Improved HPPD and PPO pesticide formulations containing drift reduction technology

Abstract

Provided herein are improved pesticide formulations and methods of treating crops, the pesticide formulations comprising at least one herbicide selected from the group consisting of 4-hydroxyphenylpyruvate dioxygenase herbicides and protoporphyrinogen oxidase inhibitor herbicides; and an organic drift control agent.

Description

[Technical field]

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS This application claims priority to pending U.S. Provisional Patent Application No. 63 / 346,591, filed May 27, 2022, which is incorporated herein by reference.

[0002] FIELD OF THEINVENTION The present disclosure relates to improved formulations for use in treating crops. More specifically, the present invention relates to improved crop treatment formulations having improved drift control properties. [Background technology]

[0003] background Existing technology utilizes 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibiting and protoporphyrinogen oxidase (PPO) inhibiting herbicides and drift control agents (DRAs) added separately to the tank mix. DRAs are effective in controlling the spray pattern during herbicide application. Oil-based DRAs are sometimes most preferred because they reduce the amount of fine particles while limiting the impact on the average spray particle size, which can be important for herbicide deposition and performance. Common HPPD and PPO inhibiting herbicides, such as mesotrione and sulfentrazone, when formulated alone, are typically formulated as concentrated suspensions. The inclusion of oil-based products typically requires the formulation type to be adjusted to a suspoemulsion. Suspoemulsion-based formulations are known in the art to have formulation stability issues, and the use of different additives, including copper chelating additives and additives that encapsulate oil-based materials, has been required to overcome chemical and physical stability challenges. It is also expected that the inclusion of oil-based DRA will require a suspoemulsion-type formulation, which is often associated with accelerated herbicide degradation. Driven by the challenge of physical and chemical stability in the presence of oil, most formulation manufacturers have explored the use of water-based drift-reducing polymers, such as polyacrylamides, polyacrylates, and guar gum, with these herbicides. However, as has been recently discovered, water-based drift-reducing polymers can adversely affect the stability of the formulation, in particular by causing high viscosity and gelling, so that formulations containing them are less effective at reducing the fraction of fine particles. There has been a need in the art for a stable canned product that combines oil-based DRA and HPPD- and / or PPO-inhibiting herbicides in an aqueous system without degradation of the active substances, yet exhibits acceptable physical stability and reduces spray particle size for the purpose of reducing drift. Such a need has not been met in the art. Summary of the Invention [Means for solving the problem]

[0004] Summary of the Invention The present invention relates to an improved crop treatment formulation comprising an HPPD-inhibiting herbicide and a PPO-inhibiting herbicide, and an oil-based drift reducing agent. The HPPD and PPO-inhibiting herbicide can be formulated separately or together in a formulation containing multiple active herbicides.

[0005] One particular feature of the present invention is stability, particularly chemical and physical stability, without unacceptable separation of the components of the formulation or degradation of the herbicidal active ingredient.

[0006] Another particular feature of the present invention is the reduction of fines, defined as particles less than 150 microns, resulting in less off-target deposition.

[0007] These and other embodiments, as will be appreciated, at least one herbicide selected from the group consisting of 4-hydroxyphenylpyruvate dioxygenase herbicides and protoporphyrinogen oxidase inhibitor herbicides; and Oil-based drift control agent The present invention is provided in an agrochemical formulation comprising:

[0008] Yet another embodiment is a method of treating a crop comprising: at least one herbicide selected from the group consisting of 4-hydroxyphenylpyruvate dioxygenase-inhibiting herbicides and protoporphyrinogen oxidase-inhibiting herbicides; and Oil-based drift control agent spraying said crop with an agrochemical formulation. The method includes: [Brief description of the drawings]

[0009] [Figure 1] Figure 1 shows a graph of downwind deposition. [Diagram 2] Figure 2 shows a graph of downwind deposition. [Diagram 3]Figure 3 shows a graph of downwind deposition. [Figure 4] FIG. 4 plots the wt% of fine particles less than 150 μm. [Diagram 5] FIG. 5 plots the wt% of fine particles less than 150 μm. [Figure 6] FIG. 6 plots the wt% of fine particles less than 150 μm. [Figure 7] FIG. 7 plots the wt% of fine particles less than 150 μm. [Figure 8] FIG. 8 plots the wt% of fine particles less than 150 μm. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0010] explanation The present invention relates to improved crop treatment formulations, particularly crop treatment formulations that are stable and provide good drift control properties. More specifically, the present invention relates to a stable canned product that combines oil-based DRA with HPPD and PPO-inhibiting herbicides in an aqueous system without degradation of the active ingredients, which is then diluted and preferably applied by spraying.

