Insecticide composition comprising a macrolide active ingredient

Abstract

The invention relates to a suspension concentrate composition, the suspension concentrate comprising: a) at least one macrolide active substance; b) at least one aromatic hydrocarbon sulfonate condensed with formaldehyde; and c) ammonium sulfate. The invention also relates to the use of the suspension concentrate composition in pest control. The invention further relates to a method for increasing the stability of a macrolide active compound in a suspension concentrate formulation, the method comprising the use of a combination of an aromatic hydrocarbon sulfonate condensed with formaldehyde and ammonium sulfate in the formulation.

Description

Title of the invention: Insecticidal composition comprising a macrolide active ingredient

[0001] The present invention relates to an insecticidal composition comprising a macrolide active substance, more particularly an insecticidal suspension concentrate. The present invention further relates to the preparation of the suspension concentrate and its use.

[0002] Macrolide-based insecticidal substances are well known in the field of agrochemicals. Examples of substances in this group of insecticidal substances include avermectin, emamectin, pleocidin, ethyl pleocidin, ivermectin, abamectin, and methylamino avermectin. These macrolide compounds have relatively large molecular masses, complex spatial structures, a large number of oxygen atoms and / or hydroxyl groups, and all contain lactone rings. Consequently, macrolide insecticidal compounds tend to agglomerate when combined with compounds having polyhydroxyl and / or polyoxygen structures, due to the action of hydrogen bonds.

[0003] A common form of agrochemical formulation applied on a commercial scale is a suspension concentrate. Suspension concentrates comprise a suspension of solid particles of the active agrochemical ingredient in a suitable liquid medium, most often water. Suspension concentrate products tend to settle. The rate of settling conforms to Stokes' law of sedimentation:

[0004] [Math 1]

[0005] w = [2g (ps - p) gr2] / 9 p

[0006] where ps is the density of the particles, p is the density of the liquid, p is the viscosity of the liquid, r is the radius of the particles, and g is the acceleration due to gravity.

[0007] To counteract the tendency to sedimentation, it is known to add a thickener to a suspension concentrate product in order to adjust the fluid viscosity of the system and slow the sedimentation rate. This in turn reduces water separation and stratification during product storage and improves the physical stability of the product.

[0008] The most commonly used thickeners in suspension concentrate products are polymer compounds, such as xanthan gum, guar gum, cellulose, hydroxymethylcellulose, starch, polyvinyl alcohol, polyvinyl- Pyrrolidone and its derivatives. Such thickeners all contain a relatively large number of hydroxyl groups and / or oxygen atoms. Consequently, macrolide-based insecticidal molecules tend to aggregate with these thickening molecules due to hydrogen bonding, as described above. Therefore, these organic polymeric thickeners are not suitable for use in suspension concentrates containing macrolides as the active ingredient. This leads to a reduction in the physical stability of the suspension concentrate formulation, which in turn reduces the product's efficacy.

[0009] There is therefore a need for a technique to improve the stability and effectiveness of macrolide insecticide compounds when formulated as a suspension concentrate.

[0010] The present invention provides a suspension concentrate composition, the suspension concentrate comprising:

[0011] a) at least one macrolide active substance;

[0012] b) at least one aromatic hydrocarbon sulfonate condensed with formaldehyde; and

[0013] c) ammonium sulfate.

[0014] It was unexpectedly discovered that the combination of a condensed aromatic hydrocarbon sulfonate with formaldehyde and ammonium sulfate significantly improves the storage stability of a suspension concentrate containing an active macrolide compound.

[0015] In particular, it has been discovered that combining condensed aromatic hydrocarbon sulfonate with formaldehyde and ammonium sulfate in the suspension concentrate of the present invention slows the rate of particle settling in the suspension concentrate. Thus, the storage stability of the suspension concentrate of the present invention is significantly improved without requiring the addition of further thickeners, particularly polymeric organic thickeners, to the suspension concentrate. The use of a combination of condensed aromatic hydrocarbon sulfonate with formaldehyde and ammonium sulfate in a suspension concentrate prevents undesirable phenomena such as macrolide particle settling, water separation, flocculation, stratification, and similar phenomena during storage, thereby improving the physical stability of the suspension concentrate.This in turn improves the effectiveness of the suspension concentrate, particularly by maintaining the activity level of the macrolide component.

[0016] The use of a combination of a condensed aromatic hydrocarbon sulfonate with formaldehyde and ammonium sulfate according to the present invention makes it possible to use a suspension concentrate containing a low-viscosity macrolide, without that phenomena such as macrolide settling, water separation, flocculation, stratification, and others do not occur during storage, thus significantly improving the storage stability of the macrolide-containing suspension concentrate. In particular, the present invention allows the suspension concentrate to have a viscosity of less than 800 mPa·s, preferably less than 600 mPa·s, more preferably less than 400 mPa·s, and especially less than 300 mPa·s, which is technically advantageous for the preparation, handling, and use of the suspension concentrate.

[0017] The suspension concentrate formulation comprises solid particles of the macrolide active ingredient suspended in a liquid medium. The liquid medium may comprise any suitable liquid component or a mixture of two or more such components. Suitable liquid components are those that cannot dissolve the macrolide active ingredient. Suitable liquid components may be any one or a combination of at least two of the following: soybean oil, corn oil, rapeseed oil, epoxidized soybean oil, methyl oleate, ethyl laurate, methyl linoleate, palmitic acid, linseed oil, mineral oil, and water. Water is a preferred liquid medium for many embodiments.

