DE3105453A1 - Phenyl- or phenoxysulphonylpyrimidylureas, their preparation, and their use as herbicides and plant growth regulators - Google Patents

Abstract

Phenyl- or phenoxysulphonylpyrimidylureas of the formula I <IMAGE> in which R1 and R2 denote H or alkyl, R3 denotes H, (substituted)alkyl, (substituted)alkoxy, (substituted)alkylthio, alkoxycarbonyl, alkyl- or dialkylamino or CF3, R4 denotes halogen, NO2, CN, CF3, CHO, (substituted)alkyl, (substituted)alkoxy, (substituted)alkylthio, dialkylamino, alkoxycarbonyl or an oxime group, R5 denotes H, (substituted)alkyl, (substituted)alkoxy, (substituted)alkylthio, alkyl- or dialkylamino, R6 radicals (which are identical or different) denote halogen, alkyl, alkoxy, alkylthio, NO2, NH2, CF3, alkoxycarbonyl, alkylsulphonyl or dialkylamino, X denotes O or S, m denotes zero or 1 and n denotes zero to 3, and their salts are potent herbicides.

Description

Phenyl or phenoxysulfonyl pyrimidyl ureas,

Process for their preparation and their use as herbicides and Plant Growth Regulators The present invention relates to new phenyl / phenoxysulfonyl pyrimidyl ureas with herbicidal or plant growth-regulating effect, process for their preparation and herbicidal or plant growth regulating agents containing these new compounds contained as active ingredients.

It is already known that heterocyclically substituted sulforylureas, such as N- (4-chloro-6-i-propylamino-1,3,5-triazin-2-yl> -N-i-propyl-N '- (4-chlorophenylsulfonylurea, have herbicidal or plant growth-regulating properties (cf. NL-PS 121 78d, DE-OS 27 15 786, EP 1 485, EP 1 514, EP 1 5'5, EP 4 163, EP 7 687, EP 9 41q, EP 10 560).

It is also known that Sufonylureas with a bicyclic Pyrimluitirest to be used as a heterocyclic component as herbicidal active ingredients (see EP 15 683).

The present invention relates to phenyl or

Phenoxy-sulfonyl-pyrimidyl-ureas of the general formula I, in which R1 is hydrogen or, if m = 0, also (C1-C3, alkyl; R2 is hydrogen or (C1-C2) alkyl; R3 is hydrogen, an optionally substituted by halogen, (C1-C4) alkoxy, (C1-C4) alkylthio, (C1-C4) alkylamino or di- (C1-C4) alkylamino substituted (C1-C1I) alkyl, (01-C4) alkoxy or (C1-C4) alkylthio; (C1-C4) alkoxycarbonyl, (C1-C4 ) Alkylamino, di- (C1-C4) alkylamino or trifluoromethyl; R4 halogen, nitro, cyano, trifluoromethyl, formyl, one optionally substituted by halogen, (C1-C4) alkoxy, (C1-C4) alkylthio or di (C1-C4) alkylamino-substituted (C1-C4) alkyl, (C1-C4) alkyloxy or (C1-C4) alkylthio radical; di- (C1-C4) alkylamino, (C1-C4) alkoxycarbonyl or the grouping where R7 is hydrogen or (C1-C4) alkyl and R8 is (C1-C4) alkyl, R5 is hydrogen, one optionally substituted by halogen, (C1-C4) -alkoxy, (C1-C4'-alkylthio, (C1-C4) alkylamino) or di- (C1-C4) alkylamino substituted (C1-C4) alkyl-, (C1-C4) -alkoxy- or (C1-C4) alkylthio radical: (C1-C4) alkylamino or di- (C1-C4) alkylamino: R6 independently of one another identical or different radicals from the group consisting of halogen, (C1-C48-alkyl, (C1-C4) alkoxy, (C1-C4) alkylthio, (C1-C4) alkoxycarbonyl, nitro, (C1-C4) alkylsulfonyl, di- ( C1-C4) alkylamino, amino, or trifluoromethyl; X is oxygen or sulfur; m is 0 or 1 and n is 0-3, and, if R1 is hydrogen, their physiologically acceptable salts.

