DE10015015A1 - New oxyalkanimidoylphenyl-substituted N-(heterocyclyl)-alkanoamide derivatives, are bactericides, fungicides, insecticides, acaricides and nematocides, useful e.g. in plant or material protection or as antimycotic agents - Google Patents

Abstract

Oxyalkanimidoylphenyl-substituted N-(isothiazolyl, thiadiazolyl or pyridyl)-alkanoamide derivatives (I) are new. Oxyalkanimidoylphenyl-substituted N-(isothiazolyl, thiadiazolyl or pyridyl)-alkanoamide derivatives (I) are new. [Image] A : alkanediyl; R1>1,2-thiazolyl, 1,2,4-thiadiazolyl or pyridyl (all optionally substituted); R2>H, alkyl or optionally substituted phenyl; R3>H, alkyl, alkoxyalkyl, alkenyl or alkylcarbonyl; or (all optionally substituted) aryl, aralkyl, arylcarbonyl, heterocyclyl, heterocyclylalkyl or heterocyclylcarbonyl; R4>H, halo, alkyl, alkoxy, CN or NO2. An independent claim is included for the preparation of (I). - ACTIVITY : Antibacterial; fungicide; insecticide; acaricide; nematocide. 2-(3-((1-N-Tert. butoxyethanimidoyl)-phenyl)-N-(3-ethyl-1,2,4-thiadia zol-5-yl)-acetamide (Ia) at 100 g/ha gave more than 90% protection of apple trees against Podosphaera leuchotricha. - MECHANISM OF ACTION : None given.

Description

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

It has already become known that numerous N- (5-isothiazolyl) amides or N- (5- Thiadiazolyl) amides have insecticidal and fungicidal properties (cf. WO 97- 18 198, WO 97-26 251 and WO 95-31 448). The effectiveness of these substances is good but leaves something to be desired in some cases at low application rates.

There have now been new oxime derivatives of the formula

in which
A represents alkanediyl,
R ¹ represents optionally substituted 1,2-thiazolyl, 1,2,4-thiadiazolyl or pyridyl,
R ^{2 represents} hydrogen, alkyl or optionally substituted aryl,
R ^{3 represents} hydrogen, alkyl, alkoxyalkyl, alkenyl, alkylcarbonyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted arylcarbonyl, optionally substituted heterocyclyl, optionally substituted heterocyclylalkyl or optionally substituted heterocyclylcarbonyl and
R ^{4 represents} hydrogen, halogen, alkyl, alkoxy, cyano or nitro.

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

in which
A, R ¹ , R ² and R ^{4 have} the meanings given above,
with an oxyamine of the formula

R ³ -O-NH ₂ (III),

in which
R ^{3 has} the meaning given above,
or their acid addition complexes,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.

Finally, it was found that the new oxime derivatives of formula (I) are very good to combat unwanted microorganisms and animal pests  are suitable. In particular, they show a strong fungicidal and insecticidal we kung.

Surprisingly, the oxime derivatives of the formula (I) according to the invention have a much better fungicidal and insecticidal activity than the constitutional most similar, previously known substances with the same direction of action.

Formula (I) provides a general definition of the oxime derivatives according to the invention. You can optionally as mixtures of various possible isomeric For Men, especially of stereoisomers such. B. E- and Z-, and optical isomes ren, but possibly also of tautomers. The invention relates both the E and the Z isomers, and also the optical isomers, any Mixtures of these isomers, as well as the possible tautomeric forms.

