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US20080076667A1 - Substituted fluoroalkoxyphenylsulfonylureas - Google Patents

Substituted fluoroalkoxyphenylsulfonylureas Download PDF

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Publication number
US20080076667A1
US20080076667A1 US11/899,364 US89936407A US2008076667A1 US 20080076667 A1 US20080076667 A1 US 20080076667A1 US 89936407 A US89936407 A US 89936407A US 2008076667 A1 US2008076667 A1 US 2008076667A1
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Prior art keywords
methoxy
och
methyl
chlorine
ethoxy
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US11/899,364
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Klaus-Helmut Muller
Ernst-Rudolf Gesing
Joachim Kluth
Mark Drewes
Peter Dahmen
Dieter Feucht
Rolf Pontzen
Ulrike Wachendorff-Neumann
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Individual
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Individual
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Priority to US11/899,364 priority Critical patent/US20080076667A1/en
Publication of US20080076667A1 publication Critical patent/US20080076667A1/en
Priority to US12/837,747 priority patent/US20100285963A1/en
Abandoned legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D521/00—Heterocyclic compounds containing unspecified hetero rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
    • C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom

Definitions

  • the invention relates to novel substituted fluoroalkoxyphenylsulfonylureas, to a process for their preparation and to their use as crop treatment agents, in particular as herbicides and as fungicides.
  • a very particularly preferred group are those compounds of the formula (D) in which
  • a further very particularly preferred group are those compounds of the formula (I) in which
  • n 3 or 4
  • n 3 or 4
  • the invention furthermore preferably provides 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 -cycloalkylammonium and di-(C 1 -C 2 -alkyl)benzylammonium salts of compounds of the formula (I), in which n, A, R 1 , R 2 , R 3 and R 4 have the meanings given above as being preferred.
  • radical definitions listed above apply both to the end products of the formula (I) and, correspondingly, to the starting materials or intermediates required in each case for the preparation. These radical definitions can be combined with one another as desired, i.e. including combinations between the given preferred ranges.
  • Saturated or unsaturated hydrocarbon radicals such as alkyl or alkenyl
  • alkyl or alkenyl are in each case straight-chain or branched as far as this is possible—including in combination with heteroatoms, such as in alkoxy.
  • Optionally substituted radicals may be mono- or polysubstituted, where in the case of polysubstitution the substituents may be identical or different.
  • novel substituted fluoroalkoxyphenylsulfonylureas of the general formula (I) have interesting biological properties. In particular, they have strong herbicidal and fungicidal activity.
  • novel substituted fluoroalkoxyphenylsulfonylureas of the general formula (I) are obtained when substituted aminoazines of the general formula (II) in which A, R 1 and R 2 are as defined above, Z represents halogen, alkoxy or aryloxy and R 3 is as defined above or represents the grouping —C(O)—Z, are reacted with fluoroalkoxybenzenesulfonamides of the general formula (III) in which n and R 4 are as defined above, if appropriate in the presence of one or more reaction auxiliaries and if appropriate in the presence of one or more diluents, and the resulting compounds of the general formula (I) are, if appropriate, converted into their salts by customary methods.
  • novel substituted fluoroalkoxyphenylsulfonylureas of the general formula (I) can also be obtained as shown schematically below:
  • the formula (II) provides a general definition of the aminoazines to be used as starting materials in the process according to the invention for preparing compounds of the general formula (I).
  • A, R 1 and R 2 preferably or in particular have those meanings which have already been mentioned above, in connection with the description of the compounds of the general formula (I) according to the invention, as being preferred or as being particularly preferred for A, R 1 and R 2 ;
  • 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 prepared by processes known per se (cf. DE-A-19 501 174, U.S. Pat. No. 4 690 707).
  • the formula (III) provides a general definition of the fluoroalkoxybenzene-sulfonamides further to be used as starting materials in the process according to the invention for preparing compounds of the general formula (I).
  • n and R 4 preferably or in particular have those meanings which have already been mentioned above, in connection with the description of the compounds of the general formula (I) according to the invention, as being preferred or as being particularly preferred for n and R 4 .
  • starting materials of the general formula (III) are known by disclosure in the form of a generic formula (cf. WO 97/03056). However, the starting materials of the formula (III) are a novel selection from among the prior-art compounds and therefore also form part of the subject matter of the present application. As a preferred group of the starting materials of the formula (III) according to the invention, mention may be made of those compounds in which n and R 4 do not simultaneously represent 2 and unsubstituted alkyl, respectively.
  • novel fluoroalkoxybenzenesulfonamides of the general formula (III) are obtained when hydroxybenzenesulfonamides of the general formula (VII) in which R 4 is as defined above, are reacted with ⁇ -fluoro- ⁇ -haloalkanes of the general formula (VIII) in which
  • hydroxybenzenesulfonamides of the general formula (VII) are known and/or can be prepared by processes known per se (cf. EP-A-44807, WO-A-97/03056).
  • ⁇ -fluoro- ⁇ -haloalkanes of the general formula (VIID further required as precursors are known organic chemicals for synthesis.
  • reaction auxiliaries suitable for the process according to the invention are, in general, the customary inorganic or organic bases or acid acceptors.
  • alkali metal or alkaline earth metal acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkoxides such as, for example, sodium acetate, potassium acetate or calcium acetate, lithium amide, sodium amide, potassium amide or calcium amide, sodium carbonate, potassium carbonate or calcium carbonate, sodium bicarbonate, potassium bicarbonate or calcium bicarbonate, lithium hydride, sodium hydride, potassium hydride or calcium hydride, lithium hydroxide, sodium hydroxide, potassium hydroxide or calcium hydroxide, sodium methoxide, ethoxide, n- or i-propoxide, n-, i-, s- or t-butoxide or potassium methoxide, ethoxide, n- or i-propoxide, n-, i-, s- or t-butoxide; furthermore also basic organic nitrogen compounds, such as, for example, trimethylamine, tri-ethy
  • phase-transfer catalysts examples include phase-transfer catalysts.
  • Such catalysts which may be mentioned are: tetrabutylammonium bromide, tetrabutylammonium chloride, tetraoctylammonium chloride, tetrabutylammonium hydrogen sulfate, methyltrioctylammonium chloride, hexadecyltrimethylammonium chloride, hexadecyltrimethylammonium bromide, benzyltrimethylammonium chloride, benzyltriethylammonium chloride, benzyl-trimethylammonium hydroxide, benzyltriethylammonium hydroxide, benzyltributyl-ammonium chloride, benzyltributylammonium bromide, tetrabutylphosphonium bromide, tetrabutylphosphonium chloride, tribut
  • the process according to the invention for preparing the compounds of the general formula (I) is preferably carried out using one or more diluents.
  • Suitable diluents for carrying out the process according to the invention are, in addition to water, especially inert organic solvents.
  • aliphatic, alicyclic or aromatic optionally halogenated hydrocarbons, such as, for example, benzine, 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 ether or ethylene glycol 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-methylformanilide, N-methylpyrrolidone or
  • reaction temperatures can be varied within a relatively wide range.
  • the process is carried out at temperatures between 0° C. and 150° C., preferably between 10° C. and 120° C.
  • the process according to the invention is carried out under atmospheric pressure. However, it is also possible to carry out the process according to the invention under elevated or reduced pressure—in general between 0.1 bar and 10 bar.
  • the starting materials are generally employed in approximately equimolar amounts. However, it is also possible to use a relatively large excess of one of the components.
  • the reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary, and the reaction mixture is generally stirred at the required temperature for a number of hours. Work-up is carried out by customary methods (cf. the Preparation Examples).
  • salts may be prepared from the compounds of the general formula (I) according to the invention.
  • Such salts are obtained in a simple manner by customary methods for forming salts, for example by dissolving or dispersing a compound of the formula (I) in a suitable solvent, such as, for example, methylene chloride, acetone, tert-butyl methyl ether or toluene, and adding a suitable base, such as, for example, sodium hydroxide.
  • a suitable solvent such as, for example, methylene chloride, acetone, tert-butyl methyl ether or toluene
  • a suitable base such as, for example, sodium hydroxide.
  • the salts can then—if appropriate after prolonged stirring—be isolated by concentration or by filtration with suction (cf. the Preparation Examples).
  • the active compounds according to the invention can be used as defoliants, desiccants, haulm killers and, especially, as weed killers. Weeds in the broadest sense are understood to mean all plants which grow in locations where they are undesired. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.
  • the active compounds according to the invention can be used, for example, in connection with the following plants:
  • Monocotyledonous crops of the genera Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea.
  • the active compounds according to the invention are suitable, depending on the concentration, for the total control of weeds, for example on industrial terrain and rail tracks, and on paths and areas with and without trees.
  • the active compounds according to the invention can be employed for controlling weeds in perennial crops, for example forests, decorative tree plantations, orchards, vineyards, citrus groves, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, soft fruit plantings and hop fields, on lawns, turf and pastureland, and for the selective control of weeds in annual crops.
  • the compounds of the formula (I) according to the invention have strong herbicidal activity and a broad activity spectrum when used on the soil and on above-ground parts of plants. To a certain extent they are also suitable for the selective control of monocotyledonous and dicotyledonous weeds in monocotyledonous and dicotyledonous crops, both by the pre-emergence and by the post-emergence method.
  • the active compounds according to the invention can also be employed for controlling animal pests and fungal or bacterial plant diseases. To a certain extent, they also induce resistance. If appropriate, they can also be used as intermediates or precursors for the synthesis of other active compounds.
