Use of sulfur compounds in crops for the control of tobamovirus viruses

Abstract

The present invention relates to the use of a compound of formula (1) or a composition (C) comprising a compound of formula (1) for the treatment and / or prevention of crop infections caused by a Tobamovirus. The present invention also relates to a method for the treatment and / or prevention of crop infections caused by a Tobamovirus, comprising applying to the growing medium or cultivation soil a compound of formula (1) or a composition (C) comprising a compound of formula (1): R-S(O)n-SX-R' (1).

Description

Technical Field

[0001] This invention relates to the field of controlling Tobacco Mosaic Virus (TMV) viruses, and more particularly to the use of sulfur-containing compounds, preferably dimethyl disulfide (DMDS), for controlling TMV viruses.

[0002] The present invention also relates to a method for controlling tobacco mosaic virus in crops using such a sulfur-containing compound, preferably by drip application. Background Technology

[0003] The genus *Tobacco Mosaic Virus* belongs to the family Virgaviridae. It includes various viruses such as Tobacco Mosaic Virus (TMV), Tomato Mosaic Virus (ToMV), Ryegrass Mosaic Virus (HRV), Mild Mottle Virus of Pepper (PMMV), Mild Mottle Virus of Red Pepper, and Tomato Brown Curly Fruit Virus (ToBRFV).

[0004] These different viruses pose a real problem for crops, especially market horticultural crops. For example, they can reduce crop yields, render fruits and vegetables inedible, and spread rapidly.

[0005] In particular, Tomato Brown Curly Fruit Virus (ToBRFV) was first observed in Israel in 2014 as a tobacco mosaic virus. Since then, ToBRFV has also been detected in Europe, Asia, and the Americas. It causes typical symptoms of tobacco mosaic virus, including mosaic patterns and yellowing of leaves, as well as discoloration and deformity of fruit. These symptoms render the fruit unsellable and reduce crop yield. Furthermore, ToBRFV can overcome the tomato TM-22 gene, which confers resistance to both tobacco mosaic virus (TMV) and tomato mosaic virus (ToMV) in tomatoes. ToBRFV is also known to cause significant losses in pepper cultivation.

[0006] The rapid international spread of this virus, coupled with its ability to break down resistance genes, is causing increasing concern in the fruit and vegetable production industry, particularly among tomato producers worldwide. Measures are being taken and research is underway to try to prevent its spread and protect crops. For example, in the case of hydroponics, substrates contaminated with Tobacco Mosaic Virus (TMN) viruses must be replaced annually, and this process is very expensive.

[0007] Therefore, there is a real need to provide solutions for the prevention and / or treatment of crop infections caused by Tobacco Mosaic Virus (ToBRFV) viruses, particularly ToBRFV. There is also a real need to treat crop soil and / or substrates to eliminate Tobacco Mosaic Virus (ToBRFV) viruses.

[0008] One object of the present invention is to provide a compound that enables the prevention and / or treatment of tobacco mosaic virus, particularly ToBRFV virus, infection of crops.

[0009] One of the objectives of this invention is to provide a formulation of the compound that can be readily applied to crops, particularly by application to soil and / or substrate.

[0010] One object of the present invention is to provide a compound and / or a formulation thereof, which is suitable for drip administration, particularly compatible with irrigation systems.

[0011] Another object of the present invention is to provide a method for preventing and / or treating (particularly by drip application) crop infections caused by Tobacco Mosaic Virus (TMV) viruses, more particularly ToBRFV virus. Summary of the Invention

[0012] The present invention fully or partially satisfies the above objectives.

[0013] This invention relates to the use of compounds of formula (1) for the treatment and / or prevention of crop infections caused by Tobacco Mosaic Virus (TMN) viruses:

[0014] RS(O) n -S x -R'(1)

[0015] in:

[0016] - R is selected from straight-chain or branched alkyl groups containing 1 to 4 carbon atoms and straight-chain or branched alkenyl groups containing 2 to 4 carbon atoms;

[0017] - n equals 0, 1, or 2;

[0018] - x is an integer selected from 0, 1, 2, 3 or 4; preferably, x represents 1, 2, 3 or 4;

[0019] - R' is selected from straight-chain or branched alkyl groups containing 1 to 4 carbon atoms, and straight-chain or branched alkenyl groups containing 2 to 4 carbon atoms, or only when n=x=0, it is a hydrogen atom or an alkali metal atom. In fact, the inventors have discovered that the compounds of formula (1) have antiviral activity against Tobacco Mosaic Virus (TMN) viruses.

