MXPA01003564A - 3-phenyl-pyrones - Google Patents

Abstract

The invention relates to novel 3-phenyl-pyrones of formula (I), wherein A, D, X and Y have the meanings given in the description, to a method for producing these substances and to their use as pesticides, fungicides and herbicides.

Description

3-PHENYL-PYRONS Field of the invention The present invention relates to novel 3-phenyl-pyrones, to a process for their preparation and to their use as pesticides, fungicides and herbicides.

BACKGROUND OF THE INVENTION A large number of oximetoxy-3-phenyl-pyrone derivatives with pesticidal, fungicidal and herbicidal properties have already been disclosed (see WO 97-19 941). The activity of these products is good but it leaves much to be desired in some cases due to low application quantities or for certain indications. The 3- (2-methyl-4-fluoro-phenyl) -4-hydroxy-5-methyl-6- (pyrid-2-yl) -pyrone and the 3- (2-methyl-4-chloro) have already been described. phenyl) -4-hydroxy-5-rr? ethyl-6- (4-fluoro-phenyl) -pyrone as intermediates (see WO 97-19 941). Of course, no biological properties of these substances are mentioned.

Detailed description of the invention. We have now found new 3-phenyl-pyrones REF .: 128133 of the formula wherein X means alkyl and Y means halogen or X means halogen and Y means alkyl, A means hydrogen, alkyl or aryl if substituted and D means hydrogen, alkyl, optionally substituted cycloalkyl, optionally substituted aryl or heterocyclyl if substituted, or D means a remainder of the formula where R stands for substituted phenyl, or A and D together with the carbon atoms, to which they are attached, means a substituted carbocycle, if any, or they mean a substituted heterocycle, the compounds of the formulas being excluded The compounds of the formula (I) can be present, depending on the type of the substituents, as geometrical and / or optical isomers or as mixtures of isomers, of variable composition, which can be separated, if appropriate, in a customary manner. The present invention relates both to the pure isomers as well as to the mixtures of the isomers. However, the 3-phenyl-pyrones of formula (I) will always be discussed below, in order to simplify, even when both pure isomers and, where appropriate, mixtures with various proportions in isomers are indicated.

The 3-phenyl-pyrones of the formula (I) can be represented graphically by means of the formula The dotted line indicates that these products may be present in the two tautomeric forms The 3-phenyl-pyrones according to the invention can be present in the form of mixtures of compounds of the formulas (I) and (la) or else in the form of the pure isomers. The mixtures of the compounds of the formulas (I) and (la) can be separated by physical means, for example by chromatographic methods. In order to facilitate understanding, only one of the possible isomers is indicated below. This does not exclude that the compounds can, if appropriate, be present in the form of the isomeric mixtures or in the other correspng isomeric form. It has also been found that the 3-phenyl-pyrones of the formula (I) can be obtained, if they are reacted a) either carbonyl compounds of the formula where A and D have the meanings indicated above, silyl ethers of the formula wherein A and D have the meanings given above and Alk means alkyl having 1 to 4 carbon atoms, respectively with keten-derivatives of the formula (IV) wherein X and Y have the meanings indicated above and Hal means chlorine or bromine, if appropriate in the presence of a diluent and, if appropriate, in the presence of an acid acceptor. Finally, it has been found that the 3-phenyl-pyrones according to the invention of the formula (I) have a very good pesticidal, fungicidal and herbicidal activity. Surprisingly the 3-phenyl-pyrones according to the invention of the formula (I) are more suitable as pesticides, fungicides and herbicides than the previously known active compounds, similar from the point of view of their constitution, with the same sense of activity. The 3-phenyl-pyrones according to the invention are generally defined by the formula (I). Preference is given to compounds of the formula (I), in which X means alkyl having 1 to 6 carbon atoms and And it means fluorine, chlorine or bromine, or X means fluorine, chlorine or bromine and Y means alkyl with 1 to 6 carbon atoms. Preferably, A means hydrogen, alkyl having 1 to 12 carbon atoms or phenyl, which may be substituted one to three times, in the same or different ways by halogen, by alkyl having 1 to 6 carbon atoms, by haloalkyl with 1 to 6 carbon atoms, for alkoxy with 1 to 6 carbon atoms, for halogenalkoxy with 1 to 6 carbon atoms, for cyano and / or for nitro. Preferably, D means hydrogen, alkyl having 1 to 12 carbon atoms, cycloalkyl with 3 to 8 carbon atoms, optionally substituted by halogen, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms and / or halogenalkyl with 1 to 4 carbon atoms, or means phenyl, which may be substituted one to three times, in the same or in different ways, by halogen, by alkyl with 1 to 6 carbon atoms, by halogenalkyl with 1 to 6 carbon atoms, by alkoxy with 1 to 6 carbon atoms, by haloalkoxy with 1 to 6 carbon atoms, by cyano, by nitro, by phenyl and / or by phenoxy, which may be The two residues mentioned last, on the one hand, once or twice, are replaced by halogen, by alkyl with 1 to 4 carbon atoms, by alkoxy with 1 to 4 carbon atoms, by halogenalkyl with 1 to 4 carbon atoms and / or by halogenalkoxy with 1 to 4 carbon atoms, 0 means heteroaryl with 5 or 6 members with 1 or 2 heteroatoms of the series consisting of oxygen, sulfur and nitrogen, these residues can be substituted once or twice, by halogen, by alkyl with 1 to 6 carbon atoms, for halogenalkyl with 1 to 6 carbon atoms, for alkoxy with 1 to 6 carbon atoms, for halogenalkoxy with 1 to 6 carbon atoms, for cyano and / or for nitro, or means a radical of the formula -CHj-O-C- O where R means phenyl which may be substituted one to three times, in the same or different ways by halogen, by alkyl having 1 to 6 carbon atoms, by halogenalkyl with 1 to 6 carbon atoms, by alkoxy with 1 to 6 carbon atoms, by haloalkoxy with 1 to 6 carbon atoms, by cyano and / or by nitro. Preferably, A and D also together also mean an alkanediyl group having 3 to 6 carbon atoms, alkenodiyl having 3 to 6 carbon atoms or alkanediyl with 4 to 6 carbon atoms, where a methylene group may be replaced by oxygen, respectively. or by sulfur, and which are respectively substituted, if appropriate, by halogen, by alkyl with 1 to 6 carbon atoms, by haloalkyl with 1 to 6 carbon atoms, by alkoxy with 1 to 6 carbon atoms, by halogenoalkoxy with 1 to 6 carbon atoms, or another alkanediyl group with 3 to 6 carbon atoms, alkenodiyl with 3 to 6 carbon atoms or alkanediyl with 4 to 6 carbon atoms that forms a fused ring, in which it is respectively replaced, if necessary a methylene group by oxygen or by sulfur and which are optionally substituted by alkyl with 1 to 6 carbon atoms. In the compounds of the formula (I), with particular preference, X means alkyl with 1 to 4 carbon atoms and And it means fluorine, chlorine or bromine, or X means chlorine or bromine and Y means alkyl with 1 to 4 carbon atoms. Particularly preferably, A means hydrogen, alkyl having 1 to 8 carbon atoms or means phenyl, which may be substituted one to three times, in the same or different ways by fluorine, chlorine, bromine, alkyl with 1 to 4 carbon atoms, for halogenalkyl with 1 to 4 carbon atoms, for alkoxy with 1 to 4 carbon atoms, for halogenalkoxy with 1 to 4 carbon atoms, for cyano and / or for nitro. Particularly preferably D denotes hydrogen, alkyl having 1 to 10 carbon atoms, cycloalkyl with 3 to 7 carbon atoms, optionally substituted one to three times, in the same or in different forms by fluorine, by chlorine, by alkyl with 1 to 3 carbon atoms, by alkoxy with 1 to 2 carbon atoms, by halogen alkyl with 1 to 2 carbon atoms, or means phenyl which may be substituted one to three times, in the same or different ways by fluorine, by chlorine, by bromine, by alkyl with 1 to 4 carbon atoms, by halogenalkyl with 1 to 4 carbon atoms, by alkoxy with 1 to 4 atoms of carbon, by halogenalkoxy with 1 to 4 carbon atoms, by cyano, by nitro, by phenyl and / or by phenoxy, the two latter moieties, one or two times per fluorine, may be replaced by chlorine, by bromine, by methyl, by ethyl, by methoxy, by trifluoromethyl, by trifluoromethoxy and / or by difluoromethoxy, or means furanyl, pyridyl, imidazolyl, triazolyl, pyrazolyl, pyrimidinyl, thiazolyl or thienyl, these residues can be substituted once or twice , by fluorine, by chlorine, by bromine, by alkyl with 1 to 4 carbon atoms, for halogenalkyl with 1 to 4 carbon atoms, for alkoxy with 1 to 4 carbon atoms, for halogenalkoxy with 1 to 4 carbon atoms, for cyano and / or for nitro, or for especially preferred, D means a residue of the formula -CHj-O-C-R O wherein R is particularly preferably phenyl, which may be substituted one to three times, in the same or different ways by fluorine, chlorine, bromine, alkyl with 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms, for alkoxy with 1 to 4 carbon atoms, for haloalkoxy with 1 to 4 carbon atoms, for cyano and / or for nitro. Particularly preferably A and D together represent an alkanediyl group with 3 to 5 carbon atoms or an alkenodiyl group with 3 to 5 carbon atoms, where a carbon atom may be replaced, respectively, by oxygen or by sulfur, and which are substituted, if appropriate, by fluorine, by. chlorine, by bromine, by alkyl having 1 to 4 carbon atoms, by alkoxy with 1 to 4 carbon atoms, by halogenalkyl with 1 to 4 carbon atoms and / or by halogenalkoxy with 1 to 6 carbon atoms, or by another C 4 -dienediienyl group forming a fused ring, which may be substituted by C 1 -C 4 -alkyl. In the compounds of the formula (I), very particularly preferably, X means methyl or ethyl and Y means fluorine, or chlorine X means chlorine or bromine and Y means methyl or ethyl. Very particularly preferably, A means hydrogen, alkyl having 1 to 6 carbon atoms or means phenyl, which may be substituted once or twice, in the same or in different ways by fluorine, by chlorine, by methyl, by ethyl, by n-propyl, by iso-propyl, by trifluoromethyl, by methoxy, by ethoxy, by trifluoromethoxy, by cyano and / or by nitro. Very particularly preferably, D means hydrogen, alkyl having 1 to 8 carbon atoms, or cycloalkyl with 3 to 7 carbon atoms, optionally substituted once or twice, in the same or different way by fluorine, by chlorine , by methyl, by ethyl, by methoxy, by ethoxy and / or by trifluoromethyl, or by phenyl, which may be substituted once or twice, in the same or in different ways by fluorine, by chlorine, by bromine, by methyl, by ethyl, by n-propyl, by isopropyl, by n-butyl, by sec. -butyl, by iso-butyl, by tere. -butyl, by trifluoromethyl, by methoxy by ethoxy, by trifluoromethoxy, by cyano, by nitro, by phenyl and / or by phenoxy, the two latter moieties may be substituted, on the one hand, once or twice, by fluorine by chlorine, by methyl, by methoxy, by trifluoromethyl and / or by trifluoromethoxy, or means furanyl, pyridyl or thienyl, these residues may be substituted once or twice by fluorine, by chlorine, by bromine, by methoxy, by ethyl, by n-propyl, by iso-propyl, by trifluoromethyl, by trifluoromethoxy, by cyano and / or by nitro, or very particularly preferably, D means a radical of the formula -CH ^ -O-C-RO in which R is particularly preferably phenyl, which may be substituted once or twice, in the same or in different ways by fluorine, by chlorine, by methyl, by ethyl, by trifluoromethyl, by methoxy, by trifluoromethoxy, by cyano and / or by nitro. Very particularly preferably, A and D together also mean an alkanediyl group having 3 to 5 carbon atoms or an alkenodiyl group having 3 to 5 carbon atoms, where a methylene group is replaced, respectively, by oxygen or, respectively, by sulfur and which is optionally substituted one to four times, in the same or different ways by fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, per sec. -butyl, by tere. -butyl, by methoxy, by trifluoromethyl and / or by trifluoromethoxy, or by another butadyendiyl group, which forms a fused ring, which may be substituted once or twice, by methyl. The definitions of the remains or the explanations given above in a general manner or in the preferred ranges can be combined arbitrarily with each other, that is to say even between the respective ranges and the preferred ranges. These are valid for the final products as well as for the starting products and for the corresponding intermediate products. In addition, individual definitions can also be imagined. As already indicated above, the compounds of the formulas are excluded from the 3-phenyl-pyrones according to the invention, respectively In particular, in addition to the 3-phenyl-pyrones indicated in the preparation examples, the products of the following formula (I).

