DE10035855A1 - Pyrazolyl benzyl ether - Google Patents

Abstract

The invention relates to new pyrazolylbenzyl ethers, a process for their preparation and their use for controlling harmful organisms.

Description

The invention relates to new pyrazolylbenzyl ethers, a process for their preparation and their use to control harmful organisms.

Certain compounds with a similar substitution pattern, as well as their fungicidal Effect has already become known (compare, for example, WO 95/04728 and WO 99/33812). The action of these previously known compounds is, however, in particular at low application rates and concentrations not in all applications offer completely satisfactory.

The new pyrazolylbenzyl ethers of the general formula (I) have now been found

in which
R represents in each case optionally substituted alkyl, alkenyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl,
L ¹ , L ² , L ³ and L ^{4 are the} same or different and each independently represent hydrogen, halogen, cyano, nitro, each optionally substituted by halogen substituted alkyl, alkoxy, alkylthio, alkylsulfinyl or alkyl sulfonyl.

In the definitions are the saturated or unsaturated hydrocarbon chains, such as alkyl, alkanediyl, alkenyl or alkynyl, also in combination with heteroatoms,  such as in alkoxy, alkylthio or alkylamino, in each case straight-chain or branches. Unless otherwise stated, hydrocarbon chains are preferred with 1 to 6 carbon atoms.

Aryl stands for aromatic, mono- or polycyclic hydrocarbon rings, such as e.g. B. phenyl, naphthyl, anthranyl, phenanthryl, preferably phenyl or naphthyl, especially phenyl.

Heterocyclyl stands for saturated or unsaturated, as well as aromatic, ring-shaped Compounds in which at least one ring member has a heteroatom, i.e. H. one of Carbon is different atom. If the ring contains several heteroatoms, you can these be the same or different. Heteroatoms are preferably oxygen, nitrogen or sulfur. If the ring contains several oxygen atoms, these are not adjacent beard. If necessary, the ring-shaped compounds form with other carbo cyclic or heterocyclic, fused or bridged rings ge together a polycyclic ring system. A polycyclic ring system can over ver the heterocyclic ring or a fused carbocyclic ring be knotted. Mono- or bicyclic ring systems are preferred, in particular mono- or bicyclic aromatic ring systems.

Cycloalkyl stands for saturated, carbocyclic, ring-shaped compounds, the ge optionally with other carbocyclic, fused or bridged Rings form a polycyclic ring system.

Furthermore, it was found that the new pyrazolylbenzyl ethers of the general formula (I) can be obtained if benzyl halides of the formula (II)

in which
L ¹ , L ² , L ³ and L ^{4 have} the meanings given above and
X represents halogen,
with a substituted pyrazolone of the general formula (III),

in which
R has the meaning given above,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid acceptor.

Finally, it was found that the new pyrazolylbenzyl ethers of the general Formula (I) a strong action against harmful organisms, especially a very strong fungicidal activity, show. Be among harmful organisms especially understood microorganisms and animal pests.

The compounds according to the invention can optionally be mixed various possible isomeric forms, in particular stereoisomers, such as. B.  E- and Z-. Both the E and the Z isomers, as well as be arbitrary mixtures of these isomers.

The invention preferably relates to compounds of the formula (I) in which
R for alkyl with 1 to 8 carbon atoms,
for alkenyl with 2 to 6 carbon atoms,
for cycloalkyl with 3 to 7 carbon atoms or cycloalkylalkyl with 3 to 7 ring members and 1 to 4 carbon atoms in the alkyl part which are optionally mono- to disubstituted by halogen, cyano, alkyl or hydroxyl;
or stands for phenyl, naphthyl, phenylalkyl or naphthylalkyl, each of which is optionally mono- to tetrasubstituted, identically or differently, in the aryl part, each having 1 to 4 carbon atoms in the alkyl part, the possible substituents preferably being selected from the list below:
Halogen, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl;
each straight-chain or branched alkyl, hydroxyalkyl, oxoalkyl, alkoxy, alkoxyalkyl, alkylthioalkyl, dialkoxyalkyl, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 8 carbon atoms;
each straight-chain or branched alkenyl or alkenyloxy each having 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 haloalkenyl oxy each having 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms;
each straight-chain or branched alkylamino, dialkylamino,
Alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, arylalkylaminocarbonyl, dialkylaminocarbonyloxy, alkenylcarbonyl or alkynylcarbonyl, with 1 to 6 carbon atoms in the respective hydrocarbon chains;
Cycloalkyl or cycloalkyloxy each having 3 to 6 carbon atoms;
each optionally monosubstituted to tetrasubstituted, identically or differently, by fluorine, chlorine, oxo, methyl, trifluoromethyl or ethyl and in each case doubly linked alkylene having 3 or 4 carbon atoms, oxyalkylene having 2 or 3 carbon atoms or dioxyalkylene having 1 or 2 carbon atoms;
or a grouping

wherein
A ^{1 represents} hydrogen, hydroxy or alkyl having 1 to 4 carbon atoms or cycloalkyl having 1 to 6 carbon atoms and
A ² for hydroxyl, amino, methylamino, phenyl, benzyl or for alkyl or alkoxy with 1 to 4 carbon atoms optionally substituted by cyano, hydroxy, alkoxy, alkylthio, alkylamino, dialkylamino or phenyl, or for alkenyloxy or alkynyloxy each with 2 to 4 carbon atoms,
and in each case optionally in the ring part monosubstituted to trisubstituted by halogen, and / or straight-chain or branched alkyl or alkoxy having 1 to 4 carbon atoms, phenyl, phenoxy, phenylthio, benzoyl, benzoylethenyl, cinnamoyl, heterocyclyl or phenylalkyl, phenylalkyloxy, phenylalkylthio, or heterocyclylalkyl, or heterocyclylalkyl, with 1 to 3 carbon atoms in each alkyl part,
L ¹ , L ² , L ³ and L ^{4 are the} same or different and are each independently of one another hydrogen, halogen, cyano, nitro, in each case alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl optionally substituted by 1 to 5 halogen atoms, each having 1 to 6 Carbon atoms.

