DE10063109A1 - Dichlorpyridymethylimine - Google Patents

Abstract

The invention relates to novel dichloropyridyl methylamines of formula (I) wherein R<1> represents hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl or optionally substituted heterocyclyl and R<2> represents hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl or optionally substituted heterocyclyl, or R<1> and R<2> together with the carbon atom to which it is connected, represent an optionally substituted carbocyclic ring or an optionally substituted heterocyclic ring. The invention also relates to a method for producing said novel substances and the use thereof for combating undesired micro-organisms.

Description

The present invention relates to new dichloropyridylmethylimines, a process for their manufacture and their use to combat undesirable Microorganisms.

It has already become known that certain dichloropyridyhnethylimine possess 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 26 20 781). However, the effectiveness of these substances is not always sufficient.

There have now been new dichloropyridylmethylimines of the formula

in which
R ^{1 represents} hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl or optionally substituted heterocyclyl and
R ^{2 represents} hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl or optionally substituted heterocyclyl, or
R ¹ and R ² together with the carbon atom to which they are attached represent an optionally substituted carbocyclic ring or an optionally substituted heterocyclic ring,
found.

It has also been found that dichloropyridylmethylimines of the formula (I) can be prepared by using dichloropyridylmethylamine of the formula

with carbonyl compounds of the formula

in which
R ¹ and R ^{2 have} the meanings given above,
if appropriate in the presence of a diluent and if appropriate in the presence of a catalyst.

Finally, it was found that the new dichloropyridylmethylimines of the formula (I) are very well suited for controlling unwanted microorganisms. she show in particular a very strong fungicidal activity and can be both to mobilize the plant's own defenses against infestation by phytopathogenic  Fungi as well as fungicides for the direct control of phytopathogenic fungi deploy.

In the present case, aryl stands for aromatic, mono- or polycyclic Hydrocarbon rings, such as. B. phenyl, naphthyl, anthranyl, phenanthryl, preferably phenyl or naphthyl.

In the present case, heterocyclyl stands for saturated or unsaturated, as well aromatic, ring-shaped compounds in which at least one ring member Heteroatom, i. H. is an atom other than carbon. Contains the ring several heteroatoms, these can be the same or different. heteroatoms are preferably oxygen, nitrogen or sulfur. If necessary, form the ring-shaped compounds with other carbocyclic or heterocyclic, fused or bridged rings together a polycyclic Ring system. Mono- or bicyclic ring systems are preferred, in particular mono- or bicyclic aromatic ring systems.

In the present case, cycloalkyl stands for saturated, carbocyclic, ring-shaped Compounds that may be fused with other carbocyclic compounds or bridged rings form a polycyclic ring system.

