Formulation

Abstract

The present invention relates to a composition comprising: (a) isoxtolfenpyrad, and (b) a lignin compound having an average molecular weight of up to 10000 g / mol.

Description

[0001] The present invention relates to a composition comprising isocycloseram. More particularly, the invention relates to formulations, such as dispersible concentrates; to dilutions of such formulations, more particularly in a farmer's spray tank; and to the use of such compositions for combating and / or controlling animal pests.

[0002] Isotriazole is an insecticide agricultural chemical. However, it has been found that conventional formulation methods for such active ingredients have many problems, such as the difficulty in stabilizing the formulations when diluted, because the use of water-miscible solvents promotes the crystal growth of active ingredients with low water solubility, and these formulations are generally not very tolerant to changes in conditions, such as changes in parameters such as dilution rate, temperature and water quality.

[0003] The object of the present invention is to overcome the problems of the prior art by proposing a composition comprising isoxathiapiprolin which has a stable dilution while ensuring good solubility, especially at 100 g / l of isoxathiapiprolin.

[0004] To this end, the object of the present invention is to provide a composition comprising:

[0005] (a) isoxathiapiprolid, and

[0006] (b) Lignin compounds having an average molecular weight of up to 10 000 g / mol.

[0007] Thanks to the combination of the lignin compound and isoxathiapiprolin, all of the above problems have been overcome.

[0008] Isotrione is an insecticidal agricultural chemical with the following CAS number: 2061933-85-3 and has the following chemical formula:

[0009]

[0010] Isoxafenamide may include 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 No.: 1309959-62-3), 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-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)- 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 isoxathiapiprolin further comprises at least one isomer selected from isomer (5S, 4S), isomer (5R, 4R), isomer (5R, 4S), and any combination thereof, isoxathiapiprolin may comprise a molar proportion of isomer (5S, 4R) greater 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).

[0011] The composition according to the invention may contain 0.01% to 70% by weight of isoxathiapyr, preferably 0.1% to 50% by weight of isoxathiapyr, preferably 1% to 30% by weight of isoxathiapyr, and more preferably 5% to 20% by weight of isoxathiapyr, relative to the total weight of the composition.

[0012] The lignin compound according to the present invention may have an average molecular weight of up to 5000 g / mol. In a preferred embodiment, the lignin compound may have an average molecular weight of at least 1000 g / mol.

[0013] In the present invention, the expression "average molecular weight" means a molecular weight of approximately ... The molecular weight, or in other words the molar mass, of a lignin compound can be easily determined by methods well known in the art, such as gel permeation chromatography (GPC).

[0014] The lignin compound according to the invention may more particularly be kraft lignin.

[0015] In another specific embodiment, the lignin compound may be unsulfonated lignin. In a preferred embodiment, the lignin compound may be unsulfonated kraft lignin.

[0016] Unsulfonated kraft lignin can be defined as lignin separated from cellulose using the kraft process (also known as the kraft process), i.e., separated using sodium hydroxide (NaOH) and sodium sulfide (Na2S). Unlike lignin produced via the acid sulfite process, unsulfonated lignin is produced using this process.

[0017] The composition according to the invention may comprise 0.01 to 30% by weight of lignin compounds, preferably 0.1 to 20% by weight of lignin compounds and more preferably 0.1 to 10% by weight of lignin compounds relative to the total weight of the composition.

[0018] The composition according to the present invention may further comprise (c) an acrylic graft copolymer.

[0019] The acrylic graft copolymer typically has a comb-like or star-like structure, and preferably a comb-like structure.

[0020] A graft copolymer is a branched copolymer in which the components forming the side chains are structurally different from the components forming the main chain.

[0021] Comb polymers comprise a main chain (backbone) containing branching points, from each of which emanate linear side chains.

[0022] Star polymers contain a multifunctional center from which at least three polymer chains radiate.

[0023] In a preferred embodiment, the acrylic graft copolymer may be an amphiphilic copolymer.

[0024] More particularly, the acrylic graft copolymer comprises at least one component A (hydrophilic part), which is soluble by the aqueous medium, and at least one other component B, which is hydrophobic.

