WO2025217477A1 - Herbicidal compositions - Google Patents

Abstract

Oil dispersion compositions comprising sulfonylurea-florpyrauxifen-benzyl mixtures, having improved stability, are disclosed.

Description

HERBICIDAL COMPOSITIONS

PRIORITY

[0001] This application claims priority to United States Application 63/633,124 filed April 12, 2024, which is hereby incorporated herein by reference in its entirety.

BACKGROUND

[0002] Florpyrauxifen-benzyl and its herbicidal formulations typically comprise oil-liquid- based compositions because they are easier to handle when measuring, pumping, diluting and dispersing in water for spraying. In addition, oil-liquid compositions generally exhibit superior biological efficacy. Typical oil-based liquid formulations include oil dispersions (OD) and emulsifiable concentrates (EC) where one or more active ingredients are dissolved in and/or suspended in the liquid media of the formulation.

[0003] Amidosulfuron and rimsulfuron herbicides are members of the sulfonylurea family, which is a well-known and important class of herbicides comprising more than 30 active ingredients that are widely used for controlling a range of annual and perennial broad-leaved weeds and grasses. However, sulfonylurea herbicides are known to be unstable as they tend to hydrolyze via cleavage at the sulfonylurea bridge. This instability poses serious problems for the storage stability of formulated products and makes the development of liquid formulations comprising sulfonylurea herbicides challenging. Instead, sulfonylurea compounds are normally formulated as powders, granules, and tablets.

[0004] Efforts to stabilize liquid formulations of sulfonylurea herbicides have been reported. For example, various stabilizers have been employed, i.e. Sodium carbonate

(W02005011382A1), sodium silicate and potassium silicate (WO2021152391A1), metal carbonates and metal phosphates (WO2016102499 Al), inorganic or C1-C12 organic lithium salts (US20190110468A1), and urea (W02008108973A1).

[0005] Despite the art described above, the inherent chemical instability of sulfonylurea herbicides has limited their widespread use in liquid formulations. There remains a clear need for improved liquid formulation compositions comprising sulfonylurea herbicides having improved chemical storage stability. It has been surprisingly found that the addition of phenolic stabilizers to oil-liquid-based formulation compositions of florpyrauxifen-benzyl and sulfonylurea herbicides provides compositions having excellent storage stability.

BRIEF DESCRIPTION

[0006] The stability of sulfonylurea herbicides in oil dispersion formulations has long presented challenges. For example, a study of Battelle Institutes produced the following data:

SULFONYLUREA STABILITY

[0007] Sulfonylurea stability in 5% OD (oil dispersion) formulations, % remaining after 2 weeks at 54 °C in 5% non-stabilized oil dispersion formulation. (Source https://www.battelle.org/)

[0008] We have discovered novel, stable, oil dispersion formulations comprising florpyrauxifen-benzyl and at least one sulfonylurea herbicide. Embodiments disclosed herein have improved sulfonylurea stability. Embodiments disclosed herein comprise solvent in which sulfonylurea herbicides are poorly soluble. A preferred embodiment of an oil dispersion has a sulfonylurea solubility of 500 PPM or less. A more preferred embodiment has a sulfonylurea solubility of 200 PPM or less. Suitable embodiments of oil dispersions comprise solvents and/or adjuvants. Suitable solvents/adjuvants may comprise a mixture of methylated seed oil, mineral oil, paraffin oil, and mixtures thereof. Embodiments further comprise at least one flavonoid or phenolic compound such as gallate quercetin, epigallocatechin gallate, gallate ester, tannic acid, and mixtures thereof. These flavonoid and phenolic compounds have unexpectedly been shown to inhibit the hydrolysis of sulfonylurea herbicides in oil dispersion formulations - a long standing problem. Embodiments disclosed herein may also comprise dispersants (surfactants), ionic emulsifiers (surfactants), non-ionic emulsifiers (surfactants), organic rheology modifiers, inorganic rheology modifiers, anti-foaming agents, and mixtures thereof.

