WO1999052906A1 - Substituted oxazolyle and thiazolyl uracil herbicides - Google Patents

Abstract

The invention relates to novel substituted oxazolyle and thiazolyle uracils of general formula (I), wherein Q stand for oxygen or sulfur; R1 stands for hydrogen, amino or optionally cyano, halogen or C¿1?-C4-alkoxy-substituted alkyl with 1 to 4 carbon atoms; R?2¿ represents formyl, hydroximinomethyl, cyano, carboxy, C¿1?-C4 alkoxy-carbonyl, carbamoyl, thiocarbamoyl or optionally halogen-substituted alkyl with 1 to 4 carbon atoms; R?3¿ stands for hydrogen, cyano, halogen or optionally halogen-substituted alkyl with 1 to 4 carbon atoms; R4 represents hydrogen, halogen or optionally halogen-substituted alkyl with 1 to 4 carbon atoms and R5 stands for optionally substituted phenyl, naphthyl or pyridyl, whereby the substituents are chosen from amongst the following: nitro, amino, hydroxy, mercapto, carboxy, cyano, carbamoyl, thiocarbamoyl, halogen (optionally cyano, halogen, C¿1?-C4-alkoxy, C1-C4-alkoxy-carbonyl, C1-C4-alkylamino-carbonyl, di-(C1-C4-alkyl)-amino-carbonyl, phenylamino-carbonyl or N-(C1-C4-alkyl)-phenyl-amino-carbonyl substituted) alkyl, alkoxy, alkythio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonylamino, alkylsulfonylamino, N,N-bis-alkylcarbonyl-amino, N,N-bis-alkylsulfonyl-amino and N-alkylcarbonyl-N-alkylsulfonyl-amino with up to 6 carbon atoms in the alkyl groups and cycloalkylcarbonylamino and cycloalkylsulfonylamino with 3 to 6 carbon atoms in the cycloalkyl groups. The invention also relates to several methods for the production of said substances and their use in the treatment of plants, more particularly as herbicides and insecticides.

Description

SUBSTITUTED OXAZOLYL AND THIAZOLYL URACIL HERBICIDES

The present invention relates to new substituted oxazolyl- and thiazolyl-uracils, several processes for their preparation and their use as plant treatment agents, in particular as herbicides and insecticides.

Numerous heterocyclyluracils with herbicidal or insecticidal properties have already become known (cf. JP-A 91287585, JP-A 93202031, Chem. Abstr. J36, 235 650 and Chem. Abstr. 120, 107 048). For example, Use l- (3-chloro-5-trifluoromethyl-pyridin-2-yl) -3,6-dihydro-2,6-dioxo-4-trifluoromethyl-l (2H) -pyrimidine to control weeds. At low application rates, the effectiveness of this substance is not always satisfactory.

New substituted oxazolyl- and thiazolyl-uracils of the general formula (I)

R ¹

R I

(I),

R ^' r R ^D

Q

in which

Q represents oxygen or sulfur,

R ^{1 represents} hydrogen, amino or alkyl having 1 to 4 carbon atoms which is optionally substituted by cyano, halogen or CC ^ alkoxy, R ^{2 represents} formyl, hydroximinomethyl, cyano, carboxy, C 4 -C 4 -alkoxy-carbonyl, carbamoyl, thiocarbamoyl or alkyl which has 1 to 4 carbon atoms and is optionally substituted by halogen,

R ^{3 represents} hydrogen, cyano, halogen or alkyl which has 1 to 4 carbon atoms and is optionally substituted by halogen,

R ^{4 represents} hydrogen, halogen or alkyl which has 1 to 4 carbon atoms and is optionally substituted by halogen, and

R ^{5 represents} in each case optionally substituted phenyl, naphthyl or pyridyl, the possible substituents being selected from the following list:

Nitro, amino, hydroxy, mercapto, carboxy, cyano, carbamoyl, thiocarbamoyl, halogen, (each optionally by cyano, halogen, C1-C4-alkoxy, C, -C ₄ -alkoxy-carbonyl, C, -C ₄ -alkylamino- carbonyl, di (C, -C ₄ alkyl) amino carbonyl, phenylamino carbonyl or N- (C, -C ₄ alkyl) phenyl amino carbonyl substituted) alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl , Alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl,

Alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonylamino, alkylsulfonylamino, N, N-bis-alkylcarbonylamino, N, N-bis-alkylsulfonylamino and N-alkylcarbonyl-N-alkylsulfonylamino, each with up to 6 carbon atoms in the alkyl groups as well as cycloalkylcarbonylamino and cyclo - Alkylsulfonylamino, each with 3 to 6 carbon atoms in the cycloalkyl groups.

In the definitions, the hydrocarbon chains, such as alkyl, are also straight-chain or branched, in each case in conjunction with heteroatoms, such as in alkoxy. R ¹ preferably represents hydrogen, amino or methyl, ethyl, n- or i-propyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy;

R ² preferably represents formyl, hydroximinomethyl, cyano, carboxy, methoxycarbonyl, ethoxycarbonyl, carbamoyl, thiocarbamoyl or methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine and / or chlorine;

R ³ preferably represents hydrogen, cyano, fluorine, chlorine, bromine or methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine and / or chlorine;

R ⁴ preferably represents hydrogen, fluorine, chlorine, bromine or methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, which is optionally substituted by fluorine and / or chlorine;

R ⁵ preferably represents in each case optionally substituted phenyl, naphthyl or pyridyl, the possible substituents preferably being selected from the following list:

Nitro, amino, hydroxy, mercapto, carboxy, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine (each optionally by cyano, fluorine and / or chlorine, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, n -, i-, s- or t-butoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylaminocarbonyl, phenylaminocarbonyl or N-methyl-phenylaminocarbonyl 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, methylsulfinyl,

Ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, acetylamino, propionylamino, n- or i-butyroylamino, methylsulfonylamino, ethylsulfonylamino, n- or i- propylsulfonylsulfonylamino - or t-butylsulfonylamino, N, N-bis-acetyl-amino, N, N-bis-propionyl-amino, N, N-bis-methylsulfonyl-amino, N, N-bis-ethylsulfonyl-amino, N-acetyl- N-methylsulfonyl-amino, N-acetyl-N-ethylsulfonyl-amino, N-propionyl-N-methylsulfonyl-amino, N-propionyl-

N-ethylsulfonyl-amino, Nn-butyroyl-N-methylsulfonyl-amino, Nn-butyro-yl-N-ethylsulfonyl-amino, Ni-butyroyl-N-methylsulfonyl-amino, Ni-buty-royl-N-ethylsulfonyl-amino, N-pivaloyl-N-methylsulfonylamino, N-pivaloyl-N-ethylsulfonylamino, cyclopropylcarbonylamino, cyclopropylsulfonylamino.