[0020] The present invention also relates to a method for treating and / or preventing crop infections caused by Tobacco Mosaic Virus (TMV) viruses, comprising applying a compound of formula (1) as defined above to a crop substrate and / or soil.

[0021] Preferably, the compound of formula (1) is dimethyl disulfide (DMDS, formula CH3-SS-CH3).

[0022] Preferably, the virus is the tomato brown wrinkle virus.

[0023] Specifically, the crop is the tomato crop.

[0024] Specifically, the compound of formula (1) is formulated in composition (C), which comprises:

[0025] - At least 80% by weight, preferably at least 90% by weight, and more preferably between 90% and 95% by weight of the total weight of the composition (C);

[0026] - At least one surfactant, comprising, by weight, between 0.1% and 20%, preferably between 1% and 10%, relative to the total weight of the composition (C); and

[0027] - Optionally, an odor masking agent, such as an odor masking agent weighing between 0.1% and 1.5% by weight relative to the total weight of the composition (C). Detailed Implementation Plan

[0028] The invention will now be described in more detail in a non-limiting manner in the following description.

[0029] Unless otherwise stated, all percentages are mass percentages.

[0030] In this paper, the quantities indicated for a given species may be applied to that species according to all of its definitions (as mentioned herein), including more restrictive definitions.

[0031] Therefore, this invention relates to the use of compounds of formula (1) as defined below for the treatment and / or prevention of crop infections caused by Tobacco Mosaic Virus (TMN) viruses. This invention also relates to a method for treating and / or preventing crop infections caused by TMN viruses, comprising applying a compound of formula (1) as defined below to a crop substrate and / or soil.

[0032] Compound of formula (1)

[0033] The compound of formula (1) is defined according to the following formula:

[0034] RS(O) n -S x -R'(1)

[0035] in:

[0036] -R is selected from straight-chain or branched alkyl groups containing 1 to 4 carbon atoms and straight-chain or branched alkenyl groups containing 2 to 4 carbon atoms;

[0037] -n equals 0, 1, or 2;

[0038] -x is an integer selected from 0, 1, 2, 3 or 4; preferably, x represents 1, 2, 3 or 4;

[0039] -R' is selected from straight-chain or branched alkyl groups containing 1 to 4 carbon atoms, and straight-chain or branched alkenyl groups containing 2 to 4 carbon atoms, or, only when n=x=0, a hydrogen atom or an alkali metal atom.

[0040] Non-limiting examples of groups R and R' include methyl, propyl, allyl, and 1-propenyl.

[0041] Preferably, in the compound of formula (1), n=0; the compound then corresponds to formula (1'):

[0042] RSS x -R'(1')

[0043] Wherein R and R' may be the same or different, preferably the same, each independently representing a straight-chain or branched alkyl group containing 1 to 4 carbon atoms, or a straight-chain or branched alkenyl group containing 2 to 4 carbon atoms, and x represents 1, 2, 3 or 4.

[0044] The most particularly preferred compound of formula (1) or (1') according to the present invention is dimethyl disulfide (DMDS).

[0045] The compound of formula (1) can be applied by plowing (by fumigation) or by dripping to the crop substrate and / or soil. It is more preferably applied by dripping to the substrate of soilless crops.

[0046] The compound of formula (1) can be applied alone or as a mixture with one or more other active compounds (e.g., other pesticides) known to those skilled in the art.

[0047] Composition (C)

[0048] Whether in the context of the use or method according to the invention, the compound of formula (1) can be formulated in composition (C) comprising:

[0049] - Relative to the total weight of the composition (C), at least 80% by weight, preferably at least 90% by weight, preferably between 90% and 95% by weight, of at least one compound of formula (1) as defined above;

[0050] - At least one surfactant, comprising, by weight, between 0.1% and 20%, preferably between 1% and 10%, relative to the total weight of the composition (C); and

[0051] -Optional odor masking agent, such as an odor masking agent weighing between 0.1% and 1.5% by weight relative to the total weight of the composition (C).

[0052] In particular, the composition (C) comprises a compound of formula (1).