[0011] With the advent of herbicide-tolerant (HT) crops, new use patterns are emerging for HPPD and PPO-inhibiting herbicides. Expanded use windows and new uses across crops may increase the potential for off-target migration of these herbicides. The present invention reduces the number of fine particles from the spray, and therefore the amount of product that can migrate off-target due to particle drift. This type of oil-based drift reducing agent is preferred for use with these products, as it is less likely to increase the average spray particle size while reducing fine particles compared to water-based polymers such as polyacrylamide, which may mean less impact on herbicide efficacy. The presence of the oil-based drift reducing technology in the herbicide ensures its use in all applications and reduces the need for additional products. Combining the herbicide and the oil-based drift reducing technology in a common package also improves storage and distribution. The present invention overcomes stability challenges that previously made this infeasible.

[0012] In one embodiment of the present invention, the oil-based DRA is provided as an agrochemical formulation to be diluted at the time of use, either alone or in combination with an HPPD-inhibiting herbicide and / or a PPO-inhibiting herbicide. The agrochemical formulation preferably contains about 10-70 wt%, more preferably 20-60 wt%, and even more preferably 30-50 wt% of a herbicide, and about 10-30 wt% of an oil-based DRA, with the remainder being adjusted by other components. If necessary, other herbicides may also be used. In one embodiment, the agrochemical formulation does not contain an auxin-based herbicide.

[0013] One aspect of the present invention is the reduction of fine particles. The percentage of fine particles can come from two techniques. One technique is to increase the average particle size without changing the particle size distribution. This technique, often employed in the art, reduces fine particles, but the average particle size increases, which can adversely affect spray characteristics. A particular feature of the present invention is the ability to reduce the percentage of fine particles without significantly increasing the average particle size or particle size distribution. Fine particle reduction is defined according to industry standards, where fine particle reduction is defined relative to the percentage of fine particles in the same herbicide formulation excluding the drift reducing agent being tested. The present invention provides a fine particle reduction of at least 5 wt% to 75 wt% or less without increasing the average particle size by 25% or more. More preferably, the fine particle reduction is at least 5 wt% to 50 wt% or less, even more preferably at least 10 wt% to 40 wt%, even more preferably at least 15 wt% to 30 wt% or less, and most preferably at least 20 wt% to 25 wt% or less. Further increase in fine particle reduction may adversely affect the average particle size or particle size distribution.

[0014] A preferred oil-based DRA is a blend comprising organic compounds selected from vegetable oil or methylated vegetable oil, ethoxylated fatty acids and ethoxylated polyols esterified with fatty acids. In a preferred embodiment, the oil-based DRA comprises soybean oil or methylated soybean oil, ethoxylated oleate, and ethoxylated glycerin esterified with poly(hydroxystearic acid). An oil-based DRA particularly suitable for demonstration of the present invention comprises 85-94.5 wt% methylated soybean oil, 0.5-3 wt% polyethoxylated (POE) tall oil fatty acid, and 5-12 wt% POE glycerin esterified with 12 hydroxystearic acid. The POE tall oil fatty acid is preferably ethoxylated with 3-20 ethylene oxide groups. The glycerin is preferably ethoxylated with 3-35 ethylene oxide groups. Not all DRAs are suitable for co-formulation with the described invention. To be eligible for inclusion, a DRA must have acceptable physical stability, chemical stability, and drift reduction performance at relevant commercial concentrations.

[0015] HPPD inhibitors are a class of herbicides that prevent plant growth by inhibiting the enzyme HPPD, which breaks down the amino acid tyrosine in plants into molecules that can be used by plants to produce other molecules they need. HPPD inhibitors are in the 27th group of herbicides, which includes isoxazoles, isoxaflutoles, pyrazoles, benzofenap, pyrasulfotole, pyrazolinates, pyrazoxyfen, topramezone, tolpyralate, triketones, benzobicyclones, bicyclopyrones, fenquinotrione, mesotrione, sulcotrione, tembotrione, and tefuryltrione.

[0016] PPO inhibitors are a class of herbicides that impair plant growth by inhibiting PPO, the plant enzyme that produces both chlorophyll and heme precursors required for photosynthesis and the electron transport chain within cells. In addition to inhibiting the production of chlorophyll and heme, PPO inhibitors cause the formation of highly reactive molecules that lead to the breakdown of cell membranes and the disintegration of organelles. PPO is a group 14 herbicide that includes diphenyl ether; lactofen; acifluorfen; bifenox; chlornitrofen; fomesafen; fluorodifen; fluoroglycofen-ethyl; fluoronitrofen; nitrofen; oxyfluorfen; clomethoxyfen; phenylpyrazole; pyraflufen-ethyl; N-phenyloxadiazolone; oxadiargyl; oxadiazone; N-phenyltriazolinone; azafenidin; carfentrazone-ethyl; sulfentrazone; N-phenylimide; fluthiacet-methyl; butafenacil; saflufenacil; pentoxazone; chlorphthalim; cinidon-ethyl; flumiclorac-pentyl; flumioxazin; flumipropyne; trifludimoxazin; thiafenacil, and pyraclonil.