Q preferably represents sulfur;

R ¹ particularly preferably represents hydrogen, amino, methyl or ethyl;

R ² particularly preferably represents trifluoromethyl;

R ³ particularly preferably represents hydrogen, chlorine or methyl;

R ⁴ particularly preferably represents hydrogen, fluorine, chlorine, bromine or methyl;

R ⁵ particularly preferably represents in each case optionally substituted phenyl or pyridyl, the possible substituents being selected in particular from the following list: Nitro, amino, hydroxyl, mercapto, carboxy, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine (methyl in each case optionally substituted by fluorine and / or chlorine, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl), Ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methyl sulfinyl, ethyl sulfinyl, methyl sulfonyl, Ethylsulfonyl, methylamino, ethylamino, n- or i-propylamino, dimethylamino, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, dimethylaminocarbonyl, acetylamino, propionylamino, n- or i-butyroylylamino, methylsilylamino, methylsilylamino, -

Propylsulfonylamino, n-, i-, s- or t-butylsulfonylamino, N, N-bis-acetyl-amino, N, N-bis-propionyl-amino, N, N-bis-methylsulfonyl-amino, N, N-bis - ethylsulfonyl-amino, N-acetyl-N-methylsulfonyl-amino, N-acetyl-N-ethylsulfonyl-amino, N-propionyl-N-methylsulfonyl-amino, N-propionyl-N-ethylsulfonyl-amino, Nn Butyroyl-N-methylsulfonylamino; Nn-butyroyl-N-ethylsulfonyl-amino, Ni-butyroyl-N-methylsulfonyl-amino, Ni-butyroyl-N-ethylsulfonyl-amino, N-pivaloyl-N-methylsulfonyl-amino, N-pivaloyl-N-ethylsulfonyl-amino, Cyclopropylcarbonylamino, cyclopropylsulfonylamino.

According to the invention, preference is given to the compounds of the formula (I) in which one

A combination of the meanings listed above as preferred is present.

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

A very particularly preferred group are those compounds of the formula (I) in which R ^{1 is} amino and Q, R ² , R ³ , R ⁴ and R ^{5 have} the meaning given above. Another very particularly preferred group are those compounds of the formula (I) in which R ^{1 is} methyl and Q, R ² , R ³ , R ⁴ and R ^{5 have} the meaning given above as being particularly preferred.

The general or preferred radical definitions listed above apply both to the end products of the formula (I) and correspondingly to the starting or intermediate products required in each case for the preparation. These radical definitions can be combined with one another, that is to say also between the specified preferred ranges.

The new substituted oxazolyl- and thiazolyl-uracils of the general formula (I) have interesting biological properties. They are particularly characterized by strong herbicidal and insecticidal activity.

The new substituted oxazolyl- and thiazolyl-uracils of the general type are obtained

Formula (I) if one

(a) aminoalkenates of the general formula (II)

O

(II)

Ό

A '

in which

R ² and R ^{3 have} the meanings given above and

A ^{1 represents} alkyl, aryl or arylalkyl,

with substituted oxazolyl or thiazolyl urethanes (oxazolyl or thiazolyl carbamates) of the general formula (III) ^A \ V

° - ^ - ^N - _N ^ ^N _{S 5}

(III) o Q-

in which

Q, R ⁴ and R ^{5 have} the meanings given above and

A ^{2 represents} alkyl, aryl or arylalkyl,

- or with corresponding oxazolyl or thiazolyl isocyanates -

if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,

or if you

(b) substituted oxazolyl- or thiazolyl-uracils of the general formula (Ia),

H

R 2 \ IL r / £>

(la)

R ^J "rT ^ Xf

O

in which

Q, R ² , R ³ , R ⁴ and R ^{5 have} the meanings given above, with l-aminooxy-2,4-dinitro-benzene or with alkylating agents of the general formula (IV)

X! -A ³ (IV)

in which

A ^{3 represents} optionally substituted alkyl and

X ^{1 represents} halogen or the grouping -0-S0 ₂ -0-A ³ ,

if appropriate in the presence of reaction auxiliaries and if appropriate in the presence of diluents,

and, if appropriate, subsequently carries out electrophilic or nucleophilic substitution reactions, addition or cleavage reactions, oxidation or reduction reactions as part of the definition of substituents in the context of the definition of substituents.

If, for example, 3-amino-2,4,4,4-tetrafluoro-crotonic acid methyl ester and N- (5-chloro-4-phenylthiazol-2-yl) -0-methyl-carbamate are used as starting materials, the course of the reaction can be as follows Process (a) according to the invention can be outlined by the following formula:

If, for example, 1- [4- (2,6-dichloropyridin-4-yl) thiazol-2-yl] -5-chloro-4-chlorodifluoromethyl-3,6-dihydro-2,6-dioxo-l is used (2H) pyrimidine and methyl bromide as Starting materials, the course of the reaction in process (b) according to the invention can be outlined using the following formula:

Br-CH,

- HBr

Formula (II) provides a general definition of the aminoalkenic acid esters to be used as starting materials in process (a) according to the invention for the preparation of compounds of the formula (I). In the formula (II), R ² and R ³ preferably have those meanings which have already been given as preferred, particularly preferred or very particularly preferred for R ² and R ³ in connection with the description of the compounds of the formula (I); A ¹ preferably represents C ¹ -C 4 -alkyl, phenyl or benzyl, in particular methyl or ethyl.

