WO2001072726A1

WO2001072726A1 - Oxime derivatives for controlling undesired microorganisms and animal pests

Info

Publication number: WO2001072726A1
Application number: PCT/EP2001/002860
Authority: WO
Inventors: Markus Heil; Hans-Christian Militzer; Olaf Gebauer; Gerd Hänssler; Karl-Heinz Kuck; Astrid Mauler-Machnik; Ulrike Wachendorff-Neumann
Original assignee: Bayer Aktiengesellschaft
Priority date: 2000-03-27
Filing date: 2001-03-14
Publication date: 2001-10-04
Also published as: EP1274696A1; AU2001252197A1; DE10015015A1; JP2003528866A

Abstract

The invention relates to novel oxime derivatives of formula (I), in which A, R?1, R2, R3 and R4¿ have the meanings as cited in the description. The invention also relates to a method for producing these novel substances and to their use for controlling undesired microorganisms and animal pests.

Description

OXIM DERIVATIVES FOR CONTROLLING UNWANTED MI CROORGANISMS AND ANIMAL PEST

The present invention relates to new oxime derivatives, a process for their preparation and their use for controlling unwanted microorganisms and animal pests.

It has already become known that numerous N- (5-isothiazolyl) -amides or N- (5-thiadiazolyl) -amides have insecticidal and fungicidal properties (cf. WO 97-188, WO 97-26 251 and WO 95 -31 448). The effectiveness of these substances is good, but leaves something to be desired in some cases at low application rates.

There have now been new oxime derivatives of the formula

in which

A represents alkanediyl,

R.1 stands for optionally substituted 1, 2-thiazolyl, 1,2,4-thiadiazolyl or pyridyl,

R.2 represents hydrogen, alkyl or optionally substituted aryl,

R.3 represents hydrogen, alkyl, cycloalkyl, alkoxyalkyl, alkenyl, alkylcarbonyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted arylcarbonyl, optionally substituted heterocyclyl, optionally substituted heterocyclylalkyl or optionally substituted heterocyclylcarbonyl and R ^{4 represents} hydrogen, halogen, alkyl, alkoxy, cyano or nitro.

Furthermore, it has been found that oxime derivatives of the formula (I) can be prepared by using carbonyl compounds of the formula

R_ in which

A, R, R ² and R ^{4 have} the meanings given above,

with an oxyamine of the formula

R ³ -O-NH ₂ (III), in which

R3 has the meaning given above,

or their acid addition complexes,

optionally in the presence of a diluent and optionally in

In the presence of an acid binder.

Finally, it was found that the new oxime derivatives of the formula (I) are very suitable for controlling unwanted microorganisms and animal pests. In particular, they show a strong fungicidal and insecticidal action. Surprisingly, the oxime derivatives of the formula (I) according to the invention have a substantially better fungicidal and insecticidal activity than the constitutionally most similar, known substances of the same action.

Formula (I) provides a general definition of the oxime derivatives according to the invention.

They can optionally be used as mixtures of various possible isomeric forms, in particular stereoisomers, such as e.g. E and Z as well as optical isomers, but optionally also tautomers are present. The invention relates to both the E and the Z isomers, and also the optical isomers, any mixtures of these isomers, and also the possible tautomeric forms.

Oxime derivatives of the formula (I) are preferred in which

A represents alkanediyl having 1 to 4 carbon atoms,

R in each case represents 1,2-thiazolyl, 1,2,4-thiadiazolyl or pyridyl which is optionally mono- or disubstituted by alkyl having 1 to 4 carbon atoms and / or halogen,

R ^ stands for hydrogen, alkyl with 1 to 4 carbon atoms or for aryl with 6 to 10 carbon atoms which is optionally monosubstituted to tetrasubstantially, identically or differently, substituted by halogen and / or alkyl with 1 to 4 carbon atoms,

R ^{3 represents} hydrogen, alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 8

Carbon atoms, alkoxyalkyl having 1 to 4 carbon atoms in the alkoxy part and 1 to 4 carbon atoms in the alkyl part, alkenyl having 2 to 6 carbon atoms or alkylcarbonyl having 1 to 6 carbon atoms in the alkyl part, or represents aryl having 6 to 10 carbon atoms, where each of these radicals can be monosubstituted to tetrasubstituted, identical or different, by halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 4 carbon atoms, each straight-chain or branched Haloalkyl, haloalkoxy or haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms,

or

represents aralkyl having 6 to 10 carbon atoms in the aryl part and 1 to 4 carbon atoms in the alkyl part, where each of these radicals can be substituted up to four times, in the same way or differently, by halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkylthio with each 1 to 4 carbon atoms, each straight-chain or branched

Haloalkyl, haloalkoxy or haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms,

or

represents arylcarbonyl having 6 to 10 carbon atoms in the aryl part, each of these radicals being able to be substituted one to four times, in the same way or differently, by halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 4 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy or haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms,

or represents heterocyclyl with 5 or 6 ring members and 1 to 3 heteroatoms, such as oxygen, nitrogen and / or sulfur, it being possible for these radicals to be monosubstituted to triple, identical or differently substituted by halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 4 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy or haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms,

or

represents heterocyclylalkyl having 5 or 6 ring members and 1 to 3 heteroatoms, such as oxygen, sulfur and / or nitrogen, and 1 to 4 carbon atoms in the alkyl part, where these radicals can optionally be mono- to trisubstituted, identical or differently substituted by halogen, cyano,

Nitro, each straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 4 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy or haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms,

or

represents heterocyclylcarbonyl having 5 or 6 ring members and 1 to 3 heteroatoms, such as oxygen, nitrogen and / or sulfur, it being possible for these radicals to be monosubstituted to triple, identical or differently substituted by halogen, cyano, nitro, in each case straight-chain or branched alkyl , Alkoxy or alkylthio each having 1 to 4 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy or haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, and

R ^{4 represents} hydrogen, alkyl having 1 to 4 carbon atoms or alkoxy having 1 to 4 carbon atoms.

Oxime derivatives of the formula (I) in which

A represents methylene or ethanediyl,

R ^{1 represents} 1,2-thiazolyl which is optionally mono- or disubstituted by methyl, ethyl and / or chlorine or represents 1,2,4-thiadiazolyl which is optionally substituted by methyl, ethyl or chlorine or optionally mono- or disubstituted by methyl, ethyl and / or chlorine-substituted pyridyl,

R represents hydrogen, methyl, ethyl or phenyl which is optionally mono- or disubstituted, identical or different, substituted by methyl, ethyl and / or chlorine,

R ³ for hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, sec-butyl, i-butyl, tert-butyl, cyclopentyl, cyclohexyl, methoxymethyl, allyl, acetyl, propionyl, pivaloyl or 3, 3-dimethyl-butanoyl, or

represents phenyl, benzyl, benzoyl, pyridyl, pyridylmethyl or pyridylcarbonyl, where each of these radicals can be substituted once to three times, identically or differently, by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, methylthio, ethylthio, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio and / or trifluoromethyl and

R ^{4 represents} hydrogen, methyl, ethyl, methoxy or ethoxy.

