GB2241699A - Herbicidally active urea derivatives and a process for the preparation thereof - Google Patents

Abstract

Novel, herbicidally active substituted sulfonylurea derivatives of the general formula (I), <IMAGE> wherein R1 stands for hydrogen, halogen, C1-4 alkoxy, halo-C1-4 alkoxy, C1-3 alkylsulfonyl or a group of the formula COR6; R2 means hydrogen, C1-3 alkyl or phenyl; R3 represents C1-6 alkyl, C3-6 alkenyl, C1-3 alkoxyalkyl group, C2-4 alkyl substituted by one or more halogen(s) or benzyl; R4 and R5 mean independently of each other a C1-4 alkyl, C1-4 alkoxy group, halogen, C1-3 alkylamino or di(C1-3alkyl) amino or C1-3 alkylthio; R6 stands for a C1-4 alkoxy, C3-6 alkenyloxy, C1-3 alkylamino, di(C1-3 alkyl) amino, piperazinyl or morpholinyl group; X means oxygen of sulfur; and E stands for a methine group or nitrogen, their salts as well as herbicide compositions containing these compounds optionally together with an antidote are disclosed. The compositions are highly effective against a number of weeds and selective when used in cultures of cultivated @.

Description

:2 2.4 -1- EE 9E3P --) T. j HERBICIOALLY ACT T IVE UREA DERIVATIVES AND A

PROCESS FOR THE PREPARATION THEREOF This invention relates to novel, herbicidally active substituted sulfonylurea derivatives of the general formula (I) R' R4 X 4 1 f 11 3::

C( "50 -NH-C-N-oE L - 2 k -- N --41 \ R5 2 ' 3 R - CH - OR wherein R 1 R 2 R 3 R 4 R X (I) stands for hydrogen, halogen, C 1-4 alkoxy, halo-C 1-4 alkoxy, c 1-3 alkylsulfonyl or a group of the formula COR 6; means hydrogen, C 1-3 alkyl or phenyl; represents C 1-6 alkyl, C 3-6 alkenyl, C 1-3alkoxyalkyl group; c 2-4 alkyl substituted by one or more halogen(s); or benzyl group; and R 5 mean independently of each other a C 1-4 alkyl, C 1-4 alkoxy group; halogen; C 1-3 alkylemino or di(C 1-3 alkyl)amino; or C 1-3 alkylthio stands for a C 1-4 alkoxy, C 3-6 alkenyloxy, C 3-6 alkoxyalkyl, C 1-3 alkyl amino, di(C 1-3 alkyl)amino, piperazinyl or morpholinyl group; means oxygen or sulfur; and E stands for a methine group or nitrogen, their salts formed with alkaline metals, alkaline-earth metals, @mines or quaternary ammonium bases. The invention is further directed to herbicide compositions containing such compounds optionally together with an antidote.

The invention further relates to a process for the preparation of novel compounds of the general formula (I), wherein R,, R 21 R3, R4, R 51 R 61 X and E are as defined above.

In the above definitions (throughout the specification):

"alkyl group" is meant to include a straight or branched chain alkyl group, such as methyl, ethyl, propyl, isopropyl, as well as any of the isomeric butyl groups; - "alkoxy group" usually means mettioxy, ettioxy, propoxy, isopropoxy or any of the four isomeric butoxy groups, particularly mettioxy, ettioxy, or propoxy group; 4 0 - 2 - "alkenyl group" may be e.g. allyl, isopropenyl, 1-propenyl, 1- butenyl, 2-butenyl, 3-butenyl, 1-isobutenyl or a pentenyl group, particularly allyl or 4-pentenyl group; - "halogen" in itself or halogen of a haloalkoxy group may be fluorine. chlorine or bromine, particularly chlorine.

Suitable alkaline metal or alkaline-earth metal hydroxides forming salts with the compounds of the general formula (I) are potassium, sodium, magnesium or calcium hydroxide, mainly sodium and potassium hydroxide.

Useful amines for salt formation include primary, secondary or tertiary 2Mines, such as methylamine, ethylamine, propylamine, isopropyl2mine, any of the four isomeric butylamines, dimethylamine, diethylamine, isopropylamine, diisopropylamine, pyrrolidine, piperidine, morpholine, trimethylamine, pyridine, quinoline or isoquinoline, particularly isopropylamine and dieth2nolamine.

Quaternary ammonium bases used for salt formation are e.g. tetraethylammonium, triethylbenzylammonium, trimethylbenzylammonium halide or any kind of tetr2butylammonium halides.

Herbicidally active sulfonylurea derivatives are commonly known compounds.

The known sulfonylureas are characterized thereby that the nitrogen in 3position, substituted by a heterocyclic group, bears hydrogen or a C 1-4 alkyl group, preferably a methyl group; or a C 1-4 alkoxy group, preferably a methoxy group; or a C 2-8 alkenyl, C 2-4 alkynyl group or an ar2lkyl group. Other substituents have been published in a surprisingly low number of patent specifications.

Sulfonylureas of such type are e.g. discribed in the European Patent Specification No. 152,378 and in the published Japanese Patent Applications Nos. J5 8126872 and J6 0076981.

Sulfonylureas exert an excellent herbicidal effect against a number of mono- and dicotyledonous weeds, chiefly broad-leaf and grass weeds /-J.M. Green et al.: Proc. S. Weed Sci. Soc. 34, 214 (1961)7, particularly in wheat and barley cultures. Their advantage consists in the very low effective doses (usually 5 to 50 g/hectare). Their disadvantage appears therein that upon the use thereof cultivated plants are damaged to a higher or lower degree. It has turned out in the practice of their use that their antidotation is advisable in cereals and essential in maize cultures. In the European Patent Application No. 127,469 antidotes Q, 1 ..t G are published which can be used after sowing in the preemergent period and are capable to protect wheat and millet from the harmful effect of 5Ulfonylurea-type herbicides. Methyl 2/-(aminocarbonyl)aminosulfony. L7benzoate and its ammonium salt as well as methyl 3-/(aminocarbonyl)aminosulfony.L7-2-ttiioptienecarboxylate were found to be most favourable.

According to the United States Patent Specification Nn. 4,34,3,649 1,8naphthalic acid anhydride, c,,, (cyanomettioxyimino) benzene: ace toni tr 11 e or N,N-diallyl-dictiloroacetanlide may be used to give a favourable result in the increase of selectivity of the herbicidally active 2ctiloro-Pl- -/-(4-mettioxy-6-mettiyl-1,3,5-triazin-2-yl)aminocarbony. L7benzenesulfonamide, 2,5dictiloro-N-/-(4,6-dimettioxypyridin-2yl)aminocarbony.17benzenesulfonamide or 2-carbomettioxy-N-/- (4, 6 dimethylpyrimi din- 2 -yl) aminoca rbony17 benzenesulfonamide.

Herbicide compositions containing a sulfonylurea derivative as active ingredient together with glycine derivatives as antidotes are published in the Hungarian Patent Specification No. 201,445.

The aim of the present invention was to develop herbicide compositions containing novel active ingredients, which possess more favourable physical and chemical properties, higher selectivity and lower persistency in comparison to the known sulfonylureas.

In the course of our investigations, compositions containing novel sulfonylurea derivatives of the general formula (I) have been developed which are characterized in that the N 3 atom (nitrogen in 3-position) of the sulfonylurea group substituted by a heterocyclic group bears an R 2 CH-OR 3 group wherein R 2 and R 3 are as defined above.

It has been found that compositions containing the novel compounds of the general formula (I) are particularly useful for weed control purposes since they show an excellent herbicidal effect in a suitable low dose, are appropriately selective against cultivated plants or can be made selective by using known antidotes and simultaneously, they are easily decomposed in the soil.

According to another aspect of the invention, there is provided a process for the preparation of the new compounds of general Formula (I) in inert organic solvents or a mixture thereof. This process comprises a) reacting an isocyanate or isothiocyanate of the general Formula (IV) 1 --p c-11 1 R 1 "'S02 - N C X (IV) wherein R I is as defined above, with an aminopyrimidine or aminotriazine derivative of the general formula (III) N R 4 HN -o E 2 N 1 / R 5 3 R CH - OR (III) wherein R 21 R 31 R 41 R 5 and E are as defined for formula (I), optionally in the presence of a base as catalyst, at a temperature of 0 to 50 0C, preferably between 20 0 C and 30 0 C; or b) reacting a sulfonylcarbamate derivative of the general formula (V), R 1 1 S02 - NH - COOR (V) wherein R 1 is as defined for formula (I) and R stands for phenyl group, with an aminopyrimidine or aminotriazine derivative of the general formula (III), wherein R 2, R 3, R 41 R 5 and E are as defined above, at a temperature of 25 to 120 OC, preferably between 60 0 C and 90 0 C; or c) reacting a carbamoyl chloride of the general formula (VI) R 4 7 N E O-N-COCI --, N R 5 R2- CH-OR3 i i V (VI) Z1 wherein R 2' R 3' R 4' R 5 and E are as defined above and R means phenyl group, with an alkaline metal salt of a sulfonamide of the general formula (II) R1 (0 c S02 - NH2 G I) wherein R 1 is as defined for formula (I), in the presence of a base as catalyst at a temperature between -10 0 C and 50 0 C, perferably between 0 0 C and 50 0 C; or d) reacting a N-pyrimidinyl- or N-triazinylcarbamate of the general formula (VII) R4 - N E o- N - COOR (Vii) P5 N 1 R2- CH -0p,3 wherein R 21 R 31 R41 R 5 and E are as defined above and R means phenyl group, with a sulfonamide of the general formula (II), wherein R 1 is as defined for formula (I), in the presence of a catalytic amount of a base at a temperature of 20 to 80 OC, preferably between 20 0 C and 40 0 C; or e) reacting a sulfonyl chloride of the general formula (VIII) R1 0 CO S02 - C' (VIII) wherein R 1 is as defined for formula M, with an aminopyrimidine or aminotriazine derivative of the general formula (III), wherein R 21 R 3 I. R 4 and R 5 are as defined above, and alkaline metal cyanates at a temperature of 20 0 C to 120 0 C, preferably between 60 0 C and 90 0 C.

1.

