DE10200605A1 - Substituted thiazolylsulfonylureas - Google Patents

Abstract

The invention relates to substituted thiazolyl sulfonyl urea compounds of general formula (I), in which A, R<sp>1</sp>, R<sp>2</sp>, R<sp>3</sp>, R<sp>4</sp>, and R<sp>5</sp> have the meaning indicated in the description, the use of said compounds as herbicides, and a method for producing said compounds.

Description

The invention relates to new substituted thiazolylsulfonylureas, processes for their production and their use as plant treatment agents, in particular as herbicides.

It is already known that certain substituted thiazolylsulfonylureas have herbicidal properties (cf. EP-A-95925, JP-A-5816587 - cited in Chem. Abstracts 100: 139151, JP-A-6045572 - cited in Chem. Abstracts 103: 104974). The herbicidal activity and the tolerance towards Cultivated plants of these compounds, however, are not satisfactory in all respects.

The new substituted thiazolylsulfonylureas of the general formula (I)


in which
A stands for nitrogen or the grouping CX, where
X represents hydrogen, halogen or in each case optionally substituted by halogen alkyl or alkoxy each having 1 to 6 carbon atoms, or together with R ¹ or R ² for one of the groupings -CH ₂ CH ₂ O-, -CH ₂ CH ₂ S-, -CH ₂ CH ₂ CH ₂ - stands,
R ^{1 stands} for hydrogen, for halogen or for alkyl, alkoxy, alkylthio, alkylamino or dialkylamino, each optionally substituted by halogen or C ₁ -C ₄ alkoxy, each having 1 to 6 carbon atoms in the alkyl groups,
R ^{2 represents} hydrogen, halogen or alkyl, alkoxy, alkylthio, alkylamino or dialkylamino, each optionally substituted by halogen or C ₁ -C ₄ alkoxy, each having 1 to 6 carbon atoms in the alkyl groups,
R ^{3 represents} hydrogen or alkyl having 1 to 6 carbon atoms which is optionally substituted by cyano, halogen, C ₁ -C ₄ alkoxy or C ₁ -C ₄ alkoxycarbonyl,
R ^{4 represents} alkyl having 1 to 6 carbon atoms, alkenyl or alkynyl each having 3 to 6 carbon atoms or cycloalkyl having 3 to 6 carbon atoms, and
R ^{5 represents} alkyl with 1 to 6 carbon atoms optionally substituted by halogen or C ₁ -C ₄ alkoxy,
as well as salts of compounds of formula (I) found.

Preferred substituents or ranges of the radicals present in the formulas listed above and below are described below:
A preferably represents nitrogen or the grouping CX, where
X represents hydrogen, fluorine, chlorine, bromine or in each case optionally substituted by fluorine and / or chlorine, methyl, ethyl, methoxy or ethoxy, or together with R ¹ or R ² for one of the groupings -CH ₂ CH ₂ O-, -CH ₂ CH ₂ S-, -CH ₂ CH ₂ CH ₂ - stands,
R ¹ preferably represents hydrogen, fluorine, chlorine, bromine or methyl, ethyl, n- or i-propyl, n-, i-, n- or i-propyl, which are optionally substituted by fluorine, chlorine, methoxy, ethoxy or n- or i-propoxy. s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino.
R ² preferably represents hydrogen, fluorine, chlorine, bromine, or methyl, ethyl, n- or i-propyl, n-, i-, n- or i-propyl, which are each optionally substituted by fluorine, chlorine, methoxy, ethoxy or n- or i-propoxy. s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino.
R ³ preferably represents hydrogen or methyl, ethyl, n- or i- which is optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy-carbonyl. Propyl, n-, i- or s-butyl.
R ⁴ preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, propenyl, butenyl, propynyl, butynyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
R ⁵ preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each optionally substituted by fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy.
A particularly preferably represents nitrogen or the grouping CX, where
X represents hydrogen, fluorine, chlorine, methyl or methoxy, or together with R ¹ or R ^{2 represents} one of the groupings -CH ₂ CH ₂ O-, -CH ₂ CH ₂ S-, -CH ₂ CH ₂ CH ₂ - ,
R ¹ particularly preferably represents hydrogen, fluorine, chlorine, bromine, or methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n which is in each case optionally substituted by fluorine, chlorine, methoxy, ethoxy or n- or i-propoxy - or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino.
R ² particularly preferably represents hydrogen, fluorine, chlorine, bromine, or methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n which is optionally substituted by fluorine, chlorine, methoxy, ethoxy or n- or i-propoxy - or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino.
R ³ particularly preferably represents hydrogen or methyl, ethyl, n- or i, each optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy-carbonyl propyl.
R ⁴ particularly preferably represents methyl, ethyl, n- or i-propyl, propenyl, butenyl, propynyl, butynyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
R ⁵ particularly preferably represents methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine, chlorine, methoxy or ethoxy.
A very particularly preferably represents nitrogen or a CH group.
R ¹ very particularly preferably represents chlorine, methyl, trifluoromethyl, ethyl, methoxy, difluoromethoxy, trifluoromethoxy, ethoxy, fluoroethoxy, difluoroethoxy, trifluoroethoxy, methylthio, ethylthio, methylamino, ethylamino or dimethylamino.
R ² very particularly preferably represents chlorine, methyl, trifluoromethyl, ethyl, methoxy, difluoromethoxy, trifluoromethoxy, ethoxy, fluoroethoxy, difluoroethoxy, trifluoroethoxy, methylthio, ethylthio, methylamino, ethylamino or dimethylamino.
R ³ very particularly preferably represents hydrogen or methyl.
R ⁴ very particularly preferably represents methyl, ethyl, n- or i-propyl, or cyclopropyl.
R ⁵ very particularly preferably represents methyl, ethyl, n- or i-propyl, each optionally substituted by fluorine and / or chlorine.
R ⁴ most preferably represents methyl or ethyl.

