Hydrophobic and hydrophilic modified maleated natural oils and their agricultural compositions

Abstract

The present invention provides an agricultural composition comprising (A) a reaction product of a maleated natural oil and a functionalized or non-functionalized site selected from the group consisting of hydrophobic sites, hydrophilic sites and combinations thereof; further comprising (B) one or more agricultural active ingredients; and (C) one or more components. In yet another aspect of the present invention, the present invention provides compounds useful for agricultural compositions represented by the structures (I) and (II) below: JPEG2026511038000054.jpg204166

Description

Technical Field

[0001] This application provides an agricultural composition containing a modified maleated natural oil. The modified maleated natural oil does not exhibit many of the limited properties of maleated natural oil. The modified maleated natural oil is useful in a variety of agricultural compositions and applications.

Background Art

[0002] Modified natural oils may not disperse in water or alcohol. As a result, these oils can be incorporated into a variety of compositions. Such compositions include, but are not limited to, personal care (e.g., sun care, skin care, oral care), adhesives, coatings, paints, electronic devices, household, industrial and institutional (HI&I) compositions, inks, films, metalworking oils, oilfield chemicals, plastics and plasticizers, fibers, industrial products, biocides, pharmaceuticals / nutritional agents, and agricultural chemical compositions.

[0003] Natural oils such as soybean oil and linseed oil are one of the most promising raw materials in the synthesis of renewable compounds such as polymers, plastics, and plasticizers. These natural substances are inexpensive, very abundant, obtained from reliable and sustainable sources, and highly modifiable. Natural oils are generally mixtures of various triglycerides that are esterification products of fatty acids and glycerol, and have different degrees of unsaturation (i.e., double bonds). Oils can be characterized by their hydroxyl value and fatty acid composition. Both natural fatty acids and natural oils need to be chemically modified in order to have sufficient reactivity to allow for structural changes and polymerization. This is because olefin functional groups are relatively unreactive. The unsaturated double bonds in these compounds have been converted into epoxide functional groups and succinic anhydride functional groups, making it possible to introduce many hydroxyl-containing species into natural oils.

[0004] Maleated natural oils are natural oils that have been chemically functionalized by the chemical addition of epoxide (oxirane) and succinic anhydride functional groups. Examples include epoxidized and maleated soybean oil and linseed oil, and unsaturated natural oils are suitable for these chemical functionalizations.

[0005] U.S. Patent No. 9,809,538 describes modified natural compounds synthesized from epoxidized natural fatty acids, maleized natural fatty acids, epoxidized natural oils, or maleized natural oils and lactam compounds having hydroxyl groups, which form, for example, adhesives and beverage compositions.

[0006] The reaction scheme for the maleation reaction in vegetable oils is described in "Maleated soybean oil and its multifunctional properties" by Gripp, Anna A., Steinberg, David C. (Cosmetics Exhibition & Conference Conference Proceedings, Barcelona, ​​March 22-24, 1994).

[0007] The reaction scheme for maleation reactions in vegetable oils is described in the paper "Microwave Assisted Syntheses of Vegetable Oil Based Monomer" by Rafael T. Alarcon et al. (Journal of Polymers and the Environment 28:1265-1278, 2020).

[0008] The general reactions of maleic anhydride with unsaturated vegetable oils are described in "Handbook of Maleic Anhydride Based Materials - Syntheses, Properties and Applications" by Osama M. Musa (Springer International Publishing Switzerland, 2016, Chapter 3, p. 166).

[0009] U.S. Patent No. 2,754,306 describes providing an improved plasticizer for nitrocellulose compositions by the reaction of soybean oil, maleic anhydride, and isooctyl alcohol.

[0010] International Publication Nos. 2019113068 and 2005071050 describe technologies relating to metalworking fluids containing maleated soybean oil derivatives.

[0011] Polymerization of maleic anhydride and modification of plant oils with polyols are described in the paper "Polymerization of Maleic Anhydride-Modified Plant Oils with Polyols" by Tarik Eren, Selim H. Kusefoglu, and Richard Wool (Journal of Applied Polymer Science, Barcelona, ​​Volume 90, Issue 1, Pages 197-202, 2003).

[0012] European Patent No. 2754306 describes an adhesive comprising a polycondensate and a dienophile-modified fatty acid as a crosslinking agent.

[0013] U.S. Patent Application Publication No. 2018 / 0070584 describes an auxiliary composition for which maleated natural oil derivatives are incorporated into agricultural chemical formulations and applied to target substrates to kill, suppress, or repel pests.

[0014] International Publication No. 2005 / 071050 describes metalworking oils comprising water-in-oil emulsions derived from the reaction product of maleic anhydride with triglyceride oils of plant or terrestrial animal origin, further reacted with water, group IA and group IIA metals, ammonium hydroxide, various amines, alkanolamines, polyols, alkoxylated alkanolamines, poly(alkylene oxides) or polyamines, or mixtures thereof.

[0015] U.S. Patent No. 1,0889,693 discloses compositions used for the treatment of agricultural plants, comprising modified oil alkyl esters and / or modified oil aryl esters having a transesterification product of an oil (soybean oil) and a surfactant having a hydroxyl group.

[0016] U.S. Patent No. 5,733,970 discloses a water-dispersible epoxy crosslinked maleinated oil (maleinated glyceride oil) microgel polymer for protective coatings.

[0017] U.S. Patent Application Publication No. 20040 / 197363 discloses that the coated granular material is selected from fertilizers, crop protectants, insecticides, pesticides, fungicides, desiccants and mixtures, and the material has a curing agent such as maleic anhydride / soybean oil adduct.

[0018] U.S. Patent No. 9,809,538 discloses modified natural compounds synthesized from epoxidized natural fatty acids, maleized natural fatty acids, epoxidized natural oils or maleized natural oils and lactam compounds having hydroxyls, for use in agriculture.

[0019] U.S. Patent Application Publication No. 2013 / 0210630 discloses a self-emulsifying oil, which is modified by reacting a vegetable oil (e.g., maleated soybean oil) with a more polar portion than the vegetable oil; and contains an active ingredient (e.g., a herbicide).

[0020] Despite the renewable, biodegradable, sustainable, and beneficial properties of natural fatty acids, natural oils, and their maleated counterparts, they exhibit characteristics that can limit their applications. For example, maleated soybean oil is insoluble in water or alcohol and does not disperse. As a result, these oils tend to leach or undergo phase separation from formulations. This characteristic makes formulation difficult and often requires additional components to facilitate solutions, emulsions, or dispersions. Natural oils and maleated natural oils may not impart the desired properties required for their end use (such as solubility, glass transition, flexibility, gloss, and / or plasticity). Consequently, performance (including, but not limited to, stability, phase separation resistance, absorption, washability, solubility, stain resistance, lubricity, film formation, spreadability, comedogenicity, and ease of removal) may not reach the desired level. Finally, while such natural oils are important renewable materials, they are not always the first choice for compounders and are often not considered at all.

[0021] Mineral oils and vegetable oils are frequently used as components in agricultural compositions. Therefore, there is a need for renewable, natural, and biodegradable materials with different and controllable chemical, physical, and / or mechanical properties that can minimize or eliminate the limitations found in natural oils and maleated natural oils. Most agricultural compositions contain multiple inert components in combination with auxiliaries used in plant treatments to aid in the delivery of active ingredients with fungicidal, bactericidal, insecticidal, and herbicidal activity. Agricultural compositions containing modified maleated natural oils in combination with agricultural active ingredients and specific components can improve the efficiency of the active ingredients themselves and be used in agriculture. Therefore, there is a need for the development of novel functionalized maleated natural oils for use in therapeutic crop treatments and in non-toxic, renewable resource-inspired or derived agricultural compositions. [Overview of the project] [Problems that the invention aims to solve]

[0022] The present invention provides an agricultural composition comprising a reaction product of (A) maleated natural oil and a functionalized or non-functionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof.

[0023] In another aspect of the present invention, the present application provides an agricultural composition comprising: (A) a reaction product of maleated natural oil and a functionalized or non-functionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof; (B) one or more agricultural active ingredients; and (C) one or more components.

[0024] In another aspect of the present invention, the present application provides an agricultural composition comprising: (A) a reaction product of maleated natural oil, at least one functionalized or non-functionalized hydrophobic moiety, and at least one functionalized or non-functionalized hydrophilic moiety; (B) one or more agricultural active ingredients; and (C) one or more components.

[0025] In another aspect of the present invention, the present application provides an agricultural composition comprising a reaction product of (A) maleated soybean oil, octyldodecyl alcohol, and glycerol.

[0026] In another aspect of the present invention, the present application provides an agricultural composition comprising: (A) maleated soybean oil; a reaction product of octyldodecyl alcohol and glycerol; (B) one or more agricultural active ingredients; and (C) one or more components.

[0027] In yet another aspect of the present invention, the present invention provides a compound useful for an agricultural composition represented by the following structure:

Chemical formula

[0028] ​In yet another aspect of the present invention, the present application provides a compound represented by the following structure:

Chemical formula

[0029] In another aspect of the present invention, the present application provides an agricultural composition selected from the group consisting of an adjuvant composition, a fertilizer composition, a nutritional composition, a plant strengthening composition, a seed coating composition, a soil improvement composition, a livestock composition, a granular composition, a sustained release composition, a film coating composition, a pesticide composition (selected from the group consisting of rodenticides, insecticides, acaricides, algicides, molluscicides, mite control agents, avicides, fungicides and herbicide compositions), a bactericide composition, an antibiotic composition, an antibacterial composition, an antiviral composition, an antifungal composition, an antiprotozoal composition, an antiparasitic composition, a wood preservation composition, a wood preservation composition, an antimicrobial composition or a plant yield improvement composition applied to soil.

[0030] <00001用組成物を提供する。In yet another aspect of the present invention, the present application provides an agricultural composition for external application to animals or plants, in a safe and effective amount, containing (A) from about 0.01% to about 20.0%; (B) from about 1.0% to about 90.0%; (C) from about 1.0% to about 99.0%.

[0031] In yet another aspect of the present invention, the present application provides an agricultural composition comprising: (A) from about 0.01% to about 20.0% of maleated natural oil; a reaction product with a functionalized or non-functionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties and combinations thereof; (B) from about 1.0% to about 90.0% of one or more agricultural active ingredients; and (C) from about 1.0% to about 99.0% of one or more components.

[0032] In yet another aspect of the present invention, the present application provides an agricultural composition comprising: (A) about 0.01% to about 20.0% of maleated natural oil, a reaction product of at least one functionalized or unfunctionalized hydrophobic moiety and at least one functionalized or unfunctionalized hydrophilic moiety; (B) about 1.0% to about 90.0% of one or more agricultural active ingredients; and (C) about 1.0% to about 99.0% of one or more ingredients.

[0033] In yet another aspect of the present invention, the present application provides an agricultural composition comprising: (A) a reaction product of maleated soybean oil, octyldodecyl alcohol, and glycerol; (B) one or more agricultural active ingredients in an amount of about 1.0% to about 90.0%; and (C) one or more ingredients in an amount of about 1.0% to about 99.0%.

[0034] In yet another aspect of the present invention, the present application provides a seed coating composition comprising: (A) about 0.01% to about 20.0% of maleated natural oil; a reaction product of a functionalized or non-functionalized site selected from the group consisting of hydrophobic sites, hydrophilic sites and combinations thereof; (B) about 1.0% to about 90.0% of one or more agricultural active ingredients; and (C) about 1.0% to about 99.0% of one or more components.

[0035] In yet another aspect of the present invention, the present application provides a livestock composition comprising: (A) about 0.01% to about 20.0% of maleated natural oil; a reaction product of a functionalized or non-functionalized site selected from the group consisting of hydrophobic sites, hydrophilic sites and combinations thereof; (B) about 1.0% to about 90.0% of one or more agricultural active ingredients; and (C) about 1.0% to about 99.0% of one or more components.

[0036] In yet another aspect of the present invention, the present application provides a granular composition comprising: (A) about 0.01% to about 20.0% of maleated natural oil; a reaction product of a functionalized or non-functionalized site selected from the group consisting of hydrophobic sites, hydrophilic sites and combinations thereof; (B) about 1.0% to about 90.0% of one or more agricultural active ingredients; and (C) about 1.0% to about 99.0% of one or more components.

[0037] In yet another aspect of the present invention, the present application provides a sustained-release composition comprising: (A) about 0.01% to about 20.0% of maleated natural oil; a reaction product between a functionalized or non-functionalized site selected from the group consisting of aqueous sites, hydrophilic sites and combinations thereof; (B) about 1.0% to about 90.0% of one or more agricultural active ingredients; and (C) about 1.0% to about 99.0% of one or more components.

[0038] In yet another aspect of the present invention, the present application provides a film coating composition comprising: (A) about 0.01% to about 20.0% of maleated natural oil; a reaction product of a functionalized or non-functionalized site selected from the group consisting of hydrophobic sites, hydrophilic sites and combinations thereof; (B) about 1.0% to about 90.0% of one or more agricultural active ingredients; and (C) about 1.0% to about 99.0% of one or more components.

[0039] Modified maleated natural oils are useful in a variety of agricultural compositions and their applications. [Modes for carrying out the invention]

[0040] This application provides agricultural compositions containing modified maleinated natural oil that do not exhibit many of the limiting properties of maleinated natural oil. Modified maleinated natural oil is useful in a variety of agricultural compositions and their applications.

[0041] Natural oils are abundant, inexpensive, and obtainable from sustainable sources. They are useful in the synthesis of renewable compounds such as polymers, plastics, and plasticizers, which are useful in a variety of agricultural compositions. A challenge in the use of natural oils is that they are mixtures of triglycerides containing varying degrees of unsaturated groups, which are relatively unreactive. To make these natural oils reactive, these unsaturated groups are generally chemically modified to enhance their reactivity. For example, these unsaturated groups can be reacted to impart epoxide or succinic anhydride functional groups. Despite these chemical modifications, maleated natural oils may still exhibit limited properties, such as insolubility or nondispersibility in water and alcohol. Therefore, there is a need for further modified maleated natural oils that do not exhibit these limited properties.

[0042] Unless otherwise defined herein, technical terms used in connection with the disclosed and / or claimed inventive concepts shall have the meaning generally understood by those skilled in the art. Furthermore, unless otherwise specifically required by context, singular terms shall include plural forms and plural terms shall include singular forms.

[0043] The singular forms “a,” “an,” and “the” include the plural form unless clearly distinguishable in the context in which they are referred. “Comprising” and “Comprises of” include more restrictive claims such as “Consisting essentially of” and “Consisting of.”

[0044] In the following detailed description, except for the examples of operation, or unless otherwise specifically indicated, numerical values ​​representing amounts of components etc. described in the specification and claims are understood to be modified in all examples by the term “approximately.” Numerical parameters described in the specification and appended claims are approximations that may vary depending on the desired characteristics obtained in the practice of the invention.

[0045] All percentages, parts, ratios, and proportions used herein are based on the weight of the entire composition unless otherwise specified. All weights relating to the listed components are based on their activity levels and, therefore, do not include solvents or by-products present in commercially available materials unless otherwise specified.

[0046] All publications, articles, patents, patent publications, and other references cited herein are incorporated herein to the extent that they do not conflict in their entirety with this disclosure.

[0047] The use of the term "at least one" is understood to include not just one, but any quantity greater than one, such as 1, 2, 3, 4, 5, 10, 15, 20, 30, 40, 50, 100, etc. The term "at least one" may extend to 100 or 1000 or more, depending on the accompanying terminology. Furthermore, the quantity 100 / 1000 is not limiting, and satisfactory results may be obtained with smaller or larger threshold values.

[0048] The term "branched and unbranched alkyl groups" refers to alkyl groups, which may be linear or branched. Examples of branched groups include isopropyl and tert-butyl.

[0049] As used herein, “comprising” (and any other form such as “comprise” or “comprises”), “having” (and any other form such as “have” or “has”), “including” (and any other form such as “includes” or “include”), or “containing” (and any other form such as “contains” or “contain”) are comprehensive or open-ended and do not exclude any additional undescribed elements or method steps.

[0050] The phrase "each independently selected from the group consisting of ~" means that if a group appears multiple times in a structure, each time that group appears, it can be independently selected.

[0051] The term "polymer" refers to a compound containing repeating structural units (monomers) linked by covalent chemical bonds. Polymers can be further derivatized, crosslinked, grafted, or end-capped. Non-limiting examples of polymers include copolymers, terpolymers, quaternary copolymers, quaternary polymers, and homologs. The term "polymer" refers to a polymer that is essentially made up of polymers obtained by polymerizing two or more different monomers.

[0052] The term "reaction product" refers to a substance produced from a chemical reaction between one or more reactants.

[0053] The term "natural oil" refers to compounds containing triglycerides, which may include various levels of fatty acids, monoglycerides, diglycerides, and triglycerides, and refers to oils of plant or animal origin. Natural oils also include fatty acid glyceryl esters synthesized by reacting glycerol with 1, 2, or 3 molar equivalents of fatty acids or fatty acid mixtures. These compounds may be mono, di, or triglycerides of a single fatty acid or fatty acid mixture.

[0054] As used herein, the term "maleinized natural oil" refers to a natural oil containing at least one or more maleinated functional groups.

[0055] In the following context, "maleinization" or "maleinized" means "the addition of one or more succinic anhydride moieties" and "having one or more succinic anhydride moieties."

[0056] As used herein, the terms "part" or "part group" refer to a part or functional group of a molecule.

