GB2625702A - Insecticidal composition comprising a macrolide active ingredient - Google Patents

Insecticidal composition comprising a macrolide active ingredient Download PDF

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Publication number
GB2625702A
GB2625702A GB2213846.5A GB202213846A GB2625702A GB 2625702 A GB2625702 A GB 2625702A GB 202213846 A GB202213846 A GB 202213846A GB 2625702 A GB2625702 A GB 2625702A
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suspension concentrate
aromatic hydrocarbon
formaldehyde
ammonium sulfate
macrolide
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GB202213846D0 (en
Inventor
Timothy Bristow James
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Rotam Agrochem International Co Ltd
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Rotam Agrochem International Co Ltd
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Priority to GB2213846.5A priority Critical patent/GB2625702A/en
Publication of GB202213846D0 publication Critical patent/GB202213846D0/en
Priority to ES202330764A priority patent/ES2967107A2/en
Priority to FR2309863A priority patent/FR3139975A1/en
Publication of GB2625702A publication Critical patent/GB2625702A/en
Pending legal-status Critical Current

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P7/00—Arthropodicides
    • A01P7/04—Insecticides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P1/00—Disinfectants; Antimicrobial compounds or mixtures thereof

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  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Zoology (AREA)
  • Engineering & Computer Science (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Wood Science & Technology (AREA)
  • Agronomy & Crop Science (AREA)
  • Dentistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Toxicology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Insects & Arthropods (AREA)
  • Dispersion Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Suspension concentrate (e.g. aqueous SC) composition comprising: a) at least one macrolide active substance; b) at least one aromatic hydrocarbon sulfonate condensed with formaldehyde; and c) ammonium sulfate. Preferably, the macrolide active is pleocidin. The sulfonate may be an alkylnapthalene sulfonate. The macrolide may be suspended in a liquid medium, e.g. soybean oil, corn oil, rapeseed oil. The SC may be free of a polymeric organic thickener. Preferably, the macrolide is present in the suspension concentrate at 1 to 600 g.l-1, the aromatic hydrocarbon sulfonate is present at 1 to 200 grams per litre and the ammonium sulphate is present at 0.1 to 100 g/l. Use of composition as defined in the control of pest infestations is also provided. There is further provided a method of increasing the stability of a macrolide active compound in a suspension concentrate formulation, the method comprising employing a combination of a formaldehyde-condensed aromatic hydrocarbon sulfonate and ammonium sulfate in the formulation.

Description

Intellectual Property Office Application No G132213846.5 RTM Date:22 February 2023 The following terms are registered trade marks and should be read as such wherever they occur in this document: Tersperse Tamol Morwet Dispersogen Atlox Intellectual Property Office is an operating name of the Patent Office www.gov.uk/ipo
INSECTICIDAL COMPOSITION COMPRISING A MACROLIDE ACTIVE
INGREDIENT
The present invention relates to an insecticidal composition comprising a macrolide active substance, more particularly to an insecticidal suspension concentrate. The present invention further relates to the preparation of the suspension concentrate and its use.
Macrolide-based insecticidally active substances are well known in the field of agrochemicals. Examples of members of this group of insecticidally active substances include avermectin, emamectin, pleocidin, ethyl pleocidin, ivermectin, abamectin, and methylamino avermectin. These macrolide compounds have relatively large molecular weights, complex spatial structures, a large number of oxygen atoms and/or hydroxyl groups, and all contain lactone rings. As a result, macrolide insecticidal compounds are prone to agglomeration when combined with compounds having polyhydroxyl and/or polyoxygen structures, due to the action of hydrogen bonds.
One common form of agrochemical formulation applied on a commercial scale is a suspension concentrate. Suspension concentrates comprises a suspension of solid particles of the agrochemical active ingredient in a suitable liquid medium, very often water. Suspension concentrate products are prone to sedimentation. The rate of sedimentation conforms to Stokes' sedimentation law: w = [2g (ps -p) gr2]/9p where ps is the particle density, p is the liquid density, p is the liquid viscosity, r is the particle radius, and g is the acceleration due to gravity.
To counter the tendency for sedimentation to occur, it is known to add a thickener to a suspension concentrate product to adjust the fluid viscosity of the system and slow down the rate of sedimentation. This in turn reduces water separation and stratification during storage of the product and improves the physical stability of the product.