  • Plants are to be understood as meaning in the present context all plants and plant populations such as desired and undesired wild plants or crop plants (including naturally occurring crop plants).
  • Crop plants may be plants which can be obtained by conventional plant breeding and optimization methods or by biotechnological and recombinant methods or by combinations of these methods, including the transgenic plants and inclusive of the plant cultivars protectable or not protectable by plant breeders' rights.
  • Plant parts are to be understood as meaning all parts and organs of plants above and below the ground, such as shoot, leaf, flower and root, examples which may be mentioned being leaves, needles, stalks, stems, flowers, fruit bodies, fruits, seeds, roots, tubers and rhizomes.
  • the plant parts also include harvested material, and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offsets and seeds.
  • the treatment according to the invention of the plants and plant parts with the active compounds is carried out directly or by allowing the compounds to act on the surroundings, habitat or storage space by the customary treatment methods, for example by immersion, spraying, evaporation, fogging, scattering, painting on and, in the case of propagation material, in particular in the case of seeds, also by applying one or more coats.
  • the active compounds can be converted into the customary formulations such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic materials impregnated with active compound, and microencapsulations in polymeric materials.
  • formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is, liquid solvents and/or solid carriers, optionally with the use of surfactants, that is, emulsifiers and/or dispersants, and/or foam formers.
  • extenders that is, liquid solvents and/or solid carriers
  • surfactants that is, emulsifiers and/or dispersants, and/or foam formers.
  • organic solvents as cosolvents.
  • aromatics such as xylene, toluene or alkylnaphthalenes
  • chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, for example mineral oil 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, or else water.
  • Suitable solid carriers are: for example, ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic materials such as highly-disperse silica, alumina and silicates;
  • suitable solid carriers for granules are: for example, crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, or else synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks;
  • suitable emulsifiers and/or foam formers are: for example nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, aryl
  • Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic colorants such alizarin colorants, azo colorants and metal phthalocyanine colorants, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • the formulations generally comprise between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used as mixtures with known herbicides and/or substances which improve the compatibility with crop plants (“safeners”), finished formulations or tank mixes being possible. Also possible are mixtures with weed-killers comprising one or more known herbicides and a safener.
  • Possible components for the mixtures are known herbicides, for example
  • safeners 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.
  • safeners for example AD-67, BAS-145138, benoxacor, cloquintocet (-mexyl), cyometrinil, 2,4-D, DKA-24, dichlormid, dymron, fenclorim, fenchlorazol (-ethyl), flurazole, fluxofenim, furilazole, is
  • a mixture with other known active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellents, plant nutrients and agents which improve soil structure, is also possible.
  • the active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in a customary manner, for example by watering, spraying, atomizing or broadcasting.
  • the active compounds according to the invention can be applied both before and after emergence of the plants. They can also be incorporated into the soil before sowing.
  • the amount of active compound used can vary within a relatively wide range. It depends essentially on the nature of the desired effect. In general, the amounts used are between 1 g and 10 kg of active compound per hectare of soil surface, preferably between 5 g and 5 kg per ha.
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • Seeds of the test plants are sown in normal soil. After 24 hours, the soil is sprayed with the preparation of active compounds such that the particular amount of active compound desired is applied per unit area.
  • the concentration of active compound in the spray liquor is chosen such that the particular amount of active compound desired is applied in 1000 liters of water per hectare.
  • Test plants of a height of 5-15 cm are sprayed with the preparation of active compound such that the particular amounts of active compound desired are applied per unit area.
  • the concentration of the spray liquor is chosen such that the particular amounts of active compound desired are applied in 1000 l of water/ha. After three weeks, the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control.
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Evaluation is carried out 10 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.

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  • Organic Chemistry (AREA)
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  • Life Sciences & Earth Sciences (AREA)
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  • Engineering & Computer Science (AREA)
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  • Wood Science & Technology (AREA)
  • Zoology (AREA)
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  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • General Chemical & Material Sciences (AREA)
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  • Communicable Diseases (AREA)
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  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
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  • Plural Heterocyclic Compounds (AREA)

Abstract

The invention relates to substituted fluoroalkoxyphenylsulfonylureas of the general formula (I)
Figure US20080076667A1-20080327-C00001
 in which
n, A, R1, R2, R3 and R4 are as defined in the description, to their use as plant treatment agents, in particular as herbicides and fungicides, and to a process and intermediates for their preparation.

Description

  • The invention relates to novel substituted fluoroalkoxyphenylsulfonylureas, to a process for their preparation and to their use as crop treatment agents, in particular as herbicides and as fungicides.
  • It is already known that certain substituted sulfonylureas have herbicidal properties (cf. EP-A-1514, EP-A-23422, EP-A-44807, EP-A-44808, WO-A-97/32861). However, the herbicidal activity and the compatibility of these compounds with crop plants are not entirely satisfactory. A fungicidal activity of these compounds has hitherto not been disclosed. The present invention provides the novel substituted fluoroalkoxyphenylsulfonylureas of the general formula (I)
    Figure US20080076667A1-20080327-C00002
    in which
    • n represents the numbers 2, 3 or 4,
    • A represents nitrogen or the grouping C—X, where
      • X represents hydrogen, halogen or in each case optionally halogen-substituted alkyl or alkoxy having in each case 1 to 4 carbon atoms, or together with R1 or R2 represents one of the groupings —CH2CH2O—, —CH2CH2S—, —CH2CH2CH2—,
    • R1 represents hydrogen, represents halogen or represents in each case optionally halogen- or C1-C4-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups,
    • R2 represents hydrogen, represents cyano, represents halogen or represents in each case optionally halogen- or C1-C4-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups, or represents cycloalkyl having 3 to 6 carbon atoms,
    • R3 represents hydrogen or represents optionally cyano-, halogen-, C1-C4-alkoxy- or C1-C4-alkoxycarbonyl-substituted alkyl having 1 to 4 carbon atoms, and
    • R4 represents halogen, represents in each case optionally cyano-, halogen- or C1-C4-alkoxy-substituted alkyl or alkoxy having in each case 1 to 4 carbon atoms, represents in each case optionally cyano- or halogen-substituted alkenyl, alkynyl, alkenyloxy or alkynyloxy having in each case 2 to 4 carbon atoms, or represents optionally cyano-, halogen- or C1-C4-alkyl-substituted cycloalkyl having 3 to 6 carbon atoms,
      and also salts of compounds of the formula (I).
  • Preferred substituents or ranges of the radicals present in the formulae shown above and below are described below:
    • n preferably represents the numbers 2, 3 or 4.
    • A preferably represents nitrogen or the grouping C—X, where
      • X preferably represents hydrogen, fluorine, chlorine, bromine or in each case optionally fluorine- and/or chlorine-substituted methyl, ethyl, methoxy or ethoxy, or together with R1 or R2 represents one of the groupings —CH2CH2O—, —CH2CH2S—, —CH2CH2CH2—,
    • R1 preferably represents hydrogen, fluorine, chlorine, bromine, or represents in each case optionally fluorine-, chlorine-, methoxy-, ethoxy- or n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, 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-propyl-amino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino.
    • R2 preferably represents hydrogen, cyano, fluorine, chlorine, bromine, represents in each case optionally fluorine-, chlorine-, methoxy-, ethoxy- or n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, 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-propyl-amino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino or represents cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
    • R3 preferably represents hydrogen or represents in each case optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.
    • R4 preferably represents fluorine, chlorine, bromine, or represents in each case optionally fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n- or i-propoxy-, n-, i-, s- or t-butoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, represents in each case optionally fluorine-, chlorine- and/or bromine-substituted ethenyl, propenyl, butenyl, ethynyl, propynyl, butynyl, propenyloxy, butenyloxy, propynyloxy or butynyloxy, or represents in each case optionally fluorine-, chlorine- or methyl-substituted cyclopropyl, cyclobutyl or cyclopentyl.
    • n particularly preferably represents the numbers 2, 3 or 4.
    • A particularly preferably represents nitrogen or the grouping C—X, where
      • X represents hydrogen, fluorine, chlorine, methyl or methoxy, or together with R1 or R2 represents one of the groupings —CH2CH2O—, —CH2CH2S—, —CH2CH2CH2—.
    • R1 particularly preferably represents hydrogen, fluorine, chlorine, bromine, or represents in each case optionally fluorine-, chlorine-, methoxy-, ethoxy- or n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino.
    • R2 particularly preferably represents hydrogen, cyano, fluorine, chlorine, bromine, represents in each case optionally fluorine-, chlorine-, methoxy-, ethoxy- or n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methyl-amino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino or represents cyclopropyl.
    • R3 particularly preferably represents hydrogen or represents in each case optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-substituted methyl, ethyl, n- or i-propyl.
    • R4 particularly preferably represents fluorine, chlorine, bromine, or represents in each case optionally fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, represents in each case optionally fluorine-, chlorine- and/or bromine-substituted propenyl, butenyl, propynyl, butynyl, propenyloxy, butenyloxy, propynyloxy or butynyloxy, or represents optionally fluorine-, chlorine- or methyl-substituted cyclopropyl.
    • n very particularly preferably represents the number 2 or 3.
    • A very particularly preferably represents nitrogen or a CH grouping.
    • R1 very particularly preferably represents cyano, chlorine, methyl, trifluoromethyl, ethyl, methoxy, difluoromethoxy, trifluoromethoxy, ethoxy, fluoroethoxy, difluoroethoxy, trifluoroethoxy, methylthio, ethylthio, methyl-amino, ethylamino, dimethylamino or cyclopropyl.
