阅读说明：本技术 苯唑草酮的含水组合物 (Aqueous compositions of topramezone ) 是由 S·狄更斯 D·A·奥斯特 于 2019-08-12 设计创作，主要内容包括：本发明涉及一种包含苯唑草酮的含水除草组合物。本发明特别涉及一种苯唑草酮在有或没有助剂的缓冲溶液中的水溶液。本发明还涉及这些组合物在作物和非作物中控制不希望的植物生长的用途。(The present invention relates to an aqueous herbicidal composition comprising topramezone. The invention particularly relates to an aqueous solution of topramezone in a buffer solution with or without an auxiliary agent. The invention also relates to the use of these compositions for controlling undesirable vegetation in crops and non-crops.)

1. An aqueous composition comprising 0.1 to 1.0 wt% topramezone or an agriculturally acceptable salt thereof, based on the total weight of the aqueous composition, wherein the pH of the composition is in the range of 6.5 to 7.5.

2. An aqueous composition according to claim 1, wherein the amount of topramezone or an agriculturally acceptable salt thereof is in the range of from 0.1 to 0.5% by weight, based on the total weight of the aqueous composition.

3. An aqueous composition according to claim 1, wherein the pH of the composition is in the range of 6.8-7.2.

4. An aqueous composition according to claim 1, wherein the pH of the composition is in the range of 6.9-7.1.

5. An aqueous composition according to claim 1, comprising at least one buffering agent.

6. The aqueous composition according to claim 5, wherein the at least one buffer is selected from the group consisting of phosphate buffers, phosphate-acetate buffers, citrate-phosphate buffers, BES (N, n-bis (2-hydroxyethyl) -2-aminoethanesulfonic acid) buffered saline, EBSS (Earle balanced salt solution) buffer, Hanks balanced buffer solution, HEPPSO (N- (2-hydroxyethyl) piperazine-N' - (2-hydroxypropanesulfonic acid) buffer, Hank buffer with HEPES, imidazole-HCl buffer, maleic acid buffer, MOPS (3- (N-morpholino) propanesulfonic acid) buffer, phosphate buffered saline, phosphate buffer, potassium phosphate, TBS (Tris buffered saline) buffer, and Tris (hydroxymethyl) aminomethane) buffer.

7. The aqueous composition according to any one of claims 1 to 6, further comprising at least one auxiliary agent.

8. The aqueous composition according to claim 7, wherein said at least one adjuvant is a nonionic surfactant.

9. An aqueous composition according to claim 8 wherein the nonionic surfactant is selected from the group consisting of alkyl polyglycosides, alkoxylated alcohols, alkoxylated natural oils, glycerol esters, alkoxylated reduced sugar esters, alkoxylated glycerol mono cocoate esters, esters of polyhydric alcohols, alkoxylated amines, alkoxylated esters, alkoxylated alkyl or aryl phenols, ethylene oxide/propylene oxide copolymers and mixtures thereof.

10. An aqueous composition according to claim 9, wherein the alkylpolyglycoside is represented by formula (I):

R₁O(R₂O)_b(Z)_a (I)

wherein:

R₁is unsubstituted or substituted, straight-chain or branched C₄-C₃₀Alkyl or unsubstituted or substituted, straight-chain or branched C₄-C₃₀An alkenyl group;

R₂is unsubstituted or substituted, straight-chain or branched C₂-C₄An alkylene group;

b is in the range of 0 to 100,

z is a sugar residue having 5 to 6 carbon atoms; and

a is an integer of 1 to 6.

11. An aqueous composition according to claim 10, wherein

R₁Is unsubstituted, straight-chain or branched C₈-C₁₆An alkyl group;

b is 0;

z is glucose; and

a is an integer of 1 to 2.

12. An aqueous composition according to claim 9, wherein the alkoxylated alcohol has the formula:

R₃O-(R₄O)_xR₅ (II)

wherein

R₃Is unsubstituted or substituted, straight-chain or branched C₁-C₃₀Alkyl or unsubstituted or substituted, straight-chain or branched C₂-C₃₀An alkenyl group which is a radical of an alkylene group,

R₄at x (R)₄O) is independently in each of the radicals unsubstituted or substituted, straight-chain or branched C₂-C₄An alkylene group or a substituted alkylene group,

R₅is hydrogen or unsubstituted or substituted, straight-chain or branched C₁-C₃₀An alkyl group; and

x is an integer in the range of 1-60.

13. An aqueous composition according to claim 12, wherein

R₃Is unsubstituted, straight-chain or branched C₁₀-C₁₄An alkyl group;

R₄is unsubstituted straight chain C₂An alkylene group;

R₅is hydrogen, and

x is an integer in the range of 7 to 10.

14. An aqueous composition according to claim 9, wherein the alkoxylated natural oil is an alkoxylated castor oil.

15. Aqueous composition according to claim 8, wherein the at least one auxiliary agent is selected from C₉-C₁₁Alkyl polyglucoside, ethoxylated tridecanol and ethoxylated castor oil.

16. An aqueous composition according to any of claims 8 to 15, wherein the at least one auxiliary agent is present in an amount of from 0.1 to 10.0 wt. -%, based on the total weight of the aqueous composition.

17. The aqueous composition according to any one of claims 1 to 16, further comprising at least one adjuvant selected from the group consisting of defoamers, organic and inorganic thickeners, bactericides, antifreeze agents, colorants and binders.

18. An aqueous composition according to any one of claims 1 to 17 comprising:

0.1-1.0 wt% topramezone,

0.1 to 10.0 wt.% of at least one auxiliary agent,

0.1 to 10.0 wt.% of at least one auxiliary agent,

at least one buffering agent, and

2.0 to 99.0% by weight of water,

in each case based on the total weight of the aqueous composition,

wherein the pH of the composition is in the range of 6.5-7.5.

19. A method for controlling undesired vegetation, comprising the step of applying an aqueous composition according to any one of claims 1 to 18 to plants, their environment and/or seeds.

20. Use of a composition according to any one of claims 1 to 19 for controlling undesired vegetation.

21. A method of producing a composition according to any one of claims 1 to 19, comprising the steps of:

(a) adding 0.1-1.0 wt% topramezone to a buffer solution having a pH in the range of 6.5-7.5.

22. The method of claim 21, further comprising the steps of:

(b) adding at least one auxiliary agent in the range of 0.1-10.0 wt%; and

(c) at least one auxiliary agent is added in the range of 0.1-10.0 wt%.

23. The ready-to-spray formulation according to any one of claims 1 to 18.

Technical Field

The present invention relates to an aqueous herbicidal composition comprising topramezone. The invention also relates to the use of these compositions for controlling undesirable vegetation in crops and non-crops. Non-crop areas include grass, turf, golf courses, or parks.

Background

In crop protection, it is in principle desirable to increase the specificity and reliability of the action of active compounds. It is particularly desirable that crop protection products control harmful plants effectively and are at the same time tolerated by the useful substances.