The most commonly used thickeners in suspension concentrate products are polymer compounds, such as xanthan gum, guar gum, cellulose, hydroxymethyl cellulose, starch, polyvinyl alcohol, polyvinylpyrrolidone and derivatives thereof. Such thickeners all contain a relatively large number of hydroxyl groups and/or oxygen atoms. As a result, the macrolide-based insecticidally active substance molecules are prone to aggregation with these thickener molecules due to hydrogen-bonding action, as noted above. As a result, these polymeric organic thickeners are not suitable for use in suspension concentrates containg macrolides as an active ingredient. This leads to a reduction in the physical stability of the suspension concentrate formulation, in turn reducing the efficacy of the product.
There is therefore a need for a technique to improve the stability and efficacy of macrolide insecticide compounds when formulated as a suspension concentrate.
The present invention provides 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.
It has unexpectedly been discovered that the combination of a formaldehyde-condensed aromatic hydrocarbon sulfonate and ammonium sulfate can significantly improve the storage stability of a suspension concentrate containing an active macrolide compound.
In particular, it has been found that the combination of the formaldehyde-25 condensed aromatic hydrocarbon sulfonate and ammonium sulfate in the suspension concentrate of the present invention slows down the sinking rate of particles in the suspension concentrate. Therefore, the storage stability of the suspension concentrate of the present invention is significantly improved without the need to add additional thickeners, especially polymeric organic thickeners, to the suspension concentrate. The use of a combination of a formaldehyde-condensed aromatic hydrocarbon sulfonate and ammonium sulfate in a suspension concentrate prevents unwanted phenomena such as sinking of the macrolide particles to the bottom, water separation, flocculation, stratification and the like during storage, thereby improving the physical stability of the suspension concentrate. This in turn improves the efficacy of the suspension concentrate, in particular maintaining the level of activity of the macrolide component.
The use of a combination of a formaldehyde-condensed aromatic hydrocarbon sulfonate and ammonium sulfate according to the present invention allows a low-viscosity macrolide-containing suspension concentrate to be employed, without phenomena such as sinking fo the macrolide to the bottom, water separation, flocculation, stratification and the like occurring during storage, thereby 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, especially less than 300 mPa.s, which is technically advantageous for the preparation, handling and use of the suspension concentrate.
The suspension concentrate formulation comprises solid particles of the macrolide active component suspended in a liquid medium. The liquid medium may comprise any suitable liquid component or mixture of two or more thereof. Suitable liquid components are those that cannot dissolve the macrolide active substance. Suitable liquid components may be any one of or a combination of at least two of 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.
The suspension concentrate composition of the present invention comprises a macrolide as an active component, in particular an insecticidally active macrolide.
Such macrolides are known in the art. The macrolide is preferably selected from avermectin, emamectin benzoate, pleocidin, ethyl pleocidin, ivermectin, and abamectin. Preferred macrolides are pleocidin, ethyl pleocidin, emamectin and emamectin benzoate. Pleocidin is a particularly preferred macrolide.
The macrolide active substance may be present in the suspension concentrate of the present invention in any suitable amount. Preferably, the macrolide active substance is present in an amount of from 1 g/L, more preferably from 2 g/L, still more preferably from 5 g/L, more preferably still from 7.5 g/L, especially from 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, still more preferably up to 550 g/L, more preferably still up to 525 g/L, especially up to 500 g/L. Preferably, the macrolide active substance is present in an amount of from 1 to 600 g/L, more preferably from 5 to 550 g/L, more preferably still from 10 to 500 g/L.
The suspension concentrate composition of the present invention further comprises a formaldehyde-condensed aromatic hydrocarbon sulfonate. The term "aromatic hydrocarbon" is to be understood to include any aromatic hydrocarbon moiety, including but not limited to naphthalene, phenyl, phenol and cresol. Naphthalene is a particularly preferred aromatic hydrocarbon. The aromatic hydrocarbon moieties may also be optionally substituted with at least one alkyl group to form an alkylaromatic hydrocarbon. The aromatic hydrocarbon moieties may be mono-, di-or poly-substituted with substituent groups. Herein, the term "alkyl" includes primary, secondary and tertiary alkyl groups. In a preferred embodiment, the alkyl substituent is a Ci to C30 alkyl group, examples of which include methyl, ethyl, propyl, butyl, isopropyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl and dodecyl.
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: Ri 03S R2 R1038 R2 (I) wherein: each Ri is independently selected from hydrogen, an alkali metal, an alkaline earth metal, ammonium, a mono-, di-, or tri-Ci to C4 alkyl-amine, or a mono-, di-or tri-Ci to C4 hydroxy-alkylamine moiety; and each R2 is independently selected from hydrogen, a Ci to C30 linear or branched alkyl or alkenyl group; and n is an integer from 1 to 25.
