WO2000064895A1 - Hetaryl-substituted dithiazole dioxides used as plant protection agents - Google Patents

Abstract

The invention relates to novel hetaryl-substituted dithiazole dioxides, to a method for the production thereof, and to their use for protecting plants and materials.

Description

HETARYL SUBSTITUTED DITHIAZOLD DIOXIDES AS A PLANT PROTECTANT

The invention relates to new hetaryl-substituted dithiazole dioxides, processes for their preparation and the use in plant and material protection.

5-ring dithiazoles have already been described, a biological effect is not known (cf. K. Dickore, Lieb. Ann. Chem. 1964, 671; US 3,345,374). S-aryldithiazole dioxides are known, their range of action does not reach the required level (cf. DE 19 545 635). In addition, dithiazine oxides (6-rings) with alkyl substitution

Sulfur already described, a biological effect is not known (see Nakahashi et al., Bull. Chem Soc. Jpn. 1972, 45, 3217; Hasegawa, K. et al., Bull. Chem. Soc. Jpn. 1972, 45 , 1567).

It has now been found that the new compounds of the general formula (I)

in welcher

in which

X ^{1 represents} oxygen or sulfur,

Y stands for -CHR ⁷ - or -CHR ⁵ CHR ⁶ -,

Z 'represents sulfur, oxygen, NR ¹ ,

Z ^{2 represents} CR ² or nitrogen, Z ^{3 represents} CR ³ or nitrogen,

Z ^{4 represents} CR ⁴ or nitrogen,

R ¹ , R ² , R ³ and R ^{4 are the} same or different and are independently hydrogen, cyano, nitro, substituted or unsubstituted alkyl, alkenyl, alkynyl, alkoxy, haloalkoxy, benzylthio, alkylthio, haloalkylthio, aryl, pyridyl, pyrimidyl or Pyrazinyl stand or are optionally connected via one of these substituents and

R ⁵ , R ⁶ and R ^{7 are} identical or different and independently of one another represent hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, pyridyl, nitro, cyano or halogen,

are excellent for protecting plants and materials.

Compounds of the formula (I) in which

X ^{1 represents} oxygen or sulfur,

Y stands for -CHR ⁷ - or -CHR ⁵ CHR ⁶ -,

Z ^{1 represents} sulfur, oxygen, NR ¹ ,

Z ^{2 represents} CR ² or nitrogen,

Z ^{3 represents} CR ³ or nitrogen,

Z ^{4 represents} CR ⁴ or nitrogen, where R ¹ , R ² , R ³ , R ⁴ independently of one another are hydrogen, cyano, nitro, straight-chain or branched alkyl (C, -C ₆ ), alkenyl (C ₂ -C ₆ ), alkynyl (C ₂ -C ₆ ), which are optionally substituted one or more times, identically or differently, by halogen, nitro, cyano, alkoxy (C, -C ₆ ), haloalkoxy (C _r C ₆ ) with 1 to 9 identical or different halogen atoms, alkylthio (C, - C ₆ ),

Haloalkylthio (C, -C ₆ ) with 1 to 9 identical or different halogen atoms, phenyl, pyridyl, pyrimidyl, or pyrazinyl; for alkoxy (C _j -C ₅ ); for haloalkoxy (C _j -C ₅ ) with 1 to 6 identical or different halogen atoms; Benzylthio; Alkylthio (C | -C ₅ ); Haloalkylthio (C _r C ₅ ) with 1 to 6 identical or different halogen atoms; or for phenyl, pyridyl, pyrimidyl or pyrazinyl, which are each optionally mono- to polysubstituted by halogen, alkyl (C _r C ₅ ), haloalkyl (C, -C ₅ ) with 1 to 6 identical or different halogen atoms, alkoxy (C, -C ₅ ), haloalkoxy (CC _j ) with 1 to 6 identical or different halogen atoms, alkylthio (C, -C ₅ ), haloalkylthio (C, -C ₅ ) with 1 to 6 identical or different halogen atoms, amino, monoalkylamino with straight-chain or branched alkyl radicals (C, -C ₆ ), dialkylamino with identical or different, straight-chain or branched alkyl radicals (C, -C ₅ ), or R ² and R ^{3 are} connected via the group -CH = CH-CH = CH- which is optionally substituted one to four times by halogen, nitro, cyano, alkyl (C, -C ₅ ),

Haloalkyl (Cι-C ₅ ) with 1 to 6 identical or different halogen atoms, alkoxy (C, -C ₅ ), haloalkoxy (C, -C ₅ ) with 1 to 6 identical or different halogen atoms, alkylthio (C, -C ₅ ) , Haloalkylthio (C, -C ₅ ) with 1 to 6 identical or different halogen atoms, amino, monoalkylamino with straight-chain or branched alkyl radicals (C, -C ₆ ), dialkylamino with identical or different, straight-chain or branched alkyl radicals (C, - C ₅ ), or fused with an aryl ring,

R ⁵ , R ⁶ or R ^{7 are the} same or different and independently of one another for hydrogen, nitro, cyano, halogen, straight-chain or branched alkyl (C, -

C ₈ ), alkenyl (C ₂ -C ₈ ) or alkynyl (C ₂ -C ₈ ), which may be one to is substituted several times, identically or differently by halogen, optionally substituted phenyl, alkoxy (C, -C ₅ ), haloalkoxy (C, -C ₅ ) with 1 to 6 identical or different halogen atoms, acyl (C, -C ₅ ) or for optionally substituted aryl, pyridyl,

Compounds of the formula (I) in which

X 'represents oxygen or sulfur,

Y stands for -CHR ⁷ - or -CHR ⁵ CHR ⁶ -,

Z 'represents sulfur, oxygen, NR ¹ ,

Z ^{2 represents} CR ² or nitrogen,

Z ^{3 represents} CR ³ or nitrogen,

Z ^{4 represents} CR ⁴ or nitrogen, where

R ¹ , R ² , R ³ , R ⁴ independently of one another are hydrogen, cyano, nitro, straight-chain or branched alkyl (C, -C ₅ ), alkenyl (C ₂ -C ₅ ), alkynyl (C ₂ -C ₅ ), which are optionally substituted one or more times, identically or differently, by fluorine, chlorine, nitro, cyano, alkoxy (C, -C ₄ ), haloalkoxy (C, -C ₄ ) with 1 to 5 identical or different fluorine and / or or chlorine atoms, alkylthio (C, -C ₄ ), haloalkylthio (C, -C ₄ ) with 1 to 5 identical or different fluorine and / or chlorine atoms, phenyl, pyridyl, pyrimidyl or pyrazinyl; for alkoxy (C] -C ₄ ); for haloalkoxy (C _r C ₄ ) with 1 to 4 identical different fluorine and / or chlorine atoms; Benzylthio, alkylthio (C _j -C ₄ ); Haloalkylthio (C | -C ₄ ) with 1 to 4 identical or different fluorine or chlorine atoms, or for phenyl, pyridyl, pyrimidyl or pyrazinyl, each of which may be one to more, the same or different sub- are substituted by fluorine and / or chlorine, alkyl (C, -C ₄ ), haloalkyl (C, -C ₄ ) with 1 to 4 identical or different fluorine and / or chlorine atoms, alkoxy (C, -C ₄ ), haloalkoxy (C, -C ₄ ) with 1 to 4 identical or different fluorine and / or chlorine atoms, alkylthio (C _r C ₄ ), haloalkylthio (C, -C ₄ ) with 1 to 4 identical or different fluorine or chlorine atoms,

Amino, monoalkylamino with straight-chain or branched alkyl radicals (C, -C ₅ ), dialkylamino with identical or different, straight-chain or branched alkyl radicals (C, -C ₄ ), or R ² and R ³ via the group -CH = CH-CH = CH-, which are optionally substituted one to four times by fluorine, chlorine, nitro, cyano, alkyl

(C, -C ₄ ), haloalkyl (C, -C ₄ ) with 1 to 4 identical or different fluorine and / or chlorine atoms, alkoxy (C, -C ₄ ), haloalkoxy (C, -C ₄ ) with 1 to 4 identical or different fluorine and / or chlorine atoms, alkylthio (C, -C ₄ ), haloalkylthio (C, -C ₄ ) with 1 to 4 identical or different fluorine and / or chlorine atoms, amino, monoalkylamino with straight-chain or branched alkyl radicals (C, -C ₅ ), dialkylamino with the same or different, straight-chain or branched alkyl radicals (C, -C ₄ ), or fused with an aryl ring.

