DE19848895A1 - New pesticidal 5-halo-3-phenyl-pyrones, useful as insecticides, acaricides, nematocides, ectoparasiticides, fungicides or herbicides - Google Patents

Abstract

3-(2,4-Disubstituted phenyl)-5-halo-4-hydroxypyrones (I) are new. Pyrones of formula (I) are new: one of X, Y = alkyl and the other = F; A = halo; D = H, alkyl or -CH2OCOR; or cycloalkyl, aryl or heterocyclyl (all optionally substituted); R = optionally substituted phenyl; the compound 5-chloro-6-(4-chlorophenyl)-3-(4-fluoro-2-methylphenyl)-4-hydroxy-pyrone is excluded. An Independent claim is included for the preparation of (I).

Description

The present invention relates to new 5-halogen-3-phenyl-pyrones, a process for their manufacture and their use as pesticides.

There are already numerous 5-halopyrone derivatives with pesticidal and herbicidal Properties become known (cf. WO 97/16 436). So z. B. 3- (2-Methyl-4- fluorophenyl) -4-hydroxy-5-chloro-6- (4-chlorophenyl) pyrone to combat animal pests are used. The effectiveness of this substance is good but leaves in at low application rates or for certain indications to be desired in some cases.

There have now been new 5-halogen-3-phenyl-pyrones of the formula

in which
X represents alkyl and
Y represents fluorine, or
X stands for fluorine and
Y represents alkyl,
A stands for halogen and
D represents hydrogen, alkyl, optionally substituted cycloalkyl, optionally substituted aryl or optionally substituted heterocyclyl, or
D for a residue of the formula

stands in what
R represents optionally substituted phenyl,
found, the compound of the formula

is excluded.

The compounds of formula (I) can, depending on the type of Substituents as geometric and / or optical isomers or mixtures of isomers in different composition, which may be in the usual way and ways can be separated. The present invention relates to both pure isomers as well as isomer mixtures. The following is the simplicity for the sake of convenience, however, we always speak of 5-halo-3-phenyl-pyrones of the formula (I), although this means that both the pure isomers and optionally also mixtures with different proportions of isomers are meant.  

The 5-halogen-3-phenyl-pyrones of the formula (I) can be represented by the formula

be depicted. The dashed line is intended to indicate that these substances in the two tautomeric forms

can be present.

The 5-halogen-3-phenyl-pyrones according to the invention can either be in the form of mixtures of compounds of the formulas (I) and (Ia) or in the form of pure isomers available. Mixtures of compounds of the formulas (I) and (Ia) can be separate physical ways, for example by chromatographic methods.  

For reasons of better clarity, only one of the possible isomers listed. That doesn't rule out the connections optionally in the form of the isomer mixtures or in the other isomer Form can exist.

It has also been found that 5-halo-3-phenylpyrones of the formula (I) can be prepared by using carbonyl compounds of the formula

in which
A and D have the meanings given above,
with ketene derivatives of the formula

in which
X and Y have the meanings given above and
Hal represents chlorine or bromine,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid acceptor.

Finally, it was found that the 5-halogen-3-phenyl-pyrones according to the invention Formula (I) be a very good pesticidal, fungicidal and herbicidal activity sit.

Surprisingly, the 5-halo-3-phenylpyrones of the formula (I) according to the invention are better than pesticides, fungicides and herbicides than the constitutionally most similar, known active ingredients of the same action. The 5-halogen-3-phenyl-pyrones according to the invention are generally defined by the formula (I). Compounds of the formula (I) in which
X represents alkyl having 1 to 6 carbon atoms and
Y stands for fluorine,
or
X stands for fluorine and
Y represents alkyl having 1 to 6 carbon atoms.
A preferably represents fluorine, chlorine or bromine.
D preferably represents hydrogen, alkyl having 1 to 12 carbon atoms, cycloalkyl having 3 to 8 carbon atoms optionally substituted by halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms and / or haloalkyl having 1 to 4 carbon atoms, or for phenyl which can be substituted one to three times, in the same way or differently, by halogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, Cyano, nitro, phenyl and / or phenoxy, where the latter two radicals can in turn be substituted one or two times by halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkyl and / or C ₁ -C ₄ haloalkoxy, or for five or six-membered heteroaryl with 1 or 2 heteroatoms from the series oxygen, sulfur and nitrogen, where these radicals can be mono- or disubstituted by halogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ halo alkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, cyano and / or nitro, or for a radical of the formula

wherein
R preferably represents phenyl which can be mono- to trisubstituted, identical or differently substituted by halogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ - Haloalkoxy, cyano and / or nitro.