[0057] As used herein, the term “agricultural active ingredients” refers to chemical substances used in agriculture, horticulture, and pest control to protect crops, plants, structures, animals, and humans from unwanted organisms such as fungal and bacterial plant pathogens, weeds, insects, mites, algae, and nematodes. Specifically, active ingredients selected from the group consisting of fertilizers, herbicides, ovicidal agents, fungicides, pesticides (selected from rodenticides, acaricides, algicidal agents, mollusk repellents, mite repellents, birdicides, and insecticides), fungicides, antibiotics, antimicrobial agents, antiviral agents, antifungal agents, antiprotozoal agents, antiparasitic agents, and antimicrobial compounds are applicable to plants, seeds, soil, or other growing media for the purpose of improving physical, chemical, or biological characteristics for crop production, thereby improving crop production, plant growth, product quality, product durability, or yield before harvest.

[0058] As used herein, the term "component" refers to an adjuvant or inactive component substance that can enhance the biological activity of an active ingredient but does not possess significant biological activity itself. Agricultural components enhance the effects of an active ingredient, such as by improving the delivery of the agricultural active ingredient and its uptake by target plants or animals, thereby improving biological control.

[0059] Agricultural compositions containing these components refer to auxiliary agents selected from the group consisting of acidifiers, buffers, foam inhibitors, defoamers, transpiration inhibitors, dyes and whitening agents, compatibility agents, crop oil concentrates, oily surfactants, adhesives, drift reducers, foam markers, feeding stimulants, herbicide safers, spreading agents, extenders, adhesives, suspending agents, gelling agents, synergistic agents, wetting agents, emulsifiers, dispersants, penetrating agents, tank and equipment cleaning agents, neutralizing agents, water absorbents, water softeners, and mixtures thereof.

[0060] The agricultural composition further comprises components that may be selected from the group consisting of solvents, liquid carriers, solid carriers or fillers, surfactants, solubilizers, penetration enhancers, protective colloids, thickeners, humectants, repellents, attractants, adapting agents, bactericidal agents, antifreezes, crystallization inhibitors, colorants, tackifiers, binders, preservatives, pH adjusters, clarifiers, stabilizers, UV stabilizers, and mixtures thereof.

[0061] The term “functionalized” in relation to any site refers to the presence of one or more functional groups at that site. Various functional groups can be introduced to a site by one or more functionalization reactions known to those skilled in the art. Non-limiting examples of functionalization reactions include alkylation, epoxidation, sulfonation, hydrolysis, amidation, esterification, hydroxylation, dihydroxylation, amination, ammonia decomposition, acylation, nitration, oxidation, dehydration, elimination, hydration, dehydrogenation, hydrogenation, acetalization, halogenation, dehalogenation, Michael addition, aldol condensation, Cannizzaro reaction, Mannich reaction, Klassen condensation, and Suzuki coupling. In one non-limiting embodiment, the term “functionalized” in relation to any site refers to the presence of one or more functional groups selected from the group consisting of alkyl, alkenyl, hydroxyl, carboxyl, halogen, alkoxy, amino, imino, and combinations thereof at that site.

[0062] As used herein, the term "hydrophilic" means that a compound has an affinity for water, and "hydrophobic" means that it does not have an affinity for water.

[0063] These terms are relative; hydrophilic parts have a higher affinity for water than hydrophobic parts, but hydrophilic parts are not always completely water-soluble. Similarly, hydrophobic parts have a lower affinity for water than hydrophilic parts, but hydrophobic parts do not necessarily repel water completely. Hydrophilic parts tend to have an affinity for water and other polar solvents, while hydrophobic parts tend to have an affinity for oils and other nonpolar solvents.

[0064] The term "unreacted maleated functional group" refers to an unreacted maleic anhydride functional group in the reaction product of the present invention, where the anhydride functional group is completely unreacted and intact. Since the carbon-carbon double bond of maleic anhydride is saturated when added to the unsaturated fatty acid chain during the "ene" or "maleation" reaction, the "unreacted maleated functional group" can also be considered an intact succinic anhydride moiety or group of moieties.

[0065] The term "hydrocarbon group" includes linear and branched alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl groups and combinations thereof, which have any heteroatoms. Hydrocarbon groups are monovalent, divalent, or polyvalent, and their carbon chains contain at least two carbon atoms, preferably 2 to 100 carbon atoms.

[0066] The term "alkyl" refers to a functionalized or unfunctionalized monovalent, linear, branched, or cyclic C1-C60 hydrocarbon group, optionally having one or more heteroatoms. In one non-limiting embodiment, alkyl is a C1-C45 hydrocarbon group. In another non-limiting example, alkyl is a C1-C30 hydrocarbon group. Non-limiting examples of alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, tert-octyl, isonorbornyl, n-dodecyl, tert-dodecyl, n-tetradecyl, n-hexadecyl, n-octadecyl, n-eicosyl, cyclobutyl, cyclopentyl, and cyclohexyl. The definition of "alkyl" also includes groups obtained in combinations of linear, branched, and / or cyclic structures.

[0067] The term "aryl" refers to a functionalized or unfunctionalized monovalent aromatic hydrocarbon group that optionally contains a heteroatom. The definition of aryl includes carbocyclic and heterocyclic aromatic groups. Non-restrictive examples of aryl groups include phenyl, naphthyl, indenyl, indanyl, azlenyl, fluorenyl, anthracenyl, furyl, thienyl, pyridyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, pyrazolyl, 2-pyrazolinyl, pyrazolidinyl, isoxazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2,3-triazolyl, 1,3,4-thiadiazolyl, pyridadinyl, pyrimidinyl, pyrazinyl, 1,3,5-triazinyl, 1,3,5-trithianyl, indolidinyl, and in Examples include drill, isoindolyl, 3H-indolyl, indolinyl, benzo[b]furanyl, 2,3-dihydrobenzofuranyl, benzo[b]thiophenyl, 1H-indazolyl, benzimidazolyl, benzthiazolyl, prinyl, 4H-quinolidinyl, isoquinolinyl, sinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, 1,8-naphtholidinyl, pteridinyl, carbazolyl, acridinyl, phenazinyl, phenothiazinyl, phenoxyazinyl, and pyrazolo[1,5-c]triazinyl.

[0068] The term "aralkyl" refers to an alkyl group containing one or more aryl substituents, where "aryl" and "alkyl" are as defined above. Non-limiting examples of aralkyl groups include benzyl, 2-phenylethyl, 3-phenylpropyl, 4-phenylbutyl, 5-phenylpentyl, 4-phenylcyclohexyl, 4-benzylcyclohexyl, 4-phenylcyclohexylmethyl, and 4-benzylcyclohexylmethyl.

[0069] The term "alkylene" refers to a functionalized or unfunctionalized, divalent, linear, branched, or cyclic C1-C40 hydrocarbon group, optionally containing one or more heteroatoms. In one non-limiting embodiment, the alkylene is a C1-C30 group. In another non-limiting embodiment, the alkylene is a C1-C20 group. Non-limiting examples of alkylene groups include: [ka]

[0070] The term "alylene" refers to a functionalized or unfunctionalized divalent aromatic hydrocarbon group that optionally contains one or more heteroatoms. The definition of "alylene" includes carbocyclic and heterocyclic groups. Examples of non-restrictive allylene groups include phenylene, naphthylene, and pyridinylene.

[0071] The term "heteroatom" refers to oxygen, nitrogen, sulfur, silicon, phosphorus, or halogen. Heteroatoms may exist as part of one or more heteroatom-containing functional groups. Non-limiting examples of heteroatom-containing functional groups include ether groups, hydroxyl groups, epoxy groups, carbonyl groups, carboxamide groups, carboxylic acid ester groups, carboxylic acid groups, imine groups, imide groups, amine groups, sulfone groups, sulfonamide groups, phosphone groups, and silane groups. Heteroatoms may also exist as part of rings such as heteroaryl groups and heteroalylene groups.

[0072] The structures shown below may refer to the first, second, or third structure, or a combination thereof. The succinic anhydride group may be present in the upper, middle, or lower chain. [ka]

[0073] In one non-limiting embodiment, the hydrophobic and hydrophilic moieties are hydrocarbon alcohols, hydrocarbon amines, silicon compounds, or combinations thereof.

[0074] Hydrocarbon alcohols are classified into primary, secondary, and tertiary alcohols based on the number of carbon atoms bonded to the hydroxyl group-containing carbon atoms. Each classification of alcohol may have a general formula. For example, The general formula for primary alcohols is: [ka] The general formula for secondary alcohols is: [ka] The general formula for tertiary alcohols is: [ka] In the formula, R, R′ and R″ represent different alkyl groups, alkylene groups, aryl groups, aralkyl groups, or allylene groups.

[0075] The present invention provides an agricultural composition comprising a reaction product between maleized natural oil and a functionalized or non-functionalized site selected from the group consisting of hydrophobic sites, hydrophilic sites, and combinations thereof. In one non-limiting embodiment, the reaction product comprises unreacted maleized functional groups or maleized functional groups functionalized with hydrophobic sites, hydrophilic sites, or combinations thereof.

[0076] Preferably, the hydrophobic moiety is a moiety selected from the group consisting of: unsubstituted or substituted alkyl alcohols, cycloalkyl alcohols, alkenyl alcohols and aryl alcohols containing about 6 to about 36 carbon atoms, which may or may not have heteroatoms; unsubstituted or substituted alkylamines, cycloalkylamines, alkenylamines and arylamines containing about 6 to about 36 carbon atoms, which may or may not have heteroatoms; unsubstituted or substituted polyols containing about 37 to about 60 carbon atoms, which may or may not have heteroatoms; silicon compounds; and combinations thereof.

[0077] Preferably, the hydrophilic moiety is a moiety selected from the group consisting of: unsubstituted or substituted alkyl, cycloalkyl, alkenyl and aryl alcohols containing about 1 to about 5 carbon atoms, which may or may not have heteroatoms; unsubstituted or substituted alkyl, cycloalkyl, alkenyl and arylamines containing about 1 to about 5 carbon atoms, which may or may not have heteroatoms; unsubstituted or substituted polyols containing about 2 to about 36 carbon atoms, which may or may not have heteroatoms; poly(ethylene glycol) monomethyl ether (mPEG) containing 5 to 45 carbon atoms; silane; and combinations thereof.

[0078] Preferably, the silane is functionalized with an alcohol, an amine, or a combination thereof. Preferably, the hydrophobic alcohol is selected from the group consisting of hexanol, heptanol, nonanol, decanol, dodecanol, phenol, ethylbenzyl alcohol, 2-ethyl-1-hexanol, 1-octanol, 2-octanol, 2-butyl-1-octanol, 2-octyl-1-dodecyl alcohol, 1-tetradecanol, 2-tetradecanol, 1-hexadecanol, 2-hexadecanol, behenyl alcohol, 3,7-dimethyl-1-octanol, 2-propyl-1-pentanol, 4-methyl-1-pentanol, and mixtures thereof. Preferably, the hydrophilic alcohol is selected from the group consisting of methanol, ethanol, propanol, isopropanol, butanol, methoxypolyethylene glycol, and mixtures thereof. Preferably, the hydrophilic polyol is selected from the group consisting of ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, dibutylene glycol, polyethylene glycol, polypropylene glycol, hexylene glycol, sorbitol, neopentyl glycol, erythritol, mannitol, xylitol, sreitol, pentaerythritol, β-cyclodextrin, ribose, 2-deoxygalactose, and mixtures thereof.

[0079] Preferably, the hydrophobic amine is selected from the group consisting of benzylamine, cyclohexylamine, hexylamine, methylhexylamine, phenethylamine, octylamine, oleylamine, decylamine, dodecylamine, octadecylamine, undecylamine, pentadecylamine, 2-methylbutylamine, and mixtures thereof. Preferably, the hydrophilic amine is selected from the group consisting of diethanolamine, selinol hydrochloride, 2-amino-2-ethyl-1,3-propanediol, dimethylamine, and mixtures thereof.

[0080] Preferably, the hydrophobic polyol is selected from the group consisting of 1,6-hexanediol, 1,7-heptanediol, 1,8-octanediol, 1,9-nonanediol, 1,10-decanediol, 1,12-dodecanediol, poly(tetramethylene ether) glycol, poly(tetramethylene carbonate), poly(hexamethylene carbonate), and castor oil.

[0081] Preferably, the hydrophobic silicon compound is selected from the group consisting of aminopropylmethylsiloxane-dimethylsiloxane, N-ethylaminoisobutyl-terminated polydimethylsiloxane, poly(1,1-dimethylsilazane) telomer, aminopropyl-terminated polydimethylsiloxane, monoaminopropyl-terminated polydimethylsiloxane, (tetramethylpiperidinyloxy)propylmethylsiloxane]-dimethylsiloxane copolymer, polydimethylsiloxane, carbinol(hydroxyl)-terminated polydimethylsiloxane, monocarbinol-terminated polydimethylsiloxane, monocarbinol-terminated functional polydimethylsiloxane, [bis(hydroxyethyl)amine]-terminated polydimethylsiloxane, silanol-terminated polydimethylsiloxane, silanol-terminated polydiphenylsiloxane, dodecylmethylsiloxane-hydroxypolyalkyleneoxypropylmethylsiloxane, and mixtures thereof. Preferably, the hydrophilic silane is selected from the group consisting of 3-aminopropylsilanetriol, N-(2-aminoethyl)-3-aminopropylsilanetriol, and mixtures thereof.

[0082] In one non-limiting embodiment, the hydrophobic moiety is a linear, branched, saturated, unsaturated, aliphatic, aromatic, monofunctional, or polyfunctional hydrocarbon alcohol moiety containing about 6 to about 36 carbon atoms.

[0083] In one non-limiting embodiment, the hydrophilic polyol is selected from the group consisting of ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, dibutylene glycol, polyethylene glycol, polypropylene glycol, hexylene glycol, sorbitol, neopentyl glycol, erythritol, mannitol, xylitol, sreitol, pentaerythritol, β-cyclodextrin, ribose, 2-deoxygalactose, and mixtures thereof.

[0084] In one non-limiting embodiment, the hydrocarbonamine is selected from the group consisting of primary amines, secondary amines, and combinations thereof.

[0085] Hydrocarbon amines are classified as primary, secondary, or tertiary based on the number of carbon atoms bonded to the amine nitrogen atom. Each class of amine may have a general formula. For example, the general formula for a primary amine is: [ka] And, The general formula for secondary amines is [ka] In the formula, R and R′ represent the same or different alkyl group, alkylene group, aryl group, aralkyl group, or arylene group.

[0086] In one non-limiting embodiment, the hydrophobic moiety is a linear, branched, saturated, unsaturated, aliphatic, aromatic, monofunctional, or polyfunctional hydrocarbonamine moiety containing about 6 to about 36 carbon atoms.

[0087] In one non-limiting embodiment, the silicon-based compound has the following structure [ka] or [ka] The compound has the following characteristics, where R represents a heterogroup functionalized with a different alkyl group, alkylene group, aryl group, aralkyl group, arylene group, at least one alcohol, amine, or combination thereof, and n has a value of 1 to 10.

[0088] In one non-limiting embodiment, the silicon-based compound is a siloxane, or a silane functionalized with an alcohol, an amine, or a combination thereof.

[0089] In one non-limiting embodiment, the silicon-based compound is a linear, branched, saturated, unsaturated, aliphatic, aromatic, monofunctional, or polyfunctional compound.

[0090] In one non-limiting embodiment, the hydrocarbon alcohol is a hydrophobic alcohol selected from the group consisting of hexanol, heptanol, nonanol, decanol, dodecanol, phenol, ethylbenzyl alcohol, 2-ethyl-1-hexanol, 1-octanol, 2-octanol, 2-butyl-1-octanol, 2-octyl-1-dodecyl alcohol, 1-tetradecanol, 2-tetradecanol, 1-hexadecanol, 2-hexadecanol, behenyl alcohol, 3,7-dimethyl-1-octanol, 2-propyl-1-pentanol, 4-methyl-1-pentanol, and mixtures thereof.

[0091] In one non-limiting embodiment, the hydrocarbon alcohol is a hydrophilic alcohol selected from the group consisting of methanol, ethanol, propanol, isopropanol, butanol, methoxypolyethylene glycol, and mixtures thereof. Preferably, the hydrophilic polyol is ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, dibutylene glycol, polyethylene glycol, polypropylene glycol, hexylene glycol, glycerol, sorbitol, octanol, methylethylpentanol, trimethylpentanol, ethylhexanol, methylheptanol, nonanol, methyloctanol, ethylheptanol, methylethylhexanol, cyclohexanol, dimethylheptanol, decanol, methylnonanol Selected from the group consisting of ethyl octanol, trimethylheptanol, undecanol, methyldecanol, ethyl nonanol, dodecanol, tetradecanol, hexadecanol, octadecanol, benzyl alcohol, phenoxyethanol, neopentyl glycol, trimethylolpropane, N-methyldiethanolamine, erythritol, mannitol, xylitol, pentaerythritol, sreitol, pentaerythritol, β-cyclodextrin, ribose, 2-deoxygalactose, and mixtures thereof.

[0092] In one non-limiting embodiment, the hydrocarbonamine is a hydrophobic amine selected from the group consisting of benzylamine, cyclohexylamine, hexylamine, methylhexylamine, phenethylamine, octylamine, oleylamine, decylamine, dodecylamine, octadecylamine, undecylamine, pentadecylamine, 2-methylbutylamine, and mixtures thereof.

[0093] In one non-limiting embodiment, the hydrocarbonamine is a hydrophilic amine selected from the group consisting of 2-methylpentane-1,5-diamine, diethanolamine, selinol hydrochloride, 2-amino-2-ethyl-1,3-propanediol, dimethylamine, and mixtures thereof.

