NZ749313B2 - Aqueous compositions for treating seeds, seeds treated therewith, and methods for treating seeds - Google Patents

Abstract

Disclosed are seed treatment compositions that include: (A) an aqueous polyurethane dispersion; and (B) an insecticide, a fungicide, a nematicide, and/or other pesticides. Also disclosed are seeds treated with such a treatment compositions and methods for treating a seed using such treatment composition.

Description

A UEOUS COMPOSITIONS FOR TREATING SEEDS SEEDS D THEREWITHz AND METHODS FOR TREATING SEEDS FIELD The t invention relates to aqueous compositions for treating seeds that include a polyurethane dispersion, seeds treated therewith, and methods of ng seeds with such compositions.

BACKGROUND INFORMATION Vacuum planters are often used to plant any of a y of seeds, including seeds with odd shapes, such as corn seeds, pumpkin seeds, soybean seeds, among others. These planters have vertical plates with holes that are smaller than the seeds being planted. The planter draws a vacuum on the side of the plate opposite the container in which the seeds are stored. When the plate rotates through the e container, atmospheric pressure holds seeds against the holes and allows the rotating plate to pick up seeds. As the plate rotates around past the seed tube, the vacuum is broken, allowing the seeds to drop down a seed tube.

A challenge associated with the use of vacuum planters to maximize seed singulation. Seed singulation refers to the ability of a planter to take one seed at a time off the al plate and drop it down the seed tube.

Maximizing seed singulation is important. Skipped seed drops can create a loss within the planting row. Doubles increase population and cause the plants to struggle for nutrients and sunlight. Historically, small ences in seed type can affect singulation percentage.

In some cases, a polymer binder is included with the active ients in the treatment of seeds to bind the active ingredient to the seed.

Seeds d in such a manner can have increased percent singulation during planting, particularly vacuum planting, relative to when a polymer binder is not used. Historically, this polymer binder has been a polyolefin, such as a carboxylated styrene/butadiene dispersion. Nevertheless, a certain amount of doubles and skips are still generated during the vacuum planting process even when seeds are treated in such a manner. Any significant se in percent singulation would be desirable in order to improve productivity and crop yield.

As a result, it would be ble to provide seed treatments that significantly improve the percent ation during planting, such as vacuum planting. The present invention was made in view of the foregoing desire.

SUMMARY In some respects, the present ion is directed to seed treatment compositions that comprise: (A) an aqueous polyurethane dispersion; and (B) an insecticide, a fungicide, a nematicide, and/or other pesticides. In these compositions, the aqueous polyurethane dispersion forms a film exhibiting: (a) a Tg of -48°C to -4°C, (b) a percent elongation of 44 to 300, and (c) a tensile strength of 2500 lb/in2 (17.2 megapascals (MPa)) to 4100 lb/in2 (28.3 MPa). In particular the t invention is directed to: (1) An aqueous seed treatment composition comprising: (A) an aqueous polyurethane dispersion mixture; and (B) one or more insecticides, fungicides, cides, and/or other ides, wherein the aqueous polyurethane dispersion forms a film exhibiting: (a) a Tg of -48°C to -4°C, (b) a percent tion of 44 to 300, (c) a tensile strength of 2500 lb/in2 (17.2 MPa) to 4100 lb/in2 (28.3 MPa), and (d) optionally a microhardness of up to 45.4 N/mm2, n the seed is selected from the group consisting of corn seed, sorghum seed, oat seed, rye seed, barley seed, soybean seed, vegetable seed, wheat seed, sugarbeat seed, rice, wer seed, e seed, and spinach seed, wherein the aqueous polyurethane dispersion mixture comprises at least two aqueous polyurethane dispersions; wherein the at least two polyurethanes are the reaction products of reactants comprising: (i) a polyisocyanate; (followed by 2A) (ii) a polyester polyol having a number average lar weight of 400 to 8,000 g/mol; (iii) a compound comprising at least one isocyanate-reactive group and an anionic group or potentially anionic group; (iv) a mono functional polyalkylene ether; (v) a polyol having a molecular weight of less than <400 g/mol; and (vi) a polyamine or amino alcohol having a molecular weight of from 32 to 400 g/mol, and wherein the at least two aqueous polyurethane dispersions comprise (A) an anionic aliphatic polyester-polyurethane that is a reaction product of components (i), (ii), (iii), (v), and (vi); and (B) an anionic aliphatic polyester-polyurethane, different from (A), that is a reaction product of ents (i), (ii), (iii), (v), and (vi); and further comprise (C) an anionic/non-ionic polyester ethane that is different from (A) and (B) and is a reaction product of ents (i), (ii), (iii), (iv), and (vi), wherein the weight ratio of (A), (B) and (C) in the composition is such that (A+B)/(C) is greater than 1. (2) The composition of (1), wherein: (a) the Tg is -48°C to -30°C, (b) the percent elongation is 100 to 300, and/or (d) the microhardness is 0.4 to 15 N/mm2. (3) The composition of (1), wherein the polyester polyol comprises a polyester diol comprising a reaction product of butanediol, neopentyl , and/or hexanediol, with adipic acid. (4) The composition of (1), wherein the aqueous polyurethane dispersion mixture is present in the treatment composition in an amount such that the total amount of ethane that is present in the treatment composition is 1% to 20% by . (5) The composition of any one of (1) to (4), wherein the one or more insecticides, fungicides, cides and/or other pesticides comprises acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, and/or abamectin. (followed by 2B) (6) The composition of any one of (1) to (5), wherein the one or more insecticides, fungicides, nematicides and/or other pesticides is present in the treatment compositions in an amount of 15% by weight to 60% by weight. (7) The composition of any one of (1) to (6), further comprising a polyethylene wax.

The present invention is also directed to, among other things, seeds, such as, but not limited to, corn seeds, treated with such a ent compositions and methods for treating a seed using such treatment itions. Thus in particular the present invention provides: (8) A method of treating a seed with the composition of any one of (1) to (7), comprising applying the composition to a seed. (9) The method of (8), wherein the seed comprises corn seed, m seed, oat seed, rye seed, barley seed, soybean seed, vegetable seed, wheat seed, sugarbeat seed, rice, sunflower seed, lettuce seed, or spinach seed. (10) The method of (8), wherein the seed comprises corn seed. (11) A seed treated by the method of (8).

It is understood that the ion disclosed and described in this specification is not limited to the embodiments ized in this Summary. The reader will appreciate the foregoing s, as well as others, upon considering the following detailed description of various non-limiting and non-exhaustive embodiments ing to this specification.

DETAILED DESCRIPTION Various embodiments are bed and illustrated herein to provide an overall understanding of the structure, function, operation, manufacture, and use of the disclosed ts and processes. The various embodiments described and illustrated herein are nonlimiting and non-exhaustive. Thus, the invention is not limited by the description of the various (followed by 3) non-limiting and non-exhaustive embodiments disclosed herein. Rather, the invention is defined solely by the claims. The features and characteristics illustrated and/or described in connection with various embodiments may be combined with the features and characteristics of other embodiments. Such cations and variations are intended to be included within the scope of this ication. As such, the claims may be amended to recite any features or characteristics expressly or inherently described in, or otherwise expressly or inherently supported by, this specification. Further, Applicant reserves the right to amend the claims to affirmatively disclaim features or characteristics that may be present in the prior art. Therefore, any such amendments comply with the requirements of 35 U.S.C. § 112 and 35 U.S.C. § 132(a). The various embodiments disclosed and bed in this ication can comprise, consist of, or consist essentially of the features and characteristics as variously bed herein.

Any patent, publication, or other disclosure al identified herein is incorporated herein by reference in its entirety unless otherwise indicated, but only to the extent that the incorporated material does not con?ict with existing definitions, ents, or other disclosure material expressly set forth in this specification. As such, and to the extent necessary, the express disclosure as set forth in this specification supersedes any con?icting material incorporated by reference herein. Any material, or n thereof, that is said to be incorporated by reference into this specification, but which con?icts with existing definitions, statements, or other disclosure material set forth herein, is only orated to the extent that no t arises between that incorporated material and the existing disclosure material. Applicant reserves the right to amend this specification to expressly recite any subject matter, or portion thereof, incorporated by reference herein.

Reference herein to "certain embodimentsas " some embodiments", us non-limiting embodiments," or the like, means that a particular feature or characteristic may be included in an embodiment. Thus, use of such phrases, and similar phrases, herein does not necessarily refer to a common embodiment, and may refer to different embodiments. r, the particular features or characteristics may be combined in any suitable manner in one or more embodiments. Thus, the particular es or characteristics illustrated or described in tion with various embodiments may be combined, in whole or in part, with the features or characteristics of one or more other embodiments.

Such modifications and variations are intended to be included within the scope of the present specification. In this manner, the various embodiments described in this specification are non-limiting and non-exhaustive.

In this specification, unless otherwise indicated, all numerical parameters are to be understood as being prefaced and modified in all instances by the term "about", in which the numerical parameters possess the inherent variability characteristic of the underlying measurement techniques used to determine the cal value of the parameter. At the very least, and not as an attempt to limit the application of the doctrine of lents to the scope of the claims, each numerical parameter described herein should at least be construed in light of the number of reported significant digits and by applying ordinary rounding techniques.

Also, any numerical range recited herein includes all sub-ranges ed within the recited range. For example, a range of "l to 10" includes all nges between (and including) the recited minimum value of 1 and the recited maximum value of 10, that is, having a minimum value equal to or greater than 1 and a maximum value equal to or less than 10. Any maximum numerical limitation recited in this specification is intended to include all lower numerical tions subsumed therein and any minimum numerical limitation recited in this specification is intended to include all higher cal limitations ed therein. Accordingly, Applicant reserves the right to amend this specification, ing the claims, to expressly recite any sub-range subsumed within the ranges sly d. All such ranges are inherently described in this specification such that amending to expressly recite any such sub-ranges would comply with the requirements of 35 U.S.C. § 112 and 35 U.S.C. § 132(a).

The grammatical articles "a", "an", and "the", as used herein, are intended to include "at least one" or "one or more", unless otherwise indicated, even if "at least one" or "one or more" is expressly used in certain instances.

Thus, the es are used herein to refer to one or more than one (i.e., to "at least one") of the grammatical objects of the article. Further, the use of a singular noun includes the plural, and the use of a plural noun includes the singular, unless the context of the usage requires otherwise.

As used herein, "polymer" encompasses prepolymers, oligomers and both homopolymers and copolymers; the prefix "poly" in this context referring to two or more. As used herein, "molecular ", when used in reference to a polymer, refers to the number e molecular weight ("Mn"), unless otherwise specified. As used herein, the Mn of a polymer containing onal groups, such as a polyol, can be calculated from the functional group number, such as hydroxyl number, which is determined by end-group analysis. As used herein, the term "binder" refers to a polymer, such as carboxylated styrene/butadiene, which is dispersed in water.

As used herein, the term "aliphatic" refers to organic nds characterized by tuted or un-substituted straight, branched, and/or cyclic chain arrangements of constituent carbon atoms. Aliphatic nds do not contain aromatic rings as part of the molecular structure thereof. As used herein, the term "cycloaliphatic" refers to organic compounds characterized by arrangement of carbon atoms in closed ring structures. Cycloaliphatic nds do not contain aromatic rings as part of the molecular structure thereof.

Therefore, cycloaliphatic compounds are a subset of aliphatic compounds. ore, the term "aliphatic" asses aliphatic nds and/or cycloaliphatic compounds.

As used herein, "diisocyanate" refers to a compound containing two isocyanate groups. As used herein, "polyisocyanate" refers to a compound containing two or more isocyanate groups. Hence, diisocyanates are a subset of polyisocyanates.

As previously indicated, n embodiments of the present ion are directed to seed treatment compositions. As used herein, the term "seed ent composition" refers to a mixture of chemical components that will provide icidal, fungicidal, nematicidal and/or other pesticidal properties when applied to the surface of a seed.

As ted, the seed treatment compositions of the present invention comprise an aqueous polyurethane dispersion. As used herein, the term "aqueous polyurethane dispersion" means a sion of polyurethane particles in a continuous phase comprising water. As used herein, the term "polyurethane" refers to any polymer or oligomer comprising urethane (i.e., carbamate) groups, urea groups, or both. Thus, the term rethane" as used herein refers collectively to polyurethanes, polyureas, and polymers containing both urethane and urea groups, unless otherwise indicated.

The aqueous polyurethane dispersion used in the compositions of the present invention is selected so as to form a film exhibiting: (a) a Tg of —48°C to -40C, such as -480C to -300C, (b) a percent elongation of 44 to 300, such as 100 to 300, and (c) a tensile strength of 2500 1b/in2 (17.2 scals (MPa)) to 4100 lb/in2 (28.3 megapascals), and (d) optionally a microhardness of up to 45.4 Nlmmz, such as up to 15 N/mmz. ardness, Tg, percent elongation, and tensile strength of a film formed from an aqueous ethane dispersion, for purposes of the present invention, are determined according to the methods that are described in the Examples below. It will be understood that the foregoing film properties refer to the film properties of a film formed from the s polyurethane dispersion itself, which is thereafter used as a component in a seed treatment composition of the present invention, rather than the properties of a seed treatment composition itself.

It has been singly discovered that when an aqueous polyurethane dispersion (or mixture of two or more aqueous polyurethane dispersions) that forms a film exhibiting such properties is used in a seed treatment composition of the type described herein, the percent singulation may be significantly high, and, in fact, increased from when an identical treatment ition is used in which a polyolefin latex, such as a carboxylated styrene/butadiene polymer, is used as the polymeric component of the composition rather than the aqueous polyurethane dispersion or as compared to an identical treatment composition in which no polymeric component is used in the composition, each of which being determined when ing the same type of seed. The extent of such increase in percent singulation is described in more detail below.

In certain embodiments, the aqueous polyurethane dispersion that is used in the seed treatment compositions of the present invention ses one or more ethanes that are the reaction product of reactants comprising, consisting essentially of, or, in some cases, consisting of: (i) a polyisocyanate; (ii) a polymeric polyol having a number e molecular weight ("Mn") of 400 to 8,000 g/mol; (iii) a compound sing at least one isocyanate-reactive group and an anionic group or potentially anionic group; (iv) optionally a mono functional polyalkylene ether; (v) optionally a polyol having a molecular weight of less than <400 g/mol, and (vi) optionally a polyamine or amino alcohol having a lar weight of from 32 to 400 g/mol; provided that the reactants and their respective amounts are selected so that a film formed from the polyurethane or mixture of polyurethanes exhibits: (a) a Tg of -480C to -40C, such as -480C to - °C, (b) a percent elongation of 44 to 300, such as 100 to 300, and (c) a tensile th of 2500 lb/in2 (17.2 megapascals (MPa)) to 4100 lb/in2 (28.3 megapascals), and (d) optionally a microhardness of up to 45.4 N/mmz, such as up to 15 N/mmz. le polyisocyanates (i) include aromatic, araliphatic, tic and cycloaliphatic polyisocyanates, such as, for example, 1,4-butylene diisocyanate, 1,6-hexamethylene diisocyanate (HDI), pentamethylene diisocyanate (PDI), isophorone diisocyanate (IPDI), 2,2,4- and/or 2,4,4-trimethylhexamethylene diisocyanate, the isomeric bis-(4,4'-isocyanatocyclohexyl)- methanes or mixtures thereof of any desired isomer content, 1,4-cyclohexylene diisocyanate, 1,4-phenylene diisocyanate, 2,4- and/or 2,6-toluene diisocyanate or hydrogenated 2,4- and/or 2,6-toluene diisocyanate, 1,5-naphthalene diisocyanate, 2,4‘— and/or iphenylmethane diisocyanate, 1,3— and 1,4—bis-(2-isocyanato- propyl)—benzene (TMXDI), l,3-bis(isocyanato-methyl)benzene (XDI), (S)- alkyl 2,6-diisocyanato-hexanoates or kyl 2,6-diisocyanatohexanoates.

Polyisocyanates having a functionality >2 can also be used if desired. Such polyisocyanates include modified diisocyanates having a uretdione, nurate, urethane, allophanate, biuret, iminooxadiazinedione and/or oxadiazinetrione structure, as well as unmodified polyisocyanates having more than 2 NCO groups per molecule, for example 4-isocyanatomethyl-1,8-octane diisocyanate e triisocyanate) or triphenylmethane-4,4‘,4"-triisocyanate.