[0053] Composition (C) preferably comprises:

[0054] - Relative to the total weight of the composition (C), at least 90% by weight, for example, between 90% and 95% by weight, of the compound of formula (1) as defined above, preferably DMDS;

[0055] - At least one surfactant, by weight, between 1% and 10% relative to the total weight of the composition (C); and

[0056] - Optionally, an odor masking agent at a weight of between 0.1% and 1.5% relative to the total weight of the composition (C).

[0057] Preferably, composition (C) comprises, or even consists of, the following:

[0058] - At least 90% by weight of the compound of formula (1) as defined above, preferably DMDS, relative to the total weight of the composition (C);

[0059] - At least one of the following (C) components, comprising between 1% and 10% by weight, preferably between 1% and 6% by weight, relative to the total weight of the composition (C). 10 -C 13 )alkylbenzene sulfonates; and

[0060] - Optionally, an odor masking agent at a weight of between 0.1% and 1.5% relative to the total weight of the composition (C).

[0061] The composition (C) according to the invention can very preferably correspond to the dimethyl disulfide compositions sold by Arkema under the names Paladin® EC, Accolade® EC, Atomal® 13, and Sekamteau®. Sekamteau® is the most particularly preferred. According to one embodiment, the composition (C) does not contain water.

[0062] The composition (C) according to the invention can be prepared by any method known to those skilled in the art, such as by simply mixing its components, optionally accompanied by stirring and heating, the order of addition of the components not affecting the composition (C).

[0063] Preferably, composition (C) is used when the compound of formula (1) is administered by drip infusion.

[0064] surfactants

[0065] The surfactants included in composition (C) are, in particular, primarily hydrophilic surfactants, i.e., those with an HLB (hydrophilic-lipophilic balance) value greater than or equal to 8. They can be anionic, cationic, nonionic, or amphoteric in nature.

[0066] Non-limiting examples of anionic surfactants include:

[0067] -alkyl-, aryl- or alkylaryl-sulfonic acids, fatty acids with basic pH, sulfosuccinic acid or alkyl, dialkyl, alkylaryl or alkali metal, alkaline earth metal, ammonium or triethanolamine salts of sulfosuccinic acid or sulfosuccinic acid of alkyl, dialkyl, alkylaryl or polyoxyethylene-alkylaryl esters.

[0068] - Alkali metal or alkaline earth metal salts of esters of sulfuric acid, phosphoric acid, phosphonic acid or sulfoacetic acid and saturated or unsaturated fatty alcohols, as well as their alkoxylated derivatives.

[0069] Alkali metal or alkaline earth metal salts of alkylaryl sulfuric acid, alkylaryl phosphoric acid and alkylaryl sulfonate, and their alkoxylated derivatives.

[0070] Cationic surfactants that can be used include, for example, those from the quaternary alkylammonium, sulfonium, or fatty amine classes, which are acidic at pH, as well as their alkoxylated derivatives. Non-limiting examples of nonionic surfactants include alkoxylated alkylphenols, alkoxylated alcohols, alkoxylated fatty acids, fatty derivatives of sugars, or glycerol fatty esters.

[0071] Amphoteric surfactants that can be used include, for example, alkyl betaine or alkyl taurine.

[0072] The preferred surfactants according to the present invention are compounds based on alkylbenzene sulfonates and / or alkoxylated alkylphenols. More particularly, (C) 10 -C 13 ) Alkylbenzene sulfonates (also known as C66 benzenesulfonic acid) 10 -C 13 Salts of alkyl derivatives, such as the C4 salt of benzenesulfonic acid. 10 -C 13 Calcium salts of alkyl derivatives (CAS No. 1335202-81-7), and especially mixtures thereof in any proportion. Optionally, in the presence of an organic solvent such as 2-ethylhexyl-1-ol, the (C 10 -C 13 Alkylbenzene sulfonates may be mixed with other surfactants (e.g., with nonionic surfactants) or not.

[0073] The surfactant used may be in the form of a commercial composition, such as Atlox™ 4851B sold by Croda or T-Mulz® TE-CP sold by Harcros Chemicals.

[0074] Odor masking agent:

[0075] Some compounds of formula (1) have a strong, unpleasant, or even corrosive odor. In particular, DMDS has a strong and corrosive odor, partly due to the presence of highly odorous impurities and partly due to the inherent garlic and ether-like odor of the molecule. The same is true for most organosulfur compounds.

