WO1998038172A1 - Phenyl-amino-sulfonyl-urea derivatives as fungicides and pesticides - Google Patents

Abstract

The invention relates to new phenyl-amino-sulfonyl-urea derivatives, a method for producing said derivatives, and the use thereof as fungicides.

Description

PHENYLAMINOSULFONYL URINE IVATE AS A FUNGICIDE AND PESTICIDE

The invention relates to new phenylaminosulfonylurea derivatives, a process for their preparation and their use as fungicides.

The new phenylaminosulfonylurea derivatives of the general formula (I)

in which

Rl for optionally substituted alkyl or a group

stands in what

R * represents hydrogen or optionally substituted alkyl, alkoxy, dialkylarnino, cycloalkyl, cycloalkenyl, phenyl or heterocyclyl.

R9 and R * ^υ each stand for alkyl or together for alkanediyl,

Rl 1 represents optionally substituted alkyl,

R ^, R ^ and R ^ are the same or different and each represents hydrogen, halogen, cyano, nitro, each optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkenyl, alkenyloxy, cycloalkyl or cycloal- are koxy, but one of the radicals R ^, R3 or R4 is different from hydrogen,

R5 for halogen, cyano, nitro, each optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkenyl, alkenyloxy, cycloalkyl or

Cycloalkoxy stands,

R ^ and R ^ are the same or different and are each for halogen or for alkyl, alkenyl, alkynyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, each optionally substituted by halogen or alkoxy,

Cycloalkyl or heterocyclyloxy and

G for nitrogen or

stands in what

Rl2 represents hydrogen, halogen, cyano or alkyl optionally substituted by halogen or alkoxy,

and their salts found.

In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkanediyl, alkenyl or alkynyl, are in each case straight-chain or branched, also in combination with heteroatoms, such as in alkoxy, alkylthio or alkylamino.

Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.

Aryl stands for aromatic, mono or polycyclic hydrocarbon rings, such as 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 is a hetero atom, ie an atom other than carbon. If the ring contains several heteroatoms, these can be the same or different. Heteroatoms are preferably oxygen, nitrogen or sulfur. If appropriate, the ring-shaped compounds together with other carbocyclic or heterocyclic, fused or bridged rings together form a polycyclic ring system. Mono- or bicyclic ring systems are preferred, in particular mono- or bicyclic aromatic ring systems.

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

Cycloalkenyl stands for carbocyclic, ring-shaped compounds which contain at least one double bond and optionally form a polycyclic ring system with other carbocyclic, fused or bridged rings.

It has also been found that the new phenylaminosulfonylurea derivatives of the general formula (I) are obtained if aminotriazines or -pyrimidines of the general formula (II),

R "

N

H ₂ N ^* N ^{' •} R'

(II)

in which

R6, R ^ and G have the meanings given above, with chlorosulfonyl isocyanate, optionally in the presence of a diluent, and the chlorosulfonylureas of the general formula formed

in which

R ^, R ^ and G have the meanings given above,

with anilines of the general formula (IV),

in which

R, R ^, R3 _; R4 and R ^ have the meanings given above,

if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent and if appropriate converting the compounds of the formula (I) thus obtained into salts by customary methods.

Finally, it was found that the fused azole derivatives of the formula (I) and their acid addition salts and metal salt complexes have very good microbicidal properties and can be used both in crop protection and in material protection. The invention preferably relates to compounds of the formula (I) in which

R ^Ϊ for ^{alkyl optionally substituted} by halogen, thioalkyl having 1 to 6 carbon atoms or sulfonylalkyl having 1 to 6 carbon atoms or a group

stands in what

R ^ for hydrogen, for optionally substituted by fluorine, chlorine, bromine, alkoxy having 1 to 3 carbon atoms, alkylthio having 1 to 3 carbon atoms, alkylsulfinyl having 1 to 3 carbon atoms or alkylsulfonyl having 1 to 3 carbon atoms, or dial- kylamino, each with 1 to 6 carbon atoms in the individual alkyl parts, for each optionally by fluorine, chlorine, bromine and / or

Alkyl with 1 to 3 carbon atoms substituted cycloalkyl, cycloalkenyl, cycloalkylalkyl or cycloalkenylalkyl each with 3 to 6 carbon atoms in the cycloalkyl or cycloalkenyl groups and 1 to 3 carbon atoms in the respective alkyl parts, each optionally by fluorine, Chlorine, bromine, alkyl with 1 to 3 carbon atoms or haloalkyl with 1 to 3 carbon atoms and 1 to 5 halogen atoms substituted phenyl or phenylalkyl with 1 to 3 carbon atoms in the alkyl part or for each optionally by fluorine, chlorine, bromine, alkyl with 1 to 3 carbon atoms or halogenoalkyl having 1 to 3 carbon atoms and 1 to 5 halogen atoms, substituted heterocyclyl or heterocyclylalkyl having 3 to 7 ring members and having 1 to 3 carbon atoms in the alkyl part,

R9 and RIO each represent alkyl having 1 to 3 carbon atoms or together represent alkanediyl having 1 to 3 carbon atoms, Rl ^ represents alkyl with 1 to 4 carbon atoms optionally substituted by halogen or phenyl,

R2, R3 and R ^ are the same or different and each represents hydrogen, halogen, cyano, nitro, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4

Carbon atoms, alkylthio with 1 to 4 carbon atoms, alkylsulfinyl with 1 to 4 carbon atoms, alkylsulfonyl with 1 to 4 carbon atoms, alkenyl with 2 to 4 carbon atoms, alkenyloxy with 2 to 4 carbon atoms, haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl with each 1 to 6 carbon atoms and 1 to 5 identical or different halogen atoms, cycloalkyl with 3 to 6 carbon atoms or cycloalkoxy with 3 to 6 carbon atoms, but one of the radicals R ^, R- or R ^ is different from hydrogen,

R5 for halogen, cyano, nitro, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, alkylsulfinyl with 1 to 4 carbon atoms, alkylsulfonyl with 1 to 4 carbon atoms, alkenyl with 2 to 4 carbon atoms, Alkenyloxy having 2 to 4 carbon atoms, haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 5 identical or different halogen atoms, cycloalkyl having 3 to 6 carbon atoms or cycloalkoxy having 3 to 6 carbon atoms,

R6 and R ^ are the same or different and are each for halogen or for alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino or dialkylamino each with 1 to 4 carbon atoms in each individual, optionally substituted by halogen or alkoxy having 1 to 4 carbon atoms Alkyl parts, alkenyl or alkynyl each having 2 to 4 carbon atoms, cycloalkyl having 3 to 6 carbon atoms or heterocyclyloxy having 3 to 6 ring members and 1 to 3 heteroatoms and G represents nitrogen or where

Rl2 represents hydrogen, halogen, cyano or alkyl having 1 to 4 carbon atoms optionally substituted by halogen or alkoxy having 1 to 4 carbon atoms.

The invention further preferably comprises sodium, potassium, magnesium, calcium, ammonium, C 1 -C 4 alkyl ammonium, di (C 1 -C 4 alkyl) ammonium, tri (C 1 -C 4 alkyl) -ammonium-, C5- or Cg-cycloalkyl-ammonium and di- (C,; - C2-alkyl) -benzyl-ammonium salts of compounds of formula (I), in which R, R ^, R ³ , R4, R5 _} R6 _; R7 _{un (} j Q <have the meanings preferably given above.