A very particularly preferred group are those compounds of the formula (I) in which
A stands for nitrogen,
R ^{1 represents} chlorine, methyl, trifluoromethyl, ethyl, methoxy, difluoromethoxy, trifluoromethoxy, ethoxy, fluoroethoxy, difluoroethoxy, trifluoroethoxy, methylthio, ethylthio, methylamino, ethylamino or dimethylamino,
R ^{2 represents} chlorine, methyl, trifluoromethyl, ethyl, methoxy, difluoromethoxy, trifluoromethoxy, ethoxy, fluoroethoxy, difluoroethoxy, trifluoroethoxy, methylthio, ethylthio, methylamino, ethylamino or dimethylamino,
R ^{3 represents} hydrogen or methyl,
R ^{4 represents} methyl, ethyl, n- or i-propyl, and
R ^{5 represents} methyl or ethyl.

Another very particularly preferred group are those compounds of the formula (I) in which
A stands for a CH grouping,
R ^{1 represents} methyl, trifluoromethyl, ethyl, methoxy, difluoromethoxy, trifluoromethoxy, ethoxy, fluoroethoxy, difluoroethoxy, trifluoroethoxy, methylthio, ethylthio, methylamino, ethylamino or dimethylamino,
R ^{2 represents} methyl, trifluoromethyl, ethyl, methoxy, difluoromethoxy, trifluoromethoxy, ethoxy, fluoroethoxy, difluoroethoxy, trifluoroethoxy, methylthio, ethylthio, methylamino, ethylamino or dimethylamino,
R ^{3 represents} hydrogen,
R ^{4 represents} methyl, ethyl, n- or i-propyl, and
R ^{5 represents} methyl or ethyl.

The invention further preferably relates to sodium, potassium, magnesium, calcium, ammonium, C ₁ -C ₄ alkylammonium, di (C ₁ -C ₄ alkyl) ammonium, tri ( C ₁ -C ₄ -alkyl) -ammonium, tetra- (C ₁ -C ₄ -alkyl) -ammonium, tri- (C ₁ - C ₄ alkyl) -sulfonium-, C ₅ - or C ₆ cycloalkyl -ammonium- and di- (C ₁ -C ₂ -alkyl) benzylammonium salts of compounds of formula (I) in which A, R ¹ , R ² , R ³ , R ⁴ and R ⁵ are preferably the above have the meanings given.

The general or preferred areas listed above Residual definitions apply both to the end products of the formula (I) and accordingly for the starting or intermediate products required for the production. This Residual definitions can be among themselves, that is, between the specified ones preferred areas can be combined as desired.

Those compounds of the formula (I) are preferred according to the invention which are a combination of those listed above as preferred ("preferred") Meanings exist.

According to the invention, particular preference is given to those compounds of the formula (I) in which a combination of those listed as particularly preferred above Meanings exist.

According to the invention, those compounds of the Formula (I) in which a combination of the above is particularly preferred listed meanings is present.

Most preferred according to the invention are those compounds of the formula (I), in which a combination of the above is most preferred listed meanings is present.

Saturated or unsaturated hydrocarbon radicals such as alkyl or alkenyl - also in connection with heteroatoms, such as in alkoxy - as far as possible each straight-chain or branched.

Optionally substituted radicals can be mono- or polysubstituted, in the case of multiple substitution, the substituents are the same or different can.

The new substituted thiazolylsulfonylureas of the general formula (I) have interesting biological properties. They stand out in particular from strong herbicidal activity.

The new substituted thiazolylsulfonylureas of the general formula (I) are obtained if substituted aminoazines of the general formula (II)


in which
A, R ¹ and R ^{2 have} the meaning given above,
Z represents halogen, alkoxy or aryloxy and
R ^{3 has} the meaning given above or represents the group -C (O) -Z,
with thiazole sulfonamides of the general formula (III)


in which
R ⁴ and R ^{5 have} the meaning given above,
if appropriate in the presence of one or more reaction auxiliaries and if appropriate in the presence of one or more diluents,
and optionally the compounds of the general formula (I) thus obtained are converted into their salts by customary methods.

