CS18891A2 - As herbicide active substituted derivative of sulfonyl-urea and method of its preparation - Google Patents

Description

ItWT JOfifcPetr KALENSKf

The herbicidally substituted substituted method of its preparation

The invention relates to a herbicidal composition and to a process for its preparation.

Background Art

The herbicidally active derivatives of the active sulfonyl-sulfonylurea derivative are generally known compounds.

Known sulfonylureas are characterized in that the nitrogen in the 3-position substituted by a heterocyclic group has a hydrogen atom or a C 1 -C 4 alkyl group, preferably a methyl group, or a C 1 -C 4 alkoxy group, preferably a methoxy group, or an alkenyl group. C 2 -C 8, C 2 -C 4 alkynyl or aralkyl. Other substituents have been published at a surprisingly low number, and there are few patent claims that would relate to such derivatives. A sulfonylurea of the type is described, for example, in European Patent No. 142378 and Japanese Patent Publication No. J5 8126872 and J6 0078981.

The sulfonylureas have excellent herbicidal action on the dicotyledonous weed plants, especially broadleaf plants and weed grasses. Green and Coib: Prcc. S.Weed Sci. Soc. 34, 214 (1981), particularly in wheat and barley. Their advantage is their effectiveness in very low doses, generally 5 to 50 g / ha. The disadvantage is that, according to their use, the cultivated plants are also damaged to a greater or lesser extent. Therefore, in practice, it is appropriate to use antidote in cereal crops and especially in corn crops. According to European Patent Specification No. 12746? antibodies / an- ΡΛ'ρ tip / t k & „" are / are given prior to the protection of wheat and millet from the adverse action of the sulfonylurea herbicidal compositions

2 new type. Most preferred is methyl-N-aminocarbonyl-aminosulfonyl-7-benzoate and its ammonium salt, as well as ethyl-3- [aminocarbonyl] aminosulfonyl-7-thiophenecarboxylate.

According to U.S. Pat. No. 4,334,349, 1,8-naphthalanhidide, [cyanomethoxyimino] benzeneacetonitrile or .beta.-diallyldichloroacetamide, can be used with the advantage of increasing the selectivity of the herbicidally active 2-chloro-N- (74-methoxy-6-). Methyl-1,3,5-triazin-2-yl-aminocarbonyl-7-benzenesulfonamide, 2,5-dichloro-N - (4 ', 6'-dimethoxy-pyridin-2-yl) -aminocarbonyl-7-benzenesulfonamide or 2-carbamoyl-7-benzenesulfonamide methoxy-N - [(4,6-dimethylpyrimidin-2-yl) aminocarbonyl] -2-benzenesulfonamide.

SUMMARY OF THE INVENTION It is an object of the present invention to provide herbicidal compositions containing novel active ingredients which have more favorable chemical and physical properties, as well as the sulfonylurea derivatives as the active ingredient together with glycine derivatives. higher selectivity and lower retention of alignment with known sulfonylureas.

SUMMARY OF THE INVENTION

SUMMARY OF THE INVENTION The present invention relates to novel herbicidally active substituted sulfonylureas having the general formula Derivatives

AND

(1) wherein a hydrogen atom, a halogen atom, an alkoxy group having 1 to 4 carbon atoms, a haloalkoxy group having 1 to 4 carbon atoms, an alkylsulfonyl group having 1 to 3 carbon atoms or a group of the formula COR & R 2 is hydrogen, alkyl and 1 to 3 carbon atoms or phenyl,

R 1 is (C 1 -C 6) alkyl, (C 3 -C 6) alkenyl, (C 1 -C 3) alkoxyalkyl, (C 2 -C 4) alkyl substituted by one or more halogen atoms or benzyl (R) R @ 1 and R @ 6 are each independently C1 -C4 alkyl, C1 -C4 alkoxy, halogen, C1 -C3 alkylamphamoyl or (C1 -C3) alkyl alkylamino or C1 -C3 alkylthio; 3 carbon atoms,

R @ 8 is (C1 -C4) alkoxy, (C3 -C6) alkenyloxy, (C3 -C6) alkoxyalkyl, (C1 -C3) alkylamino, (C1 -C3) alkylamino; , piperazinyl or morpholinyl, X is oxygen or sulfur and E is a methine or nitrogen atom of an alkali metal, alkaline earth metal, amine or quaternary ammonium salt thereof.

The invention also relates to herbicidal compositions comprising said substituted sulfonylureas of the general formula and optionally together with antidotes.

The invention also relates to a process for the preparation of substituted sulfonylurea derivatives of the general formula I, wherein the symbols are as defined above.

Alkyl groups are always straight-chain or branched-chain alkyl groups such as methyl, ethyl, propyl, isopropyl and isomeric butyl groups.

Alkoxy groups in each case are methoxy, ethoxy, propoxy, isopropoxy or any isomeric butoxy group, especially methoxy, ethoxy and propoxy.

Alkenyl groups include, for example, allyl, isopropenyl, 1-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-isobutenyl or pentenyl, especially allyl and 4-pentenyl.

Halogen is in each case meant the halogen atom or haloalkoxy group, for example, fluorine, chlorine or bromine, especially chlorine.

Alkali or alkaline earth metal salts of the compounds of formula (I) include potassium, sodium, magnesium, or calcium, which are used in the form of a hydroxide, especially sodium hydroxide or potassium hydroxide, to form salts.

The amines used to form salts of the compounds of formula (I) include primary, secondary or tertiary amines,

Such as, for example, methylamine, ethylamine, propylamine, isopropylamine, any of the four isomeric butylamines, dimethylamine, diethylemine, isopropylamine, diisopropylamine, pyrrolidine, piperidine, morpholine, trimethylemine, pyridine, quinoline or isoquinoline, especially isopropylamine and diethanolamine.

Quaternary ammonium bases useful in the addition of the salts of Formula I include, for example, tetraethylammonium, triethylbenzylammonium, trimethylbenzyl ammonium halide, or any of the tetrabutylammonium halides. Surprisingly, it has been found that the herbicidal compositions containing the novel sulfonylurea derivatives of formula I, characterized in that the nitrogen at the 3-position of the sulfonylurea moiety substituted with a heterocyclic group carrying the formula j is R2 - CH - OR3 where a R 1 are as defined above, exhibit enhanced activity. and meet the above requirements.

It has been found that the herbicidal compositions containing the novel compounds of the formula I, where the individual symbols of the above-mentioned meanings are particularly useful for destroying large plants, since they have excellent herbicidal action at appropriately low doses and are suitable for selective cultivation. or selectivity may be provided by the use of known antidotes / antibodies, and these novel compounds are readily degradable in the soil.

