DE2511897A1 - 2,6-DINITROANILINE, METHOD FOR MANUFACTURING IT AND HERBICIDAL AGENTS CONTAINING IT - Google Patents

Description

The invention relates to new 2,6-dinitroanilines, in particular new, 4-substituted 2,6-dinitroanilines, processes for the preparation of this new class of compounds and herbicidal compositions containing these new compounds and methods of weed control using these novel compounds.

As has been found, the novel compounds according to the invention are distinguished by excellent selective herbicidal properties Effectiveness off, d. H. they are phytotoxic to many classes of weeds, to many important crops (Crops), such as B. Cotton, soybeans,

509839/1052

edible beans and the like., harmless. Therefore, the new compounds according to the invention for the selective Weed control can be used in such crops or crops.

The invention relates to new 2,6-dinitroanilines general formula

where mean:

R an ethyl? Propyl or allyl group and

R is a C ₁ -C, -alkyl, trifluoromethyl, difluoromethyl, methylsulfonyl or sulfamoyl group.

The new compounds according to the invention are 2,6-dinitroanilines which are replaced by a methaiylamino substituent are characterized. The other amino substituent is selected from the group ethyl, propyl and allyl, and the New compounds according to the invention have a 4-substituent which is selected from the groups indicated above. In the 3 and 5 positions of the phenyl ring, those according to the invention have Compounds hydrogen atoms. In the above

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In the formula given in the formula, the term ¹¹ C -C -alkyl "refers to those alkyl groups which contain 1 to 4 carbon atoms, such as, for example, methyl, ethyl, propyl, isopropyl, n-butyl, s-butyl and t-butyl .

For the sake of clarity, it should be pointed out that all of the compounds according to the invention described below to 2,6-Dinitroaniline is, even if some of these compounds according to different nomenclature rules of the organic Chemistry can also be called differently.

The invention also relates to a new process for the preparation of the 2,6-dinitroanilines of the general types given above Formula I, which is characterized in that a dinitrobenzene of the general formula

X.

, NO ₂

wherein X is a halogen atom, preferably a chlorine atom, and R has the meanings given above,

reacts with an amine of the general formula R-NH-CH ₂ -C = CH ₂

50 9 83 9 / 1OS 2

wherein R has the meanings given above.

The invention also relates to herbicidal compositions which are characterized in that they contain at least one Compound of the general formula I given above together with at least one inert carrier or a diluent included for it.

Further objects of the invention are a process for the production of a herbicidal composition as defined above, in the at least one compound of the formula I with at least one suitable carrier or diluent therefor is mixed, as well as a method for inhibiting or preventing the growth of weeds and / or for preventing the growth of weed seeds or germs on arable land, which is characterized in that one before the emergence the weeds a herbicidally effective amount of at least one compound of the general formula I given above to the Arable land.

The synthesis of the new compounds according to the invention will preferably in an organic solvent or in a basic aqueous medium at a temperature from 0 to about 100 C or above. The response times are generally within the range from about 1 to about 24 hours, depending on the reaction temperature. All as an exit smat er i alien in the synthesis of the compounds according to the invention Compounds used are commercially available or can be according to known in the chemical literature

5ΠΠΠ39 / 1 U 5 2

Process are produced.

Suitable organic solvents include aromatic hydrocarbons such as benzene and toluene, alcohols such as Ethanol and isopropanol, and other inert reaction solvents, such as tetrahydrofuran and dimethyl sulfoxide. The organic solvent should be an acid binder, such as triethylamine, be added, which binds (absorbs) the hydrogen halide released during the reaction (e.g. HCl), The reaction works well in a basic aqueous medium away; Sodium carbonate is preferably used as the base, although other bases such as sodium hydroxide or potassium carbonate are also used. are suitable.

The reaction temperature can vary from 0 to about 100 C or even above if high pressure equipment is used will. As usual, it is most convenient to carry out the reaction at the reflux temperature of the reaction mixture. Carrying out the reactions at elevated temperatures does not lead to any side reactions or to any thermal decomposition.

In general, the realizations proceed at speeds that depend on the temperature until they are complete. The rate of reaction can be increased by adding a high-boiling reaction solvent and operating at the reflux temperature. One hour is sufficient to achieve a substantial yield of any of the compounds of the invention. Even at low temperatures, 24 hours are sufficient to achieve a maximum yield of each of the invention - fi -

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proper connections.

