Pesticide composition

Abstract

The present invention provides a co-crystal of sulfentrazone and a triazinone herbicide and a method for preparing the same. The present invention also provides a pesticide composition containing the co-crystal, a method for preparing the pesticide composition, and a method for controlling weeds using the composition.

Description

[Technical Field]

[0001] The present invention relates to a pesticide composition. More specifically, the present invention relates to a pesticide composition comprising a cocrystal of sulfenthrazone and a triazinon herbicide. [Background technology]

[0002] A cocrystal is a multi-component crystalline system formed by intermolecular interactions that do not involve the movement of hydrogen ions. A cocrystal or crystalline complex of an organic compound is a multi-component system containing at least two different organic compounds. Cocrystallization is an expression of directed self-assembly of different components.

[0003] A pesticide cocrystal can be defined as a crystalline material composed of two or more different active ingredients, or having one or more active substances together with other co-forming agents. These compounds can be formed by intermolecular forces such as hydrogen bonding, π-stacking, and van der Waals forces. Cocrystals can alter or enhance several important physicochemical properties of a substance, such as solubility, bioavailability, stability, hygroscopicity, surface free energy, zeta potential, crystal hardness, filterability, and flowability. These properties significantly affect pesticide formulations.

[0004] The use of pesticide compositions is a widely practiced and documented custom in the agricultural sector. These pesticide compositions offer significant advantages beyond individual applications, including improved long-term control, reduced application rates and costs, shorter contact times for improved results, less stringent use restrictions, improved selectivity, an improved spectrum of controlled fungi, insects, weeds, etc., and reduced residue issues.

[0005] However, the combined use of multiple active substances can lead to physical and biological incompatibility, such as a lack of physical stability in the co-formulation, degradation of the active substances, or antagonism of the active substances, and therefore should be approached with caution.

[0006] Triazinones are heterocyclic compounds with potential biological activity. Their primary mode of action is the inhibition of electron transport in photosystem II (Hill reaction).

[0007] Sulfenthrazone is a phenyltriazinon (also known as aryltriazinon) herbicide that acts by inhibiting protoporphyrinogen oxidase (protox). Sulfenthrazone mimics half of the tetrapyrrole ring of protoporphyrinogen (a substrate of Protox) and competes for the catalytic site on the enzyme. The active compound sulfenthrazone is also known to have a long-lasting effect (U.S. Patent No. 4,818,275), is absorbed by roots and leaves, and mainly moves to the apoplasum, restricting phloem movement. It is used to control annual broadleaf weeds of soybeans, sugarcane, and tobacco, as well as some grass and sedge species. It is applied as a pre-emergence or pre-plant incorporation.

[0008] Metrivudine is a triazinon herbicide that inhibits photosynthesis in susceptible plants by binding to proteins in the photosystem II complex, which ultimately leads to a series of events in which plant lipids and proteins are attacked and oxidized by highly reactive free radicals. The active compound metrivudine is known for its long-lasting action (U.S. Patent No. 3,905,801) and is used both pre-emergence and post-emergence, proving particularly useful for selective weed control in soybeans and potatoes.

[0009] In particular, liquid compositions of sulfenthrazone and triazinon herbicides (e.g., metrivudine) have been observed to form stable compositions, but the physical incompatibility of these two active substances can lead to unstable compositions. Such unstable compositions are unacceptable from the standpoint of formulation and applicability. During formulation, such liquid compositions may fail quality checks due to non-uniform dispersion. Furthermore, during application, such liquid compositions may not deliver a uniform concentration of the active substance to the field, potentially causing applicator nozzle clogging.

[0010] Therefore, there is a need to develop a stable system that allows sulfenthrazone to be formulated as a binary mixture with other triazinon herbicides. Furthermore, there is a need to develop a stable system in which sulfenthrazone and triazinon herbicides do not exhibit crystal growth when formulated together, and remain stable during formulation and storage.

[0011] Object of the invention An objective of the present invention is to provide a cocrystal of sulfenthrazone and a triazinon herbicide.

[0012] Another object of the present invention is to provide a pesticide composition of sulfenthrazone and a triazinon herbicide.

[0013] An objective of the present invention is to provide an agricultural chemical composition of sulfenthrazone and a triazinon herbicide that has long-term storage stability.

[0014] Another object of the present invention is to provide a pesticide composition containing a cocrystal of sulfenthrazone and a triazinon herbicide.

[0015] Another object of the present invention is to provide a pesticide composition containing a cocrystal of sulfenthrazone and metrivudine.

[0016] Another object of the present invention is to provide a process for preparing a pesticide composition containing a cocrystal of sulfenthrazone and a triazinon herbicide. [Overview of the project]

[0017] In one aspect of the present invention, a cocrystal of sulfenthrazone and a triazinon herbicide is provided.

[0018] In other aspects, the present invention provides a process for preparing cocrystals of sulfenthrazone and triazinon herbicides.

[0019] In other aspects, the present invention provides an agrochemical composition comprising a co-crystal of sulfentrazone and a triazinone herbicide.

[0020] In other aspects, the present invention provides a process for preparing an agrochemical composition comprising a co-crystal of sulfentrazone and a triazinone herbicide.

[0021] In other aspects, the present invention provides a process for preparing an agrochemical composition comprising a co-crystal of sulfentrazone and a triazinone herbicide, comprising: a) pretreating sulfentrazone and a triazinone herbicide to form a co-crystal; and b) optionally mixing the co-crystal of step (a) with an agrochemical excipient to obtain a mixture; and c) further treating the obtained mixture of step (b) to obtain the composition. A process is provided.

[0022] In one aspect of the present invention, there is provided a process for preparing a liquid agrochemical composition comprising a co-crystal of sulfentrazone and a triazinone herbicide, comprising: a) pretreating sulfentrazone and a triazinone herbicide to form a co-crystal; and b) optionally mixing the co-crystal of step (a) with an agrochemical excipient in aqueous conditions to obtain a mixture; and c) further treating the obtained mixture of step (b) to obtain the composition. A process is provided.

[0023] In still other aspects of the present invention, the agrochemical composition comprises a co-crystal of sulfentrazone and metribuzin.

[0024] In other aspects of the present invention, there is provided an agrochemical composition comprising a co-crystal of sulfentrazone and metribuzin, wherein the composition comprises 10-90 wt% of sulfentrazone and 90-10 wt% of metribuzin.

[0025] In another aspect of the present invention, an agrochemical composition comprising a cocrystal of sulfenthrazone and metrivudine, wherein the cocrystal exhibits at least one characteristic XRD reflection at 2θ values ​​(±0.2) of 7.8°, 11.8°, 14.1°, 17.8°, 22.1°, 23.4°, and 24.4°.

[0026] In one aspect of the present invention, a cocrystal of sulfenthrazone and metrivudine is provided.

[0027] In another aspect of the present invention, the following method: i. Solution crystallization, ii. Dry grinding, iii. Solvent droplet pulverization technology, iv. Melt crystallization, or v. Mix sulfenthrazone and triazinon herbicides under aqueous conditions, followed by supplying energy. A process for preparing a cocrystal of sulfenthrazone and metrivudine by using one of the following methods.

[0028] In yet another aspect of the present invention, a process for preparing a pesticide composition comprising a cocrystal of sulfenthrazone and metrivudine, a) A step of pretreatment with sulfenthrazone and metrivudine to form a cocrystal; b) a step of mixing the cocrystal from step (a) with a pesticide excipient to obtain a mixture, if necessary; and c) A step of further processing the mixture obtained in step (b) to obtain the composition A process including the following is provided.

[0029] In another aspect of the present invention, a process for preparing a liquid pesticide composition comprising a cocrystal of sulfenthrazone and metrivudine, (a) A step of pre-treating sulfenthrazone and metrivudine to form a cocrystal; (b) A step of mixing the cocrystal from step (a) with an agricultural excipient in aqueous conditions to obtain the composition. A process including the following is provided.

[0030] Another aspect of the present invention is a method for controlling weeds, comprising applying a composition containing a cocrystal of sulfenthrazone and a triazinon herbicide in an effective amount for weed control to a plant or its habitat, plant seeds, or soil.

[0031] Another aspect of the present invention is a method for controlling weeds, comprising applying a composition containing a cocrystal of sulfenthrazone and metrivudine in an effective amount for herbicidal control to a plant or its habitat, plant seeds, or soil.

[0032] Another aspect of the present invention provides the use of a liquid pesticide composition comprising a cocrystal of sulfenthrazone and a triazinon herbicide.

[0033] The present invention can be understood by referring to the following figures. [Brief explanation of the drawing]

[0034] [Figure 1] High-performance liquid chromatography (HPLC) chromatogram of a cocrystal of sulfenthrazone and metrivudine. [Figure 2] Fourier transform infrared (FTIR) spectrum of a cocrystal of sulfenthrazone and metrivudine. [Figure 3] Powder X-ray diffraction (P-XRD) diffractogram of a cocrystal of sulfenthrazone and metrivudine. [Figure 4] Differential scanning calorimetry (DSC) thermogram of a cocrystal of sulfenthrazone and metrivudine. [Figure 5] FTIR spectra of cocrystals of sulfenthrazone and metrivudine in a suspension concentrate. [Figure 6] P-XRD diffractogram of a cocrystal of sulfenthrazone and metrivudine in a suspension concentrate. [Figure 7] Single crystal structure (ball-stick model) of a cocrystal of sulfenthrazone and metrivudine. [Modes for carrying out the invention]

[0035] Detailed description of the invention Surprisingly, the inventors have found that a pesticide composition of sulfenthrazone and metrivudine can be formed when both active substances are pre-treated, including interactions between the two active substances, and further formulated using surfactants and other pesticide excipients. Such pre-treatment promotes intermolecular interactions between the active substances, resulting in the formation of a cocrystal of the two active substances. Such a pre-formed cocrystal can then be formulated into a desired product using surfactants and other pesticide excipients. Furthermore, the inventors have observed that when the pesticide composition is formulated as a liquid composition containing a cocrystal of sulfenthrazone and a triazinon herbicide, it does not suffer from the particle growth problems associated with liquid compositions, and they have also noted that the composition remains extremely stable during long-term storage.

