Isocycloceramic formula

Abstract

The present invention: (a) Isocycloceram, (b) polyoxyalkylene copolymers, (c) an acrylic graft copolymer, and (d) Oxygenated hydrocarbon compounds The present invention relates to a composition comprising:

Description

Technical Field

[0001] The present invention relates to a composition containing isocycloseram. More specifically, the present invention relates to formulations such as milibase, or suspension concentrate (SC), flowable suspension (FS), suspoemulsion (SE), suspension concentrate capsule suspension blend (ZC), ready-to-use bait (RB), water-soluble granule (SG), water-dispersible granule (WG) and water-dispersible tablet (WT); more specifically, dilutions or dispersions of such formulations in the spray tank of farmers; and the use of such compositions for controlling and / or preventing animal pests.

Background Art

[0002] Isocycloseram is an insecticidal pesticide, and more specifically, it is a solid at room temperature (25°C). Typically, a milibase is formed by grinding isocycloseram, and then isocycloseram can be easily prepared as a fine suspension of particles dispersed in a liquid medium by adding other components or by further processing, such as in a drying stage.

[0003] However, in the case of isocycloseram, in the conventional milibase approach, for example, it is difficult to form a milibase in large-scale processing (especially at the manufacturing site) due to the low wettability of isocycloseram, and a number of problems have been found, such as an increase in the viscosity of the milibase when exposed to temperature changes (e.g., when exposed to freezing / thawing cycles).

Summary of the Invention

Problems to be Solved by the Invention

[0004] An object of the present invention is to overcome the problems of the prior art by proposing a composition containing isocycloseram that is easy to process on a large scale while ensuring temperature stability when exposed to temperature changes.

Means for Solving the Problems

[0005] For this purpose, the present invention: (a) Isocycloceram, (b) Polyoxyalkylene copolymer, (c) Acrylic graft copolymers, and (d) Oxygenated hydrocarbon compounds The objective is to provide a composition containing [the specified element].

[0006] The combination of (b), (c), and (d) with isocycloceram overcomes all of the above problems. [Brief explanation of the drawing]

[0007] [Figure 1] The results for Examples 14-23 are shown. [Modes for carrying out the invention]

[0008] The composition of the present invention may contain, based on the total weight of the composition, 0.01% to 70% by weight of isocycloceramic, preferably 0.1% to 70% by weight of isocycloceramic, preferably 5% to 70% by weight of isocycloceramic, preferably 10% to 70% by weight of isocycloceramic, preferably 20% to 60% by weight of isocycloceramic, and more preferably 40% to 60% by weight of isocycloceramic.

[0009] Isocycloceram is an insecticide with the following CAS number: 2061933-85-3 and the following chemical formula: [ka] It holds.

[0010] More specifically, isocycloceram is solid at room temperature (25°C) and has low water solubility, typically less than 5 mg / l at 20°C.

[0011] More specifically, the melting point of isocycloceram may be 135 to 150°C, preferably 138 to 148°C, and more preferably 141 ± 2°C.

[0012] The melting point of isocycloceram can be easily determined using differential scanning calorimetry (DSC) at a heating rate of 10°C / min.

[0013] Isocycloceram may contain the isomer (5S,4R) which is 4-[(5S)-5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4H-isoxazole-3-yl]-N-[(4R)-2-ethyl-3-oxo-isoxazolidine-4-yl]-2-methyl-benzamide, and optionally at least one isomer selected from isomer (5S,4S), isomer (5R,4R), isomer (5R,4S), and any combination thereof. In the present invention, the isomer (5S,4S) is 4-[(5S)-5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4H-isoxazole-3-yl]-N-[(4S)-2-ethyl-3-oxo-isoxazolidine-4-yl]-2-methyl-benzamide; the isomer (5R,4R) is 4-[(5R)-5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4H The isomer (5R,4S) is 4-[(5R)-5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4H-isoxazole-3-yl]-N-[(4S)-2-ethyl-3-oxoisoxazolidine-4-yl]-2-methyl-benzamide. If isocycloceram further comprises at least one isomer selected from isomer (5S,4S), isomer (5R,4R), isomer (5R,4S), and any combination thereof, isocycloceram may contain isomer (5S,4R) in a molar ratio of more than 50%, for example, at least 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95%, 96%, 97%, 98%, or 99% relative to the total amount of isomers (5S,4R), (5S,4S), (5R,4R), and (5R,4S).