The invention relates in particular to compounds of the formula (I) in which
R represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, pentyl or hexyl,
for vinyl, alkyl,
for cyclopentyl, cyclohexyl or cyclohexylmethyl, each of which is optionally mono- to disubstituted by fluorine, chlorine, bromine, cyano, methyl, ethyl and / or i-propyl, n-, i-, s- or t-butyl or hydroxyl
or represents phenyl, benzyl or naphthyl which is optionally monosubstituted to tetrasubstituted, identically or differently, in the aryl part, the possible substituents preferably being selected from the list below:
Fluorine, chlorine, bromine, iodine, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl,
Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, 1-, 2-, 3-, neo-pentyl, 1-, 2-, 3-, 4- (2nd -Methylbutyl), 1-, 2-, 3-hexyl, 1-, 2-, 3-, 4-, 5- (2-methylpentyl), 1-, 2-, 3- (3-methylpentyl), 2nd Ethylbutyl, 1-, 3-, 4- (2,2-dimethylbutyl), 1-, 2- (2,3-dimethylbutyl), hydroxymethyl, hydroxyethyl, 3-oxobutyl, methoxymethyl, dimethoxymethyl,
Methoxy, ethoxy, n- or i-propoxy, methoxymethyl, ethoxymethyl,
Methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, methylthiomethyl, ethylthiomethyl,
Vinyl, allyl, 2-methylallyl, propen-1-yl, crotonyl, propargyl, vinyloxy, allyloxy, 2-methylallyloxy, propen-1-yloxy, crotonyloxy, propargyloxy;
Trifluoromethyl, trifluoroethyl,
Difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl,
Methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethyl amino,
Acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, dimethylaminocarbonyloxy, diethylaminocarbonyloxy, benzylamino carbonyl, acryloyl, propioloyl,
Cyclopentyl, cyclohexyl,
in each case optionally up to four times, the same or differently substituted by fluorine, chlorine, oxo, methyl or trifluoromethyl, in each case two times linked propanediyl, ethyleneoxy, methylenedioxy, ethylenedioxy
or a grouping

in which
A ^{1 represents} hydrogen, methyl or hydroxy and
A ^{2 represents} hydroxy, methoxy, ethoxy, amino, methylamino, phenyl, benzyl or hydroxyethyl, and
phenyl, phenoxy, phenylthio, benzoyl, benzoylethenyl, cinnamoyl, benzyl, phenylethyl, phenylpropyl, benzyloxy, benzylthio, 5,6 in each case optionally in the ring part monosubstituted to triple by halogen, and / or straight-chain or branched alkyl or alkoxy having 1 to 4 carbon atoms -Dihydro-1,4,2-dioxazin-3-ylmethyl, triazolylmethyl, benz oxazol-2-ylmethyl, 1,3-dioxan-2-yl, benzimidazol-2-yl, dioxol-2-yl, oxadi azolyl and
L ¹ , L ² , L ³ and L ^{4 are the} same or different and are each independently hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s -, or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluoro chloromethylthio, trifluoromethylthio, trifluoromethylsulphinyl or Trifluor methylsulfonyl stand.

The invention particularly relates to compounds of the formula (I) in which
R represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, pentyl or hexyl,
for cyclopentyl or cyclohexyl which is optionally mono- to disubstituted by fluorine, chlorine, methyl, ethyl or hydroxy;
or is in each case optionally monosubstituted to tetrasubstituted, identical or differently substituted phenyl or naphthyl, the possible substituents preferably being selected from the list below:
Fluorine, chlorine, bromine, iodine, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl,
Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, 1-, 2-, 3-, neo-pentyl, 1-, 2-, 3-, 4- (2nd -Methylbutyl), 1-, 2-, 3-hexyl, 1-, 2-, 3-, 4-, 5- (2-methylpentyl), 1-, 2-, 3- (3-methylpentyl), 2nd Ethylbutyl, 1-, 3-, 4- (2,2-dimethylbutyl), 1-, 2- (2,3-dimethylbutyl), hydroxymethyl, hydroxyethyl, 3-oxobutyl, methoxymethyl, dimethoxymethyl,
Methoxy, ethoxy, n- or i-propoxy, methoxymethyl, ethoxymethyl,
Methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, methylthiomethyl, ethylthiomethyl,
Vinyl, allyl, 2-methylallyl, propen-1-yl, crotonyl, propargyl, vinyloxy, allyloxy, 2-methylallyloxy, propen-1-yloxy, crotonyloxy, propargyloxy;
Trifluoromethyl, trifluoroethyl,
Difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl,
Methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethyl amino,
Acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, dimethylaminocarbonyloxy, diethylaminocarbonyloxy, benzylamino carbonyl, acryloyl, propioloyl,
Cyclopentyl, cyclohexyl,
in each case optionally up to four times, the same or differently substituted by fluorine, chlorine, oxo, methyl or trifluoromethyl, in each case two times linked propanediyl, ethyleneoxy, methylenedioxy, ethylenedioxy
or a grouping