Herbicides are widely used in commercial agriculture and can increase crop yield and product quality. They are commonly used to control a variety of weeds, such as grasses and broadleaf weeds such as amaranth, green bristlegrass and others, which invariably pose a risk to crop yield.

Topramezone (4- [3- (4, 5-dihydro-1, 2-)Azol-3-yl) -2-methyl-4-methylsulfonylbenzoyl]-2-methyl-1H-pyrazol-3-one) and their agriculturally acceptable salts are well-known herbicidally active compounds [ see c.d. s Tomlin (ed.), The Pesticide Manual, 14 th edition, 2006, BCPC Alton, Hampshire, UK, page 1047]. General procedures for topramezone and its preparation are known from PCT publications WO 98/31681 and WO 99/58509.

Topramezone is known to be a 4-hydroxyphenylpyruvate dioxygenase inhibitor (4-HPPD inhibitor) and provides highly effective control of annual warm season grasses such as barnyard grass (Echinochloa), Setaria (Setaria), Digitaria (Digitaria) and Panicum (Panicum) varieties, as well as dicotyledonous weeds such as Chenopodium (Chenopodium), Atriplex (Atriplex), Amaranthus (Amaranthus), Solanum (Solanum), galileonura (galinoga), chickweed (stellariia media), Lamium (Lamium) and Veronica (Veronica) varieties. However, herbicidal activity and activity spectrum are sometimes limited. Commercial formulations of topramezone with adjuvants such asCombined application to achieve reliable herbicidal action. Formulations of topramezone are sold under the trade name BASF SEAndsuper (a combination of topramezone and dimethenamid-P).

Topramezone is typically formulated as a water dispersible granule (WG) or as a Suspension Concentrate (SC), i.e., a solid suspension. In such formulations, the active ingredient may be ground to a specific size and the solid subsequently suspended in a water-based carrier vehicle. Such WG formulations are typically prepared with few inert compounds with adjuvant effect and may make it difficult to make the active ingredients bioavailable to control weeds. The particle size of the active ingredient in these formulations and during application is generally kept too large so that significant amounts of the formulation must be applied per acre to control weeds. Similarly, suspension concentrate formulations have the disadvantage that the adjuvants are difficult to incorporate at useful rates and they provide little irritation to foliar absorption and biotransfer, so a significant amount of the formulation must be applied per acre to control weed infestation.

It is therefore an object of the present invention to provide an aqueous solution formulation of topramezone, which is easy to use and easy to bioavail-able.

Summary of The Invention

It has surprisingly been found that topramezone is readily soluble in an aqueous solution having a pH of 6.5 to 7.5 when measured at 25 ℃.

Accordingly, in one aspect the invention relates to an aqueous solution comprising 0.1 to 1.0 wt% topramezone and which solution has a pH in the range of 6.5 to 7.5 when measured at 25 ℃.

Another aspect of the invention relates to an aqueous solution comprising 0.1 to 1.0 wt% topramezone and a buffer.

Yet another aspect of the invention relates to an aqueous buffered solution comprising 0.1 to 1.0 wt% topramezone and an adjuvant, wherein the solution has a pH in the range of 6.5 to 7.5 when measured at 25 ℃.

In another embodiment of the present invention, the adjuvant is a nonionic surfactant present in the range of 0.1 to 10.0% based on the total weight of the composition.

In another embodiment of the invention, the nonionic surfactant is selected from the group consisting of alkyl polyglycosides, alkoxylated alcohols, alkoxylated natural oils, glycerol esters, alkoxylated reduced sugar esters, alkoxylated glycerol mono-cocoate esters, esters of polyhydric alcohols, alkoxylated amines, alkoxylated esters, alkoxylated alkyl or aryl phenols, and ethylene oxide/propylene oxide copolymers.

In one aspect of the invention, an aqueous buffered solution comprising 0.1 to 1.0 wt% topramezone and an adjuvant is stable for a period of at least 135 days when stored at 50 ℃, wherein the solution has a pH of 6.5 to 7.5 when measured at 25 ℃.

In one aspect, the invention relates to a method of controlling undesirable vegetation by applying an aqueous buffered composition comprising 0.1 to 1.0 weight percent topramezone with or without an adjuvant.

A further aspect of the invention relates to the use of an aqueous buffered composition comprising 0.1 to 1.0 wt% topramezone, with or without an adjuvant, for controlling undesired plant growth.

Detailed Description

Before the present compositions and formulations are described, it is to be understood that this invention is not limited to such compositions and formulations, as such compositions and formulations may, of course, vary. It is also to be understood that the terminology used herein is not intended to be limiting, since the scope of the present invention will be limited only by the appended claims.

If a group is defined below as comprising at least a certain number of embodiments, this is also intended to include groups preferably consisting of only these embodiments. Furthermore, the terms "first", "second", "third" or "(a)", "(b)", "(c)", "(d)" etc. in the description and in the claims are used for distinguishing between similar elements and not necessarily for describing a sequential or chronological order. It is to be understood that the terms so used are interchangeable under appropriate circumstances and that the embodiments of the invention described herein are capable of operation in other sequences than described or illustrated herein. Where the terms "first", "second", "third" or "(a)", "(B)" and "(C)" or "(a)", "(B)", "(C)", "(d)", "i", "ii", etc. relate to steps of a method or use or assay, there is no time or time interval coherence between the steps, i.e. the steps may be performed simultaneously or there may be time intervals of seconds, minutes, hours, days, weeks, months or even years between the steps, unless otherwise indicated in the present application as above and below.

The different aspects of the invention are defined in more detail in the following paragraphs. Aspects so defined may be combined with any one or more other aspects unless clearly indicated to the contrary. Any feature shown as being preferred or advantageous may particularly be combined with any other feature or features shown as being preferred or advantageous.

Reference throughout this specification to "one embodiment" or "an embodiment" means that a particular feature, structure, or characteristic described in connection with the embodiment is included in at least one embodiment of the present invention. Thus, appearances of the phrases "in one embodiment" or "in an embodiment" in various places throughout this specification are not necessarily all referring to the same embodiment, but may. Furthermore, the particular features, structures, or characteristics may be combined in any suitable manner in one or more embodiments, as would be apparent to one of ordinary skill in the art from this disclosure. Furthermore, although certain embodiments described herein include some but not other features included in other embodiments, combinations of features of different embodiments are intended to be within the scope of the invention and form different embodiments, as will be understood by those of skill in the art. For example, in the appended claims, any of the claimed embodiments may be used in any combination.

In addition, the ranges defined throughout this specification are also inclusive, i.e., a range of 1 to 10 indicates that both 1 and 10 are included in the range. For the avoidance of doubt, the applicant shall be entitled to any equivalent under the applicable law.

The term "stable" as used herein relates to an aqueous composition comprising topramezone, wherein the formulation remains unchanged, i.e. without any precipitation or turbidity or phase separation.