[0018] According to some embodiments, the suspension concentrate formulation does not include an organic polymer thickener, and / or the suspension concentrate does not include xanthan gum, guar gum, cellulose, hydroxymethylcellulose, starch, polyvinyl alcohol, polyvinylpyrrolidone and derivatives thereof.

[0019] The suspension concentrate composition of the present invention comprises a macrolide as an active component, in particular a macrolide with insecticidal activity. Such macrolides are known in the art. The macrolide is preferably selected from avermectin, emamectin benzoate, pleocidin, ethyl pleocidin, ivermectin, and abamectin. Preferred macrolides include pleocidin, ethyl pleocidin, emamectin, and emamectin benzoate. Pleocidin is a particularly preferred macrolide.

[0020] The macrolide active substance may be present in the suspension concentrate of the present invention in any appropriate quantity. Preferably, the macrolide active substance is present in an amount of 1 g / L, more preferably 2 g / L, even more preferably 5 g / L, even more preferably 7.5 g / L, in particular 10 g / L. Preferably, the macrolide active substance is present in an amount of up to 600 g / L, more preferably up to 575 g / L, even more preferably up to 550 g / L, even more preferably up to 525 g / L, in particular up to 500 g / L. Preferably, the macrolide active substance is present in an amount from 1 to 600 g / L, more preferably from 5 to 550 g / L, even more preferably from 10 to 500 g / L.

[0021] The suspension concentrate composition of the present invention further comprises an aromatic hydrocarbon sulfonate condensed with formaldehyde. The term "aromatic hydrocarbon" should be understood as comprising any aromatic hydrocarbon fragment, including, but not limited to, naphthalene, phenyl, phenol, and cresol. Naphthalene is a particularly preferred aromatic hydrocarbon. The aromatic hydrocarbon fragments may also optionally be substituted with at least one alkyl group to form an alkyl-romatic hydrocarbon. The aromatic hydrocarbon fragments may be mono-, di-, or poly-substituted with substituent groups. Here, the term "alkyl" includes primary, secondary, and tertiary alkyl groups.In a preferred embodiment, the alkyl substituent is an alkyl group at C1 to C30, examples of which include methyl, ethyl, propyl, butyl, isopropyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, and dodecyl.

[0022] In a particularly preferred embodiment of the present invention, the alkyl sulfonate is a naphthalene sulfonate condensed with formaldehyde or a salt thereof as shown in formula I:

[0023] [Chem.l] 111 1 1 . L II .... V

[0024] in which:

[0025] each Ri is chosen independently from hydrogen, an alkali metal, an alkaline earth metal, ammonium, a mono-, di- or tri-alkylamine fragment in C1 to C4, or a mono-, di- or tri-hydroxyalkylamine fragment in C1 to C4; and

[0026] each R2 is independently chosen from hydrogen, a linear or branched alkyl or alkenyl group from C1 to C30; and

[0027] n is an integer from 1 to 25.

[0028] Preferably, Ri is selected from an alkali metal, an alkaline earth metal, ammonium, a mono-, di- or tri-alkylamine fragment in C1 to C4, or a mono-, di- or tri-hydroxyalkylamine fragment in C1 to C4.

[0029] Preferably R2 is an alkyl group at C1 to C20, more preferably an alkyl group at C1 to C15, even more preferably an alkyl group at C1 to C12, in particular an alkyl group at C1 to C6. Examples of suitable alkyl groups include methyl, ethyl, isopropyl, n-butyl and sec-butyl.

[0030] Each naphthalene fragment may contain one or more R2 substituents. Each R 2 may be present in a single position or any combination of multiple positions on the naphthalene fragment.

[0031] As mentioned above, the aromatic hydrocarbon sulfonate condensed with formaldehyde can be supplied in the composition as a salt. Examples of suitable salts include: alkali metal salts, i.e., Ri in formula I is an alkali metal, such as sodium and potassium; and alkaline earth metal salts, i.e., Ri in formula I is an alkaline earth metal, such as magnesium and calcium; and amine salts, i.e., Ri in formula I is an amine group, such as monomethylamine, dimethylamine, and triethylamine. Alkali metal salts, especially sodium salts, are particularly preferred.

[0032] As previously stated, naphthalene is a preferred aromatic hydrocarbon fragment. Examples of commercially available sodium salts of naphthalene-sulfonates condensed with formaldehyde include: Tersperse™ 2001, Tersperse™ 2100, Tersperse™ 2105 and Tersperse™ 2158 available from Huntsman; and the Tamol™ NH and NN series available from BASF.

[0033] In the composition of the present invention, alkylnaphthalene sulfonates condensed with formaldehyde, i.e. compounds of formula I in which R2 is an alkyl group, are particularly preferred. Sodium salts of alkylnaphthalene sulfonates condensed with formaldehyde are more particularly preferred. The sodium salts may have an average molecular weight ranging from 300 to 2000, preferably from 400 to 1000, and most preferably from 500 to 750. Examples of commercially available sodium salts of alkyl-substituted naphthalene sulfonates condensed with formaldehyde include: Morwet™ D-425, Morwet™ D-450, and Morwet™ D-809 available from AkzoNobel; Tersperse™ 2425 and Tersperse™ 2020 are available from Huntsman Corporation, and Supragil™ MNS-90 and MNS-425 from Rhodia Inc.

