NL8202973A - HERBICIDE PHENOXYBENZOIC ACID COMPOUNDS. - Google Patents

Description

♦ * - 1 - £

Herbicidal phenoxybenzoic acid compounds.

The invention relates to certain phenoxy-benzoic acid derivatives, which contain a sulfonamide group and are useful as herbicides, especially as herbicides to control weeds in soy plantations.

Herbicides derived from phenoxybenzoic acids and their esters are well known from U.S. Pat. Nos. 3,652,645, 3,784,635, 3,789,276, 3,873,302, 3,907,866, 3,928,416, 3,983,168, 4,063. 929 and European Patent Nos. 3416 and 23,392.

The invention now relates to benzoic acid derivatives with sulfone amino groups, which have the general formula of the formula sheet, which are 15 - X 1, and X 1 each have a halogen atom, for example a fluorine, chlorine or bromine atom, a polyhalogenated alkyl group with 1-4 carbon atoms, in particular CF ^, NO ^ »CN, an alkyl group with 1-4 carbon atoms, a SO ^ alkyl group with 1-4 carbon atoms, SO ^ NH ^, NO, COOalkyl with 1 - 4 carbon atoms in the alkyl portion, - Yj is the group -N = or -CH =, - represents the group -N = or -CX, _ =, provided Y is not -N =, from Yg the group is -CX ^ = - Y ^ is an oxygen or zvav atom, - a hydrogen atom or an alkyl group with 1 to 4 carbon atoms, which is optionally substituted with in particular halogen atoms, - X ^ is a hydrogen atom or an alkali metal atom, in particular is a sodium or potassium atom, or a cationic optionally quaternary ammonium group, or an alkyl group of 1-4 carbon atoms, optionally containing in the b especially halogen atoms, or a halogen atom, especially a chlorine atom, - Xg is an optionally substituted alkyl group with 8202973

V

- 2 - is preferably 1-U carbon atoms or an optionally substituted aryl group, particularly in the phenyl group, the substituents being halogen atoms or alkyl, amino, cyano, nitro, alkoxy, hydroxy, formyl or mercapto groups are eligible, and 5-Xj is a hydrogen atom or a halogen atom.

A preferred class of the compounds of the invention is characterized by X ^ = CP ^ s Xg = »^ 3 = preferred NO ^, X = H, Na or

Cl and Y.j and Y ^ each -CH-. The process for preparing the compounds of the general formula T are also part of the invention.

According to a first embodiment of the procedure, an acid chloride of the general formula 2 is reacted with a sulfonamide of the general formula 3, the different groups and / or substituents having the meaning given in connection with the general formula 1.

The reaction proceeds advantageously at temperatures of 50-150 ° C, preferably 80-110 ° C in a solvent, such as, for example, an optionally halogenated aliphatic or aromatic hydrocarbon. The concentration of compounds of the general formulas 2 and 1 is generally in the range of 1-80%, preferably 10-30 l. Preferably, the operation is carried out in the presence of an acid lacquer septor, for example a tertiary amine, such as in particular triethrylamine and pyridine.

In the conversion between the compounds of the general formulas 2 and 3 just described, X 1 preferably does not represent a halogen atom. The compounds of the general formula 1, wherein X 1 represents a halogen atom, are generally prepared by reacting a hypohalogen not on the corresponding compound, wherein X represents a hydrogen atom. This reaction generally takes place in an aqueous medium at a pH of more than 10, preferably of more than 11.5 and at a temperature of 0-50 °. C.

The acid chloride of the general formula II is prepared in the usual manner by the action of SOCl2 on the 8202973 * * - 3 -

V

corresponding acid of the general formula

The acid of the general formula K and the sulfonamide of the general formula 3 are prepared by methods known from the literature.

According to a second embodiment of the method according to the invention, the compounds, in which no halogen atom represents, are prepared by reacting an acid of the general formula with an isocyanate of the general formula 5, wherein in the formulas the different substituents The groups have the same meaning as in the general formula 1, respectively. This reaction advantageously takes place in the presence of a solvent and preferably in the presence of a catalytic amount of an organic base. The reaction temperature is usually in the range of 20-100 ° C, preferably U0-80 ° C. The concentration of products of the general formulas I and 1 is generally 5-70% by weight.