[0014] The composition of the present invention can contain 0.0005% to 50% by weight of a polyoxyalkylene copolymer, preferably 0.1% to 30% by weight of a polyoxyalkylene copolymer, and more preferably 1% to 20% by weight of a polyoxyalkylene copolymer, based on the total weight of the composition.

[0015] In the present invention, the polyoxyalkylene copolymer can be obtained from at least two different alkylene oxides such as ethylene oxide and propylene oxide monomers.

[0016] More preferably, the polyoxyalkylene copolymer can be an AB, ABA, BAB, or ABABA type polyoxyalkylene block copolymer.

[0017] More specifically, the polyoxyalkylene copolymer can be prepared by ring-opening polymerization of the corresponding cyclic ethylene oxide and propylene oxide monomers.

[0018] Typically, the ring-opening polymerization is initiated by the addition of water and an alkali hydroxide such as sodium hydroxide and potassium hydroxide. The block structure of the copolymer is formed by first polymerizing a polymer block using the first monomer and then adding the second monomer to form a further polymer block.

[0019] In a preferred embodiment, the polyoxyalkylene copolymer can be an ethylene oxide-propylene oxide-ethylene oxide block copolymer (EO-PO-EO block copolymer), or, in other words, a poly(ethylene oxide)-poly(propylene oxide)-poly(ethylene oxide) block copolymer or a poly(ethylene glycol)-poly(propylene glycol)-poly(ethylene glycol) block copolymer.

[0020] The polyoxyalkylene copolymer of the present invention, and more specifically, the EO-PO-EO block copolymer can have a molecular weight of 1,000 to 15,000 g / mol, and more preferably 3,000 to 7,000 g / mol.

[0021] In the present invention, the notation "molecular weight" means the average molecular weight (i.e., the approximate molecular weight). The molecular weight of the polymer, or in other words the molar mass, can be easily determined by a method well-known in the technical field such as gel permeation chromatography (GPC).

[0022] In the first embodiment, the EO-PO-EO block copolymer can have a polypropylene oxide molecular weight of 900 to 4,000 g / mol, and preferably 2,000 to 4,000 g / mol. In other words, the polypropylene oxide molecular weight is the molecular weight of the poly(propylene oxide) block of the EO-PO-EO block copolymer.

[0023] In the second embodiment, the EO-PO-EO block copolymer can have an ethylene oxide content of 10 to 80%, and preferably 30 to 50% with respect to the total weight of the copolymer. In other words, the ethylene oxide content is the proportion of the poly(ethylene oxide) block in the EO-PO-EO block copolymer.

[0024] In the third aspect, the EO-PO-EO block copolymer can have the characteristics of the first embodiment and the characteristics of the second embodiment.

[0025] Examples include GENAPOL® PF series (CLARIANT), PLURONIC® series (BASF), SYNPERONIC® PE series (CRODA) or TOXIMUL® series (STEPAN).

[0026] The composition of the present invention may contain, based on the total weight of the composition, 0.0005% to 30% by weight of an acrylic graft copolymer, preferably 0.01% to 30% by weight of an acrylic graft copolymer, and more preferably 0.1% to 20% by weight of an acrylic graft copolymer.

[0027] Acrylic graft copolymers typically have a comb-like or star-shaped structure, and preferably a comb-like structure.

[0028] Graft copolymers are branched copolymers in which the components that form the side chains are structurally different from the components that form the main chain.

[0029] Comb-shaped polymers are composed of a main chain (backbone) that has branching points from which linear side chains extend.

[0030] Star-shaped polymers are composed of a polyfunctional center from which at least three polymer chains radiate outwards.

[0031] In preferred embodiments, the acrylic graft copolymer can be an amphiphilic copolymer.

[0032] More specifically, the acrylic graft copolymer comprises at least one component A (hydrophilic portion) that is solubilized by an aqueous medium, and at least one other component B that is hydrophobic.

[0033] Suitable acrylic graft copolymers may include polyethylene glycol, monomethyl ether of polyethylene glycol, poly(vinylpyrrolidone), poly(acrylamide), or poly(vinyl alcohol) as hydrophilic side chains, while the hydrophobic backbone may include polymers and copolymers of styrene, methyl acrylate, methyl methacrylate, ethyl acrylate, 2-ethylhexyl acrylate, lauryl methacrylate, or vinyl acetate.

