DE3900300A1 - L-[2-Halo-4-amino-6-(1-methyl-2,2,2-trifluoroethyl-amino)-s-triazi nes], process for their preparation, and their use as herbicides - Google Patents

Abstract

The invention relates to the novel optically active [2-halo-4-amino-6-(1-methyl-2,2,2-trifluoroethyl-amino)-s-triazines] in the L form, of the formula <IMAGE> in which R<1> represents chlorine or fluorine, R<2> represents hydrogen or alkyl and R<3> represents alkyl, alkoxyalkyl, haloalkyl, alkenyl or optionally halogen-substituted phenylalkyl, to a process for their preparation and to their use as herbicides. The herbicidal activity of the L enantiomers are markedly superior to that of the corresponding racemates.

Description

The invention relates to the new optically active 2- Halogen-4-amino-6- (1-methyl-2,2,2-trifluoroethylamino) -s- L-form triazines, a process for their preparation and their use as herbicides.

It is known that the racemic mixtures of 2- Halogen-4-amino-6- (1-methyl-2,2,2-trifluoroethylamino) -s- have triazine herbicidal properties (cf. DE-A- 32 18 201 and DE-A-32 18 966). The herbicidal effectiveness of these known racemates against harmful plants or their selectivity in certain crops but not always fully satisfactory.

The new optically active L- [2-halogen-4- amino-6- (1-methyl-2,2,2-trifluoroethylamino) -s-triazine] of the general formula (I)  

in which

R¹ represents chlorine or fluorine,
R² represents hydrogen or alkyl and
R³ represents alkyl, alkoxyalkyl, haloalkyl, alkenyl or phenyl alkyl which is optionally substituted by halogen,

found.

It was also found that the optically active s-triazine derivatives of the above formula (I) in the L-form is obtained when the cyanuric chloride or cyanuric fluoride Formulas (IIa) and (IIb)

initially with the approximately equimolar amount of 2-amino 1,1,1-trifluoropropane (L form) of the formula (III)

or with its hydrochloride in the presence of an acid binding agent and optionally in the presence of a Diluent (1st stage) and this formed L- [2,4-dihalogen-6- (1-methyl-2,2,2-trifluoro- ethylamino) -s-triazine] of the formula (IV)

in which the remains
R¹ are the same and represent either chlorine or fluorine,
with the approximately equimolar amount of an amine of the formula (V)

in which

R² represents hydrogen or alkyl and
R³ represents alkyl, akoxyalkyl, haloalkyl, alkenyl or phenyl alkyl which is optionally substituted by halogen,

in the presence of an acid-binding agent and given if reacted in the presence of a diluent (2nd stage).

It was also found that the new optically active s-triazine derivatives of the formula (I) are strong in the L form Have herbicidal properties and more surprising the corresponding previously known racemic ver bindings, but also - as far as this has been determined so far could be - the corresponding (not prescribed) D-enantiomers, in the herbicidal effect are superior.

Of the compounds of the formula (I) according to the invention those in which are preferred

R¹ represents chlorine or fluorine,
R² represents hydrogen or C₁-C₄-alkyl and
R³ is C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, halogen-C₁-C₄-alkyl, C₃-C₆-alkenyl or optionally halogen-substituted phenyl-C₁-C₄-alkyl.

Such compounds of the formula are particularly preferred (I) in which

R¹ represents chlorine or fluorine,
R² represents hydrogen or C₁-C₂-alkyl and
R³ for C₁-C₃-alkyl, C₁-C₃-alkoxy-C₁-C₂-alkyl, fluoro-C₁-C₃-alkyl, chloro-C₁-C₃-alkyl, bromo-C₁-C₃-alkyl, C₃-C₄-alkenyl or optionally chlorine-substituted phenyl-C₁-C₂-alkyl.

When using cyanuric fluoride, L- [2-amino-1,1,1-tri- fluoropropane] and 2-ethoxyethylamine as starting materials can the course of the reaction after Ver can be sketched using the following formula scheme:

The L- [2-amino-1,1,1-trifluoropropane] of the formula (III) and a method for its production, starting from L-Alanine, are the subject of their own older patent application (cf. German patent application P 38 00 178.0 from 07.01.1988) as well as manufacturing examples.