• a) durch Umsetzung von Aminoazinen der allgemeinen Formel (IV) mit Thiazolylsulfonylisocyanaten der allgemeinen Formel (V); n, R¹, R², R³ und R⁴ wie oben (vgl. WO-A-97/32861):
  
  
  
• b) durch Umsetzung von Aminoazinen der allgemeinen Formel (IV) mit substituierten Fluoralkoxybenzolsulfonamiden der allgemeinen Formel (VI); n, R¹, R², R³ und R⁴ wie oben, Z: Halogen, C₁-C₄-Alkoxy oder Phenoxy (vgl. WO-A-97/32861):
  
  
  

In principle, the new substituted thiazolylsulfonylureas of the general formula (I) can also be obtained as shown schematically below:

• a) by reacting aminoazines of the general formula (IV) with thiazolylsulfonyl isocyanates of the general formula (V); n, R ¹ , R ² , R ³ and R ⁴ as above (see WO-A-97/32861):
  
  
  
• b) by reacting aminoazines of the general formula (IV) with substituted fluoroalkoxybenzenesulfonamides of the general formula (VI); n, R ¹ , R ² , R ³ and R ⁴ as above, Z: halogen, C ₁ -C ₄ alkoxy or phenoxy (cf. WO-A-97/32861):
  
  
  

If, for example, 2-methoxycarbonylamino-4-methoxy-6-trifluoromethyl-1,3,5-triazine and 2-ethylamino-4-trifluoromethyl-thiazole-5-sulfonamide are used as starting materials, the course of the reaction in the process according to the invention can be illustrated by the following formula are outlined:

The aminoazines to be used as starting materials in the process according to the invention for the preparation of compounds of the general formula (I) are generally defined by the formula (II). In the general formula (II), A, R ¹ , R ² and R ³ preferably or in particular have those meanings which, in connection with the description of the compounds of the general formula (I) according to the invention, are preferred or particularly preferred for A. , R ¹ , R ² and R ^{3 have been} given; Z preferably represents fluorine, chlorine, bromine, C ₁ -C ₄ -alkoxy or phenoxy, in particular chlorine, methoxy, ethoxy or phenoxy.

The starting materials of the general formula (II) are known and / or can be according to known processes can be prepared (see. DE-A-195 01 174, US-A-4 690 707).

Formula (III) provides a general definition of the thiazolesulfonamides to be used as starting materials in the process according to the invention for the preparation of compounds of the general formula (I). In the general formula (III), R ⁴ and R ⁵ preferably or in particular have those meanings which have been given above or in connection with the description of the compounds of the general formula (I) according to the invention as preferred or as particularly preferred for R ⁴ and R ⁵ have been.

The starting materials of the general formula (III) are known and / or can be according to processes known per se can be produced (cf. WO-A-01/47904).

The process according to the invention for the preparation of the new substituted Thiazolylsulfonylureas of the general formula (I) is preferably in the presence of a or several reaction aids. As a reaction aid for that Processes according to the invention generally come from the customary inorganic or organic bases or acid acceptors. This includes preferably alkali metal or alkaline earth metal acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkanolates, such as sodium, Potassium or calcium acetate, lithium, sodium, potassium or calcium amide, Sodium, potassium or calcium carbonate, sodium, potassium or calcium hydrogen carbonate, lithium, sodium, potassium or calcium hydride, lithium, Sodium, potassium or calcium hydroxide, sodium or potassium methanolate, -ethanolate, -n- or -i-propanolate, -n-, -i-, -s- or -t-butanolate; continue too basic organic nitrogen compounds, such as trimethylamine, Triethylamine, tripropylamine, tributylamine, ethyl-diisopropylamine, N, N-dimethylcyclohexylamine, dicyclohexylamine, ethyl-dicyclohexylamine, N, N-dimethyl-aniline, N, N-dimethyl-benzylamine, pyridine, 2-methyl, 3-methyl, 4-methyl, 2,4-dimethyl-, 2,6-dimethyl-, 3,4-dimethyl- and 3,5-dimethyl-pyridine, 5-ethyl-2-methylpyridine, 4-dimethylamino-pyridine, N-methyl-piperidine, 1,4-diazabicyclo [2.2.2] octane (DABCO), 1,5-diazabicyclo [4.3.0] non-5-ene (DBN), or 1.8 diazabicyclo- [5.4.0] -undec-7-en (DBU).