[0034] Such acrylic graft copolymers can be prepared, for example, by converting a monomethyl ether of polyethylene glycol to an acrylic acid ester or methacrylic acid ester, and then subjecting this to radical polymerization with other unsaturated monomers such as styrene, ethyl acrylate, or methyl methacrylate. Such acrylic graft copolymers can also be prepared by reacting a hydrophobic polymer backbone consisting of chemically reactive sites such as carboxyl, hydroxyl, or amine groups with monomeric alkylene oxides such as ethylene oxide and propylene oxide to form hydrophilic side chains.

[0035] More preferably, the acrylic graft copolymer is a nonionic polymer, and more specifically, has a comb-like structure.

[0036] In the present invention, the acrylic graft copolymer may contain polyethylene glycol and / or mono-ether polyethylene glycol side chains.

[0037] Acrylic graft copolymers may also contain a backbone derived from acrylate and / or methacrylate monomers.

[0038] More preferably, the acrylic graft copolymer may include a backbone obtained from acrylate and / or methacrylate monomers, as well as side chains containing polyethylene glycol and / or mono-ether polyethylene glycol, thereby giving the polymer a comb-like structure.

[0039] For example, the acrylic graft copolymer of the present invention may be Atlox 4913 (trademark) provided by CRODA, or Tersperse 2500 (trademark) provided by HUNTSMAN.

[0040] The composition of the present invention may contain, based on the total weight of the composition, 0.0001% to 30% by weight of an oxygen-containing hydrocarbon compound, preferably 0.01% to 30% by weight of an oxygen-containing hydrocarbon compound, and more preferably 0.1% to 20% by weight of an oxygen-containing hydrocarbon compound.

[0041] The oxygen-containing hydrocarbon compound can be selected from alkyl ether compounds, alkyl ester compounds, and any mixture thereof; and preferably from polyethylene glycol alkyl ethers, sulfonated alkyl ester compounds, and any mixture thereof. In other words, the oxygen-containing hydrocarbon compound (d) is preferably different from the polyoxyalkylene copolymer (b) and the acrylic graft copolymer (c).

[0042] Polyethylene glycol alkyl ethers can be obtained by reacting an alcohol with ethylene oxide. Suitable alcohols are C2-C2. 15 Chain length, preferably C7~C 11 The chain length, and more preferably C9 or C 10 It is a straight-chain or branched-chain aliphatic alcohol having a chain length of . One example is Rhodasurf DA / 630-E(trademark) provided by SOLVAY-RHODIA.

[0043] The sulfonated alkyl ester compound can be a sulfosuccinate ester or a salt of a sulfosuccinate ester. One example is Aerosol® OT-B, provided by SOLVAY-RHODIA.

[0044] In the present invention, the composition may further contain water.

[0045] In particular embodiments of the present invention, the composition for forming the mill base is: (a) 20 to 70% by weight of isocycloceram, and more preferably 30 to 60% by weight of isocycloceram, relative to the total weight of the composition; (b) a polyoxyalkylene copolymer, preferably in an amount of 0.1% to 10.0% by weight, and more preferably in an amount of 1.0% to 4.0% by weight, relative to the total weight of the composition; (c) an acrylic graft copolymer, preferably in an amount of 0.1% to 10.0% by weight, and more preferably in an amount of 0.2% to 2.0% by weight, relative to the total weight of the composition; (d) an oxygen-containing hydrocarbon compound, preferably in an amount of 0.01% to 10.0% by weight, and more preferably in an amount of 0.1% to 2.0% by weight, relative to the total weight of the composition; and (e) Water (optional) It may include.

[0046] In the aforementioned specific embodiments, isocycloceram, polyoxyalkylene copolymer, acrylic graft copolymer, and oxygen-containing hydrocarbon are compounds described herein.