[0017] The formulations of the present invention exhibit excellent stability. For example, no separation of the formulations of the present invention was observed after two weeks of freeze / thaw cycles and storage at 4° C. for up to six weeks. A thin layer of separation was observed on the top of the products using the formulations of the present invention at 35° C. for up to 12 weeks, but this thin layer easily returned to a homogenous state with a few inversions.

[0018] A particular feature of the present invention is the ability to provide pesticide formulations, particularly spray formulations, with improved drift control properties without the inclusion of additives selected from polymers, particularly polymers selected from the group consisting of polyacrylamides and polyacrylates; natural product thickeners such as guar gum. A second feature of the present invention is the ability to provide chemically stable formulations, without degradation of the active ingredient, even without metal additives such as copper. More specifically, the present invention provides pesticide formulations with additives of 25 wt% or less, preferably 10 wt% or less, more preferably 5 wt% or less, even more preferably 2 wt% or less, and most preferably 0.5 wt% or less. The ability to avoid the use of substances typically considered necessary in HPPD and PPO pesticide formulations minimizes the chemicals applied to crops, reduces costs, and simplifies the overall manufacturing and supply chain for the production and use of pesticide formulations.

[0019] Another particular feature of the present invention is stability. For the purposes of the present invention, a formulation is defined as stable if the herbicide concentration decreases by less than 10 wt% after 12 weeks of storage at 35° C. More preferably, the herbicide concentration decreases by less than 5 wt%, and even more preferably, by less than 3 wt% after 12 weeks of storage at 35° C. EXAMPLES

[0020] [Table 1]

[0021] The general method used to prepare the HPPD inhibitor formulations involved four steps. The first step was the preparation of a large mill base by mixing 40.82% mesotrione (98%), 30.55-30.95% water, 4% propylene glycol, a dispersant (3.75% Ethox 5037), a wetting agent (1.25% Ethox 4420), and 0.15% SAG 1572. This mixture was milled to the desired herbicide particle size. The second step involved the addition of a slurry containing a thickening agent. In the second step, the mill base was split in half so that two thickening agents could be evaluated. Slurry 1 contained 5% propylene glycol, 0.13% Proxel GXL, and 0.2% xanthan gum. For formulations using Slurry 1, 5.33% of Slurry 1 was added to the mesotrione mill base prepared in the first step. Slurry 2 contained 0.2% xanthan gum, 0.4% Attagel 50, 5% propylene glycol, and 0.13% Proxel GXL. For formulations using Slurry 2, 5.73% of Slurry 2 was added to the mesotrione millbase prepared in step 1. After it was determined that the slurry was properly mixed, the third step was to mix in the DRA material. A paddle blade was used to separate each batch of millbase containing thickeners so that the various drift reducing agents could be mixed in. After it was determined that the DRA was fully incorporated, the fourth step was to buffer the final product to the desired pH with phosphoric acid.

[0022] The following mesotrione formulations were prepared using 12% Ethox OB DRA from the general procedure described in the previous paragraph and are listed in Table 2.

[0023] [Table 2]

[0024] The following formulations were prepared using SC-1604 or polyacrylamide at 0.1 wt %, and are listed in Table 3.

[0025] [Table 3]

[0026] The following formulations were prepared using SC-1604 or polyacrylamide at 1 wt %, and are listed in Table 4.

[0027] [Table 4]

[0028] For mesotrione formulations with the commercial DRA product InterLock®, the following procedure was used. The first step was the preparation of a large mill base by mixing 40.82% mesotrione (98%), 19.95%-30.95% water, 4% propylene glycol, 3.75% dispersant (Ethox 5037), and 1.25% wetting agent (Ethox 4420), and 0.15% SAG 1572. This mixture was milled to the desired herbicide particle size. The second step involved the addition of Slurry 1. After ensuring that the slurry was properly mixed, the third step was to mix InterLock® at 12 wt% for BP6-020 and 23 wt% for LAH22-59 using a paddle blade mixer. After it was determined that InterLock® was fully incorporated, the fourth step was to buffer the final product to the desired pH using phosphoric acid. The target concentration of mesotrione was 40% in both BP6-020 and LAH22-59. The stability of these formulations is described in Table 5.