Suitable solvents for this are aliphatic or aromatic solvents, which may be halogenated, for example benzene, toluene and xylene.

The organic base is, for example, p- (dimethylamino} pyridine.

The isocyanates of the general formula (5) can be prepared by methods known per se.

The first embodiment of the process according to the invention, in which a compound of the general formula III is reacted, is preferred when Xg is an aliphatic group. To the second method, wherein an isocyanate of the formula 5 in. reaction is preferred, when Xg is an aromatic group.

The compounds of the general formula 1, wherein X 1 represents a hydrogen atom, can be converted in the known compounds, in which X 1 is an alkali metal atom, in known manner, into the compound without the aid of the methods used on the known derivatives of 8202973 • »

V

k-phenoxybenzoic acids with sulfonic acid groups can be used.

The invention is now illustrated with the following examples:

Example I

3 g (6.9 mmol) of 1- (1-carboxyethyl) 5/2-chloro-U-trifluoromethylphenoxy / 2-nitrobenzoate are dissolved in 15 ml of toluene, which contains 2 g of thionyl chloride.

The solution is refluxed for one hour and then cooled. The solvent and excess thionyl chloride are distilled off under reduced pressure. The residue is taken up in 25 ml of tetrahydrofuran. 0.9 g of methanesulfonamide (CH2 SO2 NH2) and a catalytic amount (about 5 Dig) of p-dimethylaminopyridine are added. A further 10 ml of a solution of 0.77 g of triethylamine in vessel-free tetrahydrofuran are added dropwise. When everything has been added, the mixture is stirred for an additional 2 hours, 50 ml of tetrahydrofuran is added again, and the solution is fixed twice with 25 ml of 5% aqueous hydrochloric acid each and with brine. It is then dried over magnesium sulfate, filtered and the solvent is filtered off under reduced pressure.

The residue is purified by chromatography using a SiO 4 column (solvent 10% acetic acid in CHCl 4). 0.5 g of the compound of the formula VI are obtained.

25

Example II

150 ml of a solution of 50 g (261 mmol) of p-toluenesulfonyl isocyanate in toluene are added dropwise and with stirring to 350 ml of a solution of 100 g (239 of 30 mmol) carboxymethyl 5- / 2-chloro U- (trifluoromethyl) phenoxy / 2-nitro benzoate and a catalytic amount (about 5 mg) of p- (dimethylamino) pyridine in toluene. When everything has been added, it is boiled in a reflux condenser for 6 hours. It is then cooled and the solvent is distilled off in vacuo. A crude compound is obtained, which is recrystallized from 8202973 *.

V

- a mixture of toluene and hexane. 115 mg (209 mmol) (U-methylphenyl) sulfonylaminocarbonylmethyl 5- / 2-chloro (trifluoromethyl) -phenoxy / 2-nitrobenzoate of the formula 7 are obtained.

He melts this compound at about 130 ° C and 5 shows infrared. absorption bands (in KBr) at 3205, 1705 and. 1580 cm-1.

In the nuclear magnetic resonance spectrum (recorded in CD ^ -CO-CD ^ with tetrametbylsilan as standard), peaks were found at 2.35 ppm (singlet for 3 protons), 5 ppm 10 (singlet for 2 protons) and 7 »3- 8.5 ppm (multiplet for 10 protons).

Figure III

The sodium salt of the compound is obtained

15 from example II (group N-Na), from which one is described in example II

obtained compound in vessel-free tetrahydrofuran reacts with sodium hydride. The solvent is then distilled off in vacuo. The infrared spectrum shows absorption bands -1 at 1600 and 1735 cm.

20

Example Illb

Starting from the compound of Example 1 and proceeding in the same manner as in Example III, the sodium salt (group H-Na) is obtained.

