DE3626860A1 - Acylated 1-(2-oxyaminosulphonylphenylsulphonyl)-3-heteroarylureas - Google Patents

Abstract

The invention relates to novel acylated 1-(2-oxyaminosulphonylphenylsulphonyl)-3-heteroarylureas of the general formula (I) <IMAGE> (in which R<1>, R<2>, R<3> and R<4> have the meanings given in the description), to a process for their preparation and to their use as herbicides.

Description

The invention relates to new acylated 1- (2-oxyaminosulfonylphenylsulfonyl) - 3-heteroaryl ureas, a process for their preparation and their use as herbicides.

It is known that certain 1-arylsulfonyl-3-heteroaryl ureas, such as B. 1- (2-methoxyaminosulfonylphenylsulfonyl) - 3- (4,6-dimethyl-pyrimidin-2-yl) urea and 1- (2- Methoxyaminosulfonylphenylsulfonyl) -3- (4,6-dimethoxy- pyrimidin-2-yl) urea, are herbicidal. The effect however, these connections are not always entirely satisfactory (see EP-A 1 53 601 and EP-A 1 73 322).  

New acylated 1- (2-oxyaminosulfonylphenylsulfonyl) - 3-heteroaryl ureas of the general formula (I)

in which
R ^{1 represents} an optionally substituted radical from the series alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aralkyl and aryl,
R ^{2 represents} hydrogen or an optionally substituted radical from the series alkyl, alkenyl, alkynyl and aralkyl,
R ^{3 stands} for an optionally substituted and / or optionally fused six-membered aromatic heterocycle which contains at least one nitrogen atom and
R ^{4 represents} hydrogen or optionally substituted radicals from the series alkyl, cycloalkyl, cycloalkylalkyl, alkenyl, alkynyl, aryl, aralkyl, hetaryl, alkoxy, aralkoxy, aryloxy, alkylamino, aralkylamino, cycloalkylamino, arylamino, dialkylamino, alkylcarbonyl, arylcarbonyl and alkoxycarbonyl,
found.

The new acylated 1- (2-oxyaminosulfonylphenylsulfonyl) - 3-heteroarylureas of the formula (I), if 1- (2-oxyaminosulfonylphenylsulfonyl) -3-heteroaryl- ureas of the formula (II)

in which
R ¹ , R ² and R ^{3 have} the meanings given above,
with acylating agents of the formula (III)

Q-CO-R ⁴ (III)

in which
R ^{4 has} the meanings given above and
Q represents a leaving group customary in acylating agents,
if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent.

The new acylated 1- (2-oxyaminosulfonylphenylsulfonyl) - 3-heteroaryl ureas of the formula (I) are notable for strong herbicidal activity.

Surprisingly, the new connections show the  Formula (I) significantly better herbicidal activity than previously known Urea derivatives with the same direction of action.

The invention preferably relates to compounds of the formula (I) in which
R ¹ for C ₁ -C ₁₂ alkyl [which may be replaced by fluorine, chlorine, cyano, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ - alkylsulfinyl, C ₁ -C ₄ - Alkylsulfonyl, C ₁ -C ₄ alkylcarbonyl, C ₁ -C ₄ alkoxycarbonyl, C ₁ -C ₄ alkylaminocarbonyl or di- (C ₁ -C ₄ alkyl) aminocarbonyl is substituted] , for C ₃ -C ₆ alkenyl [which is optionally substituted by fluorine, chlorine or bromine], C ₃ -C ₆ alkynyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ cycloalkyl- C ₁ -C _2- alkyl, phenyl-C ₁ -C ₂ -alkyl [which is optionally substituted by fluorine, chlorine, nitro, cyano, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy or C ₁ -C ₄ -alkoxy-carbonyl is substituted], for benzhydryl, or for phenyl [which is optionally substituted by fluorine, chlorine, nitro, cyano, C ₁ -C ₄ -alkyl, trifluoromethyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₂ -fluoroalkoxy, C ₁ -C ₄ alkylthio, trifluoromethylthio or C ₁ -C ₄ alkoxycarbonyl is substituted],
R ² for hydrogen, C ₁ -C ₄ alkyl [which may be replaced by fluorine, chlorine, cyano, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₁ - C ₄ -alkyl-carbonyl, C ₁ -C ₄ -alkoxy-carbonyl, C ₁ -C ₄ alkylamino carbonyl or di- (C ₁ -C ₄ -alkyl) -amino-carbonyl substituted is] for C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl or phenyl-C ₁ -C ₂ alkyl [which may be replaced by fluorine, chlorine, nitro, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ alkoxy carbonyl is substituted],
R ³ for the rest