If desired, the compounds of general formula (I) prepared by using the above process variants may be converted to ttieir salts with alkaline metal or alkaline-earth metal hydroxides, amines or quaternary ammonium halides, e.g. by reacting the desired compound with the appropriate base in a suitable solvent, which is then evaporated.

In the preparation of compounds of the general formula (I) methylene chloride, chloroform, carbon tetrachloride, dichloroethane, trichloroethane, tetrahydrofuran, acetonitrile, dioxane, benzene, toluene, xylene, chlorobenzene, dimethylformamide, nitromethane, nitroethane, Nmettlylpyrrolidone, dimettioxyettiane, diethyl ether, diisopropyl ether, dibutyl ether, hexane, petroleum ether, ethyl acetate, butyl acetate, dibutyl phthalate as well as mineral and vegetable oils may be used as inert organic solvents but useful solvents are not restricted to those listed above.

In the above process variants the reaction temperature may be varied in a wide range usually from -20 0 C up to the boiling of the solvent used; however, it is preferred to react the components at a temperature between 0 0 C and 90 0 C, particularly at 15 to 45 OC since this temperature range is useful to prepare also the heat-sensitive derivatives of the general formula (I). The reactions are suitably carried out under atmospheric pressure, however an elevated or reduced pressure may also be used; the reactions can further be performed in the presence of air or unefer an inert gas e.g. nitrogen.

For shortening the reaction time or for completing the reaction a few drops of a base should be used as catalyst.

As catalytically active bases particularly tertiary amines such as triethylamine, tributylamine, N,N-dimethylaniline as well as nitrogencontaining heterocyclic compounds, e.g. pyridine or 1,4diazabicyclo-/2.2.27octane (DABCO) may be employed although alkaline metal hydroxides or alkaline metal alkoxides such as sodium hydroxide or sodium mettioxide are also useful. The catalysts being useful in the practice of the process variants are not restricted to those listed above.

The products prepared by using the above process variants can be separated by the complete or partial evaporation of the solvent and recrystallization; or by triturating an evaporation residue with a solvent or solvent mixture weakly dissolving the product. If necessary, the compounds obtained can be purified by chromatography on a suitable load, such as aluminium oxide, silica gel and the like.

i G The herbicide compositions according to the invention usually contain the active ingredient of general formula (I) in an amount of 0.01 to 95 % by weight, preferably 2 to 80 % by weight in the form of known formulations, e.g. solutions, emulsions, dusting powders, suspensions, wettable powders, pastes, soluble powders, granules, suspension concentrates or eMUlSifi2ble concentrates, natural or synthetic materials impregnated with the active ingredient or compositions encapsulated in polymeric substances.

The compositions are prepared by mixing and/or triturating the active ingredients with binding agents, solvents and/or carriers, optionally by the simultaneous use of surf2Ctants and/or dispersing as well as adhesionpromoting agents.

Useful solvents are: aromatic hydrocarbons, preferably C 7-12 fractions, e.g. toluene, xylene mixtures or substituted naphthalenes; chlorinated aliphatic or aromatic hydrocarbons, preferably chloroethylene, methylene chloride or chlorobenzene; aliphatic hydrocarbons such as cyclohexane, paraffins or mineral oil fractions; mineral or vegetable oils; alcohols, e.g. ethanol or ethylene glycol; or their ethers such as ethylene glycol monomethyl ether, ethyl ether; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone; strongly polar solvents, e. g. N-methylpyrrol i done, dimethylformamide, dimethylacetamide, dimethyl sulfoxide; plithalic acid esters, e.g. dibutyl phth2late or dioleyl phthal2te; as well as epoxidized vegatable oils such as epoxidized cocus oil or soybean oil; or water.

Suitable carriers are: inorganic powders such as kaolin, calcite, talc, chalk, quartz, attapulgite, montmorillonite, diatomaceous earth, perlite, amorphous silicon dioxide, aluminium oxide, highly disperse silicic acid, pumice, brick powder, sepiolite, bentonite, or sand; organic powders, e.g. flour-like powders prepared from plant parts such as corn-stalk or coconut-shell as well as corn flour; various types of starch, processed starch; sugar, e.g. glucose; powdered or ground synthetic resins, e.g. phenol or urea resins, In addition, a high number of inorganic or organic pre-granulated materials may be used.

Nonionic, cationic and/or anionic tensides may be employed as surfactants which possess favourable emulsifying, dispersing and wetting properties. Mixtures of tensides may also be used. The anionic tensides are watersoluble soaps, e.g. sodium or potassium salt of 0 oleic or stearic acid as well as the salts of natural fatty acid mixtures; however, it is mcre suitable to use synthetic tensides. particularly fatty alcohol SUlfonates, fatty alcohol sulfates, sulfonate-benzimidazole derivatives or alkylarylsulfonates. The calcium or triethanolamine salts of ligninsulfonic acid, dodecyl'SUlf uric acid esters, sulfonic acids prepared from natural fatty acids as well as sulfuric acid esters and sulfanic acids of fatty alcohol-ethylene oxide adducts, dodecylbenzenesulfonic acid or tributy1naphthalenesulfonic acid may be mentioned as examples. In addition, phosphates, e.g. salts of the phosphate ester of p-nonylphenol-(4-14)ethylene oxide adduct are also suitable.

As cationic tensides quaternary ammonium salts may be taken in consideration which contain lower alkyl groups substituted by halogen or hydroxyl group and/or a benzyl group bound to the quaternary nitrogen in addition to a C B-20 alkyl group. Examples of tensides of this type are e. g. stearyltrimethyl- ammonium chloride or benzyl-bis(2ctiloroettlyl)ettlylammonium bromide.

The nonionic tensides are mainly polyoxyethylene glycol ethers, polyoxyethylene glycol esters as well as esters of polyvalent alcohols and their condensation products, nonylphenol polyethoxyethanols, castor oil polyglycol ethers and polypropylene-polyethylene oxide adducts.

Ligninsulfonate, sulfite liquor and methylcellulose are e.g. useful dispersing agents.

The compositions may contain adhesion-promoting agents, e.g. carboxymethylcellulose, natural and artificial, powder-like, granular or latex-like polymers, e.g. polyvinyl alcohol, polyvinyl acetate as well as native phospholipids such as cephalin, lecithin or synthetic phospholipids.

In addition, the compositions according to the invention may contain other additives such as stabilizers, antifoam agents, viscosityregulating substances, preserving agents as well as inorganic or organic pigments.

Activating, synergistic, antidoting substances may also be incorporated to the compositions according to the invention.

The herbicide compositions containing known antidotes " such as DKA-24 (N-dictiloroacetyl-N-allylglycine N'-allylamide), AD-67 (N dictiloroacetyl-l-oxa-4-azaspiro/4,57decane), R-25788 (N,N-diallyl-di chloroacetamide), MG-191, TI-35 or CGA-92194 are also within the scope of the invention. (TI-35 is N-(dictiloroacetyl)-fiexamettiylene imine, CGA-92194 is N-(1,3-dioxolan-2-ylmettioxy)-imino-benzeneacetonitrile.) 1; _TC) 9 T If desired. t- compounds of the general formula M according to the invention and the compositions containing Same can be used in combination With other agrochemicals, which may be herbicides. fungicides, insecticides, miticides, nematocides, antiviral agents, plant gmfUica?ulating agents or attractants.

The compositions according to the invention preferably contain 0,01 to 95 %, more preferably 2 to 80 % by weight of active ingredient of the general formula (I) or a total of active ingredient and antidote, 5 to 99. 9 % by weight of liquid or solid carrier and 0 to 30, preferably 0.1 to 25 % by weight of surfactant and other additives. In the compositions containing also an antidote, the ratio of the antidote to the active ingredient may be 1:1 to 50:1.

Compositions with the components listed hereinafter are particularly preferred (percentages are throughout given by weight): 1. Solutions Active ingredient Solvent Surfact2nt 2. Emulsifiable concentrate Active ingredient Surf2Ct2nt Liquid Carrier 3. Wettable powder Active ingredient Surfactant Solid carrier 4. Suspension concentrate Active ingredient Water Surfactant Powder Active ingredient Solid carrier Granules Active ingredient Solid carrier 5.

6.

1 to 30 %, preferably 5 to 25 % 1 to 90 preferably 0 to 85 % 0 to 99 preferably 0 to 95 % 1 to 20 preferably 5 to 10 % 1 to 30 preferably 5 to 20 % to 94 preferably 70 to 85 0.5 to 90 preferably 20 to 80 % 0.5 to 20 preferably 5 to 15 % to 95 preferably 15 to 90 % to 75 %, preferably 10 to 50 % to 95 preferably 30 to 80 % 1 to 40 preferably 5 to 20 % 0.5 to 10 %, preferably 0.5 to 5 % to 99.5 %, preferably 95 to 99 % 0.5 to 30 %, preferably 1 to 15 % to 99.5 %, preferably 85 to 95 i The compositions according to the invention can be diluted to an active ingredient concentration of 0.01 % by weight with water before the use. The compositions may be applied onto the locus to be treated after or without dilution by using the common methods. e.g. spraying, dusting, atomization, spreading, sprinkling or the ultra low volume method. The compositions containing the novel sulfonylureas of the general formula (I) according to the invention possess an excellent herbicidal effect against both monocotyledonous and dicotyledonous, annual as well as perennial weeds. The compositions according to the invention can be applied before sowing or both in the preemergent or postemergent period.

When carrying out the treatment before emergence of the weeds on the soil without plants, the sprouting Plants shoot up and develop up to the cotyledon (seed-leaf) phase, then their growth stops and they perish partially or totally after 3 to 6 weeks. When carrying out the treatment after shooting up (emergence) of the weeds, the growth of the weeds stops after the treatment and the weeds perish partially or totally after 1 to 4 weeks. It is characteristic of the compositions according to the invention that they already show effect in an extraordinarily low applied amount. Depending on the weeds treated, the herbicidal effect is very good in doses of as low as 0.01 to 2.0 kg/hectare. The important large- scale cultures, e.g. wheat, maize, barley, rice and soy sorts were found to be resistant; tilUS, the compositions according to the invention are excellently useful for the control of both mono- and di.cotyledonous, annual and perennial weeds, which are difficult to kill or cannot be killed at all in the above cultures. Cultivated plants are not restricted to those mentioned above. Depending on the active ingredient employed, 0. 05 to 2.0 kg/flectare doses of compositions according to the invention can be used for a total weed control, too.

