EP1501832A1

EP1501832A1 - Triazolopyrimidines

Info

Publication number: EP1501832A1
Application number: EP03722463A
Authority: EP
Inventors: Olaf Gebauer; Nico Jörg GREUL; Ulrich Heinemann; Fritz Maurer; Bernd-Wieland Krüger; Hans-Ludwig Elbe; Herbert Gayer; Ralf Dunkel; Arnd Voerste; Stefan Hillebrand; Christiane Boie; Ulrike Wachendorff-Neumann; Astrid Mauler-Machnik; Karl-Heinz Kuck
Original assignee: Bayer CropScience AG
Current assignee: Bayer CropScience AG
Priority date: 2002-04-26
Filing date: 2003-04-14
Publication date: 2005-02-02
Also published as: JP2005536460A; DE10218592A1; AU2003229657A1; US20050234076A1; BR0309568A; PL372989A1; WO2003091254A1

Abstract

Novel triazolopyrimidines of formula (I) where G, R and X have the meanings given in the description, a method for production of said substances and use thereof for the treatment of undesired microorganisms.

Description

triazolopyrimidines

The present invention relates to new triazolopvrimidines, a process for their preparation and their use for controlling unwanted microorganisms.

It has already become known that certain triazolopyrimidines have fungicidal properties (cf. EP-A-0 550 113, WO 94/20501, EP-A-0 613 900, US 5 612 345, EP-A-0 834 513, FR -A-2 784 991, WO 98/46607 and WO 98/46608).

However, the action of these compounds is unsatisfactory in many cases.

There have now been new triazolopyrimidines of the formula

in which

G represents optionally substituted, mono- or polycyclic, saturated, unsaturated or aromatic heterocyclyl which is bonded via a nitrogen atom, this nitrogen atom in the heterocycle being connected to a further nitrogen or oxygen atom, and where the heterocycle may also contain one or contains two further oxygen, nitrogen and / or sulfur atoms, but no two oxygen atoms can be directly adjacent,

R represents aryl which is optionally mono- to pentasubstituted and X represents halogen,

as well as acid addition salts of those compounds of formula (I) in which

G represents optionally substituted, mono- or polycyclic, saturated or unsaturated heterocyclyl which is bonded via a nitrogen atom, this nitrogen atom in the heterocycle being connected to a further nitrogen atom, and where the heterocycle optionally also has one or two further oxygen, nitrogen and / or contains sulfur atoms, but no two oxygen atoms can be directly adjacent,

found.

Depending on the substitution pattern, the compounds according to the invention can optionally be mixtures of various possible isomeric forms, in particular stereoisomers, such as e.g. E and Z, threo and erythro, and optical isomers, but optionally also of tautomers are present. If R is unequally substituted on both atoms which are adjacent to the binding site, the compounds in question can exist in a special form of stereoisomerism, namely as atropisomers.

Furthermore, it was found that the triazolopyrimidines of the formula (I) can be obtained if -

Dihalotriazolopyrimidines of the formula

in which R and X have the meanings given above and

Y represents halogen,

with heterocycles of the formula

G-H (III) in which

G has the meaning given above,

or with acid addition salts of heterocycles of the formula (III),

optionally in the presence of a diluent and optionally in

Implemented in the presence of an acid acceptor.

Finally, it was found that the triazolopyrimidines of the formula (I) or their acid addition salts are very suitable for controlling unwanted microorganisms. Above all, they show a strong fungicidal activity and can be used both in crop protection and in material protection.

Surprisingly, the triazolopyrimidines of the formula (I) according to the invention have a significantly better microbicidal activity than the constitutionally similar, previously known substances with the same direction of action.

The triazolopyrimidines according to the invention are generally defined by the formula (I).

G preferably represents mono- or bicyclic, saturated, unsaturated or aromatic heterocyclyl with a total of up to 12 members, which has a Nitrogen atom is bound, this nitrogen atom in the heterocycle being connected to a further nitrogen or oxygen atom, and wherein the heterocycle optionally also contains one or two further oxygen, nitrogen and / or sulfur atoms, but no two oxygen atoms are directly adjacent can,

where the heterocycles can be monosubstituted to trisubstituted, identical or different, by cyano, halogen, alkyl having 1 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms or by alkoxycarbonyl

1 to 4 carbon atoms in the alkoxy group.

is preferably phenyl, which is optionally monosubstituted to tetrasubstituted by:

Halogen, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl;

in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms;

each straight-chain or branched alkenyl or alkenyloxy each with

2 to 6 carbon atoms;

each straight-chain or branched haloalkyl, haloalkoxy,

Haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms; each straight-chain or branched haloalkenyl or haloalkenyloxy each having 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms;

in each case straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroximinoalkyl or alkoximinoalkyl each having 1 to 6 carbon atoms in the individual alkyl parts;

each by single or multiple, the same or different

Halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, substituted and in each case doubly linked alkylene with 3 or 4 carbon atoms or dioxyalkylene with 1 or 2 carbon atoms, or

Cycloalkyl of 3 to 6 carbon atoms.

