openings such as stomata or wounds, but can also involve the formation of specialized penetration structures or the secretion of cell wall digesting enzymes. The most effective strategy we have to control fungal pathogens on crops is based on the use of fungal toxic chemicals (fungicides). Over the past decades, many fungicides have been developed and are commercially available.

[0004] Intensive farming practices, such as monoculture planting (under which large fields are planted with genetically uniform cultivars) and fast generation times, have facilitated the development of fungicide resistance in fungal pathogens. This resistance can occur within a few years of field use of a fungicide. In fact, the rate of emergence of fungicide resistance exceeds the rate of discovery of fungicides.

[0005] Currently only a few new fungicides are in development and regulatory approval, but these are derivatives of commonly used chemicals, such as those targeting specific complexes of ergosterol biosynthesis, cell wall biosynthesis, or the mitochondrial respiratory chain. However, the state-of-the-art fungicides are unsatisfactory in all aspects, and thus there is a need for improved fungicides.

[0006] There is a continuous need for more effective treatments against crop pathogens to ensure our future food production. The rapid development of fungicide resistance in market-leading chemicals makes the identification of new fungicides a priority. These should (i) be active against pathogens that destroy crops, (ii) target fundamental processes at multiple sites to reduce resistance development, (iii) have low toxicity to humans and the environment.

[0007] One potential target for new fungicides is the fungal mitochondrion. Fungal mitochondria differ from their mammalian counterparts in the composition and function of respiratory enzymes, making them attractive targets for new fungicides. In the typical respiratory chain in eukaryotic mitochondria, four basic protein complexes enable electron transfer and proton pumping, which leads to electrochemical gradient generation and ATP synthesis. Unlike animals, fungi contain specific types of complexes, including rotenone-insensitive type II NAD(P)H dehydrogenases or alternative NAD(P)H dehydrogenases (NDH-2) and cyanide-insensitive alternative oxidases (AOX), which both belong to the mitochondrial energy dissipation system (see, e.g., Nina Antos-Krzeminska et al., Protist, vol. 170, 21-37, February 2019).

[0008] Mitochondria are involved in a broad range of cellular processes, but most importantly, they provide a host for the enzymes used in oxidative phosphorylation. Oxidative phosphorylation depends on a proton gradient across the inner mitochondrial membrane, which is maintained by electron transfer through membrane-bound mitochondrial respiratory chain complexes. During this process, mitochondria produce reactive oxygen species (mROS), which in fungi have been shown to occur at complex I and complex III (Murphy, M. P. How mitochondria produce reactive oxygen species. Biochem. J. 417, 1-13 (2009). These mROS appear to act as intracellular signaling agents and, if dysregulated, damage proteins and lipids in the mitochondrial inner membrane and trigger apoptotic cell death. There is increasing evidence that such a pathway of programmed cell death exists in fungi, and targeting this pathway is a promising strategy for developing new antifungal agents. (Li, D. et al. Enzymatic dysfunction of mitochondrial complex I of the Candida albicans goal mutant is associated with increased reactive oxidants and cell death. Eukaryot. Cell 10, 672-682 (2011)

[0009] The electron transfer through the respiratory chain triggers the proton transport across the inner mitochondrial membrane. This makes the matrix negatively charged, thus it becomes a target for lipophilic cations. These molecules, which combine a cationic head group with a lipophilic moiety, cross the cell membrane and accumulate in the inner membrane of the mitochondria, and expose their cationic part to the matrix. This behavior allows the delivery of therapeutic agents into the mitochondria, but also inhibits the respiratory enzymes. While this effect on mitochondrial function challenges the medical application of lipophilic cations, it can be the key to using lipophilic cations as plant fungicides / antifungals (G. Steinberg et al. A lipophilic cation protects crops against fungal pathogens by multiple modes of action. Nature Communications 11 : 1608 (2020)). However, the amphiphilic structure of these molecules also indicates that they are inserted into the plasma membrane. In fact, until recently, antifungal lipophilic n-alkyl chain cations (=cationic surfactants) were thought to kill fungal cells by altering the permeability or function of the plasma membrane. However, recent publications convincingly demonstrate that lipophilic n-alkyl chain cations, i.e. the fungicides dodine, C18-sulfonium and C18- ammonium salts, inhibit fungal oxidative phosphorylation (G. Steinberg et al.).

[0010] The most studied lipophilic n-alkyl chain cation is dodecyl guanidinium, which carries a positively charged guanidinium group and is currently used as the fungicide Syllit (dodine).

[0011] FR 1 182 709 A relates to salts of dodecyl guanidine as fungicides. US 2,867,562 A relates to mono-carboxylic acid salts of dodecyl guanidine, which are highly effective in controlling fungal organisms harmful to the fruit and foliage of fruit trees; and to fungicidal compositions containing these compounds. US 3,143,459 A relates to non-foaming wettable powder compositions containing active fungicides such as dodecyl guanidine acetate and to methods of making such compositions. US 3,157,695 A relates to cyclododecyl guanidine and its organic and inorganic salts, which are said to have parasiticidal, particularly fungicidal, properties.

[0012] Dodine is a protective fungicide widely used to control fruit black spot disease and leaf diseases in orchards. The mode of action of dodine is controversial, with some supporting an osmotic effect in fungal cells, while others report inhibition of important metabolic enzymes. Recent studies suggest that the main mode of action of dodine is inhibition of mitochondrial respiration (G. Stein-berg et al.). While dodine can be used as a fungicide, it has some toxicity problems in aquatic organisms. Thus, if it is used as a fungicide on crops or soil, it can cause environmental problems, as this can lead to water loss into water bodies such as lakes and rivers.

[0013] Trialkyl sulfonium iodide salts (n-octadecyldimethyl sulfonium iodide) were shown to provide enhanced protection against fungal diseases (i.e. Septoria tritici blotch and rice blast in wheat; G. Steinberg et al.). The trialkyl sulfonium iodide salts block oxidative phosphorylation, but also induce mROS development at the respiratory complex I, which in turn induces fungal cell death (apoptosis; G. Steinberg et al.). In addition, the compound also induces natural plant defense systems (G. Steinberg et al.). In almost all aspects tested, n-octadecyldimethyl sulfonium iodide outperformed dodecylguanidinium and showed lower toxicity than dodecylguanidinium. No n-octadecyldimethyl sulfonium salts other than iodide salts are disclosed.

[0014] Trialkyl sulfonium salts are also known in the prior art for various purposes.

[0015] Certain trialkyl sulfonium salts have been used in the textile industry. FR 2 256 278 Al relates to trialkyl sulfonium salts as fabric softening agents. US 3,666,403 and US 3,826,609 relate to methods of dyeing textile fibers in the presence of sulfonium salts such as dimethylstearylsulfonium salts.

[0016] It has been found that many sulfonium salts inhibit specific cellular enzymes and prevent them from performing their normal physiological functions. In addition to inhibiting the electron transfer system in the NAD-cytochrome b region of the respiratory chain, triphenylsulfonium chloride has also been found to inhibit oxidative phosphorylation and adenosine triphosphate activity. Several alkyl sulfonium and alkyl disulfonium salts, such as decamethylenebis(dimethylsulfonium) and n-octadecyldimethylsulfonium bromide, are potent phospholipase inhibitors. Sulfonium compounds of similar structure can also inhibit cholinesterase (S. Mitchell, Biological Interactions of Sulfur Compounds, Taylor & Francis, 1996, pp. 208-210; PR. Young et al., Lipids, 26(11), 1991, 957-959).

[0017] US 3,235,356 discloses a method for controlling the growth and reproduction of plants by applying alkyl dimethyl sulfonium salts such as octadecyl dimethyl sulfonium methyl sulfate. US 4,475,941 A relates to a method for destroying or / and inhibiting the growth of microorganisms with tin organic derivatives to which a compound with a sulfonium function such as tetradecyldimethylsulfonium methyl sulfate is added. US 4,753,961 A discloses a bactericidal composition comprising a trialkyl sulfonium salt such as tetradecyldimethylsulfonium methyl sulfate (TDSM).

[0018] It is reported that certain trialkyl sulfonium salts exhibit fungicidal activity. FR 2 467 547 A1 relates to sulfonium compounds such as tetradecyldimethylsulfonium halides or methylsulfates which are said to be useful as bactericides, fungicides, algicides and corrosion inhibitors. US 4,088,781 A relates to sulfonium compounds having a 2-hydroxy-ethyl group with a sulfur atom which, in addition to having advantageous surface-active properties, also have fungicidal activity which can be utilized without damaging plants.

[0019] US 4,542,023 A relates to fungicidal salts of organic phosphorus derivatives. The cation of these salts can be a trialkyl sulfonium cation.

[0020] US 4,464,194 A relates to mixed alkyl sulfonium salts of N-phosphonomethylglycine such as dimethyloctadecyl sulfonium salt of N-phosphonomethylglycine.

[0021] P.R. Young et al., Lipids, Springer, Vol. 26 (11), 1991, 957-959 discloses that hexadecyltrimethylammonium and n-octadecyldimethylsulfonium bromide inhibit the hydrolysis of 1-S-phosphocholine-2-O-hexadecanoyl-1-mercapto-2-ethanol catalyzed by Clostridium perfringens phospho-lipase C at pH 7.5, 37°C, μ = 0.15 in the presence of KCl.

[0022] JP S45 36830 B relates to cellulose acetate fibers which can contain 1% to 30% diethylstearylsulfonium chloride.

[0023] J. Feihua et al., synthesis of new cationic surfactant containing sulfur and study on their physico-chemical properties, chemical abstracts service, 1994; 194520, 1-2 discloses the preparation of sulfonium cationic surfactants in high yield from high aliphatic alcohols such as octadecanol. The product has good bacteriostatic effect on staphylococcus and escherichia coli.

[0024] FR 810 437 relates to antimicrobial sulfonium salts such as octadecyldimethylsulfmethylsulfate.

[0025] WO 93 / 17723 relates to biodegradable surface disinfectants comprising dimethyloctadecylsulfonium methosulfate.

[0026] K. Negoro et al., journal of the Japan oil chemists'society, 27(1), 1978, 47-51 relates to the preparation of alkyl ethyl methyl sulfonium iodides and their physical-chemical, antimicrobial properties. One of the synthesized substances is alkyl: C 18 H 37 i.e. ethyl methyl octadecyl sulfonium iodide.