The amines to continue to be used as starting materials are generally defined by formula (V). To this Formula R² and R³ preferably or particularly be prefers the same meanings as already mentioned above in the Connection with the description of the invention Compounds of formula (I) as preferred or special were preferably given for R² and R³.

The amines of the formula (V) are known. Suitable Ver treads are methyl, ethyl, n-propyl, isopropyl, n- Butyl, isobutyl, tert-butyl, hexyl, allyl, di ethyl, diallyl and dibutylamine, also benzylamine, 1- Phenylethylamine, 1-methyl-1-phenylethylamine, 1- (4-chlorine phenyl) ethylamine, 1- (2-chlorophenyl) ethylamine, 2- Methoxy-ethylamine, 3-methoxy-propylamine, 4-methoxy butylamine, 2-chloroethylamine, 2,2,2-trichloroethylamine, 2,2,2-trifluoroethylamine as well as (D-), (L-) and racemic 2-amino-1,1,1-trifluoropropane.

The reaction temperatures can be at the two above written stages of the inventive method in can be varied within a certain range. In general you work at the first level between -10 and + 25 ° C (preferably between 0 and 20 ° C) and at the second  Stage generally between 0 and 50 ° C (preferably between 10 and 45 ° C).

The following general information regarding the Molar ratios, diluents and acid binders each refer to the two described above Procedural stages.

When carrying out the method according to the invention you set the starting materials and, if necessary, the Acid binder in approximately equimolar amounts.

The reactions are preferred in the presence of a ver performed fertilizer. Com. As diluent all inert organic solvents. These preferably include hydrocarbons such as Benzene and xylene, chlorinated hydrocarbons such as Chlorobenzene and carbon tetrachloride; Ketones like Ace clay and methyl ethyl ketone; Ethers such as tetrahydrofuran and Dioxane; Amides such as dimethylformamide.

The reactions can also be carried out in the presence of water be performed, e.g. B. in the presence of aqueous Alkali hydroxide solution as an acid binding agent.

All customary acid binders can be used as acid binders be used. These preferably include the tertiary ferrous amines, such as trimethylamine, triethylamine and pyridine, Alkali hydroxides such as sodium hydroxide and potassium hydroxide as well as alkali carbonates such as sodium carbonate and Ka  lium carbonate. In the second stage of the process, too an equimolar excess of amine of formula (V) as Serve acid binders.

According to a special embodiment of the invention The two process stages can be used as "One-pot reaction" are carried out, the Intermediates of formula (IV) are not isolated will need.

The processing and isolation of the reaction products takes place in the usual way. When adding water to the Reaction mixture generally fall the reaction products already mean crystalline if solvent ver have been used that mix with water.

The active substances according to the invention influence the plant zen growth and can therefore as Defoliants, Desi cants, herbicides, germ inhibitors and ins especially used as a weed killer. All plants are under weeds in the broadest sense to understand who grow up in places where they are immature are desired. Whether the substances according to the invention as total or selective herbicides act essentially depends depends on the amount applied.

The active compounds according to the invention can, for. B. at the following plants can be used:  

Dicotyledon weeds of the genera: Sinapis, Lepidium, Ga lium, stellaria, matricaria, anthemis, galinsoga, cheno podium, urtica, senecio, amaranthus, portulaca, xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cir sium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Linder nia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Ga leopsis, papaver, centaurea.

Dicotyledon cultures of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cu cumis, cucurbita.

Monocotyledon weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Bra chiaria, lolium, bromus, avena, cyperus, sorghum, agro pyron, cynodon, monochoria, fimbristylis, sagittatria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera.

Monocot cultures of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ana nas, asparagus, allium.

The use of the active compounds according to the invention is dependent by no means limited to these genres, but extends to other plants in the same way Zen.

The connections are suitable depending on the con center for total weed control z. B. on industrial  and track systems and on paths and squares with and without Tree growth. Likewise, the connections to weeds control in permanent crops, e.g. B. forest, ornamental wood, Fruit, wine, citrus, nut, banana, coffee, tea, Gum, oil palm, cocoa, berry fruit and hop plants and for selective weed control in annuals Cultures are used.

The compounds of formula (I) according to the invention are suitable in particular for selective weed control of mono- and dicotyledon weeds in mono- and dicotyledons Cultures, pre- and post-emergence.

