巴西专利BR112015009806B1 WATER ADJUVANT COMPOSITION UNDERSTANDING A MIXTURE OF OCTANOIL-N-METHYLGLUCAMIDE AND DECANOIL-N-METH

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专利摘要:
aqueous adjuvant compositions. the present invention relates to an adjuvant composition containing: a) one or more alkyl glucamides of formula (i) (i) wherein r1 is a linear or branched alkyl group with five to nine carbon atoms and r2 is an alkyl group with one to three carbon atoms; b) water; c) optionally a cosolvent. the invention further relates to the use of such compositions to increase the biological activity of pesticides, preferably herbicides, and to produce an aqueous pesticide composition.
公开号:BR112015009806B1
申请号:R112015009806-1
申请日:2013-11-01
公开日:2020-09-15
发明作者:Andreas Wacker
申请人:Clariant Finance (Bvi) Limited；
IPC主号:

专利说明:

[001] The present invention relates to aqueous adjuvant compositions including alkylglucamides, their use for the production of aqueous pesticidal compositions and to aqueous pesticidal compositions containing alkylglucamides.
[002] Pesticides (primarily fungicides, herbicides and insecticides) are chemical substances produced synthetically or of natural origin, which penetrate the cells of plants, plant tissues, or parasitic organisms within or on the plant, causing their damage and / or destruction. Most pesticides are herbicides. Pesticides are commonly used in the form of concentrated liquid or solid preparations (formulations) in agriculture. These preparations make handling easier for the user or guarantee greater activity by the active ingredient. The formulations are usually diluted with water before use and then delivered by spray application.
[003] Water-soluble concentrates (Soluble Liquids, abbreviated from SL) are a particularly important form of pesticide preparations. They play a large role particularly for herbicides, with pesticides generally being used as water-soluble salts that are converted to their alkali metal salts or ammonium salts by neutralizing the acidic form of the herbicides with appropriate bases.
[004] A particularly important role is played by the water-soluble salts of herbicides such as glyphosates, glufosinates, or auxin herbicides such as 2,4-D or dicamba. They are used preferably as the alkali metal salt or in the form of various ammonium salts, or as a mixture of these salts, usually as aqueous formulations.
[005] A general problem with the use of pesticides is that only a fraction of the active ingredient develops the desired activity. Most of it is usually lost unused, with the active ingredient failing to reach the leaves or roots of the plant when the sprayed mixture is delivered, being instead infiltrated and rendered useless in the soil, washed by rain, or simply not being properly absorbed by the plant.
[006] This environmental and economic disadvantage can be reduced by the addition of auxiliaries, identified in the context of the present patent application as "adjuvants", for pesticide formulations. These auxiliaries can, for example, reduce unwanted spray diffusion, improve plant wetting, or ensure that the active ingredient is adhered to the plant's surface for a longer time and / or is absorbed more efficiently. Particularly in the case of water-soluble pesticides, such as, for example, in the case of glyphosate, the nature and also the quantity of adjuvants used have a critical influence on the training activity.
[007] By far the adjuvants most commonly used in aqueous herbicidal formulations are fatty amine ethoxylates, mainly tallow fatty amine ethoxylates. Due to their toxic and ecotoxicological properties, however, such as, for example, severe eye irritation or toxicity to aquatic organisms, these products are classified as objectionable and are increasingly being replaced by adjuvants having a better toxicological and ecotoxicological profile.
[008] Adjuvants that are used in aqueous pesticide formulations are usually in liquid form, that is, as water-miscible solutions, in order to simplify the production of the pesticide formulation. Adjuvant solutions can include water and / or water-miscible solvents which together with the pesticide produce a homogeneous and storage-stable aqueous formulation. Water is used as a solvent if possible, being preferred for reasons not only of cost, but also for the environment. Co-solvents can be used, capable of improving solubility or stability.
[009] The use of sugar-based surfactants, such as alkyl-N-methylglucosamides, in cleaning products and cosmetic products, for example, is described in the literature (FW Lichtenthaler, "Carbohydrates as Organic Raw Materials" in Ullmann's Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH Verlag, 2010).
[0010] WO 96/16540 describes pesticidal compositions which are long chain alkylamides which have a polyhydroxycarbonyl substituent in the amide nitrogen having at least three hydroxyl groups. Emulsifiable concentrated water-dispersible powders and granules of dodecanoyl-N-methylglucamide, dodecanoyletradecanoyl-N-methylglucamide, and cetylesteraryl-N-methylglucamide are described in the examples.
[0011] The requirements for adjuvants in aqueous pesticidal compositions have grown steadily over the years. In addition to high biological activity and irreproachable, from the point of view of both the user and the environment, performance properties are becoming increasingly more advantageous. Adjuvants must allow very high loading of the formulation with the active ingredient, and must be compatible as much as possible with different active ingredients. The formulations must be stable in storage and must have a very low viscosity, in order to guarantee greater ease of handling, and they must also facilitate the complete or almost complete emptying of the containers. Additional requirements are for efficient miscibility and rapid dissolution capacity, including and particularly in ice water, when the sprayable mixture is being prepared.
[0012] The objective, according to this, was the supply of new aqueous adjuvant compositions that are highly active, that are distinguished by a toxicological and environmental profile very advantageous, and that have advantageous properties from a performance point of view.
[0013] The goal is surprisingly achieved by new adjuvant compositions including a) one or more alkylglucamides of formula (I)