[0027] K. Yamanauchi et al., J. Am. Chem. Soc. 1983, 105, 538-545 relates to micellar reactions and a three-phase model for methylation of thymidine by (long-chain alkyl)dimethylsulfonium iodides.

[0028] However, the prior art fungicides are not satisfactory in all respects, and thus there is a need for improved fungicides with improved properties, particularly with respect to any one or a combination of the following properties: (a) pesticidal activity, preferably fungicidal activity; (b) biological activity; (c) compatibility with the environment and toxicity; (d) weather resistance, such as resistance to UV radiation and solubility in runoff water; (e) compatibility with agricultural additives; (f) solubility in water and in aqueous media at various pH values; (g) dissolution rate in water and in aqueous media; (h) behavior in the solid state, such as crystallinity and polymorphism; (i) physical properties, such as density; (j) chemical properties, such as degradation; (k) spectroscopic and optical properties; (1) thermal properties, such as melting and boiling points; (m) olfactory properties; (n) electrical properties and ionic strength; (o) mechanical properties, such as hardness; (p) surface tension; (q) hygroscopicity; (r) pH; (s) salinity, cation-anion interaction, covalency; (t) aging; (u) traceability; (v) processability; (w) storage stability and shelf life; (x) synthetic availability; and / or (y) economic aspects.

[0029] It would be advantageous to provide cationic surfactant-based antifungal compounds that improve the efficacy of known cationic surfactant-based antifungal compounds against specific fungi or against a broad range of fungi. It would also be advantageous to provide additional cationic surfactant-based antifungal compounds with environmental toxicity. Furthermore, it would be advantageous to provide more effective cationic surfactant-based antifungal compounds, compositions, and treatments that target the metabolism of fungi at multiple sites in one or more metabolic pathways. Such fungicides desirably employ novel multi-site modes of action that target fundamental processes in the pathogenic cell.

[0030] Furthermore, it would be advantageous to provide cationic surfactant-based antifungal compounds that are easy to manufacture at limited cost, have good compatibility with additives typically included in compositions, and contribute to overall fungicidal performance not only in terms of biological activity, efficacy, and potency, but also in terms of applicability, release kinetics, weather resistance, and the like.

[0031] Furthermore, it would be advantageous to provide cationic surfactant-based antifungal compounds in the form of highly concentrated formulations that can be diluted into agricultural formulations by the addition of a suitable diluent, such as water, shortly before use. The highly concentrated formulations can then be shipped at reduced cost. However, the highly concentrated formulations should exhibit sufficient stability of the ingredients contained therein at high concentrations.

[0032] It is an object of the present invention to provide insecticides, in particular fungicides, which have advantages over the prior art. They should be environmentally harmless, specific to the pests to be treated or prevented, suitable for treating a variety of different plants and for combating a variety of different harmful pests, in particular fungi. Furthermore, they should have a prolonged eradication lasting effect, such that within a certain time after treatment, the pests, in particular fungi, do not retain their initially harmful effects.

[0033] This object has been achieved by the subject matter of the patent claims.

[0034] A first aspect of the present invention relates to a trialkylsulfonium chloride according to the general formula (A) or a solvate thereof:

[0035]

[0036] wherein

[0037] R1represents -CH3, -CH2CH3, -CH2CH2CH3or -CH(CH3)2;

[0038] R2represents -CH3, -CH2CH3, -CH2CH2CH3or -CH(CH3)2; and

[0039] R3represents -(CH2) n -CH3, wherein n is an integer in the range of 17 to 31.

[0040] Thus, the trialkylsulfonium salt according to the present invention differs from the n-octadecyldimethylsulfonium iodide according to G. Steinberg et al. cited above in the counter anion (chloride vs. iodide).

[0041] Four alternative NAD(P)H dehydrogenases have been cloned and characterized in the mitochondria of the filamentous fungus Neurospora crassa. One of these enzymes is directed to the mitochondrial matrix (NDI1), while the other three are directed to the outside (NDE1-3). Among these alternative dehydrogenases, NDE2 has been considered to play a major role in ROS generation in N. crassa mitochondria (see for example Nina Antos-Krzeminska et al., Protist, Vol. 170, 21-37, February 2019). However, recent work on the wheat pathogen Zymoseptoria tritici (Z. tritici) suggests that the respiratory complex I is another major source of mROS in fungi (G. Steinberg et al.).

[0042] Surprisingly, the trialkylsulfonium chlorides according to the present application, preferably octadecyldimethylsulfonium chloride, outperform the corresponding bromides and iodides. While no significant differences between chlorides, bromides and iodides were observed in terms of depolarization of mitochondria and the ability to induce mitochondrial ROS formation, the chlorides according to the present application provide a significant benefit in inducing apoptotic cell death compared to the corresponding bromides and iodides.

[0043] Furthermore, it was surprisingly found that trialkylsulfonium salts with the smallest alkyl chain length C18 (octadecyl, stearyl) at residue R3 are able to inhibit mitochondrial activity, while comparative trialkylsulfonium salts with shorter alkyl chain lengths at residue R3 do not show the corresponding effect, regardless of the counter anion.

[0044] Experiments have shown that certain trialkylsulfonium salts, in particular trialkylsulfonium chlorides, are more stable than other salts, especially under UV light.

[0045] When the trialkylsulfonium chloride, preferably octadecyldimethylsulfonium chloride, is present in the form of a solvate, the type and stoichiometry of the solvate is not particularly limited. In preferred embodiments, the trialkylsulfonium chloride, preferably octadecyldimethylsulfonium chloride, is a hydrate, which is preferably selected from the group consisting of a hemihydrate, a monohydrate and a dihydrate. In other preferred embodiments, the trialkylsulfonium chloride, preferably octadecyldimethylsulfonium chloride, is an anhydrous substance, preferably a solvate-free substance.

[0046] Preferably, the trialkylsulfonium chloride according to the present application is selected from the group consisting of n-octadecyldimethylsulfonium chloride, n-octadecylmethylethylsulfonium chloride, n-octadecyldiethylsulfonium chloride, n-octadecylmethylpropylsulfonium chloride, n-octadecylethylpropylsulfonium chloride, n-octadecyldipropylsulfonium chloride; n-eicosyldimethylsulfonium chloride, n-eicosylmethylethylsulfonium chloride, n-eicosyldiethylsulfonium chloride, n-eicosylmethylpropylsulfonium chloride, n-eicosylethylpropylsulfonium chloride, n-eicosyldipropylsulfonium chloride; n-docosyldimethylsulfonium chloride, n-docosylmethylethylsulfonium chloride, n-docosyldiethylsulfonium chloride, n-docosylmethylpropylsulfonium chloride, n-docosylethylpropylsulfonium chloride and n-docosyldipropylsulfonium chloride.

[0047] Preferably, the trialkylsulfonium chloride according to the present application is n-octadecyldimethylsulfonium chloride:

[0048]

[0049] In a preferred embodiment, the trialkylsulfonium chloride, preferably n-octadecyldimethylsulfonium chloride, is a solid, preferably amorphous, crystalline or semi-crystalline.

[0050] In another preferred embodiment, the trialkylsulfoxonium chloride, preferably n-octadecyldimethylsulfoxonium chloride, is a liquid or a semi-solid.

[0051] It is envisaged that the trialkylsulfoxonium chloride according to general formula (A), preferably octadecyldimethylsulfoxonium chloride, can be present in mixture with one or more other trialkylsulfoxonium chlorides according to general formula (A).

[0052] Another aspect of the present application relates to a composition comprising a trialkylsulfoxonium chloride according to the present application or a solvate thereof as described above.

[0053] It is envisaged that the composition according to the present application can contain two or more trialkylsulfoxonium chlorides according to general formula (A).

[0054] Preferably, the composition according to the present application comprises an agriculturally acceptable carrier, wherein the content of the carrier is at least 1.0 wt.-% relative to the total weight of the composition.

[0055] In a preferred embodiment of the composition according to the present application, the content of the carrier is at least 2.5 wt.-%; preferably at least 5.0 wt.-%, preferably at least 7.5 wt.-%, preferably at least 10 wt.-%, preferably at least 15 wt.-%, preferably at least 20 wt.-%, preferably at least 25 wt.-%, preferably at least 30 wt.-%, preferably at least 40 wt.-%, preferably at least 50 wt.-%, preferably at least 60 wt.-%, preferably at least 70 wt.-%, preferably at least 80 wt.-%, preferably at least 90 wt.-%; in each case relative to the total weight of the composition.

[0056] In a preferred embodiment, the content of the carrier is at most 97.5 wt.-%, preferably at most 95 wt.-%, preferably at most 92.5 wt.-%, preferably at most 90 wt.-%, preferably at most 87.5 wt.-%, preferably at most 85 wt.-%, preferably at most 82.5 wt.-%, preferably at most 80 wt.-%, in each case relative to the total weight of the composition.

[0057] In a preferred embodiment, the content of the carrier is in the range of 10 ± 5.0 wt.-%, preferably 20 ± 15 wt.-%, preferably 20 ± 10 wt.-%, preferably 20 ± 5.0 wt.-%, preferably 30 ± 25 wt.-%, preferably 30 ± 20 wt.-%, preferably 30 ± 15 wt.-%, preferably 30 ± 10 wt.-%, preferably 30 ± 5.0 wt.-%, preferably 40 ± 35 wt.-%, preferably 40 ± 30 wt.-%, preferably 40 ± 25 wt.-%, preferably 40 ± 20 wt.-%, preferably 40 ± 15 wt.-%, preferably 40 ± 10 wt.-%, preferably 40 ± 5.0 wt.-%, preferably 50 ± 45 wt.-%, preferably 50 ± 40 wt.-%, preferably 50 ± 35 wt.-%, preferably 50 ± 30 wt.-%, preferably 50 ± 25 wt.-%, preferably 50 ± 20 wt.-%, preferably 50 ± 15 wt.-%, preferably 50 ± 10 wt.-%, preferably 50 ± 5.0 wt.-%, preferably 60 ± 35 wt.-%, preferably 60 ± 30 wt.-%, preferably 60 ± 25 wt.-%, preferably 60 ± 20 wt.-%, preferably 60 ± 15 wt.-%, preferably 60 ± 10 wt.-%, preferably 60 ± 5.0 wt.-%, preferably 70 ± 25 wt.-%, preferably 70 ± 20 wt.-%, preferably 70 ± 15 wt.-%, preferably 70 ± 10 wt.-%, preferably 70 ± 5.0 wt.-%, preferably 80 ± 15 wt.-%, preferably 80 ± 10 wt.-%, preferably 80 ± 5.0 wt.-%, preferably 90 ± 5.0 wt.-%, in each case relative to the total weight of the composition.