A particular advantage of compositions containing sulfonylureas of the general formula M as active ingredient appears therein that, after getting to the soil, they are rapidly decomposed therefore, when the compositions are postemergently used, the field area employed can be sown with other cultivated plants immediately after harvesting the host-plant or after a shorter period in comparison to the compositions containing known, commercially available sulfonylureas.

The preparation and use of the active ingredients /compounds of the general formula (I)/ and compositions according to the invention 11 are illustrated in detail in the following, non-limiting Examples.

Example 1 Preparation of 3-ettioxymettiyl-l-(2mettioxycarbonylptienylsulfonyl)-3(4-mettioxy-6-mettiy1-1, 3, 5 -tr i az in-2-yl)urea (compound No. 8) After adding 0.01 g of DABCO catalyst to a solution containing 3.96 9 (20 mmol) of 2-ettioxymettlylamino-4-mettioxy-6-mettiyl-1,3,5-triazine in 50 ml of anhydrous diethyl ether, 5.3 g (22 mmol) of 2mettioxycarbonylphenyIsulfonyl isocyanate dissolved in 20 ml of anhydrous diethyl ether are dropped to the above solution at room temperature under stirring. The reaction mixture is stirred for 6 hours while precipitation of the product begins. Next day the crystalline precipitate is filtered, washed with a little diethyl ether and then dried at room temperature to give 6.5 9 (74 % yield) of the title product, m.p.: 105-106 0 C.

Example 2 Preparation of 3-ettioxymettiyl-l-(2-ctiloroptienylsulfonyl)-3(4-mettioxy-6-methyl-1, 3, 5-tri azin-2-yl)urea (compound No. 4) 3.96 g (20 mmol) of 2-(ettioxymetfiyl)amino-4-mettioxy-6-met[iyl1,3,5- tri2zine are added to the solution of 6.23 g (20 mmol) of phenyl-N-(2cliloroptienylsulfonyl)carbamate in 120 ml of anhydrous benzene. The mixture is stirred at 75 to 80 0 C for 8 hours, then evaporated to dryness. After recrystallizing the residue from diethyl ether 5.06 g (61 %) of the title compound are obtained, m.p.: 123-123 0 C.

Example 3 Preparation of 3-(4,6-dimettlylpyrimidin-2-yl)-1-(2ctiloroptienylsulfonyl)-3- (ettioxymettiyl) urea (compound No. 2) 4.87 g (20 mmol) of N-(4,6-dimettiylpyrimidin-2-yl)-N- (ettioxymettlyl)carbamoyl chloride dissolved in 10 ml of dimethy1formamide are dropwise added to a solution containing 4.27 g (20 mmol) of 2-chlorobenzenesulfonamide sodium salt in 25 ml of anhydrous, redistilled dime thyl formami de at 5 to 10 OC while stirring. After the addition, the mixture is stirred at room temperature for 3 hours, then poured onto 250 ml of icewater. The precipitate is filtered, washed with a little water, dried and then C) recrystallized from a mixture of ethyl acetate and diethyl ether to obtain the title product in a yield of 3.34 g (42 %), m.p.: 118-119 0 C.

Example 4 Preparation of 3-(4,6-dimettiylpyrimidin-2-yl)-3-ettioxymettlyll-(2-mettic)xycarbonylphenylsulf onyl) urea (compound No. 6) After adding 3.1 g (10 mmol) of phenyl-N- (4, 6 -dimethylpyrimi din-2-yl)-N-(ettioxymettiyl)carbamate to the solution of 2.15 g (10 mmol) of 2-mettioxycarbonylbenzenesulfonamide and 1.52 g (10 mmol) of 1,Bdiazabicyclo/-5.4.0 - 7undec-7-ene in 25 ml of anhydrous dioxane, the reaction mixture is stirred at 30 to 35 0 C for 10 hours, then poured into 200 ml of water. After adjusting the pH value to 6.5 the precipitate is filtered, dried and then recrystallized from a mixture of chloroform and hexane to give 1.59 g (37.6 %) of the title compound, m.p.: 124 to 126 0 C.

Example 5 Preparation of 3-(4,6-dimettiylpyrimidin-2-yl)-3mettioxymettlyl-l-(2-mettioxycarbonylphenylsulf onyl) urea (compound No. 5) A mixture containing 4.3 g (20 mmol) of 2-methoxycarbonylbenzenesulfonyl chloride, 3.67 g (22 mmol) of 4,6-dimettlyl-2- (mettioxymetfiyl)aminopyrimidine and 3.24 g (40 mmol) of potassium cyanate in 30 ml of anhydrous acetonitrile is heated at 81 0 C under vigorous stirring for 2 hours. After filtering off the precipitated inorganic salt, the filtrate is evaporated, the residue is resuspended in 30 ml of water, then the precipitate filtered off is dried and recrystallized from a mixture of ethyl acetate and diethyl ether to give the title oompound in a yield of 5.4 g (66.2 Q, m.p.: 133-135 0 C.

The compounds listed in Table I are prepared similarly as described in the above Examples.

C - 13 Table I Compounds of the general formula (I), wherein X = oxygen Compound R 1 R 2 R3 R4 R 5 E M.p.

No. OC 1 cl H CH 3 CH 3 CH 3 CH 126-8 2 H H C2 H 5 CH 3 CH 3 CH 118-9 3 cl H CH 3 CH 3 CH 3 0 N 130-5 4 cl H C2 H 5 CH 3 CH 3 0 N 123-4 COOCH 3 H CH 3 CH 3 CH 3 CH 133-5 6 COOCH 3 H c 2 H 5 CH 3 CH 3 N 124-6 7 COOCH 3 H CH 3 CH 3 CH 30 N 112-5 8 COOCH 3 H c 2 H 5 CH 3 CH 3 0 N 105-6 9 COOCH 3 H C4 H 9 CH 3 CH 3 0 N 100-2 COOCH 3 H C4 H 9 CH 3 CH 3 0 N 103-4 11 H H CH 3 CH 3 CH 3 0 N 125-7 Example 6 Preparation of a wettable powder (10 WP) Components weighed in: Active ingredient prepared according to Example 2 Silicate carrier (Zeolex 444) Siliceous earth (diatomaceous earth) 9 20 80 Sodium aliphatic sulfonate wetting agent (Netzer IS) 4 Cresol formaldehyde sulfonate dispersing agent (Dispergiermittel 1494) 6 Sulfite liquor powder (Borresperse NA) 10 The powder mixture is crushed in a laboratory ball mill for 30 minutes, then ground to fine particles in an Alpine 63 C-type laboratory contraplex mill at a speed degree of 70. The thus obtained wettable powder composition contains the compound No. 4 of Table I as active ingredient in an amount of 10 % by weight.

Floatability (in 1 % concentration): 86.5 %.

Wet sieve residue (on a sieve of DIN 10): 0.27 %.

Example 7 Preparation of a wettable powder (50 WP) c - 14 Components weighed in: Active ingredient prepared according to Example 3 Synthetic silicate carrier (Zeolex 444) Siliceous earth Sodium aliphatic sulfonate (Netzer IS) Cresol-formaldehydesulfonate Sulfite liquor powder The process described in Example 6 is followed The thus obtained wettable powder composition contains the compound No. 2 of Table I as active ingredient in an amount of 50 % by weight.

Floatability (in 1 % concentration): 82.9 %.

Wet sieve residue (on a sieve of DIN 100): 0.43 %.

Example 8 Preparation of a wettable powder (85 WP) Components weighed in: q Active ingredient prepared according to Example 4 170 Synthetic silica carrier (Sipq! rnat. 50 S) 20 Sodium oleyl methyl laurate (Arkopon T plv.) 4 Cresol-formaldehydesulfonate 6 The process described in Example 6 is followed.

The thus obtained wettable powder composition contains the compound No. 6 of Table I as active ingredient in an amount of 85 by weight.

Floatability (in 1 % concentration): 82.9 P-2.

Wet sieve residue (on a sieve of DIN 100): 0.43 Example 9 Preparation of an emulsifiable concentrate (5 EC) Components weighed in: Active ingredient prepared according to Example 1 Xylene Cyclohexanone Calcium dodecylbenzenesulfonate (Emulsogen IP 400) Fatty acid polyglycol ester (Emulsogen EL 400) 1 9 5 70 15 8 2 C The active ingredient is dissolved in the mixture of xylene and cyclohexanone under stirring and 8 g of Emulsogen IP 400 as well as 2 g of Emulsogen EL 400 emulsifying agents are added. After homogenization the mixture is filtered.

The thus obtained emulsifiable concentrate contains the compound No. 8 of Table I as active ingredient in an amount of 5 % by weight.

Emulsion stability (1 % concentrate in CIPAC A and CIPAC D water): stable after 2 hours.

A reversible creamifiC2tion is observed after 24 hours.

Example 10 Preparation of dusting powder (5 D) Components weighed in: Talc Silicate (Sipernat 50 S) Active ingredient prepared according to Example 5 Limestone grist (M 10) 9 20 30 50 900 The mixture of the active ingredient prepared according to Example 5, the synthetic silicate carrier and talc are crushed in a laboratory ball mill, then ground to fine particles in an Alpine 63 C-type laboratory contraplex mill. The grist is homogenized with limestone grist in a laboratory powder mixer.

The thus obtained dusting powder contains the compound No. 5 of Table I as active ingredient in an amount of 5 % by weight.

Sieve residue (on a sieve of DIN 100): 0.12 %.

Example 11 Preparation of a suspension concentrate (5 FW) Components weighed in: Active ingredient prepared according to Example 2 Sunflower oil Organophilic bentonite (Ivegel) Polyethylene alkyl ether, polyoxyethylene castor oil, ettioxylated fatty acids and sodium sulfosuccinate (Sorpol 3615) q 10 168 2 j -1" 16 - The active ingredient, sunflower oil, organophilic bentonite (Ivegel) and Sorpol 3815 emulsifyingagent are weighed into a laboratory bead-mill. The suspension concentrate is ground together with 65 % by volume of glass-bead load of 1.0 to 1.5 mm in diameter at 775 rpm for 30 minutes.

