DE19707580A1 - Phenylaminosulfonylurea derivatives - 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

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

The new phenylaminosulfonylurea derivatives of the general formula (I)

in which
R ^{1 represents} optionally substituted alkyl or a group

stands in what
R ^{8 represents} hydrogen or optionally substituted alkyl, alkoxy, dialkylamino, cycloalkyl, cycloalkenyl, phenyl or heterocyclyl,
R ⁹ and R ¹⁰ each represent alkyl or together represent alkanediyl,
R ^{11 represents} optionally substituted alkyl,
R ² , R ³ and R ^{4 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 them Radicals R ² , R ³ or R ^{4 are} different from hydrogen,
R ^{5 represents} halogen, cyano, nitro, in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkenyl, alkenyloxy, cycloalkyl or cycloalkoxy,
R ⁶ and R ^{7 are the} same or different and each represents halogen or represents alkyl, alkenyl, alkynyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, cycloalkyl or heterocyclyloxy, optionally substituted by halogen or alkoxy
G for nitrogen or

stands in what
R ^{12 represents} hydrogen, halogen, cyano or alkyl optionally substituted by halogen or alkoxy,
and their salts found.

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

Halogen generally represents fluorine, chlorine, bromine or iodine, preferably Fluorine, chlorine or bromine, especially for fluorine or chlorine.

Aryl stands for aromatic, mono- or polycyclic hydrocarbon rings, such as. 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 necessary, the ring-shaped connections form with others carbocyclic or heterocyclic, fused or bridged rings together a polycyclic ring system. Mono- or bicyclic are preferred Ring systems, especially mono- or bicyclic, aromatic ring systems.

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

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

Furthermore, it was found that the new phenylaminosulfonylurea derivatives of the general formula (I) are obtained if aminotriazines or -pyrimidines of the general formula (II),

in which
R ⁶ , R ⁷ and G have the meanings given above,
with chlorosulfonyl isocyanate, optionally in the presence of a diluent, and the chlorosulfonylureas of the general formula (III) formed in this process

in which
R ⁶ , R ⁷ and G have the meanings given above,
with anilines of the general formula (IV),

in which
R ¹ , R ² , R ³ , R ⁴ and R ^{5 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 very good microbicidal Have properties and in both crop protection and material protection can be used.  

The invention preferably relates to compounds of the formula (I) in which
R ¹ 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 ^{8 represents} hydrogen, alkyl, alkoxy or dialkylamino 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 each with 1 to 6 carbon atoms in the individual alkyl, for each optionally substituted by fluorine, chlorine, bromine and / or alkyl with 1 to 3 carbon atoms substituted cycloalkyl, cyclo alkenyl, cycloalkyl-alkyl or cycloalkenyl-alkyl each with 3 to 6 carbon atoms in the cycloalkyl or cycloalkenyl groups and 1 to 3 carbon atoms in the respective alkyl moieties, for phenyl or phenyl 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 with 1 to 3 carbon atoms in the alkyl part or for each optionally by fluorine, chlorine, bromine, alkyl 1 to 3 carbon atoms or halo genalkyl with 1 to 3 carbon atoms and 1 to 5 halogen atoms substituted heterocyclyl or heterocyclyl-alkyl with 3 to 7 rings and 1 to 3 carbon atoms in the alkyl part,
R ⁹ and R ¹⁰ each represent alkyl having 1 to 3 carbon atoms or together represent alkanediyl having 1 to 3 carbon atoms,
R ^{11 represents} alkyl with 1 to 4 carbon atoms optionally substituted by halogen or phenyl,
R ² , R ³ and R ^{4 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 having 1 to 4 carbon atoms , Alkylsulfonyl having 1 to 4 carbon atoms, alkenyl having 2 to 4 carbon atoms, alkenyloxy having 2 to 4 carbon atoms, haloalkyl, haloalkoxy, haloalkylthio, haloalkyl sulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 5 identical or different halogen atoms, cycloalkyl 3 to 6 carbon atoms or cycloalkoxy having 3 to 6 carbon atoms, but one of the radicals R ² , R ³ or R ^{4 is} different from hydrogen,
R ⁵ 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, alkyl sulfinyl 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 ,
R ⁶ and R ^{7 are the} same or different and are each halogen or for ge optionally substituted by halogen or alkoxy having 1 to 4 carbon atoms substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino or dialkylamino each having 1 to 4 carbon atoms in the individual 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 for nitrogen or

stands in what
R ^{12 is} hydrogen; Halogen, cyano or alkyl with 1 to 4 carbon atoms optionally substituted by halogen or alkoxy having 1 to 4 carbon atoms.

The invention further preferably relates to 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, C ₅ or C ₆ cycloalkyl ammonium and di (C ₁ -C ₂ alkyl) benzyl ammonium salts of compounds of the formula (I), in which R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and G have the meanings preferably given above.

