EP1173428A1 - O-aryl dithiazole dioxides - Google Patents

Abstract

The invention relates to novel O-aryl dithiazole dioxides, to two methods for producing the same and to the use thereof as pesticides for protecting plants and materials.

Description

O-aryldithiazole dioxides

The invention relates to new O-aryldithiazole dioxides, two processes for their preparation and their use as pesticides in crop protection and

Material protection.

Certain aryldithiazole dioxides with a similar substitution pattern and their action against organisms which damage plants and materials have already become known (cf. DE-19545635 and WO98-29400). The effect of this previously known

However, especially in the case of low application rates and concentrations, compounds are not completely satisfactory in all fields of application.

The new compounds of the general formula (I) have now been found.

in which

Ar stands for substituted or unsubstituted aryl and

Y represents substituted or unsubstituted, straight-chain or branched alkanediyl.

In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, are also straight-chain or branched, also in combination with heteroatoms, such as in alkoxy or alkylthio. Aryl stands for aromatic, mono or polycyclic hydrocarbon rings, such as phenyl, naphthyl. Anthranyl, phenanthryl. preferably phenyl or naphthyl, especially phenyl.

Substituents of the present application are to be understood in particular as those mentioned in the individual preferred areas.

Substituents for aryl or for alkanediyl, in particular for aryl, are: halogen, cyano, thiocyano, nitro, amino, formyl, carbamoyl, thiocarbamoyl, hydrogen, hydroxy; each straight-chain or branched alkyl, cyanoalkyl, hydroxyalkyl, alkoxy, alkoxyalkyl, hydroxyalkoxy, alkylthioalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 8 carbon atoms; each straight-chain or branched, optionally mono- or disubstituted by cyano, nitro, phenyl, nitrophenyl, dinitrophenyl, alkoxycarbonylamino, phthalimidyl, bis- (alkoxycarbonylamino) or dioxobenzimidazolyl-substituted alkenyl, alkenyloxy or alkenylcarbonyl, each with 2 to 6 carbon atoms in the alkenyl part; in each case straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms; each straight-chain or branched halogenaikenyl or haloalkenyloxy each having 2 to 6 carbon atoms and 1 to 1 1 identical or different halogen atoms; each straight-chain or branched alkylamino, dialkylamino,

Alkylcarbonyl, thiocyanoalkylcarbonyl, haloalkylcarbonyl (with 1 to 3 halogen atoms), alkoxycarbonyl, alkoxycarbonylazoalkyl, alkylaminocarbonyl, dialkylaminocarbonyl or arylalkylaminocarbonyl with 1 to 6 carbon atoms in the respective hydrocarbon chains or optionally cycloalkylcarb- substituted by up to four times by halogen or alkyl with 1 to 4 carbon atoms onylamino or cycloalkyl with 3 to 6 carbon atoms in the cycloalkyl part; Cycloalkyl or cycloalkyloxy each having 3 to 6 carbon atoms; each optionally by halogen, alkyl, phenyl, alkoxy, alkylthio. Alkylsulfinyl or alkylsulfonyl with 1 to 4 carbon atoms, haloalkyl, haloalkoxy. Haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl with 1 to 4 carbon atoms and 1 to 9 halogen atoms substituted phenyl, phenoxy, phenylzo, phenylthio, phenylsulfonyl, phenylcarbonyl, phenylalkylcarbonyl, or phenylalkoxy with 1 to 4 carbon atoms in the alkyl part, in each case optionally by halogen, oxo, alkyl , Alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl having 1 to 4 carbon atoms, haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl having 1 to 4 carbon atoms and 1 to 9 halogen atoms or phenyl substituted heterocyclyl, heterocyclylalkyl having 1 to 4 carbon atoms in the alkyl part, heterocycyllyl , Heterocyclylsulfinyl, Heterocyclylsulfonyl, Heterocyclylcarbonyl, Heterocyclylthiocarbonyl, Benzoheterocyclyl, Benzoheterocyclylaikyl with 1 to 4 carbon atoms in the alkyl part, Benzoheterocyclyloxy, Benzoheterocyclylthio,

Benzoheterocyclylsulfinyl, benzoheterocyclylsulfonyl, benzoheterocyclylcarbonyl or benzoheterocyclylthiocarbonyl each having 5 or 6 ring members in the heterocyclic part,

A ¹ or a grouping _j . wherein

A ² ^ T represents CH or nitrogen

A represents hydrogen or alkyl having 1 to 4 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, phenyl, heterocyclyl having 5 or 6 ring members, alkoxycarbonyl having 1 to 4 carbon atoms in the alkyl part, benzylaminocarbonyl, benzyloxyaminocarbonyl or aminocarbonyl and

A-2 for hydroxy, amino, alkyl, phenyl, benzyl, alkoxy, cyanoalkoxy, benzyloxy, alkylamino, dialkylamino, alkoxycarbonylamino, alkoxycarbonylphenyl, each with 1 to 4 carbon atoms in the respective alkyl chains or alkenyloxy having 2 to 4 carbon atoms.

Haloalkyl stands for partially or completely halogenated alkyl. In the case of polyhalogenated haloalkyl, the halogen atoms can be the same or different. Preferred halogen atoms are fluorine and chlorine and especially fluorine. Wearing that

Haloalkyl still further substituents, the maximum possible number of halogen atoms is reduced to the remaining free valences.

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

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. is an atom other than carbon. If the ring contains several heteroatoms, these can be the same or different. Heteroatoms are preferably oxygen, nitrogen or sulfur. If the ring contains several oxygen atoms, they are not adjacent. If appropriate, the ring-shaped compounds together with other carbocyclic or heteroeyclic, fused or bridged rings together form a polycyclic ring system. A polycyclic ring system can be linked via the heteroeyclic ring or a fused-on carbocyclic ring. Mono- or bicyclic ring systems are preferred, in particular mono- or bicyclic aromatic ring systems.

Furthermore, it was found that the new compounds of the general formula (I) are obtained (process a) if dithiazole dioxides of the general formula (II)

in which Y has the meaning given above and

X represents halogen, alkyl or arylsulfonyl.

with phenols of the general formula (III)

Ar-OH (III) in which

Ar has the meaning given above and

if appropriate in the presence of a diluent, if appropriate in the presence of an acid acceptor and if appropriate in the presence of a catalyst.

Finally, it was found that the new compounds of the general formula (I) have a very strong fungicidal and insecticidal activity.

The compounds according to the invention can optionally be in the form of mixtures of various possible isomeric forms, in particular stereoisomers, such as e.g.

E and Z, or optical isomers are present. Both the E and the Z isomers, the individual enantiomers, the racemates and any mixtures of these isomers are claimed.