in which
A ^{1 represents} hydrogen, methyl or hydroxy and
A ^{2 represents} hydroxy, methoxy, ethoxy, amino, methylamino, phenyl, benzyl or hydroxyethyl, and
phenyl, phenoxy, phenylthio, benzoyl, benzoylethenyl, cinnamoyl, benzyl, phenylethyl, phenylpropyl, benzyloxy, benzylthio, 5,6 in each case optionally in the ring part monosubstituted to triple by halogen, and / or straight-chain or branched alkyl or alkoxy having 1 to 4 carbon atoms -Dihydro-1,4,2-dioxazin-3-ylmethyl, triazolylmethyl, benz oxazol-2-ylmethyl, 1,3-dioxan-2-yl, benzimidazol-2-yl, dioxol-2-yl, oxadi azolyl and
L ¹ , L ² , L ³ and L ^{4 are the} same or different and are each independently hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s - or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoromethylthio, trifluoromethylthio, trifluoromethylthio, trifluoromethylthio, trifluoromethylthio, trifluoromethylthio, trifluoromethylthio, trifluoromethyl, trifluoromethylthio, trifluoromethylthio, trifluoromethylthio, trifluoromethylthio, trifluoromethylthio, trifluoromethylthio, trifluoromethylthio, trifluoromethylthio, trifluoromethylthio, trifluoromethylthio, trifluoromethylthio, trifluoromethylthio, trifluoromethylthio, or trifluoromethylsulfonyl.

The invention particularly preferably relates to compounds of the formula (I)
in which
R for allyl, cyclohexylmethyl, naphthyl
stands for phenyl or benzyl, which is optionally monosubstituted to tetrasubstantially or differently, the possible substituents preferably being selected from the following list:
Fluorine, chlorine, bromine, iodine, cyano, methoxy, ethoxy, trifluoromethyl,
Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,
L ¹ and L ^{3 represent} hydrogen, and
L ² and L ^{4 are} independently hydrogen or methyl.

Another particularly preferred group of compounds
L ¹ and L ³ for hydrogen and
L ² and L ^{4 are} independently hydrogen or methyl.

The radicals listed above or specified in preferred ranges definitions apply both to the end products of the formula (I) and correspondingly for the raw materials or intermediate products required for the production.

Those in the respective combinations or preferred combinations of residues radical definitions given in detail for these radicals are independent of the respectively specified combination of the residues, arbitrarily also by residue definitions tion of other preferred areas replaced.

Formula (II) provides a general definition of the benzyl halides required as starting materials for carrying out the process according to the invention. In this formula (II), L ¹ , L ² , L ³ and L ⁴ preferably or in particular have those meanings which, in connection with the description of the compounds of the formula (I) according to the invention, are preferred or particularly preferred for L ¹ , L ² , L ³ and L ^{4 were} given. X represents halogen, preferably chlorine or bromine.

The starting materials of the formula (II) are known and can be prepared according to known ones Processes are prepared (see, for example, WO 98/19312).  

Those used to carry out the method according to the invention as a starting point Substances required pyrazolones are generally defined by the formula (III). In this Formula (III) R preferably or in particular has the meaning that already in connection with the description of the compounds of the invention Formula (I) was indicated as preferred or as particularly preferred for R.

The starting materials of the formula (III) are known and / or can be known Methods are prepared (see, for example, Chem. Pharm. Bull. 19, 1389 (1971)).

Coming as a diluent for carrying out the process according to the invention all inert organic solvents. These include preferential as aliphatic, alicyclic or aromatic hydrocarbons, such as as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, Xylene or decalin; halogenated hydrocarbons, such as chlorine benzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; Ethers, such as, for example, diethyl ether, diisopropyl ether, Methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2- Dimethoxyethane, 1,2-diethoxyethane or anisole; Ketones such as Acetone, butanone, methyl isobutyl ketone or cyclohexanone; Nitriles, such as acetonitrile, Propionitrile, n- or i-butyronitrile or benzonitrile; Amides such as N, N- Dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methyl pyrrolidone or hexamethylphosphoric triamide; Esters such as vinegar acid methyl ester or ethyl acetate; Sulfoxides such as dimethyl sulfoxide; Sulfones such as sulfolane; Alcohols, such as methanol, ethanol, n- or i-propanol, n-, i-, sec- or tert-butanol, ethanediol, propane-1,2-diol, ethoxy ethanol, methoxyethanol, diethylene glycol monomethyl ether, diethylene glycol mono ethyl ether, their mixtures with water or pure water.

The process according to the invention is optionally used in the presence of a ten acid acceptor performed. All the usual inorganic ones come as such or organic bases. These preferably include alkaline earth metal or  Alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hyd roe carbonates, such as sodium hydride, sodium amide, sodium methylate, Sodium ethylate, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, ammonia umhydroxid, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, natri umcarbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate or ammonium carbonate, and also tertiary amines, such as trimethylamine, Triethylamine, tributylamine, N, N-dimethylaniline, N, N-dimethylbenzylamine, Pyridine, N-methylpiperidine, N-methylmorpholine, N, N-dimethylaminopyridine, Diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecene (DBU).

