MXPA99004748A - Quarternary ammonium salts and their use in agricultural formulations - Google Patents

Abstract

Novel agrichemical quaternary salts, compositions and a method to prepare them are disclosed.

Description

QUATERNARY AMMONIUM SALTS AND Sü USE IN AGRICULTURE FORMULATIONS.

Field of the invention.

The present invention relates to novel agrochemical quaternary salts, compositions of said salts and to a method for their preparation.

Background of the Invention Bioactive pesticides can be formulated for the purpose of useful application. Typically, bioactive pesticides can be prepared in liquid formulations for reasons of economy, but suffer from a number of problems including chemical instability of the bioactive pesticide or physical instability (eg, sedimentation of the bioactive pesticide) and these problems limit their potential. In the case of bioactive herbicides, these liquid formulations are not as stable as desired. More particularly, the sulfonylurea herbicides that are well known, extremely potent classes of herbicides generally consist of a bridging REE: 30405 sulfonylurea, -S02NHCONH- which binds two aromatic or heteroaromatic rings, and several salts of said sulfonylureas lack, conveniently, the liquid economic formulations which limit the commercial utility of the sulfonylurea herbicides or the salts of the same.

The sulfonylureas and the formulations thereof are known to have herbicidal activity and regulate the growth of the plant. Such formulations are useful as pre- and post-emergent herbicides and regulators of plant growth, especially where homogeneous liquid formulations are particularly advantageous. The liquid sulfonylurea or salts thereof are unstable in formulations and are decomposed by aqueous impurities or nucleophilic reagents in either organic and aqueous solvents. Maintaining the stability of a sulfonylurea formulation is extremely important since an unstable formulation can be considered to be of low effectiveness when used.

The stabilization methods of sulfonylureas are known in the literature. For example, U.S. 4,936,900 describes suspended sulfonylureas or salts suitable for the agriculture of sulfonylureas in water saturated with carboxylate salts (eg, ammonium, substituted ammonium, or alkali metal) or salts of inorganic acids (eg, phosphate) to make chemically stable suspensions to a pH 6-10. The salts of the present invention are not described.

Description of the invention It has been found that the stability of the liquid formulations of various pesticides can be increased using the quaternary ammonium salts of this invention. Pesticides that are within the scope of the invention are those pesticides that are in unstable liquid formulations. Among such pesticides, sulfonylurea herbicides are preferred. The quaternary sulfonylurea salts of this invention, when compared to the sulfonylureas described, give a high solubility in water or in organic solvents (depending on the quaternary salt chosen) and increase the stability of storage j e.

Accordingly, this invention involves novel quaternary agro-chemical salts, of pesticides which allow homogeneous stable formulations of chemically stable pesticides in hydrophobic liquids and in water to prepare them for the first time (for example, as emulsifiable concentrate formulations or self-expanding oils). on the surface of the water in a rice field).

The novel quaternary salts of pesticides are compounds represented by Formula I: Rl,. ©. N- I R3 wherein R is a substituted or unsubstituted benzyl or a substituted or unsubstituted methylnaphthyl group and the remaining groups R2, R3 and R4 are a substituted or unsubstituted C1-C25 alkyl or a substituted or unsubstituted alkaryl group; and A is defined as any known bioactive pesticide with a pKa from about 3 to about 7, with the proviso that when pesticide A is a sulfonylurea herbicide of the formula JS02NHCONR6Q and R1 is an unsubstituted benzyl, then one of R2, R3 or R4 is other than methyl or ethyl.

Representative examples of substituted or unsubstituted benzyl or substituted or unsubstituted methylnaphthyl groups of R1 include but are not limited to: where R is C 1 -C 3 alkyl, C 1 -C 3 alkoxy or halogen, and n is 0-2.

Representative examples of the substituted C? -C25 alkyl groups include but are not limited to C1-C25 haloalkyl and C1-C25 alkyl substituted with C1-C3 alkoxy, N02 or CN.