[0047] In other specific embodiments of the present invention, the composition is particularly used to form formulations such as suspension concentrates (SC), flowable formulation suspensions (FS), suspension emulsions (SE), suspension concentrate capsule suspension blends (ZC), ready-to-use feeds (RB), water-soluble granules (SG), water-dispersible granules (WG), and water-dispersible tablets (WT): (a) 0.01% to 50.0% by weight of isocycloceramic acid, and more preferably 0.1% to 40.0% by weight of isocycloceramic acid, based on the total weight of the composition; (b) a polyoxyalkylene copolymer, preferably in an amount of 0.0005% to 50.0% by weight, and more preferably in an amount of 0.002% to 25.0% by weight, relative to the total weight of the composition; (c) an acrylic graft copolymer, preferably in an amount of 0.0005% to 20.0% by weight of the total weight of the composition, and more preferably in an amount of 0.001% to 10.0% by weight of the acrylic graft copolymer; (d) an oxygen-containing hydrocarbon compound, preferably in an amount of 0.0001% to 10.0% by weight, and more preferably in an amount of 0.001% to 5.0% by weight, relative to the total weight of the composition; and (e) Water (optional) It may include.

[0048] In the aforementioned specific embodiments, isocycloceram, polyoxyalkylene copolymer, acrylic graft copolymer, and oxygen-containing hydrocarbon are compounds described herein.

[0049] The compositions of the present invention may further comprise one or more compounding additives that are well known in the art. In particular, the compounding additives can be selected from antifreezes, defoaming agents, antimicrobial agents (or biocides), viscosity modifiers (or thickeners), pH modifiers, and any mixture thereof.

[0050] In preferred embodiments, the composition of the present invention may further contain at least a silicone compound as an antifoaming agent. An example of a silicone compound may be polydimethylsiloxane.

[0051] The defoaming agent can be added to the composition in an appropriate amount to obtain the desired properties. For example, the composition of the present invention may contain 0.0001% to 5% by weight of the defoaming agent, preferably 0.0001% to 1% by weight of the defoaming agent, and more preferably 0.01% to 1% by weight of the defoaming agent, based on the total weight of the composition.

[0052] Other suitable compounding additives, among those known to those skilled in the art, include antioxidants, emulsifiers, colorants (or pigments), fragrances, auxiliaries, attractants, binders, buffers, solid supports (carriers), coatings, deodorants, emetics, inorganic fillers, toxicity mitigators, organic solvents, photoprotective agents, and any mixtures thereof.

[0053] The composition of the present invention may further contain additional pesticides. These additional pesticides may be insecticides, fungicides, herbicides, synergists, plant growth regulators, nematicides, plant nutrients, plant fertilizers, and mixtures thereof.

[0054] In certain embodiments, the compositions of the present invention may contain additional insecticides selected from abamectin, chlorantraniliprole, chlorfenapyr, cyantraniliprole, emamectin benzoate, ethiprole, γ-cyhalothrin, lambda-cyhalothrin, lufenuron, methoxyfenozide, pymetrozine, spinetoram, spinosad, sulfoxaflor, thiamethoxam, and any mixtures thereof; and more preferably, additional insecticides selected from chlorantraniliprole, chlorfenapyr, cyantraniliprole, emamectin benzoate, ethiprole, lambda-cyhalothrin, lufenuron, spinosad, and any mixtures thereof. The weight ratio of isocycloceram to additional insecticide can be 1:100 to 100:1, preferably 1:20 to 20:1, preferably 1:10 to 10:1, preferably 1:1 to 1:10, and more preferably 1:1 to 1:6.

[0055] When emamectin benzoate is used as an additional insecticide, it is preferable to add a photoprotective agent to the composition.

[0056] The compositions of the present invention may contain one or more of the above-mentioned components in suitable amounts to obtain their respective properties as appropriate.

[0057] For other purposes of the present invention, the compositions can be advantageously used to prepare suspension concentrates (SC), flowable suspensions (FS), suspension emulsions (SE), suspension concentrate capsule suspension blends (ZC), ready-to-use feeds (RB), water-soluble granules (SG), water-dispersible granules, or water-dispersible tablets (WT).

[0058] In a particular embodiment, the compositions of the present invention may relate to the following: - A concentrate designed for addition to water spray tanks used by agricultural workers, or a concentrate that can be applied as is without further dilution, - A suspension produced when a concentrate is mixed with water in a water spray tank used by agricultural workers.

[0059] In another object of the present invention, the present invention relates to a method for controlling and / or controlling animal pests, comprising the step of applying a composition according to the present invention to a pest, a habitat of a pest, or a plant susceptible to attack by a pest.