The invention preferably relates to compounds of the formula (I-a),

in which

R ¹ . R ² , R \ R ⁴ and R 'are identical or different and independently of one another represent the following substituents: halogen, cyano. Thiocyano. Nitro, amino, formyl. Carbamoyl, thiocarbamoyl, hydrogen, hydroxy; each straight-chain or branched alkyl, cyanoalkyl, hydroxyalkyl, alkoxy, alkoxyalkyl, hydroxyalkoxy, alkylthioalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 8 carbon atoms; each straight-chain or branched, optionally mono- or disubstituted by cyano, nitro, phenyl, nitrophenyl, dinitrophenyl, alkoxycarbonylamino, phthalimidyl, bis- (alkoxycarbonylamino) or dioxobenzimidazolyl-substituted alkenyl, alkenyloxy or alkenylcarbonyl, each with 2 to 6 carbon atoms in the alkenyl part; each straight-chain or branched haloalkyl. Haloalkoxy. Haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms; each straight-chain or branched halogenaikenyl or haloalkenyloxy each having 2 to 6 carbon atoms and 1 to 1 1 identical or different halogen atoms; in each case straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, thiocyanoalkylcarbonyl, haloalkylcarbonyl (with 1 to 3 halogen atoms), alkoxycarbonyl, alkoxycarbonylazoalkyl, alkylaminocarbonyl, dialkylaminocarbonyl or arylalkylaminocarbonyl with 1 to 6 carbon atoms in the respective hydrocarbon chains or, if appropriate, single to four-chain or by simple cycloalkylcarbonylamino or cycloalkyl having 3 to 6 carbon atoms in the cycloalkyl part substituted by 1 to 4 carbon atoms;

Cycloalkyl or cycloalkyloxy each having 3 to 6 carbon atoms; each optionally by halogen, alkyl, phenyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl having 1 to 4 carbon atoms. Haloalkyl, haloalkoxy, haloalkylthio. Haloalkylsulfinyl or haloalkylsulfonyl with 1 to 4 carbon atoms and 1 to 9 halogen atoms substituted phenyl, phenoxy, phenylazo. Phenylthio. Phenylsulfonyl, phenylcarbonyl, phenylalkylcarbonyl, or phenylalkoxy having 1 to 4 carbon atoms in the alkyl part, in each case optionally by halogen, oxo, alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl having 1 to 4 carbon atoms, haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl having 1 to 4 carbon atoms and 1 to 9 halogen atoms or phenyl-substituted heterocyclyl, heterocyclylalkyl with 1 to 4 carbon atoms in the alkyl part, heterocyclyloxy, heterocyclylthio, heterocyclylsylfinyl, heterocyclylsulfonyl, heterocyclylcarbonyl, heterocyclyl benzyl with benzyl, benzyl Benzoheterocyclyl-sulfinyl, benzoheterocyclylsulfonyl, benzoheterocyclylcarbonyl or benzoheterocyclylthiocarbonyl, each with 5 or 6 ring members in the heterocylyl part,

A ¹ or a grouping T, wherein

A ² ^

T represents CH or nitrogen,

A * for hydrogen or alkyl with 1 to 4 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, phenyl, heterocyclyl with 5 or 6

Ring members, alkoxycarbonyl having 1 to 4 carbon atoms in the alkyl part, benzylaminocarbonyl, benzyloxyaminocarbonyl or aminocarbonyl, A- for hydroxy, amino, alkyl, phenyl. Benzyl. Alkoxy. Cyanoalkoxy. Benzyloxy. Λlkylamino, dialkylamino. Alkoxycarbonylamino. Alkoxycarbonylphenyl each having 1 to 4 carbon atoms in the respective alkyl chains or alkenyloxy having 2 to 4 carbon atoms, and

Y represents alkylene which has 1 to 8 carbon atoms and is optionally mono- or disubstituted by phenyl, the connecting sites of the alkylene chain being particularly preferably on the same or on directly adjacent carbon atoms.

The invention also preferably relates to compounds of the formula (I-b).

in which

Ar 'represents one of the following groups:

which are each bonded via the phenyl ring and in turn can be mono- to disubstituted, the possible substituents preferably being selected from the following list: halogen, cyano, thiocyano, nitro, amino, formyl, carboxy, carbamoyl, thiocarbamoyl; in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 8 carbon atoms; each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms; in each case straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl or arylalkylaminocarbonyl having 1 to 6 carbon atoms in the respective hydrocarbon chains or optionally cycloalkylcarbonylamino or cycloalkyl having 3 to 4 times substituted by halogen or alkyl having 1 to 4 carbon atoms up to 6 carbon atoms in the cycloalkyl part;

Cycloalkyl or cycloalkyloxy each having 3 to 6 carbon atoms; each optionally by nitro, halogen, alkyl, phenyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl having 1 to 4 carbon atoms, haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or Haloalkylsulfonyl with 1 to 4 carbon atoms and 1 to 9 halogen atoms substituted phenyl, phenoxy, phenylthio. Phenylsulfone l. Phenylcarbonyl, phenylalkylcarbonyl, or phenylalkoxy with 1 to 4 carbon atoms in the alkyl part. and

Y represents alkylene which has 1 to 8 carbon atoms and is optionally mono- or disubstituted by phenyl, the connecting sites of the alkylene chain being particularly preferably on the same or on directly adjacent carbon atoms.

The present application relates in particular to compounds of the formula (I-a) in which

R ', R \ R \ R and R ^{5 are} identical or different and independently of one another represent the following substituents:

Fluorine, chlorine, bromine, cyano, thiocyano, nitro, amino, formyl, carbamoyl,

Thiocarbamoyl, hydrogen, hydroxy,

Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl. Methoxymethyl.

Cyanomethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl. Hydroxybutyl. Hydroxypentyl, hydroxyhexyl,

Methoxy, ethoxy, n- or i-propoxy, hydroxyethoxy,

Methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl,

Methylsulfonyl or ethylsulfonyl,

Methylaminomethyl, dimethylaminomethyl, in each case optionally single or double by cyano, nitro, phenyl,

Nitrophenyl, dinitrophenyl, methoxycarbonylamino, phthalimidyl, bis-

(methoxycarbonylamino) or dioxobenzimidazolyl substituted vinyl,

Allyl, 2-methylallyl, propen-1-yl, crotonyl, propargyl, vinyloxy, allyloxy,

2-methylallyloxy, propen-1-yloxy, crotonyloxy, propargyloxy, vinylcarbonyl, allylcarbonyl, 2-methylallylcarbonyl, propen-1 -ylcarbonyl, crotonylcarbonyl, propargylcarbonyl; Trifluoromethyl, trifluoroethyl,

Difluoromethoxy, trifluoromethoxy. Difluorochloromethoxy. Trifluoroethoxy, pentafluoroethoxy, 2-chloro-l, 1,2-trifluoroethoxy, difluoromethylthio. Trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl,

Methylamino, ethylamino, n- or i-propylamino, dimethylamino. Diethylamino,

Methylcarbonyl, acetyl, propionyl, thiocyanomethylcarbonyl, chloro-t-butylcarbonyl, methoxycarbonyl, ethoxycarbonyl, ethoxycarbonylazo-methyl, methylaminocarbonyl, ethylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, optionally up to four times substituted by chlorine, bromine, methyl or ethylopropyl cyclopropyl, cyclopropyl , Cyclobutyl, Cyclopentyl or Cyclohexyl, Cyclopentyl, Cyclohexyl, Cyclopentyloxy, Cyclohexyloxy, Cyclohexylcarb- onylamino, each optionally by nitro, fluorine, chlorine, methyl. Trifluoromethyl, phenyl or methoxy substituted phenyl, phenoxy, phenylazo. Phenylthio. Phenylsulfonyl, phenylcarbonyl, benzylcarbonyl or benzyl, for optionally single to triple by methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, O o, fluorine, chlorine, bromine. Trifluoromethyl or phenyl substituted dithiazole, dithiazoloxy, oxadiazole. Benzofuranyl, benzofuranylcarbonyl, pyridazine, benzoxazole, pyrimidyl, morpholinyl, morpholinylthiocarbonyl, thienyl, imidazolyl, thiadiazolyl, pyridyl, pyridazinone, furyl, piperazinyl, pyrimidylthio, thiazolyl, diazazylylthio-thiazolylthio;

A ¹ . or a grouping _j in which

A ² ^

represents CH or nitrogen, A 'for hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopentyl, cyclohexyl, phenyl, dioxazinyl. Methoxycarbonyl. Ethoxycarbonyl, benzylaminocarbonyl. Benzyloxyaminocarbonyl or aminocarbonyl.