The starting materials of the general formula (II) are known and / or can be prepared by known processes (cf. J. Heterocycl. Chem. 9 (1972), 513- 522).

Formula (III) provides a general definition of the oxazolyl- or thiazolyl-urethanes to be used as starting materials in process (a) according to the invention. In formula (III), Q, R ⁴ and R ⁵ preferably have those meanings which are preferred, particularly preferred or very particularly preferred for Q, R ⁴ and R already in connection with the description of the compounds of the formula (I) according to the invention ^{5 were} specified; A ² preferably represents C 1 -C 4 -alkyl, phenyl or benzyl, in particular methyl or ethyl. The starting materials of the general formula (III) are known and / or can be prepared by processes known per se (cf. DE-A-2132431, DE-A-2453106, WO-A-8202384, WO-A-9724343, Indian J. Chem., Sect. B 28B (1989), 786-789, preparation examples).

Formula (Ia) generally defines the substituted oxazolyl- and thiazolyluracils to be used as starting materials in process (b) according to the invention for the preparation of compounds of the formula (I). In the formula (Ia), Q, R ² , R ³ , R ⁴ and R ⁵ preferably have those meanings which have already been mentioned above in connection with the description of the compounds of the invention

Formula (I) has been given as preferred, particularly preferred or very particularly preferred for Q, R ² , R ³ , R ⁴ and R ⁵ .

The starting materials of the general formula (Ia) for process (b) are also the subject of the present application as new substances; they can be prepared by process (a) according to the invention.

Formula (IV) provides a general definition of the alkylating agents to be used further as starting materials in process (b) according to the invention. In the formula (IV), A ³ preferably represents optionally by cyano, halogen or

C1 -C4 alkoxy substituted alkyl having 1 to 4 carbon atoms and X ¹ for chlorine, bromine, iodine, methylsulfonyloxy or ethylsulfonyloxy; in particular, A ³ represents methyl, ethyl, n- or i-propyl, each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, and X ^{1 represents} chlorine, bromine, iodine, methylsulfonyloxy or ethylsulfonyloxy.

The starting materials of formula (IV) are known organic synthetic chemicals.

The processes according to the invention for the preparation of the compounds of the general formula (I) are preferably carried out using diluents. As a diluent for carrying out the inventive

10 Processes (a) and (b) are primarily inert organic solvents. These include in particular ahphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers, such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones, such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or butyronitrile; Amides, such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric acid 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 monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, their mixtures with water or pure water.

The usual inorganic or organic bases or acid acceptors are generally suitable as reaction auxiliaries for processes (a) and (b). These preferably include alkali metal or alkaline earth metal acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkanolates, such as, for example, sodium, potassium or calcium acetate, lithium, sodium or potassium - or

Calcium amide, sodium, potassium or calcium carbonate, sodium, potassium or calcium hydrogen carbonate, lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium hydroxide, Sodium or potassium methoxide, ethanolate, n or i propanolate, n, i, s or t butanolate; basic organic nitrogen compounds, such as trimethylamine, triethylamine, tripropylamine, tributylamine, ethyldiisopropylamine, N, N-dimethylcyclohexylamine, dicyclohexylamine, ethyldicyclohexylamine, N, N-dimethylaniline, N, N-dimethyl-benzylamine, pyridine, 2-methyl, 3-methyl, 4-methyl, 2,4-dimethyl, 2,6-dimethyl, 3,4-dimethyl and 3,5-dimethyl pyridine, 5-ethyl-2-methyl-pyridine, 4-dimethylamino-pyridine, N-methyl-piperidine, 1, 4-diazabicyclo-

11 [2,2,2] octane (DABCO), 1,5-diazabicyclo [4,3,0] non-5-ene (DBN), or 1,8-diazabicyclo [5,4,0] -undec-7-en (DBU).

The reaction temperatures can be varied within a substantial range when carrying out processes (a) and (b) according to the invention. In general, temperatures between -20 ° C and + 200 ° C, preferably between 0 ° C and 180 ° C.

Processes (a) and (b) according to the invention are generally carried out under atmospheric pressure. However, it is also possible to carry out the processes according to the invention under elevated or reduced pressure - generally between 0.1 bar and 10 bar.

To carry out the process according to the invention, the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess. The 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 several hours. The work-up is carried out using customary methods (cf. the manufacturing examples).

The active compounds according to the invention can be used as defoliants, desiccants, haulm killers and in particular as weed killers. Weeds in the broadest sense are all plants that grow in places where they are undesirable. 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 e.g. can be used in the following plants:

12 Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduippum, Sonuanum , Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium,

Ranunculus, Taraxacum.

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

Monocotyledon weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Iochasumirumum, Scalumumum, Scalumumum , Sphenoclea, Dactyloctenium, Agrostis, Alopecurus,

Apera.

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

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

Depending on the concentration, the compounds are suitable for total weed control, e.g. on industrial and track systems and on paths and squares with and without tree cover. Likewise, the compounds for weed control in permanent crops, e.g. Forest, ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants, on ornamental and sports turf and pastures and for selective weed control in annual crops.

13 The compounds of the formula (I) according to the invention are particularly suitable for the selective control of monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon crops both in the pre-emergence and in the post-emergence process.

The active ingredients are also suitable for controlling animal pests, preferably arthropods and nematodes, in particular insects and arachnids, which occur in agriculture, in forests, in the protection of stored goods and materials and in the hygiene sector. They are effective against normally sensitive and resistant species as well as against all or individual stages of development. The pests mentioned above include:

From the order of the Isopoda e.g. Oniscus asellus, Armadillidium vulgare, Porcellio scaber.

From the order of the Diplopoda e.g. Blaniulus guttulatus.

From the order of the Chilopoda e.g. Geophilus carpophagus, Scutigera spec.

From the order of the Symphyla e.g. Scutigerella immaculata.

From the order of the Thysanura e.g. Lepisma saccharina.