The compounds of the formula (I) are particularly preferred
X for alkyl with 1 to 4 carbon atoms and
Y for fluorine
or
X for fluorine and
Y is alkyl of 1 to 4 carbon atoms.
A also particularly preferably represents fluorine, chlorine or bromine.
D particularly preferably represents hydrogen, alkyl having 1 to 10 carbon atoms, optionally single to quadruple, identical or different by fluorine, chlorine, C ₁ -C ₃ alkyl, C ₁ -C ₂ alkoxy, C ₁ -C ₂ - Haloalkyl-substituted cycloalkyl with 3 to 7 carbon atoms, or for phenyl, which can be mono- to triple, identical or differently substituted by fluorine, chlorine, bromine, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, cyano, nitro, phenyl and / or phenoxy, where the latter two radicals in turn can be mono- or disubstituted by fluorine, chlorine, bromine, methyl, ethyl, Methoxy, trifluoromethyl, trifluoromethoxy and / or difluoromethoxy, or for furanyl, pyridyl, imidazolyl, triazolyl, pyrazolyl, pyrimidinyl, thiazolyl or thienyl, these radicals can be mono- or disubstituted by fluorine, chlorine, bromine, C ₁ -C ₄ - Alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ -haloalkoxy, cyano and / or nitro,
or
D particularly preferably represents a radical of the formula

wherein
R particularly preferably represents phenyl which can be monosubstituted to trisubstituted in the same manner or differently by fluorine, chlorine, bromine, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ - haloalkoxy, cyano and / or nitro.

The compounds of the formula (I) are very particularly preferred
X is methyl or ethyl and
Y for fluorine
or
X for fluorine and
Y is methyl or ethyl.
A very particularly preferably represents fluorine, chlorine or bromine.
D very particularly preferably represents hydrogen, alkyl having 1 to 8 carbon atoms, or optionally optionally up to four times, identical or different, cycloalkyl having 3 to 7 carbon atoms substituted by fluorine, chlorine, methyl, ethyl, methoxy, ethoxy and / or trifluoromethyl, or for phenyl, which can be mono- to triple, identical or differently substituted by fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, iso-butyl, tert.- Butyl, trifluoromethyl, methoxy, ethoxy, trifluoromethoxy, cyano, nitro, phenyl and / or phenoxy, where the latter two radicals can in turn be mono- or disubstituted by fluorine, chlorine, methyl, methoxy, trifluoromethyl and / or tri fluoromethoxy, or for Furanyl, pyridyl or thienyl, where these radicals can be mono- or disubstituted by fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, trifluoromethyl, trifluoromethoxy, cyano and / or nitro,
or
D very particularly preferably represents a radical of the formula

wherein
R particularly preferably represents phenyl which can be monosubstituted to trisubstituted in the same manner or differently by fluorine, chlorine, methyl, ethyl, trifluoromethyl, methoxy, trifluoromethoxy, cyano and / or nitro.

The radicals listed above or listed in preferred areas Definitions or explanations can be made with each other, i.e. also between the respective areas and preferred areas can be combined as desired. they seem for the end products as well as for the preliminary and intermediate products accordingly. Except individual definitions can also be omitted.

Excepted from the 5-halo-3-phenyl-pyrones according to the invention, as already mentioned above, in each case the compound of the formula

In particular, apart from the 5-halogeno-3- phenyl-pyrones called the following substances of formula (I).  

Table 1

Table 2

Table 3

wherein
D has the meanings given in Table 1.

If (chlorocarbonyl) -2- (2-methyl-4-fluorophenyl) ketene and chloromethyl- (4-fluorophenyl) ketone are used as starting substances, the course of the process according to the invention can be illustrated by the following formula become.

The carbonyls required as starting materials in the process according to the invention Compounds are generally defined by formula (II). Have in this formula A and D preferably have those meanings that are already related to the description of the 5-halogen-3-phenyl-pyrones of the formula (I) according to the invention were mentioned as preferred for these residues.  

The carbonyl compounds of the formula (II) are known or can be reduced produce known methods.

The reaction compo when carrying out the method according to the invention The ketene derivatives required are generally defined by the formula (III). In of this formula, X and Y preferably have those meanings which are already in Connection with the description of the 5-halogen-3-phenyl- pyrones of the formula (I) were mentioned as preferred for these radicals. Hal also stands preferably for chlorine or bromine.

The ketene derivatives of the formula (III) are known or can be prepared by known processes (cf. Org. Prep. Proced. Int. 7, 155-158 (1975) and DE-A 19 45 703). Thus, ketene derivatives of the formula (III) are obtained by using substituted phenylmalonic acids of the formula

in which
X and Y have the meanings given above,
with acid halides, such as thionyl chloride, phosphorus (V) chloride, phosphorus (III) chloride, oxalyl chloride, phosgene or thionyl bromide, if appropriate 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 . As 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 (IV) are known or can be prepared by known methods (see, for example, Organikum, VEB Deutscher Verlag der Wissenschaften, Berlin 1977, p. 517 ff). So you get substituted Phenylma lonic acids of formula (IV) by substituted phenylmalonic acid esters of the formula

in which
X and Y have the meanings given above and
R ^{1 represents} 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 formula (V), X and Y preferably have those meanings which have already been mentioned as preferred for these radicals in connection with the description of the 3-phenylpyrones of the formula (I) according to the invention. R ¹ preferably represents methyl or ethyl.

The substituted phenylmalonic acid esters of the formula (V) are known or have not been used are produced by known methods (cf. Tetrahedron Letters 27, 2763 (1986) and VEB German Publishing House of Sciences, Berlin 1977, pp. 587 ff.).  

Suitable diluents for carrying out the Ver according to the invention driving all common organic sol inert to the reactants ventien in question. Hydrocarbons, such as o-dichlor, are preferably usable benzene, tetralin, toluene and xylene, furthermore ethers, such as dibutyl ether, glycol dime ethyl ether and diglycol dimethyl ether, and also polar solvents, such as dimethyl sulfoxide, sulfolane, dimethylformamide or N-methylpyrrolidone.