[0058] In a preferred embodiment of the composition according to the application, especially when the composition is a liquid, the carrier is selected from the group consisting of:

[0059] (a) water;

[0060] (b) a monohydric alcohol, such as methanol, ethanol, propanol, isopropanol, cyclohexanol or benzyl alcohol;

[0061] (c) a dihydric alcohol, such as ethylene glycol, propylene glycol, diethylene glycol or dipropylene glycol;

[0062] (d) a monoalkyl glycol ether, such as triethylene glycol monobutyl ether;

[0063] (e) a dialkyl glycol ether, such as ethylene glycol dimethyl ether;

[0064] (f) a dihydric alcohol ester;

[0065] (g) glycerol and glycerol ethers, such as isopropylidene glycerol;

[0066] (h) cyclic ethers, such as tetrahydrofuran or dioxolane;

[0067] (i) ketones, such as acetone, butanone or cyclohexanone;

[0068] (j) a monoester such as ethyl lactate, ethyl acetate or gamma-butyrolactone;

[0069] (k) a diester such as dimethyl glutarate or dimethyl succinate;

[0070] (l) an alkylene carbonate such as ethylene carbonate or propylene carbonate;

[0071] (m) a dialkyl sulphoxide such as dimethyl sulphoxide;

[0072] (n) an alkyl sulphone such as sulfolane;

[0073] (o) an alkyl amide such as N-methyl pyrrolidone, N-ethyl pyrrolidone or dimethyl formamide

[0074] (p) an alkanolamine such as monoethanolamine, diethanolamine, triethanolamine, an alkyl diethanolamine or a dialkyl monoethanolamine;

[0075] (q) a fatty acid, a fatty acid ester, a fatty acid amide;

[0076] (r) an oil such as an oil of vegetable or animal origin, a phytobland oil, a crop oil, a crop oil concentrate, a plant oil, a methylated seed oil, a petroleum oil and a silicone oil;

[0077] and combinations thereof.

[0078] In a preferred embodiment of the composition according to the application, the carrier is water or comprises water.

[0079] In a preferred embodiment of the composition according to the application, the carrier is a solvent. Preferably, the trialkylsulphonium chloride, preferably octadecyldimethylsulphonium chloride, is completely dissolved in the carrier.

[0080] In a preferred embodiment of the composition according to the application, especially when the composition is solid, the carrier is selected from the group consisting of:

[0081] (a) natural soil minerals and mineral earths such as silicates, calcite, marble, pumice, sepiolite, talc, kaolin, clay, talc, limestone, lime, calcium carbonate, chalk, earthenware clay, loess, quartz, perlite, attapulgite, montmorillonite, vermiculite, bentonite, dolomite or diatomaceous earth;

[0082] (b) synthetic minerals such as silicon dioxide, silica gel, aluminium oxide or silicates such as aluminium silicate or magnesium silicate;

[0083] (c) inorganic salts such as aluminium sulphate, calcium sulphate, copper sulphate, iron sulphate, magnesium sulphate, silicon sulphate, magnesium oxide;

[0084] (d) synthetic particles of inorganic or organic fine powders;

[0085] (e) particles of organic material, such as sawdust, coconut shells, corn cobs or hulls, or tobacco stems;

[0086] (f) diatomaceous earth;

[0087] (g) tricalcium phosphate;

[0088] (h) polysaccharides, such as cellulose, cellulose ethers, starch, xanthan gum, pullulan, guar gum;

[0089] (i) products of vegetable origin, for example grain meals, tree bark meal, wood meal, nut shell meal;

[0090] (j) grain fines, such as fines from corn, rice, wheat, barley, sorghum, millet, oat, triticale, rye, buckwheat, fonio or quinoa;

[0091] (k) other organic substances, such as cork powder, adsorptive carbon black, charcoal, peat, soil mixtures, compost, agricultural industrial residues; water-soluble polymers, resins or waxes;

[0092] (l) solid fertilizers, such as urea or ammonium salts, such as ammonium sulfate, ammonium phosphate, ammonium nitrate;

[0093] and combinations thereof.

[0094] The composition of the composition according to the present application is not particularly limited. Preferably, the composition is selected from the group consisting of solutions, suspensions, emulsions, gels, mousses, pastes, powders and granules. Preferably, the composition is an aqueous suspension.

[0095] In a preferred embodiment, the composition according to the present application is a liquid or a paste.

[0096] Preferably, the composition according to the present application has a dynamic viscosity of at least 0.5 mPa-s at 23 °C; preferably at least 0.6 mPa-s, preferably at least 0.7 mPa-s, preferably at least 0.8 mPa-s, preferably at least 0.9 mPa-s, preferably at least 1.0 mPa-s.

[0097] Preferably, the composition according to the application has a dynamic viscosity at 23 °C of at most 10,000 mPa-s; preferably at most 9,000 mPa-s, preferably at most 8,000 mPa-s, preferably at most 7,000 mPa-s, preferably at most 6,000 mPa-s, preferably at most 5,000 mPa-s, preferably at most 4,000 mPa-s, preferably at most 3,000 mPa-s, preferably at most 2,000 mPa-s, preferably at most 1,000 mPa-s, preferably at most 900 mPa-s, preferably at most 800 mPa-s, preferably at most 700 mPa-s, preferably at most 600 mPa-s, preferably at most 500 mPa-s, preferably at most 400 mPa-s, preferably at most 300 mPa-s, preferably at most 200 mPa-s, preferably at most 100 mPa-s, preferably at most 90 mPa-s, preferably at most 80 mPa-s, preferably at most 70 mPa-s, preferably at most 60 mPa-s, preferably at most 50 mPa-s, preferably at most 40 mPa-s, preferably at most 30 mPa-s, preferably at most 20 mPa-s, preferably at most 10 mPa-s.

[0098] This dynamic viscosity is preferably determined according to EN ISO 3104 or ASTM D7042.

[0099] Preferably, the composition according to the application is aqueous and it has a pH value which achieves a satisfactory balance between the solubility of the trialkylsulfonium chloride, the stability of the trialkylsulfonium chloride and the compatibility with the environment, typically after dilution of the composition having a relatively high concentration of trialkylsulfonium chloride into an agricultural composition having the desired lower concentration of trialkylsulfonium chloride to be used for agricultural purposes, i.e. to be brought into contact with crops. The pH dependence of the solubility of the trialkylsulfonium chloride, preferably octadecyldimethylsulfonium chloride, can play an important role. It is mainly desirable that for the trialkylsulfonium chloride, preferably octadecyldimethylsulfonium chloride, on the one hand its solubility is relatively high when it is provided in a form suitable for deployment in the field and on the other hand its solubility is relatively low when it is subsequently subjected to weathering in the field, thereby preventing it from being quickly carried away and washed away by rain and other runoff water.

[0100] Surprisingly, it was found that the aqueous solubility of trialkylsulfonium chlorides, preferably octadecyldimethylsulfonium chloride, has a minimum around pH 7.0, i.e. its aqueous solubility increases at pH values below 7.0 as well as at pH values above 7.0. This solubility behavior is particularly advantageous, because highly concentrated compositions to be deployed in the field can be prepared at pH values below 7.0 or above 7.0. Once such compositions have been deployed in the field, the trialkylsulfonium chloride, preferably octadecyldimethylsulfonium chloride, is exposed to environmental conditions, e.g. rain, which change the pH value towards neutral pH values. The resulting pH shift relatively reduces the aqueous solubility of the trialkylsulfonium chloride, preferably octadecyldimethylsulfonium chloride, and thus its tendency to be washed away.

[0101] Preferably, the composition according to the present application is aqueous and has a pH value in the range of 2 to 14, preferably 3 to 13, more preferably 8 to 13.

[0102] In a preferred embodiment, the composition according to the present application has a pH value of at least 1.0; preferably at least 1.5, preferably at least 2.0, preferably at least 2.5, preferably at least 3.0, preferably at least 3.5, preferably at least 4.0, preferably at least 4.5, preferably at least 5.0, preferably at least 5.5, preferably at least 6.0, preferably at least 6.5, preferably at least 7.0, preferably at least 7.5, preferably at least 8.0, preferably at least 8.5, preferably at least 9.0, preferably at least 9.5, preferably at least 10, preferably at least 10.5, preferably at least 11.

[0103] In a preferred embodiment, the composition according to the present application has a pH value of at most 14, preferably at most 13.5, preferably at most 13, preferably at most 12.5, preferably at most 12, preferably at most 11.5, preferably at most 11.0, preferably at most 10.5, preferably at most 10.0, preferably at most 9.5, preferably at most 9.0, preferably at most 8.5, preferably at most 8.0, preferably at most 7.5.

[0104] In a preferred embodiment, the composition according to the present application has a pH value in the range of 2.0 ± 1.0, preferably 3.0 ± 2.0, preferably 3.0 ± 1.0, preferably 4.0 ± 3.0, preferably 4.0 ± 2.0, preferably 4.0 ± 1.0, preferably 5.0 ± 4.0, preferably 5.0 ± 3.0, preferably 5.0 ± 2.0, preferably 5.0 ± 1.0, preferably 6.0 ± 5.0, preferably 6.0 ± 4.0, preferably 6.0 ± 3.0, preferably 6.0 ± 2.0, preferably 6.0 ± 1.0, preferably 7.0 ± 6.0, preferably 7.0 ± 5.0, preferably 7.0 ± 4.0, preferably 7.0 ± 3.0, preferably 7.0 ± 2.0, preferably 7.0 ± 1.0, preferably 8.0 ± 5.0, preferably 8.0 ± 4.0, preferably 8.0 ± 3.0, preferably 8.0 ± 2.0, preferably 8.0 ± 1.0, preferably 9.0 ± 4.0, preferably 9.0 ± 3.0, preferably 9.0 ± 2.0, preferably 9.0 ± 1.0, preferably 10 ± 3.0, preferably 10 ± 2.0, preferably 10 ± 1.0, preferably 11 ± 2.0, preferably 11 ± 1.0, preferably 12 ± 1.0.