Oxime derivatives of the formula (I) in which

A represents methylene or ethanediyl,

R ^{1 represents 1} , 2-thiazol-5-yl which is optionally mono- or disubstituted by methyl, ethyl and / or chlorine, or is optionally substituted by methyl,

Stands for ethyl or chlorine-substituted 1,2,4-thiadiazol-5-yl, or for pyridyl which is optionally mono- or disubstituted by methyl, ethyl and / or chlorine,

R ^{2 represents} hydrogen, methyl, ethyl or phenyl,

R ^{3 is} hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, sec-butyl, i-butyl, tert-butyl, cyclopentyl, cyclohexyl, methoxymethyl, allyl, acetyl, propionyl, pivaloyl or 3,3 , -Dimethylbutanoyl, or represents phenyl, benzyl, benzoyl, pyridyl, pyridylmethyl or pyridylcarbonyl, where each of these radicals can be monosubstituted to triple, identical or differently substituted by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl , n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, methylthio, ethylthio, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethyl or trifluoromethyl / trifluoromethyl .

and

R ^{4 represents} hydrogen, methyl or methoxy. The aforementioned radical definitions can be combined with one another in any way. In addition, individual meanings can also be omitted.

If 2- (3-acetyl-phenyl) -N- (3-methyl-1, 2,4-thiadiazol-5-yl) acetamide and methoxyamine hydrochloride are used as starting materials, the course of the process according to the invention can be determined by the following Formula scheme can be illustrated.

Formula (II) provides a general definition of the carbonyl compounds required as starting materials when carrying out the process according to the invention. In this formula, A, R ¹ , R ² and R ⁴ preferably or particularly preferably have those meanings which, in connection with the description of the substances of the formula (I) according to the invention, are preferred or particularly preferred for these radicals or this index were called.

The carbonyl compounds of the formula (II) are known or can be prepared by known methods (cf. DE-A 198 46 008). This gives carbonyl compounds of the formula (II) if carboxylic acid halides of the formula

in which

A, R, R ² and R ^{4 have} the meanings given above and

X represents halogen,

with amines of the formula

R! -NH (V), in which

R has the meaning given above,

if appropriate in the presence of a diluent and if appropriate in the presence of a base.

Formula (IV) provides a general definition of the carboxylic acid halides required as starting materials for the preparation of the carbonyl compounds of the formula (II). In this formula, A and R ^ and R ^ preferably have those meanings which have already been mentioned as preferred for these radicals or this index in connection with the description of the substances of the formula (I) according to the invention. X preferably represents chlorine or bromine.

The carboxylic acid halides of the formula (IV) are known or can be prepared by known methods (cf. Bull.Soc.Chim.Belg. 70, (1961) 95 or

Bull.Soc.Chim.Fr. 1970, 4452-4456). Formula (V) provides a general definition of the amines which are further required as starting materials for the preparation of the carbonyl compounds of the formula (II). In this formula (V), R preferably has those meanings which have already been mentioned as preferred for this radical in connection with the description of the compounds of the formula (I) according to the invention.

The amines of the formula (V) are known or can be prepared by known methods (cf., for example, DE-A 4 328 425, DE-A 2 249 162, WO 93-19 054, WO 94-21 617, J. Het. Chem. 26, 1575 (1989), Gazz. Chim. Ital. 107, 1 (1977), Chem. Ber. 195, 57, EP-A 0 455 356 and Chem. Pharm. Bull. 45 (1997) , 1027-1038).

Formula (III) provides a general definition of the oxyamines required as starting materials for carrying out the process according to the invention. In this formula (III), R ³ preferably has those meanings which have already been mentioned as preferred for this radical in connection with the description of the compounds of the formula (I) according to the invention.

The oxyamines of the formula (III) and also their acid addition complexes, such as hydrogen chloride addition complexes, are known or can be prepared by known methods.

Suitable diluents for carrying out the process according to the invention are all inert, organic solvents. Aliphatic, alicyclic or aromatic hydrocarbons such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin can preferably be used; halogenated hydrocarbons, such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; Ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; Nitriles, such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; Esters such as methyl acetate or ethyl acetate; Sulfoxides such as dimethyl sulfoxide; Sulfones such as sulfolane; Alcohols, such as methanol, ethanol, n- or i-propanol, n-, i-, sec- or tert-butanol, ethanediol, propane-1,2-diol, ethoxyethanol, methoxyethanol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, and also mixtures thereof Water or pure

Water.

Suitable acid binders for carrying out the process according to the invention are all customary inorganic and organic bases. Alkaline earth metal or alkali metal hydrides, hydroxides, amides,

alcoholates, acetates, carbonates or bicarbonates, such as sodium hydride, sodium amide, sodium methylate, sodium ethylate, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, sodium acetate, potassium acetate, calcium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate and sodium hydrogen carbonate, furthermore ammonium compounds, such as ammonium hydroxide, ammonium acetate and ammonium carbonate, and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, N-dimethylbenzylamine, pyridine, N- Methylpiperidine, N-methylmorpholine, N, N-dimethylaminopyridine, diazabicycloctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecene (DBU) or polymeric bases, such as basic ion exchangers.

The reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between 0 ° C and 150 ° C, preferably between 0 ° C and 80 ° C.

The process according to the invention is generally carried out under atmospheric pressure. However, it is also possible to work under increased or reduced pressure.

When carrying out the process according to the invention, 1 mol is used

Carbonyl compound of formula (II) generally 1 to 15 mol, preferably 1 up to 8 moles of oxyamine of the formula (III) or of its acid addition complex. The processing takes place according to usual methods.

The substances according to the invention have a strong microbicidal action and can be used to control unwanted microorganisms, such as fungi and

Bacteria can be used in crop protection and material protection.

Fungicides can be used to protect plants against Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.

Bactericides can be used in crop protection to combat Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.

Some pathogens of fungal and bacterial diseases that fall under the generic names listed above may be mentioned as examples, but not by way of limitation:

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 fact that the active compounds are well tolerated by plants in the concentrations required to combat plant diseases allows treatment above ground

Parts of plants, of seedlings, and of the soil.

The active compounds according to the invention can be particularly successful

Combating cereal diseases, such as against Erysiphe or Puccinia species, diseases in wine, fruit and vegetable growing, such as against Venturia, Uncinula and Podosphaera species, or rice diseases, such as against Pyricularia species, use , The active compounds according to the invention are also suitable for increasing the crop yield. They are also less toxic and have good plant tolerance.

If appropriate, the active compounds according to the invention can also be used in certain concentrations and application rates as herbicides, for influencing plant growth and for controlling animal pests. If appropriate, they can also be used as intermediates and precursors for the synthesis of further active compounds.