The invention also relates to a process for the preparation of said novel compounds of the formula I in inert organic solvents or in mixtures thereof. In this way, the

and / or reacting the isocyanate or isothiocyanate of formula IV

wherein Rj is as defined above, with an aminopyrimidine or an aminotriazine derivative of Formula III

and; £ / ni / |

! .V &amp; wherein I < 2, R &lt; 6 &gt;, R &lt; 1 &gt; for general formula (I), optionally in the presence of a base as catalyst, at 0 ° C, preferably at 20 to 30 ° C, or

b.) The general formula (V) salfonylcarbamate derivative is reacted

(V) wherein R 1 is as defined above for formula I and R is phenyl, with an aminopyrimidine or amidriazine derivative of formula III wherein R 2, R 6, R 6, R 6 and E are as defined above, at a temperature of 25 to 120 ° C, preferably at 60 to 90 ° C;

c) reacting the carbamoyl chloride of formula VI

wherein R 2, R 4, R 4 and E are as defined above, with an alkali metal salt of sulfone.

amide of formula II

/ 11 /?

Wherein R i is as defined above for formula I, in the presence of a base as catalyst and at a temperature of -10 to 50 ° C, preferably 0 to 50 ° C, or

d) reacting N-pyrimidinylcarbamate or N-triazinylcarbamate of formula VII

wherein R 3 and R 4 are as defined above and wherein R is phenyl, with sulfonamide of Formula II wherein R 1 is as defined above for Formula I, in the presence of a catalytic amount of base at a temperature of 20 to 80 ° C, preferably at 20 to 40 ° C;

e) reacting the sulfonyl chloride of formula VIII

(VIII) wherein R 1 is as defined above for formula (I) with an aminopyrimidine or aminotriazine derivative of formula (III) wherein R 1, R 4 and R 4 are as defined above with alkali metal cyanates at 20 to 120 ° C, preferably at 60 to 90 ° C.

Optionally, the compounds of general formula (I) prepared by one of the aforementioned methods can be converted by their action of alkali metal hydroxides or alkaline earth metals, amines or quaternary ammonium halides, for example by reacting the desired compound with a suitable base in a suitable solvent, which is then evaporated. The following solvents can be used as inert organic solvents in the preparation of compounds of formula I, although this should not be construed as limiting: methylene chloride, chloroform, carbon tetrachloride, dichloroethane, trichloroethane, tetrahydrofuran, acetonitrile, dioxane, ben -zen, toluene, xylene, chlorobenzene, dimethylformamide, nitromethane, nitroethane, N-methylpyrrolidone, dimethoxyethane, diethyl ether, diisopropyl ether, dibuttylether, hexane, petroleum ether, ethyl acetate, butyl acetate, dibutyl phthalate as well as also mineral and vegetable oils. In the aforementioned possible ways of preparation, the reaction temperature in the wide range should be -20 ° C to the boiling point of the solvent used; however, it is preferable to react the reaction component at a temperature of 0 to 90 ° C and especially at a temperature of 15 to 45 ° C, since this temperature range is also suitable for temperature-sensitive derivatives of the compounds of the formula I. The reaction is preferably carried out under ambient pressure, but a higher or lower pressure may equally be used. The reactions can be carried out in the presence of air or in an inert gas environment, for example in a nitrogen atmosphere.

Several drops of base as catalyst can be used to reduce the reaction time or to terminate the reaction. Particularly tertiary amines, such as triethylamine, tribethylamine, ty, Ν-dimethylaniline, as well as nitrogen-containing heterocyclic compounds such as pyridine or 1,4-diazabicyclo [72.2.2] octane, can be used as catalytically active bases. (DABCO), although alkali metal hydroxides or alkali metal alkoxides such as sodium hydroxide or sodium methoxide are also useful for this purpose. However, the catalysts useful in the above-mentioned variations of the preparation method are not limited to the above list.

The products prepared by the above-mentioned preparation process variants can be isolated by complete or partial evaporation of the solvent and recrystallization; or by triturating the evaporation residue with a solvent or a solvent-dissolving solvent mixture. Optionally, the compounds obtained can be purified by chromatography on a suitable medium such as alumina or silica gel.

The herbicidal compositions of the present invention comprise a generally active compound of the formula I in which the individual symbols are as defined above in an amount of 0.01 to 95% by weight, preferably 2 to 80% by weight. These compositions are known in the art, for example solutions, emulsions, dusts, suspensions, wettable powders, pastes, soluble powders, granules, suspension concentrates or emulsion concentrates, natural or synthetic impregnated materials. of formula (I), or the active compound of formula (I) is encapsulated and the composition is in the form of a microcapsule.

Such formulations are prepared by mixing and / or triturating the active ingredient with binders, solvents and / or carriers, optionally with the use of surfactants and / or dispersing auxiliaries and / or adhesion promoters.

Useful solvents for this purpose include: aromatic hydrocarbons, preferably 7-12 carbon atoms, such as toluene, xylene mixtures and substituted naphthalenes; chlorinated aliphatic or aromatic hydrocarbons, preferably chlorinated ethylene, methylene chloride or chlorobenzene; aliphatic hydrocarbons such as cyclohexane, paraffins or mineral oil fractions; mineral or vegetable oils; alcohols, for example ethanol or ethylene glycol, or ethers thereof, for example ethylene glycol monomethyl ether, ethylene glycol ether; ketones, for example acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone; strongly polar solvents such as N-methylpyrrolidone, dimethylformamide, dimethylacetic acid, diffithylsulfoxide esters of phthalic acid, for example dibutyl phthalate or dioleyl phthalate; as well as epoxidized plant oils such as epoxidized coconut oil or soybean oil; avoda.

Suitable carriers are, for example, inorganic powders such as kaolin, calcite, talc, lime, quartz, atta-pulgite, montmorillonite, kieselguhr, perlite, amorphous silica, alumina, highly disperse silicic acid, pumped silica. , brick powder, sepiolite, bentonite or sand organic powders, for example flour-like powders, prepared from plant parts such as straw or coconut shells and fine meal; various types of starch, processed starch; sugar, for example glucose; a powdered or ground synthetic resin such as phenolic or urea resin. A variety of inorganic or organic pre-granulated materials can also be used.

A variety of nonionic, cationic and / or anionic surfactants can be used as surfactants, having favorable emulsifying, dispersing and wetting properties. Mixtures of surfactants may also be used. The anionic surfactants are water-soluble soaps, for example sodium potassium salt-oil or stearic acids, as well as salts of natural fatty acid mixtures; However, it is preferable to use synthetic surfactants, in particular fatty alcohol sulfonates, sulfate fatty alcohols, sulfonate benzimidazole derivatives or alkylaryl sulfonates. Exemplary are lignin sulfonic acid calcium and triethanolamine salts, esters of dodecyl arylic acid, sulfonic acids prepared from naturally occurring kyyelin as well as acid esters sulfuric and adductive alcohol-ethylene sulfonic acids, dodecylbenzenesulfonic acid or tributylnaphthalenesulfonic acid. In addition, phosphates, such as the p-nonylphenol (4-14) ethylene oxide adduct, are also suitable.

Suitable cationic surfactants include quaternary ammonium salts which contain lower alkyl groups substituted by halogen or hydroxyl and / or benzyl group attached to the quaternary nitrogen atom by the alkyl groups having from 8 to 20 carbon atoms. Examples of such surfactants include, for example, stearyltrimethylammonium chloride or benzylbis (2-chloroethyl / ethylammonium-11bromide).