[0036] In the context of this invention, the term "cocrystal" is defined as "a solid crystalline material composed of two or more molecules within the same crystal lattice." A cocrystal is also defined as a crystalline material composed of two or more different molecules in a defined stoichiometric ratio within the same crystal lattice, and bonded together by nonionic and noncovalent bonds.

[0037] Therefore, in one embodiment, the present invention provides a pesticide composition comprising a cocrystal of sulfenthrazone and a triazinon herbicide.

[0038] In one embodiment of the present invention, a pesticide composition is provided that includes a cocrystal of sulfenthrazone and a triazinon herbicide, comprising 10 to 90 wt% sulfenthrazone and 90 to 10 wt% triazinon herbicide.

[0039] In one embodiment of the present invention, the triazinon herbicide of the pesticide composition is selected from the group consisting of ametridione, amivudine, ethidine, hexazinone, isomethiodin, metamitron, metrivudine, and trifludimoxazine.

[0040] In one embodiment of the present invention, the triazinon herbicide is metamitron.

[0041] In one embodiment of the present invention, the triazinon herbicide is amivudine.

[0042] In a preferred embodiment of the present invention, the triazinon herbicide is metrivudine.

[0043] In one embodiment of the present invention, the sulfenthrazone in the pesticide composition containing a cocrystal of sulfenthrazone and a triazinon herbicide is sulfenthrazone in an amount of approximately 10 w / w% to approximately 90 w / w% of the total weight of the pesticide composition.

[0044] In one embodiment of the present invention, the sulfenthrazone in the pesticide composition containing a cocrystal of sulfenthrazone and a triazinon herbicide is sulfenthrazone in an amount of about 20 w / w% to about 80 w / w% of the total weight of the pesticide composition, preferably about 40 w / w% to about 60 w / w%.

[0045] In one embodiment of the present invention, the triazinon herbicide in the pesticide composition containing a cocrystal of sulfenthrazone and a triazinon herbicide is a triazinon herbicide present in an amount of approximately 10 w / w% to approximately 90 w / w% of the total weight of the pesticide composition.

[0046] In one embodiment of the present invention, the triazinon herbicide in the pesticide composition containing a cocrystal of sulfenthrazone and a triazinon herbicide is a triazinon herbicide in an amount of about 20 w / w% to about 80 w / w% of the total weight of the pesticide composition, preferably about 40 w / w% to about 60 w / w%.

[0047] According to one aspect of the present invention, a process for preparing a liquid pesticide composition comprising a cocrystal of sulfenthrazone and a triazinon herbicide, a) A step of pretreatment with sulfenthrazone and triazinon herbicides to form cocrystals; b) A step of mixing the cocrystal from step (a) with a pesticide excipient to obtain a mixture, if necessary; and c) A step of further processing the mixture obtained in step (b) to obtain the composition. A process including the following is provided.

[0048] Whereof used herein, the term “pretreatment” refers to a process that enables the formation of cocrystals before the sulfenthrazone and triazinon herbicides are incorporated into a pesticide composition.

[0049] In one embodiment of the present invention, the pretreatment includes grinding, pulverizing, or providing a suitable form of energy sufficient to enable the formation of cocrystals of sulfenthrazone and triazinon herbicides.

[0050] In one embodiment of the present invention, the pretreatment includes heating a mixture of sulfenthrazone and a triazinon herbicide to enable the formation of a cocrystal of sulfenthrazone and the triazinon herbicide.

[0051] In one embodiment of the present invention, the pretreatment includes subjecting a mixture of sulfenthrazone and triazinon herbicides to amorphous formation by crushing, melting, grinding or other suitable means, thereby enabling the formation of cocrystals of sulfenthrazone and triazinon herbicides.

[0052] In one embodiment of the present invention, a pretreatment of sulfenthrazone and triazinon herbicides is provided for a period of time sufficient to form a cocrystal.

[0053] According to another embodiment of the present invention, in a process for preparing a pesticide composition comprising a cocrystal of sulfenthrazone and a triazinon herbicide, the order in which the cocrystal and the pesticide excipient are mixed is not fixed and can be varied according to the preference of the formulater.

[0054] According to another embodiment of the present invention, in a process for preparing a pesticide composition comprising a cocrystal of sulfenthrazone and a triazinon herbicide, the mixture obtained in step (b) is subjected to a reduction in particle size by applying shear to the mixture of the cocrystal and the pesticide excipient. Apparatus suitable for this purpose includes apparatus that provides grinding operations, e.g., high-shear mixers such as ROSS HSM, Ultra-Turrax apparatus, and dissolvers, static mixers, e.g., systems with mixing nozzles, bead mills, vibratory mills, agitator bead mills, colloidal mills, cone mills, circulating mills (agitator ball mills with pin grinding systems), disc mills, annular chamber mills, double cone mills, sprocket dispersers or homogenizers, and other homogenizers.

[0055] According to another embodiment of the present invention, in a process for preparing a pesticide composition comprising a cocrystal of sulfenthrazone and a triazinon herbicide, the further processing step (c) can be carried out under ambient temperature conditions.

[0056] According to another embodiment of the present invention, in a process for preparing a pesticide composition comprising a cocrystal of sulfenthrazone and a triazinon herbicide, the further treatment in step (c) can be carried out under high-temperature conditions having a temperature of 40°C or higher, preferably 60°C or higher.

[0057] According to another embodiment of the present invention, in a process for preparing a pesticide composition comprising a cocrystal of sulfenthrazone and a triazinon herbicide, the further treatment in step (c) can be carried out under low-temperature conditions having a temperature of 40°C or lower, preferably 20°C or lower.

[0058] According to other embodiments of the present invention, the pesticide composition of the present invention can be formulated as a granular composition and a liquid composition.

[0059] In one embodiment, a process is provided for preparing a granular composition containing a cocrystal of sulfenthrazone and a triazinon herbicide.

[0060] In one embodiment of the present invention, a granular composition comprising a cocrystal of sulfenthrazone and a triazinon herbicide is a) A step of pretreatment with sulfenthrazone and triazinon herbicides to form a cocrystal; b) A step of mixing the cocrystal from step (a) with a pesticide excipient to form a mixture, if necessary; c) Optionally, crushing and crushing; a step of further granulating the mixture to obtain a granular composition. It is prepared by a process that includes [details omitted].

[0061] The process for granulating the mixture is not particularly limited. Suitable granulation processes include conventional processes described in the granulation techniques, such as spray drying, fluidized bed granulation, flocculation, pan granulation, and extrusion granulation.

[0062] In one embodiment of the present invention, a pesticide composition is provided comprising a cocrystal of sulfenthrazone and metrivudine in an amount of about 10% to about 40 w / w% of the total weight of the pesticide composition, about 1% to about 20% of a solvent, about 0.1% to about 20% of nonionic and anionic dispersants, about 0.1% to about 10% of a wetting agent, about 0.1% to about 10% of an antifoaming agent, and about 0.1% to about 30% of a thickening agent.

[0063] In one embodiment of the present invention, a pesticide composition is provided comprising a cocrystal of sulfenthrazone and metrivudine in an amount of about 10% to about 40 w / w% of the total weight of the pesticide composition, about 1% to about 20% of a diol, about 0.1% to about 20% of an acrylic polymer, about 0.1% to about 20% of an alkali-swelling polyacrylate, about 0.1% to about 10% of a polyalkylene glycol ether, about 0.1% to about 10% of a silicone defoamer, and about 0.1% to about 30% of a thickener.

[0064] The present invention relates to a process for preparing a liquid pesticide composition comprising a cocrystal of sulfenthrazone and a triazinon herbicide, (a) A step of providing a pretreatment to sulfenthrazone and triazinon herbicides to form cocrystals; (b) a step of mixing the cocrystal from step (a) with a pesticide excipient in aqueous conditions as necessary to obtain a mixture; and (c) A step of further processing the mixture obtained in step (b) to obtain the composition This includes processes related to the process.

[0065] In one embodiment of the present invention, the pretreatment includes grinding, pulverizing, or providing a suitable form of energy sufficient to enable the formation of cocrystals of sulfenthrazone and triazinon herbicides.

[0066] In one embodiment of the present invention, the pretreatment includes heating a mixture of sulfenthrazone and a triazinon herbicide under aqueous conditions to enable the formation of a cocrystal of sulfenthrazone and the triazinon herbicide.

[0067] In one embodiment of the present invention, the pretreatment includes subjecting a mixture of sulfenthrazone and triazinon herbicides to amorphous formation by grinding, melting, abrasion or other suitable means under aqueous conditions, thereby enabling the formation of cocrystals of sulfenthrazone and triazinon herbicides.

[0068] In one embodiment of the present invention, the mixing in step b) is carried out under aqueous conditions.

[0069] In one embodiment of the present invention, the process in step c) is carried out under aqueous conditions to obtain the desired product.

[0070] Preferred methods for carrying out steps b) and c) have been described above.

[0071] In one embodiment of the present invention, the pesticide composition comprises a cocrystal of sulfenthrazone and metrivudine.

[0072] In one embodiment of the present invention, a pesticide composition comprising a cocrystal of sulfenthrazone and metrivudine, wherein the composition comprises 10 to 90 wt% sulfenthrazone and 90 to 10 wt% metrivudine.

[0073] In one embodiment of the present invention, the sulfenthrazone in the pesticide composition containing a cocrystal of sulfenthrazone and metrivudine is sulfenthrazone in an amount of about 20 w / w% to about 80 w / w% of the total weight of the pesticide composition, preferably about 40 w / w% to about 60 w / w%.