According to the invention, all plants and parts of plants can be treated. Under

Plants are understood to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeders' rights. Plant parts are to be understood to mean all above-ground and underground parts and organs of plants, such as shoots, leaves, flowers and roots, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds and roots, tubers and rhizomes become. The plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.

The treatment of the plants and parts of plants with the active compounds according to the invention is carried out directly or by acting on their surroundings, living space or storage space according to the customary treatment methods, for example by dipping, spraying, evaporating, atomizing, scattering, spreading and in the case of propagation material, in particular seeds single or multi-layer wrapping. In material protection, the substances according to the invention can be used to protect technical materials against attack and destruction by undesired microorganisms.

In the present context, technical materials include non-living ones

Understand materials that have been prepared for use in the art. For example, technical materials which are to be protected against microbial change or destruction by active substances according to the invention can be adhesives, glues, paper and cardboard, textiles, leather, wood, paints and plastic articles, cooling lubricants and other materials which can be attacked or decomposed by microorganisms , In the context of the materials to be protected, parts of production plants, for example cooling water circuits, are also mentioned which can be impaired by the multiplication of microorganisms. In the context of the present invention, technical materials are preferably adhesives, glues, papers and cartons, leather, wood, paints, cooling lubricants and heat transfer liquids, particularly preferably wood.

For example, microorganisms of the following genera may be mentioned:

Alternaria, such as Alternaria tenuis, Aspergillus, such as Aspergillus niger, Chaetomium, such as Chaetomium globosum, Coniophora, such as Coniophora puetana, Lentinus, such as Lentinus tigrinus,

Penicillium, such as Penicillium versicolor, Aureobasidium, such as Aureobasidium pullulans, Sclerophoma, such as Sclerophoma pityophila, Trichoderma, such as Trichoderma viride, Escherichia, such as Escherichia coli,

Pseudomonas, such as Pseudomonas aeruginosa, Staphylococcus, such as Staphylococcus aureus.

The active compounds according to the invention are, with good plant tolerance and favorable toxicity to warm-blooded animals, also suitable for controlling animal pests, in particular insects, arachnids and nematodes, which are used in agriculture, in forestry, in horticulture, in the protection of stocks and materials, and in the hygiene sector or in veterinary medicine Range occur. The substances are effective against normally sensitive and resistant species and against pests in all or individual stages of development. The animal pests mentioned above include:

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

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

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

From the order of the Symphyla e.g. Scutigerella immaculata. From the order of the Thysanura e.g. Lepisma saccharina.

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

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

From the order of the Dermaptera e.g. Forficula auricularia. From the order of the Isoptera e.g. Reticulitermes spp ..

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

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

From the order of the Thysanoptera, for example Hercinothrips femoralis, Thrips tabaci. From the order of the Heteroptera, for example Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.

From the order of the Homoptera e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus sppe, Phosophosumon - siphum 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 e.g. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiisispppp., Phyllocnistia. Phyllocnist.

Earias insulana, Heliothis spp., Spodoptera exigua, Mamestra brassicae, Panolis flammea, Spodoptera litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kellaelliehnelliaellaellaiellaella bella , Tinea pellionella, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella,

Homona magnanima, Tortrix viridana.

From the order of the Coleoptera, for example, Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrisousisamasppas, Atomic spp. , Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus holpp., Ptinus holpp. Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica.

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

From the order of the Diptera e.g. Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa.

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

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

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

Plant-parasitic nematodes include e.g. Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp.

The substances which can be used according to the invention can be used with particularly good success for controlling plant-damaging mites, such as against the bean spider mite (Tetranychus urticae), or for combating plant-damaging insects. as against larvae of horseradish leaf beetle (Phaedon cochleariae) and green peach aphid (Mycus persicae).

In addition, the compounds of formula (I) according to the invention also have very good antifungal effects. They have a very broad spectrum of antimycotic effects, in particular against dermatophytes and shoot fungi, mold and diphasic fungi (for example against Candida species such as Candida albicans, Candida glabrata) such as Epidermophyton floccosum, Aspergillus species such as Aspergillus niger and Aspergillus fumigatus fumigatus such as Trichophyton mentagrophytes, Microsporon species, such as Microsporon canis and audouinii. The list of these fungi is in no way a limitation of the detectable mycotic spectrum, but is only of an explanatory nature.

Depending on their respective physical and / or chemical properties, the active compounds can be converted into the customary formulations, such as

Solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in coating compositions for seeds, as well as ULV cold and warm mist formulations.

These formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents. If water is used as an extender, e.g. organic solvents can also be used as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. Petroleum fractions, 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 solution medium, such as dimethylformamide and dimethyl sulfoxide, and water. Liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide. The following are suitable as solid carriers: for example, 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. Possible solid carriers for granules are: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well as synthetic granules made from inorganic and organic flours as well as granules made from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks. Suitable emulsifiers and / or foaming agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates. As dispersants come in

Question: e.g. Lignin sulfite liquor and methyl cellulose.

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

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

The formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%. The active compounds according to the invention, as such or in their formulations, can also be used in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, in order, for example, to broaden the activity spectrum or to prevent the development of resistance. In many cases, synergistic effects are obtained, ie the effectiveness of the mixture is greater than the effectiveness of the individual components.

For example, the following substances can be used as mixing partners:

fungicides:

Aldimorph, ampropylfos, ampropylfos potassium, andoprim, anilazine, azaconazole, azoxystrobin,

Benalaxyl, benodanil, benomyl, benzamacril, benzamacrylic isobutyl, bialaphos, binapacrylic, biphenyl, bitertanol, blasticidin-S, bromuconazole, bupirimate, buthiobate,

Calcium polysulfide, capsimycin, captafol, captan, carbendazim, carboxin, carvone, quinomethionate (quinomethionate), chlobenthiazon, chlorfenazole, chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon, cufraneb, cymoxanil, cyphodaminazol, cypodaminazol, cypodamconazol, cypodamconazol

Debacarb, dichlorophene, diclobutrazole, diclofluanide, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomo h, diniconazole, diniconazol-M, dinocap, diphenylamine, dipyrithione, ditalimfos, dorphianoxin, dithianonodonone, dithianonodonone

Ediphenphos, Epoxiconazole, Etaconazole, Ethirimol, Etridiazole,

Famoxadone, fenapanil, fenarimol, fenbuconazole, fenfuram, fenitropan, fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam, ferimzone,

Fluazinam, flumetover, fluoromid, fluquinconazole, flurprimidol, flusilazole,

Flusulfamide, flutolanil, flutriafol, folpet, fosetyl-aluminum, fosetyl-sodium, Fthalide, fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole, furconazole-cis, furmecyclox, fenhexamide,

guazatine,

Hexachlorobenzene, hexaconazole, hymexazole,

Imazalil, Imibenconazol, Iminoctadin, Iminoctadinealbesilat, Iminoctadinetriacetat, Iodocarb, Ipconazol, Iprobefos (EBP), Iprodione, Irumamycin, Isoprothiolan, Isovaledione, Iprovalicarb,