25

Example IV

The procedure is as in Example II, but now carboxyethyl 5- / 2-chloro (trifluoromethyl) phenoxy / 2-nitrobenzoate is reacted with p-toluenesulfonyl isocyanate. 0.3 g of the compound of formula 8 are obtained. In the infrared spectrum an absorption band is found at 1690 cm 2. In the nuclear magnetic resonance spectrum, chemical shifts (indicated in ppm) of 13h2 (doublett, corresponding to 3 protons, coupling constant = 1¾ Hz) 35 2, U (singlet corresponding to 3 protons), 5 »2 ^ are observed. (quadruplet 8202973 - 6 -

) V

corresponding to 1 proton; coupling constant = 14 Hz), 7.2 - 8.2 (multiplet corresponding to 10 protons).

Example Y.

Example 1 is repeated, but carboxymethyl 5- / 2-chloro H-trifluoromethylphenoxy / 2-nitrobenzoate is now started from.

1 g of an oil consisting of the compound of the formula 9 are obtained. This formula was confirmed by the infrared and nuclear magnetic resonance spectrum.

10

Example VI

Example V is repeated, but now the methanesulfonaraide is replaced by CH2 -SO2 -HH-CH2. The mixture is heated for a total of 89 hours. 3 g of an oil consisting of the compound of the formula 10. This formula was confirmed by the infrared and nuclear magnetic resonance spectra.

Example VII

In containers of 20 x 25 cm, which were filled with soil, weeds and weeds were sown in rows of 10 cm long. The plant species used are listed in Table A.

For cotton, corn, soy and burdock, ^ -5 grains were laid out per row and the smaller varieties - mallow, 25 white mustard, loosestrife, hawpoot and green needle - were sown without counting the seeds, but in sufficient number to subsequently row close to each other to obtain plants.

Until the germination of the plants, the soil was supplied with water from above. Pre-germination treatment followed less than 1 day after sowing.

The desired development stage for the post-germination treatment of cotton, soy, burdock, mallow, wild mustard and goosefoot is the stage at which 1 real leaf 35 and 1 real trifold have formed. The corn plants 8202973 * * - 7 - had a height of 7-5-10 cm at the desired stage. With the other grass plants, on the other hand, the desired height was 2.5 cm,

The compounds according to the invention are sprayed under a pressure of 0.25 MPa in an amount of 375 l / ha.

The spraying agents consisted of a mixture in volume parts corresponding to 20 ml of water and 0.1% surfactant (mixture of a polyoxyethylene ether and alkali (6-6 -alkylbenzene sulfonates)).

After the treatment, the water was added from below to the plants that had already sprouted and from above to the seed grains that had not yet opened.

Two weeks after the treatment, the activity determinations were made on a scale of 0-100%. In the weeds this scale meant a degree of destruction.

In the useful crops, this scale means the extent to which the plaids are engaged by the active substances and their plant toxicity, respectively. The value 0 is attributed to the plants, which are in the same condition as the 20 blank plants. The value 100 corresponds to one with full cancellation.

Table B summarizes the results achieved with the compounds of Examples I-VI.

Example VIII

Pre-germination treatment of the plants

Large pots of 9 x 9 x 9 cm are filled with light arable soil and a number of seeds are sown, the number of which depends on the nature of the plant to be tested and the thickness of the seed grains.

The seed grains are covered with an approximately 3 mm thick layer of earth. After the soil has been moistened, the pots are sprayed with an amount corresponding to a chemical required amount of 500 l / ha.

35 The spray contained the substance to be tested in the desired concentration. 8202973 - 8 -

V

tration.

The spray was prepared by diluting a wettable powder. The wettable powder, in turn, consisted of 5 g of active ingredient, 83 g of xylene, 8 g of nonylphenol-5 decaoxyethylene and 1 g of calcium dodecylhenzenesilphonate. A1 depending on the active substance concentration of the spray, the applied dose of active substance was 0.25-2 kg / ha.