stands in what
R ⁵ for hydrogen, fluorine, chlorine, bromine, hydroxy, C ₁ -C ₄ -alkyl [which is optionally substituted by fluorine and / or chlorine], C ₁ -C ₄ -alkoxy [which is optionally substituted by fluorine and / or chlorine is], C ₁ -C ₄ -alkylthio [which is optionally substituted by fluorine and / or chlorine], amino, C ₁ -C ₄ -alkylamino or di- (C ₁ -C ₄ -alkyl) -amino,
X represents nitrogen or a methine bridge (CH),
Y represents nitrogen or an optionally substituted methine bridge CR ⁶ , where
R ^{6 represents} hydrogen, fluorine, chlorine, bromine, cyano, formyl, C ₁ -C ₄ alkyl, C ₁ -C ₃ alkoxycarbonyl or C ₁ -C ₃ alkylcarbonyl, and
Z represents nitrogen or an optionally substituted methine bridge CR ⁷ , where
R ^{7 is} hydrogen, fluorine, chlorine, bromine, hydroxy, C ₁ -C ₄ -alkyl [which is optionally substituted by fluorine and / or chlorine], C ₁ -C ₄ -alkoxy [which is optionally substituted by fluorine and / or chlorine is], C ₁ -C ₄ alkylthio [which is optionally substituted by fluorine and / or chlorine], amino, C ₁ -C ₄ alkylamino or di- (C ₁ -C ₄ alkyl) amino and
in which further
R ⁴ for hydrogen, C ₁ -C ₂₀ alkyl [which may be by fluorine, chlorine, bromine, cyano, C ₁ -C ₄ alkoxycarbonyl, C ₁ -C ₄ alkoxy, benzyloxy or by optionally fluorine, chlorine , Bromine, cyano, nitro, methyl and / or trifluoromethyl substituted phenoxy is substituted], C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ cycloalky-C ₁ - C ₂ alkyl, C ₂ -C ₆ alkenyl [ which is optionally substituted by fluorine, chlorine or bromine], C ₂ -C ₆ -alkynyl, phenyl-C ₁ -C ₂ -alkyl [which is optionally substituted by fluorine, chlorine, nitro, cyano, C ₁ -C ₄ -alkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ alkoxycarbonyl is substituted], phenyl [which is optionally substituted by fluorine, chlorine, cyano, nitro, C ₁ -C ₄ alkyl, trifluoromethyl, C ₁ -C ₄ alkoxy , C ₁ -C ₂ fluoroalkoxy or C ₁ -C ₄ alkoxy-carbonyl is substituted], pyridyl [which is optionally substituted by fluorine, chlorine, cyano, nitro, methyl or methoxy], C ₁ -C ₆ alkoxy [ which is optionally by fluorine, chlorine, cyano or C ₁ -C ₄ -A lkoxy is substituted], benzyloxy [which is optionally substituted by fluorine, chlorine, nitro, cyano, C ₁ -C ₄ alkyl, C ₁ - C ₄ alkoxy or C ₁ -C ₄ alkoxycarbonyl], phenoxy [which is optionally substituted by Fluorine, chlorine, cyano, nitro, C ₁ -C ₄ alkyl, trifluoromethyl, C ₁ - C ₄ alkoxy, C ₁ -C ₂ fluoroalkoxy or C ₁ -C ₄ alkoxy-carbonyl is substituted], C ₁ - C ₆ alkylamino [which is optionally substituted by fluorine, cyano or C ₁ -C ₄ alkoxy], benzylamino [which is optionally substituted by fluorine, chlorine, nitro, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ - Alkoxy or C ₁ -C ₄ alkoxy-carbonyl is substituted], C ₃ -C ₆ cycloalkylamino, phenylamino [which may be replaced by fluorine, chlorine, cyano, nitro, C ₁ -C ₄ alkyl, trifluoromethyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₂ -fluoroalkoxy or C ₁ -C ₄ -alkoxy-carbonyl is substituted], di- (C ₁ -C ₂ -alkyl) -amino, C ₁ -C ₄ -alkylcarbonyl, phenylcarbonyl or C ₁ -C ₄ alkoxy-carbonyl.

