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CN-116615101-B - Branched amino acid surfactants for agricultural products

CN116615101BCN 116615101 BCN116615101 BCN 116615101BCN-116615101-B

Abstract

Agricultural products, such as pesticides, plant growth regulators, fungicides, herbicides, and insecticides, can be formulated to include one or more branched chain surfactants from one or more surfactant classes, such as derivatives of amino acids having surface active properties.

Inventors

  • E. Asiwatan

Assignees

  • 艾德凡斯化学公司

Dates

Publication Date
20260512
Application Date
20210709
Priority Date
20200713

Claims (11)

  1. 1. A pesticide formulation comprising: at least one surfactant of the formula: Wherein R 1 and R 2 are independently selected from hydrogen, an oxygen atom, and a C 1 -C 6 alkyl group, wherein the C 1 -C 6 alkyl group may be substituted with carboxylate, hydroxy, sulfonyl, or sulfonate; n is an integer from 2 to 5; r 3 is C 5 -C 12 alkyl; R 4 is C 3 -C 10 alkyl; The terminal nitrogen is optionally further substituted with R 5 , wherein R 5 is selected from the group consisting of hydrogen, an oxygen atom, and a C 1 -C 6 alkyl group, wherein the C 1 -C 6 alkyl group may be substituted with carboxylate, hydroxy, sulfonyl, or sulfonate; an optional counter ion may be associated with the compound and, if present, may be selected from the group consisting of chloride, bromide, iodide, and 4-methylbenzenesulfonate, and The pesticide is used for preparing the pesticide, Wherein the surfactant comprises at least one of: 6- ((2-butyloctyl) oxy) -N, N-trimethyl-6-oxohexane-1-aminium iodide having the formula: 6- ((2-butyloctyl) oxy) -N, N-dimethyl-6-oxohexane-1-aminium 4-methylbenzenesulfonate having the formula: 4- ((6- ((2-butyloctyl) oxy) -6-oxohexyl) dimethylammonium) butane-1-sulfonate having the formula: ; 2-butyloctyl 6- (dimethylamino) hexanoate N-oxide having the formula: 6- ((2-butyloctyl) oxy) -6-oxohexane-1-amine onium chloride having the formula: And 6- ((2-Butyloctyl) oxy) -6-oxohexane-1-aminium 4-methylbenzenesulfonate having the formula: 。
  2. 2. the formulation of claim 1, further comprising a water insoluble solvent.
  3. 3. A fungicide formulation comprising: at least one surfactant of the formula: Wherein R 1 and R 2 are independently selected from hydrogen, an oxygen atom, and a C 1 -C 6 alkyl group, wherein the C 1 -C 6 alkyl group may be substituted with carboxylate, hydroxy, sulfonyl, or sulfonate; n is an integer from 2 to 5; r 3 is C 5 -C 12 alkyl; R 4 is C 3 -C 10 alkyl; The terminal nitrogen is optionally further substituted with R 5 , wherein R 5 is selected from the group consisting of hydrogen, an oxygen atom, and a C 1 -C 6 alkyl group, wherein the C 1 -C 6 alkyl group may be substituted with carboxylate, hydroxy, sulfonyl, or sulfonate; an optional counter ion may be associated with the compound and, if present, may be selected from the group consisting of chloride, bromide, iodide, and 4-methylbenzenesulfonate, and A fungicide which is used as a fungicide, Wherein the surfactant comprises at least one of: 6- ((2-butyloctyl) oxy) -N, N-trimethyl-6-oxohexane-1-aminium iodide having the formula: 6- ((2-butyloctyl) oxy) -N, N-dimethyl-6-oxohexane-1-aminium 4-methylbenzenesulfonate having the formula: 4- ((6- ((2-butyloctyl) oxy) -6-oxohexyl) dimethylammonium) butane-1-sulfonate having the formula: ; 2-butyloctyl 6- (dimethylamino) hexanoate N-oxide having the formula: 6- ((2-butyloctyl) oxy) -6-oxohexane-1-amine onium chloride having the formula: And 6- ((2-Butyloctyl) oxy) -6-oxohexane-1-aminium 4-methylbenzenesulfonate having the formula: 。