Examples of pyrimidylsulfonylureas according to the invention are specifically mentioned the following compounds of the formula I: N- (4,5-dichloro-6-methylpyrimidin-2-yl) -N '- (phenylsulfonylurea; N- (4, Ç-Dimethyl-5-chloropyrimidin-2-yl) -N '- (2-chlorophenylsulfonyl) urea; N- (4,6-dimethyl-5-bromopyrimidin-2-yl) -N '- (2-nitrophenylsulfonyl) urea; N- (4,6-dimethoxy-5-chloropyrimidin-2-yl) -N '- (5-chlorophenylsulfonyl) urea; N- (4-methoxy-5-chloro-6-methylpyrimidin-2-yl) -N '- (2-methylphenylsulfonyl) urea; N- (4-methoxy-5-chloro-6-methylthiopyrimidin-2-yl) -N '- (4-methylphenylsulfonyl) urea; N- (4-Ethyl-5-fluoro-6-methylpyrimidin-2-yl) -N '- (2-ethoxy carbonylphenylsulfonyl) urea; N- (4,6-dimethyl-5-nitropyrimidin-2-yl) -N '- (2,5-dichlorophenylsulfonyl) -urea; N- (4-chloro-5-nitro-6-methypyrimidin-2-yl) -N '- (2-nitropnenylsulfonyl) urea; N- (4-methoxy-5-nitro-6-methylpyrimidin-2-yl) -N '- (2-chlorophenylsulfonyl) urea; N- (4-ethoxy-5-nitrc-6-methylpyrimidin-2-yl) -N '- (2-methoxycarbonylphenylsulfonyl) urea; N- (4,6-dimethoxy-5-formylpyrimidin-2-yl) -N '- (2-methylphenylsulfonyl) urea; N- (4,6-Dimethylthio-5-formuylpyrimidin-2-yl) -N '- (2-chlorophenylsulfonyl) urea; N- (4,6-diethoxy-5-formylpyrimidin-2-yl) -N '- (2-ethylphenylsulfonyl) urea; N- (4-chloro-5,6-dimethylpyrimidin-2-yl) -N '- (2-chlorophenylsulfonyl-urea; N- (4,6-dimethoxy-5-methylpyrimidin-2-yl) -N '- (2,3-dichlorophenylsulfonyl) urea; N- (4s6-DiethOxy-5-ethylpyrimidin-2-ylj-Nt- (4-methylphenolphonyl) urea; N- (4-methoxy-5-methoxyethyl-6-methylpyrimiain-2-yl) - (2,6-dichlorophenylsulfonyl) urea; N- (4-chloro-5-ethoxy-6-ethoxymethylpyrlmidin-2-yl) -N '- (2-nitrophenylsulfonyl) urea; N- (4,5-Dimethyl-6-diethylaminopyrimidin-2-yl) -N '- (2-nitrophenylsulfonyl) urea; N- (4,6-dimethoxy-5-methylpyrimidin-2-yl) -N '- (3,5-dimethylphenylsulfonyl) -thiourea; N- (4,6-diethoxy-5-chloropyrimidin-2-yl) - (2-methylphenylsulfonyl) thiourea; N- (4-methyl-5-ethoxycarbonylpyrimidin-2-yl) -N '- (2-chlorophenylsulfonyl) urea; N- (4-methyl-5-methoxycarbonyl-6-methylthiopyrimidin-2-yl) -N '- (2-chlorophenylsulfonyl) urea; N- (4,5-dichloro-6-methoxycarbonylpyrimidin-2-yl) -N '- (2-chlorophenylsulfonyl) urea; N- (4,6-dimethyl-5-chloropyrimidin-2-yl) -N '- (2-chlorophenoxysulfonyl) urea; N- (4,6-Dimethyl-5-bromopyrimidin-2-yl) -N '- (2-chlorophenoxysulfonyl )-urea; N- (4-chloro-nitrc-6-methylpyrimidin-2-yi) -N1 - (4-methylphenoxysulfonyl) urea; N- (4s6-Dimethyl-5-chloropyrimidin-2-yl) -N '- (2-methoxycarbonylphenoxysulfonyl) -area; N- (4,6-dimethoxy-5-chloropyrimidin-2-yl) -N '- (2,5-dichlorophenoxysulfonyl) -urea; N- (4,6-dimethoxy-5-methoxyiminoformylpyrimidin-2-yl) -N '- (2-chlorophenoxysulfonyl) urea; N- (4,6-Dimethyl-5-chloropyrimidin-2-yl) -N '- (2-chlorophenylsulfonyl) -urea, sodium salt.