[0014] where
[0015] R1 is a straight or branched alkyl group having 5 to 9 carbon atoms,
[0016] R2 is an alkyl group having 1 to 3 carbon atoms, b) water c) optionally a cosolvent. In one or more alkylglucamides of formula (I), the radical R1 is preferably a linear or branched alkyl group having 7 to 9 carbon atoms. The radical R2 is preferably a methyl group.
More preferably, the adjuvant compositions of the invention include a mixture of octanoyl-N-methylglucamide (R1 = Cy alkyl, R2 = methyl) and decanoyl-N-methylglucamide (R1 = Cs-alkyl, R2 = methyl). The octanoyl-N-methylglucamide fraction in this mixture is 1 (at 90% by weight, preferably from 20 to 80% by weight, and more preferably from 30 to 70% by weight, based on the total amount of alkylglucamides present in the mixture. The decanoyl-N-metigucamide fraction in this mixture is 10 to 90% by weight, preferably 20 to 80% by weight, and more preferably 30 to 70% by weight, based on the total amount of alkylglucamides present in the mixture.
[0018] The pentahydroxyethyl radical in the alkylglucamides of formula (I) has different chiral centers, which means that in each case there are a plurality of possible stereoisomers. The alkylglucamides of formula (I) are usually prepared from naturally occurring sugars such as, for example, D-glucose, although in principle it is possible to use other natural or synthetic hexoses or also other Ce building blocks, resulting in different formula stereoisomers (I).
[0019] Co-solvent c) optionally included may either be present as a secondary component of the alkylglucamide preparation procedure, or it may be added subsequently to the adjuvant composition. The cosolvent can include a single solvent or a mixture of two or more solvents. All polar solvents that are compatible with the aqueous pesticide composition and form a homogeneous phase are suitable for this purpose. Examples of suitable cosolvents are monohydric alcohols such as, for example, methanol, ethanol, propanols, butanols, benzyl alcohol, or polyhydric alcohols such as, for example, ethylene glycol, diethylene glycol, propylene glycol, or glycerol, or polyglycols such as , for example, polyethylene, polypropylene, or mixed polyalkylene glycols (PAGs). Other suitable solvents are ethers such as, for example, propylene glycol monomethyl or dimethyl ether, dipropylene glycol monomethyl or dimethyl ether, amides such as, for example, N-methyl- or N-ethylpyrrolidone, for example, N, N-dimethylacetamide, N, N-dimethylcaprilamide, or N, N-dimethyldecanamide.
Particularly preferred co-solvents are mono or polyhydric alcohols, and especially suitable are dihydric or trihydric alcohols such as, for example, propylene glycol, glycerol, or mixed polyethylene, polypropylene and / or polyalkylene glycols (PAGs ).
[0021] The fraction of the cosolvent in the composition is usually 10 to 250 g / L, preferably 20 to 200 g / L, and more preferably 30 to 150 g / L.
[0022] The co-solvent can additionally contribute to the stabilization of adjuvant compositions by, for example, increasing stability at low temperature or stability at heat, or positively influencing other performance properties such as, for example, viscosity.
[0023] The alkylglucamides of formula (I) are preferably based on renewable raw materials and are notable for their toxicological and environmental profile. They have high water solubility.
The aqueous adjuvant compositions preferably include 10 to 90% by weight, more preferably 20 to 80% by weight, and especially and preferably 30 to 70% by weight, of one or more alkylglucamines of component a).
[0025] The aqueous adjuvant compositions of the alkylglucamides of formula (I) are suitable as adjuvants in aqueous pesticidal compositions for enhancing the biological activity of herbicides, insecticides, fungicides, acaricides, bactericides, molluscs, nematicides, and rodenticides.
[0026] Another subject of the invention is, therefore, the use of aqueous adjuvant compositions to boost the biological activity of pesticides, particularly herbicides.
[0027] Aqueous adjuvant compositions are excellently suitable for the production of storage-stable aqueous pesticidal compositions that have advantageous properties.
[0028] Another subject of the invention is, therefore, the use of alkylglucamide compositions for the production of aqueous pesticidal compositions. Customary methods for producing such pesticidal compositions are known to the skilled person.
[0029] In addition, another subject of the invention are pesticidal compositions including a) one or more alkylglucamides of formula (I)