R ⁵ , R ⁶ or R ^{7 are the} same or different and are independently hydrogen, nitro, cyano, fluorine, chlorine, straight-chain or branched alkyl (C, -C ₆ ), alkenyl (C ₂ -C ₆ ) or alkynyl (C ₂ -C ₆ ), which is optionally substituted one or more times, identically or differently, by fluorine, chlorine, optionally substituted phenyl, alkoxy (C, -C ₄ ), haloalkoxy (C, -C ₄ ) with 1 to 5 identical or various fluorine and / or chlorine atoms, acyl

(C, -C ₅ ) or optionally substituted aryl, pyridyl,

Compounds of the formula (I) in which

X 'represents oxygen or sulfur, Y stands for -CHR ⁷ - or -CHR ⁵ CHR ⁶ -,

Z ^{1 represents} sulfur, oxygen, NR ',

Z ^{2 represents} CR ² or nitrogen,

Z ^{3 represents} CR ³ or nitrogen,

represents CR ⁴ or nitrogen, where

R ', R ² , R ³ , R ^{4 are the} same or different and are independently hydrogen, cyano, nitro, straight-chain or branched alkyl, alkenyl, alkynyl, in particular methyl, ethyl, n-propyl, i-propyl, n-butyl , i-butyl, s-butyl, t-butyl, cyclohexyl, cyclopentyl, allyl, propargyl, which are in each case optionally substituted one to three times, identically or differently, by fluorine,

Chlorine, nitro, cyano, alkoxy, especially methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, haloalkoxy, especially difluoromethoxy, trifluoromethoxy, dichlorofluoromethoxy, difluorochloromethoxy, Pentafluoroethoxy, benzylthio, alkylthio, especially methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio, t-

Butylthio, haloalkylthio, especially difluoromethylthio, trifluoromethylthio, dichlorofluoromethylthio, difluorochloromethylthio, pentafluoroethylthio, phenyl, pyridyl, pyrimidyl, pyrazinyl; for alkoxy, in particular methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy; for haloalkoxy, in particular difluoromethoxy, trifluoromethoxy,

Dichlorofluoromethoxy, difluorochloromethoxy, pentafluoroethoxy; for benzylthio; for alkylthio, especially methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio, t-butylthio; for haloalkylthio, in particular difluoromethylthio, trifluoromethylthio, dichlorofluoromethylthio, difluorochloromethylthio, pentafluoroethylthio; or for phenyl,

Pyridyl, pyrimidyl, pyrazinyl, which are optionally one to three times the same or are differently substituted by fluorine, chlorine, alkyl, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, haloalkyl, in particular difluoromethyl, trifluoromethyl, dichlorofluoromethyl, difluorochloromethyl. Pentafluoroethyl, alkoxy, especially methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, haloalkoxy, especially difluoromethoxy, trifluoromethoxy, dichlorofluoromethoxy, difluorochloromethoxy, pentafluoroethoxy, alkylthio, in particular methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio, t-butylthio, haloalkylthio, in particular difluoromethylthio, trifluoromethylthio, dichlorofluoromethylthio, difluorochloromethylthio, pentafluoro. Amino,

Monoalkylamino or dialkylamino with the same or different, straight-chain or branched alkyl radicals, in particular methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, or are

R ² and R ^{3 are} connected via the group -CH = CH-CH = CH-, which is optionally substituted one to three times by fluorine and / or chlorine, nitro, cyano, alkyl, in particular methyl, ethyl, n-propyl, i -Propyl, n-butyl, i-butyl, s-butyl, t-butyl, haloalkyl, especially difluoromethyl, trifluoromethyl, dichlorofluoromethyl, difluorochloromethyl, pentafluoroethyl, alkoxy, in particular methoxy, ethoxy, n-propoxy, i-propoxy, n -Butoxy, i-butoxy, s-butoxy, t-butoxy, haloalkoxy, especially difluoromethoxy, trifluoromethoxy, dichlorofluoromethoxy, difluorochloromethoxy, pentafluoroethoxy, alkylthio, such as methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio , s-butylthio, t-butylthio, haloalkylthio, especially difluoromethylthio, trifluoromethylthio, dichlorofluoromethylthio, difluorochloromethylthio, pentafluoroethylthio, amino, monoalkylamino or dialkylamino with the same or different, straight-chain or branched alkyl radicals, especially methyl, especially methyl i-propyl, n-butyl, i-butyl, s-butyl, t-butyl,

R ⁶ or R ^{7 are the} same or different and independently of one another are hydrogen, nitro, cyano, fluorine, chlorine, straight-chain or branched alkyl, Alkenyl, alkynyl, especially methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, allyl, propargyl, which is optionally substituted by fluorine and / or chlorine, optionally substituted Phenyl, alkoxy, especially methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, haloalkoxy, especially difluoromethoxy, trifluoromethoxy, dichlorofluoromethoxy, difluorochloromethoxy, pentafluoroethoxy, acyl, especially formyl , Acetyl, n-propionyl, i-propionyl, n-butyryl, i-butyryl, s-butyryl, or optionally substituted aryl, pyridyl.

Compounds in which

X ^{1 represents} sulfur.

Y represents -CH ₂ - or -CH ₂ CH ₂ -, in particular CH ₂ .

Z ^{l represents} sulfur or NR ¹ .

Z ^{2 represents} CR ² or nitrogen.

Z ^{3 represents} CR ³ or nitrogen.

Z ^{4 represents} CH or nitrogen.

The radical definitions given for these radicals in the respective combinations or preferred combinations of radicals are independently replaced by radical definitions of other combinations, irrespective of the respectively specified combination. In addition, residual definitions from each preferred area can also be omitted. The compounds of the formula (I) are obtained if (process a) compounds of the general formula (II)

in which

Y has the meaning given above and

X ^{2 represents} bromine or chlorine,

with compounds of the general formula (III),

in which

X ¹ , Z ¹ , Z ² , Z ³ and Z ^{4 have} the meanings given above,

if appropriate in the presence of a base and if appropriate in the presence of a diluent.

The reaction temperatures can be varied over a wide temperature range in this process. In general, one works between -30 ° C and + 100 ° C, preferably between -10 ° C and + 60 ° C. If appropriate, the reactions are carried out in the presence of bases; all customary bases can be used here. These preferably include tertiary amines, such as triethylamine, diisopropylethylamine or pyridine; Alkali hydroxides such as sodium and potassium hydroxide and alkali carbonates and hydrogen carbonates such as potassium carbonate and sodium hydrogen carbonate.

Possible diluents which can be used are both water and all organic solvents. These preferably include hydrocarbons such as toluene, xylene or hexane, chlorinated hydrocarbons such as

Chlorobenzene and chloroform, ketones such as acetone, ethers such as tetrahydrofuran, diethyl ether, methyl tert-butyl ether and dioxane, nitriles such as acetonitrile, and DMSO, DMF and NMP.

The compounds of the formula (II) are known (cf. WO 98/52945) or can be prepared by analog processes.

The compounds of formula (III) are known synthetic chemicals.

It has also been found that the compounds of the formula (I) with X 'in its meaning as sulfur are in many cases also obtained (process b) if the salts of the general formula (IV)

V

(IV)

M ⁺ S

in which

Y has the meaning given above and M ^{+ represents} an alkali or alkaline earth metal ion, in particular Na ⁺ or K ⁺ ,

with diazonium salts of the general formula (V)

in which

Z ', Z ² , Z ³ and Z ^{4 have} the meanings given above and

A ^"stands for the anion of a mineral acid,

in aqueous / alkaline solution, if appropriate in the presence of a catalyst.

A base and optionally a catalyst and then the diazonium salt solution (V) are preferably added to a solution of (IV). Alkali metal hydroxides such as potassium hydroxide or sodium hydroxide are preferably used as bases. All catalysts which promote the exchange of the diazonium function for sulfur-containing radicals can be used as catalysts.

Cu (I) salts or copper powder are preferably used. The temperature during the addition of the diazonium salt solution can be varied over a wide range. In general, one works between -30 ° C and + 60 ° C, preferably between -20 ° C and + 40 ° C. The diazonium salt solution is prepared using literature methods. The compounds of the formula (IV) are known (cf. DE 19 545 635; WO-98/29400) or can be prepared analogously.

Furthermore, it was found that compounds of the general formula (I) can also be obtained (process c) if compounds of the general formula (IV)

M ⁺ S in which

Y and M ^{+ have} the meanings given above,

with compounds of the general formula (VI)

in which

Z ¹ , Z ² , Z ³ and Z ^{4 have} the meanings given above and

X ³ for a leaving group, in particular for mesyl, tosyl, fluorine, chlorine or

Bromine stands,

if appropriate in the presence of a base and if appropriate in the presence of diluents. The reaction temperatures can be varied over a wide temperature range in this process. Generally one works between -30 ° C and + 150 ° C, preferably between -10 ° C and + 100 ° C.

If appropriate, the reactions are carried out in the presence of bases; all customary bases can be used here. These preferably include tertiary amines, such as triethylamine, diisopropylethylamine or pyridine; Alkali hydroxides such as sodium and potassium hydroxide and alkali carbonates and hydrogen carbonates such as potassium carbonate and sodium hydrogen carbonate.

Possible diluents which can be used are both water and all organic solvents. These preferably include hydrocarbons such as toluene, xylene or hexane, chlorinated hydrocarbons such as chlorobenzene and chloroform, ketones such as acetone, ethers such as tetrahydrofuran, diethyl ether, methyl tert-butyl ether and dioxane, nitriles such as acetonitrile and

DMSO, DMF and NMP.

All of the processes according to the invention are generally carried out under normal pressure. However, it is also possible to work under increased or reduced pressure - generally between 0.1 bar and 10 bar.

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 in crop protection to combat Plasmodiophoromyces, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes. Bactericides can be used in crop protection to combat Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.

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

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

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

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

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

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

Pseudoperonospora cubensis;

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

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

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

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

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

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

(Conidial form: Drechslera, Syn: Helminthosporium);

Cochliobolus species, such as, for example, Cochliobolus sativus

(Conidial form: Drechslera, Syn: Helminthosporium); Uromyces species, such as, for example, Uromyces appendiculatus;

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

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

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

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

Pyricularia species, such as, for example, Pyricularia oryzae; Fusarium species, such as, for example, Fusarium culmorum; Botrytis species, such as, for example, Botrytis cinerea; Septoria species, such as, for example, Septoria nodorum; Leptosphaeria species, such as, for example, Leptosphaeria nodorum; Cercospora species, such as, for example, Cercospora canescens;

Alternaria species, such as, for example, Alternaria brassicae; Pseudocercosporella species, such as, for example, Pseudocercosporella herpotrichoides.

The fact that the active compounds are well tolerated by plants in the concentrations required to combat plant diseases allows treatment of above-ground parts of plants, of propagation stock and seeds, and of the soil.