A ~ for hydroxy, amino, methyl, ethyl. Phenyl, benzyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, cyanomethoxy, benzyloxy, methylamino, ethylamino, dimethylamino, diethylamino, methoxycarbonylamino, ethoxycarbonylamino, methoxycarbonylphenyl, Ethoxycarbonylphenyl or allyloxy, and

Y for optionally mono- or disubstituted by phenyl

Methylene, 1,1-ethylene, 1,2-ethylene 1,1-, 1,2-, 1,3- or 2,2-propylene, 1,1-, 1,2-, 1,3-, 1 , 4-, 2,2-, 2,3-butylene or 1,1-, 1,2- or 1,3- (2-methyl-propylene).

The present application also relates in particular to compounds of the formula (I-b) in which

Ar ^{1 represents} one of the following groups:

which are each bonded via the phenyl ring and in turn can be substituted up to six times, the possible substituents preferably being selected from the following list:

Fluorine, chlorine, bromine, cyano, thiocyano, nitro, amino, formyl, carboxy, carbamoyl, thiocarbamoyl,

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, pentafluoroethoxy, 2-chloro-l, l, 2-trifluorethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylfluoromethylfluoromethyl, trifluoromethyl

Methylamine ethylamino, n- or i-propylamino, dimethylamino, diethylamino,

Acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, optionally cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl which is monosubstituted to tetrasubstituted by chlorine, bromine, methyl or ethyl, Cyclopentyl, cyclohexyl, cyclopentyloxy. Cyclohexyloxy. each optionally by nitro, fluorine, chlorine. Methyl. Trifluoromethyl, phenyl or methoxy substituted phenyl. Phenoxy. Phenylthio, phenylsulfonyl, phenylcarbonyl. Benzylcarbonyl or benzyl, and

Y for optionally mono- or disubstituted by phenyl

Methylene. 1, 1-ethylene, 1, 2-ethylene 1, 1 -, 1, 2-, 1, 3- or 2,2-propylene. 1, 1 -, 1, 2-, 1, 3-, 1, 4-, 2,2-, 2,3-butylene or 1, 1 -, 1, 2- or l, 3- (2-methyl- propylene).

Compounds in which

R2 stands for chlorine, methyl, methoxy, hydroxymethyl, hydroxyethyl, trifluoromethoxy, methylcarbonyl or methoxycarbonyl, in particular for hydrogen.

Compounds in which

R ^J for fluorine, chlorine, trifluoromethyl, methyl. Nitro. Methoxy. Methylcarbonyl or methoxycarbonyl, in particular represents hydrogen.

Compounds in which

R ^{5 represents} hydrogen, chlorine, methyl, methoxy, especially hydrogen.

Compounds in which

R ^{4 represents} halogen, nitro, methoxy, carbonylmethyl, halomethyl, methoximinoethyl, in particular hydrogen.

Compounds of the formula (I) in which Y for methylene, 1, 2-ethylene. phenyl-substituted 1, 2-ethylene, 1, 1-ethylene. stands especially for methylene.

The general or preferred radical definitions given above apply both to the end products of the formula (I) and correspondingly to the starting materials or intermediates required in each case for the preparation.

The radical definitions specified for these radicals in the respective combinations or preferred combinations of radicals are independently replaced by radical definitions of other preferred ranges, irrespective of the respectively specified combination of the radicals.

Formula (II) provides a general definition of the di-thiazole dioxides required to carry out process a) according to the invention for the preparation of the compounds of formula (I) according to the invention. In this formula (II), Y preferably or in particular has the meaning which has already been stated as preferred or as particularly preferred for Y in connection with the description of the compounds of the formula (I) according to the invention. X represents halogen, preferably chlorine or bromine, or alkyl or arylsulfonyl. preferably for methyl or p-tolylsulfonyl.

Some of the starting materials of the formula (II) are known and can be prepared by known processes (compare, for example, WO 98-52945 or Bull. Chem. Soc. Jap. (1972), 45 (10), 3217-18). New and also the subject of the present

Invention are dithiazole dioxides of the formula (II-a),

in which

Y 'for methylene or 1, 2-ethylene substituted once or twice by phenyl or for 1, 1-ethylene, 1, 1 -, 1, 2- or 2,2-propylene which is optionally mono- or disubstituted by phenyl, 1.1 -, 1.2-. 2,2-, 2,3-butylene or 1,1- or 1,2- (2-methyl-propylene) is and

X ^{1 represents} halogen, preferably chlorine or bromine.

They are obtained (process b) if alkylthiodithiazoles of the general

Formula (IV),

in which

Y 'has the meaning given above and

Alk stands for alkyl,

with a halogenating agent, preferably a conventional chlorinating, brominating or iodinating agent, such as chlorine, bromine. Iodine, sulfuryl chloride, chlorosuccinimide, bromosuccinimide, 1,3-dibromo-5,5-dimethylhydantoin or iodosuccinimide, optionally in the presence of a diluent.

Those required to carry out process b) according to the invention for the preparation of the intermediates of the formula (II) according to the invention as starting materials

Formula (IV) generally defines alkylthiodithiazole dioxides. In this formula (IV), Y ¹ preferably or in particular has the meaning which has already been associated with the description of the compounds according to the invention. gene of the formula (II) was indicated as preferred or as particularly preferred for Y ¹ . Alk stands for alkyl, preferably methyl or ethyl.

Some of the starting materials of the formula (IV) are known and can be prepared by known methods (compare, for example, US 3345374).

Formula (III) provides a general definition of the phenols which are furthermore required as starting materials for carrying out process a) according to the invention for the preparation of the compounds of formula (I) according to the invention. In this formula (III), Ar preferably or in particular has the meaning which has already been stated as preferred or as particularly preferred for Ar in connection with the description of the compounds of the formula (I) according to the invention.

The starting materials of the formula (III) are known synthetic chemicals.