As acid acceptors come when carrying out the Ver according to the invention drive all common acid binders into consideration. Are preferably usable tertiary amines, such as triethylamine, pyridine, diazabicyclooctane (DABCO), diazabi cycloundecene (DBU), diazabicyclonones (DBN), Hünig base or N, N-dimethyl aniline.

The reaction temperatures can be carried out when carrying out the process according to the invention Process can be varied within a wide range. Conveniently one works at temperatures between 0 ° C and 250 ° C, preferably between 50 ° C and 220 ° C.

The process according to the invention is preferably carried out under atmospheric pressure.

When carrying out the invention, 1 mol of carbonyl ver is used Compounds of formula (II) generally an equimolar amount of ketene derivative of formula (III) and optionally also an equimolar amount of acid acceptor on. However, it is also possible to use one or the other component in a larger one Use excess (up to S mol).

The 3-phenylpyrones of the formula (I) according to the invention have a very good one pesticidal activity and have a very good tolerance to crops on.  

The active ingredients are suitable for controlling animal pests, preferably wise arthropods and nematodes, especially insects and arachnids, which in in agriculture, in forestry, in the protection of stocks and materials, and on the Hygiene sector occur. They are against normally sensitive and resistant species effective against all or individual stages of development. To the above mentioned Pests include:

From the order of the Isopoda z. B. Oniscus asellus, Armadillidium vulgare, Porcellio scaber.

From the order of the Diplopoda z. B. Blaniulus guttulatus
From the order of the Chilopoda z. B. Geophilus carpophagus, Scutigera spec.
From the order of the Symphyla z. B. Scutigerella immaculata.
From the order of the Thysanura z. B. Lepisma saccharina.
From the order of the Collembola z. B. Onychiurus armatus.

From the order of Orthoptera z. B. Blatta orientalis, Periplaneta americana, Leu cophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria.

From the order of the Dermaptera z. B. Auricular Forficula.
From the order of the Isoptera z. B. Reticulitermes spp.

From the order of the Anoplura z. B. Phylloxera vastatrix, Pemphigus spp., Pediculus humanus corporis, Haematopinus spp., Linognathus spp.
From the order of the Mallophaga z. B. Trichodectes spp., Damalinea spp.
From the order of the Thysanoptera z. B. Frankliniella occidentalis, Hercinothrips femoralis, Thrips palmi, Thrips tabaci.
From the order of Heteroptera z. B. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.

From the order of Homoptera z. B. Aleurodes brassicae, Bemisia tabaci, Trialeu rodes vaporariorum, Aphis gossypü, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosi phum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantü, Aspidiotus hederae, Pseudococcus spp. Psylla spp.

From the order of the Lepidoptera z. B. 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., 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 magnanima, Tortrix viridana.

From the order of the Coleoptera z. B. Anobium punctatum, Rhizopertha dominica, Acanthoscelides obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes ehrysocephala, Epilachna varive stis, Atomaria spp., Oryzaephilus surinamensis, Antho nomus 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., Cono derus spp., Melolontha melolontha, Amphimallon solsti tialis, Costelytra zealandica.  

From the order of the Hymenoptera z. B. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.

From the order of the Diptera z. B. 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 fit, Phorbia spp., Pegomyia hyoscyami, ceratitis capitata, Dacus oleae, Tipula paludosa.

From the order of the Siphonaptera z. B. Xenopsylla cheopis, Ceratophyllus spp. From the order of the Arachnida z. B. Scorpio maurus, Latrodectus mactans.

From the order of Acarina z. B. Acarus siro, 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 compounds according to the invention are notable for high insecticidal and acaricidal activity after leaf and soil application.

They can be used with particularly good results in combating plant damage the insects, such as against the larvae of the horseradish leaf beetle (Phaedon cochleariae), against the larvae of the green leafhopper (Nephotettix cincticeps) and against the larvae of the green peach aphid (Myzus persicae). The active compounds according to the invention also have a herbicidal activity and can be used as defoliants, desiccants, haulm killers and especially as Weed killers are used. Among weeds in the broadest sense are all plants that grow in places where they are undesirable.  

It depends on whether the substances according to the invention act as total or selective herbicides depends essentially on the amount applied.

The dosages of the inventive weed control necessary Active substances are between 0.001 and 10 kg / ha, preferably between 0.005 and 5 kg / ha.

The active compounds according to the invention can, for. B. ver in the following plants be applied:

Dicotyledon weeds of the genera: 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.

Dicot cultures of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, lactuca, cucumis, cucurbita.

Monocotyledonous weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cycnodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera.

Monocot cultures of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Secale, sorghum, panicum, saccharum, pineapple, asparagus, allium.  

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

Depending on the concentration, the compounds are suitable for the total weed control z. B. on industrial and track systems and on paths and squares with and without tree cover. Likewise, the connections to weed control fungus in permanent crops, e.g. B. forest, ornamental wood, fruit, wine, citrus, nut, banana, Coffee, tea, gum, oil palm, cocoa, berry fruit and hop plants Ornamental and sports turf and pastures and for selective weed control in annual cultures are used.