[0034] Other aromatic hydrocarbon sulfonates condensed with formaldehyde include: phenol salts condensed with formaldehyde, for example BASF's commercial products Tamol™ PP and DN; and sodium salts of cresol condensed with formaldehyde, for example Clariant's commercial products Dis-persogen™ 1494 and Rapidaminreserve™ CL.

[0035] In the suspension concentrate of the present invention, the content of aromatic hydrocarbon sulfonate condensed with formaldehyde can be any amount suitable for providing the required stability of the macrolide active component. Preferably, the aromatic hydrocarbon sulfonate condensed with formaldehyde is present in an amount of 1 g / L, more preferably 2 g / L, and even more preferably 5 g / L, more preferably 7.5 g / L, in particular 10 g / L. Preferably, the aromatic hydrocarbon sulfonate condensed with formaldehyde is present in an amount of up to 200 g / L, more preferably up to 175 g / L, more preferably up to 150 g / L, more preferably up to 125 g / L, in particular up to 100 g / L, more particularly up to 80 g / L, even more particularly up to 60 g / L. Preferably, the aromatic hydrocarbon sulfonate condensed with formaldehyde is present in an amount of 1 to 200 g / L, more preferably 5 to 150 g / L, more preferably 10 to 100 g / L, in particular 10 to 60 g / L.

[0036] The suspension concentrate of the present invention further comprises ammonium sulfate. The ammonium sulfate may be present in any amount suitable for providing the required stability of the macrolide active component. Preferably, the ammonium sulfate is present in an amount of 0.1 g / L, more preferably 1 g / L, even more preferably 5 g / L, more preferably still 7.5 g / L, in particular 10 g / L. Preferably, the ammonium sulfate is present in an amount of up to 100 g / L, more preferably up to 80 g / L, even more preferably up to 50 g / L, more preferably still up to 40 g / L, in particular up to 30 g / L, more particularly up to 25 g / L, even more particularly up to 20 g / L.Preferably, ammonium sulfate is present in an amount ranging from 0.1 to 100 g / L, more preferably from 1 to 80 g / L, more preferably still from 5 to 50 g / L, in particular from 10 to 30 g / L, more particularly from 10 to 20 g / L.

[0037] The weight ratio of the macrolide active component and the aromatic hydrocarbon sulfonate condensed with formaldehyde can be any suitable range. Preferably, the macrolide active component is present in excess of the weight of the aromatic hydrocarbon sulfonate condensed with formaldehyde. Preferably, the weight ratio of the macrolide active component and the aromatic hydrocarbon sulfonate condensed with formaldehyde in the suspension concentrate is 2:1, more preferably 2.5:1, even more preferably 3:1, and even more preferably 3.5:1. Preferably, the weight ratio of the macrolide active component and the aromatic hydrocarbon sulfonate condensed with formaldehyde in the suspension concentrate is up to 18:1, more preferably up to 15:1, even more preferably up to 14:1, and even more preferably up to 13:1, particularly up to 12:1.Preferably, the weight ratio of the macrolide active component and the condensed aromatic hydrocarbon sulfonate with formaldehyde in the suspension concentrate ranges from 2:1 to 18:1, more preferably from 2.5:1 to 15:1, even more preferably from 3:1 to 14:1, more preferably still from 3.5:1 to 12:1, in particular from 4:1 to 12:1.

[0038] The weight ratio of the macrolide active component and ammonium sulfate can be any suitable range. Preferably, the macrolide active component is present in excess of weight relative to the ammonium sulfate. Preferably, the weight ratio of the macrolide active component and ammonium sulfate in the suspension concentrate is 6:1, more preferably 8:1, even more preferably 10:1, and even more preferably 12:1. Preferably, the weight ratio of the macrolide active component and ammonium sulfate in the suspension concentrate is up to 35:1, more preferably up to 30:1, even more preferably up to 28:1, and even more preferably up to 26:1, particularly up to 24:1. Preferably, the weight ratio of the macrolide active component and ammonium sulfate in the suspension concentrate is from 6:1 to 35:1, more preferably from 8:1 to 30:1, even more preferably from 10:1 to 28:1, more preferably still from 12:1 to 26:1, in particular from 12:1 to 24:1.

[0039] The weight ratio of the condensed aromatic hydrocarbon sulfonate with formaldehyde and ammonium sulfate can be any suitable range. Preferably, the condensed aromatic hydrocarbon sulfonate with formaldehyde is present in excess of weight relative to the ammonium sulfate. Preferably, the weight ratio of the condensed aromatic hydrocarbon sulfonate with formaldehyde and ammonium sulfate in the suspension concentrate is 1:1, more preferably 1.1:1, even more preferably 1.2:1, and even more preferably 1.3:1. Preferably, the weight ratio of the condensed aromatic hydrocarbon sulfonate with formaldehyde and ammonium sulfate in the suspension concentrate is up to 5:1, more preferably up to 4.5:1, even more preferably up to 4:1, and even more preferably up to 3.5:1, particularly up to 3:1.Preferably, the weight ratio of the condensed aromatic hydrocarbon sulfonate with formaldehyde and ammonium sulfate in the suspension concentrate is from 1:1 to 5:1, more preferably from 1.1:1 to 4.5:1, even more preferably from 1.2:1 to 4:1, more preferably still from 1.3:1 to 3.5:1, in particular from 1.3:1 to 3:1.