From the order of the Collembola e.g. Onychiurus armatus.

From the order of the Orthoptera e.g. Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria.

From the order of the Dermaptera e.g. Forficula auricularia.

14 From the order of the Isoptera, for example Reticulitermes spp.

From the order of the anoplura e.g. Pediculus humanus corporis, Haematopinus spp., Linognathus spp.

From the order of the Mallophaga e.g. Trichodectes spp., Damalinea spp.

From the order of the Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci.

From the order of the Heteroptera e.g. Eurygaster spp., Dysdercus intermedius,

Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.

From the order of the Homoptera e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis,

Macrosiphum avenae, Myzus spp., Pemphigus spp., Phorodon humuli, Phylloxera vastatrix, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatataidia, aphidium, Aspiatellus lp . Psylla spp.

From the order of the Lepidoptera e.g. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp. Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Spodoptera exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplocapsia n. , Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona viridima, Homona magnidana.

15 From the order of the Coleoptera, for example, Anobium punctatum, Rhizopertha dominica, Acanthoscelides obtectus, Bruchidius obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysoisusamamysppas, Atomic spp. , Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus,

Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Agribiole spp., Tenebrio molitor. Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica.

From the order of the Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.

From the order of the Diptera e.g. Aedes spp., Anopheles spp., Culex spp.,

Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tabanus spp. Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa.

From the order of the Siphonaptera e.g. Xenopsylla cheopis, Ceratophyllus spp.

From the order of the Arachnida e.g. Scorpio maurus, Latrodectus mactans.

From the order of the Acarina e.g. Acarus siro, Argas spp., Omithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Chorioptes spp ., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp.

16 The plant-parasitic nematodes include, for example, Pratylenchus spp., Radopholus spp., Ditylenchus spp., Tylenchulus spp., Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp.,. Tylenchus spp., Helicotylenchus spp., Rotylenchus spp., Tylenchulus spp.

The compounds of the general formula (I) according to the invention are very suitable for controlling plant-damaging insects, such as e.g. Rice leafhoppers (Nephotettix spp.).

To a certain extent, the compounds of the general formula (I) according to the invention also have fungicidal activity, in particular against Phytophthora spp.

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, active substance-impregnated natural and synthetic substances and very fine encapsulations in polymeric substances.

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

If water is used as an extender, e.g. organic solvents can also be used as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated ahphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, ahphatic hydrocarbons, such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable

17 Oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.

Possible solid carriers are: e.g. Ammonium salts and natural

Rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours and granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; as emulsifying and / or foaming agents are possible: e.g. non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersants are: e.g. Lignin sulfite leaching and methyl cellulose.

Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations. Other additives can be mineral and vegetable oils.

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

The formulations generally contain between 0.1 and 95 percent by weight

Active ingredient, preferably between 0.5 and 90%. The active compounds according to the invention, as such or in their formulations, can also be used for combating weeds, in a mixture with known herbicides, finished formulations or tank mixes being possible.

Known herbicides are suitable for the mixtures, for example

Acetochlor, Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Ametryne, Amidochlor, Amidosulfuron, Anilofos, Asulam, Atrazine, Azafenidin, Azimsulfuron, Benazolin (-ethyl), Benfuresate, Bensulfuron (-methyl)

Benzofenap, Benzoylprop (-ethyl), Bialaphos, Bifenox, Bispyribac (-sodium), Bromobutide, Bromofenoxim, Bromoxynil, Butachlor, Butroxydim, Butylate, Cafenstrole, Caloxydim, Carbetamide, Carfentrazone (-ethyl), Chlomethoxyonaz (Chloron, Chloramben, Chloramben, Chloramben, Chloramben, Chloramben, Chloramben, Chloramben, Chlorambene -ethyl), chloronitrofen, chlorosulfuron, chlorotoluron, cinmethylin, cinosulfuron, clethodim, clodinafop (-propargyl),

Clomazone, Clomeprop, Clopyralid, Clopyrasulfuron (-methyl), Cloransulam (- methyl), Cumyluron, Cyanazine, Cycloate, Cyclosulfamuron, Cycloxydim, Cyhalofop (-butyl), 2,4-D, 2,4-DB, 2, 4-DP, Desmedipham, Diallate, Dicamba, Diclofop (-methyl), Diclosulam, Diethatyl (-ethyl), Difenzoquat, Diflufenican, Difluefenzopyr, Dimefuron, - Dimepiperate, Dimethachlor, Dimethametryn, Dimethenamid, Dimeitramine , Diphenamide, Diquat, Dithiopyr, Diuron, Dymron, Epoprodan, EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron (-methyl), Ethofumesate, Ethoxyfen, Ethoxysulfüron, Etobenzanid, Fenoxaprop (-P-ethyl), Flamprop (-isopropyl), Flamprop isopropyl-L), flamprop (-methyl), flazasulfuron, fluazifop (-P-butyl), flumetsulam, flumiclorac (-pentyl), flumioxazin, flumipropyn, flumetsulam, fluometuron, fluorochloridone, fluoroglycofen (-ethyl), flupacilox , Flurpyrsulfuron (-methyl, -sodium), Flurenol (-butyl), Fluridone, Fluroxypyr (-meptyl), Flurprimidol, Flurtamone, Fluthiacet (-methyl), Fluthiam ide, Fomesafen, Glufosinate (-ammonium), Glyphosate (-isopropyl-ammonium), Halosafen, Haloxyfop (-ethoxyethyl), Haloxyfop (-P-methyl), Hex-azinone, Imazamethabenz (-methyl), Imazamethapyr, Imazamox, Imazapyr, Imaza-

19 quin, Imazethapyr, Imazosulfuron, Ioxynil, Isopropalin, Isoproturon, Isouron, Isoxaben, Isoxaflutole, Isoxapyrifop, Lactofen, Lenacil, Linuron, MCPA, MCPP, Mefenacet, Metamitron, Metazachlor, Metabenzthomouron) Metolachlor, Metosulam, Metoxuron, Metribuzin, Met- sulfuron (-methyl), Molinate, Monolinuron, Naproanilide, Napropamide, Neburon,