The treated pots were then set up in vats and received the necessary water from underneath and were kept at 70-22 ° C under 70% relative humidity for 10 days. After 21 days, the number of surviving plants in the treated pots was counted, as was the number of surviving plants in the blank pots, which were treated with a spray without active substance under the same conditions, for comparison. In this way, the percentage destruction of the treated plants was determined, with respect to a blank test without active substance. A degree of destruction of 100% means that the plant species considered has been completely destroyed. 0% eradication means that the number of surviving plants in the pot treated with active substance was equal to the number of plants in the blank test.

Example IX

Post-germination treatment of plants In 9x9 / 9 cm3 pots filled with soft arable soil, seeds were sown, in a number depending on the type of plant used and the thickness of the seed grains.

The seed grains were covered with an approximately 3 mm thick layer of earth and the seed grains were allowed to germinate until the plants reached a height of 5-10 cm.

Then the pots were sprayed in an amount corresponding to a required amount of 500 l / ha. The spray contained the active ingredient at the desired concentration and was prepared in the same manner as 8202973 * 9 in Example VIII.

A1 depending on the active dust concentration in the spray, the applied active dust dose was 0.125-1 kg / ha.

The treated jars were then placed in tubs, which were watered from below, and kept at 22-200 ° C under 70% relative humidity for 1¾ days.

After 1¾ days the number of surviving plants in the pots treated with the spray is counted and 10 is compared with the number of plants that were present in a pot treated on the same soil, without active substance. In this way, the percent destruction of the plants with respect to a hlanko test was determined. 100% extermination means that the reviewed plant species was completely destroyed and 0% extermination means that the number of surviving plants in the treated pot were identical to the number of plants in the hlanko pot.

The results of Examples VIII and IX are summarized in Tahel C and D.

Each of these tahelles C and D comprises, on the one hand, the pre-germination data according to Example VIII and, on the other hand, the post-germination data according to Example IX.

Tahel C represents the results achieved with the active ingredient of pre-II, while D represents the results achieved with the active ingredient of pre-V

The tests carried out thus show the advantageous properties of the compounds according to the invention in the treatment of crops and, in particular, soya and cereals including corn, as well as in the pre-germination as well as the post-germination treatment.

In the case of soy, the activity of the compounds of the invention is particularly interesting when the soy plantations of bivalve weeds such as mallow, burdock, dayflower and bindweed suffer. In the case of cereals, the activity of the compounds is particularly interesting, since the cereal cultures suffer from bilobed weeds, in particular goosefoot, loosestrife, high ambrosia, bindweed, chrysanthemum, wild mustard and in particular wall and cleavers.

In practice, the compounds of the invention are rarely used alone. They are usually part of herbicides. These herbicidal agents contain as active substance a compound according to the invention as described above in combination with the agricultural compatible solid or liquid carriers, as well as surfactants. In particular, the inert and conventional carriers are suitable and the usual surfactants. These means are also part of the invention.

These agents may also contain any other components, such as protective colloids, adhesives, thickeners, thixotropic agents, penetrants, stabilizers, scavengers and other agents as well as further known active substances with harmful organisms, especially insecticides, fungicides. and herbicides or with properties that favor plant growth, especially fertilizers or with plant growth regulating properties. In general, the compounds according to the invention can be combined with all solid and liquid additives which are usual for the preparation of agents against harmful organisms.

The application doses or amounts required for the compounds according to the invention can vary within wide limits and depend mainly on which weeds are involved and to what extent the plantings of the crops usually suffer from this. In general, the agents of the invention contain 0.05-95 wt% of one or more of the active substances of the invention, 1-95 wt% of one or more solid or liquid carriers, and optionally 0.1-20 wt% of one or more surfactants.

As already mentioned, the compounds according to the invention are generally combined with carriers and optionally with surfactants.