The new compounds of the general formula I can be prepared by several processes. These processes are characterized in that a) compounds of the formula II in which X is oxygen or, if m = 0, also sulfur, with aminopyrimidines of the formula III or b) compounds of formula IV in which m represents zero reacts with compounds of the formula III, or c) compounds of the formula V in which m stands for zero, with compounds of the formula VI converts, and if desired, the compounds of formula I obtained by converting the C = S group into a C = 0 group or

by alkylation in the R1 position into other compounds of the formula I converts and / or compounds of the formula I in which R1 is H into physiological compatible inorganic or organic salts transferred.

Re a) and b): The compounds II are reacted with III and IV, respectively preferably in inert aprotic solvents such as acetonitrile, dichloromethane, Tetrahydrofuran, toluene or dioxane at temperatures between 0 ° C. and the boiling point of the solvent: in case b) in the presence of an acid acceptor such as e.g.

Potassium carbonate, pyridine or triethylamine.

To c) For the reaction of sulfonamides of the formula V with isothiocyanates of the formula VI are preferably used the same solvents as in a) under Basic compounds, e.g. potassium carbonate. You work at temperatures between OOC and the boiling point of the solvent.

If desired, compounds in which R1 = H can be alkylated, preferably in inert aprotic solvents such as dioxane or dimethylformamide Addition of an anoerganic base, e.g. sodium hydride or potassium carbonate Temperatures from 200C to the boiling point of the solvent. As an alkylating agent For example, dimethyl sulfate, methyl iodide or ethyl bromide are used.

The sulfur atom can also be used in compounds of the formula I where X = S Replace (X = S, m = 0) with an oxygen atom. This implementation is preferred in organic solvents such as acetone or acetonitrile, e.g. by treatment with oxides of heavy metals, e.g. with mercury oxide, at temperatures between 200C and the boiling point of the solvent carried out.

Compounds of the formula I in which R1 is hydrogen can Form salts in which H is replaced by a physiologically compatible cation. Inorganic and organic bases are suitable for salt formation, e.g. sodium methylate, Potassium carbonate, ammonia, ethanolamine, triethylamine, trimethylamine, etc.

For the preparation of the compounds according to the invention of the formula I required aminopyrimidine derivatives of the formula III are known or can be according to processes known in principle, e.g. by cyclization of corresponding guanidine derivatives with appropriately substituted 1,3-diketones (see e.g. D.J.Brown: "The Pyrimidines", Vol.XVI, John Wiley & Sons., Inc. (1962); D.J. Brown: 'The Pyrimidines, Supplement I, Wiley-Interscience (1970)).

The sulfonyl isocyanates, isothiocyanates and phenoxysulfonyl isocyanates of the formula II are largely known (cf. US-P 3,371,114, US-P 3,346,590 and DE-AS 12 30 017) or can be according to the method known in principle manufacture in a simple manner.

The arylsulfonyl-N-alkylcarbamoyl chlorides and arylsulfonyl-N-alkylthiocarbamoyl chlorides of the formula IV are known or can be prepared from the potash salts using customary methods the corresponding sulfonamides of the formula V, which are also known from the literature are represented by reaction with phosgene or with thiophosgene.

The pyrimidyl isothlocyanates required for the implementation of c) Formula VI are known or by known processes (cf. Tetrahedron 29, 691 (1973)) accessible.

