Pesticide composition

Abstract

The present invention relates to pesticide compositions, methods for preparing pesticide compositions, pesticide formulations, methods for preparing pesticide formulations, and methods for protecting crops using pesticide formulations.

Description

[Technical Field]

[0001] The present invention relates to pesticide compositions, methods for preparing pesticide compositions, pesticide formulations, methods for preparing pesticide formulations, and methods for protecting crops using pesticide formulations. [Background technology]

[0002] Pesticide formulations are routinely used to protect crops. Among these are capsule suspensions, which are formulations in which the active ingredient of the pesticide is dispersed in droplets in the form of microcapsules enclosed in a polymer wall.

[0003] These microcapsule formulations are typically formed by interfacial polymerization, using monomers that react at the droplet interface to form a polymer consisting of a polyurea shell. This polymer not only controls the release of the active ingredient upon application, but also provides protection from chemical or photodegradation if necessary. The incorporation of synthetic polymers into these formulations inevitably results in the inclusion of non-biodegradable polymers in the form of tiny plastic particles known as microplastics, which can have adverse environmental effects when sprayed on crops. A further drawback of these capsule suspensions is the need for additional ingredients to prevent premature release of the active ingredient during storage and deterioration of the product's physical properties prior to use.

[0004] In "Ethyl cellulose polymer microspheres for controlled release of nofluazon," by Jose I. Perez-Martinez, Esmeralda Morillo, Celia Maqueda, and Juan M. Gines, Pest Manag Sci 57:688-694 (2001), DOI: 10.1002 / ps.339, microcapsules were prepared by a solvent evaporation method. In this method, the pesticide active ingredient and polymer are co-dissolved in a volatile, water-immiscible solvent such as chloroform or o-xylene. This solution is emulsified in an aqueous phase, and the microspheres are recovered via solvent diffusion / evaporation and polymer precipitation. This complex process involves the use of a non-biodegradable solvent, its evaporation, and the filtration, washing, and drying of the formed microcapsules. Summary of the Invention [Problem to be solved by the invention]

[0005] It is an object of the present invention to overcome at least some of the shortcomings of the prior art, or to provide a commercially useful alternative.

[0006] A further object of the present invention is to provide stable compositions of agrochemical active ingredients that form microcapsules upon dilution with water immediately prior to application and / or avoid the use of non-biodegradable polymers that lead to the introduction of microplastics into the environment.

[0007] It is a further object of the present invention to provide a composition that forms microcapsules upon dilution with water without the need for evaporation of a solvent to dissolve the biodegradable polymer and / or subsequent isolation and / or drying of the microcapsules.

[0008] It is a further object of the present invention to provide a biodegradable formulation comprising a microcapsule suspension of an active pesticide ingredient that can effectively reduce the amount of active pesticide ingredient lost through volatilization to the same extent as known capsule suspension formulations, such as the standard clomazone CS formulation, Clomate®.

[0009] It is a further object of the present invention to provide a biodegradable formulation comprising a microcapsule suspension of an active pesticidal ingredient that provides comparable or improved control, i.e., efficacy against weeds, pests, insects, etc., compared to known capsule suspension formulations such as Chromate®. [Means for solving the problem]

[0010] Summary of the Invention In a first aspect, the present invention provides a method for producing a medicament for the treatment of a pulmonary arthritis, comprising: pesticide active ingredients; Water-miscible organic solvents; a first water-immiscible organic solvent; emulsifier; biodegradable polymers; and optionally a second water-immiscible organic solvent; a composition comprising: Here, the active agricultural chemical ingredient is soluble in the water-miscible organic solvent and / or the first water-immiscible organic solvent and / or a mixture of the water-miscible organic solvent and the first water-immiscible organic solvent.

[0011] In a second aspect, the present invention provides a method of making the composition of the first aspect, the method comprising: combining a biodegradable polymer and a first water-immiscible organic solvent to form a first mixture; adding a water-miscible organic solvent and optionally a second water-immiscible organic solvent to the first mixture to form a second mixture; adding an active pesticide ingredient to the second mixture to form a third mixture; and adding an emulsifier to the third mixture; Including, Here, the active agricultural chemical ingredient is soluble in the water-miscible organic solvent and / or the first water-immiscible organic solvent and / or a mixture of the water-miscible organic solvent and the first water-immiscible organic solvent.

[0012] In a third aspect, the present invention provides a method of making a composition of the first aspect, the method comprising: combining a biodegradable polymer and a water-miscible organic solvent to form a first mixture; adding a first water-immiscible organic solvent and optionally a second water-immiscible organic solvent to the first solution to form a second mixture; adding an active pesticide ingredient to the second mixture to form a third mixture; and adding an emulsifier to the third mixture; Including, Here, the active agricultural chemical ingredient is soluble in the water-miscible organic solvent and / or the first water-immiscible organic solvent and / or a mixture of the water-miscible organic solvent and the first water-immiscible organic solvent.

[0013] In a fourth aspect, the present invention provides a formulation comprising water, an active agricultural chemical ingredient, a water-miscible organic solvent, a first water-immiscible organic solvent, an emulsifier, a biodegradable polymer, and optionally a second water-immiscible organic solvent; wherein the pesticidal active ingredient is soluble in the water-miscible organic solvent and / or the first water-immiscible organic solvent and / or a mixture of the water-miscible organic solvent and the first water-immiscible organic solvent; wherein the formulation comprises microcapsules having walls formed at least in part from a biodegradable polymer, wherein the microcapsules contain at least a portion of the pesticidal active ingredient; Here, the microcapsules have a D50 median diameter of 5 to 50 μm.

[0014] In a fifth aspect, the present invention provides a method of making a formulation of the fourth aspect, the method comprising adding a composition of the first aspect to water.

[0015] In a sixth aspect, the present invention provides a method of protecting crops, the method comprising applying to the crops a formulation of the fourth aspect.

[0016] In a seventh aspect, the present invention provides a method of making a composition of the first aspect, the method comprising: combining a biodegradable polymer and a first water-immiscible organic solvent to form a first mixture; adding a water-miscible organic solvent and optionally a second water-immiscible organic solvent to the first mixture to form a second mixture; adding an emulsifier to the second mixture to form a third mixture; and adding a pesticide active ingredient to the third mixture; Including, Here, the active agricultural chemical ingredient is soluble in the water-miscible organic solvent and / or the first water-immiscible organic solvent and / or a mixture of the water-miscible organic solvent and the first water-immiscible organic solvent.

[0017] In an eighth aspect, the present invention provides a method of making a composition of the first aspect, the method comprising: combining a biodegradable polymer and a water-miscible organic solvent to form a first mixture; adding a first water-immiscible organic solvent and optionally a second water-immiscible organic solvent to the first solution to form a second mixture; adding an emulsifier to the second mixture to form a third mixture; adding a pesticide active ingredient to the third mixture; Including, Here, the active agricultural chemical ingredient is soluble in the water-miscible organic solvent and / or the first water-immiscible organic solvent and / or a mixture of the water-miscible organic solvent and the first water-immiscible organic solvent.

[0018] In a ninth aspect, the present invention provides a composition for mixing with an active pesticide ingredient, the composition comprising: Water-miscible organic solvents; a first water-immiscible organic solvent; emulsifier; biodegradable polymers; and optionally a second water-immiscible organic solvent; Including, Here, the active agricultural chemical ingredient is soluble in the water-miscible organic solvent and / or the first water-immiscible organic solvent and / or a mixture of the water-miscible organic solvent and the first water-immiscible organic solvent.

[0019] It has been found that by preparing a formulation using a biodegradable polymer, a water-miscible organic solvent, a first water-immiscible organic solvent, and an emulsifier, a composition containing an active pesticide can be diluted in water to form biodegradable microcapsules that reduce the volatility of the active pesticide and protect it from degradation when the formulation is applied to crops.

[0020] The present invention involves dissolving an agriculturally active ingredient in a mixture of a biodegradable polymer and a water-miscible organic solvent and a first water-immiscible organic solvent, and then adding an emulsifier to dilute with water to obtain a fine emulsion. Surprisingly, and without wishing to be bound by theory, upon dilution with water, the biodegradable polymer precipitates from the solution and forms a membrane at the emulsion droplet interface, thereby producing microcapsules of the agriculturally active ingredient contained in the water-miscible and / or first water-immiscible solvent.