Representative examples of substituted or unsubstituted alkaryl groups include but are not limited to: where R7 is C1-C12 alkyl, C1-C3 alkoxy, N02 or CN, m is 0 or 1, n is 1, 2 or 3.

The preferred alkaryl groups are Representative examples of pesticides with a pKa from about 3 to about 7 include but are not limited to insecticidal and fungicidal herbicides. Representative examples of the herbicides include but are not limited to ureas, sulfonylureas, glyphosate and (2, -dichlorophenoxy) acetic acid. Representative examples of insecticides include but are not limited to methomyl and oxamyl. Representative examples of fungicides include weight are not limited to carbendazi, fusilazole and cymoxanil.

Preferred pesticides of the invention are sulfonylurea herbicides wherein "A" of Formula I is JS02NHCONR6Q where J is substituted or unsubstituted phenyl or a heterocyclic group, Q is a substituted or unsubstituted pyrimidino or a triazine group substituted or not substituted and R6 is H or methyl.

Representative examples of the preferred sulfonylureas include but are not limited to • chlorosul furon, metsulfuron methyl, etamet sul furon, methyl tribenuron methyl, t i fensulduron methyl, t ri flusul furon methyl, nicosul furon, rimsulfuron, chlorimuron ethyl, sul fameturon, benzosulfuron methyl, az imsul furon, and f 1 upi sul sulon.

Preferred for reasons of high herbicidal activity, low cost or ease of synthesis are the compounds of Formula I wherein R 1 is unsubstituted benzyl or unsubstituted methylnaphthyl.

The most preferred sulfonylureas are: N - [[(4,6-dimethoxy-2-pyrimidinyl) amino] carbonyl] -3- (ethyl sulphonyl) -2-pyridinesulfonamide, 2- [[[[[4- (dimethylamino)] -6- (2,2,2-trifluoroethoxy) -1, 3, 5-triazin-2-yl] amino] carbonyl] amino] sulfonyl] -3-methyl-methyl-benzoate, 2- [[[[(4-chloro Ethyl 6-methoxy-2-pyrimidinyl) amino] carbonyl] amino] -sulfonyl] benzoate, 2- [[[[(4,6-dimethoxy-2-pyrimidinyl) amino] carbonyl] amino] sulfonyl] -N , N-dimethyl-3-pyridinecarboxamide, 2-chloro-N- [[(4-methoxy-6-methyl-1, 3, 5-triazin-2-yl) amino] carbonyl] -benzenes, ulfonamide, 2- [ [[[(-metox-6-methyl) -l, 3,5-triazin-2-yl) amino] carbonyl] amino-sulfonyl-benzoic acid methyl, 3- [[[[(4-methyl) -6- met il) -1, 3, 5-triazin-2-yl) amino] carbonyl] amino-sulfonyl] -2-t io phenoxane methyl 1-methyl, 2- [[[[(4-methoxy-6-methyl) ) -1, 3, 5-triazin-2-yl) methylamino] carbonyl] amino] sulfonyl] methyl benzoate, N - [[(, 6-dimethoxypyrimidine -2-il ) amino] carbonyl] -l-methyl-4- (2-methyl-2-Te-tetrazol-5-yl) -lH-pyrazole-5-sulfonamide.

Another embodiment of the invention is a non-aqueous or aqueous formulation comprising, as the active ingredient, a compound of Formula I: wherein A, R1, R2, R3 are as defined above.

These compounds of Formula I are referred to as quaternary ammonium salts of Formula I or, in the case of the preferred herbicide, quaternary salts of sulfonylurea.

Substituted or unsubstituted benzyl or substituted or unsubstituted methylnaphthyl group of R 1 is required for chemical stability of the compounds of Formula I and are further defined as the stabilizing group. Substituted or unsubstituted (C1-C25) alkyl or substituted or unsubstituted alkaryl group of one or more of R2, R3 or R4 is useful for the solubility of the compounds of Formula I in organic solvents or oil. One or more of an alkyl (C10-C25) or an alkaryl group of R2, R3 or R4 is preferred for the solubility of the compounds of Formula I in organic solvents or oils.