[0030] where
[0031] R1 is a straight or branched alkyl group having 5 to 9 carbon atoms,
[0032] R2 is an alkyl group having 1 to 3 carbon atoms, b) water c) optionally a cosolvent d) one or more water-soluble pesticides.
[0033] Water-soluble pesticides for the purposes of the invention are to be understood as pesticides which at room temperature (25 ° C) must have a solubility of 50 g / L or more and preferably more than 100 g / L in water.
[0034] Preferred water-soluble pesticides are the water-soluble herbicides, among which preference is given to the water-soluble salts of acifluorfen, aminopyralide, amitrole, asulam, benazoline, bentazone, bialafos, bispiribac, bromacila, bromoxynil, bambopirone, bicyclopirone, bicyclopirone , clopyralid, 2,4-D, 2,4-DB, dicamba, dichorprop, difenzoquat, diquat, endotal, fenoxaprop, flamprop, flumichlorac, fluoroglycofen, fomesafen, phosamine, glufosinate, glyphosate, imizamet, imazametabenz, imazomox, imazapic, imazapic, imazapic, , imazaquine, imazetapyr, MCPA, MCPB, mecoprop, octanoic acid, paraquat, pelargonic acid, picloram, quizalofop, 2,3,6-TBA, and triclopyr. The precise structure and chemical composition of all these compounds are known and can be consulted on the Internet at: http://www.alanwood.net/pesticides/index_cn_frame.html.
[0035] Water-soluble salts of 2,4-D, bentazone, dicamba, fomesafen, glyphosate, glufosinate, MCPA, and paraquat are particularly preferred. Glyphosate water-soluble salts are exceptionally preferred.
[0036] The preference among the water-soluble salts is given in particular to the alkali metal salts and ammonium salts, and of these instead of the potassium, ammonium, dimethylammonium, isopropylammonium, and (2-hydroxyethyl) trimethylammonium salts.
[0037] The water-soluble pesticides of component d) may include a combination of two or more pesticides. Such combinations are important especially when the target, for example, is to broaden the activity spectrum of the pesticidal composition or, more efficiently, to prevent resistance to particular pesticides.
[0038] The combination of two or more water-soluble pesticides in a formulation, however, is a difficult undertaking. This is due to the fact that the active ingredients are not compatible with each other, and the aqueous mixtures are therefore not stable in phase. Very surprisingly, however, the alkylglucamides of formula (I) are suitable for the stabilization of such fundamentally incompatible compositions, a fact that was hitherto unknown.
[0039] In a further embodiment of the invention, therefore, the pesticidal compositions of the invention include at least two water-soluble pesticides of component d).
[0040] Preferably, at least two pesticides are selected from glyphosate, glufosinate, 2,4-D, dicamba, and fomesafen.
[0041] Particularly preferred compositions are those water-soluble pesticides of component d) include the combinations of the two herbicides glyphosate and 2,4-D, glyphosate and dicamba, glyphosate and fomesafen, glyphosate and glufosinate, 2,4-D and dicamba , glufosinate and 2,4-D, and glufosinate and dicamba.
[0042] The preparation of the alkylglucamides of formula (I) has been well described before and is known to the skilled person. It is achieved, for example, by condensing carboxylic esters with a secondary N-alkylglucamine, which in turn can be prepared by reductive amination of a sugar such as, for example, D-glucose.
[0043] The alkylamides of formula (I) described above can be used to produce the pesticidal compositions of the invention, especially aqueous herbicidal formulations having excellent performance properties.
[0044] In formulating aqueous pesticidal compositions, a concern is to load the composition with as high an active ingredient concentration as possible. Doing this reduces packaging, transportation, storage and disposal costs. An adjuvant composition must therefore be able to allow stable highly charged compositions, known as "high-load" formulations. This is achieved surprisingly well with the alkylglucamides of formula (I).
[0045] In a preferred embodiment of the invention, the amount of one or more water-soluble pesticides of component d) in the compositions of the invention is greater than 100 g / L, preferably greater than 200 g / L, and more preferably greater than 300 g / L. These quantity figures are based on the total weight of the pesticidal composition of the invention, and the amount of free acid, or "acid equivalents" (ae) in the case of pesticides used in the form of their water-soluble salts (such as, for example, usually glyphosate or 2,4-D).
[0046] In an additional preferred embodiment of the invention, the amount of one or more alkylglucamides of formula (I) in the pesticidal compositions of the invention is from 20 to 250 g / L, preferably from 40 to 200 g / L, and more preferably from 50 to 150 g / L. These quantity figures are based on the total amount of the pesticidal composition of the invention.
[0047] The alkylglucamides of formula (I) are commonly used in the form of solutions. For clarification, it should be noted that the quantity figures mentioned above are based in this case on the active content of the alkylglucamides of formula (I) in the solution.
[0048] A particularly important criterion for the storage stability of aqueous pesticidal compositions, such as glyphosate formulations and 2,4-D formulations, is phase stability. A composition is characterized as having a sufficiently stable phase when it remains homogeneous over a wide temperature range and when there is no formation of two or more separate phases or precipitates (formation of an additional solid phase). Phase stability - both at high temperature, as it can occur, for example, in the case of storage in the sun or in hot countries, as well as at low temperature, for example, in winter or in cold climate regions, for example - is a critical prerequisite for a stable formulation in storage.
[0049] The pesticidal compositions of the invention are notable in that they have a stable phase even at a temperature preferably greater than 55 ° C, more preferably greater than 70 ° C, and especially and preferably greater than 80 ° C.
[0050] In addition, the pesticidal compositions of the invention are notable in that they have a stable phase even at a temperature preferably below 10 ° C, more preferably below 0 ° C, and especially and preferably below -10 ° C.
[0051] The pH of the pesticidal compositions of the invention is usually in the range of 3.5 to 8.0, preferably from 4.0 to 7.0, and more preferably from 4.5 to 6.5 (measured in the form of a 1% by weight aqueous dilution). The pH is determined primarily by the pH values of the aqueous pesticide solutions, present in the form of weak acid salts. By adding acids or bases, the pH can be adjusted to a different value than the original pH of the mixture.
[0052] The high salt solubility of the pesticidal composition of the invention in an aqueous medium, even in the case of a high concentration of pesticide, constitutes a great performance advantage. It also makes it possible for agrochemical salts, such as fertilizers, to be included in the composition.
[0053] In another preferred embodiment of the invention, therefore, the pesticidal compositions include one or more agrochemical salts, preferably ammonium salts.
[0054] With particular preference, the pesticidal compositions include ammonium sulfate, ammonium nitrate, ammonium phosphate, ammonium thiocyanate and / or ammonium chloride.
[0055] The pesticidal compositions of the invention may include one or more auxiliaries additional to one or more alkylglucamides of formula (I), and in this case, the additional auxiliaries may be, for example, preservatives, surfactants, defoamers, functional polymers, or additional adjuvants.