The thus obtained suspension concentrate contains the compound No. 4 of Table I as active ingredient in an amount of 5 % by weight.

Stability (1 % concentrate in CIPAC and CIPAC D water): stable after 30 minutes.

Example 12 Preparation of suspension concentrate (40 FW) Components weighed in: Active ingredient prepared according to Example 1 Synthetic silicate (Zeolex 444) Sodium oleyl methyl tauride (Arkopon T plv.) Nonylphenyl polyglycol ether (Arkopal N 100) 2 % Xanthan gum (Kelzen S) solution Water 9 80 6 10 80 9 of the active ingredient prepared according to Example 1, synthetic silicate (Zeolex 444), sodium oleyl methyl tauride (Arkopon T) and nonylphenyl polyglycol ether (Arkopal N 100) wetting dispersing agent as well as 80 9 of water are weighed in a laboratory bead-mill. After homogeinization, the suspension concentrate is ground together with 70 % by volume of glass-bead load of 1.0 to 1.5 mm in diameter for 30 minutes. After grinding and separating from the load, the mixture is homogenized with 20 9 of 2 % xanthan gum (Kelzen S) solution in an Ultra turrax equipment under vigorous stirring.

The thus prepared suspension concentrate contains the compound No. 8 of Table I as active ingredient in an amount of 40 % by weight. Floatability (in 1 % concentration): 97.3 % Particle size (below 10 /u): 91.6 % 1 1 17 Example 13 Preparation of water-dispersible granules (75 WDG) Components weighed in: Compound No. 3 of Table I as active ingredient Synthetic silicate carrier Polyvinylpyrrolidone (K 30 product of BASF) Alkylphenol ether phosphate (Atlox 5330 product of ICI) Mixture of polyalkylene glycol ether and polymethylene alkylaryl ether (Atlox 4896 product of ICI) Water 9 375 55 20 30 180 375 g of compound No. 3 of Table I as active ingredient are pre-crushed (pre-ground) with 55 g of synthetic silicate carrier in a laboratory ball mill, then the mixture is ground to fine P2rticles in an Alpine 63 C-type contraplex mill at a speed degree of 80. The granulating liquid is prepared by dissolving 20 g of polyvinylpyrrolidone, 30 9 of alkylphenol ether phosphate and 20 g of a mixture Of pOly2lkylene glycol ether and polymethylene alkylaryl ether in 180 ml of water. The ground powder mixture is introduced to an FPG 0.5 type batch-operation (periodically operated) granulating apparatus with fluidizing atomization and brought into 2 fluidized. state by regulating the air stream entering with a temperature of 60 to 65 0 C. When the inlet temperature reaches 30 0 C, the evaporation of the granulating liquid is started under a pressure of 1.5 bar and the volume of the air flow is increased depending on the particle growth. After introducing the granulating liquid the drying is continued until the outlet temperature reaches 36 to 38 oc.

The thus prepared granules contain the compound No. 3 of Table I as active ingredient in an amount of 75 % by weight.

Floatability (in 1 % concentration after 30 minutes): 93.7 % Particle size between 0.2 and 1 mm: at least 75 % Example 14 Preparation of water-dispersible granules (25 WOG) _.e n Components weighed in: Compound No. 7 of Table I as active ingredient Synthetic silicate carrier Maltodextrin binding agent Ligninsulfonate (Sorpol 9D 47 K product of Toko) Polyoxyethylene polyalkylaryl phenyl ether sulfate (Sorpol 5096 product of Toko) p 125 250 75 30 The compound No. 7 of Table I as active ingredient, synthetic silicate carrier, maltodextrin binding agent as svell as ligninsulfonate (Sorpol 90 47 K product of Toko) and polyoxyethylene polyalkylaryl phenyl sulfate (Sorpol 5096 product of Toko) tenside are weighed in a laboratory ball mill. After grinding for 30 minutes, the powder mixture is ground to fine particles in an Alpine 63 C-type contraplex mill. The grist is introduced into an FPG 0.5-type batch-operation (periodically operated) fluidization apparatus with fluidizing atomization and brought into a fluidized state by regulating the air stream having an inlet temperature of about 60 0 C.

The granulation is carried out by atomized water when the outlet temperature reaches 28 to 30 0 C. After obtaining the desired particle size of about 0.5 mm, the atomization of the water is stopped and the drying is continued until the outlet temperature reaches 36 to 36 0 C.

The thus prepared granules contain the compound No. 7 of the Table I as active ingredient in an amount of 25 % by weight.

Floatability (in 1 % concentration after 30 minutes): 91.85 % Particle size between 0.2 and 1.0 mm: at least 95 %.

Example 15 Preparation of a suspension concentrate (14.5 FW) Components weighed in: Compound No. 8 of Table I as active ingredient OKA- 24 (N-dictiloroacetyl-N-allylglycine W-allylamide) as antidote Zeolex 444 carrier Monoethylene glycol Arkopon T wetting agent Arkopol N-090 (nonylptien)tl polygl.6o'L ether) dispersing agent 12.5 11.6 15 3 6 C.

Water 2 % by weight xanthan gum solution as thickening agent 39.9 g The suspension concentrate containing the active ingredient (compound No. 8 of Table I) and the OKA-24 antidote in a total amount of 14.5 % by weight in a weight ratio of 1:6.25 is prepared as described in Example 12.

Example 16 Preparation of a suspension concentrate (27.0 FW) Components weighed in: Compound No. 8 of Table I as active ingredient R- 25788 (N,N-diallyl-dictiloroacetamide) as antidote Zeolex 444 carrier Monoethyleneglycol Arkopon T wetting agent Arkopol N-090 dispersing agent Water 2 % by weight xanthan gum solution thickening agent q 2 25 5 10 2.5 5.5 42 8 The process describe in Example 12 is followed to obtain a suspension concentrate containing the active ingredient (compound No. 8 of Table 1) and the R-25788 antidote in a total amount of 27 % by weight in a weight ratio of 1:12.5.

Example 17 Preparation of a wettable powder (20.25 WP) Components weighed in: Compound No. 4 of Table I as active ingredient AD- 67 (N-dictilaroacetyl-l-oxa-4-azaspiro/4.57decane) as antidote Zeolex 444 carrier Siliceous (diatomaceous) earth Netzer IS wetting agent Dispergiermittel 1494 dispersing agent q 1.5 18.75 34.75 33.0 3 4 0 Sulfite liquor powder dispersing agent g The process described in Example 6 is followed to obtain a wettable powder composition containing the active ingredient (No. 4 of Table I) and the AD-67 antidote in a total amount of 20.25 % by weight in a weight ratio of 1:12.5.

Example 18 Preparation of water-dispersible granules (13.5 WOG) Components weighed in: Compound No. 6 of Table I as active ingredient CGA- 92194 /N-(1,3-dioxolan-2-ylmettioxy)imino-benzeneacetonitrile7 as antidote Synthetic silicate carrier Maltodextrin binding agent Ligninsulfonate (Sorpol 90 47 K) Polyoxyethylene polyalkylaryl. phenyl. ether sulfate (Sorpol 5096) 9 1 12.5 6M 5 15 6 4 The process described in Example 14 is followed to obtain waterdispersible granules containng the active ingredient (compound No. 6 of Table I) and the antidote (CGA-92194) in a total amount of 13.5 % by weight in a weight ratio of 1:12.5.

Example 19 Preparation of a wettable powder (51.2 WP) Components weighed in: Compound No. 2 of Table I as active ingredient OKA- 24 as antidote Zeolex 444 carrier Siliceous earth carrier Netzer IS wetting agent Cresol-formaldellydesulfonate Sulfite liquor powder dispersing agent g 20 31.2 14.4 24.4 2 3 5 The process described in Example 6 is followed to obtain a wettabl powder composition containing the active ingredient (compound No. 2 of 1 Y 0 Table I) and the antidote (OKA-24) in a total amount of 51.2 % by weight in a weight ratio of 1:1.56.

Example 20 Preparation of a wettable powder (24.75 WP) Components weighed in: Compound No. 2 of Table 1 as active ingredient MG- 191 (2-dictiloromettiyl-2-mettiyl-1,3-dioxolane) as antidote Zeolex 444 carrier Siliceous earth carrier Netzer IS wetting agent Dispergiermittel 1494 dispersing agent Sulfite liquor powder dispersing agent 6 18.75 33 32.25 2 3 5 The process described in Example 6 is followed to give a wettable powder composition containing the active ingredient (compound No. 2 of Table I) and the antidote (MG-191) in a total amount of 24.75 % by weight in a weight ratio of 1:3.125.

Example 21 Preparation of a dusting power (5.2 0) Components weighed in: Compound No. 5 of Table I as active ingredient AD- 67 as antidote Talc Synthetic silicate carrier (Sipernat 50 S) Limestone grist (M 10-type) q 2 50 19 29 900 The process described in Example 10 is followed to give a dusting powder containing the active ingredient (compound No. 5 of Table I) and the antidote (AD-67) in a total amount of 5.2 % by weight in a weight ratio of 1:25.

-we 0 Example Preparation of a wettable powder (21 WP) Components weighed in: Compound No. 6 of Table I as active ingredient DKA- 24 as antidote Zeolex 444 carrier Siliceous earth carrier Dispergiermittel 1494 dispersing agent Netzer IS wetting agent Sulfite liquor powder p 1 20 30 39.5 3 4.5 The process described in Example 6 is followed to obtain a wettable powder containing the active ingredient (compound No. 6 of Table I) and the antidote (DKA-24) in a total amount of 21 % by weight in a weight ratio of 1:20.

Example 23 Preparation of a dusting powder (6 0) Components weighed in: Compound No. 4 of Table I as active ingredient DKA- 24 as antidote Talc Synthetic silicate carrier (Sipernat 50 S) Limestone grist (M 10-type) 50 15 25 900 The process described in Example 10 is followed to give a dusting powder composition containing the active ingredient (compound No. 4 of Table I) and the antidote (DKA-24) in a total amount of 6 % by weight in a weight ratio of 1:5.