The active ingredients can be in the usual formulations are transferred, such as solutions, emulsions, spray powder ver, suspensions, powders, dusts, pastes, soluble Powders, granules, suspension emulsion concentrates, Active substance-impregnated natural and synthetic substances as well as very fine encapsulation in polymeric substances

These formulations are produced in a known manner provides, e.g. B. by mixing the active ingredients with stretch means, i.e. liquid solvents and / or solid Carriers, optionally using upper surfactants, i.e. emulsifiers and / or Dispersing agents and / or foaming agents.

In the case of the use of water as an extender z. B. also organic solvents as auxiliary sol be used. As a liquid solvent essentially come into question: aromatics, such as xylene,  Toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorine benzenes, chloroethylene or methylene chloride, alipha table hydrocarbons, such as cyclohexane or paraffins, e.g. B. petroleum fractions, mineral and vegetable oils, Alcohols, such as butanol or glycol, and their ethers and Esters, ketones such as acetone, methyl ethyl ketone, methyl iso butyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulfoxide, and water.

The following are suitable as solid carriers: e.g. B. ammonium salts and natural rock powders, such as Kaolins, clays, talc, chalk, quartz, attapulgite, Montmorillonite or diatomaceous earth and synthetic Ge stone powders such as finely divided silica, aluminum oxide and silicates, come as solid carriers for granules in question: e.g. B. broken and fractionated natural Ge stones such as calcite, marble, pumice, sepiolite, dolomite as well synthetic granules from inorganic and organic Flours and granules made from organic material such as a saw flour, coconut shells, corn cobs and tobacco stalks; as Emulsifying and / or foaming agents are possible: e.g. B. nonionic and anionic emulsifiers, such as poly oxyethylene fatty acid ester, polyoxyethylene fatty alcohol Ethers, e.g. B. alkylaryl polyglycol ethers, alkyl sulfonates, Alkyl sulfates, aryl sulfonates and protein hydrolyzates; as dispersants come into question: z. B. Lignin-Sul lye and methyl cellulose.

Adhesives such as carboxy can be used in the formulations methyl cellulose, natural and synthetic powder,  granular or latex-shaped polymers can be used, such as Gum arabic, polyvinyl alcohol, polyvinyl acetate.

Dyes such as inorganic pigments, e.g. B. Iron oxide, titanium oxide, ferrocyan blue and organic color substances such as alizarin, azo and metal phthalocyanine color substances and trace nutrients such as salts of iron, manganese, Boron, copper, cobalt, molybdenum and zinc can be used.

The formulations generally contain between 0.1 and 95 percent by weight of active ingredient, preferably between 0.5 and 90%.

The active compounds according to the invention can be used as such or in their formulations also in mixtures with known ones Find herbicides for weed control, wherein Ready formulations or tank mixes possible are.

Known herbicides come into question for the mixtures, e.g. B. aryloxyalkanoic acids such as 2,4-D, 2,4-DP, 2,4-DB, MCPA, MCPP and fluoroxypyr;
Aryloxy-phenoxy-alkanoic acid esters such as diclofop-methyl and fenoxaprop;
Aryl carboxylic acids such as clopyralide;
Chloroacetanilides, such as alachlor, metolachlor or propa chlorine;
Dinitroanilines such as pendimethalin and trifluralin;
Diphenyl ethers such as bifenox and oxyfluorfen;
Ureas such as chlorotoluron, isoproturon and methabenzthiazuron;
Imidazolinones such as imazamethabenz;
Nitriles such as bromoxynil and ioxynil;
Oxyacetamides such as mefenacet;
Sulfonylureas, such as chlorosulfuron, metsulfuron or thiameturon;
Thiol carbamates such as EPTC and triallates;
Triazines such as atrazine, cyanazine, simazin and terbutryne;
Triazinones such as ethiozine, metamitron and metribuzin;
also Bentazone and Pyridate.

Also a mixture with other known active ingredients, such as fungicides, insecticides, acaricides, nematicides, Protective substances against bird damage, growth regulators, Plant nutrients and soil structure improvement averaging is possible.