[0056] Condoms that can be used include organic acids and their esters, such as, for example, ascorbic acid, ascorbyl palmitate, sorbate, benzoic acid, methyl and propyl 4-hydroxybenzoate, propionates, phenols such as 2- phenylphenate, 1,2-benzoisothiazolin-3-one, formaldehyde, sulfurous acid, and salts thereof.
[0057] Surfactants can generally be all nonionic, amphoteric, cationic, or anionic surfactants that are compatible with the composition.
[0058] Examples of nonionic surfactants are ethoxylated and alkoxylated from relatively long chain aliphatic or aromatic alcohols, fatty amine ethoxylates, relatively long chain ether alkoxylates, sorbitan esters (optionally ethoxylated), and alkyl polyglycosides. Suitable amphoteric surfactants include long-chain alkyldimethylbetaines or alkyldimethylamine oxides, or alkyldimethylaminamidopropylamine oxides. Suitable among anionic surfactants, for example, are ethoxylated fatty alcohol ether sulfates, reaction products of long chain alcohols (optionally ethoxylated) with phosphoric acid derivatives. Appropriately under "long chain" are included straight or branched hydrocarbon chains having at least 6 and not more than 22 carbon atoms.
[0059] Suitable defoamers are alkoxylated from fatty acid alkyl ester, organopolysiloxanes such as, for example, polydimethylsiloxanes and mixtures of these with microfine and optionally silanized silica; perfluoroalkylphosphonates and phosphinates, paraffins, waxes and microcrystalline waxes, and mixtures of these with silanized silica. They are also advantageous to mixtures of different foam inhibitors, examples being those composed of silicone fluid, liquid paraffin and / or waxes.
[0060] The functional polymers that can be present in the pesticidal composition of the invention are high molecular weight compounds of synthetic or natural origin with a molar mass greater than 10,000. Functional polymers can, for example, act as an agent against unwanted diffusion or can boost resistance to rain.
[0061] In a further preferred embodiment of the invention, the pesticidal compositions of the invention include one or more adjuvants in addition to one or more alkylglucamides of component a), such adjuvants being those that can be conventionally used in aqueous pesticidal compositions.
These are preferably amine grease ethoxylates, amine ethoxylates, alkyl betaine or amidoalkyl betaine, amine oxides or amidoalkylamine oxides, alkyl polyglycosides, or copolymers of glycerol, coconut fatty acid, and phthalic acid.
[0063] These adjuvants are known in the literature as adjuvants in aqueous pesticidal compositions and are described in W02009 / 029561, for example.
[0064] In an additional preferred embodiment of the invention, the pesticidal compositions of the invention take the form of concentrated formulations that are diluted before use, in particular with water (examples being "ready-to-use", "canned" formulations, or "incorporated"), and they include one or more water-soluble pesticides of component d) in amounts of 5 to 80% by weight, preferably 10 to 70% by weight, and more preferably 20 to 60% by weight, and one or more alkylglucamides of formula (I) in amounts of 1 to 25% by weight, preferably 2 to 20% by weight, and more preferably 3 to 15% by weight. These quantity figures are based on the overall concentrated formulation, and on the amount of free acid, the "acid equivalent" (a.e.), in the case of pesticides that are used in the form of their water-soluble salts.
[0065] The pesticidal compositions of the invention are applied to the fields preferably in the form of sprayable mixtures. These sprayable mixtures are produced by diluting concentrated formulations with a defined amount of water.
[0066] In an additional preferred embodiment of the invention, the compositions of the invention are in the form of sprayable mixtures and include from 0.001 to 10% by weight, preferably from 0.02 to 3% by weight, and more preferably from 0.025 to 2% by weight of one or more water-soluble pesticides of component d) and 0.001 to 3% by weight, preferably from 0.005 to 1% by weight, and more preferably from 0.01 to 0.5% by weight of one or more alkylglucamides of formula (I). The quantity figures cited are based on the global sprayable mixture, and the amount of free acid, the "acid equivalent" (a.e.), in the case of pesticides that are used in the form of their water-soluble salts.
[0067] The invention additionally relates to the use of the inventive pesticide compositions to check and / or to control weeds, fungal diseases, or insect infestation. Preference is given to the use of the compositions of the invention for the control and / or checking of weeds.
[0068] These uses can also occur preferably by the so-called tank mixing method. In this scenario, then, one or more water-soluble pesticides of component d) and one or more alkylglucamides of formula (I), as well as water, can take the form of the so-called "tank mixture" preparation. In such a preparation, both one or more water-soluble pesticides and one or more alkylglucamides of formula (I) - the latter optionally together with additional adjuvants - are present separately from each other. Before application, generally shortly before application, the two preparations are mixed with each other, producing a pesticidal composition of the invention. FUNCTIONAL EXAMPLES
[0069] The invention is further illustrated below for the skilled person, using examples which, however, should not be considered in any way as confining the invention to the modalities shown. Example 1: Production of an inventive aqueous alkylglucamide composition
[0070] The alkylglucamide was prepared from a Cs / Cw methyl carboxylic acid ester (55% by weight Cs fraction, 45% by weight Cio fraction) commercially available by reaction with N-methylglucamine in propylene glycol as described in WO 92/06073. A mixture was formed that as well as 90% by weight of the alkylglucamide of formula (I), with R1 = CsHi and C10H21, and R2 = CH3, also contained 10% by weight of propylene glycol in the reaction mixture. 60 g of this mixture was dissolved in 40 g of water. This generated a stable aqueous solution of C8 / 10-N-metiglucamide with a content of 54% by weight of water / propylene glycol. Example 2: Attempted to produce a non-inventive aqueous alkylglucamide composition (comparative example)
[0071] The alkylglucamide was prepared from a commercially available C12 / C14 methyl ester (C12 fraction of 69% by weight, C14 fraction of 25% by weight, and 6% by weight of other chain constituents) by reaction with N-methylglucamine in propylene glycol as described in WO 92/06073. This generated a mixture that as well as 90% by weight of the alkylglucamide of formula (I), with R1 = C12H23 and C14H29, and R2 = CH3, also contained 10% by weight of propylene glycol in the reaction mixture. An attempt was made to dissolve this mixture in water, in analogy to example 1, but no stable solutions were obtained. The results are compiled in Table 1. Example 3: Attempted to produce a non-inventive aqueous alkylglucamide composition (comparative example)
[0072] The alkylglucamide was prepared from a commercially available Cw / Cw methyl ester (38% by weight Ciβ fraction, 60% by weight Cw fraction, and 2% by weight of other chain constituents) by reaction with N-methylglucamine in propylene glycol as described in WO 92/06073. This generated a mixture that as well as 90% by weight of the alkylglucamide of formula (I), with R1 = C16H33 and C18H37, and R2 = CH3, also contained 10% by weight of propylene glycol in the reaction mixture. An attempt was made to dissolve this mixture in water, in analogy to example 1, but no stable solutions were obtained. The results are compiled in Table 1. Table 1: Dissolution tests of relatively long chain alkylglucamides in water