[0029] Methods to determine physical stability were initial and subsequent tests for appearance, activity assays, and dilution stability. Acceptable appearance specifications are little or no visible bleed layer after a period of time and resuspension with minimal applied force. Dilution stability indicates how stable the herbicide is when diluted in water. To ensure that the spray solution is sufficiently homogenous upon application, no separation, less than 1 mL of settling (ppt), or clumping should be detectable after a 5 wt% dilution in hard water is stirred and allowed to sit for 30 minutes. Temperature stability of the samples was tested by placing the samples at 4°C for up to 6 weeks, at 35°C for up to 12 weeks, and by subjecting them to freeze / thaw (F / T) cycles, which means putting them in and taking them out of a freezer set at approximately -16°C for 2 weeks. The results are shown in Tables 5, 6, 7, and 8.

[0030] [Table 5]

[0031] Due to the viscosity of the formulations, the mesotrione formulations prepared with InterLock® were deemed unsuitable for commercial use at the concentrations prepared. Viscosity was measured using a Brookfield® DVE Viscometer using spindle LV2 at 12 rpm. BP6-020 measured at 1498 cP, while LAH22-59 could not be measured due to its high viscosity.

[0032] [Table 6]

[0033] [Table 7]

[0034] [Table 8]

[0035] The general method used to prepare the PPO inhibitor suspension concentrate included three steps. In the first step, a large mill base was prepared by mixing 42.13% sulfentrazone (98%) with 40.81% water, 0.5% Cab-O-Sil M5, 5% dispersant (3.75% Ethox 5037) and wetting agent (1.25% Ethox 4420), and 0.20% SAG 1572. The mill base was then milled until the herbicide reached the desired particle size. In the second step, a slurry containing thickeners, including 5% propylene glycol, 0.16% xanthan gum, and 0.2% Proxel GXL, was added to the mill base prepared in the first step. The slurry was agitated using a paddle blade. Once the slurry was deemed adequately mixed, 6% Ethox OB DRA was added with mixing until adequately uniform, as in step 3.

[0036] According to the above general procedure, formulations of sulfentrazone were prepared, and the formulations and their corresponding stability are listed in Table 9.

[0037] [Table 9]

[0038] Mesotrione-containing formulations formulated with Ethox OB DRA were also tested for chemical stability at elevated temperatures to demonstrate that the formulations maintained the chemical stability of the herbicide. Formulations were prepared as described above for BP5-044A and BP5-044B. Samples were divided into three aliquots and placed under initial (freshly prepared), 4°C, and 35°C conditions. Mesotrione concentrations were measured from the initial freshly prepared samples, samples stored at 4°C for 6 weeks, and samples stored at 35°C for 6 weeks.

[0039] Mesotrione was measured by HPLC with detection at 230 nm. Samples were prepared in 40% acetonitrile and water. Separation was performed on an Agilent 1100 Series HPLC equipped with a Thermo Scientific BDS Hypersil Phenyl column using isocratic conditions with a mobile phase of 60% 10 mM phosphoric acid and 40% acetonitrile. Data are presented in Table 10.

[0040] [Table 10]

[0041] The results indicate that the active concentration of mesotrione is within the US EPA OPPTS certified initial result limits and is chemically stable. According to OPPTS 830.1750, the certification limits for active ingredients between 20.0 and 100.0% are ±3% of the nominal concentration of the active ingredient. For mesotrione formulations, the nominal concentration is set at 41.30%, so the limits are 40.06-42.54%.

[0042] To test the performance of DRA, a commercial 40% mesotrione-containing product (meso SC) and a proven commercial DRA (CDRA) were used as tank-mix (TM) standards (std) against an all-in-one experimental product with OB DRA. A tank-mix containing glyphosate, Roundup PowerMAX® 3 (RUPM3) was also sprayed with HPPD and PPO inhibitors with DRA to evaluate the interaction of multiple active systems in a single spray. AIXR 11004 nozzles were used at 40 psi for spray testing. Spray concentrations were as follows: meso SC at 3 oz / acre (0.14 wt%), RUPM3 at 30 oz / acre (1.57 wt%), sulfentrazone at 10 oz / acre (0.49%), and CDRA at 4 oz / acre (0.20%). All mixes were formulated to achieve the specified application rates at a spray volume of 15 gallons per acre (gpa). The % fines and DV50 results were measured using a Sympatec HELOS Laser fitted with an R7 lens and the results were analysed using Sympatec software.

[0043] In spray studies of sulfentrazone and 6% OB DRA, the fine particles generated were comparable to those obtained with mesotrione, confirming that OB DRA also functions as a PPO inhibitor.

[0044] At 0.1%, the aqueous polyacrylamides and polyacrylates in mesotrione formulations produced 2-2.7 times more microparticles than the oil-based polymers at 12%. When combined with RUPM3, 2.7-3.3 times more microparticles were present. At 1%, the WB polyacrylamides and polyacrylates produced 2.2-2.6 times more microparticles. When added to RUPM3, 2.6-3.2 times more microparticles were present.