    • R2 very particularly preferably represents chlorine, methyl, trifluoromethyl, ethyl, methoxy, difluoromethoxy, trifluoromethoxy, ethoxy, fluoroethoxy, difluoroethoxy, trifluoroethoxy, methylthio, ethylthio, methylamino, ethyl-amino or dimethylamino.
    • R3 very particularly preferably represents hydrogen or methyl.
    • R4 very particularly preferably represents fluorine, chlorine, bromine, methyl, trifluoromethyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, or represents cyclopropyl.
  • A very particularly preferred group are those compounds of the formula (D) in which
    • n represents the numbers 2 or 3,
    • A represents nitrogen,
    • R1 represents chlorine, methyl, trifluoromethyl, ethyl, methoxy, difluoromethoxy, trifluoromethoxy, ethoxy, fluoroethoxy, difluoroethoxy, trifluoroethoxy, methylthio, ethylthio, methylamino, ethylamino or dimethylamino,
    • R2 represents chlorine, methyl, trifluoromethyl, ethyl, methoxy, difluoromethoxy, trifluoromethoxy, ethoxy, fluoroethoxy, difluoroethoxy, trifluoroethoxy, methylthio, ethylthio, methylamino, ethylamino or dimethylamino,
    • R3 represents hydrogen or methyl, and
    • R4 represents fluorine, chlorine, bromine, methyl, trifluoromethyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy.
  • A further very particularly preferred group are those compounds of the formula (I) in which
    • n represents the numbers 2 or 3,
    • A represents a CH grouping,
    • R1 represents methyl, trifluoromethyl, ethyl, methoxy, difluoromethoxy, trifluoromethoxy, ethoxy, fluoroethoxy, difluoroethoxy, trifluoroethoxy, methylthio, ethylthio, methylamino, ethylamino or dimethylamino,
    • R2 represents methyl, trifluoromethyl, ethyl, methoxy, difluoromethoxy, trifluoromethoxy, ethoxy, fluoroethoxy, difluoroethoxy, trifluoroethoxy, methylthio, ethylthio, methylamino, ethylamino or dimethylamino,
    • R3 represents hydrogen or methyl, and
    • R4 represents fluorine, chlorine, bromine, methyl, trifluoromethyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy.
  • The compounds in which n represents 3 or 4 may be mentioned as a further preferred group according to the invention.
  • The invention furthermore preferably provides sodium, potassium, magnesium, calcium, ammonium, C1-C4-alkylammonium, di-(C1-C4-alkyl)ammonium, tri-(C1-C4-alkyl)ammonium, tetra-(C1-C4-alkyl)ammonium, tri-(C1-C4-alkyl)-sulfonium, C5- or C6-cycloalkylammonium and di-(C1-C2-alkyl)benzylammonium salts of compounds of the formula (I), in which n, A, R1, R2, R3 and R4 have the meanings given above as being preferred.
  • The general or preferred radical definitions listed above apply both to the end products of the formula (I) and, correspondingly, to the starting materials or intermediates required in each case for the preparation. These radical definitions can be combined with one another as desired, i.e. including combinations between the given preferred ranges.
  • Preference according to the invention is given to those compounds of the formula (I) which contain a combination of the meanings listed above as being preferred (“preferable”).
  • Particular preference according to the invention is given to those compounds of the formula (I) which contain a combination of the meanings listed above as being particularly preferred.
  • Very particular preference according to the invention is given to those compounds of the formula (I) which contain a combination of the meanings listed above as being very particularly preferred.
  • Most preference according to the invention is given to those compounds of the formula (I) which contain a combination of the meanings listed above as being most preferred.
  • Saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl, are in each case straight-chain or branched as far as this is possible—including in combination with heteroatoms, such as in alkoxy.
  • Optionally substituted radicals may be mono- or polysubstituted, where in the case of polysubstitution the substituents may be identical or different.
  • The novel substituted fluoroalkoxyphenylsulfonylureas of the general formula (I) have interesting biological properties. In particular, they have strong herbicidal and fungicidal activity.
  • The novel substituted fluoroalkoxyphenylsulfonylureas of the general formula (I) are obtained when substituted aminoazines of the general formula (II)
    Figure US20080076667A1-20080327-C00003
    in which
    A, R1 and R2 are as defined above,
    Z represents halogen, alkoxy or aryloxy and
    R3 is as defined above or represents the grouping —C(O)—Z,
    are reacted with fluoroalkoxybenzenesulfonamides of the general formula (III)
    Figure US20080076667A1-20080327-C00004
    in which
    n and R4 are as defined above,
    if appropriate in the presence of one or more reaction auxiliaries and if appropriate in the presence of one or more diluents,
    and the resulting compounds of the general formula (I) are, if appropriate, converted into their salts by customary methods.
  • In principle, the novel substituted fluoroalkoxyphenylsulfonylureas of the general formula (I) can also be obtained as shown schematically below:
    • (b) by reacting aminoazines of the general formula (IV) with fluoroalkoxyphenyl-sulfonyl isocyanates of the general formula (V); n, R1, R2, R3 and R4 as above
      Figure US20080076667A1-20080327-C00005
    • (c) by reacting aminoazines of the general formula (IV) with substituted fluoro-alkoxybenzenesulfonamides of the general formula (VI); n, R1, R2, R3 and R4 as above, Z: halogen, C1-C4-alkoxy or phenoxy (cf WO-A-97/32861):
      Figure US20080076667A1-20080327-C00006
  • Using, for example, 2-methoxycarbonylamino-4-methoxy-6-trifluoromethyl-1,3,5-triazine and 2-(2-fluoroethoxy)-6-methylbenzenesulfonamide as starting materials, the course of the reaction in the process according to the invention can be illustrated by the formula scheme below:
    Figure US20080076667A1-20080327-C00007
  • The formula (II) provides a general definition of the aminoazines to be used as starting materials in the process according to the invention for preparing compounds of the general formula (I). In the general formula (II), A, R1 and R2 preferably or in particular have those meanings which have already been mentioned above, in connection with the description of the compounds of the general formula (I) according to the invention, as being preferred or as being particularly preferred for A, R1 and R2; Z preferably represents fluorine, chlorine, bromine, C1-C4-alkoxy or phenoxy, in particular chlorine, methoxy, ethoxy or phenoxy.
  • The starting materials of the general formula (II) are known and/or can be prepared by processes known per se (cf. DE-A-19 501 174, U.S. Pat. No. 4 690 707).
  • The formula (III) provides a general definition of the fluoroalkoxybenzene-sulfonamides further to be used as starting materials in the process according to the invention for preparing compounds of the general formula (I). In the general formula (III), n and R4 preferably or in particular have those meanings which have already been mentioned above, in connection with the description of the compounds of the general formula (I) according to the invention, as being preferred or as being particularly preferred for n and R4.
  • Some of the starting materials of the general formula (III) are known by disclosure in the form of a generic formula (cf. WO 97/03056). However, the starting materials of the formula (III) are a novel selection from among the prior-art compounds and therefore also form part of the subject matter of the present application. As a preferred group of the starting materials of the formula (III) according to the invention, mention may be made of those compounds in which n and R4 do not simultaneously represent 2 and unsubstituted alkyl, respectively.
  • The novel fluoroalkoxybenzenesulfonamides of the general formula (III) are obtained when hydroxybenzenesulfonamides of the general formula (VII)
    Figure US20080076667A1-20080327-C00008
    in which
    R4 is as defined above,
    are reacted with ω-fluoro-α-haloalkanes of the general formula (VIII)
    Figure US20080076667A1-20080327-C00009
    in which
    • n is as defined above and
    • X represents halogen, preferably chlorine, bromine or iodine, in particular bromine, or represents methylsulfonyloxy, phenylsulfonyloxy or tolyl-sulfonyloxy,
      if appropriate in the presence of a diluent, such as, for example, acetone, butanone, acetonitrile, propionitrile, N,N-dimethylformamide or N,N-dimethylacetamide, and if appropriate in the presence of an acid acceptor, such as, for example, potassium carbonate, at temperatures between 0° C. and 150° C. (cf. the Preparation Examples).
  • The hydroxybenzenesulfonamides of the general formula (VII) are known and/or can be prepared by processes known per se (cf. EP-A-44807, WO-A-97/03056).
  • The ω-fluoro-α-haloalkanes of the general formula (VIID further required as precursors are known organic chemicals for synthesis.