[0021] Advantageously, the compositions and formulations of the present invention have reduced or similar volatility of the pesticidal active ingredients, e.g., Clomazone and Acetochlor, when compared to capsule suspension formulations of the same active agents prepared by interfacial polymerization, while maintaining the weed control and crop safety profiles of such formulations.

[0022] Advantageously, the compositions and formulations of the present invention extend the residual activity of the pesticidal active ingredient by reducing the rate of decomposition compared to known formulations, thereby reducing the application rate required for effective pest control.

[0023] Advantageously, the compositions and formulations of the present invention provide equivalent or improved control, i.e., efficacy against weeds, pests, insects, etc., compared to known capsule suspension formulations such as Chromate®.

[0024] Other preferred embodiments of the compositions, formulations, and methods provided herein are described throughout the specification, particularly in the Examples.

[0025] Each aspect or embodiment defined herein may be combined with other aspects or embodiments unless expressly indicated to the contrary. In particular, any feature indicated as being preferred or advantageous may be combined with any other feature indicated as being preferred or advantageous. [Brief explanation of the drawings]

[0026] (Not stated in the original text) DETAILED DESCRIPTION OF THE INVENTION

[0027] Detailed Description of the Invention Unless otherwise defined herein, scientific and technical terms used in connection with the present invention shall have the meanings that are commonly understood by those skilled in the art. The meaning and scope of the terms should be clear, but in the event of potential ambiguity, the definitions provided herein shall take precedence over any dictionary or external definitions.

[0028] Terms used in this specification and the appended claims have the following meanings unless otherwise specified.

[0029] As used herein, "pesticidally active ingredient" refers to an ingredient that is agriculturally active against crop pests or diseases and / or promotes plant growth. For example, "pesticidally active ingredient" includes biologically active ingredients or plant protection products such as herbicides, insecticides, fungicides, etc.

[0030] As used herein, the term "water-miscible organic solvent" refers to an organic solvent that can be mixed with water in any proportion without separating into multiple phases, such as two phases.

[0031] Conversely, the term "water-immiscible organic solvent" as used herein refers to an organic solvent that cannot be mixed with water in any proportion without separating into multiple phases, such as two phases.

[0032] As used herein, the term "biodegradable" refers to the breakdown of an entity by natural factors such as microorganisms (e.g., bacteria and fungi) and / or abiotic factors such as temperature, ultraviolet light, and oxygen, resulting in the formation of new biomass.

[0033] For example, as used herein, a biodegradable polymer is a polymer that can be broken down by natural factors, such as microorganisms (e.g., bacteria and fungi), and / or abiotic factors, such as temperature, ultraviolet light, and oxygen, to form new biomass.

[0034] For example, as used herein, a biodegradable organic solvent is an organic solvent that can be decomposed by natural factors, such as microorganisms (e.g., bacteria and fungi), and / or abiotic factors, such as temperature, ultraviolet light, and oxygen, to form new biomass.

[0035] As used herein, the term "soluble" with respect to a chemical substance means that the substance is dissolvable in a solvent, cannot be recovered by ordinary filtration means that at least 30 parts of the substance dissolve in 100 parts of the solvent. For example, an active pesticide ingredient is soluble in a water-miscible organic solvent and / or a first water-immiscible organic solvent and / or a mixture of a water-miscible organic solvent and a first water-immiscible organic solvent, meaning that at least 30 parts of the active pesticide ingredient dissolve in 100 parts of the water-miscible organic solvent and / or the first water-immiscible organic solvent and / or a mixture of a water-miscible organic solvent and a first water-immiscible organic solvent.

[0036] As used herein, the term "emulsifier" refers to an agent that enables an aqueous phase and an organic phase to mix in an emulsified state.

[0037] As used herein, the unit "% w / w" means a weight percentage based on the total weight of the composition.

[0038] In a first aspect, pesticide active ingredients; Water-miscible organic solvents; a first water-immiscible organic solvent; emulsifier; biodegradable polymers; and optionally a second water-immiscible organic solvent; A composition comprising: Here, a composition is provided in which the agriculturally active ingredient is soluble in a water-miscible organic solvent and / or a first water-immiscible organic solvent and / or a mixture of a water-miscible organic solvent and a first water-immiscible organic solvent.

[0039] Preferably, the agriculturally active ingredient comprises a herbicide, insecticide, and / or fungicide. More preferably, the agriculturally active ingredient comprises a herbicide. In one embodiment, the agriculturally active ingredient comprises a herbicide that is effective in controlling or reducing chickweed growth.

[0040] In a preferred embodiment, the active ingredient comprises chloroacetanilide. In a preferred embodiment, the pesticidal active ingredient comprises chloroacetanilide that is effective in controlling or suppressing the growth of chickweed. In a preferred embodiment, the chloroacetanilide comprises acetochlor.

[0041] In a preferred embodiment, the pesticidal active ingredient comprises clomazone and / or acetochlor. In a preferred embodiment, the pesticidal active ingredient comprises clomazone. In a further preferred embodiment, the pesticidal active ingredient consists of clomazone. In a preferred embodiment, the pesticidal active ingredient comprises acetochlor. In a further preferred embodiment, the active ingredient consists of acetochlor.

[0042] Clomazone is a commercially available agricultural herbicide with the chemical formula: [ka] CAS number 81777-89-1.

[0043] Acetochlor is a commercially available agricultural herbicide with the chemical formula: [ka] CAS number 34256-82-1.

[0044] Preferably, the pesticidal active ingredient is present in an amount of 30-50% w / w, more preferably 32-50% w / w, even more preferably 32-49% w / w, and most preferably 35-48% w / w. Preferably, when the pesticidal active ingredient comprises or consists of clomazone, the pesticidal active ingredient is present in an amount of 30-50% w / w, more preferably 32-49% w / w, and most preferably 35-48% w / w. Preferably, when the pesticidal active ingredient comprises or consists of acetochlor, the pesticidal active ingredient is present in an amount of 30-50% w / w, more preferably 35-50% w / w, and most preferably 38-50% w / w.

[0045] Preferably, the kinematic viscosity of the biodegradable polymer is 2.0 to 20.0 mPa·s. More preferably, the kinematic viscosity of the biodegradable polymer is 3.0 to 18.0 mPa·s, or 4.0 to 16.0 mPa·s, or 5.0 to 15.0 mPa·s, or 6.0 to 14.0 mPa·s, or 7.0 to 13.0 mPa·s. Even more preferably, the kinematic viscosity of the biodegradable polymer is 8.0 to 12.0 mPa·s, or 9.0 to 11.0 mPa·s. The kinematic viscosity of the biodegradable polymer is measured at 25°C by preparing a 5% w / w solution of the biodegradable polymer in 80% toluene / 20% ethanol. Without wishing to be bound by theory, biodegradable polymers having kinematic viscosities within these preferred ranges are useful for promoting the formation of stable microcapsules of a desired size (e.g., 5 to 50 μm) when diluted with water.

[0046] Preferably, the biodegradable polymer comprises a polysaccharide. More preferably, the biodegradable polymer comprises cellulose and / or starch. Even more preferably, the biodegradable polymer comprises ethyl cellulose. In a further preferred embodiment, the biodegradable polymer consists of ethyl cellulose. Ethyl cellulose is available, for example, from DuPont under the trade name Ethocel. TM It is available commercially under the trade name Standard 10 Premium. TM Standard 10 Premium is Ethocel in 80% toluene / 20% ethanol. TM In the form of a 5% w / w solution of Standard 10 Premium, it has a kinematic viscosity of 9.0-11.0 mPa·s when measured at 25°C using an Ubbelohde viscometer, specifically an Anton-Paar MCR 102 viscometer.

[0047] Preferably, the biodegradable polymer is present in an amount of 1-5% w / w, more preferably 1.5-4.5% w / w, and most preferably 2.0-4.0% w / w. Without wishing to be bound by theory, it is believed that the presence of the biodegradable polymer in these preferred ranges promotes the formation of stable microcapsules of a desired size (e.g., 5-50 μm) upon dilution with water.