According to the invention, all plants and parts of plants can be treated. Plants are understood here to mean all plants and plant populations, such as desired and unwanted wild plants or crop plants (including naturally occurring crop plants). Cultivated plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeders' rights. Under

Plant parts are to be understood to mean all above-ground and underground parts and organs of plants, such as shoots, leaves, flowers and roots, examples of which are leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, tubers and rhizomes. The plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.

The treatment of the plants and parts of plants according to the invention with the active compounds is carried out directly or by acting on their surroundings, living space or storage space using the customary treatment methods, for example by dipping, spraying, Evaporation, nebulization, scattering, spreading and, in the case of propagation material, in particular in the case of seeds, furthermore by means of single or multi-layer coating.

The active compounds according to the invention can be used with particularly good results in combating cereal diseases, for example against Erysiphe species, or for diseases in wine, fruit and vegetable cultivation, for example against Plasmopara species.

Other diseases in wine, fruit and vegetable cultivation, such as Phytophthora species, are also combated with great success. The active compounds according to the invention are also suitable for increasing the crop yield. They are also less toxic and have good plant tolerance.

In material protection, the substances according to the invention can be used to protect technical materials against attack and destruction by undesired microorganisms.

In the present context, technical materials are to be understood as non-living materials that have been prepared for use in technology. For example, technical materials made by the invention

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

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

Alternaria, such as Alternaria tenuis,

Aspergillus, such as Aspergillus niger, Chaetomium, such as Chaetomium globosum,

Coniophora, such as Coniophora puetana,

Lentinus, such as Lentinus tigrinus,

Penicillium, such as Penicillium glaucum,

Polyporus, such as Polyporus versicolor, Aureobasidium, such as Aureobasidium pullulans,

Sclerophoma, such as Sclerophoma pityophila,

Trichoderma, like Trichoderma viride,

Escherichia, such as Escherichia coli,

Pseudomonas, such as Pseudomonas aeruginosa, Staphylococcus, such as Staphylococcus aureus.

Depending on their respective physical and / or chemical properties, the active 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 mist formulations.

These formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants. agents and / or foaming 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 alkylnaphthahn, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, alcohols, such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water. Liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide. The following are suitable as solid carriers: for example, 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. Possible solid carriers for granules are: eg 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 stalks. Suitable emulsifiers and / or foaming agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkyl aryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolysates. Possible dispersing agents are, for example, lignin sulfite waste liquor and methyl cellulose.

Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, 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. Dyes such as inorganic pigments, for example iron oxide, titanium oxide, ferrocyan blue and organic dyes, such as alizarin, azo and metal phthalocyanine dyes and trace nutrients, such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc, can be used .

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

The active compounds according to the invention, as such or in their formulations, can also be used in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, in order, for example, to broaden the spectrum of activity or to prevent the development of resistance. In many cases, synergistic effects are obtained, i.e. the effectiveness of the mixture is greater than the effectiveness of the individual components.

The following compounds can be considered as mixing partners for crop protection applications:

Fungicides:

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

Benalaxyl, benodanil, benomyl, benzamacril, benzamacrylic isobutyl, bialaphos, binapacrylic, biphenyl, bitertanol, blasticidin-S, bromuconazole, bupirimate, buthio-bat,

Calcium polysulfide, capsimycin, captafol, captan, carbendazim, carboxin, carvone, quinomethionate (quinomethionate), chlobenthiazone, chlorfenazole, chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon, cufraneb, cymoxanil, cyphodaminazol, cypodaminazol, cypodinconol

Debacarb, dichlorophene, diclobutrazole, diclofluanide, diclomezin, dicloran. Diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, diniconazol-M, dinocap, diphenylamine, dipyrithione, ditalimfos, dithianon, dode-moφh, dodine, drazoxolon, ediphenphos, epoxiconazole, etamolazole, ethazolazole, ethazolazole

Famoxadone, Fenapanil, Fenarimol, Fenbuconazol, Fenfuram, Fenitropan, Fenpiclonil, Fenpropidin, Fenpropimoφh, Fentinacetat, Fentinhydroxyd, Ferbam, Ferimzon, Fluazinam, Flumetover, Fluoromid, Fluquinconazol, Flusrimidol, Flusrimidol, Flusrimidol, Folus Fosetyl-aluminum, fosetyl sodium, fthalide, fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole, furconazole-cis, furmecyclox, guazatin,

Hexachlorobenzene, Hexaconazole, Hymexazol, Imazalil, Imibenconazol, Iminoctadin, Iminoctadinealbesilat, Iminoctadinetriacetat, Iodocarb, Ipconazol, Iprobefos (IBP), Iprodione, Irumamycin, Isopro thiolan, Iso-valedione

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,

Metconazole, methasulfocarb, methfuroxam, metiram, metomeclam, metsulfovax,

Mildiomycin, myclobutanil, myclozolin,

Nickel dimethyldithiocarbamate, Nitrothal-isopropyl, Nuarimol, Ofürace, Oxadixyl, Oxamocarb, Oxolinicacid, Oxycarboxim, Oxyfenthiin,

Paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen, pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz, procymidon, propamocarb,

Propanosine sodium, propiconazole. Propineb, pyrazophos, pyrifenox, pyrimethanil,

Pyroquilon, Pyroxyfur, Quinconazol, Quintozen (PCNB),

Sulfur and sulfur preparations,

Tebuconazole, tecloftalam, tecnazen, tetcyclacis, tetraconazole, thiabendazole, thycyofen, thifluzamide, thiophanate-methyl, thiram, dioxymid, tolclofos-methyl,

Tolylfluanid, triadimefon, triadimenol, triazbutil, triazoxid, trichlamid, tri-cyclazol, tridemoφh, 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-dichloφhenyl) -ß-methoxy-a-methyl-1 H-1, 2,4-triazole-1 -ethanol, α- (5-methyl-1, 3-dioxan-5-yl) -ß - [[4- (trifluoromethyl) phenyl] methylene] - 1 H- 1, 2,4-triazol-1 - ethanol,

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

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

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

1 - (2,4-dichlorothenyl) -2- (1 H-1, 2,4-triazole-1-yl) -ethanone-O- (phenylmethyl) -oxime, 1 - (2-methyl-1-naphthalenyl) - 1 H-pyrrole-2,5-dione, l- (3,5-dichloro-phenyl) -3- (2-propenyl) -2,5-pyrrolidinedione, l- [ (Diiodomethyl) sulfonyl] -4-methyl-benzene, l - [[2- (2,4-dichloro-phenyl) -l, 3-dioxolan-2-yl] methyl] -lH-imidazole, l - [[2nd - (4-chloro-phenyl) -3-phenyloxiranyl] -methyl] -IH-l, 2,4-triazole, 1- [l- [2 - [(2,4-dichloro-xhenyl) methoxy] phenyl] ethenyl] -lH-imidazole,

1-methyl-5-nonyl-2- (phenylmethyl) -3-pyrrolidinol,

2 ', 6'-dibromo-2-methyl-4'-trifluoromethoxy-4'-trifluoromethyl-l, 3-thiazole-5-carboxanilide, 2,2-dichloro-N- [l- (4- chloφhenyl) -ethyl] -l-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 - [(l-methylethyl) sulfonyl] -5- (trichloromethyl) -l, 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-chloro-N- (2,3-dihydro-1,3,3-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] -1 H-pyrrole-2,5-dione,

3,5-dichloro-N- [cyan [(1-methyl-2-propynyl) -oxy] -methyl] -benzamide, 3- (1,1-dimethylpropyl-1-oxo-1 H-indene-2-carbonitrile ,

3- [2- (4-chloro-phenyl) -5-ethoxy-3-isoxazolidinyl] pyridine,

4-chloro-2-cyan-N, N-dimethyl-5- (4-methylphenyl) -1 H-imidazole-1-sulfonamide,

4-methyl-tetrazolo [1,5-a] quinazolin-5 (4H) -one,

8- (l, l-dimethylethyl) -N-ethyl-N-propyl-l, 4-dioxaspiro [4.5] decane-2-methanamine, 8-hydroxyquinoline sulfate,

9H-xanthene-9-carboxylic acid 2 - [(phenylamino) carbonyl] hydrazide, bis- (l-methylethyl) -3-methyl-4 - [(3-methylbenzoyl) -oxy] -2,5-thiophene dicarboxylate, ice-1 - (4-chloro-phenyl) -2- (1 H-1, 2, 4-triazol-1 -yl) -cycloheptanol, cis-4- [3- [4- (l, l-dimethylpropyl) phenyl-2-methylpropyl] -2,6-dimethyl-morpholine hydrochloride, 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) -l-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-l - [(chloroacetyl) amino] ethyl] benzamide, N- [3-chloro-4,5-bis (2-propynyloxy) phenyl] -N ' -methoxy-methanimidamide,

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

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

O-methyl-S-phenyl-phenylpropylphosphoramidothioate,

S-methyl-1, 2,3-benzothiadiazole-7-carbothioate, spiro [2H] -l-benzopyran-2, r (3Η) -isobenzofuran] -3'-one,

Bactericides:

Bronopol, dichlorophene, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furan carboxylic acid, oxytetracycline, probenazole, streptomycin, teclofalam, copper sulfate and other copper preparations. Insecticides / acaricides / nematicides:

Abamectin, Acephate, Acetamiprid, Acrinathrin, Alanycarb, Aldicarb, Aldoxycarb, Alpha-cypermethrin, Alphamethrin, Amitraz, Avermectin, AZ 60541. Bacillus thuringiensis, Baculoviren, Beauveria bassiana, Beauveria tenella, Bendiocarb, Benfuracarb, Bensul-tap, Benzoximate, Betacyfluthrin, Bifenazate, Bifenthrin, Bioethanomethrin, Bio-permethrin, BPMC, Bromophos A, Bufenosim, Buprofin, Bufenobin, Buf Butylpyridaben, Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, Chloetho- carb, Chlorethoxyfos, Chlorfenapyr, Chlorfenvinphos, Chlorfluazuron, Chlormephos, Chloφyrifos, Chlorpyrifos M, Chlovaporthrin, Cis-Resmetethinocininin Cyanophos, Cycloprene, Cycloprothrin, Cyfluthrin, Cyhalothrin, Cyhexatin, Cypermethrin, Cyromazine, Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, diazinon,