[0094] In one non-limiting embodiment, the silicon-based compound is a hydrophobic compound selected from the group consisting of aminopropylmethylsiloxane-dimethylsiloxane, N-ethylaminoisobutyl-terminated polydimethylsiloxane, poly(1,1-dimethylsilazane) telomer, aminopropyl-terminated polydimethylsiloxane, monoaminopropyl-terminated polydimethylsiloxane, (tetramethylpiperidinyloxy)propylmethylsiloxane]-dimethylsiloxane copolymer, polydimethylsiloxane, carbinol(hydroxyl)-terminated polydimethylsiloxane, monocarbinol-terminated polydimethylsiloxane, monocarbinol-terminated functional polydimethylsiloxane, [bis(hydroxyethyl)amine]-terminated polydimethylsiloxane, silanol-terminated polydimethylsiloxane, silanol-terminated polydiphenylsiloxane, dodecylmethylsiloxane-hydroxypolyalkyleneoxypropylmethylsiloxane, and mixtures thereof.

[0095] [ka] Aminopropylmethylsiloxane-dimethylsiloxane (aminosiloxane)

[0096] [ka] N-ethylaminoisobutyl-terminated polydimethylsiloxane (aminosiloxane)

[0097] [ka] Poly(1,1-dimethylsilazane) telomer

[0098] [ka] Aminopropyl-terminated polydimethylsiloxane (aminosiloxane)

[0099] [ka] Monoaminopropyl-terminated polydimethylsiloxane (aminosiloxane)

[0100] [ka] (tetramethylpiperidinyloxy)propylmethylsiloxane]-dimethylsiloxane copolymer

[0101] [ka] Polydimethylsiloxane

[0102] [ka] Carbinol (hydroxyl)-terminated polydimethylsiloxane

[0103] [ka] Monocarbinol-terminated polydimethylsiloxane

[0104] [ka] Monocarbinol-terminated polydimethylsiloxane

[0105] [ka] [bis(hydroxyethyl)amine]terminated polydimethylsiloxane

[0106] [ka] Silanol-terminated polydimethylsiloxane

[0107] [ka] Silanol-terminated polydiphenylsiloxane

[0108] [ka] Dodecylmethylsiloxane-hydroxypolyalkyleneoxypropylmethylsiloxane

[0109] In one non-limiting embodiment, the silicon compound is a hydrophilic compound selected from the group consisting of 3-aminopropylsilanetriol, N-(2-aminoethyl)-3-aminopropylsilanetriol, and mixtures thereof.

[0110] [ka] 3-aminopropylsilanetriol (silica-based alcohol)

[0111] [ka] N-(2-aminoethyl)-3-aminopropylsilanetriol

[0112] Preferably, the maleated natural oil is selected from the group consisting of maleated avocado oil, maleated coconut oil, maleated corn oil, maleated cottonseed oil, maleated jojoba oil, maleated linseed oil, maleated nut oil, maleated olive oil, maleated palm oil, maleated raisin oil, maleated rapeseed oil, maleated safflower oil, maleated sesame oil, maleated soybean oil, maleated pumpkin oil, maleated sunflower oil, maleated almond oil, maleated canola oil, maleated flaxseed oil, maleated grapeseed oil, maleated palm oil, maleated palm kernel oil, maleated peanut oil, maleated walnut oil, maleated chickpea oil, maleated clary sage oil, and mixtures thereof. More preferably, the maleated natural oil is maleated soybean oil.

[0113] Preferably, agricultural compositions are selected from the group consisting of auxiliary compositions, fertilizer compositions, nutritional compositions, plant strengthening compositions, seed coating compositions, soil improvement compositions, livestock compositions, granular compositions, sustained-release compositions, film coating compositions, pesticide compositions (selected from the group consisting of rodenticides, insecticides, acaricides, algaecides, mollusk repellents, mite repellents, birdicides, fungicides, and herbicides), fungicide compositions, antibiotic compositions, antimicrobial compositions, antiviral compositions, antifungal compositions, antiparasitic compositions, wood preservation compositions, antimicrobial compositions, or plant yield-improving compositions applied to soil.

[0114] In one non-limiting embodiment, the present invention provides an agricultural composition comprising: (A) a reaction product of a maleated natural oil having a maleated functional group and a functionalized or non-functionalized site selected from the group consisting of hydrophobic sites, hydrophilic sites and combinations thereof; (B) one or more agricultural active ingredients; and (C) one or more components.

[0115] In one non-limiting embodiment, the present invention provides a seed coating composition comprising: (A) a maleated natural oil having a maleated functional group; a reaction product of a functionalized or non-functionalized site selected from the group consisting of hydrophobic sites, hydrophilic sites and combinations thereof; (B) one or more agricultural active ingredients; and (C) one or more components.

[0116] In one non-limiting embodiment, the present invention provides a livestock composition comprising: (A) a maleated natural oil having a maleated functional group; a reaction product of a functionalized or non-functionalized site selected from the group consisting of hydrophobic sites, hydrophilic sites and combinations thereof; (B) one or more agricultural active ingredients; and (C) one or more components.

[0117] In a non-limiting embodiment, the present invention provides a sustained-release composition comprising: (A) a maleized natural oil having a maleated functional group; a reaction product of a functionalized or non-functionalized site selected from the group consisting of hydrophobic sites, hydrophilic sites and combinations thereof; (B) one or more agricultural active ingredients; and (C) one or more components.

[0118] In a non-limiting embodiment, the present invention provides a granular composition for topical application to animals or plants, comprising, in safe and effective amounts, about 0.01% to about 20.0% of (A); about 1.0% to about 90.0% of (B); and about 1.0% to about 99.0% of (C).

[0119] In one non-limiting embodiment, the present invention provides a film coating composition comprising: (A) about 0.01% to about 20.0% of a reaction product between maleated natural oil and a functionalized or non-functionalized site selected from the group consisting of hydrophobic sites, hydrophilic sites and combinations thereof; (B) about 1.0% to about 90.0% of one or more agricultural active ingredients; and (C) about 1.0% to about 99.0% of one or more components.

[0120] In a non-limiting embodiment, the present invention provides an agricultural composition comprising (A) maleated soybean oil; a reaction product of octyldodecyl alcohol and glycerol; (B) one or more agricultural active ingredients in an amount of about 1.0% to about 90.0%; and (C) one or more ingredients in an amount of about 1.0% to about 99.0%.

[0121] A preferred agricultural composition comprises a compound selected from the group of structures represented by the following structures: [ka] (wherein R is ethyl, butyl, hexyl, octyl, 2-ethylhexane-1-yl, 2-butyloctan-1-yl, 2-hexyldecane-1-yl, 2-octyldodecane-1-yl, or a mixture thereof).

[0122] A preferred agricultural composition comprises a compound selected from the group of structures represented by the following structures: [ka]

[0123] In a non-limiting embodiment, the present invention provides an agricultural composition comprising: (A) about 0.01% to about 20.0% of a reaction product between maleated natural oil and a functionalized or non-functionalized site selected from the group consisting of hydrophobic sites, hydrophilic sites and combinations thereof; (B) about 1.0% to about 90.0% of one or more agricultural active ingredients; and (C) about 1.0% to about 99.0% of one or more components.

[0124] In one non-limiting embodiment, the present invention provides a method for treating vegetation, comprising applying an agricultural composition to plants, plant leaves, flowering parts, foliage, stems, fruits, adjacent areas of the plants, soil, seeds, germinating seeds, roots, liquid and solid growing media, flowers, buds, and hydroponic solutions.

[0125] In one non-limiting embodiment, the present invention provides a method for treating animals, which includes applying an agricultural composition topically to a portion of the animal's skin.

[0126] The reactions relating to this application can be readily synthesized by procedures known to those skilled in the art, namely, without limitation, free radical solution polymerization, dispersion polymerization, emulsion polymerization, ionic chain polymerization, living polymerization, bulk polymerization, suspension polymerization, or precipitation polymerization. In particular, polymerization is carried out by any of the methods disclosed in "Principles of Polymerization," 4th edition (2004, Wiley, George Odian), which is incorporated herein by reference in its entirety, as is described in "Decomposition Rate of Organic Free Radical Polymerization" (KW Dixon, Polymer Handbook, Vol. 1, 4th edition, Wiley-Interscience, 1999, Section II), which is also incorporated herein by reference in its entirety.

[0127] Maleation in natural oils can occur in three different ways under heating. The first is known as the "Ene" reaction (a circumcyclic reaction between an allyl moiety with an allyl hydrogen and an enophil), which generates a triglyceride structure with an anhydride moiety (succinic anhydride) and involves the movement of a double bond in the fatty acid. The second is radical addition, which consumes the double bond in the fatty acid and incorporates succinic anhydride into the natural oil structure. The last reaction is also radical addition, incorporating maleic anhydride into the natural oil structure without consuming the C=C bond (fatty acid chain and maleic anhydride). This reaction occurs by the deprotonation of hydrogen between two alkene groups. Subsequently, maleated natural oils can be reacted with hydrocarbon alcohols, hydrocarbon amines, or the hydrophobic or hydrophilic moieties of silicon compounds.

[0128] The reactions described above in the non-limiting examples are for illustrative purposes only and can be carried out at high temperatures, for example, about 150°C to about 300°C, or about 170°C to about 230°C, or about 200°C to about 220°C. The reaction time can be about 0.5 hours to about 10 hours. In one embodiment, the reaction time is about 1 hour to about 5 hours, in another embodiment about 2 hours to 4 hours, and in yet another embodiment about 6 hours to 10 hours.

[0129] During maleation, in some embodiments, the molar ratio of maleic anhydride to natural oil is 1:1. In other embodiments, the molar ratio of maleic anhydride to natural oil is 1:1 to 2:1, in other embodiments 1:1 to 2.8:1, and in yet another embodiment 1:1 to 3.2:1.

[0130] In some embodiments of the reaction between maleized natural oil and hydrophobic, hydrophilic, or combination thereof, the maleized natural oil having an average of about 2 equivalents or more of maleated functional groups and the molar ratio of hydrophobic, hydrophilic, or combination thereof is about 1:1, thereby forming a reaction product containing at least about one unreacted maleated functional group.

[0131] In another embodiment of the present application, it is envisioned that at least one agricultural active ingredient selected from the group consisting of fertilizers, herbicides, ovicidal agents, fungicides, and pesticides (selected from the group consisting of rodenticides, acaricides, algaecides, mollusk repellents, mite repellents, birdicides, insecticides, fungicides, antibiotics, antibacterial agents, antiviral agents, antifungal agents, antiprotozoal agents, antiparasitic agents, and antimicrobial compounds) is used.

[0132] According to another embodiment of the present invention, the pesticides intended for use in the present invention include fungicides, herbicides, insecticides, acaricides, nematodeicides, mite control agents, and mollusk control agents.

[0133] The fertilizers intended for use in this application may include inorganic fertilizers, nitrogen fertilizers, potassium fertilizers, phosphate fertilizers, organic fertilizers, compost, phosphate rock, bone meal, alfalfa, wood chips, Langebeinnit, cover crops, potassium sulfate, rock powder, ash, blood meal, fish meal, fish emulsion, algae, chitosan, and molasses.

[0134] Examples of herbicides intended for use in this application may include glyphosate and glyphosate salt forms (isopropylamine salt, ammonium salt, potassium salt, trimesium salt), phenoxycarboxylic acids (e.g., 2,4-D acid, MCPA), benzoic acid (e.g., dicambaic acid), urea (e.g., diurone), sulfonylurea (e.g., methylsulfuron-methyl, limsulfuron), triazines (e.g., atrazine, simazine, ametrine), triazolinones (e.g., amicarbazone), and pyridinecarboxylic acids (e.g., triclopyr).

[0135] Examples of antifungal agents intended for use in this application include triazole-based (e.g., tebuconazole, tetraconazole, cyproconazole, epoxyconazole, diphenconazole, propiconazole, prothioconazole, mycrobutanil), strobilurin-based (e.g., trifloxystrobin, azoxystrobin, fluoxastrobin, pyraclostrobin), alkylenebis(dithiocarbamate) compounds (e.g., mancozeb), and benzimidazole-based (e.g., carbendazim) antifungal agents.

[0136] Examples of insecticides intended for use in the present invention include neonicotinoids (e.g., thiamethoxam, clothianidin, thiacloprid, dinotefuran, acetamiprid, nitenpyram, imidacloprid), amidines (e.g., amitraz), organophosphates (e.g., chlorpyrifos), and pyrethroids (e.g., permethrin, bifenthrin, deltamethrin).

[0137] Antimicrobial agents suitable for agricultural chemical compositions according to the present invention include fungicides, antibiotics, antibacterial agents, antiviral agents, antifungal agents, antiprotozoal agents, and antiparasitic agents. The most commonly used fungicides and disinfectants are activated chlorine (i.e., hypochlorite, chloramine, dichloroisocyanurate and trichloroisocyanurate, wet chlorine, chlorine dioxide, etc.), active oxygen (peroxides such as peracetic acid, potassium persulfate, sodium perborate, sodium percarbonate, urea hydrogen peroxide, etc.), iodine (iodopovidone (povidone-iodine, betadine), Lugol's solution, iodine tincture, iodized nonionic surfactants), high-concentration alcohols (mainly ethanol, 1-propanol (also called n-propanol), 2-propanol (also called isopropanol) and mixtures thereof; furthermore, 2-phenoxyethanol and 1-,2-phenoxypropanol are also used), phenolic substances (phenol (also called carbolic acid), cresol The following are used: ru (called "Rizol" when combined with liquid potassium soap), halogenated (chlorinated, brominated) phenols (hexachlorophene, triclosan, trichlorophenol, tribromophenol, pentachlorophenol, dibromol and their salts), cationic surfactants such as quaternary ammonium cations (benzalkonium chloride, cetyltrimethylammonium bromide or chloride, didecyldimethylammonium chloride, cetylpyridinium chloride, benzethonium chloride, etc.), non-quaternary compounds (chlorhexidine, glucoprotamine, octenidine dihydrochloride, etc.), strong oxidizing agents (ozone, permanganate solution, etc.); heavy metals and their salts (colloidal silver, silver nitrate, mercury chloride, phenylmercury salt, copper sulfate, copper chloride oxide, etc.). Heavy metals and their salts are the most toxic and environmentally harmful disinfectants, and their use is strongly restricted or prohibited. Furthermore, it also includes strong acids (phosphoric acid, nitric acid, sulfuric acid, amidosulfonic acid, toluenesulfonic acid) and alkalis (sodium, potassium, calcium hydroxide) in appropriate concentrations.

[0138] Suitable examples of plant growth regulators intended for use in the present invention include, but are not limited to, phosphonic acids (e.g., etephon), gibberellins, cytokinins (e.g., 6-benzylaminopurine), auxins (e.g., 1-naphthylacetic acid, triazole, strobilurin, alkylenebis(dithiocarbamate) compounds, benzimidazole, phenoxycarboxylic acid, benzoic acid, urea, sulfonylurea, triazine, pyridinecarboxylic acid, neonicotinoids, amidine, organophosphorus compounds, and pyrethroids).

[0139] In another embodiment of the present application, it is envisioned that at least one auxiliary agent selected from the group consisting of acidifying agents, buffering agents, foam inhibitors, defoaming agents, transpiration inhibitors, dyes and whitening agents, compatibility agents, crop oil concentrates, oily surfactants, adhesives, drift reducers, foam markers, feeding stimulants, herbicide safers, spreading agents, extenders, adhesives, suspending agents, gelling agents, synergistic agents, wetting agents, emulsifiers, dispersants, penetrating agents, tank and equipment cleaning agents, neutralizing agents, water absorbents, water softeners, and mixtures thereof may be used.

[0140] In another embodiment of the present application, it is envisioned that at least one component further selected from the group consisting of solvents, liquid carriers, solid carriers or fillers, surfactants, solubilizers, penetration enhancers, protective colloids, thickeners, humectants, repellents, attractants, adapting agents, bactericides, antifreezes, crystallization inhibitors, colorants, tackifiers, binders, preservatives, pH adjusters, clarifiers, stabilizers, UV stabilizers, and mixtures thereof may be used.

[0141] According to another embodiment of the present invention, the agricultural composition may contain an acidifying agent that enhances its effect. The acidifying agent may be a suitable organic or inorganic acid selected from the group consisting of hydrochloric acid, nitric acid, acetic acid, phosphoric acid, polyphosphate, perchloric acid, and combinations thereof.

[0142] According to another embodiment of the present invention, the agricultural composition may include a buffering agent for reducing pH. The buffering agent may include mineral acids such as sulfuric acid, sulfonic acid, sulfite, nitric acid, or nitrite; or organic acids such as glutaric acid, gluconic acid, lactic acid, glycolic acid, acrylic acid, or a combination thereof.

[0143] According to another embodiment of the present invention, the agricultural composition comprises an effective transpiration-inhibiting compound that reduces water loss. The transpiration-inhibiting compound includes sorbitol, mannitol and sucrose, silicone, polyethylene, polyvinyl chloride, paraffin, and turpentinediene (terpene resin).

[0144] According to another embodiment of the present invention, an agricultural composition includes a suitable "adapter" that facilitates the mixing of two or more components in solution, thereby making two or more chemical substances that are not normally mixable available for use in a tank. Preferred adapters are alkali metal acetates, alkaline earth metal acetates, and mixtures thereof.

[0145] According to another embodiment of the present invention, an agricultural composition comprising a suitable crop oil concentrate (COC) can be used to improve the herbicidal effect of the agricultural composition, reduce volatility, decrease water solubility, decrease surface tension, and improve surface coating and penetration effects. The crop oil concentrate (COC) may be an aromatic or paraffinic solvent, a fatty acid, one or more lower alkyl fatty acid esters, a polyoxyalkylene sulfate, a phosphate, or a carboxylate.