In one aspect of the invention, the invention relates to an aqueous solution comprising 0.1 to 1.0% topramezone and which solution has a pH in the range of 6.5 to 7.5 when measured at 25 ℃.

Topramezone is a selective herbicide from the phenylpyrazolone chemical family used primarily for post-emergence control of broadleaf weeds and some grasses in field corn, sweet corn, and popcorn corn. It is represented by the following structure:

the solubility of topramezone in water at 25 ℃ is about 0.305 g/L. In addition, the solubility of topramezone in various organic solvents is limited.

It has surprisingly been found that topramezone is readily soluble in an aqueous solution having a pH of 6.5 to 7.5 when measured at 25 ℃.

Another aspect of the invention relates to an aqueous solution comprising 0.1 to 1.0 wt% topramezone and a buffer. In one embodiment, the amount of topramezone is in the range of 0.1 to 1.0% or 0.1 to 0.9% or 0.1 to 0.8% or 0.1 to 0.7% or 0.1 to 0.6% or 0.1 to 0.5% or 0.1 to 0.4% or 0.1 to 0.3% or 0.1 to 0.2%, in each case based on the final weight of the composition.

In one embodiment of the invention, the at least one buffer is selected from the group consisting of phosphate buffer, phosphate-acetate buffer, citrate-phosphate buffer, BES (N, N-bis (2-hydroxyethyl) -2-aminoethanesulfonic acid) buffered saline, EBSS (Earle balanced salt solution) buffer, Hanks balanced buffer solution, HEPPSO (N- (2-hydroxyethyl) piperazine-N' - (2-hydroxypropanesulfonic acid) buffer, Hank buffer with HEPES, imidazole-HCl buffer, maleic acid buffer, MOPS (3- (N-morpholino) propanesulfonic acid) buffer, phosphate buffered saline, potassium phosphate, TBS (Tris buffered saline) buffer and Tris (hydroxymethyl) aminomethane) buffer.

In one embodiment of the invention, the at least one buffer is a phosphate buffer.

The phosphate buffer may optionally contain other buffers in addition to phosphate.

For example, the phosphate buffer may contain citrate. However, in one embodiment the phosphate buffer is free of other buffers.

The phosphate buffer used in the formulations of the present invention may be an alkali metal or alkaline earth metal phosphate buffer such as a sodium phosphate buffer.

Thus, in another embodiment, the present invention provides a composition wherein the phosphate buffer comprises disodium hydrogen phosphate, sodium hydroxide, potassium dihydrogen phosphate and has a pH of 7 ± 0.01 when measured at 25 ℃.

The sodium phosphate used to prepare the formulations of the present invention may be, for example, sodium dihydrogen phosphate or disodium hydrogen phosphate or mixtures thereof.

Sodium phosphate (e.g., sodium dihydrogen phosphate or disodium hydrogen phosphate or mixtures thereof) can be used in anhydrous form or in hydrated form or mixtures of anhydrous and hydrated forms. For example, sodium dihydrogen phosphate may be used in its monohydrate form, while disodium hydrogen phosphate may be used in its dihydrate form.

Thus, in one embodiment, the phosphate buffer is monosodium phosphate (e.g., a monohydrate).

In another embodiment, the phosphate buffer is disodium phosphate (e.g., its dihydrate).

In another embodiment, the phosphate buffer is a combination of more than one sodium phosphate buffer. For example, the phosphate buffer may be a combination of two sodium phosphate buffers. In a particular embodiment, the formulation contains first and second sodium phosphate buffers, wherein the first sodium phosphate buffer is monosodium phosphate (e.g., in the monohydrate form) and the second sodium phosphate buffer is disodium phosphate (e.g., in the dihydrate form).

It is understood that the ratio of monobasic sodium phosphate and dibasic sodium phosphate may be varied to provide the desired pH for the formulation. If necessary, an acid or base may be added to adjust to the final pH.

Similarly, when the formulation is prepared using only one of sodium dihydrogen phosphate and disodium hydrogen phosphate, an acid or base may be added to adjust the pH of the formulation to the desired value.

In one embodiment of the invention, the pH of the aqueous composition is in the range of 6.5 to 7.5, more preferably 6.8 to 7.2, even more preferably 6.9 to 7.1 when measured at 25 ℃.

In another embodiment of the invention, the pH of the aqueous composition is 6.5. + -. 0.01, 6.6. + -. 0.01, 6.7. + -. 0.01, 6.8. + -. 0.01, 6.9. + -. 0.01, 7.0. + -. 0.01, 7.1. + -. 0.01, 7.2. + -. 0.01, 7.3. + -. 0.01, 7.4. + -. 0.01 or 7.5. + -. 0.01, when measured at 25 ℃.

In another embodiment, the invention relates to an aqueous solution comprising 0.1 to 1.0 wt% topramezone and an adjuvant, wherein the solution has a pH in the range of 6.5 to 7.5 when measured at 25 ℃.

An 'adjuvant' is understood to be a compound that increases the effectiveness of the active ingredient when applied to the treated soil and plants. The term 'effective' means that the adjuvant produces one or more of the following effects:

the activity of the active ingredient is increased and,

increased absorption and spreading of the active ingredient on the target surface,

improving the rain resistance of the active ingredient,

improving the compatibility of the active ingredient with the fertiliser and/or micronutrient and/or other components of the spray solution

A reduction in the light conversion of the active ingredient,

reduce the amount of drifting droplets from the spray solution,

reduce the amount of foam in the spray solution.

In one embodiment of the invention, the adjuvant is a nonionic surfactant.

The nonionic surfactant is preferably selected from alkyl polyglycosides, alkoxylated alcohols, alkoxylated natural oils, glycerol esters, alkoxylated reduced sugar esters, alkoxylated glycerol mono-cocoate esters, esters of polyhydric alcohols, alkoxylated amines, alkoxylated esters, alkoxylated alkyl or aryl phenols and ethylene oxide/propylene oxide copolymers.

In one embodiment of the present invention, the nonionic surfactant is an alkyl polyglycoside represented by formula (I):

R₁O(R₂O)_b(Z)_a (I)

wherein:

R₁is unsubstituted or substituted, straight-chain or branched C₄-C₃₀Alkyl or unsubstituted or substituted, straight-chain or branched C₄-C₃₀An alkenyl group;

R₂is unsubstituted or substituted, straight-chain or branched C₂-C₄An alkylene group;

b is a number of 0 to 100,

z is a sugar residue having about 5 to 6 carbon atoms; and

a is an integer of 1 to 6.