The dichloropyridylmethylimines according to the invention are generally defined by the formula (I). Preferred compounds of the formula (I) are those in which
R ^{1 represents} hydrogen or alkyl having 1 to 6 carbon atoms, where the alkyl radicals can be substituted once to three times, in the same way or differently, by halogen, alkoxy having 1 to 4 carbon atoms, alkoxy carbonyl having 1 to 4 carbon atoms in the alkoxy part and / or dialkoxy phosphoryl with 1 to 4 carbon atoms in each alkoxy part, or
R ^{1 represents} cycloalkyl having 3 to 7 carbon atoms, where the cycloalkyl radicals can be substituted once to three times, in the same way or differently, by halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkoxycarbonyl having 1 to 4 carbon atoms in the Alkoxy part, dialkoxyphosphoryl with 1 to 4 carbon atoms in each alkoxy part, cycloalkylidene with 3 to 6 ring members and / or alkylcyclo alkylidene with 3 to 6 carbon atoms in the cycloalkylene part and 1 to 4 carbon atoms in the alkyl part, or
R ^{1 represents} phenyl or naphthyl, where these radicals can be substituted once to three times, identically or differently by
Halogen, cyano, nitro, alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 4 carbon atoms;
Haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms;
or
can be monosubstituted by double-linked alkylene having 3 or 4 carbon atoms, oxyalkylene having 2 or 3 carbon atoms or dioxyalkylene having 2 carbon atoms, where these groups can be monosubstituted to tetrasubstituted, identical or different, by fluorine, chlorine, methyl, ethyl and / or Trifluoromethyl, or
can be monosubstituted by doubly linked dioxymethylene, which can be mono- or disubstituted, identical or differently substituted by fluorine, chlorine, methyl, ethyl and / or trifluoromethyl, or
R ^{1 represents} heterocyclyl with 3 to 7 ring members and 1 to 4 heteroatoms, such as oxygen, nitrogen and / or sulfur, it being possible for the heterocycles to be monosubstituted to triple, identical or differently substituted by halogen, alkyl having 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, alkylsulfinyl with 1 to 4 carbon atoms and / or alkylsulfonyl with 1 to 4 carbon atoms,
and, if the heterocycle is a saturated ring, cycloalkylidene with 3 to 6 carbon atoms or alkylcycloalkylidene with 1 to 4 carbon atoms in the alkyl part and 3 to 6 carbon atoms in the cycloalkylidene part are also suitable as substituents, and
R ^{2 represents} hydrogen or alkyl having 1 to 6 carbon atoms, where the alkyl radicals can be substituted once to three times, identically or differently, by halogen, alkoxy having 1 to 4 carbon atoms, alkoxy carbonyl having 1 to 4 carbon atoms in the alkoxy part and / or dialkoxy phosphoryl with 1 to 4 carbon atoms in each alkoxy part, or
R ^{2 represents} cycloalkyl having 3 to 7 carbon atoms, where the cycloalkyl radicals can be substituted once to three times, identically or differently, by halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkoxycarbonyl having 1 to 4 carbon atoms in the Alkoxy part, dialkoxyphosphoryl with 1 to 4 carbon atoms in each alkoxy part, cycloalkylidene with 3 to 6 ring members and / or alkylcyclo alkylidene with 3 to 6 carbon atoms in the cycloalkylene part and 1 to 4 carbon atoms in the alkyl part, or
R ^{2 represents} phenyl or naphthyl, where these radicals can be substituted once to three times, identically or differently by
Halogen, cyano, nitro, alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 4 carbon atoms;
Haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms; or
can be monosubstituted by double-linked alkylene having 3 or 4 carbon atoms, oxyalkylene having 2 or 3 carbon atoms or dioxyalkylene having 2 carbon atoms, where these groups can be monosubstituted to tetrasubstituted, identical or different, by fluorine, chlorine, methyl, ethyl and / or Trifluoromethyl, or
can be monosubstituted by doubly linked dioxymethylene, which can be mono- or disubstituted, identical or differently substituted by fluorine, chlorine, methyl, ethyl and / or trifluoromethyl, or
R ^{2 represents} heterocyclyl with 3 to 7 ring members and 1 to 4 heteroatoms, such as oxygen, nitrogen and / or sulfur, it being possible for the heterocycles to be monosubstituted to triple, identical or differently substituted by halogen, alkyl having 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, alkylsulfinyl with 1 to 4 carbon atoms and / or alkylsulfonyl with 1 to 4 carbon atoms,
and, if the heterocycle is a saturated ring, cycloalkylidene with 3 to 6 carbon atoms or alkylcycloalkylidene with 1 to 4 carbon atoms in the alkyl part and 3 to 6 carbon atoms in the cycloalkylidene part are also suitable as substituents, or
R ¹ and R ² together with the carbon atom to which they are attached represent a carbocyclic ring having 3 to 7 carbon atoms, where these carbocycles can be monosubstituted to trisubstituted, identical or different, by halogen, alkyl having 1 to 4 carbon atoms, Alkoxy with 1 to 4 carbon atoms, alkoxycarbonyl with 1 to 4 carbon atoms in the alkoxy part, dialkoxyphosphoryl with 1 to 4 carbon atoms in each alkoxy part, cycloalkylidene with 3 to 6 ring members and / or alkylcycloalkylidene with 3 to 6 carbon atoms in the cycloalkylene part and 1 to 4 carbon atoms in the alkyl part , or
R ¹ and R ² together with the carbon atom to which they are attached represent a heterocyclic ring with 3 to 7 ring members and 1 to 4 heteroatoms, such as oxygen, nitrogen and / or sulfur, the heterocycles being simple to triple, similar or can be substituted differently by halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, alkylsulfinyl having 1 to 4 carbon atoms and / or alkylsulfonyl having 1 to 4 carbon atoms,
and, if the heterocycle is a saturated ring, cycloalkylidene with 3 to 6 carbon atoms or alkylcycloalkylidene with 1 to 4 carbon atoms in the alkyl part and 3 to 6 carbon atoms in the cycloalkylidene part are also suitable as substituents.