The invention relates in particular to compounds of the formula (I) in which
R ^{1 is} C ₁ -C ₈ -alkyl [which is optionally substituted by fluorine or chlorine], C ₃ -C ₄ -alkenyl, C ₁ -C ₂ -alkoxycarbonylmethyl, phenyl, phenylethyl or benzyl [which is optionally substituted by fluorine, Chlorine, nitro, cyano, methyl, methoxy or methoxycarbonyl is substituted],
R ^{2 represents} hydrogen,
R ³ for the rest

stands in what
R ^{5 represents} chlorine, methyl, ethyl, methoxy, difluoromethoxy or ethoxy,
X represents nitrogen,
Y represents nitrogen or a methine bridge (CH), and
Z stands for an optionally substituted methine bridge CR ⁷ , where
R ^{7 represents} hydrogen, chlorine, methyl, methoxy, ethoxy, methylthio, ethylthio, dimethylamino or diethylamino and
R ^{4 is} hydrogen, C ₁ -C ₄ alkyl [which is optionally substituted by fluorine, chlorine, cyano, C ₁ -C ₂ alkoxycarbonyl or C ₁ -C ₂ alkoxy], cyclopropyl, C ₂ -C ₄ - alkenyl [which is optionally substituted by fluorine or chlorine], benzyl, phenyl [which is optionally substituted by fluorine, chlorine, nitro, methyl, trifluoromethyl, methoxy or trifluoromethoxy], C ₁ -C ₄ -alkoxy, phenoxy, C ₁ - C ₄ alkylamino, benzylamino, cyclohexylamino, phenylamino, dimethylamino or C ₁ -C ₂ alkoxycarbonyl.

The manufacturing method according to the invention specified above ongoing chemical reaction can for example can be outlined by the following formula:

Formula (II) provides a general definition of the 1- (2-oxyaminosulfonylphenylsulfonyl) -3-heteroarylureas to be used as starting materials in the process according to the invention. In this formula (II), R ¹ , R ² and R ³ preferably represent those radicals which have already been mentioned as preferred for these substituents in connection with the description of the substances of the formula (I) according to the invention.

Examples are the compounds of formula (II) called:

Table 1

The compounds of the formula (II) are known (cf. e.g. B. EP-A 1 73 322).

Formula (III) provides a general definition of the acylating agents to be used as starting materials in the process according to the invention. In this formula (III), R ⁴ preferably represents those radicals which have already been mentioned for these substituents in connection with the description of the substances of the formula (I) according to the invention. Q in this formula represents a leaving group customary in acylating agents, preferably halogen, such as fluorine, chlorine and bromine, phenoxy, C ₁ -C ₄ -alkoxy such as methoxy and ethoxy or the radical R ⁸ -COO-, in which R ^{8 represents} C ₁ -C ₄ alkyl. Q particularly preferably represents fluorine, chlorine, bromine, methoxy, ethoxy or phenoxy.

Examples are the compounds of formula (III) called:

Q-CO-R ⁴ (III)

Table 2

The compounds of formula (III) are known and / or can be produced by known processes.

The inventive method for producing the new Compounds of formula (I) is preferably used carried out by diluents. As a diluent practically all inert organic Solvent in question. These preferably include aliphatic and aromatic, optionally halogenated Hydrocarbons such as pentane, hexane, heptane, cyclohexane, Petroleum ether, petrol, ligroin, benzene, toluene, xylene, methylene chloride, Ethylene chloride, chloroform, carbon tetrachloride, Chlorobenzene and o-dichlorobenzene, ethers such as diethyl and dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, Tetrahydrofuran and dioxane, ketones such as acetone, Methyl ethyl, methyl isopropyl and methyl isobutyl ketone, Esters such as methyl and ethyl acetate, nitriles such as B. acetonitrile and propionitrile, amides such as e.g. B. dimethylformamide, dimethylacetamide and N-methyl-pyrrolidone as well as dimethyl sulfoxide, tetramethylene sulfone and Hexamethylphosphoric triamide.

