HK1015360A - Substituted aminophenyluracils as herbicides and insecticides - Google Patents

Description

Substituted aminophenyluracils as herbicides and insecticides

The present invention relates to novel substituted aminophenyluracils, to processes for their preparation and to their use as herbicides and insecticides.

Certain substituted aminophenyluracils are known to have herbicidal properties (cf. EP 408382/US 5084084/US 5127935/US 5154755, EP 563384, DE 4412079), but they have not gained any significance hitherto as herbicides or as pesticides.

It has now been found that novel substituted aminophenyluracils of the general formula (I):wherein Q represents oxygen or sulfur, R¹Represents hydrogen, cyano or halogen, R²Represents cyano, thiocarbamoyl, halogen or represents optionally substituted alkyl, R³Represents each optionally substituted alkyl, cycloalkyl, aryl, aralkyl or heteroaryl radical, R⁴Represents each optionally substituted cycloalkyl, aryl or heteroaryl, R⁵Represents hydrogen, halogen or represents optionally substituted alkyl or alkoxy, R⁶Represents optionally substituted alkyl, and R⁷Represents hydrogen, hydroxyl, amino or represents in each case optionally substituted alkyl, alkoxy, alkenyl or alkynyl.

Novel substituted aminophenyluracils of the general formula (I) are obtained as follows: reacting a suitable sulfonylaminophenyluracil of formula (II) with an acid derivative of formula (III), optionally in the presence of a reaction auxiliary and optionally in the presence of a diluent,wherein

Q、R¹、R²、R³、R⁵、R⁶And R⁷Each as defined above, is preferably a mixture of,

R⁴-CO-X (III)

wherein

R⁴As defined above, and

x represents halogen or a group-O-CO-R⁴。

Novel substituted aminophenyluracils of the general formula (I) have strong herbicidal and insecticidal activity.

In the definition, a saturated or unsaturated hydrocarbon chain such as an alkyl group, an alkenyl group or an alkynyl group is each a straight chain or a branched chain.

Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.

The present invention preferably provides compounds of formula (I) wherein Q represents oxygen or sulphur, R¹Represents hydrogen, cyano, fluorine or chlorine, R²Represents cyano, thiocarbamoyl, fluorine, chlorine, bromine, or represents optionally fluorine/and or chlorine-substituted alkyl having 1 to 4 carbon atoms, R³Represents optionally cyano, fluoro, chloro, bromo or C₁-C₄-alkoxy or C₁-C₄Alkyl radical substituted by alkylthio having 1 to 6 carbon atoms, R³And also represents optionally cyano, fluorine, chlorine, bromine or C₁-C₄-alkyl-substituted cycloalkyl having 3 to 8 carbon atoms, R³And also represents phenyl, naphthyl, benzyl, phenethyl, thienyl, pyrazolyl, pyridyl or quinolinyl,

possible substituents are in each case: fluorine, chlorine, bromine, cyano, nitro, carboxyl, carbamoyl, thiocarbamoyl, C₁-C₄Alkyl radical, C₁-C₄-alkoxy, C₁-C₄Alkylthio, dimethylaminosulfonyl, diethylaminosulfonyl, C each optionally substituted by fluorine and/or chlorine₁-C₄-alkylsulfinyl or C₁-C₄Alkylsulfonyl, C optionally substituted by fluorine, chlorine, bromine, cyano, methoxy or ethoxy₁-C₄-alkoxycarbonyl or phenyl, phenoxy or phenylthio each optionally substituted by fluorine, chlorine, bromine, cyano, methyl, methoxy, trifluoromethyl and/or trifluoromethoxy; r⁴Represents optionally cyano, fluoro, chloro, bromo or C₁-C₄Alkyl-substituted having 3 to 8 carbonsCycloalkyl of an atom, R⁴Also represents each optionally substituted phenyl, naphthyl, furyl, thienyl, oxazolyl, isoxazolyl, pyrazolyl, pyridyl, pyrimidinyl or quinolinyl, possible substituents in each case being: fluorine, chlorine, bromine, cyano, nitro, carboxyl, carbamoyl, thiocarbamoyl, dimethylamino, dimethylaminosulfonyl, diethylaminosulfonyl, C each optionally substituted by fluorine and/or chlorine₁-C₄Alkyl radical, C₁-C₄-alkoxy, C₁-C₄Alkylthio radical, C₁-C₄-alkylsulfinyl or C₁-C₄Alkylsulfonyl, or C each optionally substituted by fluorine, chlorine, bromine, cyano, methoxy or ethoxy₁-C₄-an alkoxycarbonyl group; r⁵Represents hydrogen, fluorine, chlorobromine or represents alkyl or alkoxy having 1 to 4 carbon atoms which are in each case optionally substituted by fluorine and/or chlorine, R⁶Represents an alkyl radical having 1 to 4 carbon atoms which is optionally substituted by fluorine and/or chlorine, and R⁷Represents hydrogen, hydroxy, amino or represents each optionally fluorine, chlorine or C₁-C₄Alkoxy-substituted alkyl, alkoxy, alkenyl or alkynyl groups each up to 6 carbon atoms.