Kasugamycin, Kresoxim-methyl, copper preparations, such as: copper hydroxide, copper phthalate, copper oxychloride, copper sulfate, copper oxide, oxy-copper and Bordeaux mixture,

Mancopper, Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl,

Metconazole, methasulfocarb, methfuroxam, metiram, metomeclam, metsulfovax, mildiomycin, myclobutanil, myclozolin,

Nickel dimethyldithiocarbamate, nitrothal isopropyl, Nuarimol,

Oftirace, Oxadixyl, Oxamocarb, Oxolinicacid, Oxycarboxim, Oxyfenthiin,

Paclobutrazole, Pefürazoat, Penconazol, Pencycuron, Phosdiphen, Pimaricin, Piperalin, Polyoxin, Polyoxorim, probenazole, Prochloraz, Procymidon, Propamocarb, Propanosine-Sodium, Propiconazole, Propineb, Pyrazophos, Pyrifenox, Pyrimethanil

Pyroquilon, Pyroxyfur,

Quinconazole, quintozen (PCNB), quinoxyfen,

Sulfur and sulfur preparations, spiroxamines,

Tebuconazole, tecloftalam, tecnazene, Tetcyclacis, tetraconazole, thiabendazole, Thicyofen, Thifluzamide, thiophanate-methyl, thiram, Tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, Triazbutil, triazoxide, Trichlamid, tricyclazole, Tridemoφh, triflumizole, triforine, triticonazole, trifloxystrobin, uniconazole

Validamycin A, vinclozolin, viniconazole,

Zarilamid, Zineb, Ziram as well

Dagger G, OK-8705,

OK-8801, α- (1, 1-dimethylethyl) -ß- (2-phenoxyethyl) - 1 H-1, 2,4-triazole-1-ethanol, α- (2,4-dichloφhenyl) -ß-fluorine -b-propyl-1 H-1, 2,4-triazole-1-ethanol, α- (2,4-dichloφhenyl) -ß-methoxy-a-methyl-1 H-1, 2,4-triazole-1 -ethanol, α- (5-methyl-1, 3-dioxan-5-yl) -ß - [[4- (trifluoromethyl) phenyl] methylene] - 1 H- 1, 2,4-triazol-1 - ethanol,

(5RS, 6RS) -6-hydroxy-2,2,7,7-tetramethyl-5- (lH-l, 2,4-triazol-l-yl) -3-octanone,

(E) -a- (methoxyimino) -N-methyl-2-phenoxy-phenylacetamide, l- (2,4-dichloro-phenyl) -2- (lH-l, 2,4-triazol-l-yl) -ethanone- O- (phenylmethyl) oxime, 1 - (2-methyl-1-naphthalenyl) - 1 H-ρyrrol-2,5-dione, l- (3,5-dichloro-phenyl) -3- (2-propenyl) -2 , 5-pyrrolidinedione, l - [(diiodomethyl) sulfonyl] -4-methyl-benzene, l - [[2- (2,4-dichloφhenyl) -l, 3-dioxolan-2-yl] methyl] -lH -imidazole, l - [[2- (4-Chlθφhenyl) -3-phenyloxiranyl] methyl] -lH-l, 2,4-triazole, 1 - [1 - [2- [(2, 4-dichloφhenyl) - methoxy] phenyl] ethenyl] - 1 H-imidazole, 1-methyl-5-nonyl-2- (phenylmethyl) -3-pyrrolidinol,

2 ', 6'-dibromo-2-methyl-4'-trifluoromethoxy-4'-trifluoro-methyl-l, 3-thiazol-5-carboxanilide,

2,6-dichloro-5- (methylthio) -4-pyrimidinyl thiocyanate,

2,6-dichloro-N- (4-trifluoromethylbenzyl) benzamide, 2,6-dichloro-N - [[4- (trifluoromethyl) phenyl] methyl] benzamide,

2- (2,3,3-triiodo-2-propenyl) -2H-tetrazole,

2 - [(l-methylethyl) sulphonyl] -5- (trichloromethyl) -l, 3,4-thiadiazole,

2 - [[6-Deoxy-4-O- (4-O-methyl-ß-D-glycopyranosyl) -aD-glucopyranosyl] -amino] -4- methoxy-lH-pyrrolo [2,3-d] pyrimidine- 5-carbonitrile, 2-aminobutane, 2-bromo-2- (bromomethyl) -pentandinitril,

2-chloro-N- (2,3-dihydro-l, l, 3-trimethyl-lH-inden-4-yl) -3-pyridine carboxamide,

2-chloro-N- (2,6-dimethylphenyl) -N- (isothiocyanatomethyl) -acetamide,

2-phenylphenol (OPP), 3, 4-dichloro-1 - [4- (difluoromethoxy) phenyl] - 1 H-pyrrole-2,5-dione,

3,5-dichloro-N- [cyano [(l-methyl-2-propynyl) -oxy] -methyl] -benzamide,

3- (1,1-dimethylpropyl-1-oxo-1 H-indene-2-carbonitrile,

3- [2- (4-Chlθφhenyl) -5-ethoxy-3-isoxazolidinyl] -pyridine,

4-chloro-2-cyan-N, N-dimethyl-5- (4-methylphenyl) -lH-imidazole-l-sulfonamide, 4-methyl-tetrazolo [1, 5-a] quinazolin-5 (4H) -one .

8-hydroxyquinoline sulfate,

9H-xanthene-9-carboxylic acid 2 - [(phenylamino) carbonyl] hydrazide, bis- (l-methylethyl) -3-methyl-4 - [(3-methylbenzoyl) -oxy] -2,5-thiophene dicarboxylate, ice-1 - (4-chloro-phenyl) -2- (1 H-1, 2,4-triazole-1-yl) -cycloheptanol, cis-4- [3- [4- (1,1-dimethylpropyl) -phenyl -2-methylpropyl] -2,6-dimethyl-moφholin hydrochloride,

Ethyl - [(4-chloφhenyl) azo] cyanoacetate,

potassium bicarbonate,

Methane tetrathiol sodium salt, methyl 1 - (2,3-dihydro-2,2-dimethyl-1H-inden-1-yl) - 1 H-imidazole-5-carboxylate,

Methyl-N- (2,6-dimethylphenyl) -N- (5-isoxazolylcarbonyl) -DL-alaninate,

Methyl N- (chloroacetyl) -N- (2,6-dimethylphenyl) -DL-alaninate,

N- (2,6-dimethylphenyl) -2-methoxy-N- (tetrahydro-2-oxo-3-furanyl) acetamide,

N- (2,6-dimethylphenyl) -2-methoxy-N- (tetrahydro-2-oxo-3-thienyl) acetamide, N- (2-chloro-4-nitrophenyl) -4-methyl-3-nitro- benzenesulfonamide,