[0048] Preferably, the kinematic viscosity of the water-miscible organic solvent is 2 to 10 mPa·s at 25°C. More preferably, the kinematic viscosity of the water-miscible organic solvent is 3 to 8 mPa·s at 25°C. Even more preferably, the kinematic viscosity of the water-miscible organic solvent is 4 to 7 mPa·s at 25°C. Most preferably, the kinematic viscosity of the water-miscible organic solvent is 4 to 6 mPa·s at 25°C. Without wishing to be bound by theory, it is believed that kinematic viscosities in these preferred ranges are useful for promoting the formation of stable microcapsules of a desired size (e.g., 5 to 50 μm) upon dilution with water.

[0049] Preferably, the water-miscible organic solvent is biodegradable. The use of a biodegradable solvent obviates the need for evaporation of the solvent used to dissolve the biodegradable polymer and / or the active agricultural chemical ingredient, and the subsequent separation and drying of the microcapsules.

[0050] In a preferred embodiment, the water-miscible organic solvent comprises 2-hydroxy-N,N-dimethylpropanamide. In a more preferred embodiment, the water-miscible organic solvent consists of 2-hydroxy-N,N-dimethylpropanamide. 2-Hydroxy-N,N-dimethylpropanamide is commercially available, for example, from BTC / BASF under the trade name Agnique® AMD 3L, and has a kinematic viscosity of about 5.1 mPa·s at 25°C.

[0051] Preferably, the water-miscible organic solvent is present in an amount of 2 to 20% w / w. More preferably, the water-miscible organic solvent is present in an amount of 4 to 15% w / w. Most preferably, the water-miscible organic solvent is present in an amount of 5 to 13% w / w. Without wishing to be bound by theory, it is believed that the water-miscible organic solvent present in these preferred ranges helps promote the formation of stable microcapsules of a desired size (e.g., 5 to 50 μm) upon dilution with water.

[0052] Preferably, the molecular weight of the first water-immiscible organic solvent is 100 to 300 g / mol. More preferably, the molecular weight of the first water-immiscible organic solvent is 110 to 250 g / mol. More preferably, the molecular weight of the first water-immiscible organic solvent is 120 to 225 g / mol. Without wishing to be bound by theory, it is believed that molecular weights in these preferred ranges help promote the formation of stable microcapsules of a desired size (e.g., 5 to 50 μm) upon dilution with water.

[0053] In a preferred embodiment, the molecular weight of the first water-immiscible organic solvent is 130 to 160 g / mol, and in another preferred embodiment, the molecular weight of the first water-immiscible organic solvent is 185 to 215 g / mol.

[0054] Preferably, the kinematic viscosity of the first water-immiscible organic solvent is 1.0 to 20.0 mPa·s at 20°C. More preferably, the kinematic viscosity of the first water-immiscible organic solvent is 3.0 to 10.0 mPa·s at 20°C. Even more preferably, the kinematic viscosity of the first water-immiscible organic solvent is 3.5 to 8.0 mPa·s at 20°C. Without wishing to be bound by theory, it is believed that a kinematic viscosity in these preferred ranges promotes the formation of stable microcapsules of a desired size (e.g., 5 to 50 μm) when diluted with water.

[0055] In a preferred embodiment, the kinematic viscosity of the first water-immiscible organic solvent is 3.0 to 5.0 mPa·s at 20° C., or 3.5 to 4.5 mPa·s at 20° C. In another preferred embodiment, the kinematic viscosity of the first water-immiscible organic solvent is 6.5 to 8.5 mPa·s at 20° C., or 7.0 to 8.0 mPa·s at 20° C.

[0056] Preferably, the first water-immiscible organic solvent is biodegradable. The use of a biodegradable solvent eliminates the need for evaporation of the solvent used to dissolve the biodegradable polymer and / or the active agricultural chemical ingredient, and the subsequent separation and drying of the microcapsules.

[0057] Preferably, the first water-immiscible organic solvent comprises n-butyl L-lactate or 2-ethylhexyl L-lactate. n-Butyl L-lactate is commercially available, for example, from Corbion under the trade name Purasolv® BL. Purasolv® BL has a molecular weight of 146 g / mol and a kinematic viscosity at 20°C of 3.9 mPa·s. 2-Ethylhexyl L-lactate is commercially available, for example, from Corbion under the trade name Purasolv® EHL. Purasolv® EHL has a molecular weight of 202 g / mol and a kinematic viscosity at 20°C of 7.6 mPa·s.

[0058] Preferably, the first water-immiscible organic solvent is present in an amount of 10 to 50% w / w. More preferably, the first water-immiscible organic solvent is present in an amount of 15 to 45% w / w. Most preferably, the first water-immiscible organic solvent is present in an amount of 20 to 40% w / w. Without wishing to be bound by theory, it is believed that the presence of the first water-immiscible organic solvent in these preferred ranges promotes the formation of stable microcapsules of a desired size (e.g., 5 to 50 μm) upon dilution with water.

[0059] In a preferred embodiment, the composition comprises a second water-immiscible organic solvent, wherein the second water-immiscible organic solvent comprises n-butyl L-lactate or 2-ethylhexyl L-lactate, with the proviso that the first water-immiscible organic solvent is different from the second water-immiscible organic solvent.

[0060] Preferably, the second water-immiscible organic solvent is biodegradable. The use of a biodegradable solvent eliminates the need for evaporation of the solvent used to dissolve the biodegradable polymer and / or the active agricultural chemical ingredient, and the subsequent separation and drying of the microcapsules.

[0061] Preferably, the second water-immiscible organic solvent is present in an amount of 0-10% w / w, more preferably, the second water-immiscible organic solvent is present in an amount of 0-7.5% w / w, and most preferably, the second water-immiscible organic solvent is present in an amount of 0-5.0% w / w.

[0062] Alternatively, if present, the second water-immiscible organic solvent is preferably present in an amount of 0.5 to 10% w / w, more preferably 1.0 to 7.5% w / w, and most preferably 1.4 to 5.0% w / w or 2.0 to 5.0% w / w.

[0063] Preferably, the total amount of water-immiscible organic solvents in the composition is 10 to 60% w / w, more preferably 15 to 50% w / w, and most preferably 20 to 40% w / w.

[0064] Preferably, the weight ratio of the water-miscible organic solvent to the first water-immiscible organic solvent and the second water-immiscible organic solvent is 1:10 to 1:1. More preferably, the weight ratio of the water-miscible organic solvent to the first water-immiscible organic solvent and the second water-immiscible organic solvent is 1:8 to 1:1.5. Even more preferably, the weight ratio of the water-miscible organic solvent to the first water-immiscible organic solvent and the second water-immiscible organic solvent is 1:5 to 1:2. Most preferably, the weight ratio of the water-miscible organic solvent to the first water-immiscible organic solvent and the second water-immiscible organic solvent is 1:4 to 1:3. Without being bound by theory, it is believed that when the weight ratio of the water-miscible organic solvent to the first water-immiscible organic solvent and the second water-immiscible organic solvent is within these preferred ranges, the formation of stable microcapsules of a desired size (e.g., 5 to 50 μm) is promoted upon dilution with water.

[0065] Preferably, the emulsifier has a kinematic viscosity of 500 to 2500 mPa·s at 20° C., or 750 to 2000 mPa·s at 20° C. More preferably, the emulsifier has a kinematic viscosity of 1000 to 1800 mPa·s at 20° C. Most preferably, the emulsifier has a kinematic viscosity of 1100 to 1500 mPa·s at 20° C.

[0066] Preferably, the emulsifier comprises an ethoxylated propoxylated polyarylphenol. In a more preferred embodiment, the emulsifier consists of an ethoxylated propoxylated polyarylphenol. The ethoxylated propoxylated polyarylphenol has a kinematic viscosity of 1300 mPa·s at 20°C and is available from Azelis under the trade name Soprophor® 796 / P. Without wishing to be bound by theory, it is believed that the use of an ethoxylated propoxylated polyarylphenol as an emulsifier promotes the formation of stable microcapsules of a desired size (e.g., 5-50 μm) upon dilution with water.