[0146] According to another embodiment of the present invention, an agricultural composition can utilize a drift reducer as a soil or foliar penetrant, which can reduce scattering or spray drift by increasing the droplet size of a spray solution selected from the group consisting of at least one phospholipid, plant colloid, underived guar gum, noncationic derived guar gum, cationic guar gum, polyethylene oxide, poly(vinylpyrrolidone), polyacrylamide, nonionic emulsifier, cationic emulsifier, and anionic emulsifier.

[0147] According to another embodiment of the present invention, an “adhesion agent” that promotes the adhesion of agricultural compositions helps prevent drift from the target area during spraying or drift after adhesion to plants or animals. Adhesion agents include modified cellulose (e.g., carboxymethylcellulose), plant-derived materials (e.g., grain flour, ground plant parts), natural minerals (talc, vermiculite, diatomaceous earth), natural clays (e.g., attapulgite, bentonite, kaolinite, montmorillonite) or synthetic materials (e.g., laponite) or proteins (soy protein, potato protein, soy flour, potato flour, fish meal, bone meal, yeast extract, blood meal).

[0148] According to another embodiment of the present invention, the herbicide safener maintains an acceptable level of efficacy against target species (e.g., weeds) while reducing or eliminating the phytotoxic effects of the active ingredient against non-target plant species (e.g., crops). Examples of herbicide safeners include benoxacol, (RS)-4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine; croquintoset, (5-chloroquinoline-8-oxy)acetic acid; croquintoset-mexyl, (RS)-1-methylhexyl(5-chloroquinoline-8-yloxy)acetate; siomethrinyl, (Z)-cyanomethoxyimino(phenyl)acetonitrile; cyprosulfamide, N-[4-(cyclopropylcarbamoyl)phenyl [Sulfonyl]-o-anisamide or N-[4-(cyclopropylcarbamoyl)phenylsulfonyl]-2-methoxybenzamide; dichloramide, N,N-diallyl-2,2-dichloroacetamide; dicyclonone, (RS)-1-dichloroacetyl-3,3,8a-trimethylperhydropyrrolo[1,2-a]pyrimidine-6-one; diethrate, O,O-diethyl-O-phenylphosphorothioate, fenchlorazole, 1-(2,4-dichlorophenyl)-5-trichloromethyl- 1H-1,2,4-triazole-3-carboxylic acid; fenchlorim, 1-(2,4-dichlorophenyl)-5-trichloromethyl-1H-1,2,4-triazole-3-carboxylic acid; flurazole, benzyl 2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylic acid or benzyl 2-chloro-4-trifluoromethylthiazole-5-carboxylic acid; fluxofenim, 4′-chloro-2,2,2-trifluoroacetophenone (EZ)-O -1,3-dioxalan-2-ylmethyloxime; frillazole, (RS)-3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyl-1,3-oxazolidine; isoxadefen, 4,5-dihydro-5,5-diphenyl-1,2-oxazole-3-carboxylic acid; isoxadefen-ethyl, ethyl 4,5-dihydro-5,5-diphenyl-1,2-oxazole-3-carboxylic acid ester; jekaowan, 2-(dichloromethyl)-2-methyl-1,3-dioxolane;This includes, but is not limited to, jiecaoxi, N-allyl-N-(allylcarbamoylmethyl)-2,2-dichloroacetamide; mephenate, 4-chlorophenylmethylcarbamate; naphthalene anhydride, naphthalene-1,8-dicarboxylic acid anhydride; oxavethrinyl, (Z)-1,3-dioxolane-2-ylmethoxyimino(phenyl)acetonitrile; mefenyr, (RS)-1-(2,4-dichlorophenyl)-5-methyl-2-pyrazoline-3,5-dicarboxylic acid; mefenyr-diethyl, diethyl(RS)-1-(2,4-dichlorophenyl)-5-methyl-2-pyrazoline-3,5-dicarboxylic acid ester, MG-191, 2-(dichloromethyl)-2-methyl-1,3-dioxolane, and combinations thereof.

[0149] According to another embodiment of the present application, a suitable suspension agent is selected from the group consisting of attapulgite clay, fumed silica, and mixtures thereof.

[0150] According to another embodiment of the present application, adhesives used in agricultural compositions may be waxes such as carnauba wax, beeswax, Chinese wax, shellac wax, whale wax, candelilla wax, castor oil wax, hollyhock wax, and rice bran wax; polysaccharides (e.g., starch, dextrin, maltodextrin, alginate, chitosan); fats; oils; proteins (e.g., gelatin, zein); gum arabic; and shellac. The adhesive may also be a non-natural compound, such as a polymer, copolymer, or wax. For example, non-limiting examples of polymers that can be used as adhesives include polyvinyl acetate, polyvinyl acetate copolymers, ethylene-vinyl acetate (EVA) copolymers, polyvinyl alcohol, polyvinyl alcohol copolymers, cellulose (e.g., ethylcellulose, methylcellulose, hydroxymethylcellulose, hydroxypropylcellulose, carboxymethylcellulose), polyvinylpyrrolidone, vinyl chloride, vinylidene chloride copolymers, calcium lignosulfonates, acrylic copolymers, polyvinyl acrylates, polyethylene oxide, acrylamide polymers and copolymers, polyhydroxyethyl acrylate, methylacrylamide monomers, and polychloroprene.

[0151] According to another embodiment of the present application, the gelling agent may be selected from gelling clay or polysaccharide gum, bentonite clay, xanthan gum, guar gum, locust bean gum, algal oligosaccharides, and combinations thereof.

[0152] According to another embodiment of the present application, suitable water absorbents include crosslinked polyacrylic acid polymers, hydrolyzed starch-acrylonitrile graft polymers; neutralized starch-acrylic acid graft polymers; saponified vinyl acetate-acrylic ester copolymers; crosslinked carboxymethylcellulose; hydrolyzed or crosslinked acrylonitrile copolymers or acrylamide copolymers; crosslinked cationic monomers; crosslinked isobutylene-maleic acid copolymers; 2-acrylamido-2-methylpropanesulfonic acid and acrylic acid crosslinked polymers, etc.

[0153] According to another embodiment of the present application, the water softener may be selected from sodium tripolyphosphate and tetrapotassium pyrophosphate.

[0154] In another embodiment of the present application, it is assumed that at least one solvent is used in the agricultural composition, the solvent exhibiting desirable solubility in the agricultural composition. Furthermore, the solvent may include alkylbenzenes, alkylnaphthalenes (e.g., isophorone, cyclohexanone, methylcyclohexanone, etc.), methyl esters of fatty acids, aliphatic hydrocarbons, cycloaliphatic hydrocarbons, fuel oils, isophorone, methyl ethyl ketone, N-methylpyrrolidone, butyl lactate, dimethyl sulfoxide, acetophenone or petroleum-derived toluene, xylene, chlorotoluene, benzene, methyl isobutyl ketone, cyclohexanone, naphthalene, ketone, for example, chlorolated hydrocarbons (e.g., chlorobenzene, trichloroethane), alcohols (e.g., benzyl alcohol, furfuryl alcohol, butanol, glycol ethers), and combinations thereof.

[0155] According to another embodiment of the present application, solid and liquid carriers are available in the present application and are used to coat seeds with the modified maleated soybean oil composition or to disperse the oil composition in a field. Solid carriers include, for example, diatomaceous earth, finely ground limestone, or magnesium carbonate or calcium carbonate. Sugars such as sucrose, maltose, maltodextrin, or dextrose can also be used as solids. The carriers also include gases or vapors such as steam, air, or inert gases such as diatomic nitrogen, which can be used to fluidize the solid composition. Other suitable carrier examples include talc, bentonite, clay, kaolin, white carbon, vermiculite, slaked lime, silica sand, ammonium sulfate, urea, etc., and liquid carriers include methylnaphthalene, isopropyl alcohol, xylene, cyclohexanone, water, methanol, ethanol, acetone, dimethylformaldehyde, ethylene glycol, etc.

[0156] According to one embodiment, the "filler" may be selected from the group consisting of bentonite, subbentonite, attapulgite, kaolinite, montmorillonite, bauxite, hydrated alumina, calcined alumina, diatomaceous earth, chalk, Fuller's earth, dolomite, keessulgull, leth, prophyllite, talc, vermiculite, limestone, natural and synthetic silicates, silica, and kaolin.

[0157] In one embodiment, “surfactant” as used herein means a compound that reduces the surface tension of a liquid and facilitates diffusion. Suitable auxiliary surfactants include, but are not limited to, nonionic, cationic, amphoteric, and polymeric surfactants.

[0158] Nonionic surfactants include alkoxylates, mainly ethoxylates, nonionic surfactants, especially fatty alcohol polyoxyethylene esters, such as lauryl alcohol polyoxyethylene ether acetate, alkyl polyoxyethylene ethers and alkyl polyoxypropylene ethers (e.g., those of linear fatty alcohols), alkylaryl alcohol polyoxyethylene ethers, such as octylphenol polyoxyethylene ether, alkoxylated animal and / or plant fats and / or oils, such as corn oil ethoxylate, castor oil ethoxylate, tallow ethoxylate, glycerol esters, such as glycerol monostearate, fatty alcohol alkoxylates and oxo alcohol alkoxylates, oleyl alcohol This includes polyoxyethylene ethers, alkylphenol alkoxylates, such as ethoxylated isooctylphenol, octylphenol or nonylphenol, tributylphenyl polyoxyethylene ethers, fatty amine alkoxylates, fatty acid amide alkoxylates and fatty acid diethanolamide alkoxylates, especially their ethoxylates, carbohydrate surfactants, sorbitol esters, such as sorbitan fatty acid esters (sorbitan monooleate, sorbitan tristearate), polyoxyethylene sorbitan fatty acid esters, alkyl polyglycosides, N-alkylgluconamides, -alkylmethyl sulfoxides, and alkyldimethylphosphine oxides, such as tetradecyldimethylphosphine oxide.

[0159] Amphoteric surfactants include, for example, sulfobetaine, carboxybetaine, and alkyldimethylamine oxides, such as tetradecyldimethylamine oxide.

[0160] Polymeric surfactants include, for example, (AB), ABA, and BAB type di, tri, and multiblock polymers, such as ethylene oxide / propylene oxide block copolymers with end caps, such as ethylenediamine-EO / PO block copolymers, polystyrene block polyethylene oxide, and AB comb polymers, such as polymethacrylate comb polyethylene oxide.

[0161] Furthermore, surfactants include perfluorosurfactants, silicone surfactants (e.g., polyether-modified siloxanes), phospholipids (e.g., lecithin or chemically modified lecithin), amino acid surfactants (e.g., N-lauroyl glutamic acid), and surfactant homopolymers and copolymers (e.g., polyvinylpyrrolidone, polyacrylic acid in salt form, polyvinyl alcohol, polypropylene oxide, polyethylene oxide, maleic anhydride / isobutene copolymer, and vinylpyrrolidone / vinyl acetate copolymer). Unless otherwise specified, the alkyl chains of the surfactants are linear or branched and typically have 8 to 25 carbon atoms.

[0162] As used herein, the term “dispersant” refers to a substance added to a suspension to improve the separation of particles and prevent sedimentation or aggregation. According to one embodiment, dispersants that can be used in agricultural compositions include polyvinylpyrrolidone, polyvinyl alcohol, lignosulfonates, phenylnaphthalene sulfonates, ethoxylated alkylphenols, ethoxylated fatty acids, alkoxylated linear alcohols, polyaromatic sulfonates, sodium alkylaryl sulfonates, glyceryl esters, maleic anhydride copolymers, phosphate esters, condensation products of aryl sulfonic acid and formaldehyde, condensation products of alkylaryl sulfonic acid and formaldehyde, addition products of ethylene oxide and fatty acid esters, and ethylene The group may be selected from the following: salts of addition products of oxides and fatty acid esters, condensed naphthalene sulfonates, addition products of ethylene oxide and fatty acid esters, salts of addition products of ethylene oxide and fatty acid esters, condensed naphthalene sulfonates, lignin derivatives, naphthalene formaldehyde condensates, sodium isodecyl sulfosuccinate half-ester salts, polycarboxylates, sodium alkylbenzene sulfonates, sodium sulfonated naphthalene salts, sulfonated naphthalene ammonium salts, polyacrylates, phenol sulfonates, and naphthalene sulfonates.

[0163] As used herein, the term “emulsifier” refers to a substance that stabilizes an emulsion, i.e., a mixture of two or more liquids. The emulsifier may be a single emulsifier or a combination of two or more emulsifiers capable of producing agricultural compositions. The emulsifier may be anionic, cationic, or nonionic, or may include a combination of anionic, cationic, and nonionic emulsifiers.

[0164] Examples of nonionic emulsifiers include alkoxylated castor oil, alkoxylated polyarylphenols, alkoxylated alkylphenols, alkoxylated alkylarylphenols, alkoxylated fatty alcohols, and mixtures thereof. More specific examples include alkoxylated acetylenediol, polyoxyalkylene mono and di(alkyl)phenyl ethers, polyoxyalkylenes, and tristyrylphenyl ethers, block copolymers of ethylene oxide and propylene oxide and their C2-C6 alkyl adducts, sorbitan C8-C20 mono, di, and tri(C8-C20 fatty acid) esters, polyoxyalkylene sorbitan mono, di, and tri(C8-C20 fatty acid) esters, sucrose esters, and C8-C20 alkyl polyglycosides.

[0165] Examples of commercially available nonionic emulsifiers include the trade names POLYSORBATE80 (also known as Tween80; polyoxyethylene (20) sorbitan monooleate) (HLB=15), Tween20 (polyoxyethylene sorbitan monolaurate), Tween85 (also known as emulsifier T-85) (HLB=11.0), and TRITON X-100 (also known as octylphenol ethoxylate) (HLB=13.4).

[0166] Useful anionic emulsifiers include calcium-dodecylbenzenesulfonates, dioctyl sulfosuccinates, sulfonated or phosphorylated alkoxylated fatty alcohols, sulfonated or phosphorylated alkoxylated alkylarylphenols and combinations thereof. More specific examples include alkyl carboxylates (including fatty acids), alcohol sulfates, alcohol phosphate mono and diesters, (alkyl)phenol polyoxyethylene ether carboxylates, sulfates and sulfonates, (alkyl)phenol polyoxyethylene phosphate mono and diesters, alkylbenzenesulfonates, naphthalene sulfonates and their formaldehyde condensates, lignosulfonates, alkyl sulfosuccinates and sulfosuccinate amide salts, alkyl polyoxyethylene sulfosuccinates and sulfosuccinate amide salts, as well as C8-20 acyl glutamates, sarcosinates, isethionates and taurates. The cationic counterion associated with the anionic emulsifier is preferably monovalent, such as hydrogen, sodium, potassium, ammonium, or monovalent organic ammonium cation (isopropylamine).

[0167] Examples of emulsifiers that exhibit cationic properties under acidic conditions include fatty amines, amine oxides, and amine ethoxylates. Amphoteric emulsifiers such as betaine may also exhibit these properties. Preferably, the cationic emulsifier is selected from dimethyl cocamine, dimethyl laurylamine oxide, alkyltrimethylammonium chloride, alkyldimethylbenzylammonium chloride, alkylpyridinium chloride, alkylimidazolium chloride, or mixtures thereof.

[0168] Preferably, the nonionic emulsifier is an alkyl polysaccharide, a sorbitan emulsifier, or an alkyl or fatty alkanolamide having an ethoxylate. Alkyl polysaccharides are also called alkyl polyglucosides, alkyl glucosides, or alkyl saccharides. The sorbate emulsifier is a sorbitan fatty acid mono(or sesqui) ester, and includes sorbitan monooleate and sorbitan monolaurate.

[0169] According to one embodiment, humectants that can be used in agricultural compositions include carbinol (hydroxyl)-terminated polydimethylsiloxane (CAS 67674-67-3), Silwet 408 type humectants, phenylnaphthalene sulfonates, alkylnaphthalene sulfonates, sodium alkylnaphthalene sulfonates, sodium sulfonated alkylcarboxylates, polyoxyalkylated ethylphenols, polyoxyethoxylated fatty alcohols, polyoxytoxylated fatty amines, lignin derivatives, alkane sulfonates, alkylbenzene sulfonates, polycarboxylates, sulfosuccinate esters, alkylnaphthalene sulfonates, alkylbenzene sulfonates, alkyl polyglycol ether sulfonates, alkyl ether phosphates, alkyl ether sulfates, and alkyl sulfosuccinate monoesters. Examples of wetting agents include polyoxyethylene alkylphenyl ethers, sodium alkylbenzene sulfonates, dioctyl sulfosuccinates, sodium alkylnaphthalene sulfonates, sodium alkyl sulfates, sodium alkyl sulfosuccinates, polyoxyethylene alkylaryl ethers, or Break-thru DA 675 (an aqueous solution of an organically modified polymer having a pigment-binding group), which can be used individually or in combination of two or more.

[0170] Agricultural compositions may contain solubilizers to ensure good solubilization and / or dissolution of active ingredients such as fungicides and / or lipopeptides. Solubilizers may also be added to increase the solubility of other components such as fungicides and / or lipopeptides and / or surfactants, or to maintain the composition as a stable or homogeneous solution or dispersion.