Those dichloropyridylmethylimines of the formula (I) in which
R ^{1 is} hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, 1-, 2-, 3-, neo-pentyl, 1-, 2-, 3- , 4- (2-methylbutyl), 1-, 2-, 3-hexyl, 1-, 2-, 3-, 4-, 5- (2-methylpentyl), 1-, 2-, 3- (3- Methylpentyl), 2-ethylbutyl, 1-, 3-, 4- (2,2-dimethylbutyl), 1-, 2- (2,3-dimethylbutyl), where these radicals can be substituted one to three times, identically or differently by fluorine, chlorine, bromine, iodine, methoxy, ethoxy, n-propoxy, i-propoxy, methoxy carbonyl, ethoxycarbonyl, dimethoxyphosphoryl and / or diethoxy phosphoryl, or
R ^{1 represents} cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, where these radicals can be substituted once to three times, identically or differently, by fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or i-propyl, n-, i- , s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, dimethoxyphosphoryl, diethoxyphosphoryl, cyclopentylidene and / or methylcyclopentylidene, or
R ^{1 represents} phenyl, which can be mono- to triple, identical or differently substituted by fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, trifluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluorethoxy, difluoromethylthio, trifluoromifluoromifluoromifluoromifluoromifluoromifluoromifluoromifluoromifluoromifluoromifluoromifluoromifluoromifluoromifluoromifluoromifluoromifluoromifluoromifluoromifluoromifluoromifluoromifluoromifluoromifluoromifluoromethyl (F)
can be monosubstituted by doubly linked propane-1,3-diyl, ethyleneoxy or ethylenedioxy, where each of these radicals can be monosubstituted to quadrupled, identical or differently substituted by fluorine, chlorine, methyl and / or trifluoromethyl, or
can be monosubstituted by doubly linked methylenedioxy, this radical being monosubstituted or disubstituted, identical or differently substituted by fluorine, chlorine, methyl and / or trifluoromethyl, or
R ^{1 represents} pyridyl, furyl or thienyl, where these radicals can be monosubstituted to trisubstituted, identical or different, by fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or i-propyl, n-, i-, s - or t-butyl, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl and / or ethylsulfonyl, and
R ^{2 is} hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, 1-, 2-, 3-, neo-pentyl, 1-, 2-, 3- , 4- (2-methylbutyl), 1-, 2-, 3-hexyl, 1-, 2-, 3-, 4-, 5- (2-methylpentyl), 1-, 2-, 3- (3- Methylpentyl), 2-ethylbutyl, 1-, 3-, 4- (2,2-dimethylbutyl), 1-, 2- (2,3-dimethylbutyl), where these radicals can be substituted one to three times, identically or differently by fluorine, chlorine, bromine, iodine, methoxy, ethoxy, n-propoxy, i-propoxy, methoxy carbonyl, ethoxycarbonyl, dimethoxyphosphoryl and / or diethoxy phosphoryl, or
R ^{2 represents} cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, where these radicals can be substituted once to three times, identically or differently, by fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or i-propyl, n-, i- , s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, dimethoxyphosphoryl, diethoxyphosphoryl, cyclopentylidene and / or methylcyclopentylidene, or
R ^{2 represents} phenyl, which can be mono- to triple, identical or differently substituted by fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, trifluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluorethoxy, difluoromethylthioifluorifluorifluoromethylthioiflififluorifluoromifluoromifluorifluorifluoromifluoromifluorifluorifluoromifluoromifluorifluorifluoromifluoromifluorifluorifluoromifluoromifluorifluorifluoromifluoromifluorifluorifluoromifluoromethylrifluorifluoromifluoromifluorifluorifluoromifluoromethyltrifluorifluoromifluoromethyltrifluoromethyltrifluoromethyltrifluoromethyl, Fifluoromethyltrifluorofluorofluoromethyl, Trifluoromethoxy
can be monosubstituted by doubly linked propane-1,3-diyl, ethyleneoxy or ethylenedioxy, where each of these radicals can be monosubstituted to quadrupled, identical or differently substituted by fluorine, chlorine, methyl and / or trifluoromethyl, or
can be monosubstituted by doubly linked methylenedioxy, this radical being monosubstituted or disubstituted, identical or differently substituted by fluorine, chlorine, methyl and / or trifluoromethyl, or
R ^{2 represents} pyridyl, furyl or thienyl, where these radicals can be monosubstituted to trisubstituted, identical or different, by fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or i-propyl, n-, i-, s - or t-butyl, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl and / or ethylsulfonyl, or
R ¹ and R ² together with the carbon atom to which they are attached represent cyclopentane, cyclohexane or pyran, where these radicals can be substituted one to three times, in the same way or differently, by methyl, ethyl, n- or i-propyl, n -, i-, s- or t-butyl, cyclopentylidene, methylcyclopentylidene, methoxycarbonyl, ethoxycarbonyl, dimethoxyphosphoryl and / or diethoxyphosphoryl.

If 2,6-dichloropyrid-4-yl-methylamine and 2-chlorobenzaldehyde are used as starting materials and toluenesulfonic acid as a catalyst, the course of the process according to the invention can be illustrated by the following formula.

That when starting the process according to the invention as a starting material required 2,6-dichloropyrid-4-yl-methylamine is characterized by the formula (II). The 2,6-dichloropyrid-4-yl-methylamine is known (cf. Rec. Trav. Chim. Pays-Bas 52 (1933), 55-56).  

Formula (III) provides a general definition of the carbonyl compounds which are further required as starting materials when carrying out the process according to the invention. In this formula, R ¹ and R ² preferably have those meanings which have already been mentioned as preferred for these radicals in connection with the description of the substances of the formula (I) according to the invention.

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

Suitable diluents for carrying out the Ver according to the invention drive all usual inert, organic solvents into consideration. Preferably usable are aliphatic, alicyclic or aromatic hydrocarbons, such as for example 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.

The catalysts used in carrying out the process according to the invention inorganic and organic protonic or Lewis acids as well as polymers Acids in question. Hydrogen chloride, sulfuric acid, Phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, methanesulfonic acid, Trifluoromethanesulfonic acid, toluenesulfonic acid, boron trifluoride (also as etherate), boron tribromide, aluminum trichloride, titanium tetrachloride, tetrabutyl orthotitanate, zinc chloro rid, ferric chloride, antimony pentachloride, acidic ion exchangers, acidic clays and acidic silica gel.