[0105] In a preferred embodiment, the composition according to the application has a pH value in the range of 3.0 ± 2.5, more preferably 3.0 ± 2.0, still more preferably 3.0 ± 1.5, yet more preferably 3.0 ± 1.0, even more preferably 3.0 ± 0.5. In another preferred embodiment, the composition according to the application has a pH value in the range of 4.0 ± 3.5, more preferably 4.0 ± 3.0, still more preferably 4.0 ± 2.5, yet more preferably 4.0 ± 2.0, and most preferably 4.0 ± 1.0. In yet another preferred embodiment, the composition according to the application has a pH value in the range of 5.0 ± 4.0, more preferably 5.0 ± 3.0, still more preferably 5.0 ± 2.0, and most preferably 5.0 ± 1.0. In still another preferred embodiment, the composition according to the application has a pH value in the range of 6.0 ± 5.0, more preferably 6.0 ± 4.0, still more preferably 6.0 ± 3.0, even more preferably 6.0 ± 2.0, and most preferably 6.0 ± 1.0. In a preferred embodiment, the composition according to the application has a pH value in the range of 7.0 ± 6.0, more preferably 7.0 ± 5.0, still more preferably 7.0 ± 4.0, yet more preferably 7.0 ± 3.0, even more preferably 7.0 ± 2.0, and most preferably 7.0 ± 1.0. In another preferred embodiment, the composition according to the application has a pH value in the range of 8.0 ± 5.0, more preferably 8.0 ± 4.0, still more preferably 8.0 ± 3.0, yet more preferably 7.0 ± 2.0, and most preferably 8.0 ± 1.0. In yet another preferred embodiment, the composition according to the application has a pH value in the range of 9.0 ± 4.0, more preferably 9.0 ± 3.0, still more preferably 9.0 ± 2.0, and most preferably 9.0 ± 1.0. In still another preferred embodiment, the composition according to the application has a pH value in the range of 10 ± 4.0, more preferably 10 ± 3.0, still more preferably 10 ± 2.0, and most preferably 10 ± 1.0. In another preferred embodiment, the composition according to the application has a pH value in the range of 11 ± 3.0, more preferably 11 ± 2.0, still more preferably 11 ± 1.0. In yet another preferred embodiment, the composition according to the application has a pH value in the range of 12 ± 2.0, more preferably 12 ± 1.0.

[0106] In a preferred embodiment, the composition according to the application has a pH value below 7.0, preferably at most 6.5.

[0107] In other preferred embodiments, the composition according to the application has a pH value above 7.0, preferably at least 7.5.

[0108] Preferably, the content of trialkylsulfoxonium chloride, preferably octadecyldimethylsulfoxonium chloride, is greater than 0.1 wt.%, relative to the total weight of the composition.

[0109] In a preferred embodiment, the content of trialkylsulfonium chloride, preferably octadecyldimethylsulfonium chloride, is at least 0.5 wt.-%, preferably at least 1.0 wt.-%, preferably at least 2.5 wt.-%, preferably at least 5 wt.-%, preferably at least 7.5 wt.-%, preferably at least 10 wt.-%, preferably at least 12.5 wt.-%, preferably at least 15 wt.-%, preferably at least 17.5 wt.-%, preferably at least 20 wt.-%, in each case relative to the total weight of the composition.

[0110] In a preferred embodiment, the content of trialkylsulfonium chloride, preferably octadecyldimethylsulfonium chloride, is at most 97.5 wt.-%, preferably at most 95 wt.-%, preferably at most 92.5 wt.-%, preferably at most 90 wt.-%, preferably at most 87.5 wt.-%, preferably at most 85 wt.-%, preferably at most 82.5 wt.-%, preferably at most 80 wt.-%, in each case relative to the total weight of the composition.

[0111] Preferably, the content of trialkylsulfonium chloride, preferably octadecyldimethylsulfonium chloride, is in the range from 10 to 80 wt.-%, relative to the total weight of the composition.

[0112] In a preferred embodiment, the content of trialkylsulfonium chloride, preferably octadecyldimethylsulfonium chloride, is in the range from 10 ± 5.0 wt.-%, preferably 20 ± 15 wt.-%, preferably 20 ± 10 wt.-%, preferably 20 ± 5.0 wt.-%, preferably 30 ± 25 wt.-%, preferably 30 ± 20 wt.-%, preferably 30 ± 15 wt.-%, preferably 30 ± 10 wt.-%, preferably 30 ± 5.0 wt.-%, preferably 40 ± 35 wt.-%, preferably 40 ± 30 wt.-%, preferably 40 ± 25 wt.-%, preferably 40 ± 20 wt.-%, preferably 40 ± 15 wt.-%, preferably 40 ± 10 wt.-%, preferably 40 ± 5.0 wt.-%, preferably 50 ± 45 wt.-%, preferably 50 ± 40 wt.-%, preferably 50 ± 35 wt.-%, preferably 50 ± 30 wt.-%, preferably 50 ± 25 wt.-%, preferably 50 ± 20 wt.-%, preferably 50 ± 15 wt.-%, preferably 50 ± 10 wt.-%, preferably 50 ± 5.0 wt.-%, preferably 60 ± 35 wt.-%, preferably 60 ± 30 wt.-%, preferably 60 ± 25 wt.-%, preferably 60 ± 20 wt.-%, preferably 60 ± 15 wt.-%, preferably 60 ± 10 wt.-%, preferably 60 ± 5.0 wt.-%, preferably 70 ± 25 wt.-%, preferably 70 ± 20 wt.-%, preferably 70 ± 15 wt.-%, preferably 70 ± 10 wt.-%, preferably 70 ± 5.0 wt.-%, preferably 80 ± 15 wt.-%, preferably 80 ± 10 wt.-%, preferably 80 ± 5.0 wt.-%, preferably 90 ± 5.0 wt.-%, in each case relative to the total weight of the composition.

[0113] In other preferred embodiments, the composition according to the present application is a solid.

[0114] In a preferred embodiment of the composition according to the present application, the content of trialkylsulfonium chloride, preferably octadecyldimethylsulfonium chloride, is at least 2.5 pg / g; preferably at least 5.0 pg / g, preferably at least 7.5 pg / g, preferably at least 10 pg / g, preferably at least 15 pg / g, preferably at least 20 pg / g, preferably at least 25 pg / g, preferably at least 30 pg / g, preferably at least 40 pg / g, preferably at least 50 pg / g, preferably at least 60 pg / g, preferably at least 70 pg / g, preferably at least 80 pg / g, preferably at least 90 pg / g, in each case relative to the total weight of the composition.

[0115] In a preferred embodiment of the composition according to the present application, the content of trialkylsulfonium chloride, preferably octadecyldimethylsulfonium chloride, is at most 200 pg / g, preferably at most 190 pg / g, preferably at most 180 pg / g, preferably at most 170 pg / g, preferably at most 160 pg / g, preferably at most 150 pg / g, preferably at most 140 pg / g, preferably at most 130 pg / g, preferably at most 120 pg / g, preferably at most 110 pg / g, preferably at most 100 pg / g, preferably at most 90 pg / g, preferably at most 80 pg / g, preferably at most 70 pg / g, preferably at most 60 pg / g, preferably at most 50 pg / g, preferably at most 40 pg / g, preferably at most 30 pg / g, preferably at most 20 pg / g, preferably at most 10 pg / g, in each case relative to the total weight of the composition.

[0116] In addition to trialkylsulfonium chloride, preferably octadecyldimethylsulfonium chloride, and preferably the agriculturally acceptable carrier present, the composition according to the present application can comprise one or more additives. Preferred additives include, but are not limited to, pH buffers, thickeners, deposition agents (stickers), water conditioning agents, wetting agents, spreading agents, humectants, leaf cuticle and / or cell membrane penetration aids, surfactants, plant growth enhancers, foaming agents, antifoaming agents, drift control agents, spray drift reduction agents, evaporation reduction agents, dyes, UV absorbers, and combinations thereof. Such additives are known to the person skilled in the art and are commercially available as individual compounds or as mixtures (masterbatches). They can be contained in the composition according to the present application in the amounts customary therefor.

[0117] The additive can be in the form of a crop protection agent spray additive and / or a surfactant. The additive can increase the permeability of the plant cuticle and / or cell membrane. The additive can be a non-ionic spreading and penetration aid; and / or can function to reduce the surface tension of the composition.

[0118] The additive can enhance the fungicidal activity of the trialkylsulfonium chloride, for example, by increasing the permeability of the cuticle and / or cell membrane. The additive can enhance the fungicidal activity of the trialkylsulfonium chloride, for example, by increasing the permeability of the plant cuticle and / or cell membrane.

[0119] In preferred embodiments, the composition according to the present application comprises a surfactant in addition to the trialkylsulfonium chloride according to the present application, preferably octadecyldimethylsulfonium chloride, which can be considered a cationic surfactant in its own right. Surfactants reduce the surface tension in the spray droplets of the composition when it is applied to a material, such as a surface, a plant leaf, etc., which helps the composition to spread out and cover the target material with a thin film, resulting in the composition being more effectively or more quickly absorbed into the material. Surfactants can also influence the absorption of the composition when sprayed on the stems or leaves of a plant by altering the viscosity and crystal structure of the waxes on the leaf and stem surfaces, making them more easily permeable to the trialkylsulfonium chloride. The surfactant can be selected to enhance the antifungal properties of the composition by any one or more of:

[0120] a) causing the composition to spread more evenly over the material to which the composition is applied;

[0121] b) increasing the retention (or'stickiness') of the composition on the material;

[0122] c) for plant or crop protection applications, increasing the penetration of the composition through the hairs, scales or other leaf surface structures of the plant;

[0123] d) preventing crystallisation of the composition; and / or

[0124] e) slowing the drying of the composition.

[0125] It is envisaged that the composition according to the present application comprises, in addition to the trialkylsulfonium chloride, a single surfactant, or a combination of two or more surfactants. Each surfactant can be independently selected from non-ionic surfactants, ionic surfactants, amphoteric surfactants, zwitterionic surfactants, and combinations thereof.