Dichlorvos, diflubenzuron, dimethoate, dimethylvinphos, diofenolan, disulfoton, docusat-sodium, doenapyn,

Eflusilanate, Emamectin, Empenthrin, Endosulfan, Entomopfthora spp., Esfenvalate, Ethiofencarb, Ethion, Ethoprophos, Etofenprox, Etoxazole, Etrimfos, Fenamiphos, Fenazaquin, Fenbutatin oxide, Fenitrothion, Fenothimocarb, Fenacroth

Fenoxycarb, fenpropathrin, fenpyrad, fenpyrithrin, fenpyroximate, fenvalerate, fipronil, fluazinam, fluazuron, flubrocythrinate, flucycloxuron, flucythrinate, fluefenoxuron, flutenzine, fluvalinate, fonophos, fosmethxate, firomethenos, furosti, fosmethilan, fostriloshenf, furosti

Halofenozide, HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene, Imidacloprid, Isazofos, Isofenphos, Isoxathion, Ivermectin, Kernpolyederviruses Lambda-cyhalothrin, Lufenuron Malathion, mecarbam, metaldehyde, methamidophos, metharhilic anisopliae, metharithic flavoviride, methidathione, methiocarb, methomyl, methoxyfenozide,

Metolcarb, Metoxadiazone, Mevinphos, Milbemectin, Monocrotophos,

Naled, Nitenpyram, Nithiazine, Novaluron Omethoat, Oxamyl, Oxydemethon M

Paecilomyces fumosoroseus, Parathion A, Parathion M, Permethrin, Phenthoat,

Phorat, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos A, Pi rimiphos M, Profenofos, Promecarb, Propoxur, Prothiofos, Prothoat, Pymetrozine,

Pyraclofos, Pyresmethrin, Pyrethrum, Pyridaben, Pyridathion, Pyrimidifen, Pyriproxyfen,

Quinalphos,

Ribavirin

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

Tau fluvalinate, tebufenozide, tebufenpyrad, tebupirimiphos, teflubenzuron, tefuthrin, temephos, temivinphos, terbufos, tetrachlorvinphos, theta-cypermethrin,

Thiamethoxam, thiapronil, thiatriphos, thiocyclam hydrogen oxalate, thiodicarb,

Thiofanox, thuringiensin, tralocythrin, tralomethrin, triarathenes, triazamates, triazophos, triazuron, trichlophenidines, trichlorfon, triflumuron, trimethacarb,

Vamidothion, Vaniliprole, Verticillium lecanii YI 5302

Zeta-cypermethrin, zolaprofos

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

(3-phenoxyphenyl) methyl 2,2,3,3-tetramethylcyclopropane decarboxylate l - [(2-chloro-5-thiazolyl) methyl] tetrahydro-3,5-dimethyl-N-nitro-l, 3,5-triazine -2 (lH) - imine

2- (2-chloro-6-fluoro-phenyl) -4- [4- (1,1-dimethylethyl) phenyl] -4,5-dihydro-oxazole

2- (acetyloxy) -3-dodecyl-1,4-naphthalenedione

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

3-methylphenyl propyl carbamate 4- [4- (4-ethoxyphenyl) -4-methylpentyl] -1-fluoro-2-phenoxy-benzene

4-chloro-2- (1,1-dimethylethyl) -5 - [[2- (2,6-dimethyl-4-phenoxyphenoxy) ethyl] thio] -

3 (2H) pyridazinone

4-chloro-2- (2-chloro-2-methylpropyl) -5 - [(6-iodo-3-pyridinyl) methoxy] -3 (2H) - pyridazinone

4-chloro-5 - [(6-chloro-3-pyridinyl) methoxy] -2- (3, 4-dichloro-phenyl) -3 (2H) -pyridazinone

Bacillus thuringiensis strain EG-2348

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

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

[3 - [(6-chloro-3-pyridinyl) methyl] -2-thiazolidinylidene] cyanamide

Dihydro-2- (nitromethylene) -2H-l, 3-thiazine-3 (4H) carboxaldehyde

Ethyl [2 - [[1,6-dihydro-6-oxo-1- (phenylmethyl) -4-pyridazinyl] oxy] ethyl] carbamate

N- (3,4,4-trifluoro-1-oxo-3-butenyl) glycine N- (4-chloro-phenyl) -3- [4- (difluoromethoxy) phenyl] -4,5-dihydro-4-phenyl- lH-pyrazole

1-carboxamide

N - [(2-chloro-5-thiazolyl) methyl] -N'-methyl-N "-nitro-guanidine

N-methyl-N '- (1-methyl-2-propenyl) - 1, 2-hydrazinedicarbothioamide

N-methyl-N'-2-propenyl-1, 2-hydrazinedicarbothioamide O, O-diethyl- [2- (dipropylamino) -2-oxoethyl] ethylphosphoramidothioate

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

For applications in material protection, e.g. the following mixing partners as particularly cheap:

Triazoles such as:

Azaconazole, Azocyclotin, Bitertanol, Bromuconazole, Cyproconazole, Diclobutrazole, Difenoconazole, Diniconazole, Epoxyconazole, Etaconazole, Fenbuconazole, Fenchlorazole, Fenethanil, Fluquinconazole, Flusilazole, Flutriafol, Flutriafol azoles, hexaconazole, imibenconazole, ipconazole, isozofos, myclobutanil, metconazole, paclobutrazole, penconazole, propioconazole, (+) - cis-l- (4-chloφhenyl) -2- (lH- l, 2,4-triazole-l -yl) -cycloheptanol, 2- (l-tert-butyl) -l- (2-chlθφhenyl) -3- (l, 2,4-triazol-l-yl) -propan-2-ol, tebuconazole, tetraconazole, Triadimefon, Triadimenol, Triapenthenol, Triflumizole, Triticonazole, Uniconazole as well as their metal salts and

Acid adducts;

Imidazoles such as:

Clotrimazole, Bifonazole, Climbazole, Econazole, Fenapamil, Imazalil, Isoconazole, Ketoconazole, Lombazole, Miconazole, Oxpoconazole, Pefurazoate. Prochloraz, triflumizole, thiazolcar 1 -imidazolyl-1 - (4'-chlorophenoxy) -3,3-dimethylbutan-2-one and their metal salts and acid adducts;

Pyridines and pyrimidines such as: ancymidol, buthiobate, fenarimol, nuarimol, triamirol;

Succinate dehydrogenase inhibitors such as:

Benodanil, Carboxim, Carboximsulfoxid, Cyclafluramid, Fenfuram, Flutanil, Furcarbanil, Furmecyclox, Mebenil, Mepronil, Methfuroxam, Metsulfovax, Pyrocarboid, Oxycarboxin, Shirlan, Seedvax;

Naphthalene derivatives such as:

Terbinafine, naftifine, butenafine, 3-chloro-7- (2-aza-2,7,7-trimethyl-oct-3-en-5-in);

Sulfenamides such as:

Dichlorfluanide, tolylfluanid, folpet, fluorfolpet; Captan, Captofol;

Benzimidazoles such as:

Carbendazim, benomyl, fuberidazole, thiabendazole or their salts; Morpholine derivatives such as:

Aldimoφh, Dimethomoφh, Dodemoφh, Falimoφh, Fenpropidin Fenpropimoφh, Tridemoφh, Trimoφhamid and their arylsulfonic acid salts, e.g. p-toluenesulfonic acid and p-dodecylphenyl sulfonic acid;

Benzothiazoles such as: 2-mercaptobenzothiazole;

Benzothiophene dioxides such as: benzo [b] thiophene-S, S-dioxide-carboxylic acid cyclohexylamide;

Benzamides such as:

2,6-dichloro-N- (4-trifluoromethylbenzyl) benzamide, tecloftalam;

Boron compounds such as:

Boric acid, boric acid ester, borax;

Formaldehyde and formaldehyde releasing compounds such as:

Benzyl alcohol mono- (poly) -hemiformal, n-butanol-hemiformal, Dazomet, ethylene-glycol-hemiformal, hexa-hydro-S-triazine, hexamethylenetetramine, N-hydroxymethyl-N ^' -methylthiourea, N-methylolchloroacetamide, oxazolidine, paraform - aldehyde, tauroline, tetrahydro-l, 3-oxazine, N- (2-hydroxypropyl) amine-methanol;

Isothiazolinones such as: N-methylisothiazolin-3-one, 5-chloro-N-methylisothiazolin-3-one, 4,5-dichloro-N-octylisothiazolin-3-one, 5-chloro-N-octylisothiazolinone, N-octyl -isothiazolin-3-one, 4,5-trimethylene-isothiazolinone, 4,5-benzisothiazolinone, Nn-butylisothiazolinone;

Aldehydes such as: cinnamaldehyde, formaldehyde, glutardialdehyde, β-bromocinnamaldehyde; Thiocyanates such as:

Thiocyanatomethylthiobenzothiazole, methylene bisthiocyanate;

quaternary ammonium compounds such as: benzalkonium chloride, benzyldimethyltetradecylammonium chloride, benzyldimethyldodecylammonium chloride, dichlorobenzyldimethylalkylammonium chloride, dodecyldimethylammonium chloride, dioctyldimethylammonium chloride, N-hexadecyldimethylammidium chloride;

Iodine derivatives such as:

Diiodomethyl-p-tolyl sulfone, 3-iodo-2-propynyl alcohol, 4-chlorophenyl-3-iodopropargyl formal, 3-bromo-2,3-diiodo-2-propenylethyl carbamate, 2,3,3-triiodallyl alcohol, 3- Bromo-2,3-diiodo-2-propenyl alcohol, 3-iodo-2-propynyl-n-butyl carbamate, 3-iodo-2-propynyl-n-hexyl carbamate, 3-iodo-2-propynyl cyclohexyl carbamate, 3-iodo 2-propynylphenyl carbamate;

Phenols such as:

Tribromophenol, tetrachloφhenol, 3-methyl-4-chloro-phenol, 3,5-dimethyl-4-chlorophenol, phenoxyethanol, dichloro-phenol, 2-benzyl-4-chloro-phenol, 5-chloro-2- (2,4-dichloro-phenoxy) - phenol, hexachlorophene, p-hydroxybenzoic acid ester, o-phenylphenol, m-phenylphenol, p-phenylphenol and their alkali and alkaline earth metal salts;

Microbicides with activated halogen group such as: Bronopol, Bronidox, 2-bromo-2-nitro-l, 3-propanediol, 2-bromo-4'-hydroxy-acetophenone, 1-bromo-3-chloro-4,4,5 , 5-tetramethyl-2-imidazoldinone, ß-bromo-ß-nitrostyrene, chloroacetamide, chloramine T, l, 3-dibromo-4,4,5,5-tetrametyl-2-imidazoldinone, dichloramine T, 3,4-dichloro - (3H) -l, 2-dithiol-3-one, 2,2-dibromo-3-nitrile-propionamide, 1, 2-dibromo-2,4-dicyanobutane, halanes, halazones, mucochloric acid, phenyl- (2- chloro-cyan-vinyl) sulfone, phenyl- (1,2-dichloro-2-cyanovinyl) sulfone, trichloroisocyanuric acid; Pyridines such as:

1-hydroxy-2-pyridinthione (and its Na, Fe, Mn, Zn salts), tetrachloro-4-methylsulfonylpyridine, pyrimethanol, mepanipyrim, dipyrithione, 1-hydroxy-4-methyl-6-

(2,4,4-trimethylpentyl) -2 (1 H) pyridine;

Methoxyacrylates or similar like:

Methyl (E) methoximino [alpha- (o-tolyloxy) -o-tolyl] acetate, (E) -2-methoxyimino-N-methyl-2- (2-phenoxyphenyl) acetamide,

(E) -2- {2- [6- (2-cyanophenoxy) pyrimidin-4-yloxy] phenyl} -3-methoxyacrylate, O-methyl-2 - [([3-methoximino-2-butyl) imino] oxy ) o-tolyl] -2-methoximinoacetimidate,

2 - [[[[l- (2,5-dimethylphenyl) ethylidene] amino] oxy] methyl] -. Alpha .- (methoximino) -

N-methyl-benzeneacetamide, alpha- (methoxyimino) -N-methyl-2 - [[[[[l- [3- (trifluoromethyl) phenyl] ethyl-idene] amino] oxy] methyl] -benzeneacetamide, alpha- (methoxyimino) -2 - [[[[l- [3- (trifluoromethyl) phenyl] ethyl-idene] amino] oxy] methyl] -benzeneaceticacid-methyl ester, alpha- (methoxymethylene) -2 - [[[[l- [3- ( trifluoromethyl) phenyl] ethyl-idene] amino] oxy] methyl] -benzeneaceticacid-methyl ester, 2 - [[[5-chloro-3- (trifluoromethyl) -2-pyridinyl] oxy] methyl] -. alpha .- (methoxyimino) -N-methyl-benzeneacetamide,

2 - [[[cyclopropyl [(4-ethoxyphenyl) imino] methyl] thio] methyl] -. Alpha .- (methoxy-imino) -benzeneaceticacid-methyl ester, alpha- (methoxyimino) -N-methyl-2- (4- methyl-5-phenyl-2,7-dioxa-3,6-diazaocta-3,5-dien-l-yl) -benzeneacetamide, alpha- (methoxymethylene) -2- (4-methyl-5-phenyl-2, 7-dioxa-3,6-diazaocta-3,5-dien-l-yl) -benzeneaceticacid-methyl ester, alpha- (methoxyimino) -N-methyl-2 - [[[l- [3- (trifluoromethyl) phenyl] - ethoxy] imino] methyl] -benzeneacetamide, 2 - [[(3,5-dichloro-2-pyridinyl) oxy] methyl] -. alpha .- (methoxyimino) -N-methyl-benzeneacetamide, 2- [4,5-dimethyl-9- (4-moφholinyl) -2,7-dioxa-3,6-diazanona-3,5-dien-l-yl] -. Alpha.- (methoxymethylene) -benzeneaceticacid- methyl ester;

Metal soaps such as: tin, copper, zinc naphtenate, octoate, 2-ethylhexanoate, oleate, phosphate, benzoate;

Metal salts such as:

Copper hydroxycarbonate, sodium dichromate, potassium dichromate, potassium chromate, copper sulfate, copper chloride, copper borate, zinc fluorosilicate, copper fluorosilicate;

Oxides like:

Tributyltin oxide, Cu2θ, CuO, ZnO;

Dithiocarbamates such as: Cufraneb, Ferban, potassium N-hydroxymethyl-N ^' -methyldithiobarbamate, Na- or K-dimethyldithiocarbamate, Macozeb, Maneb, Metam, Metiram, Thiram, Zineb, Ziram;

Nitriles such as:

2,4,5,6-tetrachloroisophthalonitrile, disodium cyano-dithioimidocarbamate;

Quinolines such as:

8-hydroxyquinoline and its Cu salts;

other fungicides and bactericides such as: 5-hydroxy-2 (5H) furanon; 4,5-benzdithiazolinone, 4,5-trimethylene dithiazolinone, N-

(2-p-chlorobenzoylethyl) hexaminium chloride, 2-oxo-2- (4-hydroxyphenyl) acethydr oximic acid chloride, tris-N- (cyclohexyldiazeniumdioxy) aluminum, N- (cyclo-hexyldiazeniumdioxy) - tributyltin or K salts, bis-N- (cyclohexyldiazeniumdioxy) copper;

Zeolites containing Ag, Zn or Cu alone or enclosed in polymeric materials. Material protection mixtures with azaconazole, bromuconazole, cyproconazole, dichlobutrazole, diniconazole, hexaconazole, metaconazole, penconazole, propiconazole, tebuconazole, dichlofluanide, tolylfluanid, fluorfolpet, methfuroxam [b2], carboxin, dioxoxin, benzoxhen, carboxylic acid cyclohexylamide, fenpiclonil, 4- (2, 2-difluoro-1,3-benzodioxol-4-yl) - 1 H-pyrrole-3-carbonitrile, butenafine, imazalil, N-methyl-isothiazolin-3-one, 5-chlorine -N-methylisothiazolin-3-one, N-octylisothiazolin-3-one, dichloro-N-octylisozhiazolinon, mercaptobenthiazole, thiocyanatomethylthiobenzothiazol, benzisothiazolinone, Nn-butylisothiazolinone, N- (2-hydroxypropyl) amino-methanol (hemi) methanol, benzyl alcohol - Formal, N-methylolchloroacetamide, N- (2-hydroxypropyl) amine-methanol, glutaraldehyde, omadine, dimethyl dicarbonate, and / or 3-iodo-2-propynyl-n-butyl carbamate.

In addition to the above-mentioned fungicides and bactericides for material protection applications, well-effective mixtures with other active ingredients are also produced:

Insecticides / acaricides / nematicides:

Abamectin, Acephat, Acetamiprid, Acrinathrin, Alanycarb, Aldicarb, Aldoxycarb, Aldrin, Allethrin, Alpha-cypermethrin, Amitraz, Avermectin, AZ 60541, Azadirach- tin, Azinphos A, Azinphos M, Azocyclotin,

Bacillus thuringiensis, Barthrin, 4-Bromo-2 (4-chloro-phenyl) -l- (ethoxymethyl) -5- (trifluoromethyl) -lH-pyrrole-3-carbonitrile, Bendiocarb, Benfüracarb, Bensultap, Betacyfluthrin, Bifenthrin, Bioresmethrin, Bioallesmethrin, Bio Bromophos A, Bromophos M, Bufencarb, Buprofezin, Butathiophos, Butocarboxin, Butoxycarboxim,

Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, Chinomethionat, Cloethocarb, Chlordane, Chlorethoxyfos, Chlorfenvinphos, Chlorfluazuron, Chlormephos, N - [(6-Chloro-3-pyridinyl) -methyl] -N'-cyano-N -methyl-ethane-imidamide, Chloφicrin, Chloφyrifos A, Chloφyrifos M, Cis-Resmethrin, Clocythrin, Cypophenothrin Clofentezin, Coumaphos, Cyanophos, Cycloprothrin,

Cyfluthrin, cyhalothrin, cyhexatin, cypermethrin, cyromazine, Decamethrin, Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthi- uron, Dialiphos, Diazinon, l, 2-Dibenzoyl-l (l, l-dimethyl) -hydrazine, DNOC, Dichlofenthion, Dichlorvos, Dicliphos , Dicrotophos, Diflubenzuron, Dimethoat, Dimethyl- (phenyl) -silyl-methyl-3-phenoxybenzylether, Dimethyl- (4-Ethoxyphenyl) -silyl- methy 1-3 -phenoxybenzy lether, Dimethylvinphos, Dioxathione, Disulfoton,

Eflusilanate, Emamectin, Empenthrin, Endosulfan, EPN, Esfenvalerat, Ethiofencarb, Ethion, Ethofenprox, Etrimphos,