Tibia 1, X = Br: Y = CH3 Table 1 (Continued).

Table 1 (Continuation).

Table 2 X = CH3; Y-Cl Table 2 (Continuation).

Table 3 X-Cl; Y = CH3 Table 3 (Continued).

If (chlorocarbonyl) -2- (2-methyl-4-chloro-phenyl) -ketene and ethyl- (pyrid-2-yl) -ketone are used as starting substances, the development of the process according to the invention (variant) may be illustrated. a) by means of the following formulas scheme: If (chlorocarbonyl) -2- (2-methyl-4-chloro-phenyl) -ketene and 1- (pyrid-2-yl) -1-trimethyl-silyloxy-prop-1-ene are used as starting substances, you can The development of the process according to the invention (variant β) is represented by means of the following formula scheme: The carbonyl compounds, which are necessary as starting materials in carrying out the process according to the invention according to variant a, are generally defined by means of formula (II). In this formula, A and D preferably have those meanings which have already been mentioned for these residues preferably in relation to the description of the 3-phenyl-pyrones of the formula (I) according to the invention. The carbonyl compounds of the formula (II) are known and / or can be prepared by processes known per se. The silyl ethers, which are necessary as starting materials, in carrying out the process according to the invention according to the variant β, are generally defined by means of formula (III). In this formula, A and D preferably have those meanings which have already been mentioned for these residues preferably in relation to the description of the 3-phenyl-pyrones of the formula (I) according to the invention. Preferably Alk means methyl or ethyl, especially preferably methyl. The silyl ethers of the formula (III) are known or can be prepared by processes known per se.

The cetene derivatives which are necessary as components of the reaction in carrying out the process according to the invention are generally defined by means of formula (IV). In this formula, X and Y preferably have those meanings which have already been mentioned for these residues preferably in relation to the description of the 3-phenyl-pyrones according to the invention of the formula (I). Also preferably Hal means chlorine or bromine. The keten-derivatives of the formula (IV) are known or can be prepared according to processes known per se (see Org. Prep. Int.Ex. Procedure 1, 155-15.8 (1975) and DE-A 1 945 703). In this way, the keten-derivatives of the formula (IV) are obtained if substituted phenylmalonic acids of the formula are reacted wherein X and Y have the meanings given above, with acyl halides, such as, for example, thionyl chloride, phosphorus chloride (V), phosphorus chloride (III), oxalyl chloride, phosgene or thionyl bromide optionally in the presence of catalysts, such as, for example, diethylformamide, methyl steryl formamide or triphenylphosphine and, if appropriate, in the presence of bases, such as, for example, pyridine or triethylamine, at a temperature between - 20 ° C and + 200 ° C, preferably between 0 ° C and 150 ° C. The substituted phenylmalonic acids of the formula (V) are known or can be prepared by processes known per se (see for example Organikum, VEB Deutscher Verlag der issenschaften, Berlin 1977, pages 517 et seq.). In this way, the substituted phenylmalonic acids of the formula (V) are obtained if substituted phenylmalonic acid esters of the formula are reacted wherein X and Y have the above indicated meanings and R1 means alkyl with 1 to 4 carbon atoms, with alkali metal hydroxides, such as sodium hydroxide or potassium hydroxide, in the presence of a diluent, such as water, at temperatures between 0 ° C and 30 ° C. In the formula (VI), X and Y preferably have those meanings which have already been mentioned for these radicals as preferred in relation to the description of the 3-phenyl-pyrones of the formula (I) according to the invention. Preferably R1 means methyl or ethyl. The substituted esters of phenylmalonic acid of the formula (VI) are known or can be prepared by processes known per se (see Tetrahedron Letters, 27_, 2763 (1986) and Organikum, VEB Deutscher Verlag der Wissenschaften, Berlin 1977, pages 587 et seq.) . Suitable diluents in carrying out the process according to the invention according to variant a and ß are all inert organic solvents with respect to the reaction partners. Preferably hydrocarbons such as o-dichlorobenzene, tetralin, toluene and xylene can be used, in addition ethers, such as dibutyl ether, glycol dimethyl ether and diglycoldimethyl ether, in addition polar solvents, such as dimethyl sulfoxide, sulfolane, dimethylformamide or N-methylpyrrolidone. Suitable acid acceptors in carrying out the process according to the invention according to variants a and ß are all customary acid acceptors. Preference may be given to tertiary amines, such as triethylamine, pyridine, diazabicyclooctane (DABCO), diazabicycloundecene (DBU), diazabicyclononene (DBN), Hunig's bases or N, N-dimethyl-aniline. The reaction temperatures in carrying out the process according to the invention according to variants a and ß can vary within wide limits. It is expedient to work at temperatures between 0 ° C and 250 ° C, preferably between 50 ° C and 220 ° C. In carrying out the process according to the invention according to variants a and ß, preference is given to working under atmospheric pressure.