The invention relates in particular to compounds of the formula (I) in which

R for methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, n-, i- or s-pentyl or one optionally substituted by fluorine, chlorine, thiomethyl and / or sulfonylmethyl grouping

stands in what

R ^ for hydrogen, for methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, n-, i- or s-pentyl, methoxy, ethoxy, each optionally substituted by fluorine and / or chlorine, n- or i-propoxy, dimethylamino, diethylamino, for methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, methylthioethyl, ethylthiomethyl, ethylthioethyl, methylsulfinylmethyl, ethylsulfinylmethyl, methylsulfonylmethyl, ethylsulfonylmethyl or meth for optionally , Chlorine and / or methyl substituted cyclopropyl, cyclopropylmethyl, cyclobutyl, cyclobutylmethyl, cyclopentyl, cyclopentylmethyl, cyclopentenylmethyl, cyclohexyl, cyclohexenyl methyl, phenyl, benzyl, phenylethyl, furyl, furylmethyl, thienyl, thienylmethyl, tetrahydrofüryl or tetrahydrofürylmethyl,

R9 and R ^υ each represent methyl, ethyl, n- or i-propyl or together for methylene, 1,1-ethanediyl, 1,2-ethanediyl 1,1-, 1,2-, 1,3- or 2,2 -Pro- pandiyl stand,

R represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or benzyl,

R ^, R3 and R ^ are the same or different and each represents hydrogen, fluorine, chlorine, bromine, cyano, nitro, 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, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy,

Trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, di-fluorochloromethylthio, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl, vinyl, allyl, allyloxy or cyclopropyl, but one or the radicals ^, R is hydrogen, but is different from ^, R is hydrogen,

R5 for fluorine, chlorine, bromine, cyano, nitro, 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, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoromethyl, difluoromethylfluifluoromethyl, difluoromethyl, difluoromethyl, difluoromethyl, difluoromethyl Allyl, allyloxy or cyclopropyl,

R6 and R are the same or different and each represents chlorine, methyl, ethyl, vinyl, allyl, 2-methylethen-l-yl, ethinyl, 2-methylethin-l-yl, propargyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoroethoxy, Methylthio, ethylthio, methylamino, ethylamino, dimethylamino, cyclopropyl or oxethan-1-yloxy and represents nitrogen or where

Rl2 represents hydrogen, fluorine, chlorine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, trifluoroethyl, methoxymethyl or ethoxymethyl.

The general or preferred radical definitions listed above apply both to the end products of the formula (I) and correspondingly to the starting or intermediate products required in each case for the preparation. The radical definitions specified for these radicals in the respective combinations or preferred combinations of radicals are independently replaced by radical definitions of other preferred ranges, regardless of the combination specified in each case.

If, for example, 2-amino-4,6-dimethoxy-s-triazine, chlorosulfonyl isocyanate and 2-fluoro-5-methyl-6-propionyl-aniline are used as starting materials, the course of the reaction in the process according to the invention can be outlined using the following formula :

Formula (II) provides a general definition of the aminotriazines or pyrimidines required to carry out process a) according to the invention for the preparation of the compounds of formula (I) according to the invention. In this formula (II) R ^, R ^ and G preferably or in particular have those meanings which have already been in connection with the description of the compounds of the invention

Formula (I) was given as preferred or as particularly preferred for R, R ^ and G.

The aminotriazines or pyrimidines of the formula (II) are known (compare, for example, EP-A 476554) and can be prepared by known methods.

The chlorosulfonyl isocyanate also required to carry out the process according to the invention for the preparation of the compounds of the formula (I) is a generally known laboratory chemical.

Formula (IV) provides a general definition of the anilines which are further required to carry out the process according to the invention for the preparation of the compounds of the formula (I) according to the invention. In this formula (IV) R, R ^, R3 _; R4 _{un (j} R5 preferably or in particular have those meanings which have already menhang together with the description of the compounds of formula (I) as being preferred or as particularly preferred for R, R ^, R3 R4 _{un d?} Specified R5 .

The anilines of the formula (IV) are known and / or can be prepared by processes known per se (compare, for example, US Pat. No. 5405998 and DE-A 4414476).

The process according to the invention for the preparation of the new compounds of the formula (I) is preferably carried out using diluents. Practically all inert organic solvents can be used as diluents. These preferably include aliphatic and aromatic, optionally halogenated hydrocarbons such as pentane, hexane, heptane, cyclohexane, petroleum ether, gasoline, ligroin, benzene, toluene, xylene, methylene chloride, ethylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, ethers such as diethyl and dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, tetrahydrofuran and dioxane, ketones such as acetone, methyl ethyl, methyl isopropyl and methyl isobutyl ketone, esters such as methyl acetate and ethyl acetate, nitriles such as acetonitrile and propionitrile, amides such as dimethylformamide, dimethylacetamide and N-methylpyrrolidone and dimethyl sulfoxide, tetramethylene sulfone and hexamethyl phosphoric acid triamide.

Acid acceptors which can be used in the process according to the invention are all acid binders which can customarily be used for such reactions. Alkali metal hydroxides such as e.g. Sodium and potassium hydroxide,

Alkaline earth hydroxides such as Calcium hydroxide, alkali carbonates and alcoholates such as sodium and potassium carbonate, such as sodium and potassium tert-butoxide, also aliphatic, aromatic or heterocyclic amines, for example triethylamine, trimethylamine, dimethylaniline, dimethylbenzylamine, pyridine, 1,5-diazabicyclo [4 , 3,0] - non-5-ene (DBN), 1,8-diazabicyclo- [5,4,0] -undec-7-ene (DBU) and 1,4-diazabicyclo-

[2,2,2] octane (DABCO) into consideration.

The reaction temperatures can be varied within a wide range in the process according to the invention. In general, temperatures between -30 ° C and + 80 ° C, preferably at temperatures between -10 ° C and

+ 60 ° C.

The process according to the invention is generally carried out under normal pressure. However, it is also possible to work under increased or reduced pressure.

To carry out the process according to the invention, the starting materials required in each case are generally used in approximately equimolar amounts. However, it is also possible to use one of the two components used in each case in a larger excess. The reactions are generally carried out in a suitable diluent in the presence of an acid acceptor, and the reaction mixture is kept at the required temperature for several hours. door stirred. Working up in the process according to the invention is carried out in each case by customary methods (cf. the preparation examples).

If appropriate, salts can be prepared from the compounds of the general formula (I) according to the invention. Such salts are obtained in a simple manner by customary salt formation methods, for example by dissolving or dispersing a compound of the formula (I) in a suitable solvent, e.g. Methylene chloride, acetone, tert-butyl methyl ether or toluene, and addition of a suitable base. The salts can then be isolated - if necessary after prolonged stirring - by concentrating or suctioning off.

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

Fungicides can be used to protect plants against Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.

Bactericides can be used in plant protection to combat Pseudomonadaceae,

Use Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.

Some pathogens of fungal and bacterial are exemplary but not limiting

Diseases that fall under the generic names listed above:

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

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

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

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

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

Pseudoperonospora cubensis;

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

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

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

Sphaerotheca species, such as, for example, Sphaerotheca Fülliginea; 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 he otrichoides.

The fact that the active compounds are well tolerated by plants in the concentrations required to combat plant diseases allows treatment above ground

Parts of plants, of seedlings, and of the soil.

The active compounds according to the invention can be particularly successful

Combat diseases in wine, fruit and vegetable cultivation, such as against Venturia, Sphaerotheca and Podosphaera species. Cereal diseases, such as Erysiphe species, are also successfully combated. 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.

With good plant tolerance and favorable warm-blood toxicity, the active substances are suitable for combating animal pests, in particular insects, arachnids and nematodes, which occur in agriculture, in forests, in the protection of stored goods and materials, and in the hygiene sector. They can preferably be used as pesticides. They are effective against normally sensitive and resistant species as well as against all or individual stages of development. The pests mentioned above include:

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

From the order of the Chilopoda e.g. Geophilus carpophagus, Scutigera spec.

From the order of the Symphyla e.g. Scutigerella immaculata.

From the order of the Thysanura e.g. Lepisma saccharina.

From the order of the Collembola e.g. Onychiurus armatus. From the order of the Orthoptera e.g. Blatta orientalis, Periplaneta americana,

Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp.,

Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria.

From the order of the Dermaptera e.g. Forficula auricularia.

From the order of the Isoptera e.g. Reticulitermes spp .. From the order of the Anoplura e.g. Pediculus humanus corporis, Haematopinus spp.,

Linognathus spp.

From the order of the Mallophaga e.g. Trichodectes spp., Damalinea spp.

From the order of the Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci.

From the order of the Heteroptera e.g. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.