  4. 4. The formulation of claim 3, further comprising a cosurfactant and/or a carrier agent.
  5. 5. A herbicide formulation comprising: at least one surfactant of the formula: Wherein R 1 and R 2 are independently selected from hydrogen, an oxygen atom, and a C 1 -C 6 alkyl group, wherein the C 1 -C 6 alkyl group may be substituted with carboxylate, hydroxy, sulfonyl, or sulfonate; n is an integer from 2 to 5; r 3 is C 5 -C 12 alkyl; R 4 is C 3 -C 10 alkyl; The terminal nitrogen is optionally further substituted with R 5 , wherein R 5 is selected from the group consisting of hydrogen, an oxygen atom, and a C 1 -C 6 alkyl group, wherein the C 1 -C 6 alkyl group may be substituted with carboxylate, hydroxy, sulfonyl, or sulfonate; an optional counter ion may be associated with the compound and, if present, may be selected from the group consisting of chloride, bromide, iodide, and 4-methylbenzenesulfonate, and The herbicide is used as a seed of the plant, Wherein the surfactant comprises at least one of: 6- ((2-butyloctyl) oxy) -N, N-trimethyl-6-oxohexane-1-aminium iodide having the formula: 6- ((2-butyloctyl) oxy) -N, N-dimethyl-6-oxohexane-1-aminium 4-methylbenzenesulfonate having the formula: 4- ((6- ((2-butyloctyl) oxy) -6-oxohexyl) dimethylammonium) butane-1-sulfonate having the formula: ; 2-butyloctyl 6- (dimethylamino) hexanoate N-oxide having the formula: 6- ((2-butyloctyl) oxy) -6-oxohexane-1-amine onium chloride having the formula: And 6- ((2-Butyloctyl) oxy) -6-oxohexane-1-aminium 4-methylbenzenesulfonate having the formula: 。
  6. 6. the formulation of claim 5, further comprising a second herbicide.
  7. 7. The formulation of claim 5, further comprising a water insoluble solvent or water.
  8. 8. An insecticide formulation comprising: at least one surfactant of the formula: Wherein R 1 and R 2 are independently selected from hydrogen, an oxygen atom, and a C 1 -C 6 alkyl group, wherein the C 1 -C 6 alkyl group may be substituted with carboxylate, hydroxy, sulfonyl, or sulfonate; n is an integer from 2 to 5; r 3 is C 5 -C 12 alkyl; R 4 is C 3 -C 10 alkyl; The terminal nitrogen is optionally further substituted with R 5 , wherein R 5 is selected from the group consisting of hydrogen, an oxygen atom, and a C 1 -C 6 alkyl group, wherein the C 1 -C 6 alkyl group may be substituted with carboxylate, hydroxy, sulfonyl, or sulfonate; an optional counter ion may be associated with the compound and, if present, may be selected from the group consisting of chloride, bromide, iodide, and 4-methylbenzenesulfonate, and The chemical composition of the pesticide, Wherein the surfactant comprises at least one of: 6- ((2-butyloctyl) oxy) -N, N-trimethyl-6-oxohexane-1-aminium iodide having the formula: 6- ((2-butyloctyl) oxy) -N, N-dimethyl-6-oxohexane-1-aminium 4-methylbenzenesulfonate having the formula: 4- ((6- ((2-butyloctyl) oxy) -6-oxohexyl) dimethylammonium) butane-1-sulfonate having the formula: ; 2-butyloctyl 6- (dimethylamino) hexanoate N-oxide having the formula: 6- ((2-butyloctyl) oxy) -6-oxohexane-1-amine onium chloride having the formula: And 6- ((2-Butyloctyl) oxy) -6-oxohexane-1-aminium 4-methylbenzenesulfonate having the formula: 。
  9. 9. the formulation of claim 8, further comprising an antifoaming agent.
  10. 10. The formulation of claim 8 or claim 9, further comprising an anti-freeze agent.
  11. 11. The formulation of any one of claims 8 to 10, further comprising water.