  • The process according to the invention for preparing the novel substituted fluoro-alkoxyphenylsulfonylureas of the general formula (III) is preferably carried out in the presence of one or more reaction auxiliaries. Reaction auxiliaries suitable for the process according to the invention are, in general, the customary inorganic or organic bases or acid acceptors. These preferably include alkali metal or alkaline earth metal acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkoxides, such as, for example, sodium acetate, potassium acetate or calcium acetate, lithium amide, sodium amide, potassium amide or calcium amide, sodium carbonate, potassium carbonate or calcium carbonate, sodium bicarbonate, potassium bicarbonate or calcium bicarbonate, lithium hydride, sodium hydride, potassium hydride or calcium hydride, lithium hydroxide, sodium hydroxide, potassium hydroxide or calcium hydroxide, sodium methoxide, ethoxide, n- or i-propoxide, n-, i-, s- or t-butoxide or potassium methoxide, ethoxide, n- or i-propoxide, n-, i-, s- or t-butoxide; furthermore also basic organic nitrogen compounds, such as, for example, trimethylamine, tri-ethylamine, tripropylamine, tributylamine, ethyldiisopropylamine, N,N-dimethylcyclohexylamine, dicyclohexylamine, ethyldicyclohexylamine, N,N-dimethylaniline, N,N-dimethylbenzylamine, pyridine, 2-methyl-, 3-methyl-, 4-methyl-, 2,4-dimethyl-, 2,6-dimethyl-, 3,4-dimethyl- and 3,5-dimethylpyridine, 5-ethyl-2-methylpyridine, 4-dimethylaminopyridine, N-methylpiperidine, 1,4-diaza-bicyclo[2.2.2]octane (DABCO), 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) or 1,8 di-azabicyclo[5.4.0]-undec-7-ene (DBU). Further suitable reaction auxiliaries for the process according to the invention include phase-transfer catalysts. Examples of such catalysts which may be mentioned are: tetrabutylammonium bromide, tetrabutylammonium chloride, tetraoctylammonium chloride, tetrabutylammonium hydrogen sulfate, methyltrioctylammonium chloride, hexadecyltrimethylammonium chloride, hexadecyltrimethylammonium bromide, benzyltrimethylammonium chloride, benzyltriethylammonium chloride, benzyl-trimethylammonium hydroxide, benzyltriethylammonium hydroxide, benzyltributyl-ammonium chloride, benzyltributylammonium bromide, tetrabutylphosphonium bromide, tetrabutylphosphonium chloride, tributylhexadecylphosphonium bromide, butyltriphenylphosphonium chloride, ethyltrioctylphosphonium bromide, tetraphenyl-phosphonium bromide.
  • The process according to the invention for preparing the compounds of the general formula (I) is preferably carried out using one or more diluents. Suitable diluents for carrying out the process according to the invention are, in addition to water, especially inert organic solvents. These include, in particular, aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, benzine, 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 ether or ethylene glycol 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-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; 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 mono-ethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, mixtures thereof with water or pure water.
  • When carrying out the process according to the invention, the reaction temperatures can be varied within a relatively wide range. In general, the process is carried out at temperatures between 0° C. and 150° C., preferably between 10° C. and 120° C.
  • In general, the process according to the invention is carried out under atmospheric pressure. However, it is also possible to carry out the process according to the invention under elevated or reduced pressure—in general between 0.1 bar and 10 bar.
  • For carrying out the process according to the invention, the starting materials are generally employed in approximately equimolar amounts. However, it is also possible to use a relatively large excess of one of the components. The reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary, and the reaction mixture is generally stirred at the required temperature for a number of hours. Work-up is carried out by customary methods (cf. the Preparation Examples).
  • If appropriate, salts may be prepared from the compounds of the general formula (I) according to the invention. Such salts are obtained in a simple manner by customary methods for forming salts, for example by dissolving or dispersing a compound of the formula (I) in a suitable solvent, such as, for example, methylene chloride, acetone, tert-butyl methyl ether or toluene, and adding a suitable base, such as, for example, sodium hydroxide. The salts can then—if appropriate after prolonged stirring—be isolated by concentration or by filtration with suction (cf. the Preparation Examples).
  • The active compounds according to the invention can be used as defoliants, desiccants, haulm killers and, especially, as weed killers. Weeds in the broadest sense are understood to mean all plants which grow in locations where they are undesired. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.
  • The active compounds according to the invention can be used, for example, in connection with the following plants:
  • Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.
  • Dicotyledonous crops 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, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.
  • Monocotyledonous crops of the genera: Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea.
  • However, the use of the active compounds according to the invention is in no way restricted to these genera, but also extends in the same manner to other plants.
  • The active compounds according to the invention are suitable, depending on the concentration, for the total control of weeds, for example on industrial terrain and rail tracks, and on paths and areas with and without trees. Similarly, the active compounds according to the invention can be employed for controlling weeds in perennial crops, for example forests, decorative tree plantations, orchards, vineyards, citrus groves, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, soft fruit plantings and hop fields, on lawns, turf and pastureland, and for the selective control of weeds in annual crops.
  • The compounds of the formula (I) according to the invention have strong herbicidal activity and a broad activity spectrum when used on the soil and on above-ground parts of plants. To a certain extent they are also suitable for the selective control of monocotyledonous and dicotyledonous weeds in monocotyledonous and dicotyledonous crops, both by the pre-emergence and by the post-emergence method.
  • At certain concentrations or application rates, the active compounds according to the invention can also be employed for controlling animal pests and fungal or bacterial plant diseases. To a certain extent, they also induce resistance. If appropriate, they can also be used as intermediates or precursors for the synthesis of other active compounds.
  • All plants and plant parts can be treated in accordance with the invention. Plants are to be understood as meaning in the present context all plants and plant populations such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants may be plants which can be obtained by conventional plant breeding and optimization methods or by biotechnological and recombinant methods or by combinations of these methods, including the transgenic plants and inclusive of the plant cultivars protectable or not protectable by plant breeders' rights. Plant parts are to be understood as meaning all parts and organs of plants above and below the ground, such as shoot, leaf, flower and root, examples which may be mentioned being leaves, needles, stalks, stems, flowers, fruit bodies, fruits, seeds, roots, tubers and rhizomes. The plant parts also include harvested material, and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offsets and seeds.
  • The treatment according to the invention of the plants and plant parts with the active compounds is carried out directly or by allowing the compounds to act on the surroundings, habitat or storage space by the customary treatment methods, for example by immersion, spraying, evaporation, fogging, scattering, painting on and, in the case of propagation material, in particular in the case of seeds, also by applying one or more coats.
  • The active compounds can be converted into the customary formulations such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic materials impregnated with active compound, and microencapsulations in polymeric materials.
  • These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is, liquid solvents and/or solid carriers, optionally with the use of surfactants, that is, emulsifiers and/or dispersants, and/or foam formers.
  • If the extender used is water, it is also possible, for example, to use organic solvents as cosolvents. The following are essentially suitable as liquid solvents: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example mineral oil 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, or else water.
  • Suitable solid carriers are: for example, ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic materials such as highly-disperse silica, alumina and silicates; suitable solid carriers for granules are: for example, crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, or else synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks; suitable emulsifiers and/or foam formers are: for example nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates, or else protein hydrolysates; suitable dispersants are: for example, lignosulfite waste liquors and methylcellulose.
  • Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations. Other additives can be mineral and vegetable oils.
  • It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic colorants such alizarin colorants, azo colorants and metal phthalocyanine colorants, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • The formulations generally comprise between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • For controlling weeds, the active compounds according to the invention, as such or in their formulations, can also be used as mixtures with known herbicides and/or substances which improve the compatibility with crop plants (“safeners”), finished formulations or tank mixes being possible. Also possible are mixtures with weed-killers comprising one or more known herbicides and a safener.
  • Possible components for the mixtures are known herbicides, for example
      • acetochlor, acifluorfen (-sodium), aclonifen, alachlor, alloxydim (-sodium), ametryne, amicarbazone, amidochlor, amidosulfuron, amitrole, anilofos, asulam, atrazine, azafenidin, azimsulfuron, beflubutamid, benazolin (-ethyl), benfuresate, bensulfuron (-methyl), bentazone, benzfendizone, benzobicyclon, benzofenap, benzoylprop (-ethyl), bialaphos, bifenox, bispyribac (-sodium), bromacil, bromobutide, bromofenoxim, bromoxynil, butachlor, butafenacil (-allyl), butenachlor, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone (-ethyl), chlomethoxyfen, chloramben, chloridazon, chlorimuron (-ethyl), chlornitrofen, chlorsulfuron, chlorthiamid, chlortoluron, cinidon (-ethyl), cinmethylin, cinosulfuron, clefoxydim, clethodim, clodinafop (-propargyl), clomazone, clomeprop, clopyralid, cloransulam (-methyl), cumyluron, cyanazine, cybutryne, cycloate, cyclosulfamuron, cycloxydim, cy-halofop (-butyl), 2,4-D, 2,4-DB, desmedipham, diallate, dicamba, dichlobenil, dichlorprop (—P), diclofop (-methyl), diclosulam, diethatyl (-ethyl), difeno-penten (-ethyl), difenzoquat, diflufenican, diflufenzopyr, dikegulac (-sodium), dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid (—P), dimexyflam, dinitramine, diphenamid, diquat (-dibromide), dithiopyr, diuron, dymron, epropodan, EPTC, esprocarb, ethalfluralin, ethametsulfuron (-methyl), ethiozin, ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanid, fenoxaprop (—P-ethyl), fentrazamide, flamprop (-M-isopropyl, -M-methyl), flazasulfuron, florasulam, fluazifop (—P-butyl), fluazolate, flucarbazone (-sodium), fluchloralin, flufenacet, flumetsulam, flumiclorac (-pentyl), flumi-oxazin, flumipropyn, fluometuron, fluorochloridone, fluoroglycofen (-ethyl), flupoxam, flupropacil, flurpyrsulfuron (-methyl, -sodium), flurenol (-butyl), fluridone, fluoroxypyr (-butoxypropyl, -meptyl), flurprimidol, flurtamone, flu-thiacet (-methyl), fomesafen, foramsulfuron, glufosinate (-ammonium), gly-phosate (-ammonium, -isopropylammonium), halosafen, halosulfuron (-methyl), haloxyfop (-ethoxyethyl, —P-methyl), hexazinone, imazamethabenz (-methyl), imazamethapyr, imazamox, imazapic, imazapyr, imazaquin, imaz-ethapyr, imazosulfuron, iodosulfuron (-methyl, -sodium), ioxynil, isopropalin, isoproturon, isouron, isoxaben, isoxachlortole, isoxadifen (-ethyl), isoxa-flutole, isoxapyrifop, ketospiradox, lactofen, lenacil, linuron, MCPA, meco-prop (—P), mefenacet, mesotrione, metamitron, metazachlor, methabenzthiaz-uron, methyldymron, metobenzuron, metobromuron, (S—) metolachlor, meto-sulam, metoxuron, metribuzin, metsulfuron (-methyl), molinate, monolin-uron, naproanilide, napropamide, neburon, nicosulfuron, norflurazon, orben-carb, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluor-fen, paraquat, pelargonic acid, pendimethalin, pendralin, pentoxazone, pethoxamid, phenmedipham, picolinafen, piperophos, pretilachlor, primisulfuron (-methyl), profluazol, profoxydim, prometryn, propachlor, propanil, propaquizafop, propisochlor, propoxycarbazone (-sodium), propyzamide, pro-sulfocarb, prosulfuron, pyraflufen (-ethyl), pyrazogyl, pyrazolate, pyrazosulfuron (-ethyl), pyrazoxyfen, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyridatol, pyriftalid, pyriminobac (-methyl), pyrithiobac (-sodium), quin-chlorac, quinmerac, quinoclamine, quizalofop (—P-ethyl, —P-tefuryl), rimsulf-uron, sethoxydim, simazine, simetryn, sulcotrione, sulfentrazone, sulfomet-uron (-methyl), sulfosate, sulfosulfuron, tebutam, tebuthiuron, tepraloxydim, terbuthylazine, terbutryn, thenylchlor, thiazopyr, thidiazimin, thifensulfuron (-methyl), thiobencarb, tiocarbazil, tralkoxydim, triallate, triasulfuron, tribenuron (-methyl), triclopyr, tridiphane, trifloxysulfuron, trifluralin, triflusulfuron (-methyl), tritosulfuron.