The active ingredients as such, in the form of their formu or the resulting from further dilution riding application forms, such as ready-made solutions, Suspensions, emulsions, powders, pastes and gra nulate can be applied. The application happens in practice Licher way, e.g. B. by pouring, spraying, spraying, Scatter or dust.

The active compounds according to the invention can be used both before and can also be applied after the plants have emerged. They can also be worked into the soil before sowing will.  

The amount of active ingredient used can be in larger ranges vary. It essentially depends on the type of the desired effect. In general, the Application rates between 0.01 and 10 kg of active ingredient per ha, preferably between 0.05 and 5 kg / ha.

The production and use of the invention Active ingredients are derived from the examples below in front.  

Manufacturing examples

Unless otherwise stated, tetrahydrofuran (layer thickness c = 1 cm) was used as the solvent for the measurement of all optical rotation values [ α ] listed below.

Example 1

To 36.9 g (0.2 mol) of cyanuric chloride suspended in 200 ml Toluene, at 8 to 10 ° C 22.6 g (0.2 mol) 2-amino-1,1,1-trifluoropropane (L-form) and then at 10 to 12 ° C a solution of 8.0 g (0.2 mol) sodium hydroxide added dropwise in 20 ml of water. After 15 to 30 Wed grooves are first in this suspension at 15 to 20 ° C 17.8 g (0.2 mol) of 1-amino-3-methoxypropane and then ß at 20 ° C a solution of 8.0 g (0.2 mol) of sodium hydroxide added dropwise in 20 ml of water. At 25 ° C approx. Stirred for 1 hour. Then with 20% hydrochloric acid Adjustment to pH 3 to 4. Subsequent heating up 75 ° C gives two clear phases, one of which is the toluene phase is separated off and concentrated in vacuo. The first one oily colorless residue crystallized.

59.6 g (95% of theory) of L (+) - {2-chloro-4- [N- (3-methoxypropyl)] - amino-6- [N- (1-methyl-2, 2,2-trifluoroethyl)] - amino-1,3,5-triazine} melting point 65-66 ° C; Rotation value [ α ] = + 18.0.

Analogously to Example 1, the following in Table 1 Compounds of formula (I) listed will:

Table 1

Example 8

To 36.9 g (0.2 mol) of cyanuric chloride suspended in 200 ml Toluene, at 8 to 10 ° C 22.6 g (0.2 mol) 2-amino-1,1,1-trifluoropropane (L-form) and then at 10 to 12 ° C a solution of 8.0 g (0.2 mol) sodium hydroxide added dropwise in 20 ml of water. After 15 to 30 Wed grooves are first in this suspension at 15 to 20 ° C 18.0 g (0.2 mol) aqueous ethylamine solution (50%) and then a solution of 8.0 g (0.2 mol) at 20 ° C. Sodium hydroxide added dropwise in 20 ml of water. At 25 ° C is stirred for about 1 hour. With 20% hydrochloric acid The pH is then adjusted to 3 to 4. Then, at Stirred at 75 ° C. After cooling to 40 ° C with water added and the solid reaction product is suctioned off. The The residue is washed with water and dried.

47.0 g (87.2% of theory) of L (+) - {2-chloro-4-ethylamino-6- [N- (1-methyl-2,2,2-trifluoroethyl)] amino are obtained. 1,3,5-triazine} melting point 153-154 ° C; Rotation value [ α ] = + 16.4.

Example 9

To 36.9 g (0.2 mol) of cyanuric chloride suspended in 200 ml Toluene, at 8 to 10 ° C 22.6 g (0.2 mol) 2-amino-1,1,1-trifluoropropane (L-form) and then at 10 to 12 ° C a solution of 8.0 g (0.2 mol) sodium hydroxide added dropwise in 20 ml of water.  

After 15 to 30 minutes, be in this suspension 15 to 20 ° C 41.4 g (0.4 mol) aqueous methylamine solution (30%) added dropwise. At 20 ° C is about 1 hour after stirred With 20% hydrochloric acid adjust to pH 3 to 4. Then the mixture is stirred at 40 ° C. with water added and the solid reaction product is suctioned off. The The residue is washed with water and dried.

44.0 g (86.1% of theory) of L- {2-chloro-4- are obtained. methylamino-6- [N- (1-methyl-2,2,2-trifluoroethyl)] - amino- 1,3,5-triazine} melting point 175-176 ° C.