[0040] An advantage of the suspension concentrate of the present invention is that it is not necessary to use thickeners, in particular organic polymer thickeners. Therefore, the suspension concentrate can be formed with a low system viscosity. The viscosity of the suspension concentrate will depend on factors such as the concentration of the macrolide active ingredient in the composition. The viscosity is preferably less than 800 mPa·s, more preferably less than 600 mPa·s, more preferably still less than 400 mPa·s, in particular less than 300 mPa·s, and more particularly less than 200 mPa·s. References to viscosity herein refer to the viscosity of the suspension concentrate measured using a Brookfield DV-II Pro viscometer, mobile No. 2.

[0041] The suspension concentrate of the present invention can remain stable for a Prolonged storage even when exhibiting low viscosity. This is due to the combined action of alkylnaphthalene sulfonate and ammonium sulfate stabilizing the suspended particles of the macrolide active substance, for example slowing the sedimentation rate of the macrolide particles.

[0042] The suspension concentrate of the present invention can be any form of formulation in which solid particles of the macrolide active component are suspended in a liquid medium. Examples of such formulations include suspension concentrates (SC), suspoemulsions (SE), and microcapsule-suspension concentrates.

[0043] The components for formulating a suspension concentrate composition and the techniques for their use are known in the art. The suspension concentrate of the present invention may further comprise one or more agrochemically acceptable auxiliaries. Suitable auxiliaries include one or more dispersants, wetting agents, emulsifiers, preservatives, antifoaming agents, coloring agents, pH regulators, an inert vehicle, and solvents.

[0044] The suspension concentrate formulation may include one or more solvents. Suitable solvents are those that cannot dissolve the macrolide active substance. Suitable solvents may be any one or a combination of at least two of the following: soybean oil, corn oil, rapeseed oil, epoxidized soybean oil, methyl oleate, ethyl laurate, methyl linoleate, palmitic acid, linseed oil, mineral oil, and water. Water is a preferred solvent for many embodiments.

[0045] The suspension concentrate may comprise one or more dispersants. Suitable dispersants are any substances used for this purpose in agrochemical formulations. The dispersant may be one or more nonionic, amphoteric, cationic, and anionic (polymer) surfactants.Preferred dispersants include fatty alcohol ethoxylates, fatty alcohol alkoxylates, EO / PO sequence copolymers, ethoxylated alcohol sulfonic acids, sulfosuccinates, fatty acid methyl taurates, tristyryl phenol ethoxylates and alkoxylates, tri-sec-butyl phenol ethoxylates, sulfated cresol-formaldehyde condensates, sulfated naphthalene and alkyl naphthalene condensates, lignosulfonates, ethoxylated fatty alcohol phosphates, tristyryl phenol and tri-sec-butyl phenol, and ethoxylated fatty alcohol copolymers, polyacrylic acid, polymethacrylic acid and acrylates, tristyryl phenol and tri-sec-butyl phenol ether sulfates, and Polymer dispersants.

[0046] Suitable wetting agents that can be included in the suspension concentrate formulation are any substances that are used for this purpose in agrochemical formulations. Suitable wetting agents include anionic wetting agents, for example, alkali metal salts, alkaline earth metal salts, or ammonium salts of anionic wetting agents. Preferred wetting agents include naphthalene sulfonates, for example, disodium methylene dinaphthalene sulfonates, sodium naphthalene sulfonate-formaldehyde condensates, and ammonium naphthalene sulfonate-formaldehyde condensates; alkylnaphthalene sulfonates, for example, alkyl-naphthalene sulfonates; benzene sulfonates; alkylbenzene sulfonates, for example, sodium cumene sulfonates, potassium cumene sulfonates, sodium xylene sulfonates, and sodium toluene sulfonates; alkanesulfonates, for example, sodium tetradecene sulfonates; α-olefin sulfonates, for example, sodium α-olefin sulfonates;sulfosuccinates, for example sodium dioctyl sulfosuccinates; alkyl phosphates, for example lauryl and myristyle phosphates; and alkyl sulfates, for example sodium lauryl sulfate, sodium cetyl and stearyl sulfates, sodium cetyl sulfates, sodium myristyle sulfates, and sodium cetyl and stearyl sulfates.

[0047] Suitable emulsifiers to be included in the suspension concentrate are all substances which are used for this purpose in agrochemical formulations and include the reaction products of alkylphenol with ethylene oxide and / or propylene oxide, ethoxylated nonylphenols, castor oil ethoxylates, polyalkoxylated alcohol mixtures (Atlox 4894), alkyl calcium salts, calcium alkylbenzene sulfonate salts, sorbitan derivatives or polyethylene sorbitan oxide fatty acid esters.

[0048] Suitable preservatives are all substances which are used for this purpose in agrochemical formulations, for example alkyl isothiazolinones and benzisothiazolinones.

[0049] Suitable antifoaming agents are all substances used for this purpose in agrochemical formulations, for example silicone salts, long chain alcohols and fatty acids.

[0050] Suitable colouring agents are any substances used for this purpose in agrochemical formulations, for example titanium dioxide, zinc oxide, blue pigments or BBN red pigment (everbright fast red BBN).

[0051] Suitable pH regulators are all substances which are used for this purpose in agrochemical formulations and include phosphoric acid, acetic acid, citric acid, sodium carbonate, sodium bicarbonate, potassium phosphate, potassium hydrogen phosphate, and potassium dihydrogen phosphate.