The reaction temperatures can be carried out when carrying out the process according to the invention Process can be varied over a wide range. Generally you work at temperatures between 0 ° C and 150 ° C, preferably between 0 ° C and 80 ° C.  

When performing the inventive method one works in generally under atmospheric pressure. But it is also possible to increase or to work under reduced pressure, e.g. B. at pressures between 0.1 bar and 10 bar.

When carrying out the process according to the invention, the starting point is 1 mol 2,6-dichloropyrid-4-yl-methylamine of the formula (II) in general from 1 to 15 mol, preferably from 1 to 8 mol of carbonyl compound of the formula (III). The Refurbishment is carried out using customary methods.

The substances according to the invention have a strong microbicidal action and can fight unwanted microorganisms, such as fungi and Bacteria can be used in crop protection and material protection.

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

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

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 sclerotionum;
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 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 infestation by unwanted microorganisms.  

Among plant-strengthening (resistance-inducing) substances are in the present Zu context to understand such substances that are able to Defense system of plants to stimulate the treated plants subsequent inoculation with undesirable microorganisms Develop resistance to these microorganisms.

In the present case, undesirable microorganisms include phytopathogenic Understand fungi, bacteria and viruses. The substances according to the invention can therefore used to plant plants within a certain period of time after loading protect the action against infestation by the named pests. Of time space within which protection is provided generally extends from 1 to 10 days, preferably 1 to 7 days after the treatment of the plants with the Agents.

The good plant tolerance of the active ingredients in the control of plants Concentrations necessary for diseases allow treatment above ground Parts of plants, of seedlings, and of the soil.

The active compounds according to the invention can be particularly successful Control of cereal diseases, such as against Erysiphe species, or of rice diseases, such as against Pyricularia 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.

The active compounds according to the invention can optionally be used in certain concentrations trations and application rates also as herbicides, to influence the plants growth, as well as for controlling animal pests. she can optionally also be used as intermediates and precursors for the synthesis use other active ingredients.  

According to the invention, all plants and parts of plants can be treated. Under Plants are understood here as all plants and plant populations desired and undesirable wild plants or crops (including naturally occurring crops). Cultivated plants can be plants that by conventional breeding and optimization methods or by organic technological and genetic engineering methods or combinations of these Methods can be obtained, including transgenic plants and including those that can or cannot be protected by plant variety rights Plant varieties. Under plant parts, all above-ground and underground Parts and organs of plants, such as shoot, leaf, flower and root understood with leaves, needles, stems, stems, flowers, fruiting bodies, Fruits and seeds as well as roots, tubers and rhizomes are listed. To the Plant parts also include crops as well as vegetative and generative Propagation material, for example cuttings, tubers, rhizomes, offshoots and Seeds.

The treatment of plants and parts of plants according to the invention with the Active substances take place directly or by influencing their environment, living space or storage room according to the usual treatment methods, e.g. B. by diving, Spraying, vaporizing, atomizing, scattering, spreading and when propagating material, especially in the case of seeds, continues with one or more layers Envelop.

In material protection, the substances according to the invention can be used to protect tech African materials against infestation and destruction by unwanted micro use organisms.

In the present context, technical materials include non-living ones Understand materials that have been prepared for use in engineering are. For example, technical materials made by the invention Active substances are to be protected against microbial change or destruction,  Adhesives, glue, paper and cardboard, textiles, leather, wood, paints and Plastic items, coolants and other materials can be made by micro organisms can be attacked or decomposed. As part of the to be protected Materials are also parts of production plants, such as cooling water cycles, called, impaired by the multiplication of microorganisms can be. In the context of the present invention are considered technical Materials preferably adhesives, glues, papers and boxes, leather, wood, Paints, cooling lubricants and heat transfer liquids called particularly preferably wood.

As microorganisms that break down or change the technical Materials such as bacteria, fungi, yeasts, algae and 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 mucous 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, like Trichoderma viride,
Escherichia, such as Escherichia coli,
Pseudomonas, such as Pseudomonas aeruginosa,
Staphylococcus, such as Staphylococcus aureus.

The active ingredients can depend on their respective physical and / or chemical properties can be converted into the usual formulations, such as Solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, Fine encapsulation in polymeric substances and in coating compositions for seeds, as well ULV cold and warm fog formulations.