[0025] Suitable acrylic graft copolymers may include polyethylene glycol, monomethyl ether of polyethylene glycol, poly(vinyl pyrrolidone), 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.

[0026] Such acrylic graft copolymers can be prepared, for example, by converting the monomethyl ether of polyethylene glycol into an acrylate or methacrylate, which is then subjected to free radical polymerization together with other unsaturated monomers such as styrene, ethyl acrylate, or methyl methacrylate. It is also possible to prepare such acrylic graft copolymers 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.

[0027] More preferably, the acrylic graft copolymer is a nonionic polymer, and more particularly has a comb-like structure.

[0028] In the present invention, the acrylic graft copolymer may contain polyethylene glycol and / or monoether polyethylene glycol side chains.

[0029] The acrylic graft copolymer may also comprise a backbone derived from acrylate and / or methacrylate monomers.

[0030] Even more preferably, the acrylic graft copolymer may comprise a backbone obtained from acrylate and / or methacrylate monomers and side chains comprising polyethylene glycol and / or monoether polyethylene glycol, so as to more particularly impart a comb-like structure to the polymer.

[0031] For example, the acrylic graft copolymer of the present invention can be Agrilan 755 supplied by Nouryon, Atlox 4913 supplied by CRODA, or TM , or Tersperse 2500 supplied by HUNTSMAN TM .

[0032] The composition according to the invention may contain 0.01 to 30% by weight of acrylic graft copolymer, preferably 0.1 to 20% by weight of acrylic graft copolymer and more preferably 0.1 to 10% by weight of acrylic graft copolymer relative to the total weight of the composition.

[0033] The composition according to the present invention may further comprise (d) a lactamide compound.

[0034] The lactamide compound may more particularly have the formula I

[0035] CH3CH(OH)C(=O)NR1R2(I)

[0036] wherein R1 and R2 are each independently hydrogen; or C 1-6 Alkyl, C 2-6 Alkenyl or C 3-6 cycloalkyl, each of which is optionally substituted by up to three independently selected groups consisting of phenyl, hydroxy, C 1-5 Alkoxy, morpholinyl and NR3R4 (wherein R3 and R4 are each independently C 1-3 alkyl) substituents; or phenyl, which is optionally substituted by up to three independently selected C 1-3 or R1 and R2 together with the nitrogen atom to which they are attached form a morpholinyl, pyrrolidinyl, piperidinyl or azepanyl ring, each of which is optionally substituted by up to three independently selected C 1-3 The alkyl group is substituted with a substituent.

[0037] In a preferred embodiment, R1 and R2 of the lactamide compound of formula I can each independently be hydrogen or C 1-6 alkyl, and more preferably hydrogen or C 1-3 Alkyl groups, such as lactic acid dimethylamide or lactic acid diethylamide.

[0038] The composition according to the invention may comprise 10 to 90% by weight of lactamide compounds, preferably 20 to 80% by weight of lactamide compounds and more preferably 30 to 70% by weight of lactamide compounds relative to the total weight of the composition.

[0039] The composition according to the present invention may further comprise (e) an ether type solvent.

[0040] The ether type solvent may be selected from dialkyl ethers, dialkylamide ethers, glycol ethers, aliphatic ethers, and cyclic ethers.

[0041] For example, the ether type solvent may 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.

[0042] The composition according to the present invention may contain 1 to 70% by weight of ether type solvents, preferably 1 to 60% by weight of ether type solvents and more preferably 10 to 50% by weight of ether type solvents relative to the total weight of the composition.

[0043] When the composition comprises a lactamide compound as defined in the present invention, the amount of the ether type solvent is preferably lower than the amount of the lactamide compound.

