Derivatives of mepiquate borate, methods for their preparing, electrochemical method for preparing n,n-dimethylpiperidinium, suspension concentrate possessing plant growth-regulating effect

FIELD: chemistry of metalloorganic compounds, agriculture.

SUBSTANCE: invention describes derivatives of mepiquate borate of the general formula (I): wherein DMP means N,N-dimethylpiperidinium (mepiquate); M means metal cation acceptable for agriculture and chosen from a series comprising sodium, potassium, magnesium, calcium, zinc, manganese or copper, hydrogen atom or NH4+; O means oxygen atom; A means chelate of complex-forming fragment bound with one boron atom and representing (lower)-alkylglycols or sugars; n and m mean similar whole numbers in the range from 1 to 6; x means a whole or fraction number in the range from 0 to 10; y means a whole or fraction number in the range from 1 to 48; z means a whole or fraction number in the range from 0 to 48; v means a whole or fraction number in the range from 0 to 24, and w means a whole or fraction number in the range from 0 to 24. Also, invention describes methods for preparing compound of the formula (I) by interaction of N,N-dimethylpiperidinium hydroxide with boric acid and/or boron-containing oxides and optionally with metal hydroxides acceptable for agriculture indicated above or electrochemical method involving interaction of N,N-dimethylpiperidinium halide in the presence of water and boric acid and in the presence metal hydroxides acceptable for agriculture by bipolar electrodialysis. Invention describes electrochemical method for preparing N,N-dimethylpiperidinium hydroxide and a suspension concentrate possessing the plant growth-regulating effect prepared by mixing N,N-dimethylpiperidinium hydroxide, boron-containing compound chosen from boric acid and borate salt with a thickening agent and water, or by mixing compound of the formula (I) with Na2B8O13 x 4 H2O, a thickening agent and water. Prepared derivatives of mepiquate borate possess the improved indices of hygroscopicity and corrosion activity.

EFFECT: improved preparing methods, valuable properties of derivatives.

22 cl, 7 tbl, 16 ex

 

The technical field of the invention

The present invention relates to new compositions of plant growth regulators and their use. In particular, it relates to compositions comprising boron-containing compounds of mepiquat, and to methods of regulating plant growth, in particular the regulation of plant growth of cotton.

Background of invention

The plant growth regulators (PPP) affect the growth and differentiation of plants. In particular, various PPP can, for example, reduce the height of the plants, to stimulate the germination of seeds, to induce flowering, call the darker colouring of the leaves, to minimize the lodging of cereal crops, to change the speed of plant growth and modify the time and efficiency of fruiting.

It is known that PPPs are an important tool in modern cotton production. Mepiquat (name according to IUPAC: N,N-dimethylpiperidine) represents the first widely used on cotton plants RRR, which is usually applied to plants of cotton in the form of its chloride, i.e. mepiquat-chloride (chloride N,N-dimethylpiperidine, DMP) by sheet metal processing.

The most visible effect of the PPP on the basis of mepiquat-chloride on plants of cotton is to reduce the total height of the plant, reducing the distance between nodes and reducing the width of the age of the Oia. This, in turn, increases the penetration of light to the lower leaves of the plant, causing the preservation and development of the lower boxes.

Related advantage, which can often be obtained by using PPP-based mepiquat-chloride, is the increase of the weight of bolls at the time of harvest. Another very valuable quality, which often get when using PPP-based mepiquat-chloride, is increasing "precocity", i.e. an earlier opening of bolls (see, for example, Khafaga, Angew. Botanik 57, 257-265 (1983); Sawan, etc., J. Agronomy & Plant Science, 154, 120-128 (1985); Ray, Deciphering PGRs, Cotton Farming, June 1997, 18-20; Cotton Production, 1995 Delta Agricultural Digest, 22-24 (published Argus Agronomics, a division of Argus, Inc.); patents US 3905798 and 4447255; Pix Official Handbook).

As described in patent US 3905798 name Zeeh with co-authors, all well-known salts of mepiquat are hygroscopic solids. Therefore, during preparation of dry fluid forms of plant growth regulators on the basis of mepiquat you must use various solid carriers such as clay, fertilizers or the like, or to apply special methods of preparation preparative forms and their packaging that provides isolation of solid particles from any humidity environment. In addition, in EP-A 710071 described method of processing and drying hygroscopic mepiquat-chloride, proposed for the preparation of t is erdich compositions and especially for the preparation of tablets.

In addition, in EP-A 573177, for example, described the waterless cooking method mepiquat-chloride, characterized in that the resulting product must be packaged in water soluble bag of polyvinyl alcohol for protection against moisture and dissolution as a result of penetration of water vapor.

In WO 09/09627 described getting dispersible in water pellets mepiquat-chloride. Proposed ways of overcoming hygroscopicity problems with certain auxiliary substances, for example, synthetic calcium silicates, binders and mixtures of different sulfonates and/or sodium carboxylates.

For the cooking process preparative forms hygroscopic nature of the salts of mepiquat is undesirable for a number of reasons. In particular, moisture promotes the decomposition of the compositions on the basis of mepiquat-chloride ions that, in turn, leads to a relatively low pH values. The result is a very strong corrosive effect, resulting in the storage of wet solids for a sufficiently long period of time. In addition, higher concentrations of anions of chlorine in the water lead to the manifestation of corrosive action in relation to many types of steel and metals. In the result in order to solve the problems associated with corrosion effect is Olga of mepiquat, as a rule, apply special access and special devices.

In addition, monoparty of mepiquat, primarily monolaurate, including monolaurate chelates or complexes, used as toners for Electrophotography (cf. for example, JP-A 05/265257; JP-A 02/166713). Aliphatic open chain monolaurate Quaternary ammonium salts described in Electrochim. Acta, 39, 18 (1994); Z. Naturforsch. B (Chim. Sci.) 48, 7 (1983); Z. Naturforsch. B (Anorg. Chem. Org. Chem.) 33B, 20 (1978); J. Nonmetals 2 (2), 103 (1974); JP-A 89/322006; US 3403304). These known monolaurate ammonium is used as electrolytes, catalytic agents, polymerization inhibitors ignition or boron-containing biocides.

However, there are no data on the use of these compounds in the field of agriculture.

Although the hygroscopic and corrosive nature mepiquat-chloride is a known problem, not proposed any alternative containing mepiquat connections that would have no hygroscopicity or corrosive action. The search for such compounds is complicated by the requirement that the modification of the connection in order to reduce its corrosive action, and hygroscopic properties should not have a negative impact on regulating the growth of plants connection properties. Otherwise, the applicability of mepiquat will be limited or even to a large degree the Yeni reduced.

In light of the problems associated with biological activity, as well as considering the fact that all known salt of mepiquat have hygroscopic nature, in the present invention proposed a modified connection of mepiquat that minimize or completely solve these problems, while maintaining the highest biological activity.

Summary of the invention

The present invention relates to new regulating plant growth compositions on the basis of mepiquat, which have improved characteristics corrosive and hygroscopic. New regulating plant growth compositions on the basis of mepiquat according to the invention can be easily obtained from commercially available technical mepiquat-chloride, among other things, using electrochemical ion exchange processes or by quaternization of N-methylpiperidine using dimethylcarbonate as the original product.

New regulating plant growth compositions on the basis of mepiquat according to the invention include borate salts of mepiquat, partial borate salt of mepiquat or mixed borate salt of mepiquat, including hydrated forms. These borate salts of mepiquat, partial borate salt of mepiquat or mixed borate salt of mepiquat have the formula I

where:

DMPdenotes N,N-dimethylpiperidine;Mindicates the acceptable cation for agriculture metal, hydrogen or NH4;Inrepresents boron;Aboutdenotes oxygen;Anddenotes a chelating or complexing fragment associated with at least one boron atom, or acceptable for agriculture cation;n and mrepresent the same integers in the range from 1 to 6;xdenotes an integer or fractional number ranging from 0 to 10;denotes an integer or fractional number ranging from greater than 1 to 48;zdenotes an integer or fractional number ranging from 0 to 48;vdenotes an integer or fractional number ranging from 0 to 24; andwdenotes an integer or fractional number ranging from 0 to 24.

Water components in the formula I denotes free or ordered intracrystalline water or "bound" water, which is usually in the structures of borates is a condensed water, which is included in the composition associated with boron hydroxyl groups.

According to PR is doctitle variant implementation And indicates the molecule from class 1-hydroxycarbonic acids, for example lactic acid, almond acid or malic acid; mono - or oligohydramnios-, di - or tricarboxylic acids, for example tartaric acid or citric acid; glycols, especially villalvilla, for example 1,2-propylene glycol, 2,3-butyleneglycol; alcohols, such as ethanol, pentanol or benzyl alcohol; mono-, di - or tricarboxylic acids, such as acetic acid, oxalic acid or benzoic acid; aminoalcohols, such as ethanolamine or diethanolamine; polyalcohol or sugars and their derivatives such as sugar alcohols, polygalacturonase acid, such as glycerol, sorbitol, mannitol, fructose and glucose or glucuronic acid; and derivatives of the above classes of compounds, such as derivatives in the form of simple or complex esters which can form at least one proton-nucleophilic configuration relative to the boron atom, for example, refers to a molecule as simple or complex ester with additional functionally active amino-, hydroxy-group or carboxylic acid.

According to one of preferred embodiments of the invention new regulating plant growth compositions on the basis of mepiquat according to the invention contain borate salt of mepiquat formula II, including hydrated forms (≤I, where x is 0):

where:

DMPdenotes N,N-dimethylpiperidine;
Inrepresents boron;
Aboutdenotes oxygen;
Anddenotes a chelating or complexing fragment associated with at least one boron atom;
n and mrepresent the same integers in the range from 1 to 6;
denotes an integer or fractional number ranging from greater than 1 to 48;
zdenotes an integer or fractional number ranging from 0 to 48;
vdenotes an integer or fractional number ranging from 0 to 24; and
wdenotes an integer or fractional number ranging from 0 to 24.

Especially preferred are the compounds of formula II in which y represents an integer or fractional number ranging from 2 to 20, more preferably in the range of from 2 to 10, particularly preferably in the range of from 3 to 10.

