Complex

Abstract

The present invention relates to a composition comprising: (a) isocycloceram and (b) a lignin compound having an average molecular weight of 10,000 g / mol or less.

Description

[Technical field]

[0001] The present invention relates to compositions comprising isocycloceram, more particularly to formulations such as dispersible concentrates, dilutions of such formulations, more particularly in agricultural spray tanks, and the use of such compositions to combat and / or control animal pests. [Background technology]

[0002] Isocycloceram is an insecticidal pesticide. However, it has been found that the use of such active ingredients poses many problems when using traditional formulation techniques, such as the fact that dilution of the formulation with water-miscible solvents promotes crystal growth of the less water-soluble active ingredients, and that dilutions of the formulation are difficult to stabilize, as the formulations are often not very tolerant of changes in conditions such as changes in dilution ratio, temperature, and water quality, among other parameters. Summary of the Invention [Problem to be solved by the invention]

[0003] The present invention aims to overcome the problems associated with the prior art techniques by proposing an isocycloceram-containing composition having dilution stability, in particular ensuring good solubility of isocycloceram even at 100 g / l.

[0004] To this end, the present invention provides: (a) isocycloceram, and (b) a lignin compound having an average molecular weight of 10,000 g / mol or less The present invention provides a composition comprising: [Means for solving the problem]

[0005] By combining said lignin compounds with isocycloceram, all of the above problems were overcome. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0006] Isocycloceram is an insecticidal pesticide with the following CAS number: 2061933-85-3 and the following chemical formula: [ka] has.

[0007] Isocycloserum can include the isomer (5S,4R) which is 4-[(5S)-5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-[(4R)-2-ethyl-3-oxo-isoxazolidin-4-yl]-2-methyl-benzamide (CAS number: 1309959-62-3), and optionally at least one of the isomers selected from the isomer (5S,4S), the isomer (5R,4R), the isomer (5R,4S), and any combination thereof. In the present invention, the isomer (5S,4S) is 4-[(5S)-5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-[(4S)-2-ethyl-3-oxo-isoxazolidin-4-yl]-2-methyl-benzamide; the isomer (5R,4R) is 4-[(5R)-5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H -isoxazol-3-yl]-N-[(4R)-2-ethyl-3-oxo-isoxazolidin-4-yl]-2-methyl-benzamide; and the isomer (5R,4S) is 4-[(5R)-5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-[(4S)-2-ethyl-3-oxo-isoxazolidin-4-yl]-2-methyl-benzamide. When isocycloserum further comprises at least one isomer selected from the isomer (5S,4S), the isomer (5R,4R), the isomer (5R,4S), and any combination thereof, it may comprise the isomer (5S,4R) in a molar proportion of more than 50%, for example at least 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95%, 96%, 97%, 98% or 99%, based on the total amount of isomers (5S,4R), (5S,4S), (5R,4R) and (5R,4S).

[0008] The composition of the present invention may contain from 0.01% to 70% by weight of isocycloserum, preferably from 0.1% to 50% by weight of isocycloserum, preferably from 1% to 30% by weight of isocycloserum, more preferably from 5% to 20% by weight of isocycloserum, based on the total weight of the composition.

[0009] The lignin compounds of the present invention may have an average molecular weight of up to 5000 g / mol. In a preferred embodiment, the lignin compounds may have an average molecular weight of at least 1000 g / mol.

[0010] In the present invention, the expression "average molecular weight" means an approximate molecular weight. The molecular weight, or in other words the molar mass, of a lignin compound can be easily determined by methods known in the art, such as gel permeation chromatography (GPC).

[0011] The lignin compound of the present invention can more specifically be kraft lignin.

[0012] In other particular embodiments, the lignin compound can be a non-sulfonated lignin. In a preferred embodiment, the lignin compound can be a non-sulfonated kraft lignin.

[0013] Non-sulfonated Kraft lignin is produced using the Kraft process (also known as the sulfate process), i.e., with sodium hydroxide (NaOH) and sodium sulfide (Na 2 S) which produces lignin that is not sulfonated, unlike that produced by the acid sulfite process.

[0014] The composition of the present invention may contain, relative to the total weight of the composition, 0.01% to 30% by weight of the lignin compound, preferably 0.1% to 20% by weight of the lignin compound, and more preferably 0.1% to 10% by weight of the lignin compound.