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 from -20 ° C to 100 ° C, preferably at temperatures from -10 ° C up to 80 ° C.

To carry out the method according to the invention for producing the verbin The formula (I) is used per mole of the benzyl halide of the formula (II) in generally 0.5 to 15 mol, preferably 0.8 to 8 mol of substituted pyrazolone Formula (III).

The process according to the invention is generally carried out under normal pressure leads. However, it is also possible, under increased or reduced pressure - in general generally between 0.1 bar and 10 bar - to work.

Carrying out the reaction, working up and isolating the reaction products takes place according to generally accepted methods (compare also the manufacturing examples).  

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, Sphaerotheca, Phytophtora or Plasmopara species, or of rice diseases, such as against Pyricularia species.

The active compounds according to the invention are also suitable for increasing the crop yield. They are also less toxic and have good plant tolerance.  

The active compounds according to the invention can optionally be used in certain concentrations trations and application rates also as herbicides, or to influence the Plant growth can be used. If necessary, they can also be used as Use intermediates and precursors for the synthesis of other active ingredients.

The active ingredients are suitable for good plant tolerance and cheaper Warmblood toxicity to control animal pests, in particular Insects, arachnids and nematodes, which are used in agriculture, in forests, in Storage and material protection as well as in the hygiene sector. You can are preferably used as pesticides. You are against normal sensitive and resistant species as well as against all or individual stages of development effective. The 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 spp ..

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. Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp., Schistocerca gregaria.

From the order of the Blattaria z. B. Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica.  

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 Phthiraptera z. B. Pediculus humanus corporis, Haematopinus spp., Linognathus spp., Trichodectes spp., Damalinia spp ..

From the order of the Thysanoptera z. B. Hercinothrips femoralis, Thrips tabaci, Thrips palmi, Frankliniella accidentalis.

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, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus spp., Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum 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 xylostella, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Mamestra brassicae, Panolis flammea, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana,  Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana, Cnaphalocerus spp., Oulema oryzae.

From the order of the Coleoptera z. B. Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica, Lissorhoptrus oryzophilus.

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., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa, Hylemyia spp., Liriomyza spp ..

From the order of the Siphonaptera z. B. Xenopsylla cheopis, Ceratophyllus spp.

From the class of the Arachnida z. B. Scorpio maurus, Latrodectus mactans, Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp.,  Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Hemitarsonemus spp., Brevipalpus 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., Bursaphelenchus spp ..

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

The treatment according to the invention of the plants and parts of plants with the active ingredients substances takes place directly or by influencing their surroundings, living space or Storage room according to the usual treatment methods, e.g. B. by diving, spraying, Evaporation, misting, scattering, spreading and, in the case of propagation material, ins especially in the case of seeds, still by wrapping them in one or more layers.  

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

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

As microorganisms that break down or change the technical Materials such as bacteria, fungi, yeasts, algae and Called slime organisms. The active compounds according to the invention preferably act against fungi, in particular mold, wood-discoloring and wood-destroying fungi (Basidiomycetes) and against mucous organisms and algae.

For example, microorganisms of the following genera may be mentioned:
Alternaria, such as Alternaria tenuis,
Aspergillus, such as Aspergillus niger,
Chaetomium, like Chaetomium globosum,
Coniophora, such as Coniophora puetana,
Lentinus, such as Lentinus tigrinus,
Penicillium, such as Penicillium glaucum,
Polyporus, such as Polyporus versicolor,
Aureobasidium, such as Aureobasidium pullulans,
Sclerophoma, such as Sclerophoma pityophila,
Trichoderma, like Trichoderma viride,
Escherichia, such as Escherichia coli,
Pseudomonas, such as Pseudomonas aeruginosa,
Staphylococcus, such as Staphylococcus aureus.

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

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

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

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

The formulations generally contain between 0.1 and 95 percent by weight Active ingredient, preferably between 0.5 and 90%.

The active compounds according to the invention can be used as such or in their formulations also in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides can be used, e.g. B. to broaden the spectrum of activity or to prevent the development of resistance. In many cases you get synergistic  Effects, d. H. the effectiveness of the mixture is greater than the effectiveness of the individual components.

The following connections can be considered as mixed partners:

Fungicides

Aldimorph, ampropylfos, ampropylfos potassium, andoprim, anilazine, azaconazole, azoxystrobin,
Benalaxyl, benodanil, benomyl, benzamacril, benzamacrylic isobutyl, bialaphos, binapacrylic, biphenyl, bitertanol, blasticidin-S, bromuconazole, bupirimate, buthiobate,
Calcium polysulfide, capsimycin, captafol, captan, carbendazim, carboxin, carvone, quinomethionate (quinomethionate), chlobenthiazon, chlorfenazole, chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon, cufraneb, cymoxanil, cyphodinconol, cypodinconol, cypodinconol
Debacarb, dichlorophene, diclobutrazole, diclofluanide, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, diniconazol-M, dinocap, diphenylamine, dipyrithione, ditalimfos, dithorphoxinodonine, dithorphononodine
Ediphenphos, Epoxiconazole, Etaconazole, Ethirimol, Etridiazole,
Famoxadone, fenapanil, fenarimol, fenbuconazole, fenfuram, fenitropan, fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam, ferimzon, fluazinam, flumetover, fluoromid, fluquinconazole, flurprimolol, flusulfazolutol, flusulfazolutol, flusulfazolutol, 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, Methfuroxam, 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-1,4-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) -isobenzofuran] -3'-one,

Bactericides

Bronopol, dichlorophene, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, Octhilinone, furan carboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, Copper sulfate and other copper preparations.