The nonionic surfactants are mainly polyoxyethylene glycol ethers, polyoxyethylene glycol esters, as well as polyhydric alcohol esters and condensation products thereof, nonylphenol polyethoxyethanols, castor oil polyglycol ethers, and polypropylene polyethylene oxide adducts.

Suitable dispersants include lignin sulphonate, sulphite caustic, and methyl cellulose.

The compositions may also include adhesion promoters such as carboxymethylcellulose, natural, synthetic, powder, granular or latex polymers, such as polyvinyl alcohol, polyvinyl acetate, but also natural phospholipids such as cephalin, lecithin, or synthetic phospholipids.

In addition, the herbicidal compositions according to the invention may be used in the present invention. other additives such as stabilizers, anti-foaming agents, viscosity-controlling additives, preservatives as well as inorganic or organic pigments may also be used. to

The compositions of the invention may also contain an activating, ergonomic and antidote additive. £

The invention also encompasses herbicidal compositions which both have known antidotes, such as LKA-24 / N-dichloro-. acetyl-N-allylglycine-N &apos; -allylamide, AD-67 (N-dichloroacetyl-1-oxa-4-azaspiro [4.5.1] decane), R-25788 (N, N-diallyl-dichloro-ecetamide) (MG-191, TE-35 or CGA-92194. / T1-35 is N- (dichloro-acetyl) hexamethyleneimine, CGA-92194 is N- (1,3-dioxolane-2-ylmethoxy) iminobenzeneacetonitrile). N is 2-dichloromethyl-2-methyl-1,3-dioxo-2-yl

Optionally, the compounds of the formula I according to the invention and compositions containing them as active ingredient can be used together with other agrochemicals such as herbicides, fungicides, insecticides, miticides, nematocides, | antiviral agents, plant growth regulating agents and ata- raktanty. | ř.

I 12

The compositions according to the invention preferably contain from 0.01 to 95% by weight, and in particular from 2 to 80% by weight, of the active compound of the general formula (I) according to the invention, or only the active ingredient and the antidote, by weight of 5 to 5%. 99.9% of a liquid or solid carrier and from 0 to 30%, preferably 0.1 to 25% by weight of surfactant or other additives. In compositions containing antidote, the antidote to the active ingredient may be in a weight ratio of 1: 1 to 50: 1. 1. Subsequently, particularly preferred compositions of the present invention are mentioned, with the percentages being by weight:

Solutions 1 to 301 to 90O to 99 preferably 5 to 25% preferably 0 to 85% preferably 0 to 95% of active ingredient surfactant solvent 2. Emulsifiable concentrates 1 to 20%, preferably 5 to 1 to 30%, preferably 5 to 5%. from about 50% to about 94%, preferably from about 70% to about 10%, of active ingredient 20% surfactant 85% liquid carrier

Wettable powders of from 0.5 to 90%, preferably from 20 to 80%, from 0.5 to 20%, preferably from 5 to 15%, from 5 to 95%, preferably from 15 to 90%. 50% 25 to 95%, preferably 30 to 80% 1 to 40%, preferably up to 20% of the active ingredient of the surface active solid carrier of the surfactant water 5. up to 5% of active ingredient90 to. 99.5%, preferably 95-99% of the solid carrier 6. Granules 0.5 to 30%, preferably 1 to 15% of the active ingredient70 to 99.5%, preferably 85 to 95% of the solid carrier

The herbicidal compositions of the invention may be diluted to an active ingredient content of 0.01% by weight prior to use. 13

The compositions may be applied to the treatment site after dilution or dilution in a manner known per se, for example by spraying, dusting, spraying, spraying, or ultra-low volume. The herbicidal compositions containing the novel sulfonylurea derivatives of the formula I as active ingredient have excellent herbicidal activity with respect to both monocotyledonous and dicotyledonous, annual or multi-yearly weed plants. The compositions of the invention may be used prior to emergence or enhancement. In the treatment before emergence of weed plants in the case of vegetation-free soil, the plants develop and develop into the cotyledonous phase, then their growth stops and they partially or fully disappear within 3 to 6 weeks. In the treatment after emergence of pleural plants, the growth of these plants is stopped after application of the herbicidal composition, and the plants disappear completely or partially within 1-4 weeks. It is characteristic for the herbicidal composition according to the invention that it exhibits an effect even when applied in an extremely small amount. Depending on the treated weeds, the herbicidal action is very good even in such small doses as 0.01 to 2.0 kg / ha. Important cultivated plants such as wheat, maize, barley, rice and soybean herbicide compositions of the present invention fully resist; the compositions according to the invention are therefore of excellent use for destroying monocotyledonous and dicotyledonous weeds of one-year-olds which have not yet been destroyed or are particularly difficult to destroy in the aforementioned crops. However, crop plants are not limited to the foregoing. Depending on the active compound used, in doses of 0.05 to 2.0 kg / ha, the compounds of the invention may be used for total weed control. as particularly preferred herbicidal compositions containing sulfonylureas of the formula I as active ingredient. compounds appear to decompose rapidly in the soil when used after emergence, so that treated plots can be sown with another crop immediately after the crop is harvested. This 1 decomposition of the active substance in the soil is faster than in the fall. known commercially available sulfonylureas.

The process for the preparation and use of the active compounds / compounds of the formula I and the herbicidal compositions according to the invention is illustrated by the following examples, but are not intended to limit the invention. EXAMPLE 1 Preparation of 3-Ethoxymethyl-1- (2-methoxycarbonylphenylsulfonyl) -3- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) urea (compound number 8)

After addition of 0.01 g of DABCO catalyst to a solution containing 3.96 g (20 mmol) of 2-ethoxymethylamino-4-methoxy-6-methyl-1,3,5-triazine in 50 ml of anhydrous diethyl ether, 5, 3 g (22 mmol) of 2-methoxycarbonylphenylsulfonyl isocyanate dissolved in 20 ml of anhydrous diethyl ether are added dropwise to the above solution at room temperature with stirring. The reaction mixture was stirred for 6 hours, whereupon the product began to precipitate. The next day, the crystalline precipitate is filtered off, washed with a small amount of diethyl ether and dried at room temperature to give 6.5 g (74% of theory) of 3-ethoxymethyl-1- (2-methoxycarbonylphenylsulfonyl) -3- (4-). of methoxy-6-methyl-1,3,5-triazin-2-yl / urea, m.p. 105-106 ° C. Example 2 Preparation of 3-ethoxymethyl-1- (2-chlorophenylsulfonyl) -3- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) urea (Compound No. 4) 3.96 g. (20 mmol) 2- (ethoxymethyl) amino-4-methoxy-6-methyl-1,3,5-triazine to a solution of 6.23 g (20 mmol) of phenyl N- [2-chlorophenylsulfonyl] carbamate in 120 ml of anhydrous benzene.