In carrying out the process according to the invention, 1 equimolar carbonyl compound of the formula (I) or 1 mol of silyl ether of the formula (III) is generally an equimolar amount of the keten derivative of the formula (IV) and, if appropriate, also an equimolar amount of acid acceptor. However, it is also possible to use one or other of the components in a larger excess (up to 5 moles). The 3-phenyl-pyrones of the formula (I), according to the invention, have a very good pesticidal activity and have a very good compatibility with the crop plants. The active products are suitable for the fight against animal pests, preferably against arthropods and nematodes, especially insects and arachnids, which occur in agriculture, in forestry, for the protection of stored products and materials as well as in the field of hygiene. They are active against normally sensitive and resistant species as well as against all or some of the stages of development. The aforementioned pests include: From the order of the isopods, for example, Oniscus asellus, Armadillidium vulgare, Porcellio scaber. From the order of the diplópodos, for example, Blaniulus guttulatus. From the order of the chilopoda, for example, Geophilus carpophagus, Scutigera spec .. From the order of the syphilis, for example, Scutigerella immaculata. From the order of the tisane, for example, Lepisma saccharina. From the order of springtails, for example, Onychiurus armatus. From the order of the Orthoptera, for example, Blatta orientalis, Periplaneta americana, Leucophaea maderae, Germanic Blattella, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria. From the order of dermápteros, for example, Forfícula auricularia. From the order of the Isoptera, for example, Reticulitermes spp. From the order of the anopplura, for example, Phylloxera vastatrix, Pemphigus spp., Pediculus humanus corporis, Haematopinus spp., Linognathus spp. From the order of the malophagus, for example, Trichodectes spp., Damalinea spp. From the order of Thysanoptera, for example, Frankliniella occidentalis, Hercinothrips femoralis, Thrips palmi, Thrips tabaci. Of the order of the heteroptera, for example, Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex Lectularius, Rhodnius prolixus, Triatoma spp. From the order of Homoptera, for example, Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Doralis po i, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens; Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp. From the order of the lepidoptera, for example, Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella aculipennis, 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., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp. Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanimous, Tortrix viridana. From the order of coleoptera, for example, Anobium punctatum, Rhizopertha dominica, Acanthoscelides obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus 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., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica. From the order of Hymenoptera, for example, Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis and Vespa spp. From the order of the dipterans, for example, Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp. , Hyppobosca spp., Liriomyza spp. Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitana, Dacus oleae and Typula paludosa. From the order of the siphonoptera, for example, Xenopsylla cheopis, Ceratophyllus spp. From the order of arachnids, for example Scorpio maurus, Latrodectus mactans From the order of mites, for example Acarus siró, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp. The active products are characterized by high insecticidal and acaricidal activity after use in the leaves and in the field. They can be used with an especially good success in the fight against insects harmful to plants, such as, for example, against larvae of the horseradish leaf beetle (Phaedon cochleariae), against the larvae of the green rice cicada (Nephotettix cinticeps). ) and against the larvae of the green leaf louse of the peach tree (Myzus persicae). The active compounds according to the invention also have a herbicidal activity and can be used as defoliants, desiccants, agents for removing broad-leaved plants and, especially, for destroying weeds. By weeds, in the broadest sense, we must understand the plants that grow in places where they are unwanted. The fact that the substances according to the invention act as total or selective herbicides depends essentially on the amount used. The doses necessary for combating weeds of the active compounds according to the invention are between 0.001 and 10 kg / ha, preferably between 0.005 and 5 kg / ha. The active compounds according to the invention can be used, for example, in the following plants: Dicotyledonous weeds of the following types: Sinapis Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium , Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotola, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum. Dicotyledonous crops of the classes: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisu, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita. Bad monocotyledonous herbs of the following kinds: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Oats, Cyperus, Sorghum, Agropyron, Cycnodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum , Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera. Cultures of monocotyledonous classes: Oryza, Zea, Triticum, Hordeum, Avena, Sécale, Sorghum, Panicum, Saccharum, Ananas, Asparagus, Allium. The use of the active compounds according to the invention is not, however, limited in any way to these classes, but it extends in the same way also on other plants. The compounds are suitable, depending on the concentration, to completely combat the weeds, for example, in industrial and road installations and in roads and squares, with and without tree growth. Likewise, the compounds can be used to control weeds in permanent crops, for example, in forest installations, ornamental trees, fruit trees, vineyards, citrus trees, walnut trees, bananas, coffee, tea, gum tree, oil palms, cocoa, berries and hops, on ornamental and sports paths and surfaces for meadows and to selectively control weeds in mono-annual crops. Furthermore, the 3-phenyl-pyrones of the formula (1) / according to the invention have a potent fungicidal effect and can be used to combat unwanted fungal microorganisms in the protection of plants and in the protection of materials. Fungicides can be used to protect plants against plamodioforomycetes, oomycetes, chytridiomycetes, zygomycetes, ascomycetes, basidiomycetes and deuteromycetes. Some pathogens of fungal and bacterial diseases that fall within the general definitions listed above may be cited by way of example, but without any limiting character: types of xanthomonas, such as, for example, Xanthomonas campestris pv. oryzae; pseudomonas types, such as, for example, Pseudomonas syringae pv. lachrymans; types of erwinia, such as for example Erwinia amylovora; types of pitium, such as, for example, Pythium ultimum; phytophthora types, such as for example Phytophthora infestans; types of pseudoperonospora, such as for example Pseudoperonospora humuli or Pseudoperonospora cubensis; types of plasmopara, such as for example Plasmopara viticola; types of bremia, such as for example Bremia lactucae; types of peronospora, such as for example Peronospora pisi or P. brassicae; types of erisife, such as for example Erysiphe graminis; types of esfaeroteca, such as for example Spaherotheca fuliginea; types of podosfaera, such as for example Podosphaera leucotricha; types of venturia, such as, for example, Venturia inaequalis; Pyrenophora species, such as, for example, Pyrenophora teres or P. gramínea; (form of conidia: Drechslera, synonym: Helminthosporium); types of cocliobolus, such as for example Cochliobolus sativus (form of conidia: Drechslera, synonym: Helminthosporium); types of uro ices, such as for example Uromyces appendiculatus; types of pucinia, such as for example Puccinia recondita; types of sclerotinia, such as for example Sclerotinia sclerotiorum; types of tilletia, such as for example Tilletia caries; types of ustylago, such as, for example, Ustilago nuda or Ustilago avenae; types of pelicularia, such as, for example, Pellicularia sasakii; types of blasting, such as for example Pyricularia oryzae; fusarium types, such as, for example, Fusarium culmorum; Botrytis types, such as, for example, Botrytis cinerea; Septoria types, such as, for example, Septoria nodorum; types of leptosphaeria, such as for example Leptosphaeria nodorum; types of cercospora, such as for example Cercospora canescens; alternating types, such as, for example, Alternarla brassicae; types of pseudocercosporela, such as, for example, Pseudocercosporella herpotrichoides. The good compatibility with plants and active products at the concentrations necessary for the fight against plant diseases allows a treatment of the aerial parts of the plants, of seedlings and seeds and of the soil. In this case, the active compounds according to the invention can be used with particularly good success in combating diseases in vineyard, fruit and vegetable plantations, such as, for example, against Plasmopara. These also have a good effect against Pyricularia oryzae in rice and have a broad fungicidal effect both in vitro and in vivo. The active ingredients can be converted into the customary formulations, such as solutions, emulsions, sprayable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic materials impregnated with the active compound , as well as micro-encapsulations in polymer materials. These formulations are prepared in a known manner, for example by mixing the active ingredients with spreading materials, that is, with liquid solvents and / or liquefied gases or solid diluents, optionally employing surfactants, that is, emulsifiers and / or dispersants and / or foam generating means. In the case of using water as a filler, it is also possible, for example, to use organic solvents as auxiliary solvents. Particularly preferred liquid solvents are aromatic hydrocarbons, such as xylene, toluene or alkyl naphthalenes, chlorinated aromatic hydrocarbons and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example crude oil fractions, alcohols such as butanol or glycol, as well as their esters and ethers, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethylsulfoxide as well as water. Suitable solid excipients are: for example, ammonium salts and natural mineral flours, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and molten synthetic