From the order of the Homoptera, for example Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, -AS

Aphis fabae, aphis pomi, eriosoma lanigerum, hyalopterus arundinis, phylloxera vastatrix, pemphigus spp., Macrosiphum avenae, myzus spp., Phorodon humuli, rhopalosiphum padi, empoasca spp , Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp.

From the order of the Lepidoptera e.g. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiisispppp., Phyllocnistia. Phyllocnist.

Earias insulana, Heliothis spp., Spodoptera exigua, Mamestra brassicae, Panolis flammea, Spodoptera litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chi o spp., Pyrausta nubilalis, Ephestia kuehnellella, Ephestia kuehnellella, Tinea pellionella, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fümiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana.

From the order of the Coleoptera e.g. Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephususpp sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psioloides , Agriotes spp.,

Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica.

From the order of the Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.

From the order of the Diptera, for example Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia • λ- 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.

From the order of the Siphonaptera e.g. Xenopsylla cheopis, Ceratophyllus spp ..

From the order of the Arachnida e.g. Scorpio maurus, Latrodectus mactans.

From the order of the Acarina e.g. 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., Tarsonaia spp., Tarsonaia spp ., Tetranychus spp ..

Plant-parasitic nematodes include e.g. Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp.

The compounds of the formula (I) according to the invention are notable in particular for their action against insects which damage plants, such as, for example, against the larvae of the horseradish leaf beetle (Phaedon cochleariae) and the onion fly (Hylemyia antiqua).

Depending on their respective physical and / or chemical properties, the active ingredients can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in coating compositions for seeds, and ULV - Cold and warm fog formulations.

These formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents, under pressure, AI liquid gases and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents. If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene or

Alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. Petroleum fractions, alcohols, such as butanol or glycol, and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, highly polar solvents, such as dimethylformamide and dimethyl sulfoxide, and water. Liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and pressure, e.g. Aerosol propellants such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide. Possible solid carriers are: e.g. natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates. The following are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well as synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and

Tobacco stem. Possible emulsifiers and / or foaming agents are: e.g. nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates. Possible dispersants are: e.g. Lignin liquor and methyl cellulose.

Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as cinimiarabicum, polyvinyl alcohol, polyvinyl acetate, and also natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations. Other additives can be mineral and vegetable oils. Λ2

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

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

As such or in their formulations, the active compounds according to the invention can also be mixed with known fungicides, bactericides, acaricides, nematicides or

Insecticides can be used, e.g. to broaden the spectrum of activity or to prevent the development of resistance. In many cases, synergistic effects are obtained, i.e. the effectiveness of the mixture is greater than the effectiveness of the individual components.

The following connections can be considered as mixed partners:

Fungicides:

Aldimorph, ampropylfos, ampropylfos potassium, andoprim, anilazine, azaconazole,

Azoxystrobin,

Benalaxyl, Benodanil, Benomyl, Benzamacril, Benzamacryl-Isobutyl, Bialaphos, Binapacryl, BiphenyL Bitertanol, Blasticidin-S, Bromuconazol, Bupirimat, Buthiobat,

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, diclora, diethofencarb, difenoconazole, dimetliirimol, dimethomorph, diniconazole, diniconazole M, Dinocap, Diphenylamine, Dipyrithione, Ditalimfos, Dithianon, Dodemorpn, Dodine, Drazoxolon,

Ediphenphos, Epoxiconazole, Etaconazole, Ethirimol, Etridiazole,

Famoxadone, Fenapanil, fenarimol, fenbuconazole, Fenfüram, Fenitropan, fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, Fentinhydroxyd, ferbam, ferimzone, fluazinam, flumetover, fluoromide, fluquinconazole, Fluφrimidol, flusilazole, flusulfamide, flutolanil, flutriafol, folpet, fosetyl-Alininium, 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, Methfüroxam, Metiram, Metomeclam, Metsulfovax,

Mildiomycin, myclobutanil, myclozolin,

Nickel dimethyldithiocarbamate, nitrothal isopropyl, Nuarimol,

Ofürace, Oxadrxyl, Oxamocarb, Oxolinicacid, Oxycarboxim, Oxyfenthiin,

Paclobutrazole, pefürazoate, penconazole, pencycuron, phosdiphen, pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz, procymidon, propamocarb, propanosine Sodium, propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil, pyroquilon, pyroxyfur,

Quinconazole, quintozen (PCNB),

Sulfur and sulfur preparations,

Tebuconazole, Tecloftalam, Tecnazen, Tetcyclacis, Tetraconazole, Thiabendazole, Thicyofen, Thifluzamide, Thiophanate-methyl, Thirarn, Tioxymid, Tolclofos-methyl, Tolylfluanid, Triadimefon, Triadimenol, Triazbutichlamidium, Triazoxid, Triazoxid, Triazoxid, Triazoxid, Triazoxid

Triflumizole, triforin, triticonazole,

Uniconazole,

Validamycin A, vinclozolin, viniconazole,

Zarilamid, Zineb, Ziram as well

Dagger G, OK-8705,

OK-8801, α- (1, 1-dimethylethyl) -ß- (2-phenoxyethyl) - 1 H-1, 2,4-triazole-1-ethanol, α- (2,4-dichloφhenyl) -ß-fluorine -b-propyl-1 H-1, 2,4-triazole-1-ethanol, α- (2,4-dichloro phhenyl) -ß-methoxy-a-methyl-1 H-1, 2,4-triazole-1 -ethanol, α- (5-methyl-l, 3-dioxan-5-yl) -ß - [[4- (trifluoromethyl) -phenyl] methylene] -lH-l, 2,4-triazole-

1-ethanol,

(5RS, 6RS) -6-hydroxy-2,2,7,7-tetramethyl-5- (1H-1, 2,4-triazol-1-yl) -3-octanone,

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

(2-Methyl-1 - [[[[- (4-methylphenyl) -ethyl] -ammo] -carbonyl] -propyl} -carbamic acid 1-isopropyl ester

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

1 - (2-methyl-1-naphthalenyl) - 1 H-pyrrole-2, 5-dione, IΛ

1 - (3, 5 -Dichloφhenyl) -3 - (2-propenyl) -2, 5-pyrrolidinedione, l - [(diiodomethyl) sulfonyl] -4-methyl-benzene,

1 - [[2- (2,4-dichlorothenyl) -1,3-dioxolan-2-yl] methyl] - 1H-imidazole, l - [[2- (4-chlorophenyl) -3-phenyloxiranyl] methyl ] -lH-l, 2,4-triazole, l- [l- [2 - [(2,4-dichloφhenyl) methoxy] phenyl] ethenyl] -lH-imidazole, l-methyl-5-nonyl- 2- (phenylmethyl) -3-pyrrolidinol,

2 ^, 6'-dibromo-2-memyl-4 ^, -trifluoromethoxy-4'-trifluoromethyl-1,3-t-wazole-5-carboxanilide,

2,2-dichloro-N- [1- (4-chloro-phenyl) -ethyl] -l-ethyl-3-methyl-cyclopropanecarboxamide,

2,6-DicWor-5- (methyltMo) -4-pyrimidinyl-thiocyanate, 2,6-DicMor-N- (4-trifluoromethylbenzyl) benzamide,

2,6-DicUor-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-1 H-pyrrolo [2, 3-d] pyrimidine -5-carbonitrile,

2-aminobutane,

2-bromo-2- (bromomethyl) pentandinitrile,

2-Cuor-N- (2,3-dihydro-l, l, 3-trimethyl-lH-mden-4-yl) -3-pyridinecarboxamide,

2-chloro-N- (2,6-dimethylphenyl) -N- (isothiocyanatomethyl) acetamide, 2-phenylphenol (OPP),

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

3,5-dichloro-N- [cyan [(1-methyl-2-propynyl) oxy] methyl] benzamide,

3- (1,1-dimethylpropyl-1-oxo-lH-indene-2-carbonitrile,

3- [2- (4-CUoφhenyl) -5-ethoxy-3-isoxazoüdinyl] pyridine, 4-chloro-2-cyano-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-hydroxycholine sulfate,