In addition, the 5-halogen-3-phenyl-pyrones of the formula (I) also have a strong fungicidal effect and can be used to combat wanted fungal microorganisms in crop protection and material protection be used.

Fungicides can be used to control Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Use Deuteromycetes.

Some pathogens of fungal diseases are exemplary but not limiting, which fall under the generic terms listed above, called:

Xanthomonas species, such as, for example, Xanthomonas campestris pv. Oryzae;
Pseudomonas species, such as, for example, Pseudomonas syringae pv. Lachrymans;
Erwinia species, such as, for example, Erwinia amylovora;
Pythium species, such as, for example, Pythium ultimum;
Phytophthora species, such as, for example, Phytophthora infestans;
Pseudoperonospora species, such as, for example, Pseudoperonospora humuli or Pseudoperonospora cubensis;
Plasmopara species, such as, for example, Plasmopara viticola;
Bremia species, such as, for example, Bremia lactucae;
Peronospora species, such as, for example, Peronospora pisi or P. brassicae;
Erysiphe species, such as, for example, Erysiphe graminis;
Sphaerotheca species, such as, for example, Sphaerotheca fuliginea;
Podosphaera species, such as, for example, Podosphaera leucotricha;
Venturia species, such as, for example, Venturia inaequalis;
Pyrenophora species, such as, for example, Pyrenophora teres or P. graminea (conidial form: Drechslera, Syn: Helminthosporium);
Cochliobolus species, such as, for example, Cochliobolus sativus (conidial form: Drechslera, Syn: Helminthosporium);
Uromyces species, such as, for example, Uromyces appendiculatus;
Puccinia species, such as, for example, Puccinia recondita;
Sclerotinia species, such as, for example, Sclerotinia sclerotiorum;
Tilletia species, such as, for example, Tilletia caries;
Ustilago species, such as, for example, Ustilago nuda or Ustilago avenae;
Pellicularia species, such as, for example, Pellicularia sasakii;
Pyricularia species, such as, for example, Pyricularia oryzae;
Fusarium species, such as, for example, Fusarium culmorum;
Botrytis species, such as, for example, Botrytis cinerea;
Septoria species, such as, for example, Septoria nodorum;
Leptosphaeria species, such as, for example, Leptosphaeria nodorum;
Cercospora species, such as, for example, Cercospora canescens;
Alternaria species, such as, for example, Alternaria brassicae;
Pseudocercosporella species, such as, for example, Pseudocercosporella herpotrichoides.

The good plant tolerance of the active ingredients in the control of the plant Concentrations necessary for diseases can be treated above ground parts of plants, plant and seed, and the soil.  

The substances according to the invention can be used with particularly good results Combating diseases in wine, fruit and vegetable growing, such as wise against Plasmopora. They also show a good effect against Pyricularia oryzae on rice and have a wide range both in -vitro and in -vivo fungicidal effect.

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

These formulations are prepared in a known manner, e.g. B. by mixing of the active ingredients with extenders, i.e. liquid solvents and / or solid carriers gerstoffe, optionally using surfactants, so Emulsifiers and / or dispersants and / or foaming agents.

In the case of the use of water as an extender, e.g. B. also organic Solvents are used as auxiliary solvents. As a liquid solvent essentially come into question: aromatics, such as xylene, toluene, or alkylnaph thalines, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as Chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. B. petroleum fractions, mineral and vegetable Oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as Acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar Solvents such as dimethylformamide and dimethyl sulfoxide, and water.

The following are suitable as solid carriers:
For example, 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, as solid carriers for granules are possible: z. B. broken and fractured 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 foam-generating agents come into question: z. B. nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. B. alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; as dispersants come into question: z. B. lignin sulfite and methyl cellulose.

Adhesives such as carboxymethyl cellulose, natural, can be used in the formulations and synthetic powdery, granular or latex-shaped polymers are used, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholi pide, such as cephalins and lecithins and synthetic phospholipids. Other additives can be mineral and vegetable oils.

Dyes such as inorganic pigments, e.g. B. iron oxide, titanium oxide, ferro cyan 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% by weight of active ingredient fabric, preferably between 0.5 and 90% and in addition preferably extenders and / or surfactants.

The active compounds according to the invention can be in commercially available formulations and in the use forms prepared from these formulations in a mixture with other active ingredients, such as insecticides, attractants, sterilants, acaricides, Ne maticidal, fungicidal, growth-regulating substances or herbicides are present. Insecticides include, for example, phosphoric acid esters, carbamates, carbon  acid esters, chlorinated hydrocarbons, phenylureas, by microorganisms manufactured fabrics u. a.