Insecticides / acaricides / nematicides

Abamectin, Acephate, Acetamiprid, Acrinathrin, Alanycarb, Aldicarb, Aldoxycarb, Alpha-cypermethrin, Alphamethrin, Amitraz, Avermectin, AZ 60541, Azadirachtin, Azamethiphos, Azinphos A, Azinphos M, Azocyclotin,
Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillus thuringiensis, Baculoviruses, Beauveria bassiana, Beauveria tenella, Bendiocarb, Benfuracarb, Bensultap, Benzoximate, Betacyfluthrin, Bifenazate, Bifenthrin, 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., Esfenvalerate, Ethiofencarb, Ethion, Ethoprophos, Etofenprox, Etoxazole, Etrimfos,
Fenamiphos, Fenazaquin, Fenbutatin oxide, Fenitrothion, Fenothiocarb, Fenoxacrim, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyrithrin, Fenpyroximate, Fenvalerate, Fipronil, Fluazinam, Fluazuron, Flubrocythrinate, Flucycloxoxinon, Flutoxinoxuron, Fluutinoxuron, Fluutinoxuron, Fluutinoxuron, , Furathiocarb,
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, Oxydemethon M
Paecilomyces fumosoroseus, Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos A, Pirimiphos M, Profenofos, Promecarb, Propoxur, Prothiofos, Prothoat, Pyromhrhridosine, Pymmethrofinos, Pymmethrofinos , Pyridathione, pyrimidifen, pyriproxyfen,
Quinalphos,
Ribavirin
Salithion, Sebufos, Silafluofen, Spinosad, Sulfotep, Sulprofos,
Tau fluvalinate, tebufenozide, tebufenpyrad, tebupirimiphos, teflubenzuron, tefluthrin, temephos, temivinphos, terbufos, tetrachlorvinphos, theta-cyper methrin, thiamethoxam, thiapronil, thiatriphos hydrogen, thiocalinoxinoxinoxinoxinoxinoxinoxinoxinoxaline, thiaphenol , 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 (1 H) - 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.

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 fumigatus, Trichophyton species such as Trichophyton mentagrophytes,
Microsporon species such as Microsporon canis and audouinii. The list of these fungi is in no way a limitation of the detectable mycotic spectrum, but is only of an explanatory nature.

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. The effort involved in treating the floor amounts of active ingredient generally between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha.

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

When used as insecticides, the active compounds according to the invention can also be used in their commercial formulations as well as in those formulations prepared application forms in a mixture with synergists. Synergists are compounds that increase the effectiveness of the active ingredients without the added synergist itself must be active.

The active ingredient content of the prepared from the commercially available formulations Application forms 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 stands out Active ingredient through an excellent residual effect on wood and clay as well as through good stability to alkali on limed substrates.

The following examples serve to explain the invention. The invention is but not limited to the examples.

Manufacturing examples

example 1

1.9 g (0.01 mol) of 1- (4-chlorophenyl) -1,2-dihydro-3H-pyrazol-3-one are mixed with 1.5 g (0.011 mol) of potassium carbonate in 50 ml of dry acetonitrile for 1 hour stirred at room temperature. Then 2.7 g (0.01 mol) of [2- (chloromethyl) phenyl] - (5,6-dihydro-1,4,2-dioxazin-3-yl) methanone O-methyloxime are added and the mixture is added overnight heated to boiling under reflux. After cooling, the solvent is distilled off under reduced pressure. The residue is taken up in ethyl acetate and washed several times with water. The organic phase is dried over sodium sulfate and concentrated under reduced pressure. The oily residue is chromatographed on silica gel using cyclohexane / ethyl acetate (9: 1 to 4: 1). 1.97 g (46% of theory) [2 - ({[1- (4-chlorophenyl) -1H-pyrazol-3-yl] oxy} methyl) phenyl] (5,6-dihydro-1,4 , 2-dioxazin-3-yl) methanone O-methyloxime.
Melting point: 117-118 ° C

Analogous to Example 1, and according to the information in the general procedure description, the compounds listed in Table 1 below of formula (I-a) obtained.  

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)  

Examples of use Example A Phytophthora test (tomato) / 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 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 an aqueous spore suspension from Phyto phthora infestans inoculated. The plants are then in an incubation cabin set up at approx. 20 ° C and 100% relative humidity.

Evaluation is carried out 3 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.

This test shows those listed in Examples (1), (4), (5) and (16) Substances according to the invention have an effect at an application rate of 100 g / ha degree of 89% or more.  

Example B Plasmopara 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 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 an aqueous spore suspension of Plasmopara viticola inoculated and then remain in an incubation cabin for 1 day at approx. 20 ° C and 100% relative humidity. Then the plants Set up in a greenhouse for 4 days at approx. 21 ° C and approx. 90% humidity. The Plants are then moistened and placed in an incubation cabin for 1 day.

Evaluation is carried out 6 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.