The compounds according to the invention differ from the known heterocyclic sulfonylureas by an obligatory substitution in the p-position of the heterocyclic ring, i.e. in the R4 position of the formula I. They show an excellent herbicidal effect and, in important large-scale crops, a much higher selectivity than these and are therefore suitable for the selective control of numerous dicotyledons and grassy annual and perennial weeds in agriculturally significant Crops such as wheat, barley, rye, rice, maize, sugar beet, soy and cotton in the pre-sowing, pre-emergence and post-emergence method.

Are the compounds of the invention before the weed plants germinate Applied to the surface of the earth in the pre-sowing or pre-emergence process, this is how Emergence of the seedlings is not prevented. The weeds grow to the cotyledon stage but then stop growing and eventually die after a few Weeks off completely.

When applying the active ingredients to the green parts of the plant using the post-emergence method A drastic growth stop also occurs very quickly after the treatment and the weed plants remain in the growth stage present at the time of application stand or die completely after a certain time, so that in this way a Weed competition that is harmful to the cultivated plants is eliminated very early and sustainably can be.

In addition, the substances according to the invention have excellent properties growth-regulatory properties in cultivated plants. They act regulating in the plants own metabolism and can thus be used for targeted influencing of plant ingredients and to facilitate harvesting, e.g. by triggering Desiccation and stunted growth are used. Furthermore, they are also suitable for the general control and inhibition of unwanted vegetative growth, without that they kill the plants in the process. An inhibition of vegetative growth plays a role in many monocotyledonous and dicotyledonous crops this plays an important role, as it causes storage can be reduced or completely prevented. The compounds according to the invention thus represent a valuable addition to technology.

The invention therefore also relates to herbicidal or

growth-regulating agents, which are characterized by a Content of a compound of the formula I in combination with customary formulation auxiliaries and inert substances and their use in the agricultural sector.

The agents according to the invention contain the active ingredients of the formula I. generally from 2 to 95% by weight. They can be used as wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules in the usual preparations can be used.

Wettable powders are preparations that can be dispersed evenly in water, which in addition to the active ingredient besides a diluent or inert substance also wetting agents e.g. polyoxethylated alkylphenols, polyoxethylated fatty alcohols, alkyl or alkylphenyl sulfonates and dispersants, e.g., sodium lignin sulfonic acid, 2,2'-dinaphthylmethane-6,6'-disulfonic acid Sodium, dibutyl; sodium laphthalenesulfonic acid or oleylmethyltauric acid Contain sodium.

Emulsifiable concentrates are made by dissolving the active ingredient in an organic solvent e.g. butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons with the addition of one or several emulsifiers. As emulsifiers, for example be: alkylarylsulfonic acid calcium salts such as calcium dodecylbenzosulmonate or non-ionic Emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, Propylene oxide-ethylene oxide condensation products, fatty alcohol-propylene oxide-ethylene oxide condensation products, Alkyl polyethers, sorbitan fatty acid esters, polyoxethylene sorbitan fatty acid esters or Polyoxethylene sorbent tested dusts are obtained by grinding the active ingredient with finely divided, solid substances e.g. talc, natural clays such as kaolin, Bentonite, pyrophillite or diatomaceous earth.

Granules can either be sprayed onto adsorptive, granulated inert material are produced or by applying active ingredient centrates by means of adhesives e.g. polyvinyl alcohol, polyacrylic acid sodium or mineral oils on the surface of carrier materials such as sand, kaolinite or granulated inert material. Suitable active ingredients can also be used in the production of fertilizer granules in the usual way - if desired in a mixture with fertilizers.

In the case of herbicidal agents, the concentrations of the active ingredients can be in be different from the commercial formulations.

In wettable powders, the active ingredient concentration varies e.g.

between about 10% and 80%, the remainder being those given above Formulation additives. In the case of emulsifiable concentrates, the active ingredient concentration can also be about 10% to 80%. Dust-like formulations mostly contain 5 - 20% active ingredient, sprayable solutions around 2 - 20%. Granules hangs the active ingredient content depends in part on whether the active compound is liquid or is solid and which granulating aid.

Fillers, etc. can be used.