Example 24 Preparatiop of a suspension concentrate (22 N) 41 0 Components weighed Compound No. 2 of Table I as active ingredient DKA-24 as antidote Zeolex 444 carrier Arkopon T wetting agent Arkopol N-100 wetting agent 2 % by weight xanthan gum solution as thickening agent Water 9 2 20 6 4 10 48 The process described in Example 12 is followed to give a suspension concentrate containing the active ingredient (compound No. 5 of Table I) and the antidote (DKA-24) in a total amount of 22 % by weight in a weight ratio of 1:10.

Example 25 Greenhouse test of the postemergent effect (effect on emerged plants) The seeds of the test plants were sowed into a mixture containing 1/3 part of sand, 1/3 part of clay and 1/3 part of floresca chernozem soil placed in 200 ml. plastic bottles containing 4 holes at their bottom.

After sowing, the soil and the sm517 plants, respectively emerged were daily sprinkled at a temperature of 20 to 26 OC under natural illumination supplemented with an illumination of 4 hours. The 10 WP composition prepared from the compounds Nos. 3, 5, 6, 7 and 8, respectively of Table I according to Example 6 were sprayed by using 1000 litres per hectare of water under a pressure of 4 bar onto the 2 to 4- leaf plants by using a greenhouse sprayer.

The damages (injuries) of the test plants were evaluated in the 2nd and 4th weeks following the spraying. The damages of the various test plants are given as percentage; 0 % means no damage and 100 % means total perishment.

The results are summarized in Table II. It can be seen that the compositions according to the invention possess a good herbicidal effect and a favourable selectivity against the cultivated plants. The compounds Nos. 3, 7 and 8 proved to be particularly effective.

In the first column of Table II and the following Tables, the Roman numeral I refers to Table I and the Arabic numeral refers to the i c - 24 number of the compound in Table I.

Table II

Postemergent effect Compbund No. Dose Perishment of the test plants (%) (in Table I) g/ha ORYS STEM ECHC GALA MATI ZEAM HELA GLYM TRIE 1/3 270 30 100 80 100 100 20 100 80 0 0 100 60 80 100 0 100 30 0 0 100 0 40 90 0 40 30 0 0 100 0 30 30 0 0 0 0 1/5 270 100 100 100 80 100 100 100 100 100 1/6 270 90 100 100 35 70 100 100 80 100 80 100 100 30 50 90 100 50 90 1/7 270 10 100 100 60 100 10 100 70 0 10 100 100 50 100 10 100 60 0 0 100 20 25 90 0 40 0 0 0 100 0 0 30 0 40 0 0 1/8 270 20 100 100 70 100 100 100 90 0 20 100 90 50 100 20 100 60 0 0 100 30 40 90 10 100 40 0 0 100 0 30 90 0 70 10 0 Abbreviations in Table II:

DRYS Oryza sativa STEM Stellaria media ECHC Echinochloa c.g. GALA Galium aparine MATI Matricana inodor ZEAM Zea mays HELA Helianthus annuus GLYM Glycine max THE Triticum aesticum c Example 26 Greenhouse test of the preemergent effect The seeds of the test plants were sowed in 3 repetitions into a medium- impermeable forest soil placed in a bottom-perforated paper 2 box of 7 cm in height with a footing area of 200 cm. The boxes of the separate treatments were placed on plastic trays equipped with a wetting cloth. After sowing, before the emergence of the plants, the 10 WP composition prepared from compound No. 7 of Table I according to Example 6 was applied with a water amount corresponding to 1200 litres per hectare onto the soil surface in the boxes by using a greenhouse microsprayer. The supplementation with water was ensured by maintaining the wetting cloth in a wet state. The experiment was carried out at a temperature of 20 to 28 OC under natural illumination supplemented with an illumination of 4 hours. The herbicidal effect of the compound No. 7 of Table I was evaluated in the 4th and 6th weeks after spraying. The results are summarized in Table III.

Table III

Preemerqent effect Compound No. Dose Perishment of test plants (%) (in Table I) g/ha Solanum Digitaria ECHC STEM TRIE miqrum adans 1/7 250 70 50 20 100 0 1000 100 60 40 100 0 Example 27 Investigation of the effect on cultivated plants in the plant- cultivating chamber 400 9 of field top soil each (with a pH value of 6.5, permeability of 50 and humus content of 1.4 %) were weighed in plastic cultivating bottles of O.B dm 2 surface each lined with PVC foil. Onto this soil 10 seeds of Pi-3737 maize each, 100 seeds of streaked sunflower "IREG", each. 50 seeds of SA-114 sorghum each and 1 9 of red millet each were sowed.

After covering the seeds with 100 g of soil each, the treatments were carried out. In the course of these treatments 10, 20, 40, 80, 160 or 320, respectively g per hectare doses of water -di spers ible granules (75 WDG) prepared according to Example 13 from the compounds Nos. 2, 4, 5, 6 and 8, respectively, as well as of Ally, Tell, Granstar, Glean, Logran and SL-950, respectively, control compositions were applied in four repetitions. The treated soil surface was again covered with additional 100 g of soil in each bottle.

The bottles were placed in plant-cultivating chambers, sprinkled daily up to their water capacity and cultivated under HGMF/D 400 sunshinesubsituting lamps with a daily illumunaion period of 16 hours. The experiment was evaluated on the 10th day after sowing when the green weight of sunflower, sorghum and millet as well as the green weight and shoot length of maize were determined. The results obtained are summarized in Table IV with the designation "Sowing I".

The seeds of maize, sunflower and millet were repeatedly sowed 6 times into the soil of the experiment evaluated. The results of evaluation of these latter experiments are summarized in Tables V to IX with the designations "Sowing II, III, IV, V, VI".

From sowing I up to the evaluation of sowing VI 76 days elapsed.

11 I.)' Table IV

Development of the green weight of Pi-3737 maize and the sunflower "IREG" under effect of the treatments (given as percentage of the untreated control) Treatments Green weight of maize Green weight of sunflower Dose of active ingredient 160 320 10 20 40 80 320 Ally 59 48 18 8 1 7o 77 67 58 68 4o 1/ 8 77 78 76 56 44 12 119 91 79 88 68 6o 1/4. 01 81 82 56 33 29 145 112 112 81 72 68 1/6 84 6o 22 lo 3 11 121 1o7 97 53 65 6o 1/2 98 1o7 95 86 71 55 125 112 109 88 53 84 1/5 62 74 22 6 a - 83 86 61 74 7o 59 Glean 66 37 16 lo 7 6o 56 49 47 53 77 Tell loS 1o7 65 82 81 7o 65 67 82 63 58 51 Logran 8o 81 62 4o 37 41 61 67 74 7o 6o 56 SL-95o 96 112 ill 108 99 96 ill 114 1o2 81 5o 56 Granstar 84 86 loo 88 57 3o 119 1o2 1o7 97 98 6o n 4 Continuation of Table IV Development of the green weight of millet and sorghum upon effect of the treatments (given as percentage of the untreated control) Treatments Green weight of maize Green weight of sunflower Dose of active ingredient (g/ha) 20 40 80 160 320 10 20 40 80 160 320 Ally 2, 76 46 67 26 13 97 B3 77 56 27 7 1/8 9 21 28 52 18 14 147 126 152 141 Bo B4 1/4 66 32 41 27 62 26 '153 144 169 125 115 165 1/6 15 61 43 5o 22 6 132 1o2 68 14 - - 1/2 66 69 65 B9 67 35 136 1o7 1o7 116 94 111 1/5 78 61 88 45 6 6 115 58 19 8 - 2 Glean 48 67 96 42 39 21 129 85 67 67 75 46 Tell 66 16 51 7 45 31 80 63 16 - - 1 SL-95o BO 4o 55 34 57 15 11B 91 108 54 21 17 Granstar 23 77 77 69 81 64 133 1o3 158 139 127 91 Logran 38 19 3 50 73 45 104 97 117 113 90 80 0 ' Table V Results of sowing II Green weight of maize Green weight of sunflower Treatments Oose of active ingredient (g/ha) 20 40 80 160 320 10 20 40 Ally 133 1o5 1o7 51 35 5B 46 53 72 1/8 126 109 116 loo 109 65 75 72 56 1/4 1o4 84 125 90 12o 84 loo 117 121 1 1/6 1o2 137 12o 03 35 lo 75 loo 1o2 m 1/2 91 ill 127 123 118 116 65 BB 124 1/5 137 121 127 58 19 23 88 129 B3 Glean 98 88 65 46 19 12 7o 6o 63 Tell 127 147 13o 132 118 121 56 93 61 Logran 133 114 116 12o loo 47 46 56 56 SL-95o 93 loo 1o7 127 1o2 13o 77 88 82 Granstar 1o7 13o 137 so 116 139 61 77 112 C) Table V continued Green weight of sunflower Green weight of sorghum Treatments Dose of active ingredient (g/ha) so 160 320 10 20 40 80 160 320 Ally 50 42 47 1o5 F37 74 62 17 13 1/6 68 75 97 82 1o2.. 35. 76 loo 1/4 128 122 113 99 05 B5 129 129 1o4 116 61 7o 58 1o7 51 96 41 lo 1/2 114 79 82 - 58 3o 97 86 98 1/5 56 51 47 88 61 B2 38 2 - Glean 53 58 79 - 136 85 95 72 6o Tell 77 56 68 4o 96 84 64 8 - Logran 49 74 67 - 1o6 91 73 65 69 SL-95o 58 66 50 42 84 89 65 34 32 Granstar 95 95 '1 LL B7 91 99 73 129 (7) ' Table VI Results of sowing III Treatments Ally 1/8 1/4 1/6 1/2 1/5 Glean Tell Logran SI-950 Granstar 90 85 107 113 93 97 75 100 118 100 81 40 92 60 107 88 93 108 103 68 92 86 100 83 79 76 95 100 117 97 97 115 10B 92 Green weight of maize Green weight of sunflower Dose of active ingredient (g/ha) 160 320 10 20 40 80 160 320 10 73 89 97 79 86 53 54 113 71 17 22 66 93 81 81 75 1 78 105 32 24 34 32 97 93 93 86 98 109 76 86 49 46 81 77 106 11(1 93 76 107 127 102 71 54 39 112 96 54 74 83 120 57 108 4B 43 73 56 107 67 70 80 96 107 81 53 67 49 84 70 51 67 100 107 BB 110 Green weight of sorghum 40 61 51 69 63 76 48 100 84 54 32 54 47 53 51 56 43 64 61 97 59 99 90 92 83 89 108 99 116 83 104 78 B9 64 77 25 61 60 86 85 113 113 00 61 126 96 96 62 122 98 76 67 16 80 71 67 36 101 54 96 22 93 36 77 320 36 74 121 107 4 53 4 74 12 96 1 W 1-1 1 -0,., Table VII