[0067] Preferably, the emulsifier is biodegradable.

[0068] Preferably, the emulsifier is present in an amount of 5 to 30% w / w. More preferably, the emulsifier is present in an amount of 7.5 to 27.5% w / w. Even more preferably, the emulsifier is present in an amount of 10 to 25% w / w. Most preferably, the emulsifier is present in an amount of 12 to 22.5% w / w or 12 to 20% w / w. Without wishing to be bound by theory, it is believed that the presence of the emulsifier in these preferred ranges promotes the formation of stable microcapsules of a desired size (e.g., 5 to 50 μm) upon dilution with water.

[0069] Preferably, the composition further comprises a UV stabilizer.

[0070] Preferably, when the composition of the first aspect is added to water, microcapsules having a median diameter of 5 to 50 μm are formed, at least a portion of the microcapsule walls are formed from a biodegradable polymer, and the microcapsules contain at least a portion of the active pesticide ingredient.More preferably, when the composition of the first aspect is added to water, microcapsules having a median diameter of 5 to 50 μm are formed, at least a portion of the microcapsule walls are formed from a biodegradable polymer, and the microcapsules contain the active pesticide ingredient.

[0071] Preferably, the composition comprises: 30-50% w / w of pesticide active ingredient; 2-20% w / w of a water-miscible organic solvent; 10-50% w / w of a first water-immiscible organic solvent; 10-25% w / w emulsifier; - 1-5% w / w of a biodegradable polymer; and 0-10% w / w of a second water-immiscible organic solvent; Comprising, consisting essentially of, or consisting of.

[0072] More preferably, the composition comprises: 32-50% w / w pesticide active ingredient; 4-15% w / w of a water-miscible organic solvent; 10-50% w / w of a first water-immiscible organic solvent; 10-25% w / w emulsifier; 1.5 to 4.5% w / w of a biodegradable polymer; and 0-7.5% w / w of a second water-immiscible organic solvent; Comprising, consisting essentially of, or consisting of.

[0073] More preferably, the composition comprises: 32-49% w / w pesticide active ingredient; 4-15% w / w of a water-miscible organic solvent; 15-45% w / w of a first water-immiscible organic solvent; 10-25% w / w emulsifier; 1.5 to 4.5% w / w of a biodegradable polymer; and 0-7.5% w / w of a second water-immiscible organic solvent; Comprising, consisting essentially of, or consisting of.

[0074] Most preferably, the composition comprises: 35-48% w / w pesticide active ingredient; 5-13% w / w of water-miscible organic solvent; 20-40% w / w of a first water-immiscible organic solvent; 12-20% w / w emulsifier; 2.0 to 4.0% w / w of a biodegradable polymer; and 0-5.0% w / w of a second water-immiscible organic solvent; Comprising, consisting essentially of, or consisting of.

[0075] Alternatively, the composition comprises: 35-50% w / w of pesticide active ingredient; 5-13% w / w of water-miscible organic solvent; 20-40% w / w of a first water-immiscible organic solvent; 12-22.5% w / w emulsifier; 2.0 to 4.0% w / w of a biodegradable polymer; and 0-5.0% w / w of a second water-immiscible organic solvent; Comprising, consisting essentially of, or consisting of.

[0076] In a preferred embodiment, the composition essentially comprises: pesticide active ingredients; Water-miscible organic solvents; a first water-immiscible organic solvent; emulsifier; biodegradable polymers; optionally a second water-immiscible organic solvent; and Optionally, UV stabilizers; It consists of Here, the active agricultural chemical ingredient is soluble in the water-miscible organic solvent and / or the first water-immiscible organic solvent and / or a mixture of the water-miscible organic solvent and the first water-immiscible organic solvent.

[0077] In a preferred embodiment, the composition comprises: pesticide active ingredients; Water-miscible organic solvents; a first water-immiscible organic solvent; emulsifier; biodegradable polymers; optionally a second water-immiscible organic solvent; and Optionally, UV stabilizers; It consists of Here, the active agricultural chemical ingredient is soluble in the water-miscible organic solvent and / or the first water-immiscible organic solvent and / or a mixture of the water-miscible organic solvent and the first water-immiscible organic solvent.

[0078] Preferably, the composition does not include non-biodegradable polymers.

[0079] Preferably, the composition does not contain non-biodegradable organic solvents.

[0080] Preferably, the composition does not include non-biodegradable emulsifiers.

[0081] Preferably, the composition is free of non-biodegradable polymers, free of non-biodegradable organic solvents, and free of non-biodegradable emulsifiers.

[0082] Preferably, the composition of the first aspect is a clear (ie, transparent) solution.

[0083] The active pesticide ingredient, the water-miscible organic solvent, the first water-immiscible organic solvent, the emulsifier, the biodegradable polymer, and the optional second water-immiscible organic solvent are chemically distinct from one another, e.g., the water-immiscible organic solvent is chemically distinct from the emulsifier.

[0084] In a second aspect, the present invention provides a method of making the composition of the first aspect, the method comprising: combining a biodegradable polymer and a first water-immiscible organic solvent to form a first mixture; adding a water-miscible organic solvent and optionally a second water-immiscible organic solvent to the first mixture to form a second mixture; adding an active pesticide ingredient to the second mixture to form a third mixture; and adding an emulsifier to the third mixture; Including, Here, the active agricultural chemical ingredient is soluble in the water-miscible organic solvent and / or the first water-immiscible organic solvent and / or a mixture of the water-miscible organic solvent and the first water-immiscible organic solvent.

[0085] Preferred characteristics of the pesticide active ingredient, the water-miscible organic solvent, the first water-immiscible organic solvent, the emulsifier, the biodegradable polymer, and the optional second water-immiscible organic solvent are as described above in relation to the composition of the first aspect.

[0086] Preferably, the composition formed by the method of the second aspect is a clear solution.

[0087] Preferably, the method does not include evaporating or otherwise removing the first water-immiscible organic solvent and / or the water-miscible organic solvent and / or any second water-immiscible organic solvent. More preferably, the method does not include evaporating or otherwise removing any of the first water-immiscible organic solvent, the water-miscible organic solvent, and any second water-immiscible organic solvent.

[0088] In a third aspect, the present invention provides a method of making a composition of the first aspect, the method comprising: combining a biodegradable polymer and a water-miscible organic solvent to form a first mixture; adding a first water-immiscible organic solvent and optionally a second water-immiscible organic solvent to the first solution to form a second mixture; adding a pesticide active ingredient to the second mixture to form a third mixture; and adding an emulsifier to the third mixture; Here, the pesticide active ingredient is soluble in the water-miscible organic solvent and / or the first water-immiscible organic solvent and / or a mixture of the water-miscible organic solvent and the first water-immiscible organic solvent.

[0089] Preferred characteristics of the pesticide active ingredient, the water-miscible organic solvent, the first water-immiscible organic solvent, the emulsifier, the biodegradable polymer, and the optional second water-immiscible organic solvent are as described above in relation to the composition of the first aspect.

[0090] Preferably, the composition formed by the method of the third aspect is a clear solution.

[0091] Preferably, the method does not include evaporating or otherwise removing the first water-immiscible organic solvent and / or the water-miscible organic solvent and / or any second water-immiscible organic solvent. More preferably, the method does not include evaporating or otherwise removing any of the first water-immiscible organic solvent, the water-miscible organic solvent, and any second water-immiscible organic solvent.

[0092] In a fourth aspect, the present invention provides a method for producing a composition comprising: water; pesticide active ingredients; Water-miscible organic solvents; a first water-immiscible organic solvent; emulsifier; biodegradable polymers; and optionally a second water-immiscible organic solvent; providing a formulation comprising wherein the pesticidal active ingredient is soluble in the water-miscible organic solvent and / or the first water-immiscible organic solvent and / or a mixture of the water-miscible organic solvent and the first water-immiscible organic solvent; wherein the formulation comprises microcapsules having walls formed at least in part from a biodegradable polymer, the microcapsules containing at least a portion of the pesticidal active ingredient; Here, the microcapsules have a median diameter of 5 to 50 μm.