The mixture is stirred at 75-80 ° C for 8 hours, then evaporated to dryness. After recrystallization of the residue from diethyl ether, 15 g of 5.06 g (61% of theory) of 3-ethoxymethyl-T- (2-chlorophenylsulfonyl) -3- (4-methoxy-6-methyl-1,3,5-) were obtained. triazin-2-yl / urea mp 123 ° C. Example 3 Preparation of 3- (4,6-dimethylpyrimidin-2-yl) -1- (2-chlorophenylsulfonyl) -3- (ethoxymethyl) urea (Compound No. 2) 4.87 g (20 mmol) N- (4) 6-dimethylpyrimidin-2-yl) -N- (ethoxymethyl) carbamoyl chloride dissolved in 10 ml of dimethylformamide was added dropwise to a solution containing 4.27 g (20 mmol) of 2-chlorobenzenesulfonamide sodium salt in 25 ml. ml of anhydrous, distilled dimethylformamide, at 5-10 ° C with stirring. After the addition was complete, the mixture was stirred at room temperature for three hours, then poured into a 250 mL ice-water condenser. The precipitate was filtered off, washed with a little water, dried and then recrystallized from ethyl acetate / methyl ether to give 3.34 g (42%) of 3- (4,6-dimethylpyrimidin-2-yl). 1- (2-chlorophenylsulfonyl) -3- (ethoxymethyl) urea, m.p. 118-119 ° C. Example 4 Preparation of 3- (4,6-dimethylpyrimidin-2-yl) -3-ethoxymethyl-1- (2-methoxycarbonylphenylsulfonyl) urea (Compound No. 6)

After addition of 3.1 g (10 mmol) of phenyl N- (4,6-dimethylpyrimidin-2-yl) -N- (ethoxymethyl) carbamate to a solution of 2.15 g (10 mmol) of 2-methoxycarbonylbenzenesulfonamide and 1.52 g (10 mmol) of 1,8-diazabicyclo [5.4.0] undec-7-ene in 25 ml of anhydrous dioxane is stirred at 30 to 35 ° C for 10 hours, then poured into 200 ml of water. After adjusting to pH 6.5, the precipitate was filtered off, dried and recrystallized from chloroform / hexane to give 1.59 g (37.6%) of 3- (4,6-dimethylpyrimidin-2-yl) -3. ethoxymethyl-1- (2-methoxycarbonylphenylsulfonyl) urea, m.p. 124-126 ° C. Example 5 Preparation of 3- (4,6-dimethylpyrimidin-2-yl) -3-methoxymethyl-1- (2-methoxycarbonylphenylsulfonyl) urea (Compound No. 5)

A mixture containing 4.3 g (20 mmol) of 2-methoxycarbonylbenzenesulfonyl chloride, 3.67 g (22 mmol) of 4,6-dimethyl-2- (methoxymethyl) aminopyrimidine and 3.24 g (40 mmol) of potassium cyanate in acetonitrile (30 ml) was maintained at 81 ° C with vigorous stirring for two hours. After filtration of the precipitated inorganic salt, the filtrate is evaporated, the residue is resuspended in 30 ml of water, then the precipitate is filtered off, dried and recrystallized from ethyl acetate / diethyl ether to give 5.4 g / 66. 2% of theory [3- (4,6-dimethyl-pyrimidin-2-yl) -3-methoxymethyl-2- (2-methoxycarbonyl-phenylsulfonyl) -urea m.p. 133-135 ° C.

Similarly as described in the above examples, the following compounds are prepared: Oxygen Compounds of formula I wherein X is gt Compound Rfnina number r2 E3 R4 E5 E Melting point. 1 Cl H CE3 CH3 CH3 CH 126 - 128 2 H C2H5 ch3 CH3 CE 118 - 119 W Cl E CH3 CH3 CH3O N 130 - 135 4 Cl E c2h5 CH3 CB ^ ON 123 - 124 5 C.OOCH3 H ck3 ch3 CH3 CH 133 - 135 6 cooch ^ E C2H5 CK3 CH3 irtf 124 - 126 7 COOCH3 H CH3 0 3 CH3O N 112 - 115 8 COOCH3 E C4H9 ce3 CH3O TT 100 - 102 10 COOCH3 and CEL ch30 N 103 - 104 11 HE CH-, CH-> CE.CN 125 - 127 17 Example 6 Preparing a Wettable Tray

Ingredients in grams Active ingredient prepared according to Example 2 20 Silicate carrier / Zeolex 444/80 Diatomaceous earth 80 Aliphatic sodium sulfonate as a wetting agent / Netzer IS / 4Cresol formaldehyde sulfonate as dispersant / dispersant 1494/6 Powdered sulfite liquor / Borresperse NA / 10

The pulverulent mixture is crushed in a laboratory ball mill for 30 minutes, then milled into fine particles in an Alpine 63 C laboratory mill at a speed of 70. The wettable powder thus obtained contains Compound 4 of Table I as active ingredient in a weight of 10%. % .Volume. / in 1% concentration /: 86.5%

Wet sieve / sieve DIN 10 /: 0.27% · Example 7 Preparation of wettable powder / 50 WP /

Ingredients in grams active ingredient according to Example 3 150 synthetic silicate carrier / Zeolex 444/30 siliceous sodium 50aliphatic sodium sulphonate / Netzer IS / 4resolformaldehyde sulphonate 6 powdery sulphite lye 10

The procedure of Example 6 was followed to give a wettable powder containing 50% by weight of Compound 2 of Table I.

Buoyancy. / in 1% concentration /: 82.9%

Wet residue on sieve / sieve DIN 100 /: 0,043% · 18 Example 8 Preparation of wettable powder / 85 WP /

Ingredients in grams The active ingredient according to Example 4 170Silicate-based synthetic carrier / Sipernat 50S / 20-Sodiumoleylmethyl laurate / Arkopon T beer / 4Color formaldehyde sulfonate 6

The procedure of Example 6 was followed to give a dusty product containing Compound 6 of Table I as the active ingredient in an amount of 85%.

Rebound / in 1% concentration /: 82.9%

Wet sieve / sieve DIN 100 /: 0.43 Example 9 Preparation of emulsifiable concentrate / 5 EC /

Ingredients in grams Active ingredient according to Example 1 5 xylene 70 cyclohexanone 15 kaleium dibasylbenzene sulphonate / Emulsogen IP 400/8 fatty acid polyglycol ester / Eqiulsogen EL 400/2 The active substance is dissolved in a mixture of xylene and cyclohexane under stirring and 8 g of Emulsogen IP is added 400 and 2 g of Emulsion EL 400 as emulsifier. After homogenization, the mixture is filtered.

The emulsifiable concentrate thus obtained contains Compound (8) of Table I as active ingredient in weight 5.

Emulsion stability / 1% CIPAC A concentrate and CIPAG D water /: stable after two hours.

Reversible curability is observed after 24 hours.