Suitable diluents for carrying out process a) according to the invention are all inert organic solvents. These preferably include aliphatic, alicyclic or aromatic hydrocarbons, such as petroleum ether, hexane. Heptane. Cyclohexane. Methylcyclohexane. Benzene. Toluene, xylene or decalin; halogenated hydrocarbons, such as

Chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; Ethers such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1, 2-dimethoxyethane, 1, 2-diethoxyethane or anisole; Ketones such as acetone, butanone, methyl isobutyl ketone or cyclohexanone; Nitriles, such as acetonitrile, propionitrile, n- or i-butyronitrile or

Benzonitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; Esters such as methyl acetate or ethyl acetate; Sulfoxides such as dimethyl sulfoxide; Sulfones such as sulfolane; or alcohols, such as tert-butanol. Process a) according to the invention is optionally carried out in the presence of a suitable acid acceptor. All conventional inorganic or organic bases are suitable as such. These preferably include alkaline earth metal or alkali metal hydrides or hydroxides, such as sodium hydride, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, and tertiary amines. such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, N-dimethylbenzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N, N-dimethylamino-pyridine, diazabicyclooctane (DABCO), diazabicyclonones ( DBN) or diazabicycloundecene (DBU).

The reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures from 0 ° C to 150 ° C, preferably at temperatures from 0 ° C to 80 ° C.

To carry out the process according to the invention for the preparation of the compounds of the formula (I), 1 to 15 moles, preferably 1 to 8 moles, of phenol of the formula (III) are generally employed per mole of the dithiazole of the formula (II).

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 reaction is carried out, worked up and isolated using generally customary processes (see also the preparation examples).

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 Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes. Ascomycetes. Use Basidiomycetes and Deuteromycetes.

Bactericides can be used in crop 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, 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 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 permits treatment of above-ground parts of plants, of propagation stock and seeds, and of the soil.

The active compounds according to the invention can be used particularly successfully to combat diseases in wine, fruit and vegetable cultivation, such as, for example, against Venturia. Use Phytophtora and Plasmopara species.

Other diseases in wine, fruit and vegetable cultivation, such as, for example, Pythium species, or rice diseases, such as, for example, Pyricularia species, are also combated with good success.

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 cause degradation or a change in the technical materials. The active compounds according to the invention preferably act against fungi, in particular mold, wood-discoloring and wood-destroying fungi (Basidiomycetes) and against 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 compounds 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 materials for seeds. as well as ULV cold and warm fog formulations.

These formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-producing agents Means. If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, alcohols, such as butanol or Glycol and its ethers and esters, ketones. such as acetone, methyl ethyl ketone, methyl isobutyiketone 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. Possible emulsifiers and / or foam-generating agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters. Polyoxyethylene fatty alcohol ethers, for example alkylaryl 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 powdery, granular or latex-shaped polymers can be used in the formulations. such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids. Mineral and vegetable oils can also be used as additives.

Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes, such as alizarin, azo and metal phthalocyanine dyes and trace nutrients, such as salts of iron, manganese, boron, copper, cobalt. Molybdenum and zinc 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. A propylfos potassium. Andoprim. Anilazine. Λzaconazole. 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), chlobenthiazon, chlorfenazole, chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon, cufraneb, cyymoxanilin, cymoxanilin, cymoxanilin, cymoxanil

Debacarb. Dichlorophene, diclobutrazole, diclofluanide, diclomezin, dicloran, diethofencarb, difenoconazole. Dimethirimol, dimethomorph, diniconazole. Dinicazole-M, Dinocap, Diphenylamine, Dipyrithione, Ditalimfos, Dithianon, Dodemorph, Dodine, Drazoxolon, Ediphenphos, Epoxiconazole, Etaconazole, Ethirimol. Etridiazole,

Famoxadone, fenapanil, fenarimol, fenbuconazole. Fenfuram, Fenitropan, Fenpiclonil, Fenpropidin, Fenpropimoφh, Fentinacetat, Fentinhydroxyd, Ferbam. Ferimzon, Fluazinam, Flumetover, Fluoromid. Fluquinconazole. Flurprimidol, flusilazole, fluorosulfamide, flutolanil. Flutriafol. Folpet. Fosetyl aluminum. Fosetyl sodium. Fthalid. Fuberidazole, furalaxyl. Furametpyr. Furcarbonil. Furconazole. Furconazole-cis, fur-mecyclox, guazatin,

Hexachlorobenzene, Hexaconazole, Hymexazol, Imazalil, Imibenconazol, Iminoctadin, Iminoctadinealbesilat, Iminoctadinetriacetat, Iodocarb, Ipconazol, Iprobefos (IBP), Iprodione, Irumamycin, Isoprothiolan, 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 dimethyl dithiocarbamate, nitrothal isopropyl, Nuarimol. Ofurace. Oxadixyl, oxamocarb, oxolinicacid, oxycarboxim, oxyfenthiin,

Paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen, pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz, procymidon, propamocarb. Propanosine sodium, propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil,

Pyroquilon, Pyroxyfur, Quinconazol, Quintozen (PCNB),

Sulfur and sulfur preparations,

Tebuconazole, tecloftalam, tecnazen, tetcyclacis, tetraconazole, thiabendazole,

Thicyofen, Thifluzamide, Thiophanate-methyl, Thiram, Tioxymid, Tolclofos-methyl,

Tolylfluanid, Triadimefon, Triadimenol, Triazbutil, Triazoxid, Trichlamid, Tricyclazol, Tridemoφh, Triflumizol, Triforin, Triticonazol,

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-dichloφheny l) -ß- fluoro-b-propyl-1 H-1, 2,4-triazole-1-ethanol, α- (2,4-dichloro phhenyl) -ß-methoxy-a-methyl- 1 H-1, 2,4-triazole- 1-ethanol, α- (5-methyl-l, 3-dioxan-5-yl) -ß - [[4- (trifluoromethyl) phenyl] methylene] - 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-phenoxyphenyIacetamide,

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

1 - (2,4-dichloro phhenyl) -2- (1 H-1, 2,4-triazol-1-yl) -ethanone-0- (phenolmethyl) oxime, l- (2-methyl-l-naphthalenyl) -l H-pyrrole-2,5-dione, l- (3,5-dichlorophenyl) -3- (2-propenyl) -2,5-pyrrolidinedione, l - [ (Diiodomethyl) sulfonyl] -4-methyl-benzene, l - [[2- (2,4-dichloro-phenyl) -l, 3-dioxolan-2-yl] methyl] -l H-imidazole, 1 - [[ 2- (4-chloro-phenyl) -3-phenyloxiranyl] methyl] - 1 H- 1, 2,4-triazole,

1 - [1 - [2 - [(2,4-dichlorophenyl) methoxy] phenyl] ethenyl] -1 H-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- [1 - (4-chlθφhenyl) -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 - [(l-methylethyl) sulfonyl] -5- (trichloromethyl) -l, 3,4-thiadiazole,

2 - [[6-Deoxy-4-0- (4-0-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-methylpheny 1) - 1 H-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- (l -methylethyl) -3-methyl-4 - [(3-methylbenzoyl) -oxy] -2.5-thiophene dicarboxylate. ice-1 - (4-Chloφheny l) -2- (1 H- 1, 2,4-triazol-1-yl) -cycloheptanol. cis-4- [3- [4- (l, l-dimethylpropyl) phenyl-2-methylpropyl] -2,6-dimethylmorpholine hydrochloride, ethyl - [(4-chlθφhenyl) azo] cyanoacetate,

Potassium hydrogen carbonate,

Methane tetrathiol sodium salt,

Methyl 1 - (2,3-dihydro-2,2-dimethyl-1 H-inden-1-yl) - 1 H-imidazole-5-carboxylate,

Methyl N- (2,6-dimethylphenyl) -N- (5-isoxazolylcarbonyl) -DL-alaninate, methyl-N- (chloroacetyl) -N- (2,6-dimethylphenyl) -DL-alaninate.