X preferably represents fluorine, chlorine or bromine.

Those compounds of the formula (I) in which

G for a heterocyclyl radical of the formula

or stands

where # stands for the point of attachment and where each of the radicals can be monosubstituted to triple, identical or differently substituted by cyano, fluorine, chlorine, methyl, ethyl, methoxycarbonyl and / or ethoxycarbonyl,

represents phenyl which can be monosubstituted to tetrasubstituted, identical or different, by fluorine, chlorine, bromine, cyano, nitro, formyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t- Butyl, allyl, propargyl,

Methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, allyloxy, propargyloxy, trifluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluoromethyl Difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl, trichloroethynyloxy, trifluoroethynyloxy, chloroallyloxy, iodopropargyloxy, methylamino, ethylamino, n- or i-propylamino, dimethylamino, hydroxylyloxy, methoxyl, methylethyloxyethyl, methylethyloxyoxy, methylethyloxyethyl, methylethyloxyethyl, methylethyloxyethyl, methylethyloxyethyl, methylethyloxyethyl, methylethyloxyethyl, methylethyloxyoxy, methylethyloxy, methylethyl, methylethyl iminoethyl, ethoximinoethyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl,

trimethylene (propane-l, 3-diyl) substituted in the 2,3-position or 3,4-position substituted by fluorine, chlorine, methyl, trifluoromethyl, ethyl, n- or i-propyl, in each case optionally one or more times, identically or differently. , Methylenedioxy or ethylenedioxy, and

X represents bromine or chlorine.

Those compounds of the formula (I) in which

G and X have the meanings which have already been mentioned as particularly preferred, and

R represents phenyl, which can be monosubstituted to tetrasubstituted, identical or different, by fluorine, chlorine, trifluoromethyl, trifluoromethoxy and / or trifluoromethylthio, or

R for the rest of the formula

stands.

Acid addition salts of those compounds of the formula (I) in which G is mono- or bicyclic, saturated or unsaturated are also preferred Heterocyclyl with up to 12 ring members, which is bonded via a nitrogen atom, this nitrogen atom in the heterocycle being connected to a further nitrogen atom, and wherein the heterocycle optionally contains one or two further oxygen, nitrogen and or sulfur atoms, but none two oxygen atoms can be directly adjacent, where the heterocycles can be monosubstituted to trisubstituted, identical or different by cyano, halogen, alkyl having 1 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms or by alkoxycarbonyl 1 to 4 carbon atoms in the alkoxy group, and R and X have those meanings which have been mentioned as preferred for these radicals.

The acids that can be added preferably include hydrohalic acids, e.g. hydrochloric acid and hydrobromic acid, in particular hydrochloric acid, also phosphoric acid, nitric acid, mono- and bifunctional carboxylic acids and hydroxycarboxylic acids, e.g. Acetic acid, maleic acid, succinic acid, fumaric acid, tartaric acid, citric acid, salicylic acid, sorbic acid and lactic acid, as well as sulfonic acids, e.g. p-toluenesulfonic acid, 1,5-naphthalenedisulfonic acid, saccharin and thiosaccharin.

Particularly preferred are salts which are formed by adding hydrochloric acid, phosphoric acid, p-toluenesulfonic acid, 1,5-naphthalenedisulfonic acid or saccharin to triazolopyrimidines of the formula (I) in which

G for a heterocyclyl radical of the formula

stands,

where each of these radicals can be substituted once to three times, identically or differently, by cyano, fluorine, chlorine, methyl, ethyl, methoxycarbonyl and / or ethoxycarbonyl, and

R and X have the meanings which have been mentioned as particularly preferred for these radicals.

The aforementioned radical definitions can be combined with one another in any way. In addition, individual meanings can also be omitted.

The general or preferred radical definitions given above apply both to the end products of the formula (I) and correspondingly to the starting materials or intermediates required in each case for the preparation.

If 5,7-dichloro-6- (2,4,6-trifluoφhenyl) [1,2,4] triazolo [1,5a] pyrimidine and 3-methyl-isoxazolidine hydrochloride are used as starting materials, the course of the method according to the invention are illustrated by the following formula.

Formula (II) provides a general definition of the dihalotriazolopyrimidines required as starting materials for carrying out the process according to the invention. In this formula (II), R and X preferably, or in particular, have those meanings which have already been given as preferred or as particularly preferred for R and X in connection with the description of the compounds of the formula (I) according to the invention. Y preferably represents fluorine, chlorine or bromine, in particular fluorine or chlorine.

The dihalotriazolopyrimidines of the formula (II) are known or can be prepared by known methods (see, for example, US Pat. No. 5,612,345).