Preferred compounds according to the invention, which are also used with preference for carrying out the herbicidal processes, the production of the herbicidal compositions and in the processes for their production, are N-ethyl-N-methallyl-4-trifluoromethyl-2,6-dinitroaniline, N- Methallyl-N-propyl-4-trifluoromethyl-2,6-dinitroanil in, N-ethyl-N-methallyl-4-sulfamoyl-2,6-dinitroaniline, N-ethyl-4-isopropyl-N-methallyl-2,6 -dinitroaniline, 4-isopropyl-N-methallyl-N-propyl-2 _i 6-dinitroaniline, 4- (t-butyl) -N-methallyl-N-propyl-2,6-dinitroaniline and N-allyl-N-methallyl -4-trifluoromethyl-2,6-dinitroaniline. The particularly preferred compound according to the invention is N-ethyl-N-methallyl-4-trifluoromethyl-2,6-dinitroaniline.

The following examples serve to illustrate the simple reactions after which the compounds according to the invention can be produced, but the invention is not limited thereto.

example 1

A reaction mixture containing 5.05 g of 4-chloro-3,5-dinitro-α, α-benzodifluoride, 4.5 g of N-propylmethaiIylamine and 4 g of triethylamine in 100 ml of benzene was refluxed overnight with stirring. After the completion of the reaction, the reaction mixture became washed first with dilute hydrochloric acid and then with water and the organic phase became

509839/1052 " ⁷ "

dried over magnesium sulfate. The solvent was then removed in vacuo and the oily residue was dissolved in Dissolved hexane and purified with a 100 g column filled with Magnesium silicate, chromatographed. The purified product was eluted with hexane, the increasing amounts, up to 20%, contained benzene. The fractions containing the product were collected and evaporated in vacuo to give 4.8 g of an oil which by NMR analysis to be 4-difluoromethyl-N-methallyl-N-propyl-2,6-dinitroaniline identified became. The elemental analysis gave the following values:

calc .: C 51.06 H 5.20 N 12.76 found: C 50.81 H 5.45 N 12.71 %

NMR maxima occurred at 0.83, 1.56, 1.7, 2.93, 3.52, 4.94, 6.61 and 7.89 ppm.

Example 2

N-ethyl-N-methally! -4-sulfamoy_l-2,6-dinitroaniline

To a solution of 2.82 g of 4-chloro-3,5-dinitrobenzenesulfone ~ amide in 100 ml of denatured ethanol was 2.0 g of N-ethylmethallylamine and 2.0 g of triethylamine were added. The mixture was refluxed with stirring for 2 hours. then the solution was cooled and by diluting the mixture with water and allowing it to stand for several days on one The crude product was crystallized in a cool place. The yellow crystals were collected and air dried. To the recrystallization of the crude product from aqueous ethanol

509 H 3 9/1052 " ⁸ "

1.62 g of N-ethyl-N-methallyl ^ -sulfamoyl ^, 6-dinitroaniline, mp 123 to 125 ° C. were obtained. The NMR analysis confirmed that this was this compound. Elemental microanalysis gave the following values: calc .: C 41 £ 6 H 4.68 N 16.29 found: C 42.05 H 4.82 N 15.98 %

Example 3

4-IsOE ^ opyJ ^ N-methallYl-N-propYl-2 _f 6-dinitroaniline

To a suspension of 2.45 g of 4-chloro-3,5-dinitrocurnol in in 75 ml of denatured ethanol were 2.3 g of N-propylmethallylamine and 2.0 g of triethylamine were added. The mixture was refluxed for 16 hours and cooled. the The reaction mixture was then diluted with 300 ml of water and extracted with 500 ml of ether. The ether extract was used once with water ^ twice with dilute hydrochloric acid, then washed once again with water and dried over anhydrous MgSO ^. The organic phase was then concentrated to dryness under vacuum and the residue was dissolved in hexane. The solution was purified on magnesium silicate chromatographed and eluted with more hexane. The fraction containing the product was collected and the Solvent was evaporated, giving 1.4 g of 4-isopropyl-N-methallyl-N-propyl-2,6-dinitroaniline received in the form of a yellow oil. The identity was confirmed by NMR analysis. NMR maxima occurred at 0.78, 1.28, 1.47, 1.68, 2.88, 2.98, 3.52, 4.89 and 7.63 ppm. Elemental microanalysis gave the following values:

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calc .: C 59.69 H 7.21 N 13.08 found: C 59.69 H 7.03 N 13.28 %

The examples given above represent typical syntheses by which the compounds according to the invention are prepared can be. The person skilled in the art is not faced with any difficulties by slightly changing the above syntheses described to produce all compounds according to the invention. The one described in the examples above general procedures were used to prepare the compounds enumerated in the examples below. The characteristic data for each compound are given in the following examples.

Example 4

N-allyl-N-methallyl-4-trifluoromethyl-2,6 ~ dinitroaniline, F. 53 to 54 ° C.

Example 5

N-methallyl-N-propyl-4-sulfamoyl-2,6-dinitroaniline, M.p. 93 to 95 ° C.

Example 6

N-ethyl-N-methallyl-4-trifluoromethyl-2,6-dinitroaniline,

F. 54 to 57 ⁰ C.

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5098 3 9/1052

Example 7

N-methallyl-N-propyl-4-trifluoromethyl-2,6-dinitroaniline,

41 to 43 ° C.

Example 8

4- (t-butyl) -N-methallyl-N-propyl-2,6-dinitroaniline,

M.p. 59 to 61 ° C.

Example 9 '

4- (t-butyl) -N-ethyl-N-methaIyl-2,6-dinitroaniline,

M.p. 68 to 70 ° C.

Example 10

4- (s-butyl) -N-ethyl-N-methallyl-2,6-dinitroaniline,

Oil; NMR maxima at 0.89, 1.04, 1.28, 1.63, 1.68, 2.71, 3.02,

3.48, 4.87 and 7.53 ppm.

Example 11

N-ethyl ^ -isopropyl-N-methallyl- ^ jö-dinitroaniline, M.p. 52 to 54 ° C.

- 11 -

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- 11 - Example 12 251 • 1897 1.68, 2.73, 3.03, 3, 50, 4.88 N-ethyl-N-methallyl ^ -methyl- ^, 6-dinitroaniline, M.p. 48 to 50 ° C. Example 13 , 6-dinitroaniline, 3.50, 3.60, 4.84, 4, 92 to N-ethyl-4-difluoromethyl-N-methallyl-2,6-dinitroaniline, M.p. 68 to 70 ° C. Example 14 , 6-dinitroaniline, 1.47, 1.68, 2.70, 2, 89, 3.52, N, 4-diethyl-N-methallyl-2,6-dinitroaniline, - 12 - Oil; NMR maxima at 1.04, 1.28, and 7.61 ppm. Example 15 N-allyl-N-methallyl-4-methyl-2 Oil; NMR maxima at, 1.63, 2.43, 5.28, 5.85, 7.64 ppm. Example 16 4-ethyl-N-methallyl-N-propyl-2 Oil; NMR maxima at 0.79, 1.28, 4.88, 7.59 ppm.

9-83 9/10 5 2

Example 17

4- (s-Buty1) -N-methallyl-N-propyl-2,6-dinitroaniline,

oil; NMR maxima at 0.82, 0.88, 1.30, 1.13 to 1.90, 1.68,

2.73, 2.87, 3.50, 4.88 and 7.54 ppm.

Example 18

N-allyl-4- (s-butyl) -N-methallyl-2,6-dinitroaniline,

Oil; NMR maxima at 0.88, 1.29, 1.63, 1.64, 2.72, 3.48, 3.58,

4.83, 4.89 to 5.28, 5.83 and 7.55 ppm.

Example 19

N-allyl-4-difluoromethyl-N-methallyl-2,6-dinitroaniline, Oil; NMR peaks at 1.68, 3.54, 3.67, 4.93, 4.97 to 5.35, 5.85, 6.69, 8.00 ppm.

Example 20

N-allyl-4-ethyl-N-methallyl-2,6-dinitroaniline, M.p. 37 to 38 ° C.

Example 21

N-methallyl-4-methyl-N-propyl-2,6-dinitroaniline, M.p. 48 to 50 ° C.