[0015] The composition of the present invention may further comprise (c) an acrylic graft copolymer.

[0016] The acrylic graft copolymers typically have a comb or star structure, and preferably a comb structure.

[0017] Graft copolymers are branched copolymers in which the components that form the side chains are structurally different from the components that form the backbone.

[0018] Comb polymers are comprised of a main chain (backbone) having branch points from each of which extend linear side chains.

[0019] Star polymers comprise a multifunctional center from which at least three polymer chains radiate out.

[0020] In a preferred embodiment, the acrylic graft copolymer can be an amphiphilic copolymer.

[0021] More specifically, the acrylic graft copolymer comprises at least one component A (hydrophilic part) that is solubilized by an aqueous medium, and at least one other component B that is hydrophobic.

[0022] Suitable acrylic graft copolymers may contain as the hydrophilic side chains polyethylene glycol, mono-methyl ether of polyethylene glycol, poly(vinylpyrrolidone), poly(acrylamide) or poly(vinyl alcohol), while the hydrophobic backbone may contain polymers and copolymers of styrene, methyl acrylate, methyl methacrylate, ethyl acrylate, 2-ethylhexyl acrylate, lauryl methacrylate or vinyl acetate.

[0023] Such acrylic graft copolymers can be prepared, for example, by converting mono-methyl ethers of polyethylene glycol to acrylic or methacrylic acid esters, which are then subjected 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.

[0024] More preferably, the acrylic graft copolymer is a nonionic polymer, more particularly one having a comb structure.

[0025] In the present invention, the acrylic graft copolymer can contain polyethylene glycol and / or mono-ether polyethylene glycol side chains.

[0026] The acrylic graft copolymer can also include a backbone derived from acrylate and / or methacrylate monomers.

[0027] Even more preferably, the acrylic graft copolymer may comprise a backbone derived from acrylate and / or methacrylate monomers and side chains comprising polyethylene glycol and / or mono-ether polyethylene glycol, which more particularly gives the polymer a comb structure.

[0028] For example, the acrylic graft copolymer of the present invention can be Agrilan 755 offered by Nouryon, Atlox 4913™ offered by CRODA, or Tersperse 2500™ offered by HUNTSMAN.

[0029] The composition of the present invention can comprise from 0.01% to 30% by weight of the acrylic graft copolymer, preferably from 0.1% to 20% by weight of the acrylic graft copolymer, and more preferably from 0.1% to 10% by weight of the acrylic graft copolymer, based on the total weight of the composition.

[0030] The composition of the present invention may further comprise (d) a lactamide compound.

[0031] The lactamide compound is more specifically represented by formula I: CH 3 CH(OH)C(=O)NR 1 R 2 (I) (In the formula, R 1 and R 2 are each independently hydrogen; or phenyl, hydroxy, C 1-5 Alkoxy, morpholinyl, and NR 3 R 4 (In the formula, R 3 and R 4 are each independently C 1-3 each of which is optionally substituted with up to three substituents independently selected from 1-6 Alkyl, C 2-6 Alkenyl or C 3-6 cycloalkyl; or C 1-3 phenyl optionally substituted with up to three substituents independently selected from alkyl; or R 1 and R 2 These, together with the nitrogen atom to which they are attached, form C 1-3 The alkyl group may be a morpholinyl, pyrrolidinyl, piperidinyl, or azepanyl ring, each of which may be optionally substituted with up to three substituents independently selected from alkyl.

[0032] In a preferred embodiment, R of the lactamide compound of formula I 1 and R 2are each independently hydrogen or C 1-6 Alkyl, more preferably hydrogen or C 1-3 It can be an alkyl, such as lactic acid dimethylamide or lactic acid diethylamide.

[0033] The composition of the present invention can contain 10% to 90% by weight of a lactamide compound, preferably 20% to 80% by weight of a lactamide compound, and more preferably 30% to 70% by weight of a lactamide compound, based on the total weight of the composition.

[0034] The composition of the present invention may further comprise (e) an ether-type solvent.

[0035] The ether type solvent can be selected from dialkyl ethers, dialkylamide ethers, glycol ethers, aliphatic ethers, and cyclic ethers.

[0036] For example, the ether type solvent can be methyl-5-(dimethylamino)-2-methyl-5-oxopentanoate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, diethylene glycol monophenyl ether, tetrahydrofuran, or dibutyl ether.