Acid acceptors in the process according to the invention all commonly used for such implementations Acid binders are used. Preferably Alkali metal hydroxides such as z. B. sodium and potassium hydroxide, alkaline earth metal hydroxides such as e.g. B. calcium hydroxide, Alkali carbonates and alcoholates such as sodium and Potassium carbonate, sodium and potassium methylate or ethylate, furthermore aliphatic, aromatic or heterocyclic amines, for example triethylamine, trimethylamine, dimethylaniline,  Dimethylbenzylamine, pyridine, 4-dimethylamino-pyridine, 1,5-diazabicyclo- [4,3,0] -non-5-ene (DBN), 1,8-diazabicyclo- [5,4,0] -undec-7-ene (DBU) and 1,4-diazabicyclo- [2,2,2] octane (DABCO).

The reaction temperatures can in the inventive Procedures can be varied over a wide range. in the generally one works at temperatures between -20 ° C and + 60 ° C, preferably at temperatures between 0 ° C and + 40 ° C. The process according to the invention is general carried out under normal pressure.

To carry out the process according to the invention, 1 to 10, preferably 2 to 8 mol of acylating agent of the formula (III) and 1 to 10 mol, preferably 2 to 8 mol, of acid acceptor are used per 1 mol of the compound of the formula (II). When using acid anhydrides of the formula (III) (Q = R ⁸ -COO-) as starting materials for the process according to the invention, it is also possible to work without an acid acceptor.

The reaction components are usually at room temperature or put together under external cooling and that The reaction mixture is stirred until the end of the reaction.

The workup can be carried out in the usual way; for example, if necessary, and / or with an organic that is practically immiscible with water Solvents such as B. methylene chloride, diluted, washed with water, dried, filtered and concentrated. The Crystalline product of formula (I) can by Suction be isolated.  

The active compounds according to the invention can be used as defoliants, Desiccants, herbicides and especially as Weed killers are used. Under weeds in the broadest sense, all plants are to be understood that growing up in places where they are undesirable. If she Substances according to the invention as total or selective herbicides work depends essentially on the applied Amount off.

The active compounds according to the invention can, for. B. in the following Plants are used:

Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, ipomoea, polygonum, sesbania, ambrosia, cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea.

Dicotyledon cultures of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita.

Monocotyledon weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera.  

Monocot cultures of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Pineapple, Asparagus, Allium.

However, the use of the active compounds according to the invention is by no means limited to these genres, but extends to other plants in the same way.

The compounds are suitable depending on the concentration for total weed control z. B. on industrial and track systems and on paths and squares with and without Tree growth. Likewise, weed control compounds in permanent crops, e.g. B. forest, ornamental wood, Fruit, wine, citrus, nut, banana, coffee, tea, Gum, oil palm, cocoa, berry fruit and hop plants and for selective weed control in annuals Cultures are used.

The active compounds according to the invention are suitable for selective Control of mono- and dicotyledon weeds in particular in pre-and post-emergence monocot cultures.

The active ingredients can be in the usual formulations are transferred, such as solutions, emulsions, wettable powders, Suspensions, powders, dusts, pastes, soluble Powders, granules, suspension emulsion concentrates, Active substance-impregnated nature and synthetic substances as well as very fine encapsulation in polymeric substances.  

These formulations are prepared in a known manner e.g. B. by mixing the active ingredients with extenders, So liquid solvents and / or solid Carriers, optionally using surfactants Agents, i.e. emulsifiers and / or Dispersing agents and / or foaming agents.

In the case of the use of water as an extender e.g. B. also organic solvents as auxiliary solvents be used. As a liquid solvent essentially come into question: aromatics, such as xylene, Toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, Chlorethylene or methylene chloride, aliphatic Hydrocarbons, such as cyclohexane or paraffins, e.g. B. petroleum fractions, mineral and vegetable oils, Alcohols, such as butanol or glycol, and their ethers and Esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulfoxide, and water.

The following are suitable as solid carriers: e.g. B. ammonium salts and natural rock powders, such as Kaolins, clays, talc, chalk, quartz, attapulgite, Montmorillonite or diatomaceous earth and synthetic rock powder,  such as finely divided silica, aluminum oxide and silicates, come as solid carriers for granules in question: e.g. B. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well synthetic granules from inorganic and organic Flours and granules from organic material such as sawdust,  Coconut shells, corn cobs and tobacco stems; as Emulsifying and / or foaming agents are possible: e.g. B. non-ionic and anionic emulsifiers, such as polyoxyethylene Fatty acid esters, polyoxyethylene fatty alcohol Ethers, e.g. B. alkylaryl polyglycol ethers, alkyl sulfonates, Alkyl sulfates, aryl sulfonates and protein hydrolyzates; as dispersants come into question: z. B. Lignin sulfite liquor  and methyl cellulose.