According to another preferred variant of the invention, the borate salt or partial borate salt of mepiquat can be mixed, i.e. included in combination with other acceptable for agriculture salts, before occhialino borate salts. Representing complex or mixed salts of the composition according to the invention have the General formula III (≤I, where x is not equal to 0):

where:

DMPdenotes N,N-dimethylpiperidine;
Mindicates the acceptable cation for agriculture metal, type of sodium, potassium, magnesium, calcium, zinc, manganese or copper, hydrogen or NH4;
Inrepresents boron;
Aboutdenotes oxygen;
Anddenotes a chelating or complexing fragment associated with at least one boron atom, or acceptable for agriculture cation;
n and mrepresent the same integers in the range from 1 to 6;
xdenotes an integer or fractional number ranging from greater than 0 to 10;
denotes an integer or fractional number ranging from greater than 1 to 48;
zdenotes an integer or fractional number ranging from 0 to 48;
vdenotes an integer or fractional number ranging from 0 to 24; and
wdenotes an integer or fractional number in the range is f from 0 to 24.

Especially preferred are the compounds of formula III in which y represents an integer or fractional number ranging from 2 to 20, more preferably in the range of from 2 to 10, particularly preferably in the range of from 3 to 10.

According to another preferred variant implementation of the new regulating plant growth compositions on the basis of mepiquat contain borate salt of mepiquat formula I, preferably a borate salt of mepiquat formula II, including hydrated forms, where

denotes an integer or fractional number ranging from 3 to 7;
zdenotes an integer or fractional number ranging from 6 to 10;
vdenotes zero;
wdenotes an integer or fractional number ranging from 2 to 10.

Especially preferred are compositions comprising the compounds of formula II, where

denotes an integer or fractional number ranging from 3 to 5;
zdenotes an integer or fractional number in the range from 6 to 8;
vdenotes zero;
wdenotes an integer or fractional number in the range is the region from 2 to 8.

Most preferred are compositions comprising the compounds of formula II, where

means 5;
zmeans 8;
vdenotes zero;
wdenotes an integer or fractional number in the range from 2 to 3.

Borate, partial borate and mixed borate salt of mepiquat according to the invention have improved characteristics corrosive and hygroscopic. They are biologically active compositions with regulating plant growth properties comparable to or greater than the activity of mepiquat-chloride. According to one of the objects of the invention new borates of mepiquat can be easily obtained by transformation of salts, such as halides, carbonates, bicarbonates, sulphates, bisulfate, Monos1-C4the alkyl sulphates or formate of mepiquat, preferably the halides, sulfates, monomethylaniline and formate of mepiquat, most preferably mepiquat-chloride, basic salts of mepiquat, such as the hydroxide of mepiquat, using a new electrochemical methods. The above basic salt of mepiquat then subjected to interaction with boric acid to produce new salts ti is and borate of mepiquat, corresponding to the formula II, and to obtain the compounds of formula III above basic salt of mepiquat then subjected to interaction with boric acid and other compounds. According to another object of the invention is the conversion of the above-mentioned salts of mepiquat in the hydroxide of mepiquat can be carried out using any of the ion-exchange processes. Preferably salts of mepiquat, such as halides, carbonates, bicarbonates, sulphates, bisulfate, Monos1-C4the alkyl sulphates or formate of mepiquat, preferably the halides, sulfates, monomethylaniline and formate of mepiquat, most preferably mepiquat-chloride, is converted into a hydroxide of mepiquat using methods of electrochemical ion exchange and devices for this process.

Furthermore, according to another one of the objects of the invention new borates of mepiquat can be easily obtained by direct transformation of mepiquat-chloride in the borates of mepiquat using a new electrochemical method, which will be described in detail later.

Borates of mepiquat can also be obtained with the use of hydroxide, bicarbonate or carbonate of mepiquat as doctow using the classical reactions of inorganic chemistry. Preferably the above new carbonates or bicarbonates can be obtained Quat what Risala N-methylpyridine and/or piperidine using dimethylcarbonate when heated, preferably under pressure and with the use of methanol and/or water as solvents. The carbonate and/or bicarbonate of mepiquat then subjected to interaction with boric acid and/or with the corresponding borates. Alternatively can be used alkali metal salts acceptable for agriculture metals specified for formula III, particularly preferably their hydroxides or carbonates of alkali metals.

In all the above options can be added chelating or complexing fragment And to obtain compositions comprising the compounds of formula I-III, in which v is not zero.

According to preferred variants of implementation of the composition comprising borate, partial borate and mixed borate salt (together denoted hereinafter as "the borates of mepiquat)almost do not contain chlorine or other halide ions.

Typically, the concentration of trace amounts of halogen or halide impurities are in the range from 0 to 1 wt.%, preferably from 0 to 0.5 wt.% in terms of dry weight of the borate of mepiquat.

Also preferably, the borates of mepiquat according to the invention have a pH in aqueous solution from about 5 to about 9, preferably approximately neutral pH value.

Preferred borates of mepiquat on izobreteny shall include such number of boron, to the ratio of elemental boron and cation of mepiquat was in the range of from about 1:2 to about 20:1, more preferably from about 2:1 to about 20:1, particularly preferably from about 2:1 to about 10:1, in particular from about 3:1 to about 10:1. At least in a few cases, probably borate anions or fragments included in the system or associated with the cation of mepiquat, have the ability to potenzirovti or any other way to strengthen regulating plant growth properties of mepiquat, as described in detail in application for U.S. patent entitled "Regulating plant growth compositions on the basis of mepiquat enhanced action" in the name of Kenneth E. Fersch, Scott W. Gibson and David G. Hobbs, PCT/EP/98/05149, which is incorporated into this description by reference.

New regulating plant growth compositions on the basis of mepiquat according to the invention are especially valuable because of their nephroscopes and lack of corrosion activity, as described above. In addition, borate fertilizers in the form of a simple borate salts, such as SOLUBOR® (firm U.S.Borax Co.) (Na2B8O13·H2O) for a long period of time can be used to process plants, such as cotton.

Boron also is a component of a complex mixed fertilizer or preparations of trace elements, such Basoliar™ or Nitrobor™ (BASF AG). Thus, when using the preferred borates of mepiquat according to the invention does not introduce new chemical components in the environment or on an agricultural crop, such as cotton. Thus, the number of cation of mepiquat that is applied to agricultural crops such as cotton, when using the preferred compositions according to the invention are comparable or, typically, exactly the same quantity, which is applied using conventional PPP-compositions on the basis of mepiquat-chloride, and the amount of boron that is applied to crops is in the range, including the lower number compared to those that are introduced by the use of conventional treatments boric fertilizers, and a higher number compared to those that are introduced by the use of boron as a component of other micronutrients fertilizers.

Detailed description of the invention

Composition based on borate of mepiquat according to the invention, in their various forms may generally be referred to as "salt", "coordination compounds" or "complexes". Similarly, their cationic and anionic forms can be designated as "ions" or "complex ions". As should be obvious to experts in the field, theoretical the definition of the differences between "connection", "coordination compound", "complex" and "salt" are generally considered insignificant; and similarly theoretical differences, if they exist at all, between the "ion" and "complex ion" generally regarded as insignificant. This is primarily applicable to inorganic compositions and complexes on the basis of anionic fragments containing boron-oxygen. Thus, the term "salt" in the context of the present description includes "salt", "coordination compounds" and "complexes"; and the concept of "ion", "cation" and "anion" in the context of the present description includes "ions" or "complex ions". The concept of "acceptable for agriculture in the context of the present description refers to compatible with plants applications in agriculture, industry and buildings.

It is implied that the term "borate salt of mepiquat" in the context of the present description includes salts, coordination compounds and complexes of cations of mepiquat (N,N-dimethylpiperidine) boron anion. It is implied that the concept of "partial borate salt of mepiquat" in the context of the present description includes coordination compounds, complexes and salts based cations of mepiquat with mixed types of anions, including both anions boron, and at least one other type of anion, which does not contain boron. Means is I, that the concept of "mixed borate salt of mepiquat" in the context of the present description includes coordination compounds, complexes and salts on the basis of mixed species of cations such as cations of mepiquat, and at least one other type of cation other than cations of mepiquat, only anions boron or mixed types of anions, which include both anions boron, and at least one other type of anion other than boron.

It is implied that the concept of "Borat" in the context of the present description includes the hydrated and anhydrous forms of the anions, which are based on compounds of boron-oxygen in various forms, including in the form of chains and rings, including their oligomorphic and polymorphic forms, for example, double rings.

As is well known to specialists in this field, a particular form or structure of the borate anion or polyanion can easily vary depending on the chemical environment of the types of anions. In particular, it is known that many patterns borate anions vary at different pH values and/or depending on the presence of these species in solid form or in aqueous solution.

In particular, borate anions in aqueous solution at pH values in the range of 7-9 tend to be in the form of rings and double rings. Determination of boron using NMR showed that depending on the concentration of the above-mentioned borate anions mainly represent the equilibrium mixture of mono-, three - and pentaborate structures (on this issue see C.G.Salentine, Inorg. Chem., 22, 3920 (1983)).

On the other hand, at pH values lower than about 6, borate anions tend to be in the form of boric acid or circuits having the formula [IN2]q-where q, as a rule, has a value greater than 1. This usually occurs when heated, e.g., drying spray, and condensation and removal of water. However, under normal conditions of spray drying (inlet temperature from 50 to 200°C, preferably from 80 to 150° (C) mainly get three - and pentaborate anionic structure.

In addition, various kinds of anionic borate, as a rule, hydrates, i.e. reacting with water and/or in complex with water, quickly lose their original structure in aqueous solution, resulting anionic structure of a particular borate in aqueous solution may be not the same as anionic structure in crystalline or amorphous non-aqueous form, because a smaller number of complex anions can easily be combined during the crystallization process.

Similarly, it is known that various polyols and α-hydroxycarbonate acid, and various polyamine extremely quickly form very stable complexes (including chelate complexes with boron is AMI in aqueous and nonaqueous solutions. Preferably as a complexing/chelating agents are used, for example, the following connections A.