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5 0 9 8 3 9/1 0 5

Example 22

N-allyl-N-methallyl ^ -sulfamoyl ^, 6-dinitroaniline,

M.p. 128 to 129 ° C.

Example 23

N-methailyl-4-methylsulfcmyl-N-propyl-2,6-dinitroaniline, M.p. 110.5 to 112.5 ° C.

Example 24

N-allyl-4-: bopropyl-N-methallyl-2,6-dinitroaniline,

Oil; NMR maxima at 1.32, 1.63, 3.03, 3.47, 3.58, 4.83, 4.90

to 5.30, 5.83, 7.64 ppm.

Example 25

N-allyl-4- (t-butyl) -N-methallyl-2,6-dinitroaniline,

Oil; NMR maxima at 1.38, 1.63, 3.46, 3.57, 4.83, 4.90 to

5.28, 5.83, 7.78 ppm.

To evaluate the compounds according to the invention, the Herbicidal test methods described below carried out:

Acted on the soil in which the test plants were grown it is a mixture of equal volumes of sand and medium-weight humus. The plants were in shallow Galvanized steel bowls 35 cm long, one

509839/1052

Width of 25 cm and a depth of 8 cm drawn. The floors the trays were ribbed and perforated for drainage.

The test compound was prepared by dissolving 120 mg of the same in 2.5 ml of an emulsifying agent containing 10 g Solution in a mixture of 1 liter of acetone and 1 liter of ethanol. The 2.5 ml solution was then dissolved in 22.5 ml of water, containing 0.045% emulsifier, dispersed. The aqueous dispersion was appropriately diluted for preparation of formulations that provided the correct amounts of test compound when adding 12.5 ml of the dispersion applied to each area.

3.79 liters (1 gallon) of the mixing soil was applied to each area and leveled. Seeds of each of the test plants became seeds planted in the earth in rows perpendicular to the long axis of the plane and covered with earth. 0.47 1 (1 pint) one 2.5 g of the liquid fertilizer containing soluble fertilizer 18-25-18 was added to each area after planting.

The compound to be tested was sprayed evenly on the same day the seeds were planted of the compound dispersion on the ground is applied to the surface using an atomizing spray gun.

After the treatment, the samples (areas) were placed in a greenhouse brought, which was kept at a temperature and humidity suitable for the growth of the plants. The plants were observed 12 days after treatment

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and each of the plant species was prepared using one of Rated 1 to 5 going scale. The rating 1 indicates that the plants emerged and grew normally, and the rating 5 indicates that the plants did not emerge or died soon after emergence. The ratings 2,3 and 4 indicate weak, moderate or severe damage. The after application of the to be examined according to the invention Compounds in an amount of 0.454 to 1.81 kg (1 to 4 lbs) per acre are observed in results indicated in the table below. The compounds are identified therein by the number of the respective above Production examples designated. To remove misunderstandings are below the German names of the plants and the corresponding Latin names opposite posed.

Corn

Cotton soybean wheat alfalfa sugar beet rice

cucumber

tomato

Barn yard grass (barnyard grass)

white goosefoot large fingergrass mustard

Goosefoot Foxtailgrass Oatgrass Grieswurz Morning glory zinnia

Zea mays Gossypium hirsutum Glycine max Triticum vulgar Medicago sativa Beta vulgaris Oryza sativa Cucumis sativus Lyeopersicon esculentum Echinochloa crusgalli

Chenopodium album Digitaria sanguinalis Brassica sp. Amaranthus retroflexus Setaria sp. Avena sp.

Abutilon theophrasti Ipomea sp. Zinnia sp.

5 o a a * 9/1 ο 5

co co co

• -Λ - 3 Crops
Crops I soybean !Wheat ! ■ Alfalfa respectively. 1 ¹ cucumber ! tomato Barn
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O β O 3 finished O nkwi 1 1 φ 1 CO υ 1 2 2. unen
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I. - 3 uaz erne 2 ι ■ 1 1 ü μ
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Compound crowd in co 2 1 1 1 3 1 1 1 I ' 1* it- 3 1 3 2 No. 0.454 kg 2 3 2 1 ι · 2 3 2 k 2 3 2 2 1 per morning 1 1 1 2 3 · 3 • k 1 3 3 3 2 22 1 2- 1 1 2 2 K 2 3 1 -p- 1 1 1 3 1 3. 2 23 1 2 2 3 1 k 1 1 3 2 2lT 1 1 2 2 · I.
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The novel compounds of the present invention become the most useful as part of the herbicide treatment procedures described below used. The herbicide treatment methods of the present invention are methods for stunting the growth of weeds and preventing weed seeds from germinating on cultivated farmland, the are characterized in that there is a herbicidally effective Amount of a compound according to the invention before rising who brings weeds to the cultivated arable land. Preferred embodiments of these methods are those in using the preferred compounds given above.