The present invention particularly preferably provides compounds of formula (I) wherein Q represents oxygen or sulphur, R¹Represents hydrogen, cyano, fluorine or chlorine, R²Represents cyano, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n-or i-propyl, n-, i-, s-or t-butyl or trifluoromethyl, R³Represents optionally cyano-, fluorine-, chlorine-, methoxy-or ethoxy-substituted methyl, ethyl, n-or i-propyl, n-, i-, s-or t-butyl, R³And also represents cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, optionally substituted by cyano, fluoro, chloro, bromo, methyl, ethyl, n-or isopropyl, R³Also represents optionally substituted phenyl, naphthyl, benzyl, phenethyl, thienyl, pyrazolyl, pyridyl or quinolyl, possible substituents being: fluorine, chlorine, bromine, cyano, nitro, carboxyl, carbamoyl, thiocarbamoyl, methyl, ethyl, n-or i-propyl,Trifluoromethyl, methoxy, ethoxy, n-or isopropoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n-or isopropylthio, methylsulfinyl, ethylsulfinyl, n-or isopropylsulfinyl, methylsulfonyl, ethylsulfonyl, n-or isopropylsulfonyl, dimethylaminosulfonyl, diethylaminosulfonyl, methoxycarbonyl, ethoxycarbonyl, n-or isopropoxycarbonyl, R⁴Represents cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, optionally cyano-, fluoro-, chloro-, bromo-, methyl-, ethyl-, n-or isopropyl-substituted, R⁴And each optionally substituted phenyl, naphthyl, furyl, thienyl, oxazolyl, isoxazolyl, pyrazolyl, pyridyl or pyrimidinyl, possible substituents being: fluorine, chlorine, bromine, cyano, nitro, carboxyl, carbamoyl, thiocarbamoyl, dimethylamino, dimethylaminosulfonyl or diethylaminosulfonyl, methyl, ethyl, n-or i-propyl, methoxy, ethoxy, n-or i-propoxy, methylthio, ethylthio, n-or i-propylthio, methylsulfinyl, ethylsulfinyl, n-or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n-or i-propylsulfonyl, methoxycarbonyl, ethoxycarbonyl, n-or i-propoxycarbonyl, phenyl, phenoxy or phenylthio, each optionally substituted by fluorine, chlorine, bromine, cyano, methyl, methoxy, trifluoromethyl and/or trifluoromethoxy, R is⁵Represents hydrogen, fluorine, chlorine, bromine or represents methyl, ethyl, n-or isopropyl, each of which is optionally substituted by fluorine and/or chlorine, R⁶Represents methyl, ethyl, n-or isopropyl optionally substituted by fluorine and/or chlorine, and R⁷Represents hydrogen, amino or represents methyl, ethyl, n-or i-propyl, n-, i-, or s-butyl, methoxy, ethoxy, n-or i-propoxy, n-, i-or s-butoxy, propenyl, butenyl, propynyl or butynyl, each of which is optionally substituted by fluorine and/or chlorine.

The general or preferred radical definitions listed above apply to the end products of the formula (I) and in the same way to the starting materials or intermediates required for each preparation. The definitions of these radicals can be combined with one another as desired, i.e. also within the preferred ranges given.

If, for example, 1- (4-chloro-2-fluoro-5-methylsulfonylaminophenyl) -3, 6-dihydro-2, 6-dioxo-3, 4-dimethyl-1 (2H) -pyrimidine and 2-fluoro-benzoyl chloride are used as starting materials, the reaction route in the process of the invention can be illustrated by the following reaction scheme:

formula (II) provides a general definition of the sulfonamidophenyluracils used as starting materials in the process of the invention for preparing the compounds of formula (I). In formula (II), Q, R¹、R²、R³、R⁵、R⁶And R⁷Each preferably or in particular has the meaning already mentioned in the description relating to the compounds of the formula (I) according to the invention for Q, R¹、R²、R³、R⁵、R⁶And R⁷By preferred or particularly preferred.

The starting materials of the formula (II) are known and/or can be prepared by methods known per se (cf. EP 408382/US 5084084/US 5127935/US 5154755, EP 563384, DE 4412079).

Formula (III) provides a general definition of the acid chloride used as another starting material in the process of the invention for preparing the compound of formula (I). In this formula (III), R⁴Preferably or in particular with the meaning already mentioned in connection with the description of the compounds of the formula (I) according to the invention for R⁴By preferred or particularly preferred; x preferably represents fluorine, chlorine or bromine, in particular chlorine.

The starting materials of the formula (III) are compounds which are known for synthesis.

The process of the invention for preparing the compounds of formula (I) is preferably carried out in the presence of suitable reaction assistants. Suitable reaction auxiliaries are generally customary inorganic or organic bases or acid acceptors. These reaction assistants include alkali metal or alkaline earth metal acetates, amides, carbonates, hydrogen carbonates, hydrides, hydroxides and alkoxides, 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 hydrogen carbonate, potassium hydrogen carbonate or calcium hydrogen carbonate, lithium hydride, sodium hydride, potassium hydride or calcium hydride, lithium hydroxide, sodium hydroxide, potassium hydroxide or calcium hydroxide, sodium methoxide or potassium methoxide, sodium ethoxide or potassium ethoxide, sodium N-or isopropoxide, potassium N-or isopropoxide, sodium N-, iso-, sec-or tert-butoxide, and also alkali organic nitrogen compounds, for example trimethylamine, triethylamine, tripropylamine, tributylamine, ethyldiisopropylamine, N-dimethylcyclohexylamine, dicyclohexylamine, N, n-dimethylaniline, N-dimethylbenzylamine, pyridine, 2-methyl, 3-methyl-, 4-methyl-, 2, 4-dimethyl-, 2, 6-dimethyl-, 3, 4-dimethyl-and 3, 5-dimethyl-pyridine, 5-hexyl-2-methyl-pyridine, 4-methylamino-pyridine, N-methylpiperidine, 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-ene (DBU).