[0171] Suitable solubilizers for agricultural compositions include, but are not limited to, the following: alcohols and polyols, e.g., ethanol, isopropanol, butanol, benzyl alcohol, ethylene glycol, propylene glycol, butanediol and its isomers, glycerol, pentaerythritol, sorbitol, mannitol, transcutol, dimethyl isosorbide, polyethylene glycol, polypropylene glycol, polyvinyl alcohol, hydroxypropyl methylcellulose and other cellulose derivatives, cyclodextrins and cyclodextrin derivatives, etc.; polyethylene glycol ethers with an average molecular weight of about 200 to about 6000, e.g., tetrahydrofurfuryl alcohol PEG ether (glycoflor) or methoxyPEG; amides and other nitrogen-containing compounds, e.g., 2-pylori. Done, 2-piperidone, ε-caprolactam, N-alkylpyrrolidone, N-hydroxyalkylpyrrolidone, N-alkylpiperidone, N-alkylcaprolactam, dimethylacetamide, and polyvinylpyrrolidone, etc.; esters, such as ethyl propionate, tributyl citrate, acetylated triethyl citrate, acetylated tributyl citrate, triethyl citrate, ethyl oleate, ethyl caprylate, ethyl butyrate, triacetin, propylene glycol monoacetate, propylene glycol diacetate, ε-caprolactone and its isomers, δ-valerolactone and its isomers, β-butyrolactone and its isomers, etc.; and other solubilizers known in the art, such as dimethylacetamide, dimethyl isosorbide, N-methylpyrrolidone, monooctanoin, diethylene glycol monoethyl ether, and water, etc.

[0172] The solubilizer used in the present invention may be any substance that enhances the solubility of the agricultural composition in water. Preferred solubilizers include benzyl acetate; N-methylpyrrolidone; propylene carbonate; alcohols such as benzyl alcohol, ethanol, methanol; and mixtures thereof. In some embodiments, the solubilizer includes sorbitol, triacetin, ethyl alcohol, PEG-400, glycoflore, and propylene glycol.

[0173] As used herein, the term “osmotic enhancer” refers to a compound that accelerates the uptake, i.e., absorption rate, of active ingredients into the plant through the plant cuticle, and / or increases the amount of active ingredients absorbed into the plant body. A classification of substances known as osmotic enhancers includes alkyl phosphate esters such as tributyl phosphate and tripropyl phosphate, as well as naphthalene sulfonates.

[0174] Suitable stickers / adhes include block copolymer EO / PO surfactants, as well as polyvinyl alcohol, polyvinylpyrrolidone, polyacrylate, polymethacrylate, polybutene, polyisobutylene, polystyrene, polyethyleneamine, polyethyleneamide, polyethyleneimine (Lupasol®, Polymin®), polyethers, and copolymers derived from these polymers.

[0175] Thickeners are a type of auxiliary rheological agent, and their rheological properties play a crucial role in hierarchical control, improving the viscosity of a system and maintaining it in a stable suspension or uniform emulsion state; or they can form gels, imparting excellent physical and chemical stability to the product. There are many types of thickeners, which can be classified according to their application into aqueous thickeners, oily thickeners, acidic thickeners, and alkaline thickeners. When selecting these thickeners, product characteristics should be considered in addition to fluidity, transparency, density, gelling ability, and suspension particle retention ability. Examples of thickeners / stabilizers include natural polymers such as carboxymethylcellulose (CMC), guar gum, locust bean gum, xanthan gum, natural gum, hydroxyethylcellulose (HEC), HPMC, etc., or acrylate-based synthetic polymers, polyacrylamide (PAM), PVP, or combinations of synthetic polymers and carbomers.

[0176] Examples of thickeners include organic thickeners such as xanthan gum, polyvinylpyrrolidone, polyvinyl alcohol, polyethylene glycol, methylcellulose, and alginic acid, and inorganic thickeners such as bentonite. Depending on the preference, other thickeners, such as the one known as Aqualon, may also be added. Aqualon is a trademark of Hercules Inc. of Wilmington, Delaware, USA. Aqualon is a cellulose ether-based adhesive thickener. Other thickeners include hydroxyethylcellulose and carboxymethylpropylcellulose.

[0177] According to another embodiment of the present invention, the humectant absorbs moisture during periods of high humidity, and during dry, hot periods (e.g., dry, hot days), the moisture retained in the humectant is extracted by the strong osmotic action of root hairs. Humidifiers that have shown significant advantages in improving water supply to plant roots include sorbitol, glycerol, molasses, potassium lactate, sodium lactate, and potassium acetate.

[0178] According to another embodiment of the present invention, repellents are known to cause insects to stay away from or reject food sources (which insects could otherwise consume). The repellent may be in the form of a gas (olfactory), a liquid, or a solid (gustatory). Insect repellents include benzyl; benzyl benzoate; 2,3,4,5-bis(butyl-2-ene)tetrahydrofurfural (MGK Repellent 11); butoxypolypropylene glycol; N-butylacetanilide; n-butyl-6,6-dimethyl-5,6-dihydro-1,4-pyrone-2-carboxylate (Indalone); dibutyl adipate; dibutyl phthalate; di-n-butylsuccinate (Tabatrex); N,N-diethyl-methatoluamide (also known as Delphone, Detamide, Autan, or simply Deet); dimethylcarbate (cis-bicyclo-[2.2.1]-5-heptene-2,3-dicarboxylate); dimethyl phthalate; 2-ethyl-2-butyl-1,3-propanediol; 2-ethyl-1,3-hexanediol (Rutgers) This includes 612); di-n-propyl isocinecomelonate (MGK Repellent 326); 2-phenylcyclohexanol; and n-propyl N,N-diethyl succinate. Standard repellents for mosquitoes, ticks, etc., are citronella oil, dimethyl phthalate, n-butyl mesityl oxide oxalate, and 2-ethylhexanediol-1,3. Certain groups of insect repellents include terpenoid compounds, where terpenoid alcohols or terpene-ols are terpenoids having at least one hydroxyl group. Examples of terpene-ols include periryl alcohol, carveol, myrtenol, and cis-verbenol; myrtenol, iso-pinocampheol, dihydrocarbeol, isopulegol, terpineol, terpinen-4-ol, nerol, geraniol, and linalool, menthol, β-citronellol, and dihydro-mircenol.

[0179] Agricultural compositions may further include feeding stimulants or attractants. These may include floral scents, light, pheromones, plant extracts, sugars, honey, molasses, proteins, or combinations of various amounts of amino acids; or other attractants adaptable to multiple insect species that induce insects to ingest or be exposed to the active ingredient. Food substances may include plant extracts, sugars, honey, molasses, proteins, or combinations of various amounts of amino acids; or other liquids or substances adaptable to be ingested by multiple insect species.

[0180] The agricultural compositions of the present invention may contain a feeding stimulant (so-called taste stimulant) for the insects to be controlled, and a 1-arylpyrazole and / or nicotinyl insecticide. Suitable feeding stimulants include proteins such as animal and plant proteins (e.g., in the form of meat meal, fish meal, fish extract, marine products, marine product extracts, or blood meal), insect parts, cricket powder, yeast extract, egg yolk, protein hydrolysates, yeast autolysis products, and gluten hydrolysates; carbohydrates and hydrogenated carbohydrates, especially monosaccharides and disaccharides, e.g., glucose, arabinose, fructose, mannose, sucrose, lactose, galactose, maltose, maltotriose, maltotetraose, maltopentaose, or mixtures thereof (molasses, corn syrup, maple syrup, invert sugar, honey, etc.); and polysaccharides such as starch (e.g., potato Examples include modern starch, corn starch, and starch-based materials such as cereal flour (e.g., wheat flour, corn flour, malt flour, rice flour, rice bran, etc.), pectin, and glycerol; hydrogenated monosaccharides and oligosaccharides (sugar alcohols) such as xylitol, sorbitol, mannitol, isomaltose, trehalose, and maltitol, as well as syrups containing maltitol; fats and oils such as vegetable oils (e.g., corn oil, olive oil, caraway oil, flaxseed oil, canola oil, peanut oil, rapeseed oil, sesame oil, soybean oil, sunflower oil, etc.); animal fats and oils (e.g., fish oil, etc.); and fatty acids derived from these fats and oils.

[0181] A suitable adapting agent may be either a non-reactive or reactive adapting agent. Specific examples of reactive adapting agents, though not limited to them, include long-chain fatty acids such as stearic acid (octadecanoic acid); long-chain fatty acid chlorides such as stearoyl chloride (octadecanoyl chloride); long-chain fatty acid anhydrides such as stearic acid anhydride (octadecanoic acid anhydride); epoxidized oils and fatty acid esters; styrene-maleic acid anhydride copolymers; maleic acid anhydride-grafted polypropylene; copolymers of maleic acid anhydride with olefins and / or acrylic esters (e.g., terpolymers of ethylene, acrylic esters, and maleic acid anhydride); and copolymers of glycidyl methacrylate with olefins and / or acrylic esters (e.g., terpolymers of ethylene, acrylic esters, and glycidyl methacrylate).

[0182] Examples of non-reactive compatible agents include, but are not limited to, ethoxylated alcohols, ethoxylated alkylphenols, ethoxylated fatty acids, block polymers of propylene oxide and ethylene oxide, polyglycerol esters, polysaccharide esters, and sorbitan esters. Examples of ethoxylated alcohols include C11-C15 secondary alcohol ethoxylates, polyoxyethylene cetyl ethers, polyoxyethylene stearyl ethers, and C12-C14 natural linear alcohols ethoxylated with ethylene oxide. C11-C15 secondary ethoxylates are available from Dow Chemical Company as Dow Tergitol® 15S. Polyoxyethylene cetyl ethers and polyoxyethylene stearyl ethers are available from ICI Surfactants as products in the Brij® series. C12-C14 natural linear alcohols ethoxylated with ethylene oxide are available from Hoechst Celanese as products in the Genapol® series. Examples of ethoxylated alkylphenols include octylphenoxypoly(ethyleneoxy)ethanol and nonylphenoxypoly(ethyleneoxy)ethanol. Octylphenoxypoly(ethyleneoxy)ethanol is available from Rhodia as part of the Igepal® CA series, and nonylphenoxypoly(ethyleneoxy)ethanol is available from Rhodia as part of the Igepal CO series, or from Dow Chemical Company as Tergitol® NP. Ethoxylated fatty acids include polyethylene glycol monostearate or monolaurate, available from Henkel as part of the Nopalcol® series. Block polymers of propylene oxide and ethylene oxide are available from BASF as part of the Pluronic® series. Polyglycerol esters are available from Stepan as part of the Drewpol® series. Polysaccharide esters are available from Henkel as part of the Glucopon® series, which are alkyl polyglucosides.Sorbitan esters are available from ICI as part of their Tween® series of products.

[0183] Antifungal or antibacterial agents include organosulfur-based antifungal or antibacterial agents (such as zineb, maneb, thyram, mancozeb, polycarbamate, and propineb), benzimidazole-based antifungal or antibacterial agents (such as benomyl and thiophanate-methyl), dicarboxylic acid-based antifungal or antibacterial agents (such as iprodione and procymidone), and other synthetic antifungal or antibacterial agents (such as triazine and iminoctadine triethylacetate). (e.g., antifungal agents, isoprothiolanes, TPN agents, probenazole agents, captans, fluoromids, DPC agents, iminoctadine albesylate agents, etc.), sterol biosynthesis inhibitors (e.g., triflumisole, vitertonal, pyrifenox, phenalimol, triforin, triadimefone, mycrobutanil, difenoconazole, imibenconazole, etc.), acid amide antifungal agents or bactericides (e.g., metalaxyl agents, (e.g., mepronil), copper-based fungicides or bactericides (inorganic copper, organic copper, etc.), antibiotic fungicides or bactericides (e.g., streptomycin, polyoxin, brarhidin S, kasugamycin, validamycin, oxytetracycline), soil fungicides or bactericides (e.g., etridiazole, himexazole), melamine biosynthesis inhibitors (e.g., phthalides, carpropamide), organophosphate fungicides or bactericides This includes fungicides (such as IBP agents, EDDP agents, and fosetyl agents), inorganic insecticides (such as inorganic sulfur agents and bicarbonate agents), methoxyacrylate-based fungicides or bactericides (such as azoxystrobin and kresoxim methyl agents), anilinopyrimidine-based fungicides or bactericides (such as mepanipyrim agents), synthetic antibiotics (such as oxolinic acid agents), naturally derived fungicides or bactericides (such as soybean lecithin), and biologically derived bactericides (such as antagonistic bactericides).

[0184] In at least one embodiment, the agricultural compositions described herein may comprise one or more antifreeze agents. Examples of non-limiting antifreeze agents include ethylene glycol, propylene glycol, urea, glycerin, and combinations thereof.

[0185] Examples of suitable solvent crystallization inhibitors include, but are not limited to, NMP, DMA, DMSO, or PEG. Examples of crystallization inhibitors include ethylene glycol, propylene glycol, glycerin, cyclodextrin, and alkylene oxide adducts of glycerin.

[0186] Antifoaming agents and foam inhibitors are used to reduce foaming during spraying. These include oily antifoaming agents such as silicone-based antifoaming agents, organically modified siloxanes, kerosene-based antifoaming agents, wax-based antifoaming agents, turkey red oil, and fatty acid-based antifoaming agents.

[0187] Examples of suitable foam inhibitors include, but are not limited to, silicone-based foam inhibitors (e.g., aqueous emulsions of dimethylpolysiloxane, Dow-Corning®'s FG-10, Trans-Chemo Inc.'s Trans 10A, etc.) and non-silicone-based foam inhibitors such as octanol, nonanol, and silica. Examples of foam inhibitors include silicone emulsions, silicone oils, acetylenediol, and PO / EO block polymers.

[0188] Examples of suitable colorants or dyes and whitening agents include one or more azo dyes, azo dyes, acridine, aniline dyes, aniline black, indanthrene, eosin, Congo red, dihydroindole, methylene blue, phenazine derivative dyes, neutral red, phenolphthalein, fuchsin, fluorescein, para red, mauve, carotenes; carotenoids such as xanthophyll, cryptoxanthin, zeaxanthin, fucoxanthin, lycopene, lutein; flavonoids such as flavones, flavanones, anthococci, anthocyanins, catechins; quinones such as melanin; chlorophyll, chlorophyllide, bacteriochlorophyll, cytochrome, pheophorbide, Feoporphyrin, hemerisrin, hemoglobin, hemovanadin, hemocyanin, porphyrin Examples include porphyrin pigments such as phosphorus, porphyrin, and myoglobin; phycobilin pigments such as phycocyanin, phycobilin, phycoerythrin, phytochrome, biliverdin, and bilirubin; and alizarin, anthocyanin, anthraquinone, indigo, urobilin, erythrocruorin, carthamine, hexanecretintin, curcumin, crocetin, chlorin, chlorocruorin, genistein, cochineal, gosipor, comelinin, shikonin, stercopyrin, tannin, tulacin, bixin, hypericin, pinnaglobin, brazilin, purpurin, betacyanin, berberine, forbilin, mangosteen, moringin, laminaran, leghemoglobin, litmus, rhodopsin, rhodoxanthine, rhodomycin, carbon black, and red iron oxide.

[0189] Appropriate examples of various tackifiers include, but are not limited to, aliphatic resins, polyethylene resins, hydrogenated resins, aliphatic-aromatic mixed resins, styrene / α-methylenestyrene resins, pure monomer hydrocarbon resins, hydrogenated pure monomer hydrocarbon resins, modified styrene copolymers, pure aromatic monomer copolymers, and hydrogenated aliphatic hydrocarbon resins.

[0190] Examples of suitable binders include gum arabic, glue, gelatin, casein, starch, cellulose esters, aliphatic polyesters, polyalkanoates, aliphatic-aromatic polyesters, sulfonated aliphatic-aromatic polyesters, polyesteramides, rosin / polycaprolactone ternary block copolymers, rosin / polyadipate secondary diester ternary block copolymers, rosin / polysuccinate secondary diester ternary block copolymers, polyvinyl acetate, EVA esters, polyethylene-co-acrylate ethyl ester, polyethylene-co-acrylate methyl ester, polyethylene-copropylene, polyethylene-co-1-butylene, polyethylene-co-1-amylene, polystyrene, acrylic compounds, polyurethanes, urethane-styrene polymer dispersions, nonionic polyester urethane dispersions, and acrylic acid dispersions. Examples include silane-type anionic acrylic ester-styrene polymer dispersions, anionic acrylic ester-styrene-acrylonitrile dispersions, acrylic ester-acrylonitrile dispersions, vinylpyrrolidone / styrene copolymer latex (e.g., ISP Chemical 430), carboxylated and noncarboxylated vinyl acetate-ethylene dispersions, vinyl acetate homopolymer dispersions, polyvinyl chloride emulsions, polyvinylidene fluoride dispersions, ethylene acrylic dispersions, polyamide dispersions, anionic carboxylated or noncarboxylated acrylonitrile-nitrile-butadiene-styrene emulsions and acrylonitrile emulsions, styrene-derived resin dispersions, aliphatic and / or aromatic hydrocarbons derived from resin dispersions, styrene maleic anhydride, and mixtures thereof.

[0191] According to one embodiment of the present invention, binders usable in agricultural compositions may be selected from the group comprising polyvinyl alcohol, phenylnaphthalene sulfonate, lignin derivatives, polyvinylpyrrolidone, polyalkylpyrrolidone, carboxymethylcellulose, xanthan gum, polyethoxylated fatty acids, polyethoxylated fatty alcohols, ethylene oxide copolymers, propylene oxide copolymers, polyethylene glycol, and polyethylene oxide.

[0192] According to one embodiment, examples of preservatives include, but are not limited to, an aqueous solution of 1,2-benzisothiazolin-3-one dipropylene glycol, propionic acid and its salts, salicylic acid and its salts, 2,4-hexadienoic acid (sorbic acid) and its salts, formaldehyde and paraformaldehyde, 2-xynol ether and its salts, 2-zinc sulfphenylpyridine N-oxide, benzoic acid, its esters and salts, and p-hydroxybenzoic acid (p-hydroxybenzoate), its esters and salts.