Phase transfer catalysts are also suitable as further reaction aids for the process according to the invention. Examples of such catalysts are:
Tetrabutylammonium bromide, tetrabutylammonium chloride, tetraoctylammonium chloride, tetrabutylammonium hydrogen sulfate, methyl trioctylammonium chloride, hexadecyl trimethylammonium chloride, hexadecyl trimidium, benzyl trimethylammonium, benzyl trimethylammonium, benzyl trimethylammonium, benzyl trimethylammonium Benzyl-triethylammonium-hydroxide, benzyl-tributylammonium-chloride, benzyl-tributylammonium-bromide, tetrabutylphosphonium-bromide, tetrabutylphosphonium-chloride, tributyl-hexadecylphosphonium-bromide, butyl-triphenylphosphonium-bromide, ethyl

The process of the invention for the preparation of the compounds of general Formula (I) is preferably made using one or more Diluent carried out. As a diluent to carry out the In addition to water, the process according to the invention in particular includes inert organic solvents into consideration. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as gasoline, benzene, Toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, Dichloromethane, chloroform, carbon tetrachloride; Ethers, such as diethyl ether, Diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones such as acetone, butanone or methyl isobutyl ketone; Nitriles, such as acetonitrile, Propionitrile or butyronitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-formanilide, N-methyl-pyrrolidone or hexamethylphosphoramide; Esters such as methyl acetate or ethyl acetate, sulfoxides such as Dimethyl sulfoxide, alcohols, such as methanol, ethanol, n- or i-propanol, Ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, Diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, their mixtures with water or pure water.

The reaction temperatures can be carried out when carrying out the inventive Process can be varied over a wide range. Generally you work at temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° C.

The process according to the invention is generally carried out under normal pressure carried out. However, it is also possible to increase the process according to the invention or reduced pressure - generally between 0.1 bar and 10 bar - perform.

To carry out the process according to the invention, the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess. The The reaction is generally carried out in a suitable diluent carried out a reaction auxiliary and the reaction mixture is in generally stirred for several hours at the required temperature. The Working up is carried out according to customary methods (cf. the production examples).

From the compounds of general formula (I) according to the invention optionally salts are produced. Such salts are obtained in a simple manner usual salt formation methods, for example by dissolving or dispersing one Compound of formula (I) in a suitable solvent, such as. B. Methylene chloride, acetone, tert-butyl methyl ether or toluene, and addition of a suitable one Base such as B. sodium hydroxide. The salts can then - if necessary longer stirring - be isolated by concentration or suction (see Preparation Examples).

The active compounds according to the invention can be used as defoliants, desiccants, Herbicides and especially as weed killers. Weeds in the broadest sense are understood to mean all plants that are in places grow up where they are undesirable. Whether the substances according to the invention as total or Selective herbicides act essentially depends on the amount used.

The active compounds according to the invention can, for. B. can be used in the following plants:
Dicotyledon weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Gupopsis, Euphorbia , Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsesb, Senania, , Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.
Dicotyledon cultures of the genera: Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia.
Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Fistula, Eriochaimis, Antherocho, Eriocha, Antherocho , Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.
Monocot cultures of the genera: Allium, pineapple, asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea.

However, the use of the active compounds according to the invention is by no means limited to them Limited genres, but extends in the same way to others Plants.

The active compounds according to the invention are suitable depending on the Total weed control concentration, e.g. B. on industrial and track systems and on Because of and places with and without tree cover. Likewise, the Active compounds according to the invention for weed control in permanent crops, for. B. forest, ornamental wood, Fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, Berry fruit and hop plants, on ornamental and sports turf and pastures as well for selective weed control in annual crops.

The compounds of formula (I) according to the invention show strong herbicides Efficacy and a wide range of effects when used on the floor and on aerial parts of plants. To a certain extent, they are also suitable for selective use Control of monocot and dicot weeds in monocotyledon and dicotyledon cultures, both pre-emergence and post-emergence.

The active compounds according to the invention can be used in certain concentrations or Application rates also to control animal pests and fungal or bacterial plant diseases can be used. You let yourself be optionally also as intermediates or precursors for the synthesis of further active ingredients deploy.

According to the invention, all plants and parts of plants can be treated. Under Plants are understood here as all plants and plant populations desired and undesirable wild plants or crops (including naturally occurring crops). Crop plants can be plants that are caused by conventional breeding and optimization methods or by biotechnological and obtained genetic engineering methods or combinations of these methods can be, including the transgenic plants and including by Plant variety rights of protectable or non-protectable plant varieties. Under Plant parts are said to be all above-ground and underground parts and organs of the Plants such as sprout, leaf, flower and root are understood to be exemplary Leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well Roots, tubers and rhizomes are listed. One of the plant parts also crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, cuttings and seeds.

The treatment of the plants and plant parts according to the invention with the Active substances take place directly or by influencing their environment, habitat or Storage room according to the usual treatment methods, e.g. B. by diving, spraying, Evaporation, atomization, scattering, spreading and in the case of propagation material, especially in the case of seeds, further by single or multi-layer coating.

The active ingredients can be converted into the usual formulations, such as Solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, Active ingredient-impregnated natural and synthetic substances as well as very fine encapsulation in polymers Substances.

These formulations are prepared in a known manner, e.g. B. by mixing of the active ingredients with extenders, i.e. liquid solvents and / or solid Carriers, optionally using surface-active agents, So emulsifiers and / or dispersants and / or foam-generating Means.

In the case of the use of water as an extender, e.g. B. also organic Solvents are used as auxiliary solvents. As a liquid solvent essentially come into question: aromatics, such as xylene, toluene, or Alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as Chlorobenzenes, chlorethylenes 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.