[0052] In one embodiment of the present invention, the suspension concentrate understand :

[0053] 1) 1 to 600 g / L of at least one macrolide active substance,

[0054] 2) 1 to 200 g / L of at least one condensed aromatic hydrocarbon sulfonate with formaldehyde, and

[0055] 3) 0.1 to 100 g / L of ammonium sulfate.

[0056] In a preferred embodiment of the present invention, the suspension concentrate comprises:

[0057] 1) 1 to 600 g / L of at least one macrolide active substance,

[0058] 2) 1 to 200 g / L of at least one condensed aromatic hydrocarbon sulfonate with formaldehyde,

[0059] 3) 0.1 to 100 g / L of ammonium sulfate.

[0060] 4) 0 to 100 g / L of an agrochemically acceptable surfactant, and

[0061] 5) water up to 1 L.

[0062] In one embodiment of the present invention, the suspension concentrate comprises:

[0063] 1) 1 to 600 g / L of pleocidin,

[0064] 2) 1 to 200 g / L of at least one condensed aromatic hydrocarbon sulfonate with formaldehyde, and

[0065] 3) 0.1 to 100 g / L of ammonium sulfate.

[0066] In another embodiment of the present invention, the suspension concentrate comprises:

[0067] 1) 50 to 500 g / L of pleocidin,

[0068] 2) 1 to 200 g / L of at least one sodium alkylnaphthalene sulfonate condensed with formaldehyde, and

[0069] 3) 0.1 to 100 g / L of ammonium sulfate.

[0070] In yet another embodiment of the present invention, the suspension concentrate comprises:

[0071] 1) 50 to 500 g / L of pleocidin,

[0072] 2) 10 to 50 g / L of at least one sodium alkylnaphthalene sulfonate condensed with formaldehyde,

[0073] 3) 10 to 30 g / L of ammonium sulfate,

[0074] 4) 0 to 80 g / L of an agrochemically acceptable surfactant, and

[0075] 5) water up to 1 L.

[0076] The average particle size of the macrolide particles in the suspension concentrate of the present invention can be 0.1 pm, preferably 0.3 pm, more preferably 0.5 pm, and even more preferably 1 pm. The average particle size of the macrolide particles in the suspension concentrate of the present invention can be up to 15 pm, preferably up to 10 pm, and more preferably up to 8 pm, even more preferably up to 5 pm. The average particle size of the macrolide particles in the suspension concentrate of the present invention can be in the range of about 0.1 to about 10 pm, preferably about 0.5 to 8 pm, and more preferably about 1 to 5 pm.

[0077] The techniques for forming the suspension concentrate formulations of the present invention are known in the art.

[0078] According to another aspect, the present invention relates to a method of pest control at a location, the method comprising the application to the location of a suspension concentrate formulation as described above.

[0079] Generally, the suspension concentrate is diluted with a solvent, most appropriately water, before being applied to the location. Techniques for applying the concentrate or a dilution thereof to a location are known in the technique and include spraying.

[0080] The suspension concentrate can be applied to control insect infestations of plants. The suspension concentrate can be applied directly to the plants, to parts of the plants, or to the location where the plants are growing or will be cultivated.

[0081] According to another aspect, the present invention relates to the use of a suspension concentrate as described above in the control of insects.

[0082] The amount of suspension concentrate used will depend on a number of factors, such as the habits of the pests being controlled, the timing of application, the number of applications, and environmental conditions. Typically, the amount of macrolide active ingredient required for pest control ranges from 5 to 100 g / ha.

[0083] As used herein, the term “location” means any place where pests can grow, including stems, leaves, plant roots, seeds or soil.

[0084] The suspension concentrate of the present invention can be used to control pests in a wide range of plants, in particular valuable crops such as wheat, rice, soybeans, maize, cotton, cucumbers, tomatoes, and cabbage.

[0085] As discussed previously, the present invention is based on the discovery that the combination of a condensed aromatic hydrocarbon sulfonate with formaldehyde and ammonium sulfate can significantly improve the stability of a macrolide active compound in a suspension concentrate.

[0086] Thus, according to another aspect, the present invention relates to the use of a combination of a condensed aromatic hydrocarbon sulfonate with formaldehyde and ammonium sulfate to increase the stability of a macrolide active compound in a concentrated suspension formulation.

[0087] Furthermore, the present invention provides a method for increasing the stability of a macrolide active compound in a suspension concentrate formulation, the method comprising: the use of a combination of an aromatic hydrocarbon sulfonate condensed with formaldehyde and ammonium sulfate in the formulation.

[0088] Embodiments of the present invention will now be described by means of the following working examples.

[0089] EXAMPLES

[0090] Example 1 - pleocidin suspension concentrate at 240 g / L

[0091] A suspension concentrate was prepared from the following components:

[0092] Pleocidine 240 g

[0093] Propylene glycol 50 g

[0094] Alkylnaphthalene sulfonate and formaldehyde condensation product (Morwent™ D-425) 20 g

[0095] Methacrylic acid copolymer 30 g

[0096] Ammonium sulfate 10 g

[0097] Antimicrobial agent isothiazolinone 2 g

[0098] Water up to IL

[0099] The suspension concentrate was prepared by the following process:

[0100] The components listed above were combined and mixed under stirring at room temperature until a uniform suspension was obtained. The resulting suspension was ground in a sand mill at a temperature of up to 40 °C to obtain a final concentrate of aqueous pleocidin suspension. The pleocidin particles had an average particle size of 4 µm or less.