Fenamiphos, Fenazaquin, Fenbutatinoxid, Fenfluthrin, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fensulfothion, Fenthion, Fenvalerate, Fipronil, Fluazuron, Flucycloxuron, Flcyufenurionin, Flucythrinforminate, Flucythrinate, Flucythrinate, Flucythrininate, Flucythrinate, Flucythrinate, Flucythrinate, Flucythrininate, Flucythrininate, Flucythrinate, Flucythrinate, Flucythrinone, Flucythrinate, Flucythrinate, Flucythrinate, Flucythrinformin , Fosmethilan Fosthiazat, Fubfenprox, Furathiocarb,

HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydramethylnon, Hydroprene, Imidacloprid, Iodfenfos, Iprobefos, Isazophos, Isoamidophos, Isofenphos, Isoprocarb, Isoprothiolane, Isoxathion, Ivermectin, Lama-cyhalonothrin, Lufen

Kadedrin

Lambda-cyhalothrin, lufenuron,

Malathion, Mecarbam, Mervinphos, Mesulfenphos, Metaldehyde, Methacrifos, Methamidophos, Methidathion, Methiocarb, Methomyl, Metalcarb, Milbemectin, Monocrotophos, Moxiectin,

Naled, NC 184, NI 125, Nicotine, Nitenpyram,

Omethoate, Oxamyl, Oxydemethon M, Oxydeprofos,

Parathion A, Parathion M, Penfluron, Permethrin, 2- (4-phenoxyphenoxy) ethyl ethyl carbamate, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos M, Pirimiphos A, Prallethrin, Profenophos, Promecarb, Pro paphos, Propoxur, Prothiophos, Prothoat, Pymetrozin, Pyrachlophos, Pyridaphenthion, Pyresmethrin, Pyrethrum, Pyridaben, Pyrimidifen, Pyriproxifen, Quinalphos, Resmethrin, RH-7988, Rotenone, Salithion, Sulufos, Silafluofenof, Sulfot Tau-fluvalinate, Taroils, Tebufenozide, Tebufenpyrad, Tebupirimphos, Teflubenzuron, Tefluthrin, Temephos, Terbam, Terbufos, Tetrachlorvinphos, Tetramethrin, Tetramethacarb, Thiacloprid, Thiafenox, Thiafenox, Thiafenox, Thiafenox, Thiafenox, Thiafenox, Thiafenox, Thiafenox, Thiafenox, Thiafenox, Thiafenox, Thiafenox, Thiafenox, Thiafenox, Thiafenox, Thiafenox, Thiafenox, Thiafenox, Thiafenox, Thiafenox, Thiafenox, Thiafenox, Thiafenox, Thiafenox, Thiafenox, Thiafenox, Thiafenox, Thiafenox, Thiafenox, Thiafenox, Thiafenox, Thiafenox, Thiafenox, Thiafoxi Thuringiensine, tralomethrin, triarathes, triazophos, triazamates, triazuron, trichlorfon, triflumuron,

Trimethacarb, vamidothione, XMC, xylylcarb, zetamethrin;

Molluscicides: fentin acetates, metaldehydes, methiocarb. Niclosamide;

Herbicides and algicides

Acetochlor, acifluorfen, aclonifen, acrolein, alachlor, alloxydim, ametryn, amidosulfuron, amitrole, ammonium sulfamate, anilofos, asulam, atrazine, aziptrotryne, azimsulfuron,

Benazolin, benfluralin, benfuresate, bensulfuron, bensulfide, bentazone, benzofencap, benzthiazuron, bifenox, borax, bromacil, bromobutide, bromofenoxim, bromoxynil, butachlor, butamifos, butralin, butylate, bialaphos, benzoyl-prop, bromobutamide, bromobutamide, bromobutamide Chloramben, Chlorbromuron, Chlorflurenol, Chloridazon, Chlorimuron, Chlornitrofen, Chloroacetic acid, Chlorotoluron, Chloroxuron, Chloφropham, Chlorsulfuron, Chlorthal, Chlorthiamid, Cinmethylin, Cinofulsuron, Clethodim, Clomazone, Chlomyroxoxyl, Chlomidoxyloxyloxyloxyloxyloxyloxyloxyloxyloxynyl , Clodinafop-propargyl, cumyluron, CGA 248757, clometoxyfen, cyhalofop, clopyrasuluron, cyclosulfamuron,

Dichloφrop, Dichloφrop-P, Diclofop, Diethatyl, Difenoxuron, Difenzoquat, Diflufenican, Dimefuron, Dimepiperate, Dimethachlor, Dimethipin, Dinitramine, Dinoseb, Dinoseb Acetate, Dinoterb, Diphenamid, Dipropetryn, DOC, DidMA, DOC, DMA, Dithiopyron , 4-D, Daimuron, Dalapon, Dazomet, 2,4-DB, Desmedipham, Desmetryn, Dicamba, Dichlobenil, Dimethamid, Dithiopyr, Dimethametryn, Eglinazine, Endothal, EPTC, Esprocarb, Ethalfluralin, Ethidimuron, Ethofumesate,

Ethobenzanide, ethoxyfen, ET 751, ethametsulfuron,

Fenoxaprop, Fenoxaprop-P, Fenuron, Flamprop, Flamprop-M, Flazasulfuron,

Fluazifop, Fluazifop-P, Fuenachlor, Fluchloralin, Flumeturon, Fluorocglycofen, Fluoronitrofen, Flupropanate, Flurenol, Fluridone, Flurochloridone, Fluroxypyr,

Fomesafen, fosamine, flamprop-isopropyl, flamprop-isopropyl-L, flumiclorac-pentyl, flumipropyn, flumioxzim, flurtatone, flumioxzim,

Glyphosate, glufosinate-ammonium

Haloxyfop, Hexazinone, Imazamethabenz, Isoproturon, Isoxaben, Isoxapyrifop, Imazapyr, Imazaquin,

Imazethapyr, ioxynil, isopropalin, imazosulfuron,

KUH 91 1, KUH 920

Lactofen, Lenacil, Linuron, LS830556,

MCPA, MCPA-thioethyl, MCPB, Mecoprop, Mecoprop-P, Mefenacet, Mefluidide, Metam, Metamitron, Metazachlor, Methabenzthiazuron, Methazole, Methoroptryne,

Methyldymron, methylisothiocyanate, metobromuron, metoxuron, metribuzin,

Metsulfuron, Molinate, Monalide, Monolinuron, MSMA, Metolachlor, Metosulam,

Metobenzuron,

Naproanilide, Napropamide, Naptalam, Neburon, Nicosulfuron, Norflurazon, sodium chlorate,

Oxadiazon, oxyfluorfen, orbencarb, oryzalin, quinchlorac, quinmerac,

Propyzamides, prosulfocarb, pyrazolates, pyrazolesulfuron, pyrazoxyfen, pyributicarb,

Pyridates, paraquat, pebulates, pendimethalin, pentachlorophenol, pentanochlor,

Petroleum oils, Phenmedipham, Picloram, Piperophos, Pretilachlor, Primisulfuron, Prodiamine, Prometryn, Propachlor, Propanil, Propaquizafob, Propazine, Propham,

Pyrithiobac,

Quinmerac, Quinocloamine, Quizalofop, Quizalofop-P,

Rimsulfuron

Sethoxydim, Sifuron, Simazine, Simetryn, Sulfometuron, Sulfentrazone, Sulcotri- one, Sulfosate, Tar oils, TCA, tebutam, tebuthiuron, terbacil, terbumetone, terbuthylazine, ter-butryn, thiazafluoron, thifensulfuron, thiobencarb, thiocarbazil, tralkoxydim, triallate, triasulfuron, tribenuron, triclopyropyrinid, triclopyropyrinid, triclopyropyrinid, triclopyropyrinid, triclopyropyrinid, triclopyropyrinid Vernolate.

The active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules. They are used in the usual way, e.g. by pouring, splashing. Spraying, scattering, dusting, foaming, brushing, etc. It is also possible to apply the active ingredients using the ultra-low-volume process or to inject the active ingredient preparation or the active ingredient itself into the soil. The seeds of the plants can also be treated.

When the active compounds according to the invention are used as fungicides, the application rates can be varied within a relatively wide range, depending on the type of application. When treating parts of plants, the active compound application rates are generally in the range from 0.1 to 10,000 g / ha, preferably from 10 to 1,000 g / ha. In the case of seed treatment, the active compound application rates are generally in the range from 0.001 to 50 g per kg of seed, preferably from 0.01 to 10 g per kg of seed. When treating the soil, the active compound application rates are generally in the range from 0.1 to 10,000 g / ha, preferably from 1 to 5,000 g / ha.

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

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

With good plant tolerance and favorable toxicity to warm-blooded animals, 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 caφophagus, Scutigera spp ..

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

From the order of the Blattaria, for example Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica. From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Isoptera e.g. Reticulitermes spp ..

From the order of the Phthiraptera e.g. Pediculus humanus coφoris, Haematopinus spp., Linognathus spp., Trichodectes spp., Damalinia spp ..

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

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 e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis,

Aphis fabae, aphis pomi, eriosoma lanigerum, hyalopterus arundinis, phylloxera vastatrix, pemphigus spp., Macrosiphum avenae, myzus spp., Phorodon humuli, rhopalosiphum padi, empoasca spp , 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 xylostella, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiisispppp., Phyllocnist.

Earias insulana, Heliothis spp., Mamestra brassicae, Panolis flammea, Spodoptera spp., Trichoplusia ni, Caφocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonellaella, Tineolaeaellellaella, Tineolaeaellaella , Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima. Tortrix viridana, Cnaphalocerus spp .. From the order of the Coleoptera, for example, Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysozaisamaso - mus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meliginus spp., Pt , Gibbium psylloides, Tribolium spp., Tenebrio molitor, 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 e.g. Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Sto- moxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa, Hylemyia spp., Liriomy ..