An example of an embodiment of this invention is a stable formulation comprising compounds of Formula I in hydrophobic organic solvents optionally with emulsifiers and other formulation ingredients. Another example of this embodiment is the stable formulation comprising compounds of Formula I in water optionally with surfactants and other formulation ingredients.

Another embodiment of this invention are stable formulations derived from mixtures of compounds of Formula I with other herbicides such as bromoxynil.

In the above reactions, the term "alkyl" includes straight or branched chain alkyl, for example, methyl, ethyl, n-propyl, 1-propyl, octyl, dodecyl, hexadecyl, octadecyl or, for example, the different butyl isomers, pentyl, or hexyl.

The term "alkoxy" includes, for example, methoxy, ethoxy, n-propyloxy and isopropyloxy.

The term "halogen" includes fluorine, chlorine, bromine or iodine.

Detailed description of the invention.

The novel quaternary ammonium salts of Formula I, aqueous stabilizers and non-aqueous solution formulations containing these salts and optional mixtures of said salts of Formula I with other pesticides are prepared in water or organic solvents. Solution formulations are desirable because of the ease with which they can be measured, emptied, molded or diluted into dispersion preparations. Additionally, the process and equipment necessary to prepare the solution formulations are simple and the low cost you need to make dry formulations or dispersions in a real solution system. Many pesticides that include sulfonylurea herbicides are susceptible to the moisture degrading effects and impurities that nevertheless present a hint of levels in virtually all solvent systems. Therefore, the storage stability of these formulations can be a limiting factor in these utilities over a period of time. Due to the high herbicidal activity of pesticides, for example, sulfonylureas, pesticides may be required in only low concentrations in a formulation that aggravates the stability problem by the relative concentration of contaminants, which promotes decomposition that contributes to the decomposition of the unstable solutions.

The quaternary ammonium salts of the pesticides of this invention are described below with reference to the preferred pesticides that are a sulfonylurea herbicide. However, the invention is directed to said salts of any pesticide with a pKa from about 3 to about 7.

Additionally for stability, the quaternary sulfonylurea salt of potential advantages and herbicidal compositions thereof include: 1) better coverage of the foliage of the plants and less washing, since the physical form of the sulfonylurea can be altered from a solid, or a solid waxy to a liquid form, 2) the increase in the translocation resumed in the plant, results in a high efficiency or an expansion of the spectrum of activity, 3) construct in adjuvance a premixed formulation, where the adjuvants of the mixing tank are not necessarily long (for example, with N - [[(4,6-dimethoxy-2-pyrimidinyl) amino] carbonyl] -3- (ethylsulfonyl) -2-pyridine sulphonamide), 4) allow mixtures with other pesticides in a liquid formulation (for example, solution), where the effectiveness of either "is reduced.

The bioactive sulfonylureas can be prepared by methods known in the art. For example, U.S. Patent Nos. 4,127,405 and 4,169,719 describe sulfonylureas herbicides, and Lonza is a commercial source of quaternary halides that are reacted with the bioactive sulfonylureas as illustrated in the Example to form the compounds of the invention Other bioactive pesticides of the invention can be prepared by methods known in the art, for example, U.S. Patent Nos. 3,657,443, and 3,799,758, The Hormone.

Weedk i l l ers, C. Kirby (1980), and the Patent United States No. 3,576,834.

The stabilizing solution formulations that include the compounds of the invention can be prepared in s i t u in the desired solvent.