[0073] Since it was not possible to produce stable and manageable solutions of Ci2 / i4-glucamide, a solution with a concentration of 20% by weight in polyethylene glycol was prepared for biological tests and for formulation experiments. With C16 / 18-glucamide, the preparation of a solution of propylene glycol in the same concentration was not possible. Example 4: Biological activity of adjuvant compositions
[0074] For the purpose of determining biological activity, greenhouse tests were performed with glyphosate on Echinochloa crus-galli (L.) Beauv. (ECHCG), Cirsium arvense L. (CIRAR), and Solanum nigrum L. (SOLNI). The plants were grown in a greenhouse under 14 hours of irradiation with a light at a temperature of 19/14 (± 0.5) ° C (day / night) and a relative humidity of 70/80 (± 5)% (day /night). The light was provided through high pressure sodium lamps, high pressure mercury lamps, and fluorescent tubes, producing a power of 70 W / m2 at the leaf level. The plants were grown in plastic pots 12 cm in diameter filled with a mixture of sand and humus in a sand: humus ratio of 1: 2 by volume.
[0075] The pots were placed on an irrigation mattress under the soil, which was moistened daily with a medium concentration nutrient solution. After their appearance on the substrate surface, the seeds were reduced to five (ECHCG), two (CIRAR), or one (SOLNI) plant per pot for the activity tests.
[0076] The sprayable solutions were applied using a laboratory sprayer operated with compressed air and equipped with a Teejet nozzle TP8003E at an application rate of 200 L / ha for plants at 303 kPa. ECHCG was treated in the two to three leaf stage; CIRAR and SOLNI were treated in the four-leaf stage.
[0077] For a more differentiated examination of the adjuvant effect, the active ingredient of glyphosate was underdosed, meaning that the plants were not completely killed. This was done using aqueous solutions of the glyphosate-isopropylammonium salt (glyphosate IPA). The amount of glyphosate used was 33.8 g ae / ha of glyphosate IPA (corresponding to 1.0 mmol or 0.17 g ae / ha for a net volume of 200 L / ha) in the case of ECHCG, and to 20.3 g ae / ha of glyphosate IPA (corresponding to 0.6 mmol or 0.10 g ae / L in a net volume of 200 L / ha) for CIRAR and SOLNI.
[0078] The amount of adjuvant in each sprayable solution was 0.25%. Differences in the active content of the products used were taken into account. The amounts used have been corrected - that is, the figure of 0.25% by weight referred in all cases to 100% of active content of adjuvants - and are therefore comparable with each other.
[0079] An overview of alkylglucamides and the comparison substances tested is given below in Table 2. Table 2: Overview of used A1 to A4 adjuvants