Example 1 O Powder Powder Preparation (5D)

Ingredients in grams of talc silicate / Sjpernat 50 S / active ingredient according to Example 5lime / Ml 0/20 30 50 900 A mixture of the active ingredient of Example 5, a synthetic silicate carrier and talc was prepared and crushed in a laboratory ball mill, then gently ground in a laboratory mill Alpine 63C. The mixture is then homogenized with limestone in a laboratory powder mixer.

Thus, a dusting powder containing the compound number 5 according to Table I in an amount of 5% by weight is obtained.

Sieve / sieve residue DIN 100 /: 0.12%, Example 11 Preparation of suspension concentrate / 5 FW /

Ingredients in grams active ingredient according to example 2 10 sunflower oil 168 organophilic bentonite / Ivegel / 2 polyethylene alkyl ether, polyoxyethylene castor oil, ethoxylated fatty acids and sulphosuccinate sodium / Sorpol 3815/20 emulsifier, sunflower oil, organophilic bentonite / Ivegel / and Sorpol 3815 the reagent is weighed into a laboratory ball mill. The suspension concentrate together with 65% by volume glass beads of 1.0 to 1.5 mm diameter at 775 rpm for 30 minutes. The suspension concentrate thus obtained contains, as active ingredient, a compound of formula (4) according to Table I in an amount of 5% by weight.

Stable / 1% concentrate in CIPAC and CIPAC D water /: stable after 30 minutes. Example 12 Preparation of Suspension Concentrate / 40 Fit /

Compound in grams Active ingredient according to Example 1 80 Synthetic silicate / Zeolex 444/6 Sodiumoleylmethyltauride / Arkopon T beer / 4 nonyifenol polyglycol ether / Arkopal W 100/10 2% solution, xanthan gum / Kelzen S / 10 water 80

80 g of the active substance prepared according to the method of Example 1 are weighed, synthetic silicate (Zeolex 444), sodium oleyl methyl auride (Ahkopon T) and nonylphenyl polyglycol ether (Arcolol 100) as a wetting dispersant and 80 g of water into a laboratory ball mill . After homogenization, the suspension suspension concentrates together with a volume of 70% glass beads of 1.0 to 1.5 mm diameter for 30 minutes. After milling and separating the beads, the mixture is homogenized with 20 g of a 2% solution of xanthan gum (Kelzen S) under vigorous stirring.

Thus, a suspension concentrate containing compound (8) according to Table I in an amount of 40% by weight is obtained.

Buoyancy / in 1% concentration /: 97.3%

Particle size / below 10 micrometers /: 91.6% Example 13 Preparation of water-dispersible granules / 75 WDG / 21

Ingredients in grams

Compound No. 3 of Table I as active ingredient 375 synthetic silicate carrier 55polyvinylpyrrolidone / K30f product of SASF / 20alkylphenol ether phosphate / Atlox 5330, product ICI / 30 mixture of polyalkylene glycol ether and polymethylenealkyl-aryl ether / Atlox 4896, ICI product 20water 180 preformed with 375 g compound number 3 according to Table I, as an active ingredient with 55 S synthetic silicate support to a laboratory ball mill, and then the mixture is milled into fine particles in an Alpine 63 C mill at 8®. Prepare the granulating liquid by dissolving 20 g of polyvinylpyrrolidone, 30 g of alkylphenol ether phosphate and 20 g of a mixture of polyalkylene glycol ether and polymethylene alkylaryl ether in 180 ml of water. The powder mixture is introduced into a FPG 0.5 granulation unit operating periodically under fluidization atomization and brought into a fluidized state by regulating the air flow introduced at 60 to 65 ° C. When the inlet temperature reaches 30 ° C, the evaporation of the granulation liquid at a pressure of 0.15 MPa and volume begins

the air flow increases depending on the particle growth. After the granulation liquid has been introduced, drying is continued up to an outlet temperature of 36-38 ° C. ;

The granules thus prepared contain, as active ingredient, compound (3) according to Table I in an amount of 75%.

Buoyancy. / at 1% concentration after 30 minutes /: 93.7%

Particle size between 0.2 and 1.0 MM: at least 75% · - i Example 14 - j Preparation of water-dispersible granules / 25 WPG /

Ingredients in grams; - 22 compound number 7 according to Table I as active ingredient 125 synthetic silicate carrier 250 maltodextrin binder 75 ligninsulfonates / Sorpol 9D 47 K product Toko / 30polyoxyethylenepolyalkylarylphenol ether sulfate / Sorpol 5096 product Toko / 20

Compound No. 7 of Table I as active ingredient, synthetic silicate carrier, maltodextrin binder, and lignin sulfonate. (Sorpol 90 47 K, product Toko) and polyoxyethylene polyalkylarylphenol sulfate / Sorpol 5096, the product Toko / as a surfactant is weighed into a laboratory ball mill. Melese for 30 minutes, whereupon the powder mixture is milled on a Alpine 63 G laboratory mill. The mixture is then fed into a PPG 0.5 fluidizing unit operating periodically with fluidization and placed in a fluidized state by controlling the inlet temperature of 60 °. C.

Granulation is carried out by spraying water when the outlet temperature reaches 28-30 ° C. Upon reaching the desired particle size of 0.5 mm, water spraying is stopped and drying is continued until the outlet temperature reaches 36-38 ° C. As the granules obtained contain 25% as the active ingredient, the compound of the formula (7) in Table I is present.

Buoyancy. (at 1% concentration after 30 minutes): 91.85% Particle size between 0.2 and 1.0 mm: at least 95%. Example 15 Preparation of Suspension Concentrate / 14.5 FW /

Ingredients in grams Compound No. 8 according to Table I as active ingredient 2,0DKA-24 / N-dichloroacetyl-N-allylglycine-N 2 -allylamide / as an antidote of 12.5

Zeolex 444 as carrier 11> 6 - 23 monoethylene glycol 15.0 Arkopon T, wetting agent 3.0 Arkopol N-090 / nonylphenylpolyglycol ether / as dispersing agent 6.0 water 39.9% by weight 2% xanthan gum solution hahus &amp; In a method as described in Example 12, a suspension concentrate containing Compound (8) of Table I and DKA-24 Antidote in the total amount of 14.5 in a weight ratio of 1: 6.25 was prepared. Example 16 Preparation of Suspension Concentrate / 27.0 FW /

Ingredients in grams Compound 8 according to Table 1 as active ingredient 2.0 R-25788 / N, N-diallyldichloroacetamide / as antidote 25,0Zeolex 444 as carrier 5,0monoethylene glycol 10,0Arkopon T as wetting agent 2,5Arkopol N-090 as dispersing agent a composition of 5.5% by weight of a 2% xenthan gum solution as a 8.0 thickener

The procedure of Example 12 was followed to obtain a suspension concentrate containing as active ingredient Compound 8 according to Table I and R-25788 antidotes in a total amount of 27% in a weight ratio of 1: 12.5. Example 17 Preparation of wettable powder / 20.25 WP / Ingredients in grams - 24 Compound No. 4 of Table 1 as active ingredient 1.50 AD-67 / N -diclorecetyl-1-oxa-4-azaspiro / as * 4,5_7dekan/ as antidote 18,75Zeolex 444 as carrier 34,75cellulose 33,00Netzer IS as a wetting agent 3,00Dispergiermittel 1494 as a dispersing agent 4,00 sulfite lye as a dispersing agent 5,00