The commercially available concentrates are optionally used for use Diluted in the usual way, e.g. with wettable powders and emulsifiable concentrates by means of water. Jam-shaped and granulated preparations as well as sprayable solutions are no longer diluted with other inert substances before use. With the External conditions such as temperature, humidity, etc., the required varies Application rate. It is generally between 0.01 and 10 kg / ha, preferably about 0.1 to 5.0 kg / ha of active ingredient.

The active compounds according to the invention can be used with other herbicides, insecticides and fungicides are combined.

Preparation Examples Example 1 N- (4-Methoxy-5-chloro-6-methyl-pyrimidin-2-yl) -N '- (2-chlorophenylsulfonyl) urea 17.4 g (0.1 mol) of 2-amino-4-methoxy-5-chloro-6-methylpyrimidine are dissolved in 250 ml of dichloromethane suspended and at 00 to 50C dropwise with a solution of 21.8 (3.1 mol) 2-chlorophenylsulfonyl isocyanate in 100 ml of dichloromethane was added. The mixture is stirred for 18 hours at room temperature, the reaction mixture cools to OOC and sucks the accumulated Solid from. This product is dissolved in dilute aqueous sodium hydroxide solution. Man treats this solution with activated charcoal, filtered and acidified with dilute aqueous solution Hydrochloric acid. After filtering off with suction and drying, 3a, 1 g (87.3 % of theory) of N- (4-methoxy-5-chloro-6-methylpyrimidqn-2-y;) - N '- (2-chlorophenylsulfonylj-urea from melting point 220-222 ° C.

Example 2 N- (4-Methyl-5-ethoxy-carbonyl-pyrimidin-2-yl) -N '- (2-chlorophenoxysulfonyl) -urea A suspension of 18.1 g (0.1 mol) of 2-amino-4-methyl-pyrimidine-5-carboxylic acid ethyl ester A solution is added dropwise to 200 ml of dichloromethane at OOC while stirring of 23.5 g (0.1 mol) of 2-chlorophenoxysulfonyl isocyanate in 100 ml of dichloromethane are added. The mixture is stirred for a further 12 hours at room temperature, cooled to OOC and added dropwise with 100 ml of n-hexane. The precipitated reaction product is filtered off with suction with n-hexane washed and dried. 36.9 g (89% of theory) of N- (4-methyl-5-ethoxycarbonylpyrimidin-2-yl) are obtained -N '- (2-chlorophenoxysulfonyl) urea, melting point 14600.

Example 3 N- (4,6-Dimethyl-5-chloro-pyrimidin-2-yl) -N '- (4-chlorophenylsulfonyl) -thiourea A solution of 9.9 g (0.05 mol) of 4-chlorophenylsulfonamide in 200 ml of acetone is 2 Stirred with 6.9 g (0.05 mol) of potassium carbonate at 50 ° C. for hours. After cooling down on OOC, 9.9 g (0.05 mol) of 2-isothiocyanato-4,6-dimethyl-5-chloropyrimidine are added. The mixture is stirred for about 24 hours at room temperature and 2 hours at 40 ° C., poured the reaction mixture in water and acidified with dilute aqueous hydrochloric acid at. The reaction product is then filtered off with suction and dried in vacuo. Man obtained in this way 14.2 g (73% of theory) of N- (4,6-dimethyl-5-chloropyrimidin-2-yl) -N '- (4-chlorophenylsulfonyl) thiourea with a melting point of 182 ° C.

Example 4 N -. (4,5-Dimethyl-5-chloro-pyrimidin-2-y1) -N§- (4-chlorophenylsulfonyl urine peat A solution of 11.7 g (0.03 mol) of N- (4,6-dimethyl-5-chloropyrimidin-2-yl) -N '- (4-chlorophynylsulfonyl'-thiourea (See. Example 3) in 200 ml of acetone with 13.0 g (0.06 mol) of mercury oxide and mixed with a spatula tip of potassium carbonate. The mixture is stirred for about 48 hours at room temperature, sucks off the precipitated mercury sulfide, the filtrate is concentrated in vacuo and crosslinked with n-hexane. In this way, 9.1 g (81% of theory) of N- (4,6-dimethyl-5-chloropyrimidin-2-yl) -N '- (4-chlorophenylsulfonyl) urea are obtained with a melting point of 218-220 ° C.