Nicosulfuron, norflurazon, orbencarb, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat, pelargonic acid, pendimethalin, pentoxazone, phenmedipham, piperophos, pretilachlor, primisulfuron, propynach, methynilis, methynil, methynil) Propyzamides, prosulfocarb, prosulfuron, pyraflufen (-ethyl), pyrazolates, pyrazosulfuron (-ethyl),

Pyrazoxyfen, pyribenzoxim, pyributicarb, pyridate, pyriminobac (-methyl), pyrithiobac (-sodium), quinchlorac, quinmerac, quinoclamine, quizalofop (-P-ethyl), quizalofop (-P-tefuryl), rimsulfuron, simethane, sethoxydimim Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (-methyl), Sulfosate, Sulfosulfuron, Tebutam, Tebuthiuron, Terbuthylazine, Terbutryn, Thenylchlor, Thiafluamide, Thiazopyr,

Thidiazimin, Thifensulfuron (-methyl), Thiobencarb, Tiocarbazil, Tralkoxydim, Triallate, Triasulfuron, Tribenuron (-methyl), Triclopyr, Tridiphane, Trifluralin and Triflusulfuron.

A mixture with other known active ingredients, such as fungicides,

Insecticides, acaricides, nematicides, bird repellants, plant nutrients and soil structure improvers are possible.

The active ingredients as such, in the form of their formulations or the use forms prepared therefrom by further dilution, such as ready-to-use

Solutions, suspensions, emulsions, powders, pastes and granules are used. They are used in the usual way, e.g. by pouring, spraying, spraying, sprinkling.

20th The active compounds according to the invention can be applied both before and after emergence of the plants. They can also be worked into the soil before sowing.

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

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

21 Manufacturing examples:

example 1

(Method (a))

7.3 g (30 mmol) of 3-amino-4,4,4-trifluoro-crotonic acid ethyl ester are placed in 50 ml of N-methyl-pyrrolidone, mixed in portions with 1.1 g of sodium hydride and 30 minutes at room temperature (approx. 20 ° C) stirred. Then 0.55 g (30 mmol) of N- [4- (2,6-dichloropyridin-4-yl) thiazol-2-yl] -0-ethyl-urethane are added and the reaction mixture is opened for 6 hours Heated 160 ° C. After cooling to room temperature, the mixture is diluted to about three times the volume with approximately equal volumes of aqueous IN sodium hydroxide solution and ethyl acetate, and after shaking, the aqueous phase is separated off and acidified with hydrochloric acid. Then it is shaken with ethyl acetate, the organic phase is separated off, washed with water, dried with sodium sulfate and filtered. The filtrate is concentrated in a water jet vacuum, the residue is digested with ether / petroleum ether and the crystalline product is isolated by suction.

7.1 g (58% of theory) of l- [4- (2,6-dichloropyridin-4-yl) thiazol-2-yl] -4-trifluoromethyl-3,6-dihydro-2 are obtained, 6-dioxo-l (2H) -pyrimidine, melting point 293 ° C.

22 Example 2

(Method (b))

A mixture of 2.0 g (4.9 mmol) of l- [4- (2,6-dichloropyridin-4-yl) thiazol-2-yl] -4-trifluoromethyl-3,6-dihydro-2 , 6-dioxo-l (2H) -pyrimidine, 1.2 g (4.9 mmol) 1-amino-oxy-2,4-dinitro-benzene, 0.5 g sodium hydrogen carbonate and 10 ml N, N-dimethyl- formamide is stirred for four days at room temperature (approx. 20 ° C). After adding a further 0.7 g of l-aminooxy-2,4-dinitro-benzene and 0.3 g of sodium hydrogen carbonate, the mixture is stirred for a further eight days at room temperature. The mixture is then diluted to about twice the volume with 1% aqueous sodium hydroxide solution and shaken with diethyl ether. The organic phase is separated off, washed successively with 2N sodium hydroxide solution, water, 2N hydrochloric acid and saturated aqueous sodium chloride solution, dried with sodium sulfate and filtered. The filtrate is concentrated in a water jet vacuum, the residue is digested with diethyl ether and the crystalline product is isolated by suction.

0.9 g (43% of theory) of 3-amino-l- [4- (2,6-dichloropyridin-4-yl) thiazol-2-yl] -4-trifluoromethyl-3,6- dihydro-2,6-dioxo-l (2H) pyrimidine of melting point

250 ° C.

23 Example 3

(Method (b))

A mixture of 1.5 g (3.7 mmol) of l- [4- (2,6-dichloropyridin-4-yl) thiazol-2-yl] -4-trifluoromethyl-3,6-dihydro-2 , 6-dioxo-l (2H) -pyrimidine, 0.5 g of dimethyl sulfate, 0.55 g of potassium carbonate and 20 ml of acetone is heated under reflux for 45 minutes and then concentrated in a water jet vacuum. The residue is stirred with approximately equal volumes of water, 2N hydrochloric acid, diethyl ether, ethyl acetate and the crystalline product obtained is isolated by suction.

0.7 g (45% of theory) of l- [4- (2,6-dichloropyridin-4-yl) thiazol-2-yl] -3-methyl-4-trifluoromethyl-3,6- dihydro-2,6-dioxo-l (2H) -pyrimidine, melting point 271 ° C.

Example 4

(Follow-up implementation)

24 A mixture of 1.5 g (3.7 mmol) of l- [4- (2,6-dichloropyridin-4-yl) thiazol-2-yl] -4-trifluoromethyl-3,6-dihydro-2 , 6-dioxo-l (2H) -pyrimidine, 0.4 g methanesulfonic acid amide, 1 g potassium carbonate and 10 ml N-methyl-pyrrolidone is stirred for two hours at 180 ° C. and, after cooling, poured onto ice water acidified with hydrochloric acid . Then it is extracted with ethyl acetate, the organic phase with

Washed water, dried with sodium sulfate and filtered. The solvent is carefully distilled off from the filtrate in a water jet vacuum.