First, the inorganic salt of the bioactive sulfonylurea compound is generated by the addition of an inorganic base such as an alkaline hydroxide or alkaline hydroxide to a suspension of the bioactive sulfonylurea in the chosen solvent. This is followed by the addition of a quaternary halide. Similarly, a quaternary hydroxide can be mixed with a suspension of the bioactive sulfonylurea in the chosen solvent. The compounds of Formula I can also be prepared by exchanging one cation for another, wherein the side reaction product such as the inorganic halide or water is separated. The cation exchange can be effected by mixing an aqueous solution of the quaternary halide with an aqueous solution of the inorganic salt of the sulfonylurea. The quaternary sulfonylurea salt is then isolated by filtration (if it is solid) or extraction with a water-immiscible organic solvent chosen. Organic solutions free of organic halides are preferred to be made in the selected organic solvent followed preferably by complete filtration of the solid halides. The exchange can also be effected by passing a solution of the inorganic salt of the sulfonylurea through a column packed with a cation exchange resin containing the quaternary cation to be exchanged. In this method, the cation of the resin is exchanged for the inorganic cation of the original sulfonylurea salt, and the quaternary sulfonylurea of Formula I is eluted from the column by dissolving in the chosen solvent and releasing the inorganic halides.

The liguid formulation of the sulfonylureas is desirable because of the ease with which they can be measured, emptied, molded or diluted in aqueous slurry preparations.

Generally, however, the bioactive sulfonylurea compounds have limited solubility in water and in viable organic solvents and are chemically unstable in storage.

Additionally, the known salts of sulfonylureas have either low solubility in the chosen solvent or are chemically unstable in the solution.

It has surprisingly been found that the quaternary salts of sulfonylureas of the invention can be formulated with appreciable solubility in desired solvents together with improved gum stability. This chemical stabilization is carried out by selecting a benzyl or methylnaphthyl group as one of the substituents linked to the quaternary nitrogen. The desired solubility in the chosen solvent is achieved by selecting, in addition to the stabilizer group, short chain carbon groups for water solubility or long chain carbon groups for oil solubility. The judicious choice of the balance of the substituent groups in the nitrogen can impart surface activity for the final quaternary sulphonylurea salt.

Preferred nitrogen substituents of R 2, R 3 or R 4 of Formula I for formulations containing hydrophobic oils are one, two, or preferably three groups of long chain or alkaryl (C 10 -C 25) alkyls in addition to the stabilizing group.

Preferred nitrogen substituents of said R2, R3 and R4 for water-soluble formulations are C1-C3 alkyl and optionally an alkaryl group in addition to the stabilizing group.

The combination of one or two methyl groups with one or two long chain alkyl or alkaryl groups can impart surface activity to the quaternary salts of methylnaphthyl or benzyl. These are useful in simple pre-blended formulations for imparting adjuvant constructs to the sulfonylurea, where separately purchased adjuvants are ordinarily required to be a blender tank to perform such adjuvant.

In addition, the selection of substituents can improve the effectiveness of the herbicide or a selective spectrum to increase the solubility of the quaternary salt of sulfonylurea in the leaf wax, and thereby promoting a biotransport in the leaf.

One embodiment of the formulation of this invention is where the quaternary sulfonylurea compounds of the invention are dissolved in a hydrophobic oil, optionally in the presence of a surfactant, and the resulting solution is then applied to the surface of a paddy field where it extends into a thin surface layer in the water.

Another embodiment of formulation is where an organic solution of the quaternary sulfonylurea compound of the invention in the presence of an emulsifier is formulated as an emulsifiable concentrate (EC). The EC is subsequently mixed in a mixing tank with water to form an oil in an aqueous emulsion for application of foliar dispersion in crops.

Another embodiment of the formulation is the quaternary sulfonylurea compound of the invention in an organic or aqueous base gel which can be added to a water mixing tank for application of foliar dispersion.

In some cases, bioactivity is improved by increasing the solubility of the solvent (in water or oil) where the sulfonylurea is present in a solution form for the sheet instead of as a particle, for example, for a dry fluid (DF) or a concentrated suspension (SC).