[0045] Figure 4 compares the wt% of particles <150 μm between commercial and OB DRA. Figure 5 compares the wt% of particles <150 μm between OB DRA and water-based polyacrylate DRA. Figure 6 compares the wt% of particles <150 μm between OB DRA and water-based polyacrylate DRA with RUPM3. Figure 7 compares the wt% of particles <150 μm between OB DRA and water-based polyacrylamide DRA. Figure 8 compares the wt% of particles <150 μm between OB DRA and water-based polyacrylamide DRA with RUPM3.

[0046] To confirm the results, a second round of spray chamber testing was conducted using the same equipment described in paragraph 39. These tests focused on formulations containing 40% mesotrione and spiked with various substances to test the effect on the percentage of fine particles (less than 150 microns) and the mean particle size (DV50). To conduct the spray chamber tests, concentrated formulations were diluted as described below. In some cases, spray chamber tests were conducted with the addition of a second herbicide, RUPM3, to the diluted spray mix. Three or more replicates per treatment were performed using concentrated 2 liter mix sizes. Tables 11 and 12 show the averages of three consistent replicates. Mesotrione products - Callisto®, LAH24-07 A1&C1, and LAH24-03 A1-I1 were formulated at 3 fl oz / a (equivalent to 3.1 ml / 2L at 15 gpa). InterLock® was prepared at 4 fl oz / a (equivalent to 4.2 ml / 2 L at 15 gpa). Roundup PowerMax® 3 was prepared at 30 fl oz / a (equivalent to 31.3 ml / 2 L at 15 gpa).

[0047] Table 11. Median diameter by volume (Dv50) and percentage of droplets less than 150 μm (Pct<150 μm) for mesotrione treatments sprayed by AIXR11004 at 40 psi, 15 gpa.

[0048] [Table 11]

[0049] Table 12 shows the median diameter by volume (Dv50) and percentage of droplets less than 150 μm (Pct<150 μm) for mesotrione + Roundup PowerMax® 3 (RUPM3) treatments sprayed with AIXR11004 at 40 psi, 15 gpa.

[0050] [Table 12]

[0051] Particle drift testing was performed in the low-velocity wind tunnel at the Pesticide Application Technology Laboratory (University of Nebraska-Lincoln). All treatments tested were formulated with 1,3,6,8-pyrenetetrasulfonic acid tetrasodium salt (PTSA) fluorescent tracer at 3 g / L. In the low-velocity wind tunnel, tank mixes were sprayed with three different nozzles (AIXR11004, GA11004, TDXL11004) at 40 psi for 3 seconds under 10 m airflow. The nozzles were positioned perpendicular to the wind tunnel and wind flow, similar to a real-world application scenario. Mylar cards (4 × 4 inches) were used to collect particle drift deposition 1, 2, 3, 6, 8, and 12 meters (m) downwind from the nozzle. Deposition data at 12 m downwind is not shown as deposition was not collected for all treatments. Applications were made at a height of 20 inches against the Mylar cards. Each treatment (tank mix with nozzle) was replicated three times.

[0052] The Mylar cards were collected 30 seconds after application and placed in a pre-labeled plastic zip-lock bag. To avoid photodegradation of PTSA, the zip-lock bag containing the Mylar cards was placed in a dark container immediately after collection. The spray particle drift deposition of each Mylar card was measured by fluorescence analysis at the Pesticide Application Technology Laboratory. The Mylar cards were washed with 40 ml of a 9:1 solution of distilled water and 91% isopropyl alcohol. With the tracer fully suspended, 5 ml aliquots were transferred to glass cuvettes and analyzed by flame spectrofluorimetry. Data in relative fluorescence units were calculated using a calibration curve for the tracer at 1 cm 2 The results were converted to micrograms of PTSA per Mylar card. Figures 1-3 show the spray deposition (mg / cm) at 1, 2, 3, 6, and 8 m downwind for the AIXR11004, GA11004, and TDXL11004 nozzles. 2 ) are shown. In each figure, the samples at each distance are repeated from left to right in the following order at each distance: Callisto®, Callisto®+InterLock®, Callisto®+Reign®, Callisto®+RUPM3, Callisto®+RUPM3+InterLock®, Callisto®+RUPM3+Reign®, LAH24-07A, and LAH24-07A+RUPM3. The data indicate that the LAH24-07A formulation is at least as effective at reducing off-target deposition as the commercially available oil-based DRT, InterLock®, and both are more effective than the commercially available water-based drift reducer, Reign®.

[0053] As shown in the examples, the formulations of the present invention provide less than 6 wt. % sub-150 μm particulates, more preferably less than 4 wt. % sub-150 μm particulates, along with an oily drift control agent, without the need for additional ingredients.