In particular, in formula I a represents a molecule of class 1-hydroxycarbonic acids, such as lactic acid, almond acid or malic acid; mono - or oligohydramnios-, di - or tricarboxylic acids, for example tartaric acid or citric acid; glycols, especially villalvilla, for example, 1,2-propylene glycol, 2,3-butyleneglycol; alcohols, such as ethanol, pentanol or benzyl alcohol; mono-, di - or tricarboxylic acids, for example acetic acid, oxalic acid or benzoic acid; and aminoalcohols, for example ethanolamine or diethanolamine; polyalcohol or sugars and their derivatives such as sugar alcohols, polygalacturonase acid, for example, glycerol, sorbitol, mannitol, fructose and glucose or glucuronic acid; and derivatives of the above classes of compounds, for example, derivatives in the form of simple or complex esters which can form at least one proton-nucleophilic coordination relative to the boron atom, for example, refers to a molecule as simple or complex ester with additional functionally active amino-, hydroxy-group or carboxylic acid.

Furthermore, it was assumed that the concept of "Borat" in the context of n the present description also includes hydrates, complexes with polyols, complexes with carboxylic acids and complexes with amines, which can easily be derived from borates and hydrated borates. Chemistry of borates described in more detail in various monographs, known in the art, including such as Cotton and Wilkinson, "Advanced Inorganic Chemistry, A Comprehensive Text", section 8-5, str-233 (3rd ed., 1972) and in Hollemann-Wiberg, "Lehrbuch der Anorg. Chemie", 81-90 ed. str and forth, "Boron, Metallo-Boron compounds and Boranes", Intersciences Publishers, John Wiley and Sons, 1964, and Wolfgang Kliegel, "Bor in Biologie, Medizin and Phatmazie", Springer Verlag, 1980, which is incorporated into this description by reference.

The compounds of formula I-III according to the present invention includes as a structural element at least one piece of boron-oxygen-boron.

Borates of mepiquat according to the invention can be easily obtained from the known salts of mepiquat, including halides and the like, which, in turn, can be obtained by known processes described, for example, in patent US 3905798 name Zeeh, etc. included in the present description by reference. Preferably borates of mepiquat according to the invention is produced by conversion of readily available salts of mepiquat, preferably mepiquat-chloride, a basic salt of mepiquat, such as the hydroxide of mepiquat, and subsequent neutralization of the basic salt of mepiquat boric acid, and optionally mixing with borates acceptable for rural what about the economy salts, the type of salts of sodium, potassium, ammonium, calcium, magnesium or zinc, to provide new compounds of formula I.

In addition, basic salts of the above is acceptable for agriculture cations, for example, oxides, hydroxides, carbonates or bicarbonates of sodium, potassium, calcium, magnesium, zinc or ammonium can be used in combination with boric acid or other borate salts.

The conversion of salts of mepiquat, for example, halides, carbonates, bicarbonates, sulfates, bisulfates, Monos1-C4of alkyl sulphates or formate of mepiquat, preferably halides, sulfates, monomethyl-sulfate and formate of mepiquat, most preferably mepiquat-chloride, a hydroxide of mepiquat according to the present invention preferably can be carried out using any of various chemical or electrochemical ion exchange processes, including ion-exchange processes on the basis of various ion-exchange resins and electrochemical ion exchange processes. Preferably mepiquat-chloride is converted into a hydroxide of mepiquat using electrochemical processes and devices for their implementation.

Currently, the preferred processes hydroxide of mepiquat are electrochemical processes on the basis of the microporous membrane separators. Such electrochemical what their processes can be performed in various ways using a variety of known devices. For example, the processes of bipolar electrodialysis can be carried out by a method similar to that described in .Stratmann and others, Chemtech (6) (1993) pp.17-24, publication included in the present description by reference.

According to this process the bipolar electrodialysis cell for fill several bipolar membranes and several anion-exchange membranes having alternate location. The alternating arrangement of the membranes of two types allows you to get a few, i.e. n acid and n main zones, where n can range from 1 to about 300. Membrane supported hermetic seals at a distance of from about 0.05 to about 3 mm from each other.

The process of the bipolar electrodialysis can be carried out in the presence of water or alkaline path (using alkaline solution such as sodium hydroxide)or acid way (using acid solution, including, for example, sulfuric acid). When using alkaline paths are preferred Nickel anodes and steel cathodes. When using the acid path preference is given TO (wear-free (stable) anodes used for chlor-alkali electrolysis), i.e. the anodes in the form of a metal grid made of titanium with various mixed oxides, such as oxides of transition metals Ir, Ru, Rh, etc.) or the anode and the platinum and steel or platinum cathodes. The applied current density is in the range from 1 to 14 A/DM2, preferably in the range of from 4 to 10 a/DM2. The reaction temperature is in the range from 10 to 60°C.

The process begins by pumping diluent, for example, 1-60 wt.%-aqueous, preferably 5-30 wt.%-aqueous solution of salt of mepiquat, preferably a solution of a halide of mepiquat, particularly preferably solution mepiquat-chloride, through a system of alkaline areas. At the same time through the acid system zones filled with dilute acid (for example, 0.5 wt.%-percent hydrochloric acid). After creating the electric field chlorine ions migrate through the anion-exchange membrane in accordance with the direction of the field from alkaline cells to acid cameras. At the same time, the water dissociates in bipolar membranes with the formation of H+(acid cameras) and HE-(alkaline cells). The pH value in the acid loop can be maintained at an acidic or neutral or alkaline by the addition of alkali. Preferably the pH value in the acid loop support at the level of acid. The concentration of the salts obtained in the acid loop typically is in the range from 1 to 35 wt.%. The use of bipolar electrodialysis allows you to get 1-60 wt.%-tion, preferably 1-35 wt.%-tion, particularly preferably 5-30 wt.%-hydrated hydroxide solution menu is wool, which practically does not contain chloride.

Especially preferred is if the borates of the formula I are synthesized directly without phase selection hydroxide of mepiquat. During this process, the product obtained in alkaline loop above devices for bipolar electrochemical dialysis, is subjected to the interaction with the corresponding quantities of boric acid (crystalline or concentrated solution of boric acid, boron oxides, and optionally in the presence acceptable for agriculture, metal hydroxides, metal oxides, metal carbonate, bicarbonate metals, ammonium hydroxide, ammonium carbonate or ammonium bicarbonate or mixtures thereof, while the compounds of formula I are formed directly. For this purpose, alkali loop system for bipolar electrodialysis download an aqueous solution of a halide of mepiquat, preferably mepiquat-chloride having a concentration of 1-60 wt.%, preferably with a concentration 1-35 wt.%, especially preferably having a concentration of 5-30 wt.%. A dilute solution (approximately 0.5 wt.%) acid, alkali or alternatively mineral salts, preferably hydrochloric acid, sulfuric acid, sodium hydroxide, potassium hydroxide, sodium chloride or potassium chloride, especially prefer the Ino hydrochloric acid or sodium chloride, download acid in a loop so that it was adequate initial conductivity. By passing an electric current through the electrodes chlorine ions selectively migrate depending on the direction of the electric field through the anion exchange membrane in the acid loop, while multivalent anions and cations are held. At the same time, also under the influence of an electric field, the water dissociates in bipolar membranes with the formation of N+(acid loop) and HE-(alkaline loop). The released ions hydroxide deprotonized boric acid, and the compounds of formula I are formed directly.

In this process, the pH value of the acid loop support in the range of 14, preferably 6 to 9, by adding alkali. For the electrodes can be used all known from the literature materials. The current density is in the range from 1 to 14 A/DM2, preferably in the range of from 4 to 10 a/DM2and most preferably in the range of from 4 to 6 A/DM2.

The concentration of the salts obtained in the acid loop, as a rule, are in the range of 1-35 wt.%, preferably 5-15 wt.%. The reaction is carried out at a temperature of 10-60°C, preferably 30-50°C. Obtained borate salt of mepiquat contain a maximum of 1 wt.% and preferably 0.5 wt.% chloride, calculated on the dry weight of B. the rata of mepiquat.

Alternative electrochemical synthesis process of the hydroxide of mepiquat from the corresponding salts are primarily chloride, can generally be carried out using ion-exchange process of electrolysis, as described generally in GB-A 1066930 (in the name of Monsanto company). According to this process the normal cell plate (flat) electrodes in turn consists of two parts of the cell using a cation exchange membrane (e.g., cation-exchange membrane Nafion type®), which is placed between the anode and cathode. Preferred used for the manufacture of anode material is a material for the electrodes, and the preferred used for the manufacture of cathode material is a material alloy steel (RA4) or Nickel.

The chain pump anode solution zapityvat aqueous solution of chloride of mepiquat with a concentration of 5-60 wt.%. The chain pump cathode solution filled in, for example, 0.5 to 1 wt.%-NYM hydroxide solution of mepiquat.

In the electrolytic process is the selective transfer of cations of mepiquat through the cation exchange membrane in the direction of the cathode solution, where both the cathode of the electrolysis of water hydrogen ions are formed and HE-. The latter, together with the cation of mepiquat transferred from the anode solution, forms require the hydroxide of mepiquat. Anodic reaction proceeds in the form of electrolytic oxidation of chloride ions with the formation of elemental chlorine, which is continuously removed by continuous cleaning of the anode solution.

In addition, the borates of mepiquat according to the invention can easily be obtained from carbonates and bicarbonates of mepiquat, which are new compounds. They, in turn, can be obtained by quaternization respectively piperidine and N-methylpiperidine using dimethylcarbonate. Carbonates and bicarbonates of mepiquat can be used directly, i.e. without the formation of a hydroxide of mepiquat to obtain borates of mepiquat.

Then new borate salt of mepiquat, partial borate salt of mepiquat and mixed borate salt of mepiquat receive according to the invention by reacting a basic salt of mepiquat (for example, a hydroxide of mepiquat, carbonate of mepiquat, bicarbonate of mepiquat) with boric acid or boron oxide or acceptable for agriculture borate salt and/or chelating reagent (see definitions). Such borate salts include any of various known borate salts, including sodium borate, metaborate sodium, tribaret sodium, pentaborate sodium, polyborate, borax, decahydrate borax, borax pentahydrate, tetrahydrate of dynatricarbonate (marketed under n is the rank of SOLUBOR® (firm U.S.Borax .Valencia, CA), etc. the Amount of boric acid or borate salt is chosen in such a way as to provide the desired ratio of elemental boron and cation of mepiquat end of Borat mepiquat. Preferably borates of mepiquat according to the invention include the mass ratio of mepiquat and boron (in terms of elemental boron and cation of mepiquat) at least 2:1 to 1:20, preferably at least 1:2 to 1:20, even more preferably at least 1:3 to 1:10. On the other hand, the amount of elemental boron may be considerably higher than the number of cation of mepiquat, and may be in the range up to 1:50 or even more. It is also possible to mix the compounds of formula II with additional sources of boron, type Solubor® or borax, or with mixtures of boric acid and basic salts acceptable for agriculture metals, for example, oxides, hydroxides, carbonates or bicarbonates of sodium, potassium, calcium or magnesium, to obtain the compounds of formula III.