Analogously to Examples 8 and 9, the following can be used Compounds of formula (I) listed in Table 2 be put.

Table 2

Example 15

If cyanuric fluoride is used instead of cyanuric chloride, analogously to Example 1, L (+) - {2-fluoro-4- [N- (3-methoxypropyl)] - amino-6- [N- (1-methyl- 2,2,2-trifluoroethyl)] - amino-1,3,5-triazine} melting point 101-102 ° C; Rotation value [ α ] = + 18.4.

Preparation of the starting compound (III) L- (2-amino-1,1,1-trifluoropropane) a) 2-Amino-1,1,1-trifluoropropane hydrochloride, L-form

100 g (1.12 mol) of L-alanine are mixed with 280 g of weld feltetrafluoride and 140 ml HF for 8 hours in a V₄A stirred autoclave at 120 ° C under autogenous pressure (approx. 21 bar) implemented. After distilling off the volatile constituents the residue is in 500 ml of water added, with 45% sodium hydroxide solution made alkaline and then the product separated by steam distillation. The Steam distillate is made with concentrated salt acidified. After concentration and drying 80 g (47.6%) of 2-amino-1,1,1-trifluoropropane isolated as hydrochloride in the L-form.  

b) (-) - 2-Amino-1,1,1-trifluoropropane, L-form

To 59.8 g (0.4 mol) of L (-) - 2- [amino-1,1,1-trifluoro propane hydrochloride] from Example a) are 40 g (0.45 mol) 45% aqueous sodium hydroxide solution at 75 to 80 ° C oil bath temperature dropped in about 15 minutes. At the same time, the free amine at 42 to 48 ° C. distilled off. After drying over magnesium sulfate is redistilled. The product obtained is:

41.1 g (91%) L - (-) - [2-amino-1,1,1-trifluoropropane]
Bp: 47-48 ° C.
n : 1.3215.
Purity according to gas chromatogram: 100%. Rotary value: -9.712 (undiluted).

Isolation of the intermediate of formula (IV), R¹ = Cl

To 36.9 g (0.2 mol) of cyanuric chloride suspended in 200 ml Toluene, at 8 to 10 ° C 22.6 g (0.2 mol) 2-amino-1,1,1-trifluoropropane (L-form) and then at 10 to 12 ° C a solution of 8.0 g (0.2 mol) sodium hydroxide added dropwise in 20 ml of water.  

At 15 ° C, stirring is continued for about 1 hour. With 20% Hydrochloric acid is then adjusted to pH 3 to 4. After Adding water, the toluene phase is separated and in Vacuum concentrated.

46.0 g (88.1% of theory) of L (+) - {2,4-di chloro-6- [N- (1-methyl-2,2,2-trifluoroethyl) amino] -1 are obtained , 3,5-triazine} in the form of a colorless viscous oil; Rotation value [ α ] = + 4.2.

The intermediate of formula (IV), R¹ = F, L- {2,4- Difluoro-6- [N- (1-methyl-2,2,2-trifluoroethyl) amino] - 1,3,5-triazine} can be prepared in an analogous manner will.  

Example A Pre-emergence test / greenhouse

Solvent: 5 parts by weight of acetone
Emulsifier: 1 part by weight of alkylaryl polyglycol ether

For the preparation of a suitable active ingredient preparation is mixed 1 part by weight of active ingredient with the specified Amount of solvent, gives the specified amount of emul gator and dilute the concentrate with water to the desired concentration.

Seeds of the test plants are sown in normal soil and after 24 hours with the drug preparation poured. You keep the amount of water per area expediently constant. The drug concentration in the preparation doesn't matter, crucial is only the application rate of the active ingredient per area Ness. After three weeks, the degree of damage to the Plant rated in% damage compared to Ent winding of the untreated control. It means:

0% = no effect (like untreated control)
100% = total annihilation

Active ingredients, application rates, test plants and test results Table A shows the results.  

Table A

Pre-emergence test / greenhouse

Example B Post emergence test / greenhouse

Solvent: 5 parts by weight of acetone
Emulsifier: 1 part by weight of alkylaryl polyglycol ether

For the preparation of a suitable active ingredient preparation is mixed 1 part by weight of active ingredient with the specified Amount of solvent, gives the specified amount of emul gator and dilute the concentrate with water to the desired concentration.