These formulations are prepared in a known manner, e.g. B. by mixing of the active substances with extenders, i.e. liquid solvents, under pressure liquefied gases and / or solid carriers, optionally using of surface-active agents, i.e. emulsifiers and / or dispersants and / or foam-generating agents. In the case of using water as a stretch means can e.g. B. also used organic solvents as auxiliary solvents become. 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, alipha table hydrocarbons, such as cyclohexane or paraffins, e.g. B. 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. With liquefied gaseous extenders or carriers are meant such liquids which are gaseous at normal temperature and pressure, e.g. B. Aerosol Propellants, such as halogenated hydrocarbons and butane, propane, nitrogen and Carbon dioxide. As solid carriers come into question: B. natural stone powder, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diato sea earth and synthetic rock powder, such as highly disperse silica, aluminum oxide and silicates. Possible solid carriers for granules are: B. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, Dolomite and synthetic granules from inorganic and organic flours as well as granules of organic material such as sawdust, coconut shells, corn piston and tobacco stem. As emulsifiers and / or foaming agents come in Question: e.g. B. non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid  ester, polyoxyethylene fatty alcohol ether, e.g. B. alkylaryl polyglycol ethers, alkyl sulfonates, Alkyl sulfates, aryl sulfonates and protein hydrolyzates. As dispersants come in Question: e.g. B. lignin sulfite and methyl cellulose.

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

Dyes such as inorganic pigments, e.g. B. iron oxide, titanium oxide, ferro cyan and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients, such as salts of iron, manganese, boron, copper, cobalt, Molybdenum and zinc can be used.

The formulations generally contain between 0.1 and 95 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 insecticides can be used, e.g. B. to broaden the spectrum of activity or to prevent the development of resistance. In many cases you get syner gistic effects, d. H. the effectiveness of the mixture is greater than the effectiveness of the individual components.