Preferred according to the present invention borates of mepiquat have a mass ratio of boron and mepiquat in the range from about 2:1 to about 10:1 (in terms of elemental boron and cation of mepiquat).

The ratio of boron and mepiquat control enabling containing no boron anionic reagents or compounds of clicks is relevant complexes with borate, in the process of interaction of basic salts of borate of mepiquat with boric acid or borate salt; or by adding an excess borate anionic ingredients in the composition or in the form of boric acid neutralized, either directly in the form acceptable for agriculture borate salt. Acceptable chelating agents or compounds that form complexes with borates include polyols, in particular (ness.)alkylphenol and sugar; α-hydroxycarbonate acid, such as lactic acid and mandelic acid; 2,3-dihydroxycinnamate acid, such as tartaric acid, or acid type Anthranilic acid, various polyamine, such as etc etc.

Preferably, the composition including a borate, a partial borate salt and mixed borate salt of mepiquat (together designated in the context of the present description as "the borates of mepiquat"), which is substantially free of ions of chlorine or other Halogens, as mentioned previously, the content of chlorine or other Halogens was in the range of 0-1 wt.%, preferably 0-0,5 wt.% compared with the compounds of formula (I). For example, carbonate obtained by borates contain about 1 part./million or less halogen.

In General, after recrystallization and purification of borates in the water practically does not contain chlorine.

Also preferably, the borates Maika is and according to the invention had approximately neutral pH value in aqueous solution, i.e. that which is in the range from about 5 to about 9.

In order to regulate the plant growth composition of plant growth regulators on the basis of the borate of mepiquat according to the invention, applied to the aerial parts of plants, i.e. by sheet metal processing. Plants which may be treated by the compositions or preparative forms according to the invention include any plant listed in the above U.S. patent 3905798 name Zeeh with co-workers, and other plants that normally process known compositions based mepiquat, including wheat, barley and other Miloserdie culture, grapes, Poinsettia and other ornamental crops, primarily cotton. Such a sheet processing can be conducted by various conventional methods and using devices well known in this field, including spraying, processing in the form of a mist, dusting, coating using a rod or hand sprayer, nozzles for hydraulic spraying, electrostatic atomized sprayers, randomly drills, etc. If necessary, the composition may be applied with the use of airplanes or helicopters, equipped with a hydraulic system or a system for processing grains. It is desirable to apply the composition according to the invention in the form of aquatic plants is ora.

The composition or formulation according to the invention can be applied to the plants of cotton or other plants with a single treatment, but it is preferable to use multiple processing, distributed during the growing season, and the timeline for the processing and concentration of active ingredients varies depending on such factors as the species and varieties of plants; development stage of the plant and time of year; the geographical area and the place of treatment; climatic conditions, such as temperature, rainfall and day length and light intensity; and soil features, including the applied fertilizer. When creating the present invention found that a composition or formulation according to the invention is best applied on plants of cotton on the basis of consumption norms for each treatment from about 1 g/ha to about 100 g/ha in terms of the cation of mepiquat. When creating the present invention also found that the composition or formulation according to the invention is best applied on plants of cotton in accordance with the same methods of application that are used for compositions of plant growth regulators on the basis of PIX®described, for example, PIX® Plant Regulator, Official Handbook, 1996, BASF Corporation, Research Triangle Park, NC, included in the present description in widescale.

According to well-known conventional means on the basis of mepiquat, function borates of mepiquat according to the invention consists in the inhibition of vegetative growth of cotton plants, which manifests itself in particular in reducing the growth in height. As a result, the treated plants are characterized by slow growth; in addition, as a rule, there is a darker colouring of the leaves. Among other effects, it also provides an opportunity to implement a fully mechanized harvesting of this important culture. It can also reduce the destruction of various diseases (such as fungal diseases) due to the fact that after the sheet weight and the weight of the plants are relatively small. Inhibition of vegetative growth also allows you to more closely accommodate individual plants that increases yields obtained from the planting area.

At least in some cases, probably borate anions or fragments included in the system or associated with the cation of mepiquat, have the ability to potenzirovti or any other way to strengthen regulating plant growth properties of mepiquat. The term "amplify" (potenzirovti) or "enhanced" in the context of the present description includes both the improvement of the quantitative characteristics and the quality of the public improvements, when one or more of various characteristics or traits of plants strengthened in comparison with the processing of one traditional mepiquat-chloride, especially with regard to the plants of cotton. So, in some cases, the composition of the invention may provide increased yields of cotton fiber, stronger, but still controlled, the development of plants and/or to shorten the time required for opening of the bolls of cotton, from one day to seven days or more, depending on the specific period of vegetation, location and weather conditions and an appropriate system of cultivation of cotton.

The composition or formulation on the basis of mepiquat-borate according to the invention can be used in agriculture in various forms, including their packaging, i.e. in the form of concentrated and designed for use in tank mixtures, i.e. in the form of ready-to-use forms, as well as compositions having different concentrations and in different physical forms. The composition or formulation on the basis of the borate of mepiquat according to the invention can be applied directly in the form of dry granules, tablets or in powder form due to the hygroscopic nature of the compositions. However, they can also be used in a concentrated liquid form or in liquid form Tr the required concentration (full strength).

It is advisable that the composition of the invention, which are used in agriculture in the form of liquid required concentration or diluted form, included active substance in an amount of from about 0.01 to about 40 wt.% in terms of the mass of the cation of mepiquat.

Concentrates borates of mepiquat obtained using different methods of cooking, can be applied directly in the form of ready mixes intended for use in agriculture.

In addition, the concentrates of the borates of mepiquat can be dried under vacuum by removing water or spray dried to obtain water-soluble powders or granules.

If necessary, the composition or formulation may also be in the form of liquid and dense suspensions, in which all or part of one or both active ingredients are dissolved or suspended in a liquid.

A thick slurry or suspension concentrates are often preferred because they contain higher concentrations of active ingredient and Packed in smaller volumes.

Preferably the composition is delivered to the consumer for use in agriculture in the form of a concentrate in a sealed package. Such packaging include glass and plastic bottles and reminiscent of bottle containers, cardboard, containers the market, containers in the form of bags of various film, foil and/or paper or laminated materials, etc. that should be obvious. In such cases, the composition in the form of concentrate before use, the consumer is diluted as described in the label instructions in order to make active substances, based on the specific consumption norms, described in detail below. Typically, the composition is in the form of a concentrate is diluted at the rate of from about 2:1 to about 800:1 (diluent to the concentrate).

In a typical composition in the form of a concentrate having a form intended for application to plants, may also be included one or more acceptable for agriculture diluents known in this field, including: in the case of liquid compositions, water, dimethylsulfoxide, n-organic, ketones, such as cyclohexanone, aromatic and aliphatic hydrocarbon oils, vegetable oils, modified vegetable oils, such as esterified vegetable oils, alcohols, such as isopropyl and ethanol, polyols such as ethylene or propylene glycols, esters, etc.

However, some of these alcohols and polyols can as a chelating agent in solution to react with borate anions.

In addition, in the liquid composition is also can be included thickeners, for example xanthan gum type Kelzan S (Kelco/Monsanto Performance Materials Company), with natural-based agents, such as guar gum, carob bean gum or alginate such as sodium alginate, suspension concentrates minerals type bentonites or hectorite, technical polymers-type polymers or copolymers of acrylic acid, sodium acrylate or monomers of acrylamide or derivatives of sugar type of carboxymethyl cellulose (CMC) or methylcellulose and/or other derivatives, technical salt, or a mixture of these compounds. They are used in the range from 0 to 10 wt.%. However, xanthane used is preferably in the range from 0 to 1 wt.%.

In the case of solid compositions using various clays, binders and fillers, such as diatomaceous earth, attapulgite etc., fertilizers such as ammonium sulfate, ammonium nitrate and urea, solid polyols, such as sorbitol, mannitol and other sugars, as well as other solid media, such as salt, earth, wood, or other consisting of particles of cellulosic materials and the like, Various other preferred acceptable for agriculture carriers described above in such documents as U.S. patent 4447255, issued may 8, 1984 in the name of Schott and others; and the patent USA 3905798, issued September 16, 1975 in the name of Zeeh and other

In addition, the compositions of the present invention also mightcreate other active substances such as herbicides, fungicides, insecticides or PPP or other adjuvants normally used in this field, including substances that promote infiltration, surfactants, vegetable oils, agents, controlling fluidity, defoamers, preservatives, wetting agents, adhesives, antimicrobial agents and the like, including mixtures thereof, which are also known in this field and are described, for example, in the above U.S. patents 4447255 and 3905798.

To improve the effectiveness of the new borates primarily can be used ionic or nonionic surfactants, dispersing agents and surfactants.

Under the concept of surfactants, wetting agents and dispersing agents fall, for example, the following auxiliary agents of the following product groups:

Anionic surfactants and dispersing agents:

Soap (salts of alkali metals/alkaline earth metal and ammonium salts of fatty acids), such as potassium stearate; alkyl sulphates; simple alkalemia ether sulfates, for example ethers, sulfated hexa-, hepta - and octadecanol or glycol ethers of fatty alcohols; alkyl/italconsult; salts of alkaline metals, alkaline earth metals and ammonium salts arylsulfonate the acids and alkylbenzenesulfonic acids, such as, for example, lignosulphonic, phenolsulfonic acid, naphthalenesulfonate and dibutylaminoethanol acid, or dodecylbenzenesulfonate sodium; alkylnaphthalenes; methylalkylcyclenes; acellularity; alkylbenzenesulfonate; alkylene/diphosphate; sarcosinate, for example, laurylsarcosine sodium; taurate; furthermore condensates of sulfonated naphthalene and its derivatives with formaldehyde, condensates naphthalenesulfonic acids, phenols and/or phenolsulfonic acids and their salts with formaldehyde and/or urea; protein hydrolysates, and above all, as dispersing agents: exhaust lignosulfonic solution and methylcellulose.