[0044] In a specific embodiment of the present invention, especially to form a dispersible concentrate (DC), the composition may comprise:

[0045] (a) 0.01% to 70% by weight of isoxathiapyr, preferably 0.1% to 50% by weight of isoxathiapyr, preferably 1% to 30% by weight of isoxathiapyr, and more preferably 5% to 20% by weight of isoxathiapyr relative to the total weight of the composition;

[0046] (b) 0.01% to 30% by weight of lignin compounds, preferably 0.1% to 20% by weight of lignin compounds, and more preferably 0.1% to 10% by weight of lignin compounds relative to the total weight of the composition;

[0047] (c) optionally, 0.01% to 30% by weight of an acrylic graft copolymer, preferably 0.1% to 20% by weight of an acrylic graft copolymer, and more preferably 0.1% to 10% by weight of an acrylic graft copolymer relative to the total weight of the composition;

[0048] (d) optionally, 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 relative to the total weight of the composition; and

[0049] (e) Optionally, 1 to 70% by weight of an ether type solvent, preferably 1 to 60% by weight of an ether type solvent, and more preferably 10 to 50% by weight of an ether type solvent relative to the total weight of the composition.

[0050] In the specific embodiment, isoxathiapiprole, the lignin compound, the acrylic graft copolymer, the lactamide compound and the ether solvent are the compounds described in the present specification.

[0051] The composition of the present invention may further comprise one or more formulation additives well known in the art. In particular, the formulation additive may be selected from antifreeze agents, defoamers, antibacterial agents (or biocides), viscosity modifiers (or thickeners), pH modifiers, and any mixtures thereof. More preferably, the formulation additive may be selected from defoamers, pH modifiers, and any mixtures thereof.

[0052] Other suitable formulation additives include, in particular, antioxidants, emulsifiers, colorants (or pigments), fragrances, adjuvants, attractants, buffers, coating agents, deodorants, emetics, inorganic fillers, safeners, organic solvents, light protectants, and any mixtures thereof known to those skilled in the art.

[0053] The composition of the present invention may contain one or more of the above-mentioned one or more formulation additives in appropriate amounts to obtain corresponding properties as appropriate.

[0054] The composition of the present invention may further comprise additional agricultural chemicals. The additional agricultural chemicals may be insecticides, fungicides, herbicides, synergists, plant growth regulators, nematicides, plant nutrients, plant fertilizers, and mixtures thereof.

[0055] The composition of the present invention may contain one or more of the above-mentioned additional agricultural chemicals in suitable amounts to obtain corresponding properties where appropriate.

[0056] For example, the additional agrochemical may be selected from the group consisting of acibenzolar-s-methyl, metalaxyl-M, metalaxyl, tetrazolylpyrazone, fluthiazolin, ethaboxam, fludioxonil, azoxystrobin, thiabendazole, difenoconazole, tebuconazole, ipconazole, clofoconazole, prothioconazole, trichlorfon, sedaxane, inpyrfluxam, penflulen, fluopyram, fluopyram, pydifulmetofen, cylobutrifluram, thiamethoxam, isoflurane, chlothianidin, benzovinflumazole, cymoxanil, phosphites (phosphonates), silthiopyram, pyraclostrobin, isothiazine, tolprocarb, quinofumelin, ipflufenoquin, metyltetraprole, florylpicoxamid, fenpicoxamid, fluoxyt ioconazole), fluindapyr, isoflurane, fluoxapiprolin, broflanilide, imidacloprid, acetamiprid, cyantraniliprole, chlorantraniliprole, tetrazobactam, fluoxazolidinone, penthiopyrad, dimethomorph, dimpropyridaz, flupyrimin, triflumezopyrim, oxa zosulfyl), dichlobentiazox, benzpirimoxan, oxamexazole, pyrapropoyne, cyclobromofenamide, mandestrobin, copper, lambda-cyhalothrin, cyproconazole, avermectin, tefluthrin, picoxystrobin, spiropidion, oligosaccharins, Melaleuca alternifoliaalternifolia, thiathioate, fenamifos, oxamyl, fluensulfone, fluazanindolizine, spirotetramat, spidoxamat, fluazinam, indazapyroxamet, thiophanate methyl, zoxamide, fluoxastrobin, pirimifos, tetrachlorantraniliprole, bifenthrin, and emamectin.

[0057] In another object of the present invention, the composition can be advantageously used for the preparation of dispersible concentrates (DC).