Possible solid carriers are: B. ammonium salts and natural Rock flours, such as kaolins, clays, talc, chalk, quartz, attapulgite, Montmorillonite or diatomaceous earth and synthetic rock powder, such as highly disperse Silicic acid, aluminum oxide and silicates, as solid carriers for granules come into question: z. B. broken and fractionated natural rocks such as calcite, Marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, Coconut shells, corn cobs and tobacco stems; as emulsifying and / or Foaming agents are possible: z. 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 as well as 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 are used, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural Phospholipids such as cephalins and lecithins and synthetic phospholipids. Further 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 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 herbicides and / or with substances which Improve crop tolerance ("safeners") for weed control can be used, whereby ready formulations or tank mixes are possible. It So mixtures with weed control agents are also possible, which a or contain several known herbicides and a safener.

Known herbicides are suitable for the mixtures, for example
Acetochlor, Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Ametryne, Amicarbazone, Amidochlor, Amidosulfuron, Anilofos, Asulam, Atrazine, Azafenidin, Azimsulfuron, Beflubutamid, Benazolin (-ethyl), Benulfuronate ), Bentazon, Benzfendizone, Benzobicyclon, Benzofenap, Benzoylprop (-ethyl), Bialaphos, Bifenox, Bispyribac (-sodium), Bromobutide, Bromofenoxim, Bromoxynil, Butachlor, Butafenacil (-allyl), Butroxydim, Butylate, Cafenstrole Carbamide, Calox Carfentrazone (-ethyl), Chlomethoxyfen, Chloramben, Chloridazon, Chlorimuron (-ethyl), Chlornitrofen, Chlorsulfuron, Chlortoluron, Cinidon (-ethyl), Cinmethylin, Cinosulfuron, Clefoxydim, Clethodim, Clodinafop (-proropazone), Clodinafop (-proropazone), Clomidomop, Clopyrasulfuron (-methyl), Cloransulam (-methyl), Cumyluron, Cyanazine, Cybutryne, Cycloate, Cyclosulfamuron, Cycloxydim, Cyhalofop (-butyl), 2,4-D, 2,4-DB, Desmedipham, Diallate, Dicamba, Dichlorprop ( -P), diclofop (-methyl), diclosulam, diethatyl (-ethyl), D ifenzoquat, Diflufenican, Diflufenzopyr, Dimefuron, Dimepiperate, Dimethachlor, Dimethametryn, Dimethenamid, Dimexyflam, Dinitramine, Diphenamid, Diquat, Dithiopyr, Diuron, Dymron, Epropodan, EPTC, Esprocarb, Ethalethyl Sulfuron, Ethamethyl Sulfuron, Ethal Ethulfuronoxamate, Ethal Methyl Sulfurone, Ethal Ethulfuron Oxide Etobenzanide, fenoxaprop (-P-ethyl), fentrazamide, flamprop (-isopropyl, -isopropyl-L, -methyl), flazasulfuron, florasulam, fluazifop (-P-butyl), fluazolate, flucarbazone (-sodium), flufenacet, flufenpyr, Flumetsulam, flumiclorac (-pentyl), flumioxazin, flumipropyn, flumetsulam, fluometuron, fluorochloridone, fluoroglycofen (-ethyl), flupoxam, flupropacil, flurpyrsulfuron (-methyl, -sodium), flurenol (-butyl, flutyl), fluroxypuryl, fluroxypuryl -meptyl), Flurprimidol, Flurtamone, Fluthiacet (-methyl), Fluthiamide, Fomesafen, Foramsulfuron, Glufosinate (-ammonium), Glyphosate (-isopropylammonium), Halosafen, Haloxyfop (-ethoxyethyl, -P-methyl), Hexazinone (- Imazamethaben methyl), imazamethapyr, imazamox, imaza pic, Imazapyr, Imazaquin, Imazethapyr, Imazosulfuron, Iodosulfuron (-methyl, -sodium), Ioxynil, Isopropalin, Isoproturon, Isouron, Isoxaben, Isoxachlortole, Isoxaflutole, Isoxapyrifop, Ketospiradox, Mact Linefuronac, Mact Linefuronac, Lactofenuronac, Lenox, Lactofenonenoc, Lactofen, Lenox, Lactofen, Lenoc, Lactofen, Lenoc , Metamitron, Metazachlor, Methabenzthiazuron, Metobenzuron, Metobromuron, (alpha-) Metolachlor, Metosulam, Metoxuron, Metribuzin, Metsulfuron (-methyl), Molinate, Monolinuron, Naproanilide, Napropamide, Neburon, Oxosulfuronz, Orfluronz, Orfluronz, Norfluronz, Norfluronz, Orfluronz, Orfluronz, Orfluronz, Norfluronz, Orfluronz, Orfluronz, Orfluronz, Norfluronz, Orfluronz, Orfluronz, Norfluronz, Or , Oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat, pelargonic acid, pendimethalin, pendralin, penoxysulam, pentoxazone, pethoxamide, phenmedipham, picolinafen, piperophos, pretilachlor, primisulfuron (-methyl), profluazole, propanoxafiloxylchloros, propoxydachloroquone, propoxydachloroquone, propoxydachloroquone, propoxydachloroquone, propoxydoxyl chloros (-sodium), propyzamide, prosulfocarb, prosulfuron, pyraflufen (-ethyl), pyrazogyl, pyrazolates, pyrazosulfuron (-ethyl), pyrazoxyfen, pyribenzoxime , Pyributicarb, Pyridate, Pyridatol, Pyriftalid, Pyriminobac (-methyl), Pyrithiobac (-sodium), Quinchlorac, Quinmerac, Quinoclamine, Quizalofop (-Pethyl, -P-tefuryl), Rimsulfuron, Sethoxydim, Simazine, Simetrynentra, Sulzone Sulfometuron (-methyl), sulfosate, sulfosulfuron, tebutam, tebuthiuron, tepraloxydim, terbuthylazine, terbutryn, thenylchlor, thiafluamides, thiazopyr, thidiazimin, thifensulfuron (-methyl), thiobencarb, triocarbimulfonium, trioxydimonulfonil, tralloxydazonyl, tralloxydimonium, tri-oxydimonium, tri-oxoximazil, tralloximazon, tri Triclopyr, Tridiphane, Trifluralin, Trifloxysulfuron, Triflusulfuron (-methyl), Tritosulfuron.