Oxime derivatives of the formula (I) are preferred in which
A represents alkanediyl having 1 to 4 carbon atoms,
R ¹ represents 1,2-thiazolyl, 1,2,4-thiadiazolyl or pyridyl which is optionally mono- or disubstituted by alkyl having 1 to 4 carbon atoms and / or halogen,
R ^{2 represents} hydrogen, alkyl having 1 to 4 carbon atoms or optionally optionally up to four times, identical or different, aryl having 6 to 10 carbon atoms substituted by halogen and / or alkyl having 1 to 4 carbon atoms,
R ^{3 represents} hydrogen, alkyl having 1 to 6 carbon atoms, alkoxyalkyl having 1 to 4 carbon atoms in the alkoxy part and 1 to 4 carbon atoms in the alkyl part, alkenyl having 2 to 6 carbon atoms or alkylcarbonyl having 1 to 6 carbon atoms in the alkyl part, or
represents aryl with b to 10 carbon atoms, where each of these radicals can be substituted one to four times, in the same way or differently, by halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 4 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy or haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms,
or
represents aralkyl having 6 to 10 carbon atoms in the aryl part and 1 to 4 carbon atoms in the alkyl part, where each of these radicals can be substituted up to four times, in the same way or differently, by halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkylthio each 1 to 4 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy or haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms,
or
represents arylcarbonyl having 6 to 10 carbon atoms in the aryl part, each of these radicals being able to be substituted up to four times, identically or differently by halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkylthio, each having 1 to 4 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy or haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms,
or
represents heterocyclyl with 5 or 6 ring members and 1 to 3 heteroatoms, such as oxygen, nitrogen and / or sulfur, where these radicals can optionally be monosubstituted to trisubstituted, identical or different, by halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 4 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy or halogenoalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms,
or
represents heterocyclylalkyl having 5 or 6 ring members and 1 to 3 heteroatoms, such as oxygen, sulfur and / or nitrogen, and 1 to 4 carbon atoms in the alkyl part, where these radicals can optionally be mono- to trisubstituted, identical or differently substituted by halogen, cyano, Nitro, each straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 4 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy or haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms,
or
represents heterocyclylcarbonyl with 5 or 6 ring members and 1 to 3 heteroatoms, such as oxygen, nitrogen and / or sulfur, where these radicals can optionally be mono- to trisubstituted, identical or differently substituted by halogen, cyano, nitro, in each case straight-chain or ver branched alkyl, alkoxy or alkylthio each having 1 to 4 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy or haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms,
and
R ^{4 represents} hydrogen, alkyl having 1 to 4 carbon atoms or alkoxy having 1 to 4 carbon atoms.

Oxime derivatives of the formula (I) in which
A represents methylene or ethanediyl,
R ^{1 represents} 1,2-thiazolyl which is optionally mono- or disubstituted by methyl, ethyl and / or chlorine or represents 1,2,4-thiadiazolyl which is optionally substituted by methyl, ethyl or chlorine or optionally mono- or disubstituted by methyl, Ethyl and / or chlorine substituted pyridyl,
R ^{2 represents} hydrogen, methyl, ethyl or phenyl optionally substituted once or twice, in the same way or differently, by methyl, ethyl and / or chlorine,
R ^{3 represents} hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, sec-butyl, i-butyl, tert-butyl, methoxymethyl, allyl, acetyl, propionyl, pivaloyl or 3,3-dimethylbutanoyl , or
represents phenyl, benzyl, benzoyl, pyridyl, pyridylmethyl or pyridylcarbonyl, where each of these radicals can be monosubstituted to triple, identical or differently substituted by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl , n-, i-, s- or t-butyl, methoxy, ethoxy, methylthio, ethylthio, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio and / or trifluoromethyl
and
R ^{4 represents} hydrogen, methyl, ethyl, methoxy or ethoxy.

Oxime derivatives of the formula (I) in which
A represents methylene or ethanediyl,
R ^{1 represents} 1,2-thiazol-5-yl which is optionally mono- or disubstituted by methyl, ethyl and / or chlorine, or represents 1,2,4-thiadiazol-5-yl which is optionally substituted by methyl, ethyl or chlorine, or represents pyridyl which is optionally mono- or disubstituted by methyl, ethyl and / or chlorine,
R ^{2 represents} hydrogen, methyl, ethyl or phenyl,
R ^{3 represents} hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, sec-butyl, i-butyl, tert-butyl, methoxymethyl, allyl, acetyl, propionyl, pivaloyl or 3,3, -dimethylbutanoyl , or represents phenyl, benzyl, benzoyl, pyridyl, pyridylmethyl or pyridylcarbonyl, where each of these radicals can be monosubstituted to triple, identical or differently substituted by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i Propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, methylthio, ethylthio, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluorethoxy, difluoromethylthio, difluorochloro or trifluoromethyl or trifluoromethyl
and
R ^{4 represents} hydrogen, methyl or methoxy.

The above-mentioned radical definitions can be used with each other in any way be combined. In addition, individual meanings can also be omitted.

If 2- (3-acetyl-phenyl) -N- (3-methyl-1,2,4-thiadiazol-5-yl) acetamide is used and methoxyamine hydrochloride as starting materials, the course of the method according to the invention illustrated by the following formula become.

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

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

in which
A, R ¹ , R ² and R ^{4 have} the meanings given above and
X represents halogen,
with amines of the formula

R ¹ -NH ₂ (V),

in which
R ^{1 has} the meaning given above,
if appropriate in the presence of a diluent and if appropriate in the presence of a base.

Formula (IV) provides a general definition of the carboxylic acid halides required as starting materials for the preparation of the carbonyl compounds of the formula (II). In this formula, A and R ² and R ⁴ preferably have those meanings which have already been mentioned as preferred for these radicals or this index in connection with the description of the substances of the formula (I) according to the invention. X preferably represents chlorine or bromine.