[0037] The composition of the present invention can contain 1 wt % to 70 wt % of an ether type solvent, preferably 1 wt % to 60 wt % of an ether type solvent, and more preferably 10 wt % to 50 wt % of an ether type solvent, based on the total weight of the composition.

[0038] When the composition comprises a lactamide compound as defined in the present invention, the amount of ether type solvent is preferably less than the amount of the lactamide compound.

[0039] In certain embodiments of the present invention, particularly for forming a dispersible concentrate (DC), the composition comprises: (a) isocycloceram, which is present in an amount of 0.01% to 70% by weight, preferably 0.1% to 50% by weight, preferably 1% to 30% by weight, more preferably 5% to 20% by weight, based on the total weight of the composition; (b) a lignin compound, the lignin compound being present in an amount of 0.01% by weight to 30% by weight, preferably 0.1% by weight to 20% by weight, more preferably 0.1% by weight to 10% by weight, based on the total weight of the composition; (c) optionally, an acrylic graft copolymer, wherein the acrylic graft copolymer is present in an amount of from 0.01% to 30% by weight, preferably from 0.1% to 20% by weight, more preferably from 0.1% to 10% by weight, based on the total weight of the composition; (d) optionally, a lactamide compound, which is present in an amount of from 10% to 90% by weight, preferably from 20% to 80% by weight, more preferably from 30% to 70% by weight, based on the total weight of the composition; and (e) optionally, an ether type solvent, the ether type solvent being 1% by weight to 70% by weight, preferably 1% by weight to 60% by weight, more preferably 10% by weight to 50% by weight, based on the total weight of the composition; may include.

[0040] In said particular embodiment, the isocycloceram, the lignin compound, the acrylic graft copolymer, the lactamide compound, and the ether type solvent are compounds described herein.

[0041] The composition of the present invention may further comprise one or more formulation additives that are well known in the art. In particular, the formulation additives can be selected from antifreeze agents, antifoam agents, antimicrobial agents (or biocides), viscosity modifiers (or thickeners), pH modifiers, and any mixtures thereof. More preferably, the formulation additives can be selected from antifoam agents, pH adjusters, and any mixtures thereof.

[0042] Other suitable formulation additives include antioxidants, emulsifiers, colorants (or pigments), fragrances, adjuvants, attractants, buffers, coatings, deodorants, emetics, inorganic fillers, emollients, organic solvents, light protectants, and any mixtures thereof, among others known to those skilled in the art.

[0043] The compositions of the invention may contain one or several of the above mentioned formulation additives in suitable amounts to obtain the respective properties where appropriate.

[0044] The compositions of the present invention may further comprise an additional pesticide, which may be an insecticide, a fungicide, a herbicide, a synergist, a plant growth regulator, a nematicide, a plant nutrient, a plant fertilizer, and mixtures thereof.

[0045] The compositions of the invention may contain one or several of the above mentioned additional pesticides in suitable amounts to obtain the respective properties where appropriate.

[0046] For example, additional pesticides are: acibenzolar-S-methyl, metalaxyl M, metalaxyl, picarbutrazox, oxathiapiproline, ethaboxam, fludioxonil, azoxystrobin, thiabendazole, difenoconazole, tebuconazole, ipconazole, mefentrifluconazole, prothioconazole, triticonazole, sedaxane, impirfluxam, penflulen, fluopyram, fluxapyroxad, pydifulmetofen, cylobutrifluram, thiamethoxam, isoflucypyram, chlothianidin, benzovindiflupyr, cymoxanil, phosphites (phosphonates), silthiofam, pyraclostrobin, isotianil, tolprocarb, quinofumelin, Ipflufenoquine, methyltetraprole, florylpicoxamide, fenpicoxamide, fluoxythioconazole, flindapyr, isoflucipram, fluoxapiproline, broflanilide, imidacloprid, acetamiprid, cyantraniliprole, chlorantraniliprole, tetraniliprole, fluxamethamide, penthiopyrad, mandipropamide, ginpropyridaz , flupirimine, triflumezopyrim, oxazosulfil, diclobentizox, benzpirimoxan, hymexazole, pyrapropoin, cyclaniliprole, mandestrobin, copper agents, lambda-cyhalothrin, fenamacril, abamectin, tefluthrin, picoxystrobin, spiropydione, oligosaccharin, tea tree (Melaleuca alternifolia) alternifolia), fosthiazate, fenamifos, oxamyl, fluensulfone, fluazanindolizine, spirotetramat, spidoxamat, fluazinam, indazapiroxamet, thiophanate methyl, zoxamide, fluoxastrobin, pirimifos, tetrachlorantraniliprole, bifenthrin, and emamectin.