Cationogenic surfactants:

The halides of alkylenediamine/alkyl sulphates; the halides alkylpyridine; halides of diallylmethylamine/alkyl sulphates.

Nonionic surfactants:

Poly(etilenglikolevye) esters of fatty acids, such as lauric alcohol.

Simple poly(etilenglikolevye) ether acetate; simple alkalol(etilenglikolevye) or poly(propylene glycol) ethers, for example, isotridecyl alcohol and ethers of fatty alcohol and poly(ethylene glycol); ethers alkylsilanes alcohol and poly(ethylene glycol), such as octylphenoxy ether poly(ethylene glycol); alkoxyl rowanne animal/vegetable fats and oils, for example, corn oil ethoxylates, castor oil ethoxylates, ethoxylates taly oil; a complex of glycolic esters, such as glycerylmonostearate; alkoxylated fatty alcohols and alkoxylates of oxaspiro; alkoxylated fatty acids, such as ethoxylates of oleic acid; alkylphenolethoxylate, such as the ethoxylated isooctyl, octyl or nonyphenol, esters of tributyltin and poly(ethylene glycol); alkoxylated fatty amines; alkoxylated amides of fatty acids; surfactants of the type of sugars, esters of sorbitol, for example esters sorbitan and fatty acids (servicemanual, corbettreport), esters of poly(ethylene glycol)sorbitan and fatty acids, alkylpolyglycoside, N-Alkylglucoside; alkylarylsulfonate; oxides alkylpiperazine, such as oxide tetradecyltrimethylammonium.

Zwitterionic surfactants:

Sulfobetaine; carboxybutyl; oxides of alkyldiphenylamine, such as oxide tetradecyltrimethylammonium.

Polymeric surfactants:

Di-, tri - and multi-block copolymers of the type (AB)x, AVA and VAV: for example, a block copolymer of poly(ethylene oxide) -poly(propylene oxide)block copolymer of polystyrene-poly(ethylene oxide); AB - comb-copolymer, for example, comb-copolymer polymethacrylate-poly(ethylene oxide); and other surfactants: that is their like, for example, perforadora surfactants, silicone surfactants, phospholipids, such as lecithin or chemically modified lecithins; amino acid surfactants, for instance N-laurylsulfate; surface-active homopolymers and copolymers such as polyvinylpyrrolidone, polyacrylic acid, poly(vinyl alcohol), poly(ethylene oxide), copolymers of maleic anhydride-isobutene, copolymers of vinylpyrrolidone-(vinyl acetate).

In this case, the alkyl chain of the above auxiliary agents may be linear or branched. The length of the alkyl chains, as a rule, is in the range of 8<n<20.

The composition of the invention include compounds of formula I and 0-60 wt.% other active substances and/or surfactants and/or other auxiliary products.

Preference is given to new preparative solid forms, which include a new regulating plant growth composition, which contains compounds of the formula I. They include from 5 to 100 wt.% compounds of formula I, particularly compounds of the formula II.

Preference is also given to the new suspension concentrates. They include a composition comprising a compound of formula I and the above-mentioned thickener. You can also add other active substances, etc is continued only in the range from 0 to 50 wt.%, preferably in the range from 0 to 30 wt.% surfactants and/or other auxiliary substances.

These suspension concentrates include the compounds of formula I in the range from 30 to 90 wt.%, first of all, from 50 to 80 wt.% and thickeners in the range of 0-10 wt.%, preferably 0-1 wt.%. Preferably, the thickeners of the type xanthan gum, for example, Kelzan S (Kelco/Monsanto Performance Materials Company) is used in the range of 0-1 wt.%.

Thus, another object of the invention are compositions comprising monolaurate salt of mepiquat formula IV which are used as PPP.

where:

DMPdenotes N,N-dimethylpiperidine (mepiquat)
Mindicates the acceptable cation for agriculture metal, hydrogen or NH4;
Inrepresents boron;
Aboutdenotes oxygen;
Anddenotes a chelating or complexing fragment associated with at least one boron atom;
n and mrepresent the same integers in the range from 1 to 6;
xdenotes an integer or fractional number ranging from 0 to 10;
zthe convoy is achet integer or fractional number ranging from 0 to 48;
vdenotes an integer or fractional number ranging from 0 to 24; and
wdenotes an integer or fractional number ranging from 0 to 24.

Fragments of water in the formula IV represent free or coordination intracrystalline water or "associated" water which, as a rule, in borate structures known as condensed water associated with the boron atom of hydroxyl groups.

These compositions can be used as plant growth regulators. For them fit the above parameters, including the norms of consumption, process plants, etc.

As for the composition of these compounds, it can also be used above adjuvants, settings, etc.

The following examples serve to illustrate suitable compositions according to the invention and the improvements of the growth characteristics of plants. However, it should be obvious that they are not intended to limit the scope of the invention.

Example 1

Getting hydroxide solutions of N,N-dimethylpiperidine by bipolar electrodialysis

In this example, the electrochemical process is carried out according to the General method described in Stratmann and others, Chemtech (6), 17-24 (1993).

The cell for bipolar electrodialysis design by alternating 5 is polyarnyj membranes (marketed under the name "Neosepta BP1" from the company Tokuyama Corp., Japan) and 5 anion-exchange membranes (marketed under the name "AMS"-membranes from the company Tokuyama Corp., Japan), each of which has a size of 13 cm × 6 see Total active area of the membrane is approximately 3,78 DM2. The distance between the membranes of 0.5 mm In alkaline camera load of 1000 g of 10 wt.%-aqueous solution of chloride N,N-dimethylpiperidine. In acidic camera load 1000 g of 0.5 wt.%-Noah hydrochloric acid. After connecting power for electrodialysis (3,78) two liquid recycle a flow rate of about 20 l/h at 40°C.

After conducting electrodialysis within 240 min initial concentration of chloride in alkaline cells (2,37 wt.%) reduced to less than 0.1 wt.%, this means that the concentration of Cl-reduced by 99.5%. As a result, the output of alkaline cells is 923 g of 9.1 wt.%-aqueous hydroxide solution in N,N-dimethylpiperidine, and the yield of acid cameras 994 g to about 3 wt.%-Noah hydrochloric acid.

Example 2

Electrochemical getting hydroxide N,N-dimethylpiperidine by oxidation of chloride to elemental chlorine using anodic reaction

In this example, the electrochemical process is carried out according to the General method described in GB-A 1066930 (in the name of Monsanto company).

The normal cell plate (flat) electrodes turn in SOS is ojasuu of the two parts of the cell using a cation exchange membrane (e.g., cation-exchange membrane, marketed under the name Nafion® 430 firm Du Pont), which is placed between the anode and cathode.

The active area of the anode and the cathode area of close to DM2each. The electrode is a reference electrode, and the cathode is an electrode alloy steel (RA4).

Catholyte (cathode solution) is present in the form of 1000 g of 0.5 wt.%-aqueous hydroxide solution in N,N-dimethylpiperidine. The anolyte (anode solution) consists of 1000 g of 30 wt.%-aqueous solution of chloride N,N-dimethylpiperidine. At 40°and 10 And when the cell voltage 6-10 occurs In the transfer of cations of N,N-dimethylpiperidine of anolytes chain Catalano chain. At the same time the anode is formed chlorine.

After 8 h the output catholyte is 1370,7 g of 15.6 wt.%-aqueous hydroxide solution in N,N-dimethylpiperidine. The residual content of chlorine in a solution of 140 ppm million based on the obtained conversion factor equal to 71.3 per cent, the total useful output was 54.7%.

Example 3

Getting [5About6(OH)4] a solution of N,N-dimethylpiperidine with bipolar electrodialysis Connection No. 1.0

Cell for bipolar electrodialysis comprises characterized by alternating 5 bipolar membranes (for example, Aqualytics polysulfonamide type) and 5 anion-exchange membranes (for example, type S-3, f is my Tokuyama Corp., Japan), and the total area of the membrane is 10 DM2and the distance between the membranes of 0.5 mm In alkaline loop built-receiving chamber with a mixing device, in which the pre-start electrolysis load of 13.3 kg of boric acid. In alkaline circuit load 50 kg 12 wt.%-aqueous solution mepiquat-chloride. In the acid loop quickly get 0.5 wt.%-cent solution of sodium chloride, the pH value of which is in the process of electrodialysis support in the range of 6 to 8 by metered injection 29,0 kg of 10 wt.%-aqueous sodium hydroxide solution. In the electrode circuit circulates 5 wt.%-hydrated sodium sulphate solution. The anode and cathode are made of plate. After conducting electrodialysis for 48 h at 40°at a flow rate of 100 l/h and an initial current density of 5.7 A/DM2the concentration of chlorine ions is decreased from 2.86 wt.% up to 0.12 wt.%, which corresponds to the coefficient of demineralization of 96.2%. Boric acid in the receiving chamber is completely dissolved in the electrolysis process. In alkaline loop contains 59.2 kg to 22.7 wt.%-aqueous solution of DMP+[B5O6(OH)4]-. The output in terms of the number of DMP is 99.5%, and the efficiency of the process - 93,2%.

Example 4

Example 4A

Synthesis of a mixture of bicarbonate of N,N-dimethylpiperidine and carbonate N,N-dimethylpiperidine (bicarbonate of mepiquat and carbonate of mepiquat)/p>

A mixture containing 68,1 g N methylpiperidine (purity 80%, the water content 20%) (0,551 mole of N-methylpiperidine, 0,756 mole of water), 99,3 g dimethylcarbonate (1,103 mol) and 88.3 g of methanol (2,759 mol) was pumped at a temperature of 160°and a pressure of 60 bar at a rate of 100 ml/h in a tubular flow type reactor with a volume of 50 ml (diameter = 4 mm; length = 4 m, wall thickness 1 mm, stainless steel).

Then the reaction mixture was transferred into a distillation flask with a 20-centimeter column Vigreux type and controlled manually by the head of the column and subjected to distillation under normal pressure. Distilled fractions with low boiling point was replaced by the constant addition of water (340 g). In the distillation of the bottom of the distillation flask was heated to 72-102°With, at the head of the column measured temperature was 67-99°.