[0060] Animal pests can be invertebrate pests such as insects, mites, nematodes, or mollusks. The term "plant" as used herein includes seedlings, shrubs, and trees.

[0061] The compositions according to the present invention can be used to eradicate and / or control (i.e., contain or destroy) the above-mentioned types of pests that occur particularly on plants, especially plants useful in agriculture, horticulture and forestry, and ornamental plants, or on organs such as fruits, flowers, clusters of leaves, stems, tubers or roots of such plants, and in some cases, protection from these pests is maintained even on plant organs that are formed at a later time.

[0062] Suitable target crops include, in particular, cereals such as wheat, barley, rye, oats, rice, maize (e.g., feed maize, popcorn, corn), millet, or sorghum; sugar or beets such as feed beets; pome, stone, or soft fruits such as apples, pears, plums, peaches, almonds, and cherries, or berries such as strawberries, raspberries, or blackberries; kidney beans, lentils, peas, or soybeans. Leguminous crops such as beans; oil crops such as rapeseed, mustard, poppy, olive, sunflower, coconut, castor, cocoa or peanut; cucurbitaceous plants such as pumpkin, cucumber, melon, watermelon, cucumber or squash; fiber plants such as cotton, flax, hemp or jute; citrus fruits such as orange, lemon, grapefruit or tangerine; vegetables such as spinach, lettuce, asparagus, cabbage, broccoli, cauliflower, carrot, onion, tomato, potato or bell pepper; laurel family plants such as avocado, cinnamon or camphor; and tobacco, nuts, coffee, eggplant, sugarcane, tea, pepper, grape, hops, plantain family and latex plants.

[0063] In this method, the composition can generally be applied together with an effective amount of isocycloceram.

[0064] More preferably, the method described above is applied to the spraying of the composition of the present invention supplied from, for example, a spray container.

[0065] The above method allows for the effective application of the composition in an amount of 0.01 to 5 liters / hectare (L / ha), and more preferably 0.02 to 3.0 L / ha.

[0066] In other objects of the present invention, the composition may be a seed treatment formulation, or in other words, plant propagation material may be treated with the composition according to the present invention. The term "plant propagation material" is understood to mean all reproductive parts of a plant, such as seeds, including asexual plant materials such as cuttings, that can be used for propagation. Examples of plant propagation material include seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes, and parts of plants. Plant propagation material may be treated with the composition of the present invention before sowing or planting. Alternatively, plant propagation material may be treated with the composition of the present invention during sowing or planting. Furthermore, the composition of the present invention may be applied to already treated propagation material before or during planting. The composition of the present invention may be applied during seed sowing. The composition may also be used for plant propagation material derived from plants grown in greenhouses and / or plants being transplanted. The seed treatment formulation can be applied in an amount ranging from 10 mg to 1 g of the active substance (isocycloceram) per 1 kg of seeds, preferably from 10 mg to 500 mg of the active substance (isocycloceram) per 1 kg of seeds, and more preferably from 10 mg to 100 mg of the active substance (isocycloceram) per 1 kg of seeds.

[0067] For other purposes of the present invention, the composition may also be used as a treatment for the health of animals.

[0068] The following non-limiting examples illustrate improved behavior related to compositions according to the present invention.

[0069] The compounds used in the following examples are described in detail below. Isocycloceram is an insecticide that is solid at room temperature (25°C) and has a melting point of 141±2°C (CAS number: 2061933-85-3). Pluronic™ PE 10400 is an EO-PO-EO block copolymer (CAS number: 9003-11-6) supplied by BASF. -Atlox(trademark)4913-LQ-(MV) is a solution containing approximately 35% by weight of an acrylic graft copolymer, provided by CRODA. -Rhodasurf DA / 630-E is a polyethylene glycol alkyl ether (CAS number: 78330-20-8) supplied by SOLVAY-RHODIA. -Aerosol(trademark) OT-B contains a mixture of sodium dioctyl sulfosuccinate (80-90%) and sodium benzoate (15-20%) and is supplied by SOLVAY-RHODIA. [Examples]

[0070] Example 1 This example provides a composition according to the present invention, which is a mill base (i.e., isocycloceram mill base) and can be used to prepare further compositions or formulations according to the present invention. The mill base of Example 1 may contain well-known compounding additives such as viscosity modifiers, biocides, and defoamers.