The invention relates in particular to compounds of the formula (I) in which
R ¹ 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 sulfonyl methyl grouping

stands in what
R ⁸ 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, eth oxyethyl, methylthiomethyl, methylthioethyl, ethylthiomethyl, ethyl thioethyl, methylsulfinylmethyl, ethylsulfinylmethyl, methylsulfonylmethyl, ethylsulfonylmethyl or fluorine, methoxyethoxyfalls, in each case by methoxyethoxy and / or methyl substituted cyclopro pyl, cyclopropylmethyl, cyclobutyl, cyclobutylmethyl, cyclopentyl, cyclopentylmethyl, cyclopentenylmethyl, cyclohexyl, cyclohexenyl methyl, phenyl, benzyl, phenylethyl, furyl, furylmethyl, thienyl, thienylmethyl, tetrahydrofuryl or tetrahydrofuryl or
R ⁹ and R ¹⁰ 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, Stand 2-pandiyl,
R ^{11 represents} methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or benzyl,
R ² , R ³ and R ^{4 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-, 5- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methyl thio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethyl, trifluorethoxy, diifluoromifluoromethylfluoromethylfluoromethylfluoromifluoromethylfluoromethylfluoromethylfluoromethylfluoromethylfluoromethylfluoromethylfluoromethylfluoromethylfluoromethyl, Vinyl, allyl, allyloxy or cyclopropyl, but one of the radicals R ² , R ³ or R ^{4 is} different from hydrogen,
R ⁵ 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, ethyl- thio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoromethylchlorofluoromethyl, fluifluoromethyl Vinyl, allyl, allyloxy or cyclopropyl,
R ⁶ and R ^{7 are the} same or different and each represents chlorine, methyl, ethyl, vinyl, allyl, 2-methylethen-1-yl, ethinyl, 2-methylethin-1-yl, propargyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy , Trifluoroethoxy, methylthio, ethyl thio, methylamino, ethylamino, dimethylamino, cyclopropyl or oxethan-1-yloxy and
G for nitrogen or

stands in what
R ^{12 is} hydrogen; Fluorine, chlorine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, trifluoroethyl, methoxymethyl or ethoxymethyl.

The general or priority ranges listed above nitions apply both to the end products of formula (I) and accordingly to the starting or intermediate products required for the production. The in the respective combinations or preferred combinations of residues in detail radical definitions given for these radicals are independent of the respective specified combination, arbitrarily also by residual definitions of other preferred terms rich replaced.

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 by 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 the formula (I) according to the invention. In this formula (II), R ⁶ , R ⁷ and G 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 as particularly preferred for R ⁶ , R ⁷ and G were given.

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

The to carry out the inventive method for producing the inventions Compounds of formula (I) according to the invention also require chlorosulfonyl isocyanate is a well 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 ¹ , R ² , R ³ , R ⁴ and R ⁵ preferably or in particular have those meanings which are already preferred in connection with the description of the compounds of the formula (I) according to the invention or as in particular were preferably given for R ¹ , R ² , R ³ , R ⁴ and R ⁵ .

The anilines of the formula (IV) are known and / or can be prepared per se Processes are prepared (see, for example, US-P 5405998 and DE-A 44 14 476).

The inventive method for producing the new compounds of For mel (I) is preferably carried out using diluents. Practically all inert organic solutions come as diluents medium in question. These preferably include aliphatic and aromatic ones if 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 iso butyl ketone, esters such as methyl acetate and ethyl ester, nitriles such as. B. Aceto nitrile and propionitrile, amides such as e.g. B. dimethylformamide, dimethylacetamide and N- Methyl pyrrolidone and dimethyl sulfoxide, tetramethylene sulfone and hexamethyl phosphoric triamide.

All of the customary acid acceptors can be used in the process according to the invention acid binders that can be used for such reactions are used. Before preferably come alkali metal hydroxides such. B. sodium and potassium hydroxide, Alkaline earth metal hydroxides such. As calcium hydroxide, alkali carbonates and alcoholates such as Sodium and potassium carbonate such as sodium and potassium tert-butoxide, further 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 in one in the process according to the invention larger range can be varied. Generally one works at 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 leads. However, it is also possible to work under increased or reduced pressure ten.

To carry out the method according to the invention, the respectively required ones are used Starting materials are generally used in approximately equimolar amounts. It is however, it is also possible to use one of the two components used in one size use excess. The reactions are generally in a ge suitable diluent carried out in the presence of an acid acceptor, and the reaction mixture is at the required temperature for several hours door stirred. The process according to the invention is carried out in each case according to usual methods (cf. the manufacturing examples).

From the compounds of the general formula (I) according to the invention, if necessary salts are produced. Such salts are obtained in a simple manner usual salt formation methods, for example by dissolving or dispersing one Compound of formula (I) in a suitable solvent, such as. B. methylene chloride, acetone, tert-butyl methyl ether or toluene, and addition of a suitable one Base. The salts can then - if necessary after prolonged stirring - by Ein narrow or suction isolated.

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

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, Use Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.  

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

Xanthomonas species, such as, for example, Xanthomonas campestris pv. Oryzae;
Pseudomonas species, such as, for example, Pseudomonas syringae pv. Lachrymans;
Erwinia species, such as, for example, Erwinia amylovora;
Pythium species, such as, for example, Pythyn 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;
Botiytis 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 Combating diseases in wine, fruit and vegetable growing, such as against Venturia, Sphaerotheca and Podosphaera species. With good success cereal diseases, such as Erysiphe species, are also combated.