In some embodiments of the present invention, polyisocyanates or polyisocyanate mixtures containing only aliphatically and/or cycloaliphatically bonded isocyanate groups are used that have a mean functionality of from 2 to 4, such as 2 to 2.6 or 2 to 2.4.

In n embodiments, ent (i) is used in an amount of at least 5% by weight, such as at least 10 or at least 20% by weight and/or no more than 60% by , such as no more than 50% or, in some cases, no more than 45% by weight, based on the total weight of reactants used to make the polyurethane.

Polymeric polyols (ii) have a molecular weight Mn of from 400 to 8000 g/mol, such as 400 to 6000 g/mol or, in some cases, 500 to 3000 g/mol, 1000 to 3000 g/mol or 1500 to 3000 g/mol. In certain embodiments, these polymeric polyols have a hydroxyl number of from 20 to 400 mg KOH/g of nce, such as 20 to 300 mg KOH/g of substance, 20 to 200 mg KOH/g of substance or 20 to 100 mg KOH/g of substance. In certain embodiments, these polymeric polyols have a hydroxyl functionality of 1.5 to 6, such as 1.8 to 3 or 1.9 to 2.1. As will be appreciated, the Mn of a r containing functional groups, such as a polyol, can, as discussed earlier, be calculated from the functional group number, such as hydroxyl number, which is determined by end-group analysis. "Hydroxyl number", as used herein, is determined according to DIN 53240.

Exemplary polymeric polyols include, for example, polyester polyols, polyacrylate polyols, polyurethane polyols, polycarbonate polyols, polyether polyols, polyester polyacrylate polyols, polyurethane rylate polyols, polyurethane ter polyols, polyurethane polyether polyols, polyurethane polycarbonate polyols, polyester polycarbonate polyols, phenol/formaldehyde resins, on their own or in mixtures.

Suitable her polyols e, for example, the polyaddition products of the styrene , of ethylene oxide, propylene oxide, ydrofuran, butylene oxide, epichlorohydrin, as well as their mixed-addition and graft products, as well as the polyether polyols obtained by condensation of polyhydric alcohols or mixtures f and those obtained by lation of polyhydric alcohols, amines and amino alcohols. le polyether polyols often have a hydroxyl functionality of 1.5 to 6.0, such as 1.8 to 3.0, a hydroxyl number of 20 to 700 mg KOH/g solid, such as 20 to 100, 20 to 50 or, in some cases 20 to 40 mg KOH/g solid, and/or a M.1 of 400 to 4000 g/mol, such as 100 to 4000 or 1000 to 3000 g/mol.

Exemplary polyester polyols are the polycondensation products of di- as well as optionally tri- and tetra-01s and di- as well as optionally tri- and tetra-carboxylic acids or hydroxycarboxylic acids or lactones. Instead of the free polycarboxylic acids it is also possible to use the corresponding polycarboxylic acid anhydrides or corresponding polycarboxylic acid esters of lower alcohols to prepare the ters. Examples of suitable diols are ethylene glycol, butylene glycol, diethylene , triethylene glycol, polyalkylene glycols such as polyethylene glycol, further 1,2-propanediol, l,3-propanediol, l,3-butanediol, 1,4- diol, l,6-hexanediol and isomers, l,8-octanediol, neopentyl glycol, 1,4- bishydroxymethylcyclohexane, 2-methyl- l ,3-propanediol, 2,2,4-trimethyl- 1,3 - pentanediol, dipropylene glycol, polypropylene glycols, lene glycol, polybutylene glycols, bisphenol A, tetrabromobisphenol A, lactone-modified diols, or hydroxypivalic acid neopentyl glycol ester. In order to achieve a functionality >2, polyols having a functionality of 3 can optionally be used proportionately, for example trimethylolpropane, glycerol, erythritol, pentaerythritol, trimethylolbenzene or trishydroxyethyl isocyanurate.

Suitable dicarboxylic acids are, for example, ic acid, isophthalic acid, terephthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, cyclohexane-dicarboxylic acid, adipic acid, azelaic acid, c acid, glutaric acid, tetrachlorophthalic acid, maleic acid, fumaric acid, itaconic acid, malonic acid, suberic acid, 2—methy1succinic acid, 3,3-diethylglutaric acid, and/or 2,2-dimethylsuccinic acid. Anhydrides of those acids can likewise be used, where they exist. Thus, for the es of the present invention, anhydrides are included in the expression "acid". Monocarboxylic acids, such as benzoic acid and hexanecarboxylic acid, can also be used, ed that the mean functionality of the polyol is 22. Saturated aliphatic or aromatic acids can be used, such as adipic acid or isophthalic acid. Trimellitic acid is a polycarboxylic acid which can also optionally be used.

Hydroxycarboxylic acids which can be used as reactants in the preparation of a ter polyol having terminal hydroxyl groups are, for example, hydroxycaproic acid, ybutyric acid, ydecanoic acid, hydroxystearic acid and the like. Suitable lactones are, for example, 8- caprolactone, butyrolactone and their homologues.

In n embodiments of the present invention, polymer polyol (ii) comprises or, in some cases, consists ially of or consists of a polyester diol that is a reaction product of butanediol and/or neopentyl glycol and/or hexanediol and/or ethylene glycol and/or diethylene glycol with adipic acid and/or phthalic acid and/or isophthalic acid, such as polyester polyols that are a reaction product of diol and/or neopentyl glycol and/or hexanediol with adipic acid and/or phthalic acid.

Suitable polyester polyols, such as the ing polyester diols, often have a hydroxyl functionality of 1.5 to 6.0, such as 1.8 to 3.0, a hydroxyl number of 20 to 700 mg KOH/gram solid, such as 20 to 100, 20 to 80 or, in some cases 40 to 80 mg KOH/g solid, and/or a Mn of 500 to 3000 g/mol, such as 600 to 2500 g/mol.

Exemplary polycarbonate polyols are obtainable by reaction of carbonic acid derivatives, for e diphenyl carbonate, yl carbonate or phosgene, with diols. Suitable diols include the diols mentioned earlier with respect to the preparation of polyester polyols. In some cases, the diol ent contains from 40 to 100 wt. % 1,6-hexanediol and/or hexanediol derivatives, often containing ether or ester groups in addition to terminal OH groups, for example products which are obtained by reaction of one mole of diol with at least one mole, preferably from one to two moles, of s-caprolactone or by etherification of hexanediol with itself to form di— or tri-hexylene glycol. Polyether polycarbonate polyols can also be used.

In certain embodiments, component (ii) is used in an amount of at least 20% by weight, such as at least 30 or at least 40% by weight and/or no more than 80% by weight, such as no more than 70% by weight, based on the total weight of reactants used to make the polyurethane.

Component (iii) is a compound comprising at least one isocyanate- reactive group and an anionic group or potentially anionic group. ary such compounds are those which contain, for example, carboxylate, sulfonate, phosphonate groups or groups which can be converted into the above-mentioned groups by salt formation (potentially anionic groups), and which can be incorporated into the macromolecules by isocyanate-reactive , such as hydroxyl or amine groups, that are present.

Suitable anionic or potentially anionic compounds (iii) are, for example, mono- and di-hydroxycarboxylic acids, mono- and di-aminocarboxylic acids, mono- and di-hydroxysulfonic acids, mono— and di—aminosulfonic acids as well as mono- and di-hydroxyphosphonic acids or mono- and nophosphonic acids and their salts, such as dimethylolpropionic acid, dimethylolbutyric acid, hydroxypivalic acid, N-(2-aminoethyl)-B-alanine, 2—(2-amino-ethylamino)- ethanesulfonic acid, ethylene-diamine-propyl- or -butyl-sulfonic acid, 1,2- or 1,3- propylenediamineethylsulfonic acid, malic acid, citric acid, glycolic acid, lactic acid. In certain embodiments, the anionic or potentially anionic compounds have carboxy or ylate and/or sulfonate groups and have a functionality of from 1.9 to 2.1, such as the salts of 2-(2—amino-ethylamino)ethanesulfonic acid.

In certain embodiments, component (iii) is used in an amount of at least 0.1% by weight, such as at least 1, or at least 3% by weight and/or no more than 10% by weight, such as no more than 7% by weight, based on the total weight of reactants used to make the polyurethane. al component (iv) is a mono functional polyalkylene ether that contains at least one, in some cases one, hydroxy or amino group. In some embodiments, component (4) comprises a compounds of the formula: H—Y'—X—Y—R in which R is a lent hydrocarbon radical having 1 to 12 carbon atoms, such as an tituted alkyl radical having 1 to 4 carbon atoms; X is a polyalkylene oxide chain having 5 to 90, such as 20 to 70 chain members, which may comprise at least 40%, such as at least 65%, ethylene oxide units and which in addition to ethylene oxide units may comprise propylene oxide, butylene oxide and/or styrene oxide units; and Y and Y' are each independently oxygen or —NR'— in which R' is H or R, in which R is defined above.

Mono onal polyalkylene ethers suitable for use in component (iv) may, in some cases, contain 7 to 55 ethylene oxide units per molecule, and can be obtained by lation of suitable starter molecules, such as, for example, saturated monoalcohols, such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, sec-butanol, the isomeric pentanols, hexanols, ls and nonanols, n-decanol, n-dodecanol, n-tetradecanol, n-hexadecanol, n- octadecanol, cyclohexanol, the ic methyl-cyclohexanols or hydroxymethylcyclohexane, 3-ethylhydroxymethyloxetan or tetrahydrofurfuryl alcohol; diethylene glycol monoalkyl ethers, such as, for example, diethylene glycol monobutyl ether; unsaturated alcohols, such as allyl alcohol, 1,1- dimethylallyl alcohol or oleic l; aromatic alcohols, such as phenol, the isomeric cresols or methoxyphenols; araliphatic alcohols, such as benzyl alcohol, anis alcohol or ic alcohol; ary monoamines, such as dimethylamine, diethylamine, dipropylamine, ropylamine, dibutylamine, bis-(2-ethylhexyl)- amine, N—methyl— and N—ethyl-cyclohexylamine or dicyclohexylamine; as well as heterocyclic secondary amines, such as morpholine, pyrrolidine, piperidine or 1H- pyrazole, including mixtures of two or more of any of the foregoing.

Alkylene oxides suitable for the alkoxylation reaction include, for example, ethylene oxide and ene oxide, which can be used in the alkoxylation reaction in any desired sequence or alternatively in ure. In some embodiments, ent (iv) comprises a copolymer of ethylene oxide with propylene oxide that contains ethylene oxide in an amount of at least 40% by , such as at least 50% by weight, at least 60% by weight or at least 65% by weight and/or up to 90% by weight or up to 80% by weight, based on the total weight of ethylene oxide and propylene oxide. In certain embodiments, the Mn of such a copolymer is 300 g/mol to 6000 g/mol, such as 500 g/mol to 4000 g/mol, such as 1000 g/mol to 3000 g/mol.

In n embodiments, component (iv) is used in an amount of at least 1% by weight, such as at least 5, or at least 10% by weight and/or no more than 30% by , such as no more than 20% by weight, based on the total weight of reactants used to make the polyurethane.

Optional component (v) comprises a polyol having a molecular weight of less than <400 grams/mole. Examples of such polyols include, without limitation, the diols mentioned r with respect to the preparation of polyester s. In some cases, the polyol having a molecular weight of less than <400 g/mol has up to 20 carbon atoms, such as is the case with, for example, ethylene glycol, diethylene glycol, ylene glycol, 1,2-propanediol, 1,3-propanediol, 1,4-butanediol, 1,3-butylene glycol, cyclohexanediol, l,4-cyclohexanedimethanol, 1,6-hexanediol, neopentyl glycol, hydroquinone dihydroxyethyl ether, bisphenol A (2,2-bis(4-hydroxyphenyl)propane), hydrogenated nol A, (2,2-bis(4— hydroxycyclohexy1)propane), trimethylolpropane, glycerol, pentaerythritol and also any desired mixtures of two or more thereof. Also suitable are ester diols of the specified molecular weight range such as (x-hydroxybutyl—s—hydroxycaproic acid ester, 0)-hydroxyhexyl-y-hydroxybutyric acid ester, B-hydroxyethyl adipate or bis(B-hydroxyethy1) terephthalate.

In certain embodiments, component (v) is used in an amount of at least 1% by weight, such as at least 2, or at least 3% by weight and/or no more than 20% by weight, such as no more than 10 or no more than 5% by weight, based on the total weight of reactants used to make the polyurethane.

Optional component (vi) is used for chain extension and es di— or poly—amines as well as hydrazides, for example ethylenediamine, 1,2- and 1,3-diaminopropane, 1,4-diaminobutane, l,6-diaminohexane, isophoronediamine, isomer mixture of 2,2,4- and 2,4,4-trimethyl—hexamethylenediamine, 2-methyl- ethylenediamine, lenetriamine, 1,3- and 1,4-xylylenediamine, d,0t,(x',(x'-tetramethyl—1,3- and -1,4-xylylenediamine and aminodicyclohexyl- methane, dimethylethylenediamine, hydrazine or adipic acid dihydrazide. Also suitable for use are compounds which contain active hydrogen of different reactivity s NCO groups, such as compounds which contain, in addition to a primary amino group, also secondary amino groups or, in addition to an amino group (primary or secondary), also OH groups. Examples thereof are primary/secondary amines, such as 3-amino—l-methyl-aminopropane, 3-amino-lethylaminopropane , 3-amino- ohexylaminopropane, o— 1- methylaminobutane, also alkanolamines such as N-aminoethylethanol-amine, ethanolamine, 3-aminopropanol or neopentanolamine.

In certain embodiments, component (vi) is used in an amount of at least 1% by weight, such as at least 3 or at least 5% by weight and/or no more than 10% by weight, such as no more than 8 or, in some cases, no more than 7% by weight, based on the total weight of reactants used to make the polyurethane.

In some embodiments, the sum of components (i)-(Vi) is 100 percent by weight, based on the total weight of the reactants used to make the polyurethane.

Any of a variety of ses can be used to prepare the aqueous polyurethane dispersions used in embodiments of the present invention, such as the prepolymer mixing method, acetone method or melt dispersing , each of which will be understood by a person skilled in the art of making aqueous polyurethane dispersions. For example, in some embodiments, one or more aqueous polyurethane dispersion included in the compositions of the present invention may be ed by the acetone method, such as is described, for e, in U.S. Patent Application Publication No. 2007/0167565 A1 at [0057]- , the cited portion of which being incorporated herein by reference.

In certain embodiments, the resin solids content of the aqueous ethane dispersions ed by any of these methods is at least 20% by weight, such as at least 25 or at least 30% by weight and/or no more than 65% by weight, such as no more than 50 or no more than 45% by weight, based on the total weight of the dispersion.

As indicated above, in the seed treatment compositions of the present invention the s ethane sion forms a film that exhibits: (a) a Tg of —480C to -4OC, such as -480C to —300C, (b) a percent tion of 44 to 300, such as 100 to 300, and (c) a tensile strength of 2500 lbg’in2 (17.2 MPa) to 4100 lb/in2 (28.3 MPa), and (d) optionally a microhardness of up to 45.4 N/mmz, such as up to 15 N/mmz. s polyurethane dispersions that are suitable for use in the treatment compositions of the present invention are commercially ble and e, for example, (A) IMPRANIL DL 2611 (Covestro LLC), which is an anionic aliphatic polyester-polyurethane dispersion and is a reaction product of components (i), (ii), (iii), (v), and (vi) described above and/or (B) BAYHYDROL UH XP 2719 (Covestro LLC) which is also an aliphatic, polyester-based, c polyurethane dispersion and is different from IMPRANIL DL 2611. In certain embodiments, such an aqueous polyurethane dispersion is used in combination with a different aqueous ethane dispersion, such as, for example, (C) BAYBOND PU 330 (Covestro LLC), which is an anionic/non-ionic polyester polyurethane dispersed in water and is a reaction product of components (i), (ii), (iii), and (iv) described above. In certain embodiments using a blend of dispersions such as those described above, the weight ratio of the aqueous polyurethane dispersions in the seed treatment compositions of the present invention is (A+B)/(C) is greater than 1:1, such as greater than 2:1.