In another embodiment, the alkylpolyglycoside of formula (I) has the following substitution pattern:

R₁is unsubstituted or substituted, straight-chain or branched C_4-22Alkyl or unsubstituted or substituted straight or branched C₄-C₂₂An alkenyl group which is a radical of an alkylene group,

R₂is straight chain C₂-C₄An alkylene group;

b is a number from 0 to about 12,

z is a sugar residue having about 5 to 6 carbon atoms. Z can be glucose, mannose, fructose, galactose, talose, gulose, altrose, allose, apiose, gallose, idose, ribose, arabinose, xylose, lyxose or mixtures thereof;

'a' is an integer of from 1 to about 3,

even more preferably, the alkylpolyglycoside of formula (I) has the following substitution pattern:

R₁is unsubstituted, straight-chain or branched C₈-C₁₆An alkyl group;

b is 0;

z is glucose; and

a is an integer of 1 to 2.

Typical compounds of formula (I) are compounds of formula (Ia):

wherein n is the degree of polymerization and is 1 to 3, preferably 1 or 2, and P is a branched or straight chain alkyl group having 4 to 18 carbon atoms or a mixture of alkyl groups having 4 to 18 carbon atoms. Most typically the Alkyl Polyglucoside (APG) comprises an alkyl group containing from 8 to 10 carbon atoms and has an average degree of polymerisation of 1.7; an alkyl group having 9 to 11 carbon atoms and having an average degree of polymerization of 1.3 to 1.6; or mixtures thereof. APG also includes embodiments that have been anionically or cationically modified, such as those described above.

Exemplary alkylpolyglycosides include325(BASF) (alkylpolyglycoside in which the alkyl group has 9 to 11 carbon atoms and the average degree of polymerization is 1.6),2000(BASF) (alkylpolyglycoside in which the alkyl group contains 8 to 16 carbon atoms and has an average degree of polymerization of 1.4),1300(BASF) (alkylpolyglycoside in which the alkyl group has 12 to 16 carbon atoms and the average degree of polymerization is 1.6),PG 8107(BASF) (an alkylpolyglycoside in which the alkyl group has 8 to 10 carbon atoms and an average degree of polymerization of 1.7),PG9116 (BASF) (an alkylpolyglycoside in which the alkyl group has 9 to 11 carbon atoms and the average degree of polymerization is 1.6) andPG 8105(BASF) (an alkylpolyglycoside in which the alkyl group contains 8 to 10 carbon atoms and has an average degree of polymerization of 1.5).

In one embodiment, the alkylpolyglycoside is C₉-C₁₁An alkyl polyglucoside.

In another embodiment of the present invention, the nonionic surfactant is an alkoxylated alcohol represented by formula (II):

R₃O-(R₄O)_xR₅ (II)

wherein:

R₃is unsubstituted or substituted, straight-chain or branched C₁-C₃₀Alkyl or unsubstituted or substituted, straight-chain or branched C₂-C₃₀An alkenyl group which is a radical of an alkylene group,

R₄at x (R)₄O) is independently in each of the radicals unsubstituted or substituted, straight-chain or branched C₂-C₄An alkylene group or a substituted alkylene group,

R₅is hydrogen or unsubstituted or substituted, straight-chain or branched C₁-C₃₀Alkyl radicals, and

x is an integer from 1 to 60.

In one embodiment of the present invention, the alkoxylated alcohol of formula II has the following substitution pattern:

R₃is unsubstituted, straight-chain or branched C₁₀-C₁₄An alkyl group;

R₄is unsubstituted straight chain C₂An alkylene group;

R₅is hydrogen, and

x is an integer in the range of 7 to 10.

Non-limiting examples include ethoxylated long chain C₁₀Guerbet alcohol, e.g. produced by BASF and sold under the trade markXL100，XL80，XL70，XL60 andXP 80. Examples include LUTENSOL XL80, an ethoxylated C having an average of 8 Ethylene Oxide (EO) groups₁₀The alcohol of the guerbet group is,XL 100-an ethoxylated C having an average of 10 EO groups₁₀Guerbet alcohol, and ethoxylated C with an HLB of about 13₁₀Guerbet alcohols, e.g. produced by BASF Corp. and under the trade markSurfactant sold under XL 70.

Other examples of suitable nonionic surfactants include ethoxylated linear alcohols, such as those having C₁₀-C₁₅N-alkyl ethoxylated linear alcohols. Non-limiting examples includeTDA 10 (from BASF) -an ethoxylated tridecanol having an average of 10 EO groups,LA 070S-an ethoxylated lauryl alcohol with an average of 7 EO groups,91-6-A C with an average of 6 EO groups₉-C₁₁Ethoxylated alcohols andAO-8-A synthetic C having an average of 8 EO groups₁₃-C₁₅An alcohol is synthesized by ethoxylation of carbonyl.

In another embodiment of the invention, the alkoxylated alcohol is an ethoxylated tridecyl alcohol.

In one embodiment of the invention, the nonionic surfactant is an alkoxylated natural oil.

The natural oil is selected from castor oil, soybean oil, peanut oil, sunflower oil, rapeseed oil, palm oil, cottonseed oil, peanut oil, palm kernel oil, coconut oil, olive oil, corn oil, grape seed oil, linseed oil, safflower oil, sesame oil, corn oil, raschel oil, sesame oil, cotton oil, jatropha oil, fish oil, herring oil, sardine oil, beef tallow, lard or mixtures thereof.

By "alkoxylated natural oil" is meant a natural oil which has been treated with a compound of the formula- (L-O)_n-H or-A-O- (L-O)_nA natural oil functionalized with a group of-H, where L is a linear or branched C₂-C₃An alkylene group, n is an integer greater than or equal to 1 (e.g., n is an integer selected from 1 to 100), and a is a bond or a divalent linking group. The divalent linking group may be any suitable chemical group that links the remainder of the functional group to the natural oil. Examples of divalent linking groups include C₁-C₆Alkylene, such as methylene. Several chemical methods known to those skilled in the art can be used to alkoxylate natural oils. Certain natural oils, such as castor oil, comprise triglycerides containing hydroxylated fatty acids (e.g., ricinoleic acid) and may be alkoxylated without further modification. Other natural oils that do not contain sufficient amounts of hydroxylated fatty acids, but do contain unsaturated fatty acids, can be modified to introduce hydroxyl groups that can be alkoxylated. The term "alkoxylated natural oil" as used herein is intended to include both natural oils that can be alkoxylated without further modification, such as castor oil, as well as natural oils that must be modified to introduce hydroxyl groups that can be subsequently alkoxylated. Such modifications include modifications at the carbon-carbon double bond to introduce hydroxyl groups, for example by epoxidation and nucleophilic ring opening, hydroxylation, ozonolysis andreduction, and hydroformylation and reduction (introduction of hydroxymethyl). Such modifications are generally known in the art and are described, for example, in U.S. Pat. nos. 4,534,907, 4,640,801, 6,107,433, 6,121,398, 6,897,283, 6,891,053, 6,962,636, 6,979,477 and PCT publications WO 2004/020497, WO 2004/096744, WO 2004/096882 and WO 2004/096883.