[0074] In one embodiment of the present invention, the metrivudine in the pesticide composition containing a cocrystal of sulfenthrazone and metrivudine is approximately 20 w / w% to approximately 80 w / w% of the total weight of the pesticide composition, preferably approximately 40 w / w% to approximately 60 w / w% of metrivudine.

[0075] In another embodiment of the present invention, an agrochemical composition comprising a cocrystal of sulfenthrazone and metrivudine, wherein the cocrystal exhibits at least one characteristic XRD reflection at 2θ values ​​(±0.2) of 7.8°, 11.8°, 14.1°, 17.8°, 22.1°, 23.4°, and 24.4°.

[0076] In one embodiment of the present invention, the pesticide composition comprises a cocrystal of sulfenthrazone and metrivudine in an amount of about 10% to about 40 w / w% of the total weight of the pesticide composition, about 1% to about 20% of a solvent, about 0.1% to about 20% of nonionic and anionic dispersants, about 0.1% to about 10% of a wetting agent, about 0.1% to about 10% of an antifoaming agent, and about 0.1% to about 30% of a thickening agent, and the pesticide composition is formulated as a suspension concentrate.

[0077] In one embodiment of the present invention, the pesticide composition comprises a cocrystal of sulfenthrazone and metrivudine in an amount of about 10% to about 40 w / w% of the total weight of the pesticide composition, about 1% to about 20% of a diol, about 0.1% to about 20% of an acrylic polymer, about 0.1% to about 20% of an alkali-swellable polyacrylate, about 0.1% to about 10% of a polyalkylene glycol ether, about 0.1% to about 10% of a silicone defoamer, and about 0.1% to about 30% of xanthan gum, and the pesticide composition is provided as a suspension concentrate.

[0078] In another embodiment of the present invention, an agrochemical composition comprising a cocrystal of sulfenthrazone and metrivudine, wherein the cocrystal exhibits at least one characteristic XRD reflection at 2θ values ​​(±0.2) of 7.8°, 11.8°, 14.1°, 17.8°, 22.1°, 23.4°, and 24.4°.

[0079] In one embodiment of the present invention, the pesticide composition contains a cocrystal of sulfenthrazone and metrivudine, wherein the molar ratio of sulfenthrazone to metrivudine is 1:9 to 9:1.

[0080] In one embodiment of the present invention, the pesticide composition contains a cocrystal of sulfenthrazone and metrivudine, wherein the molar ratio of sulfenthrazone to metrivudine is 1:5 to 5:1.

[0081] In one embodiment of the present invention, the pesticide composition contains a cocrystal of sulfenthrazone and metrivudine, wherein the molar ratio of sulfenthrazone to metrivudine is generally 2:1 to 1:2, preferably 1.5:1 to 1:1.5, and particularly 1:1.

[0082] In one embodiment of the present invention, the pesticide composition contains a cocrystal of sulfenthrazone and metrivudine, wherein the molar ratio of sulfenthrazone to metrivudine is 1:9 to 9:1.

[0083] In one embodiment of the present invention, the pesticide composition contains a cocrystal of sulfenthrazone and metrivudine, wherein the molar ratio of sulfenthrazone to metrivudine is generally 2:1 to 1:2, preferably 1.5:1 to 1:1.5, and particularly 1:1.

[0084] In one aspect, the present invention provides a cocrystal comprising sulfenthrazone and at least one triazinon herbicide.

[0085] In one aspect of the present invention, a cocrystal of sulfenthrazone and metrivudine is provided.

[0086] In one embodiment, sulfenthrazone and metrivudine exist as cocrystals in a molar ratio of 2:1 to 1:2.

[0087] In another embodiment of the present invention, a cocrystal of sulfenthrazone and metrivudine is used, the cocrystal exhibiting at least one characteristic XRD reflection at 2θ values ​​(±0.2) of 7.8°, 11.8°, 14.1°, 17.8°, 22.1°, 23.4°, and 24.4°.

[0088] In one embodiment, the cocrystal is characterized by at least one of the following: i. Powder X-ray diffraction pattern containing at least one peak at diffraction angle 2θ values ​​of 7.8°, 11.8°, 14.1°, 17.8°, 22.1°, 23.4° and 24.4° (±0.2), or ii. A DSC thermogram containing an endothermic peak that starts at 107.3°C and reaches its peak at 110.5°C, or iii. Single crystal X-ray diffraction with lattice constants a=22.2825(4)Å, b=10.5240(2)Å, c=11.4659(2)Å, α=90°, β=93.5058°(7), and γ=90°.

[0089] In another embodiment of the present invention, the following method: i. Mix sulfenthrazone and triazinon herbicides under aqueous conditions, followed by supplying energy; ii. Solution crystallization, iii. Dry grinding, iv. Solvent droplet pulverization technology, v. Melt crystallization A process for preparing a cocrystal of sulfenthrazone and metrivudine by using one of the following methods.

[0090] In one embodiment of the present invention, a cocrystal of sulfenthrazone and metrivudine herbicide can be obtained by any conventional process known to those skilled in the art used to prepare such a cocrystal.

[0091] The present invention further provides a process for preparing cocrystals of sulfenthrazone and triazinon herbicides.

[0092] In one embodiment, a process is provided for preparing a cocrystal of sulfenthrazone and a triazinon herbicide, wherein the cocrystal is obtained by solution crystallization or grinding or heating or solvent droplet grinding or melt crystallization or mixing of sulfenthrazone and a triazinon herbicide under aqueous conditions.

[0093] In one embodiment of the present invention, a process for preparing a cocrystal of sulfenthrazone and metrivudine by mixing sulfenthrazone and metrivudine includes suspending sulfenthrazone and metrivudine in water, and then supplying sufficient energy to promote intermolecular interactions between sulfenthrazone and metrivudine.

[0094] In one embodiment of the present invention, a process for preparing a cocrystal of sulfenthrazone and metrivudine includes mixing sulfenthrazone and metrivudine under aqueous conditions, followed by supplying energy.

[0095] In one embodiment of the present invention, a process for preparing a cocrystal of sulfenthrazone and metrivudine includes preparing a solution of sulfenthrazone and a triazinon herbicide using an organic solvent, water, or a mixture of water and an organic solvent, and polishing or precipitation with a poor solvent to obtain the cocrystal of sulfenthrazone and the triazinon herbicide.

[0096] The solvent is selected from aliphatic alcohols, ketones, esters, ethers, polar protic solvents, polar aprotic solvents, halogenated solvents, aliphatic hydrocarbons, or aromatic hydrocarbons, and the poor solvent is selected from aliphatic or aromatic hydrocarbon solvents.

[0097] In one embodiment, a process for preparing a cocrystal of sulfenthrazone and metrivudine includes heating and melting a mixture of sulfenthrazone and a triazinon herbicide to obtain the cocrystal of sulfenthrazone and the triazinon herbicide.

[0098] In one embodiment of the present invention, a process for preparing a cocrystal of sulfenthrazone and metrivudine by solution crystallization comprises completely dissolving sulfenthrazone and metrivudine in a suitable solvent, and further inducing cocrystallization by cooling, evaporation, or precipitation.

[0099] In one embodiment, the solvent may be selected from aliphatic alcohols, ketones, esters, ethers, polar protic solvents, polar aprotic solvents, halogenated solvents, aliphatic hydrocarbons, or aromatic hydrocarbons.

[0100] In one embodiment, the solvent may be selected from methanol, ethanol, isopropyl alcohol, acetone, dichloromethane, dichloroethane, dichloropropane, trichloroethane, chloroform, and ethyl acetate.

[0101] In one embodiment of the present invention, cocrystallization induced by cooling includes separately preparing saturated solutions of sulfenthrazone and metrivudine at a high temperature. The two solutions are then combined at the same temperature and cooled to 0°C to 20°C, preferably 3°C to 8°C (e.g., 5°C). The cocrystals thus formed can be separated from the resulting suspension by conventional techniques (e.g., filtration).

[0102] In one embodiment of the present invention, the cocrystallization induced by evaporation includes partial or complete removal of the solvent by using commonly used evaporation techniques (e.g., heating or reduced pressure).

[0103] In one embodiment of the present invention, cocrystallization induced by precipitation involves the complete dissolution of sulfenthrazone and metrivudine in a suitable solvent. Crystallization is induced by reducing the solubility of the solutes by adding a solvent, such that the solubility of sulfenthrazone and metrivudine is preferably less than 10 g / l, and particularly less than 2 g / l, at room temperature (hereinafter referred to herein as the "poor solvent"). Convenient and suitable poor solvents are nonpolar solvents, such as n-hexane, n-heptane, diethyl ether, petroleum ether, 1,4-dioxane, cyclohexanone, toluene, or xylene.

[0104] In one embodiment of the present invention, a process for preparing a cocrystal of sulfenthrazone and metrivudine by dry grinding includes combining sulfenthrazone and metrivudine, followed by the application of shear force.

[0105] In one embodiment of the present invention, the dry grinding process for preparing a cocrystal of sulfenthrazone and metrivudine by applying shear force is preferably carried out at a temperature of at least 15°C, often at least 20°C, preferably at least 30°C, particularly at least 35°C, for example, at a temperature of 15°C to 80°C.

[0106] One embodiment of the present invention provides a process for preparing a cocrystal of sulfenthrazone and metrivudine by solvent droplet pulverization technology.

[0107] In one embodiment of the present invention, the process for preparing a cocrystal of sulfenthrazone and metrivudine by solvent droplet pulverization technology comprises an organic solvent or a mixture of water and an organic solvent, wherein sulfenthrazone and metrivudine have equivalent solubility.

[0108] Organic solvents of Group 1 and mixtures thereof with water are more preferred. In the mixture with water, the relative amounts of organic solvent to water can vary from 200:1 to 1:200 (v / v), and particularly from 1:5 to 1:100 (v / v).

[0109] The appropriate solvent is a polar organic solvent as defined above.

[0110] Organic solvents particularly suitable for use alone or in mixture with water are the alcohols (C1-C4 alkanols, e.g., methanol, ethanol, n-propanol, or isopropanol) mentioned above.