[0076] Generally, the oxides of these organosulfur compounds, especially DMSO, have a less aggressive odor. However, depending on the concentration of impurities, this odor can be unpleasant and bothersome to the end user.

[0077] Any type of known odor masking agent may be used in the compositions of the present invention. The term "odor masking agent" refers to a compound or a composition comprising several compounds that is capable of reducing, suppressing or masking the odor of the compound of formula (1) used.

[0078] One example that can be mentioned is chloropicrin, which is commonly used to flavor methyl bromide.

[0079] In particular, odor masking agents as described in application WO 2011 / 012815 may be used, which is incorporated herein by reference.

[0080] The odor masking agent may comprise at least one monoester, at least one diester and / or triester, at least one alcohol, at least one ketone, and optionally at least one terpene.

[0081] According to a preferred embodiment, the odor masking agent comprises:

[0082] a1) at least one monoester, ranging from 1% to 40% by weight;

[0083] a2) 10% to 70% by weight of at least one diester and / or triester;

[0084] a3) at least one alcohol, ranging from 1% to 30% by weight;

[0085] a4) 0.5% to 20% by weight of at least one ketone of the formula Ra-CO-Rb, wherein Ra represents a straight-chain or branched hydrocarbon chain comprising 1 to 6 carbon atoms, optionally containing one or more double bonds for unsaturation, and Rb represents a cyclic hydrocarbon chain or a straight-chain or branched hydrocarbon chain, optionally but preferably substituted with a cyclic structure, wherein Rb comprises 6 to 12 carbon atoms, optionally containing one or more double bonds for unsaturation, and optionally substituted with one or more hydroxyl groups; and

[0086] a5) Optionally up to 20% by weight of at least one terpene.

[0087] The percentages of a1, a2, a3, a4, and a5 are weight percentages expressed relative to the total weight of the odor masking agent.

[0088] Unless otherwise stated, the term "ppm" means parts per million by weight.

[0089] Therefore, the odor masking agent may contain at least one monoester described in a1) at 1% to 40%, preferably 2% to 35%, more preferably 5% to 30% of the total weight of the odor masking agent.

[0090] Illustrative but non-limiting examples of monoesters described under a1) include saturated or unsaturated C2-C... 20 Esters of acids, such as ethyl, propyl, butyl, pentyl, 2-methylbutyl, isopentyl, hexyl, benzyl, phenylethyl, menthyl and carvacrol acetates, propionates, butyrates, methylbutyrates, valerates, hexanoates, heptanoates, oleates, linoleates and linolenic acid esters, and mixtures thereof.

[0091] More particularly preferred are isoamyl acetate, hexyl acetate, 2-methylbutyl butyrate, isoamyl butyrate, benzyl acetate, phenethyl acetate, and mixtures thereof.

[0092] The odor masking agent may further comprise at least one diester and / or triester (a2), in an amount of 10% to 70% by weight, preferably 15% to 65% by weight, more preferably 20% to 60% by weight, relative to the total weight of the odor masking agent. At least one diester and / or triester may be mentioned in a non-limiting manner, selected from phthalates such as diethyl phthalate; citrates such as triethyl citrate; and malonates such as diethyl malonate.

[0093] The odor masking agent may also contain at least one alcohol (a3) ​​at 1% to 30%, preferably 5% to 25% by weight of the total odor masking agent, advantageously at least one monohydric alcohol containing 1 to 30 carbon atoms, preferably 6 to 20 carbon atoms, more preferably 8 to 11 carbon atoms, the carbon atoms forming a straight chain or a branched chain, the straight chain or branched chain optionally containing one or more double bonds in the form of unsaturation, and optionally containing a saturated, or fully or partially unsaturated 5 or 6-membered ring structure.

[0094] The alcohols defined above are preferably monohydric alcohols, wherein the hydroxyl functional group is preferably carried by an sp2 carbon atom. It should be understood that the hydroxyl functional group can also be carried by a carbon atom contained in a cyclic structure as defined above.

[0095] The alcohol used in odor masking agents and as defined above is advantageously selected, by way of non-limiting examples, from menthol, neomenthol, phenylethyl alcohol, benzyl alcohol, citronellol, dihydromyrcene alcohol, dihydroterpineol, diethanol, ethyl linalool, geraniol, linalool, tetrahydrolinalool, tetrahydromyrcene alcohol, nerol, and mixtures of two or more thereof.