Particularly cheap mixing partners are e.g. B. the following:

Fungicides:
2-aminobutane; 2-anilino-4-methyl-6-cyclopropyl-pyrimidine; 2,6'-dibromo-2-methyl-4'-trifluoromethoxy-4'-trifluoromethyl-1,3-thiazole-5-carboxanilide; 2,6-di chloro-N- (4-trifluoromethylbenzyl) benzamide; (E) -2-methoxyimino-N-methyl-2- (2-phenoxyphenyl) acetamide; 8-hydroxyquinoline sulfate; Methyl- (E) -2- {2- [6- (2-cyanophenoxy) pyrimidin-4-yloxy] phenyl} -3-methoxyacrylate; Methyl (E) methoximino [alpha- (o-tolyloxy) -o-tolyl] acetate; 2-phenylphenol (OPP), aldimorph, ampropylfos, anilazine, azaconazole,
Benalaxyl, Benodanil, Benomyl, Binapacryl, Biphenyl, Bitertanol, Blasticidin-S. Bromuconazole, Bupirimate, Buthiobate,
Calcium polysulfide, captafol, captan, carbendazim, carboxin, quinomethionate (quinomethionate), chloroneb, chloropicrin, chlorothalonil, chlozolinate, cufraneb, cymoxanil, cyproconazole, cyprofuram,
Dichlorophen, diclobutrazole, diclofluanid, dic1omezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, dinocap, diphenylamine, dipyrithione, ditalimfos, dithianon, dodine, drazoxolone,
Edifenphos, epoxyconazole, ethirimol, etridiazole,
Fenarimol, Fenbuconazole, Fenfuram, Fenitropan, Fenpiclonil, Fenpropidin, Fen propimorph, Fentinacetat, Fentinhydroxyd, Ferbam, Ferimzone, Fluazinam, Fludi oxonil, Fluoromide, Fluquinconazole, Flusilazole, Flusulfamide, Flutolanyl, Folut, Futuberafl Furalaxyl, Furmecyc lox,
Guazatine,
Hexachlorobenzene, hexaconazole, hymexazole,
Imazalil, Imibenconazol, Iminoctadin, Iprobefos (IBP), Iprodione, Isoprothiolan,
Kasugamycin, copper preparations such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxy-copper and Bordeaux mixture,
Mancopper, Mancozeb, Maneb, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Metrifuroxam, Metiram, Metsulfovax, Myclobutanil,
Nickel dimethyldithiocarbamate, nitrothal isopropyl, Nuarimol,
Ofurace, oxadixyl, oxamocarb, oxycarboxin,
Pefurazoate, penconazole, pencycuron, phosdiphen, phthalide, pimaricin, piperalin, polycarbamate, polyoxin, probenazole, prochloraz, procymidon, propamocarb, propi conazole, propineb, pyrazophos, pyrifenox, pyrimethanil, pyroquilone,
Quintozen (PCNB),
Sulfur and sulfur preparations,
Tebuconazole, Tecloftalam, Tecnazen, Tetraconazole, Thiabendazole, Thicyofen, Thio phanat-methyl, Thiram, Tolclophos-methyl, Tolylfluanid, Triadimefon, Triadimenol, Triazoxid, Trichlamid, Tricyclazol, Tridemorph, Triflumitolizol, Triflumitolizol, Triflumizol
Validamycin A, vinclozolin,
Zineb, ziram.

Bactericides:
Bronopol, dichlorophene, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furan carboxylic acid, oxytetracycline, probenazole, streptomycin, teclof talam, 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, Azo cyclotin,
Bacillus thuringiensis, Bendiocarb, Benfuracarb, Bensultap, Betacyfluthrin, Bifen thrin, BPMC, Brofenprox, Bromophos A, Bufencarb, Buprofezin, Butocarboxim, Butylpyridaben,
Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, CGA 157 419, CGA 184699, Chloethocarb, Chlorethoxyfos, Chlorfenvinphos, Chlorfluazuron, Chlormephos, Chlorpyrifos, Chlorpyrifos M, Cis-Resmethrin, Clocythrinhrhrothrinhrhrinhrinhrinhrinothrinothrinothrinothrinothrinothrinothrinothrinothrinothrinothrinothrinothrinothrinothrinothrinothrinothrinothrinothrinothrinothrinothrinothrinothrinothrinothrinothrinothrinothrinothrinophrinothrinophrinothrinophrinothrinophrine , Cyhexatin, cypermethrin, cyromazine,
Deltamethrin, Demeton M, Demeton S. Demeton-S-methyl, Diafenthiuron, Diazinon, Dichlofenthion, Dichlorvos, Dicliphos, Dicrotophos, Diethion, Diflubenzuron, Di methoat, Dimethylvinphos, Dioxathion, Disulfoton,
Edifenphos, Emamectin, Esfenvalerat, Ethiofencarb, Ethion, Ethofenprox, Etho prophos, Etrimphos,
Fenamiphos, Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil, Fluazinam, Flucycloxuron, Flucythrinat, Flufenoxuron, Flufenothxatophion, Fufionophon, Fufionophon, Fufionophon, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufon, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufox
HCH, heptenophos, hexaflumuron, hexythiazox,
Imidacloprid, Iprobefos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivermectin,
Lambda cyhalothrin, lufenuron,
Malathion, Mecarbam, Mevinphos, Mesulfenphos, Metaldehyde, Methacrifos, Meth amidophos, Methidathion, Methiocarb, Methomyl, Metolcarb, Milbemectin, Mono crotophos, Moxidectin,
Naled, NC 184, NI 25, Nitenpyram,
Omethoate, Oxamyl, Oxydemethon M, Oxydeprofos,
Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos M, Pirimiphos A, Profenofos, Promecarb, Propaphos, Propoxur, Prothiofos, Prothoat, Pymetrozin, Pyrachlophhion, Pyrachlophhion, Pyrachlophhion, Pyrachlophhion, Pyrachlophion, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophion Pyridaben, pyrimidifen, pyriproxifen,
Quinalphos,
RH 5992,
Salithion, Sebufos, Silafluofen, Sulfotep, Sulprofos,
Tebufenozid, Tebufenpyrad, Tebupirimiphos, Teflubenzuron, Tefluthrin, Temephos, Terbam, Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thiofanox, Thio methon, Thionazine, Thuringiensin, Tralometichoniazon, Triaromenhroniaz, Triaratheniazon, Triaratheniazin
Vamidothione, XMC, xylylcarb, YI 5301/5302, zetamethrin.