By carriers in the present description are meant organic and inorganic substances of natural or synthetic origin, with which the active substance is combined, after its application to the plants, to the seeds. or on the bottom. These carriers are therefore generally inert and must be tolerable for the landscaping, especially for the treated plants. The carriers can be solids such as: clays, natural or synthetic silicates, silicic acid, resins, waxes, solid fertilizers and the like; or it is liquid such as "water, alcohols, in the butanol, esters, in particular methyl glycol acetate, ketones in particular cyclohexanone and isophorone, petroleum fractions, aromatic hydrocarbons, in particular the xylenes or paraffinic hydrocarbons, aliphatic chlorinated hydrocarbons, in particular trichloroethane or aromatic chlorohydrocarbons, in particular the chlorobenzenes, water-soluble or water-miscible solvents such as dimethylformamide, dimethylsulfoxide, N-methylpyr roll don, liquefied gases and the like.

The surfactant can be an emulsifying agent, a dispersing agent or a wetting agent, as well as ionic or nonionic or a mixture of such agents. Examples of these are the salts of polyacrylic acids, the salts of lignosulfonic acids, salts of phenol sulfonic acids or naphthalene sulfonic acids, polycondensation products from ethylene oxide and fatty acid alcohols or fatty acids or fatty acid amines, substituted phenols, especially alkyl phenols or aryl phenols, salts of ethyl ester of sulfosuccinic acid taurates, esters from phosphoric acid and alcohols or polyoxyethylated phenols, esters from fatty acids and polyols, as well as the derivatives of the above compounds with sulfate, sulfonate and phosphate groups. The presence of at least one surfactant is generally necessary if the active substance and / or the inert carrier are not water-soluble and water is required as an aid to the application.

Thus, compounds of the general formula I can be used in the form of preparations which can have very different solid or liquid forms.

Examples of solids are spray powders with a compound content of the general formula 1 to 100% and granulates, in particular. those obtained by extrusion, by pressing by impregnation of a granulated carrier or granulation from a powder. The compound content of the general formula 1 in these granulates is 0.5-80% in the latter cases. The solids usually contain 20-80% active substance.

Examples of liquid agents, ie agents which are liquid in use, are solutions, in particular emulsifiable concentrates, emulsions, concentrated suspensions, aerosols, wettable powders or spray powders, self-dispersible granules and pastes.

The liquid agents usually contain 10-80% active substance.

The emulsifiable or soluble concentrates usually contain 10-80% active substance. The finished emulsions or solutions contain 0.01-20% active substance. In addition to the solvent, the emulsifiable concentrates may contain, if necessary, 2-20% suitable additives, for example, stabilizers, surfactants, penetrants, corrosion inhibitors, dyes and adhesives.

Starting from these concentrates, emulsions or solutions of any desired concentration can be prepared by dilution with water, which are particularly well suited for use on plants.

The following are some examples of the compositions of emulsifiable concentrates: a) active substance 250 g 35 polyethoxylated alkylphenol 30 g 8202973 -13- calcium alkylarylsulfonate 50 g

petroleum fraction, which at 160-185 ° C

boils 670 g 5 b) active substance 350 g polyethoxylated castor oil 60 g sodium alkylarylsulfonate 1) 0 g cyclohexanone 150 g xylene 1) 00 g 10 c) active substance 1) -00 g polyethoxylated alkyl phenol 100 g ethylene glycol methyl ether 250 g aromatic petroleum 160-185 ° C boils 250 gd) active substance 1) -00 g polyethoxylated tristyrene phenol phosphate 50 g 20 polyethoxylated alkyl phenol phosphate 65 g sodium alkylbenzenesulfonate 35 g cyclohexanone 300 g aromatic petroleum fraction with boiling point 160-185 ° c 150 g 25 e) active substance U00 g / 1 alkyl dodecylbenzene sulfonate 2b g / 1 oxyethylated nonylphenyl with 10 ethylene oxide units 16 g / l 30 cyclohexanone 200 g / l supplemented with aromatic ·. solvent to 1 l f) active substance 250 g of 35 epoxidized vegetable oil. 25 g 8202973 -11 + - mixture of alkylarylsulphonate and polyglycol fatty acid ether 100 g dimethylformamide 50 g xylene 575 g 5

The concentrated suspensions, which can be sprayed, are prepared in such a way that a stable, flowable product is obtained, because the individual components do not settle (fine grinding). Side 10 usually contains 10-75% active agent, 0.5-15% surfactant, 0.1-10% thixotropic agent, 0-10% further additives such as anti-foaming agent 1, corrosion inhibitor, stabilizers, penetrants and adhesives and as lower water or an organic liquid in which the active substance has little or no solubility. Certain organic solids or inorganic salts can be dissolved in a carrier to further prevent deposition or serve as an antifreeze for the water.