Preferably, Ri is selected from an alkali metal, an alkaline earth metal, ammonium, a mono-, di-, or tri-Ci to Ca alkyl-amine, or a mono-, di-or tri-Ci to Cit hydroxy-alkylamine moiety.
Preferably R2 is a Ci to C2o alkyl group, more preferably a Ci to Cm alkyl group, still more preferably a Ci to C12 alkyl group, especially a Ci to C6 alkyl group. Examples of suitable alkyl groups include methyl, ethyl, isopropyl, n-butyl and sec-butyl.
Each naphthalene moiety may contain one or more R2 substituents. Each R2 may be present in any single or combination of multiple positions on the naphthalene moiety.
As mentioned above, the aromatic hydrocarbon sulfonate condensed with formaldehyde may be provided in the composition as a salt. Examples of suitable salts include: alkali metal salts, that is Ri in formula I is an alkali metal, such as sodium and potassium; and alkaline earth metals, that is Ri in formula I is an alkaline earth metal, such as magnesium and calcium; amine salts, that is Ri in formula I is an amine group, such as monomethylamine, dimethylamine and triethylamine. Alkali metal salts, in particular sodium salts are particularly preferred.
As indicated above, naphthalene is a preferred aromatic hydrocarbon moiety. Examples of commercially available sodium salts of formaldehyde-condensed naphthalene sulfonates include: TersperseTm 2001, TersperseTm 2100, TersperseTm 2105 and TersperseTm 2158 available from Huntsman; and TamolTm NH and NN series available from BASF.
In the composition of the present invention, alkylnaphthalene sulfonates condensed with formaldehyde, that is 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 of from 300 to 2,000, preferably from 400 to 1,000, and most preferably from 500 to 750. Examples of commercially available sodium salts of alkyl-substituted naphthalene sulfonates condensed with formaldehyde include: MorwetTM D-425, MorwetTM D-450, and MorwetTM D-809 available from AkzoNobel; TersperseTm 2425 and TersperseTm 2020 available from Huntsman Corporation, and SupragilTm MNS-90 and MNS-425 from Rhodia Inc. Other aromatic hydrocarbon sulfonates condensed with formaldehyde include: salts of phenol condensed with formaldehyde, for example the commercial products TamolTm PP and DN from BASF; and sodium salts of cresol condensed with formaldehyde, for example the commercial products DispersogenTM 1494 and RapidaminreserveTM CL from Clariant.
In the suspension concentrate of the present invention, the content of the aromatic hydrocarbon sulfonate condensed with formaldehyde may be any suitable amount to provide the required stability of the macrolide active component.
Preferably, the aromatic hydrocarbon sulfonate condensed with formaldehyde is present in an amount of from 1 g/L, more preferably from 2 g/L, still more preferably from 5 g/L, more preferably still from 7.5 g/L, especially from 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, still more preferably up to 150 g/L, more preferably still up to 125 g/L, especially up to 100 g/L, more especially up to 80 g/L, still more especially up to 60 g/L. Preferably, the aromatic hydrocarbon sulfonate condensed with formaldehyde is present in an amount of from 1 to 200 g/L, more preferably from 5 to 150 g/L, more preferably still from 10 to 100 g/L, especially from 10 to 60 g/L.
The suspension concentrate of the present invention further comprises ammonium sulfate. Ammonium sulfate may be present in any suitable amount to provide the required stability of the macrolide active component. Preferably, ammonium sulfate is present in an amount of from 0.1 g/L, more preferably from 1 g/L, still more preferably from 5 g/L, more preferably still from 7.5 g/L, especially from 10 g/L. Preferably, ammonium sulfate is present in an amount of up to 100 g/L, more preferably up to 80 g/L, still more preferably up to 50 g/L, more preferably still up to 40 g/L, especially up to 30 g/L, more especially up to 25 g/L, still more especially up to 20 g/L. Preferably, ammonium sulfate is present in an amount of from 0.1 to 100 g/L, more preferably from 1 to 80 g/L, more preferably still from 5 to 50 g/L, especially from 10 to 30 g/L, more especially from 10 to 20 g/L.
The weight ratio of the macrolide active component and the aromatic hydrocarbon sulfonate condensed with formaldehyde may be any suitable range.
Preferably, the macrolide active component is present in a weight excess compared with 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 from 2:1, more preferably from 2.5:1, still more preferably from 3:1, more preferably still from 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, still more preferably up to 14:1, more preferably still up to 13:1, especially up to 12:1. Preferably, the weight ratio of the macrolide active component and the aromatic hydrocarbon sulfonate condensed with formaldehyde in the suspension concentrate is from 2:1 to 18:1, more preferably from 2.5:1 to 15:1, still more preferably from 3:1 to 14:1, more preferably still from 3.5:1 to 12:1, especially from 4:1 to 12:1.