Herbicides:
for example anilides, such as. B. Diflufenican and Propanil; Arylcarboxylic acids, such as. B. dichloropicolinic acid, dicamba and picloram; Aryloxyalkanoic acids, such as. B. 2.4 D, 2.4 DB, 2.4 DP, fluroxypyr, MCPA, MCPP and triclopyr; Aryloxy-phenoxy alkanoic acid esters, such as. B. diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl and quizalofop-ethyl; Azinones, such as B. Chloridazon and Norflurazon; Carbamates, e.g. B. Chlorpropham, Desmedipham, Phenmedipham and Propham; Chloroacetanilides such as e.g. B. alachlor, acetochlor, butachlor, metazachlor, metolachlor, pretilachlor and propachlor; Dinitroanilines such as e.g. B. Oryzalin, Pendimethalin and Trifluralin; Diphenyl ether, such as. B. acifluorfen, bifenox, fluoroglycofen, fomesafen, halosafen, lactofen and oxyfluorfen; Urine, such as B. chlorotoluron, diuron, fluometuron, isoproturon, linuron and methabenzthiazuron; Hydroxylamines, such as. B. Alloxydim, Clethodim, Cycloxydim, Sethoxydim and Tralkoxydim; Imidazolinones, e.g. B. Imazethapyr, Imaza methabenz, Imazapyr and Imazaquin; Nitriles such as B. bromoxynil, dichlobenil and ioxynil; Oxyacetamides such as e.g. B. Mefenacet; Sulfonylureas, such as. B. amidosul furon, bensulfuron-methyl, chlorimuron-ethyl, chlorosulfuron, cinosulfuron, metsul furon-methyl, nicosulfuron, primisulfuron, pyrazosulfuron-ethyl, thifensulfuron methyl, triasulfuron and tribenuron-methyl; Thiol carbamates such as e.g. B. butylates, cycloates, dialallates, EPTC, esprocarb, molinates, prosulfocarb, thiobencarb and tri allates; Triazines, e.g. B. Atrazin, Cyanazin, Simazin, Simetryne, Terbutryne and Terbutylazin; Triazinones such as e.g. B. hexazinone, metamitron and metribuzin; Others, such as B. aminotriazole, benfuresate, bentazone, cinmethylin, clomazone, clopy ralid, difenzoquat, dithiopyr, ethofumesate, fluorochloridone, glufosinate, glyphosate, isoxaben, pyridate, quinchlorac, quinmerac, sulphosate and tridiphane.

The active compounds according to the invention can also be used in their commercially available form formulations and in the use forms prepared from these formulations in  Mix with synergists. Synergists are connections through which the Effect of the active ingredients is increased without the added synergist itself must be active.

The active substance content of the users prepared from the commercially available formulations Forms of application can vary widely. The drug concentration of the Use forms can be from 0.0000001 to 95% by weight of active ingredient, preferably are between 0.0001 and 1% by weight.

The application takes place in a customary manner adapted to the application forms Wise.

When used against hygiene and storage pests, the effects stand out fabrics through an excellent residual effect on wood and clay as well as through a good stability to alkali on limed substrates.

The active compounds according to the invention act not only against plant, hygiene and Storage pests, but also in the veterinary sector against tie nical parasites (ectoparasites) such as tortoise ticks, leather ticks, mite mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, hair linge, featherlings and fleas. These parasites include:

From the order of the Anoplurida z. B. Haematopinus spp., Linognathus spp., Pedi culus spp., Phtirus spp., Solenopotes spp ..

From the order of the Mallophagida and the subordinates Amblycerina as well Ischnocerina e.g. B. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp.

From the order Diptera and the subordinates Nematocerina as well Brachycerina e.g. B. Aedes spp., Anopheles spp., Culex spp., Simulium spp.,  Eusimulium spp., Phlebotomus spp., Lutzomyia 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., Melophagus spp ..

From the order of the Siphonapterida z. B. Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp.

From the order of the Heteropterida z. B. Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp.

From the order of the Blattarida z. B. Blatta orientalis, Periplaneta americana, Blattela germanica, Supella spp.

From the subclass of Acaria (Acarida) and the orders of the Meta and Mesostigmata e.g. B. Argas spp., Ornithodorus spp., Otabius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemaphysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneu monyssus spp., Sternostoma spp., Varroa spp ..

From the order of the Actinedida (Prostigmata) and Acaridida (Astigmata) z. B. 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., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp ..

The active compounds of the formula (I) according to the invention are also suitable for combating of arthropods, the farm animals, such as. B. cattle, sheep, goats,  Horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese, Bees, other pets such as B. dogs, cats, house birds, aquarium fish as well as so-called experimental animals, such as. B. hamsters, guinea pigs, rats and Infest mice. By fighting these arthropods, deaths and Reductions in performance (for meat, milk, wool, skins, eggs, honey, etc.) ver be reduced, so that by using the active compounds according to the invention more economical and easier animal husbandry is possible.