9H-xanthene-9-carboxylic acid 2- [φhenylamino) carbonyl] hydrazide, bis- (l-methylethyl) -3-methyl-4 - [(3-methylbenzoyl) -oxy] -2,5-thiophene dicarboxylate, ice - 1 - (4-Chlθφhenyl) -2- (1 H- 1, 2,4-triazol-1-yl) -cycloheptanol, cis-4- [3- [4- (l, l-dimethylpropyl) -phenyl- 2-methylpropyl] -2,6-dimethyl-moφholin hydrochloride, IV

Ethyl - [(4-chloro-phenyl) -azo] cyanoacetate,

Potassium hydrogen carbonate,

Methane tetrathiol sodium salt,

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

Methyl N- (chloroacetyl) -N- (2,6-dimethylphenyl) -DL-alaninate,

N- (2,3-dichloro-4-hydroxyphenyl) -1-methylcyclohexane 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-pyrimidamine,

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 - [(cMoracetyl) -ammo] ethyl] benzamide,

N- [3-CUor-4,5-bis (2-propynyloxy) phenyl] -N ^, -methoxy-methaniramidamide,

N-formyl-N-hydroxy-DL-alanine sodium salt,

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

O-methyl-S-phenyl-phenylpropylphosphoramidothioate, S-methyl-l, 2,3-benzothiadiazole-7-carbothioate, spiro [2H] - 1-benzopyran-2, 1 '(3 Η) -isobenzofüran] -3'- on,

Bactericides:

Bronopol, dichlorophene, nitrapyrin, nickel dimethyldithiocarbamate, ICasugamycin, octhilinon, furan carboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulfate and other copper preparations.

Insecticides / acaricides / nematicides:

Abamectin, Acephat, Acrinathrin, Alanycarb, Aldicarb, Alphamethrin, Amitraz, Avermectin, AZ 60541, Azadirachtin, Azinphos A, Azinphos M, Azocyclotin, Bacillus thuringiensis, 4-bromo-2- (4-chlθφhenyl) -l- (ethoxymethyl) -5- (trifluoromethyl) - 1H-pyrrole-3-carbonitrile, bendiocarb, benftiracarb, bensultap, betacyfluthrin, bifenthrin, BPMC, brofenprox, bromine A, Bufencarb, Buprofezin, Butocarboxim, Butylpyridaben,

Cadusafos, Carbaryl, Carbofüran, Carbophenothion, Carbosulfan, Cartap, Chloethocarb, Chlorethoxyfos, Chlorfenapyr, Chlorfenvinphos, Chlorfluazuron, Chlormephos, N - [(6- CWoro-3-pyrid yl) -methyl] -N-cyano-N-memyl-ethanimide , Chloφyrifos, Chlorpyrifos M, Cis-Resmethrin, Clocythrin, Clofentezin, Cyanophos, Cycloprothrin, Cyfluthrin, Cyhalothrin, Cyhexatin, Cypeπnethrin, Cyromazin,

Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Diazinon, Dichlofenthion, Dichlorvos, Dicliphos, Dicrotophos, Diethion, Diflubenzuron, Dimethoat, Dimethylvinphos, Dioxathion, Disulfoton,

Edifenphos, Emamectin, Esfenvalerat, Ethiofencarb, Ethion, Ethofenprox, Ethoprophos, Etrimphos,

Fenamiphos, Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil,

Fluazinam, Fluazuron, Flucycloxuron, Flucythrinat, Flufenoxuron, Flufenprox, Fluvalinate, Fonophos, Formothion, Fosthiazat, Fubfenprox, Furathiocarb,

HCH, heptenophos, hexaflumuron, hexythiazox,

Imidacloprid, Iprobefos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivermectin,

Lamda-cyhalothrin, Lufenuron,

Malathion, Mecarbam, Mevinphos, Mesulfenphos, Metaldehyde, Methacrifos, Methamidophos, Methidathione, Methiocarb, Methomyl, Metolcarb, Milbemectin, Monocrotophos, Moxidectin, Naled, NC 184, Nitenpyram

Omethoate, Oxamyl, Oxydemethon M, Oxydeprofos,

Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos M, Pirimiphos A, Profenophos, Promecarb, Propaphos, Propoxur, Prothiophos, Prothoat, Pymethionos, Pyridaphrinophone, Pyridaphrinin, Pyridaphrin Pyrethrum, Pyridaben, Pyrimidifen, Pyriproxifen,

Quinalphos,

Salithion, Sebufos, Silafluofen, Sulfotep, Sulprofos,

Tebufenozide, Tebufenpyrad, Tebupirimiphos, Teflubenzuron, Tefluthrin, Temephos, Terbam, Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thiofanox, Thiomethon,

Thionazin, Thuringiensin, Tralomelbiin, Triarathen, Triazophos, Triazuron, Trichlorfon, Triflumuron, Trimethacarb,

Vamidothione, XMC, xylylcarb, zetamethrin.

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

The active compounds according to the invention can also be used in their commercially available formulations and in the use forms prepared from these formulations

Mix with synergists. Synergists are compounds through which the action of the active ingredients is increased without the added synergist itself having to be active.

The active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges. The active substance concentration of the use forms can be from 0.0000001 to 95% by weight of active substance, preferably between 0.0001 and 1% by weight. 15

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

When used against hygiene and storage pests, the stands out

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

The active compounds according to the invention act not only against plant, hygiene and stored-product pests, but also in the veterinary sector against animal parasites (ectoparasites) such as tick ticks, leather ticks, mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, hair lice, Featherlings and fleas. These parasites include:

From the order of the Anoplurida e.g. Haematopinus spp., Linognathus spp.,

Pediculus spp., Phtirus spp., Solenopotes spp ..

From the order of the Mallophagida and the subordinates Amblycerina and Ischnocerina e.g. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp ..

From the order Diptera and the subordinates Nematocerina and Brachycerina z iχ..Bx-> .. s upfp _f -X.- ,, A lnuo _j pjhi.evile-s s "pfpf. •,>

S wimuiuuuliuumiu s up _j jpj -, .. ,, E J.uUÜsiHmUuUliuUmU1 s np ypj .. ,,

Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp ., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp ..

From the order of the Siphonapterida, for example Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp .. From the order of the Heteropterida, for example Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp ..

From the order of the Blattarida e.g. Blatta orientalis, Periplaneta americana, Blattela germanica, Supella spp ..

From the subclass of Acaria (Acarida) and the orders of the Meta and Mesostigmata e.g. Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemophysahs spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietssia spp., .,

Sternostoma spp., Varroa spp ..

From the order of the Actinedida (Prostigmata) and Acaridida (Astigmata) e.g. Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp.,

Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp ..

The active compounds of the formula (I) according to the invention are also suitable for controlling arthropods which are used in agricultural animals, e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as e.g. Dogs, cats, house birds, aquarium fish and so-called experimental animals, such as Infest hamsters, guinea pigs, rats and mice. By fighting these arthropods, deaths and

Reductions in performance (for meat, milk, wool, skins, eggs, honey, etc.) are reduced, so that the use of the active compounds according to the invention enables more economical and simple animal husbandry.

The active compounds according to the invention are used in the veterinary sector in a known manner by enteral administration in the form of, for example, tablets, capsules, drinkers, drenches, granules, pastes, boluses, the feed-through method, suppositories, by parenteral administration, for example by Injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants, by nasal application, by dermal application in the form of, for example, diving or bathing (dipping), spraying (spray), pouring on (pour-on and spot-on), washing, powdering and with the aid of shaped articles containing active ingredients, such as necklaces, ear tags, tail tags, limb tapes, holsters, marking devices, etc.

When used for cattle, poultry, pets etc., you can use the active ingredients in

Formula (I) as formulations (for example powders, emulsions, flowable agents) which contain the active compounds in an amount of 1 to 80% by weight, directly or after

Apply 100 to 10,000-fold dilution or use it as a chemical bath.

It has also been found that the compounds of the formula (I) according to the invention have a high activity against insects and microorganisms which destroy industrial materials.