After modifying the natural oil, the modified product may be obtained by using C including Ethylene Oxide (EO), Propylene Oxide (PO) and a mixture of EO and PO₂-C₃The alkylene oxides are alkoxylated according to methods well known to those skilled in the art, such as base-catalyzed or acid-catalyzed ring-opening polymerization (see, for example, U.S. Pat. No.2,870,220; U.S. Pat. No.2,133,480; U.S. Pat. No.2,481,278). Alternatively, the dehydrating agent hydroxyl-containing natural oil or the modified natural oil containing hydroxyl groups may be alkoxylated by reaction with an alkylene glycol (e.g., ethylene glycol or propylene glycol or mixtures thereof) or a hydroxyl-terminated oligo-and poly (alkylene glycol) (e.g., hexaethylene glycol, a Mn-300 polyethylene glycol available from Sigma-Aldrich co., st.louis, Missouri (Sigma-Aldrich cat.no. 202371)) in the presence of a dehydrating agent or a hydroxyl-containing modified natural oil (Sigma-Aldrich cat.no.202398), or a Mn-400 polyethylene glycol available from Sigma-Aldrich co., st.louis, Missouri (Sigma-Aldrich cat.202398)). Suitable reaction conditions are well known in the art, see, for example, U.S.2,056,830 and EP 2080778.

In certain embodiments, the alkoxylated natural oil is ethoxylated (i.e., L is ethylene). In certain embodiments, the ethoxylated natural oil contains an average of from about 15 to about 50 moles of ethylene oxide per mole of natural oil (e.g., n is from about 15 to about 50). In certain other embodiments, the ethoxylated natural oil contains an average of from about 25 to about 40 moles of ethylene oxide per mole of natural oil (e.g., n is from about 25 to about 40). In certain other embodiments, the ethoxylated natural oil contains an average of from about 30 to about 40 moles of ethylene oxide per mole of natural oil (e.g., n is from about 30 to about 40). In certain other embodiments, the ethoxylated natural oil contains an average of from about 30 to about 36 moles of ethylene oxide per mole of natural oil (e.g., n is from about 30 to about 36). In certain other embodiments, the ethoxylated natural oil contains an average of about 36 moles of ethylene oxide per mole of natural oil (e.g., n is about 36). In certain other embodiments, the ethoxylated natural oil contains an average of about 30 moles of ethylene oxide per mole of natural oil (e.g., n is about 30).

In another embodiment of the invention, the alkoxylated natural oil is ethoxylated castor oil.

The ethoxylated castor oil may be one or more ethoxylated castor oils selected from ethoxylated castor oils having an EO number of from 8 to 50. Preferably the ethoxylated castor oil has an EO number of from 15 to 40. In one embodiment, the ethoxylated castor oil has an EO number of from 20 to 40, for exampleCSO-25 andCSO-36 (from BASF).

In one embodiment of the invention, the amount of auxiliaries is from 0.1 to 10% or from 0.1 to 9% or from 0.1 to 8% or from 0.1 to 7% or from 0.1 to 6% or from 0.1 to 5% or from 0.1 to 4% or from 0.1 to 3% or from 0.1 to 2% or from 0.1 to 1%, more preferably in the range from 0.1 to 2.5% or from 0.1 to 2.25% or from 0.1 to 1.75% or from 0.1 to 1.5% or from 0.1 to 1.25%, in each case based on the final weight of the composition.

In another embodiment of the invention, the pH of the aqueous composition comprising 0.1 to 1.0 wt% topramezone and 0.1 to 10.0 wt% adjuvant is 6.5 ± 0.01, 6.6 ± 0.01, 6.7 ± 0.01, 6.8 ± 0.01, 6.9 ± 0.01, 7.0 ± 0.01, 7.1 ± 0.01, 7.2 ± 0.01, 7.3 ± 0.01, 7.4 ± 0.01, 7.5 ± 0.01, when measured at 25 ℃.

In one embodiment of the invention, an aqueous buffered solution comprising 0.1 to 1.0 wt% topramezone and an adjuvant is stable for a period of at least 135 days when stored at 50 ℃, wherein the solution has a pH of 6.5 to 7.5 when measured at 25 ℃.

Additive/adjuvant

The composition of the invention may further comprise at least one additive/auxiliary compound selected from defoamers, thickeners, biocides, antifreeze, colorants and binders.

The composition includes an anti-foaming agent. Non-limiting examples of suitable defoamers include silicone emulsions such as Silikon SRE from Wacker, germany or Rhodorsil from Rhodia, france; a long chain alcohol; a fatty acid; a fatty acid salt; organofluorine compounds and mixtures thereof.

Suitable thickeners are polysaccharides, such as xanthan gum, carboxymethylcellulose, organoclays (organically modified or unmodified), polycarboxylates and silicates.

Suitable anti-freeze agents are ethylene glycol, propylene glycol, urea and glycerol.

Suitable fungicides are bronopol and isothiazolinone derivatives such as alkylisothiazolinone and benzisothiazolinone.

Suitable colorants include both sparingly water-soluble pigments and water-soluble dyes. Non-limiting examples are rhodamine B, c.i. pigment red 112 and c.i. solvent red 1, pigment blue 15:4, pigment blue 15:3, pigment blue 15:2, 35 pigment blue 15:1, pigment blue 80, pigment yellow 1, pigment yellow 13, pigment red 48:2, pigment red 48:1, pigment red 57:1, pigment red 53:1, pigment orange 43, pigment orange 34, pigment orange 5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25, basic violet 10, basic violet 49, acid red 51, acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red 108, iron oxide, titanium oxide, iron hexacyanoferrate.

Suitable binders are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, polyacrylates, biological or synthetic waxes and cellulose ethers.

In one embodiment of the invention, the amount of adjuvant is in the range of 0.1 to 10% or 0.1 to 9% or 0.1 to 8% or 0.1 to 7% or 0.1 to 6% or 0.1 to 5% or 0.1 to 4% or 0.1 to 3% or 0.1 to 2% or 0.1 to 1%, more preferably in the range of 0.1 to 2.5% or 0.1 to 2.25% or 0.1 to 1.75% or 0.1 to 1.5% or 0.1 to 1.25%, in each case based on the final weight of the composition.

In another embodiment, the individual components of the composition of the invention may be mixed in a spray tank and, if appropriate, further additives/adjuvants may be added.

The compositions of the present invention may be applied from a pre-dosing device, a backpack sprayer, a spray can, a spray plane, or an irrigation system.