[0093] Preferred characteristics of the pesticide active ingredient, the water-miscible organic solvent, the first water-immiscible organic solvent, the emulsifier, the biodegradable polymer, and the optional second water-immiscible organic solvent are as described above in relation to the composition of the first aspect.

[0094] Preferably, the formulation comprises microcapsules having walls formed from a biodegradable polymer, the microcapsules containing an active pesticide ingredient.

[0095] Preferably, the D50 median diameter of the microcapsules is 10 to 30 μm, more preferably 10 to 20 μm.

[0096] Preferably, the formulation does not include non-biodegradable polymers.

[0097] Preferably, the formulation does not contain non-biodegradable organic solvents.

[0098] Preferably, the formulation does not include non-biodegradable emulsifiers.

[0099] Preferably, the formulation is free of non-biodegradable polymers, free of non-biodegradable organic solvents, and free of non-biodegradable emulsifiers.

[0100] In one preferred embodiment, the formulation comprises: water; pesticide active ingredients; Water-miscible organic solvents; a first water-immiscible organic solvent; emulsifier; biodegradable polymers; and optionally a second water-immiscible organic solvent; any UV stabilizers; consisting essentially of or consisting of wherein the pesticidal active ingredient is soluble in the water-miscible organic solvent and / or the first water-immiscible organic solvent and / or a mixture of the water-miscible organic solvent and the first water-immiscible organic solvent; wherein the formulation comprises microcapsules having walls formed at least in part from a biodegradable polymer, the microcapsules containing at least a portion of the pesticidal active ingredient; Here, the microcapsules have a median diameter of 5 to 50 μm.

[0101] In a fifth aspect, the present invention provides a method of making a formulation of the fourth aspect, the method comprising adding a composition of the first aspect to water.

[0102] Preferably, the method of making the formulation of the fourth aspect does not involve evaporating or otherwise removing the first water-immiscible organic solvent and / or the water-miscible organic solvent and / or the optional second water-immiscible organic solvent. More preferably, the method does not involve evaporating or otherwise removing any of the first water-immiscible organic solvent, the water-miscible organic solvent, and the optional second water-immiscible organic solvent.

[0103] Preferably, the process for producing the formulation of the fourth aspect does not involve filtering and / or washing and / or drying the microcapsules, more preferably the process does not involve filtering, washing or drying the microcapsules.

[0104] Preferably, the method of making the formulation of the fourth aspect comprises adding the composition of the first aspect to water.

[0105] In a sixth aspect, the present invention provides a method of protecting crops, the method comprising applying to the crops a formulation of the fourth aspect.

[0106] In one preferred embodiment, the crop comprises oilseed rape.

[0107] In a seventh aspect, the present invention provides a method of making a composition of the first aspect, the method comprising: combining a biodegradable polymer and a first water-immiscible organic solvent to form a first mixture; adding a water-miscible organic solvent and optionally a second water-immiscible organic solvent to the first mixture to form a second mixture; adding an emulsifier to the second mixture to form a third mixture; and adding a pesticide active ingredient to the third mixture; Including, Here, the pesticide active ingredient is soluble in the water-miscible organic solvent and / or the first water-immiscible organic solvent and / or a mixture of the water-miscible organic solvent and the first water-immiscible organic solvent.

[0108] Preferred characteristics of the pesticide active ingredient, the water-miscible organic solvent, the first water-immiscible organic solvent, the emulsifier, the biodegradable polymer, and the optional second water-immiscible organic solvent are as described above in relation to the composition of the first aspect.

[0109] Preferably, the composition formed by the method of the seventh aspect is a clear solution.

[0110] Preferably, the method does not include evaporating or otherwise removing the first water-immiscible organic solvent and / or the water-miscible organic solvent and / or any second water-immiscible organic solvent. More preferably, the method does not include evaporating or otherwise removing any of the first water-immiscible organic solvent, the water-miscible organic solvent, and any second water-immiscible organic solvent.

[0111] In an eighth aspect, the present invention provides a method of making a composition of the first aspect, the method comprising: combining a biodegradable polymer and a water-miscible organic solvent to form a first mixture; adding a first water-immiscible organic solvent and optionally a second water-immiscible organic solvent to the first solution to form a second mixture; adding an emulsifier to the second mixture to form a third mixture; adding a pesticide active ingredient to the third mixture; Including, Here, the pesticide active ingredient is soluble in the water-miscible organic solvent and / or the first water-immiscible organic solvent and / or a mixture of the water-miscible organic solvent and the first water-immiscible organic solvent.

[0112] Preferred characteristics of the pesticide active ingredient, the water-miscible organic solvent, the first water-immiscible organic solvent, the emulsifier, the biodegradable polymer, and the optional second water-immiscible organic solvent are as described above in relation to the composition of the first aspect.

[0113] Preferably, the composition formed by the method of the eighth aspect is a clear solution.

[0114] Preferably, the method does not include evaporating or otherwise removing the first water-immiscible organic solvent and / or the water-miscible organic solvent and / or any second water-immiscible organic solvent. More preferably, the method does not include evaporating or otherwise removing any of the first water-immiscible organic solvent, the water-miscible organic solvent, and any second water-immiscible organic solvent.

[0115] In a ninth aspect, the present invention provides a composition for mixing with an active pesticide ingredient, the composition comprising: Water-miscible organic solvents; a first water-immiscible organic solvent; emulsifier; biodegradable polymers; optionally a second water-immiscible organic solvent; Including, Here, the active agricultural chemical ingredient is soluble in the water-miscible organic solvent and / or the first water-immiscible organic solvent and / or a mixture of the water-miscible organic solvent and the first water-immiscible organic solvent.

[0116] The composition of the first aspect may be formed by mixing the composition of the ninth aspect with an active agricultural chemical ingredient, preferably by emulsifying the composition of the ninth aspect with the active agricultural chemical ingredient; A composition according to the first aspect is prepared.

[0117] Preferably, before being mixed with the pesticide active ingredient, the composition of the ninth aspect comprises: 10-20% w / w of a water-miscible organic solvent; 40-60% w / w of a first water-immiscible organic solvent; 15-40% w / w emulsifier; 4-6% w / w of a biodegradable polymer; and 0-10% w / w of a second water-immiscible organic solvent; Includes.

[0118] Preferably, the composition of the ninth aspect is for mixing with an active pesticide ingredient comprising clomazone and / or acetochlor.

[0119] When introducing elements of this disclosure or preferred embodiments thereof, the articles "a," "an," "the," and "said" are intended to mean that there are one or more of the elements. The terms "comprising," "including," and "having" are intended to be inclusive and mean that there may be additional elements other than the listed elements.

[0120] The above detailed description has been provided for purposes of explanation and illustration and is not intended to limit the scope of the appended claims. Many variations of the presently preferred embodiments set forth herein will be apparent to those skilled in the art and remain within the scope of the appended claims and their equivalents.

[0121] These and other aspects of the present invention are described below with reference to the accompanying drawings: Figures 1a-1h show the phytotoxic effects of a comparative standard clomazone CS formulation and a clomazone ICS formulation of the present invention at four different application rates on oilseed rape after 14 days, and are described in more detail in the Examples section below. Figures 2a-2h show the efficacy of a comparative standard clomazone CS formulation and the clomazone ICS formulation of the present invention at four different application rates on chickweed after 17 days, and are described in more detail in the Examples section below.

[0122] Examples Section Unless otherwise stated, kinematic viscosity was measured at 25° C. using a standard viscometer (e.g., an Ubbelohde viscometer or an Anton-Parr MCR 102 viscometer).

[0123] Ethocel used in the examples TM The kinematic viscosity of Standard 10 Premium is Ethocel in 80% toluene / 20% ethanol. TM It was measured in the form of a 5% w / w solution of Standard 10 Premium at 25°C using an Anton-Parr MCR 102 viscometer.

[0124] The median diameter of the microcapsules (D50 median particle size) was measured by laser diffraction using a Malvern 300 Mastersizer. The solubility was measured at 20°C according to OECD Test Guideline 105. [Example]

[0125] The present invention will now be described with reference to several examples.