In the formulations, adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers can be used, such as Gum arabic, polyvinyl alcohol, polyvinyl acetate, as well natural phospholipids such as cephalins and lecithins and synthetic phospholipids. Other additives can be mineral and vegetable oils.

Dyes such as inorganic pigments, e.g. B. Iron oxide, titanium oxide, ferrocyan blue and organic dyes, such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, Boron, copper, cobalt, molybdenum and zinc can be used.

The formulations generally contain between 0.1 and 95 percent by weight of active ingredient, preferably between 0.5 and 90%.

The active compounds according to the invention can be used as such or in their formulations also in a mixture with known ones Find herbicides for weed control, wherein Ready formulations or tank mixes are possible.  

Known herbicides can be used for the mixtures are such. B. N- (2-benzothiazolyl) -N, N'-dimethylurea, 3- (3-chloro- 4-methylphenyl) -1,1-dimethylurea, 3- (4-isopropylphenyl) - 1,1-dimethylurea, 2-chloro-N - {[(4-methoxy-6-methyl- 1,3,5-triazin-2-yl) amino] carbonyl} benzenesulfonamide, 2-hydroxycarbonyl-N - {[(4-methoxy-6-methyl-1,3,5- triazin-2-yl) -amino] -carbonyl} -benzenesulfonamide, 2-ethylamino- 6- (1,1-dimethylethylamino) -4-methylthio-1,3,5- triazine, 4-amino-6- (1,1-dimethylethyl) -3-methylthio-1,2,4- triazin-5 (4H) -one, 4-amino-6- (1,1-dimethylethyl) -3-ethylthio- 1,2,4-triazin-5 (4H) -one, 1-amino-6-ethylthio-3- (2,2- dimethylpropyl) -1,3,5-triazine-2,4- (1H, 3H) -dione, 2- [4- (2,4- Dichlorophenoxy) -phenoxy] -propionic acid methyl ester, the R- Enantiomers of 2- {4 - [(3,5-dichloro-2-pyridinyl) oxy] phenoxy} - trimethylsilyl methyl propionate, 2,4- Dichlorophenoxyacetic acid, 2- (2,4-dichlorophenoxy) propionic acid, 4-chloro-2-methylphenoxyacetic acid, 2- (4-chloro-2- methyl-phenoxy) -propionic acid, 3,5-diiodo-4-hydroxy-benzonitrile, 3,5-dibromo-4-hydroxy-benzonitrile, N- (1-ethylpropyl) - 3,4-dimethyl-2,6-dinitroaniline, N, N-diisopropyl 2,3,3-trichloroallyl thiol carbamate, 2- (2-benzothiazolyloxy) - N-methyl-N-phenylacetamide, 3- (2,4-dichlorophenoxy) -6-nitrobenzoic acid methyltr, 2- [4,5-dihydro-4-methyl-4- (1-methylethyl) - 5-oxo-1H-imidazol-2-yl] -4 (5) -methyl-benzoic acid methyl ester, [(4-amino-3,5-dichloro-6-fluoro-2-pyridyl) - oxy] acetic acid and 3-isopropyl-2,1,3-benzothiadiazinon- (4) -2,2-dioxide. Surprisingly, some mixtures have also synergistic effect.

Also a mixture with other known active ingredients, such as fungicides, insecticides, acaricides, nematicides,  Protection against bird feed, plant nutrients and Soil improvers are possible.

The active ingredients as such, in the form of their formulations or the one prepared therefrom by further dilution Application forms, such as ready-to-use solutions, Suspensions, emulsions, powders, pastes and Granules can be applied. The application happens in the usual way, e.g. B. by pouring, spraying, spraying, Scatter.

The active compounds according to the invention can be used both before and can also be applied after the plants have emerged.

They can also be worked into the soil before sowing will.

The amount of active ingredient used can be greater Fluctuate range. It essentially depends on the type of the desired effect. In general, the Application rates between 5 g and 5 kg of active ingredient per hectare Soil area, preferably between 10 g and 1 kg per ha.