Example 5 N- (4-chloro-5-nitro-6-methylpyrimidin-2-yl) -N '- (2-chlorophenylsulfonyl) urea 5.7 g (0.03 mol) of 2-amino-4-chloro-5-nitro-6-methylpyrimidine will suspended in 150 ml of dichloromethane and at 0 0C dropwise with a solution of 6.5 g (0.03 mol) of 2-chlorophenylsulfonyl isocyanate were added in 50 ml of dichloromethane.

The mixture is stirred for about 18 hours at room temperature and heated for 2 hours under reflux and filtered off from undissolved material.

The filtrate is cooled to 0 ° C. and treated with n-hexane.

The product precipitates in crystalline form. 10.2 is obtained g (83.7% of theory) of N- (4-chloro-5-nltro-6-methylpyrimidin-2-yl) -N '- (2-chlorophenylsulfonyl) urea from melting point 182-1850C.

In an analogous manner, those in the following table are listed Sulphonylureas of the formula I produced.

Table 1 At- R m R, R, R, rR, R, melting Npriel cm 2 ° cJ 6 C1 OHH CH3 C1 CH 202-4 7 l 0 HH CH3 Br CH5 190-2 3 QNO2 OHH OCH C1 STILL,; 140-1 9 1 HH CH; s C1 CH3 95-102 10 1 QHH STILL, C1 STILL, 208-10 11 21 OHH OCH3 CH3 CH3 232-3 12 S H3 O j H | H | HOLES | CH ° STILL, 196-9 13 OHH CH3 COOC2H "H 162-4 CH Table (continued) At- R m Rl R2 Ra R4 R5 melting game point No. Loc 7 14 CH3-- 1 l HH CH CH3 OC2H5 145-7 15 C1 1 HH CH3 Br CH3 i58-9 16 9 H3 OHH OCH: Cl CH3 209-1G 17 - 1 HH CM3 NO2 Ci 162-165 Cl 18 Cl o -; O CM3 H i CHs Cl CM3 95-100 Formulation Examples Example A An emulsifiable concentrate is obtained from: 15 parts by weight of active ingredient, 75 parts by weight of cyclohexane as solvent and 10 parts by weight of ethoxylated nonylphenol (10 AeO) as emulsifier.

Example B A wettable powder readily dispersible in water is received. by adding 25 parts by weight of active ingredient 64 parts by weight of kaolin-containing quartz as an inert substance 10 parts by weight of lignosulfonic acid potassium and t part by weight of oieylmethyltaurinsaures Mixes sodium as a wetting and dispersing agent and grinds it in a pin mill.

Example C A dust is obtained by adding 13 parts by weight Mixes active ingredient and 90 parts by weight of talc as an inert substance and in a hammer mill crushed.

Example D A granulate consists, for example, of about 2-15 parts by weight of active ingredient 98 - 85 parts by weight of inert granulate materials such as attapulgite, pumice stone and quartz sand.

Biological examples a) Herbicidal effect 1. Pre-emergence method Seeds of monocotyledon and dicotyledon weeds were placed in clay in plastic pots (8 cm) laid out and covered with earth. Those according to the invention formulated as wettable powders Compounds were in the form of aqueous suspensions or emulsions on the earth's surface applied. The amount of water applied per pot corresponded to the equivalent of 600 - 800 1 / ha After the treatment, the test pots were placed in the greenhouse and the test plants under good growth conditions (temperature: 23 # 1 ° C: rel. Humidity 60-80%). After about 3 weeks, the plant was damaged optically botinated. As a comparison, the controls were untreated.

The damage to the weed plants or the crop plant tolerance was rated in a key of O - 5.

0 = no effect (damage) 1 = 0 - 20% effect 2 = 20 - 40% effect 3 = 40 - 60% effect 4 = 60 - 80% effect 5 = 80 - 100% effect.

Table 2 summarizes the pre-emergence results. It will clearly that the compounds according to the invention have a good herbicidal action both against monocotyledonous as well as against dicotyledonous harmful plants, if the active ingredients be applied pre-emergence.