DETAILED DESCRIPTION

[0009] Suitable sulfonylurea compounds useful in methods and compositions described herein include amidosulfuron, azimsulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron- methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron-methyl sodium, foramsulfuron, halo- sulfuronmethyl, imazosulfuron, iofunsulfuron, iodosulfuron-methyl sodium, mesosulfuron- methyl, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron-methyl, propyrisulfuron, prosulfuron, pyrimisulfan, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron- methyl, sulfosulfuron, thifensulfuron-methyl, triasulfuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron-methyl, tritosulfuron, sulfosulfuron, foramsulfuron and iodosulfuron. [0010] Suitable ingredients for preparing compositions described herein include, but are not limited to, Genagen 4166 (mixture of N,N-dimethyloctanamide and N,N-dimethyldecan-l- amide, available from Clariant Corp., Muttenz, Switzerland), Hallcomid 1025 (N,N-diemthyl-9- decenamide, available from Stepan, Northfield, IL), Halcomid M-12-14 (mixture of N,N- dimethyldodecanamide and N,N-dimethyltetradecanamide, available from Stepan, Northfield IL), Jeffsol AG 1555 Carbonate (propylene carbonate, available from Huntsman International LLC; The Woodlands, TX.), Calument 6970 LP oil (CAS Number 8042-47-5, white mineral oil, available from Calumet Specialty Products Partners, Indianapolis, IN), Rhodiasolv RPDE (mixture of diemthyhlglutarate, adipate, and succinate, available from Solvay), Acetophenone (CAS Number 98-86-2, available from Sigma Aldrich), Surfonic AG-1700 and Surfonic AG- 1705 (aromatic ester solvent, available from Indorama Ventures, Bangkok, Thailand), Dowanol DPM (dipropylene glycol methyl ether, available from DOW Chemical, Midland, MI), Tamisolve NxG (N-butyl-2-pyrrolidone, available from Eastman Chemicals, Kingsport, TN), polyglycol 26-2 (blend of ethylene oxide, propylene oxide and di -sec-butyl phenol polymer, CAS #69029-39-6, available from Dow Inc., Midland, MI), and isobomyl acetate (CAS 125-12-2, available from SigmaAldrich, St. Louis, MO).

[0011] Naturally derived oils useful as solvents and adjuvants with the methods and compositions described herein may be derived from or made from plant or animal sources and include, for example, triglyceride fatty acid esters such as vegetable oils, seed oils, or animal oils, or monoesters derived from vegetable, seed, or animal oils, and mixtures thereof. Examples of monoesters derived from vegetable, seed, or animal oils useful with the methods and composition described herein include fatty acid alkyl esters such as methyl caproate, methyl caprylate, methyl caprate, methyl laurate, methyl myristate, methyl palmitate, methyl stearate, methyl oleate, methyl linoleate, methyl linolenate, and mixtures thereof. Examples of triglyceride fatty acid esters useful with the methods and composition described herein include vegetable or seed oils selected from soybean oil, rape seed oil, olive oil, almond oil, canola oil, omega-9 canola oil, castor oil, sunflower seed oil, coconut oil, com oil, cotton seed oil, linseed oil, palm oil, peanut oil, safflower oil, sesame oil, tung oil, and mixtures thereof. Examples of commercially available, naturally derived oils useful with the methods and compositions described herein include: Stepan® 108, a caprylic/capric triglyceride and Steposol® C42, (a methyl laurate/methyl myristate ester derived from coconut oil), which are both available from Stepan (Northfield, Ill ), and Agnique ME12-18, (mixture of C12 _18 fatty acid methyl esters), Agnique ME 18 RD-F (rapeseed oil methyl ester), and Aqnique ME18-SU (methyl oleate), which are available from BASF (Florham Park, N.J.).