Results of sowing IV Treatments Green weigtit of maize Green weight of sunflower Dose of active ingredient (9/ha) 320 10 20 40 80 160 320 10 Ally 75 56 39 44 14 14 43 43 37 34 40 35 1/0 95 97 62 66 66 74 63 40 55 1/4 81 90 70 1/6 97 1/2 92 1/5 Glean Tell 63 60 55 99 Granstar 78 Logran SL-950 1, 81 74 102 73 77 71 04 53 93 99 99 95 92 124 109 117 04 53 77 37 56 30 67 1 128 70 51 100 106 84 48 77 21 94 57 79 83 65 69 75 54 93 63 52 56 73 66 44 67 56 97 76 75 72 68 55 83 72 66 52 53 77 76 Green weight.of sorghum 37 38 53 43 87 74 32 36 47 46 57 50 41 61 106 108 09 70 38 55 36 55 32 40 120 40 101 30 58 72 84 98 73 98 40 93 59 96 93 92 109 86 88 90 94 81 108 72 94 74 76 107 69 101 93 86 ill 82 08 70 44 61 26 89 99 320 46 42 93 104 12 19 90 122 7 66 24 89 37 110 103 2 64 3 81 29 1 W N 1 0-, Treatments Table VIII Results of sowing V Green weight of maize Green weight of sunflower Dose of the active ingredient (g/ha) Green weight of sorghum 20 40 80 160 320 10 20 40 80 160 320 10 20 40 80 160 320 Ally 76 87 76 71 60 31 79 71 56 69 46 63 134 137 109 84 105 52 1/8 109 93 93 97 87 86 86 89 90 100 74 73 101 124 144 106 134 138 1/4 94 107 91 96 85 85 97 131 130 114 114 71 76 96 102 124 130 118 116 96 108 101 91 57 44 66 91 86 89 76 61 50 80 79 60 54 22 1/2 95 86 97 83 99 94 99 104 111 115 105 81 114 123 109 121 100 108 1/5 119 95 107 92 87 41 107 108 115 83 82 57 64 109 73 63 24 4 Glean 89 83 79 57 29 24 80 98 67 51 54 51 139 59 104 144 109 93 Jell 93 100 80 117 103 99 71 B4 98 91 87 41 87 75 72 86 63 36 Logran 92 108 102 98 102 92 73 70 83 79 70 148 134 86 107 105 95 117 51-950 87 95 98 106 117 93 162 94 70 128 105 71 01 79 86 86 34 33 Granstar 95 110 98 100 99 87 115 71 80 94 120 101 151 80 87 95 106 122 0 Table IX Results of sowing VI Green weight of maize Green weight of sunflower Green weight of sorghum Treatments Dose of the active ingredient (g/ha) 20 40 80 160 320 10 20 40 80 160 320 10 20 40 80 160 320 Ally 108 113 87 83 61 50 60 79 74 77 01 52 93 123 119 104 70 53 1/8 100 90 92 76 86 85 04 86 100 97 79 71 105 103 101 B2 101 95 1/4 101 91 96 101 81 81 81 109 102 132 71 66 139 110 112 90 88 86 1/6 101 102 100 97 58 93 98 135 125 109 88 79 100 106 65 89 2 54 1/2 100 103 100 89 93 85 148 88 124 96 85 90 101 127 120 115 113 89 1/5 100 113 104 91 81 29 87 82 116 140 92 69 65 112 116 B7 30 7 Glean 99 100 83 96 46 29 81 90 65 72 66 82 130 129 123 96 106 102 Tell 100 89 96 126 120 124 112 137 92 90 95 81 106 93 105 122 99 52 Logran 97 96 93 10B 122 102 50 92 73 55 50 56 106 119 139 103 106 95 SL-950 97 105 106 98 115 109 134 95 103 98 76 9If 92 104 95 71 58 24 Granstar 95 101 93 96 97 97 92 B7 102 84 105 98 112 92 105 80 106 83 1 1 Example 28 Test of the herbicidal activity in a field experiment carried out in a winter-wheat culture

A postemergent weed control experiment was performed on Winterwheat in parcels of 10 m 2 each near to the river Sebes-Kdrbs.

The test was carried out on a meadow-clay soil-type having pH value of 6. 3 containing 3.4 % of organic material. Winter-wheat was used as green crop. The seeds were sovied on 24th October in a well-processes dry seedbed to a depth of 6 to 7 cm with a row distance formed by direct sowing.

The test was performed postemergently on 20th April. The weed species and their development stage at the time of treatment were: burweed (Galium aparine, abbreviated GALAP) in 4 to 6-leaf-vitiorl stage; red blindnettle (Lamium purpureum, LAMPU) in flowering stage; meadow-veronica (Veronica arvensis, VERAR) in budding period at the beginning of flowering; medicinal earth-gall (Fumaria officinalis, FUMOF) in the 61eaf stage; chickweed (Stellaria media, STEME) in the flowering state; eastern larkspur (Consolida orientalis, CONOR) of 10 cm in height, in the stemforming period; white goosefoot (Chenopodium album, CHEAL) in 2 to 6-leaf stage; fallow bindweed (Bilderdyckia convolvulus, BILCO) in a 2 to 3-leaf stage. On establishing the experiment a parcelspraying machine was used with propane-butane gas pressure. Doses of 10 to 30 g of active ingredient per hectare of the compounds Nos. 4, 5, 6 and 8, respectively, of Table I were applied in 500 litres per hectare of spray liquid in the form of 5 FW suspension concentrates formulated according to Example 11. The same doses of Logran 75 OF and Granstar 75 OF, respectively, were used for comparison.

The herbicidal and phytotoxic effects of the treatments carried out within these examinations were evaluated by using a score (scale) from 0 (inactive) up to 100 (total perishment). These evaluations were performed 4 times (on27th April, 4th May, 25th May and 18th June) in the vegetative period following the treatment by measuring the number 2 of spikes (piece/ m), spike-length (cm) and the weight of 1000 grains (g). The results, which are the average values of 4 repetitions, are summarized in Tables X to XVI.

k. 1) Table X

Herbicidal effect Phytotoxytity Treatment Oose ' Time 6f GALAP LAMAM LAMPU VERAR FUMOF STEME CONOR CHEAL BILCO % g/ha evaloation 1/0 10 11 0 0 20 0 4 0 11 21 0 34 20 34 16 19 15' 0 50 35, 0 111. 53 79 89 91 30 72 0 85 91 0 IV. 46 90 94 96 20 - 0 90 1/0 20 1. 20 0 0 14 0 5 0 15 23 0 25 5 21 23 33 8 53 46 0 85 90 91 43 93 0 99 98 0 IV. 56 90 94 99 23 - 0 99 99 0 1/8 40 1. 213 0 6 18 0 8 4 20, 33 13 48 29 39 31 5 35 0 53 56 14 7B 93 92 95 57 99 4 99 99 - 0 IV. 75 99 99 99 30 0 100 100 0 33 0 10 21 0 4 8 33 33 18 5B 38 43 38 30 16 18 55 60 15 94 93 96 98 8B 99 13 99 99 0 IV. 96 100 100 100 66 15 100 100 0 r) Table XI

Bose Time of Herbicidal effect % PhytotoxicjEy Treatment g/ha evaluation GALAP LAMAM LAMPU VERAR FUMOF STEME CONOR CHEAL BILCO 1/4 10 1. 13 0 0 13 0 0 0 15 11 0 1/4 11. 44 25 16 21 ' 35 15 0 36 43 0 111. 72 79 86 72 58 74 0 85 92 0 IV. 66 86 92 75 40 - 0 90 90 0 1/4 20 1. 19 0 0 15 0 0 0 16 16 0 11. 48 16 33 24 34 25 0 23 29 20 1 111. 91 88 89 87 80 94 0 69 94 0 A IV. 80 92 96 90 66 - 0 96 100 0 --j 1/4 40 1. 20 0 0 19 0 0 6 18 19 75 11. 55 39 30 33 34 17 10 60 63 20 M. 92 96 95 88 61 99 0 99 99 0 iv. 90 100 100 94 75 0 100 100 0 1/4 80 1. 23 0 5 21 0 0 5 16 28 15 11. 49 23 31 16 15 25 6 44 58 30 111. 97 97 98 98 84 100 16 99 99 35 IV. 100 100 100 100 75 15 100 100 33 a 1 1 0 1 Table XII

Dose. Time of. - Treatment g/ha evaluation GALAP LAMAM Herbicidal effect LAMPU VERAR FUMOF STEME CONOR CHEAL BILCO 1/6 10 1..0 0 0 0 0 0 0 15 11 19 11. 13 0 18 13 38 21 0 30 33 33 111. 20 10 0 0 25 25 0 41 46 35 IV. 20 0 0 0 28 - 0 37 56 30 Ptiytntrixicity 1/6 20 1. 0 0 0 0 0 0 0 14 17 20 11. 5 21 0 10 28 23 0 40 41 33 111. 24 0 0 0 25 38 0 66 68 46 IV. 27 0 0 0 31 0 72 80 54 %-4 CO I / 6-:- 40 1. 5 0 14 5 0 0 0 26 20 24 11. 25 21 29 3 20 15 0 45 45 36 111. 28 18 26 9 51 48 0 76 75 70 IV. 2B 10 23 0 46 - 0 80 82 86 1/6 80 1. 11 0 14 8 8 0 0 34 31 21 11. 32 23 9 20 14 15 0 73 53 25 111. 30 24 32 15 61 50 0 95 99 76 IV. 25 17 20 13 60 - 0 99 100 89 - 1 0' Table XIII

Dose Time of Herblcidal effect o,- Treatment GALAP Pbytotoccity g/ha evaluation LAMAM LAMPU VERAR FUMOF STNE CONOR CHEAL VLCO 1/5 10 0 0 0 0 0 0 0 14 11 5 0 8 0 0 36 0 0 36 26 40 19 0 0 0 34 0 0 59 54 46 IV. 20 0 0 0 37 - 0 64 66 54 1/5 20 1. 5 0 0 0 0 0 0 14 16 5 8 5 0 5 40 0 0 13 23 33 0 a 0 34 0 0 60 69 59 IV. 33 0 0 0 40 - 0 72 80 66.

