WO2003026416A2

WO2003026416A2 - Methods and compositions for use in agriculture

Info

Publication number: WO2003026416A2
Application number: PCT/US2002/029793
Authority: WO
Inventors: David W. Brown; Kenneth Breindel; Ronald W. Broadbent; Michael S. Wiggins
Original assignee: Cognis Corporation
Priority date: 2001-09-21
Filing date: 2002-09-19
Publication date: 2003-04-03
Also published as: WO2003026416A3; AU2002336630A1

Abstract

Compositions comprising. A) at least one base-catalyzed reaction product of the following reactants: a) a linking compound of formula I R1(X)3 (I) wherein each X group is a halogen atom or one X group is a halogen atom and two X groups represent an epoxy oxygen atom, which is attached to two adjacent carbon atoms in the R1 group to form an epoxy group, and R1 is an alkanetriyl group containing from 3 to 10 carbon atoms; and b) at least one compound having the formula II R2X(AO)nY (II) wherein R2 is a substituted or unsubstituted, saturated or unsaturated, organic group having from 1 to 36 carbon atoms; X is -0-, -S-, or -NR3- where R3 is hydrogen or a C¿1?-C18 alkyl group; each AO group is independently an ethyleneoxy, 1,2-propyleneoxy, or 1,2-butyleneoxy group, n is a number of from 0 to 200; and Y is hydrogen, or Y can be a mercapto group or an amino group or a C1-C6 alkylamino group in place of a terminal -OH group, provided that when Y is mercapto or an amino group or a C1-C6 alkylamino group, n is at least 1; wherein the mole ratio of A)a) to A)b) is from about 0.1:1 to about 5:1; and B) at least one substance having utility in the agricultural field.

Description

TITLE OF THE INVENTION

Methods And Compositions For Use In Agriculture

FIELD OF THE INVENTION

This invention relates to compositions useful in the agricultural field and to methods for their application.

BACKGROUND OF THE INVENTION

In the preparation and use of compositions having utility in the field of agriculture, such compositions typically include surfactants to improve the wetting of the plants, bushes, and trees to which they are applied, and to enhance soil penetration. Such surfactants should be chemically stable yet biodegradable, possess low toxicity, be low foaming, have high wetting capability, and perform independently of temperature. Many surfactants do not possess all of the above attributes.

SUMMARY OF THE INVENTION

The present invention relates to compositions for use in agriculture comprising the following components:

A) at least one surfactant which is the base-catalyzed reaction product comprised of the following reactants: a) a linking compound of formula I

R¹(X)₃ (I) wherein each X group is a halogen atom or one X group is a halogen atom and two X groups represent an epoxy oxygen atom which is attached to two adjacent carbon atoms in the R¹ group to form an epoxy group, and R¹ is an alkanetriyl group containing from 3 to 10 carbon atoms; and b) at least one compound having the formula II R²X(AO)_nY (II) wherein R² is a substituted or unsubstituted, saturated or unsaturated, organic group having from 1 to 36 carbon atoms; X is -0-, -S-, or -NR³- where R³ is hydrogen or a C1-C18 alkyl group; each AO group is independently an ethyleneoxy, 1 ,2-propyleneoxy, or 1 ,2-butyleneoxy group, n is a number of from 0 to 200, preferably from 1 to 100, more preferably from 2 to 20; and Y is hydrogen, or Y can be a mercapto group or an amino group (amino or C Cβ alkylamino group) in place of a terminal -OH group, provided that when Y is mercapto or an amino group, n is at least 1 ; and

B) at least one substance having utility in the agricultural field. The mole ratio of the linking compound A)a) to A)b) is from 0.1:1 to 5:1 , preferably from 0.6:1 to 2:1, more preferably from 0.8:1 to 2:1 and most preferably from 1.0:1 to 1.5:1. This invention also relates to methods for using the above compositions.

DETAILED DESCRIPTION Other than in the operating examples, or where otherwise indicated, all numbers expressing quantities of ingredients or reaction conditions used herein are to be understood as modified in all instances by the term "about". In the above compounds of component A) a), the linking compound of formula I is preferably epichlorohydrin or another epihalohydrin. Also, trihaloalkanes can be used, such as 1 ,2,3-trichloropropane, 1 ,2,4- trichlorobutane, 1 ,3,6-trichlorohexane, and the like. Instead of chlorine in the epihalohydrins and the trihaloalkanes, the corresponding bromine and iodine compounds can also be used, including compounds containing two or even all three of the above halogens.