[0071] Water and biocide were placed in a double-jacketed mixing container and stirred with a sawtooth mixer starting at ambient temperature (20°C). A viscosity modifier was quickly added, and the mixture was continued to stir until the viscosity modifier was completely dispersed and no lumps were visible. While continuing to mix, the defoaming agents Rhodasurf DA / 630-E, Atlox® 4913-LQ-(MV), and Pluronic® PE 10400 (as a 25% aqueous solution) were added in a given order. The container was connected to a cooling unit and cooled to 10°C, after which isocycloceram was added to the container.

[0072] Once the isocycloceram was completely wetted, high-shear mixing (Silverson high-shear mixer, 5000 rpm) was started. The mixture was continuously sheared until it was confirmed that it could pass through a 150 μm sieve. The mixture was then transferred to a horizontal bead mill and ground until the following median particle size was achieved: D(v,50)<2 μm, with 70% being less than 3 μm (measured with a Malvern Mastersizer 2000, laser diffraction particle size analyzer).

[0073] The concentrations of the components added to form the isocycloceramyl base in Example 1 are listed in Table 1 below, and these are expressed as weight percentages (%w / w) of the total weight of the isocycloceramyl base.

[0074] [Table 1]

[0075] Example 2 This example provides a suspension concentrate according to the present invention. The following components were placed in a container in the order of water, biocide, antifreeze, and viscosity modifier, and mixed with a paddle stirrer. Then, the isocycloceramyl base from Example 1 was added. The resulting composition was mixed with a paddle stirrer under low shear for 1 hour. The pH was adjusted to the target value (pH 5) using an acidifying agent (pH modifier). The biocide, antifreeze, viscosity modifier, and pH modifier added to form the suspension concentrate are well-known compounding additives.

[0076] The concentrations of the components added to form the suspension concentrate of Example 2 are listed in Table 2 below, and these are expressed as weight percentages of the total volume of the suspension concentrate (%w / v).

[0077] [Table 2]

[0078] Examples 3-13 5 g of aqueous solutions of Pluronic PE 10400, Atlox 4913-LQ-(MV), Rhodasurf DA / 630E, and Aerosol OT-B were charged into a 50 ml glass beaker with an inner diameter of 40 mm, with the concentrations of each component as shown in Table 3 below. 5 g of isocycloceram was added to the solution within 10 seconds. The beaker was allowed to stand. The wettability of the solid isocycloceram was visually evaluated after 1 minute, 2 minutes, and 8 minutes.

[0079] A sample was considered fully wetted if no isocycloceram was floating on the surface of the liquid and all of it had sunk to the bottom of the beaker.

[0080] Table 3 summarizes the concentrations of the components in Examples 3 to 13, expressed as a weight percentage (%w / w) relative to the total weight of the composition, as well as the wettability evaluation.

[0081] [Table 3]

[0082] Examples 14-23 To prepare 10 g of a given mill base, the components listed in Table 4 below were placed in a 30 ml glass jar. First, Pluronic PE 10400, Atlox 491-LQ-(MV), Rhodasurf DA / 630E, and Aerosol OT-B were dissolved in water. Next, an antifoaming agent (a compounding additive well known in the art) and isocycloceram were added. Finally, 15 ml of zirconium silicate beads (type Z, diameter 0.8-1.0 mm) were added for wet grinding. The jar was ground using a Retsch MM200 vibrating mill for 30 seconds. -1 Shake for 15 minutes. Let the jar stand for 75 minutes to cool, then 30 seconds -1 The mixture was then shaken for a further 15 minutes. After that, the sample was allowed to cool, and then poured into a sieve (150 μm) to remove the zirconium silicate beads. To confirm the efficiency of the grinding process, the particle size was measured using a Malvern Mastersizer 2000 laser diffraction particle size analyzer. A sufficient grinding process yields D[4,3] particle sizes of 1 to 10 μm, and preferably 1 to 5 μm (D[4,3] is known as the De Brouckere mean diameter or volume-weighted mean diameter).

[0083] Table 4 summarizes the concentrations of the components in Examples 14-23, expressed as weight percentages (%w / w) relative to the total weight of the composition, as well as the particle sizes.