The process of the invention for preparing the compounds of formula (I) is preferably carried out in the presence of a diluent. Suitable diluents are generally conventional organic solvents. These solvents include: in particular aliphatic, cycloaliphatic or aromatic, optionally halogenated hydrocarbons, such as pentane, hexane, heptane, petroleum ether, ligroin, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, cyclohexane, methylcyclohexane, dichloromethane, chloroform or carbon tetrachloride; ethers, such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, hexyl tert-butyl ether, methyl tert-amyl ether (MTBE), Tetrahydrofuran (THF), 1, 4-dioxane or ethylene glycol dimethyl ether and diethylene glycol dimethyl ether, diethylene glycol dimethyl ether or diethylene glycol diethyl ether; dialkyl ketones such as acetone, butanone or methyl isopropyl ketone or methyl isobutyl ketone; nitriles such as acetonitrile, propionitrile, butyronitrile or benzonitrile; amides such as N, N-Dimethylformamide (DMF), N-diethylformamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide or esters such as methyl acetate, ethyl acetate, N-or i-propyl acetate, N-, i-or t-butyl acetate; or sulfoxides such as dimethyl sulfoxide; alkyl alcohols such as methanol, ethanol, n-or isopropanol, n-, iso-, sec-or tert-butanol, ethylene glycol monomethyl ether or ethylene glycol monoethyl ether, diethylene glycol monomethyl ether or diethylene glycol monoethyl ether; mixtures thereof with water or water alone.

The reaction temperature can be varied within a relatively wide range in carrying out the process of the invention. In general, the reaction is carried out at a temperature of between-10 ℃ and +150 ℃, preferably between 0 ℃ and +100 ℃.

The process of the invention is generally carried out at atmospheric pressure. However, it is also possible to work at elevated or reduced pressures-generally between 0.1 bar and 10 bar.

In carrying out the process of the present invention, the starting materials are generally employed in approximately equimolar amounts. However, one of the components may also be used in relatively large excess. The reaction is usually carried out in the presence of a reaction auxiliary in a suitable diluent and the reaction mixture is usually stirred for several hours at the desired temperature. Working up is carried out by customary methods (cf. the preparation examples).

The active compounds according to the invention can be used as defoliants, desiccants, stem killers and, in particular, as herbicides. By weeds, in their broadest sense, it is understood all plants which grow where they are not desired. The compounds of the invention are acting as biocidal or selective herbicides, depending essentially on the amounts used.

The compounds of the invention may be used in relation to the following plants: dicotyledonous weeds of the following genera: mustard, striga, cleavers, Stellaria, Matricaria, Chamomilla, achyranthes, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Potentilla, Arthropoda, Matricaria, Massa, Veronica, Abutilon, Rumex, Viola, Mucuna, Papaveris, Centaria, Trifolium, Ranunculus, Taraxacum, dicotyledon of the following genera: cotton, soybean, beet, carrot, phaseolus, pea, eggplant, flax, sweetpotato, Vicia, tobacco, tomato, peanut, Brassica, lettuce, cucumber and cucurbita, monocotyledonous weeds of the following genera: barnyard grass, setaria, panicum, large crabgrass, echelle, poachy, festuca, cricket grass, brachiaria, ryegrass, bromus, oat, sedge, sorghum, agropyron, bermudagrass, monocrotoria, pennywort, fimbria, arrowhead, chufa, grass, paspalum, duckbilled, cuspidate, cogongrass, agrostis, alopecurus, and efflorescence, monocotyledonous crops of the following genera: oryza, Zea, Triticum, Hordeum, Avena, Secale, sorghum, Panicum, Saccharum, Ananadis, Asparagus and Allium.

However, the use of the compounds of the invention is in no way limited to these genera and can also be extended in the same way to other crops.

Depending on their concentration, the compounds of the formula (I) are biocidal for control, for example, in industrial areas and railway lines, and also on roads or squares with or without plantation forests. Likewise, the compounds of the present invention may be employed to control weeds in perennial cultures such as forests, ornamental forests, orchards, vineyards, citrus orchards, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, berry plantations and beer plantations, lawns, turf and pasture, and to selectively control weeds in annual crops.

The compounds (I) according to the invention are particularly suitable for selectively controlling monocotyledonous and dicotyledonous weeds in monocotyledonous crops in a pre-or post-emergence manner.