N- (2,3-dichloro-4-hydroxyphenyl) -1 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) -l, 4,5,6-tetrahydro-2-pyrimidinamine,

N- (4-hexylphenyl) -l, 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,

0.0-diethyl [2- (dipropylamino) -2-oxoethyl] ethyl phosphoramidothioate,

O-methyl-S-phenyl-phenylpropylphosphoramidothioate,

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

Azadirachtin, Azamethiphos, Azinphos A, Azinphos M, Azocyclotin, Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillus thuringiensis.

Baculoviruses, Beauveria bassiana, Beauveria tenella, Bendiocarb. Benfuracarb,

Bensultap, Benzoximate, Betacyfluthrin, Bifenazate, Bifenthrin. Bioethanomethrin.

Biopermethrin, BPMC, Bromophos A. Bufencarb, Buprofezin, Butathiofos,

Butocarboxim, Butylpyridaben, Cadusafos, Carbaryl, Carbofuran. Carbophenothione, carbosulfan, cartap,

Chloethocarb, Chlorethoxyfos, Chlorfenapyr, Chlorfenvinphos, Chlorfluazuron.

Chlormephos, Chloφyrifos, Chloφyrifos M, Chlovaporthrin, Cis-Resmethrin,

Cispermethrin, clocythrin, cloethocarb, clofentezine, cyanophos, cycloprene.

Cycloprothrin, Cyfluthrin, Cyhalothrin, Cyhexatin, Cypermethrin, Cyromazine, Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Diazinon,

Dichlorvos, diflubenzuron, dimethoate, dimethylvinphos, diofenolan, disulfoton,

Docusat-sodium, Dofenapyn,

Eflusilanate, Emamectin, Empenthrin, Endosulfan. Entomopfthora spp.,

Esfenvalerate, Ethiofencarb, Ethion, Ethoprophos, Etofenprox, Etoxazole. Etrimfos. Fenamiphos. Fenazaquin, fenbutatin oxide, fenitrothion, fenothiocarb, fenoxacrim,

Fenoxycarb, fenpropathrin, fenpyrad, fenpyrithrin. Fenpyroximate, Fenvalerate,

Fipronil, fluazinam, fluazuron, flubrocythrinate, flucycloxuron, flucythrinate,

Flufenoxuron, Flutenzine, Fluvalinate, Fonophos, Fosmethilan, Fosthiazate, Fubfen- prox, Furathiocarb, Granuloseviruses

Halofenozide, HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene,

Imidacloprid, isazofos, isofenphos, isoxathion, ivermectin,

Nuclear polyhedron viruses

Lambda cyhalothrin, lufenuron Malathion, mecarbam, metaldehyde, methamidophos, metharhilic anisopliae. Metharithium flavoviride, methidathione, methiocarb. Methomyl. Methoxyfenozide, Metolcarb. Metoxadia zone. 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, Pirimiphos M, Profenofos, Promecarb, Propoxur, Prothiofos, Prothoine, Pyymetroz-, Pymetroz , Pyresmethrin, pyrethrum, pyridaben, pyridathione, pyrimidifen, pyriproxyfen, quinalphos,

Ribavirin

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

Tau fluvalinate, Tebufenozide, Tebufenpyrad, Tebupirimiphos, Teflubenzuron, Tefluthrin, Temephos, Temivinphos, Terbufos, Tetrachlorvinphos, Theta-cypermethrin, Thiamethoxam, Thiapronil, Thiatriphamiodoxinoxinoxinoxinoxinoxinoxinoxinoxinoxinoxinoxinoxinoxinoxinoxaline, tri Triarathenes, Triazamates, Triazophos, Triazuron, Trichlophenidines, Trichlorfon, Triflumuron, Trimethacarb, Vamidothion, Vaniliprole, Verticillium lecanii YI 5302 Zeta-cy permethrin, Zolaprofos

(l R-cis) - [5- (phenylmethyl) -3-furanyl] methyl-3 - [(dihydro-2-oxo-3 (2H) - furanylidene) methyl] -2,2-dimethylcyclopropane carboxylate (3- Phenoxyphenyl) methyl 2,2,3,3-tetramethylcyclopropanecarboxylate l - [(2-chloro-5-thiazolyl) methyl] tetrahydro-3,5-dimethyl-N-nitro-l, 3,5-triazine-2 ( lH) - imin

2- (2-chloro-6-fluoφhenyl) -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-1,1-difluoroethoxy ) -phenyl] -amino] -carbonyl] -benzamide 3-methylphenyl-propylcarbamate

4- [4- (4-ethoxyphenyl) -4-methylpentyl] -1-fluoro-2-phenoxy-benzene 4-chloro-2- (1, 1-dimethylethyl) -5 - [[2- (2,6-dimethyl-4-phenoxyphenoxy) ethyl] thio] -

3 (2H) pyridazinone

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

Bacillus thuringiensis strain EG-2348

Benzoic acid [2-benzoy 1- 1 - (1, 1-dimethyl ethyl) hydrazide

Butanoic acid 2,2-dimethyl-3- (2,4-dichloφhenyl) -2-oxo-l-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-l - (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-1H-pyrazole-1-carboxamide

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

N-Methyl 1-N '- (1-methyl-2-propenyl) - 1, 2-hydrazine dicarbothioamide

N-methyl-N'-2-propenyl-1, 2-hydrazine dicarbothioamide

0.0-Diethyl- [2- (dipropylamino) -2-oxoethyl] ethyl phosphoramidothioate

A mixture with other known active ingredients, such as herbicides or with

Fertilizers and growth regulators are possible.

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

Triazoles such as:

Azaconazole, Azocyclotin, Bitertanol, Bromuconazole, Cyproconazole, Diclobutrazole, Difenoconazole, Diniconazole, Epoxyconazole, Etaconazole, Fenbuconazole, Fenchlorazole, Fenethanil, Fluquinconazole, Flusilazole, Flutriafol, Flutriafol,

Hexaconazole, imibenconazole, ipconazole, isozofos, myclobutanil, metconazole, Paclobutrazole, penconazole. Propioconazole, (+) - cis-l - (4-chlorophenyl) -2- (l H- 1, 2,4-triazol-1 -yl) -cycloheptanol, 2- (1-tert-buty 1) - 1 - (2-chlθφhenyl) -3- (1, 2,4-triazol-1-yl) propan-2-ol, tebuconazole. Tetraconazole. Triadimefon, Triadimenol. Triapenthenol. Triflumizole, triticonazole. Uniconazoles and their metal salts and acid adducts;

I idazole like:

Clotrimazole, Bifonazole, Climbazole, Econazole, Fenapamil, Imazalil, Isoconazole. Ketoconazole, Lombazole, Miconazole, Oxpoconazole, Pefurazoate, Prochloraz, Triflumizole, Thiazolcar l -Imidazolyl-l - (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, carboxime, carboxime sulfoxide, cyclafluramide, fenfuram. Flutanil, Furcarbanil, Furmecyclox, Mebenil, Mepronil. Methfuroxam, metsulfovax, pyrocarbolide. Oxycarboxin, Shirlan, Seedvax;