In the manner described in Example 6, a wettable powder is obtained containing as active ingredient compound number 4 according to Table I and AD-67 antidotes in a total weight of 20.25% in a weight ratio of 1: 12.5. Example 18 Preparation of Water Dispersible Granules / 13.5 WDG /

Ingredients in grams Compound No. 6 according to Table I as active ingredient 1.0CGA-92194 (1 H-1,3-dioxolan-2-ylmethoxy) imino-benzene-acetonitrile 7 as an antidote 12,5 synthetic silicate carrier 61,5 meltodextrin as binder 15,0 lignosulfonate / Sorpol 90 47 K / 6,0 polyoxyethylenepolyalkylarylphenylether sulfate / Soropol 4,0 5096 /

The procedure of Example 14 is followed to obtain a water-dispersible granule comprising, as the active ingredient, compound number 6 according to Table 1 and as an anti-dot GGA-92194 in a total weight of 13.5% by weight. 1: 12.5 · Example 19 Preparation of Wettable Powder / 51.2 WP / - 25

Ingredients in grams Compound No. 2 according to Table I as active ingredient 20.0 DKA-24 as antidote 31, 2Zeolex 444 as carrier 14,4-silica as carrier 24,4Netzer IS as a wetting agent 2,0kiesol formaldehyde 3.0 powdered sulphite lye as dispersant 5 , 0

The method of Example 6 gives a wettable powder containing Compound 2 as active ingredient according to Table Ia ahtidot. (DKA-24) in a total weight ratio of 51.2% by weight ratio of 1: 1.56. Example 20 Preparation of Wettable Powder / 24.75 WP /

Ingredients in grams Compound No. 2 of Table I as active ingredient 6.00MG-191/2-dichloromethyl-2-methyl-1,3-dioxolane / as antidotes. 18.75

Zeolex 444 as carrier 33,00 j of carrier 32,25;

Netzer IS as a 2.00 wetting agent

Dispergiermittel 1494 as dispersing agent 3.00 sulfite liquor as a dispersing agent 5.00.

In Example 6, a wettable powder containing Compound 2 of Table I and an antidote MG-191 in a total weight of 24.75% in a weight ratio of 1: 3.125 was obtained. Example 21 - Powder Powder Preparation / 5.2 D /

Ingredients in grams - 26 Compound No. 5 according to Table I as active ingredient 2 AD-67 as antidote 50mast 19-synthetic silicate carrier / Pipernat 50 S / 29-lime / M 10 type / 900

In the method of Example 10, a dusting powder containing, as active ingredient, compound 5 according to Table I and antidotes AD-67 in a total weight of 5.2% in a weight ratio of 1: 25 is obtained. Example 22 Preparation of Wettable Powder (21 WP)

Ingredients in grams. Compound No. 6 of Table I as active ingredient 1.0 DKA-24 as an antidote 20.0Zeolex 444 as carrier 30.0 siliceous as carrier 39.5Dispergiermittel 1494 as a dispersant of 3.0Netzer IS as a wetting agent 2.0-powdered sulphite lye 4.5

Example 6 provides a wettable powder containing, as active ingredient, compound 6 according to Table I and DKA-24 as an antidote in a total weight of 21% in a weight ratio of 1: 20. Example 23 Preparation of Powder Powder (6D)

Ingredients in grams Compound No. 4 according to Table I as active ingredient 10 DKA-24 as antidote 50 Talc 15 Synthetic silicate carrier / Sipernat 50 S / 25 Copy Z / M 10 Type 900 - 27 I as active ingredient 2 20 6 4 10 acacia A suspension concentrate is obtained

Dusting is obtained by the method of Example 10. a powder containing, as active ingredient, compound 4 according to Table I and antidotes DKA-24 in a total weight of 6% in a weight ratio of 1: 5. Example 24 Preparation of Suspension Concentrate

Ingredients in grams ~ y Compound No. 2 according to Table DKA-24 as an antidote Zeolex 444 as carrierArkopon T as wetting agent Arkopol N-100 as wetting agent 2% solution xanthan thickener water

By the method of Example 12, containing, as active ingredient, the number I compound and the DKA-24 antidote in a total weight ratio of 22% in a 1: 10 weight ratio.

Testing the effect after emergence in the greenhouse / effect on emerging plants /

Seeds of the test plants are sown in a mixture containing 1/3 sand, 1/3 clay and 1/3 blacks in 200 ml plastic canisters with 4 holes in the bottom.

After sowing, the soil and the small plants or emerging plant lines are sprinkled daily at 20 DEG-26 DEG C. under natural illumination supplemented with 4 hours of illumination. Formulation 10 WP, prepared from compounds 3, 5, 6, 7 and 8 according to Table I of Example 6, was sprayed, using 1000 liters per hectare of 0.4 MPa, on plants in a 2 to 4 leaf condition using a greenhouse syringe. 28

The damage to the test plants is evaluated on the second and the fourth week after spraying. Plant damage is reported as a percentage: 0% means no damage and 100% complete destruction of the plant. The results are shown in Table II. It will be appreciated that the compositions of the present invention have good herbicidal activity and exhibit favorable selectivity with respect to cultivated plants. Compounds Nos. 3, 7 and 8 are particularly effective. Table I and Arabic numerals refer to the compound number in Table I.

Table II

Post-emergence test

Compound DoseNumber

in Table I g / haORYS 1/3 270 30 90 0 30 0 10 0 1/5 270 1 00 1/6 270 90 90 80 1/7 270 1 0 90 10 30 0 10 0 1/8 270 20 90 20 30 0 10 0 Abbreviations in Table II ORYS Gryza sativa ECHO Echinochloa c., Trick Tri-ticum aesticumGALA Galium aparineGLYM Glycine max

Percentage of test plant damage to STEM ECHC GALA MAII ZEAM HELA GLYM TRIE 1 00 80 1 00 100 20 100 80 0 100 60 80 100 0 1 00 30 0 100 0 40 90 0 40 30 0 1 00 0 30 30 0 0 O 0 100 100 80 100 100 100 100 100 100 100 35 70 100 100 80 100 100 100 30 50 100 50 90 100 100 60 100 10 100 70 0 100 100 50 100 10 100 60 0 100 20 25 90 0 40 0 0 100 0 0 30 0 4.0 0 0 100 100 70 100 100 100 90 0 100 90 50 100 20 100 60 0 100 30 40 90 10 100 40 0 100 0 30 90 0 70 10 0 MAII Matricana inodorHELA Helianthus annuusstem Stellaria mediaZEAM Zea mays - 29 - Example 26

Testing the effect before emergence in the greenhouse

The seeds of the test plants are always sown three times in a medium impermeable forest soil placed in paper boxes sponge-shaped to a height of 7 cm and 200 cm. Separately treated boxes are placed on plastic mills equipped with a wetting agent. After sowing, the plants are treated with 10 WP prepared from compound 7 of Table I of Example 6 together with water at a rate of 1200 liters per hectare of soil surface in boxes using a greenhouse microswitch prior to emergence. Water make-up ensures that the wetting agent is kept wet. The test is carried out at 0 to 28 ° C in natural light supplemented with oscillation for 4 hours. The herbicidal action of compound 7 of Table I was evaluated 4 weeks and 6 weeks after spraying.