In certain embodiments, the aqueous polyurethane dispersion is present in the treatment composition in an amount such that the total amount of polyurethane that is present in the treatment composition in some embodiments as an amount of 1% to 25%, in some ments from 2% to 20%, in some embodiments from 3% to 15%, in some embodiments from 4% to 10%, in some embodiments at least 3%, in some embodiments at least 5%, in some embodiments no more than 25%, in some embodiments no more than 20%, in some embodiments no more than 15% and in some embodiments no more than The seed treatment compositions of the t invention may r include any of a variety of coating additives such as ers, devolatilizers, thickeners, ?ow l additives, colorants (including pigments and dyes), surfactants, sants, neutralizers, biological materials (such as inoculants), nutrients, micronutrients, or e additives.

As indicated earlier, the seed treatment compositions of the present invention comprise an insecticide, a fungicide, a nematicide, and/or other pesticides. In s embodiments, the seed treatment composition comprises an insecticide. The present invention is not limited to a particular icide.

Suitable insecticides include, but are not limited to: (l) Acetylcholinesterase (AChE) inhibitors, such as, for example, carbamates, for example arb, rb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, encarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, hacarb, XMC and xylylcarb; or organophosphates, for example acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S—methyl, diazinon, dichlorvos/DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, r, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl hoxyaminothiophosphoryl) salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, ep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, triclorfon and vamidothion. (2) GABA-gated chloride channel antagonists, such as, for example, cyclodiene-organochlorines, for example chlordane and endosulfan or phenylpyrazoles (fiproles), for e ethiprole and fipronil. (3) Sodium channel modulators / voltage-gated sodium channel blockers such as, for example, pyrethroids, e.g. acrinathrin, rin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin s-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cy?uthrin, beta-cy?uthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, betacypermethrin , theta-cypermethrin, zeta-cypermethrin, cyphenothrin [(1R)-trans- isomer], deltamethrin, empenthrin [(EZ)-(1R)-isomer], esfenvalerate, etofenprox, fenpropathrin, erate, ?ucythrinate, rin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin, permethrin, hrin [(1R)—trans-isomer], prallethrin, pyrethrins (pyrethrum), resmethrin, sila?uofen, tefluthrin, tetramethrin, tetramethrin [(1R)— isomer)], tralomethrin and trans?uthrin or DDT or methoxychlor. (4) Nicotinergic acetylcholine receptor (nAChR) agonists, such as, for example, neonicotinoids, e.g. acetamiprid, clothianidin, dinotefuran, imidacloprid, yram, thiacloprid and thoxam or nicotine or sulfoxa?or. (5) eric activators of the nicotinergic acetylcholine receptor (nAChR) such as, for e, spinosyns, e.g. oram and spinosad. (6) Chloride channel activators, such as, for example, ctins/milbemycins, for example abamectin, emamectin benzoate, lepimectin and milbemectin. (7) Juvenile e imitators such as, for example, juvenile hormone analogues, e.g. hydroprene, kinoprene and methoprene or fenoxycarb or pyriproxyfen. (8) Active compounds with unknown or nonspecific mechanisms of action such as, for example, alkyl halides, e.g. methyl bromide and other alkyl halides; or chloropicrine or sulphuryl fluoride or borax or tartar emetic. (9) Selective edants, for example pymetrozine or ?onicamid. (10) Mite growth inhibitors, for example clofentezine, hexythiazox and di?ovidazin or etoxazole. (11) ial disruptors of the insect gut membrane, for example Bacillus thuringiensis subspecies israelensis, us sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies ki, Bacillus thuringiensis subspecies tenebrionis, and BT plant proteins: CrylAb, CrylAc, CrylFa, CryZAb, mCry3A, Cry3Ab, Cry3Bb, Cry34/35Ab1. (12) ive phosphorylation tors, ATP disruptors such as, for example, diafenthiuron or organotin compounds, for example azocyclotin, cyhexatin and fenbutatin oxide or gite or tetradifon; (13) Oxidative phosphorylation decouplers acting by interrupting the H proton gradient such as, for example, chlorfenapyr, DNOC and sul?uramid. (14) Nicotinergic acetylcholine receptor antagonists such as, for example, bensultap, cartap hydrochloride, thiocylam, and thiosultap-sodium. (15) Chitin thesis inhibitors, type 0, such as, for example, bistri?uron, uazuron, di?ubenzuron, flucycloxuron, ?ufenoxuron, muron, lufenuron, novaluron, noviflumuron, teflubenzuron and tri?umuron. (16) Chitin biosynthesis inhibitors, type 1, for example buprofezin. (17) Moulting inhibitors (in particular for Diptera, i.e. dipterans) such as, for e, cyromazine. (18) Ecdysone receptor agonists such as, for example, chromafenozide, nozide, methoxyfenozide and tebufenozide. (19) Octopaminergic ts such as, for example, amitraz. (20) Complex-III electron transport inhibitors such as, for example, hydramethylnone or acequinocyl or pyrim. (21) Complex-I electron transport inhibitors, for e from the group of the METI acaricides, e.g. fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad and tolfenpyrad or rotenone (Derris). (22) Voltage—gated sodium channel blockers, for example carb or meta?umizone. (23) Inhibitors of acetyl-CoA carboxylase such as, for example, tetronic and tetramic acid derivatives, e.g. spirodiclofen, spiromesifen and spirotetramat. (24) Complex-IV on transport inhibitors such as, for e, phosphines, e.g. aluminium phosphide, calcium phosphide, phosphine and zinc phosphide or cyanide. (25) Complex II electron transport inhibitors, such as, for example, yrafen and cyflumetofen. (26) Ryanodine receptor effectors, such as, for example, diamides, e.g. chlorantraniliprole, cyantraniliprole and ?ubendiamide. (27) Other active compounds such as, for e, afidopyropen, azadirachtin, benclothiaz, benzoximate, bifenazate, bromopropylate, chinomethionat, cryolite, dicofol, di?ovidazin, ?uensulfone, ?ometoquin, ?ufenerim, ?ufenoxystrobin, ?ufiprole, ?uopyram, flupyradifurone, fufenozide, hepta?uthrin, imidaclothiz, iprodione, meper?uthrin, paichongding, mide, pyri?uquinazon, pyriminostrobin, tetramethyl?uthrin and iodomethane; furthermore preparations based on Bacillus firmus (I-1582, BioNeem, ), and also the following compounds: 3-bromo-N—{2—bromo—4—Chloro—6-[(1- cyclopropylethyl)carbamoyl]pheny1}(3 -chloropyridinyl)-1H-pyrazole-5 - carboxamjde (known from W02005/077934) and uoromethyl[(2,2,2- tri?uoroethyl)sulphinyl]phenyl}(tri?uoromethyl)—1H-1,2,4-triazoleamine (known from W02006/04363 5), {1‘-[(2E)—3-(4-chlorophenyl)prop—2-enyl]—5- ?uorospiro[indol-3,4’-piperidin]-1(2H)-yl}(2-Chloropyridin—4-yl)methanone (known from W02003/106457), 2—chloro-N-[2-{1—[(2E)(4-chlorophenyl)prop- 2-enyl]piperidin—4-yl}-4—(tri?uoromethy1)phenyl]isonicotinamide (known from W02006/003494), 3-(2,5-dimethylphenyl)—4-hydroxymethoxy-1,8- piro[4.5]deC—3—enone (known from W02009/049851), 3-(2,5— ylphenyl)- 8—methoxyoxo—1,8-diazaspiro[4.5]decenyl- ethylcarbonate (known from W02009/049851), 4-(but—2-yn—1—yloxy)—6-(3,5— dimethylpiperidinyl)?uoropyrimidine (known from W02004/099160), 4- (butynyloxy)(3-Chloropheny1)pyrimidine (known from W02003/076415), PF1364 (CAS Reg. No. 12047762), 4-[5-(3,5- dichlorophenyl)—5—(tri?uoromethyl)—4,5-dihydro-1,2—oxazolyl]—2—methyl—N-{2- oxo[(2,2,2-tri?uoroethy1)amino]ethyl}benzamide (known from W02005/085216), 4- {5 - [3-chloro—5-(tri?uoromethy1)phenyl] -5 -(tri?uoromethyl)- 4,5-dihydro-1,2-oxazolyl}-N-{2—oxo[(2,2,2-tri?uoroethyl)amino]ethyl } naphthamide (known from /002809), methyl { [3-bromo(3- Chloropyridin-Z-yl)—1H-pyrazol-5 -yl]carbonyl } amino)-5 -Chloro-3 - methylbenzoyl]-2—methylhydrazinecarboxylate (known from W02005/085216), methyl 2-[2—({ [3-bromo(3-Chloropyridin—2-yl)-1H—pyrazol yl]carbonyl } amino)cyanomethylbenzoyl] ethylhydrazinecarboxylate (known from W02005/085216), methyl { [3-bromo-1—(3-chloropyridin—2- yl)—1H-pyrazolyl]carbonyl}amino)cyano-3 -methylbenzoyl] methylhydrazinecarboxylate (known from W02005/085216), methyl 2-[3,5— dibromo-2—({ [3-bromo(3-chloropyridinyl)-1H-pyrazol-5 - yl]carbony1} amino)benzoyl]ethy1hydrazinecarboxylate (known from W02005/085216), 1-(3-chloropyridinyl)-N-[4-Cyanomethyl-6— (methylcarbamoyl)phenyl]—3- { [5 -(tri?uoromethyl)-2H-tetrazolyl]methyl } - 1H- pyrazole—S-carboxamide (known from W02010/069502), N-[2—(5—amino-1,3,4- thiadiazol-Z-yl)chloro-6—methylphenyl]bromo—1-(3-chloropyridinyl)— 1H- le—S-carboxamide (known from 57925), ro-N—(2- cyanopropan-Z-yl)—N-[4-(1,1,1,2,3,3,3 -hepta?uoropropan-2—yl) methylphenyl]phthalamide (known from WO2012/034472), 8-chloro-N-[(2— methoxyphenyl)sulphony1](tri?uoromethyl)imidazo[1,2—a]pyridine carboxamide (known from W02010/129500), 4-[5—(3,5-dichlorophenyl) oromethyl)-4,5-dihydro-1,2-oxazol-3—yl]methyl-N-(1-oxidothietan-3— yl)benzamide (known from W02009/080250), N-[(2E)[(6-chloropyridin—3- yl)methy1]pyridin-2(1H)-y1idene]-2,2,2-tri?uoroacetamide (known from W02012/029672), 1-[(2-chloro-1,3-thiazolyl)methyl]oxophenyl-4H- pyrido[1,2—a]pyrimidinium—2-olate (known from WO2009/O99929), 1-[(6— chloropyridinyl)methyl]oxophenyl-4H-pyrido[1,2-a]pyrimidinium olate (known from W02009/099929), (SS,8R)[(6-chloropyn'diny1)methy1]— 9-nitro-2,3,5,6,7,8-hexahydro-1H-5,8-epoxyimidazo[1,2-a]azepine (known from W02010/069266), (2E)-1—[(6-chloropyridinyl)methyl]—N‘-nitro—2- pentylidenehydrazinecarboximidamide (known from W02010/060231), 4-(3- {2,6-dichloro [(3,3 -dichloroprop-2—en- 1 —y1)oxy]phenoxy } y)methoxy- 6-(tri?uoromethyl)pyrimidine (known from CN101337940), N-[2-(tertbutylcarbamoyl )chloro—6-methylphenyl](3 -chloropyridinyl)—3 - (fluoromethoxy)-1H-pyrazole-S-carboxamide (known from W02008/134969).

In some cases, the treatment composition comprises a fungicide.