[0101] Example 2 - pleocidin suspension concentrate at 480 g / L

[0102] A suspension concentrate was prepared from the following components:

[0103] Pleocidine 480 g

[0104] Propylene glycol 50 g

[0105] Condensation product of alkylnaphthalene sulfonate and formaldehyde (Tamol™ NN8906) 40 g

[0106] Fatty alcohol polyoxyethylene ether 50 g

[0107] Ammonium sulfate 30 g

[0108] Antimicrobial agent isothiazolinone 2 g

[0109] Water up to IL

[0110] The suspension concentrate was prepared by the following process:

[0111] The components listed above were combined and mixed under stirring at room temperature until a uniform suspension was obtained. The suspension... The sultante was ground in a sand mill at a temperature of up to 40 °C to obtain a final concentrate of aqueous pleocidin suspension. The pleocidin particles had an average particle size of 4 µm or less.

[0112] Example 3 - 60 g / L ethyl pleocidin suspension concentrate

[0113] A suspension concentrate was prepared from the following components:

[0114] Ethyl pleocidin 60 g

[0115] Propylene glycol 50 g

[0116] Naphthalene sulfonate and formaldehyde condensation product (Supragil™ MNS-90) 15 g

[0117] Methacrylic acid copolymer 20 g

[0118] Ammonium sulfate 5 g

[0119] Antimicrobial agent isothiazolinone 2 g

[0120] Water up to 1 L

[0121] The suspension concentrate was prepared by the following process:

[0122] The components listed above were combined and mixed under stirring at room temperature until a uniform suspension was obtained. The resulting suspension was ground in a sand mill at a temperature of up to 40 °C to obtain a final concentrate of aqueous ethyl pleocidin suspension. The ethyl pleocidin particles had an average particle size of 4 µm or less.

[0123] Example 4 - 50 g / L emamectin benzoate suspension concentrate

[0124] A suspension concentrate was prepared from the following components:

[0125] Emamectin benzoate 50 g

[0126] Propylene glycol 50 g

[0127] Alkylnaphthalene sulfonate and formaldehyde condensation product (Terperse™ 2425) 10 g

[0128] Methacrylic acid copolymer 25 g

[0129] Ammonium sulfate 8 g

[0130] Antimicrobial agent isothiazolinone 3 g

[0131] Water up to 1 L

[0132] The suspension concentrate was prepared by the following process:

[0133] The components listed above were combined and mixed under stirring at room temperature until a uniform suspension was obtained. The resulting suspension was ground in a sand mill at a temperature of up to 40 °C to obtain a final concentrate of aqueous emamectin suspension. The emamectin particles had an average particle size of 5 µm or less.

[0134] Comparative example 1 - pleocidin suspension concentrate at 240 g / L

[0135] A suspension concentrate was prepared from the following components:

[0136] Pleocidine 240 g

[0137] Propylene glycol 50 g

[0138] Dodecyl benzenesulfonate 20 g

[0139] Methacrylic acid copolymer 30 g

[0140] Ammonium sulfate 10 g

[0141] Antimicrobial agent isothiazolinone 2 g

[0142] Water up to 1 L

[0143] The suspension concentrate was prepared by the following process:

[0144] The components listed above were combined and mixed under stirring at room temperature until a uniform suspension was obtained. The resulting suspension was ground in a sand mill at a temperature of up to 40 °C to obtain a final concentrate of aqueous pleocidin suspension. The pleocidin particles had an average particle size of 4 µm or less.

[0145] Comparative example 2 - pleocidin suspension concentrate at 240 g / L

[0146] A suspension concentrate was prepared from the following components:

[0147] Pleocidine 240 g

[0148] Propylene glycol 50 g

[0149] Alkylnaphthalene sulfonate and formaldehyde condensation product (Morwent™ D-425) 20 g

[0150] Methacrylic acid copolymer 30 g

[0151] Urea 10 g

[0152] Antimicrobial agent isothiazolinone 2 g

[0153] Water up to 1 L

[0154] The suspension concentrate was prepared by the following process:

[0155] The components listed above were combined and mixed under stirring at room temperature until a uniform suspension was obtained. The resulting suspension was ground in a sand mill at a temperature of up to 40 °C to obtain a final concentrate of aqueous pleocidin suspension. The pleocidin particles had an average particle size of 4 µm or less.

[0156] Comparative example 3 - pleocidin suspension concentrate at 240 g / L

[0157] A suspension concentrate was prepared from the following components:

[0158] Pleocidine 240 g

[0159] Propylene glycol 50 g

[0160] Alkylnaphthalene sulfonate and formaldehyde condensation product (Morwent™ D-425) 20 g

[0161] Methacrylic acid copolymer 30 g

[0162] Antimicrobial agent isothiazolinone 2 g

[0163] Xanthan gum 2 g

[0164] Water up to IL

[0165] The suspension concentrate was prepared by the following process:

[0166] The components listed above were combined and mixed under stirring at room temperature until a uniform suspension was obtained. The resulting suspension was ground in a sand mill at a temperature of up to 40 °C to obtain a final concentrate of aqueous pleocidin suspension. The pleocidin particles had an average particle size of 4 µm or less.