This test shows that in Examples (1), (2), (4), (5), (14) and (16) led substances according to the invention at an application rate of 100 g / ha Efficiency of 95% or more.  

Example C Sphaerotheca test (cucumber) / 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 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 an aqueous spore suspension of Sphaerotheca fuliginea inoculated. The plants are then at about 23 ° C and one relative humidity of about 70% in the greenhouse.

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.

This test shows that in Examples (1), (2), (4), (5), (14) and (16) led substances according to the invention at an application rate of 100 g / ha Efficiency of 95% or more.  

Example D 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 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 activity, young plants are added with the active ingredient preparation sprayed in the specified application rate. After the spray has dried The plants are topped with an aqueous conidia suspension of the apple scab pathogen Venturia inaequalis and then remain at about 20 ° C for 1 day 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 Efficiency that corresponds to that of the control, while an efficiency 100% means that no infection is observed.

This test shows that in Examples (1), (2), (4), (5), (14) and (16) led substances according to the invention at an application rate of 10 g / ha Efficiency of 87% or more.  

Example E Pyricularia test (rice) / 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 rice plants are sprayed with the Active ingredient preparation in the specified application rate. After drying the The plants are sprayed with an aqueous spore suspension from Pyri cularia oryzae and then remain at 100% rel. for 24 h. Humidity and 26 ° C. The plants are then in a greenhouse at 80% rel. Air humidity and a temperature of 26 ° C.

Evaluation is carried out 7 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.

This test shows that in Examples (1), (4), (5), (7), (12) and (16) led substances according to the invention at an application rate of 125 g / ha Efficiency of 78% or more.  

Example F Erysiphe test (barley) / resistance induction

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, 1 weight is mixed some active ingredient with the specified amounts of solvent and emulsifier and ver thin the concentrate with water to the desired concentration.

To test for resistance-inducing effectiveness, young cereals are sprayed plant with the active ingredient preparation in the specified application rate. 4 days after the treatment, the plants are covered with spores of Erysiphe graminis f. sp. Hordei inoculated. The plants are then grown in a greenhouse at 70% relative humidity and a temperature of 18 ° C.

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

This test shows that in Examples (4), (5), (7), (8), (13) and (15) led substances according to the invention at an application rate of 750 g / ha Efficiency of 94% or more.  

Example G Erysiphe test (barley) / protective

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

To produce a suitable preparation of active compound, 1 weight is mixed some active ingredient with the specified amounts of solvent and emulsifier and ver thin the concentrate with water to the desired concentration.

To test for protective effectiveness, young plants are sprayed with the active ingredient substance preparation in the specified application rate.

After the spray coating has dried on, the plants are covered with Erysiphe spores graminis f. sp. hordei pollinated.

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

Evaluation is carried out 7 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.

This test shows that in Examples (2), (4), (8), (9), (13) and (14) led substances according to the invention at an application rate of 250 g / ha Efficiency of 98% or more.  

Example H Erysiphe test (wheat) / curative

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.

Young plants with spores from Erysiphe are used to test for curative effectiveness graminis f. sp. tritici pollinated. 48 hours after the inoculation, the plants are with sprayed the active ingredient preparation in the application rate specified.

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

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.

This test shows that in Examples (2), (4), (5), (9), (12), (13) and (14) led substances according to the invention at an application rate of 250 g / ha Efficiency of 98% or more.  

Example I Puccinia test (wheat) / curative

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.

Young plants with a condia are used to test for curative effectiveness Sprayed suspension from Puccinia recondita. The plants remain for 48 hours 20 ° C and 100% relative humidity in an incubation cabin. Subsequently the plants with the active ingredient preparation in the specified application rate sprayed.

The plants are grown in a greenhouse at a temperature of approx. 20 ° C and a relative humidity of approx. 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.

This test shows those listed in Examples (1), (4), (9) and (14) Substances according to the invention have an efficiency at an application rate of 250 g / ha of 98% or more.  

Example J Phaedon larval test

Solvent: 30 parts by weight of acetone
Emulsifier: 1 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 containing emulsifier to the desired level 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.

In this test show the fiction, listed in Examples (7) and (15) substances with an active ingredient concentration of 1000 ppm a degree of killing of 90% or more.  

Example K Myzus test

Solvent: 30 parts by weight of acetone
Emulsifier: 1 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 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 ge desired immersion 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 (1) shows an active ingredient concentration of 1000 ppm a degree of kill of 90%.  

Example L Meloidogyne test

Solvent: 30 parts by weight of acetone
Emulsifier: 1 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.

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% be indicates that the number of galls on the treated plants is that of the untreated Control corresponds.

In this test, the invention shown in Examples (1) and (12) show according to substances with an active ingredient concentration of 20 ppm a degree of killing of 100%.