[0047] In another object of the present invention, the composition may advantageously be used to prepare a dispersible concentrate (DC).

[0048] In certain embodiments, the compositions of the present invention may comprise: - concentrates designed for addition to agricultural workers' water spray tanks or that can be applied directly without further dilution; or - In the farmer's water spray tank, a suspension is produced when the concentrate is mixed with the water in the spray tank.

[0049] In another object of the present invention, the present invention relates to a method for combating and / or controlling animal pests, comprising the step of applying to the pests, to their habitat or to plants susceptible to attack by pests a composition according to the invention.

[0050] The animal pest may be an invertebrate pest such as an insect, acarid, nematode or mollusc.

[0051] The term "plant" as used herein includes seedlings, shrubs and trees.

[0052] The compositions according to the invention can be used in particular to combat and / or control (i.e. contain or destroy) pests of the above-mentioned types occurring in plants, in particular plants useful in agriculture, horticulture and forestry and ornamental plants, or in organs of such plants, such as the fruits, flowers, foliage, stems, tubers or roots, and in some cases even plant organs formed at a later time point remain protected against these pests.

[0053] Suitable target crops are in particular cereals such as wheat, barley, rye, oats, rice, maize (e.g. fodder maize, popcorn, corn), millet or sorghum; beets such as sugar or fodder beets; fruits such as pome fruits, stone fruits or soft fruits, e.g. apples, pears, plums, peaches, almonds, cherries, or berries, e.g. strawberries, raspberries or blackberries; beans, lentils, peas or soybeans (soya beans, etc.). legumes such as rapeseed, mustard, poppy, olive, sunflower, coconut, castor, cocoa or peanut; cucurbits such as pumpkin, cucumber, melon, watermelon or squash; fibre 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, eggplant, pepper or bell pepper; Lauraceae such as avocado, cinnamon or camphor; and tobacco, nuts, coffee, sugarcane, tea, grapes, hops, plantain and latex plants.

[0054] In this method, the composition is generally applied with an effective amount of isocycloceram.

[0055] More preferably, the method is applied to spraying of the composition of the invention, for example delivered from a spray container.

[0056] The method allows for the application of an effective amount of the composition in a volume of 0.01 to 5 liters per hectare (L / ha), and more preferably 0.02 to 3.0 L / ha.

[0057] In another object of the present invention, the composition can be a seed treatment formulation or, in other words, plant propagation material can be treated with the composition according to the invention. The term "plant propagation material" is understood to refer to all reproductive parts of a plant, such as seeds, including asexually propagated plant material, such as cuttings, that can be used for its propagation. Plant propagation material can include seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes, plant parts. The plant propagation material can be treated with the composition according to the invention before sowing or planting the material. Alternatively, the plant propagation material can be treated with the composition according to the invention during sowing or planting. The composition according to the invention can also be applied to already treated propagation material before or during its planting. The composition according to the invention can be applied during sowing of the seeds. The composition can also be used on plant propagation material from plants grown in greenhouses and / or plants during transplanting. The seed treatment formulation may be applied in an amount ranging from 10 mg to 1 g of active substance (isocycloceram) per kg of seed, preferably from 10 mg to 500 mg of active substance (isocycloceram) per kg of seed, and more preferably from 10 mg to 100 mg of active substance (isocycloceram) per kg of seed.

[0058] In another aspect of the present invention, the compositions may also be used as an animal health treatment.