  • Furthermore suitable for the mixtures are known safeners, 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 compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellents, plant nutrients and agents which improve soil structure, is also possible.
  • The active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in a customary manner, for example by watering, spraying, atomizing or broadcasting.
  • The active compounds according to the invention can be applied both before and after emergence of the plants. They can also be incorporated into the soil before sowing.
  • The amount of active compound used can vary within a relatively wide range. It depends essentially on the nature of the desired effect. In general, the amounts used are between 1 g and 10 kg of active compound per hectare of soil surface, preferably between 5 g and 5 kg per ha.
  • The preparation and the use of the active compounds according to the invention is shown in the examples below.
    • PREPARATION EXAMPLES Example 1
  • Figure US20080076667A1-20080327-C00010
  • At room temperature (about 20° C.), a solution of 23.4 g (154 mmol) of 1,8 diaza-bicyclo[5.4.0]undec-7-ene (DBU) in 50 ml of acetonitrile is added dropwise with stirring to a mixture of 32.7 g (140 mmol) of 2-(2-fluoroethoxy)-6-methylbenzene-sulfonamide, 53.2 g (140 mmol) of 2-(N,N-bisphenoxycarbonylamino)-4-methoxy-6-methyl-1,3,5-triazine and 300 ml of acetonitrile. The reaction mixture is stirred at room temperature for one hour and then concentrated under reduced pressure. The residue is taken up in 300 ml of methylene chloride and shaken with 1N hydrochloric acid, then with water and finally with saturated aqueous sodium chloride solution. The organic phase is then dried using sodium sulfate and filtered. The filtrate is concentrated and the residue is digested with 100 ml of diethyl ether. The resulting crystalline product is isolated by filtration with suction.
  • This gives 36.9 g (60% of theory) of N-[2-(2-fluoroethoxy)-6-methylphenylsulfonyl]-N′-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea of melting point 161° C.
    • Example 2
  • Figure US20080076667A1-20080327-C00011
  • At room temperature, 3.3 g (82 mmol) of sodium hydroxide (Micropills) are added with stirring to a mixture of 36.0 g (82 mmol) of N-[2-(2-fluoroethoxy)-6-methyl-phenylsulfonyl]-N′-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea and 250 ml of methylene chloride. The mixture is stirred at room temperature for about 20 hours; the resulting crystalline product is then isolated by filtration with suction.
  • This gives 36.9 g (100% of theory) of N-[2-(2-fluoroethoxy)-6-methylphenyl-sulfonyl]-N′-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea sodium salt of melting point 185° C.
  • Analogously to examples 1 and 2, and in accordance with the general description of the preparation process according to the invention, it is also possible to prepare, for example, the compounds of the general formula (D) listed in table I below.
    Figure US20080076667A1-20080327-C00012
    TABLE 1
    Examples of compounds of the formula (I)
    Ex. Physical
    No. n A R1 R2 R3 R4 data
    3 2 N CH3 OCH3 H CF3 m.p.: 124° C.
    4 2 CH OCH3 OCH3 H CF3 m.p.: 183° C.
    5 2 N CH3 OCH3 H CF3 m.p.: 187° C.
    (Na salt)
    6 3 CH CH3 CH3 H C2H5 m.p.: 213° C.
    7 3 N CH3 OCH3 H C3H7-n m.p.: 109° C.
    8 3 N OCH3 OCH3 H C3H7-n m.p.: 139° C.
    9 3 N OCH2CF3 N(CH3)2 H CH3 m.p.: 180° C.
    10 3 N OCH2CF3 N(CH3)2 H C2H5 m.p.: 113° C.
    11 3 N OCH2CF3 N(CH3)2 H C3H7-n m.p.: 172° C.
    12 3 CH OCH3 OCH3 H CH3 m.p.: 142° C.
    13 3 N CH3 OCH3 H CH3 m.p.: 170° C.
    14 3 CH Cl OCH3 H CH3 m.p.: 163° C.
    15 3 N OCH3 OCH3 H CH3 m.p.: 155° C.
    16 3 CH OCH3 OCH3 H C2H5 m.p.: 154° C.
    17 3 N CH3 OCH3 H C2H5 m.p.: 121° C.
    18 3 CH Cl OCH3 H C2H5 m.p.: 139° C.
    19 3 N OCH3 OCH3 H C2H5 m.p.: 130° C.
    20 2 CH Cl OCH3 H CF3 m.p.: 123° C.
    21 2 N OCH3 OCH3 H CF3 m.p.: 169° C.
    22 2 N OCH2CF3 N(CH3)2 H CF3 m.p.: 162° C.
    23 2 N OCH3 OCH3 CH3 CF3 m.p.: 176° C.
    24 2 CH OCH3 OCH3 H CH3 m.p.: 169° C.
    25 3 CH OCH3 OCH3 H C3H7-n m.p.: 114° C.
    26 2 CH OCH3 OCH3 H C3H7-n m.p.: 166° C.
    27 2 N CH3 OCH3 CH3 CF3 m.p.: 177° C.
    28 3 N CH3 OCH3 CH3 C2H5 m.p.: 124° C.
    29 3 N CH3 OCH3 CH3 CH3 m.p.: 146° C.
    30 3 N OCH3 OCH3 CH3 C2H5 m.p.: 168° C.
    31 3 N OCH3 OCH3 CH3 C3H7-n m.p.: 150° C.
    32 3 N OCH3 OCH3 CH3 CH3 m.p.: 165° C.
    33 2 CH CH3 CH3 H CH3
    34 2 N CH3 CH3 H CH3
    35 2 CH CH3 OCH3 H CH3
    36 2 N OCH3 OCH3 H CH3
    37 2 N OCH2CF3 N(CH3)2 H CH3
    38 2 CH Cl OCH3 H CH3
    39 2 CH CH3 CH3 H C2H5
    40 2 N CH3 CH3 H C2H5
    41 2 CH CH3 OCH3 H C2H5
    42 2 N CH3 OCH3 H C2H5
    43 2 CH OCH3 OCH3 H C2H5
    44 2 N OCH3 OCH3 H C2H5
    45 2 N OCH2CF3 N(CH3)2 H C2H5
    46 2 CH CI OCH3 H C2H5
    47 2 CH CH3 CH3 H C3H7-n
    48 2 N CH3 CH3 H C3H7-n
    49 2 CH CH3 OCH3 H C3H7-n
    50 2 N CH3 OCH3 H C3H7-n
    51 2 N OCH3 OCH3 H C3H7-n
    52 2 N OCH2CF3 N(CH3)2 H C3H7-n
    53 2 CH Cl OCH3 H C3H7-n
    54 2 CH CH3 CH3 R C3H7-i
    55 2 N CH3 CH3 H C3H7-i
    56 2 CH CH3 OCH3 H C3H7-i
    57 2 N CH3 OCH3 H C3H7-i
    58 2 CH OCH3 OCH3 H C3H7-i
    59 2 N OCH3 OCH3 H C3H7-i
    60 2 N OCH2CF3 N(CH3)2 H C3H7-i
    61 2 CH Cl OCH3 H C3H7-i
    62 2 CH CH3 CH3 H CF3 m.p.: 168° C.
    63 2 N CH3 CH3 H CF3
    64 2 CH CH3 OCH3 H CF3 m.p.: 176° C.