With the preparation of the active ingredient you inject test plants, which have a height of 5 to 15 cm - so that the desired amounts of active ingredient per unit area be applied. The concentration of the spray liquor is chosen so that in 1000 l of water / ha each desired amounts of active ingredient are applied. To The degree of damage to the plants is bonus for three weeks % damage compared to the development of the untreated control.

It means:

0% = no effect (like untreated control)
100% = total annihilation

Active ingredients, application rates, test plants and test results nisse are shown in Table B below.  

Table B

Post emergence test / greenhouse

List of active substances

Claims (12)

1. L- [2-halo-4-amino-6- (1-methyl-2,2,2-trifluoroethylamino) -s-triazine] of the general formula (I) in which
R¹ represents chlorine or fluorine,
R² represents hydrogen or alkyl and
R³ represents alkyl, alkoxyalkyl, haloalkyl, alkenyl or phenylalkyl optionally substituted by halogen. 2. Optically active compounds of formula (I) according to claim 1, characterized in that therein
R¹ represents chlorine or fluorine,
R² represents hydrogen or C₁-C₄-alkyl and
R³ is C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, halogen-C₁-C₄-alkyl, C₃-C₆-alkenyl or optionally halogen-substituted phenyl-C₁-C₄-alkyl. 3. Optically active compounds of formula (I) according to claim 1, characterized in that therein
R¹ represents chlorine or fluorine,
R² represents hydrogen or C₁-C₂-alkyl and
R³ for C₁-C₃-alkyl, C₁-C₃-alkoxy-C₁-C₂-alkyl, fluoro-C₁-C₃-alkyl, chloro-C₁-C₃-alkyl, bromo-C₁-C₃-alkyl, C₃-C₄-alkenyl or optionally chlorine-substituted phenyl-C₁-C₂-alkyl. 4. L (+) - {2-chloro-4- [N- (3-methoxypropyl)] - amino-6- [N- (1-methyl-2,2,2-trifluoroethyl)] - amino- 1,3,5-triazine} of the formula according to claim 1. 5. L (+) - {2-chloro-4-ethylamino-6- [N- (1-methyl-2,2,2-trifluoroethyl)] - amino-1,3,5-triazine} of the formula according to claim 1. 6. L- {2-chloro-4-methylamino-6- [N- (1-methyl-2,2,2-tri fluoroethyl)] amino-1,3,5-triazine} of the formula according to claim 1. 7. A process for the preparation of L- [2-halo-4-amino-6- (1-methyl-2,2,2-trifluoroethylamino) -s-triazines] of the general formula (I) according to claim 1, characterized in that that cyanuric chloride or cyanuric fluoride of the formulas (IIa) or (IIb) initially with the approximately equimolar amount of 2-amino-1,1,1-trifluoropropane (L-form) of the formula (III) or with its hydrochloride in the presence of an acid-binding agent and optionally in the presence of a diluent (1st stage) and the L- [2,4-dihalogen-6- (1-methyl-2,2,2-trifluoroethylamino) formed -s-triazine] of the formula (IV) in which the remains
R¹ are the same and represent either chlorine or fluorine,
with the approximately equimolar amount of an amine of the formula (V) R² represents hydrogen or alkyl and
R³ represents alkyl, alkoxyalkyl, haloalkyl, alkenyl or phenylalkyl optionally substituted by halogen,
in the presence of an acid-binding agent and, if appropriate, in the presence of a diluent (2nd stage). 8. L- [2,4-dihalogen-6- (methyl-2,2,2-trifluoroethyl amino) -s-triazine] of the formula (IV) in which the remains
R¹ are the same and represent either chlorine or fluorine. 9. Herbicidal agents, characterized by a content on an optically active compound of the formula (I) according to claim 1. 10. Use of optically active compounds Formula (I) according to claim 1 for combating un desired plant growth. 11. Weed control method, thereby ge indicates that you have an optically active connection extension of the formula (I) according to claim 1 to the Un herbs or their habitat. 12. Process for the preparation of herbicidal compositions, characterized in that optically active ver Compounds of formula (I) according to claim 1 with Extenders and / or surfactants mixed.