WO2002050035A2 - Insecticidal and fungicidal (2,6-dichloro-4-pyridyl) methylcarbamates used as plant protective agents - Google Patents

Abstract

The invention relates to novel dichloropyridyl methylamides of formula (I) in which: R1 represents hydrogen, alkyl, alkyl halide, optionally substituted heterocyclyl or optionally substituted heterocyclylalkyl, and; R2 represents alkyl, alkyl halide, alkoxyalkyl, alkenyl, optionally substituted cycloalkyl, optionally substituted heterocyclyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted aryloxyalkyl or optionally substituted heterocyclylalkyl. The invention also relates to a method for producing the novel substances and to their use for controlling unwanted microorganisms and animal pests.

Description

Dichlorpyridylniethylam.de

The present invention relates to new dichloropyridylmethylamides, a process for their production and their use to combat undesirable ones

Microorganisms and animal pests.

It has already become known that certain dichloropyridyl derivatives have fungicidal properties (cf. EP-A 0 334 813, EP-A 0 334 809, EP-A 0 334 812, EP-A 0 332 579, EP-A 0 288 976, JP-A 87-242 393 and DE-A 2 620 781). The

The effectiveness of these previously known substances is good, but in some cases leaves something to be desired at low application rates.

There have now been new dichlo yridylmethylamides of the formula

in which

R ^{1 represents} hydrogen, alkyl, haloalkyl, optionally substituted heterocyclyl or optionally substituted heterocyclylalkyl and

R ^{2 represents} alkyl, haloalkyl, alkoxyalkyl, alkenyl, optionally substituted cycloalkyl, optionally substituted heterocyclyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted aryloxyalkyl or for optionally substituted heterocyclylalkyl, found.

It has furthermore been found that dichloropyridylmethylamides of the formula (I) can be prepared by using dichloropyridylmethylamines of the formula

in which

R ^{1 has} the meaning given above,

with halocarbonyl compounds of the formula

in which

R ^{2 has} the meaning given above and

X represents halogen,

if appropriate in the presence of a ner diluent and if appropriate in the presence of an acid binder. Finally, it was found that the new dichloropyridylmethylamides 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 dichloropyridylmethylamides of the formula (I) according to the invention have a significantly better fungicidal and insecticidal action than the constitutionally most similar, known substances of the same action.

In the present context, heterocyclyl stands for saturated or unsaturated, as well as aromatic, ring-shaped compounds in which at least one ring member has a hetero atom, i.e. is an atom other than carbon. If the ring contains several heteroatoms, these can be the same or different. Heteroatoms are preferably oxygen, nitrogen or sulfur. If the ring contains several oxygen atoms, these are not adjacent.

The dichloropyridylmethylamides according to the invention are generally defined by the formula (I). Compounds of the formula (I) in which

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

1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms,

or stands for aralkyl with 6 to 10 carbon atoms in the aryl part and 1 to 4 carbon atoms in the alkyl part, it being possible for these radicals to be monosubstituted to trisubstituted, identical or different, by halogen, cyano,

Nitro, alkyl with 1 to 4 carbon atoms and / or alkoxy with 1 to 4

Carbon atoms, or represents three- to six-membered heterocyclyl with 1 to 3 heteroatoms, such as oxygen, nitrogen and / or sulfur, it being possible for these radicals to be monosubstituted to trisubstituted, identical or different, by halogen, Cyano, nitro, alkyl with 1 to 4 carbon atoms and / or alkoxy with 1 to 4 carbon atoms, or for heterocyclylalkyl with three to six ring members and 1 to 3 heteroatoms, such as oxygen, nitrogen and / or sulfur, in the heterocycle and 1 to 4 carbon atoms is in the alkyl part, where these radicals can be substituted once to three times, identically or differently by halogen, cyano, nitro, alkyl having 1 to 4 carbon atoms and / or alkoxy having 1 to 4 carbon atoms, and

for alkyl with 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms and 1 to 9 identical or different halogen 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 cycloalkyl with 3 is up to 7 carbon atoms, where the cycloalkyl radicals can be monosubstituted to trisubstituted, identical or different, by halogen, cyano, nitro, alkyl having 1 to 4 carbon atoms and / or alkoxy having 1 to 4 carbon atoms, or aryl having 6 to 10 carbon atoms , where these radicals can be substituted one to three times, in the same way or differently, by halogen, cyano, nitro, alkyl having 1 to 4 carbon atoms and / or alkoxy having 1 to 4 carbon atoms, or for aralkyl having 6 to 10 carbon atoms in the aryl part and 1 to 4 carbon atoms in the alkyl part, these radicals being single to triple, identical or different substitutes can be uiert by halogen, cyano, nitro, alkyl with 1 to 4 carbon atoms and / or alkoxy with 1 to 4

Carbon atoms, or aryloxyalkyl having 6 to 10 carbon atoms in the aryl part and 1 to 4 carbon atoms in the alkyl part, where these radicals can be substituted one to three times, identically or differently, by halogen, cyano, nitro, alkyl having 1 to 4 carbon atoms and / or alkoxy with 1 to 4 carbon atoms, or represents three to six-membered heterocyclyl having 1 to 3 heteroatoms, such as oxygen, nitrogen and / or sulfur, where these radicals can be substituted once to three times, identically or differently, by halogen, cyano, nitro, alkyl having 1 to 4 carbon atoms and / or alkoxy with 1 to 4 carbon atoms, or for heterocyclylalkyl with three to six ring members and 1 to 3 heteroatoms, such as oxygen, nitrogen and / or sulfur, in the heterocycle and 1 to 4 carbon atoms in the alkyl part, these radicals being simple to triple, may be substituted identically or differently by halogen, cyano, nitro, alkyl having 1 to 4 carbon atoms and / or alkoxy having 1 to

4 carbon atoms.