[0054] All percentages are by weight unless otherwise noted.

[0055] While the present invention has been described with reference to preferred embodiments, it is not limited thereto, and those skilled in the art will recognize additional embodiments that are described and defined in the claims appended hereto.

Claims

1. 10 to 70 wt % of at least one herbicide selected from the group consisting of 4-hydroxyphenylpyruvate dioxygenase-inhibiting herbicides and protoporphyrinogen oxidase-inhibiting herbicides; and 10-30 wt% oil-based drift control agent 5. A pesticide formulation comprising:

2. 2. The pesticide formulation of claim 1, wherein the 4-hydroxyphenylpyruvate dioxygenase inhibiting herbicide is selected from the group consisting of isoxazole; isoxaflutole; pyrazole; benzofenap; pyrasulfotole; pyrazolinate; pyrazoxyfen; topramezone; tolpyralate; triketone; benzobicyclone; bicyclopyrone; fenquinotrione; mesotrione; sulcotrione; tembotrione and tefuryltrione.

3. 2. The pesticide formulation of claim 1, wherein the protoporphyrinogen oxidase inhibiting herbicide is selected from the group consisting of diphenyl ether; lactofen; acifluorfen; bifenox; chlornitrofen; fomesafen; fluorodifen; fluoroglycofen-ethyl; fluoronitrofen; nitrofen; oxyfluorfen; clomethoxyfen; phenylpyrazole; pyraflufen-ethyl; N-phenyloxadiazolone; oxadiargyl; oxadiazone; N-phenyltriazolinone; azafenidin; carfentrazone-ethyl; sulfentrazone; N-phenylimide; fluthiacet-methyl; butafenacil; saflufenacil; pentoxazone; chlorphthalim; cinidon-ethyl; flumiclorac-pentyl; flumioxazin; flumipropyne; trifludimoxazin; thiafenacil and pyraclonil.

4. 10. The pesticide formulation of claim 1, wherein the oil-based drift control agent further comprises a vegetable oil or a methylated vegetable oil, an ethoxylated fatty acid, an ethoxylated polyol esterified with a fatty acid.

5. 5. The pesticide formulation of claim 4, wherein the oil-based drift control agent further comprises at least one material selected from the group consisting of soybean oil, methylated soybean oil, ethoxylated oleate, and ethoxylated glycerin esterified with poly(hydroxystearic acid).

6. 6. The pesticide formulation of claim 5, wherein the oil-based drift control agent further comprises at least two materials selected from the group consisting of soybean oil, methylated soybean oil, ethoxylated oleate, and ethoxylated glycerin esterified with poly(hydroxystearic acid).

7. 2. The pesticide formulation of claim 1, wherein the oily drift control agent comprises 85-94.5 wt % methylated soybean oil, 0.5-3 wt % polyethoxylated (POE) tall oil fatty acids, and 5-12 wt % POE glycerin esterified with 12 hydroxystearic acid.

8. 8. The pesticide formulation of claim 7, wherein the POE tall oil fatty acid is ethoxylated with 3 to 20 ethylene oxide groups.

9. 8. The pesticide formulation of claim 7, wherein the glycerin is ethoxylated with 3 to 35 ethylene oxide groups.

10. 10. The pesticide formulation of claim 1 comprising up to 25 wt. % of an additive selected from the group consisting of polymers, natural product thickeners, or metal additives.

11. 11. The pesticide formulation of claim 10 comprising up to 5 wt% of an additive selected from the group consisting of polymers, natural product thickeners, or metal additives.

12. 12. The pesticide formulation of claim 11 comprising up to 0.5 wt% of an additive selected from the group consisting of polymers, natural product thickeners, or metal additives.

13. 11. The pesticide formulation of claim 10, wherein the polymer is selected from the group consisting of polyacrylamides and polyacrylates.

14. 11. The pesticide formulation of claim 10, wherein the natural product thickener is guar gum.

15. 11. The pesticide formulation of claim 10, wherein the metal is copper.

16. 10. The pesticide formulation of claim 1, further comprising water.

17. 10. The pesticide formulation of claim 1 comprising 20-60 wt% of said herbicide and 10-30 wt% of said oil-based drift control agent.

18. 18. The pesticide formulation of claim 17, comprising 40 to 50 wt. % of said herbicide.

19. 10. The pesticide formulation of claim 1, wherein the formulation is free of auxinic herbicides.

20. 10. The pesticide formulation of claim 1, with a reduction in fines of at least 5 wt% to no more than 75 wt% and an increase in average particle size of no more than 25%.

21. 21. The pesticide formulation of claim 20, wherein the particulate reduction is at least 10 wt% to no more than 40 wt%.