Table III Pre-emergence Treatment Damage to the test plant in pro

Compound Number / Table Dose Solanum Digitaria 2UU ECHC STEM, TRIE 1 / migrum adans 1/7 250 70 50 20 100 0 1000 100 60 40 100 0 Example 27 Research on the Effect of Cultivated Plants in the Cultivation Chamber of the Progenitor

400 g of soil from the field surface / pH 6.5, 50 permeability and humus content of 1.4% are weighed into the plastic culture vessels each time; the surface of each container is 0.8 dm, each lined with polyvinyl chloride sheet. Ten seeds of Pi-3737 maize, 100 seeds of IREG sunflower, 50 seeds of SA-114 sorghum and 1 g of red progeny are then placed in each case. - 30

The seeds are always covered with 100 g of soil and treated. During this treatment, 10, 20, 40, 80, p.60 or 320 g / s of water-dispersible granules (75 WDH) prepared according to the method of Example 13 are each using Compound No. 2, 4, 6, 5 and 8 As well as Ally, Teli, Granstar, Glean, Logran, and SL-950. The soil treatment surface is again covered with a further 100 g of soil for each vessel. The vessels are placed in a plant growing chamber, sprinkled daily up to their water receiving capacity and grown with HGME / D 400 lamps replacing sunlight for daylight in a 16 hour period. The tests are evaluated on day 10 after sowing and the green weight of the sunflower, sorghum and pro-sa and the green weight and length of the corn stalk are determined. Results The results are given in Table IV with the designation "sowing I".

Seeds of maize, sunflower and millet are replanted6, times into the soil and the test is evaluated. The results of this evaluation are shown in Tables V to IX with the designations "sowing II, III, IV, V, VI". 76 days have passed since "sowing I" after sowing VI. Table IV shows the development of the green weight of maizePi-3737 and sunflower "IKEG" under treatment (this development is given as a percentage compared to untreated culture plant). Table IV (continued) shows the development of green weight of millet and sorghum under the influence of the treatment (this development is given as a percentage compared to untreated plant). -Βί- ο

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Field herbicidal activity test with winter wheat culture

The post-emergence herbicide test is carried out on the plots. 2 winter wheat with an area of 10 m near the Sebes-Ktirtís river.

The test is carried out on meadow soil with a pH of 6.3 containing 3.4% of organic material. Winter wheat is used as a green cultural plant. It is sucked on October 24 to a well-treated dry soil to a depth of 6 to 7 cm with a row spacing by sowing. /

The test is carried out after emergence on April 20th. Weed plants and their developmental status at the time of treatment are: Galium aparine-GALAP at stages 4-6 of the leaf; Red Deadnettle, Lamiurn purpureumLAMPU, in flowering stage; Veronica arvensis, VERAR, at the beginning of flowering; chickweed ^ Stellaria media, STEME in the flower stage, Eumaria officinalis, FUMOF in the sixth stage, Consolida orientalis, CONOR in the stage. 10.cup the height of the stem formation stage; merlik, Chenopodium album, CHEAL; Bilcerdyckia convolvulus, BIL-CO at the second and third leaf stage; to perform the test, the spray sprayed propane-butane gas under pressure. They apply 10 to 80 g of active compound per hectare using the compounds 4, 5, 6 and 8 according to Table I in 500 liters of spray liquid per hectare as a 5 FW suspension concentrate according to Example 11. The same doses of Logran 75 DF are used for comparison. and Granstar 75 DF.

The herbicidal and phytotoxic effects of the treatment were evaluated using a scale from 0 / ineffective to 100 / total destruction. This evaluation is performed four times / 27. April, May 4th, May 25th, and June 28th, that is, in the period of study, counting the number of ears / m, the length of the ears / cm / and the weight of 1000 grains / g /. The results, which are the mean of the four assays, are shown in Tables X to XVI.

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Table XVI Ear Test Results Treatment

Untreated 1/8 1/4 1/6 1/5

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Example 29 J Investigation of the effect of antidote compounds on cultivated plants in a plant growing chamber.

Always weigh 40 g of soil from the surface of the field (pH 6, 5) with a permeability of 50 and with a humus content of 1,4% / into the cultures of plastic boxes of 0,8 cm surface lined with foil polyvinyl chloride. 10 seeds of Pi-3737 and 10 seeds of "IREG" sunflower are placed on this soil. The seeds are then covered with 100 g of soil and each treatment is performed four times. In this treatment, 20 to 160 g / ha of active ingredient, 2, 4, 5, 6 or 8 according to Table I, together with 250 and 500 µl are dosed; g / ha of DKA-24, AD-67, R-25788, MG-191 or CGA-92194 antidotes in the form of the formulation of Examples 15 to 21. The treated soil surface is covered with an additional 100 g of soil 5; in each container. The flasks are introduced into the growing chamber and cultured with donn light for 16 hours. Plants are sprayed daily to their water capacity.

The assays are evaluated by measuring / measuring the length of the shoot and the green weight on day 13 after treatment. Results are given - ;;;

in Table XVII to XIX. Table XVII shows the evolution of green J

weight of Pi-3737 maize under treatment; Table XVIII evaluates the development of the stem length of the Pi-3737 maize under the influence of the investigation and the development of the green weight of the sunflower in Table XIX; "IREG under the influence of treatment. G 48 ΪΙΛΧ <Ť σ"

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Test of the effect of antidote compounds on cultivated plants in a plant growing chamber.

Weigh 400 g of soil from the surface of the field (pH 6.5, permeability 50 and humus content 1.4%) in 0.8-m &lt; 3 &gt; Ten seeds of Pi-3747a and 50 seeds of sorghum SA_114 are placed on the soil surface. The seeds are covered with 100 g of soil, followed by four treatments. For this treatment, 20, 40 or 80 grams per hectare of Compound No. 2, 4, 5, 6 or 8 of Table I, 400 grams / ha of DKA-24 as an antidote in the formulations formulated in Examples 22 to 24 are applied. doses of Glean, Granstar, Ally, or Teli are applied together with DKA-24 as a comparator. Again, the sprayed surface of the soil is covered with another 100 g of soil in each vessel. The flasks are then introduced into the plant growing chamber and cultured under an exposure period of 16 hours. Plants sprout up to their water capacity.

