Propylene oxide-capped liquid polymeric surfactants for agricultural compositions and agricultural compositions containing pesticides - Patents.com

Abstract

Agricultural compositions and propylene-capped liquid polymer surfactants for agricultural compositions containing pesticides are provided. For example, the agricultural composition may comprise (a) an agricultural oil and (b) a propylene-capped liquid polymer surfactant having the following structure: [Formula 1] and an agricultural oil-compatible propylene oxide (PO)-capped liquid polymer surfactant having the formula: JPEG2022524595000012.jpg46170, where m is an integer from about 3 to about 7, n is an integer from about 5 to about 20, o is an integer from about 3 to about 30, and R is a linear or branched C4 to C18 alkyl chain.

Description

[Technical field]

[0001] The present disclosure generally relates to agricultural compositions and agricultural compositions comprising pesticides.More specifically, but not by way of limitation, the present disclosure relates to agricultural compositions comprising agricultural oil-compatible propylene oxide (PO)-capped liquid polymeric surfactants and agricultural compositions comprising pesticides. [Background technology]

[0002] For example, various adjuvants can be used in compositions containing pesticides to enhance the performance of the active ingredients, such as herbicides, insecticides and / or fungicides. Examples of adjuvants include wetting agents, crop oil concentrates (COCs), spreaders, stickers, buffers, foaming and defoaming agents, dispersants and drift control agents.

[0003] COCs are commonly used adjuvants. Including COCs in agricultural formulations can increase the effectiveness of the active ingredients in agricultural formulations. For example, COCs can promote the movement of active ingredients, reduce the surface tension of the spray solution, and / or improve wetting.

[0004] COCs can be a combination of agricultural oils, such as oils of petroleum / vegetable origin, and surfactants. Examples of surfactants that can be used in COCs include non-ionic surfactants, such as alkylphenol ethoxylates (APEOs), alcohol ethoxylates, castor oil ethoxylates, sorbitan esters and their reaction products with ethylene oxide (EO), and block copolymers of EO and propylene oxide (PO). The surfactants emulsify the agricultural oil in response to the addition of water to the COC formulation, thereby allowing the formation of an oil / water emulsion (O / W). Additionally, the surfactants may provide additional benefits, such as reducing the surface tension of the spray solution and / or improving the wetting of surfaces, such as leaf surfaces.

[0005] However, the inclusion of surfactants in COCs can increase unwanted foaming. Additionally, some surfactants may be insoluble in agricultural oils and / or may be unable to emulsify agricultural compositions containing water. Increased foaming, insolubility in agricultural oils, and / or lack of emulsification can result in difficult delivery and / or reduced efficacy of active ingredients such as pesticides. Thus, it may be desirable for surfactants to exhibit oil solubility, low foam generation, and enhanced emulsifying properties.

[0006] Additionally, it may be desirable for the surfactant to be in a liquid state to improve processability / performance, although not all surfactants are liquid. For example, U.S. Patent Nos. 3,955,401 and 4,317,940 each describe PO-EO-PO triblock adducts that are semi-solid (slush to solid) at room temperature.

[0007] Additionally, it may be desirable for the surfactant to be readily biodegradable. However, not all surfactants are readily biodegradable. U.S. Pat. No. 4,925,587 also discloses diblock copolymers with linear aliphatic hydrocarbon ends. U.S. Pat. Nos. 3,955,401 and 4,317,940 each describe PO-EO-PO triblock copolymers prepared with linear initiators to have linear aliphatic hydrocarbons at the PO ends of the copolymer. In particular, each of the surfactants in the above references (U.S. Pat. No. 4,925,587; U.S. Pat. No. 3,955,401 and U.S. Pat. No. 4,317,940) is initiated with a linear initiator to ultimately achieve a linear hydrocarbon group on the surfactant. The reason that the linear hydrocarbon group is recognized as being so important is that it has long been believed that surfactant branching critically affects the biodegradability of the surfactant. For example, U.S. Patent Nos. 3,955,401 and 4,317,940 each teach that "the biodegradability of the product is adversely affected by branching." Thus, to achieve biodegradability, surfactants are prepared using linear alcohols as initiators. The deleterious effect of branching on biodegradability was further confirmed in a study of ethoxylate polymers that concluded that polymers initiated with single or multiple branched alcohols showed no significant degradation, but significant degradation was observed for ethoxylates containing linear and iso-alcohols. (See M.T. Muller, M. Siegfried, and Urs Bauman, "Anaerobic Degradation and Toxicity of Alcohol Ethoxylates in Anaerobic Screening Test Systems," presented at the Fourth World Surfactant Congress, 1996). None of the references describe liquid surfactants that exhibit oil solubility, low foam generation, and enhanced emulsification while also being readily biodegradable. Summary of the Invention [Problem to be solved by the invention]