The carboxylic acid halides of the formula (IV) are known or can be known ten methods are produced (cf. Bull. Soc. Chim. Belg. 70, (1961) 95 or Bull. Soc. Chim. 1970, 4452, 4456).  

The amines required for the preparation of the carbonyl compounds of the formula (II) as starting materials are generally defined by the formula (V). In this formula (V), R ¹ preferably has those meanings which have already been mentioned as preferred for this radical in connection with the description of the compounds of the formula (I) according to the invention.

The amines of the formula (V) are known or can be prepared by known methods (see e.g. DE-A 43 28 425, DE-A 22 49 162, WO 93-19 054, WO 94-21 617, J. Het. Chem. 26, 1575 (1989), Gazz. Chim. Italian 107, 1 (1977), Chem. Ber. 195, 57 and EP-A 0 455 356).

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

The oxyamines of the formula (III) and also their acid addition complexes, such as Hydrogen chloride addition complexes are known or can be according to known Create methods.

Suitable diluents for carrying out the Ver according to the invention consider all inert, organic solvents. Preferably usable are aliphatic, alicyclic or aromatic hydrocarbons, such as petroleum ether, Hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as chlorobenzene, dichlorobenzene, dichloromethane, Chloroform, carbon tetrachloride, dichloroethane or trichloroethane; Ethers such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetra hydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; Nitriles, such as Ace tonitrile, propionitrile, n- or i-butyronitrile or benzonitrile; Amides such as N, N-dime thylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone  or hexamethylphosphoric triamide; Esters such as methyl acetate or vinegar acid ethyl ester; Sulfoxides such as dimethyl sulfoxide; Sulfones such as sulfolane; Alcohols, such as methanol, ethanol, n- or i-propanol, n-, i-, sec- or tert-butanol, ethanediol, Propane-1,2-diol, ethoxyethanol, methoxyethanol, diethylene glycol monomethyl ether, Diethylene glycol monoethyl ether, and also their mixtures with water or pure Water.

The acid binders used in carrying out the process according to the invention rens all common inorganic and organic bases in question. Preferably alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or bicarbonates, such as natri anhydride, sodium amide, sodium methylate, sodium ethylate, potassium tert-butoxide, Sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate and sodium hydrogen carbonate, further ammonium compounds such as ammoni Umhydroxid, ammonium acetate and ammonium carbonate, and tertiary amines, such as Trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, N-dimethyl benzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N, N-dimethylamino pyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicyc loundecene (DBU) or polymeric bases, such as basic ion exchangers.

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 of 0 ° C and 150 ° C, preferably between 0 ° C and 80 ° C.

When carrying out the method according to the invention, one generally works under atmospheric pressure. But it is also possible to increase or decrease pressure to work.

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

The substances according to the invention have a strong microbicidal action and can 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 sclerotiorum;
Tilletia species, such as, for example, Tilletia caries;
Ustilago species, such as, for example, Ustilago nuda or Ustilago avenae;
Pellicularia species, such as, for example, Pellicularia sasakii;
Pyricularia species, such as, for example, Pyricularia oryzae;
Fusarium species, such as, for example, Fusarium culmorum;
Botrytis species, such as, for example, Botrytis cinerea;
Septoria species, such as, for example, Septoria nodorum;
Leptosphaeria species, such as, for example, Leptosphaeria nodorum;
Cercospora species, such as, for example, Cercospora canescens;
Alternaria species, such as, for example, Alternaria brassicae;
Pseudocercosporella species, such as, for example, Pseudocercosporella herpotrichoides.

The good plant tolerance of the active ingredients in the control of 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 or Puccinia species, of diseases in wine, fruit and vegetable growing, such as wise against Venturia, Uncinula and Podosphaera species, or 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.

In material protection, the substances according to the invention can be used to protect techni materials against infestation and destruction by unwanted microorganisms insert men.

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 as technical materi alien preferably adhesives, glues, papers and cartons, leather, wood, paint called medium, cooling lubricants and heat transfer fluids, especially prefers wood.