N- (4-Cyclohexyl-phenyl) -l, 4,5,6-tetrahydro-2-pyrimidinamine,

N- (4-hexylphenyl) - 1, 4,5,6-tetrahydro-2-pyrimidinamine,

N- (5-chloro-2-methylphenyl) -2-methoxy-N- (2-oxo-3-oxazolidinyl) -acetamide,

N- (6-methoxy) -3-pyridinyl) cyclopropanecarboxamide, N- [2,2,2-trichloro-l - [(chloroacetyl) amino] ethyl] benzamide,

N- [3-chloro-4,5-bis- (2-propynyloxy) -phenyl] -N'-methoxy-methanimidamid, N-formyl-N-hydroxy-DL-alanine sodium salt,

O, O-diethyl- [2- (dipropylamino) -2-oxoethyl] ethylphosphoramidothioate, O-methyl-S-phenyl-phenylpropylphosphoramidothioate, S-methyl-1, 2,3-benzothiadiazole-7-carbothioate, spiro [2H] - 1-benzopyran-2, 1 '(3Η) -isobenzofuran] -3'-one,

bactericides:

Bronopol, dichlorophene, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furan carboxylic acid, oxytetracycline, probenazole, streptomycin, teclofalam, copper sulfate and other copper preparations.

Insecticides / acaricides / nematicides:

Abamectin, Acephate, Acetamiprid, Acrinathrin, Alanycarb, Aldicarb, Aldoxycarb,

Alpha-cypermethrin, Alphamethrin, Amitraz, Avermectin, AZ 60541, Azadirachtin, Azamethiphos, Azinphos A, Azinphos M, Azocyclotin,

Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillus thuringiensis, Baculoviruses, Beauveria bassiana, Beauveria tenella, Bendiocarb, Benfüracarb,

Bensultap, Benzoximate, Betacyfluthrin, Bifenazate, Bifenthrin, Bioethanomethrin, Biopermethrin, BPMC, Bromophos A, Bufencarb, Buprofezin, Butathiofos, Butocarboxim, Butylpyridaben,

Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap,

Chloethocarb, Chlorethoxyfos, Chlorfenapyr, Chlorfenvinphos, Chlorfluazuron, Chlormephos, Chloφyrifos, Chloφyrifos M, Chlovaporthrin, Cis-Resmethrin, Cispermethrin, Clocythrin, Cloethocarb, Clofentezine, Cyanophoputhrin, Cycloprin, Cyprin, Cyprin, Cyprin Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Diazinon, Dichlorvos, Diflubenzuron, Dimethoat, Dimethylvinphos, Diofenolan, Disulfoton, Docusat-sodium, Dofenapyn,

Eflusilanate, Emamectin, Empenthrin, Endosulfan, Entomopfthora spp., Esfenvalerate, Ethiofencarb, Ethion, Ethoprophos, Etofenprox, Etoxazole, Etrimfos,

Fenamiphos, Fenazaquin, Fenbutatin oxide, Fenitrothion, Fenothiocarb, Fenoxacrim, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyrithrin, Fenpyroximate, Fenvalerate, Fipronil, Fluazuron, Flubrocythrinate, Flucycloxuron, Flucytoxin,

Flutenzine, Fluvalinate, Fonophos, Fosmethilan, Fosthiazate, Fubfenprox, Furathio-carb,

granulosis

Halofenozide, HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene,

Imidacloprid, isazofos, isofenphos, isoxathion, ivermectin,

nucleopolyhedroviruses

Lambda cyhalothrin, lufenuron

Malathion, mecarbam, metaldehyde, methamidophos, metharhilic anisopliae, metharhilic flavoviride, methidathione, methiocarb, methomyl, methoxyfenozide,

Metolcarb, Metoxadiazone, Mevinphos, Milbemectin, Monocrotophos,

Naled, Nitenpyram, Nithiazine, Novaluron

Omethoate, Oxamyl, Oxydemethon M

Paecilomyces fumosoroseus, Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos A, Pirimiphos M, Profenofos, Promecarb, Propoxur, Prothiofos, Prothoat, Pyromhrhridosine, Pymmethrofinos, Pymmethrofinos , Pyridathione, pyrimidifene,

pyriproxyfen, quinalphos,

ribavirin

Salithion, Sebufos, Silafluofen, Spinosad, Sulfotep, Sulprofos,

Tau fluvalinate, tebufenozide, tebufenpyrad, tebupirimiphos, teflubenzuron, tefluthrin, temephos, temivinphos, terbufos, tetrachlorvinphos, theta-cypermethrin, thiacloprid, thiamethoxam, thiapronilarbox, thiapronil, thiapronil, thiapronil, thiapronil, thiapronil, thiapronil, thiapronil, thiapronil, thiapronil Triazamate, triazophos, triazuron, trichlophenidines, trichlorfon, triflumuron, trimethacarb,

Vamidothion, Vaniliprole, Verticillium lecanii

Yl 5302

Zeta-cypermethrin, zolaprofos (IR-cis) - [5- (phenylmethyl) -3-furanyl] methyl-3 - [(dihydro-2-oxo-3 (2H) - furanylidene) methyl] -2,2- dimethylcyclopropanecarboxylate

(3-phenoxyphenyl) methyl 2,2,3,3-tetramethylcyclopropane decarboxylate l - [(2-chloro-5-thiazolyl) methyl] tetrahydro-3,5-dimethyl-N-nitro-l, 3,5-triazine -2 (1H) - imine 2- (2-chloro-6-fluorophene) -4- [4- (l, l-dimethylethyl) phenyl] -4,5-dihydro-oxazole

2- (Acetlyoxy) -3-dodecyl-l, 4-naphthalenedione

2-chloro-N - [[[4- (l-phenylethoxy) phenyl] amino] carbonyl] -benzamide

2-chloro-N - [[[4- (2,2-dichloro-l, l-difluoroethoxy) -phenyl] -amino] -carbonyl] -benzamide

3-methylphenyl propyl carbamate 4- [4- (4-ethoxyphenyl) -4-methylpentyl] -1-fluoro-2-phenoxy-benzene

4-chloro-2- (l, l-dimethylethyl) -5 - [[2- (2,6-dimethyl-4-phenoxyphenoxy) ethyl] thio] -

3 (2H) pyridazinone

4-chloro-2- (2-chloro-2-methylpropyl) -5 - [(6-iodo-3-pyridinyl) methoxy] -3 (2H) - pyridazinone 4-chloro-5 - [(6-chloro-3 -pyridinyl) methoxy] -2- (3,4-dichlθφhenyl) -3 (2H) -pyridazinone Bacillus thuringiensis strain EG-2348

Benzoic acid [2-benzoyl-1 - (1, 1-dimethylethyl) hydrazide

Butanoic acid 2,2-dimethyl-3- (2,4-dichloφhenyl) -2-oxo-l-oxaspiro [4.5] dec-3-en-4-yl ester [3 - [(6-chloro-3-pyridinyl ) methyl] -2-thiazolidinylidene] -cyanamide

Dihydro-2- (nitromethylene) -2H- 1,3-thiazine-3 (4H) -carboxaldehyde

Ethyl [2 - [[l, 6-dihydro-6-oxo-l- (phenylmethyl) -4-pyridazinyl] oxy] ethyl] carbamate

N- (3,4,4-trifluoro-l-oxo-3-butenyl) -glycine

N- (4-Chlorophenyl) -3- [4- (difluoromethoxy) phenyl] -4,5-dihydro-4-phenyl-1H-pyrazole-1-carboxamide

N - [(2-chloro-5-thiazolyl) methyl] -N'-methyl-N "-nitro-guanidine

N-methyl-N '- (l-methyl-2-propenyl) -l, 2-hydrazindicarbothioamid

N-methyl-N'-2-propenyl-1, 2-hydrazine dicarbothioamide

O, O-diethyl [2- (dipropylamino) -2-oxoethyl] -ethylphosphoramidothioat

A mixture with other known active ingredients, such as herbicides or with

Fertilizers and growth regulators are possible.