[0012] Organic and/or inorganic rheology modifiers useful with methods and compositions described herein include, but are not limited to, polysaccharides, such as xanthan gum, and organic and inorganic sheet minerals. Exemplary solid fillers/rheology modifiers include, but are not limited to, silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, less, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, pyrophyllite clay, attapulgus clay, kieselguhr, calcium carbonate, bentonite clay, Fuller's earth, cottonseed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell flour, lignin, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders, Aerosil R 974 (CAS # 68611-44-9, hydrophobic fumed silica, available from Evonik Industries AG, Essen, Germany) and mixtures thereof.

[0013] Petroleum derived oils useful with the methods and compositions described herein include aromatic and paraffinic hydrocarbons such as, for example, one or more of petroleum fractions or hydrocarbons such as mineral oil, kerosene, paraffinic oils including normal paraffins, isoparaffins, and cycloparaffms, mixed naphthalene and alkyl naphthalene fractions, aromatic solvents, particularly alkyl substituted benzenes such as xylene or propylbenzene fractions, and the like, and mixtures thereof. Examples of commercially available petroleum derived oils useful with the methods and compositions described herein include: Isopar™ M and Isopar™ N (high purity synthetic isoparaffinic hydrocarbons), Drakeol 13 LT MIN OIL NF (CAS Number 8042-47-5, white mineral oil, available from Calumet Specialty Products Partners, Indianapolis, IN), Exxsol™ D UO (low odor dearomatized hydrocarbon), Exxsol™ D60 (low odor dearomatized hydrocarbon), Aromatic 100 (high solvency C9 aromatic), and Aromatic 200 (high solvency Cn aromatic) which are all available from ExxonMobil Chemical (Houston, Tex ).

[0014] The compositions described herein may additionally contain surfactants. The surfactants may be anionic, cationic, or nonionic in character. For example, compositions as described herein can optionally include an efficacy enhancing surfactant. Examples of typical surfactants include alcohol-alkylene oxide addition products, such as tridecyl alcohol-C16 ethoxylate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as lauryl trimethylammonium chloride; ethoxylated amines, such as tallowamine ethoxylated; betaine surfactants, such as cocoamidopropyl betaine; fatty acid amidopropyl dimethylamine surfactants such as cocoamidopropyl dimethylamine; alkylpolyglycoside surfactants; polyethylene glycol esters of fatty acids, such as polyethylene glycol stearate; and fatty acid esters of polyglycerol. [0015] The surfactants useful with the methods and compositions described herein may be anionic or nonionic in character and include polymeric surfactants such as ABA block copolymers and AB block copolymers containing EO and PO blocks such as ethylene oxidepropylene oxide (EO-PO) block copolymers; alcohol alkoxylates; phosphate ester surfactants such as acids or salts of mono and dialkyl phosphate esters, acids or salts of ethoxylated mono and dialkyl phosphate esters, acids or salts of mono and dialkyl phosphate esters of ethoxylated tri styrylphenol and acids or salts of mono and dialkyl phosphate esters of ethoxylated phenol and ethoxylated alkylphenols; alkylbenzene sulfonates and mixtures thereof.