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 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 compounds according to the invention are also suitable for combating animal pests, in particular insects, arachnids and nematodes, which are useful in agriculture, in forestry, in horticulture, in the protection of stocks and materials and in the hygiene sector or in the case of good plant tolerance and favorable warm-blood toxicity veterinary field occur. The substances are effective against normally sensitive and resistant species and against pests in all or individual stages of development. The animal pests mentioned above include:
From the order of the Isopoda z. B. Oniscus asellus, Armadillidium vulgare, Porcellio scaber.
From the order of the Diplopoda z. B. Blaniulus guttulatus.
From the order of the Chilopoda z. B. Geophilus carpophagus, Scutigera spec.
From the order of the Symphyla z. B. Scutigerella immaculata.
From the order of the Thysanura z. B. Lepisma saccharina.
From the order of the Collembola z. B. Onychiurus armatus.
From the order of Orthoptera z. B. Blatta orientalis, Periplaneta americana, Leuco phaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria.
From the order of the Dermaptera z. B. Auricular Forficula.
From the order of the Isoptera z. B. Reticulitermes spp.
From the order of the Anoplura z. B. Pediculus humanus corporis, Haematopinus spp., Linognathus spp.
From the order of the Mallophaga z. B. Trichodectes spp., Damalinea spp.
From the order of the Thysanoptera z. B. Hercinothrips femoralis, Thrips tabaci.
From the order of Heteroptera z. B. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.
From the order of Homoptera z. B. Aleurodes brassicae, Bemisia tabaci, Trialeuro des vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus sppena, Maculiiphum spp. Rhopalo siphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp.
From the order of the Lepidoptera z. B. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiisisppa, Fpp , Heliothis spp., Spodoptera exigua, Mamestra brassicae, Panolis flammea, Spodoptera litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Tumeria bellaella, Galleria mellellaella Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana.
From the order of the Coleoptera z. B. Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephppis, Orphusus spp. , Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Giptusibbium psol. Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica.
From the order of the Hymenoptera z. B. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
From the order of the Diptera z. B. Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomox ., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa.
From the order of the Siphonaptera z. B. Xenopsylla cheopis, Ceratophyllus spp.
From the order of the Arachnida z. B. Scorpio maurus, Latrodectus mactans.
From the order of Acarina z. B. Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp.,. Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp.

The plant parasitic nematodes include z. B. Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp.

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

In addition, the compounds of formula (I) according to the invention also have very good antifungal effects. They have a very broad spectrum of antimycotic effects, especially against dermatophytes and shoot fungi, 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 fumig -Species like Trichophyton mentagrophytes,
Microsporon species such as Microsporon canis and audouinii. The list of these fungi is in no way a limitation of the detectable mycotic spectrum, but is only of an explanatory nature.

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.

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

Fungicides

Aldimorph, ampropylfos, ampropylfos potassium, andoprim, anilazine, azaconazole, azoxystrobin,
Benalaxyl, benodanil, benomyl, benzamacril, benzamacrylic isobutyl, bialaphos, binapacrylic, biphenyl, bitertanol, blasticidin-S, bromuconazole, bupirimate, buthiobate,
Calcium polysulfide, capsimycin, captafol, captan, carbendazim, carboxin, carvone, quinomethionate (quinomethionate), chlobenthiazone, chlorfenazole, chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon, cufraneb, cymoxanil, cyphodaminazol, cypodaminazol, cypodinconol
Debacarb, dichlorophene, diclobutrazole, diclofluanide, diclomezin, dicloran, dietho fencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, diniconazol-M, dinocap, diphenylamine, dipyrithione, ditalimfos, dorphianzodonone, dithianonodone,
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, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusilazolutol, flusulfazolutol, flusulfazolutol, flusilazolutol, flusilazolutol, flusilazolutolol Fosetyl sodium, fthalide, fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole, furconazole-cis, furmecyclox,
Guazatin,
Hexachlorobenzene, hexaconazole, hymexazole,
Imazalil, Imibenconazol, Iminoctadin, Iminoctadinealbesilat, Iminoctadinetriacetat, Iodocarb, Ipconazol, Iprobefos (IBP), Iprodione, Irumamycin, Isoprothiolan, Isovaledione,
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 and sulfur preparations,
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,
Uniconazole,
Validamycin A, vinclozolin, viniconazole,
Zarilamid, Zineb, Ziram as well
Dagger G,
OK-8705,
OK-8801,
α- (1,1-dimethylethyl) -β- (2-phenoxyethyl) -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,
{2-Methyl-1 - [[[1- (4-methylphenyl) ethyl] amino] carbonyl] propyl} carbamic acid 1-isopropyl ester
1- (2,4-dichlorophenyl) -2- (1H-1,2,4-triazol-1-yl) -ethanone-O- (phenylmethyl) oxime,
1- (2-methyl-1-naphthalenyl) -1H-pyrrole-2,5-dione,
1- (3,5-dichlorophenyl) -3- (2-propenyl) -2,5-pyrrolidinedione,
1 - [(diiodomethyl) sulfonyl] -4-methyl-benzene,
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,
2,2-dichloro-N- [1- (4-chlorophenyl) ethyl] -1-ethyl-3-methyl-cyclopropanecarboxamide,
2,6-dichloro-5- (methylthio) -4-pyrimidinyl-thiocyanate,
2,6-dichloro-N- (4-trifluoromethylbenzyl) benzamide,
2,6-dichloro-N - [[4- (trifluoromethyl) phenyl] methyl] benzamide,
2- (2,3,3-triiodo-2-propenyl) -2H-tetrazole,
2 - [(1-methylethyl) sulfonyl] -5- (trichloromethyl) -1,3,4-thiadiazole,
2 - [[6-Deoxy-4-O- (4-O-methyl-β-D-glycopyranosyl) -aD-glucopyranosyl] amino] -4- methoxy-1H-pyrrolo [2,3-d] pyrimidine- 5-carbonitrile,
2-aminobutane,
2-bromo-2- (bromomethyl) pentandinitrile,
2-chloro-N- (2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl) -3-pyridinecarboxamide,
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- [cyan [(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-cyan-N, N-dimethyl-5- (4-methylphenyl) -1H-imidazole-1-sulfonamide,
4-methyl-tetrazolo [1,5-a] quinazolin-5 (4H) -one,
8- (1,1-dimethylethyl) -N-ethyl-N-propyl-1,4-dioxaspiro [4.5] decane-2-methanamine,
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 hydrogen carbonate,
Methane tetrathiol 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- (2,3-dichloro-4-hydroxyphenyl) -1-methyl-cyclohexane carboxamide,
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'-methoxymanimidamide,
N-formyl-N-hydroxy-DL-alanine sodium salt,
O, O-diethyl- [2- (dipropylamino) -2-oxoethyl] ethylphosphoramidothioate,
O-methyl-S-phenyl-phenylpropylphosphoramidothioate,
S-methyl-1,2,3-benzothiadiazole-7-carbothioate,
spiro [2H] -1-benzopyran-2,1 '(3'H) -isobenzothran] -3'-one.