The compositions of the present invention are suitable for controlling a large number of harmful plants, including monocotyledonous and dicotyledonous weeds. They are particularly useful for controlling annual weeds such as grassy weeds (grasses) including barnyard grass such as barnyard grass (Echinochloa crusgalli var. crusgalli); the weed species include large amounts of weeds such as red sage (Digitaria sanguinalis), green Setaria such as Setaria viridis (Setaria vindis) and Setaria viridis (Setaria faberi), Sorghum such as johnsongrass (Sorghum halepense Pers), Avena such as Avena sativa (Avena fatua), Tribulus such as Tribulus (Cenchrus echiensis), Bromus, Lolium, Phanerochaete, Phalaris, Panicum, brachiarius, Poa pratense (Poa annua), Hordeum vulgare (Alopecurus myosuroides), Leymus chinensis (Aegirardia cylindracea), Agropyron repens (Agropyron repens), Agropyron elatus (Aperiophyceae), Eleuonymus indica (Elaeagnus roxburghii), Caryopterina indica (Amur), Amur (Amur) such as Amaranthus rosewood, and the like; chamomile genus; genus atriplex; thistle genus; convolvulus genus; alcoholic grass such as white spirit grass (Conyza canadens); cassia genus; genus Commelina; datura genus; euphorbia; geranium; achyranthes genus; morning glory (Ipomoea species); genus picrasma; a genus of mallow; matricaria genus; allium species; solanum genus; xanthium genus; veronica; viola genus; common chickweed, Abutilon (Abutilon theohrasti), Sesbania maxima (Sesbania exalta Cory), Alstonia roseoana (Andoa cristata), Bidens bipinnata (Bidens plosa), Arabidopsis thaliana (Brassica kaber), Capsella bursa-pastoris), Centaureus chinensis (Centaurea cyanus), Flammulina ferrea (Galeopsis tetrahit), Galium aparine (Galium aparine), Helianthus annuus (Helianthus annuus), Desmodium styracifolium (Desmodium turulosum), broom cypress (Kochia scoparia), Carcinia Maultflora (Mercury annua), Stephania diversicerans (Myosissia arvensis), Papaveris (Papaveris), Raphanus sativus (Raopmania sonensis), Stephania decurrens (Thalia), Medicago sativa (Thailanthus), Medicago sativa (Medicago sativa, Medicago sativa (L, Medicago sativa, and Medicago sativa (Medicago sativa, L.

The compositions of the invention are suitable for controlling/controlling undesired vegetation in plants, their environment and/or seeds. Plants include both crops and non-crops.

The compositions of the present invention are suitable for controlling undesirable vegetation in small grain cereal crops such as wheat, durum, triticale, rye and barley.

The compositions of the present invention are suitable for controlling undesirable vegetation in non-crop areas including lawns, golf courses, or parks.

The compositions according to the invention are suitable for application to any kind of crops as mentioned above, if not otherwise stated.

The compositions of the invention may also be used for crops that have been modified by breeding, mutagenesis or genetic engineering, for example as a result of conventional methods of breeding or genetic engineering, to confer tolerance to the application of a particular class of herbicides, such as auxin herbicides like dicamba or 2, 4-D; bleach herbicides such as 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors or Phytoene Dehydrogenase (PDS) inhibitors; acetolactate synthase (ALS) inhibitors, such as sulfonylureas or imidazolinones; inhibitors of enolpyruvylshikimate 3-phosphate synthase (EPSPS), such as glyphosate (glyphosate); glutamine Synthase (GS) inhibitors, such as glufosinate (glufosinate); protoporphyrinogen-IX oxidase inhibitors; lipid biosynthesis inhibitors such as acetyl-coa carboxylase (accase) inhibitors; or benzonitrile (xynil) herbicides (i.e., bromoxynil or ioxynil) herbicides; furthermore, plants have been made tolerant to multiple herbicides through multiple genetic modifications, for example to both glyphosate and glufosinate or to both glyphosate and a herbicide selected from another class such as ALS inhibitors, HPPD inhibitors, auxin herbicides or accase inhibitors. These herbicide tolerance techniques are described, for example, in Pest Management Science 61, 2005, 246; 61, 2005, 258; 61, 2005, 277; 61, 2005, 269; 61, 2005, 286; 64, 2008, 326; 64,2008, 332; weed Science 57, 2009, 108; australian Journal of Agricultural Research 58, 2007, 708; science 316, 2007, 1185, herein incorporated by reference. Tolerance to herbicides has been conferred to several cultivated plants by mutagenesis and conventional breeding methods, e.g.Summer rape (Canola, BASF SE, Germany) on imidazolinones such as imazamox orSunflower (DuPont, USA) is tolerant to sulfonylureas such as tribenuron-methyl. Genetic engineering methods have been used to confer tolerance to herbicides such as glyphosate, imidazolinones and glufosinate on cultivated plants such as soybean, cotton, corn, sugar beet and oilseed rape, some of which are under development or may be under the trade name Roundup(Glyphosate-tolerant, Monsanto, USA),(imidazolinone tolerant, BASF SE, Germany) and Liberty(glufosinate-ammonium tolerant, Bayer crop science, Germany) is commercially available.

The compositions of the invention may also be used to genetically modify crops. The term "genetically modified plant" is to be understood as a plant whose genetic material has been modified by using DNA recombination techniques to include inserted DNA sequences which are not or show deletions of the genome of the plant species itself, wherein said modifications cannot be readily obtained by cross breeding alone, by mutagenesis or by natural recombination. A particular genetically modified plant is typically one whose genetic modification is obtained by inheritance from an ancestor plant whose genome has been directly treated using DNA recombination techniques, via a natural breeding or propagation process. One or more genes are often integrated into the genetic material of a genetically modified plant to improve certain properties of the plant. Such genetic modifications also include, but are not limited to, targeted post-translational modifications of proteins, oligopeptides or polypeptides, for example by introducing therein amino acid mutagenesis which allows, reduces or facilitates glycosylation or polymer addition such as prenylation, acetylation, farnesylation moieties or PEG moiety attachment.