22. 22. The pesticide formulation of claim 21, wherein the fines reduction is at least 15 wt% to no more than 30 wt%.

23. 23. The pesticide formulation of claim 22, wherein the particulate reduction is at least 20 wt% to no more than 25 wt%.

24. 2. The pesticide formulation of claim 1, wherein said concentration decreases by less than 3 wt % after storage at 35° C. for 12 weeks.

25. 1. A method of treating a crop comprising: 10 to 70 wt % of at least one herbicide selected from the group consisting of 4-hydroxyphenylpyruvate dioxygenase-inhibiting herbicides and protoporphyrinogen oxidase-inhibiting herbicides; and 10-30 wt% organic drift control agent spraying said crop with an agrochemical formulation. A method comprising:

26. 26. The method of treating a crop according to claim 25, wherein the 4-hydroxyphenylpyruvate dioxygenase inhibiting herbicide is selected from the group consisting of isoxazole; isoxaflutole; pyrazole; benzofenap; pyrasulfotole; pyrazolinate; pyrazoxyfen; topramezone; tolpyralate; triketone; benzobicyclon; bicyclopyrone; fenquinotrione; mesotrione; sulcotrione; tembotrione and tefuryltrione.

27. 26. The method of treating a crop according to claim 25, wherein the protoporphyrinogen oxidase inhibiting herbicide is selected from the group consisting of diphenyl ether; lactofen; acifluorfen; bifenox; chlornitrofen; fomesafen; fluorodifen; fluoroglycofen-ethyl; fluoronitrofen; nitrofen; oxyfluorfen; clomethoxyfen; phenylpyrazole; pyraflufen-ethyl; N-phenyloxadiazolone; oxadiargyl; oxadiazone; N-phenyltriazolinone; azafenidin; carfentrazone-ethyl; sulfentrazone; N-phenylimide; fluthiacet-methyl; butafenacil; saflufenacil; pentoxazone; chlorphthalim; cinidon-ethyl; flumiclorac-pentyl; flumioxazin; flumipropyne; trifludimoxazin; thiafenacil and pyraclonil.

28. 26. The method of treating a crop according to claim 25, further comprising the step of diluting said pesticide formulation prior to said spraying step.

29. 29. The method of treating crops according to claim 28, wherein said dilution step is with water.

30. 26. The method of treating a crop according to claim 25, wherein the oil-based drift control agent further comprises at least one of a vegetable oil, a methylated vegetable oil, an ethoxylated fatty acid, or an ethoxylated polyol esterified with a fatty acid.

31. 31. The method of treating a crop as described in claim 30, wherein the oily drift control agent further comprises at least one material selected from the group consisting of soybean oil, methylated soybean oil, ethoxylated oleate, and ethoxylated glycerin esterified with poly(hydroxystearic acid).

32. 32. The method of treating a crop as described in claim 31, wherein the oily drift control agent further comprises at least two materials selected from the group consisting of soybean oil, methylated soybean oil, ethoxylated oleate and ethoxylated glycerin esterified with poly(hydroxystearic acid).

33. 26. The method of treating a crop of claim 25, wherein the oily drift control agent comprises 85-94.5 wt % methylated soybean oil, 0.5-3 wt % polyethoxylated (POE) tall oil fatty acids, and 5-12 wt % POE glycerin esterified with 12 hydroxystearic acid.

34. 34. The method of treating crops according to claim 33, wherein said POE tall oil fatty acid is ethoxylated with from 3 to 20 ethylene oxide groups.

35. 34. The method of treating crops according to claim 33, wherein the glycerin is ethoxylated with from 3 to 35 ethylene oxide groups.

36. 26. The method of treating a crop according to claim 25, wherein the herbicide has less than 6 wt% fine particles less than 150 μm.

37. 37. The method of treating a crop according to claim 36, wherein the herbicide has less than 4 wt% fine particles less than 150 μm.

38. 26. The method of treating a crop according to claim 25 comprising 20-60 wt% of said herbicide and 10-30 wt% of said oil-based drift control agent.

39. 39. The method of treating a crop according to claim 38 comprising 40-50 wt% of said herbicide.

40. 26. The method of treating a crop according to claim 25, wherein the formulation is free of auxinic herbicides.

41. 26. A method of treating crops as claimed in claim 25, accompanied by a reduction in fines of at least 5 wt% to no more than 75 wt% and an increase in average particle size of no more than 25%.

42. 42. The method of treating crops as claimed in claim 41, wherein the reduction in particulates is at least 10 wt% to no more than 40 wt%.

43. 43. The method of treating crops as claimed in claim 42, wherein the reduction in particulates is at least 15 wt% to no more than 30 wt%.

44. 44. A method of treating crops as claimed in claim 43, wherein the reduction in particulates is at least 20 wt% to no more than 25 wt%.