[0016] Examples of useful surfactants include: (1) ABA block copolymers having a hydrophilic portion of polyethylene oxide and a hydrophobic portion of poly(12-hydroxy stearate ), such as, for example, Atlox™ 4914 and Atlox™ 4912 (polymeric surfactant with a low HLB value which can be used in concentrated aqueous esmulsions, suspoemulsions and oil dispersion formulations, Croda; Edison, N.J.), and Termul™ 2510 (Huntsman International LLC; The Woodlands, Tex ); (2) EO-PO block copolymers, such as, for example, Atlas™ G-5000, Atlas G- 5002L (Croda; Edison, N.J.), and the Pluronic® block copolymers (BASF; Florham Park, N.J ), TOXIMUL 8320 (CAS # 9038-95-3, butyl polyalkylene oxide block copolymer, available from Stepan Company; Northfield, IL) and the like; (3) alcohol alkoxylates, such as, for example, Termul™ 5429 (Huntsman International LLC; The Woodlands, Tex.); (4) alkylbenzene sulfonates, such as Biosoft® N-411, Ninate® 411, Ninate® 100 L, and Ninate 60E (Stepan Company; Northfield, Ill.) and Tensiofix 9811HF and 9824HF (Ajinomoto-Omnichem, Louvain- la-Neuve, Belgium), Nansa 70/2E (Innospec, Salisbury, NC); (5) other surfactants include Geropon SDS (sodium dioctylsulfosuccinate), Geropon T77 (sodium methyl oleoyl taurate), Genapol C 200 (CAS #61791-13-7, fatty alcohol polyglycol ether, available from Clariant Corp., Muttenz, Switzerland), Zephrym PD 2206 (polymeric surfactant, available from Croda, Edison, N.J.), Step-flow 3000 (available from Stepan Company; Northfield, IL). Non-ionic surfactants include Synperonic 13/10 (Croda; Edison, N.J.). [0017] The additional surfactant or mixtures of surfactants optionally used in the described compositions are usually present at a concentration of from about 0.5 to about 20 weight percent of the formulation. Additionally, compositions optionally containing one or more additional compatible ingredients are provided herein. These additional ingredients may include, for example, one or more pesticides or other ingredients, which may be dissolved or dispersed in the composition and may be selected from acaricides, bactericides, fungicides, insecticides, herbicides, herbicide safeners, insect attractants, insect repellents, plant activators, plant growth regulators, and synergists. Also, any other additional ingredients providing functional utility such as, for example, dyes, stabilizers, fragrances, rheology modifiers such as viscosity-lowering additives or thickeners, compatibility agents, organic co-solvents such as, for example, propylene glycol, propylene glycol ethers and/or ethylene glycol ethers, and freeze-point depressants may be included in these compositions. The use of organic co-solvents in the concentrates and spray solutions described herein may provide freezing-point depression and/or enhanced emulsion stability to these compositions.

[0018] The pesticide spray mixtures as described herein may be applied in conjunction with one or more other active ingredients to control a wider variety of unwanted plants, fungi, or insects. When used in conjunction with the other active ingredients, the presently claimed compositions can be formulated with the other active ingredient or active ingredients as premix concentrates, tank mixed with the other active ingredient or active ingredients for spray application, applied sequentially with the other active ingredient or active ingredients in separate spray applications.

An embodiment comprises:

An embodiment comprises:

[0019] An embodiment comprises the following steps: a. preparing a millbase of sulfonylurea; and b. preparing a millbase of florpyrauxifen-benzyl; and c. preparing a phenolics slurry; and d. mixing sulfonylurea millbase, florpyrauxifen-benzyl millbase, and phenolics slurry; and e. adding surfactant to the mixture; and f. adding rheology modifier to the mixture; and g. adding solvent to the mixture; and h. optionally adding other ingredients; and i. mixing until the mixture is homogeneous.

[0020] The steps described above may be performed in any order. [0021] The following examples are presented to illustrate various aspects of the compositions and methods described herein and should not be construed as limitations to the claims.

EXAMPLES

[0022] Oil dispersions described in the examples were prepared as follows.

(i) Preparation of a 20% wt.% phenolics (or derivatives) slurry

Phenolics (or derivatives) were added to a solvent blend (optionally containing surfactants) in an amount of 20 wt.%. The mixture was heated to 50 °C and blended until homogenous.

(ii) Preparation of a 20% wt.% sulfonylurea millbase

Sulfonylurea (pre-milled powder by bench air jet mill) was added to the solvent (optionally containing surfactants) in an amount of 20% wt.%. The mixture was put into an ULTRA-TURRAX Tube Drive with stainless steel balls (5.0 mm). The suspension was milled to a provide a 20% wt.% sulfonylurea millbase having an average particle size (D90) between 7 and 9 pm.