The active compounds of the formula (I) according to the invention are suitable for controlling animal pests, preferably insects, acarids and nematodes which occur in agriculture, in forests, in the protection of stored products and materials and in hygiene. They are active against normally sensitive and resistant species and against all or some stages of growth and development. The pests include: isopoda, for example, Oncorhynchus (Oniscus asellus), Armadillidium vulgare (Armadillidium vulgare) and Armadillidium maculatum (Porcellio scaber). The class of the Diplopoda, for example, Blaniulus guttulatus. From the order of the Chilopoda, for example, Geophilus carpopophagus and Scutigera spp (Scutigerospec). The Symphyla, for example, Scutigerella immaculata. From the order of the Thysanura, for example, Lepisma saccharina (Lepisma saccharana). From the order of the Collembola, for example, Onychiurus armatus (Onychiurus armatus). From the order of the orthoptera, for example, Blatta orientalis (Blatta orientalis), Blatta americana (Periplaneta americana), Blatta maderae (Leucophaea maderae), Blattella germanica (Blatta germanica), Acheta domestica (Achatta domisticus), Gryllotalpa spp., locustaria migratoria (Locusta migratorioides), Crassocephalus (Melanoplus difficilis), and Trichosta rostrata (Schocisterculia gregaria). From the order of the Dermaptera, for example, Forficula auricularia (Forficula auricularia). From the order of the Isoptera, for example, the genus Rhinoceros (Reticulitermes spp.). From the order of the Anoplura, for example, the Pediculus humanus (Pediculus humanus murroris), the genus Haematopinus (Haematopinus spp.) and the genus Chitophagus (Linoganthus spp.). From the order of the mallophaga, for example, the genus Psorophyllum (Trichodectes spp.) and Damalinea spp. From the order of the Thysanoptera, for example, Hercinothrips femoralis (Hercinothrips femoralis) and thrips gossypii (Thripsibaci). From the order of the hemiptera, for example, the genus applanatum (Eurygaster spp.), the plant stinkbugs medicinalis (dysdermintermidis), the plant stinkbugs edulis (Piesma quadrata), the plant stinkbugs (Cimexlecteularia), the plant stinkbugs (Phdnius prolixus) and the plant stinkbugs (Triatomaspp). From the order of the homoptera, for example, cabbage whitefly (Aleurodeses brassicae), sweet potato whitefly (Bequisatabaci), greenhouse whitefly (Trialeurodes vaporariorum), cotton aphid (Aphisgostypii), cabbage aphid (Brevicoryne brassicae), Scirpus virens (Cryptomyzus), beet aphid (Aphis fabae), apple aphid (Aphis pomifera), apple aphid (Eriosoma lanigerum), peach tail aphid (Hyalopus arundinis), Myzus mairei (Macrosiphylum avenae), Phyllophora nodorum (Phyllophyceae), Phyllophora glauca (Phyllophora), Phyllophora nigra (Phyllophora), Phyllophora virginosa (Phyllophora), Phyllophora nigra, Phyllophora europa (Phyllophora), Phyllophora nigra canopilaris (Phyllophora), Phyllophora nigra, Phyllophora canopis (Phyllophora), Phyllophora nigra, Phyllophora canopis (Phyllophora), and Leostrinia (Phyllophora), rice leaf beetle. From the order of the Lepidoptera, for example, Chrysopa gossypii (Pectinophora gossypiella), Trichoplusia (Bupalusinarius), Dipper capitata (Cheimatobia brumata), Lithocolletis blandeana, Malva pomoea (Hypomeuta padela), Plutella xylostella (Plutella xylostella), Trichoplusia (Malacos neospora), Trichoplusia (Euprocystis rudis roella), Trichopsis (Eulerorhynchoides), Trichopsis (Lymanthus punctifera), Trichopsis gossypii (Bucta texthurella), Trichopsis citri (Phyllostachys citrifolia), Agrostis sp, Euxospodopp, Feltia spp, Spodoptera Spodoptera (Eisenia), Spodopteria Spodoptera (Spodopteria), Spodopteria litura), Spodopteria (Spodopterocarpus punctifera), Spodopteria (Spodopteria), Spodopteria (Spodopterocarpus punctifera), Sphae-Spodoptera (Sphae), Sphaerotheca), Spodoptera (Sphae-Spodoptera), Sphae (Sphae-Spodoptera (Sphae), Sphae (Sphae-Spodoptera-Sphae), Sphae-Spodoptera (Sphae-Spodoptera), Sphae (Sphae-Spodoptera (Sphae), Sphae (Sphae-Spodoptera (Sphae), Sphae-Spodoptera (Sp, Capua reticulana, Coloridia (Choristoneura fluminea), grape fruit moth (Clysia ambigua), tea leaf roller moth (Homona magnanima) and oak green roller moth (Tortrida), Coleoptera, e.g., the species Rhynchophorus (Anobiticum), Rhynchophorus griseus (Rhizoperthia), soybean (Acanthoscelides obtectus), Bruchidus obtusifolia, Hovenia (Hylotuphus bajuus), Dactylus purpureus (Agricus), Solanum tuberosum (Solanarticum), Solanum tuberosum (Leptotara decemlinea), Ardisia cochleariae (Ebenaria), Asparagus racemosus (Physiosphaera), Asparagus racemosus (Acanthopanax), Asparagus racemosus (Acacia), Brassica olepisifera (Acanthopanax), Brassica nigra, Brassica campestris (Acanthopanax), Brassica nigra, Acanthopanax senticospora, Brassica nigra (Acanthopanax senticospora, Acanthopanax senticospinus (Acanthopanax senticospinus, Acanthopanax, Bark beetles (Attagenius spp.), bark beetles (Lyctusspp.), coleus caucasicus (Meligethes aereus), spider beetles (Ptinus spp.), yellow spider beetles (Niptus holeucus), naked spider beetles (Gibbium psiloides), pseudoglutelinus (Tribolium spp.), yellow meal worm (Tenebrio molitor), Agriotes spp., Conoderus spp., gillygod beetles (Melolontha meloentha), Juniperus nigra (Amphimoto solotialis) and copylitra zealandica. From the order of the hymenoptera, for example, Diprion spp, Hoplocpa spp, Terminalia (Lasiusspp.), Solenopsis miri (Monomorium pharaonis) and wasp (Vespa spp.). From the order of the diptera, for example, the genera Aedes (Aedes spp.), Anopheles (Anopheles spp.), Culex (Culex spp.), Drosophila (Drosophila melanogaster), musca (Muscaspp.), latus (Fannia spp.), anthomyelidae (Callophora erythrocephala), Drosophila (Lucilia spp.), chrysomyzidae (chrysomyzilla spp.), phlegma (curvularia spp.), phlegmas (curebp), gastrophilis (gastrophilis spp.), pediculosis (hypecolac spp.), stigmas (Stomoxys spp.), Drosophila (ostrinia spp.), pyriproxyfera (hymenopsis spp.), lasia (hylocephala spb.), pyricularis (ostrinia spp.),), trypanosoma (ostrinia spp.), trypanosoma (gynura spp.), calli (gynura spp.), trypanosoma (gynura spp.), and trypanosoma (ostrea (gynura spp.). From the order of the Siphonaptera, for example, Xenopsylla cheopis and the genus Ceratophyllus (Ceratophyllusspp.), Siphonaptera (Pulex spp.) and Ctenocephalides (Ctenocephalides spp.). The Arachnida class includes, for example, Scorpion (Scorpio maurus) and Rhus succedanea (Latrodectus macrants). From the order of the Acarina, for example, Amycotes destructor (Acarus srorro), Cryptophytes rhynchophylla (Argas spp.), Tetranychus tarus (Ornithodoros spp.), Dermanyssus gallinae (Dermanyssus gallinae), Scirpus gracilis (Eriophophyes ribis), Phytopteris citri (Phyllophora oleivora), Achyriopsis (Boophilus spp.), Rhipicephalus spp (Rhipicephalus spp.), Acarinus flores (Amblymphaera spp.), Peropyrus (Hyalomma spp.), Idex spp.), Prime, Primordia (Chlorophytes spp.), Dermatophus spp., Dermatophagoides (Chlorophytes spp.), Dermatophagoides spp., Acarinus spp.), Dermatophagoides spp (Chlorophytis spp.), Acarinus spp.), and Tetranychus (Tetranychus spp.). Plant parasitic nematodes include, for example, Pratylenchus spp, endoparasitic nematodes (radiorecess spp), diptera Ditylenchus spp, Tylenchulus spp, Heterodermus spp, cyst nematodes (Globodera spp), Meloidogyne spp, Aphelodera spp, Longidoluusspp, Sword nematodes (Xipaninema spp), Thielencholia (Trichoderma spp), Tylenus spp, Tylenchus spp, Rotylenchus spp and Tychulius spp.