[0126] Nonionic surfactants are generally biodegradable and compatible with many fertilizers. Some nonionic surfactants are waxy solids and require a liquid carrier (co-solvent, such as an alcohol or glycol) to dissolve into a liquid. Glycol carriers are generally preferred over alcohols because the latter are flammable, evaporate quickly, and increase the number of fine spray droplets (making the formulation prone to drift when sprayed). Preferred nonionic surfactants include silicone surfactants (such as silicones and organosiloxanes). Silicone surfactants significantly reduce the surface tension of the composition, enabling the composition to form a thin layer on the leaf or stem surface of a plant in use. Silicone surfactants also reduce surface tension and can allow the composition to penetrate the stomata of a plant leaf. Silicone surfactants also provide a protective effect to the composition of the present invention by making it very difficult to wash off after being applied. Silicone surfactants can also affect the amount / rate of absorption of trialkylsulfonium chloride, preferably octadecyldimethylsulfonium chloride, through the leaf cuticle. Preferred nonionic surfactants also include carbamide surfactants (urea surfactants). Carbamide surfactants can include, for example, mono-carbamide dihydrogen sulfate.

[0127] Suitable ionic surfactants can be selected from cationic surfactants and anionic surfactants. Preferred cationic surfactants include tallow amine ethoxylates. Preferred anionic surfactants include sulfates, carboxylates, and phosphates attached to lipophilic hydrocarbons, including, for example, linear alkylbenzene sulfonates.

[0128] Amphoteric surfactants function similarly to nonionic surfactants. Preferred amphoteric surfactants include, for example, lecithin (phosphatidylcholine) and amidopropylamines.

[0129] Wetting or spreading agents reduce the surface tension in the composition and allow the composition to form a large thin layer on the leaves and stems of the target plant. Preferred wetting or spreading agents include nonionic surfactants, preferably diluted with water, alcohol, or glycol; polyglycerol fatty acid esters; and polyglycols.

[0130] Drift control agents or spray drift control agents are preferably used to reduce spray drift of the composition, for example, when the composition is sprayed onto a plant, which most often occurs when air currents carry fine spray droplets (diameter < 150 pm) away from the target area. Drift control agents modify the viscoelasticity of the spray solution, producing a coarser spray with larger average droplet size and weight, and minimizing the number of small, easily-foamed droplets. Suitable drift control agents include polymers, such as polyacrylamides, polysaccharides, and gums.

[0131] Preferred deposition agents (stickers) include, for example, film-forming plant gels, emulsifiable resins, emulsifiable mineral oils, waxes, and water-soluble polymers. Deposition agents can be used to reduce the loss of the composition on the target plant due to evaporation of the composition from the target surface or beading and dropping off of the composition. Deposition agents are particularly useful for the compositions of the present application in the form of dry (wettable) powders and granular formulations.

[0132] Antifoams and defoamers reduce, inhibit, or destroy the formation of foam in containers that can hold the compositions of the present application. Preferred antifoams include, for example, oils, polydimethylsiloxanes and other silicones, alcohols, stearates, and glycols.

[0133] The compositions according to the present application can comprise one or more further antifungal agents.

[0134] Preferred further antifungal agents are independently of each other selected from

[0135] (1 ) Inhibitors of the sterol biosynthesis,

[0136] (2) Inhibitors of the respiratory chain at complex I or II,

[0137] (3) Inhibitors of the respiratory chain at complex III,

[0138] (4) Inhibitors of the mitosis and cell division,

[0139] (5) Compounds capable to have a multisite action,

[0140] (6) Compounds capable to induce a host defense,

[0141] (7) Inhibitors of the amino acid and / or protein biosynthesis,

[0142] (8) Inhibitors of the ATP production,

[0143] (9) Inhibitors of the cell wall synthesis,

[0144] (10) Inhibitors of the lipid and membrane synthesis,

[0145] (11 ) Inhibitors of the melanin biosynthesis,

[0146] (12) Inhibitors of the nucleic acid synthesis,

[0147] (13) Inhibitors of the signal transduction,

[0148] (14) Compounds capable to act as an uncoupler, and

[0149] (15) Other fungicides.

[0150] The preferred further antifungal agent is independently of each other selected from the group consisting of azoles; amino derivatives; strobilurins; specific anti- chlamydospore compounds; anilino-pyrimidines; benzimidazoles and analogues; dicarboximides; multi-halogenated fungicides; systemic acquired resistance (SAR) inducers; phenylpyrroles; acylamino acids; anti-peronosporic compounds; dithio carbamates; arylamidines; phosphorous acid and its derivatives; fungicidal copper compounds; plant-based oils (botanicals); chitosan; sulphur-based fungicides; fungicidal amides; and azacyclic compounds; or any combination thereof.

[0151] The composition according to the application as described above is preferably a pre- mixed concentrate, more preferably a pre-mixed suspension concentrate, still more preferably an aqueous pre-mixed suspension concentrate.

[0152] The pre-mixed concentrate according to the application is preferably diluted prior to use, preferably with water, by a factor of 2 to 500, such as 10, preferably 20, preferably 50, preferably 100, preferably 200, preferably 250.

[0153] Another aspect of the present application relates to an agricultural composition, preferably a ready-to-use aqueous composition, comprising:

[0154] (i) the composition according to the application as described above; and

[0155] (ii) a diluent, preferably water.

[0156] Thus, both the carrier and the diluent can be water. For the purpose of the present patent specification, different terms are used, whereas in the agricultural composition prepared thereby, it can no longer be possible to distinguish between diluent and carrier, depending on the individual case.

[0157] Another aspect of the present application relates to a method for preparing an agricultural composition, preferably a ready-to-use aqueous composition, comprising adding a diluent, preferably water, to the composition according to the application as described above.

[0158] All preferred embodiments of the composition according to the application as described above apply analogously to the agricultural composition according to the application. The essential difference between the composition according to the application as described above (i.e. preferably a pre-mixed concentrate, more preferably a pre-mixed suspension concentrate, still more preferably an aqueous pre-mixed suspension concentrate) of one aspect and the agricultural composition according to the application of another aspect is the content of the ingredients relative to the total weight of the composition and relative to the total weight of the agricultural composition. When the diluent is added increasing the total weight of the agricultural composition, the content of the ingredients of the agricultural composition is relatively reduced. When the diluent is the same as the carrier or one of the components of the carrier, the content of the carrier is relatively increased by the addition of further carrier (i.e. diluent).

[0159] In a preferred embodiment of the agricultural composition according to the present application, the content of trialkylsulfonium chloride, preferably octadecyldimethylsulfonium chloride, is at least 2.5 pg / ml; preferably at least 5.0 pg / ml, preferably at least 7.5 pg / ml, preferably at least 10 pg / ml, preferably at least 15 pg / ml, preferably at least 20 pg / ml, preferably at least 25 pg / ml, preferably at least 30 pg / ml, preferably at least 40 pg / ml, preferably at least 50 pg / ml, preferably at least 60 pg / ml, preferably at least 70 pg / ml, preferably at least 80 pg / ml, preferably at least 90 pg / ml, in each case relative to the total weight of the agricultural composition.

[0160] In a preferred embodiment of the agricultural composition according to the present application, the content of trialkylsulfonium chloride, preferably octadecyldimethylsulfonium chloride, is at most 200 pg / ml, preferably at most 190 pg / ml, preferably at most 180 pg / ml, preferably at most 170 pg / ml, preferably at most 160 pg / ml, preferably at most 150 pg / ml, preferably at most 140 pg / ml, preferably at most 130 pg / ml, preferably at most 120 pg / ml, preferably at most 110 pg / ml, preferably at most 100 pg / ml, preferably at most 90 pg / ml, preferably at most 80 pg / ml, preferably at most 70 pg / ml, preferably at most 60 pg / ml, preferably at most 50 pg / ml, preferably at most 40 pg / ml, preferably at most 30 pg / ml, preferably at most 20 pg / ml, preferably at most 10 pg / ml, in each case relative to the total weight of the agricultural composition.

[0161] Another aspect of the present application relates to the use of the composition according to the present application as described above as a pesticide, preferably as a fungicide. The use according to the present application preferably encompasses contacting a pest, its habitat, a material or plant to be protected from a pest, soil, a locus where a plant is growing, a locus where a plant is to grow, or propagation material with a pesticidally effective amount of the composition according to the present application.

[0162] Another aspect of the present application relates to a method for controlling or combating pests and / or improving the health of a plant, the method comprising contacting a pest, its habitat, a material or plant to be protected from a pest, soil, a locus where a plant is growing, a locus where a plant is to grow, or propagation material with a pesticidally effective amount of the composition according to the present application as described above.

[0163] Preferably, the pest is a fungus; preferably a harmful fungus; preferably a phytopathogenic harmful fungus.

[0164] In a preferred embodiment, the fungus is selected from the group consisting of:

[0165] (a) Opisthosporidia; preferably selected from Aphelidea, Rozellidea and Microsporidia;

[0166] (b) Chytridiomycota; preferably selected from Chytridiomycetes, Monoblepharidomycetes and Hyaloraphidiomycetes;

[0167] (c) Neocallimastigomycota;

[0168] (d) Blastocladiomycota;

[0169] (e) Zoopagomycota; preferably selected from Zoopagomycotina, Entomophthoromycotina (e.g. basidiobolomycetes, Neozygitomycetes, Entomophthoromycetes) and Kickxellomycotina;

[0170] (f) Mucoromycota; preferably selected from Mortierellomycotina and Mucoromycotina;

[0171] (g) Glomeromycota; preferably selected from Paraglomerales, Archaeosporales, Diversisporales and Glomerales;

[0172] (h) Basidiomycota; preferably selected from Pucciniomycotina (e.g. Agaricostilbomycetes, Atractiellomycetes, Classiculomycetes, Cryptomycocolacomycetes, Cystobasidiomycetes, Microbotryomycetes, Mixiomycetes, Pucciniomycetes, Spiculogloeomycetes, Tritirachiomycetes), Ustilagomycotina (e.g. Ustilaginomycetes, Exobasidiomycetes, Malasseziomycetes, Moniliellomycetes) and Agaricomycotina (e.g. Tremellomycetes, Dacymycetes, Agaricomycetes);

[0173] (i) Ascomycota; preferably selected from Taphrinomycotina (e.g. Taphrinomycetes, Neolectomycetes, Schizosaccharomycetes, Pneumocystidomycetes, Archaeorhizomycetes), Saccharomycotina (e.g. Saccharomycetes, Saccharomycetales) and Pezizomycotina (e.g. Arthoniomycetes, Coniocybomycetes, Dothideomycetes, Eurotiomycetes, Geoglossomycetes, Laboulbeniomycetes, Lecanoromycetes, Leothiomycetes, Lichinomycetes, Orbiliomycetes, Pezizomycetes, Sordariomycetes, Xylonomycetes);

[0174] and combinations thereof.