The preparation and use of the active compounds according to the invention can be seen from the examples below.

Manufacturing examples example 1

10 g (0.13 mol) of acetyl chloride are added at 20-30 ° C a mixture of 8.6 g (0.02 mol) of 1- (2-methoxyaminosulfonyl- phenylsulfonyl) -3- (4-methoxy-6-methyl-pyrimidine-2- yl) urea, 12.2 g (0.1 mol) of 4-dimethylaminopyridine and 150 ml of methylene chloride added with stirring. The reaction mixture is stirred for 3 hours, washed with water, dried, filtered and concentrated.

6.5 g (74% of theory) of 1- (N-acetyl-2-methoxyaminosulfonyl- phenylsulfonyl) -3- (4-methoxy-6-methyl-pyrimidine) 2-yl) urea as a crystalline residue from Melting point 190 ° C.

Analogously to Example 1, the following compounds of the Formula (I) can be prepared:

Table 3

Example A Pre-emergence test

Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether

For the preparation of a suitable active ingredient preparation is mixed 1 part by weight of active ingredient with the specified Amount of solvent, gives the specified amount of emulsifier and dilute the concentrate with water on the desired concentration.

Seeds of the test plants are sown in normal soil and watered with the preparation of active compound after 24 hours. The amount of water per unit area is expediently kept constant. The concentration of active substance in the preparation is irrelevant, the only decisive factor is the amount of active substance applied per unit area. After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control. It means:
0% = no effect (like untreated control)
100% = total annihilation

In this test, e.g. B. the following connection of Production examples (9) have a better effect against Abutilon, Amaranthus, Solanum and Agropyron in wheat as the comparison compounds (A).  

Example B Post emergence test

Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether

For the preparation of a suitable active ingredient preparation you mix 1 part by weight of active ingredient with the specified amount of solvent, gives the specified Amount of emulsifier and dilute the concentrate with Water to the desired concentration.

With the preparation of the active ingredient you inject test plants, which have a height of 5-15 cm so that each desired amounts of active ingredient per unit area be applied. The concentration of the spray liquor is chosen so that in 2000 l of water / ha each desired amounts of active ingredient are applied. To The degree of damage to the plants is three weeks rated in% damage compared to development the untreated control.

It means:
0% = no effect (like untreated control)
100% = total annihilation

In this test, e.g. B. the following compounds the manufacturing examples (9) and (12) with good compatibility better effect against cassia in wheat, Ipomoea, Polygonum and Sinapis as the comparison compounds (A) and (B).

Claims (7)