Dichloφyridylmethylamides of the formula (I), in which

R ¹ for hydrogen, methyl, ethyl, n-propyl, i-propyl, n-, i-, sec.- or tert-

Butyl, trifluoromethyl, chloroethyl, trichloroethyl or bromoethyl, or stands for phenylalkyl with 1 to 4 carbon atoms in the alkyl part, where these radicals can be substituted one to three times, in the same or different manner, by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl , n-propyl, i-propyl, n-butyl, i-butyl, sec.-butyl, tert.-butyl, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, sec.- Butoxy and / or tert.-butoxy, or represents pyridyl, furyl, thienyl, oxetanyl or pyrimidyl, where these radicals can be substituted once to three times, identically or differently, by fluorine, chlorine, bromine, cyano, nitro, methyl,

Ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec.-butyl, tert.-butyl, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, sec. -Butoxy and / or tert-butoxy, or pyridylmethyl, furylmethyl, thienylmethyl, oxetanylmethyl or pyrimidylmethyl, where these radicals can be monosubstituted to trisubstituted, identical or different, by fluorine, chlorine, bromine, cyano, Nitro, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec.-butyl, tert.-butyl, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i- Butoxy, sec-butoxy and / or tert-butoxy, and

for hydrogen, methyl, ethyl, n-propyl, i-propyl, n-, i-, sec.- or tert.-

Butyl, trifluoromethyl, chloroethyl, trichloroethyl or bromoethyl, or stands for alkoxyalkyl with 1 or 2 carbon atoms in the alkoxy part and 1 or 2 carbon atoms in the alkyl part, or stands for alkenyl with 2 to 4 carbon atoms, or stands for cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl , where these radicals can be monosubstituted to trisubstituted, identical or different, by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec.-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, sec-butoxy and / or tert-butoxy, or represents phenyl, which is simple to triple, identical or different can be substituted by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, tert-butyl, methoxy, ethoxy, n- Propoxy, i-propoxy, n-butoxy, i-butoxy, sec-butoxy and / or tert-butoxy, or for phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety l is, where these radicals can be substituted once to three times, identically or differently by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec.- Butyl, tert-butyl, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, sec. -Butoxy and / or tert-butoxy, or represents phenoxyalkyl having 1 to 4 carbon atoms in the alkyl part, where these radicals can be substituted one to three times, identically or differently, by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, sec-butoxy and or tert.-

butoxy, or stands for pyridyl, furyl, thienyl, oxetanyl or pyrimidyl, where these radicals can be substituted one to three times, in the same way or differently, by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, i-propyl, n -Butyl, i-butyl, sec-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, sec-butoxy and or tert.-butoxy, or for Pyridylmethyl, furylmethyl, thienylmethyl, oxetanyl ethyl or pyrimidylmethyl, where these radicals can be substituted one to three times, in the same way or differently, by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, i-propyl, n- Butyl, i-butyl, sec-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, sec.-

Butoxy and / or tert-butoxy.

If (2,6-dichloropyridin-4-yl) methylamine and chloroformic acid (2-bromo) ethyl ester are used as starting materials, the course of the process according to the invention can be illustrated by the following formula.

Formula (II) provides a general definition of the dichloropyridylmethylamines required as starting materials when carrying out the process according to the invention. In this formula, R ¹ preferably has those meanings which have already been mentioned as preferred for this radical in connection with the description of the substances of the formula (I) according to the invention. The Dichloφyridylmethylamine of formula (II) are known or can be prepared by known methods (cf. Rec. Trav. Chim. Pays-Bas 52 (1933), 55-56).

Formula (III) provides a general definition of the halocarbonyl compounds required as starting materials when carrying out the process according to the invention. In this formula, R ² preferably has those meanings which have already been mentioned as preferred for this radical in connection with the description of the substances of the formula (I) according to the invention. X preferably represents chlorine.

The halocarbonyl compounds of the formula (III) are known or can be prepared by known methods.

Suitable diluents for carrying out the process according to the invention are all customary inert, organic solvents. Aliphatic, alicyclic or aromatic hydrocarbons, such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; 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. Mixtures of the aforementioned can also be used

Solvents with water, these mixtures optionally being in the form of two-phase systems.

All customary inorganic and organic bases are suitable as acid binders when carrying out the process according to the invention. Alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates, 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 or Sodium bicarbonate, also ammonium compounds, such as ammonium acetate and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N, N-dimethylamline, N, N-dimethylbenzylamine, pyridine, N-methylpiperidine, N-methylmoφholin, N, N-Di - methylaminopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecene (DBU).

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 120 ° 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, e.g. at pressures between 0.1 bar and 10 bar.