Ion chromatographic analysis of the residue after distillation (313 g) showed that the content of the cation of mepiquat is 19.5 wt.% (97.2% of theoretical). Using titration showed that the content of CO32-at the bottom is 3.3 g/100 g, and the HCO3-4.1 g/100 g as anion (100% of theoretical). Analysis by gas chromatography head fractions showed that the methanol content of 50 ppm million, and the content of dimethylcarbonate <100 ppm million

Example 4B

Synthesis of carbonate N,N-dimethylpiperidine

Dioxi the carbon missed within 1 h after 553 g 15,56%aqueous hydroxide solution in N,N-dimethylpiperidine. The solution temperature was raised from 20°to 38°C for 20 min, and then the solution was again cooled. Added 300 ml of toluene to 100 ml. The resulting mixture was boiled under reflux and the water drove in azeotropically conditions during the 11 o'clock

The precipitated solid was subjected to vacuum filtration, washed with pentane and dried at 50°With under reduced pressure. Received 14.2 g extremely hygroscopic product white color.

1H-NMR (D2O; δ [part./million]): δ=1,65 (2N), A 1.88 (4H), 3,10 (6N), TO 3.34 (4H).

13C-NMR (D2O; δ [part./million]): δ=22,4, 23,0, 53,9, 162,0 (the HCO3-).

Example 5

The uranyl nutritionalfa N,N-dimethylpiperidine ([N,N-dimethylpiperidine]+[B10NaO16]-·7H2O) - Connection # 1.1

With stirring was added a total of 22.4 g (362 mmole) of boric acid (purity 99.8%), 24.2 g (35.8 mmole) hydroxide N,N-dimethylpiperidine in the form of 19.6 wt.%-aqueous solution are 2.87 g of sodium hydroxide in the form of a 50 wt.%-aqueous solution (35,9 mmole) to 150 ml of distilled water. The mixture turned into a clear solution after stirring for about 1 h After removal of water by evaporation under vacuum, the solid residue was dried for 2 days under vacuum at 40°C. the Crude product was analyzed to confirm the proposed SOS is ava and formula of the molecule. The product contained 6 parts of water as structurally associated with boron hydrate (usually through a hydroxyl group) or crystalline hydrates (available group of water) (see, for example, in Hollemann-Wiberg, "Lehrbuch der Anorg. Chemie", 81-90 ed. str and later).

The results:

1) Elemental analysis (% C, H, and N:

calculated: 13,4, 4,8, 2,2, respectively

found: 13,5, 4,6, 2,1, respectively

2) FID analysis in % for b and Na:

calculated: 17,2, and 3.7, respectively

found: 17,8, 3,5, respectively

3) analysis of the cation [N,N-dimethylpiperidine]+

calculated: 18,7%, respectively

found: 17,97%, respectively

4) Hygroscopicity of the compound No. 1.1 in comparison with mepiquat-chloride:

Both compounds were dried to constant weight in vacuum at 40°C for 48 hours then about 1 g samples (two series of 3 samples in each; the averaged values) kept at a relative humidity between 50 and 60% air for 2 or 4 weeks. The following results are obtained in the form of relative water absorption (wt.% wt./wt.):

Relative humidity50%60%
2 weeks4 weeks2 weeks4 weeks
mepiquat-chloride52 587178
connection 1.14.1*7,8*
*not measured

5) the pH Value in aqueous solution of concentration 1 wt.% 6,78.

6) Experiments on crystallization and recrystallization

As mentioned earlier, the rapid removal of water under vacuum leads to the production of amorphous compound No. 1.1, corresponding to the expected formula, while the slow crystallization process at normal pressure and slow samosatene water of the crude concentrate of the reaction product results in large crystals, which were analysed using x-rays.

In the slow and successive crystallization and recrystallization was obtained mixture 1:1 of relatively large crystals pentaborate sodium and pentaborate of mepiquat.

A) Pentaborate sodium: B10Na2O16·10H2O Connection No. 1.1A (registration number CAS 12007-92-0, a synonym for B5NaO8·H2O)

The structure was confirmed by analysis of x-rays, and it is characterized by the following parameters of crystals:

Total weight: 590,24;

Crystal system: monoclinic;

Space group: C2/2;

The dimensions of the unit cell: a=1107,71 (11) pm; alpha = 90° ; b=1638,5 (2) pm; beta = 112,757 (8)°; = 1355,13 (9) pm; gamma = 90°;

Volume, z: 2,2640 (3) nm3;

Density (calculated) 1,732 mg/m3.

B) Dihydrate pentaborate N.N-dimethylpiperidine - Connection # b ([N,N-dimethylpiperidine]+[B5O8]-·2H2O)

The structure was confirmed by analysis of x-rays. For the structure characterized by the same serotyp as pentaborate sodium; selected crystals were dried in vacuum at 150°C for 2 days and received the following parameters of crystals:

Total weight: 332,29;

Crystal system: triclinic;

Space group: P1;

The dimensions of the unit cell: a=932,6 (2) pm; alpha = 96,063° (11); b=938,57 (14) pm; beta = 102,48 (2)°;=1846,7 (4) pm; gamma = 96,50 (2)°;

Volume, z: 1,5540 (5) nm3;

Density (calculated) 1,420 mg/m3.

Example 6

[D-dimethylpiperidine]22+[B18Na2O29l2-·8H2O - Compound No. 1.2

The above compound was obtained similarly to the compound of 1.1, using the following starting materials, in relative molar quantities: 1 part of the hydroxide dimethylpiperidine, 9 parts of boric acid (sold by the company Merck Company, Darmstadt (Germany), purity 99.8%, registration number CAS 10043-35-3)) and 1 part of sodium hydroxide. The compound was analyzed as link is 1.1, example 5, by means of elementary analysis, the following results are obtained:

1) Analysis (%) C, H, N, B, Na and Cl:

designed: 16,6, 4,5, 2,6, 18,1, 4,3, 0,0 respectively

found: 15,8, 4,7, 2,6, 17,8, 3,9, 0,088 respectively

2) appearance

vitreous solid

3) Hygroscopicity

after keeping for 4 weeks in air at 50%relative humidity: water absorption of 5.2 wt.%

after keeping for 4 weeks in air at 60%relative humidity: water absorption of 7.0 wt.%

4) the pH Value in aqueous solution of concentration 1 wt.% 7,4.

Example 7

[D-dimethylpiperidine]22+[B12Na4O21]2-·20H2O - Connection # 1.3

The above compound was obtained similarly to the compound of 1.1, using the following starting materials, in relative molar quantities: 1 part of the hydroxide dimethylpiperidine, 2 parts of boric acid and 1 part borax (supplied from the firm Riedel de Haen Company; 99.5%purity, registration number CAS 1303-96-4; Na2B4O7·10H2O)).

The compound was analyzed as well as the connection 1.1, example 5, the following results are obtained:

1) Analysis (%) C, H, N, B, Na and Cl:

designed: 14,7, 6,3, 2,4, 11,3, 8, 0,0 respectively

found: 14,6, 6,4, 2,6, 11,6, 8, 0,013 respectively

2) appearance

crystalline substances is about

3) Hygroscopicity

after keeping for 4 weeks in air at 50%relative humidity: water absorption of 13.6 wt.%

after keeping for 4 weeks in air at 60%relative humidity: water absorption of 28.8 wt.%

Example 8

[D-dimethylpiperidine]+[In9With27,6H50,6Na0,8O39,7]-·8H2O - Connection # 1.4

The above compound was obtained similarly to the compound of 1.1, using the following starting materials, in relative molar quantities: 1 part of the hydroxide dimethylpiperidine, 9 parts of boric acid, 2,3 parts of sucrose, 0.8 part of sodium hydroxide (it should be noted that used non-stoichiometric molar parts of the original products, especially sodium hydroxide to obtain pH values of the compositions to about 7; it also leads to obtaining the above non-stoichiometric formula). The compound was analyzed as well as the connection 1.1, example 5, the following results are obtained:

1) Analysis (%) C, H, N, B, Na and Cl:

designed: 29,8, 5,9, 1, 7, 1,3, 0,0 respectively

found: 29,2, 5,9, 0,9, 7, 1,3, 0,031 respectively

2) appearance

crystalline substance.

3) Hygroscopicity

I have not measured.

Example 9

[D-dimethylpiperidine]+[B8(NH4)for 0.3O12,7]-·H 2O (estimated according to the formula analysis) - Connection # 1.5

The above compound was obtained similarly to the compound of 1.1, using the following starting materials, in relative molar quantities: 1 part of the hydroxide dimethylpiperidine, 8 parts of boric acid and 0.3 part of ammonium hydroxide (same as in example 8, was used non-stoichiometric molar parts of the original products, especially ammonium hydroxide to obtain pH values of the compositions to about 7; it also leads to obtaining the above non-stoichiometric formula). The compound was analyzed as well as the connection 1.1, example 5, the following results are obtained:

1) Analysis (%) C, H, N, B, Na and Cl:

designed: 17,4, 5,5, 6,7, 18,0, 0,0, 0,0 respectively

found: 17,3, 5,6, 4,2, 17,6, 0,01, 0,015 respectively

2) appearance

crystalline substance.

3) Hygroscopicity

after keeping for 4 weeks in air at 50%relative humidity: water absorption of 0.4 wt.%

after keeping for 4 weeks in air at 60%relative humidity: water absorption 0.6%

4) the pH Value in aqueous solution of concentration 1 wt.% 6,8.

Example 10

[D-dimethylpiperidine]+[B9Nafor 0.9O14,5]-·6N2On - Connection # 1.6

The above compound was awarded the Academy of Sciences of the logical connection 1.1, using the following starting materials, in relative molar quantities: 1 part of the hydroxide dimethylpiperidine, 9 parts of boric acid and 0.9 part of sodium hydroxide (the same as in example 8, was used non-stoichiometric molar parts of the original products, especially sodium hydroxide to obtain pH values of the compositions to about 7; it also leads to obtaining the above non-stoichiometric formula). The compound was analyzed as well as the connection 1.1, example 5, the following results are obtained:

1) Analysis (%) C, H, N, B, Na and Cl:

designed: 14,7, 4,9, 21,4, 17,0, 3,6, 0,0 respectively

found: 14,4, 4,7, 21,4, 17,6, 3,9, 0,099 respectively

2) appearance

amorphous substance

3) Hygroscopicity

after keeping for 4 weeks in air at 50%relative humidity: water absorption of 2.7 wt.%

after keeping for 4 weeks in air at 60%relative humidity: water absorption of 9.0 wt.%

4) the pH Value in aqueous solution of concentration 1 wt.% 7,1.