[0126] Example 1 Clomazone 360g / l in situ capsule suspension concentrate (ICS) formulation (Formulation A) [Table 1]

[0127] Manufacturing method Ethocel 10 was weighed into a 10 mL sample vial containing Purasorb BL. The vial was sealed with a cap and transferred to a magnetic heater / stirrer plate where it was mixed using a stir bar at 600 rpm. The mixture was stirred at room temperature for 30 minutes.

[0128] Agnique AMD3L was added to the mixture, followed by clomazone. The mixture was stirred on a magnetic heater / stirrer plate for 3 hours, after which Soprophor 796 / P was added. The mixture was stirred until the ethylcellulose was completely dissolved.

[0129] Example 2 Clomazone 360g / l in situ capsule suspension concentrate (ICS) formulation (Formulation B) [Table 2]

[0130] Manufacturing method Ethocel 10 was weighed into a 10 mL sample vial containing Purasolv EHL. The vial was sealed with a cap and transferred to a magnetic heater / stirrer plate where it was mixed using a stir bar at 600 rpm. The mixture was stirred at room temperature for 30 minutes.

[0131] Purasolv BL and Agnique AMD3L were added to the mixture, followed by clomazone. The mixture was stirred on a magnetic heater / stirrer plate for 3 hours, after which Soprophor 796 / P was added. The mixture was stirred until the ethylcellulose was completely dissolved.

[0132] Example 3 Clomazone 360 ​​g / l in situ capsule suspension concentrate (ICS) formulation (Formulation C) [Table 3]

[0133] Manufacturing method Ethocel 10 was weighed into a 10 mL sample vial containing Purasolv EHL. The vial was sealed with a cap and transferred to a magnetic heater / stirrer plate where it was mixed using a stir bar at 600 rpm. The mixture was stirred at room temperature for 30 minutes.

[0134] Purasolv BL and Agnique AMD3L were added to the mixture, followed by clomazone. The mixture was stirred on a magnetic heater / stirrer plate for 3 hours, after which Soprophor 796 / P was added. The mixture was stirred until the ethylcellulose was completely dissolved.

[0135] Example 4 Clomazone 360 ​​g / l in situ capsule suspension concentrate (ICS) formulation (Formulation D) [Table 4]

[0136] Manufacturing method Ethocel 10 was weighed into a 10 mL sample vial containing Purasolv EHL. The vial was sealed with a cap and transferred to a magnetic heater / stirrer plate where it was mixed using a stir bar at 600 rpm. The mixture was stirred at room temperature for 30 minutes.

[0137] Purasolv BL and Agnique AMD3L were added to the mixture, followed by clomazone. The mixture was stirred on a magnetic heater / stirrer plate for 3 hours, after which Soprophor 796 / P was added. The mixture was stirred until the ethylcellulose was completely dissolved.

[0138] Example 5 Clomazone 360 ​​g / l in situ capsule suspension concentrate (ICS) formulation (Formulation E) [Table 5]

[0139] Manufacturing method Ethocel 10 was weighed into a 10 mL sample vial containing Purasolv EHL. The vial was sealed with a cap and transferred to a magnetic heater / stirrer plate where it was mixed using a stir bar at 600 rpm. The mixture was stirred at room temperature for 30 minutes.

[0140] Purasolv BL and Agnique AMD3L were added to the mixture, followed by clomazone. The mixture was stirred on a magnetic heater / stirrer plate for 3 hours, after which Soprophor 796 / P was added. The mixture was stirred until the ethylcellulose was completely dissolved.

[0141] Example 6 Clomazone 360 ​​g / l in situ capsule suspension concentrate (ICS) formulation (Formulation F) [Table 6]

[0142] Manufacturing method Ethocel 10 was weighed into a 10 mL sample vial containing Purasolv EHL. The vial was sealed with a cap and transferred to a magnetic heater / stirrer plate where it was mixed using a stir bar at 600 rpm. The mixture was stirred at room temperature for 30 minutes.

[0143] Purasolv BL and Agnique AMD3L were added to the mixture, followed by clomazone. The mixture was stirred on a magnetic heater / stirrer plate for 3 hours, after which Soprophor 796 / P was added. The mixture was stirred until the ethylcellulose was completely dissolved.

[0144] Example 7 Clomazone 360 ​​g / l in situ capsule suspension concentrate (ICS) formulation (Formulation G) [Table 7]

[0145] Manufacturing method Ethocel 10 was weighed into a 10 mL sample vial containing Purasolv EHL. The vial was sealed with a cap and transferred to a magnetic heater / stirrer plate where it was mixed using a stir bar at 600 rpm. The mixture was stirred at room temperature for 30 minutes.

[0146] Purasolv BL and Agnique AMD3L were added to the mixture, followed by clomazone. The mixture was stirred on a magnetic heater / stirrer plate for 3 hours, after which Soprophor 796 / P was added. The mixture was stirred until the ethylcellulose was completely dissolved.

[0147] Example 8 Clomazone 480g / l in situ capsule suspension concentrate (ICS) formulation (Formulation H) [Table 8]

[0148] Manufacturing method Ethocel 10 was weighed into a 10 mL sample vial containing Purasolv EHL. The vial was sealed with a cap and transferred to a magnetic heater / stirrer plate where it was mixed using a stir bar at 600 rpm. The mixture was stirred at room temperature for 30 minutes.

[0149] Purasolv BL and Agnique AMD3L were added to the mixture, followed by clomazone. The mixture was stirred on a magnetic heater / stirrer plate for 3 hours, after which Soprophor 796 / P was added. The mixture was stirred until the ethylcellulose was completely dissolved.

[0150] Example 9 Acetochlor 360g / l in situ capsule suspension concentrate (ICS) formulation (Formulation I) [Table 9]

[0151] Manufacturing method Ethocel 10 was weighed into a 10 mL sample vial. Purasolve BL, Agnique AMD3L, Purasolve EHL, and a stir bar were added to the vial. The vial was sealed with a lid and transferred to a magnetic heater / stirrer plate. The stir bar was used for mixing at 600 rpm. The mixture was stirred at 40°C for 30 minutes.

[0152] Acetochlor was added to the mixture, and the mixture was stirred on a magnetic heater / stirrer plate at 40°C for 3 hours, after which Soprophor 796 / P was added. The mixture was stirred at room temperature until the ethylcellulose was completely dissolved and the solution was homogeneous.

[0153] Example 10 Acetochlor 480g / l in situ capsule suspension concentrate (ICS) formulation (Formulation J) [Table 10]

[0154] Manufacturing method Ethocel 10 was weighed into a 10 mL sample vial. Purasolve BL, Agnique AMD3L, Purasolve EHL, and a stir bar were added to the vial. The vial was sealed with a lid and transferred to a magnetic heater / stirrer plate. The stir bar was used for mixing at 600 rpm. The mixture was stirred at 40°C for 30 minutes. .

[0155] Acetochlor was added to the mixture, and the mixture was stirred on a magnetic heater / stirrer plate at 40°C for 3 hours, after which Soprophor 796 / P was added. The mixture was stirred at room temperature until the ethylcellulose was completely dissolved and the solution was homogeneous.

[0156] Comparative Example 11 Acetochlor 360g / l emulsifiable concentrate (EC) formulation (Acetochlor EC control) [Table 11]

[0157] Manufacturing method Acetochlor was weighed into a 10 mL sample vial. Purasorb BL, Agnique AMD3L, Purasorb EHL, Soprophor 796 / P, and a stir bar were added to the vial. The vial was sealed with a lid, transferred to a magnetic heater / stirrer plate, and mixed using the stir bar at 600 rpm. The mixture was mixed until homogeneous.

[0158] Volatile Research Laboratory testing for the volatility of clomazone in situ capsule suspension (ICS) formulations was performed as follows: A sufficient amount of unsterilized topsoil to conduct the test was passed twice through a 14-mesh sieve to remove large particles and debris. It was then passed through a 30-mesh sieve to remove fine particles, leaving a medium-grained topsoil. 240 grams of this medium-grained topsoil was evenly spread over an area of ​​approximately 27.9 cm x 41.3 cm in a 32.4 cm x 45.7 cm x 1.9 cm tray, approximately 1-2 mm thick. The clomazone test formulation, equivalent to 0.0712 g of active ingredient in 20 mL of water, was then applied to the topsoil. The clomazone test formulation was applied to the soil at a rate of 1.0 kg ai (active ingredient) / ha. Immediately after treatment, the soil was sealed in glass bottles and stored for a period until use.