When carrying out the process according to the invention, in general 0.5 to 2.0 mol, preferably 0.8 to 1.5 mol, of halogenocarbonyl compound of the formula (III) are employed per 1 mol of dichloropyridylmethylamine of the formula (II). 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 are exemplary but not limiting

Diseases that fall under the generic names listed above:

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 heφotrichoides.

The active compounds according to the invention also have a strong strengthening effect

Plants on. They are therefore suitable for mobilizing the plant's own defenses against attack by unwanted microorganisms.

Plant-strengthening (resistance-inducing) substances are to be understood in the present context as those substances which are able to stimulate the immune system of plants in such a way that the treated plants develop extensive resistance to these microorganisms when subsequently inoculated with undesired microorganisms.

In the present case, undesirable microorganisms include phytopathogenic

Understand fungi, bacteria and viruses. The substances according to the invention can therefore be used to protect plants against attack by the named pathogens within a certain period of time after the treatment. The period of time within which protection is provided generally ranges from 1 to 10 days, preferably 1 to 7 days after the treatment of the plants with the

Agents.

The fact that the active compounds are well tolerated by plants in the concentrations required to combat plant diseases permits treatment of above-ground parts of plants, of propagation stock and seeds, and of the soil. The active compounds according to the invention can be used with particularly good success in combating cereal diseases, for example against Erysiphe species.

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 products for the synthesis of further active ingredients.

With good plant tolerance and favorable warm-blooded toxicity, the active substances are suitable for controlling animal pests, especially insects,

Arachnids and nematodes found in agriculture, in forests, in the protection of stocks and materials, and in the hygiene sector. They can preferably be used as pesticides. They are effective against normally sensitive and resistant species as well as against all or individual stages of development. The pests mentioned above include:

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

From the order of the Diplopoda e.g. Blaniulus guttulatus. From the order of the Chilopoda e.g. Geophilus caφophagus, Scutigera spp ..

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, for example Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp., Schistocerca gregaria. From the order of the Blattaria, for example Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica. From the order of the Dermaptera, for example, Forficula auricularia. From the order of the Isoptera, for example Reticuliterm.es spp .. From the order of the Phthiraptera, for example Pediculus humanus coφoris, Haematopinus spp., Linognathus spp., Trichodectes spp., Damalinia spp ..

From the order of the Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci, Thrips palmi, Frankliniella accidentalis. From the order of the Heteroptera e.g. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.

From the order of the Homoptera e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus sppe, Phrosiphodumonum., Macrosiphodumon. 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 xylostella, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp.,

Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Mamestra brassicae, Panolis flammea, Spodoptera spp., Trichoplusia ni, Caφocapsa pomonella, Pierilo s., Pieril nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana,

Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana, Cnaphalocerus spp., Oulema oryzae.

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 chrysoisisamamisysamnaisphamisusnaisphamusisnaamyszaamiszaamysaza sylasylamisusnaamphasylasphis, amphora spp. Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meliginusus seneus. Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica, Lissorhoptrus oryzophilus.

From the order of the Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp. From the order of the Diptera e.g. Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala,

Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa, Hylemyia spp., Liriomyza spp .. From the order of the Siphonaptera, for example Xenopsylla cheopis, Ceratophyllus spp ..

From the class of the Arachnida e.g. Scoφio maurus, Latrodectus mactans, Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalommodes spp., I. Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp.,

Hemitarsonemus spp., Brevipalpus 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., Bursaph.

They can be used with particularly good success for combating plant-damaging insects, such as, for example, against the larvae of the horseradish leaf beetle (Phaedon cochleariae), the caterpillars of the cockroach (Plutella maculipennis) or the green peach aphid (Mycus persicae). According to the invention, all plants and parts of plants can be treated. Plants are understood here to mean all plants and plant populations, such as desired and undesired wild plants or cultivated plants (including naturally occurring cultivated plants). Cultivated 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. 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 using the customary treatment methods, e.g. by dipping, spraying, vaporizing, atomizing, scattering, spreading and, in the case of propagation material, in particular seeds, furthermore by single- or multi-layer coating.

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 are to be understood as non-living materials that have been prepared for use in technology. For example, technical materials which are to be protected against microbial change or destruction by active substances according to the invention, adhesives, glues, paper and cardboard, textiles, leather, wood, paints and

Plastic items, cooling lubricants and other materials that are organisms can be attacked or decomposed. 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, the preferred technical materials are adhesives, glues, papers and cartons, leather, wood

Paints, coolants and heat transfer fluids called, particularly preferably wood.

Bacteria, fungi, yeasts, algae and, for example, are microorganisms which can cause degradation or a change in the technical materials

Called slime organisms. The active compounds according to the invention preferably act against fungi, in particular mold, wood-discoloring and wood-destroying fungi (Basidiomycetes) and against mucus organisms and algae.

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

Alternaria, such as Alternaria tenuis,

Aspergillus, such as Aspergillus niger,

Chaetomium, like Chaetomium globosum,

Coniophora, such as Coniophora puetana, Lentinus, such as Lentinus tigrinus,

Penicillium, such as Penicillium glaucum,

Polyporus, such as Polyporus 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.

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 solvents such as dimethylformamide and dimethyl sulfoxide, and water. Liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and pressure, e.g. Aerosol propellants, such as halogenated hydrocarbons and butane, propane, nitrogen and

Carbon dioxide. Possible solid carriers are: e.g. natural rock meals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock meals, such as highly disperse silica, aluminum oxide and silicates. The following are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite,

Dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems. Possible 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. Possible dispersants are, for example, 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 also natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations. Other additives can be mineral and vegetable oils.