The compositions of the invention are also useful for crops that can be modified, for example by using recombinant DNA techniques, to be able to synthesize one or more insecticidal proteins, especially those known from Bacillus (Bacillus) bacteria, especially those known from Bacillus thuringiensis (Bacillus thuringiensis), for example delta-endotoxins such as cryia (b), cryia (c), CryIF (a2), cryiia (b), CryIIIA, CryIIIB (b1) or Cry9 c; asexual insecticidal proteins (VIP) such as VIP1, VIP2, VIP3, or VIP 3A; insecticidal proteins of nematode-colonizing bacteria such as Photorhabdus (Photorhabdus) or Xenorhabdus (Xenorhabdus); animal-derived toxins such as scorpion toxin, spider toxin, wasp toxin, or other insect-specific neurotoxins; toxins produced by fungi such as streptomyces toxins, plant lectins such as pea or barley lectins; a lectin; protease inhibitors such as trypsin inhibitor, serine protease inhibitor, patatin, cysteine protease inhibitor or papain inhibitor; ribosome Inactivating Proteins (RIPs) such as ricin, corn-RIP, abrin, luffa seed protein, saporin or bryodin; steroid-metabolizing enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-IDP glycosyltransferase, cholesterol oxidase, ecdysone inhibitor or HMG-CoA reductase; ion channel blockers such as sodium channel or calcium channel blockers; juvenile hormone esterase; diuretic hormone receptors (helicokinin receptors);a synthetase, a bibenzyl synthetase, a chitinase or a glucanase. In the context of the present invention, these insecticidal proteins or toxins are also to be understood specifically as including protoxins, hybrid proteins, truncated or otherwiseA modified protein. Hybrid proteins are characterized by novel combinations of protein domains (see, e.g., WO 02/015701). Further examples of toxoids or genetically modified plants capable of synthesizing such toxoids are disclosed in, for example, EP-A374753, WO 93/007278, WO 95/34656, EP-A427529, EP-A451878, WO 03/18810 and WO 03/52073. Methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, for example, in the abovementioned publications. These insecticidal proteins contained in the genetically modified plants confer to the plants producing these proteins tolerance to pests of all taxonomic groups of arthropods, in particular to beetles (Coleoptera), Diptera (Diptera) and moths (Lepidoptera) and nematodes (Nematoda). Genetically modified plants capable of synthesizing one or more insecticidal proteins are described, for example, in the abovementioned publications, some of which are commercially available, for example(maize variety producing the toxin Cry1 Ab),plus (corn varieties producing the toxins Cry1Ab and Cry3Bb 1),(maize variety producing the toxin Cry9 c),RW (toxin-producing Cry34Ab1, Cry35Ab1 and the enzyme phosphinothricin-N-acetyltransferase [ PAT)]The maize variety of (a);33B (cotton variety Cry1Ac producing toxin),i (Cotton variety Cry1Ac producing toxin),II (cotton varieties producing toxins Cry1Ac and Cry2Ab 2);(VIP toxin-producing cotton variety);(potato variety producing toxin Cry 3A); bt11 (e.g. Bt 11)CB) and Bt176 of french Syngenta Seeds SAS (maize variety producing toxin Cry1Ab and PAT enzyme), MIR604 of french Syngenta Seeds SAS (maize variety producing modified version of toxin Cry3A, see WO 03/018810), MON 863 of Monsanto Europe s.a. belgium (maize variety producing toxin Cry3Bb 1), IPC 531 of Monsanto Europe s.a. belgium (cotton variety producing modified version of toxin Cry1 Ac) and 1507 of Pioneer overturas Corporation (maize variety producing toxin Cry1F and PAT enzyme).

The compositions of the invention are also useful for crops that have been modified by being able to synthesize one or more proteins to enhance the resistance or tolerance of these plants to bacterial, viral or fungal pathogens, for example by using recombinant DNA techniques. Examples of such proteins are the so-called "pathogenesis-related proteins" (PR proteins, see for example EP-A392225), plant disease resistance genes (for example potato cultivars expressing resistance genes against Phytophthora infestans from wild Mexico potato Solanum bulbocastanum) or T4 lysozyme (for example potato cultivars capable of synthesizing these proteins with increased resistance to bacteria such as Erwinia amylovora). Methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, for example, in the abovementioned publications.

The compositions of the invention are also useful for crops that have been modified by being able to synthesize one or more proteins to increase yield (e.g., biomass yield, grain yield, starch content, oil content, or protein content), tolerance to drought, salinity, or other growth-limiting environmental factors, or tolerance to pests and fungal, bacterial, or viral pathogens thereof, e.g., by using recombinant DNA techniques.

The compositions of the invention may also be used in crops modified, for example by using recombinant DNA techniques, to be able to produce increased amounts of ingredients or new ingredients suitable for improving human or animal nutrition, for example oil crops (e.g.oil crops producing long chain omega-3 fatty acids or unsaturated omega-9 fatty acids which promote health (e.g.Rape, DOW Agro Sciences, canada).

The compositions of the present invention may be applied in a conventional manner by techniques for applying herbicides well known to those skilled in the art. Suitable techniques include spraying, atomizing, dusting, broadcasting or pouring. The form of administration depends on the intended purpose in a known manner; in each case the best possible distribution of the active ingredients according to the invention should be ensured.

The compositions may be applied before or after emergence, i.e. before, during and/or after emergence of the undesirable plants. When the compositions are used in crops, they may be applied after sowing of the crop and before or after emergence of the crop. However, the compositions of the present invention may also be applied prior to sowing of the crop.

The compositions according to the invention have very good herbicidal activity after emergence, i.e. they exhibit good herbicidal activity against undesired plants after emergence. Thus, in one embodiment of the present invention, the composition is applied post-emergence, i.e. during and/or after the emergence of the undesired plants. It is particularly advantageous to apply the mixtures according to the invention after emergence (from the start of the undesired leaf development of the plants to the time of flowering). Since the compositions of the invention exhibit good crop tolerance even when the crop has emerged, they can be applied after the crop has been sown, in particular during or after the emergence of the crop.

The compositions are applied to the plants primarily by spraying, in particular foliar spraying. Application can be carried out by means of conventional spraying techniques using, for example, water as carrier and a spray ratio of from about 10 to 2000L/ha or from about 50 to 1000L/ha (for example 100-500L/ha).

In the case of post-emergence treatment of plants, the herbicidal mixtures or compositions according to the invention are preferably applied by foliar application. Application can be carried out, for example, using water as carrier and using conventional spraying techniques with an amount of the mixture sprayed from about 50 to 1000L/ha.

In the method of the invention, the application rate of the composition of the invention (calculated as topramezone) is generally from 5 to 50g/ha, preferably from 8 to 25 g/ha.

In one embodiment, 20 to 2000 liters, preferably 50 to 400 liters of ready-to-use spray liquor are applied per hectare of an agricultural utility area.

For use in treating crops, for example by foliar application, the topramezone composition of the invention can be applied at a rate in the range of from 0.0001 to 4000g/ha, for example from 1 to 2kg/ha or from 1 to 750g/ha, desirably from 1 to 100g/ha, more desirably from 10 to 50g/ha, for example from 10 to 20g/ha, from 20 to 30g/ha, from 30 to 40g/ha, or from 40 to 50 g/ha.

Detailed description of the preferred embodiments

1. An aqueous composition comprising 0.1 to 1.0% by weight, based on the total weight of the aqueous composition, of topramezone or an agriculturally acceptable salt thereof, wherein the pH of the composition is in the range of 6.5 to 7.5.

2. The aqueous composition according to embodiment 1, wherein the amount of topramezone or its agriculturally acceptable salt is in the range of from 0.1 to 0.5 percent by weight, based on the total weight of the aqueous composition.