The test is evaluated by measuring / measuring / stalk length and green weight on day 12 after treatment. The results are shown in Table XX. -52 maize shoot length (cm) maize green weight (g) sorghum green weight (g) ra t £

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Industrial usability

Herbicidal compositions containing novel sulfonylurea derivatives as active ingredients having more favorable chemical and physical properties, higher selectivity, and lower residence time in. In comparison with the sulfonylureas known from the art, herbicidal active substances act on monocotyledonous, dicotyledonous, annual and multi-year old weed plants in cereals, maize, sorghum, millet and the like.

Claims (4)

PATENT CLAIMS What is claimed is: 1. A herbicidally substituted substituted derivative of formula (I) R 2 -CH-OR 3 wherein R 1 is hydrogen, halogen, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 3 alkylsulfonyl or c R6 is hydrogen, C1 -C3 alkyl or phenyl, R1 -C6 alkyl, C3 -C6 alkenyl, C1 -C3 alkoxyalkyl. alkoxy, C 2 -C 4 alkyl substituted by one or more halogen atoms, or benzyl, R 4 and R 4 independently of each other are C 1-4 alkyl, C 1-4 alkoxy, and halogen , (C 1 -C 3) alkylamino or (C 1 -C 3) alkylamino or (C 1 -C 3) alkylthio, (C 4 -C 4) alkoxy, (C 3 -C 6) alkenyloxy; alkoxyalkyl - C 5 -C 6 alkyl, C 1 -C 3 alkylamino, C 1 -C 3 dialkylamino, piperezinyl or morpholinyl, X is O or S and E is a methine or atom nitrogen and its salts. 2. A herbicidal composition comprising, as an active ingredient, a substituted derivative, a sulfonylurea of the formula I, wherein R1 is hydrogen, halogen, alkoxy of 1 to 1. C 4 -C 4 haloalkoxy, C 1 -C 3 alkylsulfonyl or C 1-6 alkyl, R 2, C 1 -C 3 alkyl or phenyl; C 6 -C 6 alkenyl, C 1 -C 3 alkoxyalkyl, C 1 -C 4 alkoxyalkyl, C 1 -C 4 alkyl substituted by one or more halogen atoms, or benzyl, R 6 and R 6 is each independently C1 -C4 alkyl, C1 -C4 alkoxy, halogen, C1 -C3 alkylamino or C1 -C3 alkylamino or C1 -C3 alkylthio C 1 -C 4 alkoxy, C 3 -C 6 alkenyloxy, C 3 -C 6 alkoxyalkyl, C 1 -C 3 alkylamino, d C 1 -C 3 alkyl amino, piperazinyl or morpholinyl, X oxygen or sulfur and E methine or nitrogen, or a salt thereof. 3. A composition according to claim 2 wherein the composition is in the form of a wettable powder. / Priority Claim 31. 01. 1990 / 4. A composition according to claim 2, characterized in that it is in the form of granules. 5. Antidot. comprising a sulfonyl-substituted urea derivative as an active ingredient and an anti-dot, characterized in that it comprises as the active ingredient a substituted-sulfonyl-derivative / urea of the general formula (I) wherein Rp R 1, R p R p X and E are as defined in 1 or a salt thereof and as antidotes preferably DKA-24, which is chemically N-dichloroacetyl-N-allylglycine-N'-allylamide, AD-67, which is chemically N-dichloroacetyl-1-oxa-4 4.5-7dekan, R-25788, which is N, Ν-diallyldichloroacetamide, MG-191, which is chemically 2-dichloromethyl-2-methyl-1,3-dioxan, CGA-92194 which is chemically N- (1,3-dioxolane-2-ylmethoxy) iminobenzeneacetonitrile, or TI-35 in a total weight of 0.01 to 95%, especially 2 to 80% by weight in a weight ratio of 1: 1 to 1:50 A process for the preparation of a substituted sulfonylurea derivative according to clause 1 of formula IX which is chemically N-dichloroacetyl / h examethylenimine, - 58 - N 1 (1) wherein R 1 represents a hydrogen atom, a halogen atom, an alkoxy group having 1 to 4 carbon atoms, a haloalkoxy group having 1 to 4 carbon atoms, an alkylsulfonyl group having 1 to 3 carbon atoms, or a group of the general formula CCR g Rg atom hydrogen, C 1 -C 3 alkyl or phenyl, C 1 -C 6 alkyl, C 3 -C 6 alkenyl, C 1 -C 3 alkoxyalkyl, C 2 -C 6 alkyl, C 2 -C 6 alkoxy, C 2 -C 6 alkoxyalkyl; 4 carbon atoms substituted by one or more halogen atoms or benzyl group, R 1 and R 2 'are, independently of one another, an alkyl group having from 4 to 4 carbon atoms, an alkoxy group having from 1 to 4 carbon atoms, a halogen, an alkylamino group having from 1 to 4 carbon atoms, 3 carbon atoms. or dialkylamino having 1 to 3 carbon atoms in the alkyl moiety or alkylthio having 1 to 3 carbon atoms, R &amp; (C 1 -C 4) alkoxy, (C 3 -C 6) alkylene alkoxy, (C 3 -C 6) alkoxyalkyl, (C 1 -C 3) alkylamino, (C 1 -C 3) alkylamino; a group or a morpholinyl group. 55 X is an oxygen or sulfur atom and E is a methine group or a nitrogen atom and its salts, characterized in that an isocyanate or isothiocyanate of general formula IV is reacted. NCX (IV) wherein R 1 is as defined above with an aminopyrimidine derivative or an aminotriazine. of formula III Wherein the individual symbols are as defined above, preferably at 0 to 50 ° C, preferably at 20 to 30 ° C, or (b) the sulfonylcarbamate of formula (V) is reacted. wherein Rj is as defined above and wherein R is an aminopyrimidine or aminotriazine derivative of formula (III) wherein the individual moieties are as defined above at a temperature of from 25 to 120 ° C, preferably from 60 to 90 ° C. or c) reacting the carbamoyl chloride of formula VI-60 (VI) wherein the individual symbols are as defined above, the salt alkali metal of the sulfonamide derivative of formula (II) wherein the individual symbols are as defined above, at -10 to. 50 ° C, preferably 0 to 25 ° C, N-pyrimidinylcarbamate or N-triazinylcarbamate of general formula (VII) is reacted with or not. (VII) wherein the individual symbols are as defined above, at a temperature of 20 to 80 ° C, preferably at 20 to 40 ° C, or with a sulfonyl chloride of general formula (II) wherein the individual substituents are as defined above. Formula VIII 5-61 cX / VIII (wherein the individual symbols are as defined above with an aminopyrimidine or aminotriazine derivative of formula (III) in which the symbols are as defined above, preferably at 20 to 120 ° C, preferably at 60 to 100 ° C in an inert organic solvent or in a mixture of inert inorganic solvents and optionally converting the obtained compound of formula (I), wherein the individual symbols are as defined above, with an alkali metal or alkaline earth metal hydroxide, an amine or a quaternary ammonium halide, a compound of formula (I) or a salt thereof isolating the solvent or solvents and optionally recrystallizing the solvent