[0058] In a specific embodiment, the composition of the present invention may involve:

[0059] - a concentrate which is designed for addition to a farmer's water spray tank, or which can be applied directly without further dilution, or

[0060] -Suspensions, which are produced in farmers' water spray tanks when the concentrate is mixed with water in the spray tank.

[0061] In another object of the invention, the present invention relates to a method for combating and / or controlling animal pests, which method comprises applying a composition according to the invention to the pests, to the locus of the pests, or to plants susceptible to attack by the pests.

[0062] The animal pest may be an invertebrate animal pest, such as an insect, acarine, nematode or mollusc.

[0063] The term "plant" as used herein includes seedlings, shrubs and trees.

[0064] The compositions according to the invention can be used for combating and / or controlling (i.e., suppressing or destroying) pests of the abovementioned type, which occur in particular on plants, especially on useful and ornamental plants in agriculture, in horticulture and in forestry, or on organs of such plants (such as fruits, flowers, leaves, stems, tubers or roots), and in some cases, even plant organs formed at a later point in time remain protected against these pests.

[0065] In particular, suitable target crops are cereals, such as wheat, barley, rye, oats, rice, corn (e.g., field corn, popcorn corn, corn), millet or sorghum; beets, such as sugar beets or fodder beets; fruits, such as pome, stone fruit or soft fruit, such as apples, pears, plums, peaches, apricots, cherries or berries (e.g., strawberries, raspberries or blackberries); leguminous crops, such as beans, lentils, peas or soybeans (soya / soya beans); beans); oil crops such as rapeseed, mustard, poppy, olive, sunflower, coconut, castor, cocoa beans or peanuts; melons such as pumpkin, cucumber, melon, watermelon or squash; fiber plants such as cotton, flax, hemp or jute; citrus fruits such as oranges, lemons, grapefruits or tangerines; vegetables such as spinach, lettuce, asparagus, cabbage, broccoli, cauliflower, carrots, onions, tomatoes, potatoes, eggplant, peppers or bell peppers; lauraceae such as avocado, cinnamon or camphor; and also tobacco, nuts, coffee, sugar cane, tea, grapevines, hops, plantaginaceae and latex plants.

[0066] In this method, the composition may generally be applied in an effective amount of isoxathiapiprolin.

[0067] More preferably, the method is applied to spraying the composition of the invention, for example dispensing from a spray container.

[0068] The method may involve applying an effective amount of the composition at a rate of 0.01 to 5 liters per hectare (L / ha), and more preferably 0.02 to 3.0 L / ha.

[0069] In another object of the present invention, the composition can be a seed treatment formulation, or in other words, plant propagation materials can 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, which can be used for the latter's proliferation, including vegetative plant materials, such as cuttings. Seeds (strictly speaking), roots, fruits, tubers, bulbs, rhizomes, parts of plants can be mentioned as plant propagation materials. Before sowing or planting the plant propagation material, the material can be treated with the composition of the present invention. Alternatively, during sowing or planting, the plant propagation material can be treated with the composition of the present invention. In addition, before or during the planting of propagation material, the composition of the present invention can be applied to previously treated propagation materials. The composition of the present invention can be applied during the sowing of seeds. The composition can also be used for plant propagation materials derived from plants grown in greenhouses and / or during transplanting. The seed treatment formulation may be applied at a rate ranging from 10 mg to 1 g of active substance (isoxathiapiprolin) per kg of seeds, preferably 10 mg to 500 mg of active substance (isoxathiapiprolin) per kg of seeds, and more preferably 10 mg to 100 mg of active substance (isoxathiapiprolin) per kg of seeds.

[0070] In another object of the present invention, the composition can also be used as an animal health treatment agent.

[0071] The following non-limiting examples demonstrate the improved behavior associated with the compositions according to the present invention.The compounds used in the following examples are detailed below.