Formula (III) provides a general definition of the heterocycles required as starting materials for carrying out the process according to the invention. In this formula (III) G preferably, or in particular, has the meaning which has already been stated as preferred or as particularly preferred for G in connection with the description of the compounds of the formula (I) according to the invention.

The heterocycles of the formula (III) are known or can be prepared by known methods (cf., for example, BJ Chem. Soc. 1942, 432; Can. J. Chem. (1976), 54 (6), 867-70; Tetrahedron Lett. (1993), 34 (36), 5673-6; Tetrahedron Lett. (1973), 30, 2859-2862).

The heterocycles of the formula (III) can also be used in the form of their acid addition salts when carrying out the process according to the invention. As

Acid addition salts are preferably those compounds which result from the addition of those acids, which have already been mentioned in connection with the description of the acid addition salts according to the invention, to heterocycles of the formula (III). Hydrochlorides and acetates of heterocycles of the formula (III) are preferred.

Suitable diluents for carrying out the process according to the invention are all inert organic solvents. Aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, can preferably be used.

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; Amides, such as N, N-dimethylformamide, N, N-dimethylacetamide, N-

Methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; Esters such as methyl acetate or ethyl acetate; Sulfoxides, such as dimethyl sulfoxide; Sulfones such as sulfolane.

As acid acceptors come when carrying out the invention

Process all usual acid binders into consideration. Ammonia or tertiary amines, such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, N-dimethylbenzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO ), Diazabicyclonones (DBN) or diazabicycloundecene (DBU). There are also alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonate or bicarbonate in question, such as sodium hydride, sodium amide, sodium methylate, sodium ethylate, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, sodium acetate, potassium acetate, calcium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate and sodium hydrogen carbonate.

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

When carrying out the method according to the invention one works in

Generally under atmospheric pressure. However, it is also possible to work under increased pressure up to 10 bar or under reduced pressure up to 0.1 bar.

When carrying out the process according to the invention, 0.5 to 10 mol, preferably 0.8 to 2 mol, of a compound of the formula (III) are generally employed per 1 mol of dihalotriazolopyrimidine of the formula (II). The processing takes place according to usual methods.

For the preparation of acid addition salts of triazolopyrimidines of the formula (I), preference is given to those acids which have already been mentioned as preferred acids in connection with the description of the acid addition salts according to the invention.

The acid addition salts of the compounds of formula (I) can be easily prepared by conventional salt formation methods, e.g. by disconnecting the

Formula (I) can be obtained in a suitable inert solvent and addition of the acid, for example hydrochloric acid, and isolated in a known manner, for example by filtering off, and optionally purified by washing with an inert organic solvent. The substances according to the invention have a strong microbicidal action and can be used to control unwanted microorganisms, such as fungi and bacteria, in crop protection and in material protection.

Fungicides can be used to control Plasmodiophoromycetes,

Use Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.

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

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

Xanthomonas species, such as, for example, Xanthomonas campestris pv. Oryzae;

Pseudomonas species, such as, for example, Pseudomonas syringae pv. Lachrymans;

Erwinia species, such as, for example, Erwinia amylovora;

Pythium species, such as, for example, Pythium ultimum;

Phytophthora species, such as, for example, Phytophthora infestans;

Pseudoperonospora species, such as, for example, Pseudoperonospora humuli or

Pseudoperonospora cubensis;

Plasmopara species, such as, for example, Plasmopara viticola; Bremia species, such as, for example, Bremia lactucae;

Peronospora species, such as, for example, Peronospora pisi or P. brassicae;

Erysiphe species, such as, for example, Erysiphe graminis;

Sphaerotheca species, such as, for example, Sphaerotheca fuliginea;

Podosphaera species, such as, for example, Podosphaera leucotricha;

Venturia species, such as, for example, Venturia inaequalis;

Pyrenophora species, such as, for example, Pyrenophora teres or P. graminea

(Conidial form: Drechslera, Syn: Helminthosporium);

Cochliobolus species, such as, for example, Cochliobolus sativus

(Conidial form: Drechslera, Syn: Helminthosporium);

Uromyces species, such as, for example, Uromyces appendiculatus;

Puccinia species, such as, for example, Puccinia recondita;

Sclerotinia species, such as, for example, Sclerotinia sclerotiorum;

Tilletia species, such as, for example, Tilletia caries;

Ustilago species, such as, for example, Ustilago nuda or Ustilago avenae;

Pellicularia species, such as, for example, Pellicularia sasakii; Pyricularia species, such as, for example, Pyricularia oryzae;

Fusarium species, such as, for example, Fusarium culmorum;

Botrytis species, such as, for example, Botrytis cinerea;

Septoria species, such as, for example, Septoria nodorum;

Leptosphaeria species, such as, for example, Leptosphaeria nodorum;

Cercospora species, such as, for example, Cercospora canescens;

Alternaria species, such as, for example, Alternaria brassicae;

Pseudocercosporella species, such as, for example, Pseudocercosporella heφotrichoides.