Suitable fungicides e, but are not limited to: (1) Inhibitors of ergosterol biosynthesis such as, for example, aldimorph, azaconazole, bitertanol, bromuconazole, cyproconazole, diclobutrazole, difenoconazole, diniconazole, diniconazole-M, dodemorph, dodemorph acetate, epoxiconazole, etaconazole, fenarimol, fenbuconazole, fenhexamid, fenpropidin, fenpropimorph, ?uquinconazole, ?urprimidol, ?usilazole, fole, furconazole, furconazole-cis, hexaconazole, imazalil, imazalil sulphate, imibenconazole, ipconazole, metconazole, myclobutanil, naftifin, nuarimol, oxpoconazole, utrazole, pefurazoate, penconazole, piperalin, prochloraz, propiconazole, prothioconazole, pyributicarb, pyrifenox, quinconazole, simeconazole, spiroxamine, tebuconazole, terbinafin, tetraconazole, triadimefon, menol, orph, izole, triforine, triticonazole, azole, uniconazole—P, Viniconazole, voriconazole, 1-(4-chlorophenyl) (1H- 1 ,2,4-triazol- l—yl)cycloheptanol, methyl 1-(2,2—dimethyl-2,3-dihydro- 1H- indenyl)-1H-imidazole—S-carboxylate, N'-{5-(difluoromethyl)methyl[3- (trimethylsilyl)propoxy]phenyl } -N—ethyl-N—methylimidoformamide, N-ethyl—N- methyl-N'—{2-methyl(tri?uoromethyl)-4—[3-(trimethylsilyl)propoxy]- phenyl }imidoformamide, O—[1-(4-methoxyphenoxy)—3,3-dimethylbutany1]—1H- imidazole-l-carbothioate, and pyrisoxazole. (2) Respiration inhibitors (respiratory chain inhibitors) such as, for example, bixafen, id, carboxin, di?umetorim, fenfuram, ?uopyram, flutolanil, yroxad, tpyr, yclox, isopyrazam mixture of the syn- epimeric racemate lRS,4SR,9RS and the anti-empimeric racemate lRS,4SR,9SR, isopyrazam (anti-epimeric racemate ), isopyrazam (anti-epimeric enantiomer 1R,4S,9S), isopyrazam (anti—epimeric enantiomer 9R), isopyrazam (syn— epimeric racemate lRS,4SR,9RS), isopyrazam (syn-epimeric enantiomer 1R,4S,9R), isopyrazam (syn-epimeric enantiomer 15,4R,9S), mepronil, oxycarboxin, penflufen, penthiopyrad, sedaxane, thi?uzamide, 1-methyl-N-[2- (1, 1,2,2—tetra?uoroethoxy)phenyl]—3-(tri?uoromethy1)-1H—pyrazole—4- carboxamide, 3 -(difluoromethyl)- 1—methyl-N—[2-(1,1,2,2-tetra?uoro— ethoxy)phenyl]—1H-pyrazolecarboxamide, uoromethyl)-N—[4-?uoro-2— (1,1,2,3,3,3-hexa?uoropropoxy)phenyl]methyl-lH-pyrazolecarboxamide, N-[1-(2,4—dichlorophenyl)—1-methoxypropanyl]—3-(di?uoromethy1)methyl- 1H-pyrazolecarboxamide, 5,8-difluoro-N— [2-(2-?uoro { [4- (tri?uoromethyl)pyridin-2—yl]oxy}phenyl)ethyl]quinazolineamine, benzovindiflupyr, N-[(1S,4R)(dichloromethylene)-1,2,3,4—tetrahydro-1,4— onaphthalen-S-yl](difluoromethyl)methyl-1H-pyrazole carboxamide and N— [(1R,4S)(dichloromethylene)— 1 ,2,3,4—tetrahydro- 1 ,4- methanonaphthalen-S-yl](di?uoromethyl)methy1-1H-pyrazole—4- carboxann'de, 3-(di?uoromethy1)—1-methy1—N-(1,1,3—trimethyl-2,3—dihydro—1H- 4-y1)-1H-pyrazole-4—carboxan1ide, 1,3,5-trin1ethy1-N-(1,1,3-trimethy1-2,3- dihydro-1H-inden—4-y1)-1H-pyrazolecarboxamide, 1-methy1(tri?uoro— )-N—(1,1,3-trimethy1—2,3-dihydro-1H—inden-4—y1)-1H—pyrazole—4- carboxamide, 1-methy1-3 -(tri?uoromethy1)—N-[(3R)- 1 , 1,3 -trimethy1—2, 3-dihydro- 1H—inden-4—y1]—1H—pyrazole—4-carboxan1ide, 1-methy1(tri?uoron1ethy1)-N— [(3S)-1,1,3-trimethy1-2,3-dihydro-1H-indeny1]—1H-pyrazolecarboxamide, 3- oromethyl)-1—methy1—N-[(3S)—1,1,3-t1imethy1-2,3-dihydro-1H-inden-4—y1]— 1H-pyrazolecarboxan1ide, 3-(difluoromethy1)methy1-N-[(3R)-1,1,3- trimethy1-2,3-dihydro-1H-indeny1]—1H-pyrazole—4—carboxamide, 1,3,5- hyl-N-[(3R)-1,1,3-trimethy1-2,3-dihydro-1H-indenyl]—1H-pyrazole carboxamide, 1,3,5—trimethy1—N-[(3S)—1,1,3—trimet11y1—2,3-dihydro-1H—inden—4— y1]-1H-pyrazolecarboxamide, benodanil, 2-chloro-N-(1, 1,3 -trimethy1-2,3— dihydro-1H-indeny1)pyridine-3 -carboxamide, isofetamid. (3) Respiration inhibitors (respiratory chain inhibitors) acting on complex III of the respiratory chain such as, for example, ametoctradin, brom, azoxystrobin, cyazofamid, coumethoxystrobin, coumoxystrobin, dimoxystrobin, enestroburin, famoxadone, done, ?ufenoxystrobin, ?uoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyribencarb, triclopyricarb, tri?oxystrobin, (2E)(2— { chloro-2—methylphenoxy)—5-?uoropyrimidin y1]oxy }pheny1)(methoxyimino)-N—methy1ethanamide, (2E)(methoxyimino)- N-methyl—Z-(2-{ [({(1E)-1—[3 -(trifluoromethyl)phenyl]ethylidene } amino)- oxy]methy1}pheny1)ethanamide, (2E)(methoxyimino)-N-methy1-2— {2- [(E)-({ 1- [3-(tri?uoromethyl)pheny1]ethoxy }imino)methy1]pheny1}ethanamide, (2E)—2— {2- [({ [(1E)-1—(3 -{ [(E)—1-?uoropheny1ethenyl]oxy}pheny1)ethy1idene]— amino }oxy)methyl]pheny1}(methoxyimino)-N-methy1ethanamide, (2E) { 2- [({ [(2E,3E)—4-(2, 6—dichloropheny1)but-3 -en—2-y1idene]amino } oxy)n1ethy1]— phenyl } -2—(methoxyimino)—N-methylethanamide, 2-chloro—N-(1,1,3—trimethy1- hydro—1H—indeny1)pyridine—3-carboxamide, 5-methoxyn1ethy1-4—(2- { [( { ( 1E) - l — [3 -(trifluoromethyl)phenyl]ethylidene } amino)oxy]methyl }phenyl)-2,4- dihydro-3H-1,2,4—triazol—3-one, methyl — {2— [( { cyclopropyl[(4— yphenyl)imino]methyl } sulphanyl)methyl]phenyl } -3—methoxyprop enoate, N—(3 -ethyl-3 -trimethylcyclohexyl)-3 -(formylamino)-2—hydroxy— , 5 ,5 benzamide, 2- { 2- [(2, thylphenoxy)methyl]phenyl } methoxy-N- methylacetamide. (4) Inhibitors of mitosis and cell division such as, for example, benomyl, carbendazim, chlorfenazole, diethofencarb, ethaboxam, ?uopicolid, fuberidazole, uron, thiabendazole, thiophanate-methyl, thiophanate, zoxamide, 5-chloro-7—(4-methylpiperidin-l—yl)(2,4,6-tri?uorophenyl)[1,2,4]- triazolo[l,5-a]pyrimidine and ro(6-chloropyridinyl)methyl-4— (2,4,6-tri?uorophenyl)pyridazine. (5) nds having multisite activity such as, for example, Bordeaux mixture, captafol, captan, chlorothalonil, copper preparations such as copper hydroxide, copper naphthenate, copper oxide, copper oxychloride, copper sulphate, dichlo?uanid, dithianon, dodine, dodine free base, ferbam, ?uorfolpet, folpet, guazatine, guazatine acetate, iminoctadine, iminoctadine albesilate, iminoctadine tate, mancopper, mancozeb, maneb, metiram, zinc metiram, copper-oxine, propamidine, propineb, sulphur and sulphur preparations such as, for example calcium lphide, thiram, tolylfluanid, zineb, ziram and (6) Resistance inducers such as, for example, acibenzolar—S- methyl, isotianil, probenazole, tiadinil and rin. (7) Inhibitors of amino acid and protein biosynthesis such as, for example, blasticidin-S, cyprodinil, kasugamycin, kasugamycin hydrochloride hydrate, mepanipyrim, pyrimethanil, 3-(5—?uoro-3,3,4,4-tetramethyl-3,4- dihydroisoquinolin—l-yl)quinolone, oxytetracycline and streptomycin. (8) ATP production inhibitors such as, for example, fentin acetate, fentin chloride, fentin hydroxide and silthiofam. (9) Inhibitors of cell wall synthesis such as, for example, benthiavalicarb, dimethomorph, flumorph, iprovalicarb, mandipropamid, polyoxins, polyoxon'm, validamycin A, nalate and polyoxin B. (10) Inhibitors of lipid and membrane synthesis such as, for example, biphenyl, chlomeb, an, edifenphos, etridiazole, iodocarb, iprobenfos, isoprothiolane, propamocarb, propamocarb hydrochloride, prothiocarb,, pyrazophos, quintozene, tecnazene and tolclofos-methyl. (l l) Melanin biosynthesis tors, for example carpropamid, diclocymet, fenoxanil, fthalide, ilon, tricyclazole and 2,2,2-tri?uoroethyl {3-methyl- l - [(4-methylbenzoyl)amino]butanyl } carbamate. (12) Inhibitors of nucleic acid synthesis such as, for example, benalaxyl, benalaxyl-M axyl), bupirimate, clozylacon, dimethirimol, ethirimol, furalaxyl, hymexazole, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl, oxolinic acid and octhilinone. (13) Signal transduction inhibitors such as, for example, chlozolinate, lonil, ?udioxonil, iprodione, procymidone, quinoxyfen, Vinclozolin and proquinazid. (14) Decouplers such as, for example, binapacryl, p, ferimzone, ?uazinam and meptyldinocap. (15) Further compounds such as, for e, benthiazole, bethoxazine, capsimycin, carvone, chinomethionat, pyriofenone afenone), cufraneb, cy?ufenamid, cymoxanil, ulfamide, t, debacarb, dichlorophen, diclomezine, difenzoquat, difenzoquat methylsulphate, diphenylamine, EcoMate, fenpyrazamine, ?umetover, ?uorimid, ?usulfamide, ?utianil, fosetyl-aluminium, fosetyl-calcium, l-sodium, hexachlorobenzene, irumamycin, methasulfocarb, methyl isothiocyanate, enone, mildiomycin, natamycin, nickel dimethyldithiocarbamate, hal-isopropyl, octhilinone, oxamocarb, oxyfenthiin, pentachlorophenol and its salts, phenothrin, phosphoric acid and its salts, propamocarb-fosetylate, propanosine-sodium, rph, (2E)- 3-(4-tert-butylphenyl)-3 -(2—chlor0pyridin-4—yl)- 1-(morpholinyl)pr0p—2-en— 1- one, (ZZ)—3-(4-tert-butylphenyl)-3—(2-chlor0pyridinyl)-1—(m0rpholinyl)pr0p- 2-en0ne, pyrrolnitrin, tebu?oquin, tecloftalam, tolnifanide, triazoxide, trichlamide, zarilamid, (3S,6S,7R,8R)benzyl[({3-[(isobutyryloxy)meth0xy]- 4-methoxypyridin-2—yl } carbonyl)amino] -6—methyl-4,9-dioxo— 1 ,5 -dioxonan-7—yl 2- methylpropanoate, 4-[(5R)-5—(2,6-diflu0r0phenyl)-4,5-dihydr0-1,2-oxazol- 3-yl]-1,3 -thiazol-2—yl } piperidiny1)—2- [5 -methyl-3—(tn'?uoromethy1)— 1 H- pyrazol- 1-yl]ethanone, 1-(4— {4- [(5S)(2,6-di?u0r0phenyl)-4,5 -dihydr0-1,2— oxazoly1]— 1 ,3-thiazolyl idin- 1-y1)—2- [5-methyl-3—(tri?uoromethyl)— 1H- pyrazol- 1-yl]ethan0ne, 1-(4— {4- [5 -(2,6-diflu0r0phenyl)-4,5 -dihydr0-1,2-0xazol yl]-1,3 -thiaz01yl}piperidinyl)[5 -methy1-3 -(tri?uor0methyl)- azol- 1-yl]ethan0ne, 1-(4-meth0xyphenoxy)-3 ,3 hylbutanyl 1H-imidazole carboxylate, 2,3,5,6-tetrachlor0-4—(methylsulphonyl)pyridine, 2,3—dibutyl-6— chlorothieno[2,3-d]pyrimidin-4(3H)-0ne, 2,6-dimethyl-1H,5H-[1,4]dithiin0[2,3- c:5,6-c']dipyrrole—1,3,5,7(2H,6H)—tetr0ne, 2-[5-methyl(tri?u0r0methyl)—1H- pyrazolyl]—1-(4-{4-[(5R)phenyl-4,5-dihydr0-1,2-oxazolyl]-1,3-thiazol yl}piperidinyl)ethan0ne, 2- [5-methyl-3—(tri?u0romethyl)— 1H-pyrazol- 1-y1] - 1- (4—{4-[(5S)—5-phenyl-4,5-dihydr0-1,2-oxazolyl]-1,3-thiazolyl}piperidin yl)ethan0ne, ethyl(tri?u0r0methyl)-1H-pyrazol-1—yl]{4-[4-(5-phenyl- 4,5—dihydro—1,2-0xazoly1)-1,3-thiazolyl]piperidiny1}ethan0ne, 2-but0xy- 6-i0d0pr0pyl-4H-chr0men0ne, 2-chlor0[2-chlor0(2,6-diflu0r0-4— methoxyphenyl)-4—methyl-lH-imidazol-S-y1]pyridine, 2-phenylphenol and salts, 3-(4,4,5-tri?u0r0-3,3-dimethyl-3,4—dihydr0is0quinolinyl)quinoline, 3,4,5— trichloropyridine-Z,6—dicarbonitrile, 3—chloro—5-(4-chlorophenyl)(2,6- di?uorophenyl)methylpyridazine, 4-(4-chlor0phenyl)(2,6-difluor0phenyl)- 3,6-dimethy1pyridazine, 5-amino-1,3,4-thiadiazole-2—thiol, 5-Chloro-N‘-pheny1-N'- (prop-Z-ynyl)thiophenesulphonohydrazide, 5-?u0r0-2—[(4-?uor0benzy1)- oxy]pyrimidineamine, 5—?u0r0-2—[(4-methy1benzy1)0xy]pyrimidineamine, —methy1—6-octy1[1,2,4]triazolo[1,5—a]pyrimidine-7—amine, ethyl (22)amin0 3-pheny1acrylate, N'—(4-{ [3-(4-ch10r0benzy1)—1,2,4-thiadiaz01—5-y1]0xy} - 2,5-dimethylpheny1)-N—ethyl-N-methylimidoformamide, N—(4-chlorobenzy1)—3-[3- methoxy-4—(prop-Z—yn- 1-y10xy)pheny1]propanamide, N- [(4—ch10r0pheny1)- (cyano)methyl]-3—[3-meth0xy(pr0pyny10xy)pheny1]pr0panamide, N-[(5- bromochloropyridiny1)methyl] -2,4-dichlor0nicotinamide, N- [ 1 —(5-br0mo-3 - ch10r0pyridiny1)ethy1] -2,4-dich10r0nicotinamide, N- [1 -(5-br0m0—3 - chloropyridiny1)ethy1] -2—?uoro-4—iodonicotinan?de, N-{ (E)-[(cyclopropy1— methoxy)imin0] ?u0r0meth0xy)-2,3 -diflu0r0pheny1]methy1}-2— phenylacetamide, N— { (Z)- [(cyclopropylmethoxy?mjno] [6-(di?uoromethoxy)—2,3 - di?uoropheny1]methy1}pheny1acetamide, N'-{4-[(3-tert-buty1cyan0-1,2- thiazol-S-y1)oxy]-2—Chloro—5—methylpheny1}—N-ethyl—N-methylimidoformamide, N-methy1( 1 -{ [5-methy1(tri?uor0methy1)-1H-pyraz01y1]acety1}piperidin- 4-y1)-N-(1,2,3,4-tetrahydronaphthaleny1)-1,3-thiazolecarboxamide, N- methy1( 1 -{ [5 -methy1(tri?u0romethy1)—1H-pyraz01yl]acety1}piperidin yl)—N—[(1R)-1,2,3,4—tetrahydr0naphthalen—1-y1]-1,3-thiazolecarboxamide, N- ( 1 -{ [5 1(tri?u0r0methy1)—1H-pyraz01yl]acety1}piperidin y1)-N- [(1 S)- 1 ,2,3,4—tetrahydr0naphthalen- 1-y1]— 1 ,3—thiazole—4-carb0xamide, pentyl {6-[({ [(1 -methyl- 1H-tetraz01-5 heny1)methylene]amino } oxy)- methy1]pyridin-2—y1}carbamate, phenazine—l-carboxylic acid, quinolin-S-ol, quinolin-S—ol sulphate (2:1), tert-butyl {6-[({[(1-methy1-1H—tetraz01—5- y1)(pheny1)methylene]amino } oxy)methy1]pyridin-2—y1 } carbamate, 1-methy1—3 - (trifluoromethyl)-N—[2'-(tri?uoromethy1)bipheny1-2—y1]-1H-pyrazole—4- carboxamide, N-(4‘-ch10r0bipheny1y1)-3—(di?u0r0methy1)— 1-methy1- 1H- pyrazole-4—carboxamide, N—(2’,4'-dich10robipheny1—2—y1)(di?uoromethy1)—1- methyl-1H-pyrazolecarb0xamide, 3 -(diflu0r0methy1)methy1-N-[4'— (tri?uoromethy1)bipheny1-2—yl]-1H—pyrazole—4-carboxamide, N-(2’ ,5‘— di?uorobiphenyl-Z-y1)methy1-3 -(tri?u0r0methy1)-1H-pyrazolecarb0xamide, 3 uoromethyl)methy1-N-[4'—(prop—1-yny1)biphenyly1]—1H-pyrazole carboxamide, 5-?u0r0-1,3-dimethy1-N-[4'-(pr0pyny1)bipheny1—2-y1]—1H- pyrazolecarb0xamide, r0-N- [4'-(propyn— 1 -y1)bipheny1 y1]nic0tinamide, 3-(di?uoromethy1)—N—[4'—(3 ,3-dimethy1but— 1-yn- 1 —y1)bipheny1 y1]methy1-1H-pyrazolecarboxamide, N-[4'—(3,3-dimethy1but-1—yn y1)bipheny1y1]—5-?u0r0— 1,3 -dimethy1-1H-pyrazolecarboxamide, 3 - (di?uoromethyl)-N—(4'-ethyny1bipheny1y1)methy1-1H-pyrazole—4- carboxamide, N-(4‘-ethynylbiphenyly1)—5-?u0r0- 1 ,3 -dimethy1-1H-pyrazole carboxamide, 2-Ch10r0-N-(4‘-ethynylbiphenyly1)nicotinamide, r0-N—[4'- (3 ,3-dimethy1butynyl)biphenyly1]nicotinamide, 4-(di?u0r0methy1)—2- methyl-N-[4'-(trifluoromethy1)bipheny1y1]-1,3 -thiazole-5—carboxamide, 5— fluoro-N- [4‘-(3-hydr0xy-3 —methy1but- 1-yn—1-y1)bipheny1-2—y1]— 1,3-dimethy1-1H- pyrazole-4—carboxamide, 2—Chloro-N— [4'-(3—hydroxy—3 -methy1butyn y1)bipheny1y1]nicotinamide, 3-(di?u0r0methy1)-N-[4'-(3-meth0xymethy1but- 1-yn—1-y1)bipheny1—2—y1]-1—methy1—1H—pyrazolecarboxamide, 5-?uoro-N—[4‘— (3-meth0xy-3 -methy1butyny1)bipheny1y1]—1,3 -dimethy1-1H—pyrazole carboxamjde, 2-Chloro-N-[4‘-(3-methoxymethylbutyn- 1-y1)biphenyl y1]nicotinamide, (5-br0m0meth0xymethy1pyridiny1)(2,3,4-trimeth0xy methylpheny1)methan0ne, N- [2-(4— { [3 -(4—ch10r0pheny1)prop-2—yn—1-y1]0xy}-3 - ypheny1)ethy1]-N2-(methylsulph0nyl)valinamide, 4-[(2- phenylethyl)amin0]butanoic acid, butyny1 {6—[({ [(Z)—(1-methy1-1H—tetrazol- -y1)(pheny1)methylene]amino ethy1]pyridin—2-y1 }Carbamate, 4-amino-5 - fluoropyrimidin-Z—ol (tautomeric form: 4-amin0-5—?u0r0pyrimidin—2(1H)-0ne), propyl 3,4,5 -trihydroxybenzoate, 1,3-dimethy1-N-(1,1,3 -trimethy1-2,3-dihydro- 1H-inden—4-y1)-1H-pyrazolecarb0xamide, 1,3-dimethy1-N-[(3R)—1,1,3- hy1-2,3 -dihydr0-1H-indeny1]—1H-pyrazolecarb0xamide, 1,3-dimethy1- N—[(3S)-1,1,3-trimethy1-2,3-dihydr0-1H-indeny1]-1H-pyrazole-4—carb0xamide, [3—(4-Chlor0—2-?uoropheny1)—5 -(2,4—di?uoropheny1)—1,2-oxazoly1](pyridin—3- y1)methan01, (S)- [3-(4-ch10r0fluor0phenyl)-5 -(2,4-di?u0r0pheny1)-1,2-0xaz01- 4-y1](pyridin—3-y1)methanol, —(4-ch10ro—2-?uoropheny1)—5-(2,4— opheny1)- 1 ,2-oxaz01y1] (pyridiny1)methan01, 2-{ [3-(2-chlor0pheny1)- 2-(2,4-di?uoropheny1)oxirany1]methyl}-2,4-dihydro-3H-1,2,4-triazole thione, 1-{ [3-(2-ch10r0pheny1)(2,4-di?uoropheny1)0xirany1]methyl } - 1H- 1,2,4-triazoly1 thiocyanate, 5-(a11y1sulfany1){[3-(2-ch10r0pheny1)(2,4- di?uoropheny1)oxirany1]methyl }- ,4-triazole, 2-[1-(2,4-dich10r0pheny1)- -hydr0xy—2,6,6-trimethy1heptan-4—y1]-2,4-dihydro-3H-1,2,4-triazole-3 -thione, 2- { [rel(2R,3S)(2—ch10r0pheny1)-2—(2,4-di?uorophenyl)0xiranyl]methyl } -2,4- dihydr0-3H-1,2,4-triazolethione, 2- { [rel(2R,3R)(2-chlor0phenyl)(2,4- rophenyl)oxiran-Z-yl]methy1}-2,4-dihydr0-3H-1,2,4-triazolethi0ne, 1- { R,3S)(2-ch10r0pheny1)(2,4-difluorophenyl)0xirany1]methyl } — 1H- 1,2,4-triazoly1 thiocyanate, 1- { [rel(2R,3R)(2-ch10r0pheny1)-2—(2,4- di?uorophenyl)oxiran-Z-yl]methyl }—1H-1,2,4-triazol—5-y1 thiocyanate, 5 - (allylsulphany1)-1—{ [rel(2R,3S)-3 -(2-ch10r0pheny1)—2-(2,4-diflu0r0pheny1)0xiran- 2-y1]methy1}-1H-1,2,4-I;riazole, 5-(a11y1su1phany1)-1—{ [rel(2R,3R)-3—(2- ch10r0pheny1)(2,4-di?uor0pheny1)0xiranyl]methyl}-1H-1,2,4-triazole, 2- [(ZS ,4S,5 S)— 1-(2,4—dichloropheny1)—5 —hydroxy-2, 6,6—trimethy1heptan—4—y1] -2,4— 0-3H-1,2,4-triazolethione, 2-[(2R,4S,SS)(2,4-dich10r0pheny1)-5— hydroxy-Z,6,6-trimethy1heptanyl]-2,4-dihydro-3H-1,2,4-triazolethione, 2- [(2R,4R,5R)- 1-(2,4—dich10ropheny1)hydroxy-2,6,6-trimethy1heptany1]-2,4- dihydr0-3H-1,2,4-triazolethione, 2- [(25,4R,5R)(2,4-dich10ropheny1) hydroxy-Z,6,6-trimethy1heptanyl]-2,4-dihydr0-3H-1,2,4-triazole-3 -thione, 2- [(25,4S,5R)(2,4-dich10ropheny1)—5-hydroxy-2,6,6-trimethylheptanyl]—2,4- dihydr0-3H-1,2,4-triazolethione, 2-[(2R,4S,5R)(2,4-dich10r0pheny1)-5— hydroxy-Z,6,6-trimethy1heptanyl]-2,4-dihydr0-3H-1,2,4—triazole—3 -thione, 2- [(2R,4R,SS)(2,4—dich10ropheny1)—5-hydroxy-2,6,6-trimethy1heptany1]-2,4- dihydr0-3H-1,2,4-triazole—3-thione, 2-[(28,4R,SS)(2,4-dich10r0pheny1)-5— hydroxy-Z,6,6-trimethy1heptanyl]—2,4-dihydr0-3H—1,2,4-triazole-3 —thione, 2- ?u0r0(tri?u0r0methy1)-N—( 1, 1,3-trimethy1-2,3 -dihydr0-1H-inden—4- y1)benzamide, 2-(6—benzy1pyridin-2—y1)quinazoline, 2—[6-(3—?uoro-4— yphenyl)methy1pyridinyl]quinazoline, 3-(4,4-di?u0r0-3,3-dimethy1- 3,4—dihydroisoquinoliny1)quinoline, abscisic acid, 3-(di?uoromethy1)-N- methoxy- y1—N-[1-(2,4,6-trich10r0pheny1)propan-Z-yl]- 1H-pyrazole-4— carboxamjde, N'-[5-bromo(2,3-dihydro-1H-inden-Z-yloxy)rnethy1pyridin yl]-N-ethy1-N-methylimidof0rmamide, N'- {5 -br0m0[1-(3,5-di?uor0phenyl)- ethoxy]methy1pyridin-3—y1}-N-ethy1-N-methylimidoformamide, N'- {5-br0m0- )-1—(3,5-di?u0r0pheny1)ethoxy]methy1pyridin-3 —y1 } -N—ethy1-N— methylimidoformamide, N'— {5-br0m0 [(1 S)(3 ,5-di?u0rophenyl)eth0xy] pyridin-3 -yl}-N—ethy1-N-methylimid0f0rmamide, N'— {5 -br0m0 [(cis isopropylcyclohexyl)0xy]methy1pyridiny1} -N—ethy1-N—methy1imid0- formamide, N'- {5 —br0m0 [(trans—4-isopropylcyclohexy1)0xy]methy1pyridin- 3-yl}-N-ethy1-N-methylimid0f0rmamide, N—cyclopropy1-3 -(di?u0romethy1)—5- fluoro-N-(2-is0pr0py1benzy1)methy1-1H—pyrazolecarboxamide, N- cyclopropyl—N-(2-cyc10propy1benzy1)(di?uoromethy1)-5—fluoro-1—methy1—1H- pyrazole-4—carb0xamide, N-(2-tert—butylbenzy1)-N-cyclopropyl(diflu0r0- methy1)-5 -?uoro-1—methy1—1H-pyrazolecarboxamide, N-(5 —ch10ro—2- ethylbenzyl)-N-cyclopropyl(diflu0r0methy1)-5 -flu0r0methy1-1H-pyrazole carboxamide, N-(5—Chloro-2—isopropylbenzyl)—N-cyclopropy1—3-(di?uoromethy1)- -?u0r0methy1-1H-pyrazolecarb0xamide, N-cyclopropy1-3 -(di?u0r0- methy1)-N-(2-ethyl-5 obenzy1)-5 -fluoromethy1-1H—pyrazole carboxamide, N-cyclopropy1(di?uoromethy1)?u0r0-N—(5-?u0ro isopropylbenzy1)—1-methy1-1H—pyrazole-4—carboxamide, N—cyclopropyl-N—(Z- ropyl-5 -?u0robenzyl)-3 -(diflu0r0methy1)-5 -?u0r0methy1-1H-pyrazole- 4—carboxamide, N—(2-cyclopenty1—5-?uorobenzyl)—N-cyclopr0py1-3—(di?u0ro- methy1)-5 -flu0r0-1—methy1—1H-pyrazolecarb0xamide, N-cyclopropy1-3 - (di?uoromethyl)?u0r0—N—(2-flu0r0is0pr0pylbenzy1)methy1—1H-pyrazole- 4-carboxamide, N-cyclopropy1(di?uoromethy1)-N-(2-ethy1methy1benzyl) fluoromethyl- 1H-pyrazolecarb0xamide, N-cyclopropy1-3 -(diflu0r0methy1)- -?u0r0-N—(2-isopropy1methy1benzy1)-1—methy1—1H-pyrazolecarboxamide, N—cyclopropyl-N-(2-cyclopr0py1methy1benzy1)(difluoromethyl)flu0r0- 1- methyl-1H—pyrazole—4-carb0xamide, N-(2-tert-buty1—5-methy1benzy1)—N-cyclo- -3 oromethy1)?u0romethy1-1H-pyrazolecarboxamide, N- [5 - chloro(tri?uoromethy1)benzy1]-N—cyclopropy1-3—(di?uoromethy1)—5 —?uor0— 1- methyl-1H-pyrazolecarb0xamide, N-cyclopropyl(difluor0methy1)flu0r0- 1-methy1-N- [5 -methy1(tn'?uoromethyl)benzy1]-1H-pyrazolecarboxamjde, N- [2-ch10r0(tri?uoromethyl)benzyl]-N-cyc10pr0pyl(di?uor0methy1)flu0r0- yl-1H-pyrazolecarboxamide, N- [3-chlorofluoro(tri?uoromethyl )benzyl] -N—cyclopropyl-3 —(di?uoromethyl)—5-?uoro— 1-methy1- 1H- pyrazole-4—carboxamide, N-cyclopropyl(di?uoromethyl)—N-(2-ethyl-4,5- dimethylbenzyl)?uoro—1-methyl—1H—pyrazole-4—carboxamide, N—cyclopropyl- 3-(di?uoromethyl)—5-fluoro-N-(2-isopropylbenzyl)methy1-1H-pyrazol carbothioamide, 3 —(di?uoromethyl)—N-(7—fluoro-1,1,3-trimethyl-2,3-dihydro-1H- indeny1)—1-methyl- 1H-pyrazolecarboxamide, 3-(di?uoromethyl)-N- [(3R) fluoro- 1 , 1,3 -trimethyl-2,3 —dihydro—1H-indenyl]—1-methy1-1H-pyrazole-4— carboxamjde, 3 -(difluoromethyl)-N—[(3S)-7—?uoro-1 , 1,3 thyl-2,3 ro- enyl]—1-methyl-1H-pyrazolecarboxamide, N'-(2,5-dimethyl phenoxyphenyl)-N—ethyl-N—methylimidoformamide, N'-{4-[(4,5-dichloro-1,3— thiazol-Z-yl)oxy] -2,5 -dimethylphenyl } -N-ethyl-N-methylimidoformamide, N-(4- chloro-Z,6—di?uorophenyl)—4—(2-chloro?uorophenyl)-1,3—dimethy1—1H- pyrazoleamine.