The active compounds can be converted into the customary formulations, such as solutions, emulsions, suspensions, wettable powders, dusts, pastes, soluble powders, granules, suspoemulsions, natural and synthetic substances impregnated with active compound and microcapsules made of polymers in use.

These formulations can be produced in a known manner, for example by mixing the active compounds with extenders, i.e. liquids, and/or with solid carriers, and optionally using surfactants, i.e. emulsifiers and/or dispersants, and/or foam formers.

In the case of water as filler, organic solvents may also be used as co-solvents. As liquid solvents, mainly: aromatic compounds, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example mineral oil fractions, mineral and vegetable oils, alcohols, such as butanol or ethylene glycol and ethers and esters thereof, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide or dimethyl sulfoxide, and water.

Suitable solid carriers are:

for example ammonium salts and ground natural minerals such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as highly disperse silica, alumina and silicates; suitable solid carriers for granules are: for example crushed and fractionated natural minerals such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of organic and inorganic powders, and granules of organic substances such as: sawdust, coconut shells, corn cobs and tobacco stems; suitable emulsifiers and/or foaming agents 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 and albumin hydrolysates; suitable dispersants are: such as lignin sulfite waste liquor and methyl cellulose.

Binders such as carboxymethylcellulose and natural and synthetic polymers, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, in the form of powders, granules or emulsions, and natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids, can be used in the formulations. Other binders may be mineral and vegetable oils.

It is also possible to use dyes, such as inorganic pigments, for example iron oxide, titanium oxide and Prussian blue, and organic dyes, such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and micronutrients, such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

The formulations generally contain from 0.1 to 95% by weight of active compound, preferably from 0.5 to 90%.

The active compounds according to the invention can be used as such or in their formulations, which are mixtures with known herbicides for controlling weeds, in the case of mixtures, either as directly usable formulations or as tank mixes.