An example for suspension concentrate now follows.

active ingredient 50 g polyethoxylated tristyrylphenol phosphate 50 g 25 polyethoxylated alkyl phenyl 50 g sodium polycarboxylate 20 g ethylene glycol 50 g organopolysiloxane oil (anti-foaming agent) 1 g polysaccharide 12.5 g 30 water 316.5 g

The wettable powders and spray powders are usually prepared so as to contain 20-95% active substance, as well as in addition to the solid carrier, 0-5% of a wetting agent, 3-10% of a dispersing agent 8202973-15. and, if required, 0-10% of one or more stabilizers and / or other additives such as penetrants, adhesives or lump reducing agents, dyes and the like. Now according to some examples 5 of such wettable powders: a) active substance 50% calcium ligno sulphonate, flocculant 5% 10 isopropylnaphthalene silphonate, anionic humectant 1% silicic acid to reduce lump formation 5% kaolin, filler 39% 15 b) active substance 80% sodium alkylnaphthalene sulfonate 2% sodium lignosulfonate. 2% silicic acid to prevent lumps from forming 3% kaolin 13% c) active substance 50% sodium alkylnaphthalene sulfateate 2% 25 methyl cellulose of low viscosity 2% diatomaceous earth b6% d) active substance 90% 30 sodium dioctyl sulfosuecinate 0.2% synthetic silica 9 .8% e) active substance U00 g sodium lignosulfonate, 50 g 35 sodium dibutylnaphthalene sulfonate 10 g 8202973 -16-silicic acid 5 ^ -0 gf) active substance 250 g isooctylphenoxy polyoxyethylene ethanol 25 g 5 mixture of equal parts Champagne chalk and hydroxyethyl cellulose 17 g sodium aluminum -3 g silicic acid 165 g 10 g) active substance 100 g mixture of sodium salts of saturated fatty acid sulphates 30 g condensation product of naphthalin sulfonic acid and formaldehyde 50 g 15 kaolin 820 g

To prepare this spray powder or wettable powder, the active substance is thoroughly mixed with the further additives in corresponding mixers or the porous carrier is impregnated with the molten active substance or the whole is ground in mills or other suitable crushing facilities. Spray powders are obtained in this way, which are advantageously wettable and can be brought into suspension. They can be suspended in water at any desired concentration and these suspensions are particularly well suited for application to the leaves of plants.

The "dry flowable" granules have a composition essentially similar to that of the wettable powders. They can be prepared by granulation of the compositions described for the wettable powders or by the wet way, ie by contacting the finely divided active substance with the inert carrier or filler and with a little water, for example 1-20%. , or by contacting the particulate active agent with the aqueous solution of the dispersant or binder and 8202973-1T- then drying and sieving, or also by dry pressing and subsequent grinding, and reactive grinding and sieving.

The following is an example of a self-dispersible granulate: active substance 800 g sodium alkylnaphthalene sulfonate 20 g sodium methylene bis-naphthalene-10 sulfonate 80 g kaolin 100 g

Instead of wettable powders, pasta can also be prepared. The conditions and variations of the preparation and use of these pastes are the same and comparable, respectively, to those for the wettable powders and spray powders, respectively.

As already stated, the aqueous dispersions and the emulsions 5 are, for example, the agents obtained by diluting a wettable powder or an emulsifiable concentrate with water, which are intended to be used according to the invention. The emulsions can be water-in-oil or oil-in-water emulsions and have a thick mayonnaise-like consistency.

These aqueous dispersions or emulsions or spray mixtures can be applied to the cultures or plantings, respectively, which are to be weeded, by any suitable means, generally by spraying or sputtering in dosages generally of the size in the order of 100-120 1 spray per hectare.