[0008] There is a clear need in the market for liquid surfactants that exhibit oil solubility, low foam generation, and enhanced emulsifying properties.There is also a clear need in the market for liquid surfactants that exhibit oil solubility, low foam generation, and enhanced emulsifying properties, yet are readily biodegradable.

[0009] In various embodiments, the present disclosure provides a method for producing a pharmaceutical composition comprising: (a) agricultural oil; (b) the structure [ka] and an agricultural oil-compatible propylene oxide (PO)-capped liquid polymeric surfactant having the formula: wherein m is an integer from about 3 to about 7, n is an integer from about 5 to about 20, o is an integer from about 3 to about 30, and R is a straight or branched C4 to C18 alkyl chain.

[0010] In various embodiments, the present disclosure provides a method for producing a pharmaceutical composition comprising: (a) agricultural oil; (b) the structure [ka] wherein m is an integer from about 3 to about 10, n is an integer from about 5 to about 20, o is an integer from about 3 to about 30, and R is a linear or branched C4 to C18 alkyl chain; (c) a pesticide, and an agricultural composition comprising a pesticide.

[0011] As detailed herein, the agricultural oil-compatible PO-capped liquid polymeric surfactants of the present disclosure surprisingly provide improved oil solubility, low foam performance, and enhanced emulsification. That is, the advantages of the agricultural oil-compatible PO-capped liquid polymeric surfactants of the present disclosure over other surfactants may include: (1) improved oil solubility, (2) improved (low) foam performance, (3) enhanced emulsification, (4) being liquid, and / or (5) being readily biodegradable. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0012] In various embodiments, the present disclosure provides a method for producing an agricultural oil comprising the steps of: [ka] and an agricultural oil-compatible PO-capped liquid polymeric surfactant having the formula: (wherein m is an integer of from about 3 to about 10, n is an integer of from about 5 to about 20, o is an integer of from about 3 to about 30, and R is a linear or branched C4 to C18 alkyl chain.

[0013] As used herein, "propylene oxide (PO)-capped" refers to the presence of propylene oxide moieties at the end blocks of an R-PO-EO-PO triblock copolymer, in contrast to other surfactants of other approaches that lack a PO moiety or do not have PO at the end blocks of the block copolymer, such as R-PO-EO diblock copolymers with EO at the end blocks.

[0014] As used herein, the terms "a," "an," "the," "at least one," and "one or more" are used interchangeably. The terms "comprise" and "include," and variations thereof, do not have a limiting meaning when these terms appear in the specification and claims. Thus, for example, "a" substance can be interpreted to mean "one or more" substances, and a composition that "includes" or "comprises" a substance can be interpreted to mean that the composition includes something in addition to the substance.

[0015] The recitation of numerical ranges by endpoints includes all numbers subsumed within that range, for example, 1 to 5 includes 1, 1.5, 2, 2.75, 3, 3.80, 4, 5, and so on.

[0016] By "particle size" herein is meant the number average particle diameter as measured, for example, by light scattering techniques.

[0017] As used herein, the term "polymer" includes oligomers.

[0018] The term "about" as used herein means that amounts, sizes, formulations, parameters, and other quantities and characteristics are not and need not be exact, and may be approximate and / or larger or smaller, as appropriate, to reflect tolerances, conversion factors, rounding, measurement errors, and the like, and other factors known to those skilled in the art. When the term "about" is used in describing a value or an end point of a range, the disclosure should be understood to include the specific value or end point mentioned. Regardless of whether or not the end point of a numerical value or range in the specification is described as "about", the end point of the numerical value or range is intended to include both embodiments, those modified by "about" and those not modified by "about". Furthermore, it will be understood that the end points of each range are significant both in relation to the other end point and independently of the other end point.