The compounds of formula II in component A) b) are organic (optionally alkoxylated) alcohols or the corresponding sulfhydryl or amine compounds. The R² group can be a substituted or unsubstituted, saturated or unsaturated hydrocarbon group having from 1 to 36 carbon atoms. Examples of such hydrocarbon groups include linear or branched alkyl groups having from 1 to 36 carbon atoms, preferably from 4 to 22 carbon atoms, linear or branched alkenyl or alkynyl groups having from 2 to 36 carbon atoms, preferably from 4 to 22 carbon atoms, and arenyl groups having from 7 to 36 carbon atoms. Arenyl groups are alkyl-substituted aromatic radicals having a free valance at an alkyl carbon atom such as a benzylic group.

The R² group can also be a saturated carbocyclic group, an unsaturated carbocyclic group having one or more multiple bonds, a saturated heterocyclic group, or an unsaturated heterocyclic group having one or more multiple bonds. Any of the above R² groups can be environmentally-compatible substituted groups, i.e. the groups can contain single or multiple substitutions such as a sulfur functionality, e.g. a mercaptan or thio group; or a nitrogen functionality such as an amine or amide functionality; or any combination thereof. The R² group in formula II is preferably a branched chain alkyl group containing from 4 to 36 carbon atoms, preferably from 4 to 12 carbon atoms, and more preferably from 8 to 10 carbon atoms.

When the X group of formula II is an -S- group, the R² group will preferably have from about 4 to about 22 carbon atoms, examples of which include but are not limited to, dodecyl mercapto and 1-hexadecanethio.

When the R²X-group of formula II is a secondary or tertiary amino group, the group preferably contains from 4 to 22 carbon atoms, and n is preferably a number of from 1 to 50. Examples of primary and secondary amines useful for obtaining the R²X-group include, but are not limited to, dibutyl amine, cyclohexyl amine, isodecyl amine, and dioctylamine.

Optionally an additional component C) can be reacted with the linking agent of formula I and the compound of formula II. A glycidyl ether or amine can be added to the reaction of formula I and formula II. The amount of the glycidyl ether or glycidyl amine is from about 1 to about 20 mole percent based on the moles of the compounds of formula II used in the reaction. When the glycidyl ether or glycidyl amine is added, the ratio of component A)a) plus the glycidyl ether or glycidyl amine to component A)b) is preferably from about 1.2:1 to about 5:1. Examples of glycidyl ether include, but are not limited to, PEG 600 diglycidyl ether, TETRONIC™ 701 tetraglycidyl ether, triglycidyl di- or triethanolamine, polyoxyethylene (POE) 200 tallow amine diglycidyl ether, propoxylated (POP10) trimethylol propane triglycidyl ether, propoxylated (POP7) pentaerythritol tetraglycidyl ether. Examples of glycidyl amines include, but are not limited to, tetraglycidyl 1,6-hexane diamine, tetraglycidyl JEFFAMINE™ EDR-148, and tetraglycidyl isophorone diamine. When Y in formula II is an amine or sulfhydryl group, the resulting compounds can be readily prepared from the corresponding alcohols wherein the terminal hydroxy group is replaced by an -SH group or by an amine nitrogen. For example, a compound of formula II where Y is -OH can be subjected to a catalyzed ammoniation (with ammonia, or a lower alkylamine) for replacement of the hydroxyl, or to a capping of the hydroxyl with epichlorohydrin followed by ammoniation (with ammonia, or a lower alkylamine) of the resulting glycidyl group.

In the compounds of formula II, the AO groups when present are preferably all ethyleneoxy groups. However, as stated above, each OA group can be independently an ethyleneoxy (EO), 1 ,2-propyleneoxy (PO), or 1 ,2- butyleneoxy (BO) group, i.e. any one or more of such groups can be present, and they can be present in any order, as well as be present in blocks, e.g. compounds of formula III: R²0(EO)_m(PO)_p(BO)_qH (III) wherein R² has the meaning given above, m is a number of from 0 to 100, preferably from 1 to 50, p is a number of from 0 to 50, e.g. from 1 to 50, and q is a number of from 0 to 50, e.g. from 1 to 50. Compounds of formula III in which R² is a branched chain alkyl group having from 4 to 12 carbon atoms, m is a number of from 2 to 20, and p and q are 0 are preferred.