Particularly suitable seed treatment active ingredients that may be utilized in the treatment composition include iprid, clothianidin loprid, thiacloprid, thiamethoxam, abamectin, emamectin, emamectin- benzoate, rynaxypyr oantraniliprole), cyazypyr (cyntraniliprole), spinetoram, spinosad, sulfoxa?or, lambda-cyhalothrin, beta—cy?uthrin, te?uthrin, ?upyradifurone, tetraniliprole, Bacillus firmus CNCM I 1582, Bacillus subtilis QST 713, Bacillus subtilis AQ30002, prothioconazole, metalaxyl, mefenoxam, benalaxy], kiralaxyl, tri?oxystrobin, trobin, picoxystrobin, pyraclostrobin, ?uopyram, thiram, tebuconazole, fludioxonil, and ipconazole.

In some embodiments, the insecticide, fungicide, nematicide, and/or other pesticides is present in the treatment compositions of the present invention in an amount of at least 15%, such as at least 20%, such as at least 25%, such as at least 30% and/or no more than 80%, such as no more than 75%, such as no more than 60%, such as no more than 50%.

In some embodiments, the seed treatment compositions of the present invention may further include any of a variety of additives such as ers, devolatilizers, thickeners, ?ow control additives, colorants (including pigments and dyes), surfactants, dispersants, neutralizers, biological materials (such as inoculants), nutrients, micronutrients, or surface additives. Inert materials may also be ed such as, for example, to improve ng or packaging and may include, for example, silica, starches, clays and other minerals.

For example, in some embodiments, the seed treatment compositions include an inorganic lubricant, such as, for example, talc, mica, graphite, a carbide, a carbonate, an oxide of carbon, a cyanide, an allotrope of carbon, or a mixture of two or more f.

When used, such inorganic lubricant(s) are often present in the seed treatment composition in an amount of at least 0.5%, such as at least 1%, such as at least 1.5% and/or no more than 10%, such as no more than 8%, such as no more than 5%.

] In some embodiments, in addition to or in lieu of an inorganic lubricant, the seed treatment composition of the t invention may comprise an organic lubricant. Examples of such organic lubricants include, but are not limited to a wax, such as, polyethylene, powdered polyethylene, camuba, paraffin, polypropylene, an oxidized polyethylene wax, montan waxes, microcrystalline waxes, Fischer-Tropsch waxes, amide waxes, ne -Acrylic- Acid (EAA) waxes, polyolefin waxes, Ethylene bis stearamide (EBS) waxes, animal waxes (bees wax and lanolin), vegetable waxes (camauba and illa), or slac and scale waxes, polytetra?uoroethylene, ing mixtures of two or more thereof.

In some ments, the wax comprises polyethylene wax, such as MICHEM Wax 437 from Michelman, Inc. As a result, embodiments of the present invention are also directed to seed treatment compositions comprising, consisting essentially of, or, in some cases, consisting of: (A) an s polyurethane dispersion; (B) an insecticide, a fungicide, a nematicide, and/or other pesticides; and (C) a polyethylene wax.

In some embodiments, the seed treatment ition is applied to a seed and then the seed is subsequently coated with a lubricant compound.

In certain embodiments, a seed treatment ition as described herein is applied to a seed at the same time or before the planter fills the planter hopper with seed. In other embodiments, a seed treatment composition as described herein is applied to a seed as a farmer fills the planter hopper with seed.

In some embodiments, the hopper forms a component part of a planter, such as an air or vacuum planter, with a planter ism, examples of which are commercially ble from, for example, John Deere, Case IH, Kinze, AGCO White, Great Plains, or ion Planting.

In certain embodiments, the methods and seed treatment compositions described herein may increase percent singulation by at least 0.2%, such as at least 0.5%, relative to the use of an identical seed treatment composition in which a polyolefin latex, such as a carboxylated styrene/butadiene polymer, is used as the polymeric component of the seed composition rather than the aqueous polyurethane dispersion when comparing the same type of seed. There is a statistically and practically significant se in percent singulation, because the percent singulation of the seed treatment composition in which a polyolefin latex, such as a carboxylated e/butadiene polymer, is used as the polymeric component of the composition can already exceed 99%. Therefore, an increase in percent singulation by 0.2% or 0.5% is statistically and practically significant e, for example, a yield increase of 0.2% can increase a farmer’s profitability thousands of dollars in a planting season.

In certain embodiments, a seed treatment composition as described herein is applied to a seed at a rate of 0.1 - 5.0 oz/cwt (ounces/hundredweight), 0.5 - 4.0 oz/cwt, 1.0 — 3.5 , 1.5 — 3.0 oz/cwt, 2.0 — 3.0 oz/cwt, 2.0 — 2.5 oz/cwt, or 0.2 oz/cwt, 0.5 oz/cwt, 0.75 oz/cwt, 1.0 , 1.5 oz/cwt, 2.0 oz/cwt, 2.5 oz/cwt, 3.0 oz/cwt, 3.5 oz/cwt, 4.0 oz/cwt, 4.5 oz/cwt, 5.0 oz/cwt, or 0.2 oz/cwt or more, 0.5 oz/cwt or more, 0.75 oz/cwt or more, 1.0 oz/cwt or more, 1.5 oz/cwt or more, 2.0 oz/cwt or more, 2.5 oz/cwt or more, 3.0 oz/cwt or more, 3.5 oz/cwt or more, 4.0 oz/cwt or more, 4.5 oz/cwt or more, or 5.0 oz/cwt or more.