As can be seen from the above data, the herbicidal treatment methods of the present invention can be performed safely are used in many economically important crops or crops, with cotton, soybeans and Sugar beets are particularly preferred. Other crops or crops in which the compounds according to the invention can be used with advantage are, for. B. potatoes, tomatoes, tobacco, onions, melons and cucumbers.

With the help of the compounds according to the invention it is possible to control many weeds that contaminate and damage the above-mentioned and other crops and crops (to be checked) as the above data shows. With the help of certain of the compounds according to the invention it is also possible to control other harmful weeds, such as. B. Solanum nigrum, Chenopodium album, Polygonum convolvulus, Datura stramonium, Portulaca oleracea, Convolvulus

5 0 9 8 3 9/1052 - 21 -

arvensis, Fumaria officinalis, Echinaciioa crus-galli, Setaria sp., Poa annua and Phalaris minor.

In general, it is most convenient to use the herbicide treatment method carry out in such a way that the compounds before planting the cultivated or harvest seeds, however, after the arable land has been prepared for planting. It is usually most effective incorporate the compound into the top layer of soil by mixing the soil with a tool, such as. B. one Tiller, a roller cultivator or a disc harrow, after the compound is applied to the arable land (cultivated field) has been. The incorporator should cut the joint in about 2 to 6 inches (5.08 to about 15.24 cm Mix in deep layer of soil.

For carrying out the herbicide treatment methods of the invention at least a herbicidally effective amount of a compound must be applied to the arable land. herbicide effective amounts are generally within the range of about 0.11 to about 4.54 kg (0.25 to 10 lbs) per acre, the preferred application rate is within the range of about 0.23 to about 1.81 (0.5 to 4 lbs) per acre. Of the However, those skilled in the art know that amounts below or above the stated range are sometimes required in order to achieve the practice of the herbicide treatment methods of the present invention get the best results.

- 22 -

509839/1052

The compounds according to the invention, those according to the invention Herbicide treatment methods and those of the invention herbicidal agents inhibit the growth of weed seedlings and the emergence of weeds to an extent that that of the respective weed species and the applied compounds according to the invention and the amounts thereof depends. In some cases, as indicated by the herbicidal test data given above, the entire weed population will be killed. In other cases only the emerging weeds are damaged or some of the weeds are killed and part is damaged. The damage to a weed seedling growing in the cultivated farmland is highly beneficial for the crop or crop, because the normally growing crop or crop does this slowly Repel growing weeds (shade out). This displacement effect of the cultivated or harvested plant is special significant in the case of a bushy crop or harvested plant, such as cotton or one from the bean family.

Although the compounds according to the invention can be applied to the cultivated arable land in pure form it is much more convenient and convenient to apply one of the herbicidal compositions of the invention. The invention herbicidal compositions contain one or more of the compounds according to the invention in combination with at least one inert carrier. The inert carriers can be liquid or solid. In the case of the inert carriers used in the herbicidal compositions are contained, and the methods for producing the herbicidal compositions may be such as them

509839/1052 - 23 -

commonly used in agriculture. To illustrate the best processes, however, the preparation of the herbicidal compositions according to the invention is based on some examples.

The compounds according to the invention are very frequently in the form of concentrated herbicidal compositions which are applied to the soil in the form of aqueous dispersions or emulsions which contain from about 0.1 to about 1% of the compound. The water-dispersible or emulsifiable herbicidal agents are either finely divided solids, which are generally known as wettable powders, or liquids, which are generally known as emulsifiable concentrates.