The degree of hydrophilic and hydrophobic properties of the reaction products of components A)a) and A)b) can be readily controlled by controlling the type and number of alkyleneoxy groups in component A)b). For example, the greater the number of ethyleneoxy groups present, the greater the water solubility, while the presence of 1 ,2-propyleneoxy groups and/or 1 ,2-butyleneoxy groups for example, will decrease water solubility.

In general, the compounds of formula III wherein the sum of m, p, and q is at least 1 , and especially at least 2 are preferred for use herein. The above reaction products can be prepared by the process disclosed in

U.S. 5,827,453, the disclosure of which is expressly incorporated herein by reference.

In general, the components A)a) and A)b) (and C) if present) reactants are reacted together, preferably in the presence of an inert organic solvent such as toluene that will azeotrope water, and in the presence of a base, such as an aqueous sodium hydroxide, at a temperature of from 60° to 125°C. Preferably component A)b) is first mixed with the base and the organic solvent, and water is removed by azeotropic distillation. Then component A)a) (and C) if present) is slowly added and the reaction continued until the reaction is completed. The reaction mixture is filtered and vacuum stripped to remove the organic solvent. The component B) substances, i.e. those having utility in the field of agriculture, e.g. for applying to crop producing and non-crop producing plants, bushes, and trees and/or to soil, include one or more of fertilizers; natural enzymes; growth hormones such as the gibberellins (gibberellic acid and gibberellin plant growth hormones); control agents including pesticides such as acaracides and molluskicides, insecticides, fungicides, and nematocides; beneficial microorganisms; and other substances useful in agriculture.

Fertilizers include inorganic and/or organic fertilizers which are free or substantially free from toxic chemicals and toxic metals. The term "substantially free" used above means that the level of toxic chemicals and/or toxic metals in the organic fertilizer is so low that they are not detrimental to the soil or to plants growing in the soil to which the organic fertilizer is applied.

Fertilizers include conventional balanced inorganic fertilizer e.g. having an N:P:K ratio of 6:10:4; 7:5:5; 9:13:7; 18:6:12; 19:8:10; 20:3:3; 25:4:4; 28:4:4; 32:10:10, and the like. These numbers show the percentage of total nitrogen, available phosphorus pentoxide (P₂O5), and soluble potash (K₂0). This invention is of course not limited by the ratio of nitrogen to phosphorus to potassium in the inorganic fertilizer. The particular inorganic fertilizer selected will depend on the requirements of the soil to be fertilized. Nitrogen can be present in the inorganic fertilizer in any convenient form, such anhydrous ammonia, aqueous ammonia, ammonium salts such as ammonium nitrate, calcium ammonium nitrate, ammonium phosphate, ammonium sulfate, and ammonium sulfate nitrate, sodium nitrate, potassium nitrate, urea, urea-formaldehyde reaction product, and the like. Phosphorus can be present in any convenient water soluble form, such as

CaHP0 , Ca(H₂P0₄)2, single superphosphate (made by reacting ground phosphate rock with 70% sulfuric acid), ammonium phosphate, nitrophosphates, monorthophosphates such as liquid ammonium phosphate, and the like.