The active compounds according to the invention also have a very good strengthening effect in plants. 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 defense system of plants in such a way that - ^" the treated plants develop extensive resistance to these microorganisms when they are subsequently inoculated with undesirable microorganisms.

Undesired microorganisms are to be understood in the present case as phytopathogenic 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, within which protection is brought about generally ranges from 1 to 10 days, preferably 1 to 7 days after the treatment of the plants with the active compounds.

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 to combat diseases in wine, fruit and vegetable cultivation, such as, for example, against Botrytis, Venturia and Alternaria species, or rice diseases, such as, for example, 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.

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.

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 should include all above-ground and underground parts and organs the plants, such as sprout, leaf, flower and root, are understood, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as 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 according to 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 can

Adhesives, glues, paper and cardboard, textiles, leather, wood, paints and plastic articles, cooling lubricants and other materials that can be attacked or decomposed by microorganisms. In the context of the materials to be protected, parts of production plants, for example cooling water circuits, may also be mentioned which can be impaired by the multiplication of microorganisms. Within the scope of the present invention, technical materials are preferably adhesives, glues, papers and cartons, leather, wood, paints, lubricants and heat transfer liquids, particularly preferably wood. Bacteria, fungi, yeasts, algae and mucilaginous organisms may be mentioned as microorganisms which can cause degradation or a change in the technical materials. The active compounds according to the invention preferably act against fungi, in particular mold, wood-discoloring and wood-destroying fungi (Basidiomycetes) and against slime organisms and algae.

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

Alternaria, such as Altemaria 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.

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 stalks. Suitable emulsifiers and / or foam-generating 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, acyl sulfates, aryl sulfonates and protein hydrolyzates. As dispersants come in

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

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

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

The formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.

The active compounds according to the invention, as such or in their formulations, can also be used in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, in order, for example, to broaden the 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, binapacrylic, biphenyl, bitertanol, blasticidin-S, bromuconazole, bupirimate, buthiobate,

Calcium polysulfide, Caφropamid, Capsimycin, Captafol, Captan, Carbendazim, Carboxin, Carvon, Quinomethionate (Quinomethionate), Chlobenthiazon, Chlorfenazol,

Chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon, cufraneb, cymoxanil, cyproconazole, cyprodinil, cyprofuram,

Debacarb, dichlorophene, diclobutrazole, diclofluanide, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomoφh, diniconazole,

Diniconazol-M, Dinocap, Diphenylamine, Dipyrithione, Ditalimfos, Dithianon, Dodemoφh, Dodine, Drazoxolon,

Ediphenphos, Epoxiconazole, Etaconazole, Ethirimol, Etridiazole,

Famoxadon, Fenapanil, Fenarimol, Fenbuconazol, Fenfuram, Fenhexamid, Fenitropan, Fenpiclonil, Fenpropidin, Fenpropimoφh, Fentinacetat, Fentinhydroxyd, Ferbam, Ferimzon, -Fluazinam, Flumetover, Fluoromid, Fluquinconazol, Flusulfolidilololifolilililidololifilililidololifilililidolol, fulphosilutolidol, fulosolutilidol, flusulfolidilolidol, fulosolidilolidilolidilolidololifolililolidololifolililolidololifolidilololifolidilolifolidilidol, folusolutolutilofolidosilutol -Alminium, fosetyl-sodium, fthalide, fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole,

Furconazole-cis, furmecyclox, fluoxastrobin,

guazatine,

Hexachlorobenzene, hexaconazole, hymexazole, Imazalil, Imibenconazol, Iminoctadin, Iminoctadinealbesilat, Iminoctadinetriacetat, Iodocarb, Ipconazol, Iprobefos (IBP), Iprodione, Iprovalicarb, Irumamycin, Isoprothiolan, Isovaledione,

Kasugamycin, Kresoxim-methyl, copper preparations such as: copper hydroxide,

Copper phthalate, copper oxychloride, copper sulfate, copper oxide, oxine-copper and Bordeaux mixture,

Mancopper, Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Methturoxam, Metiram, Metomeclam, Metsulfovax,

Mildiomycin, myclobutanil, myclozolin,

Nickel dimethyldithiocarbamate, nitrothal isopropyl, Nuarimol,

Ofurace, Oxadixyl, Oxamocarb, Oxolinicacid, Oxycarboxim, Oxyfenthiin,

Paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen, picoxystrobin, pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz, procymidon, propamocarb, propanosine sodium, propiconazole, propineb, pyraclostroonyl, pyrazophyronyl, pyrrazole, pyrazulopyronyl, pyrazolostyron, pyrazolostyron, pyrazolostyron, pyrazolostyron, pyrazolostyron, pyrazylostyron, pyrazylostyron, pyrazylostyron, pyrazylostyron, pyrazolostyrene, pyrazolostyrene, pyrazolopyronyl, pyrazolostyrene, pyrazolostyrene, pyrazolostyrene, pyrazole pyridine, pyrazole pyridine, pyrazole pyrone, pyrazole pyrone, pyrazine pyridine, pyrazine pyridine, pyrazine pyridine, pyrazine pyridine, pyrazine pyridine, pyrazine pyridine, pyrazole, pyrazole