The granules which are used for the soil treatment are generally manufactured in such a way that their dimensions are 0.1-2 mm. They can be produced by agglomeration or impregnation. Preferably the granulates contain 1-25% active substance as well as 0-10% additives such as stabilizers, delayed active agents, binders and solvents such as 8202973-18.

An example of such a granulate follows.

5 active substance 50 g propylene glyeol 25 g clay (grain size 0.3-0.8 mm) 925 g 10. The agents according to the invention are used for accidental destruction in cultures, especially in cereal plantations, such as wheat plantations, as well as in soy. For this purpose, an effective and non-toxic amount of terminate one of the compounds according to the invention is applied to the plants and / or to the soil of the area to be cleared of weeds. These compounds are used in practice in the form of the above-described herbicidal compositions according to the invention. In general, active material quantities of 0.01-5 kg / ha, preferably of 0.1-2 kg / ha, lead to good results, the choice of active material quantity to be applied, of course, depending on the problem to be solved, of climatic conditions and of the crops under consideration. The treatment can be carried out either before the germination of the crops and the weeds or for the sowing of the crops at the bottom of the soil effect, which acts in the soil are thus an additional measure in the treatment according to the invention, or can be carried out after germination. Other treatments are also eligible. For example, it is possible to apply the active substance to the soil with or without working through and to mark off the crop plantation.

With the compounds according to the invention it is thus possible to treat both annual and perennial crops. In the latter case, the active substances are preferably localized, for instance arranged in the rows between the crops.

8202973 -19-

Table A

Case:

Maize MA

Cotton BW

Wheat WE

5 Rice RE

Soy SO

Weeds:

Cinnabar Echinochloa crus-galli EC

10 ...

Giant needle needle Setana fabern SP

Green needle needle Setaria viridis SV

Blood millet. Digitaria sanguinalis DS

Mallow AbutiIon theophrasti AT

German hay millet Setaria italica SI

^ ^ Burdock Xanthium XP

Wild mustard Sinapis arvensis SA

Loosestrife Amaranthus retroflexus AR

Dayflower Ipomea purpurea IP

Needle nose Sida spinosa SS

pn

Got Avena fatua AP

Bindweed Polygonum convolvulus PC

Ambrosia Ambrosia artemisiifolia AA

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Tab el C

_Pre-germination ..... Haontkleaiing_

Dose in kg / ha 2 1 0.5 0, 25 1 0 * 5 0.25 0.125

Kvreekgras_90 50 20 0

Millet_ί00 100 100 100 _

Hanepoot_100 100 100 90 50 20 0 0

Magic grass 100 100 100 100 80 80_0_0

Blood millet 100 100 100 100 100 90 10 0

Waive_100 100 100 60 100 80 50 20

Elis_100 0 0 0 100 100_100

Goosefoot_100 100 100 100 100 80 80 30

Loosestrife 100 100 100 100 100 100 100 90 ambrosia_100 100 100 90 100 90 90 20

Wind_100 100 100 100 100 100 100 90.

Dagbloem_100 50 100_100

Needle nose_100 100 100 100 100 100 100 90

Cleavers 100 100 90 80 90 50 20 0

Foxtail_90 80 20 10_0 0_0_0

Green needle 100 100 100 100 100 90 10_0

Giant green needle needle_100 100 100 100 90 60 20 0

Chrysantium 100 100 100 90 100 100 100 100

Wild mustard 100 100 80 80 100 100 100 100 jWall_100 100 100 100 80 20 0_0

Wheat_0_0_0_0_10 0_0_0

Barley_10 10 0 0 10 0 0_0

Mais_JO_0_0_0_0 0_0_0.