Potassium can be present as commercial potash, potassium chloride, camallite (KCI.MgCI₂.6H₂0), potassium sulfate, potassium nitrate, and the like. Dry blended urea, diammonium phosphate, and potash is a common balanced inorganic fertilizer. While urea and possibly other nitrogen sources may be considered to be organic compounds, fertilizers containing them are predominately inorganic and are commonly referred to as inorganic fertilizers. In addition to the primary nutrients, i.e. nitrogen, phosphorus and potassium, secondary nutrients can be present as needed, such as calcium, magnesium, and sulfur. Also, micronutrient elements can also be added if desired such as boron, manganese, zinc, copper, iron, and molybdenum. While balanced inorganic fertilizers are most commonly used, inorganic fertilizers deficient in one or more of nitrogen, phosphorous and potassium can be used in the practice of the invention, as soil conditions may dictate, e.g. having an N:P:K ratio of 6:2:0; 0:10:0 (bone meal); 16:20:0 (ammonium phosphate); and the like. Organic fertilizers that are free or substantially free from toxic chemicals and/or metals that can be used as component A), either alone or in combination with an inorganic fertilizer, include processed animal body and vegetable products such as blood meal, cottonseed meal, ocean kelp meal, fish fertilizers such as fish emulsion, feathermeal, and the like. Compounds useful as control agents may have one activity only, but frequently are effective in more than one category. Examples of control agents that can be used in the compositions of the invention include inorganic compounds such as elementary sulfur and inorganic sulfur compounds, e.g. calcium polysulfide and sodium thiosulfate, which are effective fungicides, copper, zinc, and other metal inorganics such as copper carbonate, copper oxychloride, copper sulfate, and copper zinc sulfate. Organometallic compounds such as iron and tin compounds, e.g. triphenyl tin hydroxide exhibit both insecticidal and pesticidal activity. Saturated higher alkyl alcohols, either straight or branched chain, such as nonyl and decyl alcohol, can be present as insecticides. Aldehydes such as metaldehyde is an effective molluskicide, e.g. useful against snails. Carbonic acid derivatives, especially their mixed esters, are potent acaracides and fungicides, and when sulfur is also present, e.g. mixed esters of thio- and di-thiocarbonic acids, activity is further increased. 6- methylquinoxaline-2,3-dithiocyclocarbonate is an effective acaricide, fungicide, and insecticide. Carbamic acid derivatives such as aryl esters of N- methylcarbamic acid, e.g. 1-naphthyl-N-methylcarbamate can also be used. Halogen substituted aliphatic monobasic and dibasic carboxylic acids are effective pesticides. Salicylanilide is effective against leaf mold and tomato brown spot. Heterocyclic compounds possessing insecticidal and/or fungicidal activity can also be used. Halogen derivatives of benzene, such as paradichlorobenzene, are effective pesticides, often used against the sugarbeet weevil. Chitin-containing products are effective nematocides. Other compounds that can be used include aliphatic mercaptans having four or fewer carbon atoms, organic sulfides and thioacetals, nitro compounds such as chloropicrin, dichloronitroethane, and chloronitropropane, copper and zinc inorganic and organic compounds, e.g. copper linoleate, copper naphthenate, etc., organophosphorous compounds of which there are well over a hundred, e.g. DDVP, tris-(2,4-dichlorophenoxyethyl) phosphite, derivatives of mono- and dithiophosphoric acids, such as 0,0-diethyl S [2-ethylthio)-ethyl] phosphorodithioate, phosphoric acid derivatives, pyrophosphoric acid derivatives and phosphonic acid derivatives, quinones, sulfonic acid derivatives, thiocyanates and isocyanates, phytoalexins, insect killing soaps such as potassium fatty acid salts, and antiallatotropins such as 7-methoxy-2,2- dimethylchromene and the 6,7-dimethoxy analog. Diatomaceous earth can also be used, which kills crawling insects. Beneficial microorganisms provide enhancement of plant growth, and where applicable, crop production, and/or provide control of pathogens in the soil. Optionally, nutrients can be included, which are selected to maintain viability of the microorganisms and/or increase their population. Such nutrients are well known to those skilled in microbiology.

Microorganisms useful in the practice of the invention can be selected from one or more of bacteria, fungi, and viruses that have utility in soil enhancement.

Beneficial microorganisms include those from genera Bacillus. Clostridium. such as Clostridium pasteurianum. Rhodopseudomonas. such as Rhodopseudomonas capsula. and Rhizobium that fix atmospheric nitrogen; phosphorus stabilizing Bacillus organisms such as Bacillus meαaterium: cytokinin producing microorganisms such as Azotobacter vinelandii; and microorganisms from the genera Pseudomonas. such as Pseudomonas flourescens. Athrobacter. such as Anthrobacter globii. Flavobacterium such as Flavobacterium sp.. Saccharomvces. such as Saccharomvces cerevisiae. and the like.