Known safeners are also suitable for the mixtures, for example
AD-67, BAS-145138, Benoxacor, Cloquintocet (-mexyl), Cyometrinil, 2,4-D, DKA-24, Dichlormid, Dymron, Fenclorim, Fenchlorazol (-ethyl), Flurazole, Fluxofenim, Furilazole, Isoxadifen (-ethyl ), MCPA, Mecoprop (-P), Mefenpyr (-diethyl), MG-191, Oxabetrinil, PPG-1292, R-29148.

A mixture with other known active ingredients, such as fungicides, Insecticides, acaricides, nematicides, bird repellants, Plant nutrients and soil structure improvers are possible.

The active substances can be used as such, in the form of their formulations or in the form thereof application forms prepared by further dilution, such as ready-to-use Solutions, suspensions, emulsions, powders, pastes and granules are used become. The application happens in the usual way, e.g. B. by pouring, spraying, Spray, sprinkle.

The active compounds according to the invention can be used both before and after emergence of the plants are applied. You can also sow in the soil before sowing be incorporated.

The amount of active ingredient used can vary over a wide range. she depends essentially on the type of effect desired. In general the application rates are between 1 g and 10 kg of active ingredient per hectare Soil area, preferably between 5 g and 5 g per ha.

As already mentioned above, according to the invention all plants and their parts can be treated. In a preferred embodiment, go wild existing or by conventional organic breeding methods, such as crossing or protoplast fusion obtained plant species and plant varieties and their Parts treated. In a further preferred embodiment, transgenes are Plants and plant varieties by genetic engineering methods, if necessary in combination with conventional methods (Genetically Modified Organisms) and their parts. The term "parts" or "parts of." Plants "or" parts of plants "was explained above.

Plants of the commercially available in each case are particularly preferred according to the invention or plant varieties in use. Among plant varieties is understood to mean plants with certain properties ("traits") that are caused by conventional breeding, by mutagenesis, or also by recombinant DNA Techniques have been obtained. These can be varieties, bio and genotypes.

Depending on the plant species or plant varieties, their location and Growth conditions (soils, climate, growing season, nutrition) can be determined by the Treatment according to the invention also results in superadditive (“synergistic”) effects. For example, reduced application rates and / or extensions of the Spectrum of activity and / or an enhancement of the effect of the invention usable substances and agents - also in combination with other agrochemicals Active ingredients, better growth of crops, increased tolerance of Crops against high or low temperatures, increased tolerance of the Crops against drought or against water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripening, higher Crop yields, higher quality and / or higher nutritional value of the crop products, higher Shelf life and / or workability of the harvested products possible via the effects that are actually to be expected.