[0059] The following non-limiting examples illustrate the improved performance associated with compositions according to the present invention. The compounds used in the following examples are detailed below. - Isocycloceram is an insecticide with the CAS number: 2061933-85-3; - lignin compound 1 is the product Indulin AT (CAS number: 8068-05-1) offered by Ingevity, which is a kraft lignin with an average molecular weight of 2700 g / mol; - lignin compound 2 is the product Borresperse NA (CAS number: 8061-51-6) offered by Borregaard, which is a lignosulfonate with an average molecular weight of 20000 g / mol; - the copolymer is the product Agrilan 755 offered by Nouryon, which contains 30% by weight of an acrylic graft copolymer, 50% by weight of propylene glycol and 20% by weight of water; - the lactamide compound is the product Agnique AMD 3L (CAS number: 35123-06-9) offered by BASF; - The ether solvent is the product Rhodiasolv Polarclean (CAS number: 1174627-68-9) offered by Solvay.

[0060] The concentrations of the components used in Examples 1-4 are summarized in Table 1 and are expressed as a percentage by weight (% w / w) relative to the total weight of the composition. EXAMPLES

[0061] Examples 1-4 are prepared as follows: the required amount of lactamide compound and ether solvent are weighed into a suitable container and mixed until homogeneous. The required amount of isocycloceram is then added with stirring and allowed to stand until the isocycloceram is visually dissolved. The mixture can optionally be heated to 40°C to increase the rate of dissolution. The acrylic graft copolymer and lignin compound are then added with continued stirring and allowed to stand until the blend is homogeneous and cooled back to ambient temperature (25°C) if necessary.

[0062] [Table 1]

[0063] Table 2 summarizes the results based on the following assessments: - Dissolution: After the formulation is prepared, the sample is visually inspected to determine if all solids in the formulation are completely dispersed. This test determines if the lignin compounds are completely dispersed in the formulation. Undispersed lignin compounds are observed as brown / black particulate matter. - Dilution Properties: The dilution properties of the formulations were evaluated according to CIPAC MT180 method by varying the type of water, temperature and dilution ratio as shown in the table below. In this test, both the opacity of the dilution and the amount of sediment were recorded. Dilution stability is good if less than 0.1 ml of sediment is present after the dispersible concentrate formulation is left undisturbed for 24 hours.

[0064] [Table 2]

Claims

1. (a) Isocycloceram and (b) Lignin compounds with an average molecular weight of 10,000 g / mol or less A composition containing the following:

2. The composition according to claim 1, characterized in that the lignin compound has an average molecular weight of 5000 g / mol or less.

3. The composition according to claim 1, characterized in that the lignin compound has an average molecular weight of at least 1000 g / mol.

4. The composition according to claim 1, characterized in that the lignin compound is Kraft lignin.

5. The composition according to claim 1, characterized in that the lignin compound is unsulfonated lignin.

6. The composition according to claim 1, characterized in that it contains 0.01% to 70% by weight of isocycloceramic, preferably 0.1% to 50% by weight of isocycloceramic, preferably 1% to 30% by weight of isocycloceramic, and more preferably 5% to 20% by weight of isocycloceramic, based on the total weight of the composition.

7. The composition according to claim 1, characterized in that it contains 0.01% to 30% by weight of the lignin compound, preferably 0.1% to 20% by weight of the lignin compound, and more preferably 0.1% to 10% by weight of the lignin compound, based on the total weight of the composition.

8. The composition according to claim 1, further comprising (c) an acrylic graft copolymer.

9. The composition according to claim 8, characterized in that it contains 0.01% to 30% by weight of the acrylic graft copolymer, preferably 0.1% to 20% by weight of the acrylic graft copolymer, and more preferably 0.1% to 10% by weight of the acrylic graft copolymer, based on the total weight of the composition.

10. The composition according to claim 1, further comprising (d) a lactamide compound.

11. The composition according to claim 10, characterized in that it contains 10% to 90% by weight of the lactamide compound, preferably 20% to 80% by weight of the lactamide compound, and more preferably 30% to 70% by weight of the lactamide compound, based on the total weight of the composition.

12. The composition according to claim 1, further comprising (e) an ether-type solvent.

13. The composition according to claim 12, characterized in that it contains 1% to 70% by weight of the ether-type solvent, preferably 1% to 60% by weight of the ether-type solvent, and more preferably 10% to 50% by weight of the ether-type solvent, based on the total weight of the composition.

14. (a) Isocycloceram, (b) Lignin compounds having an average molecular weight of 10,000 g / mol or less, (c) Acrylic graft copolymer, (d) Lactoamide compounds, and (e) Ether-type solvents A composition containing the following:

15. The composition according to claim 1, characterized in that it is used for preparing a dispersible concentrate.

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.

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