The following connections can be considered as mixed 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, chlorfenazol, chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon, cufraneb, cymoxanil, cyphodaminopol, cofodinconol, cypodamconol, cypodaminazol, cypodinconol
Debacarb, dichlorophene, diclobutrazole, diclofluanide, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, diniconazol-M, dinocap, diphenylamine, dipyrithione, ditalimfos, dithorphoxinodonine, dithorphononodine
Ediphenphos, Epoxiconazole, Etaconazole, Ethirimol, Etridiazole,
Famoxadone, fenapanil, fenarimol, fenbuconazole, fenfuram, fenitropan, fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam, ferimzon, fluazinam, flumetover, fluoromid, fluquinconazole, flurprimolol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfosolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusilazolutol, flusilazolutol, flusulfonol, flusilazolutol, flusulfazolutol, flusilazolutol, flusulfazolutol, flusilazolutol, flusulfazolutolol Fosetyl sodium, fthalide, fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole, furconazole-cis, furmecyclox, fenhexamide,
guazatine,
Hexachlorobenzene, hexaconazole, hymexazole,
Imazalil, Imibenconazol, Iminoctadin, Iminoctadinealbesilat, Iminoctadinetriacetat, Iodocarb, Ipconazol, Iprobefos (IBP), Iprodione, Irumamycin, Isoprothiolan, Isovaledione, Iprovalicarb,
Kasugamycin, Kresoxim-methyl, copper preparations, such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxine-copper and Bordeaux mixture,
Mancopper, Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Metrifuroxam, Metiram, Metomeclam, Metsulfovax, Mildiomycin, Myclobutanil, Myclozolin,
Nickel dimethyldithiocarbamate, nitrothal isopropyl, Nuarimol,
Ofurace, Oxadixyl, Oxamocarb, Oxolinicacid, Oxycarboxim, Oxyfenthiin,
Paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen, pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz, procymidon, propamocarb, propanosine sodium, propiconazole, propineb, pyrazophos, pyrifen, pyifenox, pyrroyilonil
Quinconazole, quintozen (PCNB), quinoxyfen,
Sulfur, sulfur preparations, spiroxamines,
Tebuconazole, tecloftalam, tecnazene, Tetcyclacis, tetraconazole, thiabendazole, Thicyofen, Thifluzamide, thiophanate-methyl, thiram, Tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, Triazbutil, triazoxide, Trichlamid, tricyclazole, tridemorph, triflumizole, triforine, triticonazole, trifloxystrobin,
uniconazole
Validamycin A, vinclozolin, viniconazole,
Zarilamid, Zineb, Ziram as well
Dagger G,
OK 8705,
OK 8801,
α- (1,1-dimethylethyl) -β- (2-phenoxyethenoxyethyl) -1H-1,2,4-triazole-1-ethanol,
α- (2,4-dichlorophenyl) -β-fluoro-b-propyl-1H-1,2,4-triazole-1-ethanol,
α- (2,4-dichlorophenyl) -β-methoxy-a-methyl-1H-1,2,4-triazole-1-ethanol,
α- (5-methyl-1,3-dioxan-5-yl) -β - [[4- (trifluoromethyl) phenyl] methylene] -1H-1,2,4-triazol-1-ethanol,
(5RS, 6RS) -6-hydroxy-2,2,7,7-tetramethyl-5- (1H-1,2,4-triazol-1-yl) -3-octanone,
(E) -a- (methoxyimino) -N-methyl-2-phenoxy-phenylacetamide,
1- (2,4-dichlorophenyl) -2- (1H-1,2,4-triazol-1-yl) -ethanone-O- (phenyinethyl) oxime
1- (2-methyl-1-naphthalenyl) -1H-pyrrole-2,5-dione,
1- (3,5-dichlorophenyl) -3- (2-propenyl) -2,5-pyrrolidinedione,
1 - [(diiodomethyl) sulphonyl] -4-methylbenzene,
1 - [[2- (2,4-dichlorophenyl) -1,3-dioxolan-2-yl] methyl] -1H-imidazole,
1 - [[2- (4-chlorophenyl) -3-phenyloxiranyl] methyl] -1H-1,2,4-triazole,
1- [1- [2 - [(2,4-dichlorophenyl) methoxy] phenyl] ethenyl] -1H-imidazole,
1-methyl-5-nonyl-2- (phenylmethyl) -3-pyrrolidinol, 2 ', 6'-dibromo-2-methyl-4'-trifluoromethoxy-4'-trifluoromethyl-1,3-thiazole-5-carboxanilide,
2,6-dichloro-5- (methyltbio) -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 - [(1-methylethyl) sulphonyl] -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-1,1,3-trimethyl-1H-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] -1H-pyrrole-2,5-dione,
3,5-dichloro-N- [cyano [(1-methyl-2-propynyl) -oxy] -methyl] -benzamide,
3- (1,1-dimethylpropyl-1-oxo-1H-indene-2-carbonitrile,
3- [2- (4-chlorophenyl) -5-ethoxy-3-isoxazolidinyl] -pyridine,
4-chloro-2-cyano-N, N-dimethyl-5- (4-methylphenyl) -1H-imidazol-1-sulfonamide,
4-methyl-tetrazolo [1,5-a] quinazolin-5 (4H) -one,
8-hydroxyquinoline sulfate,
9H-xanthene-9-carboxylic acid 2 - [(phenylamino) carbonyl] hydrazide,
bis (1-methylethyl) -3-methyl-4 - ((3-methylbenzoyl) oxy) -2,5-thiophene dicarboxylate,
cis-1- (4-chlorophenyl) -2- (1H-1,2,4-triazol-1-yl) cycloheptanol,
cis-4- [3- [4- (1,1-dimethylpropyl) phenyl-2-methylpropyl] -2,6-dimethylmorpholine hydrochloride,
Ethyl - [(4-chlorophenyl) azo] cyanoacetate,
potassium bicarbonate,
Methantetrathiol sodium salt,
Methyl-1- (2,3-dihydro-2,2-dimethyl-1H-inden-1-yl) -1H-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-Cyclohexylphenyl) -1,4,5,6-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-1 - [(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] -ethylphosphoramidothioat,
O-methyl-S-phenyl-phenylpropylphosphoramidothioat,
S-Methyl-1,2,3-benzothiadiazole-7-carbothioate,
spiro [2H] -1-benzopyran-2,1 '(3'H) -isobenzofuran] -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, Biethanoprofinoxhrin, Bethenomethrofin, Biobanomethrin Butyl pyridaben
Cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan, cartap, Chloethocarb, chlorethoxyfos, chlorfenapyr, chlorfenvinphos, chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos M, Chlovaporthrin, cis-resmethrin, Cispermethrin, Clocythrin, cloethocarb, clofentezine, cyanophos, Cycloprene, cycloprothrin, cyfluthrin , Cyhalothrin, cyhexatin, cypermethrin, cyromazine,
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, Floxthrinofonate, Fufenzoxinhronate, Fufenoxthhronate, Fufenoxthonate, Fufronoxin, Fufone .
granulosis
Halofenozide, HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene,
Imidacloprid, isazofos, isofenphos, isoxathion, ivermectin,
nucleopolyhedroviruses
Lambda cyhalothrin, lufenuron
Malathion, Mecarbam, Metaldehyde, Methamidophos, Metharhician anisopliae, Metharhician 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, Pyromhrhridos, Pymmethrofzin, Pymmethrofinos , Pyridathione, pyrimidifen, pyriproxyfen,
quinalphos,
ribavirin
Salithion, Sebufos, Silafluofen, Spinosad, Sulfotep, Sulprofos,
Tau-fluvalinate, oxalate hydrogen tebufenozide, tebufenpyrad, Tebupirimiphos, teflubenzuron, tefluthrin, temephos, Temivinphos, terbufos, tetrachlorvinphos, theta cypermethrin, thiamethoxam, Thiapronil, Thiatriphos, thiocyclam, thiodicarb, thiofanox, thuringiensin, Tralocythrin, tralomethrin, triarathene, Triazamate, triazophos , Triazuron, trichlophenidine, trichlorfon, triflumuron, trimethacarb,
Vamidothion, Vaniliprole, Verticillium lecanii
YI 5302
Zeta-cypermethrin, zolaprofos
(1R-cis) - [5- (phenylmethyl) -3-furanyl] methyl-3 - [(dihydro-2-oxo-3 (2H) - furanylidene) methyl] -2,2-dimethylcyclopropane carboxylate
(3-phenoxyphenyl) methyl-2,2,3,3-tetramethylcyclopropanecarboxylat
1 - [(2-Chloro-5-thiazolyl) methyl] tetrahydro-3,5-dimethyl-N-nitro-1,3,5-triazine-2 (1H) - imine
2- (2-chloro-6-fluorophenyl) -4- (4- (1,1-dimethylethyl) phenyl] -4,5-dihydro-oxazol
2- (Acetlyoxy) -3-dodecyl-1,4-naphthalenedione
2-chloro-N - [[[4- (1-phenylethoxy) phenyl] amino] carbonyl] -benzamide
2-Chloro-N - [[[4- (2,2-dichloro-1,1-difluoroethoxy) phenyl] amino] carbonyl] benzamide 3-methylphenyl propyl carbamate
4- [4- (4-ethoxyphenyl) -4-methylpentyl] -1-fluoro-2-phenoxy-benzene
4-chloro-2- (1,1-dimethylethyl) -5 - [[2- (2,6-dimethyl-4-phenoxyphenoxy) ethyl] thio] - 3 (2H) pyridazinone
4-chloro-2- (2-chloro-2-methylpropyl) -5 - ((6-10d-3-pyridinyl) methoxy] -3 (2H) - pyridazinone
4-chloro-5 - [(6-chloro-3-pyridinyl) methoxy] -2- (3,4-dichlorophenyl) -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-dichlorophenyl) -2-oxo-1-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- (phenyhnethyl) -4-pyridazinyl] oxy] ethyl] carbamate
N- (3,4,4-trifluoro-1-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 '- (1-methyl-2-propenyl) -1,2-hydrazindicarbothioamid
N-methyl-N'-2-propenyl-1,2-hydrazindicarbothioamid
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 the formula (I) according to the invention also very good antifungal effects. They have a very broad antimyko spectrum of activity, in particular against dermatophytes and shoots, Mold and diphasic fungi (e.g. against Candida species such as Candida albicans, Candida glabrata) such as Epidermophyton floccosum, Aspergillus species such as Aspergillus niger and Aspergillus fumigatus, Trichophyton species such as Trichophyton mentagrophytes, Microsporon species such as Microsporon canis and audouinii. The enumeration of this Fungi does not in any way limit the detectable mycotic spectrum represents, but is only explanatory.