[0019] Unless stated to the contrary, implied by context, or customary in the art, all parts and percentages are by weight.

[0020] The agricultural oils used in the agricultural compositions and agricultural compositions containing pesticides of this invention are typically highly pure water-immiscible compounds suitable for pesticide applications and generally consist of a single aliphatic or aromatic chemical structure. 6 ~C 26 or C 20 ~C 26The oil may be branched or linear, with a typical carbon chain length of 100 to 2000 nm. Agricultural oils are characterized by low odor, low solubility for organic and organometallic compounds, low phytotoxicity to biological species, and low volatility. Commercial examples of agricultural oils include Aromatic 200, Aromatic 150, methylated seed oil (MSO), Orchex 796, Orchex 692, Sunspray 7N, Sunspray llN, Oleo Branco, Isopar M, Isopar V, 100 Neutral, and Exxsol D-130. Other oils such as mineral oils, crop oils such as vegetable oil, peanut oil, canola oil, and cottonseed oil, or synthetic oils may be acceptable.

[0021] In various embodiments, an agricultural oil-compatible, PO-capped liquid polymeric surfactant having the structure

[0022] [ka]

[0023] (among other possibilities, where m is an integer from about 0 to about 10, n is an integer from about 5 to about 20, o is an integer from about 3 to about 30, and R is a linear or branched C4 to C18 alkyl chain; or

[0024] m is an integer from about 3 to about 7, n is an integer from about 5 to about 20, o is an integer from about 3 to about 30, and R is a linear or branched C4 to C18 alkyl chain; or

[0025] m is an integer from about 3 to about 10, n is an integer from about 5 to about 20, o is an integer from about 3 to about 30, and R is a branched C4 to C18 alkyl chain), i.e., the values ​​of m, n, and / or o can vary as detailed herein.

[0026] For example, in some embodiments, m is an integer from about 0 to about 10. All individual values ​​and subranges from about 0 to about 10 are included, for example, m can be from a lower limit of about 1, 2, 3, 4, or 5 to an upper limit of about 10, 9, 8, 7, 6, or 5. For example, in some embodiments, m can be an integer from about 3 to about 7, an integer from about 3 to about 6, or an integer from about 3 to about 5. In some embodiments, m can be equal to about 5.

[0027] In some embodiments, n is an integer from about 5 to about 20. All individual values ​​and subranges from about 5 to about 20 are included, for example, n can be from a lower limit of about 5, 6, 9, 10, or 11 to an upper limit of about 20, 15, 14, or 10. For example, in some embodiments, n can be an integer from about 3 to about 9, from about 6 to about 9, from about 9 to about 14, or from about 9 to about 15. In some embodiments, n can be equal to about 6 or 9, or equal to about 14.

[0028] In some embodiments, o is an integer from about 3 to about 30. All individual values ​​and subranges from about 3 to about 30 are included, for example, o can be from a lower limit of about 3, 5, 10, or 15 to an upper limit of about 30, 25, 20, 15, 14, or 10. For example, in some embodiments, o is an integer from about 5 to about 20, an integer from about 5 to about 30, an integer from about 5 to about 25, an integer from about 10 to about 25, or an integer from about 15 to about 25. In some embodiments, o can be equal to about 5, about 10, about 15, about 20, or about 25.

[0029] In various embodiments, R can be a branched C4-C18 alkyl chain or a linear C4-C18 alkyl chain. That is, in some embodiments, R is a branched C4-C18 alkyl chain. However, in some embodiments, R can be a linear C4-C18 alkyl chain. In some embodiments, R can be formed from branched alkyls, each branch having a length of two or more carbons.

[0030] In various embodiments, the agricultural composition can have the agricultural oil (a) present at least 60% by weight, at least 70% by weight, or at least 80% by weight per volume of the agricultural composition. That is, the agricultural oil (a) can be present in an amount of about 60% to about 99% by weight per volume of the agricultural composition. Similarly, the agricultural oil can be about 60% to about 99% by weight, at least 60%, at least 70%, or at least 80% by weight per volume of the agricultural composition comprising the pesticide described herein.