1) acylated 1- (2-oxyaminosulfonylphenylsulfonyl) -3- heteroaryl-ureas of the general formula (I) in which
R ^{1 represents} an optionally substituted radical from the series alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aralkyl and aryl,
R ^{2 represents} hydrogen or an optionally substituted radical from the series consisting of alkyl, alkenyl, alkynyl and aralkyl,
R ^{3 represents} an optionally substituted and / or optionally fused six-membered aromatic heterocycle which contains at least one nitrogen atom, and
R ^{4 represents} hydrogen or optionally substituted radicals from the series alkyl, cycloalkyl, cycloalkylalkyl, alkenyl, alkynyl, aryl, aralkyl, hetaryl, alkoxy, aralkoxy, aryloxy, alkylamino, aralkylamino, cycloalkylamino, arylamino, dialkylamino, alkylcarbonyl, arylcarbonyl and alkoxycarbonyl. 2) acylated 1- (2-oxyaminosulfonylphenylsulfonyl) -3- heteroaryl-ureas of the formula (I) according to claim 1, in which
R ¹ for C ₁ -C ₁₂ alkyl [which may be replaced by fluorine, chlorine, cyano, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ - Alkylsulfonyl, C ₁ -C ₄ alkylcarbonyl, C ₁ -C ₄ alkoxycarbonyl, C ₁ - C ₄ alkylaminocarbonyl or di- (C ₁ -C ₄ alkyl) amino carbonyl is substituted] , for C ₃ -C ₆ alkenyl [which is optionally substituted by fluorine, chlorine or bromine], C ₃ -C ₆ alkynyl, C ₃ - C ₆ cycloalkyl, C ₃ -C ₆ cycloalkyl-C ₁ -C _2- alkyl, phenyl-C ₁ -C ₂ -alkyl [which may be replaced by fluorine, chlorine, nitro, cyano, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy or C ₁ -C ₄ -alkoxy-carbonyl is substituted], for benzhydryl, or for phenyl [which is optionally substituted by fluorine, chlorine, nitro, cyano, C ₁ -C ₄ -alkyl, trifluoromethyl, C ₁ -C ₄ -alkoxy, C ₁ - C ₂ -fluoroalkoxy, C ₁ -C ₄ alkylthio, trifluoromethylthio or C ₁ -C ₄ alkoxycarbonyl is substituted],
R ² for hydrogen, C ₁ -C ₄ alkyl [which may be replaced by fluorine, chlorine, cyano, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfinyl, C ₁ -C _4- alkylsulfonyl, C ₁ -C ₄ -alkyl carbonyl, C ₁ -C ₄ -alkoxy-carbonyl, C ₁ -C ₄ -alkylamino-carbonyl or di- (C ₁ - C ₄ -alkyl) -amino-carbonyl substituted is] for C ₃ -C ₆ -alkenyl, C ₃ -C ₆ -alkynyl or phenyl-C ₁ -C ₂ -alkyl [which may be replaced by fluorine, chlorine, nitro, cyano, C ₁ -C ₄ -alkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ alkoxy carbonyl is substituted],
R ³ for the rest stands in what
R ^{5 represents} hydrogen, fluorine, chlorine, bromine, hydroxyl, C ₁ -C ₄ -alkyl [which is optionally substituted by fluorine and / or chlorine], C ₁ -C ₄ -alkoxy [which is optionally substituted by fluorine and / or chlorine is], C ₁ -C ₄ -alkylthio [which is optionally substituted by fluorine and / or chlorine], amino, C ₁ -C ₄ -alkylamino or di- (C ₁ -C ₄ -alkyl) -amino,
X represents nitrogen or a methine bridge (CH),
Y represents nitrogen or an optionally substituted methine bridge CR ⁶ , where
R ^{6 represents} hydrogen, fluorine, chlorine, bromine, cyano, formyl, C ₁ -C ₄ alkyl, C ₁ -C ₃ alkoxycarbonyl or C ₁ -C ₃ alkylcarbonyl, and
Z represents nitrogen or an optionally substituted methine bridge CR ⁷ , where
R ⁷ for hydrogen, fluorine, chlorine, bromine, hydroxyl, C ₁ -C ₄ -alkyl [which is optionally substituted by fluorine and / or chlorine], C ₁ -C ₄ -alkoxy [which is optionally substituted by fluorine and / or chlorine is], C ₁ -C ₄ alkylthio [which is optionally substituted by fluorine and / or chlorine], amino, C ₁ -C ₄ alkylamino or di- (C ₁ -C ₄ alkyl) amino and
in which further