The active substances can be used as such, in the form of their formulations or in the form thereof rode application forms, such as ready-made solutions, suspensions, spray powders, pastes, soluble powders, dusts and granules can be used. The Application happens in the usual way, e.g. B. by pouring, spraying, spraying, Scattering, dusting, foaming, brushing, etc. It is also possible to use the Apply active ingredients according to the ultra-low-volume process or the active ingredient preparation or inject the active substance yourself 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 effort can be reduced quantities can be varied within a wide range depending on the type of application. When treating parts of plants, the active compound application rates are in the 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 in general between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed. When treating the floor, there are problems wall amounts of active ingredient generally between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha.

As already mentioned above, according to the invention all plants and their parts can be treated. In a preferred embodiment, go wild existing or by conventional organic breeding methods, such as crossbreeding or protoplast fusion obtained plant species and plant cultivars and their Parts treated. In a further preferred embodiment, transgenes are Plants and plant varieties, if necessary by genetic engineering methods in combination with conventional methods (Genetic Modified Organisms) and their parts treated. The term "parts" or "parts of Plants "or" parts of plants "was explained above.

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

Depending on the plant species or plant varieties, their location and growth Conditions (soils, climate, growing season, nutrition) can be determined by the invention Treatment also occur via additive ("synergistic") effects. So are, for example, reduced application rates and / or extensions of the Spectrum of activity and / or an enhancement of the effect of the invention usable substances and agents, better plant growth, increased tolerance against high or low temperatures, increased tolerance to drought  or against 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 possible, beyond the expected effects go out.

Among the preferred transgenic (genetic engineering) to be treated according to the invention genetically preserved) plants or plant varieties belong to all plants that are affected by the Genetic engineering modification contain genetic material that this Gives plants special beneficial valuable properties ("traits"). Examples for such properties are better plant growth, increased tolerance to over high or low temperatures, increased drought tolerance or against 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 harvest products. Further and particularly highlighted examples of such Properties are an increased defense of the plants against animal and micro biological pests, such as insects, mites, phytopathogenic fungi, Bacteria and / or viruses and an increased tolerance of the plants to certain herbicidal active ingredients. The important ones are examples of transgenic plants Cultivated plants, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, Rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and Grapes) mentioned, especially corn, soybeans, potatoes, cotton and rapeseed be highlighted. As characteristics ("traits") are particularly highlighted raised the increased defense of the plants against insects by in the plants standing toxins, especially those caused by the genetic material from Bacillus Thuringiensis (e.g. through the genes CryIA (a), CryIA (b), CryIA (c), CryIIA, CryIIIA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CryIF and their combinations) in the Plants are created (hereinafter "Bt plants"). As properties ("traits") the increased tolerance of the plants are particularly emphasized against certain herbicidal active ingredients, for example imidazolinones,  Sulfonylureas, glyphosate or phosphinotricin (e.g. "PAT" gene). The each the genes imparting the desired traits can also be found in Combinations with each other occur in the transgenic plants. As examples for "Bt plants" are maize varieties, cotton varieties, soy varieties and potato varieties under the trade names YIELD GARD® (e.g. maize, Cotton, soy), KnockOut® (e.g. maize), StarLink® (e.g. maize), Bollgard® (Cotton), Nucoton® (cotton) and NewLeaf® (potato). Examples of herbicide-tolerant plants are maize, cotton and Soybeans known as Roundup Ready® (Tolerance to glyphosate e.g. corn, cotton, soy), Liberty Link® (tolerance against phosphinotricin, e.g. Rape), IMI® (tolerance to imidazolinones) and STS® (Tolerance to sulfonylureas e.g. maize). As herbicidal resistant (conventionally grown to herbicide tolerance) plants are also the varieties sold under the name Clearfield® (e.g. maize). itself understandably, these statements also apply to future developments future plant varieties with these or future ent developed genetic traits.