Claims (10)

1. Compounds of the general formula (I),
in which
R represents in each case optionally substituted alkyl, alkenyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl,
L ¹ , L ² , L ³ and L ^{4 are the} same or different and independently of one another each represent hydrogen, halogen, cyano, nitro, in each case optionally substituted by halogen, alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl. 2. Compounds of formula (I), according to claim 1, characterized in that
R for alkyl with 1 to 8 carbon atoms,
for alkenyl with 2 to 6 carbon atoms,
for cycloalkyl with 3 to 7 carbon atoms or cycloalkylalkyl with 3 to 7 ring members and 1 to 4 carbon atoms in the alkyl part which are optionally mono- to disubstituted by halogen, cyano, alkyl or hydroxyl;
or stands for phenyl, naphthyl, phenylalkyl or naphthylalkyl with 1 to 4 carbon atoms in the alkyl part, each of which is monosubstituted or substituted four times, identically or differently in the aryl part, the possible substituents preferably being selected from the list below:
Halogen, cyano, nitro, amino, hydroxy, formyl, carboxy, carb amoyl, thiocarbamoyl;
in each case straight-chain or branched alkyl, hydroxyalkyl, oxoalkyl, alkoxy, alkoxyalkyl, alkylthioalkyl, dialkoxyalkyl, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 8 carbon atoms;
each straight-chain or branched alkenyl or alkenyloxy each having 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;
each straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylamino carbonyl, dialkylaminocarbonyl, arylalkylaminocarbonyl, dialkyl aminocarbonyloxy, alkenylcarbonyl or alkynylcarbonyl, with 1 to 6 carbon atoms in the respective hydrocarbon chains;
Cycloalkyl or cycloalkyloxy each having 3 to 6 carbon atoms;
each optionally one to four times, the same or different by fluorine, chlorine, oxo, methyl, trifluoromethyl or ethyl, substituted and in each case doubly linked alkylene with 3 or 4 carbon atoms, oxyalkylene with 2 or 3 carbon atoms or dioxy alkylene with 1 or 2 carbon atoms;
or a grouping
wherein
A ^{1 represents} hydrogen, hydroxy or alkyl having 1 to 4 carbon atoms or cycloalkyl having 1 to 6 carbon atoms and
A ² for hydroxyl, amino, methylamino, phenyl, benzyl or for alkyl or alkoxy with 1 to 4 carbon atoms optionally substituted by cyano, hydroxy, alkoxy, alkyl thio, alkylamino, dialkylamino or phenyl, or for alkenyloxy or alkynyloxy each with 2 to 4 carbon atoms,
and in each case optionally in the ring part monosubstituted to trisubstituted by halogen, and / or straight-chain or branched alkyl or alkoxy having 1 to 4 carbon atoms, phenyl, phenoxy, phenylthio, benzoyl, benzoylethenyl, cinnamoyl, heterocyclyl or phenylalkyl, phenylalkyloxy, phenylalkylthio, or heterocyclylalkyl, or heterocyclylalkyl, with 1 to 3 carbon atoms in each alkyl part,
L ¹ , L ² , L ³ and L ^{4 are the} same or different and are each independently of one another hydrogen, halogen, cyano, nitro, in each case optionally substituted by 1 to 5 halogen atoms, alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl, each with 1 are up to 6 carbon atoms. 3. Compounds of formula (I), according to claim 1, characterized in that
R represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, pentyl or hexyl,
for vinyl, allyl,
for cyclopentyl or cyclohexyl which is optionally mono- to disubstituted by fluorine, chlorine, methyl, ethyl or hydroxy;
or is in each case optionally monosubstituted to tetrasubstituted, identically or differently substituted phenyl or naphthyl, the possible substituents preferably being selected from the list below:
Fluorine, chlorine, bromine, iodine, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl,
Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, 1-, 2-, 3-, neo-pentyl, 1-, 2-, 3-, 4- (2nd -Methylbutyl), 1-, 2-, 3-hexyl, 1-, 2-, 3-, 4-, 5- (2-methylpentyl), 1-, 2-, 3- (3-methylpentyl), 2- Ethylbutyl, 1-, 3-, 4- (2,2-dimethylbutyl), 1-, 2- (2,3-dimethylbutyl), hydroxymethyl, hydroxyethyl, 3-oxobutyl, methoxymethyl, dimethoxymethyl,
Methoxy, ethoxy, n- or i-propoxy, methoxymethyl, ethoxymethyl,
Methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, methylthiomethyl, ethylthiomethyl,
Vinyl, allyl, 2-methylallyl, propen-1-yl, crotonyl, propargyl, vinyloxy, allyloxy, 2-methylallyloxy, propen-1-yloxy, crotonyloxy, propargyloxy;
Trifluoromethyl, trifluoroethyl,
Difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl,
Methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethylamino,
Acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methylamino carbonyl, ethylaminocarbonyl, dimethylaminocarbonyl, diethyl aminocarbonyl, dimethylaminocarbonyloxy, diethylaminocarbonyl oxy, benzylaminocarbonyl, acryloyl, propioloyl,
Cyclopentyl, cyclohexyl,
in each case optionally up to four times, the same or different, substituted by fluorine, chlorine, oxo, methyl or trifluoromethyl, in each case twice linked propanediyl, ethyleneoxy, methylenedioxy, ethylenedioxy
or a grouping
in which
A ^{1 represents} hydrogen, methyl or hydroxy and
A ^{2 represents} hydroxy, methoxy, ethoxy, amino, methylamino, phenyl, benzyl or hydroxyethyl, and