(iii) Preparation of a 10% wt.% florpyrauxifen-benzyl millbase Florpyrauxifen-benzyl (pre-milled powder by bench air jet mill) was added to the solvent (optionally containing surfactants) in an amount of 10% wt.%. The mixture was put into an ULTRA-TURRAX Tube Drive with stainless steel balls (5.0 mm). The suspension was milled to a provide a 10% wt.% florpyrauxifen-benzyl millbase having an average particle size (D90) between 7 and 9 pm.

(iv) Preparation of Oil Dispersion

An appropriate amount of the sulfonylurea millbase (or premix of sulfonylurea millbase and florpyrauxifen-benzyl millbase) was blended with solvent or phenolics (or derivatives) slurry until homogenous, and then optionally blended with other ingredients, resulting in the oil dispersions as described in the tables below.

[0023] Oil dispersion formulations were stored in closed glass bottles. To test for aging stability, formulations were put in a thermostatically controlled oven at 54 °C for 2 weeks, control samples were stored at ambient temperature (25 °C). After storage, formulations were analyzed for active ingredient content by HPLC. Stability is reported based on the amount of active ingredient remaining relative to control sample stored at ambient temperature (25 °C) for 2 weeks.

EXAMPLE 1- SULFONYLUREA SOLUBILITY

[0024] Saturated amidosulfuron solution in different solvents are prepared at different temperature, solvents with low solubility were chosen for oil dispersion preparation. The solubility results are summarized in Table 1 below.

TABLE 1

Solvent Genagen Jeffsol Agnique Agnique Aromatic Isopar M

4166 AG ME C12- ME 18 200 ND

1555 18 RD-F

Amidosulfuron 0.50 0.56 0.02 0.01 0.04 0.0005 sol ubi 1 ity at room temperature (%)

Amidosulfuron 0.49 0.40 0.01 0.01 0.02 0.0012 solubility at -10°C (%)

Amidosulfuron 0.70 0.99 0.03 0.03 0.08 0.0016 solubility at 54°C (%)

TABLE 1 CONTINUED

Solvent 6970 Surfonic Dowanol Tamisolve Polyglycol Isobomyl

Oil AG 1700 DPM NxG 26-2 acetate

Amidosulfuron 0 0010 0 08 0 28 2 91 0 71 0 05 solubility at room temperature (%)

Amidosulfuron 0.0018 0.05 0.23 2.94 nd (frozen) 0.03 solubility at -10°C (%)

Amidosulfuron 0.0010 0.13 0.56 4.00 0.97 0.13 solubility at 54°C (%) EXAMPLE 2 - SULFONYLUREA OIL DISPERSION STABILITY

[0025] Oil dispersions were prepared and tested to determine the chemical stability of sulfonylurea after storage at 54 °C for 2 weeks. Results are summarized in Table 2.

TABLE 2

Example

Components OD1 OD2 OD3 OD4 OD5 OD6

(wt.%)

Amidosulfuron 5.0% 5.0% 5.0% 5.0% 5.0% 5.0%

Agnique ME 18 31.7% 47.5% 63.3% 31.7% 47.5% 63.3%

SU

Isopar M 63.3% 47.5% 31.7%

6970 011 63.3% 47.5% 31.7%

Surfonic AG

1700

Genagen 4166

Stability (%) 98.0% 53.0% 44.0% 0.0% 47.0% 50.0%

TABLE 2 CONTINUED

Example

Components OD7 OD8 OD9 OD10

(wt.%)

Amidosulfuron 5.0% 5.0% 5.0% 5.0%

Agnique ME 18 31.7% 47.5% 63.3%

SU

Isopar M

6970 Oil

Surfonic AG 63.3% 47.5% 31.7%

1700

Genagen 4166 95.0%

Stability (%) 35.0% 41.0% 27.0% 0.0% EXAMPLE 3 - SULFONYLUREA OIL DISPERSION STABILITY

[0026] Oil dispersions in solvent blends with different surfactants were prepared and tested to determine the chemical stability of sulfonylurea after storage at 54°C for 2 weeks. The results are summarized in Table 3 below.