Viruses such as the NPV virus (nuclear polyhedrosis virus) such as the cabbage looper nuclear polyhedrosis virus are examples of useful viruses. Microorganisms, (bacteria, fungi and viruses) that control various types of pathogens in the soil include microorganisms that control soil-born fungal pathogens, such as Trichoderma sp.. Bacillus subtilis. Penicillium sp.; microorganisms that control insects such as Bacillus SP.. e.g. Bacillus popalliae: microorganisms that act as herbicides, e.g. Alternaria sp., and the like. All of the above microorganisms are well known and are readily available from public depositories including ATCC and NRRL.

When the microorganisms are sensitive to light and/or air, the microorganisms can be separately encapsulated in water soluble coatings, e.g., dyed or undyed gelatin spheres or capsules, or by microencapsulation to a free flowing powder using one or more gelatin, polyvinyl alcohol, ethylcellulose, cellulose acetate phthalate, or styrene maleic anhydride. Encapsulation preferably includes nutrients as well as the microorganisms.

In addition to components A) and B), the compositions of the invention can also include optional ingredients, such as water, agriculturally-compatible organic solvents, other surfactants in addition to component A), alkalizing agents such as ground limestone and acidifying agents such as inorganic acids or acid salts can be added as needed or desired, and the like.

While the component A) surfactant can be used alone, since these surfactants have low toxicity, provide excellent wetting on plants, bushes, trees, and soil, are low foaming or nonfoaming, are chemically quite stable yet readily biodegradable, are usually clear liquids, and markedly enhance dispersion stability, they are readily soluble in other surfactants and can be used in combination with one or more other surfactants if desired, where they also act as defoaming agents for higher foaming surfactants.

One or more of the following surfactants can optionally be present in the compositions of the invention, provided they are biodegradable and are otherwise acceptable for use in agriculture: anionic, cationic, nonionic, polar nonionic, amphoteric, and zwitterionic surfactants. Such surfactants include surface active or detergent compounds which contain an organic hydrophobic group containing generally 8 to 26 carbon atoms and preferably 10 to 18 carbon atoms in their molecular structure, and at least one water-solubilizing group selected from the group of sulfonate, sulfate, carboxylate, phosphonate, and phosphate.

Examples of suitable anionic detergents which fall within the scope of the anionic detergent class include the water-soluble salts, e.g., the sodium, ammonium, and alkanol ammonium salts, of higher fatty acids or resin salts containing about 8 to 20 carbon atoms, preferably 10 to 18 carbon atoms. Suitable fatty acids can be obtained from oils and waxes of animal or vegetable origin, e.g., tallow, grease, coconut oil, tall oil, and mixtures thereof. Particularly useful are the sodium and potassium salts of the fatty acid mixtures derived from coconut oil and tallow, e.g., sodium coconut soap and potassium tallow soap. The anionic class of detergents also includes the water-soluble sulfated and sulfonated synthetic detergents having an alkyl radical of 8 to 26, and preferably 12 to 22 carbon atoms, in their molecular structure.

The suitable anionic detergents also include Cβ-Ciβacyl sarcosinates (e.g. sodium lauroyl sarcosinate), sodium and potassium salts of the reaction product of higher fatty acids containing 8-18 carbon atoms in the molecule esterified with isethionic acid, and sodium and potassium salts of the Cβ-Ciβ acyl N-methyl taurides, e.g., sodium cocoyl methyl taurate and potassium steroyl methyl taurate.

Anionic phosphate surfactants in which the anionic solubilizing group is an oxyacid of phosphorous are also useful in the present compositions. Suitable phosphate surfactants are the sodium, potassium and ammonium alkyl phosphate esters. The compounds formed by including about one to 40 moles of ethylene oxide in the foregoing esters are also satisfactory.

The nonionic synthetic organic detergents are generally the condensation product of an organic aliphatic or alkyl aromatic hydrophobic compound and hydrophilic ethylene oxide groups. Practically any hydrophobic compound having a carboxy, hydroxy, amido, or amino group with a free hydrogen attached to the nitrogen can be condensed with ethylene oxide or with the polyhydration product thereof, polyethylene glycol, to form a nonionic detergent. Further, the length of the polyethyleneoxy chain can be adjusted to achieve the desired balance between the hydrophobic and hydrophilic elements.