[0031] In various embodiments, the agricultural oil-compatible, PO-capped liquid polymeric surfactant (b) is present in an amount of about 0.5 to 40.0 wt.%, about 1.0 to about 20.0 wt.%, about 10.0 to about 20.0 wt.%, or 15.0 to about 20.0 wt.% per volume of the agricultural composition. That is, the agricultural oil-compatible, PO-capped liquid polymeric surfactant can be present in an amount of about 0.5 wt.% to about 40 wt.% per volume of the agricultural composition. Similarly, the agricultural oil-compatible, PO-capped liquid polymeric surfactant can be about 0.5 to 40.0 wt.%, 1.0 to about 20.0 wt.%, about 10.0 to about 20.0 wt.%, or about 15.0 to about 20.0 wt.% per volume of the agricultural composition comprising the pesticide described herein.

[0032] In various embodiments, the agricultural composition can include a pesticide. The pesticide can be a liquid pesticide or a particulate pesticide, among other types of pesticides. For example, the pesticide can be an industrial grade particulate pesticide ("technical") or a formulated particulate pesticide composition, such as, for example, wettable powders and dispersible granules. Industrial grade particulate pesticides have an active ingredient content in the range of 80-98% by weight and are solid at room temperature. Wettable powders and dispersible granules have an active ingredient content in the range of 45%-75% by weight, with a typical composition being 45-75% by weight pesticide, 20-50% by weight carrier, 2-10% by weight dispersant, and 2-10% by weight surfactant. Wettable powders and dispersible granules are typically milled to an average particle size in the range of 2-10 microns.

[0033] The selection of pesticide is not particularly important with respect to the quality of the agricultural composition containing the pesticide. Examples of pesticides that may be used herein include particulate agriculturally effective fungicides, herbicides, and insecticides, such as chlorinated nitriles, triazoles, aralkyltriazoles, triazoleanilides, benzamides, alkylbenzamides, diphenyl ethers, pyridine carboxylic acids, chloroanilines, organic phosphates, phosphonic acid glycine salts, and mixtures thereof. Also included are mixtures of pesticides and other organic or inorganic agriculturally active ingredients, such as Dithane+Indar, Dithane+chlorothalonil, Dithane+cymoxanil, and Dithane+copper hydroxide. Additional examples of pesticides can be found in U.S. Patent No. 6,210,696. Mixtures of pesticides may be used.

[0034] The agricultural composition comprising the pesticide of the present disclosure comprises (a) agricultural oil; (b) the structure [ka] wherein m is an integer from about 3 to about 10, n is an integer from about 5 to about 20, o is an integer from about 3 to about 30, and R is a branched C4 to C18 alkyl chain; (c) a pesticide.

[0035] Agricultural compositions containing the pesticides of the present disclosure are typically applied to the field as dilutions of oil or oil / water / surfactant carriers. Agricultural compositions containing the pesticides of the present disclosure and / or agricultural compositions containing the pesticides may contain other formulated agricultural additives, such as, for example, defoamers, stabilizers, fragrances, sequestering agents, neutralizing agents, buffers, corrosion inhibitors, dyes, softeners, odorants, additional surfactants, and / or surfactant adjuvants. Concentrated formulations may be diluted 1-2000 times at the time of use, depending on the intended agricultural application. Application may be made by ground or aerial spraying equipment.

[0036] The effective amount of the agricultural composition containing the pesticide of the present invention used in a typical agricultural application often depends on, for example, the type of plant, the growth stage of the plant, the severity of the environmental conditions, the weed, insect, or fungal pathogen to be controlled, and the application conditions. Typically, a plant requiring protection from a weed or insect, or control or elimination of a pathogen, is contacted with an amount of the agricultural composition containing the pesticide diluted with a carrier such as water to provide an amount of active ingredient of about 1 to about 40,000 ppm, preferably about 10 to about 20,000 ppm.

[0037] That is, in some embodiments, the agricultural compositions and / or agricultural compositions containing pesticides described herein can contain water. In particular, the agricultural compositions / agricultural compositions containing pesticides disclosed herein, in addition to being liquid and oil-soluble, also exhibit lower foaming and improved emulsion stability compared to agricultural compositions that do not contain (b) [Applicant's agricultural oil-compatible, PO-capped liquid polymeric surfactant], as described in detail in the Examples below.