Among the preferred transgenes to be treated according to the invention (Genetically preserved) plants or plant varieties include all plants that received genetic material through the genetic modification, which gives these plants particular beneficial properties ("traits"). Examples of such properties are better plant growth, increased Tolerance to high or low temperatures, increased tolerance to Dryness or against water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripening, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or Machinability of crop products. Further and particularly highlighted examples for such properties are an increased defense of the plants against animal and microbial pests, such as insects, mites, phytopathogenic fungi, Bacteria and / or viruses and an increased tolerance of the plants to certain herbicidal active ingredients. The important ones are examples of transgenic plants Crops, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, Rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and Grapes) mentioned, especially corn, soybeans, potatoes, cotton and rapeseed be highlighted. As properties ("traits") become special highlighted the increased defense of the plants against insects by in the plants emerging toxins, especially those characterized by the genetic material Bacillus thuringiensis (e.g. through the genes CryIA (a), CryIA (b), CryIA (c), CryIIA, CryIIIA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CryIF as well as their combinations) are produced in the plants (hereinafter "Bt plants"). As properties ("Traits") are also particularly emphasized the increased defense against plants against fungi, bacteria and viruses through Systemic Acquired Resistance (SAR), Systemin, phytoalexins, elicitors and resistance genes and so on expressed proteins and toxins. As properties ("traits") continue to be particularly highlighted the increased tolerance of plants to certain herbicidal active ingredients, for example imidazolinones, sulfonylureas, Glyphosate or phosphinothricin (e.g. "PAT" gene). The one you want Genes conferring traits can also be used in combinations occur together in the transgenic plants. Examples are "Bt plants" Corn varieties, cotton varieties, soy varieties and potato varieties are among the Trade names YIELD GARD® (e.g. corn, cotton, soy), KnockOut® (e.g. corn), StarLink® (e.g. corn), Bollgard® (cotton), Nucotn® (cotton) and NewLeaf® (potato). As examples of herbicide-tolerant Plants are maize, cotton and soybeans that are among the Trade names Roundup Ready® (tolerance against glyphosate e.g. maize, Cotton, soy), Liberty Link® (tolerance to phosphinothricin, e.g. rapeseed), IMI® (tolerance to imidazolinones) and STS® (tolerance to Sulfonylureas e.g. B. corn) are sold. As a herbicide-resistant (conventional on Herbicide tolerance grown plants are also those under the name Clearfield® sold varieties (e.g. maize) mentioned. Of course, these apply Statements also for those developed in the future or in the future upcoming plant varieties with these or future developed genetic Properties ("traits").

The plants listed can be particularly advantageous according to the invention with the Compounds of general formula I or those of the invention Active ingredient mixtures are treated, in addition to the good control of Weed plants have the above-mentioned synergistic effects with the transgenic Plants or plant varieties occur. The active ingredients or mixtures Preferred ranges given above also apply to the treatment of these plants. Plant treatment with those in the present text should be particularly emphasized Specially listed compounds or mixtures.

The manufacture and use of the active compounds according to the invention start out the following examples.

Preparation Examples example 1

To a solution of 0.80 g (2.9 mmol) 4,6-Dimethoxy-2-phenoxycarbonylaminopyrimidine in 50 ml acetonitrile are at room temperature (about 20 ° C) with stirring consecutively 0.66 g (3.2 mmol) of 4-methyl-2-methylamino-thiazole-5-sulfonamide and 0.97 g (6.4 mmol) of 1,8-diazabicyclo (5.4.0) undec-7-ene added in portions. The Reaction mixture is stirred at room temperature for 18 hours and then concentrated under reduced pressure. The residue is in 250 ml Methylene chloride added, with 5% aqueous hydrochloric acid and then with water washed. The organic phase is dried with magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure, the residue with Diethyl ether digested and the crystalline product isolated by suction.

0.75 g (67% of theory) is obtained 4,6-Dimethoxy-2 - [[[[(4-methyl-2-methylamino-1,3-thiazol-5-yl) sulfonyl] amino] carbonyl] amino] pyrimidine dated Melting point 186 ° C.

Analogously to Example 1 and in accordance with the general description of the production process according to the invention, for example the compounds of the general formula (I) listed in Table 1 below can also be prepared.

Table 1 Examples of the compounds of the formula (I)

applications Example A Pre-emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, 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 level Concentration.

Seeds of the test plants are sown in normal soil. After 24 hours the soil is sprayed with the active ingredient preparation so that the desired one Amount of active ingredient is applied per unit area. The drug concentration in the spray liquor is chosen so that in 1000 liters of water per hectare each desired amount of active ingredient is applied.

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, for example, shows the compound according to Production Example 1 very effective against weeds.

Example B Post-emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, 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.

The active ingredient preparation is used to inject test plants which have a height of 5-15 cm have so that the desired amounts of active ingredient per Area unit are applied. The concentration of the spray liquor is chosen so that in 1000 l water / ha the desired amounts of active ingredient are applied.

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, for example, shows the compound according to Production Example 1 very effective against weeds.

Claims (9)