R ⁴ for hydrogen, C ₁ -C ₂₀ alkyl [which may be by fluorine, chlorine, bromine, cyano, C ₁ -C ₄ alkoxycarbonyl, C ₁ -C ₄ alkoxy, benzyloxy or by optionally fluorine, chlorine , bromine, cyano, nitro, methyl and / or trifluoromethyl-substituted phenoxy] C ₃ - C ₆ cycloalkyl, C ₃ -C ₆ -Cycloalky-C ₁ -C ₂ -alkyl, C ₂ - C ₆ alkenyl [ which is optionally substituted by fluorine, chlorine or bromine], C ₂ -C ₆ -alkynyl, phenyl-C ₁ -C ₂ -alkyl [which is optionally substituted by fluorine, chlorine, nitro, cyano, C ₁ -C ₄ -alkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ alkoxycarbonyl, is substituted], phenyl [which is optionally substituted by fluorine, chlorine, cyano, nitro, C ₁ -C ₄ alkyl, trifluoromethyl, C ₁ -C ₄ - Alkoxy, C ₁ -C ₂ fluoroalkoxy or C ₁ -C ₄ alkoxy-carbonyl is substituted], pyridyl [which is optionally substituted by fluorine, chlorine, cyano, nitro, methyl or methoxy], C ₁ -C ₆ alkoxy [which may be by fluorine, chlorine, cyano or C ₁ -C ₄ -Alkoxy is substituted], benzyloxy [which is optionally substituted by fluorine, chlorine, nitro, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ alkoxycarbonyl], phenoxy [which is optionally substituted is substituted by fluorine, chlorine, cyano, nitro, C ₁ -C ₄ -alkyl, trifluoromethyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₂ -fluoroalkoxy or C ₁ -C ₄ -alkoxy-carbonyl], C ₁ -C ₆ alkylamino [which is optionally substituted by fluorine, cyano or C ₁ -C ₄ alkoxy], benzylamino [which is optionally substituted by fluorine, chlorine, nitro, cyano, C ₁ - C ₄ alkyl, C ₁ -C ₄ -Alkoxy or C ₁ -C ₄ -alkoxy-carbonyl is substituted], C ₃ -C ₆ -cycloalkylamino, phenylamino [which may be replaced by fluorine, chlorine, cyano, nitro, C ₁ -C ₄ -alkyl, trifluoromethyl, C ₁ - substituted C ₄ -alkoxy-carbonyl], di - C ₄ alkoxy, C ₁ -C ₂ -fluoroalkoxy or C ₁ (C ₁ -C ₂ - alkyl) amino, C ₁ -C ₄ -alkyl-carbonyl, Phenylcarbonyl or C ₁ -C ₄ alkoxy-carbonyl. 3) acylated 1- (2-oxyaminosulfonylphenylsulfonyl) -3- heteroaryl-ureas of the formula (I) according to claim 1, in which
R ¹ for C ₁ -C ₈ alkyl [which is optionally substituted by fluorine or chlorine], C ₃ -C ₄ alkenyl, C ₁ -C ₂ alkoxycarbonylmethyl, phenyl, phenylethyl or benzyl [which is optionally substituted by fluorine, Chlorine, nitro, cyano, methyl, methoxy or methoxycarbonyl is substituted],
R ^{2 represents} hydrogen,
R ³ for the rest stands in what
R ^{5 represents} chlorine, methyl, ethyl, methoxy, difluoromethoxy or ethoxy,
X represents nitrogen,
Y represents nitrogen or a methine bridge (CH), and
Z stands for an optionally substituted methine bridge CR ⁷ , where
R ^{7 represents} hydrogen, chlorine, methyl, methoxy, ethoxy, methylthio, ethylthio, dimethylamino or diethylamino and
R ^{4 is} hydrogen, C ₁ -C ₄ alkyl [which is optionally substituted by fluorine, chlorine, cyano, C ₁ -C ₂ alkoxycarbonyl or C ₁ -C ₂ alkoxy], cyclopropyl, C ₂ -C ₄ alkenyl [which is optionally substituted by fluorine or chlorine], benzyl, phenyl [which is optionally substituted by fluorine, chlorine, nitro, methyl, trifluoromethyl, methoxy or trifluoromethoxy], C ₁ -C ₄ alkoxy, phenoxy, C ₁ -C ₄ Alkylamino, benzylamino, cyclohexylamino, phenylamino, dimethylamino or C ₁ -C ₂ alkoxycarbonyl. 4) Process for the preparation of acylated 1- (2-oxyaminosulfonylphenylsulfonyl) -3-heteroaryl-ureas of the formula (I) according to claim 1, characterized in that 1- (2-oxyaminosulfonylphenylsulfonyl) -3- heteroaryl-ureas of the formula ( II) in which
R ¹ , R ² and R ^{3 have} the meanings given above in claim 1,
with acylating agents of the formula (III) Q-CO-R ⁴ , 6 (III) in which
R ^{4 has} the meanings given above in claim 1 and
Q represents a leaving group customary in acylating agents,
if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent. 5) Herbicidal agents, characterized by a content of at least one acylated 1- (2-oxyaminosulfonyl- phenylsulfonyl) -3-heteroaryl-urea of the general Formula (I) according to claim 1. 6) Use of acylated 1- (2-oxyaminosulfonylphenylsulfonyl) -  3-heteroaryl ureas of the general Formula (I) according to claim 1 for combating undesirable plant growth. 7) Process for the preparation of herbicidal compositions, thereby characterized in that acylated 1- (2-oxyaminosulfonylphenylsulfonyl) - 3-heteroaryl ureas of the general formula (I) according to Claim 1 with Extenders and / or surfactants mixed.