minerals, such as highly dispersed silicic acid, aluminum oxide and silicates, as solid excipients for granulates can be used natural broken and fractionated minerals such as calcite, marble, pumice, sepiolite, dolomite, as well as synthetic granules of inorganic and organic flours, as well as granulates of organic materials, such as sawdust, coconut husk shells, corn ears and tobacco stems; as emulsifiers and / or foam generators, nonionic and anionic emulsifiers, such as polyoxyethylenated fatty acid esters, polyoxyethylenated fatty alcohol ethers, for example, alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulphonates, as well as hydrolysis products can be used of albumin; Suitable dispersants are, for example, lignin sulfite residual liquors and methylcellulose. Adhesives such as carboxymethylcellulose, natural and synthetic polymers powdery, granulated or in the form of latex, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids, such as cephalin and lecithin and synthetic phospholipids can be used in the formulations. Other additives can be mineral and vegetable oils. Dyes, such as inorganic pigments, for example, iron oxide, titanium oxide, Prussian blue and organic dyes, such as alizarin dyes, metallic azo and phthalocyanine dyes and trace nutrients, such as iron salts, can be employed. manganese, boron, copper, cobalt, molybdenum and zinc. The formulations generally contain between 0.1 to 95% by weight of active compound, preferably between 0.5 and 90% by weight and furthermore, preferably, extenders and / or surfactants. The active compounds according to the invention can be present in their commercially available formulations as well as in the application forms prepared from these formulations, in admixture with other active ingredients, such as insecticides, bait products, sterilants, acaricides, nematicides, fungicides, growth regulators or herbicides. Insecticides include, for example, esters of phosphoric acid, carbamates, esters of carbonic acid, chlorinated hydrocarbons, phenylureas, products produced by means of micro-organisms, etc. Especially suitable mixing components are, for example, the following products: Fungicides: 2-Aminobutane; 2-anilino4-methyl-1-6-cyclopropyl-pyrimidine; 2 ', 6' -dibromo-2-methyl-4 '-trifluoromethoxy-4'-trifluoromethyl-1,3-thiazole-5-carboxanilide; 2,6-dichloro-N- (4-trifluoromethylbenzyl) benzamide; (E) -2-methoxyimino-N-methyl-2- (2-phenoxyphenyl) -acetamide; 8-hydroxyquinolinesulfate: methyl- (E) -2-. { 2- [6- (2-Cyanophenoxy) -pyrimidin-4-yloxy] phenyl} -3-methoxyacrylate; methyl- (E) -methoxyimino- [alpha- (o-tolyloxy) -o-tolyl] acetate; 2-Phenylphenol (OPP), Aldimorph, Ampropylfos, Anilazin, Azaconazole, Benalaxyl, Benodanil, Benomyl, Binapacryl, Biphenyl, Bitertanol, Blasticidin-S, Bromuconazole, Bupirimate, Buthiobate, Calcium Polysulfide, Captafol, Captan, Carbendazim, Carboxin, Chinomethionat (Quinomethionat), Chloroneb, Chloropicrin, Chlorothalonil, Chlozolinat, Cufraneb, Cymoxanil, Cyproconazole, Cyprofuram, Dichlorophen, Diclobutrazol, Diclofluanid, Diclomezin, Dicloran, Diethofencarb, Difenoconazole, Dimethirimol, Dimethomorph, Diniconazole, Dinocap, Diphenylamin, Dipyrithion, Ditalimfos, Dithianon, Dodin, Drazoxolon, Edifenphos, Epoxyconazole, Ethirimol, Etridiazol, Fenarimol, Fenbuconazole, Fenfuram, Fenitropan, Fenpiclonil, Fenpropidin, Fenpropimorph Fentinacetate, Fentinhydroxyd, Ferbam, Ferimzone, Fluazinam, Fludioxonil, Fluoromide, Fluquinconazole, Flusilazole, Flusulfamide, Flutolanil, Flutriafol, Folpet, Fosetyl-Aluminum, Fthalide, Fuberidazole, Furalaxil, Furmecyclox. Guazatine, Hexachlorobenzene, Hexaconazole, Hymexazole, Imazalil, Imibenconazole, Iminoctadin, Iprobenfos (IBP), Iprodion, lsoprothiolan, Kasugamycin, copper compositions, such as; copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, copper oxine and Bordeaux mixture, Mancopper, Mancozeb, Maneb Mepanipyrim, Mepronil, Metalaxyl, Metconazole, Methasulfocarb, Methfuroxam, Metiram, Metsulfovax, Myclobutanil, Nickel Dimethyldithiocarbamate, Nitrothal-isopropyl, Nuarimol, Ofurace, Oxadixyl, Oxamocarb, Oxycarboxin, Perfurazoat, Penconazole, Pencycuron, Phosdiphen, Phthalid, Pimaricin, Piperalin, Polycarbamate, Polyoxin, Probenazole, Prochloraz, Procymidon, Propamocarb, Propiconazole, Propineb, Pyrazophos, Pyrifenox, Pyrimethanil, Pyroquilon, Quintozen (PCNB), Sulfur and sulfur compositions, Tebuconazole, Tecloftalam, Tecnazen, Tetraconazole, Thiabendazole, Thicyofen, Thiophanat-methyl, Thira, Tolclophos-methyl, Tolylfluanid, Triadimefon, Triadimenol, Triazoxid, Trichlamid, Tricyclazole, Tridemorph, Triflumizol, Triforin, Tritononazole, Validamycin A, Vinclozolin, Zineb, Ziram. Bactericides: Bronopol, Dichlorophen, Nitrapyrin, nickel dimethyldithiocarbamate, Kasugamycin, Octhilinon, furanocarboxylic acid, Oxytetracyclin, Probenazol, Streptomycin, Tecloftalam, copper sulfate and other copper preparations. Insecticides / Acaricides / Nematicides: Abamectin, AC 303 630, Acephat, Acrinathrin, Alanycarb, Aldicarb, Alphamethrin, Amitraz, Avermectin, AZ 60541, Azadirachtin, Azinphos A, Azinphos M, Azocyclotin, Bacillus thuringiensis, Bendiocarb, Benfuracarb, Bensultap, Betacyfluthrin, Bifenthrin, BPMC, Brofenprox, Bromophos A, Bufencarb, Buprofezin, Butocarboxin, Butylpiridaben, Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, CGA 157 419, CGA 184699, Chloethocarb, Chlorethoxyphos, Chlorfenvinphos, Chlorfluazuron, Chlormephos, Chlorpyri fos, Chlorpyrifos M, Cis-Resmethrin, Clocythrin, Clofentezin, Cyanophos, Cycloprothrin, Cyfluthrin, Cyhalothrin, Cyhexatin, Cypermethrin, Cyromazin, Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Diazinon, Dichlofenthion, Dichlorvos, Dicliphos, Dicrotophos, Diethion, Diflubenzuron, Dimethoat, Dymethylvinphos, Dioxathioin, Disulfoton, Edifenphos, Emamectin, Esfenvalerat, Ethiophencarb, Ethion, Ethofenprox, Ethoprophos Etrimphos, Fenamiphos, Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroxymat, Fenthion, Fenvalerate, Fipronil, Fluazinam, Flucycloxuron, Flucythrinat, Flufenoxuron, Flufenprox, Fluvalinate, Fonophos, Formothion, Fosthiazat, Fubfenprox, Furathiocarb, HCH, Heptenophos, Hexaflumuron, Hexythiazox, Imidacloprid, Iprobenfos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivermectin, Lamda-cyhalothrin, Lufenuron, Malathion, Mecarbam, Mevinphos, Mesulfenphos, Metaldehyd, Methacrifos, Methamidophos, Methidathion, Methiocarb, Methomyl, Metolcarb, Milbemectin, Monocrotophos, Moxidectin. Naled, NC 184, NI 25, Nitenpyram Omethoat, Oxamyl, Oxydemethon M, Oxydeprofos, Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos M, Pirimiphos A, Profenofos, Promecarb, Propaphos, Propoxur, Prothiophos, Prothoat, Pymetrozin, Pyrachlophos, Pyridaphenthion, Pyresmethrin, Pyrethrum, Pyridaben, Pyrimidifen, Pyriproxifen, Quinalphos, RH 5992, Salithion, Sebufos, Silafluofen, Sulfotep, Sulprofos, Tebufenozid, Tebufenpyrad, Tebupirimphos, Teflubenzuron, Tefluthrin, Temephos Terbam, Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thiofanox, Thiomethon, Thionazin, Thuringienin, Tralomethrin, Triarathen, Triazophos, Triazu.ron, Tric lorphin, Triflumuron, Trimethacarb, Vamidothion, XMC, Xylylcarb, YI 5301/5302, Zeta ethrin. Herbicides: for example, anuidas, such as Diflufenican and Propanil; arylcarboxylic acids, such as dichloropicolinic acid, Dicamba and Picloram; aryloxyalkanoic acids, such as, for example, 2,4-D, 2,4-DB, 2,4-DP, Fluroxypyr, MCPA, MCPP and Triclopyr; esters of the aryloxyphenoxyalkane acids, such as Diclofop-methyl, Fenoxaprop-ethyl, Fluazifopbutyl, Haloxyfop-methyl and Quizalofop-ethyl; azinones, such as for example Chloridazon and Norflurazon; carbamates, such as for example Chlorpropham, Desmedipham, Phenmedipham and Propham; chloroacetanilides, such as for example Alachlor, Acetochlor, Butachlor, Metazachlor, Metolachlor, Pretilachlor and Propachlor; dinitroanilines, such as for example Oryzalin, Pendimethalin and Trifluralin; diphenylethers, such as for example Acifluorfen, Bifenox, Fluoroglycofen, Fomesafen, Halosafen, Lactofen and Oxyfluorfen; ureas, such as for example Chlortoluron, Diuron, Fluometuron, Isoproturon, Linuron and Methabenzothiazuron; hydroxylamines, such as for example Alloxydim, Cletodim, Cycloxydim, Sethoxydim and Tralkoxydim; imidazolinones, such as, for example, Imazethapyr, Imazemethabenz, Imazapyr and Imazaquin; nitriles, such as for example Bromoxynil, Dichlobenil and Ioxynil; Oxyacetamides, such as for example Mefenacet; sulfonylureas, such as for example Amidosulfuron, Bensul furon-methyl, Chlorimuron-ethyl, Chlorsulfuron, Cinosulfuron, Metsulfuron-methyl, Nicosulfuron, Primisulfuron, Pyrazosulfuron-ethyl, Thifensulfuron-methyl, Triasulfuron and Tribenuron-methyl; thiolcarbamates, such as for example Butylate, Cycloate, Diallate, EPTC, Esprocarb, Molinate, Prosulfocarb, Thiobencarb and Triallate; triazines such as, for example, Atrazin, Cyanazin, Simazin, Simetryna, Terbutryne and Terbutylazin; triazinones, such as, for example, Hexazinon, Metamitron and Metribuzin; others, such as for example Aminotriazole, Benfuresate, Bentazone, Cinmethilin, Clomazone, Clopyralid, Difenzoquat, Dithiopyr, Ethofumesate, Fluorchloridone, Glufosinate, Gliphosate, Isoxaben, Pyridate, Quinchlorac, Quinmerac, Sulphosate and Tridiphane. The active compounds according to the invention can be present in their commercially available formulations as well as in the application forms prepared from these formulations in a mixture with synergists. The synergists are the compounds through which the effect of the active products is increased without the added synergist having to be active in itself. The active substance content of the application forms prepared from the commercially available formulations can vary within wide limits the concentration of active compound of the application forms can be between 0.0000001 to 95% by weight of active compound, preferably between 0.0001 and 1% by weight. The application is carried out in a manner adapted to the forms of application. In the use against hygiene pests and stored products, active products are characterized by an excellent residual effect on wood and clay as well as good stability to alkalis on limed substrates. The active compounds according to the invention are not only active against plant pests, hygiene and stored products, but also in the field of veterinary medicine against animal parasites. (ectoparasites) such as hard ticks, soft ticks, scabies mites, migratory mites, flies (suckers and mincers), fly parasitic larvae, lice, hair nits, feathered nits and fleas. These parasites belong to: From the order of anopplides, for example Haematopinus spp., Linognathus spp., Pediculus, spp., Pthirus spp., Solenopotes spp.