Quinconazole, quintozen (PCNB), quinoxyfen

Sulfur and sulfur preparations, spiroxamines

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

uniconazole Validamycin A, vinclozolin, viniconazole,

Zarilamid, Zineb, Ziram as well

Dagger G,

OK-8705, OK-8801, α- (1, 1-dimethylethyl) -ß- (2-phenoxyethyl) - 1 H-1, 2,4-triazole-1-ethanol, - (2,4-dichloφhenyl) - ß-fluoropropyl-1 H-1, 2,4-triazole-1-ethanol, α- (2,4-dichlorophenyl) -ß-methoxy-α-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-2,2,7,7-tetramethyl-5- (lH-l, 2,4-triazol-l-yl) -3-octanone,

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

1 - (2,4-dichloφhenyl) -2- (1 H- 1, 2,4-triazol-1-yl) -ethanone-O- (phenylmethyl) -oxime,

1 - (2-methyl-1-naphthalenyl) - 1 H-pyrrole-2,5-dione, 1 - (3,5-dichlorophenyl) -3- (2-propenyl) -2,5-pyrrolidinedione, l- [ (Diiodomethyl) sulfonyl] -4-methyl-benzene, l - [[2- (2,4-dichloro-henyl) -l, 3-dioxolan-2-yl] methyl] -lH-imidazole,

1 - [[2- (4-chloro-phenyl) -3-phenyloxiranyl] methyl] - 1 H- 1, 2,4-triazole, l- [l- [2 - [(2,4-dichloro-phenyl) methoxy]] -phenyl] -ethenyl] -IH-imidazole, 1-methyl-5-nonyl-2- (phenylmethyl) -3-pyrrolidinol,

2 \ 6'-dibromo-2-methyl-4'-trifluoromethoxy-4-trifluoro-memyl-l, 3-tHazol-5-carboxanilide,

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

2,6-dichloro-N- (4-1rifluorme ylbeιιzyl) benzamide,

2,6-dichloro-N - [[4- (trifluoromethyl) phenyl] methyl] benzamide, 2- (2,3,3-triiodo-2-propenyl) -2H-tetrazole,

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

2 - [[6-Deoxy-4-O- (4-O-methyl-β-D-glycopyranosyl) -α-D-glucopyranosyl] amino] -4- methoxy-lH-pyrτolo [2,3-d] pyrimidine-5-carbonitrile,

2-aminobutane, 2-bromo-2- (bromomethyl) pentandinitrile,

2-chloro-N- (2,3-dihydro-l, l, 3-trimethyl-lH-mden-4-yl) -3-pyridine carboxamide, 2-chloro-N- (2,6-dimethylphenyl) -N- (isothiocyanatomethyl) acetamide, 2-phenylphenol (OPP),

3,4-dichloro-1 - [4- (difluoromethoxy) phenyl] - 1 H-pyrrole-2,5-dione, 3,5-dichloro-N- [cyan [(l-methyl-2-propynyl) - oxy] -methyl] -benzamide, 3- (1, 1-dimethylpropyl-1-oxo-1 H-indene-2-carbonitrile,

3- [2- (4-chloro-phenyl) -5-ethoxy-3-isoxazolidinyl] pyridine, 4-chloro-2-cyano-N, N-dimethyl-5- (4-methylphenyl) -1 H-imidazole-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- (l-methylethyl) -3-methyl-4 - [(3-methylbenzoyl) -oxy] -2,5-thiophene dicarboxylate, ice-1 - (4-chloro-phenyl) -2- (1 H- 1, 2,4- triazol-1 -yl) -cycloheptanol, cis-4- [3- [4- (l, l-dimethylpropyl) phenyl-2-methylpropyl] -2,6-dimethyl-moφholin hydrochloride, ethyl - [(4- chloφhenyl) azo] cyanoacetate,

Potassium hydrogen carbonate, methane tetrathiol sodium salt,

Methyl 1 - (2,3-dihydro-2,2-dimethyl-1 H-inden-1-yl) - 1 H-imidazole-5-carboxylate, methyl-N- (2,6-dimethylphenyl) -N- (5-isoxazolylcarbonyl) -DL-alaninate, methyl-N- (chloroacetyl) -N- (2,6-dimethylphenyl) -DL-alaninate,