[0096] As a non-limiting example and preferably, the one or more ketones shown in a4) above are selected from damascones, damascenones, ionones, irisones, methyl ionones, frambinone (CAS No. 5471-51-2), and mixtures thereof. The amount of ketone is advantageously from 0.5% to 20% by weight, preferably from 1% to 10% by weight, relative to the total weight of the odor masking agent.

[0097] The odor masking agent may optionally further comprise at least one terpene, comprising up to 20% by weight of the total odor masking agent, preferably 1% to 10%.

[0098] Examples of terpenes indicated under a5) that may be used include, in a non-limiting manner, terpinene, myrcene, limonene, terpinene oil, pinene, juniperene, camphene, mixtures of two or more thereof, as well as terpene-based flavorings, especially those containing these components.

[0099] Furthermore, odor masking agents that can be used in the context of this invention may contain small amounts of other reagents (fragrances) commonly used in the field of fragrances, particularly one or more compounds having cyclic ketone and / or aldehyde functional groups, of which geraniol, nerol, citronellol, menthone, isomenthone, 1,8-cineole, baicalin, dihydroflavonoids and mixtures thereof may be mentioned, but are not limited to.

[0100] Where appropriate and even when necessary, odor masking agents may further comprise one or more additives commonly used in the art. Such additives may be selected, for example, in a non-limiting manner from solvents, pigments, dyes, preservatives, biocides, etc.

[0101] Among solvents, the most particularly preferred examples are alcohols, ethers, esters, and glycols. Particularly advantageously, the solvent is selected from diethyl phthalate, ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, polyethylene glycol, polypropylene glycol, and mixtures thereof, and even more advantageously from diethyl phthalate, dipropylene glycol, and mixtures thereof.

[0102] A typical odor masking agent composition comprises (by weight relative to the total weight of the odor masking agents):

[0103] - At least one monoester (a1) from 5% to 30% by weight, selected from isoamyl acetate, ethyl methyl-2-butyrate, isoamyl butyrate, phenylethyl acetate, ethyl hexanoate, benzyl acetate, hexyl acetate and mixtures thereof;

[0104] - From 20% to 60% by weight of at least one diester and / or triester (a2), selected from phthalates such as diethyl phthalate; citrates such as triethyl citrate; and malonates such as diethyl malonate, and mixtures thereof;

[0105] - at least one alcohol, preferably at least two alcohols, more preferably at least three alcohols, in an amount of 5% to 25% by weight, as described above under a3);

[0106] - At least one ketone, preferably at least two ketones, more preferably at least three ketones, in an amount of 1% to 10% by weight, as described above under a4); and

[0107] - At least one, preferably at least two, terpenes mentioned in a5 above, from 1% to 10% by weight, preferably a mixture thereof.

[0108] The following are representative, but not limiting, examples of odor masking agents, in which each component comprises one, more, or even all of the listed compounds:

[0109] Component a1): 16.00%, including benzyl acetate, hexyl acetate, isoamyl acetate, phenethyl acetate, ethyl hexanoate, and ethyl 2-methylbutyrate.

[0110] Component a2): 50.00%, containing diethyl malonate and diethyl phthalate.

[0111] Component a3): 20.60%, containing phenylethanol, citronellol, geraniol, linalool, and cis-3-hexanol.

[0112] Component a4): 4.50%, containing 1-(4-hydroxyphenyl)but-3-one and α-ionone.

[0113] Component a5): 7.00% orange terpenes

[0114] Other: 1.90%, containing citral, ethyl maltol, and ethyl methyl phenyl glycidyl ester.

[0115] These compositions are given as examples.

[0116] Crops and substrates

[0117] The crops according to the invention can be soilless crops and field crops. Preferably, the crops are soilless crops. Preferably, the crops are garden crops and / or fruit crops (e.g., small fruit crops and red fruits such as blueberries, raspberries, strawberries and blackberries) and / or nursery plants.

[0118] Specifically, these are the following crops:

[0119] - Solanaceae family, especially tomatoes, peppers, bell peppers, black peppers, potatoes, and tobacco;

[0120] - Cucurbitaceae family, especially cucumbers and melons;

[0121] - Legumes, especially green beans and peas;

[0122] - Rosaceae family, such as strawberry, raspberry and blackberry;

[0123] - Ericaceae family, such as blueberries; and

[0124] - Ornamental flowers.