[0080] The activity of the various adjuvants was examined 4 days after application by determining the mass of the plant parts still present (fresh weight; FW), and was reported as a percentage fraction, relative to the untreated plant (Table 3). Table 3: Effect of adjuvants on glyphosate IPA activity

[0081] The results of the experiments show that the inventive adjuvant composition based on Cs / Cw-alkyl-N-methylglucamide (see A1) is much more efficient than that based on non-inventive chain Ci2 / Ci4-alkyl-N-methylglucamide higher (see A2). At the same time, an activity comparable with (or greater than) the commercial products Genamin 267 (see A3) or Synergen GL 5 (see A4) is achieved (see A4). Example 5: Aqueous glyphosate compositions
[0082] Two inventive pesticidal compositions were produced from a commercial aqueous solution of glyphosate-isopropylammonium salt (concentration of 62% by weight in water), the adjuvant composition A1, and water. The resulting compositions 11 and I2 contained 360 and 480 g / L of glyphosate a.e. (a.e .: acid equivalent).
[0083] For comparison, two non-inventive pesticidal compositions were produced with Ci2 / Ci4-alkyl-N-methylglucamide (A2) and also Genamin 267 (A3) and Synergen GL 5 (A4). The cloud point and viscosity of the compositions were determined.
[0084] The cloud point was determined by heating the composition, which was heated until cloudiness occurred. After that, the composition was cooled with stirring and continuous temperature monitoring. The temperature at which the cloudy solution became clear again was recorded as the cloud point value.
[0085] The results are shown in Tables 4 and 5 below. Table 4: Glyphosate IPA formulations at 360 g / L ae