[0038] Specific embodiments material

[0039] 2EH / 5PO / 9EO and 2EH / 5PO / 14EO have the general structure R-(PO) m -(EO) n and alcohol alkoxylated block copolymers obtained as described below, where R is 2-ethylhexanol, m=5, and n=9 or 14, respectively.

[0040] TERGITOL™ XD is a butanol-PO / EO copolymer available from Sigma-Aldrich.

[0041] DOWFAX™ 100N50 is a butanol-PO / EO copolymer available from The DOW Chemical Company.

[0042] Soybean oil was obtained from Duwest.

[0043] MSO was obtained from Stepan under the trade name STEPOSOL® ME.

[0044] Examples 1 to 7 (WE1 to 7) and Comparative Examples 1 to 4 (CE1 to 4)

[0045] For CE1-4, four different competitive surfactants were procured from the sources described above and subjected to the tests detailed herein, specifically, CE1 corresponds to a surfactant of the formula 2EH / 5PO / 9EO, CE2 corresponds to a surfactant of the formula 2EH / 5PO / 14EO, CE3 corresponds to a surfactant available under the trade name TERGITOL™ XD, and CE4 corresponds to a surfactant available under the trade name DOWFAX™ 100N50.

[0046] For WE1-7, seven different surfactants of structure (I) listed in Table 1 were prepared as follows using the following procedure, in accordance with the procedures described in U.S. Patent Application No. 2017 / 028,3742A1 (the entire contents of which are incorporated herein):

[0047] Charge a 9 liter reactor purged with nitrogen with 780.0 grams of 2-ethylhexanol and 10.81 grams of 85% potassium hydroxide pellets. Apply vacuum to the reactor gradually over 2 hours to achieve 100 millimeters of mercury. Remove 15.8 grams of mixture from the reactor and measure the moisture content by Karl Fischer titration (411 parts per million by weight (ppm)). Pressurize and evacuate the reactor seven times with dry nitrogen to remove atmospheric oxygen, then pressurize with nitrogen to 110-139 kilopascals (kPa) at 25°C. Heat the reactor contents with stirring to 130°C. Then meter in 1660 grams of propylene oxide over 4 hours. After the propylene oxide feed is complete, stir the reactor contents at 130°C for an additional 2 hours. Then cool to 60°C. Remove 142.9 grams of the reactor contents. Heat the reactor contents to 130°C. Then, 2070 grams of ethylene oxide are metered into the reactor over 4 hours. Once the ethylene oxide feed is complete, the reactor contents are stirred at 130°C for 2 hours and then cooled to 60°C. 142.9 grams of the reactor contents are removed and neutralized with acetic acid to a pH of 4-8 (in a 10% aqueous solution) to provide the CE1 surfactant. The reactor contents are heated to 130°C. Then, 1475 grams of propylene oxide are metered into the reactor over 4 hours and stirring is continued at 130°C for an additional 2 hours. The reactor contents are cooled to 60°C.

[0048] Remove 158.2 grams of the reactor contents and neutralize with acetic acid to a pH of 4-8 (in a 10% aqueous solution) to yield WE1 surfactant.

[0049] The reactor contents are heated back to 130° C. and 1170 g of propylene oxide are metered into the reactor over 4 hours. Stirring is continued at 130° C. for an additional 2 hours and then cooled to 60° C. 118.7 grams of the reactor contents are removed and neutralized to a pH of 4-8 with a 10% aqueous solution of acetic acid to provide WE2 surfactant.

[0050] The reactor contents are heated back to 130° C. and 970 grams of propylene oxide are metered in over 4 hours and stirring is continued for an additional 2 hours at 130° C. The reactor contents are cooled to 60° C. The reactor contents are neutralized with a 10% aqueous solution of acetic acid to a pH of 4-8 to provide the WE3 surfactant.

[0051] Prepare surfactants CE2 and WE4-7 in a similar manner by adjusting the feed amounts of PO and EO to the appropriate molar ratios for these specific surfactants.

[0052] Testing of surfactants CE1-4 and WE0-7 was carried out as detailed herein. The properties of each of the surfactants CE1-4 and WE1-7 are shown in Tables 1, 2, and 3. Each of the surfactants WE1-7 has the structure of Structure (I), and each structure is given by specifying the values ​​of m, n, and z for each surfactant.