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

From the class of the Arachnida, for example Scoφio maurus, Latrodectus mactans, Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyommomma spp., ., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Hemitarsonemus spp., Brevipalpus spp .. Plant-parasitic nematodes include, for example, Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Tripusichpp. Spp., Xiphinema spp. .

The compounds of the formula (I) according to the invention can be used with particularly good success for combating plant-damaging insects, for example against the caterpillars of the cockroach (Plutella maculipennis).

When used as insecticides, the active compounds according to the invention can also be present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with synergists. Synergists are compounds that increase the effectiveness of the active ingredients 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 in a range from 0.0000001 to 95% by weight of active substance, preferably from 0.0001 to 1% by weight.

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

When used against hygiene pests and pests of stored products, the active substance is distinguished by an excellent residual action on wood and clay and by a good stability to alkali on limed substrates.

The preparation and use of the active compounds according to the invention can be seen from the examples below. Manufacturing examples

example 1

1 g (6.5 mmol) Chlordithiazindioxid werden in 25 ml DMF gelöst und mit einer Lösung von 1.09 g (6.5 mmol) Mercaptobenzothiazol und 0.66 g (0.66 mmol) Tri- ethylamin in 15 ml DMF versetzt. Man rührt 4 Stunden bei Raumtemperatur, gibt auf Wasser und saugt ab. Der Rückstand wird mit Wasser und Diethylether gewaschen und im Vakuum getrocknet. Ausbeute 1.79 g (= 86 % d. Th.), Fp. = 165°C

1 g (6.5 mmol) of chlorodithiazine dioxide is dissolved in 25 ml of DMF and a solution of 1.09 g (6.5 mmol) of mercaptobenzothiazole and 0.66 g (0.66 mmol) of triethylamine in 15 ml of DMF are added. The mixture is stirred for 4 hours at room temperature, poured into water and suction filtered. The residue is washed with water and diethyl ether and dried in vacuo. Yield 1.79 g (= 86% of theory), mp = 165 ° C

Example 2

1.48 g (10.7 mmol) of mercaptotriazole Na salt are placed in 6 ml of acetonitrile and mixed with a solution of 1.8 g (10.7 mmol) of chlorodithiazole dioxide in 12 ml of acetonitrile. The mixture is stirred at room temperature for 20 h, filtered from NaCl formed and the filtrate evaporated. Yield 1.74 g (= 69% of theory), mp. 179 ° C (Z.)

Analogous to Example 1 and Example 2 and the general description, the in

Table 1 example compounds obtained. Table 1

Examples of use

The minimal inhibitory concentrations (MIC) of agents according to the invention are determined to demonstrate the activity against fungi:

Example A

An agar which is produced using malt extract is mixed with active compounds according to the invention in concentrations of 0.1 mg / 1 to 5000 mg / 1. After the agar has solidified, it is contaminated with pure cultures of those in the table

2 listed test organisms. After 2 weeks of storage at 28 ° C and 60 to 70% relative humidity, the MIC is determined. MIC is the lowest concentration of active ingredient at which no growth occurs due to the type of microbe used, it is shown in Table A below.

Example B

Plasmopara test (vine) / protective

Solvent: 24.5 parts by weight of acetone

24.5 parts by weight of dimethylacetamide

Emulsifier: 1.0 part by weight of 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 washed with an aqueous spore suspension of

Plasmopara viticola inoculated and then remain in an incubation cabin at about 20 ° C and 100% relative humidity for 1 day. The plants are then placed in a greenhouse at about 21 ° C. and about 90% relative atmospheric humidity for 5 days. The plants are then moistened and placed in an incubation cabin for 1 day.

Evaluation is carried out 6 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.

In this test, those in Examples 1, 3, 4, 5, 6, 7, 8, 9, 10, 12, 13, 15, 18, 20,

22, 25, 26 and 42 listed substances according to the invention with an application rate of 250 g / ha an efficiency of 90%> or more. Example C

Erysiphe test (barley) / protective

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

Emulsifier: 1, 2 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 effectiveness, young plants are sprayed with the active compound preparation in the stated application rate. One day after the treatment, the plants are spotted with Erysiphe graminis f.sp. Hordei inoculated. The plants are then placed in a greenhouse at 70% relative atmospheric humidity and a temperature of 18 ° C.

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

In this test, the substances according to the invention listed in Examples (22) and (27) show an efficiency of 90% or more at an application rate of 750 g / ha.

Example: D

Plutella test / artificial feed

Solvent: 100 parts by weight of acetone

Emulsifier: 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 concentrate is diluted with methanol to the desired concentration.

A specified amount of active compound preparation of the desired concentration is pipetted onto a standardized amount of synthetic feed. After the methanol has evaporated, a film can lid with about 100 plutella eggs is placed on each cavity. The newly hatched larvae migrate to the treated synthetic food.

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

In this test e.g. the compound of preparation example (14) at an exemplary active ingredient concentration of 0.1%, a kill of 95% after 7 days.

Claims

Patent claims 1. Compounds of the general formula (I)