From the order of the malofagids and the suborders to bicerine as well as to the isquirdine, for example, Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp. ., Felicola spp.

From the order of the dipterans and the nematocerine suborders as well as brachycerins, for example, Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzo yia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp. ., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp. and Melophagus spp. From the order of the siphonapterids, for example Pulex spp., Ctenocephalides spp., Xenospsylla spp. and Ceratophyllus spp. From the order of heteropterids, for example Ci ex spp., Triatoma spp., Rhodnius spp. and Panstrongylus spp.

From the order of the blataridos, for example Blatta orientalis, American periplaneta, Blattela germanica, and Supella spp. From the subclass of mites (Acarida) and the order of the meta- as well as mesostigmat, for example Argas spp., Ornithodorus spp., Otabius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemaphysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp. and Varroa spp. From the order of actinedides (Prostigmata) and acaridids (Astigmata), for example Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp. ., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Octodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp. and Laminosioptes spp. The active compounds according to the invention of the formula (I) are also suitable for the control of arthropods, which attack animals useful in agriculture, such as, for example, cows, lambs, goats, horses, pigs, donkeys, camels. , buffaloes, rabbits, chickens, turkeys, ducks, geese, bees, other domestic animals such as, for example, dogs, cats, game birds, aquarium fish as well as so-called test animals such as, for example, hamsters, guinea pigs, rats and mice. By fighting against these arthropods death cases and yield reductions (in the case of meat, milk, wool, skins, eggs, honey, etc.) are avoided so that, by using the active products according to the invention, possible a more economical and simple maintenance of the animals. The application of the active compounds according to the invention is carried out in the veterinary field in a known manner by enteral administration in the form of, for example, tablets, capsules, beverages, dragees, granules, pastes, bolis, by means of the process through the food "feed-through" of suppositories, by parenteral administration, such as for example by injection (intramuscular, subcutaneous, intravenous, intraperitoneal etc), implants, by nasal application, by dermal application in the form of eg immersion or bath (Dippen), spray (Spray), surface watering (Pour-on and Spot-on), washing, dusting as well as with the help of molded bodies containing the active product such as collars, markings for the ears, marks for the tail, bands for the extremities, halters, marking devices, etc. When they are used for domestic livestock, birds, pets, etc. the active compounds (I) can be used as formulations (for example powders, emulsions, agents capable of spreading), containing the active compounds in amounts of 1 to 80% by weight, directly or after dilution of 100 to 10,000, or they can be used as a chemical bath. Furthermore, it has been found that the compounds according to the invention of the formula (I) show a high insecticidal effect against insects, which destroy industrial materials. By way of example and preference - however without limitation - the following insects may be mentioned: Beetles, such as Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobius ollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthes rugicollis; Xyleborus spec., Tryptodendron spec., Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec., Dinoderus minutus. Hymenoptera, such as Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur. Termites, such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicala, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zooter opsis nevadensis, Coptoter is formosanus. Thysanides, such as Lepisma saccarina. By industrial materials, non-living materials will be understood in the present context, such as, preferably, synthetic materials, glues, glues, paper and cardboard, leather, wood and wood processing products and paints.