[0053] Cloud points were determined for 1 or 10 weight percent (wt%) solutions of the surfactants in deionized water (as shown in Table 1) using a Mettler Toledo FP900 Thermal System equipped with an FP90 central processor and an FP81 measuring cell conforming to ASTM D2024-09.

[0054] Loss miles (the tendency of a surfactant to produce and / or maintain foam) is measured in accordance with Loss Miles Test Protocol ASTM Designation D-1173-53 (0.1%, 70°F).

[0055] Pour point is measured using an automated MPP5Gs instrument available from Instrumentation Scientifique de Laboratoire. Pour point measurements obtained with this instrument correlate to ASTM D-97 "Standard Test Method for Pour Point of Petroleum Products."

[0056] The surface tension of surfactants is determined using a 0.1 wt% aqueous surfactant solution and a Kruss D12 tensiometer fitted with a Wilhelmy platinum plate at 25°C. The solution is made by dissolving the surfactant in deionized water. The deionized water used to make the solution has a surface tension of 72-73 millinewtons per meter. Results are reported as the average of five replicate test values ​​with a standard deviation of less than 0.1 mN / m.

[0057] Solubility was determined for each surfactant by adding 3.6 g of oil and 0.4 g of surfactant (from WE1-7 and CE1-3) to a 20 mL borosilicate glass container. The glass container was then capped and shaken by hand for 1 minute. The mixture was analyzed after 1 day, 1 week, and 2 months at room temperature and visually observed at each time interval for phase separation or turbidity. After 2 months at room temperature, samples were stored at -5°C for 14 days and samples were visually observed for phase separation. After 14 days at -5°C, samples were kept at room temperature for 14 days and visually observed for phase separation or turbidity. The solubility of the surfactants (insoluble, miscible) in Table 2 was determined based on visual observation after 14 days at room temperature. In one embodiment, after mixing the oil and surfactant, the active ingredient (pesticide) as well as any optional ingredients, such as emollients, dispersants, and emulsifiers, can be added to the container under shear conditions until a homogenous agricultural composition containing the pesticide (oil dispersion) is formed.

[0058] Foam height (FH) and emulsion stability (ES) were determined by combining 0.2 g of agricultural oil solution and surfactant [90 wt% agricultural oil + 10 wt% surfactant] in a 25 mL glass container. 19.8 g of water was added to the 25 mL glass container and the container was sealed. The glass container was shaken by hand for 1 min. The total volume of emulsion was approximately 20 mL (this corresponds to a solution height of approximately 4.2 centimeters (cm) from the bottom of the glass container). Photographs of the emulsion were taken at time 0 (after 1 min of shaking) at 25 °C and again after 30 min. Foam height (the distance of bubbles extending perpendicularly away from the liquid surface of the solution) was determined based on visual inspection and measurement after 1 min of shaking. Emulsion stability was monitored for 30 min at 25 °C using a multiple light scattering Turbiscan device (Formulaction, France). Light transmittance was used to analyze emulsion stability. The emulsion stability of the surfactants in Table 2 (emulsion, translucent) was determined with a multiple light scattering Turbiscan device initially at time (0) and at the end of 30 minutes.

[0059] The biodegradability of WE1-7 was measured according to the Organization for Economic Cooperation and Development (OECD) test method 301F.

[0060] [Table 1] a. 1.0 wt% in deionized (DI) water. bDI 10.0% by weight in water. cDI 1.0% by weight in water

[0061] [Table 2] *NM means not determined, except for examples where only z is varied (WE2, WE5, and WE7), where the NM values ​​for biodegradability are expected to be between those of similar surfactants with higher and lower z values.

[0062] [Table 3]

[0063] Liquid Surfactants: Each of the surfactants WE1-7 is liquid at room temperature and ambient atmospheric pressure, and each of the surfactants WE1-7 has been proven to have a pour point below room temperature (a pour point below about 23°C). Specifically, as shown in Table 1, the pour points of the surfactants WE1, WE2, WE3, WE4, WE5, WE6, and WE7 were -18°C, -15°C, -18°C, -3°C, 3°C, 3°C, and 3°C, respectively. That is, each surfactant has a flow temperature at least 20 degrees lower than room temperature, ensuring that the surfactants WE1-7 remain in a liquid state at room temperature. Having the surfactant in a liquid state can improve processability, improve oil solubility, etc., compared to other surfactants, such as surfactants that are in a semi-solid state at room temperature.