45. 26. The method of treating crops according to claim 25, wherein the concentration decreases by less than 3 wt% after storage at 35°C for 12 weeks.

46. 10-70 wt % of at least one herbicide selected from the group consisting of mesotrione and sulfentrazone; and 10-30 wt% oil-based drift control agent 5. A pesticide formulation comprising:

47. 47. The pesticide formulation of claim 46, further comprising at least one 4-hydroxyphenylpyruvate dioxygenase inhibiting herbicide selected from the group consisting of isoxazole; isoxaflutole; pyrazole; benzofenap; pyrasulfotole; pyrazolinate; pyrazoxyfen; topramezone; tolpyralate; triketone; benzobicyclon; bicyclopyrone; fenquinotrione; sulcotrione; tembotrione and tefuryltrione.

48. 47. The pesticide formulation of claim 46, further comprising at least one protoporphyrinogen oxidase inhibitor herbicide selected from the group consisting of diphenyl ether; lactofen; acifluorfen; bifenox; chlornitrofen; fomesafen; fluorodifen; fluoroglycofen-ethyl; fluoronitrofen; nitrofen; oxyfluorfen; clomethoxyfen; phenylpyrazole; pyraflufen-ethyl; N-phenyloxadiazolone; oxadiargyl; oxadiazone; N-phenyltriazolinone; azafenidin; carfentrazone-ethyl; N-phenylimide; fluthiacet-methyl; butafenacil; saflufenacil; pentoxazone; chlorphthalim; cinidon-ethyl; flumiclorac pentyl; flumioxazin; flumipropyne; trifludimoxazin; thiafenacil and pyraclonil.

49. 47. The pesticide formulation of claim 46, wherein the oil-based drift control agent further comprises at least one of a vegetable oil, a methylated vegetable oil, an ethoxylated fatty acid, or an ethoxylated polyol esterified with a fatty acid.

50. 50. The pesticide formulation of claim 49, wherein the oil-based drift control agent further comprises at least one material selected from the group consisting of soybean oil, methylated soybean oil, ethoxylated oleates, and ethoxylated glycerin esterified with poly(hydroxystearic acid).

51. 51. The pesticide formulation of claim 50, wherein the oil-based drift control agent further comprises at least two materials selected from the group consisting of soybean oil, methylated soybean oil, ethoxylated oleate, and ethoxylated glycerin esterified with poly(hydroxystearic acid).

52. 47. The pesticide formulation of claim 46, wherein the oily drift control agent comprises 85-94.5 wt % methylated soybean oil, 0.5-3 wt % polyethoxylated (POE) tall oil fatty acids, and 5-12 wt % POE glycerin esterified with 12 hydroxystearic acid.

53. 53. The pesticide formulation of claim 52, wherein said POE tall oil fatty acid is ethoxylated with 3 to 20 ethylene oxide groups.

54. 53. The pesticide formulation of claim 52, wherein the glycerin is ethoxylated with 3 to 35 ethylene oxide groups.

55. 47. The pesticide formulation of claim 46, comprising up to 25 wt% of an additive selected from the group consisting of a polymer, a natural product thickener, or a metal additive.

56. 56. The pesticide formulation of claim 55, comprising up to 5 wt.% of an additive selected from the group consisting of polymers, natural product thickeners, or metal additives.

57. 57. The pesticide formulation of claim 56, comprising 0.5 wt% or less of an additive selected from the group consisting of a polymer, a natural product thickener, or a metal additive.

58. 57. The pesticide formulation of claim 56, wherein the polymer is selected from the group consisting of polyacrylamides and polyacrylates.

59. 57. The pesticide formulation of claim 56, wherein the natural product thickener is guar gum.

60. 47. The pesticide formulation of claim 46, comprising 20-60 wt% of said herbicide and 10-30 wt% of said oil-based drift control agent.

61. 61. The pesticide formulation of claim 60 comprising 40-50 wt% of said herbicide.

62. 47. The pesticide formulation of claim 46, wherein the formulation is free of auxinic herbicides.

63. 47. The pesticide formulation of claim 46, with a reduction in fines of at least 5 wt% to no more than 75 wt% and an increase in average particle size of no more than 25%.

64. 64. The pesticide formulation of claim 63, wherein the particulate reduction is at least 10 wt% to no more than 40 wt%.

65. 65. The pesticide formulation of claim 64, wherein the particulate reduction is at least 15 wt% to no more than 30 wt%.

66. 66. The pesticide formulation of claim 65, wherein the particulate reduction is at least 20 wt% to no more than 25 wt%.

67. 47. The pesticide formulation of claim 46, wherein said concentration decreases by less than 3 wt % after storage at 35° C. for 12 weeks.

Images