The nonionic detergents include the polyethylene oxide condensate of one mole of alkyl phenol containing from about 6 to 12 carbon atoms in a straight-or-branched-chain configuration with about 5 to 30 moles of ethylene oxide, e.g., nonyl phenol condensed with 9 moles of ethylene oxide, dodecyl phenol condensed with 15 moles of ethylene oxide and dinonyl phenol condensed with 15 moles of ethylene oxide. Condensation products of the corresponding alkyl thiophenols with 5 to 30 moles of ethylene oxide are also suitable.

Still other suitable nonionics are the polyoxyethylene polyoxypropylene adducts of 1-butanol. The hydrophobe of these nonionics has a minimum molecular weight of 1 ,000 and consists of an aliphatic monohydric alcohol containing from 1 to 8 carbon atoms to which is attached a chain of oxyethylene and oxypropylene. The weight ratio of oxypropylene to oxyethylene covers the range of 95:5 to 85:15. Attached to this is the hydrophilic polyoxyethylene chain which is from 44.4 to 54.6 percent of the total molecular weight of 1 ,400 to 4,000. Also included in the nonionic detergent class are condensation products of a higher alcohol containing about 8 to 18 carbon atoms in a straight or branched-chain configuration condensed with about 5 to 30 moles of ethylene oxide, e.g., lauryl-myristyl alcohol condensed with about 16 moles of ethylene oxide.

Other suitable nonionics may be derived by the condensation of ethylene oxide with the product resulting from the reaction of propylene oxide and ethylene diamine. The molecular weight varies from 500 to 4,500 or more. Other nonionics are the alkyl saccharide-type surface active agents represented by formula (1 ):

RrO-(R₂0)_m-(G)_n wherein Ri represents a linear or branched alkyl group of a Cβ-iβ carbon atom content, a linear or branched alkenyl group of a Cβ-iβ carbon atom content, or an alkylphenyl group of a Cβ-iβ carbon atom content, with the alkyl group being either linear or branched, R₂ represents an alkylene group of a C2-4 carbon atom content, G represents a reduced sugar of a C₅-₆ carbon atom content, m denotes a value of 0 to 10 and n denotes a value of 1 to 10.

Cationic surface active agents may also be employed. Such agents are those surface active detergent compounds which contain an organic hydrophobic group and a cationic solubilizing group. Typical cationic solubilizing groups are amine and quaternary groups.

Examples of suitable synthetic cationic detergents are normal primary amines RNH₂ wherein R is C1₂-C15; the diamines such as those of the type RNHC2H₄NH₂ wherein R is an alkyl group of about 12 to 22 carbon atoms, such as N-2-aminoethyl stearyl amine and N-2-aminoethyl myristyl amine; amide- linked amides such as those of the type R1CONHC₂H₄NH₂ wherein R1 is an alkyl group of about 8 to 20 carbon atoms, such as N-2-amino ethylstearyl amide and N-amino ethylmyristyl amide; quaternary ammonium compounds wherein typically one of the groups linked to the nitrogen atom is an alkyl group of about 8-22 carbon atoms and three of the groups linked to the nitrogen atom are alkyl groups which contain 1 to 3 carbon atoms, including alkyl groups bearing inert substituents, such as phenyl groups, and there is present an anion such as halogen, acetate, methosulfate, etc. The alkyl group may contain intermediate linkages such as amido which do not substantially affect the hydrophobic character of the group, e.g., stearyl amido propyl quaternary ammonium chloride. Typical quaternary ammonium detergents are ethyldimethyl-stearyl ammonium chloride, benzyl-dimethylstearyl ammonium chloride, trimethyl-stearyl ammonium chloride, trimethyl-cetyl ammonium bromide, dimethyl-ethyl-lauryl ammonium chloride, dimethyl-propyl-myristyl ammonium chloride, and the corresponding methosulfates and acetates.

The amphoteric detergents which can be used in the compositions of this invention are generally water-soluble salts of derivatives of aliphatic amines which contain at least one cationic group, e.g. non-quaternary nitrogen, quaternary ammonium or quaternary phosphonium group, at least one alkyl group of 8-18 carbon atoms and may be straight chain or branched and the specific cationic atom may be part of a heterocyclic ring.