[0064] Solubility, foam height and emulsion stability:

[0065] CE3 and CE4 show that the butanol-POEO copolymers TERGITOL™ XD and DOWFAX™ 100N50, which are considered traditional POEO block copolymers, are not compatible (miscible) with agricultural oils. That is, as shown in Table 2, both TERGITOL™ XD and DOWFAX™ 100N50 are insoluble in soybean oil and / or MSO. Similarly, CE1 and CE2 show that other PO / EO copolymers are insoluble in at least one of soybean oil and / or MSO. In contrast, and surprisingly, each of WE1-7 is soluble in agricultural oils. That is, as shown in Table 2, each of the surfactants WE1-7 is soluble in both soybean oil and MSO.

[0066] Additionally, the oil-soluble WE1-7 also have minimal foaming, for example, each of WE1-7 has a foam size of less than 0.7 cm with soybean oil and less than 0.6 cm with MSO.

[0067] Additionally, WE1-7, which are oil-soluble, also have improved emulsion stability. For example, WE3, 6, and 7 show stable white emulsions in soybean oil compared to translucent CE1-3 (which do not form emulsions in soybean oil). As used herein, exhibiting emulsion stability, described in Table 2 as "emulsion," indicates that the solutions (e.g., WE3 and WE6-7 in the case of soybean oil) have a delta transmission (after 30 minutes at 0.4 cm) of 1.0% or less (shown in Table 3), while solutions designated as "translucent" (e.g., CE1-1 and WE1-2, 4-5 in the case of soybean oil) showed delta transmission of greater than 1.0 seconds (shown in Table 3).

[0068] Biodegradability: Each of the surfactants WE1-7 exhibits a biodegradability value of 80% or greater. A value of 60% is considered "readily biodegradable" in the test method. Therefore, each of the surfactants WE1-7 is considered to be readily biodegradable.

Claims

1. (a) an agricultural oil selected from the group consisting of mineral oil, soybean oil, vegetable oil, peanut oil, canola oil, cottonseed oil, and synthetic oils; (b) a compound having the structure 【Chemistry 1】 and an agricultural oil-compatible propylene oxide (PO)-capped liquid polymeric surfactant having the formula: wherein m is an integer from 3 to 7, n is an integer from 5 to 20, o is an integer from 3 to 30, and R is a linear or branched C4 to C18 alkyl chain.

2. (a) is at least 60%, at least 70%, or at least 80% by weight per volume of the agricultural composition; 2. The agricultural composition of claim 1, wherein (b) is 0.5 to 40.0% by weight, 1.0 to 20.0% by weight, 10.0 to 20.0% by weight, or 15.0 to 20.0% by weight, based on the volume of the agricultural composition.

3. 10. The agricultural composition of claim 1, further comprising water, said agricultural composition exhibiting lower foaming and improved emulsion stability compared to an agricultural composition not comprising (b).

4. 10. The agricultural composition of claim 1 further comprising a pesticide.

5. 2. The agricultural composition according to claim 1, wherein m is an integer from 3 to 6 or an integer from 3 to 5.

6. 2. The agricultural composition of claim 1, wherein m is 5.

7. 2. The agricultural composition according to claim 1, wherein n is an integer from 6 to 15, or an integer from 9 to 14.

8. 2. The agricultural composition according to claim 1, wherein o is an integer from 10 to 25.

9. 2. The agricultural composition according to claim 1, wherein R is a branched C4 to C18 alkyl chain.

10. (a) an agricultural oil selected from the group consisting of mineral oil, soybean oil, vegetable oil, peanut oil, canola oil, cottonseed oil, and synthetic oils; (b) a compound having the structure 【Chemistry 2】 wherein m is an integer from 3 to 10, n is an integer from 5 to 20, o is an integer from 3 to 30, and R is a branched C4 to C18 alkyl chain; (c) a pesticide.

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