Description

Branched amino acid surfactants for agricultural products Cross Reference to Related Applications The present application claims priority from provisional application number 63/051,197 filed on 7/13/2020, the contents of which are incorporated herein by reference in their entirety. Technical Field The present disclosure relates to branched surfactants for use in agricultural products. Such branched surfactants may include derivatives of amino acids, wherein the derivatives have surface active properties. Background Surfactants (molecules with surface-active properties) are widely used in commercial agricultural formulations. These formulations may include a variety of agriculturally active agents such as pesticides, plant growth regulators, fungicides, herbicides, and insecticides. Many such agricultural actives exhibit limited water solubility or may be prone to crystallization. Precipitation of the agriculturally active agent may lead to loss of efficacy. If the active agent is concentrated in the sediment, it may prevent the active agent from being uniformly distributed when sprayed on the field. Thus, surfactants may be included in the formulation to improve the solubility, wettability and spreadability of the active agent. The surfactant may be uncharged, zwitterionic, cationic or anionic. Although in principle any surfactant class (e.g. cationic, anionic, nonionic, amphoteric) is suitable, the formulation may comprise a combination of two or more surfactants from two or more surfactant classes. Typically, surfactants are amphiphilic molecules having a hydrophobic "tail" group that is relatively insoluble in water and a hydrophilic "head" group that is relatively soluble in water. These compounds may adsorb at interfaces such as interfaces between two liquids, a liquid and a gas, or a liquid and a solid. In systems comprising relatively polar and relatively non-polar components, the hydrophobic tail preferentially interacts with the relatively non-polar component or components, while the hydrophilic head preferentially interacts with the relatively polar component or components. In the case of an interface between water and oil, the hydrophilic head groups preferentially extend into the water, while the hydrophobic tail preferentially extends into the oil. When added to the water-gas interface, the hydrophilic head groups preferentially extend into the water, while the hydrophobic tail preferentially extends into the gas. The presence of the surfactant disrupts at least a portion of the intermolecular interactions between water molecules, replacing at least some of the interactions between water molecules with at least a portion of the interactions between water molecules and the surfactant, which are typically weaker. This results in a decrease in surface tension and may also be used to stabilize the interface. At sufficiently high concentrations, the surfactant may form aggregates that serve to limit exposure of the hydrophobic tail to polar solvents. One such aggregate is a micelle. In a typical micelle, the molecules are arranged in a sphere, with the hydrophobic tail of the surfactant or surfactants preferentially positioned inside the sphere and the hydrophilic head of the surfactant or surfactants preferentially positioned outside the micelle, with the head preferentially interacting with the more polar solvent. The effect of a given compound on surface tension and its concentration at which micelles are formed can be a defining property of a surfactant. Disclosure of Invention The present disclosure provides formulations of agricultural products such as pesticides, plant growth regulators, fungicides, herbicides, and insecticides. These products may be formulated to include one or more surfactants from one or more of the surfactant classes disclosed herein. Surfactants may be used as emulsifiers, wetting agents, dispersants and/or spreadability improving agents. In addition, surfactants can be used as adjuvants and agents for controlling spray drift (SPIN DRIFT). The present disclosure provides surfactants for agricultural products in the form of amino acid derivatives having surface active properties. Amino acids may be naturally occurring or synthetic amino acids, or they may be obtained via a ring opening reaction of a molecule, such as a lactam (e.g., caprolactam). Amino acids may be functionalized with different types of groups to form compounds having surface-active properties. Characteristically, these compounds may have a low Critical Micelle Concentration (CMC) and/or the ability to reduce the surface tension of a liquid. The present disclosure provides a formulation for a pesticide or plant growth regulator comprising at least one surfactant of formula I: Wherein R 1 and R 2 are independently selected from the group consisting of hydrogen, an oxygen atom, and a C 1-C6 alkyl group, wherein the C 1-C6 alkyl group may be substituted with carboxylate, hydroxyl, sulfonyl, or sulfonate, n i