[0175] Preferred plant pathogenic fungal and oomycete species that can be combated using the compositions according to the application include Basidiomycetes, Ascomycetes, Deuteromycetes or imperfect fungi, Chytridiomycetes, Zygomycetes, Microspolidia and Oomycetes. Among them, but not exclusively, Puccinia spp., Ustilago spp, Tilletia spp., Uromyces spp., Phakopsora spp., Rhizoctonia spp., Erysiphe spp., Sphaerotheca spp., Podosphaera spp., Uncinula spp., Helminthosporium spp., Rhynchosporium spp., Pyrenophora spp., Monilia spp., Sclerotinia spp., Septoria spp. (Mycosphaerella spp., Zymoseptoria spp.), Venturia spp., Botrytis spp., Alternaria spp., Fusarium spp., Cercospora spp., Cercosporella herpotrichoides, Colletotrichum spp., Pyricularia oryzae, Sclerotium spp., Phytophthora spp., Pythium spp., Plasmopara viticola, Peronospora spp., Pseudoperonospora cubensis, Bremia lactucae.

[0176] In preferred embodiments, the fungus belongs to the phylum Ascomycota, preferably to the class Dothideomycetes, more preferably to the order Capnodiales, yet more preferably to the family Mycosphaerellaceae, yet more preferably to the genus Septoria, and most preferably to the species Septoria tritci.

[0177] In preferred embodiments, the fungus belongs to the clade SAR, preferably to the phylum Oomycota, more preferably to the order Peronosporales, yet more preferably to the family Peronosporaceae. Preferably, the fungus belongs to the genus Plasmopara, preferably to the species Plasmopara viticola. Preferably, the fungus belongs to the genus Phytophthora, preferably to the species Phytophthora infestans.

[0178] Specific fungal species infections that can be combated using the compositions according to the application include: Ensiphe graminis in cereals, Zymoseptoria tritici in cereals, especially wheat, Magnaporthe oryzae in cereals, especially rice, Erysiphe cichoracearum and Sphaerotheca fuliginea in cucurbits, Podosphaera leucotricha in apples, Uncinula necator in vines, Venturia inaequalis (apple scab) in apples, Helminthosporium species in cereals, Septoria nodorum in wheat, Botrytis cinerea (grey mould) in strawberries and grapes, Cercospora arachidicola in peanuts, Pseudocercosporella herpotrichoides in wheat and barley, Pyricularia oryzae in rice, Fusarium and Verticillium species in various plants, and Alternaria species in fruits and vegetables.

[0179] Examples of plant fungal diseases that can be combated using the compositions according to the application include, but are not limited to, blight (particularly wheat blight), damping-off, fusarium wilt, gummy stem blight, black root rot, root rot, blast (particularly rice blast), cottony rot, smut, rust, potato blight, mildew, clubroot, anthracnose, damping-off, gummy stem blight, leaf blight, septoria spot, ling spot, black leg, stalk rot, black scab, ergot, leaf curl, scab, snow mold, tobacco black shank, and verticillium wilt.

[0180] The use according to the application and the method according to the application preferably encompass the treatment of a phytopathogenic disease, preferably caused by a fungal disease. The phytopathogenic disease can be a fungal disease of plants or seeds thereof, such as cereals (wheat, barley, rye, oat, rice, maize, sorghum, etc.), fruit trees (apple, pear, plum, peach, almond, cherry, banana, grape, strawberry, raspberry, blackberry, etc.), citrus trees (orange, lemon, mandarins, grapefruit, etc.), legumes (beans, peas, lentils, soybeans, etc.), vegetables (spinach, lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes, eggplants, peppers, etc.), cucurbits (pumpkin, zucchini, cucumber, melon, watermelon, etc.), oil plants (sunflower, rape, peanut, castor-oil plant, coconut, etc.), tobacco, coffee, tea, cocoa, sugar cane, cotton, or horticultural plants.

[0181] Preferably, the plants are selected from the group consisting of agricultural plants, horticultural plants, ornamental plants and silvicultural plants. Preferably, the plants are field crops.

[0182] For the purposes of the present specification, the term "plants" is synonymous with the term "crops", which is to be understood as plants of economic importance and / or plants which are artificially cultivated. The term "plants" as used herein includes all parts of the plants such as germinating seeds, emerged seedlings, herbaceous plants as well as rooted woody plants including all belowground parts such as roots and aboveground parts.

[0183] In preferred embodiments, the plant is an agricultural plant. For the purposes of the present specification, an "agricultural plant" is a plant whose parts (e.g. seeds) or whole are harvested or cultivated on a commercial scale, or which is used as an important source of feed, food, fiber (e.g. cotton, flax), fuel (e.g. wood, bioethanol, biodiesel, biomass) or other chemical compounds. Preferred agricultural plants are, for example, a) cereals, e.g. wheat, rye, barley, triticale, oat, sorghum or rice, sugar beets (e.g. sugar or fodder beets); b) fruits, such as pome fruits, stone fruits or berries, e.g. apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, blackberries or gooseberries; leguminous plants, such as lentils, peas, alfalfa or soybeans; c) oil plants, such as rape, oilseed rape, canola, flaxseed, mustard, olives, sunflowers, coconut, cocoa beans, castor oil plants, oil palm, peanuts or soybeans; d) cucurbits, such as squashes, cucumbers or melons; e) fiber plants, such as cotton, flax, hemp or jute; f) citrus fruits, such as oranges, lemons, grapefruits or mandarins; g) vegetables, such as spinach, lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes, cucurbits or paprika; h) lauraceae, such as avocados, cinnamon or camphor; i) energy and raw material plants, such as maize, soybean, rape, canola, sugar cane or oil palm; j) tobacco; k) nuts; 1) coffee; m) tea; n) bananas; o) vine plants (table grapes and grape juice vine plants); p) hops; q) turf grass; and r) natural rubber plants.

[0184] Preferred agricultural plants are field crops (such as potatoes, sugar beets), cereals (such as wheat, rye, barley, oat, sorghum, rice, maize, cotton, oilseed rape, and canola), leguminous plants (such as soybean, peas, and field beans), sunflowers, sugar cane, vegetables (such as cucumbers, tomatoes, onions, leeks, lettuce, and squashes). Preferred agricultural plants are selected from the group consisting of soybean, sunflower, maize, cotton, canola, sugar cane, sugar beet, pome fruit, barley, oat, sorghum, rice, and wheat. Preferred agricultural plants are selected from the group consisting of soybean, sunflower, maize, cotton, canola, sugar cane, sugar beet, pome fruit, barley, oat, sorghum, rice, and wheat. Preferred agricultural plants are selected from the group consisting of wheat, barley, maize, soybean, rice, canola, and sunflower. Preferred agricultural plants are selected from the group consisting of wheat, barley, oat, rice, sorghum, plantain, maize, potato, vegetables, and fruits.

[0185] In a preferred embodiment, the plant is a horticultural plant. For the purpose of the present specification, a "horticultural plant" is a plant that is commonly used in horticulture, such as ornamental plants, vegetables and / or fruits. Examples of ornamental plants are turf grass, geranium, pelargonium, petunia, begonia and fuchsia. Examples of vegetables are potato, tomato, pepper, cucurbit, cucumber, melon, watermelon, garlic, onion, carrot, cabbage, bean, pea and lettuce, more preferably from tomato, onion, pea and lettuce. Examples of fruits are apple, pear, cherry, strawberry, citrus, peach, apricot and blueberry.

[0186] In a preferred embodiment, the plant is an ornamental plant. For the purpose of the present specification, an "ornamental plant" is a plant that is commonly used in landscaping, such as plants on parks, gardens and balconies. Examples are turf grass, geranium, pelargonium, petunia, begonia and fuchsia.

[0187] In a preferred embodiment, the plant is a silvicultural plant. For the purpose of the present specification, a "silvicultural plant" is a tree, more specifically a tree that is used for reforestation or industrial plantations. Industrial plantations are commonly used for the commercial production of forest products, such as wood, pulp, paper, rubber trees, Christmas trees or young trees for landscaping purposes. Examples of silvicultural plants are coniferous trees, such as pines (in particular Pinus species, firs and spruces), eucalyptus, tropical trees (such as teak, rubber tree, oil palm), willows (Salix species), poplars (Populus species), beeches (Fagus species), birches, oil palm and oaks.

[0188] The trialkylsulfonium chloride according to the present application, preferably octadecyldimethylsulfonium chloride, can be synthesized along standard routes described in the literature for the synthesis of sulfonium compounds. For example, a fatty alcohol of the residue R3(C 18-32 -alkyl-OH) can be converted to the corresponding alkyl chloride C 18-32 -alkyl-Cl, for example by reaction with SOCl2or SO2Cl2. The chloroalkane thus obtained can be reacted with an alkylthiol (C 1-3 -alkyl-SH) to give the sulfide C 18-32 -alkyl-S-C 1-4 -alkyl. Subsequently, the sulfide thus obtained can be alkylated by reaction with a suitable alkylating agent such as C 1-3 -alkyl-I to give the sulfonium iodide C 18-32 -alkyl-S + (C 1-4 -alkyl)2I-. The corresponding chloride salt can be obtained by a metathesis reaction with an excess of a suitable salt such as NaCl.

[0189] The following examples further illustrate the present application, but should not be construed as limiting its scope:

[0190] Example 1 : Septoria tritci blotch on wheat Figure 1

[0191] The protective potential of octadecyldimethylsulfonium chloride (ODS-Cl) according to the present application against Septoria tritci (Zymoseptoria tritici, Z. tritici) blotch on wheat was investigated and compared to the comparative octadecyldimethylsulfonium iodide (ODS-I) known from G. Steinberg et al. Lipophilic cations protect crops from antifungal pathogens through multiple modes of action. Nature Communications 11: 1608 (2020).

[0192] The Septoria tritci species belongs to the genus Septoria within the family Mycosphaerellaceae within the order Capnodiales within the class Dothideomycetes within the phylum Ascomycota within the kingdom Fungi.