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

With good plant tolerance and favorable warm-blood toxicity, the active substances are suitable for controlling animal pests, in particular insects, arachnids and nematodes, which occur in agriculture, in forests, in the protection of stored products and materials, and in the hygiene sector. They can preferably be used as pesticides. They are effective against normally sensitive and resistant species and against all or individual stages of development. 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 spec.
From the order of the Symphyla z. B. Scutigerella immaculata.
From the order of the Thysanura z. B. Lepisma saccharina.
From the order of the Collembola z. B. Onychiurus armatus.
From the order of Orthoptera z. B. Blatta orientalls, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialls, Schistocerca gregaria.
From the order of the Dermaptera z. B. Auricular Forficula.
From the order of the Isoptera z. B. Reticulitermes spp.
From the order of the Ahoplura z. B. Pediculus humanus corporis, Haematopinus spp., Linognathus spp.
From the order of the Mallophaga z. B. Trichodectes spp., Damalinea spp.
From the order of the Thysanoptera z. B. Hercinothrips femoralis, Thrips tabaci.
From the order of Heteroptera z. B. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.
From the order of Homoptera z. B. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus sppe, Phrosiphumumonpp., Macrosiphumum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Salssetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp.
From the order of the Lepidoptera z. B. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurbriisppina, Fpp , Heliothis spp., Spodoptera exigua, Mamestra brassicae, Panolis flammea, Spodoptera litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Taniaiaolaonellellella, Galleriaineellellellella Hofmannophila pseudospretella, Cacoecia po dana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana.
From the order of the Coleoptera z. B. Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephppis, Orphusus spp. , Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Giptusibbium psol. Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica.
From the order of the Hymenoptera z. B. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
From the order of the Diptera z. B. Aedes spp., Ahopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fanhia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomox ., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa.
From the order of the Siphonaptera z. B. Xenopsylla cheopis, Ceratophyllus spp.
From the order of the Arachhida z. B. Scorpio maurus, Latrodectus mactans.
From the order of Acarina z. B. Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyliocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoropop spp.,. Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp.

The plant parasitic nematodes include z. B. Pratylenchus spp., Radopholus simllis, 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 particularly noteworthy by their action against plant-damaging insects, such as against Larvae of the horseradish leaf beetle (Phaedon cochleariae) and the onion fly (Hylemyia antiqua), from.

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 as ULV Cold and warm fog formulations.

These formulations are prepared in a known manner, e.g. B. by mixing the Active ingredients with extenders, i.e. liquid solvents, under pressure liquid gases and / or solid carriers, optionally using surface-active agents, ie emulsifiers and / or dispersants and / or foaming agents. In the case of the use of water as an extender e.g. B. organic solvents can also be used as auxiliary solvents. As a liquid Solvents are essentially possible: 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. B. petroleum fractions, alcohols, such as butanol or glycol as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfate oxide, as well as water. With liquefied gaseous extenders or carriers such liquids are meant to be soft at normal temperature and under normal pressure are gaseous, e.g. B. aerosol propellants, such as halogenated hydrocarbons and butane, Propane, nitrogen and carbon dioxide. As solid carriers come into question: B. natural  Liche rock powder, such as kaolins, clays, talc, chalk, quartz, attapulgite, Montmo rillonite or diatomaceous earth and synthetic stone powder, such as finely divided pebbles acid, aluminum oxide and silicates. The following are suitable as solid carriers for granules: e.g. B. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, Dolomite and synthetic granules from inorganic and organic flours as well Granules from organic material such as sawdust, coconut shells, corn cobs and Tobacco stem. Suitable emulsifying and / or foam-generating agents are: B. nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxy ethylene fatty alcohol ether, e.g. B. alkylaryl polyglycol ether, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates. Possible dispersants are: B. Lignin Leaches of sulfite and methyl cellulose.

Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex polymers can be used, such as Gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as Cephalins and lecithins, and synthetic phospholipids. Other additives can 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, as such or in their formulations, too 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, ampropyffos 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, diclofluanid, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, diniconazole-M, dinocap, diphenylamine, dipyrithione, ditalimfos, dithorphoxinodonine, dithorphononine
Ediphenphos, Epoxiconazole, Etaconazole, Ethirimol, Etridiazole,
Famoxadone, Fenapanil, fenarimol, fenbuconazole, fenfuram, Fenitropan, fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, Fentinhydroxyd, ferbam, ferimzone, fluazinam, flumetover, fluoromide, fluquinconazole, flurprimidol, 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, Ipconszol, Iprobefos (IBP), Iprodione, Iminamycin, Isoprothiolan, Isovaledione,
Kasugamycin, Kresoxim-methyl, copper preparations, such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxy-copper and Bordeaux mixture,
Mancopper, Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Methfroxam, Metiram, Metomeclam, Metsulfovax, Mildiomycin, Myclobutanil, Myclozolin,
Nickel dimethyldithiocarbamate, nitrothal isopropyl, Nuarimol,
Ofurace, oxadixyl, oxamocarb, oxolinicacid, oxycarboxiin, oxyfenthiin,
Paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen, pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz, procymidone, propamocarb, propanosine sodium, propiconazole, propineb, pyrazophos, pyrifenox, pyrietililon, pyrazophyne,
Quinconazole, quintozen (PCNB),
Sulfur and sulfur preparations,
Tebuconazole, tecloftalam, tecnazene, Tetcyclacis, tetraconazole, thiabendazole, Thicyofen, Thifluzamide, thiophanate-methyl, thiram, Tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, Triazbutil, triazoxide, Trichlamid, tricyclazole, tridemorph, triflumizole, triforine, triticonazole,
Uniconazole,
Validamycin A, vinclozolin, viniconazole,
Zarilamid, Zineb, Ziram as well
Dagger G,
OK-8705,
OK-8801,
α- (1,1-dimethylethyl) -β- (2-phenoxyethyl) -1H-1,2,4-triazole-1-ethanol,
α- (2,4-dichlorophenyl) -β-fluoro-b-propyl-1H-1,2,4-triazole-1-ethanol,
α- (2,4-dichlorophenyl) -β-methoxy-a-methyl-1H-1,2,4-triazole-1-ethanol,
α- (5-methyl-1,3-dioxan-5-yl) -β - [[4- (trifluoromethyl) phenyl] methylene] -1H-1,2,4-triazol-1-ethanol,
(5RS, 6RS) -6-hydroxy-2,2,7,7-tetramethyl-5- (1H-1,2,4-triazol-1-yl) -3-octanone,
(E) -a- (methoxyimno) -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 - [(diiodinethyl) 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, oc thilinone, 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-chlorophenyl) -1- (ethoxymethyl) -5- (trifluoromethyl) - 1H-pyrrole-3-carbonitrile, bendiocarb, benfuracarb, bensultap, betacyfluthrin, bifenthrin, BPMC, Brofenprox, bromophos A, Bufencarb, Buprofezin, Butocarboxim, Butylpyridaben,
Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, Chloethocarb, Chlorethoxyfos, Chlorfenapyr, Chlorfenvinphos, Chlorfluazuron, Chlormephos, N - [(6-Chloro-3-pyridinyl) -methyl] -N'-cyano-N-methyl-ethanimidamide , Chlorpyrifos, Chlor pyrifos M, Cis-Resmethrin, Clocythrin, Clofentezin, Cyanophos, Cydoprothrin, Cylluthrin, Cyhalothrin, Cyhexatin, Cypermethrin, 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,
Fenmiphos, Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fen oxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil, Fluazinam, Fluazuron, Flucycloxuron, Flucythrinat, Flufenproophion, Fufionxophonofonofon, fufonx, fufon, fufon, fufion, fufon, fufon, fufon, fufon, fufon, fufon, fufon, fufon, fufon, fufon, fufon, fufon, fufon, fufon, fufon, fufon, fufon, fuf, fufon ,
HCH, heptenophos, hexaflumuron, hexythiazox,
Imidadoprid, Iprobefos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivermectin,
Lambda cyhalothrin, lufenuron,
Malathion, Mecarbam, Mevinphos, Mesulfenphos, Metaldehyde, Methacrifos, Methamido phos, Methidathion, Methiocarb, Methomyl, Metolcarb, Milbemectin, Monocrotophos, Moxidectin,
Naled, NC 184, Nitenpyram,
Omethoate, Oxamyl, Oxydemethon M, Oxydeprofos,
Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phos phamidon, Phoxim, Pirimicarb, Pirimiphos M, Pirmiphos A, Profenophos, Promecarb, Propaphos, Propoxur, Prothiophos, Prothoat, Pymetroion, Pyridaphrinophin, Pyridaphrinophin , Pyridaben, pyrimidifen, pyriproxifen,
Quinalphos,
Salithion, Sebufos, Silafluofen, Sulfotep, Sulprofos,
Tebufenozide, Tebufenpyrad, Tebupirimiphos, Teflubenzuron, Tefluthrin, Temephos, Ter bam, Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thiofanox, Thiomethon, Thionain, Thuringiensin, Tralomethoniazon, Triaromethoniazon, Triaratheniazonium, Triaratheniazon
Vamidothione, XMC, xylylcarb, zetamethrin.

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

The active compounds according to the invention can also be used in their commercially available form formulations and in the use forms prepared from these formulations in Mix with synergists. Synergists are connections through which the Effect of the active ingredients is increased 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 active compounds according to the invention act not only against plant, hygiene and Pests, but also against the veterinary sector animal parasites (ectoparasites) such as tortoise ticks, leather ticks, mite 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 z. B. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.

From the order of the Mallophagida and the submissions Ambiycerina as well Ischnocerina e.g. B. 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 e.g. B. Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., 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 z. B. Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp.

From the order of the Heteropterida z. B. Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp.

From the order of the Blattarida z. B. Blatta orientalis, Peripianeta americana, Blattela germanica, Supella spp.  

From the subclass of Acaria (Acarida) and the orders of the Meta and Mesostigmata e.g. B. Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp.

From the order of the Actinedida (Prostigmata) and Acaridida (Astigmata) z. B. 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 combating of arthropods, the farm animals, such as. B. cattle, sheep, goats, Horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese, Bees, other pets such as B. dogs, cats, house birds, aquarium fish as well as so-called experimental animals, such as. B. hamsters, guinea pigs, rats and Infest mice. By fighting these arthropods, deaths and Reductions in performance (for meat, milk, wool, skins, eggs, honey, etc.) can be reduced so that by using the active compounds according to the invention more economical and easier animal husbandry is possible.

The active compounds according to the invention are used in the veterinary sector in in a known manner by enteral administration in the form of, for example, tablets, Capsules, watering, drenching, granules, pastes, boluses, the feed-through process, suppositories, by parenteral administration, such as by injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants, through nasal Application, by dermal application in the form of, for example, diving or Bathing (dipping), spraying (spray), pouring (pour-on and spot-on), des Washing, powdering and with the help of shaped articles containing active ingredients, such as  Collars, ear tags, tail tags, limb straps, halters, Mar 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 ingredients in an amount of 1 to 80 wt .-%, 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 the technical have a high effect against insects and microorganisms Destroy 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 carpini, Lyctus brunneus, Lyctus afticanus, Lyctus planicollis, Lyctus linearesceses, Lyctus pubescuses, Lyctus pubescuses, Lyctus pubis aescus, Lyctus pubescuses, Lyctus pubescuses, Lyctus pubescuses, 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 lucifugus, Mastotermes darwinien sis, Zootermopsis nevadensis, Coptotermes formosanus. Bristle tails, such as Lepisma saccarina.