[0084] [Table 4]

[0085] To evaluate the temperature stability of the samples (Examples 14-23), the viscosity of the samples was measured at various temperatures. The viscosity of the samples was measured using an Anton-Parr MCR 502 rheometer equipped with CC17 cup and bob shapes. The temperature was first lowered from 20°C to -10°C at a rate of 0.5°C / min while rotating the bob under a constant shear stress of 10 Pa, and then raised to 60°C at a rate of 0.5°C / min.

[0086] As the temperature decreases, the viscosity of the sample is expected to increase until it reaches its freezing point. As the temperature increases, the viscosity is expected to decrease. The phenomenon of viscosity increasing with increasing temperature indicates the breakdown of the dispersant system, which may be accompanied by irreversible aggregation of solid particles.

[0087] The results of Examples 14-23 are shown in Figure 1. More specifically, when the temperature was raised from 25°C to 60°C, Examples 17 and 21 according to the present invention showed stable viscosity up to 60°C, or in other words, Examples 17 and 21 did not show an increase in viscosity, especially above 40°C, compared to Examples 15, 18, 19, and 23 (see Figure 1).

[0088] When the temperature was raised from -10°C to 25°C, no further reduction in viscosity was observed, and therefore, it could not be measured within the range shown in Figure 1; therefore, Example 22 is not shown in Figure 1.

[0089] Therefore, as shown above, Examples 6, 10, 17, and 21 of the present invention demonstrate that the combination of polyoxyalkylene copolymer (b), acrylic graft copolymer (c), and oxygen-containing hydrocarbon compound (d) is important for the wettability of isocycloceram, and that this combination is advantageous for large-scale processing of the composition while ensuring the temperature stability of the composition. Another aspect of the present invention may be as follows: [1] (a) Isocycloceram, (b) Polyoxyalkylene copolymer, (c) Acrylic graft copolymers, and (d) Oxygenated hydrocarbon compounds A composition containing the following: [2] The composition according to [1], characterized by comprising 0.01% to 70% by weight of isocycloceramic, preferably 0.1% to 70% by weight of isocycloceramic, and more preferably 5% to 60% by weight of isocycloceramic, based on the total weight of the composition. [3] The composition according to [1] or [2], characterized by comprising 0.0005% to 50% by weight of the polyoxyalkylene copolymer and preferably 1.0% to 20% by weight of the polyoxyalkylene copolymer, based on the total weight of the composition. [4] The composition according to any one of [1] to [3], characterized in that it contains 0.0005% to 30% by weight of the acrylic graft copolymer, and preferably 0.1% to 20% by weight of the acrylic graft copolymer, based on the total weight of the composition. [5] The composition according to any one of [1] to [4], characterized in that it contains 0.0001% to 30% by weight of the oxygen-containing hydrocarbon compound, and preferably 0.1% to 20% by weight of the oxygen-containing hydrocarbon compound, based on the total weight of the composition. [6] The composition according to any one of [1] to [5], characterized in that the polyoxyalkylene copolymer is obtained from ethylene oxide and propylene oxide monomer. [7] The composition according to any one of the above [1] to [6], characterized in that the polyoxyalkylene copolymer is a poly(ethylene oxide)-poly(propylene oxide)-poly(ethylene oxide) block copolymer. [8] The composition according to any one of [1] to [7], characterized in that the polyoxyalkylene copolymer has a molecular weight of 1,000 to 15,000 g / mol, and preferably 3,000 to 7,000 g / mol. [9] The composition according to any one of [1] to [8], characterized in that the acrylic graft copolymer comprises polyethylene glycol and / or mono-ether polyethylene glycol side chains.

[10] The composition according to any one of [1] to [9], characterized in that the acrylic graft copolymer comprises a skeleton obtained from an acrylate and / or methacrylate monomer.

[11] The composition according to any one of [1] to

[10] , characterized in that the oxygen-containing hydrocarbon compound is selected from alkyl ether compounds, alkyl ester compounds, and any mixture thereof.

[12] The composition according to any one of [1] to

[11] , characterized in that the oxygen-containing hydrocarbon compound is selected from polyethylene glycol alkyl ether, sulfonated alkyl ester compound, and any mixture thereof.

[13] The composition according to any one of the above [1] to

[12] , further comprising one or more compounding additives selected from an antifreeze, an antifoaming agent, an antimicrobial agent (or biocide), a viscosity modifier, a pH modifier, and any mixture thereof.