[0167] Comparative example 4 - pleocidin suspension concentrate at 480 g / L

[0168] A suspension concentrate was prepared from the following components:

[0169] Pleocidin 480 g

[0170] Propylene glycol 50 g

[0171] Dodecyl benzenesulfonate 40 g

[0172] Fatty alcohol polyoxyethylene ether 50 g

[0173] Ammonium sulfate 30 g

[0174] Isothiazolinone 2 g antimicrobial agent

[0175] Water up to 1 L

[0176] The suspension concentrate was prepared by the following process:

[0177] The components listed above were combined and mixed under stirring at room temperature until a uniform suspension was obtained. The resulting suspension was ground in a sand mill at a temperature of up to 40 °C to obtain a final concentrate of aqueous pleocidin suspension. The pleocidin particles had an average particle size of 4 µm or less.

[0178] Comparative example 5 - pleocidin suspension concentrate at 480 g / L

[0179] A suspension concentrate was prepared from the following components:

[0180] Pleocidine 480 g

[0181] Propylene glycol 50 g

[0182] Alkylnaphthalene sulfonate and formaldehyde condensation product (Tamol™ NN8906) 40 g

[0183] Fatty alcohol polyoxyethylene ether 50 g

[0184] Urea 30 g

[0185] Antimicrobial agent isothiazolinone 2 g

[0186] Water up to 1 L

[0187] The suspension concentrate was prepared by the following process:

[0188] The components listed above were combined and mixed under stirring at room temperature until a uniform suspension was obtained. The resulting suspension was ground in a sand mill at a temperature of up to 40 °C to obtain a final concentrate of aqueous pleocidin suspension. The pleocidin particles had an average particle size of 4 µm or less.

[0189] Comparative example 6 - pleocidin suspension concentrate at 480 g / L

[0190] A suspension concentrate was prepared from the following components:

[0191] Pleocidin 480 g

[0192] Propylene glycol 50 g

[0193] Alkylnaphthalene sulfonate and formaldehyde condensation product (Tamol™ NN8906) 40 g

[0194] Fatty alcohol polyoxyethylene ether 50 g

[0195] Guar gum 2 g

[0196] Antimicrobial agent isothiazolinone 2 g

[0197] Water up to IL

[0198] The suspension concentrate was prepared by the following process:

[0199] The components listed above were combined and mixed under stirring at room temperature until a uniform suspension was obtained. The resulting suspension was ground in a sand mill at a temperature of up to 40 °C to obtain a final concentrate of aqueous pleocidin suspension. The pleocidin particles had an average particle size of 4 µm or less.

[0200] Comparative example 7 - 60 g / L ethyl pleocidin suspension concentrate

[0201] A suspension concentrate was prepared from the following components:

[0202] Ethyl pleocidin 60 g

[0203] Propylene glycol 50 g

[0204] Naphthalene sulfonate and formaldehyde condensation product (Supragil™ MNS-90) 15 g

[0205] Methacrylic acid copolymer 20 g

[0206] Xanthan gum 2 g

[0207] Antimicrobial agent isothiazolinone 2 g

[0208] Water up to 1 L

[0209] The suspension concentrate was prepared by the following process:

[0210] The components listed above were combined and mixed under stirring at room temperature until a uniform suspension was obtained. The resulting suspension was ground in a sand mill at a temperature of up to 40 °C to obtain a final concentrate of aqueous ethyl pleocidin suspension. The ethyl pleocidin particles had an average particle size of 5 µm or less.

[0211] Comparative example 8 - emamectin benzoate suspension concentrate at 50 g / L

[0212] A suspension concentrate was prepared from the following components:

[0213] Emamectin benzoate 50 g

[0214] Propylene glycol 50 g

[0215] Condensation product of alkylnaphthalene sulfonate and formaldehyde (Terperse™ 2425) 10 g

[0216] Methacrylic acid copolymer 25 g

[0217] Xanthan gum 2 g

[0218] Antimicrobial agent isothiazolinone 3 g

[0219] Water up to 1 L

[0220] The suspension concentrate was prepared by the following process:

[0221] The components listed above were combined and mixed under stirring at room temperature until a uniform suspension was obtained. The resulting suspension was ground in a sand mill at a temperature of up to 40 °C to obtain a final concentrate of aqueous emamectin benzoate suspension. The emamectin benzoate particles had an average particle size of 2 µm or less.

[0222] Performance tests

[0223] Viscosity Test

[0224] The viscosity of each of the liquid suspension concentrates prepared in the examples and comparative examples above was tested following the CIP AC MT 192 procedure. The viscosity was measured using a ROOKFIELD DV-II+Pro viscometer with spindle No. 2 selected under 30 revolution conditions.

[0225] The results are summarized in Table 1 below.

[0226] 2, Stability test

[0227] A sample of each of the suspension concentrates prepared in the examples and comparative examples above was loaded into a 100 ml graduated cylinder and placed in a constant temperature oven for storage at 54 °C for 14 days. The cylinder was then removed and placed at room temperature to observe the properties of each sample.

[0228] The results are summarized in Table 1 below.