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 tigfinus,
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 include non-living ones Understand materials, such as preferably plastics, adhesives, glues, papers and cardboard, leather, wood and wood processing products and paints.

The one to be protected against insect attack is very particularly preferably Material around wood and wood processing products.

Among wood and wood processing products, which by the invention Agents or mixtures containing them can be protected is exemplary understand: timber, wooden beams, railway sleepers, bridge parts, jetties,  Wooden vehicles, boxes, pallets, containers, telephone poles, wooden panels, wood windows and doors, plywood, particle board, carpentry or wood products, the generally used in house construction or in carpentry.

The active ingredients can be used as such, in the form of concentrates or in a conventional manner 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, e.g. B. by mixing the active ingredients with at least one solution or Diluents, emulsifiers, dispersants and / or binders or fixatives, Water repellants, optionally desiccants and UV stabilizers and, if appropriate 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 agents or concentrates used depends on the type and type come from insects or microorganisms and depend on the medium. The optimum amount can be used in each case through test series be determined. In general, however, it is sufficient from 0.0001 to 20% by weight preferably 0.001 to 10 wt .-%, of the active ingredient, based on that to be protected Material.

An organic chemical solution serves as the solvent and / or diluent medium or solvent mixture and / or an oily or oily low volatile organic chemical solvent or solvent mixture and / or a polar 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 ones Solvents with an evaporation number above 35 and a flash point above 30 ° C, preferably above 45 ° C, used. As such volatile, Water-insoluble, oily and oily solvents become corresponding mineral oils or their aromatic fractions or mineral oil-containing solvent mixtures preferably white spirit, petroleum and / or alkylbenzene used.

Mineral oils with a boiling range of 170 to 220 ° C are advantageous, test petrol with a boiling range of 170 to 220 ° C, spindle oil with a boiling range from 250 to 350 ° C, petroleum or aromatics with a boiling range from 160 to 280 ° C, Turpentine oil and the like.

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

The organic non-volatile oily or oily solvents with a Evaporation rate above 35 and a flash point above 30 ° C, preferably above half 45 ° C, can be partly due to slightly or medium volatile organic chemical Solvents are replaced, with the proviso that the solvent mixture also an evaporation number above 35 and a flash point above 30 ° C, preferably above 45 ° C, and that the insecticide-fungicide mixture in this solvent mixture is soluble or emulsifiable.

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 come aliphatic containing hydroxyl and / or ester and / or ether groups  organic chemical solvents such as glycol ether, ester or the like. to use.

As organic-chemical binders in the context of the present invention the known water-dilutable and / or in the organic chemical solvents soluble or dispersible or emulsifiable synthetic resins and / or binding drying oils, in particular binders consisting of or containing an acrylic resin, a vinyl resin, e.g. B. 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 in the form of an emulsion, dispersion or solution. Bitumen or bitumi can also be used as binders nous substances up to 10 wt .-% can be used. In addition, in itself known dyes, pigments, water repellants, odor correctors and Inhibitors or anticorrosive agents and the like are used.

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

The binder mentioned can be wholly or partly by a fixation medium (mixture) or a plasticizer (mixture) can be replaced. These additions are meant to volatilization of the active ingredients and crystallization or precipitation prevent. They preferably replace 0.01 to 30% of the binder (based on 100% of the binder used).  

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, glycerol ether or higher molecular weight glycol ether, glycerol ester and p-toluenesulfonic acid ester.

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

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

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

The ready-to-use agents can optionally also be other insecticides and / or contain fungicides.

The additional mixing partners are preferably those in WO 94/29 268 Insecticides and fungicides mentioned in question. The ones mentioned in this document Connections are an integral part of this application.

Insecticides such as chloropyriphos, phoxime, silafluofin, alphamethrin, cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25, flufenoxuron, hexaflumuron and triflumuron can be used as very particularly preferred mixing partners.
and fungicides such as epoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole, cyproconazole, metconazole, imazalil, dichlorofluoride, tolylfluanid, 3-iodo-2-propynylbutylcarbamate, N-octyl-isothiazolin-3-one and 4,5-dichloro octylisothiazolin-3-one.

The manufacture and use of the active compounds according to the invention start out the following examples.

Manufacturing examples example 1

To a solution of 6.8 g (0.0479 mol) of chlorosulfonyl isocyanate in 80 ml of dichloro methane is 8.2 g (0.053 mol) of 2-amino-4,6-dimethoxy-pyrimidine at about 0 ° C added and stirred for about an hour at 0 to 20 ° C. Then you drop one Solution of 10 g (0.0479 mol) (2-amino-4-chloro-3-methylphenyl) cyclopropyl methanone and 7.3 g (0.072 mol) of triethylamine in 15 ml of dichloromethane and stirred 15 hours at 20 ° C. The reaction mixture is diluted with hydrochloric acid added, the organic phase separated and the aqueous phase twice with Di extracted chloromethane. The combined organic phases are twice with saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated in a water jet vacuum. The residue is stirred with ethanol, which Aspirated solid, first twice with a little ethanol, then twice with diethyl ether washed and dried.

10.8 g (48% of theory) of N - {[(5-chloro-2-cyclopropylcarbonyl-6-methyl- phenyl) amino] sulfonyl} -N '- (4,6-dimethoxypyrimidin-2-yl) urea from the enamel point 153 ° C.  