The weight ratio of the macrolide active component and ammonium sulfate may be any suitable range. Preferably, the macrolide active component is present in a weight excess compared with ammonium sulfate. Preferably, the weight ratio of the macrolide active component and ammonium sulfate in the suspension concentrate is from 6:1, more preferably from 8:1, still more preferably from 10:1, more preferably still from 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, still more preferably up to 28:1, more preferably still up to 26:1, especially 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, still more preferably from 10:1 to 28:1, more preferably still from 12:1 to 26:1, especially from 12:1 to 24:1.
The weight ratio of the aromatic hydrocarbon sulfonate condensed with formaldehyde and ammonium sulfate may be any suitable range. Preferably, the aromatic hydrocarbon sulfonate condensed with formaldehyde is present in a weight excess compared with ammonium sulfate. Preferably, the weight ratio of the aromatic hydrocarbon sulfonate condensed with formaldehyde and ammonium sulfate in the suspension concentrate is from 1:1, more preferably from 1.1:1, still more preferably from 1.2:1, more preferably still from 1.3:1. Preferably, the weight ratio of the aromatic hydrocarbon sulfonate condensed with formaldehyde and ammonium sulfate in the suspension concentrate is up to 5:1, more preferably up to 4.5:1, still more preferably up to 4:1, more preferably still up to 3.5:1, especially up to 3:1. Preferably, the weight ratio of the aromatic hydrocarbon sulfonate condensed 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, still more preferably from 1.2:1 to 4:1, more preferably still from 1.3:1 to 3.5:1, especially from 1.3:1 to 3:1.
An advantage of the suspension concentrate of the present invention is that no thickeners need to be employed, in particular organic polymeric thickeners. As a result, the suspension concentrate can be formed with a low system viscosity. The viscosity of the suspension concentrate will depend upon such factors as the concentration of the active macrolide 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, especially less than 300 mPa.s, more especially less than 200 mPa.s. References herein to viscosity are to the viscosity of the suspension concentrate measured using a Viscometer: Brookfield DV-11+Fr°, Spindle #2.
The suspension concentrate of the present invention can remain stable during prolonged storage even when having a low viscosity. This is due to the the combined action of the alkylnaphthalene sulfonate and ammonium sulfate stabilizing the suspended particles of the macrolide active substance, for example slowing down the sedimentation rate of the macrolide particles.
The suspension concentrate of the present invention imay 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-suspension concentrates.
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, inert carrier, and solvents.
The suspension concentrate formulation may comprise one or more solvents. Suitable solvents are those that cannot dissolve the macrolide active substance. Suitable solvents may be any one of or a combination of at least two of 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.
The suspension concentrate may comprise one or more dispersants. Suitable dispersants are any substances that are 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 block copolymers, sulfonic acids of ethoxylated alcohols, sulfosuccinates, fatty acid methyl taurates, tristyryl phenol ethoxylates and alkoxylates, tri-sec-butyl phenol ethoxylates, sulfated cresol-formaldehyde condensates, sulfated condensates of naphthalene and alkyl naphthalenes, lignosulfonates, phosphates of ethoxylated fatty alcohols, tristyryl phenol and tri-sec-butyl phenol, and copolymers of ethoxylated fatty alcohols, polyacrylic acid, polymethacrylic acid and acrylates, ether sulfates of tristyryl phenol and tri-sec-butyl phenol, and polymeric dispersants.
Suitable wetting agents that may 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 the anionic wetting agents. Preferred wetting agents include naphthalene sulfonates, for example disodium salts of methylene dinaphthalene sulfonates, sodium naphthalene sulfonate-formaldehyde condensates, and ammonium naphthalene sulfonate-formaldehyde condensates; alkyl naphthalene sulfonates, for example sodium alkylnaphtalene sulfonates; benzenesulfonates; alkylbenzenesulfonates, for example sodium cumene sulfonates, potassium cumene sulfonates, sodium xylene sulfonates, and sodium toluene sulfonates; alkanesulfonates, for example sodium tetradecene sulfonates; a-olefin sulfonates, for example sodium a-olefin sulfonates; sulfosuccinates, for example sodium dioctyl sulfosuccinates; alkyl phosphates, for example lauryl myristyl phosphates; and alkyl sulfates, for example sodium lauryl sulfates, sodium cetyl stearyl sulfates, sodium cetyl sulfates, sodium myristyl sulfates, and sodium cetyl stearyl sulfates.