In some embodiments of the present invention, a seed treatment composition described herein is applied to a seed in a single application step. In other respects, a seed treatment ition described herein is applied in multiple ation steps. In yet another embodiment, a seed treatment composition described herein is applied in one, two, three or more ation steps to a seed.

Seeds which can be treated with the seed treatment composition described herein e, for example, any agricultural or vegetable seeds that are planted through, for example, a vacuum planter. Examples of such seeds include, but are not limited to, corn seed, cotton seed, sorghum seed, oat seed, rye seed, barley seed, soybean seed, vegetable seed, wheat seed, sugarbeat seed, rice, er seed, lettuce seed, and spinach seed. Specific examples of corn seeds capable of being treated with the treatment compositions described herein include, for example, sweet corn (for example, zea mays convar. saccharata var. Rugosa), silver queen corn, golden bantam, early sunglow, Indian corn, sugar corn, pole corn, field corn, dent corn, ?int corn, ?our corn, blue corn (for example, Zea mays amylacea), popcorn, and waxy corn.

Seeds may be treated with the described compositions by applying the disclosed compositions directly to the seed. In another embodiment, the seed may be treated ctly, for example by treating the environment or habitat to which the seed is exposed.

Conventional treatment methods may be used to treat the environment or habitat ing dipping, ng, rolling, fumigating, chemigating, fogging, ring, brushing on, shanking or injecting.

] Some embodiments of the present invention are directed to a kit comprising, consisting ially of, or consisting of any of the seed treatment compositions disclosed . In some embodiments, the kit provides instructions or ce regarding the use of the seed treatment compositions or methods described herein. In some embodiments, the instructions are included with the kit, te from the kit, in the kit, or are included on the kit packaging.

In yet another aspect, the instructions provide for application of a seed treatment composition at planting.

The present disclosure also provides for a method of increasing percent singulation in the planting of seeds by a planter, such as a vacuum planter, by applying a seed treatment ition described herein to a seed. The present disclosure also provides for use of a seed treatment ition described herein to increase percent singulation in the planting of seeds by a planter, such as a vacuum planter.

As will be appreciated by the foregoing ption, embodiments of the present invention are directed to seed treatment compositions that comprise: (A) an s polyurethane dispersion; and (B) an insecticide, a fungicide, a nematicide, and/or other pesticides, wherein the aqueous polyurethane dispersion forms a film exhibiting: (a) a Tg of —480C to —40C, such as -48°C to —300C, (b) a percent elongation of 44 to 300, such as 100 to 300, and (c) a tensile strength of 2500 lb/in2 (17.2 MPa) to 4100 lb/in2 (28.3 MPa), and (d) optionally a microhardness of up to 45.4 N/mm2, such as 0.4 to 45.4 N/mmz.

Embodiments of the present invention are directed to a seed treatment composition of the previous paragraph, wherein (a) the Tg is -48°C to - 300C, (b) the t elongation is 10 to 300, and/or (d) the microhardness is up to N/mmz, such as 0.4 to 15 N/mmz.

Embodiments of the present invention are ed to a seed treatment composition of either of the previous two paragraphs, wherein the aqueous polyurethane dispersion of the seed ent composition comprises one or more polyurethanes that are the reaction product of reactants comprising, consisting essentially of, or, in some cases, consisting of: (i) a ocyanate; (ii) a polymeric polyol having a number e molecular weight ("Mn") of 400 to 8,000 g/mol; (iii) a compound comprising at least one isocyanate-reactive group and an anionic group or potentially anionic group; (iv) optionally a mono functional polyalkylene ether; (v) optionally a polyol having a molecular weight of less than <400 g/mol, and (vi) ally a polyamine or amino l having a molecular weight of from 32 to 400 g/mol.

Embodiments of the present invention are directed to a seed treatment composition of the previous paragraph, wherein the polyisocyanate (i) of the seed treatment composition comprises an aromatic, araliphatic, aliphatic and/or cycloaliphatic polyisocyanate, such as 1,6-hexamethylene diisocyanate (HDI), pentamethylene diisocyanate (PDI), isophorone diisocyanate (IPDI), the isomeric bis-(4,4'-isocyanatocyclohexyl)methanes or a mixture thereof.

Embodiments of the present invention are directed to a seed treatment composition of either of the us two paragraphs, wherein component (i) of the seed treatment composition is included in an amount of at least 5% by weight, such as at least 10 or at least 20% by weight and/or no more than 60% by weight, such as no more than 50 or, in some cases, no more than 45% by weight, based on the total weight of reactants used to make the polyurethane.

Embodiments of the present invention are directed to a seed treatment composition of any of the previous three paragraphs, wherein the polymeric polyol of the seed treatment composition has a Mr1 of from 400 to 6000 g/mol, 500 to 3000 g/mol, 1000 to 3000 g/mol or 1500 to 3000 g/mol. ments of the present invention are directed to a seed treatment composition of any of the us four aphs, wherein the polymeric polyol of the seed treatment composition has a hydroxyl number of from 20 to 400 mg KOH/g of substance, such as 20 to 300 mg KOH/g of nce, 20 to 200 mg KOH/g of substance or 20 to 100 mg KOH/g of substance.

Embodiments of the present ion are directed to a seed treatment composition of any of the previous five paragraphs, wherein the polymeric polyol of the seed treatment composition has a hydroxyl onality of 1.5 to 6, such as 1.8 to 3 or 1.9 to 2.1.

Embodiments of the present invention are directed to a seed treatment composition of any of the previous six paragraphs, wherein the ric polyol of the seed treatment composition comprises a polyester polyol, a polyacrylate polyol, a polyurethane polyol, a polycarbonate polyol, a polyether , a polyester polyacrylate polyol, a polyurethane polyacrylate polyol, a polyurethane ter polyol, a polyurethane polyether polyol, a polyurethane polycarbonate polyol, a polyester polycarbonate polyol, a phenol/formaldehyde resin, or a mixture thereof.

Embodiments of the present invention are directed to a seed treatment composition of the previous paragraph, wherein the polymeric polyol of the seed treatment composition comprises, consists essentially of, or, in some cases, consists of a polyester polyol, such as a ter polyol that is a on t of butanediol and/or neopentyl glycol and/or hexanediol and/or ethylene glycol and/or diethylene glycol with adipic acid and/or phthalic acid and/or isophthalic acid, such as polyester polyols that are a reaction product of butanediol and/or tyl glycol and/or hexanediol with adipic acid and/or phthalic acid.

] Embodiments of the present invention are directed to a seed treatment composition of either of the previous two paragraphs, wherein the polyester polyol of the seed treatment composition has a hydroxyl functionality of 1.5 to 6.0, such as 1.8 to 3.0, a hydroxyl number of 20 to 700 mg KOH/g solid, such as 20 to 100, 20 to 80 or, in some cases 40 to 80 mg KOH/g solid, and/or a Mn of 500 to 3000 g/mol, such as 600 to 2500 g/mol.

Embodiments of the present invention are directed to a seed treatment ition of any of the previous nine paragraphs, n component (ii) of the seed treatment composition is included in an amount of at least 20% by weight, such as at least 30 or at least 40% by weight and/or no more than 80% by weight, such as no more than 70% by weight, based on the total weight of reactants used to make the polyurethane.

Embodiments of the present invention are directed to a seed treatment composition of any of the previous ten paragraphs, n component (iii) of the seed ent composition is a nd comprising consisting essentially of, or, in some cases, consisting of, carboxylate, sulfonate, and/or phosphonate groups or groups which can be converted into the above-mentioned groups by salt formation.

Embodiments of the present invention are directed to a seed treatment composition of the previous paragraph wherein the compound (iii) of the seed treatment composition comprises, consists essentially of, or, in some cases, consists of, a mono— and di—hydroxycarboxylic acid, a mono— and di- aminocarboxylic acid, a mono- and roxysulfonic acid, a mono— and di— aminosulfonic acid, a mono- and di-hydroxyphosphonic acid and/or a mono- and di—aminophosphonic acids or a salt thereof, such as dimethylolpropionic acid, dimethylolbutyric acid, hydroxypivalic acid, N-(2-aminoethyl)-B-alanine, 2—(2- amino-ethylamino)—ethanesulfonic acid, ethylene-diamine-propyl- or —butyl- sulfonic acid, 1,2- or 1,3-propylenediamineethylsulfonic acid, malic acid, citric acid, glycolic acid, lactic acid.

Embodiments of the t invention are directed to a seed treatment composition of any of the previous twelve paragraphs, wherein component (iii) of the seed treatment composition is included in an amount of at least 0.1% by weight, such as at least 1, or at least 3% by weight and/or no more than 10% by , such as no more than 7% by weight, based on the total weight of reactants used to make the polyurethane.

] Embodiments of the present invention are directed to a seed treatment ition of any of the previous thirteen paragraphs, wherein component (iv) of the seed treatment composition is included and ses a compounds of the formula: H—Y'—X—Y—R, in which R is a monovalent hydrocarbon l having 1 to 12 carbon atoms, such as an unsubstituted alkyl radical having 1 to 4 carbon atoms; X is a polyalkylene oxide chain having 5 to 90, such as 20 to 70 chain members, which may comprise at least 40%, such as at least 65%, ethylene oxide units and which in addition to ethylene oxide units may comprise propylene oxide, butylene oxide and/or styrene oxide units; and Y and Y‘ are each independently oxygen or —NR'— in which R' is H or R, in which R is defined above.

Embodiments of the present invention are directed to a seed ent composition of the previous paragraph, wherein component (iv) of the seed treatment composition contains 7 to 55 ethylene oxide units per molecule.

Embodiments of the present invention are directed to a seed treatment composition of either of the previous two paragraphs, wherein component (iv) of the seed treatment ition comprises, consists essentially of, or, in some cases, consists of, a copolymer of ethylene oxide with propylene oxide that contains ethylene oxide in an amount of at least 40% by weight, such as at least 50% by , at least 60% by weight or at least 65% by weight and/or up to 90% by weight or up to 80% by weight, based on the total weight of ne oxide and propylene oxide.

Embodiments of the present invention are directed to a seed treatment composition of any of the previous three paragraph, wherein the Mn of such a copolymer is 300 g/mol to 6000 g/mol, such as 500 g!mol to 4000 g/mol, such as 1000 g/mol to 3000 g/mol.

Embodiments of the present invention are directed to a seed treatment ition of any of the previous four paragraphs, wherein component (iv) of the seed treatment composition is included in an amount of at least 1% by weight, such as at least 5, or at least 10% by weight and/or no more than 30% by weight, such as no more than 20% by weight, based on the total weight of reactants used to make the polyurethane.

Embodiments of the present invention are directed to a seed treatment composition of any of the previous seventeen paragraphs, wherein component (v) of the seed treatment composition is included and, in some embodiments, is used in an amount of at least 1% by weight, such as at least 2, or at least 3% by weight and/or no more than 20% by weight, such as no more than or no more than 5% by weight, based on the total weight of reactants used to make the polyurethane.

Embodiments of the present invention are directed to a seed treatment composition of any of the previous en paragraphs, wherein component (vi) of the seed composition is included and comprises, consists essentially of, or, in some cases, consists of, a di- or poly-amine, a hydrazide, an aminoalcohol, or a mixture thereof and, in some embodiments, component (6) of the seed treatment composition is ed in an amount of at least 1% by weight, such as at least 3 or at least 5% by weight and/or no more than 10% by weight, such as no more than 8 or, in some cases, no more than 7% by weight, based on the total weight of reactants used to make the ethane.

Embodiments of the present invention are ed to a seed ent composition of any of the previous nineteen paragraphs, wherein the sum of components (i)-(vi) of the seed treatment composition is 100 percent by weight, based on the total weight of the reactants used to make the polyurethane.

] Embodiments of the present invention are directed to a seed treatment composition of any of the us twenty paragraphs, wherein the seed treatment composition comprises a blend of (A) an anionic aliphatic polyester- polyurethane dispersion that is a reaction product of components (i), (ii), (iii), (v), and (vi) bed above and/or (B) which is ent from (A) is an aliphatic, polyester-based, anionic polyurethane dispersion and is a reaction product of components (i), (ii), (iii), (v), and (vi) described above and/or (C) an anionic/non- ionic ter polyurethane dispersed in water and is a reaction product of ents (i), (ii), (iii), (iv), and (vi) described above. In certain embodiments, the weight ratio of the aqueous polyurethane dispersions in the blend of the seed treatment compositions of the present invention is (A+B)/(C) is r than 1:1, such as greater than 2: 1.

Embodiments of the present invention are directed to a seed treatment composition of any of the previous twenty-six paragraphs, wherein the aqueous polyurethane dispersion of the seed treatment composition is present in the treatment composition in an amount such that the total amount of polyurethane that is present in the treatment composition is at least 1%, such as at least 2% or in some cases at least 4% and/or no more than 20%, such as no more than 15% and in some cases, no more than 10%. ] ments of the present invention are directed to a seed treatment composition of any of the previous twenty-seven paragraphs, wherein the insecticide, fungicide, nematicide, and/or other pesticides ses acetamiprid, clothianidin imidacloprid, thiacloprid, thoxam, abamectin, emamectin, emamectin-benzoate, rynaxypyr (chloroantraniliprole), cyazypyr (cyntraniliprole), spinetoram, spinosad, sulfoxa?or, lambda—cyhalothrin, beta— cy?uthrin, te?uthrin, ?upyradifurone, tetraniliprole, Bacillus firmus CNCM I 1582, Bacillus subtilis QST 713, Bacillus subtilis AQ30002, oconazole, metalaxyl, mefenoxam, benalaxyl, kiralaxyl, tri?oxystrobin, azoxystrobin, strobin, pyraclostrobin, ?uopyram, thiram, tebuconazole, onil, and ipconazole.

Embodiments of the present invention are directed to a seed treatment composition of any of the previous —eight paragraphs, wherein the insecticide, fungicide, nematicide, and/or pesticide is present in the treatment compositions of the present invention in an amount of at least 15%, such as at least 20%, such as at least 25%, such as at least 30% and/or no more than 80%, such as no more than 75%, such as no more than 60%, such as no more than 50%.

Embodiments of the present ion are directed to a seed treatment composition of any of the previous twenty-nine aphs, wherein the seed treatment composition comprises an inorganic lubricant and/or an organic lubricant, such as a wax, such as a polyethylene wax. ments of the present invention are directed to a method of using a seed treatment composition of any of the previous thirty paragraphs, comprising applying the seed treatment composition to a seed, such as at the same time or before the planter fills the planter hopper with seed or as a farmer fills the planter hopper with seed.

Embodiments of the present invention are directed to a method of the previous paragraphs, wherein the hopper forms a component part of a planter, such as an air or vacuum planter, with a planter mechanism.

Embodiments of the present invention are ed to a method of either of the previous two paragraphs, wherein the method increases the t singulation during planting by at least 0.2%, such as at least 0.5%, relative to the use of an identical seed treatment ition in which a polyolefin latex, such as a carboxylated styrene/butadiene polymer, is used as the polymeric component of the seed treatment composition when comparing the same type of seed.

Embodiments of the present invention are directed to a method of any of the previous three paragraphs wherein the seed ent composition is applied to a seed at a rate of 0.1 - 5.0 oz/cwt (ounces/hundredweight), 0.5 - 4.0 oz/cwt, 1.0 - 3.5 oz/cwt, 1.5 - 3.0 oz/cwt, 2.0 - 3.0 oz/cwt, 2.0 - 2.5 oz/cwt, or 0.2 ozfcwt, 0.5 oz/cwt, 0.75 oz/cwt, 1.0 oz/cwt, 1.5 oz/cwt, 2.0 oz/cwt, 2.5 oz/cwt, 3.0 oz/cwt, 3.5 , 4.0 oz/cwt, 4.5 , 5.0 oz/cwt, or 0.2 oz/cwt or more, 0.5 oz/cwt or more, 0.75 oz/cwt or more, 1.0 oz/cwt or more, 1.5 oz/cwt or more, 2.0 oz/cwt or more, 2.5 oz/cwt or more, 3.0 oz/cwt or more, 3.5 oz/cwt or more, 4.0 ozfcwt or more, 4.5 oz/cwt or more, or 5.0 oz/cwt or more.