TABLE 3

Example

Components OD11 OD12 OD13 OD14 OD15 OD16

(wt.%)

Amidosulfuron 4.5% 4.5% 4.5% 4.5% 4.5% 4.5%

Agnique ME 18 28.5% 28.5% 28.5% 28.5% 28.5% 28.5%

SU

Isopar M 57.0% 57.0% 57.0% 57.0% 57.0% 57.0%

Ninate 60E 10.0%

Geropon SDS 10.0%

Geropon T77 10.0%

Atlox 4914 10.0%

Atlox 4912 10.0%

Atlox 4916 10.0%

Stability (%) 98.0% 50.0% 87.0% 95.0% 96.0% 92.0%

TABLE 3 CONTINUED

Example

Components OD17 OD18 OD19 OD20 OD21 OD22

(wt.%)

Amidosulfuron 4.5% 4.5% 4.5% 4.5% 4.5% 4.5%

Agnique ME 18 28.5% 28.5% 28.5% 28.5% 28.5% 28.5%

SU

Isopar M 57.0% 57.0% 57.0% 57.0% 57.0% 57.0%

Synperonic Al 1 10.0%

Synperonic 10.0%

13/10

Agnique SBO 10.0%

10 Atlas G-5002L 10.0%

Agnique CSO- 10.0%

40 Pluronic P 105 10.0%

Stability (%) 79.0% 88.0% 95.0% 81.0% 34.0% 83.0%

TABLE 3 CONTINUED

Example

Components OD23 OD24 OD25 OD26 OD27 OD28

(wt.%)

Amidosulfuron 4.5% 4.5% 4.5% 4.5% 4.5% 4.5%

Surfonic AG 28.5% 28.5% 28.5% 28.5% 28.5% 28.5%

1700

Agnique ME 18 57.0% 57.0% 57.0% 57.0% 57.0% 57.0%

SU

Ninate 60E 10.0%

Geropon SDS 10.0%

Geropon T77 10.0%

Atlox 4914 10.0%

Atlox 4912 10.0%

Atlox 4916 10.0%

Stability (%) 98.0% 64.0% 97.0% 96.0% 99.0% 93.0%

TABLE 3 CONTINUED

Example

Components OD29 OD30 OD31 OD32 OD33 OD34

(wt.%)

Amidosulfuron 4.5% 4.5% 4.5% 4.5% 4.5% 4.5%

Surfonic AG 28.5% 28.5% 28.5% 28.5% 28.5% 28.5%

1700

Agnique ME 18 57.0% 57.0% 57.0% 57.0% 57.0% 57.0%

SU

Synperonic Al 1 10.0%

Synperonic 10.0%

13/10

Agnique SBO 10.0%

10 Atlas G-5002L 10.0%

Agnique CSO- 10.0%

40 Pluronic P 105 10.0%

Stability (%) 69.0% 84.0% 96.0% 91.0% 65.0% 93.0%

EXAMPLE 4 - SULFONYLUREA STABILITY OIL DISPERSION STABILITY

[0027] Oil dispersions with or without gallate esters were prepared and tested to determine the chemical stability of sulfonylurea after storage at 54 °C for 2 weeks. The results are summarized in Table 4 below.

TABLE 4

Example

Components OD35 OD36 OD37 OD38 OD39 OD40

(wt.%)