    65 2 CH CH3 CH3 H Br
    66 2 N CH3 CH3 H Br
    67 2 CH CH3 OCH3 H Br
    68 2 N CH3 OCH3 H Br
    69 2 CH OCH3 OCH3 H Br
    70 2 N OCH3 OCH3 H Br
    71 2 N OCH2CF3 N(CH3)2 H Br
    72 2 CH Cl OCH3 H Br
    73 2 CH CH3 CH3 H OCH3
    74 2 N CH3 CH3 H OCH3
    75 2 CH CH3 OCH3 H OCH3
    76 2 N CH3 OCH3 H OCH3
    77 2 CH OCH3 OCH3 H OCH3
    78 2 N OCH3 OCH3 H OCH3
    79 2 N OCH2CF3 N(CH3)2 H OCH3
    80 2 CH Cl OCH3 H OCH3
    81 2 CH CH3 CH3 H OC2H5
    82 2 N CH3 CH3 H OC2H5
    83 2 CH CH3 OCH3 H OC2H5
    84 2 N CH3 OCH3 H OC2H5
    85 2 CH OCH3 OCH3 H OC2H5
    86 2 N OCH3 OCH3 H OC2H5
    87 2 N OCH2CF3 N(CH3)2 H OC2H5
    88 2 CH Cl OCH3 H OC2H5
    89 3 CH CH3 CH3 H CH3
    90 3 N CH3 CH3 H CH3
    91 3 CH CH3 OCH3 H CH3
    92 3 N CH3 CH3 H C2H5
    93 3 CH CH3 OCH3 H C2H5
    94 3 CH CH3 CH3 H C3H7-n
    95 3 N CH3 CH3 H C3H7-n
    96 3 CH CH3 OCH3 H C3H7-n
    97 3 CH Cl OCH3 H C3H7-n
    98 3 CH CH3 CH3 H C3H7-i
    99 3 N CH3 CH3 H C3H7-i
    100 3 CH CH3 OCH3 H C3H7-i
    101 3 N CH3 OCH3 H C3H7-i
    102 3 N CH3 OCH3 CH3 C3H7-i
    103 3 CH OCH3 OCH3 H C3H7-i
    104 3 N OCH3 OCH3 H C3H7-i
    105 3 N OCH2CF3 N(CH3)2 H C3H7-i
    106 3 CH Cl OCH3 H C3H7-i
    107 3 CH CH3 CH3 H CF3
    108 3 N CH3 CH3 H CF3
    109 3 CH CH3 OCH3 H CF3
    110 3 N CH3 OCH3 H CF3 m.p.: 68° C.
    111 3 N CH3 OCH3 CH3 CF3 m.p.: 113° C.
    112 3 CH OCH3 OCH3 H CF3 m.p.: 189° C.
    113 3 N OCH3 OCH3 H CF3 m.p.: 138° C.
    114 3 N OCH2CF3 N(CH3)2 H CF3
    115 3 CH Cl OCH3 H CF3
    116 3 CH CH3 CH3 H Br
    117 3 N CH3 CH3 H Br
    118 3 N CH3 OCH3 H Br
    119 3 CH CH3 OCH3 H Br
    120 3 N CH3 OCH3 CH3 Br
    121 3 CH OCH3 OCH3 H Br
    122 3 N OCH3 OCH3 H Br
    123 3 N OCH2CF3 N(CH3)2 H Br
    124 3 CH Cl OCH3 H Br
    125 3 CH CH3 CH3 H OCH3
    126 3 N CH3 CH3 H OCH3
    127 3 CH CH3 OCH3 H OCH3
    128 3 N CH3 OCH3 H OCH3
    129 3 N CH3 OCH3 CH3 OCH3
    130 3 CH OCH3 OCH3 H OCH3
    131 3 N OCH3 OCH3 H OCH3
    132 3 N OCH2CF3 N(CH3)2 H OCH3
    133 3 CH Cl OCH3 H OC2H5
    134 3 CH CH3 CH3 H OC2H5
    135 3 N CH3 CH3 H OC2H5
    136 3 N CH3 OCH3 H OC2H5
    137 3 N CH3 OCH3 CH3 OC2H5
    138 3 CH CH3 OCH3 H OC2H5
    139 3 CH OCH3 OCH3 H OC2H5
    140 3 N OCH3 OCH3 H OC2H5
    141 3 N OCH2CF3 N(CH3)2 H OC2H5
    142 3 CH Cl OCH3 H OC2H5
    143 4 N CH3 OCH3 H CH3
    144 4 CH CH3 OCH3 H CH3
    145 4 N CH3 OCH3 CH3 CH3
    146 4 CH OCH3 OCH3 H CH3
    147 4 N OCH3 OCH3 H CH3
    148 4 CH Cl OCH3 H CH3
    149 4 CH CH3 OCH3 H C2H5
    150 4 N CH3 OCH3 H C2H5
    151 4 N CH3 OCH3 CH3 C2H5
    152 4 CH CH3 OCH3 H C2H5
    153 4 CH Cl OCH3 H C2H5
    154 4 CH CH3 OCH3 H C3H7-n
    155 4 N CH3 OCH3 H C3H7-n
    156 4 N CH3 OCH3 CH3 C3H7-n
    157 4 CH OCH3 OCH3 H C3H7-n
    158 4 N OCH3 OCH3 H C3H7-n
    159 4 CH OCH3 OCH3 H C2H5
    160 4 N OCH3 OCH3 H C2H5
    161 4 CH CH3 CH3 H CH3
    162 4 CH CH3 CH3 H C2H5
    163 4 CH CH3 CH3 H C3H7-n
    164 4 CH CH3 CH3 H C3H7-i
    165 4 N CH3 OCH3 H C3H7-i
    166 4 N CH3 OCH3 CH3 C3H7-i
    167 4 CH CH3 OCH3 H C3H7-i
    168 4 CH OCH3 OCH3 H C3H7-i
    169 4 N OCH3 OCH3 H C3H7-i
    170 4 CH Cl OCH3 R C3H7-i
    171 4 CH CH3 CH3 H CF3
    172 4 N CH3 CH3 H CF3
    173 4 CH CH3 OCH3 H CF3
    174 4 N CH3 OCH3 H CF3
    175 4 N CH3 OCH3 CH3 CF3
    176 4 CH OCH3 OCH3 H CF3
    177 4 N OCH3 OCH3 H CF3
    178 4 CH Cl OCH3 H CF3
    179 2 CH OCHF2 OCHF2 H CH3
    180 2 CH OCHF2 OCHF2 H C2H5
    181 2 CH OCHF2 OCHF2 H C3H7-n
    182 2 CH OCHF2 OCHF2 H C3H7-i
    183 2 CH OCHF2 OCHF2 H CF3
    184 2 CH OCHF2 OCHF2 H Br
    185 2 CH OCHF2 OCHF2 H OCH3
    186 2 CH OCHF2 OCHF2 H OC2H5
    187 3 CH OCHF2 OCHF2 H CH3
    188 3 CH OCHF2 OCHF2 H C2H5
    189 3 CH OCHF2 OCHF2 H C3H7-n
    190 3 CH OCHF2 OCHF2 H C3H7-i
    191 3 CH OCHF2 OCHF2 H CF3
    192 3 CH OCHF2 OCHF2 H Br
    193 3 CH OCHF2 OCHF2 H OCH3
    194 3 CH OCHF2 OCHF2 H OC2H5
    195 4 CH OCHF2 OCHF2 H CH3
    196 4 CH OCHF2 OCHF2 H C2H5
    197 4 CH OCHF2 OCHF2 H C3H7-n
    198 4 CH OCHF2 OCHF2 H C3H7-i
    199 4 CH OCHF2 OCHF2 H CF3
    200 4 CH OCHF2 OCHF2 H Br
    201 4 CH OCHF2 OCHF2 H OCH3
    202 4 CH OCHF2 OCHF2 H OC2H5
    203 2 N C2H5 OCH3 H CF3 m.p.: 168° C.
    204 2 N CH3 OC2H5 H CF3 m.p.: 137° C.
    205 2 N CH3 N(CH3)2 H CF3 m.p.: 93° C.
    206 2 N SCH3 N(CH3)2 H CF3 m.p.: 249° C.
    207 2 N NHCH3 CN H CF3 m.p.: 220° C.
    208 2 N CH3 SCH3 H CF3 m.p.: 75° C.
    209 2 N OCH3
    Figure US20080076667A1-20080327-C00013
         		H CF3 m.p.: 189° C.
    210 2 N SCH3
    Figure US20080076667A1-20080327-C00014
         		H CF3 m.p.: 184° C.
    211 2 N SCH3 C3H7-i H CF3 m.p.: 86° C.
    212 2 N SCH3 C4H9-t H CF3 m.p.: 95° C.
    213 2 CH Cl Cl H CF3 m.p.: 84° C.
    214 2 C-Cl H CH3 H CF3 m.p.: 178° C.
    215 2 C-Br CH3 SCH3 H CF3 m.p.: 219° C.
    216 2 C-Br CH3 OCH3 H CF3 m.p.: 215° C.
    217 2 C-Cl CH3 CH3 H CF3 m.p.: 191° C.
    218 2 C-Cl CH3 OCH3 H CF3 m.p.: 229° C.
    219 2 CH OC2H5 OC2H5 H CF3 m.p.: 153° C.
    220 2 C-X OCH3 R2 + X: H CF3 m.p.: 209° C.
    —(CH2)3
    221 2 C-X Cl R2 + X: H CF3 m.p.: 212° C.
    —(CH2)3
    222 2 C-CH3 CH3 OCH3 H CF3 m.p.: 215° C.