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

The formulations generally contain between 0.1 and 95 percent by weight

Active ingredient, preferably between 0.5 and 90%.

The active compounds according to the invention can be used as such or in their formulations, also in a mixture with known fungicides, bactericides, acaricides, nematicides or insect cides, in order, for example, to broaden the spectrum of activity or to prevent the development of resistance. In many cases, synergistic effects are obtained, i.e. the effectiveness of the mixture is greater than the effectiveness of the individual components.

The following connections can be considered as mixed partners:

fungicides:

Aldimoφh, ampropylfos, ampropylfos potassium, andoprim, anilazine, azaconazole, azoxystrobin, benalaxyl, benodanil, benomyl, benzamacril, benzamacrylic isobutyl, bialaphos,

Binapacryl, 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, cypodurinophenol, cypodaminocarbol, cypodaminacol, cypodaminocarbol, cypodaminocarbol, cypodaminocarbin, cypodaminocarbin, cypodaminocarbol, cypodinocarbin, cypodinocarbin, cypodinocarbin, cypodinocarbin, cypodinocarbin, cypodinocarbin, cypodinocarbin, cypodinocarbin, cypodinocarbin, cypodinocarbin, cypodinocarbin, cypodinocarbin, cypodinocarbin , Diclobutrazole, diclofluanide, diclomezin, dicloran,

Diethofencarb, difenoconazole, dimethirimol, Dimethomoφh, diniconazole, diniconazole-M, dinocap, diphenylamine, Dipyrithione, Ditalimfos, dithianon, Dodemoφh, dodine, Drazoxolon, Ediphenphos, epoxiconazole, etaconazole, ethirimol, etridiazole, famoxadone, Fenapanil, fenarimol, fenbuconazole, fenfuram, Fenitropan, fenpiclonil,

Fenpropidin, Fenpropimoφh, Fentinacetat, Fentinhydroxyd, Ferbam, Ferimzon, Fluazinam, Flumetover, Fluoromid, Fluquinconazol, Fluφrimidol, Flusilazol, Flusulfamid, Flutolanil, Flutriafol, Folpet, Fosetyl-Alminium, Fazetylam, Fosetylamyl, Fosetylam, Furosilamyl, Fosetylam, Fosetylamyl, Fosetylam, Furosilyl, Fosetylam, Fosetylam, Fosetylamyl, Fosetylam, Fosetylam, Fosetylamyl, Fosetylam, Fosetylamyl, Fosetylam, Fosetylamyl, Fosetylam, Fosetylamyl, Fosetylam, Fosetylam, Furosol Furconazole, furconazole-cis, furmecyclox, fenhexamide,

guazatine,

Hexachlorobenzene, hexaconazole, hymexazole,

Imazalil, Imibenconazol, Iminoctadin, Iminoctadinealbesilat, Iminoctadinetriacetat, Iodocarb, Ipconazol, Iprobefos (TBP), 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, Metconazol, Methasulfocarb, Methfuroxam, Metiram, Metomeclam, Metsulfovax,

Mildiomycin, Myclobutanil, Myclozolin, Nickel-dimethyldithiocarbamat, Nitrothal-isopropyl, Nuarimol, Ofurace, Oxadixyl, Oxamocarb, Oxolinicacid, Oxycarboxim, Oxyfenthiin, Paclobutrazole, Pefurazoat, Penconuronolin, Phoxurazolin, Phonurinazolin, Phonocurazolin, Phonazonolin, Phonazonolin, Phonazonolin, Phonazonolin, Phonazonin, Phonazonolin Procymidone, propamocarb, Propanosine sodium, propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil,

Pyroquilon, Pyroxyfur,

Quinconazole, quintozen (PCNB), quinoxyfen,

Sulfur and sulfur preparations, spiroxamines, tebuconazole, tecloftalam, tecnazen, tetcyclacis, tetraconazole, thiabendazole,

Thicyofen, Thifluzamide, Thiophanate-methyl, Thiram, Tioxymid, Tolclofos-methyl,

Tolylfluanid, Triadimefon, Triadimenol, Triazbutil, Triazoxid, Trichlamid, Tricyclazol,

Tridemoφh, triflumizole, triforin, 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) - 1H- 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-l, 3-dioxan-5-yl) -ß - [[4- (trifluoromethyl) phenyl] methylene] -lH-l, 2,4-triazol-1-ethanol, (5RS, 6RS) -6-hydroxy-2,2JJ-tetramethyl-5- (lH-l, 2,4-triazol-l-yl) -3-octanone,