Example 11

[D-dimethylpiperidine]+[In6,4Nafor 0.3O10,3]-·4H2O - Connection # 1.7

The above compound was obtained similarly to the compound of 1.1, using the following starting materials, in relative molar quantities: 1 piece hydroxide, dimethylpiperidine is, of 6.4 parts of boric acid and 0.3 part of sodium hydroxide (the same as in example 8, was used non-stoichiometric molar parts of the original products, especially sodium hydroxide to obtain pH values of the compositions to about 7; it also leads to obtaining the above non-stoichiometric formula). The compound was analyzed as well as the connection 1.1, example 5, the following results are obtained:

1) Analysis (%) C, H, N, B, Na and Cl:

designed: 19,7, 5,6, 3,3, 16,2, 1,6, 0,0 respectively

found: 19,7, 5,4, 3,3, 16,5, 1,6, 0,046 respectively

2) appearance

amorphous substance

3) Hygroscopicity

after keeping for 4 weeks in air at 50%relative humidity: water absorption of 1.9 wt.%

after keeping for 4 weeks in air at 60%relative humidity: water absorption of 4.1 wt.%.

Example 12

[D-dimethylpiperidine]+[B9C9H36Na0,8O23,4]-·5H2O - Connection # 1.8

The above compound was obtained similarly to the compound of 1.1, using the following starting materials, in relative molar quantities: 1 part of the hydroxide dimethylpiperidine, 9 parts of boric acid, 0.8 part of sodium hydroxide and 4.5 parts of ethylene glycol (the same as in example 8, was used non-stoichiometric molar parts of the original PR the products, especially sodium hydroxide to obtain pH values of the compositions to about 7; it also leads to obtaining the above non-stoichiometric formula). The compound was analyzed as well as the connection 1.1, example 5, the following results are obtained:

1) Analysis (%) C, H, N, B, Na and Cl:

designed: 22,9, 7,4, 1,7, 11,6, 2,2, 0,0 respectively

found: 23,2, 6,3, 1,7, 11,7, 1,9, 0,046 respectively

2) appearance

the vitreous substance

3) Hygroscopicity

I have not measured

4) the pH Value in aqueous solution of concentration 1 wt.%

I have not measured

Example 13

The dihydrate, hemihydrate of pentaborate N,N-dimethylpiperidine ([N,N-dimethylpiperidine]+[B5O6]-·H2O) - Connection # 1.9

The above compound was obtained similarly to the compound of 1.1, using the following starting materials, in relative molar quantities: 1 part of the hydroxide dimethylpiperidine, 5 parts of boric acid. For analysis a sample of the crude product was led at room temperature by samosatene water. The resulting crystals were isolated by filtration and dried at room temperature.

The compound structure was confirmed by analysis of x-rays. It was identical to the compound structure No. 1.1, but in two crystal cell included one additional the second water molecule; this leads to the General formula: [N,N-dimethylpiperidine]+[In5About6]-·2,5H2About;

1) appearance:

Crystalline substance, tPL>400°C; a reduction in the weight of >10% at a temperature of >200°With due processes of condensation of the anion of pentaborate;

3) Hygroscopicity

after keeping for 4 weeks in air at 50%relative humidity: water absorption of 0.4 wt.%

after keeping for 4 weeks in air at 60%relative humidity: water absorption 0.6%.

Example 14 (Experiments on determination of corrosiveness)

Comparison of corrosion activity (a) mepiquat-chloride and (B) a mixture of mepiquat-chloride with tetrahydrate of dynatricarbonate (Sulubor®and (C) pentaborate of mepiquat (compound 1.9) from example 13.

Shown in this example, experiments were conducted according to DIN method (Deutsche Industrie Norm) No. 52168, part 1, November 1981, but using the modified steel plates.

Experiments on determination of the corrosion activity was performed using three different compositions obtained as described below. The activity of each composition were tested using the following three different types of steel.

The first composition indicated in the following tables as "mepiquat-chloride", represented 8,33 wt.%of the initial aqueous solution of mepiquat-chloride, obtained by diluting pre-concentrate mepiquat-chloride at a concentration of 600 g/L. the Second composition indicated in the following tables as "mepiquat-chloride plus borate salt, was obtained by adding 15 wt.%-acetate tetrahydrate of dynatricarbonate to 8,33%final water solution mepiquat-chloride, which is used in the first composition.

The third composition indicated in the following tables as "pentaborate of mepiquat," received from the connection 1.9, example 13 by dilution with water to receive 12 wt.%-aqueous solution of pentaborate of mepiquat.

All three of the above-mentioned composition containing equal amounts of the cation of mepiquat.

0.5 l of each composition were placed in polyethylene plastic containers (10 cm × 10cm × 12 cm (height)). In each container was made of a series of plates 12×5 cm2(thickness 0.2 cm), made of two types of steel.

Modification of the specified DIN method was that prepared steel plates with additional scorched oxyacetylene area of approximately 5-7 mm, located horizontally in the middle of the steel plate.

The burned area was placed down on the surface of the solution. (The purpose of this modification of the experience was the simulation of a more serious situation from the point of view of corrosion and the risk of structural damage.)

The position of the plates was such that approximately 1/3 of the plate was in contact with air. After 14 days the steel plate was evaluated, washed and cleaned, dried and weighed as described above the DIN method.

Results: the following results on the determination of corrosion activity (primarily expressed in the form of loss of material in g/m2you can set that "pentaborate of mepiquat" is a product with no corrosion activity (series 1 and 2 experiments).

Test series 1:
Steel type ST 37
TrackInitial mass in gThe final mass in gThe difference in gCorrosive activity in g/m2The pH of the initial... end
mepiquat - chloride195,239494,92130,318135,34to 7.67...of 7.96
mepiquat-chloride + borate salt295,346495,10320,243227,027,33...at 7.55
pentaborate of mepiquat396,757296,74240,01481,647,40...7,43
Note concerning the appearance of p is obtained tracks:

1the solution from yellow to orange color, cloudy, precipitation

2similarly1< / br>
3the transparent solution is almost colorless, no deposition

Test series 2:
Steel type ST 13
TrackInitial mass in gThe final mass in gThe difference in gCorrosive activity in g/m2The pH of the initial... end
mepiquat-chloride192,470892,25120,219624,4to 7.67...to 8.34
mepiquat-chloride + borate salt292,098591,90470,193821,537,33...7,46
pentaborate of mepiquat393,213993,21320,0007<0,17,40...7,43
Note concerning the appearance of the obtained compositions:

1the solution from yellow to orange color, cloudy, precipitation

2similarly1< / br>
3the transparent solution is almost colorless, no deposition

Example 15

The following three formulations described new suspension concentrates using what W as the initial products of boric acid, borax and pentaborate of mepiquat. In the present composition mepiquat and boron are in the ratio of >1:30. In all compositions the amount of the cation of mepiquat is 32 g/L.

Example 15A

To 232,9 g 15.8 wt.%-aqueous solution of hydroxide of mepiquat (0,28 mol) was added via laboratory dosing device mixture containing 182 g of boric acid (2,94 mol) and 561,4 g of borax (Na2B4O7·10H2O, 1,47 mol). After 10 min was added 16.6 g of pre-concentrate Kelsan S* (2% in water) and 288,8 g of distilled water. (*Kelsan S is a xanthan gum Kelco company/Monsanto Performance Materials Company and used as a thickener.)

The mixture was stirred for about 1 h Obtained suspension concentrate is a stable, colorless, homogeneous and can be used as ready-mix for use in cooking in the tank mixture (tank mixture) after complete dissolution of all components.

The ratio of 1:32 mepiquat and boron was confirmed using ion chromatography and elementary analysis.

Example 15B

Following the suspension concentrate was obtained similarly to the method of example 15A using the following quantities of products source: 232,9 g 15.8 wt.%-aqueous solution of hydroxide of mepiquat (0,28 mol), 544,1 g of boric acid (8,80 mol), 76,64 g Sulubor® (0,23 supposedly is), 16.6 g Kelsan S* (2 wt.% pre-concentrate in water) and 323,05 g of distilled water.

The ratio of 1:38 mepiquat and boron was confirmed using ion chromatography and elementary analysis.

Example 15V

Following the suspension concentrate was obtained similarly to the method of example 15A using the following quantities of products source: 98,35 g pentaborate of mepiquat (0,28 mol) from example 13, 383,2 g Sulubor (Na2B8O13·4H2O) (CAS registration number 12608-41-2) (1,14 mol), 16.6 g Kelsan S* (2 wt.% pre-concentrate in water) and 704 g of distilled water.

The ratio of 1:32.5 mepiquat and boron was confirmed using ion chromatography and elementary analysis.

Example 16 (Biological testing)

Not identified reduction of biological activity of new borate compositions of mepiquat compared to mepiquat-chloride. As can be seen from the tables below, certain borate compositions turned out to be even more active in reducing the height of the shoots of the plants of cotton.

In experiments a-d used the following songs G-K. as the standard used composition 3, which includes only mepiquat-chloride.