The plants listed can be particularly advantageous according to the invention with the Compounds of the general formula (I) or the active ingredient according to the invention mixtures are treated. The above for the active ingredients or mixtures given preferred ranges also apply to the treatment of these plants. Be plant treatment with those in the present text should be particularly emphasized Specially listed compounds or mixtures.

Production and use of substances according to the invention are described in the fol illustrated examples.

Preparation Examples

example 1

1.76 (10 mmol) of 2,6-dichloropyridyl-4-methylamine are dissolved in 250 ml of toluene and successively with 1.54 g (11 mmol) of 2-chlorobenzaldehyde and 50 mg of 4- Toluene sulfonic acid added. The mixture is heated under reflux for 4 hours separator and then the solvent is distilled off under reduced pressure. Ver permanent volatiles are removed at 80 ° C and 1 mbar. The back Stand is triturated with petroleum ether, whereby a crystalline. Product arises. This is suctioned off and air-dried. 2.0 g (67% of theory) are obtained N- (2-chlorobenzylidene) (2,6-dichloro-4-pyridinyl) methanimine, melting point 88 ° C.

According to the methods given above, the following in Table 1 dichloropyridylmethylimines of the formula (I) prepared.  

Table 1

use Examples Example A Pyricularia test (rice) / protective

Solvent: 50 parts by weight of N, N-dimethylformamide
Emulsifier: 1.17 parts by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, 1 Ge is mixed important part of the active ingredient with the specified amount of solvent and dilutes the Concentrate with water and the specified amount of emulsifier to the desired Concentration.

To test for protective effectiveness, young rice plants are sprayed with the Active ingredient preparation in the specified application rate. 1 day after treatment plants with an aqueous spore suspension of Pyricularia oryzae inoculated and then remain at 100% rel. Humidity and 26 ° C. Subsequently the plants in a greenhouse at 80% rel. Humidity and one Set up temperature of 26 ° C.

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

In this test, those in Examples 1, 3, 6, 12, 13, 19, 34, 36, 38 and 39 show listed substances according to the invention at an application rate of 750 g / ha Efficiency of at least 80%.  

Example B 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 weight is mixed some active ingredient with the specified amount of solvent and dilute the concentrate with water and the specified amount of emulsifier to the desired concentration.

To test for resistance-inducing effectiveness, young cereals are sprayed plant with the active ingredient preparation in the specified application rate. 4 days after the treatment, the plants are covered with spores of Erysiphe graminis f. sp. Hordei inoculated. The plants are then grown in a greenhouse at 70% relative 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 100% means that no infection is observed.

In this test, those in Examples 1, 2, 3, 12, 13, 19, 34, 36, 38 and 39 show up led substances according to the invention at an application rate of 750 g / ha Efficiency of at least 80%.

Claims (6)

1. dichloropyridylmethylimine of the formula
in which
R ^{1 represents} hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl or optionally substituted heterocyclyl and
R ^{2 represents} hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl or optionally substituted heterocyclyl, or
R ¹ and R ² together with the carbon atom to which they are attached represent an optionally substituted carbocyclic ring or an optionally substituted heterocyclic ring. 2. A process for the preparation of dichloropyridylmethylimines of the formula (I) according to claim 1, characterized in that dichloropyridylmethylamine of the formula
with carbonyl compounds of the formula
in which
R ¹ and R ^{2 have} the meanings given above,
if appropriate in the presence of a diluent and if appropriate in the presence of a catalyst. 3. Means to combat unwanted microorganisms, known characterized by a content of at least one dichloropyridylmethylimine of formula (I) according to claim 1 in addition to extenders and / or above surfactants. 4. Use of dichloropyridylmethylimines of the formula (I) according to Claim 1 for combating undesirable microorganisms. 5. Process for combating undesirable microorganisms, thereby characterized in that dichloropyridylmethylimines of the formula (I) according to Claim 1 to the microorganisms and / or their habitat. 6. Process for the preparation of agents for combating undesirable Microorganisms, characterized in that dichloropyridyl  methylimines of the formula (I) according to claim 1 with extenders and / or surface-active substances mixed.