[0086] With the non-inventive (A2) Ci2 / Ci4-alkyl-1-methylglucamid (A2), it was not possible to produce a stable glyphosate formulation (experiment C1); only a gel of firm consistency was formed. No attempt was therefore made to produce a glyphosate composition with an even greater load (experiment C4). Table 5: IPA glyphosate formulations at 480 g / L ae

[0087] The experiments make it clear that the inventive adjuvant composition (= A1) generates both glyphosate IPA formulations at 360 g / L a.e. stable as 480 g / L a.e. stable, which are distinguished by more advantageous application properties, specifically by a higher cloud point and, therefore, at the same time also a lower viscosity, in comparison with the non-inventive C2 / C14-alkyl-N-methylglucamide (A2) and commercial products Genamin 267 (A3) and Synergen GL 5 (A4). Example 6: Aqueous 2,4-D-DMA compositions
[0088] An inventive pesticidal composition was produced from 76.0 g of an aqueous solution of 2,4-D-dimethylammonium salt (concentration of 69% by weight), 15.0 g of adjuvant composition A1, and 14.5 g of water. The formulation had an active content of 440 g / L a.e. (acid equivalent) based on 2,4-D. The phase stability of the formulation was determined by checking the cloud point and also by the low temperature stability at 0 ° C and -10 ° C. The formulation showed a cloud point> 95 ° C and was homogeneous and stable in phase after storage for 24 hours at both 0 ° C and -10 ° C. Example 7: Aqueous glyphosate / 2,4-D compositions
[0089] Inventive combined glyphosate / 2,4-D formulations in three (3) different proportions (I3, I4, and I5) were produced from aqueous solutions of glyphosate-isopropylammonium salt (concentration of 62% by weight), salt 2,4-D-dimethylammonium (69% by weight concentration), and the adjuvant composition A1 (see Table 6).
[0090] Three non-inventive compositions served as a comparison in each case containing Genamin 267 (C7, C8, and C9) and Synergen GL 5 (C10, C11, and C12) instead of A1 (Table 6). Table 6: Glyphosate / 2,4-D formulations combined

[0091] For all formulations, the phase stability was checked by determining the cloud point, and also by the low temperature stability at 0 ° C and -10 ° C. The results are shown in Table 7 below. Table 7: Cloudiness and low temperature stability points of the compositions

[0092] The results of these experiments show that the inventive combined formulations were much more stable over a wider range than similar compositions based on the commercial products Genamin 267 and Synergen GL 5.