Herbicidal wettable powders consist of an intimate mixture of the active compound, an inert carrier and surfactants. The concentration of the active compound is typically from about 10 to about 90 %. The inert carrier is generally chosen from attapulgite clays, montmorillonite clays, diatomaceous earths and purified silicates. Effective surfactants, which make up about 0.5 to about 10% of the wettable powder, are found among the sulfonated lignins, the condensed naphthalene sulfonates, the naphthalene sulfonates, the alkylbenzenesulfonates, the alkyl su.lfaten and the nonionic surfactants such as ethylene oxide - Adducts of phenol.

- 24 -

5098Ί9 / 1052

Typical herbicidal emulsifiable concentrates of the compounds of the invention contain a suitable concentration of the active compound, e.g. B. about 0.23 to about 2.72 kg (0.5 to 6 lbs) per 3.79 liters (1 gallon) of liquid dissolved in an inert carrier which is a mixture of a water-immiscible organic Solvents and emulsifiers. The organic solvent is selected based on its solvency and cost. Suitable organic solvents include the aromatics, especially the X} roles, the petroleum fractions _? in particular the high-boiling naphthalene and olefinic components of petroleum, such as heavy aromatic naphtha. Other organic solvents can also be used, such as e.g. B. the terpene solvents, e.g. B. Rosin derivatives. The emulsifiers which make up from about 0.5 to about 10 percent of the emulsifiable concentrates are selected from the same types of surfactants as used for wettable powders.

Also suitable forms are granular herbicidal compositions, in which the compounds are simply distributed evenly of the herbicidal agent can be applied over the cultivated arable land. The herbicidal granules usually contain one Compound distributed on a granular inert carrier, which is usually coarsely ground clay. the Particle size of these granules is generally within the range of about 0.1 to about 3 mm. The usual manufacturing process is that the compound in a solvent such as kerosene or a heavy aroma

- 2 5 - 50 9 8 - 3 9/1 052

table naphtha, and apply the solution to the support in a suitable mixer. A less economical one The method consists in that the connection in a consisting of a wet clay or other carrier Spread the batter, which is then dried and coarsely ground to form the desired granular product.

The herbicidal compositions according to the invention can be used a conventional device can be applied to the cultivated arable land. For example, they are dispersed in water Means applied by means of spray devices that are hand-carried, mounted on the tractor, self-spraying or can be towed. The granular herbicidal compositions are prepared using any of the many Applicators, as they are currently in use, applied. When operating the application device only has to care should be taken to apply such an amount of the herbicidal agent per acre that the desired order quantity of the connection results, and that it is evenly applied to the arable land area.

The herbicidal compositions according to the invention can contain a compound of the formula I given above as the only active ingredient. Alternatively, they can also contain other herbicidally active substances, such as. B. Urea herbicides such as 3- (3,4-dichlorophenyl) -1-methoxy-1-methylurea, 3- (4-chlorophenyl) -1-methoxy-1-methylurea, 3- (4-bromophenyl) -1-methoxy -1-methylurea, 3- (3,4-dichlorophenyl) -1,1-dimethylurea, N'-4- (4-chlorophenoxy) phenyl-N, N-di- - 26 -

5 09839/1052

methyl urea and N ^t - (3-chloro-4-methoxyphenyl) -N, N-methyl urea; Triazine herbicides, such as 2-chloro-4-ethylamino-6-isopropylamino-l, 3,5-triazine, 4-amino-6-t-butyl-3- (methylthio) l, 2,4-triazine-5- one, 2-chloro-4,6-bis (ethylamino) -l, 3,5-triazine, 4-ethylamino-2-methylthio-6-t-butylamino-1,3,5-triazine; Phenoxy herbicides such as 4- (2,4-dichlorophenoxy) butyric acid, 4- (4-chloro-2-methylphenoxy) butyric acid and 2 - [(4-chloro-otolyl) oxy] propionic acid; Carbamate herbicides such as isopropyl N- (3-chlorophenyl) carbamate; Amide herbicides such as N- (4-chlorophenyl) -2,2-dimethylvaleramide and 2- (a-naphthoxy) -N, N-diethylpropionamide; or herbicides such as 2- (l-methyl-n-propyl) -4,6-dinitrophenolj3,5-dinitro-N, N-dipropylsulfanilamide, 5-amino-4-chloro-2-phenyl-3-pyridazone and 1- (5-t-Butyl-1,3,4-thiadiazol-2-yl) -1,3-dimethylurea, and thiol carbam herbicides such as S-ethyl-N, N-dipropylthiocarbamate.