Finally, other bioactive advantages can be achieved by virtue of converting the solid sulfonylurea to a waxy solid, a crystalline or oily liquid however when the solvent evaporates. Waxy solid, crystalline or oily deposit can improve protection in the foliage of the plant or to help prevent complete washing.

Another embodiment of the invention includes premixed formulations comprising, in addition to the quaternary salt of bioactive sulfonylureas, additional herbicides such as bromoxanil and acetochlor. Other herbicides that can be used in the formulations with the bioactive sulfonylurea quaternary salts include familiar herbicides such as a hormone, anticholine esterase, or glyphosate. Examples of homonal herbicides include phenoxies, such as derivatives of (2, -dichlorophenoxy) acetic acid (2,4D) and 4-chloro-2-methyl phenoxy acetic acid (MCPA). Examples of herbicidal esterase anti-cancer includes forum organophosic herbicides such as anilophos. The quaternary sulphonylurea salt and the familiar salt can be dissolved in a common solvent - containing emulsifiers and other formulation ingredients to form an EC premix. Preferably, proton scavengers such as epoxides (e.g., epoxidized soybean oil) are added for further stabilization. Calcium acetate, anhydrous, solid, can also be added to the suspension for organic, liquid formulations to eliminate water and assist the chemical stabilization of the sulfonylurea.

Preferred organic solvents are naturally grown oils such as soybean oil, corn oil, cottonseed oil, sunflower oil and epoxidized or methylated versions, propylene carbonate, triethyl phosphate, n-alkyl pi rol idonas, and culture oil esters such as methylsoyate (Henkel) or acetates such as heptyl acetate and Exxatos® (Exxon) and mixtures thereof. Hydrophobic oils such as diisodecyl adipate and Cs-C 2 alcohol can be used to extend applications in a paddy.

Aqueous solution formulations may optionally contain glycols and antifreezes such as propylene glycol.

Organic solution formulations may optionally contain surface-active solvents at concentration ranges from 0.1 to 60%. Among the useful surfactants are common non-ionic agents such as polyvinyethylene alcohols, tri-stir-phenols, nonyl or octyl phenols, esters, sorbitol diesters and esters, polyoxyethylene / propylene block copolymers, ethoxylated siloxanes, acetylenic diols, and polyalkylene glycols. iglucosides. Anionic surfactants include, for example, alkylnaphthalene sulfonates, alkylalbenzene sulphonates, alpha-olefin sulfonates, calcium and ammonium 1-ignonaphonates, dodecylbenzene sulfonates, naphthalene / formaldehyde condensates, sulphosuccinates, alkyl and aryl sulfates and phosphates, ignosul fonatos e toxi the tados, sulfonates of alkyl ethoxy lated, and ethoxylated di- and tristyrylphenols as the sulfate and phosphate salt.

The following examples are means for exemplifying but not for limiting this invention. In all examples, a slight excess (about 5%) of an equivalent amount of the reagent can be used (e.g.

NaOH > sul fonilurea > quaternary hydroxide or quaternary halide).

EXAMPLE 1 Quaternary salt of 2- [[[[(4,6-dimethoxy-2-pyrimidinyl) amino] carbonyl] amino] sulfonyl] - N, N-dimethyl-3-pyridinecarboxamide.

To 21.57 g of 2 - [[[(4,6-dimethoxy-2-pyrimidinyl) amino] carbonyl] amino] sulfonyl] -N, N-dimethyl-3-pyridinecarboxamide and 50 mL of? AOH 1.0? in 1400 mL of methylene chloride was increased by adding 22.37 g of dimethyl-dimethylbenzene-ethoxyethyl diisobutyl-phenoxyi ammonium chloride (Hyamine 1622, commercially available from Lonza), several was washed with little methylene chloride to facilitate transfer. The average reaction was filtered through a molecular sieve bed to remove mineral salts and water. The methylene chloride was stripped of electrons to coat the white powder, it was rested for 1 week at 54 ° C, 9% of the relative decomposition of the resulting sulfonylurea was measured by HPLC.