[0111] The solvent droplet milling process can be easily carried out by adding the solvent dropwise to a mixture of sulfenthrazone and metrivudine and applying shear force (for example, using a rotor stator mill).

[0112] The solvent droplet pulverization process is typically carried out at a temperature of at least 5°C, preferably at least 10°C, particularly at least 20°C, for example, 5 to 80°C, preferably 10 to 55°C, particularly 20 to 40°C.

[0113] The time required for cocrystal formation by the solvent droplet pulverization process depends on the temperature and type of solvent, but is generally 1 hour. In all cases, complete conversion is achieved after 1 week; however, complete conversion usually requires 24 hours or less.

[0114] In one embodiment of the present invention, a process for preparing a cocrystal of sulfenthrazone and metrivudine by melt crystallization includes heating a mixture of sulfenthrazone and metrivudine in a porcelain dish on a paraffin oil bath maintained at 200°C. Furthermore, the molten mass is incubated in a container containing 25 ml of water at 90°C using a water bath. The cocrystal thus obtained is dried overnight at room temperature and further analyzed for characterization.

[0115] In one embodiment of the present invention, a process for preparing a cocrystal of sulfenthrazone and metrivudine by mixing sulfenthrazone and metrivudine under aqueous conditions and subsequently supplying energy includes grinding the mixture of sulfenthrazone and metrivudine under aqueous conditions, optionally in the presence of other pesticide excipients, to enable cocrystal formation through interaction under aqueous conditions.

[0116] In one embodiment of the present invention, a process for preparing an agrochemical composition comprising a cocrystal of sulfenthrazone and metrivudine, a) A step of pretreatment with sulfenthrazone and metrivudine to form a cocrystal; b) a step of mixing the cocrystal from step (a) with a pesticide excipient to obtain a mixture, if necessary; and c) A step of further processing the mixture obtained in step (b) to obtain the composition This includes processes related to the process.

[0117] In one embodiment of the present invention, the pretreatment includes grinding, pulverizing, or providing a suitable form of energy sufficient to enable the formation of a cocrystal of sulfenthrazone and metrivudine.

[0118] In one embodiment of the present invention, the pretreatment includes heating a mixture of sulfenthrazone and metrivudine to enable the formation of a cocrystal of sulfenthrazone and a triazinon herbicide.

[0119] In one embodiment of the present invention, the pretreatment includes subjecting a mixture of sulfenthrazone and metrivudine to amorphous formation by grinding, melting, grinding or other suitable means, thereby enabling the formation of a cocrystal of sulfenthrazone and a triazinon herbicide.

[0120] In one embodiment of the present invention, the cocrystal thus formed in step (b) is then mixed with a suitable pesticide excipient to obtain a mixture, which is further processed to obtain a suitable form of pesticide composition.

[0121] Preferred methods for carrying out steps b) and c) have been described above.

[0122] In one embodiment, a process for preparing a pesticide composition comprising a cocrystal of sulfenthrazone and a triazinon herbicide: a) A step of pretreatment with sulfenthrazone and triazinon herbicides to form a cocrystal; b) A step of mixing the cocrystal from step (a) with an excipient that is pesticide-acceptable to obtain the composition. A process including the following is provided.

[0123] According to another embodiment of the present invention, a process for preparing a pesticide composition, a) A step of pre-treating the mixture by heating it and then cooling it to room temperature to obtain a cocrystal by sulfenthrazone and metrivudine; b) A step of mixing the cocrystal from step (a) with a pesticide excipient in the presence of water to obtain a homogeneous pesticide composition. A process including the following is provided.

[0124] Typically, this is a process for preparing a pesticide composition, a) A step of pre-treating sulfenthrazone and metrivudine to obtain a cocrystal by heating the mixture at a temperature in the range of approximately 70-80°C for 1 hour, and then cooling it to room temperature; b) A step of mixing the cocrystal from step (a) with a pesticide excipient in the presence of water under high shear, and adding one or more dispersants and / or wetting agents to obtain a slurry, c) Optionally, by maintaining the grinding temperature at 25°C or higher, the particle size can be reduced to the specified size, preferably 1 or less. 10 d 4 or less 50 d less than 10 90 and d 35 μm or less 100 A process of crushing the slurry to achieve, d) A step of mixing the slurry for about 1 hour to obtain a uniform pesticide composition. A process including the following is provided.

[0125] According to another embodiment of the present invention, a process for preparing a pesticide composition, a) A step of preparing an aqueous mixture of pesticide-suitable excipients to obtain a homogeneous solution, b) A step of adding metrivudine and sulfenthrazone to the homogeneous solution from step (a) to obtain a slurry; c) A step of optionally grinding the slurry, d) A step of heating the slurry from step (b) or (c) and cooling it to room temperature, e) Optionally, add other pesticide excipients to the slurry of step (d) and mix to obtain a homogeneous pesticide composition. A process including the following is provided.

[0126] According to one embodiment of the present invention, a process for preparing a pesticide composition, a) A step of preparing an aqueous solution of pesticide-appropriate excipients, preferably anionic and nonionic dispersants, and obtaining a homogeneous solution using a mixer under high shear, b) A step of adding metrivudine and sulfenthrazone to the homogeneous solution from step (a) to obtain a slurry; c) Arbitrarily, d less than or equal to 1 10 d 4 or less 50 d less than 10 90 and d 35 μm or less 100The process involves grinding the slurry to achieve the specified particle size and maintaining the grinding temperature at 25°C or higher; d) The step of heating the slurry from step (b) or (c) in the temperature range of 70-80°C, mixing for about 1 hour, and then cooling to room temperature; e) Optionally, add other pesticide excipients to the slurry of step (b) or (d) and mix to obtain a homogeneous pesticide composition. A process including the following is provided.

[0127] This process optionally includes a step following step (c) and after step (d) to achieve the particle size specification of step (c).

[0128] Step (e) includes preparing a thickening agent (2% solution) gel by adding Proxel GXL and Rhodopol23 to a container, mixing for 30 minutes, adding water, and continuing to mix for 1 hour.

[0129] In one embodiment of the present invention, the steps in the process for preparing a pesticide composition containing a cocrystal of sulfenthrazone and metrivudine are not fixed and may be in any order to achieve the pesticide composition according to the present invention.

[0130] In one embodiment of the present invention, the pesticide composition of the present invention may be in solid or liquid form.

[0131] According to a preferred embodiment, the pesticide composition of the present invention is a liquid formulation.

[0132] According to embodiments of the present invention, liquid pesticide compositions can be formulated as suspension concentrates (SC), emulsion concentrates (EW), oily suspension concentrates (OD), and / or suspension emulsions (SE).

[0133] According to a preferred embodiment of the present invention, the liquid pesticide composition is formulated as a suspension concentrate (SC).

[0134] The present invention is a process for preparing a liquid pesticide composition comprising a cocrystal of sulfenthrazone and metrivudine, (a) A step of pre-treating sulfenthrazone and metrivudine to form a cocrystal; (b) a step of mixing the cocrystal from step (a) with a pesticide excipient in aqueous conditions as necessary to obtain a mixture; and (c) A step of further processing the mixture obtained in step (b) to obtain the composition This includes processes related to the process.

[0135] In one embodiment of the present invention, the steps in the process for preparing a liquid pesticide composition containing a cocrystal of sulfenthrazone and metrivudine are not fixed and may be in any order to achieve the liquid pesticide composition according to the present invention.

[0136] In another embodiment of the present invention, the cocrystals of the liquid pesticide composition are obtained by “pretreatment,” which means a process that allows the sulfenthrazone and triazinon herbicides to form cocrystals before they are incorporated into the liquid pesticide composition.

[0137] In one embodiment of the present invention, the pretreatment of sulfenthrazone and metrivudine includes providing a suitable form of energy sufficient to enable grinding, pulverizing, heating, or the formation of a cocrystal of sulfenthrazone and metrivudine together.

[0138] In one embodiment, a slurry of pesticide excipients was first prepared and ground, then sulfenthrazone and metrivudine were added at a high temperature (54°C to 60°C) and ground together with the pesticide excipient slurry. Further processing was then carried out by adding a thickener to prepare a suspension concentrate.

[0139] In other embodiments, a slurry of pesticide excipients was first prepared, then sulfenthrazone and metrivudine were added at high temperature (54°C to 60°C), and then ground together with the pesticide excipient slurry. Further processing was carried out by adding a thickener to prepare a suspension concentrate.

[0140] In another embodiment, sulfenthrazone and metrivudine are mixed, ground, and then melted by applying heat (125°C to 140°C) to obtain a cocrystal. The cocrystal is then cooled and ground under grinding conditions. A separately prepared slurry of the pesticide excipient is then added to the mixture and ground again. Finally, further processing is performed by adding a thickener to produce a suspension concentrate.

[0141] In other embodiments, sulfenthrazone and metrivudine are mixed and ground to obtain a mixture. The mixture is dynamically heated (54°C to 70°C), and then a separately prepared slurry of pesticide excipients is added to the mixture and ground again. Finally, further processing is performed by adding a thickener to produce a suspension concentrate.

[0142] The present invention (a) Cocrystal of sulfenthrazone and triazinon herbicide; (b) Acrylates; and (c) Glycerol The present invention provides a liquid pesticide composition containing the following:

[0143] According to one embodiment of the present invention, the liquid pesticide composition comprises an acrylate polymer.

[0144] According to one embodiment of the present invention, the acrylate polymer is selected from the group consisting of polymers of methyl acrylate, methacrylate, ethyl acrylate, 2-chloroethyl vinyl ether, 2-ethylhexyl acrylate, hydroxyethyl methacrylate, butyl acrylate, butyl methacrylate, and trimethylolpropane triacrylate (TMPTA). Examples of acrylic polymers, but not limited to, include modified styrene / maleic anhydride copolymer (Envi-Pol 871), PAPI 27 polymer MDI, polymethyl methacrylate, polyacrylate, polyacrylate salts, such as sodium polyacrylate, poly(vinyl acetate) (PVAc), and polyacrylamide.