Amidosulfuron 5.0% 5.0% 5.0% 5.0% 5.0% 5.0%

Agnique ME 18 29.1% 29.1% 29.1% 29.1% 29.1% 29.1%

SU

Aerosil R974 4.0% 4.0% 4.0% 4.0% 4.0% 4.0%

Isopar M To 100% To 100% To 100% To 100% To 100% To 100%

Atlox 4912 1.6% 1.6% 1.6% 1.6% 1.6% 1.6%

Ninate 60E 3.9% 3.9% 3.9% 3.9% 3.9% 3.9%

Pluromc P 105 2.6% 2.6% 2.6% 2.6% 2.6% 2.6%

Lauryl gallate 0.5% 1.0% 2.0% 3.0% 4.0%

Lauryl gallate

Octyl gallate

Propyl gallate

Ethyl gallate

Stability (%) 94.3% 96.9% 97.7% 98.3% 98.3% 98.6%

TABLE 4 CONTINUED

Example

Components OD41 OD42 OD43 OD44

(wt.%)

Amidosulfuron 5.0% 5.0% 5.0% 5.0%

Agnique ME 18 29.1% 29.1% 29.1% 29.1%

SU

Aerosil R974 4.0% 4.0% 4.0% 4.0%

Isopar M To 100% To 100% To 100% To 100%

Atlox 4912 1.6% 1.6% 1.6% 1.6%

Ninate 60E 3.9% 3.9% 3.9% 3.9%

Pluronic P 105 2.6% 2.6% 2.6% 2.6%

Lauryl gallate 5.0%

Octyl gallate 5.0%

Propyl gallate 5.0%

Ethyl gallate 5.0%

Stability (%) 98.7% 99.8% 96.7% 97.5%

EXAMPLE 5 - SULFONYLUREA - FLORPYRAUXIFEN-BENZYL MIXTURE OIL

DISPERSION STABILITY

[0028] Oil dispersions of a sulfonylurea and florpyrauxifen-benzyl with or without gallate ester were prepared and tested to determine the chemical stability of sulfonylurea after storage at 54°C for 2 weeks. The results are summarized in Table 5 below.

TABLE 5

Example

Components OD45 OD46 OD47 OD48 OD49 OD50

(wt%)

Amidosulfuron 5.0% 5.0% 5.0% 5.0% 5.0% 5.0%

Florpyrauxifen- 1.0% 1.0% 1.0% 1.0% 1.0% 1.0% benzyl

Agnique ME 18 29.1% 29.1% 29.1% 29.1% 29.1% 29.1%

SU

Aerosil R974 4.0% 4.0% 4.0% 4.0% 4.0% 4.0%

Isopar M To 100% To 100% To 100% To 100% To 100% To 100%

Atlox 4914 1.6% 1.6% 1.6% 1.6% 1.6% 1.6%

Nansa 4.80% 4.80% 4.80% 4.80% 4.80% 4.80%

EVM70/2E

Makon TSP- 4.80% 4.80% 4.80%

16N

Ethylan NS- 4.80% 4.80% 4.80%

500LQ

Lauryl gallate 2.0% 3.0%

Octyl gallate 2.0% 3.0%

Stability (%) 93.3% 96.6% 98.1% 92.2% 95.18% 96.03% EXAMPLE 6 - SULFONYLUREA OIL DISPERSION STABILITY

[0029] Oil dispersions of various sulfonylureas with or without phenolics (or derivatives) were prepared and tested to determine the chemical stability of sulfonylurea after storage at 54°C for 2 weeks. The results are summarized in Table 6 below.

TABLE 6

Example

Components OD51 OD52 OD53 OD54 OD55 OD56

(wt.%)