EXAMPLE 2 Quaternary in situ salt of methyl 3- [[[(4-methoxy-6-methyl-1, 3, 5-triazin-2-yl) amino] carbonyl] amino] sulfonyl] -2-1-phenoxycarboxylate.

In 7.8 g of epoxidized soybean oil (ESBO) was added with stirring: 1.18 g of 3- [[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl) amino] carbonyl] amino ] sulphonyl] -2-thienide 1 carboxymethyl methylated (98.1%), 1.31 g ammonium chloride of dimethylbenzyl ethoxyethyl diisobutyl 1-phenoxy anhydrous in H20 (Hyamine 1622, available from Lonza), 0.11 g Ca (OH) 2, and 0.03 g of calcium acetate. The mixture was aged for 3 weeks at 45 ° C giving 0% relative decomposition of the sulfonylurea as measured by HPLC.

EXAMPLE 3 Quaternary salt of methyl 2- [[[(4-methyl-6-methyl-l, 3, 5-triazin-2-yl) methylamino] carbonyl] amino] sulfonyl] -benzoate.

A 15 g solution of technical methyl 2- [[[(4-methoxy-6-methyl-1, 3, 5-triazin-2-yl) methylamino] carbonyl] amino] sulfonyl] -benzoate (95.7%) and 18 g of Na 2 CO 3 in 300 g of CH 2 C 12 was treated with 1.5 g of NaOH and stirred 2 hours. 8.65 g of triethyl benzyl ammonium chloride was added to the suspension and the mixture was stirred overnight. The suspension was filtered and the filtrate stripped of electrons from the solvent in a rotary evaporator yielding the corresponding quaternary salt of sulfonylurea as a viscous yellow oil (15.7 g) using 1 g of the oil, 20% of the quaternary salt solution was made in triethyl phosphate. Resting for 1 week at 54 ° C, 1% relative decomposition of the resulting sulfonylurea was indicated by HPLC.

EXAMPLE 4 Quaternary salt of methyl 2 - [[[(4-methoxy-6-methyl-1, 3, 5-triazin-2-yl) methylamino] carbonyl] amino] sulfonyl] -benzoate.

A quaternary salt of sulfonylurea was prepared using the procedure of Example 3 with 20 g of 2- [[[[(4-methoxy-6-methyl-1, 3,5-triazin-2-yl) methylamino] carbonyl] amino] methyl sulfonyl] benzoate, 30 g of Na2CO3, 400 g of CH2C1, 2 g of NaOH and 11.5 of triethyl benzyl ammonium chloride. One gram of the resulting orange viscous oil was made with 20% of the solution in triethyl phosphate. Aged for 1 week at 54 ° C, 2% relative decomposition of the resulting sulfonylurea was indicated by HPLC.

COMPARATIVE EXAMPLE A.

Control for the quaternary salt of sulfonylurea soluble in oil.

Tetradodecyl ammonium bromide was dissolved in 5 mL of CH2C12 and stirred with 3.3 mL of 1N NaOH. To this was added 1.27 g of N - [[(4,6-dimethoxypyrimidin-2-yl) amino] carbonyl] -l-met il -4 - (2 -met 11 -2 H-tet razol-5-il) -l? -pyrazol-5-sulfonamide (97.8%) dissolved in 5 mL of CH2CI2 and stirring continued for 5 minutes at 25 ° C. The organic phase was separated, washed with water, dried and the solvent was removed under vacuum in a rotary evaporator at a maximum of 50 ° C. Colorless oilViscous resulting gave a 35% analysis of the corresponding quaternary salt of sulfonylurea (against 38% in theory) using HPLC. This oil was more than 50% soluble in epoxidized soybean oil, caprylic to methyl capra, and cottonseed oil. 50% of the solution of the quaternary sulphonylurea salt resulting in these three solvents is aged for 1 week at 54 ° C, giving 20-45% relative degradation by HPLC analysis. N- [[(4,6-dimethoxypyrimidin-2-yl) amino] carbonyl] -1-met i 1-4 - (2-methyl-2H-tetrazol-5-yl) -lH-pyrazole-5-sulfonamide It was practically insoluble in these three solvents.