Cotton_0_0_0_0_

So.ja_30 0 0 0 60 0 0 0 8202973 -22-

Tab el D

_ Pre-germination Post-germination_

Dose in kg / ha 2 1 0.5 0.25 1 0.5 0.25 0.125

Cleavers 100 100 100 60 100 90_g0_90 G-roene needle- ear_9020_20_0

Cinnabar _; _ 60 10_10_0

Magic grass_90 20_20_10

Blood millet _ "_ ^ 40 ^ -0__20

Malve_90 50 10_0_

Klis_100 100 100

Goosefoot_100 100 100 100 100 100 100_80

Loosestrife _100 100_100

Ambrosia_100 100 100_100

Wind_100 100 100 100 100 100 100 100

Dagbloem_100 100 100 100

Needle nose_1G0_90

Oot_80 20 0 0_

Foxtail_90 30 50 0_

Sowing grass_100 30 0 0_

Giant needle needle 100 100 100 100_80_10_0

Chrysanthemum 100 100 100 100 100 100 100 100

Wild mustard 100 100 100 100 100 100 100 100 V [hr_100 10_0 0 _

Wheat 30 10 0 0 20 0 0 0

Barley_10 10 0 0 20 10 0 0

Maize _ [_ 0_0_0_0 8202973

Claims (12)

10. X ^ represents a hydrogen atom or an optionally substituted alkyl group, - X_ represents a hydrogen atom or an alkali metal atom or a cationic, optionally quaternary ammonium group, or an optionally substituted alkyl group, or a halogen atom, - Xg represents an optionally substituted alkyl group or optionally substituted aryl group, in particular an optionally substituted phenyl group, and - is a hydrogen atom or a halogen atom. Compounds according to claim 1, characterized in that = CF ^, X ^ = Cl, X ^ = Cl or X ^ = H, Ha or Cl, and Y1 and Yg are the group -CH =. 3. Compounds according to any one of claims 1 or 2, characterized in that the alkyl group or alkyl groups they carry have 1-1 + carbon atoms. 1+. Compounds according to any one of Claims 1 to 3, characterized in that X 1 is substituted with halogen atoms and / or X 6 with halogen atoms or alkyl, amino, cyano, nitro, alkoxy, OH, formyl mercapto groups. Process for the preparation of compounds According to any one of the claims 1-1 +, characterized in that an acid chloride of the general formula 2 is reacted with a sulfonamide of the general formula 3, in addition to the various 8202973 s. substituents and groups, respectively, have the meanings set out in claims 1-1 +. Process according to claim 5, characterized in that the temperature is 50-150 ° C, preferably 80-110 ° C, that one is in a solvent and at a concentration of compounds of the general formulas 2 and 1 in the range of 1-80 wt%. Process for the preparation of compounds according to any one of claims 1 to 4, characterized in that an acid of the general formula U is reacted with an isocyanate of the general formula 5S, the different substituents and groups respectively being in the claims 1-1 + have indicated meanings. 8. Process according to claim 7, characterized in that the reaction is carried out at 20-100 ° C, preferably 1 + 0-80 ° C in a solvent and at a concentration of compounds of the general formulas 1+ and 1 from 5-70 wt%. Herbicide preparations, characterized in that they contain, as active substance, a compound according to any one of claims 1-1 + in combination with at least one inert carrier acceptable in agriculture. 10. A composition according to claim 9, characterized in that it contains 0.05-95% by weight of active substance. 11. Compositions according to any one of claims 9-10, 25, characterized in that they are liquid and contain 10-80% active substance. Preparations according to any one of claims 9-10, characterized in that they are solid and contain 20-80% active substance. Preparations according to any one of claims 9-12, characterized in that they contain 0.1-20% surfactant. • 11 +. A method of weed-killing in plantations, characterized in that a refrigerated and non-toxic amount of a preparation according to any one of claims 9-13 is non-beneficial to the beneficial plants. characterized in that the planting is a soy plant, which may suffer from or already suffers from at least one of the weeds mallow, burdock, day flower or wall. Method according to claim 1U, characterized in that the planting is a grain planting, which may suffer from or already suffers from at least one of the uncured goosefoot, loosestrife, ragweed or wall. 17. Process according to any one of claims 1h-16, characterized in that a compound of the general formula 1 is used in an amount of 0.1-2 kg / ha. 15 8202973