Bactericides

Bronopol, dichlorophene, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, Octhilinone, furan carboxylic acid, oxytetracycline, probenazole, streptomycin, Teclofta lam, 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, Biethanomofufoxin, Bethanomethofinoxin, Bethenomethrin 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., Esfen valerate, Ethiofencarb, Ethion, Ethoprophos, Etofenprox, Etoxazole, Etrimfos,
Fenamiphos, Fenazaquin, Fenbutatin oxide, Fenitrothion, Fenothiocarb, Fenoxacrim, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyrithrin, Fenpyroximate, Fenvalerate, Fipronil, Fluazuron, Flubrocythrinate, Flucycloxuron, Floxthrinofonate, Fufenoxthhronate, Fufenoxthonophonate, Fufenoxin, Fufone ,
Granulosis viruses,
Halofenozide, HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene,
Imidacloprid, isazofos, isofenphos, isoxathion, ivermectin,
Nuclear polyhedron viruses,
Lambda cyhalothrin, lufenuron,
Malathion, Mecarbam, Metaldehyde, Methamidophos, Metharhician anisopliae, Metharhician flavoviride, Methidathione, Methiocarb, Methomyl, Methoxyfenozide, Metolcarb, Metoxadiazone, Mevinphos, Milbemectin, Monocrotophos,
Naled, Nitenpyram, Nithiazine, Novaluron,
Omethoate, oxamyl, oxydemethone M,
Paecilomyces fumosoroseus, Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos A, Pirimiphos M, Profenofos, Promecarb, Propoxur, Prothiofos, Prothoat, Pyromhrhridosine, Pymmethrofinos, Pymmethrofinos , Pyridathione, pyrimidifen, pyriproxyfen,
Quinalphos,
Ribavirin,
Salithion, Sebufos, Silafluofen, Spinosad, Sulfotep, Sulprofos,
Tau-fluvalinate, tebufenozide, tebufenpyrad, Tebupirimiphos, teflubenzuron, tefluthrin, temephos, Temivinphos, terbufos, tetrachlorvinphos, theta cypermethrin, oxalate hydrogen thiocyclam thiacloprid, thiamethoxam, Thiapronil, Thiatriphos, thiodicarb, thiofanox, thuringiensin, Tralocythrin, tralomethrin, triarathene, Triazamate , Triazophos, triazuron, trichlophenidines, 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-tetramethylcyclopropane decarboxylate
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-oxazole
2- (acetyloxy) -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-iodo-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- (phenylmethyl) -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-hydrazinedicarbothioamide
N-methyl-N'-2-propenyl-1,2-hydrazinedicarbothioamide
O, O-Diethyl- [2- (dipropylamino) -2-oxoethyl] ethyl phosphoramidothioate.