The following insects may be mentioned by way of example and preferably, but without limitation:

Beetle like

Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobius mollis, Priobium caφini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearesceses, Lyctus pubesculuses, Lyctus pubescuses, Lyctus pubescusis, Lyctus pubescusis, Lyctus linearesces rug Xyleborus spec. Tryptodendron spec. Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec. Dinoderus minutus

Skin wings like

Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur

Termites like Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifügus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus.

Bristle tails, such as Lepisma saccarina.

Bacteria, fungi, yeasts, algae and mucilaginous organisms may be mentioned as microorganisms which can cause degradation or a change in the technical materials. The active compounds according to the invention preferably act against fungi, in particular mold, wood-discoloring and wood-destroying fungi

(Basidiomycetes) and against 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.

In the present context, technical materials are understood to mean non-living materials, such as preferably plastics, adhesives, glues, papers and cartons, leather, wood and wood processing products and paints.

The material to be protected against insect infestation is very particularly preferably wood and wood processing products. ZI

Wood and wood processing products which can be protected by the agent according to the invention or mixtures containing it are to be understood as examples of construction timber, wooden beams, railway sleepers, bridge parts, jetties, wooden vehicles, boxes, pallets, containers, telephone masts, wooden cladding, wooden windows and doors. Plywood, chipboard, carpentry or wood products that are generally used in house construction or joinery

The active compounds can be used as such, in the form of concentrates or generally customary formulations such as powders, granules, solutions, suspensions, emulsions or

Pastes can be applied

The formulations mentioned can be prepared in a manner known per se, for example by mixing the active ingredients with at least one solvent or diluent, emulsifier, dispersant and / or binder or fixative,

Water repellants, optionally desiccants and UV stabilizers and optionally dyes and pigments as well as other processing aids

The agents or concentrates used to protect wood and wood-based materials contain the active ingredient according to the invention in a concentration of 0.0001 to

95% by weight, in particular 0.001 to 60% by weight

The amount of the agents or concentrates used depends on the type and occurrence of the insects or microorganisms and on the medium. The optimum amount can be determined by using a series of tests. In general, however, it is sufficient 0.0001 to 20 % By weight, preferably 0.001 to 10% by weight, of the active ingredient, based on the material to be protected

An organic-chemical solvent or solvent mixture and / or an oily or oil-like, slightly volatile organic-chemical solvent or solvent mixture and / or a polar solvent serves as the solvent and / or diluent organic chemical solvent or solvent mixture and / or water and optionally an emulsifier and / or wetting agent.

The organic chemical solvents used are preferably oily or oily solvents with an evaporation number above 35 and a flash point above 30 ° C., preferably above 45 ° C. Corresponding mineral oils or their aromatic fractions or mineral oil-containing solvent mixtures, preferably white spirit, petroleum and / or alkylbenzene, are used as such low-volatility, water-insoluble, oily and oily solvents.

Mineral oils with a boiling range of 170 to 220 ° C, white spirit with a boiling range of 170 to 220 ° C, spindle oil with a boiling range of 250 to 350 ° C, petroleum or aromatics with a boiling range of 160 to 280 ° C, turpentine oil and Like. Used.

In a preferred embodiment, liquid aliphatic hydrocarbons with a boiling range from 180 to 210 ° C. or high-boiling mixtures of aromatic and aliphatic hydrocarbons with a boiling range from 180 to 220 ° C. and / or locker oil and / or monochloronaphthalene, preferably α-monochloronaphthalene, used.

The organic low-volatility oily or oily solvents with an evaporation number above 35 and a flash point above 30 ° C, preferably above 45 ° C, can be partially replaced by slightly or medium-volatile organic chemical solvents, with the proviso that the solvent mixture also has an evaporation number 35 and a flash point above 30 ° C, preferably above 45 ° C, and that the insecticide-fungicide mixture is soluble or emulsifiable in this solvent mixture.

According to a preferred embodiment, part of the organic chemical

Solvent or solvent mixture or an aliphatic polar organic chemical solvent or solvent mixture replaced. Preferably aliphatic organochemical solvents containing hydroxyl and / or ester and / or ether groups such as glycol ethers, esters or the like are used.

In the context of the present invention, the organic-chemical binders used are the water-thinnable and / or synthetic resins which are soluble or dispersible or emulsifiable in the organic chemical solvents used and / or binding drying oils, in particular binders consisting of or containing an acrylate resin, a vinyl resin , e.g. Polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indene-coumarone resin, silicone resin, drying vegetable and / or drying oils and / or physically drying binders based on a natural and / or synthetic resin used.

The synthetic resin used as a binder can be used in the form of an emulsion, dispersion or solution. Bitumen or bituminous substances up to 10% by weight can also be used as binders. In addition, known dyes, pigments, water-repellants, odor correctors and inhibitors or anticorrosive agents and the like can be used.

According to the invention, at least one alkyd resin or modified alkyd resin and / or a drying vegetable oil is preferably contained in the agent or in the concentrate as the organic chemical binder. Alkyd resins with an oil content of more than 45% by weight, preferably 50 to 68% by weight, are preferably used according to the invention.

All or part of the binder mentioned can be replaced by a fixing agent (mixture) or a plasticizer (mixture). These additives are intended to prevent volatilization of the active ingredients and crystallization or precipitation. They preferably replace 0.01 to 30% of the binder (based on

100% of the binder used). Z

The plasticizers come from the chemical classes of phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate, phosphoric acid esters such as tributyl phosphate, adipic acid esters such as di- (2-ethylhexyl) adipate, stearates such as butyl stearate or amyl stearate, oleates such as butyl oleate, higher glycerol glycol or glycerol glycol - ether, glycerol ester and p-toluenesulfonic acid ester.

Fixing agents are chemically based on polyvinyl alkyl ethers such as e.g. Polyvinyl methyl ether or ketones such as benzophenone, ethylene benzophenone.

Water is also particularly suitable as a solvent or diluent, optionally in a mixture with one or more of the above-mentioned organic chemical solvents or diluents, emulsifiers and dispersants.

A particularly effective wood protection is achieved through industrial impregnation processes, e.g. Vacuum, double vacuum or pressure process.

The ready-to-use compositions may also contain further insecticides and / or fungicides.

The insecticides and fungicides mentioned in WO 94/29 268 are preferably suitable as additional admixing partners. The compounds mentioned in this document are an integral part of the present application.

Insecticides such as chloropyriphos, phoxime, silafluofin, alphamethrin, cyfluthrin, cypermethrin, deltamethrin,

Permethrin, imidacloprid, NI-25, flufenoxuron, hexaflumuron and triflumuron,

as well as fungicides such as epoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole, cyproconazole, metconazole, imazalil, dichlorofluoride, tolylfluoride, 3-iodo-2-propynylbutylcarbamate, N-octyl-isothiazolin-3-one and 4,5-dichloro N-octylisothiazolin-3-one. The preparation and use of the active compounds according to the invention can be seen from the examples below.

Preparation Examples:

example 1

8.2 g (0.053 mol) of 2-amino-4,6-dimethoxy-pyrimidine is added to a solution of 6.8 g (0.0479 mol) of chlorosulfonyl isocyanate in 80 ml of dichloromethane at approx. 0 ° C and approx stirred at 0 to 20 ° C. for one hour. A solution of 10 g (0.0479 mol) of (2-amino-4-chloro-3-methylphenyl) cyclopropylmethanone and 7.3 g (0.072 mol) of triethylamine in 15 ml of dichloromethane is then added dropwise and the mixture is stirred 15 hours at 20 ° C. Dilute hydrochloric acid is added to the reaction mixture, the organic phase is separated off and the aqueous phase is extracted twice with dichloromethane. The combined organic phases are washed twice with saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated in a water jet vacuum. The residue is stirred with ethanol, the solid is suction filtered, washed twice with a little ethanol, then twice with diethyl ether and dried.