1. Compounds of the general formula (I)


in which
A stands for nitrogen or the grouping CX, where
X represents hydrogen, halogen or in each case optionally substituted by halogen alkyl or alkoxy each having 1 to 6 carbon atoms, or together with R ¹ or R ² for one of the groupings -CH ₂ CH ₂ O-, -CH ₂ CH ₂ S-, -CH ₂ CH ₂ CH ₂ - stands,
R ^{1 stands} for hydrogen, for halogen or for alkyl, alkoxy, alkylthio, alkylamino or dialkylamino, each optionally substituted by halogen or C ₁ -C ₄ alkoxy, each having 1 to 6 carbon atoms in the alkyl groups,
R ^{2 represents} hydrogen, halogen or alkyl, alkoxy, alkylthio, alkylamino or dialkylamino, each optionally substituted by halogen or C ₁ -C ₄ alkoxy, each having 1 to 6 carbon atoms in the alkyl groups,
R ^{3 represents} hydrogen or alkyl which has 1 to 6 carbon atoms and is optionally substituted by cyano, halogen, C ₁ -C ₄ alkoxy or C ₁ -C ₄ alkoxycarbonyl,
R ^{4 represents} alkyl having 1 to 6 carbon atoms, alkenyl or alkynyl each having 3 to 6 carbon atoms or cycloalkyl having 3 to 6 carbon atoms, and
R ^{5 represents} alkyl with 1 to 6 carbon atoms optionally substituted by halogen or C ₁ -C ₄ alkoxy,
and salts of compounds of the formula (I). 2. Compounds according to claim 1, characterized in that
X represents hydrogen, fluorine, chlorine, bromine or in each case optionally substituted by fluorine and / or chlorine, methyl, ethyl, methoxy or ethoxy, or together with R ¹ or R ² for one of the groupings -CH ₂ CH ₂ O-, -CH ₂ CH ₂ S-, -CH ₂ CH ₂ CH ₂ - stands,
R ¹ for hydrogen, fluorine, chlorine, bromine, or for methyl, ethyl, n- or i-propyl, n-, i-, s- which is optionally substituted by fluorine, chlorine, methoxy, ethoxy or n- or i-propoxy or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t Butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino,
R ² for hydrogen, fluorine, chlorine, bromine, or for methyl, ethyl, n- or i-propyl, n-, i-, s-, each optionally substituted by fluorine, chlorine, methoxy, ethoxy or n- or i-propoxy or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t Butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino,
R ^{3 represents} hydrogen or methyl, ethyl, n- or i-propyl which is optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy-carbonyl, is n-, i- or s-butyl,
R ^{4 represents} methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, propenyl, butenyl, propynyl, butynyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, and
R ^{5 represents} in each case optionally substituted by fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl. 3. Compounds according to claim 1, characterized in that
X represents hydrogen, fluorine, chlorine, methyl or methoxy, or together with R ¹ or R ^{2 represents} one of the groupings -CH ₂ CH ₂ O-, -CH ₂ CH ₂ S-, -CH ₂ CH ₂ CH ₂ - .
R ¹ for hydrogen, fluorine, chlorine, bromine, or for methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i, each optionally substituted by fluorine, chlorine, methoxy, ethoxy or n- or i-propoxy Propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino,
R ² for hydrogen, fluorine, chlorine, bromine, or for methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i, each optionally substituted by fluorine, chlorine, methoxy, ethoxy or n- or i-propoxy Propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino,
R ^{3 represents} hydrogen or represents methyl, ethyl, n- or i-propyl which is optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy-carbonyl .
R ^{4 represents} methyl, ethyl, n- or i-propyl, propenyl, butenyl, propynyl, butynyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, and
R ^{5 represents} in each case optionally substituted by fluorine, chlorine, methoxy or ethoxy methyl, ethyl, n- or i-propyl. 4. Compounds according to claim 1, characterized in that
R ^{1 represents} chlorine, methyl, trifluoromethyl, ethyl, methoxy, difluoromethoxy, trifluoromethoxy, ethoxy, fluoroethoxy, difluoroethoxy, trifluoroethoxy, methylthio, ethylthio, methylamino, ethylamino or dimethylamino,
R ^{2 represents} chlorine, methyl, trifluoromethyl, ethyl, methoxy, difluoromethoxy, trifluoromethoxy, ethoxy, fluoroethoxy, difluoroethoxy, trifluoroethoxy, methylthio, ethylthio, methylamino, ethylamino or dimethylamino,
R ^{3 represents} hydrogen or methyl,
R ^{4 represents} methyl, ethyl, n- or i-propyl, or cyclopropyl, and
R ^{5 represents} in each case optionally substituted by fluorine and / or chlorine methyl, ethyl, n- or i-propyl. 5. Compounds according to claim 1, characterized in that R ^{4 is} methyl or ethyl. 6. A process for the preparation of compounds according to claim 1, characterized in that aminoazines of the general formula (II)


in which
A, R ¹ and R ^{2 have} the meaning given in claim 1,
Z represents halogen, alkoxy or aryloxy and
R ^{3 has} the meaning given in claim 1 or represents the grouping -C (O) -Z,
with thiazole sulfonamides of the general formula (III)


in which
R ⁴ and R ^{5 have} the meaning given in claim 1,
if appropriate in the presence of one or more reaction auxiliaries and if appropriate in the presence of one or more diluents,
and optionally the compounds of the general formula (I) thus obtained are converted into their salts by customary methods. 7. A method of controlling unwanted vegetation, thereby characterized in that you have at least one connection according to one of the Claims 1 to 5 on the undesirable plants and / or their Living space. 8. Use of at least one compound according to one of the claims 1 to 5 for controlling unwanted plants. 9. Herbicidal agent, characterized by a content of a compound according to one of claims 1 to 5 and conventional extenders and / or surfactants.