Suitable emulsifiers for including in the suspension concentrate are any substances that 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, mixtures of polyalkoxylated alcohols (Atlox 4894), alkyl calcium salts, calcium alkylbenzene sulfonate salts, sorbitan derivatives or polyethylene oxide-sorbitan fatty acid esters.
Suitable preservatives are any substances that are used for this purpose in 10 agrochemical formulations, for example alkyl isothiazolinones and benzoisothiazolinones.
Suitable antifoaming agents are any substances that are used for this purpose in agrochemical formulations, for example the salts of silicone, long-chain alcohols and fatty acids.
Suitable coloring agents are any substances used for this purpose in agrochemical formulations, for example titanium dioxide, zinc oxide, blue pigments or Pigment Red BBN (everbright fast red BBN).
Suitable pH regulators are any substances that are used for this purpose in agrochemical formulations and include phosphoric acid, acetic acid, citric acid, 20 sodium carbonate, sodium bicarbonate, potassium phosphate, potassium hydrogen phosphate, and potassium dihydrogen phosphate.
In one embodiment of the present invention, the suspension concentrate comprises: 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.
In a preferred embodiment of the present invention, the suspension concentrate comprises: 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 that makes up to 1 L. In one embodiment of the present invention, the suspension concentrate 15 comprises: 1) 1 to 600 g/L of pleocidin, 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.
In a further embodiment of the present invention, 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.
In a still further embodiment of the present invention, the suspension concentrate comprises: 1) 50 to 500 g/L of pleocidin, 2) 10 to 50 g/L of at least one sodium alkylnaphthalene sulfonate condensed 10 with formaldehyde, 3) 10 to 30 g/L of ammonium sulfate, 4) 0 to 80 g/L of an agrochemically acceptable surfactant, and 5) water that makes up to 1 L. The average particle size of the macrolide particles in the suspension concentrate of the present invention may be from 0.1 pm, preferably from 0.3 pm, more preferably from 0.5 pm, still more preferably from 1pm. The average particle size of the macrolide particles in the suspension concentrate of the present invention may be up to 15 pm, preferably up to 10 pm, more preferably up to 8 pm, still more preferably up to 5pm. The average particle size of the macrolide particles in the suspension concentrate of the present invention may be in the range of from about 0.1 to about 10 pm, preferably from about 0.5 to 8 pm, and more preferably from about 1 to 5 pm.
Techniques for forming the suspension concentrate formulations of the present invention are known in the art.
In a further aspect, the present invention provides a method for controlling pests at a locus, the method comprising applying to the locus a suspension concentrate formulation as hereinbefore described.
In general, the suspension concentrate is diluted with a solvent, most suitably water, before being applied to the locus. Techniques for applying the concentrate or a dilution thereof to a locus are known in the art and include spraying.
The suspension concentrate may be applied to control insect infestations of plants. The suspension concentrate may be applied directly to the plants, to parts of the plants, or to the locus where the plants are growing or will be grown.
In a further aspect, the present invention provides the use of a suspension concentrate as hereinbefore described in the control of insects.
The amount of the suspension concentrate employed will depend on a number of factors, such as the habits of the pests to be controlled, the timing of application, the number of applications, and environmental conditions. Typically, the amount of macrolide active component required for pest control is from 5 to 100 g/ha.
As used herein, the term "locus" refers to any place where pests can grow, including the stems, leaves, roots of plants, seeds or soil.
The suspension concentrate of the present invention may be used to control pests in a wide range of plants, especially valuable crops such as wheat, rice, soybeans, corn, cotton, cucumbers, tomatoes, and cabbage.
As discussed above, the present invention resides in the finding that the 25 combination of a formaldehyde-condensed aromatic hydrocarbon sulfonate and ammonium sulfate can significantly improve the stability of a macrolide active compound in a suspension concentrate.
Therefore, in a further aspect, the present invention provides the use of a combination of a formaldehyde-condensed aromatic hydrocarbon sulfonate and ammonium sulfate to increase the stability of a macrolide active compound in a suspension concentrate formulation.
Still further, the present invention provides a method of increasing the stability of a macrolide active compound in a suspension concentrate formulation, the method comprising employing a combination of a formaldehyde-condensed aromatic hydrocarbon sulfonate and ammonium sulfate in the formulation.
Embodiments of the present invention will now be discussed, by way of the following working examples.