Example 2

To a solution of 1042 g (0.01 mol) of chlorosulfonyl isocyanate in 80 ml of dichloro methane becomes 108 g (0.011 mol) of 2-amino-4-chloro-6-methoxy-pyrimidine at approx. 0 ° C added and stirred for about 30 minutes at 0 to 20 ° C. Then you drop one Solution of 2.1 g (0.01 mole) (2-amino-4-chloro-3-methylphenyl) cyclopropyl methanone and 1.5 g (0.015 mol) of triethylamine in 5 ml of dichloromethane and stirred 15 hours at 20 ° C. The reaction mixture is diluted with hydrochloric acid added, the organic phase separated and the aqueous phase once with dichloro extracted methane. The combined organic phases are ge once with water wash, dried over sodium sulfate, filtered and concentrated in a water jet vacuum tight. The residue is stirred with ethanol, the solid is suctioned off with diethyl ether washed and dried.

2.2 g (46.8% of theory) of N - {[(5-chloro-2-cyclopropylcarbonyl-6- methylphenyl) amino] sulfonyl} -N '- (4-chloro-6-methoxypyrimidin-2-yl) urea from Melting point 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. For this a solution of 70.8 g (0.5 mol) of 3-chloro-2-methylaniline in 120 is added dropwise at 0.degree ml 1,2-dichloroethane and stirred for 40 minutes at 20 ° C. Then there is a solution of 52.4 g (0.77 mol) of cyclopropanecarbonitrile in 55 ml of 1,2-dichloroethane drips and stirred for another hour at 20 ° C. Now drop another 113.8 g (0.6 Mol) of titanium tetrachloride and heated under reflux for 8 hours. After cooling If 250 ml of water are carefully added dropwise while cooling with ice, the organic phase is separated and extracted the aqueous phase twice with ethyl acetate. The United 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 1- (2-amino-4-chloro-3-methylphenyl) -4-chlorobutan-1-one are obtained. This will dissolved in a sodium methoxide solution consisting of 7.9 g sodium and 300 ml methanol was freshly prepared, 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 twice with Extracted ethyl acetate. The combined organic phases are over Dried sodium sulfate, filtered and concentrated in a water jet vacuum. The back the stand 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-methyl-phenyl) -cyclopropyl-methanone with a melting point of 65 ° C.  

Example 3

To a solution of 0.62 g (0.00442 mol) of chlorosulfonyl isocyanate in 20 ml of dichloro methane is added at about 0 ° C 0.7 g (0.0045 mol) of 2-amino-4,6-dimethoxy-pyrimidine give and stirred for about 30 minutes at 0 to 20 ° C. Then you drop a Lö solution of 1.0 g (0.0042 mol) of 1- (2-amino-4-chloro-3-methylphenyl) propan-1-one-O- methyl oxime and 0.7 g (0.0663 mol) of triethylamine in 2 ml of dichloromethane and stirred 15 hours at 20 ° C. The reaction mixture is with 5% sodium dihydro Genphosphatlösung added, the organic phase separated and the aqueous phase extracted once with dichloromethane. The combined organic phases are washed twice with saturated sodium chloride solution, over sodium sulfate dries, filtered and concentrated in a water jet vacuum. The arrears with Stirred ethanol, the solid was suctioned off, first twice with a little ethanol, then washed twice with diethyl ether and dried.

1.4 g (66.7% of theory) of N - {[(5-chloro-2- (1-methoximinoprop-1-yl) -6- methylphenyl) amino] sulfonyl} -N '- (4-chloro-6-methoxypyrimidin-2-yl) urea from Melting point 154 ° C.  

Production of the starting material

To a solution of 5 g (0.0253 mol) of 1- (2-amino-4-chloro-3-methylphenyl) propan-1-one in 100 ml of dichloromethane are added dropwise 11 g (0, 101 mol) of trimethylchlorosilane and stir for one hour at 20 ° C. Then a solution of 4.2 g (0.0506 mol) Methoxyamine hydrochloride and 5.1 g (0.0506 mol) triethylamine in 2.5 ml dichloro methane, which was stirred at 20 ° C for 1 hour, and added dropwise at 20 ° C for 2 days touched. Now a solution of 2 g (0.024 mol) of methoxyamine hydro chloride and 2.4 g (0.024 mol) of triethylamine in 10 ml of dichloromethane, which was an hour was stirred at 20 ° C, added dropwise and stirred at 20 ° C for a further 8 days. The 5% sodium dihydrogen phosphate solution is added to the reaction mixture separated organic phase and the aqueous phase once with dichloromethane extracted. 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 are obtained. 1-on-O-methyl-oxime with a melting point of 93 ° C.  

Example 4

To a solution of 1.46 g (0.0104 mol) of chlorosulfonyl isocyanate in 20 ml of dichloro methane becomes 1.7 g (0.011 mol) of 2-amino-4,6-dimethoxy-pyrimidine at approx. 0 ° C added and stirred for 30 minutes at 0 to 20 ° C. Then you drop one 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 stirring is continued for 15 Hours at 20 ° C. The reaction mixture is with 5% sodium dihydrogenphos added phat solution, the organic phase separated and the aqueous phase once extracted with dichloromethane. The combined organic phases are twice washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated in a water jet vacuum. The residue is washed with ethanol stirred, the solid 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} -N '- (4,6-dimethoxypyrimidin-2-yl) urea from Melting point 167 ° C.  