[0125] Particularly preferred crops are tomatoes, tobacco, red fruits, potatoes, and ornamental flowering crops, especially soilless tomato crops.

[0126] The term "substrate" should be understood specifically to refer to any type of carrier used for cultivating plants and that is distinct from soil. In the case of soilless crops, the substrate is therefore a solid carrier on which plants can grasp and grow. Nutrients typically enter the substrate through fertilizers contained in irrigation water.

[0127] The substrate for soilless crops can be selected from:

[0128] -Inorganic matrix (sand, gravel, pebbles, perlite, rock wool, garden felt, vermiculite),

[0129] - Organic substrates (rice husks, compost, peat, sawdust, rice straw, coconut fiber), and

[0130] - Synthetic substrates (sheets, sponges, moisture-absorbing plastic fibers).

[0131] Coconut fiber (especially coconut fiber blocks), compost, peat, and rock wool can be given priority, with coconut fiber being the preferred choice.

[0132] Virus

[0133] Compounds of formula (1) as defined above can be used to control viruses of the genus *Tobacco Mosaic Virus*. In particular, they have antiviral activity against said viruses. Among the viruses of the genus *Tobacco Mosaic Virus*, the following may be mentioned: Tobacco Mosaic Virus (TMV), Tomato Mosaic Virus (ToMV), Ryegrass Mosaic Virus (HRV), Mild Mottle Virus of Pepper (PMMV), Mild Mottle Virus of Red Pepper, and Tomato Brown Curl Fruit Virus (ToBRFV), with Tomato Brown Curl Fruit Virus (ToBRFV) being preferred. Viruses of the genus *Tobacco Mosaic Virus* are specifically described in the publication Hakan Fidan et al., *Journal of Integrative Agriculture*, 2021, 20(8): 2170–2179.

[0134] Application of compound (1) or composition (C)

[0135] Whether in the context of the use or method according to the invention, the compound of formula (1) can be applied by any technique known to those skilled in the art.

[0136] Compounds of formula (1), particularly DMDS, can be fumigants. More specifically, compounds of formula (1) are in liquid form and are converted into gases (fumigation) after application to contaminated substrates and / or soil: thus, they can combat existing Tobacco Mosaic Virus viruses.

[0137] The compound of formula (1) can be applied, for example, by dripping, using a plow, by pouring directly onto the substrate and / or soil, or by injecting into the substrate (e.g., using a syringe). Preferably, it is applied by dripping. The compound of formula (1) can be applied alone or formulated, for example, in a composition (C) as defined above.

[0138] For example, when using a scraper to apply a compound of formula (1), it can be used as is or formulated with one or more surfactants (such as those mentioned above for composition (C). The amount of surfactant can be from 1% to 10% by weight relative to the total weight of the formulation.

[0139] The composition (C) can also be applied by drip application, using a plow, by direct pouring onto the substrate and / or soil, or by injection into the substrate (e.g., using a syringe). Preferably, it is applied by drip application. The composition (C) can be diluted before application, particularly in water. It can be advantageously diluted in water and distributed in the irrigation system of the crop to be treated.

[0140] Preferably, the compound or composition (C) of formula (1) according to the invention is applied to the substrate and / or soil of the crop prior to planting.

[0141] For example, a compound or composition (C) of formula (1) according to the invention is injected into an irrigation system for the substrate and / or soil of one or more crops, and then applied by drip irrigation before setting one or more crops (i.e., before planting). Therefore, the use and / or method according to the invention may include the following steps:

[0142] a) Applying the compound or composition (C) of formula (1) to the substrate and / or soil to be treated, preferably by drip application;

[0143] b) Place the crop on the substrate and / or soil.

[0144] Those skilled in the art can easily adjust the treatment according to the properties of the crop, soil and / or substrate to be treated, as well as climatic conditions.

[0145] Preferably, the compound of formula (1) according to the invention is applied at a concentration of 0.01% to 1% by weight, preferably 0.1% to 1% by weight, and more particularly 0.1% to 0.5% by weight relative to the weight of water (irrigation water), for example, by injection into an irrigation system.

[0146] Preferably, the composition (C) according to the invention is applied at a concentration between 0.01% and 1% by weight relative to the weight of water (irrigation water), for example, by injection into an irrigation system. More particularly, the composition (C) is applied at a concentration between 0.1% and 0.5% by weight relative to the weight of water (irrigation water), more preferably between 0.1% and 0.4%.