In a very special way, the materials to be protected against attack by insects are made of wood and wood products. For wood and wood processing products, which can be protected by means of the agents according to the invention or of the mixtures containing them, it should be understood, for example: construction wood, wooden beams, railway sleepers, parts for bridges, boat ribs, wooden vehicles, boxes, pallets, containers, telephone poles, wooden coverings, wooden windows and doors, wooden plywood, plywood boards, carpentry works or wood products, which find application, in a very general way, at home or in the construction industry. The active compounds can be used as such, in the form of concentrates or customary formulations in general, such as powders, granules, solutions, suspensions, emulsions or pastes. Said formulations can be prepared in a manner known per se, for example by mixing the active ingredients with at least one solvent or diluent, emulsifier, dispersants and / or binder or binding agent, water repellent, if appropriate drying agents and stabilizers against UV and, if necessary, dyes and pigments as well as other processing aids. The insecticidal agents or concentrates to be used for the protection of wood and wood materials contain the active compound according to the invention in a concentration of 0.0001 to 95% by weight, especially 0.001 to 60% by weight. The amounts of the agents or concentrates used depend on the type and origin of the insects and the environment. The optimum application quantities can be determined respectively by means of series of tests prior to the application. In general, however, it is sufficient to employ from 0.0001 to 20% by weight, preferably from 0.001 to 10% by weight of the active product, based on the material to be protected. As the solvent and / or diluent, a solvent or a mixture of organochemical solvents and / or a solvent or mixture of organo-chemical, oleaginous or oil-soluble solvents, which are difficult to volate and / or a solvent or mixture of organic solvents, is used. polar chemicals and / or water and, if appropriate, an emulsifier and / or humectant. The organochemical solvents used are preferably oleaginous or oleaginous solvents, with an evaporation value above 35 and a flame point above 30 ° C, preferably above 45 ° C. By way of such water-insoluble, oil-soluble or oleaginous-type solvents which are difficult to volatile, corresponding mineral oils or their aromatic fractions or mixtures of solvents containing mineral oils, preferably benzine for tests, petroleum and / or alkylbenzene, are used. Advantageously, mineral oils with a boiling range of 170 to 220 ° C, benzene for tests with a boiling range of 170 to 220 ° C, spindle oil with a boiling range of 250 to 350 ° C, petroleum or aromatic hydrocarbons with a boiling range of 160 to 280 ° C, terpene oil and the like. In a preferred embodiment, liquid aliphatic hydrocarbons having a boiling range of 180 to 210 ° C or a high-boiling mixture of aromatic and aliphatic hydrocarbons having a boiling range of 180 to 220 ° C and / or oil for boiling are used. spindles and / or monochloronaphthalene, preferably a-monochloronaphtal ina. The organic solvents, hardly volatile, oleaginous or of oleaginous type, with an index of evaporation located above 35 and with a point of flame located above 30 ° C. preferably above 45 ° C, they can be partially replaced by light organic or medium volatility solvents, with the proviso that the solvent mixture has an evaporation index above 35 and a flame point above 30 ° C, preferably above 45 ° C, and that the insecticide-fungicide mixture is soluble or emulsifiable in this mixture of solvents. According to a preferred embodiment, a part of the solvent or mixture of organochemical solvents or a solvent or mixture of polar aliphatic organochemical solvents will be substituted. Preference is given to using aliphatic organochemical solvents containing hydroxyl and / or ester and / or ether groups, such as, for example, glycol ether, esters or the like. As organic-chemical binders, synthetic resins and / or setting drying oils, known per se, dilutable with water and / or soluble or dispersible or emulsifiable in the organic-chemical solvents used, will be used within the scope of the present invention. especially binders consisting of or containing acrylic resin, a vinyl resin, for example polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indeno-coumaron resin, silicone resin, vegetable drying and / or drying oils and / or physical drying binders based on a natural and / or synthetic resin. The synthetic resin used as a binder can be used in the form of an emulsion, dispersion or solution. Bitumen or bituminous substances up to 10% by weight can also be used as binders. In a complementary manner, dyes, pigments, water-repelling agents, odor correctors and inhibitors or anticorrosive agents known per se and the like can be used. It is preferred to use at least one alkyd resin or a modified alkyd resin and / or a drying vegetable oil in the medium or concentrate according to the invention as an organochemical binder. Preferably, alkyd resins having an oil content of greater than 45% by weight, preferably from 50 to 68% by weight, are preferably used according to the invention. The aforementioned binder can be partially or completely replaced by a fixing agent (mixture) or by a plasticizer (mixture). These additives should avoid volatilization of active products as well as crystallization or precipitation. They preferably replace 0.01 to 30% of the binder (based on 100% of the binder used). The plasticizers are of the chemical class of phthalic acid esters such as dibutyl, dioctyl or benzylbutyl phthalate, phosphoric acid esters, such as tributyl phosphate, esters of adipic acid, such as di- (D-adipate). 2-ethylhexyl), stearates such as butyl stearate or amyl stearate, oleates such as butyl oleate, glycerin ethers or high molecular weight glycol ethers, glycerin esters as well as esters of p-toluenesulfonic acid. Fixative agents are chemically based on polyvinylalkyl ethers such as polyvinyl methyl ether or ketones such as benzophenone, ethylenebenzophenone. Suitable as solvent or diluent is water, optionally mixed with one or more of the aforementioned solvents or diluents, emulsifiers and organochemical dispersants. Especially effective protection of the wood is achieved by impregnation processes on an industrial scale, for example vacuum, double vacuum or pressure processes. The ready-for-application agents may optionally contain other insecticides and, if appropriate, one or more additional fungicides. The insecticides and fungicides mentioned in WO 94/29 268 are preferably used as additional components of the mixture. The compounds mentioned in this document constitute, expressly, integral part of the present application. Insecticides, such as Chlorpyriphos, Phoxim, Silafluofin, Alphamethrin, Cyfluthrin, Cypermethrin, Deltamethrin, Permethrin, Imidacloprid, NI-25, Flufenoxuron, Hexaflumuron and Triflumuron, as well as fungicides such as Epoxiconazole, Hexaconazole, are considered as particularly preferred mixing components. , Azaconazole, Propiconazole, Tebuconazole, Cyproconazole, Metconazole, Imazalil, Dichlorfluanid, Tolylifluanid, 3-iodo-2-propynyl-butylcarbamate, N-octyl-isothiazolin-3-one and 4,5-dichloro-N-octylisothiazolin-3-one. The preparation and use of the active compounds according to the invention is apparent from the following examples.

Preparation examples Example 1.

To a mixture consisting of 4.6 g (20 mmol) of (chlorocarbonyl) -2- (2-methyl-4-chloro-phenyl) -ethenes and 40 ml of anhydrous toluene, at room temperature, under stirring, 2.7 g are added. (20 mmol) of ethyl- (pyrid-2-yl) -ketone. The reaction mixture is heated to reflux for 8 hours. After cooling to room temperature, the formed precipitate is filtered off and washed twice with cyclohexane. This gives 3.4 g (51% of theory) of 3- (2-methyl-4-chloro-phenyl) -4-hydroxy-5-methyl-6- (pyrid-2-yl) -pyrone in the form of a solid substance with a melting point of 133-135 ° C. According to the methods indicated above, the 3-phenyl-pyrones of the formula (I) indicated in Table 4 below are prepared.

Table 4 *) The atom marked with (*) is linked respectively to the position of substituent A.

Application examples: Example A Test with Myzus. Solvent: 7 parts by weight of dimethylformamide. Emulsifier: 1 Part by weight of alkylaryl polyglycol ether. To obtain a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amount of solvent and with the indicated amount of emulsifier and the concentrate is diluted with water to the desired concentration. Cabbage leaves (Brassica oleracea), which are strongly attacked by the louse of the peach leaf (Myzus persicae), are treated by immersion in the preparation of the active compound of the desired concentration. After the desired time the destruction is determined in percentage. In this case 100%, means that all the lice on the leaf were destroyed; 0% means that no leaf louse was destroyed. In this test, for example, the products indicated in Examples 1, 42, 46, 56 and 57 show, with a concentration of active compound of 0.1% in the preparation of active compound, a degree of activity of 90%. Example B Test with Nephotettix. Solvent: 7 parts by weight of dimethylformamide. Emulsifier: 1 Part by weight of alkylaryl polyglycol ether. To obtain an active compound preparation, 1 part by weight of the active compound is mixed with the indicated amount of solvent and with the indicated amount of emulsifier and the concentrate is diluted with water to the desired concentration. Dip plates of rice (Oryza sativa) in the preparation of active product of the desired concentration and cover with green rice cicadas (Nephotettix cincticeps), while the leaves are still wet. After the desired time, the degree of death is determined in%. In this case 100%, means that all the cicadas were destroyed; 0% means that no cicada was destroyed. In this test, for example, the products indicated in Examples 28, 44, 45, 55 and 56 show, with a concentration of active compound of 0.1% in the preparation of active compound, a degree of activity of 100%. Example C Test with Phaedon larvae. Solvent: 7 parts by weight of dimethylformamide. Emulsifier: 1 Part by weight of alkylaryl polyglycol ether. To obtain a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amount of solvent and with the indicated amount of emulsifier and the concentrate is diluted with water to the desired concentration. Cabbage leaves are dipped (Brassica olerácea) in the preparation of active product of the desired concentration and are covered with leaf beetle larvae of spicy horseradish (Phaedon cochleariae), while the leaves are still moist. After the desired time, the degree of death is determined in%. In this case 100% means that all mite larvae were destroyed, 0% means that no larvae of mites were destroyed. In this test, for example, the products indicated in Examples 1 and 56 show, with an active product concentration of 0.1% in the preparation of active product, a degree of activity of 100 percent. Example D Test with Plutella. Solvent: 7 parts by weight of dimethylformamide. Emulsifier: 1 part by weight of alkylaryl polyglycol ether To obtain a convenient preparation of active compound, 1 part by weight of active compound is mixed with the indicated amount of solvent and with the indicated amount of emulsifier and the concentrate is diluted with water until The desired concentration: Cabbage leaves (Brassica oleracea) are treated by immersion with the preparation of the active compound of the desired concentration and covered with cabbage caterpillars (Plutella maculipennis), while the leaves are still moist.