in which X' stands for oxygen or sulfur, Y stands for -CHR ⁷ - or -CHR ⁵ CHR ⁶ -, Z ¹ stands for sulfur, oxygen, NR ¹ , Z ² stands for CR ² or nitrogen, Z ³ stands for CR ³ or nitrogen, Z ⁴ stands for CR ⁴ or nitrogen, R ¹ , R ² , R ³ and R ⁴ are the same or different and independently represent hydrogen, cyano, nitro, substituted or unsubstituted alkyl, alkenyl, alkynyl, alkoxy, haloalkoxy, benzylthio, alkylthio, haloalkylthio, aryl, pyridyl, pyrimidyl or Pyrazinyl or are optionally connected via one of these substituents and R ⁵ , R ⁶ and R ⁷ are the same or different and independently represent hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, pyridyl, nitro, cyano or halogen. Compounds according to claim 1, characterized in that X ¹ stands for oxygen or sulfur, Y stands for -CHR ⁷ - or -CHR ⁵ CHR ⁶ -, Z' stands for sulfur, oxygen, NR', Z ² stands for CR ² or nitrogen, Z ³ stands for CR ³ or nitrogen, Z ⁴ represents CR ⁴ or nitrogen, where R ¹ , R ² , R ³ , R ⁴ independently of each other for hydrogen, cyano, nitro, straight-chain or branched alkyl (C,-C ₆ ), alkenyl (C ₂ -C ₆ ), alkynyl (C ₂ -C ₆ ), which are each optionally substituted one to several times, identically or differently, by halogen, nitro, cyano, alkoxy (C, -C ₆ ), haloalkoxy (C, -C ₆ ) with 1 to 9 the same or different halogen atoms, alkylthio (C,-C ₆ ), haloalkylthio (C,-C ₆ ) with 1 to 9 identical or different halogen atoms, phenyl, pyridyl, pyrimidyl, or pyrazinyl; for alkoxy (C _j -C ₅ ); for haloalkoxy (Cj-C ₅ ) with 1 to 6 identical or different halogen atoms, benzylthio; alkylthio (C _r C ₅ ); Halogenalkylthio (C,-C ₅ ) with 1 to 6 identical or different halogen atoms; or for phenyl, pyridyl, pyrimidyl or pyrazinyl, each of which is optionally substituted one or more times by halogen, alkyl (C,-C ₅ ), halogen- alkyl (C,-C ₅ ) with 1 to 6 identical or different halogen atoms, alkoxy (C,-C ₅ ), haloalkoxy (C,-C ₅ ) with 1 to 6 identical or different halogen atoms, alkylthio (C,-C ₅ ), haloalkylthio (C,- C ₅ ) with 1 to 6 identical or different halogen atoms, amino, monoalkylamino with straight-chain or branched alkyl radicals (C,- C ₆ ), dialkylamino with the same or different, straight-chain or branched alkyl radicals (C,-C ₅ ), or R ² and R ³ are connected -CH=CH-CH=CH-, which is optionally substituted one to four times by halogen , nitro, cyano, alkyl (C,-C ₅ ), haloalkyl (C,-C ₅ ) with 1 to 6 identical or different halogen atoms, alkoxy (C,-C ₅ ), haloalkoxy (C,-C ₅ ) with 1 to 6 identical or different halogen atoms, alkylthio (C _r C ₅ ), haloalkylthio (C,-C ₅ ) with 1 to 6 identical or different halogen atoms, amino, monoalkylamino with straight-chain or branched alkyl radicals (C,-C ₆ ), dialkylamino with same or different, straight-chain or branched alkyl radicals (C,-C ₅ ), or fused with an aryl ring, R ⁵ , R ⁶ or R ⁷ are the same or different and independently represent hydrogen, nitro, cyano, halogen, straight-chain or branched Alkyl (C,-C ₈ ), alkenyl (C ₂ -C ₈ ) or alkynyl (C ₂ -C ₈ ), which is optionally substituted one to several times, identically or differently, by halogen, optionally substituted phenyl, alkoxy (C, -C ₅ ), haloalkoxy (C,-C ₅ ) with 1 to 6 identical or different halogen atoms, acyl (C,-C ₅ ) or for optionally substituted aryl, Pyridyl stand. 3. Compounds according to claim 1, characterized in that X ¹ stands for oxygen or sulfur, Y stands for -CHR ⁷ - or -CHR ⁵ CHR ⁶ -, Z' stands for sulfur, oxygen, NR ¹ , Z ² stands for CR ² or nitrogen, Z ³ stands for CR ³ or nitrogen, Z ⁴ represents CR ⁴ or nitrogen, where R', R ² , R ³ , R ⁴ independently of each other for hydrogen, cyano, nitro, straight-chain or branched alkyl (C,-C ₅ ), alkenyl (C ₂ -C ₅ ), alkynyl (C,-C ₅ ), which are each optionally substituted one to several times, identically or differently, by fluorine, chlorine, nitro, cyano, alkoxy (C,-C ₄ ), haloalkoxy (C,-C ₄ ) with 1 to 5 identical or different fluorine and/or or chlorine atoms, alkylthio (C,-C ₄ ), haloalkylthio (C,-C ₄ ) with 1 to 5 identical or different fluorine and/or chlorine atoms, phenyl, pyridyl, pyrimidyl or pyrazinyl; for alkoxy (Cj-C4); for haloalkoxy (Cj-C ) with 1 to 4 identical different fluorine and/or chlorine atoms; Benzylthio, alkylthio (C _j -C ); Halogenalkylthio (CC^ with 1 to 4 identical or different fluorine or chlorine atoms, or for phenyl, pyridyl, pyrimidyl or pyrazinyl, each of which is optionally substituted one to several times, identically or differently, by fluorine and/or chlorine, alkyl (C,-C ₄ ), haloalkyl (C,-C ₄ ) with 1 to 4 identical or different Fluorine and/or chlorine atoms, alkoxy (C,-C ₄ ), haloalkoxy (C,-C- ₄ ) with 1 to 4 identical or different fluorine and/or chlorine atoms, alkylthio (C,-C ₄ ), haloalkylthio ( C,-C ₄ ) with 1 to 4 identical or different fluorine or chlorine atoms, amino, monoalkylamino with straight-chain or branched alkyl radicals (C,- C ₅ ), dialkylamino with the same or different, straight-chain or branched alkyl radicals (C,-C ₄ ), or R ² and R ³ are connected via the group -CH=CH-CH=CH-, which is optionally substituted one to four times is characterized by fluorine, chlorine, nitro, cyano, alkyl (C,-C ₄ ), haloalkyl (C,-C ₄ ) with 1 to 4 identical or different fluorine and/or chlorine atoms, alkoxy (C,-C ₄ ), Halogenalkoxy (C,-C ₄ ) with 1 to 4 identical or different fluorine and/or chlorine atoms, alkylthio (C,-C ₄ ), halogenalkylthio (C,-C ₄ ) with 1 to 4 identical or different fluorine and/or chlorine atoms or chlorine atoms, amino, monoalkylamino with straight-chain or branched alkyl radicals (C,-C ₅ ), dialkylamino with the same or different, straight-chain or branched alkyl radicals (C,-C ₄ ), or are fused with an aryl ring. R ⁵ , R ⁶ or R ⁷ are the same or different and are independent of one another Hydrogen, nitro, cyano, fluorine, chlorine, straight-chain or branched alkyl (C _r C ₆ ), alkenyl (C ₂ -C ₆ ) or alkynyl (C ₂ -C ₆ ), which may optionally be substituted one or more times, identically or differently is fluorine, chlorine, optionally substituted phenyl, alkoxy (C,-C ₄ ), haloalkoxy (C,-C ₄ ) with 1 to 5 identical or different fluorine and/or chlorine atoms, acyl (C,-C ₅ ) or represent optionally substituted aryl, pyridyl. 4. Compounds according to claim 1, characterized in that X' stands for oxygen or sulfur, Y stands for -CHR ⁷ - or -CHR ⁵ CHR ⁶ -, Z ¹ stands for sulfur, oxygen, NR ¹ , Z ² stands for CR ² or nitrogen, Z ³ stands for CR ³ or nitrogen, Z ⁴ represents CR ⁴ or nitrogen, where R ¹ , R ² , R ³ , R ⁴ are the same or different and independently represent hydrogen, cyano, nitro, straight-chain or branched alkyl, alkenyl, alkynyl, in particular methyl, ethyl, n-propyl, i-propyl, n-butyl , i-Butyl, s-Butyl, t-Butyl, Cyclohexyl, Cyclopentyl, Allyl, Propargyl, each of which is optionally substituted one to three times, identically or differently, by fluorine, chlorine, nitro, cyano, alkoxy, in particular methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy , t-butoxy, haloalkoxy, in particular difluoromethoxy, trifluoromethoxy, dichlorofluoromethoxy, difluorochloromethoxy, pentafluorethoxy, benzylthio, alkylthio, in particular methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio, t -Butylthio, haloalkylthio, in particular difluoromethylthio, trifluoromethylthio, dichlorofluoromethylthio, difluorochloromethylthio, pentafluoroethylthio, phenyl, pyridyl, pyrimidyl, pyrazinyl; for alkoxy, in particular methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy; for haloalkoxy, in particular difluoromethoxy, trifluoromethoxy, dichlorofluoromethoxy, difluorochloromethoxy, pentafluoroethoxy; for benzylthio; for alkylthio, especially methylthio, ethylthio, n-propylthio, i-propylthio, n- butylthio, i-butylthio, s-butylthio, t-butylthio; for haloalkylthio, in particular difluoromethylthio, trifluoromethylthio, dichlorofluoromethylthio, difluorochloromethylthio, pentafluoroethylthio; or for phenyl, pyridyl, pyrimidyl, pyrazinyl, which are optionally substituted one to three times, identically or differently, by fluorine, chlorine, Alkyl, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t- Butyl, haloalkyl, in particular difluoromethyl, trifluoromethyl, dichlorofluoromethyl, difluorochloromethyl, pentafluoroethyl, alkoxy, in particular methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, haloalkoxy, in particular difluoro - methoxy, trifluoromethoxy, dichlorofluoromethoxy, difluorochloromethoxy, pentafluorethoxy, alkylthio, in particular methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio, t-butylthio, haloalkylthio, in particular difluoromethylthio, trifluoromethylthio , dichlorofluoromethylthio, difluorochloro-methylthio, pentafluoroethylthio, amino, monoalkylamino or dialkylamino with the same or different, straight-chain or branched alkyl radicals, in particular methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t -Butyl, stand, or R ² and R ³ are connected via the groups -CH=CH-CH=CH-, which is optionally substituted one to three times by fluorine and/or chlorine, nitro, cyano, alkyl, in particular methyl, ethyl, n-propyl, i - Propyl, n-butyl, i-butyl, s-butyl, t-butyl, haloalkyl, especially difluoromethyl, trifluoromethyl, dichlorofluoromethyl, difluorochloromethyl, pentafluoroethyl, alkoxy, especially methoxy, ethoxy, n-propoxy, i-propoxy, n -Butoxy, i-butoxy, s-butoxy, t-butoxy, haloalkoxy, such as difluoromethoxy, trifluoromethoxy, dichlorofluoromethoxy, difluorochloromethoxy, pentafluoroethoxy, alkylthio, in particular methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio , s-butylthio, t-butylthio, haloalkylthio, in particular Difluoromethylthio, trifluoromethylthio, dichlorofluoromethylthio, difluorochloromethylthio, pentafluoroethylthio, amino, monoalkylamino or dialkylamino with identical or different, straight-chain or branched alkyl radicals, in particular methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, R ⁵ , R ⁶ or R ⁷ are the same or different and independently represent hydrogen, nitro, cyano, fluorine, chlorine, straight-chain or branched alkyl, alkenyl, alkynyl, in particular methyl, ethyl, n-propyl, i-propyl, n- Butyl, i-butyl, s-butyl, t-butyl, allyl, propargyl, which is optionally substituted by fluorine and/or chlorine, optionally substituted phenyl, alkoxy, in particular methoxy, ethoxy, n-propoxy, i-propoxy, n- Butoxy, i-butoxy, s-butoxy, t-butoxy, haloalkoxy, in particular difluoromethoxy, trifluoromethoxy, dichlorofluoromethoxy, difluorochloromethoxy, pentafluoroethoxy, acyl, in particular formyl, acetyl, n-propionyl, i-propionyl, n-butyryl, i- Butyryl, s-butyryl, or optionally substituted aryl, pyridyl. 5. A process for the preparation of compounds of formula (I) as defined in claim 1, characterized in that a) compounds of the general formula (II),

in which Y has the meaning given in claim 1 and X ² represents bromine or chlorine, with compounds of the general formula (III),

in which X, Z, Z, Z and Z have the meanings given in claim 1, optionally reacted in the presence of a base and optionally in the presence of a diluent, or b) compounds of the general formula (IV),

M ⁺ in which have the meanings specified in claim 1, and M ⁺ represents an alkali or alkaline earth ion with compounds of the general formula (VI)

in which Z ¹ , Z ² , Z ³ and Z ⁴ have the meanings given in claim 1 and X ³ for a leaving group, especially for mesyl, tosyl, fluorine, chlorine or bromine, optionally reacted in the presence of a base and optionally in the presence of diluents or for the production of compounds as defined in claim 1 with X ¹ in its meaning as sulfur, the salts of the general formula (IV)

M ⁺ in which Y has the meaning given in claim 1 and M ⁺ represents an alkali or alkaline earth metal ion, in particular Na ⁺ or K ⁺ , with diazonium salts of the general formula (V)

in which Z ¹ , Z ² , Z ³ and Z ⁴ have the meanings given above and A ^~ stands for the anion of a mineral acid, in aqueous/alkaline solution, optionally in the presence of a catalyst. 6. A process for producing agents, characterized in that compounds as defined in claims 1 to 4 are mixed with extenders and/or carriers and/or surface-active agents. 7. Agents containing extenders and/or carrier substances and optionally surface-active substances, characterized by a content of at least one compound as defined in claims 1 to 4. 8. A method for combating pests, characterized in that compounds as defined in claims 1 to 4 or agents as defined in claim 7 are allowed to act on pests and / or their habitat. 9. Use of compounds as defined in claims 1 to 4 or of agents as defined in claim 7 to combat pests.