Naphthalene derivatives such as:

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

Sulfena ide like:

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

Benzimidazoles such as:

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

Aldi oφh, dimethomorph, dodemorph. Falimoφh. Fenpropidine fenpropimorph. Tridemorph, Trimoφhamid and their aryl sulfonic 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 hemiform. Hexa-hydro-S-triazine, hexamethylenetetramine, N-hydroxymethyl-N ^' -methylthiourea, N-methylolchloroacetamide, oxazolidines. Paraformaldehyde, 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, didecyldimethylammonium chloride, dioctyldimethylammonium chloride, N-hexadecyltrimethylhymidium chloride;

Iodine derivatives such as:

Diiodomethyl-p-tolyl sulfone, 3-iodo-2-propynyl alcohol, 4-chloro-phenyl-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- Iodine-2-propynylphenyl carbamate;

Phenols such as:

Tribromophenol, Tetrachloφhenol. 3-methyl-4-chlorophenol, 3,5-dimethyl-4-chlorophenol, phenoxyethanol, dichlorophene. 2-benzyl-4-chlorophenol. 5-chloro-2- (2,4-di-chlorophenoxy) 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, Dipyrithion. l -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, 0-methyl-2 - [([3-methoximino-2-butyl) imino] oxy ) o-tolyl] -2-methoximinoacet imidates,

2 - [[[[l - (2.5-dimethylphenyl) ethylidene] amino] oxy] methyl] -. Alpha .- (methoximino) -

N-methylbenzeneacetamide, alpha- (methoxyimino) -N-methyl-2 - [[[[[l - [3- (trifluoromethyl) phenyI] - ethylidene] amino] oxy] methyl] -benzeneacetamide, alpha- (methoxyimino) - 2 - [[[[1 - [3- (trifluoromethyl) phenyl] ethylidene] amino] oxy] methyl] benzene aceticacid methyl ester, alpha- (methoxymethylene) -2 - [[[[l - [3- (trifluoromethyl) phenyl] ethylidene] amino] oxy] methyl] benzene aceticacid 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.-

(methoxyimino) -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-diene-

I-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-1-yl] -. Alpha.- (methoxymethylene) -benzeneaceticacid-methyl ester;

Metal soaps Λvie: 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 ^' -methyl-dithiobarbamate. 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 are very particularly preferred. Diniconazole. Hexaconazole. Metaconazole, Penconazole, Propiconazole, Tebuconazole, Dichlofluanid, Tolylfluanid, Fluorfolpet, Methfuroxam, Carboxin. Benzo [b] thiophene-S, S-dioxide-carboxylic acid cyclohexylamide, fenpiclonil, 4- (2,2-difluoro-1,3-benzodioxol-4-yl) -l H-pyrrole-3-carbonitrile, butenafine, imazalil, N-methyl-isothiazoline -3-one, 5-chloro-N-methylisothiazolin-3-one, N-octylisothiazolin-3-one, dichloro-N-octylisozhiazolinone, mercaptobenthiazole, thiocyanatomethylthiobenzothiazole, benzisothiazolinone, Nn-butylisothiazolinone, N- (2-hydroxypropyl) amino -methanol, benzyl alcohol- (hemi) - formal, N-methylolchloroacetamide, N- (2-hydroxypropyl) amine-methanol, glutaraldehyde, omadine, dimethyl dicarbonate, and / or 3-iodo-2-propynyl-n-butylcarbamate.

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, Azadirachtin, Azinphos A. Azinphos M, Azocyclotin,

Bacillus thuringiensis, Barthrin, 4-Bromo-2 (4-chloφhenyI) -l - (ethoxymethyl) -5- (trifluoromethyl) -l H-pyrrole-3-carbonitrile, bendiocarb, benfuracarb, bensultap, betacyfluthrin, bifenthrin, bioallesmethrin , 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-ethanimidamide, 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. Diafenthiuron, Dialiphos, Diazinon. l, 2-dibenzoyl-l (l, l-dimethyl) hydrazine. DNOC. Dichlofenthion, dichlorvos, dicliphos, dicrotophos, diflubenzuron, dimethoate. Dimethyl (phenyl) silyl methyl 3-phenoxybenzyl ether. Dimethyl (4-ethoxyphenyl) silylmethyl-3-phenoxybenzyl ether. 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, Flucythrinate.

Flufenoxuron, Flumethrin Flufenprox, Fluvalinate, Fonophos. Formethanate. Formothion, Fosmethilan Fosthiazat, Fubfenprox, Furathiocarb, HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydramethylnon, Hydroprene, Imidacloprid, Iodfenfos, Iprobefos, Isazophos, Isoamidophos, Isofenphos, Isoprocarb, Isoprocarb. Isoxathione, ivermectin, llama-cyhalothrin, lufenuron,

Kadedrin

Lambda-cyhalothrin, lufenuron,

Malathion. Mecarbam, Mervinphos, Mesulfenphos, Metaldehyde. Methacrifos. Methamidophos, methidathione, methiocarb, methomyl, metalcarb, milbemectin. Monocrotophos, moxiectin.

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

Omethoat. 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,

Propaphos, 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, Thiamethoxam, Thiapronil. Thiodicarb, Thiofanox, Thiazophos. Thiocyclam. Thiomethon, Thionazin, Thuringiensin, Tralomethrin, Triarathen, Triazophos, Triazamate. 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. Butraline, butylates. Bialaphos. Benzoyl prop, bromobutide, carbetamides, chloromethoxyfen. Chloramben, Chlorbromuron, Chlorflurenol,

Chloridazon, chlorimuron, chlornitrofen, Chloroacetic acid, chlorotoluron, chloroxuron, Chloφropham, chlorsulfuron, Chlorthal, Chlorthiamid, Cinmethylin, Cinofulsuron, clethodim, clomazone, Chlomeprop, clopyralid, cyanamides cyanazine, Cycloate, cycloxydim, Chloroxynil, clodinafop-propargyl, cumyluron, CGA 248757, clometoxyfen, cyhalofop, clopyrasuluron, cyclosulfamuron,

Dichloφrop, Dichloφrop-P, Diclofop, Diethatyl, Difenoxuron, Difenzoquat, Diflufen- nican, Dimefuron, Dimepiperate, Dimethachlor, Dimethipin, Dinitramine, Dinoseb, Dinoseb Acetate, Dinoterb, Diphenamid, Dipropetryn, DOCat, DSOC, Diquat, Dithat , 4-D, Daimuron, Dalapon, Dazomet, 2,4-DB, Desmedipham, Desmetryn, Dicamba, Dichlobenil, Dimethamid, Dithiopyr, Dimethametryn, 59 -

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, loxynil, 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, Sulcotrione, Sulfosate, Tar oils, TCA, tebutam. Tebuthiuron, Terbacil, Terbumeton. Terbuthylazine, Terbutryn. Thiazafluoron, thifensulfuron. Thiobencarb. Thiocarbazil. Tralkoxydim, triallates. Triasulfuron. Tribenuron, Triclopyr, Tridiphane. Trietazines. Trifluralin. Tycor. Thdiazimin, thiazopyr, triflusulfuron, vernolates.