    223 2 C-CH3 H C2H5 H CF3 m.p.: 220° C.
    224 2 C-CH3 CH3 CH3 H CF3 m.p.: 212° C.
    225 2 N CH3 OCH3 H CF3 m.p.: 208° C.
    Na salt)
    226 3 N OCH3 OCH3 CH3 CF3 m.p.: 174° C.

    Starting Materials of the Formula (III):
    • Example (III-1)
  • Figure US20080076667A1-20080327-C00015
  • A mixture of 11.2 g (60 mmol) of 2-hydroxy-6-methylbenzenesulfonamide, 10 g (78 mmol) of 1-bromo-2-fluoroethane, 16.6 g (120 mmol) of potassium carbonate and 350 ml of acetone is heated under reflux for 48 hours and then filtered while hot. The filtrate is concentrated under reduced pressure and the residue is taken up in methylene chloride, washed with water, dried with sodium sulfate and filtered. The filtrate is concentrated, the residue is digested with diethyl ether and the resulting crystalline product is isolated by filtration with suction.
  • This gives 7.9 g (56% of theory) of 2-(2-fluoroethoxy)-6-methylbenzenesulfonamide of melting point 103° C.
  • Analogously to example (III-1), it is also possible to prepare, for example, the compounds of the general formula (III) listed in table 2 below.
    Figure US20080076667A1-20080327-C00016
    TABLE 2
    Examples of compounds of the formula (III)
    Ex. No. n R4 Melting point (° C.)
    III-2 2 C2H5 108
    III-3 2 CF3
    III-4 2 C3H7-i 114
    III-5 2 OC2H5 140
    III-6 2 C3H7-n 117
    III-7 3 C3H7-n 108
    III-8 2 Br
    III-9 3 C2H5 92
    III-10 3 CH3 118
    III-11 3 C3H7-i
    III-12 3 CF3
    III-13 3 Br
    III-14 3 OCH3
    III-15 2 OCH3
    III-16 2 OC3H7-n
    III-17 2 OC3H7-i
    III-18 3 OC2H5
    III-19 3 OC3H7-n
    III-20 3 OC3H7-i
    III-21 2 CH2CF3
    III-22 3 CH2CF3
    III-23 2 Cl
    III-24 3 Cl
    III-25 2 Br
    III-26 3 Br
    III-27 2 I
    III-28 3 I

    Use examples:
    • Example A Pre-Emergence Test
  • Solvent: 5 parts by weight of acetone
    Emulsifier: 1 part by weight of alkylaryl polyglycol ether
  • To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • Seeds of the test plants are sown in normal soil. After 24 hours, the soil is sprayed with the preparation of active compounds such that the particular amount of active compound desired is applied per unit area. The concentration of active compound in the spray liquor is chosen such that the particular amount of active compound desired is applied in 1000 liters of water per hectare.
  • After three weeks, the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control. The figures denote:
      • 0%=no effect (like untreated control)
      • 100%=total destruction
  • In this test, for example, the compounds of Preparation Example 1, 2, 3, 4, 5, 6, 7, 8, 14, 15, 17, 20, 21, 24, 25 and 26 exhibit very strong activity against weeds, and some of them are tolerated well by crop plants, such as, for example, wheat and soya.
    TABLE A1
    Pre-emergence test greenhouse
    Active compound
    according to preparation Application rate
    example No. (g of a.i./ha) Cyperus Echinochloa Abutilon Galium Solanum Stellaria Veronica
    (3) 8 100 100 100 100 100 100 100
  • TABLE A2
    Pre-emergence test greenhouse
    Active compound
    according to preparation Application rate
    example No. (g of a.i./ha) Wheat Soya Alopecurus Sorghum Chenopodium Matricaria Viola
    (4) 15 0 0 80 80 100 100 100
  • TABLE A3
    Pre-emergence test greenhouse
    Active compound
    according to preparation Application rate
    example No. (g of a.i./ha) Echinochloa Amaranthus Datura Galium Matricaria Viola
    (5) 15 100 100 100 100 100 100
  • TABLE A4
    Pre-emergence test greenhouse
    Active compound
    according to preparation Application rate
    example No. (g of a.i./ha) Wheat Echinochloa Chenopodium Galium Stellaria Viola
    (7) 30 0 90 90 90 100 100
    (8) 30 0 — 90 90 100 100
  • TABLE A5
    Pre-emergence test greenhouse
    Active compound
    according to preparation Application rate
    example No. (g of a.i./ha) Wheat Echinochloa Chenopodium Datura Stellaria Viola
    (25) 125 0 90 90 90 90 100
  • TABLE A6
    Pre-emergence test greenhouse
    Active compound
    according to preparation Application rate
    example No. (g of a.i./ha) Alopecurus Echinochloa Abutilon Amaranthus Galium Sinapis
    (14) 60 100  100  95 95 90 95
    (15) 60 95 95 95 100  95 95
    (17) 60 95 95 95 95 95 90
  • TABLE A7
    Pre-emergence test greenhouse
    Active compound
    according to preparation Application rate
    example No. (g of a.i./ha) Alopecurus Setaria Abutilon Amaranthus Galium Sinapis
    (20) 60 90 100 90 95 95 95
    (21) 60 90 100 90 95 95 100 
     (6) 60 80  95 90 90 90 90
  • TABLE A8
    Pre-emergence test greenhouse
    Active compound
    according to preparation Application rate
    example No. (g of a.i./ha) Alopecurus Avenafatua Setaria Amaranthus Galium Xanthium
    (24) 250 100 95 95 100 100 95
     (1) 250 100 100 100 100 100 100
    (25) 250 95 90 100 100 95 100
    (26) 250 100 90 100 100 95 95
     (2) 250 100 95 100 100 100 95
    • Example B Post-Emergence Test
  • Solvent: 5 parts by weight of acetone
    Emulsifier: 1 part by weight of alkylaryl polyglycol ether
  • To product a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • Test plants of a height of 5-15 cm are sprayed with the preparation of active compound such that the particular amounts of active compound desired are applied per unit area. The concentration of the spray liquor is chosen such that the particular amounts of active compound desired are applied in 1000 l of water/ha. After three weeks, the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control.
  • The figures denote:
      • 0%=no effect (like untreated control)
      • 100%=total destruction
  • In this test, for example, the compounds of Preparation Example 1, 2, 3, 4, 5, 6, 7, 8, 12, 13, 14, 15, 17, 18, 20, 21, 22, 24, 25 and 26 exhibit very strong activity against weeds, and some of them are tolerated well by crop plants, such as, for example, corn, wheat and sugar beet.
    TABLE B1
    Post-emergence test greenhouse
    Active compound
    according to preparation Application rate
    example No. (g of a.i./ha) Alopecurus Avenafatua Setaria Abutilon Amaranthus Galium Sinapis
    (24) 250 100 90 95 100 100 90 100
     (1) 250 95 95 100 100 100 100 100
    (25) 250 90 90 100 100 100 100 100
    (26) 250 95 90 90 100 100 90 95
     (2) 250 100 100 100 100 100 100 100
  • TABLE B2
    Post-emergence test greenhouse
    Active compound
    according to preparation Application rate
    example No. (g of a.i./ha) Wheat Alopecurus Abutilon Amaranthus Datura Solanum
    (25) 125 10 90 95 100 100 100
     (7) 30 0 90 100 100 100 100
  • TABLE B3
    Post-emergence test greenhouse
    Active compound
    according to preparation Application rate
    example No. (g of a.i./ha) Wheat Lolium Abutilon Ipomoea Matricaria Solanum Stellaria
    (17) 8 10 90 100 100 100 100 100
  • TABLE B4
    Post-emergence test greenhouse
    Active compound
    according to preparation Application rate
    example No. (g of a.i./ha) Wheat Abutilon Amaranthus Matricaria Xanthium
    (18) 15 15 90 95 95 90
  • TABLE B5
    Post-emergence test greenhouse
    Active compound
    according to preparation Application rate
    example No. (g of a.i./ha) Wheat Sugar beet Amaranthus Ipomoea Matricaria
    (14) 30 0 0 100 95 90
  • TABLE B6
    Post-emergence test greenhouse
    Active compound
    according to preparation Application rate
    example No. (g of a.i./ha) Wheat Maize Datura Ipomoea Matricaria Solanum Stellaria
    (8) 8 0 10 90 100 95 100 95
  • TABLE B7
    Post-emergence test greenhouse
    Active compound
    according to preparation Application rate
    example No. (g of a.i./ha) Alopecurus Abutilon Amaranthus Ipomoea Matricaria Viola
    (4) 30 90 95 100 95 100 95
  • TABLE B8
    Post-emergence test greenhouse
    Active compound
    according to preparation Application rate
    example No. (g of a.i./ha) Alopecurus Lolium Abutilon Amaranthus Matricaria Viola Xanthium
    (3) 30 95 95 100 100 100 100 100
  • TABLE B9
    Post-emergence test greenhouse
    Active compound
    according to preparation Application rate
    example No. (g of a.i./ha) Alopecurus Abutilon Amaranthus Ipomoea Xanthium
    (6) 30 90 90 90 100 95
  • TABLE B10
    Post-emergence test greenhouse
    Active compound
    according to preparation Application rate
    example No. (g of a.i./ha) Alopecurus Lolium Abutilon Amaranthus Ipomoea Matricaria Stellaria
     (5) 30 95 95 100 100 100 100 100
    (13) 30 90 90 100 100 90 100 100
    (15) 30 90 90 95 100 100 100 100
  • TABLE B11
    Post-emergence test greenhouse
    Active compound
    according to preparation Application rate
    example No. (g of a.i./ha) Echinochloa Abutilon Amaranthus Datura
    (12) 30 90 95 95 95
  • TABLE B12
    Post-emergence test greenhouse
    Active compound
    according to preparation Application rate
    example No. (g of a.i./ha) Echinochloa Ipomoea Matricaria Polygonum Xanthium
    (20) 30 90 100 95 95 100
  • TABLE B13
    Post-emergence test greenhouse
    Active compound Application
    according to preparation rate Avena
    example No. (g of a.i./ha) fatua Lolium Datura Matricaria Solanum
    (21) 30 100 100 100 100 100
  • TABLE B14
    Post-emergence test greenhouse
    Active compound
    according to preparation Application rate
    example No. (g of a.i./ha) Alopecurus Setaria Amaranthus Galium Ipomoea Sinapis
    (22) 60 90 95 100 95 100 95
    • Example C Podosphaera Test (Apple)/Protective
  • Solvent: 49 parts by weight of acetone
    Emulsifier:  1 part by weight of alkylaryl polyglycol ether
  • To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • To test for protective activity, young plants are sprayed with the preparation of active compound at the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of the apple mildew pathogen Podosphaera leucotricha. The plants are then placed in a greenhouse at about 23° C. and a relative atmospheric humidity of about 70%.