Zwitterionic surfactants include the betaines and sulfobetaines. The polar nonionic detergents are those in which the hydrophilic group contains a semi-polar bond directly between two atoms, for example, N-O, P-O, and S-O. There is charge separation between the two directly bonded atoms, but the detergent molecule bears no net charge and does not dissociate into ions.

Polar nonionic detergents include open-chain aliphatic amine oxides of the general formula R₁R₂R₃N-O, wherein Ri is an alkyl, alkenyl, or monohydroxyalkyl radical having about 10 to 16 carbon atoms. R2 and R₃ are each selected from the group consisting of hydrogen, methyl, ethyl, propyl, ethanol, and propanol radicals.

Other operable polar nonionic detergents are the open-chain aliphatic phosphine oxides having the general formula R1R₂R₃P-O wherein Ri is an alkyl, alkenyl, or monohydroxyalkyl radical ranging in chain length from 10 to 18 carbon atoms, and R₂ and R₃ are each alkyl and monohydroxyalkyl radicals containing from 1 to 3 carbon atoms.

The compositions of the invention can be in the form of solids, e.g. powders or granules, aqueous solutions or dispersions, or even as nonaqueous solutions or dispersions with agriculturally acceptable organic solvents. The granules are typically from 20 to 200 mesh.

The compositions of the invention can be applied to plants and/or soil by known techniques, such as spreading, spraying, hand casting, and the like.

The present compositions contain a surfactant-effective quantity of component A), e.g. from 0.1 to 20% by weight of the nonsolvent components of the composition, preferably from 1 to 10% by weight, and an agriculturally effective quantity of component B), which will of course depend on the nature and potency of the substances comprising component B).

When component B) comprises one or more microorganisms, such microorganisms will generally be present in from 1 x 10⁵ to 1 ,000 million microorganisms per gram of the nonsolvent components of the composition, and more preferably from 1 million to 100 million microorganisms per gram of the nonsolvent components, with or without added nutrients for the microorganisms.

The optional components can comprise from 0.001 to 10% or more by weight of the nonsolvent component of the composition.

The invention will be illustrated but not limited to the following examples.

EXAMPLES Example 1 A liquid fertilizer composition is formulated containing KNO3, Ca(H₂Pθ4)2, and KCI in a ratio of N:P:K of 18:6:12 in water in a concentration of 10% solids. To this aqueous solution is added 1% by weight of the base-catalyzed reaction product of epichlorohydrin and isodecyl alcohol ^• 4EO, prepared according to the process described in Example 1 of U.S. 5,827,453. Example 2

An aqueous composition is prepared containing 1% by weight of sodium thiosulfate and 5% by weight of the reaction product of epichlorohydrin and isodecyl alcohol ^• 4EO, prepared according to the process of Example 3 of U.S. 5,827,453. Example 3

An aqueous composition is prepared containing 2.5% by weight of the base-catalyzed reaction product of epichlorohydrin and isodecyl alcohol ^• 4EO and from 1 million to 500 million clostridium pasteurianum. per gram of the composition and 1 million - 500 million Rhodopseudomonas capsula per gram of the composition. Example 4

A powdered fertilizer composition containing ammonium sulfate, triple superphosphate, and carnallite in a ratio of 32:10:10 with a particle size of 50 mesh is intimately mixed with 1 million - 100 million Bacillus meαaterium in the form of gelatin microcapsules of about 1000 micron diameter, per gram of the composition, and 1.5% by weight of the base-catalyzed reaction product of epichlorohydrin and isodecyl alcohol ^• 4EO.

Claims

What is claimed is:

1. A composition for use in agriculture comprising:

A) at least one base-catalyzed reaction product of the following reactants: a) a linking compound of formula I

R¹(X)₃ (I) wherein each X group is a halogen atom or one X group is a halogen atom and two X groups represent an epoxy oxygen atom, which is attached to two adjacent carbon atoms in the R¹ group to form an epoxy group, and R¹ is an alkanetriyl group containing from 3 to 10 carbon atoms; and b) at least one compound having the formula II R²X(AO)_nY (II) wherein R² is a substituted or unsubstituted, saturated or unsaturated, organic group having from 1 to 36 carbon atoms; X is -0-, -S-, or -NR³- where R³ is hydrogen or a C1-C18 alkyl group; each AO group is independently an ethyleneoxy, 1 ,2-propyleneoxy, or 1 ,2-butyleneoxy group, n is a number of from 0 to 200; and Y is hydrogen, or Y can be a mercapto group or an amino group or a C Cβ alkylamino group in place of a terminal -OH group, provided that when Y is mercapto or an amino group or a Cι-Cβ alkylamino group, n is at least 1 ; wherein the mole ratio of A)a) to A)b) is from about 0.1:1 to about 5:1 ; and B) at least one substance having utility in the agricultural field.