(E) -a- (methoxyimino) -N-methyl-2-phenoxy-phenylacetamide,

1 - (2,4-dichloφhenyl) -2- (l H- 1, 2,4-triazole-1-yl) -ethanone-O- (phenylmethyl) -oxime, l- (2-methyl-l-naphthalenyl) -lH-pyrrole-2,5-dione, l- (3,5-dichloφhenyl) -3- (2-propenyl) -2,5-pyrrolidinedione, 1 - [(diiodomethyl) sulfonyl] -4-methyl-benzene , l - [[2- (2,4-dichloφhenyl) -1, 3-dioxolan-2-yl] methyl] -lH-imidazole, l - [[2- (4-chloro-phenyl) -3-ρhenyloxiranyl] - methyl] -lH-l, 2,4-triazole, l- [l- [2 - [(2,4-dichloφhenyl) methoxy] phenyl] ethenyl] -lH-imidazole, l-memyl-5-nonyl -2- (phenylmethyl) -3-pyrrolidinol, 2 ^ 6'-dibromo-2-methyl-4'-trifluoromethoxy-4-trifluoromethyl-l, 3-thiazole-5-carboxarilide,

2,6-dichloro-5- (methylthio) -4-pyrirnidinyl 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 - [(1-methylethyl) sulfonyl] -5- (trichloromethyl) -1, 3,4-thiadiazole, 2 - [[6-deoxy-4-O- (4-O-methyl-β-D-glycopyranosyl ) -aD-glucopyranosyl] -amino] -4-methoxy-1H-pyrrolo [2,3-d] pyrimidine-5-carbonitrile,

2-aminobutane,

2-bromo-2- (bromomethyl) -pentandinitril,

2-chloro-N- (2,3-dihydro-l, l, 3-methyl-lH-mden-4-yl) -3-pyridinecarboxamide, 2-chloro-N- (2,6-dimethylphenyl) -N- (isothiocyanatomethyl) -acetamide,

2-phenylphenol (OPP),

3,4-dichloro-l- [4- (difluoromethoxy) phenyl] -lH-pyrrole-2,5-dione,

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

3 - (1,1-dimethylpropyl-1-oxo-lH-indene-2-carbonitrile, 3- [2- (4-chloro-phenyl) -5-ethoxy-3-isoxazolidinyl] pyridine,

4-chloro-2-cyan-N, N-dimethyl-5- (4-methylphenyl) -1 H-imidazole-1-sulfonamide,

4-methyl-tetrazolo [l, 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-chloro-phenyl) -azo] cyanoacetate, potassium hydrogen carbonate,

Methantetrathiol sodium salt,

Methyl-l- (2,3-dihydro-2,2-dimethyl-lH-inden-l-yl) -lH-rmidazol-5-carboxylate,

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

Methyl-N- (cωoracetyl) -N- (2,6-dimemylphenyl) -DL-alaninate, N- (2,6-dimethylphenyl) -2-methoxy-N- (te1xahydro-2-oxo-3-furanyl) - acetamide,

N- (2,6-dimethylphenyl) -2-methoxy-N- (tetrahydro-2-oxo-3-t enyl) acetamide, N- (2-chloro-4-nitrophenyl) -4-methyl-3-nitro-beιιzolsulfonamid, N- (4-cyclohexylphenyl) -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-pyridyl) cyclopropanecarboxamide,

N- [2,2,2-trichloro-1 - [(chloroacetyl) amino] ethyl] benzane, N- [3-chloro-4,5-bis- (2-propmyloxy) phenyl] -N ' methoxy-methanimidamide, N-formyl-N-hydroxy-DL-alanine sodium salt,

O, O-diethyl- [2- (dipropylamino) -2-oxoethyl] ethylphosphoramidothioate, O-methyl-S-phenylphenylpropylphosphoramidothioat,

S-methyl-l, 2,3-benzothiadiazole-7-carbothioate, spiro [2H] -l-benzopyran-2, l '(3'H) -isobenzofüran] -3'-one,

Bactericides: bronopol, dichlorophene, nitrapyrin, nickel-dimethyldithiocarbamate, kasugamycin,

Octhilinone, furan carboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, 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, Benfuracarb, Bensultap, Benzoximate, Betacyfluthrin, Bifenazate, Bifenthrin, Bioethanomethrin

Biopermethrin, BPMC, Bromophos A, Bufencarb, Buprofezin, Butathiofos, Butocarboxim, Butylpyridaben,

Cadusafos, Carbaryl, Carbofüran, Carbophenothion, Carbosulfan, Cartap, Chloethocarb, Chlorethoxyfos, Chlorfenapyr, Chlorfenvinphos, Chlorfluazuron, Chlormephos, Chloφyrifos, Chloφyrifos M, Chlovaporthrin, Cis-Resmethrin, Cispermethrin, Clocythrin, Cloethocarb, Clofentezine, Cyanophos, Cycloprene, Cycloprothrin, Cyfluthrin, Cyhalothrin, Cyhexatin, Cypermethrin, Cyromazine, Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diazenzhiuron, Diml Diofenolan, Disulfoton, Docusat-sodium, Dofenapyn,

spp Eflusilanate, emamectin, empenthrin, endosulfan, Entomopfthora., esfenvalerate, ethiofencarb, Etliion, ethoprophos, etofenprox, etoxazole, etrimfos, fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion, Fenothiocarb, Fenoxacrim, fenoxycarb, fenpropathrin fenpyrad, Fenpyrithrin, fenpyroximate, fenvalerate , Fipronil, fluazuron, flubrocythrinate, flucycloxuron, flucythrinate, flufenoxuron,

Flutenzine, Fluvalinate, Fonophos, Fosmethilan, Fosthiazate, Fubfenprox, Furathiocarb, Granuloseviruses Halofenozide, HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene, Imidacloprid, Isazofos, Isofenphos, Isoxinion, Iverm