The active compounds according to the invention are used in the veterinary sector in in a known manner by enteral administration in the form of, for example, tablets, Capsules, watering, drenching, granules, pastes, boluses, the feed-through process, suppositories, by parenteral administration, such as by injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants, through nasal Application, by dermal application in the form of, for example, diving or Bathing (dipping), spraying (spray), pouring (pour-on and spot-on), des Washing, powdering and with the help of shaped articles containing active ingredients, such as Collars, ear tags, tail tags, limb straps, halters, marie devices etc.

When used for cattle, poultry, pets etc., you can use the active ingredients in Formula (I) as formulations (for example powders, emulsions, flowable Agents), which contain the active ingredients in an amount of 1 to 80 wt .-%, directly or after 100 to 10,000 times dilution, or as a chemical bath use.

It has also been found that the compounds of the formula (I) show a high insecticidal activity against insects, the technical materials to destroy.

The following are examples and preferably - but without limitation - Called insects:  

Beetle like
Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufo villosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearesces, Lyctus pubis linearis, Lyctus pubis linearis, Lyctus pubis linearis, Lyctus pubis linearis, Lyctus pubis linearis, Lyctus pubis aisles Tryptodendron spec. Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec. Dinoderus minutus.

Skin wings like
Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur.

Termites like
Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes dar winiensis, Zootermopsis nevadensis, Coptotermes formosanus.

Bristle tails like
Lepisma saccharina.

In the present context, technical materials include non-living ones Understand materials, such as preferably plastics, adhesives, glues, papers and cardboard, leather, wood and wood processing products and paints.

The one to be protected against insect attack is very particularly preferably Material around wood and wood processing products.

Among wood and wood processing products, which by the invention Agents or mixtures containing them can be protected is exemplary to understand: timber, wooden beams, railway sleepers, bridge parts, jetties, Wooden vehicles, boxes, pallets, containers, telephone poles, wooden panels,  Wooden windows and doors, plywood, chipboard, carpentry or wood products, which are generally used in house construction or in carpentry.

The active ingredients as such, in the form of concentrates or in general Chen formulations such as powders, granules, solutions, suspensions, emulsions or pastes.

The formulations mentioned can be prepared in a manner known per se the, e.g. B. by mixing the active ingredients with at least one solution or Diluents, emulsifiers, dispersants and / or binders or fixatives, Water repellants, possibly desiccants and UV stabilizers and given if dyes and pigments and other processing aids.

The insecticidal agents or used to protect wood and wood-based materials Concentrates contain the active ingredient according to the invention in a concentration of 0.0001 to 95% by weight, in particular 0.001 to 60% by weight.

The amount of agents or concentrates used depends on the type and type come from insects and depending on the medium. The optimal amount to use can be determined by test series in the application. In general however, it is sufficient 0.0001 to 20% by weight, preferably 0.001 to 10% by weight, of the active ingredient, based on the material to be protected.

An organic chemical solution serves as the solvent and / or diluent medium or solvent mixture and / or an oily or oily low volatility organic chemical solvent or solvent mixture and / or a polar organic chemical solvent or solvent mixture and / or Water and optionally an emulsifier and / or wetting agent.

The organic chemical solvents used are preferably oily or oily ones Solvents with an evaporation number above 35 and a flash point above  30 ° C, preferably above 45 ° C, used. As such a volatile thing Corresponding mineral oils become serum-insoluble, oily and oily solvents or their aromatic fractions or mineral oil-containing solvent mixtures preferably white spirit, petroleum and / or alkylbenzene used.

Mineral oils with a boiling range of 170 to 220 ° C are advantageous, test petrol with a boiling range of 170 to 220 ° C, spindle oil with a boiling range from 250 to 350 ° C, petroleum or aromatics with a boiling range from 160 to 280 ° C, Turpentine oil and the like.

In a preferred embodiment, liquid aliphatic hydrocarbons substances with a boiling range of 180 to 210 ° C or high-boiling mixtures of aromatic and aliphatic hydrocarbons with a boiling range of 180 to 220 ° C and / or spindle oil and / or monochloronaphthalene, preferably - Monochloronaphthalene used.

The organic semi-volatile oily or oily solvents with a ver Evaporation number above 35 and a flash point above 30 ° C, preferably above half 45 ° C, can be partly due to slightly or medium volatile organic chemical Solvents are replaced, with the proviso that the solvent mixture also an evaporation number above 35 and a flash point above 30 ° C preferably above 45 ° C, and that the insecticide-fungicide mixture in this solvent mixture is soluble or emulsifiable.

According to a preferred embodiment, part of the organic chemical Solvent or solvent mixture through an aliphatic polar orga niche chemical solvent or solvent mixture replaced. Preferably come aliphatic containing hydroxyl and / or ester and / or ether groups organic chemical solvents such as glycol ether, ester or the like. to use.  

As organic-chemical binders in the context of the present invention dung known per se and / or in the orga used nisch-chemical solvents soluble or dispersible or emulsifiable Synthetic resins and / or binding drying oils, in particular binders from or containing an acrylic resin, a vinyl resin, e.g. B. polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indene-coumarone resin, silicone resin, drying vegetable and / or drying oils and / or physi Kalically drying binders based on a natural and / or synthetic resin used.