[0147] In particular, the dosage of the compound or composition (C) of formula (1) applied ranges from 1 to 400 l / ha, preferably from 30 to 240 l / ha, and more preferably from 120 l / ha.

[0148] Particularly preferably, the method according to the invention comprises the following steps:

[0149] -Optionally remove as much plant material as possible from the soilless culture substrate and / or from the soil of the crop;

[0150] - Position or return the application system, preferably the drip system, to its place;

[0151] -Optional placement of soilless culture substrate and / or soil and irrigation system, as well as barrier membrane;

[0152] - Inject the compound or composition (C) of formula (1) into the irrigation system at a concentration of 0.01% to 1% and / or a dosage range of 1 to 400 l / ha (preferably 120 l / ha);

[0153] - Optionally, the barrier membrane may be removed after 14 days.

[0154] Infusion

[0155] Drip application can be carried out through any conventional drip irrigation system. These types of drip irrigation systems or devices (also known as drip irrigation systems or micro-irrigation systems) are well known and are commonly used to provide water and optional irrigation solutions (such as liquid fertilizers) to plants to be cultivated in soil in agricultural land or plantations, substrates for soilless crops, etc.

[0156] In addition to conventional irrigation devices, these systems include, for example, a supply source and / or reservoir for a compound or composition (C) of formula (1) optionally formulated as defined above, and a metering device optionally for the compound or composition (C) of the optionally formulated formula (1). The optionally formulated compound or composition (C) of formula (1) may be supplied by any means known per se, and for example from a reservoir containing it. The reservoir may be equipped with a pump and advantageously with a plunger tube, as described in International Application WO 2014 / 147034. The composition (C) of the present invention may also be applied in the form of an emulsion (F), as described in Patent Application WO 2021 / 038165, which is incorporated herein by reference.

[0157] All piping, including the drippers, or even the entire drip irrigation system, and the soil and / or substrate to be treated, can be covered with a barrier membrane (i.e., a membrane impermeable to the vapors of the fumigant) before the fumigant is applied. This prevents the fumigant from dissipating into the atmosphere, thus protecting the operator and the environment. Different types of barrier membranes exist, such as SIF (semi-impermeable membrane), VIF (virtually impermeable membrane), or TIF (completely impermeable membrane) membranes currently used for fumigation treatment of soil and / or substrates. The barrier membrane can be a photocatalytic membrane as described in application WO 2013 / 030513. For example, a “Barrier-Film NFT54-195-1 / 2Cl2” membrane can be used.

[0158] The methods and uses according to the present invention can be combined or alternated with other conventional pesticide treatments or other fumigant treatments.

[0159] The invention will be explained in more detail in the following embodiments.

[0160] Example

[0161] Unless otherwise stated, percentages are expressed by weight relative to the total weight of the composition.

[0162] Example 1: The composition (C) according to the present invention

[0163] The composition (C) according to the invention is prepared by mixing various ingredients, comprising:

[0164] - 95% by weight DMDS; and

[0165] - 5.00 wt% of benzenesulfonic acid-based C 10 -C 13 Surfactants of calcium salts of alkyl derivatives.

[0166] Example 2: The antiviral treatment according to the present invention

[0167] The efficacy of DMDS (dimethyl disulfide) formulated in composition (C) according to Example 1 was tested on tomato plants grown hydroponically and in greenhouses in Turkey. The substrate used for these plants was coconut fiber blocks (referred to as coconut blocks).

[0168] ToBRFV infection:

[0169] Coconut blocks were used in a previous tomato crop. This previous crop was then infected with Tomato Brown Curl Fruit Virus (ToBRFV). After tomato harvest, seedlings were extracted from the coconut blocks. The infected coconut blocks were reused to test the efficacy of DMDS against ToBRFV.

[0170] According to the method described in the literature "Robust molecular detection of the new tomato brown rugose fruit virus ininfected tomato and pepper plants from Turkey", the infection of coconut tubers was verified by PCR on the remaining root residues in the tubers.

[0171] I. Materials and Methods:

[0172] The infected coconut blocks were covered with a transparent TIF (completely impermeable membrane) barrier and connected to a drip irrigation system with an automated computerized system (Karaca control system).

[0173] Before application, calibration is performed to indicate the available water content for each block. The percentage of moisture content in the block is also controlled (60-70%). DMDS in the form of composition (C) of Example 1 is applied to the coconut blocks using an irrigation system.