1/5 40 L 10 0 10 0 0 0 0 20 14 14 11. 9 5 15 15 31 20 0 35 30 21 111. 24 111 29 18 45 29 0 89 94 64 IV. 3Q 10 21 19 39 - 0 96 100 70 80 1 14 0 11 11 9 0 0 21 19 19 23 15 25 20 34 15 0 23 33 34 23 21 33 25 48 29 0 99 99 70 IV. 37 19 30 20 46 0 100 100 86 4 Table XIV

PhyloToxicity Dose Time of Herbicidal effect % Treatment g/tia evaluationGALAP LAMAM LAMU VERAR FUMOF STEME CONOR CHEAL BILCO % Logran 75 OF 10 18 0 0 3 0 D 0 11 14 0 38 23 40 31 0 26 0 0 33 0 82 78 84 75 0 66 0 0 86 0 IV. 90 90 96 72 0 - 0 0 82 0 Logran 75 OF 20 1'. 19 0 3 15 0 0 0 23 18 0 24 41 36 15 28 0 6 43 0 94 90 95 89 41 83 0 0 96 0 IV. 96 -96 99 90 36 - 0 0 99 0 1 Logran 75 OF 40 1. 21 0 15 16 13 5 0 19 19 0 48 29 4 'i 36 13 25 0 21 48 0 99 9B 99 97 68 9B 0 0 99 0 iv. 100 100 100 100 50 0 0 100 0 Logran 75 OF 80 30 5 15 21 15 11 0 21 21 0 43 35 34 33 25 28 5 10 43 0 90 0 0 99 0 99 1 99 99 79 1 1V. 100 100 100 100 81 0 0 100 0 n, & Treatment. Dose g/ha Table XV

T i me of GALAP LAMAM LAMPU VERAR FUMOF STEME CONOR CHEAL BILCO evaluation ptlytotox-Lci. t. y Granstar 75 OF 10 15 0 0 0 a 0 0 6 11 ri 18 28 38 5 15 28 0.- 10 15 0 84 68 68 30 36 75 0 49 72 0 IV. 91 79 83 21 34 - 0 5 7 89 0 Granstar 75 OF 20 16 0 11 6 0 6 0 14 11 0 38 29 39 20 15 43 0 41 48 0 1 82 59 68 36 58 84 0 70 83 0 IV. 90 76 86 29 46 - 0 70 94 0 Granstar 75 OF 40 1. 19 8 20 10 0 0 0 20 23 10 38 34 35 34.21 31 15 53 53 15 94 76 83 49 68 89 9 97 95 0 IV. 98 96 96 40 50 - 0 94 95 0 Granstar 75 OF Bp 1. 25 15 19 21 0 6 0 23 19 14 43 44 30 25 28 51 6 1-8 65 15 97 04 91 48 79 97 19 96 96 0 IV. 98 96 96 50 70 10 100 100 0 a cl, 11,2 Lable XVI Results of examinations of the spikes Dose Number of Spike-length Number of Weight of Treatment g/tia spikes/m2 in cm grains/spike 1000 graind(g) Untreated 509 7,0 19,4 39,4 1/8 10 607 7,7 21,3 40,3 590 7,9 19,0 41,4 620 6,2 22,0 40,9 604 7,6 20,9 40,0 1/4 10 620 7,8 21,6 40,0 609 719 20,6 41,2 619 7,0 21,4 42,0 630 7,0 22,0 40,6 116 10 424 7,5 14,0 42,1 432 3,8 13,4 42,8 301 3,4 7,2 44,1 266 3,4 6,0 44,2 1/5 10 399 5,9 15,4 43,7 250 3,2 10,8 44,4 248 2,6 7,0 43,9 261 3,4 6,1 14410 Logran 75 WG 10 614 7,6 20,6 42,3 Logran 75 WG 20 645 7,9 21,4 40,B Logran 75 WG 40 630 6,3 21,4 42,4 Logran75 WG 80 641 7,9 22,0 41,3 Granstar 75 OF 10 600 7,6 20,8 4030 Granstar 75 OF 20 590 0,4 20,4 40,4 Granstar 75 OF 40 639 0,0 21,1 39,0 Granstar 75 OF 80 629 7,8 21,0 41,3 t 0 From the results illustrated in TablesX to XVI it can clearly be seen that a difference appeared between the effectivity of the compositions according to the invention and that of the commercially available compositions used for comparison. Compositions containing compounds Nos. 4 and 8 of Table I proved to be highly effective by late postemergent treatments on developed weeds in extremely strong infections. The selectivity against cultivated plants of both compounds is also favourable. Cue to their high phytotoxicity as well as weak, eventually unuseful weed control action, herbicide compositions containing the compounds Nos. 5 and 6 of Table I are not suitable for weed control in a winter-wheat culture.

Example 29 Investigation of the effect of antidoted compositions on cultivated plants in a plant-cultivating chamber 9 of field top soil each (witti a pH value of 6.5, permeability of 50 and humus content of 1.4 %) were weighed in plastic cultivating bottles of 0. 8 dm 2 surface each lined with PVC foil. Onto this soil 10 seeds of Pi- 3737 maize each and 10 seeds of streaked sunflower '1REG" each were sowed. The seeds were covered by 100 g of soil, then the treatments were carried out in 4 repetitions. In the course of these treatments 20 to 160 9 per hectare doses of active ingredients Nos. 2, 4, 5, 6 or 8, respectively of Table I together with 250 to 500 g per hectare of the antidotes DKA-24, AD-67, R-25788, MG-191 or CGA-92194, respectively were applied in the form of compositions formulated according to Examples 15 to 21. The treated soil surface was covered with additional 100 9 of soil in each bottle.

The bottles were placed in a plant-cultivating chamber and cultivated with a daily illumination period of 16 hours. The plants were daily sprinkled up to their water capacity.

The experiment was evaluated by determining (measuring) the shoot-length and green weight on the 13th day following the treatment. The results are summarized in Tables XVII to XIX.

c j Table XVII

Development of the green weight of Pi-3737 maize under effect of the treatments Green weight- of maize as percentage of untreated control Treatments- Dose of active DKA-24 AD-67 R-25788.

ingredient g/ha 250 5oo 25o, 500 25o, 500 1213 loo 1/8 1/4 1/6 1/2 1/5 4o, 2o, 59 27 112 62 56 91 83 113 61 91:

105..

92: 41 1o4 73 80.

97. 91 33 87 65 SC3- 96. 96 5o 104 78 82 loc 96, 37 96 72 81 90.

IdG-191 CA-,92194 250 5oo 2505oc, 7 8 67 94 71 82 83 73 80 32 75 79 1o2 78 76 87..

71 99 64 77 77 A (05,1,1 Table XVIII Development of the shoot-length of Pi-3737 maize under effect of the treatments Treatments Dose of active Shoot-length of maize as percentage of untreated control ingredient. R-25788 1AG-191 g/tia 2509 50og 2509 5oog 2509 5oog 25095009 CGA-92194 25og 5oog 1/8 4o 68 84 sa.. 9L 92. 88 97 78 78 7i 74 1 1/4 62 77 83. 83 88 88 90 69 76 81 79 1/6 2o 19 41 31 29 41x, 29 37 25 35 67 66 1/2 16o 91 96 92 83 97 '92 95 68 89 84 86 1/5 2o 48 47 53 53 62 59 6o 53 45 53 57 liogran 4o. 4o, 71 74 7.6.80 8. 87... 75 74 77 GB 1 000"t ireatments 1/8 114 1/6 1/2 1/5 Log:ran Table XIX Development of the green weight of streaked sunflower "IREG" under effect of the treatments Dose of active Green weight of sunflower as percentage of untreated control ingredient DIKA-2-4,.1 AD-67 R-25788 MG-191 g/Pa 250 5oo 250 500 25o 5oo 250 500 68 81-81.

119 68 82 7B 0 71 79 loo 48 59 61 51 89 69 71 84 6o loo 67 57 72 88 73 88 67 55 89 7o, 5,1, 69.

83 87 97 7o 59 78 61 74 1o6 102 61 55 1,06 69 9 5' 89 C G A -'9. ' 21?4 250500 51 93 61 84 61 5o, 4o 58 77 73 83 64 42 1 CY) 1 cl 47 - Example 30 Test of the effect of antidoted compositions on cultivated plants in a plant-cultivating chamber.

400 g of field top soil each (with a pH value of 6.5, permeability of 50 and humus content of 1.4 %) were weighed in plastic cultivating bottles of 0.8 dm 2 surface each lined with PVC foil. Onto this soil 10 seeds of Pi-3747 maize each and 50 seeds of SA-114 sorghum each were sowed. The seeds were covered by 100 9 of soil, then the treatments were carried out in 4 repetitions. In the course of these treatments 20, 40 or 80, respectively 9 per hectare dose of the compounds Nos. 2, 4, 5, 6 or 8, respectively, of Table I together with 400 g per hectare of DKA-24 antidote were applied in the form of compositions formulated according to Examples 22 to 24. The same doses of Glean, Granstar, Ally or Tell, respectively were applied together with DKA-24 antidote for comparison. The sprayed soil surface was again covered with additional 100 9 of soil in each bottle.

The bottles were placed in a plant-cultivating chamber and cultivated with a daily illumination period of 16 hours. The plants were daily sprinkled up to their water capacity.