[0159] For each clomazone test formulation, four 22 mm x 300 mm glass chromatography columns with a coarse sintered glass barrier at the bottom were connected at their bottoms to a multi-port air manifold, which simultaneously supplied equal air pressure to the columns. Each of the four columns was filled with 59 g of treated topsoil, filling approximately 200 mm of the column length. Immediately after soil treatment, a slow stream of air (0.5 L per minute per column) from the multi-port air manifold was passed through the soil in each column and then bubbled through an 80:20 mixture of acetonitrile and water, dissolving the volatilized clomazone into the solvent. The time between soil treatment and the start of airflow was approximately 1 hour. Airflow continued for approximately 20 hours. A 1 mL aliquot of this solution was analyzed for clomazone content using a standard high-performance liquid chromatography (HPLC) method.

[0160] The total clomazone content (in micrograms) of each sample was recorded and compared as a percentage to the clomazone content of the soil-applied sample.

[0161] The test results, shown in Table 1, demonstrate that the ICS formulation of the present invention is as effective at reducing the amount of clomazone lost due to volatilization as the standard clomazone CS formulation, Chromate®.

[0162] Table 1 [Table 12]

[0163] Laboratory testing for the volatility of acetochlor in situ capsule suspension (ICS) formulations was performed as follows: A sufficient amount of unsterilized topsoil to conduct the test was passed twice through a 14-mesh sieve to remove large particles and debris. It was then passed through a 30-mesh sieve to remove fine particles, leaving a medium-grained topsoil. 240 grams of this medium-grained topsoil was spread evenly over an area of ​​approximately 27.9 cm x 41.3 cm in a 32.4 cm x 45.7 cm x 1.9 cm tray, approximately 1-2 mm thick. The acetochlor test formulation, equivalent to 0.0712 g of active ingredient in 20 mL of water, was then applied to the topsoil. The acetochlor test formulation was applied to the soil at a rate of 1.0 kg ai (active ingredient) / ha. Immediately after treatment, the soil was sealed in glass bottles and stored for a period until use.

[0164] For each acetochlor test formulation, four 22 mm x 300 mm glass chromatography columns with a rough sintered glass barrier at the bottom were connected at their bottoms to a multi-port air manifold, which simultaneously supplied equal air pressure to the columns. Each of the four columns was filled with 40 g of treated topsoil, filling approximately 200 mm of the column length. Immediately after soil treatment, a slow stream of air (0.25 L per minute per column) from the multi-port air manifold was passed through the soil in each column and then bubbled through an 80:20 mixture of acetonitrile and water, dissolving the volatilized acetochlor into the solvent. The time between soil treatment and the start of air flow was approximately 1 hour. Air flow continued for approximately 20 hours. A 1 mL aliquot of this solution was analyzed for acetochlor content using a standard high-performance liquid chromatography (HPLC) method.

[0165] The total acetochlor content (in micrograms) of each sample was recorded and compared as a percentage to the acetochlor content of the soil-applied sample.

[0166] The test results, shown in Table 2, demonstrate that the ICS formulation of the present invention is significantly more effective at reducing the amount of acetochlor lost to volatilization than an acetochlor EC formulation containing the same solvent and emulsifier but without Ethocel.

[0167] Table 2 [Table 13]

[0168] Crop Safety Research A study to determine the phytotoxicity of the clomazone ICS formulation when applied to crops compared to the standard clomazone CS formulation was conducted as follows: One study of Formulation A was conducted on rapeseed (Brassicanapus) seeds. In this study, four seeds were sown in each of seven individual plant sponge replicates while providing constant watering and LED lighting (16 hours on, 8 hours off in a 24-hour cycle) using an AQUA LED Hydroponic System A-03. Five such hydroponic tanks were filled with 5 liters of water containing a nutrient solution (50 ml, total: 23% N, 59% PO, 30% KO, 7% MgO, 15% CaO, 0.3% EDTA-FE, 0.06% EDTA-Mn, 0.005% EDTA-Cu, 0.01% EDTA-Zn, 0.1% B) and various concentrations of Formulation A (0.129 ml, equivalent to 1 / 64 of the dose; 0.064 ml, equivalent to 1 / 128 of the dose; 0.032 ml, equivalent to 1 / 256 of the dose; and 0.016 ml, equivalent to 1 / 512 of the dose). Phytotoxic effects on the growth of rapeseed crops were evaluated after 14 days. An untreated control was also included in the study.

[0169] The test was repeated using the same volume of a standard clomazone CS formulation, prepared by conventional interfacial polymerization, diluted into the nutrient solution. To prevent cross-contamination, plastic sleeves were placed around each tank, and the sleeves were replaced before applying a new test formulation to the nutrient solution. The test was evaluated by observing the phytotoxicity of the oilseed rape plants 14 days after treatment.

[0170] Phytotoxic effects on day 14 were compared as shown in Figures 1a-1h. Figure 1a shows rapeseed plants treated with a standard clomazone CS formulation (comparison) at a rate of 1 / 64N. Figure 1c shows rapeseed plants treated with a standard clomazone CS formulation (comparison) at a rate of 1 / 128N. Figure 1e shows rapeseed plants treated with a standard clomazone CS formulation (comparison) at a rate of 1 / 256N. Figure 1g shows rapeseed plants treated with a standard clomazone CS formulation (comparison) at a rate of 1 / 512N. Figure 1b shows rapeseed plants treated with a standard clomazone ICS formulation (invention) at a rate of 1 / 64N. Figure 1d shows rapeseed plants treated with a standard clomazone ICS formulation (invention) at a rate of 1 / 128N. Figure 1f shows rapeseed plants treated with a standard clomazone ICS formulation (of the invention) at a rate of 1 / 256 N. Figure 1h shows rapeseed plants treated with a standard clomazone ICS formulation (of the invention) at a rate of 1 / 512 N.

[0171] The chlorotic areas and vigor of the rapeseed were observed and compared between the test formulations. The study showed that Formulation A provided equivalent crop safety compared to the standard clomazone CS formulation.

[0172] Efficacy studies A study to determine the weed efficacy of the clomazone ICS formulation compared to the standard clomazone CS formulation was conducted as follows: One study of Formulation A was conducted on chickweed seeds (Stellaria media). In this study, four seeds were sown in each of seven individual plant sponge replicates using an AQUA LED Hydroponic System A-03, providing constant watering and LED lighting (16 hours on, 8 hours off in a 24-hour cycle). Five such hydroponic tanks were filled with 5 liters of water containing a nutrient solution (50 ml, total: 23% N, 59% PO, 30% KO, 7% MgO, 15% CaO, 0.3% EDTA-FE, 0.06% EDTA-Mn, 0.005% EDTA-Cu, 0.01% EDTA-Zn, 0.1% B) and various concentrations of Formulation A (0.129 ml, equivalent to 1 / 64 of the dose; 0.064 ml, equivalent to 1 / 128 of the dose; 0.032 ml, equivalent to 1 / 256 of the dose; and 0.016 ml, equivalent to 1 / 512 of the dose). The effects on chickweed growth were evaluated after 17 days. An untreated control was also included in the study.

[0173] The test was repeated using the same volume of a standard clomazone CS formulation, prepared by conventional interfacial polymerization, diluted into the nutrient solution. To prevent cross-contamination, a plastic sleeve was placed around each tank, and the sleeve was replaced before applying a new test formulation to the nutrient solution. The test was evaluated by observing the effect on chickweed 17 days after treatment.