Suitable as co-components of the mixture are known herbicides, for example anilides such as diflufenican, propanil; aryl carboxylic acids such as clopyralid, dicamba and picloram; aryloxycarboxylic acids such as 2, 4-d, 2, 4-d butyric acid, 2, 4-d propionic acid, fluroxypyr, 2 m 4 chloro, 2 m 4 chloropropionic acid and triclopyr; aryloxyphenoxycarboxylic acids such as diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl and quizalofop-ethyl; azinones such as oxamyl, pyridaphyl; carbamates such as chlorpropham, desmedipham, phenmedipham and propham; chloroacetanilides such as alachlor, acetochlor, butachlor, metazachlor, propisochlor, pretilachlor and propachlor; dinitroanilines such as oryzalin, pendimethalin and trifluralin; diphenyl ethers such as acifluorfen, bifenox, fluoroglycofen, fomesafen, halosafen, lactofen and oxyfluorfen; ureas such as chlortoluron, diuron, fluometuron, isoproturon, linuron and methabenzthiazuron; hydroxylamines such as diclofop, clethodim, cycloxydim, sethoxydim and tralkoxydim; imidazolinones such as imazethapyr, imazamethabenz, imazapyr and imazaquin; nitriles such as bromoxynil, dichlobenil, and ioxynil; oxyacetamides such as mefenacet; sulfonylureas such as amidosulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, ethosulfuron, metsulfuron-methyl, nicosulfuron, primisulfuron, pyrazosulfuron-ethyl, thifensulfuron-methyl, triasulfuron and tribenuron-methyl; thiocarbamates such as butachlor, bentazon, dichlormate, endothecin, dicamba, molinate, prosulfocarb and triallate; triazines such as atrazine, cyanazine, simazine, simetryn and terbutryn; buprofezin such as hexazinone, metamitron and metribuzin; other herbicides such as, for example, methidathion, benfuresate, bentazone, cinmethylin, clomazone, clopyralid, pyrazoxazole, dithiopyr, ethofumesate, fluorochloridone, glufosinate, glyphosate, isoxaben, pyridate, quinclorac, quinmerac, phosphinothricin and imazalil.

Mixtures with other known active compounds, such as fungicides, insecticides, acaricides, bird repellents, plant growth regulators and soil conditioners, are also possible.

The active compounds can be used as such or in the form of their formulations or the use forms prepared from the formulations by further dilution, such as directly usable solutions, suspensions, emulsions, powders, pastes and granules. They are used in a conventional manner, for example by watering, spraying, atomizing or broadcasting.

The active compounds according to the invention can be used before or after germination of the plants. They may also be incorporated into the soil prior to sowing.

The amount of active compound used can vary within a relatively wide range. In general, the amounts used are in the range from 1 g to 10 kg of active compound per hectare of soil surface, optionally from 5 g to 5 kg per hectare.

The preparation and use of the active compounds according to the invention can be found in the following examples.

Preparation examples: example 1

0.90 g (5 mmol) of 4-chlorobenzoyl chloride is added at about 20 ℃ to a mixture of 2.1 g (5 mmol) of 1- (4-cyano-5-ethylsulfonamido-2-fluoro-phenyl) -3, 6-dihydro-2, 6-dioxo-3-methyl-4-trifluoromethyl-1 (2H) -pyrimidine, 0.60 g (6 mmol) of triethylamine and 50 ml of acetonitrile, and the mixture is stirred at 20 ℃ for 2 hours. The mixture was then concentrated in vacuo with a water pump, and the residue was digested with chloroform, washed with 2N hydrochloric acid, dried over sodium sulfate and filtered. The filtrate was concentrated in vacuo using a water pump, the residue was digested with diethyl ether, and the resulting crystalline product was isolated by suction filtration.

1.5 g (54% of theory) of 1- [ 4-cyano-5- (N-ethylsulfonyl-N- (4-chlorobenzoyl) amino) -2-fluorophenyl are obtained]-3, 6-di-hydro-2, 6-dioxo-3-methyl-4-trifluoromethyl-1 (2H) -pyrimidine, melting point 138 ℃. Example 2

At about 20 ℃, 1.8 g (12 mmol) of thiophene-2-acid chloride was added to a mixture of 2.1 g (5 mmol) of 1- (4-cyano-5-ethylsulfonylamino-2-fluoro-phenyl) -3, 6-dihydro-2, 6-dioxo-3-methyl-4-trifluoromethyl-1 (2H) -pyrimidine, 1.5 ml of pyridine and 50 ml of dichloromethane, and the mixture was stirred at 20 ℃ for one week. The solution was washed with 1N hydrochloride, dried over sodium sulfate and filtered. The filtrate was concentrated in vacuo using a water pump, the residue was digested with diethyl ether, and the resulting crystalline product was isolated by suction filtration.

2.1 g (84% of theory) of 1- [ 4-cyano-5- (N-ethylsulfonyl-N- (thien-2-ylcarbonyl) amino) -2-fluorophenyl ] -3, 6-dihydro-2, 6-dioxo-3-methyl-4-trifluoromethyl-1 (2H) -pyrimidine are obtained, m.p. 192 ℃.

By analogy to the procedures of examples 1 and 2 and in accordance with the general description of the preparation processes of the invention, it is also possible to prepare, for example, the compounds of formula (I) listed in Table 1.TABLE 1 examples of compounds of formula (I)The application example is as follows: example a pre-emergence test solvents: 5 parts by weight of acetone emulsifier: 1 part by weight of alkylaryl polyethylene glycol

In the preparation of suitable active compound formulations, 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.

The seeds of the test plants are sown into customary soil and, after 24 hours, are watered or sprayed with the active compound preparation. It is preferable to keep the amount of water per unit area constant. The concentration of active compound in the formulation is not critical, only the amount of active compound per unit of administration is critical. After three weeks, the extent of damage in the plants was compared to the development of untreated controls, and% damage was determined.