EXAMPLES
Example 1 -240 p/L pleocidin suspension concentrate A suspension concentrate was prepared from the following components: Pleocidin 240 g Propylene glycol 50 g Alkylnaphthalene sulfonate formaldehyde condensation product (MorwentTm D-425) 20 g Methacrylic acid copolymer 30 g Ammonium sulfate 10 g Isothiazolinone antimicrobial agent 2g Water making up to 1 L The suspension concentrate was prepared by the following method: 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 up to 40°C to obtain a final aqueous pleocidin suspension concentrate The pleocidin particles had an average particle size of 4 pm or less.
Example 2 -480 q/L pleocidin suspension concentrate A suspension concentrate was prepared from the following components: Pleocidin 480 g Propylene glycol 50 g Alkylnaphthalene sulfonate formaldehyde condensation product (TamolTm NN8906) 40g Fatty alcohol polyoxyethylene ether 50 g Ammonium sulfate 30 g Isothiazolinone antimicrobial agent 2g Water making up to 1 L The suspension concentrate was prepared by the following method: 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 up to 40°C to obtain a final aqueous pleocidin suspension concentrate. The pleocidin particles had an average particle size of 4 pm or less.
Example 3 -60 g/L ethyl pleocidin suspension concentrate A suspension concentrate was prepared from the following components: Ethyl pleocidin 60 g Propylene glycol 50 g Naphthalene sulfonate formaldehyde condensation product (SupragilTM MNS-90) 15 g Methacrylic acid copolymer 20 g Ammonium sulfate 5g Isothiazolinone antimicrobial agent 2g Water making up to 1 L The suspension concentrate was prepared by the following method: 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 up to 40°C to obtain a final aqueous ethyl pleocidin suspension concentrate. The ethyl pleocidin particles had an average particle size of 4 pm or less.
Example 4 -50 p/L emamectin benzoate suspension concentrate A suspension concentrate was prepared from the following components: Emamectin benzoate 50 g Propylene glycol 50 g Alkylnaphthalene sulfonate formaldehyde condensation product (TersperseTm 2425) 10 g 25 g Methacrylic acid copolymer Ammonium sulfate 8 g Isothiazolinone antimicrobial agent Water 3g making up to 1 L The suspension concentrate was prepared by the following method: 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 up to 40°C to obtain a final aqueous emamectin suspension concentrate. The ememectin particles had an average particle size of 5 pm or less.
Comparative Example 1 -240 q/L pleocidin suspension concentrate A suspension concentrate was prepared from the following components: Pleocidin 240 g Propylene glycol 50 g Dodecyl benzenesulfonate 20 g Methacrylic acid copolymer 30 g Ammonium sulfate 10 g Isothiazolinone antimicrobial agent 2g Water making up to 1 L The suspension concentrate was prepared by the following method: 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 up to 40°C to obtain a final aqueous pleocidin suspension concentrate. The pleocidin particles had an average particle size of 4 pm or less.
Comparative Example 2 -240 ca pleocidin suspension concentrate A suspension concentrate was prepared from the following components: Pleocidin 240 g Propylene glycol 50 g Alkylnaphthalene sulfonate formaldehyde condensation product (MorwentTm D-425) 20 g Methacrylic acid copolymer 30 g Urea 10 g Isothiazolinone antimicrobial agent 2g Water making up to 1 L The suspension concentrate was prepared by the following method: 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 up to 40°C to obtain a final aqueous pleocidin suspension concentrate. The pleocidin particles had an average particle size of 4 pm or less.
Comparative Example 3 -240 q/L pleocidin suspension concentrate A suspension concentrate was prepared from the following components: Pleocidin 240 g Propylene glycol 50 g Alkylnaphthalene sulfonate formaldehyde condensation product (MorwentIm D-425) 20 g Methacrylic acid copolymer 30 g Isothiazolinone antimicrobial agent 2g Xanthan gum 2g Water making up to 1 L The suspension concentrate was prepared by the following method: 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 up to 40°C to obtain a final aqueous pleocidin suspension concentrate The pleocidin particles had an average particle size of 4 pm or less.
Comparative Example 4 -480 QM pleocidin suspension concentrate A suspension concentrate was prepared from the following components: Pleocidin 480 g Propylene glycol 50 g Dodecyl benzenesulfonate 40 g Fatty alcohol polyoxyethylene ether Ammonium sulfate 50 g 30 g 2g making up to 1 L Isothiazolinone antimicrobial agent Water The suspension concentrate was prepared by the following method: 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 up to 40°C to obtain a final aqueous pleocidin suspension concentrate. The pleocidin particles had an average particle size of 4 pm or less.