[0072] - isoxathiapiprole is an insecticide under CAS number 2061933-85-3;

[0073] - Lignin compound 1 is the product Indulin AT (CAS No. 8068-05-1) supplied by Ingevity, which is kraft lignin with an average molecular weight of 2700 g / mol;

[0074] - Lignin compound 2 is the product Borresperse NA (CAS No. 8061-51-6) supplied by Borregaard, which is a lignin sulfonate with an average molecular weight of 20,000 g / mol;

[0075] - the copolymer is the product Agrilan 755 supplied by Nouryon, which contains 30% by weight of an acrylic graft copolymer, 50% by weight of propylene glycol, and 20% by weight of water;

[0076] - Lactamide compound is Agnique AMD 3L (CAS No.: 35123-06-9) supplied by BASF;

[0077] The ether solvent was Rhodiasolv Polarclean (CAS No. 1174627-68-9), a product supplied by Solvay.

[0078] The concentrations of the components of Examples 1-4, expressed as weight percent (% w / w) relative to the total weight of the composition, are collected in Table 1.

[0079] Examples 1-4 are prepared as follows: The desired amount of lactamide compound and ether solvent are weighed into a suitable container and mixed until uniform. The desired amount of isoxathiapiprolin is then added under mixing and left to stand until the isoxathiapiprolin has been visibly dissolved. Alternatively, the mixture may be heated to 40°C to accelerate dissolution. Then, still under mixing, the acrylic graft copolymer and lignin compound are added, and the formulation is stirred until uniform and, if necessary, cooled back to ambient temperature (25°C).

[0080]

[0081] Table 1

[0082] Table 2 collects the results based on the following evaluations:

[0083] - Dissolution: After the preparation of the formulation, the sample was visually inspected to determine whether all solid matter in the formulation had been fully dispersed. This test determines whether the lignin compound is fully dispersed in the formulation. The presence of undispersed lignin compounds is observed as brown / black particulate matter.

[0084] - Dilution characteristics: The dilution characteristics of the formulations were evaluated according to CIPAC method MT180 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. Dispersible concentrate formulations with good dilution stability present less than 0.1 ml of sediment after standing for 24 hours.

[0085] Table 2

[0086]

Claims

1. A composition comprising: (a) isoxathiapiprolid, and (b) Lignin compounds having an average molecular weight of up to 10 000 g / mol.

2. The composition according to claim 1, characterized in that The lignin compounds have an average molecular weight of up to 5000 g / mol.

3. A composition according to any one of the preceding claims, characterized in that The lignin compound has an average molecular weight of at least 1000 g / mol.

4. A composition according to any one of the preceding claims, characterized in that The lignin compound is kraft lignin.

5. A composition according to any one of the preceding claims, characterized in that The lignin compound is unsulfonated lignin.

6. A composition according to any one of the preceding claims, characterized in that It contains 0.01% to 70% by weight of isoxathiapyr, preferably 0.1% to 50% by weight of isoxathiapyr, preferably 1% to 30% by weight of isoxathiapyr, and more preferably 5% to 20% by weight of isoxathiapyr, relative to the total weight of the composition.

7. A composition according to any one of the preceding claims, characterized in that It comprises from 0.01% to 30% by weight of said lignin compounds, preferably from 0.1% to 20% by weight of said lignin compounds and more preferably from 0.1% to 10% by weight of said lignin compounds relative to the total weight of the composition.

8. A composition according to any one of the preceding claims, characterized in that The composition further comprises (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 relative to the total weight of the composition.

10. A composition according to any one of the preceding claims, characterised in that The composition further comprises (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 relative to the total weight of the composition.

12. A composition according to any one of the preceding claims, characterised in that The composition further comprises (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, relative to the total weight of the composition.

14. A composition comprising: (a) isoxathiapiprolin, (b) lignin compounds having an average molecular weight of up to 10 000 g / mol, (c) an acrylic graft copolymer, (d) a lactamide compound, and (e) Ether type solvents.

15. A composition according to any one of the preceding claims, characterised in that It is used to prepare dispersible concentrates.

16. A method of combating and / or controlling animal pests, the method comprising applying a composition according to any one of the preceding claims to the pests, to the locus of the pests, or to plants susceptible to attack by the pests.

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