A mixture with other known active ingredients, such as herbicides or with Fertilizers and growth regulators are possible.

With the substances according to the invention, all plants and parts of plants can be to treat. Plants include all plants and plant populations understood how desired and undesirable wild plants or crops (including naturally occurring crops). Cultivated plants can Plants that are grown by conventional breeding and optimization methods or through biotechnological and genetic engineering methods or combinations of these  Methods can be obtained, including transgenic plants and including those that can be estimated or not estimated 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 are understood which, for example 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, vegetative and generative crops Material, such as cuttings, tubers, rhizomes, offshoots and seeds.

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.

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

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

The effectiveness and spectrum of activity of the material according to the invention protection active ingredients to be used or the means to be produced therefrom, conc Contested or more general wording can be increased if necessary further antimicrobial compounds, fungicides, bactericides, herbicides, Insecticides or other active ingredients to enlarge the spectrum of activity or Achieving special effects such as B. added protection against insects be set. These mixtures can have a broader spectrum of activity than the compounds of the invention.

The substances according to the invention can also be used against animal pests in commercial formulations as well as in the form of these formulations Use forms mixed with synergists. Are synergists Compounds through which the action of the active ingredients is increased without the added synergist must be actively active itself.

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

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

When used against hygiene and storage pests, the effect is noticeable material through an excellent residual effect on Hilz and Ton as well as through a good alkali stability on limed substrates.

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

Manufacturing examples

example 1

413 mg (0.0015 mol) of 2- (3-acetylphenyl) -N- (3-methyl-1,2,4-thiadiazol-5-yl) acetate amide, 251 mg (0.003 mol) methoxyamine hydrochloride and 300 mg of a basic Ion exchangers in 20 ml of ethanol are stirred at room temperature for 18 hours. The reaction mixture is then filtered and the filtrate is reduced Pressure reduced. The remaining residue is stirred with diethyl ether. The the resulting solid product is filtered off, washed with diethyl ether and dried.

279 mg (99% of theory) of 2- {3 - [(1Z) -N-methoxyethanimidoyl] phenyl} - N- (3-methyl-1,2,4-thiadiazol-5-yl) acetamide are obtained.
HPLC: logP = 2.25

According to the methods given above, the following in Table 1 listed oxime derivatives of the formulas (I-a) or (I-b).  

Table 1

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

Production of intermediates of formula (II)

Example 44

In a mixture of 4.6 g (40 mmol) of 5-amino-3-methyl-1,2,4-thiadiazole and 12.8 g (162 mmol) of pyridine in 50 ml of dichloromethane are 7.9 with stirring at room temperature g (40 mmol) 3-acetyl-phenylacetic acid chloride in 20 ml dichloromethane. The reaction mixture is stirred for 16 hours at room temperature, then treated with 20 mg of 4-dimethylaminopyridine and stirred for a further 24 hours at room temperature. The reaction mixture is then washed with 1N hydrochloric acid, dried over sodium sulfate and concentrated under reduced pressure. By stirring the residue obtained with diethyl ether, 5.5 g (50% of theory) of 2- (3-acetylphenyl) -N- (3-methyl-1,2,4-thiadiazol-5-yl) acetamide in the form a solid material isolated.
Mp 91-98 ° C
HPLC: logP (pH 2.3) = 1.56

Examples of use Example A Podosphaera test (apple) / protective

Solvent: 24.5 parts by weight of acetone
24.5 parts by weight of dimethylacetamide
Emulsifier: 1.0 part by weight of alkyl aryl polyglycol ether

To produce a suitable preparation of active compound, mix 1 Part by weight of active ingredient 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 added with the active ingredient preparation sprayed in the specified application rate. After the The plants are sprayed with an aqueous spore suspension of the apple mildew pathogen Podosphaera leucotricha inoculated. The plants are then in the Greenhouse at approx. 23 ° C and a relative humidity of approx. 70% poses.

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

In this test, the inventions listed in Examples 29, 39, 35, 36 and 34 show substances according to the invention with an application rate of 100 g / ha an efficiency of more than 90%.  

Example B Uncinula test (vine) / 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, mix 1 Part by weight of active ingredient 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 added with the active ingredient preparation sprayed in the specified application rate. After the The plants are sprayed with an aqueous spore suspension from Unci nula necator inoculated. The plants are then in the greenhouse at about 23 ° C and a relative humidity of approx. 70%.

Evaluation is carried out 14 days after the inoculation. 0% means a we efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.

In this test, the inventions listed in Examples 29, 34, 35 and 39 show substances according to the invention with an application rate of 100 g / ha an efficiency of more than 90%.  