2. The composition of claim 1 wherein said mole ratio is from about 0.6:1 to about 2:1.

3. The composition of claim 1 wherein component A)b) has the formula

R²0(EO)_m(PO)_p(BO)_qH (III) wherein R² and X have the meanings given in claim 1 , m is a number of from 0 to 100, preferably from 1 to 50, p is a number of from 0 to 50, e.g. from 1 to 50, and q is a number of from 0 to 50, e.g. from 1 to 50.

4. The composition of claim 1 wherein the component A)a) is an epihalohydrin.

5. The composition of claim 3 wherein component A)a) is epichlorohydrin.

6. The composition of claim 3 wherein the sum of m, p, and q is at least 2.

7. The composition of claim 3 wherein m is a number of from about 1 to about 50.

8. The composition of claim 3 wherein R² is an alkyl group having from 4 to 12 carbon atoms.

9. The composition of claim 8 wherein the alkyl group contains from 8 to 10 carbon atoms.

10. The composition of claim 3 wherein m is a number from 2 to about 50 and p and q = 0.

11.The composition of claim 3 wherein R² is an alkyl group having from 4 to

12 carbon atoms, m is a number from 2 to about 50, and p and q = 0.

12. The composition of claim 11 wherein R² is an alkyl group having from 8 to 10 carbon atoms and m is a number from 4 to about 50.

13. The composition of claim 3 wherein component A)b) is isodecyl alcohol ^• 4EO.

14. The composition of claim 1 wherein component B) is one or more of a fertilizer, a natural enzyme, a growth hormone, a control agent, and a beneficial microorganism.

15. The composition of claim 3 wherein component B) is one or more of a fertilizer, a natural enzyme, a growth hormone, a control agent, and a beneficial microorganism.

16. In a composition having utility in the field of agriculture, the improvement wherein the composition contains a surfactant-effective quantity of at least one base-catalyzed reaction product of the following reactants: I) a linking compound of formula I

R¹(X)₃ (I) wherein each X group is a halogen atom or one X group is a halogen atom and two X groups represent an epoxy oxygen atom, which is attached to two adjacent carbon atoms in the R¹ group to form an epoxy group, and R¹ is an alkanetriyl group containing from 3 to 10 carbon atoms; and II) a compound of formula II

R²X(AO)_nY (II) wherein R² is a substituted or unsubstituted, saturated or unsaturated, organic group having from 1 to 36 carbon atoms;

X is -0-, -S-, or -NR³- where R³ is hydrogen or a C1-C₁8 alkyl group; each AO group is independently an ethyleneoxy, 1 ,2- propyleneoxy, or 1 ,2-butyleneoxy group, n is a number of from 0 to 200; and Y is hydrogen, or Y can be a mercapto group or an amino group or a Ci-Cβ alkylamino group in place of a terminal -OH group, provided that when Y is mercapto or an amino group, n is at least 1; wherein the mole ratio of A)a) to A)b) is from about 0.1:1 to about 5:1.

17. The composition of claim 16 wherein said mole ratio is from about 0.6:1 to about 2:1.

18. The composition of claim 16 wherein component II) has the formula

R²0(EO)_m(PO)_p(BO)_qH (III) wherein R² and X have the meanings given in claim 1 , m is a number of from 0 to 100, p is a number of from 0 to 50, and q is a number of from 0 to 50.

19. The composition of claim 16 wherein component I) is an epihalohydrin.

20. The composition of claim 18 wherein component I) is epichlorohydrin.

21.The composition of claim 20 wherein R² is an alkyl group having from 8 to 10 carbon atoms, m is a number of from about 4 to about 50, and p and q = 0.

22. The composition of claim 18 wherein component II) is isodecyl alcohol ^• 4EO and component I) is epichlorohydrin.