The experiment was evaluated by determining (measuring) the shootlength and green weight on the 12th day following the treatment. The results obtained are summarized in Table XX.

t Table XX

Shoot-length of maize (cm) Green weight of maize (g) Green weight of sorghum (g) Dose of active ireatments ingredient + DICA-2 4 DICA-2 Al. +DKA-214 g/tia 4oo g/ha 4.00 400-/tia I-PO 2o 7o, 86 71 74 125 128 5,1, 82 59 76 86 90 39 67 43 65. 68 129 1/4 2o 61 90 66 87 129 127 47 81 59 87 103 114 29 65 4o, 72 109 119 1/6 2o 41 56 49 67 5o 33 CD 18 25 23 3o 20 lO 10 8 30.9 7 7 1/2 2o 98 95 97 92 118 114 105 1o5 119. 109 114 104 103 9B 114 1o6 81 94 1/5 2o 68 74 77 80 57 loo 5o 39 6o 52 6o, 73 so 29 4o 38 52 26 24 Gleaa 2o, 11 51 16 6o 24 72 12 30 19 41 66 75 5 lO is 11 95 66 r Table XX continued Shoot-length of maize (cm) Green weight of maize (g) Green weight of sorghum Dose of active Treatments ingredient + OKA-24 + DKA-24 AKA-24 g/11a 400 g/ha 400 g/ha 4 0 0 g/tla Granstar 20 90 76 84 03 62 120 86 77 84 B1 115 160 04 74 85 72 79 130 Ally 20 27 49 41 63 112 58 16 34 24 43 106 53 13 24 24 33 94 46 Tell 20 98 - 105 - 75 - 90 109 15 90 - 96 - 11 1 All".1

Claims (12)

CLAIMS:

1. A subsituted sulfonylurea derivative of the general formula (I) R R 4 CSO E 2-NH-C-N-, hoc/ \ R5

2 3 R -CH-OR wherein R 1 stands for hydrogen, halogen, Cl-4 alkoxy, halo-C 1-4 alkoxy, Cl-3 alkylsulfonyl or a group of the formula COR 6; R 2 means hydrogen, C 1-3 alkyl or phenyl; R 3 represents C 1-6 alkyl, C 3-6 alkenyl, Cl-3 al'Koxyalkyl group, C2-4alkyl subsutituted by one or more halogen(s) or benzyl group, R 4 and R 5 mean independently of each other a Cl-4alkyl, Cl-4alkoxy group, halogen, C 1-3 alkylamino or di(C 1-3 alkyl)amino, or C 1-3 alkylthio; R stands for a C 1-4 alkoxy, C 3-6 alkenyloxy, C 3-6 alkoxyalkyl, C 1-3 alkyl amino, di(C 1-3alkyl)amino, piperazinyl or morpholinyl group; X means oxygen or sulfur; and E stands for a methine group or nitrogen, as well as its salts.

(1) 2. A herbicide composition containing substituted sulfonylurea derivative, which comprises as active ingredient a substituted sulfonylurea derivative of the general formula (I), wherein A 011 A I R 1 stands for hydrogen, halogen, C1-4 alkoxy, halo-C 1-4 alkoxy, c alkylsulfonyl or a group of the formula COR - 1-3 61 R 2 means hydrogen, C 1-3 alkyl or phenyl; R 3 represents C 1-6 alkyl, C 3-6 alkenyl, C 1-3 alkoxyalkyl group, c 2-4 alkyl subsutituted by one or more halogen(s). or benzyl; R 4 and R 5 mean independently of each other a C 1-4 alkyl, C 1-4 alkoxy group, halogen, C 1-3 alkylamino or dil 1-3 alkyl)amino or C 1-3 alkyl thio., R 6 stands for a C 1-4 alkoxy, C 3-6 alkenyloxy, C 3-6 alkoxyalkyl, C 1-3 alkyl amino, di(C 1-3 alkyl)amino, piperazinyl or morpholinyl group, X means oxygen or sulfur, and E stands for a methine group or nitrogen, or a salt thereof.

3. A composition as claimed in Claim 2 in the form of wettable powder.

4. A composition as claimed in Claim 2 in the form of granules.

5. An antidote-containing herbicide composition containing a substituted sulfonylurea derivative as active ingredient and an antidote, which comprises a substituted sulfonylurea derivative of the general formula (I), wherein R,, R 21 R 31 R 41 R 51 X and E are 85 defined in Claim 1 or its salt as active ingredient and an antidote, preferably DKA-24 (chemically N-dichloroacetyPNally1glycine Wallylamide), AD-67 (chemically N-dichloroacetyPT oxa-4-azaspiro/4.57decane), R-25788 (chemically Njdiallyl-dichloroacetamide), MG-191 (chemically 2-dichloromethyl-2-methyl1,3-dioxolane), CGA-92194 (chemically N-(1,3-dioxolan-2-ylmethoxy)iminobenzeneacetonitrile) or TI-35, respectively, in a total amount of 0.01 to 95 % by weight, preferably 2 to 80 % by weight in an 1:1 to 1:50 might ratio (of the active ingredient to the antidote).

4r -11 1M ' k..;

6. A process for the preparation of a substituted sulfonylurea derivative of the general formula (I)

7 ->R 1 X R4 0 '__S02-NH-C-N rE ho- :V N 4 \ 5 2 ' 3 R -CH-OR (I) wherein R stands for hydrogen, halogen, Cl-4 alkoxy, halo-C 1-4alkoxy, C alkylsulfonyl or a group of the formula COR; 1-3 61 R 2 means hydrogen, C 1-3 alkyl or phenyl; R 3 represents C 1-6 alkyl, C 3-6 alkenyl, C 1-3 a3koxyalkyl group, C2-4 alkyl subsutituted by one or more halogen(s)-. or benzyl-, R 4 and R 5 mean independently of each other a C 1-4 alkyl, C 1-4 alkoxy group, halogen, C 1-3 alkylamino or di(C 1-3 alkyl)amino, or C 1-3 alkylthio; stands for a C 1-4 alkoxy, C 3- 6 alkenyloxy, C 3-6 alkoxyalkyl, C 1-3 alkylamino, di(C 1-3 alkyl)amino, piperazinyl or morpholinyl group; X means oxygen or sulfur; and E stands for a methine group or nitrogen, as well as its salts, which comprises a) reacting an isocyanate or isothiociianate of the general formula (IV), 1 R- 0 SC)2 NW - (IV) wherein R 1 is as defined above, with an aminopyrimidire or aminotriazine derivative of the general formula III 1 .r R4 HN -O E N::! R 5 R2- CH - OR3 (III) wherein the substituents are as defined above, at a temperature of 0 to 50 0 C, preferably at 20 to 30 0 C, or b) reacting a sulfonylcarbamate of the general formula (V) p 1 0 gCS02 - NH - COOR (V) wherein R 1 is as defined above and R stands for phenyl group, with an aminopyrimidine or aminotriazine derivative of the general formula (III) at a temperature of 25 to 120 0 C, preferably at 60 to 90 0 C, or c) reacting a carbamoyl chloride of the general formula (VI) R4 N E O-N-COCI 5 /\!N (VI) R2- CH-OR3 wherein the substituents are as defined above, with an alkaline metal salt of a sulfonamide derivative of the general formula (II) R1 1 S02 - NH2 (II) C.

wherein the substituents are as defined above, at a temperature between 10 0 C and 50 0 C, preferably at 0 to 25 0 C, or d) reacting an N-pyrimidinyl- or N-triazinylcarbamate of the geeral formula (VII) R4 N E o- N - COOR N R2-1 CH -OR3 (Vii) wherein the substituents are as defined above, with a sulfonamide derivative of the general formula (II), wherein the substituents are as defined above, at a temperature between 20 to 80 0 C, preferably at 20 to 40 0 C, or e) reacting a sulfonyl chloride of the general formula (VIII) W CC (S02-Cl (VIII) wherein the substituents are as defined above, with an aminopyrimidine or aminotriazine derivative of the general formula (III), wherein the substituents are as defined above,ata temperature of 20 to 120 0 C, preferably at 60 to 90 0 C in an inert organic solvent or in a mixture of inert organic solvents, then optionally converting the compound of the general formula (I) thus obtained to its salt with an alkaline metal or alkaline-earth metal hydroxide, amine or quaternary ammonium halide, separating the compound of general. formula M or its salt obtained by evaporating the solvent(s) and, if necessary, recrystallizing it by a method known per se.

4.

I C 7. Compounds of the general formula I as set out in claim 1, wherein the substituents R, to R5t X and E are as defined in Table I.

8. A method of making the compounds of the general formula I as claimed in claim 1, substantially as hereinbefore described in any one of Examples 1 to 5.

9. Herbicidal described in any one

10.

applying compound

11. A method as of the general formula I in any one of claims 2 to 5 and 9.

12. A method as claimed in claim 11 or 12, substantially as hereinbefore described in any one of Examples 25 to 30.

of the Penera compositions substantially as hereinbefore of Examples 6 to 24.

A method of controlling weeds in a plot comprising to the plot a herbicidally effective amount of the formula I as claimed in claim 1 or 7.

claimed in claim 1, wherein the compound is applied in a composition as claimed Amendments to the claims have been filed as follows 5. An anti date-cont a in iing tlerbicide-compos it ion containing a substituted sulfonylurea derivative as active ingredient and an antidote, which comprises a substituted sulfonylurea derivative of the general formula (I), where-in R,, R,, R 31 R 4,1 R 51 X and E are as defined _n Claim 1 or its salt as active inorecient and an antidote, preferably OKA- 24 (chemically N-dichloroacetyl-Nally1glycine N'-allylamidel', AD-67 (chemically N-dichloroacetyl-loxa-4-azaspiro/4.57decane), R-2-5788 (chemically N,N-diallyl-dichlorclacetamide), MG-191 (chemically 2dictiloromettiyl-2-mettiyl-1,3-dioxolaIe) CGA-92194 (chemically N-(1,3dioxolan-2-ylmettioxy)imino-benzeneacetonitrile) or TI-35 (N(dichloroacetyl) hexalrethylene jinire) respectively, in a total a,=t of o. ol to 95% by -ueigit, prefer-ably 2 to W1. ty.%eight in an 1. -1 to 1: 50 weight ratio (of the active ingredient to the antidote).

k Gr Published 1991 at The Patent office. Concept House. Cardifr Road. Newport. Gwent NP9 1 RH Further copies may be obtained from Sale, Branch. Unit 6. Mne Mile Point. Cii-mfelinfach. Cross Keys- Newport- NPI 7HZ. Printed by Multiplex techniques lid- St Mary Cray - Kent.