Production of the starting material

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

4.4 g (72.1% of theory) of 3-chloro-6- (2-ethyl- [1,3] dioxolan-2-yl) -2-methylaniline are obtained
¹ H NMR (CDCl ₃ ): 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. For this a solution of 141.5 g (1.0 mol) of 3-chloro-2-methylaniline in 150 is added dropwise at 0.degree ml 1,2-dichloroethane and stirred for 40 minutes at 20 ° C. Then there is a solution 82.5 g (1.5 mol) of propionitrile were added dropwise and the mixture was stirred at 20 ° C. for a further hour touched. 227.6 g (1.2 mol) of titanium tetrachloride are then added dropwise and the mixture is heated to 15 Hours under reflux. 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 diluted with sodium hydroxide solution neutralized and extracted twice more with ethyl acetate. The United organic phases are washed twice with water, over sodium sulfate dries, 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.  

Example 5

To a solution of 11.6 g (0.082 mol) of chlorosulfonyl isocyanate in 100 ml of dichlor methane becomes 1.7 g (0.011 mol) of 2-amino-4,6-dimethoxy-pyrimidine at approx. 0 ° C added and stirred for 30 minutes at 0 to 20 ° C. Then you drop one Solution of 15 g (0.082 mol) of 3-chloro-2-methyl-6-propylaniline and 14.2 g (0.123 Mol) of triethylamine in 25 ml of dichloromethane and stirred for a further 15 hours at 20 ° C. The reaction mixture is mixed with dilute hydrochloric acid, the organic phase separated and the aqueous phase extracted once with dichloromethane. The unite th organic phases are washed with saturated sodium chloride solution, over Dried sodium sulfate, filtered and concentrated in a water jet vacuum. Of the The residue is stirred with ethanol and the solid formed is filtered off with suction. The raw product is stirred again with a mixture of petroleum ether and diethyl ether, again suction filtered, washed three times with petroleum ether and dried on clay.

20.1 g (55% of theory) of N - {[(3-chloro-2-methyl-6-propylphenyl) ami are obtained no] sulfonyl} -N '- (4,6-dimethoxypyrimidin-2-yl) urea, melting point 162 ° C.  

Example 6

To a solution of 1.42 g (0.01 mol) of chlorosulfonyl isocyanate in 100 ml of dichloro methane is added at about 0 ° C 1.4 g (0.01 mol) of 2-amino-4,6-dimethyl-pyrimidine and stirred at 0 to 20 ° C for 30 minutes. A solution of 1.9 is then added dropwise 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 and stirred for a further 36 hours at 20 ° C. The reaction mixture is mixed with dilute hydrochloric acid, the organic phase separated and the aq phase extracted once with dichloromethane. The combined organic phases are washed with saturated sodium chloride solution, over sodium sulfate dries, filtered and concentrated in a water jet vacuum. The arrears with Stirred ethanol, the solid was suctioned off, first twice with a little ethanol, then washed twice with diethyl ether and dried.

1.5 g (76.5% of theory) of N - {[(3-chloro-2-methyl-6-propylphenyl) ami are obtained no] sulfonyl} -N '- (4,6-dimethylpyrimidin-2-yl) urea, melting point 110 ° C.  

Preparation of the starting material for Examples 5 and 6

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

41.6 g (89.7% of theory) of 3-chloro-2-methyl-6-propylaniline are obtained
¹ H NMR (D ₆ -DMSO): δ = 2.2 (s, 3H) ppm.

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:

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 that Concentrate with water to the desired concentration.

To test for protective effectiveness, young plants are treated with the Active ingredient preparation sprayed in the application rate specified. After the The plants are sprayed with an aqueous spore suspension of Powdery mildew pathogen Podosphaera leucotricha inoculated. The plants are then in the Greenhouse set up at approx. 23 ° C and a relative humidity of approx. 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. B. the compounds of Preparation Examples 1, 5, 13 and 15 with an exemplary active ingredient application rate of 100 g / ha an 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 is mixed Active ingredient with the specified amounts of solvent and emulsifier and dilute that 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 Sphaotheca fuliginea inoculated. The plants are then at about 23 ° C and one relative humidity of about 70% in the greenhouse.

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. B. the compounds of Preparation Examples 1, 5, 13 and 15 with an exemplary active ingredient application rate of 100 g / ha an efficiency from 98 to 100% compared to the untreated control.  

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 is mixed Active ingredient with the specified amounts of solvent and emulsifier and dilute that Concentrate with water to the desired concentration.

To test for protective effectiveness, young plants are treated with the Active ingredient preparation sprayed in the application rate specified. After the The plants are sprayed with an aqueous conidia suspension of Apple scab pathogen Venturia inaequalis and then remain for 1 day at approx. 20 ° C and 100% relative humidity in an incubation cabin.

The plants are then in a greenhouse at about 21 ° C and a relative Humidity of approx. 90% set up.

Evaluation is carried out 12 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. B. the compounds of Preparation Examples 13 and 15 an exemplary active ingredient application rate of 100 g / ha 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, mix 1 Part by weight of active ingredient with the stated amount of solvent and specified amount of emulsifier and dilute the concentrate with water to the ge wanted concentration.

Cabbage leaves (Brassica oleracea) are dipped into the active ingredient preparation the desired concentration and treated with horseradish leaf beetle larvae (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 were killed.

In this test, e.g. B. the connection of manufacturing example 16 in a exemplary active ingredient application rate of 100 g / ha an efficiency of 100% compared to the untreated control.