After the desired time, the degree of death is determined in%. In this case 100% means that all the caterpillars were destroyed, 0% means that no caterpillar was destroyed. In this test, for example, the products indicated in Examples 24, 45, 46 and 50 show, with a concentration of active compound of 0.1% in the preparation of active compound, a degree of activity of 100%. EXAMPLE E Assay with Spodoptera Frugiperda Solvent: 7 parts by weight of dimethylformamide. Emulsifier: 1 Part by weight of alkylaryl polyglycol ether. To obtain a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amount of solvent and with the indicated amount of emulsifier and the concentrate is diluted with water to the desired concentration. Cabbage leaves (Brassica olerácea) are treated by being dipped into the preparation of the active compound of the desired concentration and covered with caterpillars of the corn moth (Spodoptera frugiperda), while the leaves are still moist. After the desired time, the degree of destruction in% is determined. In this case 100% means that all caterpillars were destroyed; 0% means that no caterpillar was destroyed. In this test, for example, the products indicated in Examples 44 and 56 show, with an active product concentration of 0.1% in the preparation of active product, a degree of activity of 100 percent. Example F Test with Tetranychus (OP-resistant / dip treatment). Solvent: 7 parts by weight of dimethylformamide. Emulsifier: 1 Part by weight of alkylaryl polyglycol ether. To obtain a suitable active product preparation, 1 part by weight of the active compound is mixed with the indicated amount of solvent and the indicated amount of emulsifier and the concentrate is diluted with water to the desired concentration.

Bean plants (Phaseolus vulgaris), which are strongly attacked by all stages of the development of the common red spider mite (Tetranychus urticae), are submerged in a preparation of the active product of the desired concentration. After the desired time, the degree of death is determined in%. In this case they mean 100% that all the mites of the spider mite were killed; 0% means that no spider mite was killed. In this test, for example, the products indicated in Examples 3, 29, 44, 46 and 50, with a concentration of active compound of 0.1% in the preparation of active compound, have a degree of activity of 90 percent. Example G Test limit concentration / systemic effect in the roots. Test insect: Aphis fabae. Solvent: 4 parts by weight of acetone. Emulsifier: 1 Part by weight of alkylaryl polyglycol ether. To obtain an active compound preparation, 1 part by weight of active compound is mixed with the indicated amount of solvent, the indicated amount of emulsifier is added and the concentrate is diluted with methanol to the desired concentration. The preparation of the active product is intimately mixed with the soil. In this case practically no role plays the concentration of the active product in the preparation, only the amount of active product per unit of soil volume, which is indicated in ppm (= mg / l), is decisive. The treated soils are loaded in 250 ml pots and these are planted with orchard bean. The active product can thus be absorbed by the roots of the plants from the ground and transported to the leaves. In order to demonstrate the systemic effect of the roots, the leaves with the aforementioned test animals are covered after 7 days. After another 7 days, the evaluation is carried out by counting or estimating dead animals. From the number of deaths, the systemic effect is deduced by the roots of the active product. This is 100% when all the animals have been destroyed and is 0% when exactly as many insects still live as in the untreated controls.

In this test, it shows the active product, indicated in Example 1, with an active product concentration of 1.25 ppm in the soil, a degree of activity of 100 percent. EXAMPLE H Limit concentration test / systemic e ect in the roots. Test insect: Myzus persicae. Solvent: 4 parts by weight of acetone. Emulsifier: 1 Part by weight of alkylaryl polyglycol ether. To obtain an active compound preparation, 1 part by weight of active compound is mixed with the indicated amount of solvent, the indicated amount of emulsifier is added and the concentrate is diluted with methanol to the desired concentration. The preparation of the active product is intimately mixed with the soil. In this case practically no role plays the concentration of the active product in the preparation, only the amount of active product per unit of soil volume, which is indicated in ppm (mg / ml), is decisive. The treated soils are loaded in 250 ml pots and these are planted with orchard bean. The active product can thus be absorbed by the roots of the plants from the ground and transported to the leaves. In order to demonstrate the systemic effect of the roots, the leaves with the aforementioned test animals are covered after 7 days. After another 7 days, the evaluation is carried out by counting or estimating dead animals. From the number of deaths, the systemic effect is deduced by the roots of the active product. This is 100% when all the animals have been destroyed and is 0% when exactly as many insects still live as in the untreated controls. In this test, it shows the active product, indicated in Example 1, with an active product concentration of 1.25 ppm in the soil, a degree of activity of 100 percent. Example J Test with Plasmopara (vines) / protector. Solvent: 47 parts by weight of acetone. Emulsifier: 3 parts by weight of alkylaryl polyglycol ether.

To obtain a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration. To test the protective activity, young plants are sprayed with the preparation of the active compound in the indicated application amount. After drying of the spray-applied coating, the plants are inoculated with an aqueous suspension of Plasmopara viticola and they remain for 1 day in an incubation cabin at 20 ° C and a relative humidity of 100%. Then plants are available for 5 days in the greenhouse at approximately 21 ° C and a relative humidity of approximately 90%. The plants are then moistened and kept 1 day in an incubation cabin. The evaluation is carried out 6 days after the inoculation. In this case, 0% means a degree of activity corresponding to that of the controls, while a degree of activity of 100% means that no attack of any kind is observed.

In this test it shows the active products indicated in Example 57, with an application amount of 100 g / ha, a degree of activity greater than 80 percent. It is noted that in relation to this date, the best method known to the applicant to carry out the aforementioned invention is that which is clear from the present description of the invention.

Claims (11)

R E I V I N D I C A C I O N E S Having described the invention as above, the content of the following claims is claimed as property:

1.- 3-Phenyl-pyrones of the formula Characterized because X means alkyl and Y means halogen X means halogen and Y means alkyl, A stands for hydrogen, alkyl or aryl if appropriate and D means hydrogen, alkyl, optionally substituted cycloalkyl, optionally substituted aryl or optionally substituted heterocyclyl, D means a radical of the formula -CHj-O-C-RO where R represents phenyl, optionally substituted, or A and D together with the carbon atoms, with which they are linked, mean a substituted carbocycle, if any, or mean a substituted heterocycle, the compounds of the formulas being excluded

2. - Compounds of the formula (I) according to claim 1, characterized in that X means alkyl having 1 to 6 carbon atoms and Y means fluorine, chlorine or bromine, X means fluorine, chlorine or bromine and Y means alkyl having 1 to 6 carbon atoms, A means hydrogen, alkyl having 1 to 12 carbon atoms or phenyl, which may be substituted one to three times, in the same or different ways by halogen, by alkyl having 1 to 6 carbon atoms, by haloalkyl with 1 to 6 carbon atoms, for alkoxy with 1 to 6 carbon atoms, for halogenalkoxy with 1 to 6 carbon atoms, for cyano and / or for nitro, D means hydrogen, alkyl with 1 to 12 carbon atoms, means cycloalkyl with 3 carbon atoms; up to 8 carbon atoms optionally substituted by halogen, by alkyl with 1 to 4 carbon atoms, by alkoxy with 1 to 4 carbon atoms and / or by haloalkyl with 1 to 4 carbon atoms, or means phenyl, which can be to be substituted one to three times, in the same or in different ways, by halogen, by alkyl with 1 to 6 carbon atoms, by halogenalkyl with 1 to 6 carbon atoms, by alkoxy with 1 to 6 carbon atoms, Halogenalkoxy with 1 to 6 carbon atoms, per cyano, po nitro, by phenyl and / or by phenoxy, the two radicals mentioned may be substituted, on the one hand, once or twice, by halogen, by alkyl with 1 to 4 carbon atoms, by alkoxy with 1 to 4. carbon atoms, by halogenalkyl with 1 to 4 carbon atoms and / or by halogenalkoxy with 1 to 4 carbon atoms, 0 means heteroaryl with 5 or 6 members with 1 or 2 heteroatoms of the series consisting of oxygen, sulfur and nitrogen, these residues can be substituted once or twice, by halogen, by alkyl with 1 to 6 carbon atoms, for halogen alkyl with 1 to 6 carbon atoms, for alkoxy with 1 to 6 carbon atoms, for halogenalkoxy with 1 to 6 carbon atoms, for cyano and / or for nitro, or means a radical of the formula where R means phenyl which may be substituted one to three times, in the same or different ways by halogen, by alkyl having 1 to 6 carbon atoms, by halogenalkyl with 1 to 6 carbon atoms, by alkoxy with 1 to 6 carbon atoms, by haloalkoxy having 1 to 6 carbon atoms, per cyano and / or per nitro, A and D also together also mean an alkanediyl group with 3 to 6 carbon atoms, alkenodiyl with 3 to 6 carbon atoms or alkanediyl with 4 to 6 carbon atoms, it being possible to replace a methylene group by oxygen or sulfur, and optionally substituted by halogen, by alkyl with 1 to 6 carbon atoms, by halogenalkyl with 1 to 6 carbon atoms, by alkoxy with 1 to 6 carbon atoms, by halogenalkoxy with 1 to 6 carbon atoms, or by another alkanediyl group with 3 to 6 carbon atoms, alkenodiyl with 3 to 6 carbon atoms or alkanediyl with 4 to 6 carbon atoms forming a fused ring, in which a methylene group is respectively replaced by oxygen or by sulfur and which are optionally substituted by alkyl having 1 to 6 carbon atoms, excluding the compounds of the formulas