N- (2,6-dimethylphenyl) -2-methoxy-N- (tefrahydro-2-oxo-3-furanyl) acetanide, N- (2,6-dimethylphenyl) -2-memoxy-N- (tefrahyα ^ o -2-oxo-3-tMenyl) acetamide, N- (2-chloro-4-nitrophenyl) -4-methyl-3-nitro-benzenesulfonamide, N- (4-cyclohexylphenyl) -l, 4,5,6- tefrahydro-2-pyrimidamine, N- (4-hexylphenyl) -l, 4,5,6-tetrahydro-2-pyrimidinamine,

N- (5-chloro-2-methylphenyl) -2-methoxy-N- (2-oxo-3-oxazolidmyl) 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-methanimidamide, N-formyl-N-hydroxy-DL-alanine sodium salt,

O, O-diethyl [2- (dipropylarmno) -2-oxoemyl] -emylphosphoramidothioat, O-methyl-S-phenyl-phenylpropylphosphoramidothioate, S-methyl-1, 2,3-benzothiadiazole-7-carbothioate, spiro [2H] -l-benzopyran-2, (3Η) -isobenzofuran] -3'-one, 4 - [3,4-dimethoxyphenyl) -3- (4-fluoφhenyl) acryloyl] -moφholin

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

Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, Chloethocarb, Chlorethoxyfos, Chlorfenapyr, Chlorfenvinphos, Chlorfluazuron,

Chlormephos, Chloφyrifos, Chloφyrifos M, Chlovaporthrin, Chromafenozide, Cis- Resmethrin, Cispermethrin, Clocythrin, Cloethocarb, Clofentezine, Clothianidine, Cyanophos, Cycloprene, Cycloprothrin, Cyfluthrin, Cyhalothrinomethine, Cyatin Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Diazinon, Dichlorvos, Dicofol, Diflubenzuron, Dimethoat, Dimethylvinphos, Diofenolan, Disulfoton, Docusat-sodium, Dofenapyn,

Eflusilanate, Emamectin, Empenthrin, Endosulfan, Entomopfthora spp.,

Esfenvalerate, Ethiofencarb, Ethion, Ethoprophos, Etofenprox, Etoxazole, Etrimfos,

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

Flumethrin, Flutenzine, Fluvalinate, Fonophos, Fosmethilan, Fosthiazate, Fubfenprox, Furathiocarb,

granulosis

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

Imidacloprid, indoxacarb, isazofos, isofenphos, isoxathion, ivermectin,

Kempolyederviren

Lambda cyhalothrin, lufenuron

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

Methoxyfenozide, metolcarb, metoxadiazone, mevinphos, milbemectin, milbemycin, 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, Propargite, Propoxur, Prothiofos, Prothrohrinos, Pothrohrinos, Pothrohrine, Pothrohrinate , Pyridaben, pyridathione,

Pyrimidifen, pyriproxyfen,

quinalphos,

ribavirin

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

Tau-fluvalinate, tebufenozide, tebufenpyrad, Tebupirimiphos, teflubenzuron, tefluthrin, temephos, Temivinphos, terbufos, tetrachlorvinphos, tetradifon theta cypermethrin, thiacloprid thiocyclam hydrogen oxalate, thiamethoxam, Thiapronil, Thiatriphos, thiodicarb, thiofanox, thuringiensin, Tralocythrin, tralomethrin, triarathene , Triazamates, triazophos, triazuron, trichlophenidines, trichlorfon, triflumuron, trimethacarb,

Vamidothion, Vaniliprole, Verticillium lecanii

Yl 5302

Zeta-cypermethrin, zolaprofos

(IR-cis) - [5- (phenylmethyl) -3-furanyl] methyl-3 - [(dihydro-2-oxo-3 (2H) - furanylidene) methyl] -2,2-dimethylcyclopropane carboxylate

(3-phenoxyphenyl) methyl-2,2,3,3-tetramethylcyclopropanecarboxylat l - [(2-chloro-5-thiazolyl) methyl] tetrahydro-3,5-dimethyl-N-niπO-l, 3,5-triazin-2 (1H) - imine

2- (2-Chloro-6-fluoφhenyl) -4- [4- (l, l-dimethylethyl) phenyl] -4,5-dihydro-oxazole 2- (acetyloxy) -3-dodecyl-1, 4-naphthalenedione

2-chloro-N- [[[4- (1-phenylethoxy) phenyl] amino] carbony 1] benzamide

2-Chloro-N - [[[4- (2,2-dichloro-1,1-difluoroethoxy) phenyl] amino] carbonyl] benzamide

3-methylphenyl propylcarbamate

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-dichloro-phenyl) -3 (2H) -pyridazinone Bacillus thuringiensis strain EG-2348

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

Butanoic acid 2,2-dimethyl-3- (2,4-dichloφhenyl) -2-oxo-1-oxaspiro [4.5] dec-3-en-4-yl ester

[3 - [(6-chloro-3-pyridinyl) methy 1] -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-l-oxo-3- butenyl) -glycine

N- (4-Chlθφhenyl) -3- [4- (difluoromethoxy) phenyl] -4,5-dihydro-4-phenyl-lH-pyrazol-

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

N-cyanomethyl-4-trifluoromethyl-nicotinamide

3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- [3- (5-trifluoromethylpyridin-2-yloxy) propoxyj-benzene

A mixture with other known active ingredients, such as herbicides or with fertilizers and growth regulators, is also possible.