The active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules. They are used in the usual way, e.g. by pouring, spraying, atomizing, scattering, dusting, foaming, brushing, etc. It is also possible to apply the active ingredients by the ultra-low-volume method or to inject the active ingredient preparation or the active ingredient itself into the soil. It can also do that

Seeds of the plants are treated.

When using the active compounds according to the invention as fungicides, the application rates can be varied within a relatively wide range, depending on the type of application. In the treatment of parts of plants, the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g / ha. In the case of seed treatment, the active compound application rates are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed. In the treatment of the soil, the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha.

The agents used to protect industrial materials generally contain the active ingredients in an amount of 1 to 95%, preferably 10 to 75%.

The application concentrations of the active compounds according to the invention depend on the type and the occurrence of the microorganisms to be controlled and on the composition of the material to be protected. The optimal amount can be determined by test series. In general, the application concentrations are in the range from 0.001 to 5% by weight, preferably from 0.05 to 1.0% by weight, based on the material to be protected.

The effectiveness and the spectrum of activity of the active substances to be used according to the invention in the protection of materials or of the agents, concentrates or formulations which can be prepared therefrom can be increased if further antimicrobial compounds, fungicides, bactericides, herbicides are used, if appropriate

Insecticides or other active ingredients to enlarge the spectrum of activity or to achieve special effects such as added protection against insects. These mixtures can have a broader spectrum of activity than the compounds according to the invention.

When used against animal pests, the substances according to the invention can also be present in commercially available formulations and in the use forms prepared from these formulations as a mixture with synergists. Synergists are compounds that increase the effectiveness of the active ingredients without the added synergist itself having to be active. The active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges. The active substance concentration of the use forms can be from 0.0000001 to 95% by weight of active substance, preferably between 0.0001 and 1% by weight.

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

When used against hygiene pests and pests of stored products, the active substance is distinguished by an excellent residual action on Hilz and clay as well as a good stability to alkali on limed substrates.

As already mentioned above, all plants and their parts can be treated according to the invention. In a preferred embodiment, wild or conventional conventional breeding methods, such as crossbreeding or

Protoplast fusion obtained plant species and plant varieties and their parts treated. In a further preferred embodiment, transgenic plants and plant cultivars which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (genetic modified organisms) and their parts are treated. The term "parts" or "parts of plants" or "plant parts" was explained above.

Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention.

Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, growing season, nutrition), the treatment according to the invention can also result in superadditive ("synergistic") effects. For example, reduced application rates and / or widening of the activity spectrum and / or an increase in the action of the substances and agents which can be used according to the invention, better plant growth, increased tolerance to High or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripeness, higher harvest yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvested products possible that go beyond the expected effects.

The preferred transgenic (genetically engineered) plants or plant cultivars to be treated according to the invention include all plants which, by virtue of the genetic engineering modification, contain genetic material which contains them

Gives plants special beneficial valuable properties ("traits"). Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated ripening, higher crop yields, higher quality and / or higher

Nutritional value of the harvested products, higher shelf life and / or workability of the harvested products. Further and particularly highlighted examples of such properties are an increased defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and / or viruses, and an increased tolerance of the plants to certain herbicidal active ingredients. Examples of transgenic plants are the important cultivated plants, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with corn, soybeans, potatoes , Cotton and rapeseed are particularly highlighted. The traits are particularly emphasized as the increased defense of the plants against insects by toxins arising in the plants, in particular those which are caused by the genetic material from Bacillus Thuringenisis (eg by the genes CryΙA (a), CryΙA (b ), CryΙA (c), CryllA, CrylllA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF as well as their combinations) are produced in the plants (hereinafter "Bt plants"). The increased tolerance of the plants is also particularly emphasized as traits against certain herbicidal active ingredients, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (for example "PAT" gene). The genes imparting the desired properties (“traits”) can also occur in combinations with one another in the transgenic plants. Examples of "Bt plants" are corn varieties, cotton varieties, soy varieties and potato varieties that are sold under the trade names YIELD GARD® (e.g. corn, cotton, soy), KnockOut® (e.g. corn), StarLink® (e.g. corn), Bollgard® ( Cotton), Nucoton® (cotton) and NewLeaf® (potato). Examples of herbicide-tolerant plants are maize varieties, cotton varieties and soy varieties which are sold under the trade names Roundup Ready®

(Tolerance to glyphosate e.g. corn, cotton, soy), Liberty Link® (tolerance to phosphinotricin, e.g. rapeseed), IMI® (tolerance to imidazolinones) and STS® (tolerance to sulfonylureas e.g. corn). The herbicide-resistant plants (conventionally bred to herbicide tolerance) include the varieties sold under the name Clearfield® (e.g. maize). Of course, these statements also apply to plant varieties developed in the future or coming onto the market in the future with these or future-developed genetic properties ("traits").

The plants listed can be particularly advantageous according to the invention with the

Compounds of the general formula (I) or the active compound mixtures according to the invention are treated. The preferred ranges given above for the active substances or mixtures also apply to the treatment of these plants. Plant treatment with the compounds or mixtures specifically listed in the present text should be particularly emphasized.

The preparation and use of substances according to the invention are illustrated by the following examples. Preparation Examples

example 1

413 mg (0.0015 mol) of 2- (3-acetylphenyl) -N- (3-methyl-l, 2,4-thiadiazol-5-yl) acetamide, 251 mg (0.003 mol) of methoxyamine hydrochloride and 300 mg of a basic ion exchanger in 20 ml of ethanol are stirred at room temperature for 18 hours. The reaction mixture is then filtered and the filtrate is concentrated under reduced pressure. The remaining residue is stirred with diethyl ether. The resulting solid product is filtered off, washed with diethyl ether and dried.

279 mg (99% of theory) of 2- {3 - [(lZ) -N-methoxyethanimidoyl] - phenyl} -N- (3-methyl-1, 2,4-thiadiazol-5-yl) acetamide are obtained.