[0145] In one embodiment of the present invention, the liquid pesticide composition may further contain urea.

[0146] According to one embodiment of the present invention, the liquid pesticide composition contains an acrylate polymer in an amount of about 0.1 w / w% to about 40 w / w%, preferably about 0.1 w / w% to about 30 w / w%, of the total weight of the liquid pesticide composition.

[0147] According to a preferred embodiment of the present invention, the liquid pesticide composition contains about 1 w / w% to about 30 w / w%, preferably about 0.1 w / w% to about 30 w / w%, of glycerol by weight of the total weight of the liquid pesticide composition.

[0148] According to one embodiment of the present invention, the liquid pesticide composition contains water.

[0149] According to one embodiment of the present invention, the liquid pesticide composition contains about 0.1 w / w% to about 99 w / w%, preferably about 10 w / w% to about 70 w / w%, of water by weight of the total weight of the liquid pesticide composition.

[0150] In one embodiment of the present invention, the liquid pesticide composition may further comprise a pesticide excipient selected from one or more anionic and nonionic surfactants, antifreezes, wetting agents, fillers, surfactants, anti-solidification agents, pH adjusters, preservatives, biocides, defoamers, colorants, and other formulations or auxiliary agents.

[0151] Suitable anionic surfactants include polyacrylates, alkylbenzene sulfonates (e.g., TERWET 1004), such as dodecylbenzene sulfonate, such as calcium dodecylbenzene sulfonate, ethoxylated and / or propoxylated di- or tri-styrylphenol phosphates, ethoxylated and / or propoxylated di- or tri-styrylphenol sulfates, phenyl sulfonates, alkinaphthalene sulfonates, ethoxylated and / or propoxylated alcohol phosphate esters, ethoxylated and / or propoxylated alkylaryl phosphate esters, taurates, sulfosuccinates and polycarboxylates, sodium alkylnaphthalene sulfonate formalin condensates or modified styrene-maleic anhydride copolymers. Examples of commercially available sodium alkylnaphthalene sulfonate formalin condensates include Morwet D425, TERSPERSE 2020, and Agrosurf WG-2300. An example of a commercially available modified styrene-maleic anhydride copolymer is TERSPERSE 2612.

[0152] Suitable nonionic surfactants include alkoxylated surfactants and block copolymer surfactants. Useful examples of alkoxylated surfactants for the present invention include castor oil ethoxylate, tridecyl alcohol ethoxylate, nonylphenol ethoxylate, octylphenol ethoxylate, tristylphenol ethoxylate, phosphate ester ethoxylate, taloamine ethoxylate, cocoaamine ethoxylate, and oleylamine ethoxylate.

[0153] Suitable antifreeze agents that can be added to liquid pesticide compositions are liquid polyols, such as ethylene glycol and propylene glycol.

[0154] Suitable pH adjusters may be citric acid or phosphoric acid.

[0155] Wetting agents that can be added to the liquid pesticide composition of the present invention include, but are not limited to, polyarylalkoxylated phosphate esters and their potassium salts (e.g., Soprophor® FLK, Stepfac TSP PE-K). Other suitable wetting agents include sodium dioctyl sulfosuccinate (e.g., Geropon® SDS, Aerosol® OT) and ethoxylated alcohols (e.g., Trides-6; Rhodasurf® BC610; Tersperse® 4894).

[0156] Optionally, an antifoaming agent or antifoaming agent in an amount of about 0.1 wt% to about 5.0 wt% may be used to stop unwanted foaming that occurs during the preparation of the suspension concentrate composition of this application. Preferred antifoaming agents are selected from the group consisting of silicone compounds, alcohols, glycol ethers, mineral spirits, acetylenediol, polysiloxanes, organosiloxanes, siloxane glycols, reaction products of silicon dioxide and organosiloxane polymers, polydimethylsiloxanes, or polyalkylene glycols, either alone or in combination. Suitable defoaming agents include AGNIQUE DFM 111S; SAG-10; SAG-1000AP; SAG-1529; SAG-1538; SAG-1571; SAG-1572; SAG-1575; SAG-2001; SAG-220; SAG-290; SAG-30; SAG-30E; SAG-330; SAG-47; SAG-5440; SAG-7133 and SAG-770.

[0157] Examples of thickeners based on anionic heteropolysaccharides derived from xanthan gum groups include, in particular, Rhodopol23®, Rhodopol G®, Rhodopol50 MD®, Rhodicare T®, Kelzan®, Kelzan S®, and Satiaxane CX91®.

[0158] The preservatives used may be benzoisothiazolinone (Proxel GXL) or phenol, 2-bromo-2-nitropropane-1,3-diol, 5-chloro-2-methyl-4-isothiazolinone-3-one and 2-methyl-4-isothiazolinone-3-one (Kathon CG / ICP), glutaraldehyde (Ucarcide 50), chloromethylisothiazolinone (CMIT) / methylisothiazolinone (MIT) (Isocil Ultra 1.5), 2,2-dibromo-3-nitrilopropioamide (Reputain 20), natamycin & herring, bronopol / CMIT / MIT (Mergal 721K3).

[0159] Suitable colorants (e.g., red, blue, green) are preferably pigments that are poorly soluble in water and dyes that are water-soluble. Examples include inorganic colorants (e.g., iron oxide, titanium dioxide, and iron hexacyanoferrate) and organic colorants (e.g., alizarin, azo, and phthalocyanine colorants).

[0160] According to one embodiment of the present invention, the composition comprises a cocrystal of sulfenthrazone and metrivudine, and one or more pesticides other than the two components of the cocrystal.

[0161] Pest control agents may be selected from herbicides, fungicides, insecticides, nematicides, acaricides, plant growth regulators, and toxicity mitigators.

[0162] Preferably, the herbicide is selected from isoxazolidinone herbicides, urea herbicides, triazine herbicides, hydroxybenzonitrile herbicides, thiocarbamate herbicides, pyridazine herbicides, chloroacetanilide herbicides; benzothiazole herbicides; carbanylate herbicides, cyclohexene oxime herbicides; picolinic acid herbicides; pyridine herbicides; quinoline carboxylic acid herbicides; chlorotriazine herbicides, aryloxyphenoxypropion herbicides, oxadiazolon herbicides, phenylurea herbicides, sulfoanilide herbicides, triazolopyrimidine herbicides, amide herbicides, pyridazine herbicides, dinitroaniline herbicides, or combinations thereof.

[0163] Preferably, the pesticide is a fungicide selected from amide fungicides, acyl amino acid fungicides, anilide fungicides, benzamide fungicides, sulfonamide fungicides, strobilurin fungicides, aromatic fungicides, benzimidazole fungicides, carbamate fungicides, carbanilate fungicides, conazole fungicides (imidazole triazole), copper fungicides, dithiocarbamate fungicides, imidazole fungicides, organophosphate fungicides, oxazole fungicides, pyrazole fungicides, pyridine fungicides, or combinations thereof.

[0164] Preferably, insecticides include arsenic insecticides, plant insecticides, carbamate insecticides, benzofuranylmethylcarbamate insecticides, dimethylcarbamate insecticides, insecticides, dinitrophenol insecticides, fluorine insecticides, formamidine insecticides, fumigation insecticides, inorganic insecticides, insect growth regulators, benzoylphenylurea chitin synthesis inhibitors, macrocyclic lactone insecticides, neonicotinoid insecticides, nereitoxin analog insecticides, organochlorine insecticides, organophosphate insecticides, organothiophosphate insecticides, heterocyclic organothiophosphate insecticides, and phenylorganothio The insecticides are selected from phosphate insecticides, phosphonic acid insecticides, phosphonothioate insecticides, phosphoramidate insecticides, phosphoramidethioamide insecticides, oxadiazine insecticides, oxadiazolon insecticides, phthalimide insecticides, physical insecticides, pyrazole insecticides, pyrethroid insecticides, pyrethroid ether insecticides, pyrimidinamine insecticides, pyrrole insecticides, quaternary ammonium insecticides, sulfoximine insecticides, tetramic acid insecticides, tetronic acid insecticides, thiazole insecticides, thiazolidinedione insecticides, and thiourea insecticides.

[0165] Preferably, the nematicides are abamectin, carvacrol, benomyl, carbofuran, carbosulfan, chloetocarb, alanicarb, aldicarb, aldoxycarb, oxamyl, tilpate, carbon disulfide, cyanogen, 1,2-dichloropropane, 1,3-dichloropropene, dimethyl disulfide, methyl bromide, methyl iodide, sodium tetrathiocarbonate, diamidaphos, phenamiphos, phostiethane, phosphamidone, kazusaphos, chlor The following are selected: pyrifos, diclofenthion, dimethoate, etoprofos, phensulfothion, fostiazate, heterophos, isazofos, folate, phosphocarb, terbuphos, thionazine, triazophos, imicaphos, mecarfone, acetoprol, benklothiaz, chloropicrin, dazomet, DBCP, DCIP, fluazandinidine, fluensulfone, furfural, metam, methylisothiocyanate, thioxafene, and xylenol.

[0166] Preferably, the toxicity mitigating agent is selected from benoxacol, BPCMS, croquintocet, cyanometrinil, cyprosulfamide, dichlormid, dicyclonone, dietrate, fenchlorazole, fenchlorim, flurazole, fluxofenim, flirazole, isoxadifen, diekaowan, diekaoxy, mefenpir, mefenate, metcamifen, naphthalic anhydride, and oxavetrinil.

[0167] In one embodiment of the present invention, the liquid pesticide composition comprises a cocrystal of sulfenthrazone and metrivudine in an amount of about 10 w / w% to about 40 w / w% of the total weight of the pesticide composition, an acrylic polymer in an amount of about 1% to about 20%, and a glycerol in an amount of about 1% to about 20%.