Example C 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, mix 1 Part by weight of active ingredient 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 added with the active ingredient preparation sprayed in the specified application rate. After the The plants are sprayed with an aqueous conidia suspension of Apple scab pathogen Venturia inaequalis and then remain for 1 day at approx. 20 ° C and 100% relative humidity in an incubation cabin.

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

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

In this test, the inventions listed in Examples 29, 34, 36 and 39 show substances according to the invention with an application rate of 100 g / ha an efficiency of more than 80%.  

Example D Puccinia test (wheat) / protective

Solvent: 25 parts by weight of N, N-dimethylacetamide
Emulsifier: 0.6 part by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amounts of solvent and emulsifier and dilute the concentrate with water to the desired concentration.

To test for protective effectiveness, young plants are treated with the active ingredient sprayed substance preparation in the specified application rate. After the The plants are sprayed with a conidia suspension from Puccinia sprayed recondita. The plants remain at 20 ° C and 100% relative for 48 hours Humidity in an incubation cabin.

The plants are then grown in a greenhouse at a temperature of approximately 20 ° C and a relative humidity of 80% set up to the development of Favor rust pustules.

Evaluation is carried out 10 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 shown in Examples 27, 29, 31, 38, 39, 41 and 42 show Substances according to the invention have an efficiency at an application rate of 250 g / ha of more than 90%.  

Example E Pyricularia test (rice) / protective

Solvent: 49 parts by weight of N, N-dimethylformamide
Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, mix 1 Part by weight of active ingredient with the stated amounts of solvent and emulsifier and dilute the concentrate with water 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% relative humidity and 26 ° C for 24 h. On finally the plants are grown in a greenhouse at 80% relative air humidity and a 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 show those listed in Examples 1, 17, 19, 21, 30 and 33 Substances according to the invention have an efficiency of 375 g / ha of more than 70%.  

Example F Erysiphe test (barley) / resistance induction

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

To produce a suitable preparation of active compound, mix 1 Part by weight of active ingredient with the specified amount of solvent and dilutes it Concentrate with water and the specified amount of emulsifier to the desired Concentration.

To test for resistance-inducing effectiveness, young people are sprayed Cereal plants with the active ingredient preparation in the specified application rate. 4 Days after the treatment, the plants are spotted with Erysiphe graminis f. sp. Hordei inoculated. The plants are then grown in a greenhouse 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 listed in Examples 12, 15, 25, 26 and 27 show Substances according to the invention have an efficiency at an application rate of 750 g / ha of more than 85%.  

Example G Phaedon larval test

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

To produce a suitable preparation of active compound, mix 1 Part by weight of active ingredient with the stated amounts of solvent and emulsifier and dilute the concentrate to the desired level with water containing emulsifier Concentration.

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

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

This test shows that in Examples 5, 7, 9, 11, 12, 34, 38, 39 and 40 led substances according to the invention at an active ingredient concentration of 1000 ppm a kill rate of more than 90%.  

Example H Spodoptera frugiperda test

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

To produce a suitable preparation of active compound, mix 1 Part by weight of active ingredient with the stated amounts of solvent and emulsifier and dilute the concentrate to the desired level with water containing emulsifier Concentration.

Cabbage leaves (Brassica oleracea) are dipped into the active ingredient preparation the desired concentration and treated with caterpillars of the army worm (Spo doptera frugiperda) occupied while the leaves are still moist.

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

In this test, those shown in Examples 5, 9, 11, 12, 34 and 39 show substances according to the invention at an active ingredient concentration of 1000 ppm Degree of killing of more than 90%.  

Example I Myzus test

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

To produce a suitable preparation of active compound, mix 1 Part by weight of active ingredient with the stated amount of solvent and the specified amount of emulsifier and dilute the concentrate with water containing emulsifier to the desired concentrations.

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

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

In this test, the substance according to the invention listed in Example 38 shows one Active ingredient concentration of 1000 ppm and a degree of killing of more than 80%.  

Example K Meloidogyne test

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

To produce a suitable preparation of active compound, mix 1 Part by weight of active ingredient with the stated amounts of solvent and emulsifier and dilute the concentrate with water to the desired concentration.

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

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

In this test, those according to the invention shown in Examples 38 and 39 show substances with an active ingredient concentration of 20 ppm a degree of killing of more than 90%.  

Example L Leptosphaeria nodorum test (wheat) / protective

Solvent: 10 parts by weight of N-methylpyrrolidone
Emulsifier: 0.6 part by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amounts of solvent and emulsifier and dilute the concentrate with water to the desired concentration.

To test for protective effectiveness, young plants are treated with the active ingredient sprayed substance preparation in the specified application rate. After the The plants are sprayed with a spore suspension of Leptosphaeria sprayed nodorum. The plants remain at 20 ° C and 100% relative for 48 hours Humidity in an incubation cabin.