HPLC: logP = 2.25

The oxime derivatives of the formulas (Ia) or (Ib) listed in Table 1 below are also prepared by the methods given above.

Table 1:

and

Table 1 (continued)

Table 1 (continued)

Table 1 (continued)

Table 1 (continued)

Table 1 (continued)

Example A R * R2 R logP Mp. (° C): For¬

No. mel

41 -CH ₂ - -CH ₃ -CH ₃ 2.6

H ₃ C Ib

N - S

42 -CH ₂ - -CH ₃ -C ₂ H ₅

H ₃ C - 2.99 Ib

N - S

43 -CH ₂ - -CH ₃ -H 1.87 Ib

H ₃ C

N - S

44 -CH ₂ - -CH ₃ -C 2oH ^L 5 2.51 Ia

45 -CH ₂ - -CH ₃ 6-chloro-3- 2.6 Ia pyridylmethyl

46 -CH ₂ - -CH ₃ t-butyl 3.52 Ia

47 -CH ₂ - -CH ₃ allyl 2.62 Ia

48 -CH ₂ - -CH ₃ i-butyl 3.43 Ia

Table 1 (continued)

The logP values were determined in accordance with EEC Directive 79/831 Annex V. A8 by HPLC (gradient method, acetonitrile / 0, 1% aqueous phosphoric acid).

Production of intermediates of formula (II)

Example 51

7.9 g are stirred into a mixture of 4.6 g (40 mmol) of 5-amino-3-methyl-l, 2,4-thiadiazole and 12.8 g (162 mmol) of pyridine in 50 ml of dichloromethane at room temperature (40 mmol) 3-acetyl-phenylacetic acid chloride in 20 ml dichloromethane. The reaction mixture is stirred for 16 hours at room temperature, then 20 mg of 4-dimethylaminopyridine are added and the mixture is stirred for a further 24 hours at room temperature. The reaction mixture is then washed with 1N hydrochloric acid, dried over sodium sulfate and concentrated under reduced pressure. By stirring the residue obtained with diethyl ether, 5.5 g (50% of theory) of 2- (3-acetylphenyl) -N- (3-methyl-l, 2,4-thiadiazol-5-yl) acetamide in the form of a Solid substance isolated.

Mp 91-98 ° C

HPLC: log P (pH 2.3) = 1.56

Example 52

To a solution of 1.566 g (10 mmol) of 3-chloro-2-ethyl-4-pyridinamine and 1.782 g (10 mmol) of 3-acetyl-phenylacetic acid in 50 ml of dichloroethane are added 3.661 g (11 mmol) of benzotriazol-l-yloxytris (dimethylamino) phosphonium chloride and 1.5 g triethylamine and stirred at 80 ° C for 16 hours. The reaction solution is subsequently washed first with 1N-HC1 and then with 5% aqueous sodium hydrogen carbonate solution, then dried over sodium sulfate and concentrated under reduced pressure. The residue is stirred with 5% aqueous sodium hydrogen carbonate solution and the solid product obtained is suction filtered. This is now chromatographed on silica gel using n-hexane / ethyl acetate. 1.6 g (47.5% of theory) of 2- (3-acetylphenyl) -N- (3-chloro-2-ethyl-4-pyridinyl) acetamide are obtained.

HPLC: log P (pH 2.3) = 1.33

use Examples

Example A

Podosphaera test (apple) / protective

Solvent: 24.5 parts by weight of acetone

24.5 parts by weight of dimethylacetamide emulsifier: 1.0 part by weight of alkyl aryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.

To test for protective activity, young plants are sprayed with the active compound preparation in the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of the apple mildew pathogen Podosphaera leucotricha. The plants are then placed in a greenhouse at approx. 23 ° C and a relative humidity of approx. 70%.

Evaluation is carried out 10 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.

Active substances, application rates and test results are shown in the following table. Table A

Podosphaera test (apple) / protective

Table A (continued)

Table A (continued)

Table A (continued)

Example B

Uncinula test (vine) / protective

Solvent: 24.5 parts by weight of acetone

To test for protective activity, young plants are sprayed with the active compound preparation in the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Uncinula necator. The plants are then placed in the greenhouse at about 23 ° C. and a relative humidity of about 70%.

Evaluation is carried out 14 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of

100% o means that no infection is observed.

Active substances, application rates and test results are shown in the following table. Table B

Uncinula test (vine) / protective

Example C

Venturia test (apple) / protective

Solvent: 24.5 parts by weight of acetone

To test for protective efficacy, young plants are sprayed with the active compound preparation in the stated application rate. After the spray coating has dried on, the plants are washed with an aqueous conidia suspension

Apple scab pathogen Venturia inaequalis and then remain in an incubation cabin for 1 day at approx. 20 ° C and 100% relative humidity.

The plants are then placed in a greenhouse at approx. 21 ° C and a relative humidity of approx. 90%.

Active substances, application rates and test results are shown in the following table. Table C.

Venturia test (apple) / protective

Table C (continued)

Table C (continued)

Table C (continued)

Table C (continued)

Example D

Puccinia test (wheat) / protective

Solvent: 25 parts by weight of N.N-dimethylacetamide

Emulsifier: 0.6 part by weight of alkylaryl polyglycol ether

To test for protective efficacy, young plants are sprayed with the active compound preparation in the stated application rate. After the spray coating has dried on, the plants are sprayed with a conidia suspension of Puccinia recondita. The plants remain at 20 ° C and 100% relative for 48 hours

Humidity in an incubation cabin.

The plants are then placed in a greenhouse at a temperature of approximately 20.degree. C. and a relative atmospheric humidity of 80% in order to promote the development of rust pustules.

Active substances, application rates and test results are shown in the following table. Table D

Puccina test (wheat) / protective

Table D (continued)

Table D (continued)

Example E

Pyricularia test (rice) / protective

Solvent: 49 parts by weight of N, N-dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To test for protective activity, young rice plants are sprayed with the preparation of active compound in the stated application rate. 1 day after the treatment, the plants are inoculated with an aqueous spore suspension of Pyricularia oryzae and then remain at 100% relative atmospheric humidity and 26 ° C. for 24 hours. The plants are then placed in a greenhouse at 80% relative atmospheric humidity and a temperature of 26 ° C.

Evaluation is carried out 7 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.

Active substances, application rates and test results are shown in the following table. Table E

Pyricularia test (rice) / protective

Table E (continued)

Example F

Erysiphe test (barley) / resistance induction

Solvent: 50 parts by weight of N, N-dimethylformamide

Emulsifier: 1.17 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and the mixture is diluted

Concentrate with water and the specified amount of emulsifier to the desired concentration.

To test for resistance-inducing activity, young cereal plants are sprayed with the preparation of active compound in the stated application rate. 4

Days after treatment, the plants are spotted with Erysiphe graminis f. sp. Hordei inoculated. The plants are then placed in a greenhouse at 70% relative atmospheric humidity and a temperature of 18 ° C.