Embodiments of the present invention are directed to a method of any of the previous four paragraphs wherein the seed treatment composition is applied to a seed in a single application step or in le application steps, such as one, two, three or more application steps.

Embodiments of the present invention are directed to seeds treated by a method of any of the previous five paragraphs, wherein the seed comprises corn seed, cotton seed, sorghum seed, oat seed, rye seed, barley seed, soybean seed, vegetable seed, wheat seed, eat seed, rice, sun?ower seed, lettuce seed, and/or spinach seed, such as sweet corn (for e, zea mays convar. saccharata var. ), silver queen corn, golden bantam, early sunglow, Indian corn, sugar corn, pole corn, field corn, dent corn, ?int corn, ?our corn, blue corn (for example, Zea mays amylacea), popcorn, and waxy corn.

Embodiments of the present invention are directed to a kit sing, ting essentially of, or consisting of any of any of the treatment compositions disclosed herein, such as where the kit provides instructions or guidance regarding the use of any of the compositions or methods described herein.

Embodiments of the present invention are also directed to use of any of the compositions described herein to increase the percent singulation during ng of a seed, such as any of the seeds described above, by applying a composition described herein to a seed.

EXAMPLES Example 1 Seed treatment compositions were prepared using the ingredients and amounts (in milliliters) listed in Table 1. In each case, the listed ingredients were added to a le container and then mixed using a glass rod r until a homogeneous mixture was obtained.

Table 1 Example Ingredient 1A 1C Active ingredient e1 27.91 27.92 27.92 27.92 Water 21.77 Commercial polymeric seed coating2 22.18 -- -- -- -- -- Seed coating blank3 -- IMMAM -- II— Table 1 {continuedl Example Active ingredient mixture1 27.91 Seed coating blank3 17.17 17.17 17.17 17.17 17.17 IMPRANIL DL 26116 —— --— DISPERCOLL U xp 26998 4.48 --_ DISPERCOLL C 849 -- --_ BAYBOND PU 33010 -- --_ IMPRANIL XP 153711 —— --— 1 A liquid mixture of VORTEX ide, TRILEX fungicide, /VOTIVO insecticide, and red dye, Bayer CropScience LLP. 2 PERIDIAM SEED FINISHER 1006, Bayer CropScience LLP, which is multifunctional seed g that is a al mixture composed of a dispersion of a binder comprising carboxylated styrene—butadiene polymer in water, along with other ingredients, such as suspending agents, surfactants, emulsifiers, dispersants, pigments, antimicrobial preservatives, and wax powder. 3 Same composition as Commercial polymeric seed coating but without the presence of the carboxylated styrene—butadiene polymer binder. 4 An anionic aliphatic polyether/polycarbonate polyurethane dispersion in water, 60% by weight non—volatile content, Covestro LLC.

An c aliphatic polyester-polyurethane dispersion in water, 40% by weight non—volatile t, ro LLC, which was used as a comparative example — See US. Published Patent ation No. 2014/0274685 A1. 6 An anionic aliphatic polyester-polyurethane dispersion in water, 40% by weight non-volatile content, Covestro LLC. 7 A non—ionic polyurethane polymer dispersed in water, 34.5% by weight volatile content, Covestro LLC. aqueous polyurethane dispersion, 55% by weight polymer content, Covestro aqueous dispersion of poly-2—chlorobutadiene—1,3, 55% by weight polymer content, Covestro LLC.

An anionic/non—ionic polyester polyurethane resin dispersed in water, 30% by weight non—volatile content, Covestro LLC. 11 An anionic ter polyurethane resin dispersed in water, 60% by weight volatile content, Covestro LLC.

Treatment of Com Seeds For each of the compositions of Examples 1A-1J, 3.31 pounds (1.5 kg) of corn was placed into a laboratory seed treater bowl equipped with a foot pedal to spin the bowl. While the bowl was spinning, 15.7 mL of the seed treatment composition was added to the treater using a 25 mL c syringe.

Once the seed treatment composition was added and thoroughly mixed with the corn for about 30 to 60 seconds, the corn was discharged from the treater. Seed treatments for each composition was done twice for each type of corn (Seed A and Seed B) to obtain 6.62 pounds (3.0 kg) of d corn seeds. "Seed A" refers to hybrid dent corn seed of 1564 seeds per pound with a size of 25\20 F (?at). "Seed B" refers to hybrid dent corn seed of 1729 seeds per pound with a size of 20\16 R (round).

Each of the Examples 1E, 1K, and 1L had the same composition, but the seed treatment s differed. The seed treatment process for Example 1E was as described above.

In the case of Example 1K, 3.31 pounds (1.5 kg) of corn was placed into a laboratory seed treater bowl equipped with a foot pedal to spin the treater bowl. A mixture of the water and IMPRANIL DL 2611 dispersion was pre-made, while the other seed ent components (the active ingredient mixture and seed coating blank) were combined separately. While the bowl was spinning, 9.9 mL of active ingredient mixture and seed coating blank combination was first added to the treater containing the spinning corn seed. Then, 5.7 mL of the water and IL DL 2611 dispersion combination was added to the corn seed under spinning using a 25 mL plastic syringe. The treated corn seed was thoroughly mixed for about 30 to 60 seconds, and the corn was discharged from the treater. Seed treatments were done twice for each type of corn (Seed A and Seed B) to obtain 6.62 pounds (3.0 kg) of d corn seeds.

In the case of Example 1L, 3.31 pounds (1.5 kilogram) of corn was placed into a laboratory seed treater bowl equipped with a foot pedal to spin the treater bowl. A mixture of the seed coating blank and IMPRANIL DL 2611 dispersion was pre-made, while the other seed treatment components (the active ingredient e and water) were combined separately. While the bowl was spinning, 10.6 mL of active ingredient/water mixture was first added to the treater containing the spinning corn seed. Then, 5.1 mL of the seed coating blank/IMPRANIL DL 2611 dispersion combination was added to the corn seed under spinning using a 25 mL plastic syringe. The treated corn seed was thoroughly mixed for about 30 to 60 s, and the corn was discharged from the r. Seed treatments were done twice for each type of corn (Seed A and Seed B) to obtain 6.62 pounds (3.0 kg) of d corn seeds.

The treated corn seed was tested for wet and dry ?owability, dust, and plantability. Wet ?owability was ined by passing 6.62 pounds (3.0 kg) of freshly treated corn seed through a test funnel having a 1 5/8 inch diameter orifice. Flowability was determined as the time (in seconds) that it took for all of the corn to pass through the funnel. Recorded results are the e of three measurements. Dry ?owability was determined in the same manner as wet flowability except that the test was conducted 24 hours after the seed treatment was completed. Dust (reported as grams of dust per 100 grams of corn seed) was measured using a Heubach Dustmeter (Type 1) according to German Industry Standard DIN 55 992, Part 1. Percent singulation was determined with a METERMAX Ultra Test Stand from Precision Planting LLC having a John Deere MAXEMERGE Vacuum Meter attached. Three runs of 1000 seeds each were conducted and the recorded results re?ect the average of the three runs. The test stand parameters were set to simulate the planting of 35,000 seeds per acre (4046 m2) at a speed of 5 miles (8.05 km) per hour with 30 inch (76.2 cm) rows. Results are set forth in Table 2.

Table 2 Wet Flow Dry Flow Dust Percent Singulation Example Seed A Seed B Seed A Seed B Seed A Seed B 1A 15.37 12.32 0.0005 0.0002 99.2 99.5 1B 16.43 13.04 0.0032 0.0022 97.8 99.2 1C 17.51 13.17 0.0005 0.0005 96.2 98.7 1D 16.87 12.70 0.0003 0.0004 95.1 98.8 1E 16.49 12.17 0.0007 0.0006 99.0 99.7 1F 16.86 16.29 13.13 12.65 0.0010 0.0008 98.3 99.5 1G 17.10 16.27 13.85 13.31 0.0013 0.0008 88.4 98.1 1H 17.49 12.98 0.0006 0.0004 93.5 98.8 11 17.18 12.72 0.0004 0.0002 78.2 96.4 11 15.74 12.32 0.0006 0.0006 97.7 99.6 1K 15.17 11.80 0.0007 0.0004 98.7 99.7 1L 14.90 11.92 0.0005 0.0005 99.1 99.8 Seed treatment compositions were prepared using the ingredients and amounts (in milliliters) listed in Table 3. In each case, the listed ingredients were added to a suitable container and then mixed using a glass rod stirrer until a homogeneous mixture was obtained.

Table 3 Example Ingredient 2A 2B 2C Active ingredient mixture1 27.91 27.92 27.92 Commercial polymeric seed coating2 22.18 ---- Seed coating blank3 -- BAYHYDROL UH XP 271912 -- -- 5.90 5.90 5.90 12 An aliphatic, polyester—based, c polyurethane sion in water, 40% by weight non-volatile content, Covestro LLC. ent of Corn Seeds For each of the compositions of Examples 2A-2C, corn seeds were treated in the manner bed above for Examples 1A-1J .

In the case of Example 2D, 3.31 pounds (1.5 kg) of corn was placed into a laboratory seed treater bowl equipped with a foot pedal to spin the treater bowl. A mixture of the water and BAYHYDROL UH XP 2719 dispersion was pre-made, while the other seed treatment components (the active ingredient mixture and seed coating blank) were combined separately. While the bowl was spinning, 9.9 mL of the active ingredient/seed coating blank mixture was first added to the treater containing the ng corn seed. Then, 5.7 mL of the water/ BAYHYDROL UH XP 2719 dispersion combination was added to the corn seed under spinning using a 25 mL plastic syringe. The treated corn seed was mixed thoroughly for about 30 to 60 seconds, and the corn was rged from the treater. Seed treatments were done twice for each type of corn (Seed A and Seed B) to obtain 6.62 pounds (3.0 kg) of treated corn seeds.

In the case of Example 2E, 3.31 pounds (1.5 kg) of corn was placed into a laboratory seed treater bowl ed with a foot pedal to spin the treater bowl. A mixture of the seed g blank and BAYHYDROL UH XP 2719 dispersion was pre-made, while the other seed treatment components (the water and the active ingredient mixture) were combined separately. While the bowl was spinning, 10.6 mL of the active ient mixture/water combination was first added to the treater containing the spinning corn seed. Then, 5.1 mL of the seed coating blank/BAYHYDROL UH XP 2719 dispersion combination was added to the corn seed under ng using a 25 mL plastic syringe. The treated corn seed was mixed thoroughly for about 30 to 60 s, and the corn was discharged from the treater. Seed treatments were done twice for each type of corn (Seed A and Seed B) to obtain 6.62 pounds (3.0 kg) of treated corn seeds. "Seed A" and "Seed B" were as described in Example 1.

The treated corn seed was tested for wet ?owability, dry ?owability, dust, and plantability as described above in Example 1. Results are set forth in Table 4.

Table 4 Wet Flow Percent Singulation Example 3 Seed treatment itions were prepared using the ingredients and amounts (in milliliters) listed in Table 5 using the procedure described above in Example 1.

TableS Example Ingredient 3A 3B 3C 3E 3F 3G Active ingredient mixturel 27.91 27.92 27.92 27.92 27.92 27.92 27.92 Water 21.77 25.89 21.01 21.19 2119o 20.66 21.45 Commercial polymeric seed coating2 22.18 -— 1 Seed coating blank3 -- 17.17 17.17 17.17 ,_I q . ,d \] 17.17 17.17 STYROFAN NX 6690 X13 -- __ .‘P 00 00 IMPRANIL LP DSB 106914 -— -_ __ :D‘ \JO DISPERCOLL U 5415 -- -- -- -- 4.70 __ __ DISPERCOLL U 875516 -- -- __ I I S"NU.) I I IMPRANIL DL 26116 -- -_ __ .4>A4; Table 5 gcontinuedg Example Ingredient 3H 31 3J 3L 3M 3N Active ingredient mixturel 27.93 27.92 27.92 27.92 27.92 27.92 27.92 Water 19.10 17.55 18.04 19.41 18.53 Seed coating blank3 17.17 17.17 17.17 17.17 17.17 DPU33010 2.88 3.02 6.21 -_ —— ROLUHXP271912 1.95 5.32 —— - 4.44 7.36 2.13 IMPRANILDL26116 1.95 —— 1.64 -_5.23 Table 5 {continued[ Example Ingredient 3O 3P 3Q 3R SS 3T 3U Active ingredient niixtuie1 27.92 27.91 27.92 27.93 27.93 27.92 27.91 Water 18.53 18.53 15.95 17.64 Seed g blank3 17.17 17.17 17.17 17.17 17.17 17.17 17.17 BAYBOND PU 33010 -- -- 8.12 2.88 -- 1.95 2.71 BAYHYDROL UH XP 271912 —— 5.37 1.82 1.95 1.15 3.11 —— IMPRANIL DL 26116 7.36 2.00 —— 1.95 3.28 —— 5.55 Table 5 gcontinued; Example Ingredient 3V 3W 3X 32 3AA 31313 Active ingredient e1 27.92 27.92 27.92 27.92 27.93 27.91 27.91 Water 21.45 20.83 20.43 15.07 16.00 Seed coating b1ank3 17.17 17.17 17.17 17.17 17.17 BAYBOND PU 33010 —— 1.95 3.24 10.82 7.90 BAYHYDROL UH XP 271912 3.11 —— 1.11 -_ —— IMPRANIL DL 26116 1.33 3.11 1.11 - —— 1.95 2.00 13 Carboxylated styrene/butadiene dispersion in water, 52-53% by weight solids content, BASF Corporation. 14 An anionic, aliphatic, polyether—polyurethane dispersion in water, 50% by weight non—volatile content, Covestro LLC.

An aqueous anionic dispersion of a polyurethane, 50% by weight non-volatile content, Covestro LLC. 16 An aqueous anionic dispersion of a polyurethane, 45% by weight non-volatile t, Covestro LLC. ent of Corn Seeds For each of the compositions of Examples 3A-3BB, corn seeds were treated in the manner described above for Examples lA-lJ. "Seed A" and "Seed B" were as described in Example 1. The treated corn seed was tested for wet ?owability, dry flowability, dust, and plantability as described above in Example 1. Results are set forth in Table 6.

Table6 Wet Flow Dr Flow Dust Percent Sin_ulati0n Exam-1e SeedA 3A 15.56 12.80 0.0004 0.0002 98.7 99.? 33 16.55 13.25 0.0024 0.0014 97.9 99.2 3C 15.52 12.77 0.0003 0.0002 99.4 99.? 3D 16.70 13.44 0.0003 0.0002 95.6 99.1 3E 17.01 13.14 0.0011 0.0005 96.8 99.7 3F 17.27 13.08 0.0007 0.0006 97.5 99.4 36 16.31 12.54 0.0005 0.0005 98.8 99.7 3H 17.04 13.07 0.0004 0.0003 98.5 99.6 31 16.38 15.67 13.85 13.02 0.0009 0.0006 98.1 99.7 31 17.40 16.01 14.31 12.97 0.0001 0.0002 97.0 99.4 3M 17.00 13.61 0.0038 0.0023 98.1 99.2 3N 16.48 15.45 13.77 12.80 0.0004 0.0006 98.7 99.8 16.54 15.01 13.32 12.53 0.0005 0.0004 98.8 99.7 3P 16.95 15.73 14.06 13.38 0.0015 0.0016 98.0 99.7 3Q 17.69 15.27 14.45 12.93 0.0003 0.0001 88.5 98.3 3R 16.46 12.72 0.0002 0.0002 98.5 99.7 38 16.35 12.78 0.0006 0.0006 98.6 99.6 3T 17.17 13.16 0.0014 0.0011 97.5 99.3 3U 16.95 15.10 13.30 12.57 0.0001 0.0006 98.7 99.8 3V 17.05 15.59 14.12 13.12 0.0016 0.0008 97.5 99.8 3W 16.84 12.99 0.0004 0.0004 98.4 99.9 3X 17.15 16.03 13.91 13.19 0.0004 0.0003 97.7 99.8 3Y 18.78 16.36 14.44 13.45 0.0001 0.0001 71.7 94.2 32 17.18 13.12 0.0005 0.0001 94.3 99.4 3AA 16.27 13.28 0.0006 0.0002 98.2 99.6 31313 16.78 13.26 0.0002 0.0002 90.9 98.5 -5 6- Example 4 Seed treatment compositions were ed using the ingredients and amounts (in milliliters) listed in Table 7 using the ure described above in Example 1.