Comparative Example 5 -480 g/L pleocidin suspension concentrate A suspension concentrate was prepared from the following components: Pleocidin 480 g Propylene glycol 50 g Alkylnaphthalene sulfonate formaldehyde condensation product (TamolTm NN8906) 40g Fatty alcohol polyoxyethylene ether 50 g Urea 30 g Isothiazolinone antimicrobial agent 2g Water making up to 1 L The suspension concentrate was prepared by the following method: 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 up to 40°C to obtain a final aqueous pleocidin suspension concentrate. The pleocidin particles had an average particle size of 4 pm or less.
Comparative Example 6 -480 ca pleocidin suspension concentrate A suspension concentrate was prepared from the following components: Pleocidin 480 g Propylene glycol 50 g Alkylnaphthalene sulfonate formaldehyde condensation product (TamolTm NN8906) 40 g Fatty alcohol polyoxyethylene ether 50 g Guar gum 2g Isothiazolinone antimicrobial agent 2g Water making up to 1 L The suspension concentrate was prepared by the following method: 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 up to 40°C to obtain a final aqueous pleocidin suspension concentrate. The pleocidin particles had an average particle size of 4 pm or less.
Comparative Example 7 -60 q/L ethyl pleocidin suspension concentrate A suspension concentrate was prepared from the following components: Ethyl pleocidin 60 g Propylene glycol 50 g Naphthalene sulfonate formaldehyde condensation product (SupragilTM MNS-90) 15g Methacrylic acid copolymer 20 g Xanthan gum 2g Isothiazolinone antimicrobial agent 2g Water making up to 1 L The suspension concentrate was prepared by the following method: 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 up to 40°C to obtain a final aqueous ethyl pleocidin suspension concentrate. The ethyl pleocidin particles had an average particle size of 5 pm or less.
Comparative Example 8-50 q/L emamectin benzoate suspension concentrate A suspension concentrate was prepared from the following components: Emamectin benzoate 50 g Propylene glycol 50 g Alkylnaphthalene sulfonate formaldehyde condensation product (TersperseTm 2425) 10 g Methacrylic acid copolymer Xanthan gum 25 g 2g 3g Isothiazolinone antimicrobial agent Water making up to 1 L The suspension concentrate was prepared by the following method: 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 up to 40°C to obtain a final aqueous emamectin benzoate suspension concentrate. The emamectin benzoate particles had an average particle size of 2 pm or less.
Performance Tests 1. Viscosity test The viscosity of each of the liquid suspension concentrates prepared in the 5 examples and comparative examples above was tested following the procedure of CIPAC MT192. Viscosity was measure using a ROOKFIELD DV-II+Pro viscometer with selected Spindle #2 under 30 revolution conditions.
The results are shown in Table 1 below.
2. Stability test 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. Thereafter, the cylinder was removed and placed at room temperature to observe the properties of each sample.
The results are shown in Table 1 below.
Table 1
Sample Viscosity Observerd separation after heat storage at 54°C for 14 days (mPa.$) Example 1 385 3% water separation, without aggregation, flocculation, or precipitation Example 2 585 2% water separation, without aggregation, flocculation, or precipitation Example 3 245 5% water separation, without aggregation, flocculation, or precipitation Example 4 205 5% water separation, without aggregation, flocculation, or precipitation Comparative 370 24% water separation, with slight aggregation, without flocculation, and with precipitation
Example 1
Comparative 390 25% water separation, without aggregation and flocculation, and with precipitation
Example 2
Comparative 540 20% water separation, with aggregation, severe flocculation, and slight precipitation
Example 3
Comparative 610 18% water separation, with slight aggregation, without flocculation, and with precipitation
Example 4
Comparative 580 20% water separation, without aggregation and flocculation, and with precipitation
Example 5
Comparative 780 21% water separation, without aggregation and flocculation, and precipitation
Example 6
Comparative 530 28% water separation, with aggregation, severe flocculation, and slight precipitation
Example 7
Comparative 480 30% water separation, with aggregation, severe flocculation, and slight precipitation
Example 8
The results in Table 1 show that the suspension concentrates of the present invention had a low water separation from the product, no aggregation and flocculation phenomena, and no precipitation after high temperature storage. This was particularly the case when the viscosities of the samples did not exceed 600 mPa.s. The suspension concentrates exhibited a good liquidity and a superior pourability, due to the lower viscosity.
In contrast, the suspension concentrates of the Comparative Examples exhibited severe water separation and precipitation during heat storage. Attempts to reduce these phenomena by adding a thickener to increase the viscosity of the system were not successful and still gave rise to aggregation and severe flocculation.

Claims (22)

  1. CLAIMS1. 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.
  2. 2. The suspension concentrate according to claim 1, wherein the composition is an aqueous suspension concentrate.