[0193] The pH adjusters used herein are effective in imparting an alkaline pH of about 7 to about 10 in the final spray solution applied to plants. The pH adjusters may be organic and / or inorganic. Examples of pH adjusters include triethanolamine, primary amino alcohols, ammonium hydroxides, and mixtures thereof.

[0194] Examples of suitable stabilizers, though not limited to them, include agar, alginic acid, alginate, calcium lactate, carrageenan, gellan gum, and guar gum. The compositions of the present invention may contain two or more different stabilizers.

[0195] However, those skilled in the art will understand that other agricultural components known in the art can be used without departing from the scope of the claims of the present invention.

[0196] In some embodiments, a suitable range of agricultural compositions comprising (A) of the present application may be about 0.01% to about 1.0% by weight; about 1% to about 2.5% by weight; about 2.5% to about 5% by weight; or about 5% to about 10% by weight; or about 10% to about 15% by weight; or about 15% to about 20% by weight, based on the total weight of the agricultural composition.

[0197] In some embodiments, a suitable range of the agricultural active ingredient (B) of the present application is about 1% to about 2.5% by weight; or about 2.5% to about 5% by weight; or about 5% to about 10% by weight; or about 10% to about 15% by weight; or about 15% to about 20% by weight; or about 20% to about 25% by weight; or about 25% to about 30% by weight; or about 30% to about 35% by weight; or about 35% by weight The amounts may be approximately 40% by weight; or approximately 40% by weight to approximately 45% by weight; or approximately 45% by weight to approximately 50% by weight; or approximately 50% by weight to approximately 55% by weight; or approximately 55% by weight to approximately 60% by weight; or approximately 60% by weight to approximately 65% ​​by weight; or approximately 65% ​​by weight to approximately 70% by weight; or approximately 70% by weight to approximately 75% by weight; or approximately 75% by weight to approximately 80% by weight; or approximately 80% by weight to approximately 85% by weight; or approximately 85% by weight to approximately 90% by weight.

[0198] In some embodiments, a suitable range of component (C) of the present application is about 1% to about 2.5% by weight; or about 2.5% to about 5% by weight; or about 5% to about 10% by weight; or about 10% to about 15% by weight; or about 15% to about 20% by weight; or about 20% to about 25% by weight; or about 25% to about 30% by weight; or about 30% to about 35% by weight; or about 35% to about 40% by weight; or about 40% by weight It may be approximately 45% by weight; or approximately 45% to approximately 50% by weight; or approximately 50% to approximately 55% by weight; or approximately 55% to approximately 60% by weight; or approximately 60% to approximately 65% ​​by weight; or approximately 65% ​​to approximately 70% by weight; or approximately 70% to approximately 75% by weight; or approximately 75% to approximately 80% by weight; or approximately 80% to approximately 85% by weight; or approximately 85% to approximately 90% by weight; or approximately 90% to approximately 95% by weight; or approximately 95% to approximately 99.9% by weight.

[0199] According to another embodiment of the present application, the agricultural composition is in the form of an aqueous or non-aqueous composition and comprises an emulsion selected from a capsule suspension (CS), an emulsifiable concentrate (EC), a seed treatment emulsion (ES), a concentrated aqueous emulsion (EW), a microemulsion (ME), a suspend emulsion (SE), a water-in-oil emulsion, a seed treatment flowable (FS), an oil dispersant (OD), a suspension concentrate (SC), a water-dispersible granule (WDG), or a wettable powder (WP).

[0200] According to another embodiment of the present application, the agricultural composition is formulated as a liquid, gel, paste, powder, granules, tablet, emulsion, or pellet.

[0201] According to another embodiment of the present application, a method for treating vegetation includes applying an agricultural composition to plants, plant leaves, flowering parts, foliage, stems, fruits, adjacent areas of the plants, soil, seeds, germinating seeds, roots, liquid and solid growing media, flowers, buds, and hydroponic solutions.

[0202] The reactions and compositions relating to this application can be analyzed by known techniques. Particularly preferred are techniques such as 13C nuclear magnetic resonance (NMR) spectroscopy, gas chromatography (GC), infrared spectroscopy (IR), liquid chromatography (LC), and gel permeation chromatography (GPC) for elucidating identity, residual monomer concentration, molecular weight, and molecular weight distribution.

[0203] Furthermore, specific aspects of the present application will be illustrated in detail by the following examples. These examples are provided for illustrative purposes of the present application and are not intended to limit it. [Examples]

[0204] Example A: Grafting of maleic anhydride onto natural oil

[0205] Example A1: Grafting of 1 mole of maleic anhydride into soybean oil 600 g of yellow soybean oil and 67 g of maleic anhydride (1 molar equivalent on an SBO basis) were placed in a 1-liter four-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer. The mixture was sparged with nitrogen at room temperature for only 15 minutes. The mixture was gradually heated from room temperature to 210°C and held isothermally at 210°C for approximately 6–8 hours. An amber-colored viscous product was obtained in >96% yield by a one-pot reaction without the use of catalysts or solvents, and was characterized by NMR and LC (residual maleic anhydride <1%).

[0206] [ka]

[0207] Example A2: Grafting of 2 moles of maleic anhydride into soybean oil 600 g of yellow soybean oil and 137.7 g of maleic anhydride (2 molar equivalents on an SBO basis) were added to a 1-liter four-necked kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer. The mixture was sparged with nitrogen at room temperature for only 15 minutes. The mixture was gradually heated from room temperature to 210°C and held isothermally at 210°C for approximately 6-8 hours. An amber-colored viscous product was obtained in >96% yield by a one-pot reaction without the use of catalysts or solvents, and was characterized by NMR and LC (residual maleic anhydride <1%).

[0208] [ka]

[0209] Example A3: Grafting of 3 moles of maleic anhydride into soybean oil 600 g of yellow soybean oil and 204 g of maleic anhydride (3 molar equivalents on an SBO basis) were added to a 1-liter, four-necked kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer. The mixture was sparged with nitrogen at room temperature for only 15 minutes. The mixture was gradually heated from room temperature to 210°C and held isothermally at 210°C for approximately 6–8 hours. An amber-colored viscous product was obtained in >96% yield by a one-pot reaction without the use of catalysts or solvents, and was characterized by NMR and LC (residual maleic anhydride <1%).

[0210] [ka]

[0211] Example A4: Grafting of maleic anhydride onto palm oil 100 g of palm oil and 23 g of maleic anhydride (2 molar equivalents based on palm oil) were placed in a 1-liter, 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer. The mixture was sparged with nitrogen at room temperature for only 15 minutes. The mixture was gradually heated from room temperature to 210°C and maintained isothermally at 210°C for approximately 8–10 hours. An amber-colored viscous product was obtained in >96% yield by a one-pot reaction without the use of catalysts or solvents, and was characterized by NMR and LC (residual maleic anhydride <1%).

[0212] Example A5: Grafting of maleic anhydride into canola oil 100 g of canola oil and 22.2 g of maleic anhydride (2 molar equivalents based on canola oil) were added to a 1-liter, four-necked kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer. The mixture was sparged with nitrogen at room temperature for only 15 minutes. The mixture was gradually heated from room temperature to 210°C and maintained isothermally at 210°C for approximately 8–10 hours. An amber-colored viscous product was obtained in >96% yield by a one-pot reaction without the use of catalysts or solvents, and was characterized by NMR and LC (residual maleic anhydride <1%).

[0213] Example A6: Grafting of maleic anhydride into sunflower oil 100 g of sunflower oil and 22.4 g of maleic anhydride (2 molar equivalents based on sunflower oil) were added to a 1-liter, 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer. The mixture was sparged with nitrogen at room temperature for only 15 minutes. The mixture was gradually heated from room temperature to 210°C and maintained isothermally at 210°C for approximately 8-10 hours. An amber-colored viscous product was obtained in >96% yield by a one-pot reaction without the use of a catalyst or solvent, and was characterized by NMR and LC (residual maleic anhydride <1%).

[0214] Example A7: Grafting of maleic anhydride onto castor oil 100 g of yellow castor oil and 21 g of maleic anhydride (2 molar equivalents based on castor oil) were added to a 1-liter, four-necked kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer. The mixture was sparged with nitrogen at room temperature for only 15 minutes. The mixture was gradually heated from room temperature to 210°C and maintained isothermally at 210°C for approximately 8–10 hours. An amber-colored viscous product was obtained in >96% yield by a one-pot reaction without the use of catalysts or solvents, and was characterized by NMR and LC (residual maleic anhydride <1%).

[0215] Example B: Grafting of hydrophobic alcohol onto natural oil grafted with maleic anhydride

[0216] Example B1: In a 1-liter, 4-necked kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of the amber-colored viscous product obtained from maleination reaction example A1 and 30.5 g (1 molar equivalent) of 2-octyl-1-dodecanol were mixed and heated to 90°C, where the mixture was held for 6 hours. This one-pot reaction, without the use of a catalyst or solvent, yielded an amber-colored viscous product in >96% yield, which was characterized by NMR, IR, GC (residual 2-octyl-1-dodecanol <5%), and LC (residual maleic anhydride <1%).

[0217] [ka]

[0218] Example B2: In a 1-liter, 4-necked kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of the amber-colored viscous product obtained from maleination reaction example A2 was mixed with 55.64 g (2 molar equivalents) of 2-octyl-1-dodecanol, heated to 90°C, and held for 6 hours. An amber-colored viscous product was obtained in >96% yield by a one-pot reaction without the use of a catalyst or solvent, and was characterized by NMR, IR, GC (residual 2-octyl-1-dodecanol <5%) and LC (residual maleic anhydride <1%).

[0219] Example B3: In a 1-liter, 4-necked kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of the amber-colored viscous product obtained from maleation reaction example A2 was mixed with 61.20 g (2.2 molar equivalents) of 2-octyl-1-dodecanol. The mixture was heated to 90°C and held for 6 hours. An amber-colored viscous product was obtained in >96% yield by a one-pot reaction without the use of a catalyst or solvent. The product was characterized by NMR, GC (residual 2-octyl-1-dodecanol <5%), and LC (residual maleic anhydride <1%).

[0220] Example B4: In a 1-liter, 4-necked kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of the amber-colored viscous product obtained from maleation reaction example A3 was mixed with 25.44 g (1 molar equivalent) of 2-octyl-1-dodecanol, heated to 90°C, and held for 6 hours. An amber-colored viscous product was obtained in >96% yield by a one-pot reaction without the use of a catalyst or solvent, and was characterized by NMR, IR, GC (residual 2-octyl-1-dodecanol <5%) and LC (residual maleic anhydride <1%).

[0221] Example B5: In a 1-liter, 4-necked kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of the amber-colored viscous product obtained from maleation reaction example A3 and 31.81 g (1.25 molar equivalents) of 2-octyl-1-dodecanol were mixed and heated to 90°C, where the mixture was held for 6 hours. An amber-colored viscous product was obtained in >96% yield by a one-pot reaction without the use of a catalyst or solvent, and was characterized by NMR, IR, GC (residual 2-octyl-1-dodecanol <5%) and LC (residual maleic anhydride <1%).

[0222] Example B6: In a 1-liter, 4-necked kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of the amber-colored viscous product obtained from maleation reaction example A3 was mixed with 38.17 g (1.5 molar equivalents) of 2-octyl-1-dodecanol, heated to 90°C, and held for 6 hours. An amber-colored viscous product was obtained in >96% yield by a one-pot reaction without the use of a catalyst or solvent, and was characterized by NMR, IR, GC (residual 2-octyl-1-dodecanol <5%) and LC (residual maleic anhydride <1%).

[0223] Example B7: In a 1-liter, 4-necked kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of the amber-colored viscous product obtained from maleination reaction example A3 and 50.89 g (2 molar equivalents) of 2-octyl-1-dodecanol were mixed and heated to 90°C, where the mixture was held for 6 hours. An amber-colored viscous product was obtained in >96% yield by a one-pot reaction without the use of a catalyst or solvent, and was characterized by NMR, IR, GC (residual 2-octyl-1-dodecanol <5%) and LC (residual maleic anhydride <1%).

[0224] Example B8: In a 1-liter, 4-necked kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of the amber-colored viscous product obtained from maleation reaction example A3 was mixed with 63.61 g (2.5 molar equivalents) of 2-octyl-1-dodecanol, heated to 90°C, and held for 6 hours. An amber-colored viscous product was obtained in >96% yield by a one-pot reaction without the use of a catalyst or solvent, and was characterized by NMR, IR, GC (residual 2-octyl-1-dodecanol <5%) and LC (residual maleic anhydride <1%).

[0225] Example B9: In a 1-liter, 4-necked kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of the amber-colored viscous product obtained from maleination reaction example A4 and 35 g (1 molar equivalent) of 2-octyl-1-dodecanol were mixed and heated to 90°C, where the mixture was held for 6 hours. An amber-colored viscous product was obtained in >96% yield by a one-pot reaction without the use of a catalyst or solvent, and was characterized by NMR, IR, GC (residual 2-octyl-1-dodecanol <5%) and LC (residual maleic anhydride <1%).

[0226] Example B10: In a 1-liter, 4-necked kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of the amber-colored viscous product obtained from maleation reaction example A5 and 35 g (1 molar equivalent) of 2-octyl-1-dodecanol were mixed and heated to 90°C, where the mixture was held for 6 hours. An amber-colored viscous product was obtained in >96% yield by a one-pot reaction without the use of a catalyst or solvent, and was characterized by NMR, IR, GC (residual 2-octyl-1-dodecanol <5%) and LC (residual maleic anhydride <1%).

[0227] Example B11: In a 1-liter, 4-necked kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of the amber-colored viscous product obtained from maleination reaction example A6 and 35 g (1 molar equivalent) of 2-octyl-1-dodecanol were mixed and heated to 90°C, where the mixture was held for 6 hours. The amber-colored viscous product was obtained in >96% yield by a one-pot reaction without the use of a catalyst or solvent, and was characterized by NMR, IR, GC (residual 2-octyl-1-dodecanol <5%) and LC (residual maleic anhydride <1%).

[0228] Example B12: In a 1-liter, 4-necked kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of the amber-colored viscous product obtained from maleination reaction example A7 and 35 g (1 molar equivalent) of 2-octyl-1-dodecanol were mixed and heated to 90°C, where the mixture was held for 6 hours. An amber-colored viscous product was obtained in >96% yield by a one-pot reaction without the use of a catalyst or solvent, and was characterized by NMR, IR, GC (residual 2-octyl-1-dodecanol <5%) and LC (residual maleic anhydride <1%).

[0229] Example B13: In a 1-liter, four-necked kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of the amber-colored viscous product obtained from maleination reaction Example A3 was heated to 85°C with stirring. 1.2 molar equivalents of 2-ethyl-1-hexanol were added, and the mixture was held at 85°C for 6-8 hours. The amber-colored liquid product was characterized by NMR and IR. The yield of the liquid product was >98%.

[0230] Example B14: In a 1-liter, four-necked kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of the amber-colored viscous product obtained from maleination reaction Example A3 was heated to 85°C with stirring. 2.0 molar equivalents of 2-ethyl-1-hexanol were added, and the mixture was held at 85°C for 6-8 hours. The amber-colored liquid product was characterized by NMR and IR. The yield of the liquid product was >98%.

[0231] Example B15: In a 1-liter, four-necked kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of the amber-colored viscous product obtained from maleination reaction Example A3 was heated to 85°C with stirring. 1.2 molar equivalents of behenyl alcohol were added, and the mixture was held at 85°C for 6-8 hours. The amber-colored liquid product was characterized by NMR and IR. The yield of the liquid product was >98%.

[0232] Example B16: In a 1-liter, four-necked kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of the amber-colored viscous product obtained from maleination reaction Example A3 was heated to 85°C with stirring. 2.0 molar equivalents of behenyl alcohol were added, and the mixture was held at 85°C for 6-8 hours. The amber-colored liquid product was characterized by NMR and IR. The yield of the liquid product was >98%.

[0233] Example C: Grafting of hydrophilic polyols, hydrophilic alcohols, or hydrophobic polyols onto natural oils grafted with maleic anhydride and hydrophobic alcohols.

[0234] Example C1: In a 1-liter, 4-necked kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of the amber-colored viscous product obtained from Example B6 was mixed with 5.7 g (1 molar equivalent) of glycerin, heated to 90°C, and held for 4-6 hours. An amber-colored viscous product was obtained in >96% yield by a one-pot reaction without the use of a catalyst or solvent, and was characterized by NMR and LC (residual maleic anhydride <0.05%).

[0235] [ka]

[0236] Example C2: In a 1-liter four-necked kettle equipped with a thermocouple, a condenser, a nitrogen purge adapter and a mechanical stirrer, 100 g of the amber viscous product obtained from Example B4 and 6.28 g (1 molar equivalent) of glycerin were mixed, heated to 90 °C and held for 4 - 6 hours. By a one-pot reaction without using a catalyst or a solvent, an amber viscous product was obtained in a yield of >96%, and its properties were evaluated by NMR and LC (residual maleic anhydride <0.05%).

[0237] Example C3: In a 1-liter four-necked kettle equipped with a thermocouple, a condenser, a nitrogen purge adapter and a mechanical stirrer, 100 g of the amber viscous product obtained from Example B4 and 9.42 g (1.5 molar equivalents) of glycerin were mixed, heated to 90 °C and held for 4 hours. By a one-pot reaction without using a catalyst or a solvent, an amber viscous product was obtained in a yield of >96%, and its properties were evaluated by NMR and LC (residual maleic anhydride <0.05%).