1.5 g (88% of theory) of 1- [4- (2-chloro-6-methylsulfonylamino-pyridin-4-yl) thiazol-2-yl] -4-trifluoromethyl-3,6-dihydro- 2,6-dioxo-l (2H) pyrimidine as an amorphous residue.

Example 5

(Method (b))

A mixture of 1.3 g (2.8 mmol) of 1- [4- (2-chloro-6-methylsulfonylaminopyridin-4-yl) thiazol-2-yl] -4-trifluoromethyl-3,6-dihydro -2,6-dioxo-l (2H) -pyrimidine, 0.38 g dimethyl sulfate, 0.25 g sodium hydrogen carbonate and 10 ml acetone is heated under reflux for 20 hours and then concentrated in a water jet vacuum. The residue is shaken with 2N hydrochloric acid and ethyl acetate, the organic phase is separated off, washed with water, dried with sodium sulfate and filtered. The filtrate is concentrated in a water jet vacuum and the residue is purified by column chromatography (silica gel, chloroform / ethyl acetate).

25th 0.40 g (30% of theory) of 1- [4- (2-chloro-6-methylsulfonylamino-pyridin-4-yl) thiazol-2-yl] -3-methyl-4-trifluoromethyl-3 are obtained, 6-dihydro-2,6-dioxo-l (2H) pyrimidine, melting point 160 ° C.

Analogously to preparation examples 1 to 5 and in accordance with the general description of the preparation processes according to the invention, it is also possible, for example, to prepare the compounds of the formula (I) listed in table 1 below.

(I),

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

Ex. Schmelz¬

Rl R2 R3 R R5 point (° C)

H CF HH

202

CH ₃ CFα HH 202

NH ₇ CF, HH 254

26 Ex. Schmelz¬

Q Rl R2 R3 R4 R5 point (° C)

9 SH CF ₃ HH Λ rJ ^ 225

10 s CH ₃ CF ₃ HH Λ CJ ^* \ 149

1 1 s NH ₂ CF ₃ HH Jθ 179

NO, 1 ²

12 s CH CF ₃ HH d NO, 1 ²

13 s NH ₂ CF ₃ HH d N0 ₂

14 s CH ₃ CF ₃ HH JO

CH., 1

15 s CF ₃ HH HN ²

CH ₃ d ^C 2 ^H S

1

16 s CH ₃ CF ₃ HH HN ² d OCH,

1

17 s CH ₃ CF ₃ HH

^d >

27 Ex. Schmelz¬

Q Rl R2 R3 R4 R5 point (° C)

OCH,

18 CH ₃ CF, HH

19 CH ₃ CF _q HH

OCH,

20 CH ₃ CF, HH

NO,

NO,

21 CH ₃ CF ₃ HH

188

22 CH ₃ CF, HH

CH, ^C 2 ^H S

I ^{2 5}

,so,

23 CH ₃ CF, HH or

? 2 ^H 5 ^C 2 ^H 5

24 CH ₃ CF ₃ HHO ^ N- ^S ° ²

? W., C ₂ H ₅

25 CH ₃ CF, HH ^* N '

28 Ex. Schmelz¬

Q Rl R2 R3 R4 R5 point (° C)

26 s H CF ₃ HH xd ('H NMR (D6-DMSO, δ): 6.46 ppm)

27 s CH ₃ CF ₃ HH xd "('H NMR (D6-DMSO, δ): 7.89 ppm)

^{5 2} ^ so ₂ ('H NMR

28 s CH ₃ CF ₃ HH x (D6-DMSO, δ): 8.22 ppm)

('H NMR

29 s H CF ₃ HHX (D6-DMSO

CGH ^" ₃ ,, δ): 7.86 ppm)

30 s CH ₃ CF ₃ HH ³ C3 1 18 H ₃

('H NMR

31 s NH ₂ CF ₃ HH ³ (D6-DMSO

CH ₃ ¹ ». , δ): 7.90 ppm)

('H NMR

32 s H CF ₃ HH xd "(D6-DMSO, δ): 8.14 ppm)

33 s CH ₃ CF ₃ HH

Xd

29 Ex. Schmelz¬

Q Rl R2 R3 R4 R5 point (° C)

OCH ₃

34 s CH ₃ CF ₃ HH o ^ γ ^CH xd (R enantiomer)

35 s CH ₃ CF ₃ HH xd OC ₂ H _{5 0} ^ γCH ₃

36 s CH ₃ CF ₃ HH xd (R enantiomer)

OCH _{3 0} ^ γCH ₃

37 s Me CF ₃ HH

Xd (racemate)

38 s CH ₃ CF ₃ HH Xd

39 s CH ₃ CF ₃ HH d OH

0 ^ _/ OCH ₃

40 s CH ₃ CF ₃ HH 0

6

30th Ex. Schmelz¬

Q Rl R2 R3 R4 R5 point (° C)

41 s CH ₃ CF ₃ HH ιP ι

^0; ^ _OCH3

N (CH ₃ ) ₂

42 s CH ₃ CF ₃ HHX jd

NHCH, 1

43 s CH ₃ CF ₃ HH xd NHC _R H,

44 s CH ₃ CF ₃ HH x 3d ^ _N ^ 6 5

45 s CH ₃ CF ₃ HH

jy

^ ^Br

46 s H CF ₃ HH

47 s CH ₃ CF ₃ HHG rUV ^r

48 s H CF ₃ HH Λ C ^* \ _B ,

31 Ex. Schmelz¬

Q Rl R2 R3 R4 R5 point (° C)

49 s CH ₃ CF ₃ HHA (T ^ ΛI _Br

50 s H CF ₃ H CH ₃ Λ fJ ^r

51 s CH ₃ CF ₃ H CH ₃ Λ fJY ^Br

52 s NH ₂ CF ₃ H CH ₃ Λ rJr ^Br

53 s H CF ₃ HH Λ fJγ ^c '

54 s CH ₃ CF ₃ HH Λ rJγ ^cι

55 s H CF ₃ HH IT ^ I

Cl

56 s CH ₃ CF ₃ HHG

Cl

57 s H CF ₃ HH ^/ ^ f ^ γ ^• C ^F H ₃

58 s CH ₃ CF ₃ HH γ ^F

- ^^ CH ₃

59 s H CF ₃ HH - ^ ιf ^ T ^c C ^l H ₃

32 Ex. Schmelz¬

Q Rl R2 R3 R4 R5 point (° C)

60 s CH ₃ CF ₃ HH ^/ ^ - ^ CH ₃

61 s H CF ₃ HH

Clf ^"

62 s CH ₃ CF ₃ HH £ C3l

63 s H CF ₃ HHX CfH ₃ ^"'

64 s CH ₃ CF ₃ HH xd CH ₃ -

65 s H CF ₃ HH xd-

66 s CH ₃ CF ₃ HH xd "

67 s H CF ₃ HH x?