The numerical values have the following meanings: 0%, (same as untreated) and 100%, (complete damage)

In this experiment, for example, the compounds according to examples 1 and 2 had good effects on Cyperus rotundus (60-100%), Lolium perenne (70-90%), Panicum miliaceum (70-95%), Abutilon (100%), Chenopodium quinoa (100%) and Datura stramonium (100%) at an application rate of 60 g/ha, whereas crops such as maize had good tolerance (0%). Example B post-emergence test solvents: 5 parts by weight of acetone emulsifier: 1 part by weight of alkylaryl polyethylene glycol

In the preparation of suitable active compound formulations, 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.

The test plants having a plant height of 5 to 15 cm are sprayed with a defined amount of the desired active compound preparation per unit area. The concentration of the spray liquor is chosen such that a specific amount of the desired compound is applied in an amount of 2,000 litres water per hectare. After three weeks, the extent of damage in the plants was compared to the development of untreated controls, and% damage was determined.

The numerical values have the following meanings: 0%, (same as untreated) and 100%, (complete damage)

In this experiment, for example, the compounds of preparation examples 1 and 2 had good effects on barnyard grass (95%), milo (70-80%), piemarker (100%), quinoa (100%), stramonium (100%) and solanum nigrum (100%) at an application rate of 30 g/ha, to which crops such as barley (0-10%) had good tolerance. Example C horse radish simian beetle larva test solvents: 7 parts by weight of dimethylformamide emulsifier: 1 part by weight of alkylaryl polyglycol ether

To prepare 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.

Cabbage leaves (Brassica oleracea) are treated by immersion in the preparation of active compound of the desired concentration, and, while the leaves are still moist, larvae of the mustard beetle (phaedoncochleriae) are introduced and the leaves are taken.

After a certain time, the% kill was determined. 100% means that all larvae were killed; 0% means that no larvae were killed.

In this test, 80-100% of the compounds of the preparation examples 1 and 2, for example, are killed after 7 days under the conditions of an active compound concentration of 0.1% being carried out. Example D leafhopper test solvent: 7 parts by weight of dimethylformamide emulsifier: 1 part by weight of alkylaryl polyglycol ether

To prepare 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.

Rice seedlings (Oryza sativa) are treated by immersion in the preparation of active compound of the desired concentration, and the leafhoppers are placed while the leaves are still moist.

After the desired time has elapsed, the% kill is determined. 100% means that all the leafhoppers were killed; 0% means that none of the leafhoppers were killed.

In this test, 100% of the compounds of the preparation examples 1 and 2 were killed after 6 days under the conditions of an active compound concentration of 0.1% being carried out.

Claims (9)

1. Substituted aminophenyluracils of the general formula (I)Wherein Q represents oxygen or sulphur, R¹Represents hydrogen, cyano or halogen, R²Represents cyano, thiocarbamoyl, halogen or represents optionally substituted alkyl, R³Represents each optionally substituted alkyl, cycloalkyl, aryl, aralkyl or heteroaryl radical, R⁴Represents each optionally substituted cycloalkyl, aryl or heteroaryl, R⁵Represents hydrogen, halogen or represents each optionally substituted alkyl or alkylOxy radical, R⁶Represents optionally substituted alkyl, and R⁷Represents hydrogen, hydroxyl, amino or represents in each case optionally substituted alkyl, alkoxy, alkenyl or alkynyl.

2. Substituted aminophenyluracils of the general formula (I) according to claim 1, characterized in that Q represents oxygen or sulphur, R¹Represents hydrogen, cyano, fluorine or chlorine, R²Represents cyano, thiocarbamoyl, fluorine, chlorine, bromine, or represents optionally fluorine/and or chlorine-substituted alkyl having 1 to 4 carbon atoms, R³Represents optionally cyano, fluoro, chloro, bromo, C₁-C₄-alkoxy or C₁-C₄Alkyl radical substituted by alkylthio having 1 to 6 carbon atoms, R³And also represents optionally cyano, fluorine, chlorine, bromine or C₁-C₄-alkyl-substituted cycloalkyl having 3 to 8 carbon atoms, R³Also represents phenyl, naphthyl, benzyl, phenethyl, thienyl, pyrazolyl, pyridyl or quinolinyl, possible substituents in each case being: fluorine, chlorine, bromine, cyano, nitro, carboxyl, carbamoyl, thiocarbamoyl, C₁-C₄Alkyl radical, C₁-C₄-alkoxy, C₁-C₄Alkylthio, dimethylaminosulfonyl, diethylaminosulfonyl, C each optionally substituted by fluorine and/or chlorine₁-C₄-alkylsulfinyl or C₁-C₄Alkylsulfonyl, C optionally substituted by fluorine, chlorine, bromine, cyano, methoxy or ethoxy₁-C₄-alkoxycarbonyl or phenyl, phenoxy or phenylthio each optionally substituted by fluorine, chlorine, bromine, cyano, methyl, methoxy, trifluoromethyl and/or trifluoromethoxy; r⁴Represents optionally cyano, fluoro, chloro, bromo or C₁-C₄-alkyl-substituted cycloalkyl having 3 to 8 carbon atoms, R⁴Also represents each optionally substituted phenyl, naphthyl, furyl, thienyl, oxazolyl, isoxazolyl, pyrazolyl, pyridyl, pyrimidinyl or quinolinyl, possible substituents in each case being: fluorine, chlorine, bromine, cyano, nitro, carboxyl, ammoniaCarbamoyl, thiocarbamoyl, dimethylamino, dimethylaminosulfonyl, diethylaminosulfonyl, each optionally fluorine-and/or chlorine-substituted C₁-C₄Alkyl radical, C₁-C₄-alkoxy, C₁-C₄Alkylthio radical, C₁-C₄-alkylsulfinyl or C₁-C₄Alkylsulfonyl, or C each optionally substituted by fluorine, chlorine, bromine, cyano, methoxy or ethoxy₁-C₄-an alkoxycarbonyl group; r⁵Represents hydrogen, fluorine, chlorine, bromine or represents in each case optionally fluorine-and/or chlorine-substituted alkyl or alkoxy having 1 to 4 carbon atoms, R⁶Represents an alkyl radical having 1 to 4 carbon atoms which is optionally substituted by fluorine and/or chlorine, and R⁷Represents hydrogen, hydroxy, amino or represents each optionally fluorine, chlorine or C₁-C₄Alkoxy-substituted alkyl, alkoxy, alkenyl or alkynyl groups each up to 6 carbon atoms.