Evaluation is carried out 7 days after the inoculation. 0% means a

Efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.

Active substances, application rates and test results are shown in the following table. Table F

Erysiphe test (barley) / resistance induction

Example G

Phaedon larvae test

Solvent: 30 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted to the desired amount with water containing emulsifier

Concentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with larvae of the horseradish beetle (Phaedon cochleariae) while the leaves are still moist.

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

Active substances, active substance concentrations and test results are shown in the following table.

Table G

Phaedon larvae test

Table G (continued)

Table G (continued)

Example H

Spodoptera frugiperda test

Solvent: 30 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

Concentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active ingredient of the desired concentration and populated with caterpillars of the army worm (Spodoptera frugiperda) while the leaves are still moist.

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

Table H

Spodoptera frugiperda test

Table H (continued)

Example I

Myzus Test

Solvent: 30 parts by weight of dimethylformamide emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted to the desired concentrations with water containing emulsifier.

Broad bean seedlings (Vicia faba), which are infested with the green peach aphid (Myzus persicae), are immersed in an active ingredient preparation of the desired concentration and placed in a plastic can.

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

Table I

Myzus Test

Example K

Meloidogyne Test

Vessels are filled with sand, active ingredient solution, Meloidogyne incognita egg larva suspension and lettuce seeds. The lettuce seeds germinate and the plantlets develop. The galls develop at the roots.

After the desired time, the nematicidal effect is determined in% using the formation of bile. 100% means that no galls were found; 0% means that the number of galls on the treated plants corresponds to that of the untreated control.

Table K

Meloidogyne Test

Example L

Leptosphaeria nodorum test (wheat) / protective

Solvent: 10 parts by weight of N-methyl-pyrrolidone emulsifier: 0.6 part by weight of alkylaryl polyglycol ether

To test for protective activity, young plants are sprayed with the active compound preparation in the stated application rate. After the spray coating has dried on, the plants are sprayed with a spore suspension of Leptosphaeria nodorum. The plants remain in an incubation cabin at 20 ° C. and 100% relative atmospheric humidity for 48 hours.

The plants are placed in a greenhouse at a temperature of approx. 15 ° C and a relative humidity of 80%.

Active substances, application rates and test results are shown in the following table. Table L

Leptosphaeria nodorum test (wheat) / protective

Table L (continued)

Table L (continued)

Table L (continued)

Claims

claims

Oxime derivatives of the formula

in which

A represents alkanediyl,

R 1 stands for optionally substituted 1,2-thiazolyl, 1,2,4-thiadiazolyl or pyridyl,

R2 represents hydrogen, alkyl or optionally substituted aryl,

R represents hydrogen, alkyl, cycloalkyl, alkoxyalkyl, alkenyl, alkylcarbonyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted arylcarbonyl, optionally substituted heterocyclyl, optionally substituted heterocyclicalkyl or optionally substituted heterocyclylcarbonyl and

R ^{4 represents} hydrogen, halogen, alkyl, alkoxy, cyano or nitro.

2. oxime derivatives of the formula (I) according to claim 1, in which

A represents alkanediyl having 1 to 4 carbon atoms, R 1 represents 1,2-thiazolyl, 1,2,4-thiadiazolyl or pyridyl which is optionally mono- or disubstituted by alkyl having 1 to 4 carbon atoms and or halogen,

R2 represents hydrogen, alkyl having 1 to 4 carbon atoms or aryl having 6 to 10 carbon atoms which is optionally monosubstituted to tetrasubstantially, identically or differently, substituted by halogen and / or alkyl having 1 to 4 carbon atoms,

R3 for hydrogen, alkyl with 1 to 6 carbon atoms, cycloalkyl with 3 to 8 carbon atoms, alkoxyalkyl with 1 to 4 carbon atoms in the alkoxy part and 1 to 4 carbon atoms in the alkyl part, alkenyl with 2 to 6 carbon atoms or for alkylcarbonyl with 1 to 6 carbon atoms is in the alkyl part, or

represents aryl having 6 to 10 carbon atoms, where each of these radicals can be monosubstituted to tetrasubstituted, identical or different, by halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 4 carbon atoms, each straight-chain or branched Haloalkyl, haloalkoxy or haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms,

or

represents aralkyl having 6 to 10 carbon atoms in the aryl part and 1 to 4 carbon atoms in the alkyl part, where each of these radicals can be substituted up to four times, in the same way or differently, by halogen, cyano, nitro, in each case straight-chain or branched

Alkyl, alkoxy or alkylthio each having 1 to 4 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy or haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms,

or

represents arylcarbonyl having 6 to 10 carbon atoms in the aryl part, each of these radicals being able to be substituted up to four times, in the same way or differently, by halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 4 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy or haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms,

or

represents heterocyclyl with 5 or 6 ring members and 1 to 3 heteroatoms, such as oxygen, nitrogen and / or sulfur, where these radicals can optionally be mono- to trisubstituted, identical or differently substituted by halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 4 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy or haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms,

or

for heterocyclylalkyl with 5 or 6 ring members and 1 to 3 heteroatoms, such as oxygen, sulfur and / or nitrogen, and 1 to 4 Carbon atoms in the alkyl part, where these radicals can optionally be monosubstituted to trisubstituted, identical or different, by halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkylthio, each having 1 to 4 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy or Haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms,

or

represents heterocyclylcarbonyl having 5 or 6 ring members and 1 to 3 heteroatoms, such as oxygen, nitrogen and or sulfur, where these radicals can optionally be monosubstituted to trisubstituted, identical or different, by halogen, cyano, nitro, in each case straight-chain or branched alkyl, Alkoxy or alkylthio each having 1 to 4 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy or haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms,

and

3. A process for the preparation of oxime derivatives of the formula (I) according to claim 1, characterized in that carbonyl compounds of the formula

in which

A, Rl, R ² and R ^{4 have} the meanings given above,

with an oxyamine of the formula

R ³ -O-NH ₂ (III), in which

R3 has the meaning given above,

or their acid addition complexes,

if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.

4. Means for controlling unwanted microorganisms and animal pests, characterized by a content of at least one oxime derivative of the formula (I) according to claim 1 in addition to extenders and / or surface-active substances.

5. Use of oxime derivatives of the formula (I) according to Claim 1 for combating undesired microorganisms and animal pests.

6. A method for controlling unwanted microorganisms and animal pests, characterized in that oxime derivatives of the formula (I) according to claim 1 are applied to the unwanted microorganisms or animal pests and / or their habitat.

7. A process for the preparation of agents for controlling unwanted microorganisms and animal pests, characterized in that oxime derivatives of the formula (I) according to Claim 1 are mixed with extenders and / or surface-active substances.

8. oxime derivative according to claim 1, characterized by the formula

9. oxime derivative according to claim 1, characterized by the formula

10. oxime derivative according to claim 1, characterized by the formula