Table 2 Pre-emergence effect on monocotyledon and dicotyledon weeds Example no. Dose of STM LOM AMR SIA g a.i./a 1 100 5 5 - -25 5 5 5 5 6 100 5 4 - -25 4 4 5 4 8 100 5 4 - -25 4 3 5 5 9 100 5 5 - -25 5 4 5 4 10 100 5 5 -25 5 5 5 4 11 100 5 5 - -25 5 5 5 5 12 100 - - - -25 5 1 5 4 16 100 5 5 - -25 5 5 5 4 17 100 - - - -25 5 4 4 4 Abbreviations: STM = Stellaria media LOM = Lolium multiflorum AMR = Amaranthus retroflexus SIA = Sinapis arvensis 2. Post-emergence seeds of monocotyledon and dicotyledon weeds were sown in pots and in the greenhouse attracted under good growing conditions. 3 weeks after the.

When sowing, the test plants were treated in the three-leaf stage. The formulated as wettable powders or as emulsion concentrates according to the invention Preparations were sprayed onto the green parts of the plant in various doses and after sa. 3 weeks standing in the greenhouse, the effect of the preparations optically rated in comparison to untreated controls.

The agents according to the invention had a good herbicidal activity against a wide range of economically important annual and perennial weeds and grass weeds on (Table 3 ,.

Table 3 Post-emergence effect on monocotyledonous and dicotyledonous harmful plants Example no. Dose SIA AMR ECG STM LOM CYI g a.i./a 1 100 5 5 1 5 5 -25 4 5 1 5 5 4 8 100 4 5 5 5 3 -25 4 5 5 5 3 4 9 100 5 5 5 5 5 -25 5 5 5 5 5 4 10 100 5 5 5 5 5 -25 5 5 4 5 5. 4 11 100 - - - - - -25 5 5 3 5 4 5 12 100 - - - - -25 5 5 0 5 3 0 16 100 5 5 4 5 4 -25 5 5 3 5 4 4 17 100 - - - - - -25 5 5 1 4 3 -Abbreviations: SIA = Sinapis arvensis AMR = Amaranthus retroflexus ECG = Echinochloa crus-galli STM = Stellaria media LOM = Lolium multiflorum CYI = Cyperus iria b) Plant growth regulating effect Example I (growth inhibition on cereals) In tray tests young cereal plants (wheat, barley and rye) in the 3-leaf stage were grown in the greenhouse with the compound mentioned in Table 1 in the stated active compound concentrations (kg / ha) sprayed until dripping wet. The comparison compound was 2-chloroethyltrimethylammonium chloride used. After the untreated control plants had a height of about 55 cm, the increment and the inhibition of growth were measured for all plants calculated in% of the growth of the control plants. It was also phytotoxic Effect of the compounds observed. The results are summarized in Table I. When specifying the growth inhibition, 1.00% means the stagnation of growth and 0% growth corresponding to that of the untreated control plants.

Table 4 Inhibition of growth in cereal compound application inhibition of growth example concentration in the phytotoxic concentration wheat barley rye effect (kg / ha) 11 0.62 36 31 29 no 0.31 33 30 27 damage 16 0.62 32 28 27 no damage Comparison (2-chloroethyl) - 2.5 27 8 10 no trimethylammo- 1.25 23 0 O damage nium chloride (known) Example II (growth inhibition on soybeans and French beans) 10 - 15 cm high soybean or bush beans became dripping wet with the active compound preparations splattered. After 2 weeks, the growth is measured and the inhibition of growth in% of the Increments of the control plants were calculated. The results are summarized in Table 5.

Table 5 Growth inhibition in soy and bush beans Connection Application growth inhibition in% Phyto-concentration toxic example tration Soy bush bean Effect (kg / ha) 11 0.62 23 40 none 0.31 21 38 Damage .6 0.62 21 34 none Damage 2.5 12 34 no damage (known) Example III (growth inhibition on lawn) Egg lawn mixture, consisting of 5 representative species, is sprayed to runoff with an active ingredient preparation after being cut back 3 times. After 3-4 weeks, the growth is measured and the inhibition of growth is calculated in% of the growth of the control plants. 100% denote a standstill in growth and 0 ffi a growth corresponding to that of the untreated control plants.