[14] The composition according to any one of [1] to

[13] above, characterized in that it is used for preparing a suspension concentrate, a flowable formulation suspension, a suspension emulsion, a suspension concentrate capsule suspension blend, a ready-to-use feed, a water-soluble granule, a water-dispersible granule or a water-dispersible tablet.

[15] A method for controlling and / or controlling animal pests, comprising the step of applying the composition described in any one of items [1] to

[14] above to the pest, the habitat of the pest, or a plant susceptible to attack by the pest.

Claims

1. (a) Compounds of the following formula (b) Polyoxyalkylene copolymer, (c) Nonionic acrylic graft copolymer, wherein the acrylic graft copolymer includes polyethylene glycol and / or mono-ether polyethylene glycol side chains, and (d) an oxygen-containing hydrocarbon compound selected from alkyl ether compounds, alkyl ester compounds, and any mixture thereof. A composition containing the following:

2. The composition according to claim 1, characterized by containing 0.01% to 70% by weight of compound (a), 0.1% to 70% by weight of compound (a), or 5% to 60% by weight of compound (a) based on the total weight of the composition.

3. The composition according to claim 1 or 2, characterized in that it contains 0.0005% to 50% by weight of the polyoxyalkylene copolymer, or 1.0% to 20% by weight of the polyoxyalkylene copolymer, based on the total weight of the composition.

4. The composition according to any one of claims 1 to 3, characterized in that it contains 0.0005% to 30% by weight of the acrylic graft copolymer, or 0.1% to 20% by weight of the acrylic graft copolymer, based on the total weight of the composition.

5. The composition according to any one of claims 1 to 4, characterized in that it contains 0.0001% to 30% by weight of the oxygen-containing hydrocarbon compound, or 0.1% to 20% by weight of the oxygen-containing hydrocarbon compound, based on the total weight of the composition.

6. The composition according to any one of claims 1 to 5, characterized in that the polyoxyalkylene copolymer is obtained from ethylene oxide and propylene oxide monomers.

7. The composition according to any one of claims 1 to 6, characterized in that the polyoxyalkylene copolymer is a poly(ethylene oxide)-poly(propylene oxide)-poly(ethylene oxide) block copolymer.

8. The composition according to any one of claims 1 to 7, characterized in that the polyoxyalkylene copolymer has a molecular weight of 1,000 to 15,000 g / mol or 3,000 to 7,000 g / mol.

9. The composition according to any one of claims 1 to 8, characterized in that the acrylic graft copolymer includes a skeleton obtained from acrylate and / or methacrylate monomers.

10. The composition according to any one of claims 1 to 9, characterized in that the oxygen-containing hydrocarbon compound is selected from polyethylene glycol alkyl ether, sulfonated alkyl ester compound, and any mixture thereof.

11. The composition according to any one of claims 1 to 10, further comprising one or more compounding additives selected from an antifreeze, an antifoaming agent, an antimicrobial agent (or biocide), a viscosity modifier, a pH modifier, and any mixture thereof.

12. The composition according to any one of claims 1 to 11, further comprising an additional insecticide selected from abamectin, chlorantraniliprole, chlorfenapyr, cyantraniliprole, emamectin benzoate, ethiprole, γ-cyhalothrin, lambda-cyhalothrin, lufenuron, methoxyfenozide, pymetrozine, spinetram, spinosad, sulfoxaflor, thiamethoxam, and any mixture thereof.

13. The composition according to any one of claims 1 to 12, characterized in that it is used for preparing suspension concentrates, flowable formulation suspensions, suspension emulsions, suspension concentrate capsule suspension blends, ready-to-use feeds, water-soluble granules, water-dispersible granules, or water-dispersible tablets.

14. The composition according to any one of claims 1 to 13, wherein compound (a) comprises at least 4-[(5S)-5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4H-isoxazole-3-yl]-N-[(4R)-2-ethyl-3-oxo-isoxazolidine-4-yl]-2-methyl-benzamide.

15. The composition according to any one of claims 1 to 14, wherein compound (a) is isocycloceram.

16. A method for exterminating and / or controlling animal pests, comprising the step of applying the composition described in any one of claims 1 to 15 to the pest, the habitat of the pest, or plants susceptible to attack by the pest.

Images