Thifensulfuron- 5.0% 5.0% methyl Rimsulfuron 5.0% 5.0% 5.0% 5.0%

Agnique ME 18 29.1% 29.1% 29.1% 29.1% 29.1% 29.1%

SU

Aerosil R974 4.0% 4.0% 4.0% 4.0% 4.0% 4.0%

Isopar M To 100% To 100% To 100% To 100% To 100% To 100%

Atlox 4912 1.6% 1.6% 1.6% 1.6% 1.6% 1.6%

Ninate 60E 3.9% 3.9% 3.9% 3.9% 3.9% 3.9%

Plutonic P 105 2.6% 2.6% 2.6% 2.6% 2.6% 2.6%

Octyl gallate 1.0%

Quercetin 5.0%

Epigallocatechin 5.0% gallate

Tannic acid 5.0%

Stability (%) 97.9% 99.2% 88.6% 96.0% 96.6% 94.1%

[0030] The present invention is not limited in scope by the embodiments disclosed herein which are intended as illustrations of a few aspects of the invention and any embodiments which are functionally equivalent are within the scope of this invention. Various modifications of the compositions and methods in addition to those shown and described herein will become apparent to those skilled in the art and are intended to fall within the scope of the appended claims. Further, while only certain representative combinations of the composition components and method steps disclosed herein are specifically discussed in the embodiments above, other combinations of the composition components and method steps will become apparent to those skilled in the art and also are intended to fall within the scope of the appended claims. Thus, a combination of components or method steps may be explicitly mentioned herein; however, other combinations of components and method steps are included, even though not explicitly stated. The term comprising and variations thereof as used herein is used synonymously with the term including and variations thereof and are open, nonlimiting terms.

Claims

CLAIMS We claim:

1. A herbicidal composition comprising sulfonylurea herbicide, florpyrauxifen-benzyl, stabilizer, rheology modifier, adjuvant, surfactant, and solvent.

2. The composition according to claim 1, wherein the stabilizer is a gallate ester selected from the group consisting of octyl gallate, lauryl gallate, and propyl gallate.

3. The composition according to claim 2, wherein the gallate ester is propyl gallate.

4. The composition according to claim 2, wherein the gallate ester is lauryl gallate.

5. The composition according to claim 1, wherein the rheology modifier is silica based.

6. The composition according to claim 1, wherein the solvent is a paraffinic solvent.

7. The composition according to claim 1 , where the sulfonylurea herbicide is selected from the group consisting of amidosulfuron, azimsulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron- methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron-methyl sodium, foramsulfuron, halo- sulfuronmethyl, imazosulfuron, iofunsulfuron, iodosulfuron-methyl sodium, mesosulfuron- methyl, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron-methyl, propyrisulfuron, prosulfuron, pyrimisulfan, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron- methyl, sulfosulfuron, thifensulfuron-methyl, triasulfuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron-methyl, tritosulfuron, sulfosulfuron, foramsulfuron, iodosulfuron, and mixtures thereof.

8. The composition according to claim 1, wherein the sulfonyl urea herbicide is amidosulfuron.

9. The composition according to claim 1, wherein the surfactant is selected from the group consisting of ABA block copolymers, EO-PO block copolymers, alcohol alkoxylates, alyylbenzene sulfonates, nonionic surfactants, polyglycol ethers, and mixtures thereof.

10. The composition according to claim 1, wherein the rheology modifier is selected from the group consisting of polysaccharides, xanthan gum, organic sheet materials, inorganic sheet minerals, silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, less, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, pyrophyllite clay, attapulgus clay, kieselguhr, calcium carbonate, bentonite clay, Fuller's earth, cottonseed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell flour, lignin, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders, .and mixtures thereof.

11. The composition according to claim 1 comprising from 1 to 10% sulfonylurea, from 0.25 to 7% florpyrauxifen-benzyl, from 2 to 10% rheology modifier, from 5 to 40% adjuvant, from 2 to 15% surfactant, from 0.1 to 3% stabilizer, and from 15 to 89.65% solvent.

12. The composition according to claim 1, wherein the particles of herbicide have an average particle size (D90) between 7 and 9 pm.

13. A method of preparing a herbicidal composition comprising a. preparing a millbase of sulfonylurea; and b. preparing a millbase of florpyrauxifen-benzyl; and c. preparing a phenolics slurry; and d. mixing sulfonylurea millbase, florpyrauxifen-benzyl millbase, and phenolics slurry; and e. adding surfactant to the mixture; and f. adding rheology modifier to the mixture; and g. adding solvent to the mixture; and h. optionally adding other ingredients; and i. mixing until the mixture is homogeneous.