Nuclear polyhedron viruses lambda-cyhalothrin, lufenuron

Malathion, Mecarbam, Metaldehyde, Methamidophos, Metharhician anisopliae, Metharhician flavoviride, Methidathione, Methiocarb, Methomyl, Methoxyfenozide, Metolcarb, Metoxadiazone, Mevinphos, Milbemectin, Monocrotophos,

Naled, Nitenpyram, Nithiazine, Novaluron Omethoat, 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, Pymetroz

Pyraclofos, Pyresmethrin, Pyrethrum, Pyridaben, Pyridathion, Pyrimidifen, Pyriproxyfen, Quinalphos, Ribavirin Salithion, Sebufos, Silafluofen, Spinosad, Sulfotep, Sulprofos, Tau fluvalinate, tebufenozide, tebufenpyrad, tebupirimiphos, teflubenzuron,

Tefluthrin, temephos, temivinphos, terbufos, tetrachlorvinphos, theta-cypermethrin, thiamethoxam, thiapronil, thiatriphos, thiocyclam hydrogen oxalate, thiodicarb, thiofanox, thuringiensine, tralocythrin, tralomate-zeniazin

Triflumuron, trimethacarb, thiacloprid,

Vamidothion, Vaniliprole, Verticillium lecanii

YI 5302

Zeta-cypermethrin, zolaprofos (1 R-cis) - [5- (phenylmethyl) -3-furanyl] -methyl-3 - [(dihydro-2-oxo-3 (2H) -furanylidene) - methyl] -2.2 -dimethylcyclopropancarboxylat

(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- (1,1-dimethylethyl) phenyl] -4,5-dihydro-oxazole

2- (acetyloxy) -3 -dodecyl- 1,4-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-dichloφhenyl) -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-dichloro-phenyl) -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 - [[1,6-dihydro-6-oxo-1 - (phenylmethyl) -4-pyridazinyl] oxy] ethyl] carbamate N- (3,4,4-trifluoro-1-oxo-3 - butenyl) -glycine

N- (4-chloro-phenyl) -3- [4- (difluoromethoxy) phenyl] -4,5-dihydro-4-phenyl-lH-pyrazole-1-carboxamide N - [(2-chloro-5-thiazolyl) methyl] -N-methyl-N '-nitro-guanidine

N-methyl-N '- (1-methyl-2-propenyl) - 1, 2-hydrazinedicarbothioamide N-methyl-N'-2-propenyl-1, 2-hydrazinedicarbothioamide 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.

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

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. The

Application takes place in the customary manner, for example by watering, spraying, atomizing, scattering, dusting, foaming, brushing, etc. It is also possible to apply the active ingredients by the ultra-low-volume process or to apply the active ingredient preparation or the active ingredient itself to the soil to inject. The seeds of the plants can also be treated. When the active compounds according to the invention are used 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.

When used as insecticides, the active compounds according to the invention can also be present in their commercially available formulations and in the use forms prepared from these formulations in 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 and storage pests, the stands out

Active ingredient characterized by an excellent residual effect on wood and clay as well as a good alkali stability on limed substrates.

The agents used to protect industrial materials generally contain the active substances in an amount between 5 and 95% by weight, preferably between

10 and 75% by weight. The application concentrations of the active substances according to the invention depend on the type and 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 action of the active ingredients to be used according to the invention in the material protection or of the agents, concentrates or formulations which can be prepared therefrom can be increased if further antimicrobial compounds, fungicides, bactericides, herbicides, insecticides or other active ingredients are used to increase the Spectrum of effects or achieving special effects such as added protection against insects. These mixtures can have a broader spectrum of activity than the compounds according to the invention.

As already mentioned above, all plants and their parts can be treated according to the invention. In a preferred embodiment, plant species and plant cultivars and their parts occurring wildly or obtained by conventional organic breeding methods, such as crossing or protoplast fusion, are 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" parts of plants "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 spectrum of action 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 dryness 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 storability and / or workability of the harvested products possible, which go beyond the effects to be expected.

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 gives these plants particularly advantageous properties (“traits”). Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or to water or soil salt content, increased flowering performance, easier harvesting,

Acceleration of ripeness, 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 and cotton and rapeseed are highlighted. As traits, special features are raised 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 thuringiensis (for example by the genes CryΙA (a), CryIA (b), CryΙA (c), CryllA, CrylllA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CrylF and their combinations) are produced in the plants (hereinafter "Bt plants"). As properties

("Traits") are also particularly emphasized the increased tolerance of the plants to certain herbicidal active ingredients, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (e.g. "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, cotton and

Soybean varieties named 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 ) to be expelled. 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 treated particularly advantageously according to the invention with the compounds of the general formula (I) or the active compound mixtures according to the invention. 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

1.0 g (5J mmol) (2,6-dichloro-4-pyridyl) methylamine are dissolved in 100 ml toluene and first with 60 ml 0.1 N aqueous sodium hydroxide solution and then with 1.0 g (5.3 mmol ) Chloroformic acid (2-bromethyl) ester added. The reaction mixture is stirred for 12 hours at room temperature, then the organic phase is separated off, washed once with 50 ml of water, dried over magnesium sulfate and concentrated under reduced pressure. The residue is stirred with ether, a crystalline product being obtained. This is suctioned off and air dried. 0.9 g (52% of theory) of 2-bromoethyl (2,6-dichloro-4-pyridyl) methyl carbamate with a melting point of 97 ° C. is obtained.