10.8 g (48% of theory) of N - {[(5-chloro-2-cycloproρylcarbonyl-6-methylphenyl) amino] sulfonyl} -N '- (4, 6-dimethoxypyrimidin-2-yl) are obtained. -urea from melting point 153 ° C. Example 2

108 g (0.01 1 mol) of 2-amino-4-chloro-6-methoxy-pyrimidine are added at about 0 ° C. to a solution of 1042 g (0.01 mol) of chlorosulfonyl isocyanate in 80 ml of dichloromethane and stirred for about 30 minutes at 0 to 20 ° C. A solution of 2.1 g (0.01 mol) of (2-amino-4-chloro-3-methylphenyl) cyclopropylmethanone and 1.5 g (0.015 mol) of triethylamine in 5 ml of dichloromethane is then added dropwise and stirred for a further 15 hours at 20 ° C. Dilute hydrochloric acid is added to the reaction mixture, the organic phase is separated off and the aqueous phase is extracted once with dichloromethane. The combined organic phases are washed once with water, dried over sodium sulfate, filtered and concentrated in a water jet vacuum. The residue is stirred with ethanol, the solid is filtered off with suction, washed with diethyl ether and dried.

2.2 g (46.8% of theory) of N - {[(5-chloro-2-cyclopropylcarbonyl-6-methylphenyl) amino] sulfonyl} -N '- (4-chloro-6-methoxypyrimidine-2- yl) urea with a melting point of 138 ° C. (decomposition).

Preparation of the starting material for Examples 1 and 2

75 g (0.64 mol) of boron trichloride are introduced into 200 ml of 1,2-dichloroethane. A solution of 70.8 g (0.5 mol) of 3-chloro-2-methylaniline in 120 ml of 1,2-dichloroethane is added dropwise at 0 ° C and the mixture is stirred at 20 ° C for 40 minutes. A solution of 52.4 g (0.77 mol) of cyclopropanecarbonitrile in 55 ml of 1,2-dichloroethane is then added dropwise and the mixture is stirred at 20 ° C. for a further hour. A further 113.8 g (0.6 mol) of titanium tetrachloride are then added dropwise and the mixture is heated under reflux for 8 hours. After cooling, 250 ml of water are carefully added dropwise while cooling with ice, the organic phase is separated off and the aqueous phase is extracted twice with ethyl acetate. The combined organic phases are washed twice with saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated in a water jet vacuum.

81 g of l- (2-amino-4-chloro-3-methylphenyl) -4-chlorobutan-l-one are obtained. This is dissolved in a sodium methoxide solution, which was freshly prepared from 7.9 g sodium and 300 ml methanol, and stirred at 20 ° C. for 56 hours. The reaction mixture is concentrated in a water jet vacuum, mixed with 100 ml of water and extracted twice with ethyl acetate. The combined organic phases are over

Dried sodium sulfate, filtered and concentrated in a water jet vacuum. The residue is chromatographed on silica gel using hexane / ethyl acetate (9: 1).

51 g (48.6% of theory based on 3-chloro-2-methylaniline) (2-amino-4-chloro-3-methylphenyl) cyclopropylmethanone with a melting point of 65 ° C. are obtained. a *

Example 3

0.7 g (0.0045 mol) of 2-amino-4,6-dimethoxy-pyrimidine is added to a solution of 0.62 g (0.00442 mol) of chlorosulfonyl isocyanate in 20 ml of dichloromethane at approx. 0 ° C and approx Stirred at 0 to 20 ° C for 30 minutes. A solution of 1.0 g (0.0042 mol) of l- (2-amino-4-chloro-3-methylphenyl) propan-l-one-O-methyl-oxime and 0.7 g (0 , 0663 mol) of triethylamine in 2 ml of dichloromethane and stirred for a further 15 hours at 20 ° C. 5% sodium dihydrogen phosphate solution is added to the reaction mixture, the organic phase is separated off and the aqueous phase is extracted once with dichloromethane. The combined organic phases are washed twice with saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated in a water jet vacuum. The residue is stirred with ethanol, the solid is filtered off with suction, washed first twice with a little ethanol, then twice with diethyl ether and dried.

1.4 g (66.7% of theory) of N - {[(5-chloro-2- (l-methoximinoprop-l-yl) -6-methylphenyl) amino] sulfonyl} -N '- (4- chlor-6-methoxypyrimidin-2-yl) urea with a melting point of 154 ° C. Production of the starting material

To a solution of 5 g (0.0253 mol) of l- (2-amino-4-chloro-3-methylphenyl) propane

1-one in 100 ml of dichloromethane, 11 g (0.101 mol) of trimethylchlorosilane are added dropwise and the mixture is stirred at 20 ° C. for one hour. A solution of 4.2 g (0.0506 mol) of methoxyamine hydrochloride and 5.1 g (0.0506 mol) of triethylamine in 2.5 ml of dichloromethane, which was stirred at 20 ° C. for one hour, is then added dropwise and 2 Stirred at 20 ° C for days. A solution of 2 g (0.024 mol) of methoxyamine hydrochloride and 2.4 g (0.024 mol) of triethylamine in 10 ml of dichloromethane, which was stirred for one hour at 20 ° C., is then added dropwise and the mixture is stirred at 20 ° C. for a further 8 days . The reaction mixture is mixed with 5% sodium dihydrogenphosphate solution, the organic phase is separated off and the aqueous phase is extracted once with dichloromethane. The combined organic phases are washed twice with water, dried over sodium sulfate, filtered and concentrated in a water jet vacuum. The residue is chromatographed on silica gel using hexane / ethyl acetate (30: 1).

1.8 g (31.6% of theory) of 1- (2-amino-4-chloro-3-methylphenyl) propane-1-one-O-methyl-oxime with a melting point of 93 ° C. are obtained.

33

Example 4

1.7 g (0.011 mol) of 2-amino-4,6-dimethoxy-pyrimidine is added to a solution of 1.46 g (0.0104 mol) of chlorosulfonyl isocyanate in 20 ml of dichloromethane at about 0 ° C. and for 30 minutes at 0 stirred up to 20 ° C. A solution of 2.5 g (0.0104 mol) of 3-chloro-6- (2-ethyl- [1,3] dioxolan-2-yl) -2-methylaniline and 1.6 g (0, 0156 mol) of triethylamine in 10 ml of dichloromethane and stirred for a further 15 hours at 20 ° C. The reaction mixture is mixed with 5% sodium dihydrogen phosphate solution, the organic phase is separated off and the aqueous phase is extracted once with dichloromethane. The combined organic phases are washed twice with saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated in a water jet vacuum. The residue is stirred with ethanol, the solid is suctioned off, first four times with a little ethanol, then three times with

Washed diethyl ether and finally twice with petroleum ether and dried.

1.8 g (34.6% of theory) of N - {[(3-chloro-6- (2-ethyl- [1,3] dioxolan-2-yl) -2-methylphenyl) amino] sulfonyl} are obtained. -N '- (4, 6-dimethoxypyrimidin-2-yl) urea from

Melting point 167 ° C. O

Production of the starting material

To a suspension of 5 g (0.0253 mol) of 1- (2-amino-4-chloro-3-methylphenyl) propan-1-one in 50 ml of ethane-1,2-diol, 16.5 g ( 0.152 mol) of trimethylchlorosilane and stirred at 20 ° C. for 15 hours. 50 ml of diethyl ether are added to the reaction mixture, the mixture is washed twice with saturated sodium hydrogen carbonate solution and once with water, dried over sodium sulfate, filtered and concentrated in a water jet vacuum. The residue is chromatographed on silica gel using hexane / ethyl acetate (30: 1).