Example Ingredient 4A 4B 4C n 4E 4F 4G Active ingredient mixturel 27.92 27.92 27.92 27.92 27.92 27.92 27.92 Water 20.88 25.89 19.99 22.92 20.39 19.59 22.74 Commercial polymeric seed coating2 22.18 -- -- Seed coating blank3 —— 17.17 17.17 17.17 17.17 17.17 17.17 Polyethylene Wax17 -- -- -- - 2.53 -— -— D PU 33010 -— —— —— —— —— 1.29 0.67 IMPRANIL DL 26116 -- -- 5.90 2.97 2.97 5.01 2.48 Table 7 gcontinuedl Example Ingredient 4H 41 4J 4N Active ingredient mixturel 27.92 27.92 27.92 27.92 Water 20.21 18.70 22.30 19.77 19.81 Seed coating blank3 17.17 17.17 17.17 17.17 17.17 PolyethyleneWax" 2.53 —— —— 2.53_ 2.53 DPU33010 0.67 4.26 2.13 2.13 1.91 BAYHYDROL UH XP 271912 -- -- -- -_0.31 IMPRANILDL26116 2.48 2.93 1.46 1.46 1.33 17 MICHEM Wax 437, Michelman, Inc.

Treatment of Com Seeds For each of the compositions of Examples 4A-4N, corn seeds were treated in the manner described above for Examples 1A-1J. "Seed A" and "Seed B" were as described in Example 1. "Seed C" refers to hybrid dent corn seed of 2034 seeds per pound with a size of 20\16 F (?at). The d corn seed was tested for wet ?owability, dry ?owability, dust, and plantability as described above in Example 1. Results are set forth in Table 8.

Table8 Example Seed A Seed B Seed C 4A 16.09 16.13 15.74 13.44 13.18 13.17 43 17.02 16.63 13.86 14.10 14.46 4D 16.79 16.66 16.39 13.74 13.62 13.70 4E 13.97 14.09 14.06 4F 16.45 16.52 16.56 13.69 13.58 13.54 4G 13.92 13.59 13.99 4K 16.93 16.95 17.25 14.04 13.75 14.28 4L 14.10 13.72 14.13 Table 8 {continued} "7.3mm Example Seed A Seed B Seed C 4A ---0.0004 0.0003 0.0008 98.7 99.2 96.9 4B ---0.0024 0.0020 0.0056 97.6 97.4 91.7 40 0.0005 0.0005 98.9 98.2 96.9 4D 0.0008 0.0007 0.0029 98.3 98.8 95.7 4E 0.0008 0.0009 0.0027 98.8 98.5 95.9 4F 0.0010 0.0004 0.0013 98.8 98.8 96.4 4G 0.0010 0.0007 0.0021 98.4 98.8 95.1 4H 0.0008 0.0008 0.0020 98.1 98.4 94.1 41 0.0007 0.0004 0.0009 98.0 98.1 94.5 4] ---0.0009 0.0006 0.0018 97.4 98.6 94.1 4K 0.0007 0.0011 0.0016 98.3 98.4 94.8 4L 0.0004 0.0004 0.0010 97.8 97.9 92.7 4M ---0.0012 0.0010 0.0020 94.0 4N 0.0009 0.0012 0.0021 98.0 98.4 94.7 Example 5 Films were produced from various polymeric dispersions using the ingredients and amounts (percent by weight based on resin solids) listed in Table 9. For evaluation of microhardness and glass transition temperature, a test sample was prepared by applying 8 mils (203 um) wet film thickness of the formulation onto a 3" x 6" glass panel. The formulation was left to dry for 24 hours after ation. Microhardness (Marten’s hardness) measurements were done using Fischerscope H100C instrument with the method described in DIN 14577. ardness readings were taken under a 30 mN test load run to a maximum of pm indentation depth over a 20 second application time. Results reported are an e of three readings for each formulation. Glass transition temperature (Tg) was evaluated using Differential ng calorimetry (DSC) conducted with Perkin Elmer DSC7 using a liquid nitrogen bath. The samples were evaluated from -100°C to 1000C, cooled, and reheated using a 200C/minute ramp rate. For evaluation of tensile strength and percent elongation, samples were prepared by applying 10 mils (254 um) wet film thickness of the formulation onto a 6" X 12" glass panel. The formulation was left to dry for 24 hours after application. The panel was then soaked in warm water to peel it from the glass substrate. Once peeled, the film was dried with a paper towel. Using a die , dog-bone samples were cut and tensile th and percent elongation were measured using an INSTRON 4444 apparatus at a grip distance of 2.5" at a ead speed of 20 inch/minute. Results reported for percent elongation and tensile strength are an average of three readings for each formulation. Results are set forth in Table 9.

Table 9 Ingredient 5A 5B STYROFAN NX 6690 X13 100 -- IL DLU4 -- 100 IMPRANIL DLN5 -- __ IMPRANIL DL 26116 -- __ BAYBOND PU 4067 -- __ DISPERCOLL U XP 26998 -- __ DISPERCOLL C 849 -- __ Test Results Fischer Microhardness ) 2.3 1.1 Glass tion Temperature (0C) 11 -65 Percent Elongation 301 700 1082 3600 1200 Tensile Strength (lb/in2(kg/cm2)) (76) (253) (84) Table 9 {continuedg Example Ingredient 5H 51 SJ SL SM 5N IMPRANIL DL 26116 —— -— —— -_ 33 BAYBOND PU 33010 100 —— —— -_ 33 IMPRANIL XP 153711 -— 100 -— -_ —- BAYHYDROL UH XP 271912 —— —— 100 -_ 33 IMPRANIL LP DSB 106914 -- -— -— 100_ —- DISPERCOLL U 5415 -- -— -— 100 DISPERCOLL U 875516 —— -- __ _- 100 —— Test Results Fischer Microhardness ) 0.4 0.7 Glass Transition Temperature (0C) —48 —4 Percent tion 700 650 130 2175 2471 2900 5600 3400 1335 Tensile th (lb/in2(kg/cm2)) (9) (153) (174) (204) (394) (239) (94) Table 9 gcontinued) Ingredient 50 SP IMPRANIL DL 26116 -- 28 BAYBOND PU 33010 28 72 BAYHYDROL UH XP 271912 72 -- Test Results Fischer Microhardness (N/mmz) 20.1 0.7 Glass Transition Temperature (0C) -46 -47 Percent Elongation 300 255 2452 377 Tensile Strength (lb/in2(kg/cm2)) (172) (27) Table 9 gcontinued! Ingredient 5V 5W IL DL 26116 75 30 BAYBOND PU 33010 25 -- BAYHYDROL UH XP 271912 -- 70 Test Results Fischer Microhardness (N/mmz) 4.5 344 Glass Transition Temperature (0C) -45 -42 Percent Elongation 262 210 3156 4688 2382 942 Tensile Strength (1b/in2(kg/cm2)) (222) (330) (167) (66) Table 9 nuedg Example Ingredient SCC SDD IMPRANIL DL 26116 50 45 BAYBOND PU 33010 50 45 BAYHYDROL UH XP 271912 -- 10 Test Results Fischer Microhardness (Nimmz) 2.5 3.7 Glass Transition Temperature (0C) -55 -55 Percent Elongation 383 364 927 1 176 e th (lb/in2(kg/cm2)) (65) (83) * A film sufficient for percent elongation and tensile strength evaluation was not produced.

Example 6 The data from Examples 1-4 was analyzed using multivariable regression analysis using JMP 11.1 software (SAS Institute, Cary, NC). Each model was built with the resin loading and the treatment (PUD or blend of PUD’s) as main effects, with ng on Example number and seed type (only type A and type B were used). Because of the nature of the data, the following transformations of the responses were used: (i) log of the dust and (ii) logit of singulation. No transformation was used for the ?ow data. Using the estimated parameters from the model, a predicted response was generated for each treatment at a loading of 17 g resin per 100 pounds of corn. Results are set forth in Table Table 10 Example Ingredient 6A 6B -m 6E AN NX 6690 X13 100 -- Blank -- __ IMPRANIL DLU4 -- __ IMPRANIL DLN5 -- __ IMPRANIL DL 26116 -- __ BAYBOND PU 4067 -- __ COLL U XP 26998 -- —— Test s Wet Flow (seconds) 15.55 16.48 17.31 16.64 15.6 16.82 Dry Flow (seconds) 12.75 13.34 13.92 13.22 12.7 13.39 Dust .00029 .001 .00035 .00029 .00045 .00064 Percent singulation 99.43 98.18 97.90 97.76 99.45 99.18 Table 10 nuedg Example Ingredient 6H 61 (SJ 6K 6L 6M 6N DISPERCOLL C 849 100 _— -- -- BAYBOND PU 33010 —- 100 —— _ -- -- IMPRANIL XP 153711 —— -- 100 _ -- -- BAYHYDROL UH XP 100 —— —— —— 271912 IMPRANIL LP DSB 106914 —— 100 —— —— DISPERCOLL U 5415 —— I—k OO II DISPERCOLL U 875516 -- __ I I I I I I I I )—l OO Test Results WetF10w(seconds) 17.14 16.98 15.89 15.80 16.45 16.20 DryFlow(seconds) 13.85 13.59 13.07 13.18 13.50 13.31 13.39 Dust .00038 .00015 .00045 .00171 .00026 .00073 .00064 Percent singulation 97.45 94.26 99.17 99.16 98.15 99.01 98.80 Table 10 gcontinuedg Ingredient 6O 6P 6U IMPRANIL DL 26116 33 -- 74 BAYBOND PU 33010 33 28 -- BAYHYDROL UH XP 33 72 26 271912 Test Results Wet Flow (seconds) 16.05 15.88 16.60 15.82 16.20 16.33 15.67 Dry Flow (seconds) 13.06 13.16 13.31 13.02 13.45 13.42 12.78 Dust .00028 .00088 .00012 .00058 .00177 .00025 .00048 Percent singulation 99.29 99.33 98.76 99.54 99.38 96.19 99.17 Table 10 nued) Ingredient 6V 6W IMPRANIL DL 26116 -- 75 BAYBOND PU 33010 30 25 BAYHYDROL UH XP 271912 Test Results Wet Flow (seconds) 16.28 15.88 1625 16 17 16.51 16.65 16.44 Dry Flow (seconds) 1321 12.67 1322 1279 13.16 13.26 13.24 Dust 00097 .00029 00090 00032 .00028 .00022 .00024 t singulation 9855 9954 99 17 99.57 99.27 98.23 96.84 Table9continued Example Ingredient SCC SDD SEE IMPRANIL DL 26116 85 50 45 BAYBOND PU 33010 15 50 45 BAYHYDROL UH XP 271912 -- -- 10 Test Results Wet Flow (seconds) 15.96 16.29 16.63 Dry Flow (seconds) 13.04 13.16 13.28 Dust .00052 .00046 .00052 Percent singulation 99.08 99.00 99.10 As a result of the foregoing, it is currently believed that seed treatment compositions comprising: (A) an aqueous ethane dispersion; and (B) an insecticide, a fungicide, a nematicide, and/or other pesticides, wherein the aqueous polyurethane dispersion forms a film exhibiting: (a) a Tg of -48°C to - 4°C, (b) a percent elongation of 44 to 300, (c) a tensile strength of 2500 lb/in2 (17.2 MPa) to 4100 lb/in2 (283 MPa), and (d) optionally a microhardness of up to 45.4 N/mm2 can exhibit significantly seed treatments that significantly improve the percent singulation during planting, such as vacuum planting, as compared to when an identical ent composition is used in which a polyolefin latex, such as a carboxylated styrene/butadiene polymer, is used as the polymeric component of the composition rather than the aqueous polyurethane dispersion or as compared to an identical treatment composition in which no polymeric component is used in the composition.

This specification has been written with reference to s non- ng and non-exhaustive embodiments. However, it will be ized by persons having ordinary skill in the art that various substitutions, modifications, or combinations of any of the sed embodiments (or portions thereof) may be made within the scope of this specification. Thus, it is contemplated and understood that this ication supports additional embodiments not expressly set forth herein. Such embodiments may be obtained, for example, by combining, modifying, or reorganizing any of the disclosed steps, components, ts, features, aspects, characteristics, limitations, and the like, of the various non- ng embodiments described in this specification. In this manner, Applicant(s) reserve the right to amend the claims during prosecution to add features as variously described in this specification, and such amendments comply with the requirements of 35 U.S.C. § 112, first paragraph, and 35 U.S.C. § 132(a).

Claims (14)

WHAT WE CLAIM IS:

1. An aqueous seed treatment composition comprising: (A) an aqueous ethane dispersion e; and (B) one or more insecticides, fungicides, nematicides, and/or other pesticides, wherein the aqueous polyurethane dispersion forms a film ting: (a) a Tg of -48°C to -4°C, (b) a percent elongation of 44 to 300, (c) a tensile strength of 2500 lb/in2 (17.2 MPa) to 4100 lb/in2 (28.3 MPa), and (d) ally a microhardness of up to 45.4 N/mm2, wherein the seed is selected from the group consisting of corn seed, sorghum seed, oat seed, rye seed, barley seed, soybean seed, vegetable seed, wheat seed, sugarbeat seed, rice, sunflower seed, lettuce seed, and spinach seed, wherein the aqueous polyurethane dispersion mixture comprises at least two aqueous polyurethane dispersions; n the at least two polyurethanes are the reaction products of reactants comprising: (i) a polyisocyanate; (ii) a polyester polyol having a number average lar weight of 400 to 8,000 g/mol; (iii) a compound comprising at least one isocyanate-reactive group and an anionic group or potentially anionic group; (iv) a mono functional polyalkylene ether; (v) a polyol having a molecular weight of less than <400 g/mol; and (vi) a polyamine or amino alcohol having a molecular weight of from 32 to 400 g/mol, and wherein the at least two aqueous polyurethane sions comprise (A) an anionic aliphatic polyester-polyurethane that is a reaction product of components (i), (ii), (iii), (v), and (vi); and (B) an c aliphatic polyester-polyurethane, different from (A), that is a reaction product of components (i), (ii), (iii), (v), and (vi); and r comprise (C) an anionic/non-ionic polyester polyurethane that is different from (A) and (B) and is a reaction product of components (i), (ii), (iii), (iv), and (vi), wherein the weight ratio of (A), (B) and (C) in the composition is such that (A+B)/(C) is greater than 1.

2. The composition of claim 1, wherein: (a) the Tg is -48°C to -30°C, (b) the t elongation is 100 to 300, and/or (d) the microhardness is 0.4 to 15 N/mm2.

3. The composition of claim 1, wherein the polyester polyol comprises a polyester diol comprising a reaction product of butanediol, tyl glycol, and/or hexanediol, with adipic acid.

4. The composition of claim 1, wherein the aqueous polyurethane sion e is present in the treatment composition in an amount such that the total amount of polyurethane that is present in the treatment composition is 1% to 20% by weight.

5. The composition of any one of claims 1 to 4, wherein the one or more insecticides, fungicides, nematicides and/or other pesticides ses iprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, and/or abamectin.

6. The composition of any one of claims 1 to 5, wherein the one or more insecticides, fungicides, nematicides and/or other pesticides is present in the treatment compositions in an amount of 15% by weight to 60% by weight.

7. The composition of any one of claims 1 to 6, further comprising a polyethylene wax.

8. A method of treating a seed with the composition of any one of claims 1 to 7, comprising applying the ition to a seed.

9. The method of claim 8, wherein the seed comprises corn seed, sorghum seed, oat seed, rye seed, barley seed, soybean seed, vegetable seed, wheat seed, sugarbeat seed, rice, sunflower seed, lettuce seed, or spinach seed.

10. The method of claim 8, wherein the seed comprises corn seed.

11. A seed treated by the method of claim 8.

12. A composition according to claim 1, substantially as herein described or exemplified.

13. A method according to claim 8, substantially as herein described or ified.

14. A seed according to claim 11, substantially as herein described or exemplified.