权利要求:
Claims (30)
[0001]
1. Aqueous adjuvant composition, characterized by the fact that it comprises: a) a mixture of octanoyl-N-methylglucamide and decanoyl-N-methylglucamide of formula (I):
[0002]
2. Adjuvant composition according to claim 1, characterized by the fact that the octanoyl-N-methylglucamide fraction is 30 to 70% by weight, and the decanoyl-N-methylglucamide fraction is 30 to 70% in weight, based on the total amount of alkylglucamides present in said mixture.
[0003]
Adjuvant composition according to claim 1 or 2, characterized in that the fraction of a plurality of alkylglucamides a) is 10 to 90% by weight, based on the total weight of the composition.
[0004]
4. Use of an adjuvant composition comprising: a) one or more alkylglucamides of formula (I):
[0005]
5. Use according to claim 4, characterized by the fact that, in formula (I), R1 is a linear or branched alkyl group having 7 to 9 carbon atoms, and R2 is a methyl group.
[0006]
Use according to claim 4 or 5, characterized in that the adjuvant composition is a composition as defined in any one of claims 1 to 3.
[0007]
7. Use of an adjuvant composition comprising: a) one or more alkylglucamides of formula (I):
[0008]
8. Use according to claim 7, characterized by the fact that, in formula (I), R1 is a linear or branched alkyl group having 7 to 9 carbon atoms, and R2 is a methyl group.
[0009]
Use according to claim 7 or 8, characterized in that the adjuvant composition is a composition as defined in any one of claims 1 to 3.
[0010]
10. Pesticidal composition, characterized by the fact that it comprises: a) one or more alkylglucamides of formula (I)
[0011]
Pesticidal composition according to claim 10, characterized in that, in formula (I), R1 is a linear or branched alkyl group having 7 to 9 carbon atoms, and R2 is a methyl group.
[0012]
12. Use according to claim 10 or 11, characterized in that one or more alkylglucamides of formula (I) are a mixture as defined in claim 1 or 2.
[0013]
13. Pesticidal composition according to any one of claims 10 to 12, characterized by the fact that the one or more water-soluble pesticides of component d) are selected from the group of herbicides.
[0014]
14. Pesticidal composition according to any of claims 10 to 13, characterized by the fact that the one or more water-soluble pesticides of component d) are selected from the group consisting of water-soluble salts of acifluorfen, aminopyralide, amitrola, asulam, benazolin, bentazone, bialafos, bispiribac, bromacila, bromoxynil, bicyclopyrone, chlorambene, clopyralide, 2,4-D, 2,4-DB, dicamba, dichorprop, difenzoquat, diquat, endotal, fenoxaprop, flamprop, flumiclorac, fluoroglic fomesafen, phosamine, glufosinate, glyphosate, imizamet, imazametabenz, imazomox, imazapic, imazapyr, imazaquine, imazetapyr, MCPA, MCPB, mecoprop, octanoic acid, paraquat, pelaronic acid, picloram, quizalofop, tr .
[0015]
15. Pesticidal composition according to any one of claims 10 to 14, characterized by the fact that the one or more water-soluble pesticides of component d) are selected from the water-soluble salts of 2,4-D, bentazone, dicamba , fomesafen, glyphosate, glufosinate, MCPA, and paraquat.
[0016]
16. Pesticidal composition according to any one of claims 10 to 15, characterized in that the composition comprises at least two water-soluble pesticides of component d).
[0017]
17. Pesticidal composition according to claim 16, characterized by the fact that the water-soluble pesticides of component d) are selected from glyphosate, glufosinate, 2,4-D, dicamba, and fomesafen.
[0018]
18. Pesticidal composition according to claim 17, characterized by the fact that the water-soluble pesticides of component d) are combinations of the two herbicides glyphosate and 2,4-D or glyphosate and dicamba or glyphosate and fomesafen or glyphosate and glyphosinate or 2,4-D and dicamba or glufosinate and 2,4-D or glufosinate and dicamba.
[0019]
19. Pesticidal composition according to any of claims 10 to 18, characterized by the fact that the total amount of one or more water-soluble pesticides of component d) in the composition is greater than 100 g / L, based on its equivalent acid.
[0020]
20. Pesticidal composition according to any one of claims 10 to 19, characterized in that the total amount of one or more alkylglucamides of formula (I) in the composition is 20 to 250 g / L.
[0021]
21. Pesticidal composition according to any one of claims 10 to 20, characterized in that it is a stable phase at a temperature greater than 55 ° C.
[0022]
22. Pesticidal composition according to any one of claims 10 to 21, characterized in that it is a stable phase at a temperature below 10 ° C.
[0023]
23. Pesticidal composition according to any one of claims 10 to 22, characterized in that it comprises one or more agrochemical salts.
[0024]
24. Pesticidal composition according to claim 23, characterized by the fact that the one or more agrochemical salts are ammonium salts.
[0025]
25. Pesticidal composition according to any one of claims 10 to 24, characterized in that it comprises one or more adjuvants in addition to the alkylglucamide of component a).
[0026]
26. Pesticidal composition according to any one of claims 10 to 25, characterized by the fact that one or more adjuvants are selected from the group of grease amine ethoxylates, amine ethoxylates, alkylbetaines or amidoalkylbetaines, amine oxides or oxides of amine amidoalkylamine, alkylpolyglycosides, or copolymers of glycerol, coconut fatty acid, and phthalic acid.
[0027]
27. Pesticidal composition according to any one of claims 10 to 26, characterized in that it is in the form of a concentrated formulation which is diluted before use and which comprises from 5 to 80% by weight of one or more pesticides water-soluble component d), and 1 to 25% by weight, of one or more alkylglucamides of component a).
[0028]
28. Pesticidal composition according to any one of claims 10 to 27, characterized in that it is in the form of a sprayable mixture and that includes from 0.001 to 10% by weight of one or more water-soluble pesticides of component d) , and from 0.001 to 3% by weight of one or more alkylglucamides of component a).
[0029]
29. Use of a pesticidal composition, as defined in any of claims 10 to 28, characterized by the fact that it is for checking and / or controlling weeds, diseases caused by fungus, or insect infestation.
[0030]
30. Use, according to claim 29, characterized by the fact that it is for checking and / or controlling weeds, diseases caused by fungus, or insect infestation by a tank mixing method.

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同族专利:

公开号 | 公开日

CN104918490B|2017-12-15|

EP2914108B1|2017-11-01|

AU2017258911A1|2017-11-30|

AU2017258911B2|2019-05-16|

AU2013339790A1|2015-05-21|

CA2890378C|2021-06-22|

US10772324B2|2020-09-15|

WO2014067663A1|2014-05-08|

ES2653926T3|2018-02-09|

DE102012021647A1|2014-05-08|

BR112015009806A2|2017-07-11|

EP2914108A1|2015-09-09|

CA2890378A1|2014-05-08|

CN104918490A|2015-09-16|

DK2914108T3|2017-12-11|

US20150320037A1|2015-11-12|

AU2013339790B2|2017-08-10|

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