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, spraying, spraying, scattering. Dusting, foaming. Brushing etc. It is also possible to apply the active ingredients using the ultra-low-volume method 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. In the treatment of parts of plants, the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 10 and 1000 g / ha. In the case of seed treatment, the active compound application rates are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed. When treating the soil, the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 1 and 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 carpophagus, 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 e.g. Blatta orientalis, Periplaneta americana,

Leucophaea maderae, Blattella germanica.

From the order of the Dermaptera e.g. Forficula auricularia. From the order of the Isoptera e.g. Reticulitermes spp ..

From the order of the 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, for example Aleurodes brassicae, Bemisia tabaci. Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum. Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus spp., Macrosiphum avenae. Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotoc syllas, Ppp. From the order of the Lepidoptera, for example Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella xylostella, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp.

Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Mamestra brassicae, Panolis flammea. Spodoptera spp., Trichoplusia ni, Caφocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoecia podana, Capua

Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana, Cnaphalocerus spp ..

From the order of the Coleoptera e.g. Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus. Acanthoscelides obtectus, Hylotrupes bajulus. Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp .. Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrordhynchuschop., Otiorrordhynchuschop. Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp.,

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

From the order of the Hymenoptera, for example Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp. From the order of the Diptera, for example Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus. Os- cinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae. Tipula paludosa, Hylemyia spp., Liriomyza spp .. From the order of the Siphonaptera, for example Xenopsylla cheopis, Ceratophyllus spp ..

From the class of the Arachnida e.g. Scoφio maurus, Latrodectus mactans. Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp.,. Chori ., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp.,

Hemitarsonemus spp., Brevipalpus spp ..

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

Trichodorus spp., Bursaphelenchus spp ..

The compounds of the formula (I) according to the invention can be used particularly successfully to control insects which are harmful to plants, for example against the caterpillars of the cockroach (Plutella maculipennis) or the green ones

Use peach aphids (Mycus persicae), as well as against plant-damaging mites, such as the common spider mite (Tetranychus urticae).

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 through which the action of the active ingredients is increased without the added synergist itself having to be active.

The active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges. The drug concentration of the Application forms can be from 0.0000001 to 95% by weight of active compound, preferably between 0.0001 and 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 ingredient is distinguished by an excellent residual action on wood and clay as well as 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.

- 45 -

Manufacturing examples

example

A solution of 0.89 g (6.3 mmol) of 3-chloro-5-methylphenol in 0.63 g (6.3 mmol) of triethylamine is added dropwise to a solution of 1.0 g (5.8 mmol) of chlorodithiazole dioxide in 5 ml of dimethylformamide. The mixture is stirred at room temperature for 2 hours, poured into 50 ml of ice water, the precipitated product is filtered off with suction and dried in vacuo. 1.47 g (91% of theory) of 3- (3-chloro-5-methylphenoxy) -lλ ⁶ , 4,2-dithiazol-l, l (5H) -dione with a melting point of 151.2 ° C. are obtained.

Example 2

1.0 g (6.5 mmol) of chlorodithiazine dioxide (6-ring) are dissolved in 25 ml of dimethylformamide and a solution of 0.84 g (6.5 mmol) of 3-chlorophene and 0.66 g (6.5 mmol) of triethylamine in 15 ml of dimethylformamide are added within 5 minutes. The mixture is stirred for 4 hours at room temperature, poured into water, suction filtered, washed with a little ether and dried in vacuo. 0.39 g (22% of theory) of 3- (3-chloro-phenoxy) -5,6-dihydro-1 H-1 λ ⁶ , 4,2-dithiazine-1,1-dione with a melting point of 170.2 ° C. is obtained.

Analogously to Examples 1 and 2 and the general description of the production process a) according to the invention, the compounds of the formula (I) given in Tables 1 and 2 were also obtained.

The ties marked with * mark the connection points

The carbon atoms marked with ^a) in group Y are connected with the S0 ₂ group, the carbon atoms marked with ^b) are connected with the S group.

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

Table 2

Preparation of the starting materials of the formula (II)

Example (II-l)

17 g (122 mmol) of sulfuryl chloride are initially introduced and 4.3 g (24.5 mmol) of 1,4,2-dithiazol-3-methylthio-1,1-dioxide are added within 10 minutes. The mixture is heated to 40 ° C. and stirred at this temperature for 24 hours. After evaporating off the excess sulfuryl chloride in vacuo, the mixture is stirred with diethyl ether, suction filtered and in Vacuum dried. 3.3 g (78% of theory) of 1,4,2-dithiazole-3-chloro-1,1-dioxide are obtained.

'H NMR (CDC1: δ = 4.67 ppm.

The new intermediates of the formula (II-a) listed in Table 3 were also obtained analogously:

Table 3

Preparation of the starting materials of the formula (IV)

The starting materials of the formula (IV) were made analogously to the preparation instructions

US 3345374. The following, partly new compounds were obtained analogously: 65

Table 4

Application examples:

Example A

To demonstrate the effectiveness against fungi (Penicillium brevicaule, Chaetomium globosum, Aspergillus Niger), the minimum inhibitory concentrations (MIC) of agents according to the invention are determined:

Active ingredients according to the invention are added to an agar which is produced using malt extract in concentrations of 0.1 mg / 1 to 5,000 mg / 1. After the agar has solidified, it is contaminated with pure cultures of the test organisms listed in Table 2. 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 the table below.

The compounds (1), (92), (93), (94) and (100) show in the fungi Penicillium brevicaule, Chaetomium globosum, Aspergillus Niger MIC values of 10-100 ppm.

67 -

Table A Minimum inhibitory concentrations (ppm) of compounds of the formula (I) according to the invention

Example B

Plasmopara test (vine) / protective

Solvent: 47 parts by weight of acetone

Emulsifier: 3 parts by weight of alkylaryl polyglycol ether

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

To test for protective activity, young plants are sprayed with the active compound preparation in the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Plasmopara viticola and then remain in an incubation cabin at about 20 ° C. and 100% relative atmospheric 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 a

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 (14), (21), (27), (28), (40), (41), (42), (141), (1), (95), (96 ), (98), (99), (100), (101), (102), (105), (106), (1 19) and (128) listed substances according to the invention at an application rate of 250 g / ha an efficiency of 90% or more. Table B

Plasmopara test (vine) / protective

70

Table B

Plasmopara test (vine) / protective

71

Table B

Plasmopara test (vine) / protective

Table B

Plasmopara test (vine) / protective

- 73 -

Table B

Plasmopara test (vine) / protective

Example C

Venturia test (apple) / protective

Solvent: 47 parts by weight of acetone

Emulsifier: 3 parts by weight of alkylaryl polyglycol ether

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

To test for protective activity, young plants are sprayed with the active compound preparation in the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous conidia suspension of the apple scab pathogen Venturia inaequalis and then remain for 1 day at approx.

20 ° C and 100% relative humidity in an incubation cabin.

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

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

In this test, the examples (24), (27), (28), (40), (141), (1), (94),

(95), (96), (100), (101), (105), (106), (108), (1 10), (1 1 1), (1 14), (1 15) and ( 133) listed substances according to the invention with an application rate of 250 g / ha an efficiency of 90% or more. Table C.