4.4 g (72.1% of theory) of 3-chloro-6- (2-ethyl- [1,3] dioxolan-2-yl) -2-methylaniline are obtained

^ -NM (CDCI3): δ = 7.24-7.53 (m, 4H); 8.29 (s, 1H) ppm

Production of the preliminary product

150 g (1.25 mol) of boron trichloride are introduced into 400 ml of 1,2-dichloroethane. A solution of 141.5 g (1.0 mol) of 3-chloro-2-methylaniline in 150 ml of 1,2-dichloroethane is added dropwise at 0 ° C. and the mixture is stirred at 20 ° C. for 40 minutes. A solution of 82.5 g (1.5 mol) of propionitrile is then added dropwise and the mixture is stirred at 20 ° C. for a further hour. Now 227.6 g (1.2 mol) of titanium tetrachloride are added dropwise and the mixture is heated under reflux for 15 hours. After cooling, carefully drop it under ice cooling

500 ml of water, the organic phase is separated off and the aqueous phase is extracted four times with ethyl acetate. The aqueous phase is neutralized with dilute sodium hydroxide solution and extracted twice more with ethyl acetate. The combined organic phases are washed twice with water, dried over sodium sulfate, filtered and concentrated in a water jet vacuum. The arrears with

Chromatograph hexane / ethyl acetate (9: 1) on silica gel.

143.4 g (72.6% of theory) of 1- (2-amino-4-chloro-3-methylphenyl) propan-1-one with a melting point of 58 ° C. are obtained.

L-

Example 5

1.7 g (0.011 mol) of 2-amino-4,6-dimethoxy-pyrimidine are added to a solution of 11.6 g (0.082 mol) of chlorosulfonyl isocyanate in 100 ml of dichloromethane at about 0 ° C. and for 30 minutes at 0 to Stirred at 20 ° C. A solution of 15 g (0.082 mol) of 3-chloro-2-methyl-6-ρropylaniline and 14.2 g (0.123 mol) of triethylamine in 25 ml of dichloromethane is then added dropwise and the mixture is stirred at 20 ° C. for a further 15 hours. Dilute hydrochloric acid is added to the reaction mixture, the organic phase is separated off and the aqueous phase is extracted once with dichloromethane. The combined organic phases are washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated in a water jet vacuum. The residue is stirred with ethanol and the solid formed is filtered off with suction. The crude product is stirred again with a mixture of petroleum ether and diethyl ether, suction filtered again, washed three times with petroleum ether and dried on clay.

20.1 g (55% of theory) of N - {[(3-chloro-2-methyl-6-propylphenyl) amino] sulfonyl} -N '- (4,6-dimethoxypyrimidin-2-yl) are obtained. urea, melting point 162 ° C. Example 6

1.4 g (0.01 mol) of 2-amino-4,6-dimethyl-pyrimidine are added to a solution of 1.42 g (0.01 mol) of chlorosulfonyl isocyanate in 100 ml of dichloromethane at about 0 ° C., and 30 Minutes stirred at 0 to 20 ° C. A solution of 1.9 g (0.01 mol) of 3-chloro-2-methyl-6-propylaniline and 1.5 g (0.015 mol) of triethylamine in 10 ml of dichloromethane is then added dropwise and the mixture is stirred for a further 36 hours at 20 ° C. Dilute hydrochloric acid is added to the reaction mixture, the organic phase is separated off and the aqueous phase is extracted once with dichloromethane. The combined organic phases are washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated in a water jet vacuum. The residue is stirred with ethanol, the solid is filtered off with suction, washed first twice with a little ethanol, then twice with diethyl ether and dried.

1.5 g (76.5% of theory) of N - {[(3-chloro-2-methyl-6-propylphenyl) amino] sulfonyl} -N ^, - (4,6-dimethylpyrimidine-2- yl) urea with a melting point of 110 ° C.

Preparation of the starting material for Examples 5 and 6

A solution of 50 g (0.253 mol) of l- (2-amino-4-chloro-3-methylphenyl) propan-l-one and 63.3 g (1.27 mol) of hydrazine hydrate in 150 ml of dimethyl sulfoxide is on for 15 hours Heated to 110 ° C. 56.7 g (1.012 mol) of potassium hydroxide are then added and the mixture is heated under reflux for a further 15 hours. The reaction mixture is stirred with 5% sodium dihydrogenphosphate solution and extracted three times with ethyl acetate. The combined organic phases are washed twice with saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated in a water jet vacuum. The residue is chromatographed on silica gel using n-hexane / ethyl acetate (30: 1).

41.6 g (89.7% of theory) of 3-chloro-2-methyl-6-propylaniline are obtained

! H NMR (D ₆ -DMSO): δ = 2.2 (s, 3H) ppm

S

Analogously to Examples (1) to (6) and in accordance with the general description of the production processes according to the invention, the compounds of the formula (I) according to the invention listed in Table 1 below are also obtained:

1.6

^

* Decomposition oo

Examples of use

Example A

Podosphaera test (apple) / protective

Solvent: 47 parts by weight of acetone

Emulsifier: 3 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight is mixed

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 sprayed with the active compound preparation in the stated application rate. After the

Plants are inoculated with an aqueous spore suspension of the pod mildew pathogen Podosphaera leucotricha. The plants are then placed in the greenhouse at about 23 ° C. and a relative humidity of about 70%.

Evaluation is carried out 10 days after the inoculation. 0% means a

Efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.

In this test, e.g. the compounds of preparation examples 1, 2, 4, 5, 8, 13, 15 and 17 with an exemplary active compound application rate of 100 g / ha

Efficiency of 100% compared to the untreated control. Example B

Sphaerotheca test (cucumber) / protective

Solvent: 47 parts by weight of acetone

Emulsifier: 3 parts by weight of alkylaryl polyglycol ether

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

To test for protective activity, young plants are sprayed with the active compound preparation in the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Sphaerotheca fuliginea. The plants are then placed in the greenhouse at about 23 ° C. and a relative atmospheric humidity of about 70%.

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

In this test, for example, the compounds of Preparation Examples 1, 2, 4, 5, 8, 13, 15 and 17 show an efficiency of up to 100% compared to the untreated control at an exemplary active ingredient application rate of 100 g / ha.

Example C

Venturia test (apple) / protective

Solvent: 47 parts by weight of acetone

Emulsifier: 3 parts by weight of alkylaryl polyglycol ether

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

To test for protective activity, young plants are sprayed with the active compound preparation in the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous conidia suspension of the 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 placed in the greenhouse at approx. 21 ° C. and a relative humidity of approx. 90%.

Evaluation is carried out 12 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.

In this test, for example, the compounds of preparation examples 13 and 15, with an exemplary active compound application rate of 100 g / ha, show an efficiency of 100% compared to the untreated control. Example D

Phaedon larval test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

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

Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with horseradish leaf beetle larvae (Phaedon cochleariae) while the leaves are still moist.

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

In this test, for example, the compound of preparation example 16 shows a kill of 100% after 3 days at an exemplary active ingredient concentration of 0.1%.

Example E

Hylemyia test

Solvent: 100 parts by weight of acetone

1900 parts by weight of methanol

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

Concentrations.

A specified amount of active compound preparation of the desired concentrations is pipetted onto a standardized amount of artificial feeder. After the methanol has evaporated, about 20 eggs of the onion fly (Hylemyia antiqua) are placed on the feed.

After the desired time, the death of the eggs or larvae is determined in%. 100% means that all animals have been killed; 0% means that no animals have been killed.

In this test, for example, compound (13) of the preparation examples shows a 100% degree of destruction at an active ingredient concentration of 0.05%.

Example F

The compounds 1, 13 and 15 are each incorporated in different concentrations in liquid agar culture media. After the nutrient medium has solidified, the test plates are inoculated with a cell suspension of Pseudomonas aeruginosa and with spores of Chaetonium globosum and penicillium brevicaule. The minimum inhibitory concentration is determined after an incubation period of 3 (bacteria) or 14 days (fungi). The compounds according to the invention show a pronounced antibacterial and anti-fertilizing activity (Table F).

Table F

Minimum inhibitory concentration (mg / L)

Claims

5SPate claims

1. Compounds of the general formula (I)

in which

Rl for optionally substituted alkyl or a group

stands in what

R ^ represents hydrogen or optionally substituted alkyl, alkoxy, dialkylamino, cycloalkyl, cycloalkenyl, phenyl or heterocyclyl,

R9 and RIO each stand for alkyl or together for alkanediyl,

Rl represents optionally substituted alkyl,

R ^, R ³ and R ^ are the same or different and each represents hydrogen, halogen, cyano, nitro, each optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkenyl, alkenyloxy, cycloalkyl or cycloalkoxy, but one of the radicals R ^, ³ or R ^ is different from hydrogen, R5 represents halogen, cyano, nitro, in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkenyl, alkenyloxy, cycloalkyl or cycloalkoxy,

R ^Ö and R ^ are the same or different and each represents halogen or represents alkyl, alkenyl, alkynyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, cycloalkyl or heterocyclyloxy, each optionally substituted by halogen or alkoxy, and

G for nitrogen or

stands in what

Rl2 represents hydrogen, halogen, cyano or alkyl optionally substituted by halogen or alkoxy,

and their salts found.