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

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

In this test, those shown in Examples 19, 23, 27, 29, 31, 38, 39, 41 and 42 substances listed according to the invention at an application rate of 250 g / ha Efficiency of over 70%.

Claims (7)

1. Oxime derivatives of the formula
in which
A represents alkanediyl,
R ^{1 stands} for optionally substituted 1,2-thiazolyl, 1,2,4-thiadiazolyl or pyridyl,
R ^{2 represents} hydrogen, alkyl or optionally substituted aryl,
R ^{3 represents} hydrogen, alkyl, alkoxyalkyl, alkenyl, alkylcarbonyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted arylcarbonyl, optionally substituted heterocyclyl, optionally substituted heterocyclylalkyl or optionally substituted heterocyclylcarbonyl and
R ^{4 represents} hydrogen, halogen, alkyl, alkoxy, cyano or nitro. 2. oxime derivatives of the formula (I) according to claim 1, in which
A represents alkanediyl having 1 to 4 carbon atoms,
R ¹ represents 1,2-thiazolyl, 1,2,4-thiadiazolyl or pyridyl which is optionally mono- or disubstituted by alkyl having 1 to 4 carbon atoms and / or halogen,
R ^{2 represents} hydrogen, alkyl having 1 to 4 carbon atoms or, if appropriate, single to quadruple, identical or different aryl having 6 to 10 carbon atoms substituted by halogen and / or alkyl having 1 to 4 carbon atoms,
R ^{3 represents} hydrogen, alkyl having 1 to 6 carbon atoms, alkoxyalkyl having 1 to 4 carbon atoms in the alkoxy part and 1 to 4 carbon atoms in the alkyl part, alkenyl having 2 to 6 carbon atoms or alkylcarbonyl having 1 to 6 carbon atoms in the alkyl part, or
represents aryl having 6 to 10 carbon atoms, where each of these radicals can be mono- to tetrasubstituted, identical or differently substituted by halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkylthio, each having 1 to 4 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy or haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms,
or
represents aralkyl having 6 to 10 carbon atoms in the aryl part and 1 to 4 carbon atoms in the alkyl part, where each of these radicals can be substituted one to four times, in the same way or differently, by halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkylthio each 1 to 4 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy or haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms,
or
represents arylcarbonyl having 6 to 10 carbon atoms in the aryl part, each of these radicals being monosubstituted to tetrasubstituted, identical or differently substituted by halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 4 carbon atoms, in each case straight-chain or branched haloalkyl, haloalkoxy or haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms,
or
represents heterocyclyl with 5 or 6 ring members and 1 to 3 hetero atoms, such as oxygen, nitrogen and / or sulfur, where these radicals can optionally be monosubstituted to trisubstituted or substituted by halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 4 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy or haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms,
or
represents heterocyclylalkyl with 5 or 6 ring members and 1 to 3 hetero atoms, such as oxygen, sulfur and / or nitrogen, and 1 to 4 carbon atoms in the alkyl part, where these radicals can optionally be monosubstituted to trisubstituted or substituted by halogen, cyano , Nitro, each straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 4 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy or haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms,
or
represents heterocyclylcarbonyl having 5 or 6 ring members and 1 to 3 heteroatoms, such as oxygen, nitrogen and / or sulfur, where these radicals can optionally be monosubstituted to trisubstituted or substituted by halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 4 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy or haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms,
and
R ^{4 represents} hydrogen, alkyl having 1 to 4 carbon atoms or alkoxy having 1 to 4 carbon atoms. 3. A process for the preparation of oxime derivatives of the formula (I) according to claim 1, characterized in that carbonyl compounds of the formula
in which
A, R ¹ , R ² and R ^{4 have} the meanings given above,
with an oxyamine of the formula
R ³ -O-NH ₂ (III),
in which
R ^{3 has} the meaning given above,
or their acid addition complexes,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder. 4. Means to control unwanted microorganisms and animal Pests, characterized by a content of at least one oxime Derivative of formula (I) according to claim 1 in addition to extenders and / or above surfactants. 5. Use of oxime derivatives of the formula (I) according to Claim 1 for Control of unwanted microorganisms and animal pests gene.   6. Procedure for combating undesirable microorganisms and tieri pests, characterized in that oxime derivatives of Formula (I) according to claim 1 to the undesired microorganisms or animal pests and / or their habitat. 7. Process for the preparation of agents for combating undesirable Microorganisms and animal pests, characterized in that to oxime derivatives of formula (I) according to claim 1 with extenders and / or surface-active substances mixed.