[0238] Example C4: In a 1-liter four-necked kettle equipped with a thermocouple, a condenser, a nitrogen purge adapter and a mechanical stirrer, 100 g of the amber viscous product obtained from Example B9 and 11 g (1 molar equivalent) of glycerin were mixed, heated to 90 °C and held for 4 - 6 hours. By a one-pot reaction without using a catalyst or a solvent, an amber viscous product was obtained in a yield of >96%, and its properties were evaluated by NMR and LC (residual maleic anhydride <0.05%).

[0239] Example C5: In a 1-liter four-necked kettle equipped with a thermocouple, a condenser, a nitrogen purge adapter and a mechanical stirrer, 100 g of the amber viscous product obtained from Example B10 and 11 g (1 molar equivalent) of glycerin were mixed, heated to 90 °C and held for 4 - 6 hours. By a one-pot reaction without using a catalyst or a solvent, an amber viscous product was obtained in a yield of >96%, and its properties were evaluated by NMR and LC (residual maleic anhydride <0.05%).

[0240] Example C6: In a 1-liter, 4-necked kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of the amber-colored viscous product obtained from Example B11 was mixed with 11 g (1 molar equivalent) of glycerin, heated to 90°C, and held for 4-6 hours. An amber-colored viscous product was obtained in >96% yield by a one-pot reaction without the use of a catalyst or solvent, and was characterized by NMR and LC (residual maleic anhydride <0.05%).

[0241] Example C7: In a 1-liter, 4-necked kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of the amber-colored viscous product obtained from Example B12 was mixed with 11 g (1 molar equivalent) of glycerin, heated to 90°C, and held for 4-6 hours. An amber-colored viscous product was obtained in >96% yield by a one-pot reaction without the use of a catalyst or solvent, and was characterized by NMR and LC (residual maleic anhydride <0.05%).

[0242] Example C8: In a 1-liter, 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 152 g of the amber-colored viscous product obtained from Example B4 was mixed with 4.74 g (1 molar equivalent) of ethanol, heated to 90°C, and held for 8 hours. An amber-colored product was obtained in >96% yield by a one-pot reaction without the use of a catalyst or solvent, and was characterized by NMR and LC (residual maleic anhydride <0.05%).

[0243] [ka]

[0244] Example C9: In a 1-liter, 4-necked kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 152 g of the amber-colored viscous product obtained from Example B4 was mixed with 9.47 g (2 molar equivalents) of ethanol, heated to 90°C, and held for 8 hours. An amber-colored product was obtained in >96% yield by a one-pot reaction without the use of a catalyst or solvent, and was characterized by NMR and LC (residual maleic anhydride <0.05%).

[0245] Example C10: In a 1-liter, 4-necked kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of the amber-colored viscous product obtained from Example B13 was heated to 85°C with stirring. 1 molar equivalent of castor oil was added, and the mixture was held at 85°C for 6-8 hours. The amber-colored liquid product was characterized by NMR and IR. The yield of the liquid product was >98%.

[0246] Example C11: In a 1-liter, 4-necked kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of the amber-colored viscous product obtained from Example B13 was heated to 85°C with stirring. 0.5 molar equivalents of glycerin and 0.5 molar equivalents of castor oil were added simultaneously, and the mixture was held at 85°C for 6-8 hours. The amber-colored liquid product was characterized by NMR and IR. The yield of the liquid product was >98%.

[0247] Example C12: In a 1-liter, 4-necked kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of the amber-colored viscous product obtained from Example B14 was heated to 85°C with stirring, 1 molar equivalent of castor oil was added, and the mixture was held at 85°C for 6-8 hours. The amber-colored liquid product was characterized by NMR and IR. The yield of the liquid product was >98%.

[0248] Example C13: In a 1-liter, 4-necked kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of the amber-colored viscous product obtained from Example B14 was heated to 85°C with stirring. 0.5 molar equivalents of glycerin and 0.5 molar equivalents of castor oil were added simultaneously, and the mixture was held at 85°C for 6-8 hours. The amber-colored liquid product was characterized by NMR and IR. The yield of the liquid product was >98%.

[0249] Example C14: In a 1-liter, 4-necked kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of the amber-colored viscous product obtained from Example B15 was heated to 85°C with stirring, 1 molar equivalent of castor oil was added, and the mixture was held at 85°C for 6-8 hours. The amber-colored liquid product was characterized by NMR and IR. The yield of the liquid product was >98%.

[0250] Example C15: In a 1-liter, four-outlet kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of the amber-colored viscous product obtained from Example B15 was heated to 85°C with stirring. 0.5 molar equivalents of glycerin and 0.5 molar equivalents of castor oil were added simultaneously, and the mixture was held at 85°C for 6-8 hours. The amber-colored liquid product was characterized by NMR and IR. The yield of the liquid product was >98%.

[0251] Example C16: In a 1-liter, 4-necked kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of the amber-colored viscous product obtained from Example B16 was heated to 85°C with stirring, 1 molar equivalent of castor oil was added, and the mixture was held at 85°C for 6-8 hours. The amber-colored liquid product was characterized by NMR and IR. The yield of the liquid product was >98%.

[0252] Example C17: In a 1-liter four-necked kettle equipped with a thermocouple, a capacitor, a nitrogen purge adapter and a mechanical stirrer, 100 g of the amber viscous product obtained from Example B16 was heated to 85 °C while stirring, 0.5 molar equivalents of glycerin and 0.5 molar equivalents of castor oil were added in one portion, and it was held at 85 °C for 6 to 8 hours. The amber liquid product was characterized by NMR and IR. The yield of the liquid product was >98%.

[0253] Example D: Grafting of hydrophilic polyol onto natural oil grafted with maleic anhydride and hydrophobic alcohol

[0254] Example D1: In a 1-liter four-necked kettle equipped with a thermocouple, a capacitor, a nitrogen purge adapter and a mechanical stirrer, 68.43 g of the amber viscous product obtained from Example B6 and 23.73 g (0.50 molar equivalents) of β-cyclodextrin were mixed, heated to 90 °C and held for 6 hours. A yellow product was obtained in a yield of >96% by a one-pot reaction without using a catalyst or a solvent, and was characterized by IR and LC (residual maleic anhydride <0.05%).

[0255]

Chemical formula

[0256] Example D2: In a 1-liter four-necked kettle equipped with a thermocouple, a capacitor, a nitrogen purge adapter and a mechanical stirrer, 68.43 g of the amber viscous product obtained from Example B6, 23.73 g (0.50 molar equivalents) of β-cyclodextrin and 3.85 g (1 molar equivalent) of glycerin were mixed, heated to 90 °C and held for 4 hours. A yellow product was obtained in a yield of >96% by a one-pot reaction without using a catalyst or a solvent, and was characterized by IR and LC (residual maleic anhydride <0.05%).

[0257]

Chemical formula

[0258] Example D3: In a 1-liter four-necked kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 68.43 g of the amber-colored viscous product obtained from Example B6, 23.73 g (0.50 molar equivalent) of β-cyclodextrin, and 1.93 g (0.50 molar equivalent) of glycerin were mixed and heated to 90°C and held for 4 hours. A one-pot reaction without the use of a catalyst or solvent yielded a yellow product in >96% yield, which was characterized by IR and LC (residual maleic acid <0.05%). A one-pot reaction without the use of a catalyst or solvent yielded a yellow product in >96% yield, which was characterized by IR and LC (residual maleic anhydride <0.05%).

[0259] Example E: Reaction of natural oil grafted with maleic anhydride with water

[0260] Example E1: In a 1-liter, four-necked kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of the amber-colored viscous product obtained from maleination reaction example A3 was mixed with 6.10 g (3 molar equivalents) of water, heated to 90°C, and held for 20 hours. A one-pot reaction without the use of a catalyst or solvent yielded a yellow product in a yield exceeding 90%, which was characterized by NMR, IR, and LC (residual maleic acid less than 0.05%).

[0261] [ka]

[0262] Example F: Grafting of hydrophilic glycerin onto natural oil grafted with maleic anhydride.

[0263] Example F1

[0264] In a 1-liter, four-necked kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 176 g of the amber-colored viscous product obtained from maleination reaction A3 was mixed with 6.87 g (0.5 molar equivalent) of glycerin, heated to 90°C, and held for 2 hours. A one-pot reaction without catalyst or solvent yielded a yellow product in >96% yield, which was characterized by IR and LC (residual maleic anhydride <0.05%).

[0265] [ka]

[0266] Example F2: In a 1-liter, 4-necked kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 176 g of the amber-colored viscous product obtained from maleination reaction A3 was mixed with 13.74 g (1 molar equivalent) of glycerin, and the mixture was heated to 90°C and held for 4 hours. A one-pot reaction without the use of a catalyst or solvent yielded a yellow product in >96% yield, which was characterized by IR and LC (residual maleic anhydride <0.05%).

[0267] Example G: Reaction of a natural oil grafted with maleic anhydride with castor oil, followed by a reaction with one or more alcohols.

[0268] Example G1: In a 1-liter, four-necked kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of the amber-colored viscous product obtained from maleination reaction example A3 was heated to 85°C with stirring. 0.3 molar equivalents of castor oil were added, and the mixture was held at 85°C for 4-6 hours. The amber-colored liquid intermediate was characterized by NMR and IR. Ethanol (1.2 molar equivalents) was added to the reaction mixture, and the mixture was held at 85°C for 6-8 hours. The amber-colored product was characterized by NMR and IR. The yield of the product was >98%.

[0269] Example G2: In a 1-liter four-necked kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of the amber-colored viscous product obtained from maleination reaction example A3 was heated to 85°C with stirring, 0.5 molar equivalents of castor oil were added, and the mixture was held at 85°C for 4-6 hours. The amber-colored liquid intermediate was characterized by NMR and IR. Ethanol (1.2 molar equivalents) was added to the reaction mixture, and the mixture was held at 85°C for 6-8 hours. The amber-colored product was characterized by NMR and IR. The yield of the product was >98%.

[0270] Example G3: In a 1-liter, four-necked kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of the amber-colored viscous product obtained from maleination reaction example A3 was heated to 85°C with stirring. 0.3 molar equivalents of castor oil were added, and the mixture was held at 85°C for 4-6 hours. The amber-colored liquid intermediate was characterized by NMR and IR. Behenyl alcohol (1.2 molar equivalents) was added to the reaction mixture, and the mixture was held at 85°C for 6-8 hours. The yellow, waxy, malleable product was characterized by NMR and IR. The yield of the product was >98%.

[0271] Example G4: In a 1-liter, four-necked kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of the amber-colored viscous product obtained from maleination reaction Example A3 was heated to 85°C with stirring. 0.5 molar equivalents of castor oil were added, and the mixture was held at 85°C for 4-6 hours. The amber-colored liquid intermediate was characterized by NMR and IR. Behenyl alcohol (1.2 molar equivalents) was added to the reaction mixture, and the mixture was held at 85°C for 6-8 hours. The yellow, waxy, malleable product was characterized by NMR and IR. The yield of the product was >98%.

[0272] Example G5: In a 1-liter, four-necked kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of the amber-colored viscous product obtained from maleination reaction example A3 was heated to 85°C with stirring. 0.3 molar equivalents of castor oil were added, and the mixture was held at 85°C for 4-6 hours. The amber-colored liquid intermediate was characterized by NMR and IR. Behenyl alcohol (2.0 molar equivalents) was added to the reaction mixture, and the mixture was held at 85°C for 6-8 hours. The yellow, waxy, malleable product was characterized by NMR and IR. The yield of the product was >98%.

[0273] Example G6: In a 1-liter, four-necked kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of the amber-colored viscous product obtained from maleination reaction Example A3 was heated to 85°C with stirring. 0.5 molar equivalents of castor oil were added, and the mixture was held at 85°C for 4-6 hours. The amber-colored liquid intermediate was characterized by NMR and IR. Behenyl alcohol (2.0 molar equivalents) was added to the reaction mixture, and the mixture was held at 85°C for 6-8 hours. The yellow, waxy, malleable product was characterized by NMR and IR. The yield of the product was >98%.

[0274] Example G7: In a 1-liter, 4-necked kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of the amber-colored viscous product obtained from maleination reaction example A3 was heated to 85°C with stirring. 0.3 molar equivalents of castor oil were added, and the mixture was held at 85°C for 4-6 hours. The amber-colored liquid intermediate was characterized by NMR and IR. 2-Octyl-1-dodecanol (1.2 molar equivalents) was added to the reaction mixture, and the mixture was held at 85°C for 6-8 hours. The yellow, waxy, malleable product was characterized by NMR and IR. The yield of the product was >98%.

[0275] Example G8: In a 1-liter, four-necked kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of the amber-colored viscous product obtained from maleination reaction example A3 was heated to 85°C with stirring. 0.5 molar equivalents of castor oil were added, and the mixture was held at 85°C for 4-6 hours. The amber-colored liquid intermediate was characterized by NMR and IR. 2-Octyl-1-dodecanol (1.2 molar equivalents) was added to the reaction mixture, and the mixture was held at 85°C for 6-8 hours. The yellow, waxy, malleable product was characterized by NMR and IR. The yield of the product was >98%.

[0276] Example G9: In a 1-liter, 4-necked kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of the amber-colored viscous product obtained from maleination reaction example A3 was heated to 85°C with stirring. 0.3 molar equivalents of castor oil were added, and the mixture was held at 85°C for 4-6 hours. The amber-colored liquid intermediate was characterized by NMR and IR. 2.2 molar equivalents of 2-octyl-1-dodecanol were added to the reaction mixture, and the mixture was held at 85°C for 6-8 hours. The yellow, waxy, malleable product was characterized by NMR and IR. The yield of the product was >98%.

[0277] Example G10: In a 1-liter, four-necked kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of the amber-colored viscous product obtained from maleination reaction example A3 was heated to 85°C with stirring. 0.5 molar equivalents of castor oil were added, and the mixture was held at 85°C for 4-6 hours. The amber-colored liquid intermediate was characterized by NMR and IR. 2.2 molar equivalents of 2-octyl-1-dodecanol were added to the reaction mixture, and the mixture was held at 85°C for 6-8 hours. The yellow, waxy, malleable product was characterized by NMR and IR. The yield of the product was >98%.

[0278] Example G11: In a 1-liter, 4-necked kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of the amber-colored viscous product obtained from maleination reaction example A3 was heated to 85°C with stirring, 0.4 molar equivalents of castor oil were added, and the mixture was held at 85°C for 4-6 hours. The amber-colored liquid intermediate was characterized by NMR and IR. Behenyl alcohol (1.5 molar equivalents) and 2-octyl-1-dodecanol (0.5 molar equivalents) were added to the reaction mixture all at once, and the mixture was held at 85°C for 6-8 hours. The yellow, waxy, malleable product was characterized by NMR and IR. The yield of the product was >98%.

[0279] Hydrophilic Modified Soybean Oil - Example of a Multifunctional Pesticide Polymer

[0280] Example 1: Matrix Preparation The compositions shown in the table below were prepared by weighing appropriate amounts of each component and placing them into 4-ounce stoppered bottles to make 100g samples. The contents were dispersed using an overhead mixer for 1 hour.

[0281] A 100g matrix composition was prepared by dispersing the following components in a 4-ounce stoppered bottle: 3.75g maleated soybean oil, 2.5g of a complex of PVP (polyvinylpyrrolidone) and MVE-MAHE (methyl vinyl ether / maleic acid half-ester neutralized product) copolymer, 12.5g of phosphate ester, 5.0g of methylated soybean oil, and 73.75g of paraffinic oil. Finally, 2.5g of bentonite was added to adjust the viscosity of the final liquid system. The composition was held at 54°C for 14 days and was visually stable with no phase separation, precipitation, or particle aggregation observed.

[0282] [Table 1]

[0283] Example 2: Addition of the active ingredient atrazine 20.0 g of atrazine was added to 78.0 g of the matrix from Example 1 (without bentonite SD-1). 2.0 g of bentonite was gradually added to adjust the viscosity of the final liquid system. The composition was held at 54°C for 14 days and was visually stable, with no phase separation, precipitation, or particle aggregation observed, demonstrating that it is a stable formulation.

[0284] [Table 2]

[0285] Example 3: Seed Coating 100 g of seed coating composition was prepared in a 250 mL glass beaker. 100 g of maleated soybean oil, 45.56 g of water, and 12.00 g of propylene glycol were added to the beaker and mixed at 400 rpm for 10 minutes using an overhead mixer and a propeller-type stirring blade. 0.25 g of xanthan gum was gradually added and mixed for 15 minutes or until completely hydrated. A 20% aqueous solution of dipropylene glycol containing a complex of PVP (polyvinylpyrrolidone) and MVE-MAHE (methyl vinyl ether / maleic acid half-ester neutralized), a silicone defoamer, and 1,2-benzisothiazolin-3-one GXL was added and mixed. The mixing speed was increased to 600 rpm, and zinc oxide, zinc EDTA, sodium molybdate, and red pigment were gradually added and mixed for 15 minutes.

[0286] [Table 3]

[0287] Example 4: Water-dispersible granules The active ingredients were mixed with a dispersant and a wetting agent until a uniform powder was obtained. An inert filler was added and mixed until a uniform powder was obtained. The resulting powder can be applied directly to the soil or mixed with water to create a suspension for spray application.

[0288] Formula 1: Active ingredient - pesticide (e.g., imidacloprid) 500g; humectant - nonionic surfactant (e.g., alkylphenol ethoxylate (APEO) or alcohol ethoxylate (AE) or polyoxyethylene sorbitan ester (Tween)) 10g; dispersant / binder - maleated soybean oil 5g; and inert filler - 485g (e.g., clay (kaolin or attapulgite), or talc, or calcium carbonate, or silica).