  • Evaluation is carried out 10 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.
  • In this test, for example, the compounds of Preparation Example 1, 24, 25 and 26 exhibit, at an application rate of 100 g/ha, an efficacy of 100% against mildew of apples (Podosphaera leucotricha).
    TABLE C
    Podosphaera test (apple)/protective
    Application rate of
    Active compound according to active compound in %
    preparation example No. g/ha efficacy
    Figure US20080076667A1-20080327-C00017
         		100 100
    (24)
    Figure US20080076667A1-20080327-C00018
         		100 100
    (1)
    Figure US20080076667A1-20080327-C00019
         		100 100
    (25)
    Figure US20080076667A1-20080327-C00020
         		100 100
    (26)

Claims (11)

1-10. (canceled)
11: A compound of formula (I)
Figure US20080076667A1-20080327-C00021
or a salt thereof,
in which
n represents the numbers 2, 3, or 4,
A represents nitrogen,
R1 represents hydrogen, represents halogen, or represents optionally halogen- or C1-C4-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylamino, or dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups,
R2 represents hydrogen, represents cyano, represents halogen, represents optionally halogen- or C1-C4-alkoxy-substituted alkyl, alkoxy, alkylthio, alkyl-amino, or dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups, or represents cycloalkyl having 3 to 6 carbon atoms,
R3 represents hydrogen or represents optionally cyano-, halogen-, C1-C4-alkoxy-, or C1-C4-alkoxycarbonyl-substituted alkyl having 1 to 4 carbon atoms, and
R4 represents halogen, represents optionally cyano-, halogen-, or C1-C4-alkoxy-substituted alkyl or alkoxy having in each case 1 to 4 carbon atoms, represents optionally cyano- or halogen-substituted alkenyl, alkynyl, alkenyloxy, or alkynyloxy having in each case 2 to 4 carbon atoms, or -represents optionally cyano-, halogen-, or C1-C4-alkyl-substituted cycloalkyl having 3 to 6 carbon atoms.
12: A compound according to claim 11 in which
n represents the numbers 2, 3, or 4,
A represents nitrogen,
R1 represents hydrogen, fluorine, chlorine, or bromine, or represents optionally fluorine-, chlorine-, methoxy-, ethoxy-, or n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, 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,
R2 represents hydrogen, fluorine, cyano, chlorine, or bromine, represents optionally fluorine-, chlorine-, methoxy-, ethoxy-, or n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, 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, or represents cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl,
R3 represents hydrogen or represents optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methoxycarbonyl-, ethoxycarbonyl-, or n- or i-propoxycarbonyl-substituted methyl, ethyl, n- or i-propyl, or n-, i-, s-, or t-butyl, and
R4 represents fluorine, chlorine, or bromine, represents optionally fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n- or i-propoxy-, n-, i-, s-, or t-butoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s-, or t-butyl, methoxy, ethoxy, n- or i-propoxy, or n-, i-, s-, or t-butoxy, represents optionally fluorine-, chlorine-, and/or bromine-substituted ethenyl, propenyl, butenyl, ethynyl, propynyl, butynyl, propenyloxy, butenyloxy, propynyloxy, or butynyloxy, or represents optionally fluorine-, chlorine-, or methyl-substituted cyclopropyl, cyclobutyl, or cyclopentyl.
13: A compound according to claim 11 in which
n represents the numbers 2, 3, or 4,
A represents nitrogen,
R1 represents hydrogen, fluorine, chlorine, or bromine, or represents optionally fluorine-, chlorine-, methoxy-, ethoxy-, or n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino, dimethylamino, or diethylamino,
R2 represents hydrogen, cyano, fluorine, chlorine, or bromine, represents optionally fluorine-, chlorine-, methoxy-, ethoxy-, or n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino, dimethylamino, or diethylamino, or represents cyclopropyl,
R3 represents hydrogen or represents optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methoxycarbonyl-, ethoxycarbonyl-, or n- or i-propoxycarbonyl-substituted methyl, ethyl, or n- or i-propyl, and
R4 represents fluorine, chlorine, or bromine, represents optionally fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, or n- or i-propoxy, represents optionally fluorine-, chlorine-, and/or bromine-substituted propenyl, butenyl, propynyl, butynyl, propenyloxy, butenyloxy, propynyloxy, or butynyloxy, or represents optionally fluorine-, chlorine-, or methyl-substituted cyclopropyl.
14: A compound according to claim 11 in which
n represents the number 2 or 3,
A represents nitrogen,
R1 represents cyano, chlorine, methyl, trifluoromethyl, ethyl, methoxy, difluoro-methoxy, trifluoromethoxy, ethoxy, fluoroethoxy, difluoroethoxy, trifluoro-ethoxy, methylthio, ethylthio, methylamino, ethylamino, dimethylamino, or cyclopropyl,
R2 represents chlorine, methyl, trifluoromethyl, ethyl, methoxy, difluoromethoxy, trifluoromethoxy, ethoxy, fluoroethoxy, difluoroethoxy, trifluoroethoxy, methyl-thio, ethylthio, methylamino, ethylamino, or dimethylamino,
R3 represents hydrogen or methyl, and
R4 represents fluorine, chlorine, bromine, methyl, trifluoromethyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, or cyclopropyl.
15: A compound according to claim 11 in which A represents nitrogen and
(1) n represents 2, R1 represents methoxy, R2 represents methyl, R3 represents hydrogen, and R4 represents methyl,
(2) n represents 2, R1 represents methyl, R2 represents methoxy, R3 represents hydrogen, and R4 represents trifluoromethyl,
(3) n represents 2, R1 represents methyl, R2 represents methoxy, R3 represents hydrogen, and R4 represents trifluoromethyl, as the sodium salt,
(4) n represents 3, R1 represents methyl, R2 represents methoxy, R3 represents hydrogen, and R4 represents n-propyl,
(5) n represents 3, R1 represents methoxy, R2 represents methoxy, R3 represents hydrogen, and R4 represents n-propyl,
(6) n represents 3, R1 represents methoxy, R2 represents methoxy, R3 represents hydrogen, and R4 represents methyl,
(7) n represents 2, R1 represents methoxy, R2 represents methoxy, R3 represents hydrogen, and R4 represents trifluoromethyl, or
(8) n represents 3, R1 represents methyl, R2 represents methoxy, R3 represents hydrogen, and R4 represents bromine.
16: A process for preparing a compound according to claim 11 comprising
(a) reacting substituted an aminoazine of formula (II)
Figure US20080076667A1-20080327-C00022
in which
A, R1, and R2 are as defined for formula (I) in claim 11,
Z represents halogen, alkoxy, or aryloxy, and
R3 is as defined for formula (I) in claim 11 or represents the group —C(O)-Z,
with a fluoroalkoxybenzenesulfonamide of formula (III)
Figure US20080076667A1-20080327-C00023
in which n and R4 are as defined for formula (I) in claim 11, optionally in the presence of one or more reaction auxiliaries and optionally in the presence of one or more diluents, to give a compound of formula (I), and
(b) optionally, converting the resulting compound of formula (I) into a corresponding salt.
17: A method for controlling unwanted vegetation comprising allowing one or more compounds according to claim 11 to act on an unwanted plant and/or its habitat.
18: A method for controlling unwanted microorganisms comprising allowing one or more compounds according to claim 11 to act on an unwanted microorganism and/or its habitat.
19: A herbicidal or fungicidal composition comprising a compound according to claim 11 and customary extenders and/or surfactants.
20: A compound of formula (III)
Figure US20080076667A1-20080327-C00024
in which
n represents the numbers 2, 3, or 4, and
R4 represents halogen, represents optionally cyano-, halogen-, or C1-C4-alkoxy-substituted alkyl or alkoxy having in each case 1 to 4 carbon atoms, represents optionally cyano- or halogen-substituted alkenyl, alkynyl, alkenyloxy, or alkynyloxy having in each case 2 to 4 carbon atoms, or represents optionally cyano-, halogen-, or C1-C4-alkyl-substituted cycloalkyl having 3 to 6 carbon atoms.
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