In addition, the compounds of formula (I) according to the invention also have very good antifungal effects. They have a very broad spectrum of antimycotic effects, in particular against dermatophytes and shoot fungi, mold and diphasic fungi (for example against Candida species such as Candida albicans, Candida glabrata) as well as 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 The list of these fungi does not in any way limit the mycotic spectrum that can be recorded, 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. They are used in the usual way, e.g. by pouring, spraying, atomizing, scattering, dusting, foaming, brushing, etc. It is also possible to apply the active ingredients using the ultra-low-volume method or to inject the active ingredient preparation or the active ingredient into the soil itself. It can also do that

Seeds of the plants are 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.

As already mentioned, all plants and their parts can be treated according to the invention. In a preferred embodiment, plant species and plant cultivars which occur wildly or are obtained by conventional biological breeding methods, such as crossing or protoplast fusion, and parts thereof 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. Plant cultivars are understood to mean plants with new properties (“traits”) which have been bred by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be varieties, breeds, bio and genotypes.

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 cause superadditive ("synergistic") effects. For example, reduced application rates and / or widening of the activity spectrum and / or an increase in the action of the substances and agents which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to 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 storability and or workability of the harvested products, which go beyond the effects that are actually 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, have received 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 drought or to water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripening, higher harvest yields, higher quality and / or higher nutritional value of the harvested products, higher storage 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 insects, mites, plant pathogenic 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), maize, soybeans, potatoes, cotton, rapeseed and fruit plants (with the fruits apples, pumice, citrus and

Grapes) mentioned, with corn, soybeans, potatoes, cotton and rapeseed being particularly emphasized. The traits are particularly emphasized as the increased defense of the plants against insects by toxins which arise 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), CryIA (c),

CryllA, CrylllA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF as well as their combinations) are produced in the plants (hereinafter "Bt plants"). The properties ("traits") also particularly emphasize the increased defense of plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins. The properties (“traits”) which are particularly emphasized are the increased tolerance of the plants to certain herbicidal active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (for example “PAT” gene). The genes which confer the desired properties (“traits”) can also be found in

Combinations with each other occur in the transgenic plants. Examples of "Bt plants" are corn varieties, cotton varieties, soy varieties and potato varieties that are sold under the trade names YIELD GARD® (e.g. corn, cotton, soy), KnockOut® (e.g. corn), StarLink® (e.g. corn), Bollgard® ( Cotton), Nucoton® (cotton) and NewLeaf® (potato).

Examples of herbicide-tolerant plants are maize varieties, cotton varieties and soy varieties that are sold under the trade names Roundup Ready® (tolerance to glyphosate e.g. corn, cotton, soy), Liberty Link® (tolerance to phosphinotricin, e.g. rapeseed), TI® (tolerance to Imidazolinone) and STS® (tolerance to sulfonylureas such as maize). Plants that are herbicide-resistant (conventionally grown to herbicide tolerance) are also varieties sold under the name Clearfield® (eg 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 with the compounds of the 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 specifically listed in the present text should be particularly emphasized.

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

Preparation Examples

example 1

180 mg (0.56 mmol) of 5,7-dichloro-6- (2,4,6-trifluoφhenyl) [1,2,4] triazolo [1,5-ajpyrimidine, 120 mg (0.97 mmol) 3 -Methylisoxazolidine hydrochloride and 335 mg of potassium carbonate are stirred for 18 hours under argon at room temperature in 10 ml of acetonitrile. The reaction mixture is mixed with 10 ml of water, the organic phase is separated off, washed with 10 ml of saturated ammonium chloride solution, dried over sodium sulfate and concentrated under reduced pressure. The residue is chromatographed on silica gel using petroleum ether / ethyl acetate (10: 1). 250 mg (49% of theory) of 5-chloro-6- (2,4,6-trifluoφhenyl) -7- (3-methyl-2-isoxazolidinyl) [1, 2,4] triazolo [1, 5 -a] pyrimidine. HPLC: logP = 2.76

The compounds of the formula mentioned in Table 1 below are also analogous to Example 1 and in accordance with the information in the general description of the process

contain. Table 1

Table 1 (continued)

# stands for the link in the table above.

*) The logP values were determined in accordance with EEC Directive 79/831 Annex V. A8 by HPLC (gradient method, acetonitrile / 0.1% aqueous phosphoric acid) Preparation of a precursor of formula (II)

Example 72

To a solution of 1.6 g of potassium t-butanolate in 40 ml of t-butanol, 1.83 g (17.4 mmol) of ethyl hydroxycarbamate and 1 g (4.6 mmol) of 1,3-dibromobutane are added and the mixture is stirred for 7 hours 65 ° C. The reaction mixture is concentrated under reduced pressure, the residue is mixed with ether and water and the organic phase is separated off. The aqueous phase is extracted twice more with ether, the combined organic phases are dried over sodium sulfate and concentrated under reduced pressure. 1 g of crude, approximately 80% N-ethoxycarbonyl-3-methylisoxazolidine with a logP value of 1.22 is obtained.