Composition It is a solution of dissolved compounds b or 1.9 in the water, and the composition E is a solution of compound 1.2

Table 1
IngredientFormulation compositions (g/l)
GDEW3And1To1
mepiquat-chloride (used in concentrate (627,8 g/l))----42,2--
the hydroxide of mepiquat 18,67 wt.% (in water)197,08197,08197,08197,08-394,2393,9
boric acidthe level of 121.834,817417,4-139,3173,9
borax53,84------
Solubor®-156,4-----
citric acid (to 0.33 mol)---19,68---
sodium hydroxide 50 wt.% (in water)--44,96 ----
distilled water ad. 1000 ml688696685772958523489
Analysis and other options
cation of mepiquat (detected)32,630,5the 33.431,23262,864
cation of mepiquat (calculated)32323232323264
the number of moles of boron on l2,532,812,530,28-4,492,81
the ratio (molar frequent.) mepiquat:Bor:sodium1:9:11:10:21:9:11:1:0-1:4:01:5:0
density: g/ml1,0711,0841,1001,0061,0001,0561,057
1In these compositions used double the concentration of the cation of mepiquat

Experiment and

Reducing the height of the shoots of wheat (cultivar "Ralle") of various borate compositions of mepiquat is compared with mepiquat-chloride*

Table 2
MedicationThe consumption rate of mepiquat [g cation/ha]Height of shoots [% of control]
mepiquat-chloride50074
(composition C)100067
150069
200066
G50083
100076
150076
200074
D50076
100080
150073
200073
E50077
100073
150074
200072
W50076
100072
150068
200 64
To100070
200063

*Cultivation of plants in the greenhouse. Treatment by spraying an aqueous solution of shoots height of 16 cm 750 l/ha, the Evaluation was performed 20 days after treatment, when the height of the shoots of control plants was 55 see

Experiment b

Reducing the height of the shoots of cotton (cultivar "Delta Pine") of various borate compositions of mepiquat compared to mepiquat-chloride [the rate of flow of mepiquat-chloride = 250 g of cation/ha]*.

Table 3
MedicationHeight of shoots [% of control]
mepiquat-chloride (composition C)58
G63
D56
E55
W58

*Cultivation of plants in the greenhouse. Treatment by spraying an aqueous solution of shoots height 23 cm at the rate of 400 l/ha, the Evaluation was performed in 27 days after treatment, when the height of the shoots of control plants was 53 see

Experiment

Reducing the height of the shoots of cotton (cultivar "Delta Pine") of various borate compositions of mepiquat is compared with mepiquat-chloride*.

Table 4

*Cultivation of plants in the greenhouse. Treatment by spraying an aqueous solution of shoots height of 25 cm at the rate of 400 l/ha, the Evaluation was performed 20 days after treatment, when the height of the shoots of control plants was 37 see

Experiment g

Reducing the height of the shoots of cotton (cultivar "Delta Pine") of various borate compositions of mepiquat compared to mepiquat-chloride*.

Table 5
MedicationThe consumption rate of mepiquat [g cation/ha]Height of shoots [% of control]
mepiquat-chloride2585
(composition C)5084
10076
20076
D2584
50(68)
10075
20077
To2591
5080
10073
200 76

*Cultivation of plants in the greenhouse. Treatment by spraying an aqueous solution of shoots height of 25 cm at the rate of 400 l/ha, the Evaluation was performed 21 days after treatment, when the height of the shoots of control plants was 40 cm

Experiment d

Reducing the height of the shoots of cotton (cultivar "Delta Pine") of various borate compositions of mepiquat compared to mepiquat-chloride*.

Table 6
MedicationThe consumption rate of mepiquat [g cation/ha]Height of shoots [% of control]
mepiquat-chloride2576
(composition C)5077
10079
20074
D2579
5071
10074
20070
To2579
5074
10074
20073

*Stump the licensing of plants in the greenhouse. Treatment by spraying an aqueous solution of shoots height of 20 cm at the rate of 400 l/ha, the Evaluation was performed 24 days after treatment, when the height of the shoots of control plants was 38 see

Experiment e

Reducing the height of the shoots of cotton (cultivar "Delta Pine") of various borate compositions of mepiquat compared to mepiquat-chloride*.

Table 7
MedicationThe consumption rate of mepiquat [g cation/ha]Height of shoots [% of control]
mepiquat - chloride2582
(composition C)5080
10078
20081
the composition of example2583
15A5081
10078
20073
the composition of example2580
15B5075
10076
20077

prodtable
MedicationThe consumption rate of mepiquat [g cation/ha]Height of shoots [% of control]
the composition of example2584
15V5077
10073
20074

*Cultivation of plants in the greenhouse. Treatment by spraying an aqueous solution of shoots height of 30 cm at the rate of 400 l/ha, the Evaluation was performed 21 days after treatment, when the height of the shoots of control plants was 43 see

The invention is described in sufficient detail with reference to the preferred options for implementation. However, can be made of various variations and modifications without abandoning the essence and scope of the invention, which are presented in the previous detailed description and the attached claims.

1. Derivatives of Borat mepiquat General formula (I):

where DMP refers to N,N-dimethylpiperidine (mepiquat);

M denotes a cation acceptable for agriculture metal selected from a range that contains sodium, potassium, magnesium, calcium, zinc, manganese or copper, hydrogen or NH4;

In denotes boron;

O denotes oxygen;

And indicates chelate or complexometry fragment associated with one boron atom, representing (ness.)alkylphenol or sugar;

n and m represent the same integers in the range from 1 to 6;

x denotes an integer or fractional number ranging from 0 to 10;

y denotes an integer or fractional number ranging from greater than 1 to 48;

z represents a whole or fractional number ranging from 0 to 48;

v denotes an integer or fractional number ranging from 0 to 24; and

w denotes an integer or fractional number ranging from 0 to 24.

2. The compound according to claim 1, wherein x is 0.

3. The compound according to claim 1, wherein x denotes an integer or fractional number ranging from greater than 0 to 10.

4. The compound according to any one of claims 1 to 3, characterized in that it comprises 2-20 molar equivalents of boron on 1 molar equivalent derivative N,N-dimethylpiperidine.

5. The compound according to claim 4, characterized in that it includes 2-10 molar equivalents of boron on 1 molar equivalent derivative N,N-dimethylpiperidine.

6. The compound according to claim 5, characterized in that it includes 3-10 molar equivalents of boron on 1 molar equivalent derivative N,N-dimethylpiperidine.

7. The compound according to any one of claims 1 to 3, obtained by the interaction between 1-20 molar equivalents at Lenogo boron compound with 1 mol of hydroxide N,N-dimethylpiperidine.

8. The compound according to claim 1, in which the maximum concentration of trace amounts of halogen or halide impurities is 1 wt.% in terms of dry weight.

9. The compound according to claim 1, intended for use as active substances in the composition of regulating plant growth composition in combination with not more than 60 wt.% other active substances, and/or surfactants and/or other additives.

10. The method of obtaining the compounds of formula I according to claim 1, characterized in that the hydroxide N,N-dimethylpiperidine subjected to interaction with boric acid and/or boron oxides and not necessarily acceptable for agriculture hydroxides of metals selected from a range that contains sodium, potassium, magnesium, calcium, zinc, manganese or copper, or with ammonium hydroxide, and optionally with chelating or kompleksoobrazuyushchim fragment As described in claim 1.

11. Electrochemical method of producing compounds of the formula I according to claim 1, characterized in that the halide N,N-dimethylpiperidine subjected to interaction with bipolar electrodialysis in the presence of water and boric acid and in the presence acceptable for agriculture hydroxides of metals selected from a range that contains sodium, potassium, magnesium, calcium, zinc, manganese or copper.

12. The method according to claim 1, characterized in that the applied device for electrodialysis with double loop, consisting of alternating bipolar membranes and anion exchange membranes.

13. The method according to claim 11, characterized in that the device for electrodialysis with double loop, consisting of alternating bipolar membranes and anion exchange membranes, halides, N,N-dimethylpiperidine subjected to bipolar electrodialysis in the presence of boric acid and in the presence of hydroxides of metals selected their number, containing sodium, potassium, magnesium, calcium, zinc, manganese or copper, and monovalent anions selectively pass through the anion-exchange membrane under the influence of an electric field, while the cations and multivalent anions delayed.

14. The method according to claim 11, characterized in that the average current density is in the range from 1 to 14 A/DM2.

15. Electrochemical method of producing hydroxide, N,N-dimethylpiperidine, wherein the salt of N,N-dimethylpiperidine selected from the group comprising halides, sulfates, monomethylaniline and formate, is subjected to the interaction with the bipolar electrodialysis in the presence of water.

16. Electrochemical method according to p. 15, characterized in that the device for electrodialysis with double loop, consisting of alternating bipolar membranes and anyonehere, salt N,N-dimethylpiperidine subjected to bipolar electrodialysis in the presence of water and monovalent anions selectively pass through the anion-exchange membrane under the influence of an electric field, while the cations and multivalent anions delayed.

17. Electrochemical method according to item 15, wherein as the educt used chloride N,N-dimethylpiperidine.

18. Electrochemical method according to item 15, wherein the average current density is in the range from 1 to 14 A/DM2.

19. Suspension concentrate with regulating plant growth effect, obtained by mixing 1 mole of hydroxide N,N-dimethylpiperidine with 10-32 molar equivalents of one or more acceptable boron-containing compound selected from the group comprising boric acid and borate salts, thickening agent and water, or a mixture of 1 mole of the compounds of formula I, characterized in claim 1, with 4 moles of Na2B8O13·4H2O, with the thickening agent and water.

20. The suspension concentrate according to claim 19, comprising from 30 to 90 wt.% the compounds of formula I according to claim 1, not more than 10 wt.% thickener and, if necessary, additionally comprising from 0 to 50 wt.% another active substance, and a surfactant and/or other processing AIDS.

21. Suspension to ncentral according to claim 20, comprising from 30 to 90 wt.% the compounds of formula I according to claim 1, not more than 10 wt.% thickener and, if necessary, further includes other technological additives.

22. The suspension concentrate according to claim 20, in which the maximum concentration of trace amounts of halogen or halide impurities is 1 wt.% in terms of dry weight.



 

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FIELD: organic chemistry, chemical technology, medicine, pharmacy.

SUBSTANCE: invention relates to a new biologically active compound. Invention describes quaternary ammonium derivative of lidocaine of the formula:

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2 cl, 4 tbl, 4 ex

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FIELD: agriculture.

SUBSTANCE: invention proposes using the plant roof avens (Geum urbanum L.) preparations that are prepared by pharmacopoeia method. Rood avens preparations in form of powder or extract are used for treatment of fresh-water mollusks inhabitation sites on the pasture or on the lowered pond bed that provides practically total eradication of mollusks and their egg mass for 3-6 days. Invention allows expanding assortment of agents and to realize the indicated designation.

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6 ex

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6 ex

FIELD: agriculture.

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3 tbl, 8 ex

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3 tbl, 8 ex

The invention relates to agriculture and can be used in vegetable growing in the preparation of seeds and seedlings
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