[0168] In one embodiment of the present invention, the liquid pesticide composition comprises a cocrystal of sulfenthrazone and metrivudine in an amount of about 10 w / w% to about 40 w / w% of the total weight of the pesticide composition, an acrylic polymer in an amount of about 1% to about 20%, and glycerol in an amount of about 1% to about 20%, and the pesticide composition is formulated as a suspension concentrate.

[0169] In embodiments of the present invention, the liquid pesticide composition comprises a cocrystal of sulfenthrazone and metrivudine in an amount of about 10 w / w% to about 40 w / w% of the total weight of the liquid pesticide composition, an alkali-swelling polyacrylate in an amount of about 1 w / w% to about 20 w / w%, an amount of about 0.1 w / w% to about 30% of glycerol, and an amount of about 10 w / w% to about 30% of water, and the liquid pesticide composition is formulated as a suspension concentrate.

[0170] The compositions according to the present invention can also be prepared by tank-mixing the active ingredients with auxiliary agents suitable for formulation of these active ingredients, or alternatively, they can be sold as kits of components containing active ingredients and other components that can be mixed before spraying.

[0171] In another aspect of the present invention, a method for controlling weeds is provided, comprising applying a composition comprising a cocrystal of an effective amount of sulfenthrazone and a triazinon herbicide to a plant or its habitat, plant seeds, or soil.

[0172] In another aspect of the present invention, a method for controlling weeds is provided, comprising applying a composition comprising an effective amount of sulfenthrazone and metrivudine cocrystal to a plant or its habitat, plant seeds, or soil.

[0173] The herbicide composition of the present invention is effective against crops such as corn, rice, wheat, barley, rye, oats, sorghum, cotton, soybeans, peanuts, buckwheat, beets, rapeseed, sunflowers, sugarcane, and tobacco; vegetables such as eggplant, tomato, pimento, chili peppers, potatoes, and other nightshade vegetables; cucurbitaceous vegetables such as cucumber, pumpkin, zucchini, watermelon, melon, and other cucurbitaceous vegetables; radish, turnip, horseradish, and fern. Brassicaceae vegetables such as Chinese cabbage, cabbage, mustard, and broccoli; Star vegetables such as burdock, garland chrysanthemum, Korean thistle, and lettuce; Liliaceae vegetables such as leeks, onions, garlic, and asparagus; Amomaceae vegetables such as carrots, parsley, celery, and paranip; leafy vegetables such as spinach and chard; leafy vegetables such as perilla, mint, and basil; strawberries, sweet potatoes, and yams (Dioscorea) Japonica, Colocasia, etc., flowers, ornamental plants, grass, fruits: pome fruits such as apples, pears, and quince, stone fruits such as peaches, plums, nectarines, prunus, cherries, apricots, and prunes, citrus fruits such as oranges, lemons, limes, and grapefruits, nuts such as chestnuts, walnuts, hazelnuts, almonds, pistachios, cashews, and macadamia nuts, blueberries, cranberries, blackberries, raspberries It can be used to target weeds of non-fruit trees such as berries like lees, grapes, persimmons, olives, plums, bananas, oil palms, coffee, date palms, manure palms, etc., as well as trees such as tea, mulberry, flowering trees, ash, birch, dogwood, eucalyptus, ginkgo, lilac, maple, kercus, poplar, redbud, sweetgum, plane tree, zelkova, cypress, fir, hemlock, juniper, pine, spruce, and strawberry.

[0174] Therefore, in other aspects, the present invention provides a method for controlling weeds in a particular location, comprising a cocrystal of sulfenthrazone and metrivudine for that location.

[0175] The target weed can be selected from the following: Weeds of the Urticaceae family: Urtica urens; Weeds of the Polygonaceae family: Polygonum convolvulus, Polygonum lapathifolium, Polygonum pensylvanicum, Polygonum persicaria, Polygonum longisetum, Polygonum aviculare, Polygonum arenastrum, Polygonum cuspidatum, Rumex japonicus, Rumex crispus, Rumex obtusifolius, Rumex acetosa; Portulaca oleracea (purslane), a weed belonging to the Portulacaceae family. Caryophyllaceae weeds: Stellaria media, Cerastium holostoides, Cerastium glomeratum, Spergula arvensis, Silene gallica A weed belonging to the family Pomegranate family: Mollugo verticillata; Chenopodiaceae weeds: Chenopodium album, Chenopodium ambrosioides, Kochia scoparia, Salsola kali, and other species of Chenopodium; Amaranthaceae weeds: Amaranthus retroflexus, Amaranthus viridis, Amaranthus lividus, Amaranthus spinosus, Amaranthus hybridus, Amaranthus palmeri, Amaranthus rudis, Amaranthus patulus, Amaranthus tuberculatos, Amaranthus blitoides, Amaranthus deflexus, Amaranthus chitensis Alternanthera quitensis, Alternanthera sessilis, Alternanthera sessilis, Alternanthera tenella; Papaveraceae weeds: Common poppy (Papaver rhoeas), Thistle poppy (Argemone Mexicana); Brassicaceae weeds: Raphanus raphanistrum, Raphanus sativus, Sinapis arvensis, Capsella bursa-pastoris, Brassica juncea, Brassica campestris, Descurainia pinnata, Rorippa islandica, Rorippa sylvestris, Thlaspi arvense, Myagrum rugosum, Leidium virginicum, Coronapus didymus;

[0176] Weeds such as Dinebra Americana, Dinebra aquatic, Dinebra aristidoides, Dinebra bromoides, Dinebra calycina, Dinebra caudata, Dinebra chinensis, Dinebra chloride, Dinebra chondrosioides, Dinebra coerulescens, Dinebra cristata, Dinebra curtipendula, Dinebra decipiens, and Dinebra dibaricate. Dinebra divaricate), Dinebra dura, Dinebra guineensis, Dinebra hirsute, Dinebra hirta, Dinebra juncifolia, Dinebra ligulata, Dinebra lima, Dinebra melicoides, Dinebra nealleyi, Dinebra neesii, Dinebra panicea, Dinebra panicoides, Dinebra pubescens, Dinebra repens, Dinebra scabra (Dinebra Dinebra scabra), Dinebra secunda, Dinebra simoniana, Dinebra southwoodii, Dinebra squalossa (DinebraDinebra squarrosa, Dinebra srilankensis, Dinebra tuaensis, Dinebra verticillate, Dinebra retroflexa, Dinebra haareri, Dinebra marquisensis, Dinebra perrieri, Dinebra polycarpha, Dinebra somalensis (Cleome affinis) - a weed of the family Caprifoliaceae; Leguminous weeds: Aeschynomene indica, Aeschynomene rudis, Sesbania exaltata, Cassia obtusifolia, Cassia occidentalis, Desmodium tortuosum, Desmodium adscendens, Trifolium repens, Pueraria lobata, Vicia angustifolia, Indigofera hirsuta, Indigofera tortuxilensis Vigna sinensis;

[0177] Oxalidicaceae weeds: Oxalis corniculata, Oxalis strica, Oxalis oxyptera; Geraniaceae weeds: Geranium carolinense, Erodium cicutarium; Euphorbiaceae weeds: Euphorbia helioscopia, Euphorbia maculate, Euphorbia humistrata, Euphorbia esula, Euphorbia heterophylla, Euphorbia brasiliensis, Acalypha australis, Croton glandulosus, Croton lobatus, Phyllanthus corcovadensis, Ricinus communis; Malvaceae weeds: Abutilon theophrasti, Sida rhombifolia, Sida cordifolia, Sida spinosa, Sida glaziovii, Sida santaremnensis, Hibiscus trionum, Anoda cristata, Malvastrum coromandelianum Weed of the family Sterculiaceae: Waltheria indica; Violaceae weeds: Viola arvensis, Viola tricolor; Cucurbitaceae weeds: *Sicyos angulatus*, *Echinocystis lobata*, *Momordica charantia*; Lythraceae weed: Brown planthopper (Lythrum salicaria); Brassicaceae weed: Hydrocotyle sibthorpioides; Barley family weed: Chili pepper (Cardiospermum halicacabum); Primulaceae weed: Anagallis arvensis; Morning glory family weeds: brown planthopper (Asclepias syriaca), sand louse (Ampelamus albidus); Chenopodiaceae weeds: Galium aparine, Galium spurium var. echinospermon, Spermacoce latifolia, Richardia brasiliensis, Borrelia alata; Convolvulaceae weeds: Morning glory (Ipomoea nil), American morning glory (Ipomoea hederacea), round-leaved morning glory (Ipomoea purpurea), round-leaved American morning glory (Ipomoea hederacea var. integriuscula), bean morning glory (Ipomoea lacunosa), star morning glory (Ipomoea triloba), field morning glory (Ipomoea acuminata), ivy vine (Ipomoea hederifolia), cypress vine (Ipomoea coccinea), morning glory (Ipomoea quamoclit), Ipomoea grandifolia, Ipomoea aristolochiafolia, maple-leaf morning glory (Ipomoea cairica), Convolvulus arvensis, Calystegia hederacea, Calystegia japonica, Merremia hedeacea, Merremia aegyptia, Merremia cissoides, Jacquemontia tamnifolia;