2. Compounds of formula (I) according to claim 1, in which

Rl for optionally substituted by halogen, thioalkyl having 1 to 6 carbon atoms or sulfonylalkyl having 1 to 6 carbon atoms

Alkyl with 1 to 6 carbon atoms or a grouping

stands in what

R represents hydrogen, optionally by fluorine, chlorine, bromine, alkoxy having 1 to 3 carbon atoms, alkylthio having 1 to 3

Carbon atoms, alkylsulfinyl with 1 to 3 carbon atoms or alkylsulfonyl with 1 to 3 carbon atoms substituted alkyl, alkoxy, or dialkylamino each with 1 to 6 carbon atoms St

Substance atoms in the individual alkyl parts, each for cycloalkyl, cycloalkenyl, cycloalkenyl, cycloalkyl-alkyl or cycloalkenyl-alkyl, each optionally substituted by fluorine, chlorine, bromine and / or alkyl having 1 to 3 carbon atoms, each having 3 to 6 carbon atoms in the cycloalkyl or cycloalkenyl groups and 1 to 3 carbon atoms in the respective alkyl parts, for phenyl or phenyl-alkyl with 1 to 3 each optionally substituted by fluorine, chlorine, bromine, alkyl with 1 to 3 carbon atoms or haloalkyl with 1 to 3 carbon atoms and 1 to 5 halogen atoms Carbon atoms in the alkyl part or for heterocyclyl or heterocyclyl-alkyl with 3 to 7 ring members and with 1 to 3 carbon atoms in each case optionally substituted by fluorine, chlorine, bromine, alkyl with 1 to 3 carbon atoms or haloalkyl with 1 to 3 carbon atoms and 1 to 5 halogen atoms Alkyl part stands,

R9 and RIO each represent alkyl having 1 to 3 carbon atoms or together represent alkanediyl having 1 to 3 carbon atoms,

RU for optionally substituted by halogen or phenyl

Alkyl having 1 to 4 carbon atoms,

R2, R ³ and R ^ are the same or different and each represents hydrogen, halogen, cyano, nitro, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms,

Alkylsulfinyl with 1 to 4 carbon atoms, alkylsulfonyl with 1 to 4 carbon atoms, alkenyl with 2 to 4 carbon atoms, alkenyloxy with 2 to 4 carbon atoms, haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each with 1 to 6 carbon atoms and 1 to 5 identical or different Halogen atoms, cycloalkyl with 3 to 6 carbon atoms or cycloalkoxy having 3 to 6 carbon atoms, but one of the radicals R ^, R ³ or R ^ is different from hydrogen,

R for halogen, cyano, nitro, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, alkylsulfinyl with 1 to 4 carbon atoms, alkylsulfonyl with 1 to 4 carbon atoms, alkenyl with 2 to 4 Carbon atoms, alkenyloxy having 2 to 4 carbon atoms, haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 5 identical or different halogen atoms, cycloalkyl having 3 to 6 carbon atoms or cycloalkoxy having 3 to 6 carbon atoms,

R6 and R ^ are the same or different and each represents halogen or alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino or dialkylamino each having 1 to 4 carbon atoms in the individual alkyl parts, each substituted by halogen or alkoxy having 1 to 4 carbon atoms, Alkenyl or alkynyl each having 2 to 4 carbon atoms, cycloalkyl having 3 to 6 carbon atoms or heterocyclyloxy having 3 to 6 ring members and 1 to 3

Heteroatoms stand and

G represents nitrogen or where

R 2 represents hydrogen, halogen, cyano or alkyl having 1 to 4 carbon atoms which is optionally substituted by halogen or alkoxy having 1 to 4 carbon atoms.

3. Compounds of formula (I) in which 53

Rl for methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, n-, i- or s-pentyl or a group, each optionally substituted by fluorine, chlorine, thiomethyl and / or sulfonylmethyl

stands in what

R for hydrogen, for methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, n-, i- or s-pentyl, methoxy, ethoxy, n, each optionally substituted by fluorine and / or chlorine - or i-propoxy, dimethylamino, diethylamino, for methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, methylthio-methyl, methylthioethyl, ethylthiomethyl, ethylthioethyl, methylsulfinylmethyl, ethylsulfinylmethyl, methylsulfonylmethyl, ethylsulfonylmethyl, or optionally for methoxy, methoxy, for methoxy, for methoxy, for methoxy Chlorine and / or methyl substituted cyclopropyl, cyclopropylmethyl, cyclobutyl, cyclobutylmethyl, cyclopentyl, cyclopentylmethyl, cyclopentenylmethyl, cyclohexyl, cyclohexenylmethyl, phenyl, benzyl, phenylethyl, furyl, furylmethyl, thienyl, thienylmethyl, tetrahethylmethyl, tetrahydrofuran,

R9 and RO each represent methyl, ethyl, n- or i-propyl or together for methylene, 1,1-ethanediyl, 1,2-ethanediyl 1,1-, 1,2-, 1,3- or 2,2- Stand propanediyl,

Rl 1 for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or

Benzyl stands,

R2, R ³ and R ^ are the same or different and each represents hydrogen, fluorine, chlorine, bromine, cyano, nitro, fluorine, chlorine, bromine, cyano, nitro, CO

Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, chloromethoxy difluoro-, trifluoroethoxy, difluoromethylthio, Difluorchlormethyl- thio, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl, vinyl, allyl, allyloxy or cyclopropyl, wherein, however, one of the radicals R2, ^R3 or R4 is different from hydrogen,

R5 for fluorine, chlorine, bromine, cyano, nitro, 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, n- or i-propylthio, methylsulfinyl, Ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromyloxyethyl, trifluoromyloxyethyl, trifluoromyloxyethyl, trifluoromethylloxyethyl, trifluoromyloxylyl, trifluoromethyloxylyl, trifluoromethylloxy, allyl, trifluoromethyl

R6 and R ^ are the same or different and each represents chlorine, methyl, ethyl, vinyl, allyl, 2-methylethen-l-yl, ethynyl, 2-methylethyn-l-yl, propargyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy , Trifluoroethoxy, methylthio, ethylthio, methylamino, ethylamino, dimethylamino, cyclopropyl or oxethan-1-yloxy and

G represents nitrogen or where

Rl2 represents hydrogen, fluorine, chlorine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, trifluoroethyl, methoxymethyl or ethoxymethyl. CΛ

Pesticides, characterized in that they contain at least one compound of the formula (I) according to Claim 1

Process for combating pests, characterized in that compounds of the formula (I) according to Claim 1 are allowed to act on pests and / or their habitat

Use according to compounds of formula (I) and agents according to claims 1 to 4 for controlling pests

Process for the preparation of pesticides, characterized in that compounds of the formula (I) according to Claims 1 to 3 are mixed with extenders and / or surface-active agents

A process for the preparation of compounds of formula (II) according to claim

1, characterized in that aminotriazines or pyrimidines of the general formula (II),

in which

R6, R ^ and G have the meanings given in claim 1,

with chlorosulfonyl isocyanate, optionally in the presence of a diluent, and the chlorosulfonylureas of the general formula (III) formed in this process,

in which

R6, R ^ and G have the meanings given in claim 1,

with anilines of the general formula (IV),

in which

Rl, R ^, R ³ , R4 and R ^ have the meanings given in claim 1,

optionally in the presence of an acid acceptor and optionally in

In the presence of a diluent and, if appropriate, converting the compounds of the formula (I) thus obtained into salts by customary methods.