COMPARATIVE EXAMPLE B.

Control of the quaternary salt of sulfonylurea soluble in water.

The following were liquefied in a small bottle: 0.214 g of 2- [[[[[(4,6-dimethoxy-2-pyrimidinyl) amino] carbonyl] amino] sulfonylmethyl] methyl nzoate (98.3%), 0.192 g of a 25% aqueous solution of tetramethyl ammonium hydroxide, and 4.32 g of water to produce the quaternary salt of sulfonylurea. By aging the solution at 54 ° C for one week, 52% degradation of the resulting sulfonylurea was measured by HPLC.

COMPARATIVE EXAMPLE C.

Control of sulfonylurea without salt in water Deionized water (5 g) was saturated with 2- [[[(4,6-dimethoxy-2-pyrimidinyl) amino] carbonyl] amino] sulfonyl] -N, N-dimethyl-3-pyridinecarboxamide (500 ppm) ) and aged at 25 ° C for 30 days. HPLC analysis indicated 90% relative degradation of the resulting sulfonylurea.

It is noted that in relation to this date, the best method known to the applicant to carry out the aforementioned invention, is that which is clear from the present description of the invention.

Having described the invention as above, the content of the following is claimed as property.

Claims (11)

1. Claims Compounds of Formula I characterized in that A is any active pesticidal compound with a pKa from about 3 to about 7; R1 is a substituted or unsubstituted benzyl group or a substituted or unsubstituted methylnaphthyl; R2, R3 and R4 are each a substituted or unsubstituted alkyl or substituted or unsubstituted alkaryl group, with the proviso that when the pesticide A is a sulfonylurea herbicide of the formula JS02NHCONR6Q and R1 is an unsubstituted benzyl, then one of R2, R3 or R4 is other than methyl or ethyl.
2. 2. The compounds according to claim 1, characterized in that the pesticidal active compound A is a herbicidal sulfonylurea compound generally represented by the formula JS02NHCONR6Q wherein J is substituted or unsubstituted phenyl or a heterocyclic group, Q is a substituted or unsubstituted pyrimidino or a substituted or unsubstituted triazine group and R6 is H or methyl.
3. 3. The compounds according to the rei indication 2, characterized by R1 is an unsubstituted benzyl group.
4. 4. The compounds according to claim 3, characterized in that R2, R3, R4 are C10-C25 alkyl or an alkaryl group.
5. 5. The compounds according to claim 2, characterized in that R1 is a substituted benzyl group.
6. 6. The compounds according to claim 5, characterized in that R2, R3, R4 are C10-C25 alkyl or an alkaryl group.
7. 7. A herbicidal composition for controlling the growth of unwanted vegetation, characterized in that it comprises an effective amount of a compound according to claim 1 and at least one of the following: surfactant or liquid inert diluent.
8. 8. The herbicidal composition for controlling unwanted vegetation growth, characterized by comprising an effective amount of a compound according to claim 2 and at least one of the following: surfactant or liquid inert diluent.
9. 9. The herbicidal composition to control the growth of vegetation no. desired, characterized in that it comprises an effective amount of a compound according to claim 3 and at least one of the following: surfactant or liquid inert diluent.
10. 10. The herbicidal composition for controlling the growth of unwanted vegetation, characterized in that it comprises an effective amount of a compound according to claim 3 and at least one of the following: surfactant or inert liquid diluent, wherein the surfactant is a t ris tirilfenol or octilfenol and the inert diluent liguido is water, epoxidized soybean oil or triethylphosphate.
11. 11. A method for controlling unwanted vegetation growth, characterized in that it comprises applying to the site that an effective amount of a compound according to claim 1 will be protected.