phenyl, phenoxy, phenylthio, benzoyl, benzoylethenyl, cinnamoyl, benzyl, phenyl ethyl, phenylpropyl, benzyloxy, benzylthio, 5, in each case optionally in the ring part monosubstituted to triple by halogen, and / or straight-chain or branched alkyl or alkoxy having 1 to 4 carbon atoms, 6-dihydro-1,4,2-dioxazin-3-ylmethyl, triazolylmethyl, benzoxazol-2-ylmethyl, 1,3-dioxan-2-yl, benzimidazol-2-yl, dioxol-2-yl, oxadiazolyl and
L ¹ , L ² , L ³ and L ^{4 are the} same or different and, independently of one another, each represent hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoromethylthioifluorifluoromifluorodifluoromifluorodifluoromifluoromethyl, difluoromethylthioifluoromifluoromifluoromifluoromethyl, difluoromethylfluoromifluorifluoromifluoromethyl, bifluoromethyltrifluoromethyl, bifluoromethyl, bifluoromethyl, bifluoromethyl, bifluoromethyl, bifuryl or trifluoromethylsulfonyl. 4. Compounds of formula (I) according to claim 1, characterized in that
R represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, pentyl or hexyl,
for cyclopentyl or cyclohexyl which is optionally mono- to disubstituted by fluorine, chlorine, methyl, ethyl or hydroxy;
or is in each case optionally monosubstituted to tetrasubstituted, identically or differently substituted phenyl or naphthyl, the possible substituents preferably being selected from the list below:
Fluorine, chlorine, bromine, iodine, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl,
Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, 1-, 2-, 3-, neo-pentyl, 1-, 2-, 3-, 4- (2nd -Methylbutyl), 1-, 2-, 3-hexyl, 1-, 2-, 3-, 4-, 5- (2-methylpentyl), 1-, 2-, 3- (3-methylpentyl), 2- Ethylbutyl, 1-, 3-, 4- (2,2-dimethylbutyl), 1-, 2- (2,3-dimethylbutyl), hydroxymethyl, hydroxyethyl, 3-oxobutyl, methoxymethyl, dimethoxymethyl,
Methoxy, ethoxy, n- or i-propoxy, methoxymethyl, ethoxymethyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethyl sulfinyl, methylsulfonyl or ethylsulfonyl, methylthiomethyl, ethylthiomethyl,
Vinyl, allyl, 2-methylallyl, propen-1-yl, crotonyl, propargyl, vinyloxy, allyloxy, 2-methylallyloxy, propen-1-yloxy, crotonyloxy, propargyloxy;
Trifluoromethyl, trifluoroethyl,
Difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl,
Methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethylamino,
Acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methylamino carbonyl, ethylaminocarbonyl, dimethylaminocarbonyl, diethyl aminocarbonyl, dimethylaminocarbonyloxy, diethylaminocarbonyl oxy, benzylaminocarbonyl, acryloyl, propioloyl,
Cyclopentyl, cyclohexyl,
in each case optionally up to four times, the same or different, substituted by fluorine, chlorine, oxo, methyl or trifluoromethyl, in each case twice linked propanediyl, ethyleneoxy, methylenedioxy, ethylenedioxy
or a grouping
in which
A ^{1 represents} hydrogen, methyl or hydroxy and
A ^{2 represents} hydroxy, methoxy, ethoxy, amino, methylamino, phenyl, benzyl or hydroxyethyl, and
phenyl, phenoxy, phenylthio, benzoyl, benzoylethenyl, cinnamoyl, benzyl, phenylethyl, phenylpropyl, benzyloxy, benzylthio, 5, in each case optionally in the ring part monosubstituted to triple by halogen, and / or straight-chain or branched alkyl or alkoxy having 1 to 4 carbon atoms, 6-dihydro-1,4,2-dioxazin-3-ylmethyl, triazolylmethyl, benzoxazol-2-ylmethyl, 1,3-dioxan-2-yl, benzimidazol-2-yl, dioxol-2-yl, oxadiazolyl and
L ¹ , L ² , L ³ and L ^{4 are the} same or different and are each independently hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s -, or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoro ethoxy, difluoromethylthio, difluorochloromethylthio, trifluoromethyl thio, trifluoromethylsulfinyl or trifluoromethylsulfonyl. 5. Compounds of formula (I), according to claim 1, characterized in that
R for allyl, cyclohexylmethyl, naphthyl,
represents phenyl or benzyl which is optionally monosubstituted to tetrasubstituted in the same way or differently, the possible substituents preferably being selected from the following list:
Fluorine, chlorine, bromine, iodine, cyano, methoxy, ethoxy, trifluoromethyl,
Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,
L ¹ and L ^{3 represent} hydrogen, and
L ² and L ^{4 are} independently hydrogen or methyl. 6. A process for the preparation of compounds of the general formula (I) as defined in claim 1, characterized in that compounds of the formula (II),
in which
L ¹ , L ² , L ³ and L ^{4 have} the meanings given in Claim 1
and
X represents halogen,
with a substituted pyrazolone of the general formula (III),
in which
R has the meaning given in claim 1,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid acceptor. 7. Means for controlling harmful organisms containing extenders and / or carriers and optionally surface-active substances, ge characterized by a content of at least one compound as in the Claims 1 to 5 defined. 8. Process for combating harmful organisms, thereby known records that compounds as in claims 1 to 4 or means as defined in claim 7 on harmful organisms and / or their Living space. 9. Use of compounds as in claims 1 to 5 and of Agents as defined in claim 7 for combating harmful Organisms. 10. A method for producing agents as defined in claim 7, characterized characterized in that compounds as in claims 1 to 5 defined with extenders and / or carriers and / or surfaces active funds mixed.