[0229] Table 1 Sample Viscosity (mPa.s) Separation observed after heat storage at 54 °C for 14 days Example 1 385 water separation at 3%, without aggregation, flocculation, or precipitation Example 2 585 water separation at 2%, without aggregation, flocculation, or precipitation Example 3 245 water separation at 5%, without aggregation, flocculation, or precipitation Example 4: 205 water separation at 5%, without aggregation, flocculation, or precipitation. Comparative Example 1: 370 water separation at 24%, with slight aggregation, without flocculation, and with precipitation. Comparative Example 2: 390 water separation at 25%, without aggregation and flocculation, and with precipitation. Comparative Example 3: 540 water separation at 20%, with aggregation, significant flocculation, and slight precipitation. Comparative Example 4: 610 water separation at 18%, with slight aggregation, without flocculation, and with precipitation. Comparative Example 5: 580 water separation at 20%, without aggregation and flocculation, and with precipitation. Comparative Example 6: 780 water separation at 21%, without aggregation and flocculation, and with precipitation. Comparative Example 7: 530 water separation at 28%, with aggregation, significant flocculation, and slight precipitation. 8,480 water separation at 30%, with aggregation, significant flocculation, and slight precipitation

[0230] The results in Table 1 show that the suspension concentrates of the present invention exhibited low water separation from the product, no aggregation or flocculation, and no precipitation after storage at high temperature. This was particularly true when the viscosities of the samples did not exceed 600 mPa·s. The suspension concentrates displayed good fluidity and superior flowability due to their lower viscosity.

[0231] In contrast, the suspension concentrates in the comparative examples exhibited significant water separation and precipitation during heat storage. Attempts to reduce these phenomena by adding a thickener to increase the viscosity of the system were unsuccessful and consistently resulted in significant aggregation and flocculation.

Claims

Demands

1. 1 Suspension concentrate composition, preferably aqueous suspension concentrate, the suspension concentrate comprising: a) at least one macrolide active substance; b) at least one aromatic hydrocarbon sulfonate condensed with formaldehyde; and c) ammonium sulfate.

2. 2 Concentrated suspension according to claim 1, characterized in that the macrolide active substance is selected from avermectin, emamectin, emamectin benzoate, pleocidin, ethyl pleocidin, ivermectin and mixtures of two or more of these.

3. 3 Concentrated suspension according to any one of the preceding claims, characterized in that the aromatic hydrocarbon sulfonate is an alkylnaphthalene sulfonate; and / or the aromatic hydrocarbon sulfonate is a salt of an aromatic hydrocarbon sulfonate, preferably an alkali metal salt.

4. 4 Concentrated suspension according to any one of the preceding claims, characterized in that the aromatic hydrocarbon sulfonate condensed with formaldehyde is present in an amount from 1 to 200 g / L; and / or in that the ammonium sulfate is present in an amount from 0.1 to 100 g / L.

5. 5 Suspension concentrate according to any one of the preceding claims, characterized in that: the weight ratio of the macrolide active substance and the condensed aromatic hydrocarbon sulfonate with formaldehyde in the suspension concentrate ranges from 2:1 to 18:1; and / or the weight ratio of the macrolide active substance and the ammonium sulfate in the suspension concentrate ranges from 6:1 to 35:1; and / or the weight ratio of the condensed aromatic hydrocarbon sulfonate with formaldehyde and the ammonium sulfate in the suspension concentrate ranges from 1:1 to 5:

1.

6. 6 Concentrated suspension according to any one of the preceding claims, characterized in that the macrolide active substance is suspended in a liquid medium comprising soybean oil, corn oil, rapeseed oil, epoxidized soybean oil, methyl oleate, ethyl laurate, methyl linoleate, palmitic acid, linseed oil, mineral oil, water or a mixture of these.

7. 7 Suspension concentrate according to any one of the preceding claims, characterized in that the suspension concentrate does not comprise any polymeric organic thickener, and / or the suspension concentrate does not comprise xanthan gum, guar gum, cellulose, hydroxymethylcellulose, starch, polyvinyl alcohol, polyvinylpyrrolidone and derivatives thereof.

8. 8 Suspension concentrate according to any one of the preceding claims, characterized in that the suspension concentrate contains: 1) 1 to 600 g / L of at least one macrolide active substance, 2) 1 to 200 g / L of at least one aromatic hydrocarbon sulfonate condensed with formaldehyde, and 3) 0.1 to 100 g / L of ammonium sulfate; and, preferably, in that the suspension concentrate contains: 1) 1 to 600 g / L of at least one macrolide active substance, 2) 1 to 200 g / L of at least one aromatic hydrocarbon sulfonate condensed with formaldehyde, 3) 0.1 to 100 g / L of ammonium sulfate. 4) 0 to 100 g / L of an agrochemically acceptable surfactant, and 5) water up to 1 L.

9. 9 Suspension concentrate according to any one of the preceding claims, characterized in that the suspension concentrate comprises: 1) 50 to 500 g / L of pleocidin, 2) 1 to 200 g / L of at least one sodium alkylnaphthalene sulfonate condensed with formaldehyde, and 3) 0.1 to 100 g / L of ammonium sulfate.

10. 10 Method for controlling pests at a location, the method comprising 1' application to the location of a suspension concentrate composition according to 1' any prior claim, optionally wherein the suspension concentrate composition is diluted with water.

11. 11 Use of a suspension concentrate composition according to 1' any one of claims 1 to 18 in the fight against insects.

12. 12 Use of a combination of a condensed aromatic hydrocarbon sulfonate with formaldehyde and ammonium sulfate to increase the stability of a macrolide active compound in a suspension concentrate formulation.

13. 13 Method for increasing the stability of a macrolide active compound in a suspension concentrate formulation, the method comprising the use of a combination of an aromatic hydrocarbon sulfonate condensed with formaldehyde and an ammonium sulfate in the formulation.