[0174] The effects of different application rates were compared on day 17, as shown in Figures 2a-2h. Figure 2a shows chickweed treated with a standard clomazone CS formulation (comparison) at a rate of 1 / 64N. Figure 2c shows chickweed treated with a standard clomazone CS formulation (comparison) at a rate of 1 / 128N. Figure 2e shows chickweed treated with a standard clomazone CS formulation (comparison) at a rate of 1 / 256N. Figure 2g shows chickweed treated with a standard clomazone CS formulation (comparison) at a rate of 1 / 512N. Figure 2b shows chickweed treated with a standard clomazone ICS formulation (invention) at a rate of 1 / 64N. Figure 2d shows chickweed treated with a standard clomazone ICS formulation (invention) at a rate of 1 / 128N. Figure 2f shows chickweed treated with a standard clomazone ICS formulation (invention) at a rate of 1 / 256N. Figure 2h shows chickweed treated with a standard clomazone ICS formulation (invention) at a rate of 1 / 512N.

[0175] The test results show that formulation A of the present invention provided comparable control efficacy compared to the standard clomazone CS product (comparison).

Claims

1. Pesticide active ingredients; Water-miscible organic solvents; a first water-immiscible organic solvent; emulsifier; a biodegradable polymer; and optionally a second water-immiscible organic solvent; A composition comprising: The composition, wherein the pesticide active ingredient is soluble in the water-miscible organic solvent and / or the first water-immiscible organic solvent and / or a mixture of the water-miscible organic solvent and the first water-immiscible organic solvent.

2. The composition comprises: 30-50% w / w of pesticide active ingredient; 2-20% w / w of a water-miscible organic solvent; 10-50% w / w of a first water-immiscible organic solvent; 10-25% w / w of an emulsifier; - 1-5% w / w of a biodegradable polymer; and 0-10% w / w of a second water-immiscible organic solvent; The composition of claim 1 comprising:

3. 10. The composition of any preceding claim, wherein the pesticidal active ingredient comprises a herbicide, insecticide, and / or fungicide.

4. 10. The composition of any preceding claim, wherein the pesticidal active ingredient comprises a herbicide.

5. 10. The composition of any preceding claim, wherein the pesticidal active ingredient comprises clomazone.

6. 10. The composition of any preceding claim, wherein the pesticidal active ingredient comprises acetochlor.

7. 10. The composition according to claim 1, wherein the biodegradable polymer has a dynamic viscosity of 2.0 to 20.0 mPa·s.

8. 10. The composition of claim 1, wherein the biodegradable polymer comprises a polysaccharide.

9. 10. A composition according to any preceding claim, wherein the biodegradable polymer comprises cellulose and / or starch.

10. 10. The composition of any preceding claim, wherein the biodegradable polymer comprises ethyl cellulose.

11. 10. The composition according to claim 1, wherein the water-miscible organic solvent has a kinematic viscosity of 2 to 10 mPa s at 25°C.

12. 10. The composition of claim 1, wherein the water-miscible organic solvent comprises 2-hydroxy-N,N-dimethylpropanamide.

13. 10. The composition of claim 1, wherein the molecular weight of the first water-immiscible organic solvent is from 100 to 300 g / mol.

14. 10. The composition of claim 1, wherein the first water-immiscible organic solvent has a kinematic viscosity of 3.0 to 10.0 mPa s at 20°C.

15. 2. The composition of claim 1, wherein the first water-immiscible organic solvent comprises n-butyl L-lactate or 2-ethylhexyl L-lactate.

16. 10. The composition of claim 1, wherein the composition comprises a second water-immiscible organic solvent, wherein the second water-immiscible organic solvent comprises n-butyl L-lactate or 2-ethylhexyl L-lactate, with the proviso that the first water-immiscible organic solvent is different from the second water-immiscible organic solvent.

17. 10. A composition according to any preceding claim, wherein the emulsifier has a kinematic viscosity of 1100 to 1500 mPa s at 20°C.

18. 10. The composition of any preceding claim, wherein the emulsifier comprises an ethoxylated propoxylated polyarylphenol.

19. 10. The composition of any preceding claim, further comprising an ultraviolet stabilizer.

20. 10. The composition of claim 9, wherein the weight ratio of the water-miscible organic solvent to the first water-immiscible organic solvent and the second water-immiscible organic solvent is from 1:5 to 1:

2.

21. 10. The composition of claim 9, wherein upon addition of the composition to water, microcapsules having a median diameter of 5 to 50 μm are formed, at least a portion of the microcapsule wall being formed from a biodegradable polymer, and the microcapsules contain at least a portion of the pesticidal active ingredient.

22. combining a biodegradable polymer and a first water-immiscible organic solvent to form a first mixture; adding a water-miscible organic solvent and optionally a second water-immiscible organic solvent to the first mixture to form a second mixture; adding an active pesticide ingredient to the second mixture to form a third mixture; and adding an emulsifier to the third mixture; Including, 10. The method for producing a composition according to claim 9, wherein the pesticidal active ingredient is soluble in the water-miscible organic solvent and / or the first water-immiscible organic solvent and / or a mixture of the water-miscible organic solvent and the first water-immiscible organic solvent.

23. combining a biodegradable polymer and a water-miscible organic solvent to form a first mixture; adding a first water-immiscible organic solvent and optionally a second water-immiscible organic solvent to the first solution to form a second mixture; adding an active pesticide ingredient to the second mixture to form a third mixture; and adding an emulsifier to the third mixture; Including, The method for producing a composition according to any one of claims 1 to 21, wherein the pesticidal active ingredient is soluble in the water-miscible organic solvent and / or the first water-immiscible organic solvent and / or a mixture of the water-miscible organic solvent and the first water-immiscible organic solvent.

24. combining a biodegradable polymer and a first water-immiscible organic solvent to form a first mixture; adding a water-miscible organic solvent and optionally a second water-immiscible organic solvent to the first mixture to form a second mixture; adding an emulsifier to the second mixture to form a third mixture; and adding an active pesticide ingredient to the third mixture; Including, The method for producing a composition according to any one of claims 1 to 21, wherein the pesticidal active ingredient is soluble in the water-miscible organic solvent and / or the first water-immiscible organic solvent and / or a mixture of the water-miscible organic solvent and the first water-immiscible organic solvent.

25. combining a biodegradable polymer and a water-miscible organic solvent to form a first mixture; adding a first water-immiscible organic solvent and optionally a second water-immiscible organic solvent to the first solution to form a second mixture; adding an emulsifier to the second mixture to form a third mixture; adding an active pesticide ingredient to the third mixture; Including, The method for producing a composition according to any one of claims 1 to 21, wherein the pesticidal active ingredient is soluble in the water-miscible organic solvent and / or the first water-immiscible organic solvent and / or a mixture of the water-miscible organic solvent and the first water-immiscible organic solvent.

26. water; Pesticide active ingredients; Water-miscible organic solvents; a first water-immiscible organic solvent; emulsifier; a biodegradable polymer; and optionally a second water-immiscible organic solvent; Including, wherein the agricultural chemical active ingredient is soluble in the water-miscible organic solvent and / or the first water-immiscible organic solvent and / or a mixture of the water-miscible organic solvent and the first water-immiscible organic solvent; wherein the formulation comprises microcapsules having walls formed at least in part from a biodegradable polymer, wherein the microcapsules contain at least a portion of the pesticidal active ingredient; A formulation wherein the microcapsules have a D50 median diameter of 5 to 50 μm.

27. A method for preparing a formulation according to claim 26, comprising adding a composition according to any one of claims 1 to 21 to water.

28. 27. A method of protecting crops comprising applying to the crops the formulation of claim 26.

29. 1. A composition for mixing with an active pesticide ingredient, the composition comprising: Water-miscible organic solvents; a first water-immiscible organic solvent; emulsifier; a biodegradable polymer; and optionally a second water-immiscible organic solvent; Including, The composition, wherein the pesticide active ingredient is soluble in the water-miscible organic solvent and / or the first water-immiscible organic solvent and / or a mixture of the water-miscible organic solvent and the first water-immiscible organic solvent.

30. 10-20% w / w of a water-miscible organic solvent; 40-60% w / w of a first water-immiscible organic solvent; 15-40% w / w of an emulsifier; 4-6% w / w of a biodegradable polymer; and 0-10% w / w of a second water-immiscible organic solvent; 30. The composition of claim 29, comprising:

31. 31. The composition of claim 30 for mixing with an active pesticide ingredient comprising clomazone and / or acetochlor.

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