68 s CH ₃ CF ₃ HH x?

69 s H CF ₃ HH

JO

33 Ex. Schmelz¬

Q Rl R2 R3 R4 R5 point (° C)

70 s CH ₃ CF ₃ HH Xi

71 s H CF ₃ HH XJ

72 s CH ₃ CF ₃ HH XJ

SCH ₃

73 s CH ₃ CF ₃ HH Λ / ^ cH ₃

34 Starting materials of formula (III):

Example (III-l)

H ₅ C ₂ HI

O ^ .N

10.0 g (40.6 mmol) of 2-amino-4- (2,6-dichloropyridin-4-yl) thiazole and 3.55 g of pyridine are placed in 200 ml of methylene chloride and at 0 ° C to 5 ° C with 4.88 g of ethyl chloroformate was added dropwise with stirring. The mixture is stirred at the specified temperature for four hours and then concentrated in a water jet vacuum. The residue is stirred with 2N hydrochloric acid and diethyl ether and the crystalline product isolated by suction.

10.0 g (77% of theory)) of N- [4- (2,6-dichloropyridin-4-yl) thiazol-2-yl] -O-ethyl-urethane with a melting point of 161 ° C. are obtained.

35 Examples of use:

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 about 24 hours, the active ingredient preparation is poured onto the floor. The amount of water per unit area is expediently kept constant. The concentration of active substance in the preparation is irrelevant, the only decisive factor is the amount of active substance applied per unit area.

After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control.

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

100% = total annihilation

In this test, for example, the compounds according to Preparation Examples 2, 5, 8, 10 and 11 show with good tolerance to crop plants, such as e.g. Maize and rapeseed, strong against weeds.

36 Example B

Post 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 level

Concentration.

Test plants with a height of 5-15 cm are sprayed with the active substance preparation in such a way that the desired amounts of active substance are applied per unit area. The concentration of the spray liquor is chosen so that in

1000 1 water / ha the desired amounts of active ingredient are applied.

After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control.

It means:

0% = no effect (like untreated control) 100% = total destruction

In this test, for example, the compounds according to the preparation example show

2, 5, 8, 10 and 11 with partially good tolerance to crops, such as Wheat, effective against weeds.

37 Example C

Nephotettix test

Solvent: 7 parts by weight of dimethylformamide

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 and the given amount of emulsifier, and the concentrate is diluted with water to the desired concentration.

Rice seedlings (Oryza sativa) are treated by dipping into the active ingredient preparation of the desired concentration and populated with larvae of the green rice leafhopper (Nephotettix cincticeps) while the seedlings are still moist.

After the desired time, the kill is determined in%. 100% means that all cicadas have been killed; 0% means that no cicadas have been killed.

In this test, e.g. the following compounds of the preparation examples have good activity: 1 and 6.

38

Claims

claims

1. Substituted oxazolyl- and thiazolyl-uracils of the general formula (I)

R ¹

R ^, N, -.0

(I), ι3 r NL -N

R ^J 'T -R ⁵ o Q / ⁴ in which

Q represents oxygen or sulfur,

R ¹ represents hydrogen, amino or optionally cyano-, halogen or C _j -C - alkoxy-substituted alkyl having 1 to 4 carbon atoms,

R ² for formyl, hydroximinomethyl, cyano, carboxy, -C4-alkoxycarbonyl, carbamoyl, thiocarbamoyl or for optionally by

Halogen-substituted alkyl having 1 to 4 carbon atoms,

R ^{3 represents} hydrogen, cyano, halogen or alkyl which has 1 to 4 carbon atoms and is optionally substituted by halogen,

R ^{4 represents} hydrogen, halogen or alkyl which has 1 to 4 carbon atoms and is optionally substituted by halogen, and

R ^{5 represents} in each case optionally substituted phenyl, naphthyl or pyridyl, the possible substituents being selected from the following list:

39 Nitro, amino, hydroxy, mercapto, carboxy, cyano, carbamoyl, thiocarbamoyl, halogen, (in each case optionally by cyano, halogen, C1-C4-alkoxy, C, -C ₄ -alkoxy-carbonyl, C, -C ₄ -alkylamino- carb-onyl, di- (C, -C ₄ -alkyl) -amino-carbonyl, phenylamino-carbonyl or

N- (C, -C ₄ alkyl) phenylamino-carbonyl substituted) alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonylamino, alkylsulfonylamino, N, N-bis-alkyl - carbonyl-amino, N, N-bis-alkylsulfonyl-amino and N-alkylcarbonyl-

N-alkylsulfonylamino, each with up to 6 carbon atoms in the alkyl groups, and cycloalkylcarbonylamino and cycloalkylsulfonylamino, each with 3 to 6 carbon atoms in the cycloalkyl groups.