Table 6 growth inhibition on lawn connection application con- growth inhibition Phytotoxic according to concentration in% Effect Example (kg / ha) 11 0.62 54 none 0.31 38 damage 16 0.62 41 no damage maleic 2.5 60 severe hydrazide damage known) Example IV (Increase in the proportion of sugar in sugar cane: investigation method Sugar cane plants are grown under greenhouse conditions at 25 0C - 350C and approx. 65% humidity attracted.

Different amounts of the formulated agents were in water suspended .. that in addition about 0.25% by weight of a surface-active agent (nonylphenol) contained.

In each case 0.3 ml of the suspensions were injected into applied to the spindle area at the level of the last visible leaf blade ("dewlap") (10 plants per concentration). From the treated plants as well as from the ones not Treated controls were removed and the leaves after 3 weeks of harvest the internodes analyzed in groups for their sucrose content.

The results are shown in Table 7.

Table 7 Compound application concentration Sugar content (% at according to of the harvest example (kg / ha) 11 0.62 168 16 0.62 157 control 100%

Claims (5)

Claims: 1. Compounds of the formula in which R1 is hydrogen or, if m = 0, also (C1-C3) alkyl; R2 is hydrogen or (C1-C2) alkyl; R3 is hydrogen, a (C1-C4) alkyl-, (C1-C4) optionally substituted by halogen, (C1-C4) alkoxy, (C1-C4) alkylthio, (C1-C4) alkylamino or di- (C1-C4) alkylamino ) Alkoxy or (C1-C4) alkylthio, (C1-C4) alkyloxycarbonyl, (C1-C4) alkylamino, di- (C1-C4) alkylamino or trifluoromethyl, Ru halogen, nitrc, cyano, trifluoromethyl, formyl, optionally through Halogen, (C1-C4) alkoxy, (C1-C4) alkylthio or di (C1-C4) alkylamino substituted (C1-C4) alkyl, (C1-04> alkoxy or (C1-C4) alkylthio, di- ( C1-C4) alkylamino, (C1-C4) alkoxycarbonyl or the grouping where R7 is hydrogen or (C1-C4) alkyl and R8 is (C1-C4) alkyl, R5 is hydrogen, an optionally substituted by halogen, (C1-C4) -alkoxy, (C1-C4) alkylthio, (C1-C4) Alamino or di- (C1-C4) alkylamino-substituted (C1-C4) Al.Ryl-, (C1-C4) -alkoxy- or (C1-C4) alkylthlo radical, (C1-C4) alkylamino or di- (C1-C4 ) alkylamino; R6, independently of one another, identical or different radicals from the group consisting of halogen, (Cl-C4) alkyl, (C1-C4) alkoxy, (C1-C4) alkylthio, (C1-C4) alkoxycarbonyl, nitro, (C1-C4) -alkylsulfonyl, Di- (C1-C4) alkylamino, amino, or trifluoromethyl; X oxygen or sulfur; m is 0 or 1 and n is 0-3, and, if R1 is hydrogen, their physiologically acceptable salts. 2. experienced for the preparation of compounds of the formula I, characterized in that a) compounds of the formula II in which oxygen or, if m = 0, also means sulfur, with aminopyrimidines of the formula III or b) compounds of the formula IV in which m represents zero reacts with compounds of the formula III, or c) compounds of the formula V in which m stands for zero with compounds of the formula VI converts, and if desired, the compounds of formula I obtained by converting the C = S group into a C = 0 group or by alkylation in the R1 position into other compounds of the formula I converts and / or compounds of the formula I in which R1 is H in'physiologically compatible inorganic or organic salts transferred. 3. herbicidal agents, characterized in that they contain compounds of formula I. 4. Use of compounds of the formula I for combating undesirable substances Vegetation. 5. Method of combating unwanted plants stalks, thereby characterized that one on the plants or the areas befalienen by them effective amount of a compound of formula I applies.