[0289] Formula 2: Active ingredient - 100 g of chlorpyrifos pesticide; Binder and dispersant - 10 g of functionalized maleinated soybean oil; Inert filler - 890 g (clay (kaolin or attapulgite), or talc, or calcium carbonate, or silica).

[0290] Example 5: Agricultural chemical applications of non-aqueous dispersants Herbicides: Dispersants can be used to disperse herbicides in oil-based solutions, enabling better and more uniform coverage of weeds in agricultural fields. This improves the effectiveness of the herbicide and reduces the amount of herbicide required.

[0291] For example, a formulation of an oil-based herbicide dispersion may include 20-50% by weight of the herbicide active ingredient, 5-50% by weight of an oily carrier such as mineral oil or vegetable oil, and 1-5% by weight of a non-aqueous dispersant. The specific concentration is determined by the properties of the herbicide and oil, as well as the intended use (Table 6).

[0292] [Table 4]

[0293] Insecticides: Non-aqueous dispersants can also be used to disperse insecticides in oil-based solutions. This is particularly useful in greenhouse applications where water-based sprays may not be effective or may easily damage plants.

[0294] For example, a formulation of an oil-based insecticide dispersion may include 1-10% by weight of the active insecticide, 90-99% by weight of an oily carrier such as canola oil or soybean oil, and 1-5% by weight of a non-aqueous dispersant. The specific concentrations are determined by the properties of the insecticide and oil, as well as the intended use.

[0295] [Table 5]

[0296] Antifungal agents: Non-aqueous dispersants can also be used to disperse antifungal agents in oil-based solutions, which is particularly useful for treating fungal infections in crops or soil.

[0297] For example, a formulation of an oil-based antifungal dispersion may include 10-30% by weight of the antifungal active ingredient, 70-90% by weight of an oily carrier such as vegetable oil or mineral oil, and 1-5% by weight of a non-aqueous dispersant. The specific concentration is determined by the properties of the fungicide and oil, as well as the intended use.

[0298] [Table 6]

[0299] Seed coating: Non-aqueous dispersants can also be used as components of seed coatings, improving the adhesion and coverage of pesticides to the seed surface. This improves pesticide efficiency and reduces the amount of pesticide required per seed.

[0300] For example, a seed coating formulation may include 1-20% by weight of a pesticide, 5-30% by weight of a binder such as starch or gum, 50-90% by weight of an oily carrier such as vegetable oil or mineral oil, and 1-5% by weight of a non-aqueous dispersant. The specific concentrations will be determined by the properties of the pesticide, binder, oil, and dispersant, as well as the target seeds and application.

[0301] [Table 7]

[0302] Livestock applications: Non-aqueous dispersants can also be used for livestock applications such as dispersing insecticides for treating livestock pests or dispersing drugs in oil-based solutions for treating livestock diseases.

[0303] For example, a formulation of an oil-based insecticide for livestock may contain 1-10% by weight of the active insecticide, 90-99% by weight of an oily carrier such as mineral oil or vegetable oil, and 1-5% by weight of a non-aqueous dispersant. The specific concentration is determined by the properties of the insecticide and oil, as well as the target application and type of livestock.

[0304] [Table 8]

[0305] Example 8: Agricultural chemical applications of non-aqueous binders Non-aqueous binders can be used in seed coating to adhere the active ingredient to the seed, allowing the pesticide or other treatment agent to be directly delivered to the plant at germination. The non-aqueous binder can be mixed with the active ingredient and other necessary additives and applied to the seed using a seed processing machine or other suitable device.

[0306] [Table 9]

[0307] Granular formulations are commonly used in agriculture for applying pesticides or other treatment agents to the soil. Non-aqueous binders bind the active ingredient and other necessary additives into granules, which can then be applied using a broadcast spreader or other suitable device.

[0308] [Table 10]

[0309] Non-aqueous binders are used in sustained-release formulations to allow the active ingredient to be released over a specific period, providing long-term protection to crops. Non-aqueous binders are used to coat the active ingredient and the necessary carrier, and can be applied directly to soil or plants using appropriate equipment.

[0310] [Table 11]

[0311] Non-aqueous binders can be used in film coatings to form a protective barrier around seeds or other plant materials. They are used to coat the surface of seeds or plant materials, providing protection against pests and diseases while enabling seed germination or plant growth.

[0312] [Table 12]

[0313] While compositions and methods of the inventive concept described herein and / or claimed have been described in particular aspects, it will be apparent to those skilled in the art that variations in compositions and / or methods, as well as in the steps or order of steps of the methods described herein, can be made without departing from the concept, nature and scope of the disclosure and / or claimed inventive concept. All such similar substitutions and modifications apparent to those skilled in the art shall be deemed to be included in the spirit, scope and concept of the disclosure and / or claimed inventive concept.

Claims

1. (A) An agricultural composition comprising a reaction product of maleated natural oil and a functionalized or non-functionalized site selected from the group consisting of hydrophobic sites, hydrophilic sites, and combinations thereof.

2. The agricultural composition according to claim 1, wherein the hydrophilic portion is not a polyalkylene glycol, polyetheramine, alkyleneamine, or alkanolamine.

3. The agricultural composition according to claim 1, wherein the reaction product is a reaction product of maleated natural oil, at least one functionalized or non-functionalized hydrophobic moiety, and at least one functionalized or non-functionalized hydrophilic moiety.

4. The agricultural composition according to claim 1, further comprising (B) one or more agricultural active ingredients; and (C) one or more components.

5. The agricultural composition according to claim 1, wherein the reaction product comprises a maleated functional group functionalized at a hydrophobic site, a maleated functional group functionalized at a hydrophilic site, an unreacted maleated functional group, or a combination thereof.

6. The agricultural composition according to claim 1, wherein the hydrophobic moiety is a moiety selected from the group consisting of: unsubstituted or substituted alkyl, cycloalkyl, alkenyl and aryl alcohols containing about 6 to about 36 carbon atoms, which may or may not have heteroatoms; unsubstituted or substituted alkyl, cycloalkyl, alkenyl and arylamines containing about 6 to about 36 carbon atoms, which may or may not have heteroatoms; unsubstituted or substituted polyols containing about 37 to about 60 carbon atoms, which may or may not have heteroatoms; silicon compounds; and combinations thereof.

7. The agricultural composition according to claim 1, wherein the hydrophilic moiety is a moiety selected from the group consisting of: unsubstituted or substituted alkyl, cycloalkyl, alkenyl and aryl alcohols containing about 1 to about 5 carbon atoms, which may or may not have heteroatoms; unsubstituted or substituted alkyl, cycloalkyl, alkenyl and arylamines containing about 1 to about 5 carbon atoms, which may or may not have heteroatoms; unsubstituted or substituted polyols containing about 2 to about 36 carbon atoms, which may or may not have heteroatoms; poly(ethylene glycol) monomethyl ether (mPEG) containing 5 to 45 carbon atoms; silane; and combinations thereof.

8. The agricultural composition according to claim 3, wherein the hydrophilic moiety is a moiety selected from the group consisting of: unsubstituted or substituted alkyl, cycloalkyl, alkenyl and aryl alcohols containing about 1 to about 5 carbon atoms, which may or may not have heteroatoms; unsubstituted or substituted alkyl, cycloalkyl, alkenyl and arylamines containing about 1 to about 5 carbon atoms, which may or may not have heteroatoms; unsubstituted or substituted polyols containing about 2 to about 36 carbon atoms, which may or may not have heteroatoms; poly(ethylene glycol) monomethyl ether (mPEG) containing 5 to 45 carbon atoms; silane; and combinations thereof.

9. The agricultural composition according to claim 7, wherein the silane is functionalized with an alcohol, an amine, or a combination thereof.

10. The agricultural composition according to claim 6, wherein the unsubstituted or substituted alkyl, cycloalkyl, alkenyl and aryl alcohol is selected from the group consisting of hexanol, heptanol, nonanol, decanol, dodecanol, phenol, ethylbenzyl alcohol, 2-ethyl-1-hexanol, 1-octanol, 2-octanol, 2-butyl-1-octanol, 2-octyl-1-dodecyl alcohol, 1-tetradecanol, 2-tetradecanol, 1-hexadecanol, 2-hexadecanol, 1-octanol, behenyl alcohol, 3,7-dimethyl-1-octanol, 2-propyl-1-pentanol, 4-methyl-1-pentanol and mixtures thereof.

11. The agricultural composition according to claim 6, wherein the unsubstituted or substituted alkyl, cycloalkyl, alkenyl and arylamine is selected from the group consisting of benzylamine, cyclohexylamine, hexylamine, methylhexylamine, phenethylamine, octylamine, oleylamine, decylamine, dodecylamine, octadecylamine, undecylamine, pentadecylamine, 2-methylbutylamine and mixtures thereof.

12. The agricultural composition according to claim 6, wherein the unsubstituted or substituted polyol is selected from the group consisting of 1,6-hexanediol, 1,7-heptanediol, 1,8-octanediol, 1,9-nonanediol, 1,10-decanediol, 1,12-dodecanediol, poly(tetramethylene ether) glycol, poly(tetramethylene carbonate), poly(hexamethylene carbonate), and castor oil.

13. The agricultural composition according to claim 6, wherein the silicon-based compound is a hydrophobic compound selected from the group consisting of aminopropylmethylsiloxane-dimethylsiloxane, N-ethylaminoisobutyl-terminated polydimethylsiloxane, poly(1,1-dimethylsilazane) telomer, aminopropyl-terminated polydimethylsiloxane, monoaminopropyl-terminated polydimethylsiloxane, (tetramethylpiperidinyloxy)propylmethylsiloxane)-dimethylsiloxane copolymer, polydimethylsiloxane, carbinol(hydroxyl)-terminated polydimethylsiloxane, monocarbinol-terminated polydimethylsiloxane, monocarbinol-terminated functional polydimethylsiloxane, [bis(hydroxyethyl)amine]-terminated polydimethylsiloxane, silanol-terminated polydimethylsiloxane, silanol-terminated polydiphenylsiloxane, dodecylmethylsiloxane-hydroxypolyalkyleneoxypropylmethylsiloxane, and mixtures thereof.

14. The agricultural composition according to claim 7, wherein the unsubstituted or substituted alkyl, cycloalkyl, alkenyl and aryl alcohols are selected from the group consisting of methanol, ethanol, propanol, isopropanol, butanol, methoxypolyethylene glycol and mixtures thereof.

15. The agricultural composition according to claim 7, wherein the unsubstituted or substituted alkyl, cycloalkyl, alkenyl and arylamine is selected from the group consisting of diethanolamine, selinol hydrochloride, 2-amino-2-ethyl-1,3-propanediol, dimethylamine and mixtures thereof.

16. The agricultural composition according to claim 7, wherein the unsubstituted or substituted polyol is selected from the group consisting of ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, dibutylene glycol, polyethylene glycol, polypropylene glycol, hexylene glycol, sorbitol, neopentyl glycol, erythritol, mannitol, xylitol, sreitol, pentaerythritol, β-cyclodextrin, ribose, 2-deoxygalactose, and mixtures thereof.

17. The agricultural composition according to claim 8, wherein the unsubstituted or substituted polyol is selected from the group consisting of ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, dibutylene glycol, polyethylene glycol, polypropylene glycol, hexylene glycol, sorbitol, neopentyl glycol, erythritol, mannitol, xylitol, sreitol, pentaerythritol, β-cyclodextrin, ribose, 2-deoxygalactose, and mixtures thereof.

18. The agricultural composition according to claim 7, wherein the silane is a hydrophilic compound selected from the group consisting of 3-aminopropylsilanetriol, N-(2-aminoethyl)-3-aminopropylsilanetriol, and mixtures thereof.

19. The agricultural composition according to claim 1, wherein the maleated natural oil is selected from the group consisting of maleated avocado oil, maleated coconut oil, maleated corn oil, maleated cottonseed oil, maleated jojoba oil, maleated linseed oil, maleated nut oil, maleated olive oil, maleated palm oil, maleated raisin oil, maleated rapeseed oil, maleated safflower oil, maleated sesame oil, maleated soybean oil, maleated pumpkin oil, maleated sunflower oil, maleated almond oil, maleated canola oil, maleated flaxseed oil, maleated grapeseed oil, maleated palm oil, maleated palm kernel oil, maleated peanut oil, maleated walnut oil, maleated chickpea oil, maleated clary sage oil, and mixtures thereof.

20. The agricultural composition according to claim 19, wherein the maleized natural oil is maleized soybean oil.

21. (A) An agricultural composition comprising a reaction product of maleated natural oil and a functionalized or non-functionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties and combinations thereof, However, the hydrophilic portion is not polyalkylene glycol, polyetheramine, alkyleneamine, or alkanolamine. Agricultural composition.

22. (A) An agricultural composition comprising a reaction product of maleated natural oil, at least one functionalized or unfunctionalized hydrophobic moiety, and at least one functionalized or unfunctionalized hydrophilic moiety.

23. The agricultural composition according to claim 1, wherein (A) is present in an amount of about 0.01% to about 20.0%.

24. The agricultural composition according to claim 4, wherein (B) is present in an amount of about 1.0% to about 90.0%; and (C) is present in an amount of about 1.0% to about 99.0%.

25. The agricultural composition according to claim 4, wherein the aforementioned agricultural active ingredient is selected from the group consisting of fertilizers and pesticides (selected from rodenticides, acaricides, algaecides, mollusk repellents, mite repellents, birdicides, insecticides, herbicides, ovicidal agents, fungicides, fungicides, antibiotics, antibacterial agents, antiviral agents, antifungal agents, antiprotozoal agents, antiparasitic agents, and antimicrobial compounds).

26. The agricultural composition according to claim 4, wherein one or more of the components are auxiliary agents or inert components.

27. The agricultural composition according to claim 4, wherein the auxiliary agent is selected from the group consisting of acidifying agents, buffering agents, foam inhibitors, defoaming agents, transpiration inhibitors, dyes and whitening agents, compatibility agents, crop oil concentrates, oily surfactants, adhesives, drift reducers, foam markers, feeding stimulants, herbicide safers, spreading agents, extenders, adhesives, suspending agents, gelling agents, synergistic agents, wetting agents, emulsifiers, dispersants, penetrating agents, tank and equipment cleaning agents, neutralizing agents, water absorbents, water softeners, and mixtures thereof.

28. The agricultural composition according to claim 4, wherein the aforementioned components may be further selected from the group consisting of solvents, liquid carriers, solid carriers or fillers, surfactants, solubilizers, penetration enhancers, protective colloids, thickeners, humectants, repellents, attractants, adapting agents, bactericidal agents, antifreeze agents, crystallization inhibitors, colorants, tackifiers, binders, preservatives, pH adjusters, clarifiers, stabilizers, ultraviolet stabilizers, and mixtures thereof.

29. The agricultural composition according to claim 1, wherein the agricultural composition is an auxiliary composition, a fertilizer composition, a nutritional composition, a plant strengthening composition, a seed coating composition, a soil improvement composition, a livestock composition, a granular composition, a sustained-release composition, a film coating composition, a pesticide composition (selected from rodenticides, insecticides, acaricides, algaecides, mollusk repellents, mite repellents, birdicides, fungicides, and herbicides), a fungicide composition, an antibiotic composition, an antimicrobial composition, an antiviral composition, an antifungal composition, an antiprotozoan composition, an antiparasitic composition, a wood preservation composition, an antimicrobial composition, or a plant yield-improving composition applied to the soil.

30. The agricultural composition according to claim 1, in the form of an aqueous or non-aqueous composition, comprising an emulsion selected from a capsule suspension (CS), an emulsifiable concentrate (EC), a seed treatment emulsion (ES), a concentrated aqueous emulsion (EW), a microemulsion (ME), a suspend emulsion (SE), a water-in-oil emulsion, a seed treatment flowable (FS), an oil dispersant (OD), a suspension concentrate (SC), a water-dispersible granule (WDG), or a wettable powder (WP).

31. The agricultural composition according to claim 1, formulated as a liquid, gel, paste, powder, granules, tablet, emulsion, or pellet.

32. The agricultural composition according to claim 1, wherein (A) is a reaction product of maleated soybean oil, octyldodecyl alcohol, and glycerol.

33. The agricultural composition according to claim 1, wherein the reaction product is selected from the group of structures represented by the following structures: 【Chemistry 1】 (wherein R is ethyl, butyl, hexyl, octyl, 2-ethylhexane-1-yl, 2-butyloctan-1-yl, 2-hexyldecane-1-yl, 2-octyldodecane-1-yl, or a mixture thereof).

34. The agricultural composition according to claim 4, which is applied topically to animals or plants and contains, in a safe and effective amount, about 0.01% to about 20.0% of (A); about 1.0% to about 90.0% of (B); and about 1.0% to about 99.0% of (C).

35. A method for treating vegetation, comprising applying the agricultural composition described in claim 1 to a plant, a plant's leaves, flowering parts, foliage, stems, fruit, adjacent areas of the plant, soil, seeds, germinating seeds, roots, liquid and solid growing media, flowers, buds, and hydroponic solutions.

36. A method for treating an animal, comprising applying the agricultural composition described in claim 1 topically to a portion of the animal's skin.

37. An agricultural composition comprising: (A) a reaction product of maleated natural oil in an amount of about 0.01% to about 20.0% of a functionalized or non-functionalized site selected from the group consisting of hydrophobic sites, hydrophilic sites and combinations thereof; (B) one or more agricultural active ingredients in an amount of about 1.0% to about 90.0%; and (C) one or more ingredients in an amount of about 1.0% to about 99.0%.

38. The agricultural composition according to claim 37, wherein (A) is a reaction product of maleated soybean oil, octyldodecyl alcohol, and glycerol.

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