950 mg of which are refluxed in 10 ml of 16% hydrochloric acid for 3 hours. The mixture is concentrated under reduced pressure, stirred three times with 5 ml of methanol and filtered each time. The combined filtrates are concentrated under reduced pressure. 560 mg of 3-methylisoxazolidine hydrochloride with a logP value of 1.22 are obtained

use Examples

Example A

Venturia test (apple) / protective

Solvent: 24.5 parts by weight of acetone

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

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

To test for protective activity, young plants are sprayed with the active compound preparation in the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous conidia suspension of the Venturia inaequalis apple scab pathogen and then remain in an incubation cabin at about 20 ° C. and 100% relative atmospheric humidity for 1 day.

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

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

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

Venturia test (apple) / protective

Table A (continued) Venturia test (apple) / protective

Example B

Botrytis test (bean) / protective

Solvent: 24.5 parts by weight of acetone

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 dilute the concentrate with water to the desired concentration.

To test for protective activity, young plants are sprayed with the active compound preparation in the stated application rate. After the spray coating has dried on, 2 small pieces of agar covered with Botrytis cinerea are placed on each leaf. The inoculated plants are placed in a darkened chamber at approx. 20 ° C and 100% relative humidity.

2 days after the inoculation, the size of the infection spots on the leaves is evaluated. 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 B

Botrytis test (bean) / protective

Table B (continued) Botrytis test (bean) / protective

Example C

Altemaria test (tomato) / protective

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

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To test for protective activity, young tomato plants are sprayed with the preparation of active compound in the stated application rate. 1 day after the treatment, the plants are inoculated with a spore suspension of Altemaria solani and then stand at 100% rel. Humidity and 20 ° C. Then the plants are at 96% rel. Humidity and a temperature of 20 ° 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 C.

Altemaria test (tomato) / protective

Example D

Pyricularia test (rice) / protective

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

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

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

Concentration.

To test for protective activity, young rice plants are sprayed with the preparation of active compound in the stated application rate. 1 day after the treatment, the plants are inoculated with an aqueous spore suspension of Pyricularia oryzae. The plants are then placed in a greenhouse at 100% relative atmospheric humidity and 25 ° C.

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

Pyricularia test (rice) / protective

Claims

claims

1. Triazolopyrimidines of the formula

in which

G represents optionally substituted, mono- or polycyclic, saturated, unsaturated or aromatic heterocyclyl which is bonded via a nitrogen atom, this nitrogen atom in the heterocycle being connected to a further nitrogen or oxygen atom, and the heterocycle optionally also one or two more Contains oxygen, nitrogen and / or sulfur atoms, but no two oxygen atoms can be directly adjacent,

R represents aryl which is optionally monosubstituted to pentasubstituted, and

X represents halogen,

as well as acid addition salts of those compounds of formula (I) in which

G represents optionally substituted, mono- or polycyclic, saturated or unsaturated heterocyclyl which is bonded via a nitrogen atom, this nitrogen atom in the heterocycle being connected to a further nitrogen atom, and wherein the Heterocycle optionally also contains one or two further oxygen, nitrogen and / or sulfur atoms, but no two oxygen atoms can be directly adjacent.

Process for the preparation of triazolopyrimidines of the formula (I) according to

Claim 1, characterized in that one

Dihalotriazolopyrimidines of the formula

in which

R and X have the meanings given above and

Y represents halogen,

with heterocycles of the formula

G-H (III)

in which

G has the meaning given above,

or with acid addition salts of heterocycles of the formula (III) if appropriate in the presence of a diluent and if appropriate in the presence of an acid acceptor.

3. Microbicidal agents, characterized by a content of at least one triazolopyrimidine of the formula (I) according to Claim 1 or of one

Acid addition salt thereof, in addition to extenders and / or surface-active substances.

4. Use of triazolopyrimidines of the formula (I) according to Claim 1 or of their acid addition salts for controlling unwanted microorganisms.

5. A process for combating undesirable microorganisms, characterized in that triazolopyrimidines of the formula (I) according to Claim 1 or their acid addition salts are applied to the undesired microorganisms and / or their habitat.

6. Process for the preparation of microbicidal agents, characterized in that triazolopyrimidines of the formula (I) according to Claim 1 or their acid addition salts are mixed with extenders and / or surface-active substances.