3. - Compounds of the formula (I) according to claim 1, characterized in that X means alkyl with 1 to 4 carbon atoms and Y means fluorine, chlorine or bromine, X means chlorine or bromine and Y means alkyl with 1 to 4 carbon atoms, A means hydrogen, alkyl having 1 to 8 carbon atoms or means phenyl, which may be substituted one to three times, in the same or different ways by fluorine, by chlorine, by bromine, by alkyl with 1 to 4 carbon atoms. carbon, by halogenalkyl with 1 to 4 carbon atoms, by alkoxy with 1 to 4 carbon atoms, by haloalkoxy with 1 to 4 carbon atoms, by cyano and / or by nitro, D means hydrogen, alkyl with 1 to 10 atoms of carbon, means cycloalkyl with 3 to 7 carbon atoms, optionally substituted one to three times, in the same or different ways by fluorine, by chlorine, by alkyl with 1 to 3 carbon atoms, by alkoxy with 1 to 2 carbon atoms, by halogenalkyl with 1 to 2 carbon atoms, or means phenyl which may be substituted one to three times, in the same or different ways by fluorine, by chlorine, by bromine, by alkyl with 1 to 4 carbon atoms, by haloalkyl with 1 to 4 carbon atoms no, by alkoxy with 1 to 4 carbon atoms, by haloalkoxy with 1 to 4 carbon atoms, by cyano, by nitro, by phenyl and / or by phenoxy, the latter two moieties may be substituted for their part once or twice by fluorine, by chlorine, by bromine, by methyl, by ethyl, by methoxy, by trifluoromethyl, by trifluoromethoxy and / or by difluoromethoxy, or means furanyl, pyridyl, imidazolyl, triazolyl, pyrazolyl, pyrimidinyl, thiazolyl or thienyl , these residues can be substituted once or twice, by fluorine, by chlorine, by bromine, by alkyl with 1 to 4 carbon atoms, by halogenalkyl with 1 to 4 carbon atoms, by alkoxy with 1 to 4 carbon atoms, by haloalkoxy with 1 to 4 carbon atoms, by cyano and / or by nitro, OD means a radical of the formula -CHj-O-C-RO wherein R means phenyl, which may be substituted one to three times, in the same or different ways by fluorine, by chlorine, by bromine, by alkyl with 1 to 4 carbon atoms; carbon, by halogenalkyl with 1 to 4 carbon atoms, by alkoxy with 1 to 4 carbon atoms, by haloalkoxy with 1 to 4 carbon atoms, by cyano and / or by nitro, A and D together also mean an alkanediyl group with 3 to 5 carbon atoms or an alkenodiyl group having 3 to 5 carbon atoms, where a carbon atom may be replaced, respectively, by oxygen or sulfur, and which may be substituted, if appropriate, by fluorine, chlorine, bromine , by alkyl with 1 to 4 carbon atoms, by alkoxy with 1 to 4 carbon atoms, by haloalkyl with 1 to 4 carbon atoms and / or by halogenalkoxy with 1 to 6 carbon atoms, or by another alkaddiendiyl group with 4 carbon atoms; carbon atoms that form a fused ring, which can be substituted by alkyl with 1 to 4 carbon atoms, the compounds of the formulas being excluded

4. - Compounds of the formula (I) according to claim 1, characterized in that X means methyl or ethyl and Y means fluorine, or chlorine X means chlorine or bromine and Y means methyl or ethyl, A stands for hydrogen, alkyl with 1 to 6 carbon atoms or means phenyl, which may be substituted once or twice, in the same or different ways by fluorine, by chlorine, by methyl, ethyl, n-propyl, iso-propyl, trifluoromethyl, methoxy, ethoxy, trifluoromethoxy, cyano and / or nitro, D means hydrogen, alkyl of 1 to 8 carbon atoms, or means cycloalkyl with 3 to 7 carbon atoms, optionally substituted once or twice, in the same or different ways by fluorine, chlorine, methyl, ethyl, methoxy, ethoxy and / or trifluoromethyl, or phenyl, which may be substituted once or twice, in the same or in different ways by fluorine, by chlorine, by bromine, by methyl, by ethyl, by n-propyl, by isopropyl, by n-butyl, by sec. -butyl, by iso-butyl, by tere. -butyl, by trifluoromethyl, by methoxy by ethoxy, by trifluoromethoxy, by cyano, by nitro, by phenyl and / or by phenoxy, the two latter moieties may be substituted last, on the other hand, once or twice, by fluorine , by chlorine, by methyl, by methoxy, by trifluoromethyl and / or by trifluoromethoxy, or means furanyl, pyridyl or thienyl, these residues may be substituted once or twice by fluorine, by chlorine, by bromine, by methoxy, by ethyl, by n-propyl, by iso-propyl, by trifluoromethyl, by trifluoromethoxy, by cyano and / or by nitro, or by D means a radical of the formula wherein R means phenyl, which may be substituted once or twice, in the same or in different ways by fluorine, by chlorine, by methyl, by ethyl, by trifluoromethyl, by methoxy, by trifluoromethoxy, by cyano and / or by nitro, A and D together also mean an alkanediyl group with 3 to 5 carbon atoms or an alkenodiyl group with 3 to 5 carbon atoms, where a methylene group is, respectively, replaced by oxygen or, for sulfur, and which is substituted optionally from one to four times, in the same or different ways by fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec. -butyl, by tere. -butyl, by methoxy, by trifluoromethyl and / or by trifluoromethoxy, or by another butadyendiyl group, which forms a fused ring, which may be substituted once or twice, by methyl, the compounds of the formulas being excluded

5. - Process for the preparation of 3-phenyl-pyrones of the formula (I), according to claim 1, characterized in that either a) carbonyl compounds of the formula are reacted wherein A and D have the meanings indicated above, or ß) silylethers of the formula wherein A and D have the meanings given above and Alk means alkyl having 1 to 4 carbon atoms, respectively with keten-derivatives of the formula (IV) wherein X and Y have the meanings indicated above and Hal means chlorine or bromine, if appropriate in the presence of a diluent and, if appropriate, in the presence of an acid acceptor.

6. Pesticidal / fungicidal and herbicidal agents, characterized in that they have a content in at least one 3-phenyl-pyrone of the formula (I) according to claim 1, together with extenders and / or surfactants.

7.- Use of the 3-phenyl-pyrones of the formula (I) according to claim 1, as pesticides, fungicides and herbicides.

8. Procedure for the fight against animal pests, characterized in that 3-phenyl-pyrones of the formula (I) are applied. according to claim 1, on pests and / or on their environment.

9. Procedure for the fight against fungi, characterized in that 3-phenyl-pyrones of the formula (I) are applied, according to claim 1, on the fungi and / or on their environment.

10. Procedure for the fight against weeds, characterized in that 3-phenyl-pyrones of the formula (I) are applied. according to claim 1, on weeds and / or on their environment.

11. Process for obtaining pesticides, fungicides and herbicides, characterized in that 3-phenyl-pyrones of the formula (I) according to claim 1 are mixed with extenders and / or surfactants.