Claims (8)

1. Compounds of the general formula (I)
in which
R ^{1 represents} optionally substituted alkyl or a group
stands in what
R ^{8 represents} hydrogen or optionally substituted alkyl, alkoxy, dialkylamino, cycloalkyl, cycloalkenyl, phenyl or heterocyclyl,
R ⁹ and R ¹⁰ each represent alkyl or together represent alkanediyl,
R ^{11 represents} optionally substituted alkyl,
R ² , R ³ and R ^{4 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 ² , R ³ or R ^{4 is} different from hydrogen,
R ^{5 represents} halogen, cyano, nitro, in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkenyl, alkenyloxy, cycloalkyl or cycloalkoxy,
R ⁶ and R ^{7 are} identical or different and each represent halogen or alkyl, alkenyl, alkynyl, alkynyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkyl amino, dialkylamino, cycloalkyl or heterocyclyloxy each optionally substituted by halogen or alkoxy and
G for nitrogen or
stands in what
R ^{12 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
R ¹ 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 ^{8 represents} hydrogen, optionally substituted by fluorine, chlorine, bromine, alkoxy with 1 to 3 carbon atoms, alkylthio with 1 to 3 carbon atoms, alkylsulfinyl with 1 to 3 carbon atoms or alkylsulfonyl with 1 to 3 carbon atoms, each with alkoxy, or dialkylamino 1 to 6 carbon atoms in the individual alkyl parts, for each optionally substituted by fluorine, chlorine, bromine and / or alkyl with 1 to 3 carbon atoms, cycloalkyl, cycloalkenyl, cycloalkyl-alkyl or cycloalkenyl-alkyl 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 or substituted by fluorine, chlorine, bromine, alkyl having 1 to 3 carbon atoms or haloalkyl having 1 to 3 carbon atoms and 1 to 5 halogen atoms alkyl with 1 to 3 carbon atoms in the alkyl part or for each optionally by fluorine, chlorine, bromine, alkyl 1 to 3 carbon atoms or haloalkyl having 1 to 3 carbon atoms and 1 to 5 halogen atoms substituted heterocyclyl or heterocyclyl-alkyl having 3 to 7 ring members and having 1 to 3 carbon atoms in the alkyl part,
R ⁹ and R ¹⁰ each represent alkyl having 1 to 3 carbon atoms or together represent alkanediyl having 1 to 3 carbon atoms,
R ^{11 represents} alkyl with 1 to 4 carbon atoms optionally substituted by halogen or phenyl,
R ² , R ³ and R ^{4 are the} same or different and each represents hydrogen; Halo gen, 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, alkenyl oxy 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 with 3 to 6 carbon atoms, but one the radicals R ² , R ³ or R ^{4 are} different from hydrogen,
R ⁵ 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 with 2 to 4 carbon atoms, haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkyl sulfonyl 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 with 3 to 6 carbon atoms stands,
R ⁶ and R ^{7 are the} same or different and are each halogen or for alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino or dialkylamino each having 1 to 4 carbon atoms in each case substituted by halogen or alkoxy with 1 to 4 carbon atoms the individual 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 for nitrogen or
stands in what
R ^{12 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
R ¹ 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 ⁸ 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 methoxy methyl, methoxyethyl, ethoxymethyl, ethoxyethyl, methylthio methyl, methylthioethyl, ethylthiomethyl, ethylthioethyl, methylsulfinylmethyl, ethylsulfinylmethyl, methylsulfonylmethyl, ethylsulfonylmethyl, fluorine, methoxyethoxy, in each case by methoxyethoxy and / or methyl substituted cyclopropyl, cyclopropylmethyl, cyclobutyl, cyclobutylmethyl, cyclopentyl, cyclopentylmethyl, cyclopentenylmethyl, cyclohexyl, cyclohexenylmethyl, phenyl, benzyl, phenylethyl, furyl, furylmethyl, thienyl, thienylmethyl, tetrahydrofuryl or tetrahydrofuryl or
R ⁹ and R ^{10 are} each 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-propanediyl stand,
R ^{11 represents} methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or benzyl,
R ² , R ³ and R ^{4 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, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl, vinyl, allyl, allyloxy or cyclopropyl, but one of the radicals R ² , R ³ or R ^{4 is} different from hydrogen
R ⁵ 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, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl , Vinyl, allyl, allyloxy or cyclopropyl,
R ⁶ and R ^{7 are the} same or different and each represents chlorine, methyl, ethyl, vinyl, allyl, 2-methylethen-1-yl, ethinyl, 2-methylethin-1-yl, propargyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy , Trifluoroethoxy, methylthio, ethylthio, methylamino, ethylamino, dimethylamino, cyclopropyl or oxethan-1-yloxy and
G for nitrogen or
stands in what
R ^{12 represents} hydrogen, fluorine, chlorine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, trifluoroethyl, methoxymethyl or ethoxymethyl. 4. pesticide, characterized by a content of at least one compound of formula (I) according to claim 1. 5. A method for controlling pests, characterized in that compounds of formula (I) according to claim 1 for pests and / or lets their living space take effect.   6. Use according to compounds of formula (I) and agents according to Claims 1 to 4 for controlling pests. 7. Process for the manufacture of pesticides, thereby characterized in that compounds of the formula (I) according to Claims 1 to 3 mixed with extenders and / or surfactants. 8. A process for the preparation of compounds of the formula (II) according to claim 1, characterized in that aminotriazines or pyrimidines of the general formula (II),
in which
R ⁶ , R ⁷ and G have the meanings given in claim 1,
with chlorosulfonyl isocyanate, optionally in the presence of a diluent, and the chlorosulfonylureas formed in this process of the general formula (III),
in which
R ⁶ , R ⁷ and G have the meanings given in claim 1,
with anilines of the general formula (IV),
in which
R ¹ , R ² , R ³ , R ⁴ and R ^{5 have} the meanings given in claim 1,
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.