The synthetic resin used as a binder can be in the form of an emulsion, dispersion or solution. Bitumen or bitumi can also be used as binders nous substances up to 10 wt .-% can be used. In addition, in itself known dyes, pigments, water repellants, odor correctors and Inhibitors or anticorrosive agents and the like are used.

According to the invention, preference is given to at least one organic chemical binder an alkyd resin or modified alkyd resin and / or a drying vegetable Contain oil in the medium or in the concentrate. Are preferred according to the invention Alkyd resins with an oil content of more than 45% by weight, preferably 50 to 68% by weight.

The binder mentioned can be wholly or partly by means of a fixing agent tel (mixture) or a plasticizer (mixture) can be replaced. These additions are meant to volatilization of the active ingredients as well as crystallization or precipitation bow. They preferably replace 0.01 to 30% of the binder (based on 100% of the binder used).

The plasticizers come from the chemical classes of phthalic acid esters such as Dibutyl, dioctyl or benzyl butyl phthalate, phosphoric acid esters such as tributylphos  phate, adipic acid esters such as di (2-ethylhexyl) adipate, stearates such as butyl stearate or Amyl stearate, oleates such as butyl oleate, glycerol ether or higher molecular weight glycol ether, glycerol ester and p-toluenesulfonic acid ester.

Fixing agents are chemically based on polyvinyl alkyl ethers such as. B. Polyvinylme ethyl ether or ketones such as benzophenone, ethylene benzophenone.

Water is also particularly suitable as a solvent or diluent, optionally mixed with one or more of the above organic chemical solvents or diluents, emulsifiers and dispersants.

A particularly effective wood protection is achieved through industrial impregnation processes, e.g. B. vacuum, double vacuum or printing process.

The ready-to-use agents can, if appropriate, still further insecticides and optionally contain one or more fungicides.

The additional mixing partners are preferably those in WO 94/29 268 Insecticides and fungicides mentioned in question. The ones mentioned in this document Connections are an integral part of this application.

Insecticides such as chlorpyriphos are particularly preferred mixing partners. Phoxim, Silafluofin, Alphamethrin, Cyfluthrin, Cypermethrin, Deltamethrin, Perme thrin, imidacloprid, NI-25, flufenoxuron, hexaflumuron and triflumuron, as well Fungicides such as epoxyconazole, hexaconazole, azaconazole, propiconazole, Tebuconazole, cyproconazole, metconazole, imazalil, dichlorfluanid, tolylfluanid, 3-iodo-2-propynyl butyl carbamate, N-octyl-isothiazolin-3-one and 4,5-dichloro-N-octyl called isothiazolin-3-one.  

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

Manufacturing examples example 1

In a mixture of 4.2 g (20 mmol) (chlorocarbonyl) -2- (2-methyl-4-fluorophenyl) - 3.45 g (mmol) of chloromethyl- (4- given fluorophenyl) ketone. The resulting mixture is 6 hours at 200 ° C. heated. After cooling to room temperature, the resulting product mortar and digested with cyclohexane. The remaining solid substance is removed sucks and dries. In this way, 5.6 g (80% of theory) of 3- (2- Methyl-4-fluorophenyl) -4-hydroxy-5-chloro-6- (4-fluorophenyl) pyrone in the form of a Solid substance with a melting point of 229 to 231 ° C.

Claims (8)

1. 5-halo-3-phenyl-pyrones of the formula
in which
X represents alkyl and
Y represents fluorine, or
X stands for fluorine and
Y represents alkyl,
A stands for halogen and
D represents hydrogen, alkyl, optionally substituted cycloalkyl, optionally substituted aryl or optionally substituted heterocyclyl, or
D for a residue of the formula
stands in what
R represents optionally substituted phenyl,
being the compound of formula
is excluded. 2. A process for the preparation of 5-halogen-3-phenyl-pyrones of the formula (I) according to claim 1, characterized in that carbonyl compounds of the formula

in which
A and D have the meanings given above,
with ketene derivatives of the formula

in which
X and Y have the meanings given above and
Hal represents chlorine or bromine,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid acceptor. 3. Pesticides, fungicidal and herbicidal agents, characterized by a content on at least one 5-halogen-3-phenyl-pyrone of the formula (I) according to An Proverb 1 in addition to extenders and / or surfactants. 4. Use of 5-halogen-3-phenyl-pyrones of the formula (I) according to Claim 1 as pesticides, fungicides and herbicides. 5. A method for controlling animal pests, thereby records that 5-halo-3-phenyl-pyrones of the formula (I) according to An say 1 on the pests and / or their habitat. 6. Process for combating fungi, characterized in that 5- Halogen-3-phenyl-pyrones of the formula (I) according to Claim 1 on the fungi and / or their habitat. 7. Weed control method, characterized in that one 5-halo-3-phenyl-pyrone of the formula (I) according to claim 1 on the Brings out weeds and / or their habitat. 8. Process for the preparation of pesticidal, fungicidal and herbicidal compositions, characterized in that 5-halo-3-phenyl-pyrones of the formula (I) according to claim 1 with extenders and / or surface-active substances mixed.