3. The aqueous composition according to embodiment 1, wherein the pH of the composition is in the range of 6.8-7.2.

4. The aqueous composition according to embodiment 1, wherein the pH of the composition is in the range of 6.9-7.1.

5. An aqueous composition according to embodiment 1, comprising at least one buffering agent.

6. The aqueous composition according to embodiment 5, wherein the at least one buffer is selected from the group consisting of phosphate buffers, phosphate-acetate buffers, citrate-phosphate buffers, BES (N, n-bis (2-hydroxyethyl) -2-aminoethanesulfonic acid) buffered saline, EBSS (Earle balanced salt solution) buffer, Hanks balanced buffer solution, HEPPSO (N- (2-hydroxyethyl) piperazine-N' - (2-hydroxypropanesulfonic acid) buffer, Hank buffer with HEPES, imidazole-HCl buffer, maleic acid buffer, MOPS (3- (N-morpholino) propanesulfonic acid) buffer, phosphate buffered saline, phosphate buffer, potassium phosphate, TBS (Tris buffered saline) buffer, and Tris (hydroxymethyl) aminomethane) buffer.

7. The aqueous composition according to any of embodiments 1 to 6, further comprising at least one adjuvant.

8. The aqueous composition according to embodiment 7, wherein the at least one adjuvant is a nonionic surfactant.

9. The aqueous composition according to embodiment 8, wherein the nonionic surfactant is selected from the group consisting of alkyl polyglycosides, alkoxylated alcohols, alkoxylated natural oils, glycerol esters, alkoxylated reduced sugar esters, alkoxylated glycerol mono cocoate esters, esters of polyhydric alcohols, alkoxylated amines, alkoxylated esters, alkoxylated alkyl or aryl phenols, ethylene oxide/propylene oxide copolymers, and mixtures thereof.

10. The aqueous composition according to embodiment 9, wherein the alkylpolyglycoside is represented by formula (I):

R₁O(R₂O)_b(Z)_a (I)

wherein:

R₁is unsubstituted or substituted, straight-chain or branched C₄-C₃₀Alkyl or unsubstituted or substituted, straight-chain or branched C₄-C₃₀An alkenyl group;

R₂is unsubstituted or substituted, straight-chain or branched C₂-C₄An alkylene group;

b is in the range of 0 to 100,

z is a sugar residue having 5 to 6 carbon atoms; and

a is an integer in the range of 1 to 6.

11. An aqueous composition according to embodiment 10, wherein

R₁Is unsubstituted, straight-chain or branched C₈-C₁₆An alkyl group;

b is 0;

z is glucose; and

a is an integer of 1 to 2.

12. The aqueous composition according to embodiment 9, wherein the alkoxylated alcohol has the formula:

R₃O-(R₄O)_xR₅ (II)

wherein

R₃Is unsubstituted or substituted, straight-chain or branched C₁-C₃₀Alkyl or unsubstituted or substituted, straight-chain or branched C₂-C₃₀An alkenyl group which is a radical of an alkylene group,

R₄at x (R)₄O) is independently in each of the radicals unsubstituted or substituted, straight-chain or branched C₂-C₄An alkylene group or a substituted alkylene group,

R₅is hydrogen or unsubstituted or substituted, straight-chain or branched C₁-C₃₀An alkyl group; and

x is an integer in the range of 1 to 60.

13. The aqueous composition according to embodiment 12, wherein

R₃Is unsubstituted, straight-chain or branched C₁₀-C₁₄An alkyl group;

R₄is unsubstituted straight chain C₂An alkylene group;

R₅is hydrogen, and

x is an integer in the range of 7 to 10.

14. The aqueous composition according to embodiment 9, wherein the alkoxylated natural oil is an alkoxylated castor oil.

15. The aqueous composition according to embodiment 8, wherein the at least one auxiliary agent is selected from C₉-C₁₁Alkyl polyglucoside, ethoxylated tridecanol and ethoxylated castor oil.

16. The aqueous composition according to any of embodiments 8 to 15, wherein the at least one auxiliary agent is present in an amount of 0.1 to 10.0 wt. -%, based on the total weight of the aqueous composition.

17. The aqueous composition according to any of embodiments 1 to 16, further comprising at least one adjuvant selected from the group consisting of defoamers, organic and inorganic thickeners, bactericides, antifreeze agents, colorants and binders.

18. An aqueous composition according to any of embodiments 1 to 17 comprising:

0.1-1.0 wt% topramezone,

0.1 to 10.0 wt.% of at least one auxiliary agent,

0.1 to 10.0 wt.% of at least one auxiliary agent,

at least one buffering agent, and

2.0 to 99.0% by weight of water,

in each case based on the total weight of the aqueous composition,

wherein the pH of the composition is in the range of 6.5-7.5.

19. A method of controlling undesired vegetation, comprising the step of applying an aqueous composition according to any of embodiments 1 to 18 to plants, their environment and/or seeds.

20. Use of a composition according to any of embodiments 1 to 19 for controlling undesired vegetation.

21. A method of producing a composition according to any one of embodiments 1-19, comprising the steps of:

(a) adding 0.1-1.0 wt% topramezone to a buffer solution having a pH in the range of 6.5-7.5.

22. The method according to embodiment 21, further comprising the steps of:

(b) adding at least one auxiliary agent in the range of 0.1-10.0 wt%; and

(c) at least one auxiliary agent is added in the range of 0.1-10.0 wt%.

23. The ready-to-spray formulation according to any one of claims 1 to 18.

Examples

The following examples are set forth below to illustrate the methods and results according to the disclosed subject matter. These examples are not intended to include all aspects of the subject matter disclosed herein, but rather to illustrate representative methods, compositions, and results. These examples are not intended to exclude equivalents and variations of the invention as would be apparent to one skilled in the art.

Materials:CSO 36 is ethoxylated castor oil and is available from BASF under the trademarkThe solvent and wax available from CSO 36 were water soluble emulsifiers.TDA9 is available from BASF under the trade nameTDA9 commercially available as a nonionic surfactant consisting of a 9mol ethylene oxide adduct of tridecanol.PG9116 is made by BASF under the trade markC with a degree of polymerization of 1.6 available from PG9116₉-C₁₁An alkyl polyglucoside. Phosphate buffers (pH 7.0. + -. 0.1 at 25 ℃) are prepared by known methods. Topramezone used herein was obtained from BASF Corp and had a purity of greater than 95%.

Example 1

The method for preparing the formulation comprises the following steps:

1. topramezone is added to a buffer solution having a pH of 7.0 ± 0.1 and the resulting solution is stirred for at least 30 minutes.

2. The adjuvant was added to the above solution and the solution was stirred for 1 hour to obtain the final composition.

TABLE 1

Example 2

Formulations a-G were each subjected to a stability test. The stability test results are shown in the table below.

Table 2: stability data

	A	B	C	D	E	F	G
									Sky	Sky	Sky	Sky	Sky	Sky	Sky
At room temperature	168	149	126	126	119	119	119
								40℃	168	149	126	126	119	119	119
50℃	168	149	70	126	119	119	119
								2℃	112	DND	112	112	119	119	119
Freeze-thaw cycle (7 cycles)	14	DND	14	14	14	14	14

Thus, it can be seen from table 2 that these formulations are stable.