Example 2

1.0 g (3.3 mmol) of N - [(6-chloro-3-pyridyl) methyl] -N - [(2,6-dichloro-4-pyridyl) methyl] amine are dissolved in 100 ml of toluene and first mixed with 35 ml of aqueous 0.1 N sodium hydroxide solution and 20 ml of water and then with 0.6 g (3.2 mmol) of chloroformic acid (2-bromethyl) ester. The reaction mixture is stirred for 12 hours at room temperature, then the organic phase is separated off, washed once with 20 ml of water, dries over magnesium sulfate and concentrates under reduced pressure. 0.7 g (48% of theory) of 2-bromoethyl- (6-chloro-3-pyridyl) methyl - [(2,6-dichloro-4-pyridyl) methyl] carbamate is obtained as a yellow oil.

The substances of the formula (I) listed in Table 1 below are also prepared by the methods given above.

Table 1

Production of a preliminary product

Example 19

25 g (142 mmol) (2,6-dichloro-4-pyridyl) methylamine are dissolved in 150 ml toluene and 16 g (160 mmol) triethylamine are added. A solution of 22.8 g (142 mmol) of 2-chloro-5- (chloromethyl) pyridine in 50 ml of toluene is then added dropwise at room temperature. The reaction mixture is heated under reflux for 12 hours and allowed to cool to room temperature. The mixture is washed twice with 100 ml of water each time, the organic phase is dried over magnesium sulfate and the solvent is distilled off under reduced pressure. The oily residue is chromatographed on silica gel using (hexane / ethyl acetate = 4: 1). 18.5 g (43% of theory) of N - [(6-chloro-3-pyridyl) methyl] -N-

[(2,6-dichloro-4-pyridyl) methyl] amine as a yellow solid with a melting point of 66 ° C.

applications

Example A

Phaedon larvae test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

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

Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and with larvae of the horseradish beetle

(Phaedon cochleariae) occupied 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, application rates and test results are shown in the following table.

Table A Phaedon larval test

Example B

Plutella Test

Solvent: 7 parts by weight of dimethylformamide emulsifier: 1 part by weight of alkylaryl polyglycol ether

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

Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with caterpillars of the cockroach (Plutella xylostella) 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.

Active ingredients, application rates and test results come from the following

Table.

Table B

Plutella Test

Example C

Myzus Test

Solvent: 31 parts by weight of acetone emulsifier: 1 part by weight of alkylaryl polyglycol ether

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

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

Table C.

Myzus Test

Example D

Erysiphe test (barley) / resistance induction

Solvent: 50 parts by weight of N, N-dimethylformamide emulsifier: 1.2 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 concentrate is diluted to the desired concentration with water and the stated amount of emulsifier.

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 the 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 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 D

Erysiphe test (barley) / resistance induction

Claims

Patentansprtiche

Dichloφyridylmethylamide of the formula

in which

R ^{1 represents} hydrogen, alkyl, haloalkyl, optionally substituted heterocyclyl or optionally substituted heterocyclylalkyl and

R ^{2 represents} alkyl, haloalkyl, alkoxyalkyl, alkenyl, optionally substituted cycloalkyl, optionally substituted heterocyclyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted aryloxyalkyl or for optionally substituted heterocyclylalkyl.

Dichloφyridylmethylamide of formula (I) according to claim 1, in which

R ^{1 represents} hydrogen, alkyl having 1 to 4 carbon atoms or haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms,

or stands for aralkyl with 6 to 10 carbon atoms in the aryl part and 1 to 4 carbon atoms in the alkyl part, where these radicals can be substituted by up to three, identical or different Halogen, cyano, nitro, alkyl with 1 to 4 carbon atoms and / or alkoxy with 1 to 4 carbon atoms, or for three- to six-membered heterocyclyl with 1 to 3 heteroatoms, where these radicals can be substituted by up to three, identical or different Halogen, cyano, nitro,

Alkyl with 1 to 4 carbon atoms and / or alkoxy with 1 to 4 carbon atoms, or for heterocyclylalkyl with three to six ring members and 1 to 3

Heteroatoms in the heterocycle and 1 to 4 carbon atoms in the alkyl part, where these radicals can be monosubstituted to triple, identical or differently substituted by halogen, cyano, nitro, alkyl having 1 to 4 carbon atoms and / or alkoxy having 1 to 4 carbon atoms, and

for alkyl with 1 to 4 carbon atoms, haloalkyl with 1 to 4

Carbon atoms and 1 to 9 identical or different halogen 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 cycloalkyl with 3 to 7 carbon atoms, the cycloalkyl radicals being simple to triple, similar or can be substituted differently by halogen, cyano, nitro, alkyl having 1 to 4 carbon atoms and / or alkoxy having 1 to 4 carbon atoms, or represents aryl having 6 to 10 carbon atoms, these radicals being monosubstituted to trisubstituted in the same or different manner can be halogen, cyano, nitro, alkyl having 1 to 4 carbon atoms and / or alkoxy having 1 to 4 carbon atoms, or aralkyl having 6 to 10 carbon atoms in the aryl part and 1 to 4 carbon atoms in the alkyl part, these radicals being simple to triple, may be substituted the same or different by Halogen, cyano, nitro, alkyl having 1 to 4 carbon atoms and / or alkoxy having 1 to 4 carbon atoms, or aryloxyalkyl having 6 to 10 carbon atoms in the aryl part and 1 to 4 carbon atoms in the alkyl part, these radicals being simple to triple, similar or can be substituted differently by halogen, cyano, nitro, alkyl having 1 to 4 carbon atoms and / or alkoxy having 1 to 4 carbon atoms, or represents three to six-membered heterocyclyl having 1 to '3 heteroatoms, these radicals being simple to triple, similar or can be differently substituted by halogen, cyano, nitro,