[0178] Mugiaceae weed: Millipede (Myosotis arvensis); Lamiaceae weeds: Lamium purpureum, Lamium amplexicaule, Leonotis nepetaefolia, Hyptis suaveolens, Hyptis lophanta, Leonurus sibiricus, Stachys arvensis; Solanaceae weeds: White-flowered nightshade (Datura stramonium), black nightshade (Solanum nigrum), glossy black nightshade (Solanum americanum), Solanum ptycanthum, Solanum sarrachoides, Solanum rostratum, Solanum aculeatissimum, Solanum sisymbriifolium, horse nightshade (Solanum carolinense), broad-leaved nightshade (Physalis angulata), thin-leaved nightshade (Physalis subglabrata), large nightshade (Nicandra physaloides); Cockroach family weeds: Veronica hederaefolia, Veronica persica, Veronica arvensis; Plantaginaceae weed: Plantago asiatica; Asteraceae weeds: Xanthium pensylvanicum, Xanthium occidentale, Helianthus annuus, Matricaria chamomilla, Matricaria perforata, Chrysanthemum segetum, Matricaria matricarioides, Artemisia princeps, Artemisia vulgaris, Artemisia verlotorum, Solidago altissima, Taraxacum officinale, Galinsoga ciliata), Galinsoga parviflora, Senecio vulgaris, Senecio brasiliensis, Senecio grisebachii, Conyza bonariensis, Conyza canadensis, Ambrosia artemisiaefolia, Ambrosia trifida, Bidens pilosa, Bidens frondosa, Bidens subalternans, Silybum marianum, Carduus nutans, Lactuca serriola, Sonchus Sonchus oleraceus, Sonchus asper, Wedelia glauca, Melampodium perfoliatum, Emilia sonchifolia, TagetesMinuta), Blainvillea latifolia, Tridax procumbens, Porophyllum ruderale, Acanthospermum australe, Acanthospermum hispidum, Cardiospermum halicacabum, Ageratum conyzoides, Eupatorium perfoliatum, Eclipta alba, Erectites hieracifolia, Gamochaeta spicata, Gnaphalium spicatum, Jaegeria hirta hirta), American pomelosus (Parthenium hysterophorus), common oak (Siegesbeckia orientalis), American oak (Soliva sessilis); Liliaceae weeds: Allium canadense, Allium vineale; Commelinaceae weeds: Commelina communis, Commelina bengharensis, Commelina erecta;

[0179] Grass weeds: Barnyard grass (Echinochloa crus-galli), Setaria viridis, Setaria faberi, Setaria glauca, Setaria geniculata, Digitalaria ciliaris, Digitalaria sanguinalis, Digitalaria horizontalis, Digitalaria insularis, Eleusine indica, Poa annua, Alopecurus aequalis, Alopecurus myosuroides, Avena (Japanese oat) Sorghum fatua, Sorghum halepense, Sorghum vulgare, Agropyron repens, Lolium multiflorum, Lolium perenne, Lolium rigidum, Bromus secalinus, Bromus tectorum, Hordeum jubatum, Aegilops cylindrica, Phalaris arundinacea, Phalaris minor, Apera spica-venti, Panicum dichotomiflorum, Panicum texanum, Panicum Brachiaria platyphylla, Brachiaria ruziziensis, Brachiaria plantaginea, Brachiaria decumbensdecumbens), Brachiaria brizantha, Brachiaria humidicola, Cenchrus echinatus, Cenchrus pauciflorus, Eriochloa villosa, Pennisetum setosum, Chloris gayana, Eragrostis pilosa, Rhynchelitrum repens, Dactyloctenium aegyptium, Ischaemum rugosum, Oryza sativa, Paspalum notatum, Paspalum maritimum maritimum), Pennisetum clandestinum, Pennisetum setosum, and Rottboellia cochinchinensis; Cyperaceae weeds: Cyperus microiria, Cyperus iria, Cyperus odoratus, Cyperus rotundus, Cyperus esculentus, Kyllinga gracillima; Equisetaceae weeds: Equisetum arvense, Equisetum palustre; Aizoaceae weeds, etc.

[0180] In preferred embodiments, the compositions of the present invention are applied to soybean crops and are effective against several broadleaf and grass weeds, namely velvetleaf, redroot pigweed, common lambsquater, tumble pigweed, and giant foxtail.

[0181] In one embodiment, the composition may be applied to a tank mixture or as a premixed composition.

[0182] In one embodiment, the composition of the present invention may be applied either before or after emergence. In a preferred embodiment, the composition of the present invention may be used both before emergence and before planting. The advantages of the composition are its surprisingly good residual effect and rapid weed burn-down when applied before planting or before emergence.

[0183] According to one embodiment of the present invention, the method of applying the pesticide composition and the mixture according to the present invention are not particularly limited. It may be the simultaneous application of either a premix or tank mixture of the active ingredient with an adjuvant suitable for the formulation, or it may be a continuous sequential application.

[0184] One embodiment of the present invention provides for the use of a pesticide composition comprising a cocrystal of sulfenthrazone and a triazinon herbicide.

[0185] One embodiment of the present invention provides for the use of a pesticide composition comprising a cocrystal of sulfenthrazone and metrivudine.

[0186] One embodiment of the present invention provides for the use of a liquid pesticide composition comprising a cocrystal of sulfenthrazone and metrivudine.

[0187] According to one embodiment of the present invention, a kit is provided comprising a cocrystal of sulfenthrazone and a triazinon herbicide and other pesticide excipients.

[0188] According to one embodiment of the present invention, a kit is provided that includes a cocrystal of sulfenthrazone and a triazinon herbicide.

[0189] One embodiment of the present invention provides a kit containing a cocrystal of sulfenthrazone and metrivudine.

[0190] Next, the present invention will be described with reference to the following specific examples. It should be noted that the examples attached below are illustrative rather than limiting the present invention, and those skilled in the art can design many alternative embodiments without departing from the scope of the present invention.

Example

[0191] Example 1: Preparation of a cocrystal of sulfentrazone and metribuzin For the 1:1 cocrystal of sulfentrazone and metribuzin, 193.5 g of sulfentrazone and 107 g of metribuzin were placed in a round-bottom flask. 150 ml of dichloroethane was added to this mixture. The solution was stirred at 30 °C overnight, 1000 ml of hexane was added, and stirred to obtain a solid, which was filtered and dried under vacuum to obtain 268 g of crystals. HPLC analysis: metribuzin - 33.48% (w / w) and sulfentrazone - 65.31% (w / w), which corresponds to approximately 1:1 (mol:mol) of metribuzin:sulfentrazone (Figure 1).

[0192] Spectroscopic analysis of the cocrystal The cocrystal prepared according to Example 1 was further characterized by FT-IR (Figure 2). The FT-IR spectrum of the cocrystal of sulfentrazone and metribuzin is 3314, 3264, 2970, 1736, 1685, 1630, 1521, 1494, 1467, 1420, 1392, 1367, 1348, 1332, 1303, 1262, 1193, 1163, 1116, 1098, 1072, 976, 942, 893, 877, 824, 796, 764, 740, 670, 661, 645, 602, 570, 458, particularly (±4 cm -1 ) 3314, 3264, 1736, 1685, 1630, 1521, 1494, 1467, 1420, 1392, 1367, 1348, 1332, 1163, 1116, 1098, 1072, 976 and 824 (±4 cm -1 ) and is found to exhibit at least 3 characteristic values selected therefrom, particularly at least 5 characteristic values, or all the values.

[0193] Crystallographic analysis of cocrystals The cocrystal prepared according to Example 1 is characterized by PXRD (Figure 3). The cocrystal of sulfenthrazone and metrivudine exhibits an X-ray powder diffractogram at 25°C (PXRD conditions: Instrument: Bruker make next-generation D2 Phaser Powder X-ray diffractometer; operating at 30.0kV, 10mA; radiation: Cu-Kα; wavelength: 1.54060°A, scan range: 2~40 2θ, step size: 0.02°). The cocrystal of sulfenthrazone and metrivudine exhibits at least three, particularly at least four, more preferably all, of the following reflections shown in Table 1 below as 2θ values:

[0194] [Table 1]

[0195] Single-crystal X-ray diffraction Single-crystal X-ray diffraction analysis determines the atomic and molecular structure of a cocrystal, including the molar relationships between the two compounds forming the cocrystal. Single-crystal X-ray diffraction data of a sulfenthrazone and metrivudine cocrystal were collected using a Bruker D8 QUEST PHOTON-100 detector. The structure was elucidated using direct methods and refined and expanded using Fourier techniques with the SHELXTL-PLUS software package. Figure 7 shows the single-crystal X-ray diffraction pattern illustrating the hydrogen bonding interaction that forms the sulfenthrazone and metrivudine cocrystal.

[0196] Table 2 below shows the single-crystal X-ray diffraction data and refinements of the cocrystal of sulfenthrazone and metrivudine:

[0197] [Table 2]

[0198] Thermal analysis of cocrystals DSC measurements of cocrystals were performed using a Mettler-Toledo DSC 3 STARe system, and the DSC data was analyzed using STARe software. Measurements were taken using a sealed aluminum pan with a capacity of 40 microliters, under a nitrogen stream, at a heating rate of 10°C / min, and with a sample weight of 5–10 mg.

[0199] The DSC of the cocrystal shows an endothermic peak starting at 107.3°C and peaking at 110.5°C (Figure 4), with a normalized specific heat of fusion of -69 Jg⁻¹ to -81 Jg⁻¹. The endothermic peak observed in the DSC does not coincide with the individual melting points of sulfenthrazone and metrivudine. Therefore, the analysis using DSC indicates cocrystallization.

[0200] Example 2: Composition of the suspension concentrate (SC) of sulfenthrazone and metrivudine [Table 3]

[0201] 5 g of propylene glycol, 1 g of polyalkylene glycol ether, 5 g of alkali-swellable polyacrylate, and 2 g of acrylic polymer were stirred with 42.60 g of water for at least 1 hour. 0.2 g of silicone defoamer was added to the above mixture and stirred. 13.867 g of a cocrystal of sulfenthrazone and metrivudine and 22.43 g of metrivudine were added and subjected to homogenization for at least 1 hour, after which the mixture was ground. 7.5 g of 2% xanthan gum gel was added and the mixture was subjected to homogenization for at least 1 hour. The homogenized mixture was then set for uniform gelation. The resulting composition was then characterized by analytical techniques FT-IR (Figure 5) and P-XRD (Figure 6).