[0174] After applying DMDS, flush the irrigation system.

[0175] Remove the barrier membrane 10 days after DMDS application.

[0176] A barrier membrane was also installed on the control block to allow water to be received only.

[0177] Tomato plants are then grown using plants from nurseries that have been proven to be free of viruses and bacteria.

[0178] As described below, the treatment was performed 9 times with different doses of DMDS, with each treatment repeated 4 times.

[0179] Application information is given in Table 1 below:

[0180] [Table 1]

[0181]

[0182] Then, following the method described in the literature "Robust molecular detection of the new Tomato brown rugose fruit virus ininfected tomato and pepper plants from Turkey", the roots of the treated plants and the roots of the control plants were removed to determine the infection of the tomato brown rugose fruit virus by PCR.

[0183] The results are shown in Table 2 below:

[0184] [Table 2]

[0185]

[0186] These results demonstrate the high efficacy of DMDS as a virucidal agent against Tomato Brown Wrinkle Fruit Virus: no virus was detected in any of the infected tomato plants after treatment, regardless of the tested dose and concentration.

Claims

1. The use of compounds of formula (1) for the treatment and / or prevention of crop infections caused by Tobacco Mosaic Virus (TMN) viruses: R-S(O) n -S x -R’(1) in: - R is selected from straight-chain or branched alkyl groups containing 1 to 4 carbon atoms and straight-chain or branched alkenyl groups containing 2 to 4 carbon atoms; - n equals 0, 1, or 2; - x is an integer selected from 0, 1, 2, 3 or 4; preferably, x represents 1, 2, 3 or 4; - R' is selected from straight-chain or branched alkyl groups containing 1 to 4 carbon atoms, and straight-chain or branched alkenyl groups containing 2 to 4 carbon atoms, or only when n=x=0, it is a hydrogen atom or an alkali metal atom.

2. The use according to claim 1, wherein the compound of formula (1) is a compound of formula (1'): R-S-S x -R’(1’) Where R and R' are the same or different, and each represents independently: A straight-chain or branched alkyl group containing 1 to 4 carbon atoms, or a straight-chain or branched alkenyl group containing 2 to 4 carbon atoms, where x represents 1, 2, 3 or 4.

3. The use according to claim 1, wherein the compound of formula (1) is dimethyl disulfide (DMDS).

4. The use according to any one of the preceding claims, wherein the compound of formula (1) is formulated in composition (C), the composition comprising: - At least 80% by weight of the compound of formula (1) as described in any one of claims 1 to 3, relative to the total weight of the composition (C); - At least one surfactant, by weight, between 0.1% and 20% relative to the total weight of the composition (C); and - Optional odor masking agent.

5. The use according to any one of claims 1 to 4, characterized in that, The virus is selected from tobacco mosaic virus (TMV), tomato mosaic virus (ToMV), ryegrass mosaic virus (HRV), mild mottle virus of pepper (PMMV), mild mottle virus of red pepper and tomato brown wrinkled fruit virus (ToBRFV), with tomato brown wrinkled fruit virus (ToBRFV) being preferred.

6. The use according to any one of claims 1 to 5, characterized in that... The crops are selected from those belonging to the Solanaceae, Cucurbitaceae, Fabaceae, Rosaceae, and Ericaceae families, as well as ornamental flowers; tomato is preferred.

7. A method for treating and / or preventing crop infection caused by a Tobacco Mosaic Virus virus, comprising applying a compound of formula (1) as defined in any one of claims 1 to 3 to the crop substrate and / or soil.

8. The treatment and / or prevention method according to claim 7, wherein the compound of formula (1) is formulated in composition (C), the composition comprising: - At least 80% by weight of the compound of formula (1) relative to the total weight of the composition (C); - At least one surfactant, by weight, between 0.1% and 20% relative to the total weight of the composition (C); and - Optional odor masking agent.

9. The treatment and / or prevention method according to claim 7 or 8, characterized in that, The compound of formula (1) or the composition (C) is injected into the crop irrigation system at a concentration between 0.01% and 1% by weight relative to water and / or at a dosage ranging from 1 l / ha to 400 l / ha.

10. The treatment and / or prevention method according to any one of claims 7 to 9, characterized in that, Before planting, apply the compound or composition (C) of formula (1) to the crop substrate and / or soil.

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