3. Substituted aminophenyluracils of the general formula (I) according to claim 1, characterized in that Q represents oxygen or sulphur, R¹Represents hydrogen, cyano, fluorine or chlorine, R²Represents cyano, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n-or i-propyl, n-, i-, s-or t-butyl or trifluoromethyl, R³Represents methyl, ethyl, n-or i-propyl, n-, i-, s-or t-butyl, optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, R³And also represents cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, optionally substituted by cyano, fluoro, chloro, bromo, methyl, ethyl, n-or isopropyl, R³Also represents optionally substituted phenyl, naphthyl, benzyl, phenethyl, thienyl, pyrazolyl, pyridyl or quinolyl, possible substituents being: fluorine, chlorine, bromine, cyano, nitro, carboxyl, carbamoyl, thiocarbamoyl, methyl, ethyl, n-or i-propyl, trifluoromethyl, methoxy, ethoxy, n-or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n-or i-propylthio, methylsulfinyl, ethylsulfinyl, n-or i-propylthioAlkylsulfinyl, methylsulfonyl, ethylsulfonyl, n-or isopropylsulfonyl, dimethylaminosulfonyl, diethylaminosulfonyl, methoxycarbonyl, ethoxycarbonyl, n-or isopropyloxycarbonyl, R⁴Represents cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, optionally substituted by cyano, fluoro, chloro, bromo, methyl, ethyl, n-or isopropyl, R⁴And each optionally substituted phenyl, naphthyl, furyl, thienyl, oxazolyl, isoxazolyl, pyrazolyl, pyridyl or pyrimidinyl, possible substituents being: fluorine, chlorine, bromine, cyano, nitro, carboxyl, carbamoyl, thiocarbamoyl, dimethylamino, dimethylaminosulfonyl or diethylaminosulfonyl, methyl, ethyl, n-or i-propyl, methoxy, ethoxy, n-or i-propoxy, methylthio, ethylthio, n-or i-propylthio, methylsulfinyl, ethylsulfinyl, n-or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n-or i-propylsulfonyl, methoxycarbonyl, ethoxycarbonyl, n-or i-propoxycarbonyl, phenyl, phenoxy or phenylthio, each optionally substituted by fluorine, chlorine, bromine, cyano, methyl, methoxy, trifluoromethyl and/or trifluoromethoxy, R is a phenyl, phenoxy or phenylthio group, each optionally substituted by fluorine, chlorine, bromine, cyano, methyl, methoxy, trifluoromethyl and/or trifluoromethoxy, and⁵represents hydrogen, fluorine, chlorine, bromine or represents methyl, ethyl, n-or isopropyl, each of which is optionally substituted by fluorine and/or chlorine, R⁶Represents methyl, ethyl, n-or isopropyl optionally substituted by fluorine and/or chlorine, and R⁷Represents hydrogen, amino or represents methyl, ethyl, n-or i-propyl, n-, i-or s-butyl, methoxy, ethoxy, n-or i-propoxy, n-, i-or s-butoxy, propenyl, butenyl, propynyl or butynyl, each of which is optionally substituted by fluorine and/or chlorine.

4. A process for the preparation of substituted aminophenyluracils of the general formula (I)Q, R therein¹、R²、R³、R⁴、R⁵、R⁶And R⁷Are as followsAs defined in claim 1, characterized in that the sulfonylaminophenyluracil of the general formula (II) is reacted with the acid derivative of the general formula (III), optionally in the presence of a reaction auxiliary and optionally in the presence of a diluent,q, R therein¹、R²、R³、R⁵、R⁶And R⁷Each as defined above, R⁴-CO-X (III) wherein R⁴As defined above, and X represents halogen or a group-O-CO-R⁴。

5. A method for controlling weeds, characterised in that a substituted aminophenyluracil of the general formula (I) as claimed in claims 1 to 4 is allowed to act on weeds and/or their habitat.

6. Use of substituted aminophenyluracils of the general formula (I) as claimed in claims 1 to 4 for controlling undesirable weeds and harmful insects.

7. Process for the preparation of herbicides and pesticides, characterized in that substituted aminophenyluracils of the general formula (I) according to claims 1 to 4 are mixed with extenders and/or surfactants.

8. Herbicides and pesticides, characterized in that they comprise at least one substituted aminophenyluracil of the general formula (I) according to claims 1 to 4.

9. Method for controlling harmful insects, characterized in that substituted aminophenyluracils of the general formula (I) according to claims 1 to 4 are allowed to act on the insects and/or their habitat.