Claims: - 27 -

509839/1052

Claims (18)

Claims 1. 2,6-Dinitroaniline, characterized by the general formula f ^H 3 RN- CH ₉ C = CH, (D where mean: R is an ethyl, propyl or allyl group and R is a C ₁ -C, -alkyl, trifluoromethyl, difluoromethyl, methylsulfonyl or sulfamoyl group. 2. 2,6-dinitroaniline according to claim 1, characterized in that in the,
group means. net that in the general formula (I) R is the trifluoromethyl 3. 2,6-dinitroaniline according to claim 1 and / or 2, characterized in that in the general formula (I) R is the ethyl group means. 4. N-ethyl-N-methallyl ^ -trifluoromethyl ^ je-dinitroaniline. 5. Process for the preparation of 2,6-dinitroanilines 5 Q 9 8 3 9/1 Π 5 2 general formula R-N- (D where mean: R is an ethyl, propyl or allyl group and R is a C ₁ -C, -alkyl, trifluoromethyl, difluoromethyl, methylsulfonyl or sulfamoyl group, characterized in that a dinitrobenzene of the general formula (II) wherein X is a halogen atom, preferably a chlorine atom, and R has the meanings given above, with an amine of the general formula - 29 - 5 CH) 8 3 9/1052 CH _Q R - NH - CH ₂ - C = CH ₂ (in) wherein R has the meanings given above. 6. The method according to claim 5, characterized in that there is a compound of the general formula wherein X has the meanings given in claim 5, with an amine of the general formula R - NH - CH ₂ - C = (III) 7. The method according to claim 5 and / or 6, characterized in that a compound of the formula is used as the amine CH ι J CH ₃ CH ₂ - NH - CH ₂ - C = CH ₂ (V) 8. Herbicidal agent, characterized in that it contains at least one 2,6-dinitroaniline of the general formula - 30 - 5098 3 9/1052 (D where mean: R is an ethyl, propyl or allyl group and R is a C ₁ -C ₄ -AlCyI-, trifluoromethyl, difluoromethyl, methylsulfonyl or sulfamoyl group, in a mixture with at least one inert carrier or diluent for it contains. 9. Herbicidal agent according to claim 8, characterized in that it contains a compound of the general formula (I), where R is the trifluoromethyl group. 10. Herbicidal agent according to claim 8 and / or 9, characterized in that it is a compound of the general formula (I) contains where R is the ethyl group. 11. Herbicidal agent according to claim 8, characterized in that it is used as a compound of the general formula (I) Contains N-ethyl-N-methallyl-4-trifluoromethyl-2,6-dinitroaniline. - 31 509839/1052 12. Herbicidal agent according to at least one of the claims 8 to 11, characterized in that it also contains a further herbicidally active substance. 13. Herbicidal agent according to claim 12, characterized in that there is 2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine as a further herbicidally active substance contains. 14. Method of inhibiting the growth of weeds and / or preventing the germination of weed seeds on cultivated land Arable land, characterized in that a herbicidally effective amount of a 2,6-dinitroaniline is added before the weeds emerge the general formula (D where mean: R is a C ₁ -C, alkyl, trifluoromethyl, difluoromethyl, methyl R is an ethyl, propyl or allyl group and a C ₁ -C, -alkyl, trifluorometal
sulfonyl or sulfamoyl group on the farmland. - 32 - 5 Π 983 9/1 Π 52 15. The method according to claim 14, characterized in that the 2,6-dinitroaniline is in the form of a herbicidal agent according to at least one of claims 8 to 13 applies. 16. Methods of inhibiting the growth of weeds and / or preventing the growth of weed seeds on cultivated land Arable land, characterized in that before the weeds emerge, a herbicidally effective amount of N-ethyl-N-methallyl-4-trifluoromethyl-2,6-dinitroaniline is added on the farmland. 17. The method according to claim 16, characterized in that a combination of N-ethyl-N-rnethallyl-4-trifluoromethyl-2,6-dinitroaniline is applied to the arable land and 2-chloro-4-ethylamino-6-isopropylanu.no-1,3,5-triazine brings up. 18. The method according to at least one of claims 14 to 17, characterized in that the crop is cotton. 509 8 39/1052