Substituted oxazolyl- and thiazolyl-uracils according to claim 1, characterized in that

Q represents oxygen or sulfur,

R ^{1 represents} hydrogen, amino or methyl, ethyl, n- or i-propyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy,

R ² for formyl, hydroximinomethyl, cyano, carboxy, methoxycarbonyl,

Ethoxycarbonyl, carbamoyl, thiocarbamoyl or represents methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine and / or chlorine,

40 R ^{3 represents} hydrogen, cyano, fluorine, chlorine, bromine or methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine and / or chlorine,

R ^{4 represents} hydrogen, fluorine, chlorine, bromine or methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl which is optionally substituted by fluorine and / or chlorine, and

R ^{5 represents} in each case optionally substituted phenyl, naphthyl or pyridyl, the possible substituents preferably being selected from the following list:

Nitro, amino, hydroxy, mercapto, carboxy, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine (in each case optionally by cyano, fluorine and / or chlorine, methoxy, ethoxy, methoxycarbonyl,

Ethoxycarbonyl, n- or i-propoxycarbonyl, n-, i-, s- or t-butoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i- propylaminocarbonyl, dimethylaminocarbonyl, phenylaminocarbonyl or N-methylphenylaminocarbonyl 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, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, Methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, acetyl, propionyl, n- or i- Butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylaminocarbonyl, diefhylamino-carbonyl, acetylamino, propionylamino, n- or i-butyroylamino, methylsulfonylamino, methylsulfonylamino Propylsulfonylamino, n-, i-, s- or t-butylsulfonylamino, N, N-bis-acetylamino,

41 N, N-bis-propionyl-amino, N, N-bis-methylsulfonyl-amino, N, N-bis-ethylsulfonyl-amino, N-acetyl-N-methylsulfonyl-amino, N-acetyl-N-ethylsulfonyl-amino, N-propionyl-N-methylsulfonyl-amino, N-propionyl-N-ethylsulfonyl-amino, Nn-butyroyl-N-methylsulfonyl-amino, Nn-butyroyl-N-ethylsulfonyl-amino, Ni-butyroyl-N-mefhylsulfonyl- amino, Ni-butyroyl-N-ethylsulfonyl-amino, N-pivaloyl-N-methylsulfonyl-amino, N-pivaloyl-N-ethylsulfonyl-amino, cyclopropylcarbonylamino, cyclopropylsulfonylamino.

Substituted thiazolyl uracils according to claim 1, characterized in that

Q represents sulfur,

R ^{1 represents} hydrogen, amino, methyl or ethyl,

R ^{2 represents} trifluoromethyl,

R ^{3 represents} hydrogen, chlorine or methyl,

R ^{4 represents} hydrogen, fluorine, chlorine, bromine or methyl, and

R ^{5 stands} for optionally substituted phenyl or pyridyl, the possible substituents being selected in particular from the following list:

Nitro, amino, hydroxyl, mercapto, carboxy, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine (methyl optionally substituted by fluorine and / or chlorine, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbony) methyl, Ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-

Propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl,

42 Ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methylamino, ethylamino, n- or i-propylamino, dimethylamino, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, dimethylaminocarbonyl, acetylamino, propionylamino, methyl, n- or iamonamino Ethylsulfonylamino, n- or i-propylsulfonylamino, n-, i-, s- or t-butylsulfonylamino, N, N-bis-acetyl-amino, N, N-bis-propionyl-amino, N, N-bis- methylsulfonyl-amino, N, N-bis-ethylsulfonyl-amino, N-acetyl-N-methylsulfonyl-amino, N-acetyl-N-ethylsulfonyl-amino, N-propionyl-N-methylsulfonyl-amino, N-propionyl- N-ethylsulfonyl-amino, Nn-butyroyl-N-methylsulfonyl-amino, Nn-butyroyl-N-ethylsulfonyl-amino, Ni-butyroyl-N-methylsulfonyl-amino, Ni-butyroyl-N-ethylsulfonyl-amino, N- Pivaloyl-N-methylsulfonylamino, N-pivaloyl-N-ethylsulfonylamino, cyclopropylcarbonylamino, cyclopropylsulfonylamino.

4. A process for the preparation of substituted oxazolyl and thiazolyl uracils according to any one of claims 1 to 3, characterized in that

(a) aminoalkenates of the general formula (II)

O

(II)

in which

R ² and R ^{3 have} the meanings given in claim 1 and

A ^{1 represents} alkyl, aryl or arylalkyl,

43 with substituted oxazolyl or thiazolyl urethanes (oxazolyl or thiazolyl carbamates) of the general formula (III)

(III)

O

in which

Q, R ⁴ and R ^{5 have} the meanings given in Claim 1 and

A ^{2 represents} alkyl, aryl or arylalkyl,

- or with corresponding oxazolyl or thiazolyl isocyanates -

if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,

or that one

(b) substituted oxazolyl- or thiazolyl-uracils of the general formula (Ia),

HI

R «P

Ύ N- ^ N (la)

R ³ "V ^"

OQ

in which

44 Q, R ² , R ³ , R ⁴ and R ^{5 have} the meanings given in one of Claims 1 to 3,

with l-aminooxy-2,4-dinitro-benzene or with alkylating agents of the general formula (IV)

X ^l -A ³ (IV)

in which

A ^{3 represents} optionally substituted alkyl and

X ^{1 represents} halogen or the grouping -0-S0 ₂ -0-A ³ ,

if appropriate in the presence of reaction auxiliaries and if appropriate in the presence of diluents,

and, if appropriate, subsequently carries out electrophilic or nucleophilic substitution reactions, addition or cleavage reactions, oxidation or reduction reactions as part of the definition of substituents in the context of the definition of substituents.

Substituted oxazolyl- or thiazolyl-uracils of the general formula (Ia),

H

R N

R 'Y

»-R ^a

(la)

R ⁴ in which

45 Q, R ² , R ³ , R ⁴ and R ^{5 have} the meanings given in one of claims 1 to 3.

6. Use of at least one substituted oxazolyl- or thiazolyl-uracil according to one of claims 1 to 3 for combating undesirable

Plants.

7. Use of at least one substituted oxazolyl- or thiazolyl-uracil according to one of claims 1 to 3 for combating animal pests, preferably arthropods and / or nematodes.

8. Plant treatment agent, characterized by the content of at least one oxazolyl- or thiazolyl-uracil according to one of claims 1 to 3 and conventional extenders.

46