[0193] Antifungal mutant generation using UV mutagenesis was performed according to the following procedure. Z. tritici IP0323 cells were harvested from 5-day-old yeast extract peptone dextrose (YPD) agar plates grown at 18 °C and spore cells were suspended in sterile water. Cell number was determined using a Cellometer Auto 1000 cell counter (Nexcelom Biosciences, Lawrence, USA) and cell density was adjusted to 1 x 10 7 / ml. Two million cells per plate (200 μl, 1 x 10 7 / ml) were spread onto YPD agar plates amended with antifungal agents (5x IC 100 , 10x IC 100 , 50x IC 100 , 100x IC 100 of each antifungal agent) and UV wavelength 254 nm, 50 mJ cm -2Uvitec crosslinker CL-508 (Uvitec, Cambridge, UK) to induce mutagenesis of the cells to produce ~50% lethality. Selection plates were incubated in the dark at 18°C for 14 days. Visible colonies were picked from the selection plates and confirmed on fungicide amended plates (azoxystrobin: 5x IC100: 1.5 pg / ml; fluazinam: 5x IC100: 3.0 pg / ml). A total of 4 million cells were plated for each experiment (2 plates per experiment), with 5 replicates per experiment. For controls including DMSO (0.8% final concentration) and methanol (0.3% final concentration), 1000 Z. tritici pathogen cells were spread per plate (2 plates per experiment; 5 experiments) and plates were incubated as described above.

[0194] Visible colonies were counted and survival rates determined. The protocol was adapted from G. Scalliet et al., 2012, PLoS ONE 7(4): e35429). It was found that octadecyldimethylsulfonium chloride (ODS-Cl) according to the present application was effective in inhibiting plate growth and was ~2.5 times better than comparative octadecyldimethylsulfonium iodide (ODS-I).

[0195] Thus, the antifungal effect of the sulfonium compound according to the present application, which exists as a salt with a chloride counter-anion, is superior compared to the corresponding compound forming a salt with an iodine counter-anion. While this superior antifungal activity has been shown to control Septoria tritci blotch on wheat, it is equally effective against other fungi.

[0196] The results of the experiment to determine the IC100values for Z. tritici are shown in Example 2 - Downy mildew of grapevine caused by Plasmopara viticola .

[0197] Figure 2 Example 3 - Potato late blight caused by Phytophthora infestans

[0198] It was investigated whether octadecyldimethylsulfonium chloride (ODS-Cl) according to the present application can provide a significant level of protection against P. viticola on detached grapevine leaves compared to two reference fungicides, namely Folpet 80WG and Dodine (Technical product). To this end, a dose-effect curve and ED 50 .

[0199] The species Plasmopara viticola belongs to the genus Plasmopara within the family Peronosporaceae within the order Peronosporales within the phylum Oomycota within the evolutionary clade SAR.

[0200] Materials and methods: The fungus strain (pathogen) used was Plasmopara viticola (strain name PvS). This strain was isolated in 2007 from untreated vines in France. It is known to be sensitive to all fungicides used against grape downy mildew.

[0201] The following fungicide formulations were used:

[0202]

[0203] The formulations were prepared in a water volume corresponding to 300 L / ha. No surfactant such as Tween or any other compound improving the retention on the leaves was used.

[0204] The timeline of the in planta experiment was as follows:

[0205] (a) 0 days: prophylactic treatment of detached leaves with a hand sprayer (100 L / ha); treatment of the abaxial leaf face;

[0206] (b) 1 day after treatment: use of leaf discs. Inoculation of P. viticola on the abaxial leaf face with a calibrated sporangia suspension; and

[0207] (c) 7 days after inoculation: observation of the disease severity and intensity.

[0208] Step (a) - prophylactic treatment: grapevine leaves (Chardonnay variety) were taken from young plants and surface sterilized. The abaxial face of each leaf was treated with a fungicide preparation or distilled water (control) using a hand sprayer (2 bars) calibrated to deliver 300 L / ha. For each test condition, 2 to 3 leaves were treated. One day after treatment, leaf discs were cut on untreated or treated grapevine leaves (triplicate, each including at least 7 leaf discs). The leaf discs were transferred onto Petri dishes with the abaxial face facing upwards.

[0209] Step (b) - P. viticola inoculation of grapevine leaf discs: calibrated sporangia suspension of P. viticola strain PvS was inoculated on the abaxial face of each leaf disc. After inoculation, the Petri dishes were placed in a climatic chamber: temperature was 20°C during the day / 16°C during the night - light cycle was 16 hours light / 8 hours dark and relative humidity (RH) was controlled.

[0210] Step (c) - Disease assessment: infection intensity and analysis: disease assessment at 7 dpi was performed by using any of the following disease scales:

[0211] - 0: no fungal growth

[0212] - 1 : very small lesions with sporulation

[0213] - 2: sporulated lesions smaller than the size of a droplet

[0214] - 3: sporulated lesions of the same size as the initial droplet size

[0215] - 4: sporulated lesions larger than the size of a droplet

[0216] Disease severity index (DSI) was determined using the following formula:

[0217]

[0218] DSI was converted into observed efficacy (OE) by using the following formula:

[0219] OE = ((b - a) / b) x 100,

[0220] where a corresponds to the DSI (%) of the treated plants and b corresponds to the DSI (%) of the untreated (control) plants. These values were compared by using appropriate statistical tests with the Xlstat statistical test software (threshold a = 5%).

[0221] The distribution of discs was used to determine the Disease Severity Index (DSI) and the DSI values were converted to Observed Efficiency (OE) for each product tested. Preventative treatment was performed one day prior to inoculation of P. viticola strain PvS on grapevine leaf discs under controlled conditions. To compare fungicide DSI%, ratios between 1 and 1000 mg a.i. / L (ppm) were tested in the DSI evaluation of ODS-C1 6. The reference fungicide Folpet 80WG was tested at 3333 ppm and the reference fungicide Dodine was tested at the field approved ratio of 2267 ppm. All fungicides were used directly preventative against P. viticola strain PvS on grapevine leaf discs for 24h. The statistical test used was the Fischer LSD parametric test (a = 5%).

[0222] The results are shown in Figure 3

[0223] As shown, the octadecyldimethylsulfonium chloride (ODS-C1 ) based fungicide directly tested in this study effectively protected grape leaves from downy mildew (EC 50 = 70 ppm or 21 g a.i. / ha) infestation. A robust dose effect was observed against Plasmopara viticola. The two reference products used at their field recommended ratios also showed complete protection against the development of P. viticola symptoms. Folpet 80WG (3333 ppm) and Dodine (2267 ppm) both showed complete control of downy mildew but at significantly higher doses.

[0224] Figure 4

[0225] It was further investigated whether ODS-C1 could control other oomycetes, namely Phytophthora infestans, the causative agent of potato (and tomato) late blight.

[0226] Phytophthora infestans belongs to the genus Phytophthora within the family Peronosporaceae within the order Peronosporales within the phylum Oomycota within the evolutionary clade SAR.

[0227] ​P. infestans is an oomycete, a distinct clade from the fungi, whose spores can be spread by wind and water. Within the asexual cycle, sporangia are released from infected tissue and under certain circumstances can germinate and infect plant tissue (known as indirect germination). Sporangia can also release contained zoospores which will germinate and infect tissue (known as direct germination). Zoospores have flagella which allow them to have greater mobility in water conditions on leaf surfaces or in soil. Spores generated from the asexual life cycle have high mobility but low viability, on the other hand, oospores generated from sexual reproduction are not mobile per se but can persist in the soil for several years under latent physiological conditions. At the end of the season, frost will eliminate infected residual plant material, but oospores can still survive, becoming the starting point for a new epidemic cycle when environmental conditions are more favourable.

[0228] Once inside the tissue, the first symptoms appear after a few days at the level of the foliage. Symptoms are often visible at the level of the leaf, but other organs such as stems, fruits (tomatoes) or tubers can also be infected. When tubers are infected, the disease can sometimes remain latent at harvest time and manifest itself later during storage. Infected leaves release zoospores under humid conditions, which can quickly spread throughout the plot.

[0229] As the use of fungicides is the main strategy to limit the spread of P. infestans, the pathogen has developed resistance to certain active ingredients whose mode of action is limited to a unique cellular target (so-called single-site active ingredients). The use of multi-site active ingredients can present a great benefit as their mode of action is less suspected to allow the appearance of resistance.

[0230] Materials and methods: Phytophthora infestans (strain named Pi96) was used as the fungal strain (pathogen). This strain has been isolated from an untreated European sample of potato. It is known to be sensitive to all fungicides.

[0231] The following fungicide formulations were used:

[0232]

[0233] The timeline of the plant in situ experiment was as follows:

[0234] (a) (-1) dpi: preventive treatment on potato leaves with a manual sprayer calibrated to deliver an equivalent volume of 300 L / ha;

[0235] (b) 0 dpi: P. infestans inoculation on potato detached leaves (5 leaflets) with calibrated sporangia suspension; and

[0236] (c) 3 dpi and 10 days after inoculation: disease assessment on potato leaflets.

[0237] Step (a) - Preventive treatment: Potato leaves (Bintje variety) were taken from young plants and surface sterilized. The abaxial face of each detached leaf was treated with a fungicide preparation or distilled water (control) using a manual sprayer (2 bars) calibrated to deliver 300 L / ha (preventive treatment). For each tested condition, a minimum of 3 leaves or at least 18 inoculated leaflets were treated. Preventive treatment 24h: one day after treatment, leaflets were excised on untreated or treated potato leaves (triplicates including at least 5 to 7 leaflets each). Leaflets were transferred onto Petri dishes with the abaxial face down.

[0238] Step (b) - P. infestans inoculation of potato leaflets: inoculation on treated or untreated detached leaflets with droplets of calibrated sporangia suspension of P. infestans strain Pi96. After inoculation, potato leaves were transferred into a saturated humidity atmosphere in a climatic chamber under the following conditions: 18°C during the day - 14h / night 15°C - 10h.

[0239] Step (c) - Disease assessment: infection intensity and analysis: disease assessment was performed according to example 2.

[0240] Regarding the evaluation of disease severity (DSI) and treatment efficacy, the evolution of DSI (disease severity index) obtained 24h after treatment from potato leaves inoculated with P. infestans and previously treated preventively was determined. DSI is the surface of diseased leaflets. Results are summarized in the following table:

[0241]

[0242] Results are also shown in Example 4 - Water solubility at different pH values .

[0243] To compare the % of fungicide DSI, the efficacy of the fungicide obtained 24h after treatment from potato leaves inoculated with P. infestans and previously treated preventively was calculated from the DSI values at the final assessment time (10 dpi).

[0244] Results are also shown in Solubility .