[0202] Example 3: 26.77% sulfenthrazone and 8.93% metrivudine SC [Table 4]

[0203] A homogeneous powder was prepared by mixing 27.85 g of metrivudine and 9.30 g of sulfenthrazone technology. The powder was then incubated in a 54°C incubator for 14 days to promote cocrystal formation. Separately, a slurry was prepared in water by adding 5.0 g of glycerin, 1.0 g of polyalkylene glycol ether, 2.3 g of acrylic polymer, and 4.70 g of alkali-swellable polyacrylate to the slurry preparation, and the solution was homogenized by stirring for 30 minutes. Furthermore, 0.2 g of silicone defoamer and 0.3 g of clay were added sequentially under continuous stirring. The homogeneous powder of metrivudine and sulfenthrazone, held for pretreatment, was then added to the slurry obtained in the above step under continuous stirring. The slurry was stirred for 30 minutes to break up lumps, cooled to below 15°C, and used for bead grinding. After the slurry reached the desired particle size (D90 less than 10 microns), it was used for gelation. A 2% aqueous gel was obtained by adding 8 g of xanthan gum and 0.2 g of bronopol.

[0204] Example 4: 26.77% sulfenthrazone and 8.93% metrivudine SC [Table 5]

[0205] A homogeneous powder was prepared by mixing metrivudine and sulfenthrazone. The resulting powder was melted in an oil bath at 105-110°C and then cooled to room temperature to obtain flakes. The flakes were then pulverized to obtain a powder (power). Separately, glycerin, polyalkylene glycol ether, acrylic polymer, and alkali-swellable polyacrylate were added to the slurry preparation to prepare a slurry in water, and the solution was stirred for 30 minutes to homogenize it. Furthermore, a silicone defoamer, clay, and 1,2-benzoisothiazolin-3-one were added sequentially under continuous stirring. Next, the metrivudine and sulfenthrazone powders obtained from the pretreatment were added to the slurry obtained in the above step under continuous stirring. The slurry was stirred for 30 minutes to break up any clumps, and then cooled to below 15°C and used for bead grinding. After the slurry reached the desired particle size (D90 less than 10 microns), it was used for gelation. A 2% aqueous gel was obtained by adding 8 g of xanthan gum and 1,2-benzisothiazolin-3-one.

[0206] Example 5: SC composition of sulfenthrazone and metrivudine [Table 6]

[0207] 5 g of propylene glycol, 1 g of polyalkylene glycol ether, 5 g of alkali-swellable polyacrylate, and 2 g of acrylic polymer were stirred with 42.60 g of water for at least 1 hour. 0.2 g of silicone defoaming agent was added to the above mixture and stirred. 8.98 g of sulfenthrazone and 27.22 g of metrivudine were added and the mixture was homogenized for at least 1 hour, after which it was ground. 7.5 g of 2% xanthan gum gel was added and the mixture was homogenized for at least 1 hour. The homogenized mixture was then set for uniform gelation.

[0208] Example 6: Sulfenthrazone and Metrivudine SC [Table 7]

[0209] Water was partially added to a heat-controlled vessel equipped with a high mixer and stirred. Alkali-swellable polyacrylate, acrylic polymer, polyalkylene glycol ether, silicone defoamer, partial amounts of glycerin and clay were added to obtain a solution. The solution was then cooled to below 25°C. Metrivudine and sulfenthrazone were added to the solution under high shear to obtain a mixture. The mixture was then ground at a grinding temperature of below 25°C (particle size specification of d10 ≤ 1, d50 ≤ 4, d90 ≤ 10, and d100 ≤ 35 μm) to obtain a ground base. The ground base was returned to a mixing vessel heated to 54°C and mixed for approximately 1 hour. Separately, a thickener was prepared by adding glycerin, 1,2-benzoisothiazolin-3-one, xanthan gum and water to a container and mixing for 30 minutes. The thickener was added to the ground base. The final composition was adjusted with water, and the quality check and packaging were removed.

[0210] Example 7: Sulfenthrazone and Metrivudine SC [Table 8]

[0211] Metrivudine, sulfenthrazone, glycerin, polyalkylene glycol ether, alkali-swellable polyacrylate, acrylic polymer, xanthan gum, clay, and water were mixed in the above amounts and treated according to the method shown in Example-6 to obtain a concentrated suspension composition of a cocrystal containing sulfenthrazone and metrivudine.

[0212] Example 8: Sulfenthrazone and Metrivudine SC [Table 9]

[0213] Metrivudine, sulfenthrazone, glycerin, polyalkylene glycol ether, alkali-swellable polyacrylate, acrylic polymer, silicone defoamer, xanthan gum, clay, and water were mixed in the above amounts and processed according to the method shown in Example-6 to obtain a concentrated suspension composition of a cocrystal containing sulfenthrazone and metrivudine.

[0214] Example 9: Sulfenthrazone and Metrivudine SC [Table 10]

[0215] Method: Water was partially added to a heat-controlled vessel equipped with a high mixer and stirred. Alkali-swellable polyacrylate, acrylic polymer, polyalkylene glycol ether, silicone defoamer, partial amounts of glycerin and clay were added to obtain a solution. The solution was then cooled to below 25°C. Metrivudine and sulfenthrazone were added to the solution under high shear to obtain a mixture. The material was ground to the required particle size, and the wet sieve retention rate was measured according to in-process specifications at temperatures of 25°C or below 25°C during the grinding method. A thickener was added to the ground base. The final composition was prepared with water, quality checked, and the packaging was removed.

[0216] Example 10 Stability test of suspension concentrate composition The stability characteristics associated with the compositions developed according to the present invention were studied. Further samples of the compositions described in Examples 3 and 4 were taken, and their physicochemical parameters were evaluated. The compositions of Examples 3 and 4 were found to remain stable when tested under ambient conditions, i.e., room temperature and pressure. The compositions also passed 14-day and 28-day accelerated thermal stability (AHS) tests, remaining as a fluid suspension with a grayish-white appearance. The activity content was also evaluated at all three stages (ambient, 14-day AHS, and 28-day AHS). The activity content was found to remain nearly constant without significant degradation or loss. The compositions also passed the wet sieve test, as no crystals were observed to be retained on the wet sieve. Analysis of the particle size of the compositions revealed it to be nearly constant, suggesting that particle size growth or crystal formation is negligible. (Table 3)

[0217] [Table 11]

[0218] Example 11 Biological efficacy data Pre-emergence studies were conducted on soybean crops to test the efficacy of the pesticide compositions developed according to the present invention against several broadleaf and grass weeds, namely velvetleaf, redroot pigweed, common lambsquater, tumble pigweed, and giant foxtail. The composition of Example-7, having a cocrystal of sulfenthrazone and metrivudine in a 1:2 ratio, was tested at a rate of 630 g ai in a soybean field. The composition was found to be effective against velvet leaf, redroot pigweed, common lambsquater, tumble pigweed, and giant foxtail at all intervals from 14DAA (14 days after application) to 35DAA (35 days after application). The pesticide composition of the present invention achieved over 60% control for velvet leaf; 100% control of redroot pigweed. Similarly, over 90% control was observed for redroot pigweed and giant foxtail. As shown in the table below, good control of giant foxtail was also observed from 50-83% at 35DAA-21DAA observations.

[0219] [Table 12]

[0220] Therefore, the inventors have found that a pesticide composition comprising a cocrystal of sulfenthrazone and a triazinon herbicide results in a stable composition. The formation of a cocrystal of sulfenthrazone and a triazinon herbicide, particularly metrivudine, before incorporation into the pesticide composition imparted physical stability to the system. The acrylate polymer and glycerol in the cocrystal pesticide composition provided good performance over time, with little to no sedimentation and minimal particle size degradation. It should be understood that the present invention is not limited to the details of the above embodiments, which are described only as examples.

Claims

1. A co-crystal comprising sulfentrazone and metribuzin, A powder X-ray diffraction pattern including peaks at diffraction angle 2θ values ​​of 7.8°, 11.8°, 14.1°, 17.8°, 22.1°, 23.4° and 24.4° (±0.2°); or A DSC thermogram that includes an endothermic peak with an onset at 107.3° C. and a peak at 110.5° C.; or Single crystal X-ray diffraction with lattice parameters of a = 22.2825(4) Å, b = 10.5240(2) Å, c = 11.4659(2) Å, α = 90°, β = 93.5058°(7) and γ = 90°. A cocrystal is characterized by either

2. 2. The co-crystal of claim 1, wherein the molar ratio of sulfentrazone to metribuzin in the co-crystal is from 1:9 to 9:

1.

3. 3. The co-crystal of claim 2, wherein the sulfentrazone and the metribuzin are present in a molar ratio of from 2:1 to 1:

2.

4. A pesticide composition comprising the cocrystal of claim 1, wherein the cocrystal comprises, by weight of the composition, 10-90% sulfentrazone and 90-10% metribuzin.

5. The composition of claim 4 , wherein the composition is a liquid composition.

6. 5. A pesticide formulation comprising the composition of claim 4 which is a suspension concentrate.

7. A process for preparing the pesticide composition of claim 4, comprising: a) pretreating sulfentrazone and metribuzin to form a co-crystal; b) mixing the co-crystal of step (a) with an agriculturally acceptable excipient to obtain said composition; The process includes:

8. a) pretreating sulfentrazone and metribuzin to obtain a co-crystal by heating the mixture followed by cooling to room temperature; b) mixing the co-crystal of step (a) with pesticide excipients in the presence of water to obtain a homogenous pesticide composition; The process of claim 7, comprising:

9. a) preparing an aqueous mixture of agriculturally suitable excipients to obtain a homogenous solution; b) adding metribuzin and sulfentrazone to the homogenous solution of step (a) to obtain a slurry; c) optionally milling the slurry; d) heating the slurry of step (b) or (c) and cooling to room temperature; e) optionally adding other pesticide excipients to the slurry of step (d) and mixing to obtain a homogenous pesticide composition; 8. A process for preparing the pesticide composition of claim 7, comprising:

10. 13. A method for controlling weeds comprising applying a herbicidally effective amount of the co-crystal of sulfentrazone and metribuzin of claim 1 to a plant or its habitat, a plant seed or soil.

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