Alkyl with 1 to 4 carbon atoms and / or alkoxy with 1 to 4 carbon atoms, or for heterocyclylalkyl with three to six ring members and 1 to 3 heteroatoms in the heterocycle and 1 to 4 carbon atoms in the alkyl part, these radicals being simple to triple, identical or different can be substituted by halogen, cyano, nitro, alkyl having 1 to 4 carbon atoms and / or alkoxy having 1 to 4 carbon atoms.

Dichloφyridylmethylamide of formula (I) according to claim 1, in which

R ^{1 represents} hydrogen, methyl, ethyl, n-propyl, i-propyl, n-, i-, sec- or tert-butyl, trifluoromethyl, chloroethyl, trichloroethyl or bromoethyl, or for phenylalkyl having 1 to 4 carbon atoms in the Alkyl part, where these radicals can be monosubstituted to triple, identical or differently substituted by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec.- Butyl, tert-butyl, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, sec. Butoxy and / or tert-butoxy, or represents pyridyl, furyl, thienyl, oxetanyl or pyrimidyl, these radicals can be monosubstituted to trisubstituted, identical or different, by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, tert .- Butyl, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, sec. -Butoxy and / or tert. -Butoxy, or stands for pyridylmethyl, furylmethyl, thienylmethyl, oxetanylmethyl or pyrimidylmethyl, where these residues can be substituted one to three times, in the same way or differently, by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, i- Propyl, n-butyl, i-butyl, sec-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, i-

Propoxy, n-butoxy, i-butoxy, sec-butoxy and / or tert. -Butoxy, and

represents hydrogen, methyl, ethyl, n-propyl, i-propyl, n-, i-, sec- or tert-butyl, trifluoromethyl, chloroethyl, trichloroethyl or bromoethyl, or for alkoxyalkyl having 1 or 2 carbon atoms in the alkoxy part and 1 or 2 carbon atoms in the alkyl part, or stands for alkenyl with 2 to 4 carbon atoms, or stands for cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, where these radicals can be substituted one to three times, identically or differently, by fluorine, chlorine, bromine, cyano , Nitro, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i -Butoxy, sec. -Butoxy and / or tert. -Butoxy, or represents phenyl, which can be monosubstituted to trisubstituted, identical or different, by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, sec. -Butoxy and / or tert-butoxy, or represents phenylalkyl having 1 to 4 carbon atoms in the alkyl part, where these radicals can be substituted once to three times, in the same way or differently, by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, i-propyl, n- Butyl, i-butyl, sec-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, sec. -Butoxy and / or tert-butoxy, or represents phenoxyalkyl having 1 to 4 carbon atoms in the alkyl part, where these radicals can be substituted one to three times, identically or differently, by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec. -Butyl, tert-butyl, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, sec-butoxy and / or tert-butoxy, or for pyridyl, furyl, thienyl, oxetanyl or Pyrimidyl, where these radicals can be mono- to triple, identical or differently substituted by fluorine, chlorine, bromine, cyano, nitro, methyl,

Ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec. -Butyl, tert. -Butyl, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, sec.-butoxy and or tert. -Butoxy, or stands for pyridylmethyl, furylmethyl, thienylmethyl, oxetanylmethyl or pyrimidylmethyl, where these residues can be monosubstituted to triple, identical or differently substituted by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, i- Propyl, n-butyl, i-butyl, sec. -Butyl, tert-butyl, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, sec. -Butoxy and / or tert-butoxy.

4. Dichloφyridylmethylamid according to claim 1, characterized by the formula

5. Dichloφyridylmethylamid according to claim 1, characterized by the formula

6. Dichloφyridylmethylamid according to claim 1, characterized by the formula

7. Dichloφyridylmethylamid according to claim 1, characterized by the formula

8. A process for the preparation of Dichloφyridylmethylamiden of formula (I) according to claim 1, characterized in that Dichloφyridylmethylamine of the formula

in which

R ^{1 has} the meaning given above,

with halocarbonyl compounds of the formula

in which

R ^{2 has} the meaning given above and

X represents halogen,

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

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

10. Use of Dichloφyridylmethylamiden of formula (I) according to spoke 1 to combat unwanted microorganisms and animal pests.

11. A method for controlling undesirable microorganisms and animal pests, characterized in that dichloφyridyl methylamides of the formula (I) according to spoke 1 are applied to the microorganisms or the animal pests and / or their habitat.

12. A process for the preparation of agents for combating undesired microorganisms and animal pests, characterized in that dichloφyridylmethylamides of the formula (I) according to claim 1 with

Extenders and / or surfactants mixed.