[0245] As shown, the octadecyldimethylsulfonium chloride (ODS-Cl) based fungicide directly tested in this study was effective in protecting potato leaves from late blight at doses starting from 100 ppm. When used at 1000 ppm, ODS-Cl was able to completely control the disease, similar to the effect obtained with the two reference products Dithan Neotec (Mancozeb) and SYLLIT MAX (Dodine) used at the same dose.

[0246] Figure 5

[0247] Water solubility of octadecyldimethylsulfonium chloride (ODS-Cl) and octadecyldimethylsulfonium iodide (ODS-I) according to the present application was determined at different pH values ​ . The results are summarized in the following table:

[0248]

[0249] The results are shown in ​ .

[0250] As shown, octadecyldimethylsulfonium chloride (ODS-Cl) has a higher solubility in water than octadecyldimethylsulfonium iodide (ODS-I). Moreover, the solubility of ODS-Cl depends on the pH value: only 0.28 g / L of ODS-Cl is soluble in water at pH 7, but the solubility of ODS-Cl increases significantly with increasing pH (0.94 g / L at pH 10) and decreasing pH (1.65 g / L at pH 2.2).

Claims

1. A composition comprising a trialkylsulfonium chloride according to the general formula (A): wherein R1 represents -CH3; R2 represents -CH3; and wherein the content of the trialkylsulfonium chloride is greater than 0.1 wt.%, relative to the total weight of the composition.

3. The composition of claim 1, wherein the trialkylsulfonium chloride is octadecyldimethylsulfonium chloride.

4. The composition of claim 3, wherein the trialkylsulfonium chloride is n- octadecyldimethylsulfonium chloride.

5. The composition of claim 1, comprising an agriculturally acceptable carrier. R3represents -(CH2) n -CH3, wherein n is an integer in the range of 17 to 31; 6. The composition of claim 5, wherein the carrier is selected from the group consisting of: (a) water; (b) a monohydric alcohol; (c) a diol; (d) a monoalkyl glycol ether; (e) a dialkyl glycol ether; (f) a diol ester; (g) glycerol and glycerol ethers; (h) a cyclic ether; (i) a ketone; (j) a monobasic ester; (k) a dibasic ester; (l) an alkylene carbonate; (m) a dialkyl sulfoxide; (n) an alkyl sulfone; (o) an alkyl amide; (p) an alkanol amine; (q) a fatty acid, a fatty acid ester, a fatty acid amide; (r) an oil; and combinations thereof.

2. The composition according to claim 1, wherein R3 represents -(CH2) 17 -CH3, -(CH2) 19 -CH3 or -(CH2) 21 -CH3.

7. The composition of claim 6, wherein the monohydric alcohol is selected from methanol, ethanol, propanol, isopropanol, cyclohexanol, or benzyl alcohol.

8. The composition of claim 6, wherein the diol is selected from ethylene glycol, propylene glycol, diethylene glycol, or dipropylene glycol.

9. The composition of claim 6, wherein the monoalkyl glycol ether is triethylene glycol monobutyl ether.

10. The composition of claim 6, wherein the dialkyl glycol ether is ethylene glycol dimethyl ether.

11. The composition of claim 6, wherein the glycerol ether is isopropylidene glycerol.

12. The composition of claim 6, wherein the cyclic ether is selected from tetrahydrofuran or dioxolane.

13. The composition of claim 6, wherein the ketone is selected from acetone, butanone, or cyclohexanone.

14. The composition of claim 6, wherein the monobasic ester is selected from ethyl lactate, ethyl acetate, or gamma-butyrolactone.

15. The composition of claim 6, wherein the dibasic ester is selected from dimethyl glutarate or dimethyl succinate.

16. The composition of claim 6, wherein the alkylene carbonate is selected from ethylene carbonate or propylene carbonate.

17. The composition of claim 6, wherein the dialkyl sulfoxide is dimethyl sulfoxide.

18. The composition of claim 6, wherein the alkyl sulfone is sulfolane.

19. The composition of claim 6, wherein the alkyl amide is selected from N- methylpyrrolidone, N-ethylpyrrolidone, or dimethylformamide.

20. The composition of claim 6, wherein the alkanol amine is selected from monoethanolamine, diethanolamine, triethanolamine, an alkyl diethanolamine, or a dialkyl monoethanolamine. ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ 21. The composition of claim 6, wherein the oil is selected from the group consisting of oils of plant or animal origin, vegetable oil, crop oil, crop oil concentrate, plant oil, methylated seed oil, petroleum oil, or silicone oil.

22. The composition of any one of claims 1-21, wherein the composition is aqueous and has a pH in the range of 2 to 14.

23. The composition of any one of claims 1-21, wherein the trialkylsulfonium chloride is present in an amount of at least 0.5% by weight relative to the total weight of the composition.

24. The composition of claim 23, wherein the trialkylsulfonium chloride is octadecyldimethylsulfonium chloride.

25. The composition of claim 23, wherein the trialkylsulfonium chloride is present in an amount of at least 1.0% by weight relative to the total weight of the composition.

26. The composition of claim 23, wherein the trialkylsulfonium chloride is present in an amount of at least 2.5% by weight relative to the total weight of the composition.

27. The composition of claim 23, wherein the trialkylsulfonium chloride is present in an amount of at least 5% by weight relative to the total weight of the composition.

28. The composition of claim 23, wherein the trialkylsulfonium chloride is present in an amount of at least 7.5% by weight relative to the total weight of the composition.

29. The composition of claim 23, wherein the trialkylsulfonium chloride is present in an amount of at least 10% by weight relative to the total weight of the composition.

30. The composition of claim 23, wherein the trialkylsulfonium chloride is present in an amount of at least 12.5% by weight relative to the total weight of the composition.

31. The composition of claim 23, wherein the trialkylsulfonium chloride is present in an amount of at least 15% by weight relative to the total weight of the composition.

32. The composition of claim 23, wherein the trialkylsulfonium chloride is present in an amount of at least 17.5% by weight relative to the total weight of the composition.

33. The composition of claim 23, wherein the trialkylsulfonium chloride is present in an amount of at least 20% by weight relative to the total weight of the composition.

34. The composition of claim 5, wherein the carrier is selected from the group consisting of: (a) natural soil minerals and mineral earths; (b) synthetic minerals; (c) inorganic salts; (d) synthetic granules of inorganic or organic fine powders; (e) granules of organic materials; (f) diatomaceous earth; (g) tricalcium phosphate; (h) polysaccharides; (i) products of plant origin; (j) grain fine powders; (k) other organic substances; (l) solid fertilizers; and combinations thereof.

35. The composition of claim 34, wherein the natural soil minerals and mineral earths are selected from the group consisting of silicates, calcite, marble, pumice, meerschaum, talc, kaolin, clay, talc, limestone, lime, calcium carbonate, chalk, terra-cotta, loess, quartz, perlite, attapulgite, montmorillonite, vermiculite, bentonite, dolomite, or diatomaceous earth.

36. The composition of claim 34, wherein the synthetic mineral is selected from silica, silica gel, alumina or a silicate selected from aluminum silicate or magnesium silicate.

37. The composition of claim 34, wherein the inorganic salt is selected from aluminum sulfate, calcium sulfate, copper sulfate, iron sulfate, magnesium sulfate, silicon sulfate or magnesium oxide.

38. The composition of claim 34, wherein the particles of organic material are selected from sawdust, coconut shell, corn ear or husk, or tobacco stem.

39. The composition of claim 34, wherein the polysaccharide is selected from cellulose, cellulose ether, starch, xanthan gum, pullulan, guar gum.

40. The composition of claim 34, wherein the product of plant origin is selected from grain meal, tree bark meal, wood meal, nut shell meal.

41. The composition of claim 34, wherein the grain meal is selected from corn, rice, wheat, barley, sorghum, millet, oat, triticale, rye, buckwheat, fonio or quinoa meal.

42. The composition of claim 34, wherein the other organic substance is selected from cork powder, adsorptive carbon black, charcoal, peat, soil mixtures, compost, agricultural industrial residues, water-soluble polymers, resins or waxes.

43. The composition of claim 34, wherein the solid fertilizer is selected from urea or ammonium salts.

44. The composition of claim 34, wherein the ammonium salt is selected from ammonium sulfate, ammonium phosphate, ammonium nitrate.

45. The composition of any one of claims 1-21 and 34-44, further comprising one or more additives selected independently from each other from the group consisting of pH buffers, thickening agents, deposition agents, water conditioning agents, wetting agents, humectants, leaf cuticle and / or cell membrane penetration aids, surfactants, plant growth enhancers, foaming agents, antifoaming agents, spreading agents, drift control agents, spray drift reduction agents, evaporation reduction agents, dyes and UV absorbers.

46. The composition of any one of claims 1-21 and 34-44, further comprising one or more further antifungal agents.

47. The composition of claim 46, wherein the one or more further antifungal agents are selected independently from each other from the group consisting of: (1) inhibitors of ergosterol synthesis; (2) inhibitors of the respiratory chain at complex I or II; (3) inhibitors of the respiratory chain at complex III; (4) inhibitors of mitosis and cell division; (5) compounds capable of having a multisite action; (6) compounds capable of inducing host defenses; (7) inhibitors of amino acid and / or protein biosynthesis; (8) inhibitors of ATP production; (9) inhibitors of cell wall synthesis; (10) inhibitors of lipid and membrane synthesis; (11) inhibitors of melanin biosynthesis; (12) inhibitors of nucleic acid synthesis; (13) inhibitors of signal transduction; (14) compounds capable of acting as decouplers; and (15) other fungicides.

48. The composition of any one of claims 1-21, 34-44 and 47, which is a ready- mix concentrate.

49. The composition of claim 48, which is a pre-suspended concentrate.

50. The composition of claim 48, which is an aqueous pre-suspended concentrate.

51. An agricultural composition comprising: (i) the composition of any one of claims 1-21, 34-44, and 47; and (ii) a diluent.

52. The agricultural composition of claim 51, which is a ready-to-use aqueous composition.

53. The agricultural composition of claim 51, wherein the diluent is water.

54. Use of the composition of any one of claims 1-21, 34-44, and 47 or the agricultural composition of any one of claims 51-53 as a fungicide.

55. A method for controlling or combating pests and / or improving the health of a plant, the method comprising contacting the pests, their habitat, material or plant to be protected from the pests, soil, a locus where the plant is growing or is to grow, or propagation material with a pesticidally effective amount of the composition of any one of claims 1-21, 34-44, and 47 or the agricultural composition of any one of claims 51-53.

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