  3. 3. The suspension concentrate according to either of claims 1 or 2, wherein the macrolide active substance is selected from avermectin, emamectin, ememectin benzoate, pleocidin, ethyl pleocidin, ivermectin and mixtures of two or more thereof.
  4. 4. The suspension concentrate according to claim 3, wherein the macrolide active substance is pleocidin.
  5. 5. The suspension concentrate according to claim 1, wherein the aromatic hydrocarbon sulfonate is an alkylnaphthalene sulfonate.
  6. 6. The suspension concentrate according to any preceding claim, wherein the aromatic hydrocarbon sulfonate is a salt of an aromatic hydrocarbon sulfonate.
  7. 7. The suspension concentrate according to claim 6, wherein the salt is an alkali metal salt.
  8. 8. The suspension concentrate according to any preceding claim, wherein the aromatic hydrocarbon sulfonate condensed with formaldehyde is present in an amount of from 1 to 200 g/L.
  9. 9. The suspension concentrate according to any preceding claim, wherein ammonium sulfate is present in an amount of from 0.1 to 100 g/L.
  10. 10. The suspension concentrate according to any preceding claim, wherein the weight ratio of the macrolide active substance and the aromatic hydrocarbon sulfonate condensed with formaldehyde in the suspension concentrate is from 2:1 to 18:1.
  11. 11. The suspension concentrate according to any preceding claim, wherein the weight ratio of the macrolide active substance and ammonium sulfate in the suspension concentrate is from 6:1 to 35:1.
  12. 12. The suspension concentrate according to any preceding claim, wherein the weight ratio of the aromatic hydrocarbon sulfonate condensed with formaldehyde and ammonium sulfate in the suspension concentrate is from 1:1 to 5:1.
  13. 13. The suspension concentrate according to any preceding claim, wherein 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 thereof.
  14. 14. The suspension concentrate according to any preceding claim, wherein the suspension concentrate does not comprise a polymeric organic thickener.
  15. 15. The suspension concentrate according to claim 14, wherein the suspension concentrate does not comprise xanthan gum, guar gum, cellulose, 15 hydroxymethyl cellulose, starch, polyvinyl alcohol, polyvinylpyrrolidone and derivatives thereof.
  16. 16. The suspension concentrate according to any preceding claim, wherein 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.
  17. 17. The suspension concentrate according to claim 16, wherein 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 5 formaldehyde, 3) 0.1 to 100 g/L of ammonium sulfate.
  18. 4) 0 to 100 g/L of an agrochemically acceptable surfactant, and 5) water that makes up to 1 L. 18. The suspension concentrate according to any preceding claim, wherein 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.
  19. 19. A method for controlling pests at a locus, the method comprising applying to the locus a suspension concentrate composition according to any preceding claim, optionally wherein the suspension concentrate composition is diluted with water.
  20. 20. Use of a suspension concentrate composition according to any of claims 1 to 18 in the control of insects.
  21. 21. Use of a combination of a formaldehyde-condensed aromatic hydrocarbon sulfonate and ammonium sulfate to increase the stability of a macrolide active compound in a suspension concentrate formulation.
  22. 22. A method of increasing the stability of a macrolide active compound in a suspension concentrate formulation, the method comprising employing a combination of a formaldehyde-condensed aromatic hydrocarbon sulfonate and ammonium sulfate in the formulation.
GB2213846.5A 2022-09-22 2022-09-22 Insecticidal composition comprising a macrolide active ingredient Pending GB2625702A (en)

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GB2213846.5A GB2625702A (en) 2022-09-22 2022-09-22 Insecticidal composition comprising a macrolide active ingredient
ES202330764A ES2967107A2 (en) 2022-09-22 2023-09-11 Insecticidal composition comprising a macrolide active ingredient (Machine-translation by Google Translate, not legally binding)
FR2309863A FR3139975A1 (en) 2022-09-22 2023-09-19 Insecticidal composition comprising a macrolide active ingredient

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101518242A (en) * 2008-02-28 2009-09-02 北京绿色农华植保科技有限责任公司 Emamectin benzoate-hexaflumuron water dispersible granule and preparation method thereof
CN103430950A (en) * 2013-08-22 2013-12-11 山东省联合农药工业有限公司 Nematode-killing composition containing abamectin and furfural

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101518242A (en) * 2008-02-28 2009-09-02 北京绿色农华植保科技有限责任公司 Emamectin benzoate-hexaflumuron water dispersible granule and preparation method thereof
CN103430950A (en) * 2013-08-22 2013-12-11 山东省联合农药工业有限公司 Nematode-killing composition containing abamectin and furfural

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