Venturia test (apple) / protective

Table C.

Venturia test (apple) / protective

77 -

Table C.

Venturia test (apple) / protective

Table C.

Venturia test (apple) / protective

Table C.

Venturia test (apple) / protective

Example D

Phytophthora test (tomato) / protective

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

Emulsifier: 1.17 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 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. 1 day after the treatment, the plants are inoculated with a spore suspension of Phytiphthora infestans. The plants are then grown in a climate cell at approx.

96% relative humidity and a temperature of approx. 20 ° 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 (26), (127), (128), (133) and (13) show an efficiency of 90% or more at an application rate of 750 g / ha. Table D

Phytophthora test (tomato) / protective

- 83

Example E

Myzus test

Solvent: 6 parts by weight of dimethylformamide

67 parts by weight of methanol

Emulsifier: 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 amount of solvent and the stated amount of emulsifier, and the concentrate is diluted to the desired concentrations with water containing emulsifier.

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

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, for example, the following compounds of Preparation Examples (22) and (40) show a kill rate of 90% or more.

Table E

Plant-damaging insects

Myzus test

Example F

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, for example, the compounds of preparation examples (14), with an exemplary active ingredient concentration of 0.1%, kill 95% after 7 days.

86

Table F

plant-damaging insects Plutella test / artificial feed

- 87 -

Example G

Tetranychus test (OP-resistant / immersion treatment)

Solvent: 3 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

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

Bean plants (Phaseolus vulgaris), which are heavily infested with all stages of the common spider mite (Tetranychus urticae), are immersed in an active ingredient preparation of the desired concentration.

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

In this test, for example, the combination of the preparation examples (20) with an exemplary active ingredient concentration of 0.01% causes a kill of 95% after 7 days.

Table G

plant-damaging insects

Tetranychus test (OP-resistant / immersion treatment)

Claims

- 89 -

claims

1 . Compounds of the general formula (I),

in which

Ar stands for substituted or unsubstituted aryl and

Y for substituted or unsubstituted, straight-chain or branched

Alkanediyl is.

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

Ar represents unsubstituted or substituted phenyl.

where the following substituents stand for phenyl:

Halogen, cyano, thiocyano, nitro, amino, formyl, carbamoyl, thiocarbamoyl, hydrogen, hydroxy; each straight-chain or branched alkyl, cyanoalkyl, hydroxyalkyl, alkoxy, alkoxyalkyl, hydroxyalkoxy, alkylthioalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 8 carbon atoms; each straight-chain or branched, optionally mono- or disubstituted by cyano, nitro, phenyl, nitrophenyl, dinitrophenyl, alkoxycarbonylamino, phthalimidyl, bis- (alkoxycarbonylamino) or dioxobenzimidazolyl-substituted alkenyl, alkenyloxy or Alkenylcarbonyl each having 2 to 6 carbon atoms in the alkenyl part; each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms; each straight-chain or branched halogenaikenyl or haloalkenyloxy each having 2 to 6 carbon atoms and 1 to 1 1 identical or different halogen atoms, each straight-chain or branched alkylamino, dialkylamino,

Alkylcarbonyl, thiocyanoalkylcarbonyl, haloalkylcarbonyl (with 1 to 3 halogen atoms), alkoxycarbonyl, alkoxycarbonylazoalkyl, alkylaminocarbonyl, dialkylaminocarbonyl or arylalkylaminocarbonyl with 1 to 6 carbon atoms in the respective hydrocarbon chains or optionally simply up to four times

Halogen or alkyl with 1 to 4 carbon atoms substituted cycloalkylcarbonylamino or cycloalkyl with 3 to 6 carbon atoms in the cycloalkyl part; Cycloalkyl or cycloalkyloxy each having 3 to 6 carbon atoms; each optionally by halogen. Alkyl, phenyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl with 1 to 4 carbon atoms, haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl with 1 to 4 carbon atoms and 1 to 9 halogen atoms substituted phenyl,

Phenoxy, phenylazo, phenylthio, phenylsulfonyl, phenylcarbonyl, phenylalkylcarbonyl, or phenylalkoxy having 1 to 4 carbon atoms in the alkyl part, in each case optionally by halogen, oxo, alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl having 1 to 4 carbon atoms,

Haloalkyl, haloalkoxy, haloalkylthio, halogen alkylsulfinyl or haloalkylsulfonyl having 1 to 4 carbon atoms and 1 to 9 halogen atoms or phenyl substituted heterocyclyl, heterocyclic alkyl having 1 to 4 carbon atoms in the alkyl part, heterocyclyloxy, heterocyclylthio. Heterocyclylsulfinyl. Heterocyclylsulfonyl, Fleterocyclylcarbonyl, Heterocyclylthiocarbonyl, Benzoheterocyclyl, Benzoheterocyclylaikyl with 1 to 4 carbon atoms in the alkyl part, Benzoheterocyclyloxy, Benzoheterocyclyl-thio, Benzoheterocyclylsulfinyl, Benzoheterocylcarbonyl heterylcylylsulfonyl,

or a grouping T in which

A ² ^

T represents CH or nitrogen,

A 'represents hydrogen or alkyl having 1 to 4 carbon atoms,

Cycloalkyl with 3 to 6 carbon atoms, phenyl, heterocyclyl with 5 or 6 ring members, alkoxycarbonyl with 1 to 4 carbon atoms in the alkyl part, benzylaminocarbonyl, benzyloxyaminocarbonyl or aminocarbonyl,

A ^ represents hydroxy, amino, alkyl, phenyl, benzyl, alkoxy, cyanoalkoxy, benzyloxy, alkylamino, dialkylamino, alkoxycarbonylamino, alkoxycarbonylphenyl each having 1 to 4 carbon atoms in the respective alkyl chains or alkyleneoxy having 2 to 4 carbon atoms, and

for optionally mono- or disubstituted by phenyl

Alkylene with 1 to 8 carbon atoms, the attachment represent the alkylene chain particularly preferably on the same or directly adjacent carbon atoms,

Ar also represents unsubstituted or substituted aryl, where

Ar represents one of the following groups:

which are each bonded via the phenyl ring and in turn can be mono- to disubstituted, the possible substituents preferably being selected from the following list: halogen, cyano, thiocyano, nitro, amino, formyl, carboxy, carbamoyl, thiocarbamoyl; - 93 -

each straight-chain or branched alkyl, alkoxy, alkylthio. Alkylsulfinyl or alkylsulfonyl each having 1 to 8 carbon atoms; each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms; in each case straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl or arylalkylaminocarbonyl having 1 to 6 carbon atoms in the respective hydrocarbon chains or optionally cycloalkylcarbonylamino or cycloalkyl having 3 to 6 substituted by up to four times by halogen or alkyl having 1 to 4 carbon atoms Carbon atoms in the cycloalkyl part; Cycloalkyl or cycloalkyloxy each having 3 to 6 carbon atoms; each optionally by nitro, halogen, alkyl, phenyl, alkoxy. Alkylthio, alkylsulfinyl or alkylsulfonyl having 1 to 4 carbon atoms, haloalkyl, haloalkoxy, haloalkylthio. Haloalkylsulfinyl or haloalkylsulfonyl having 1 to 4 carbon atoms and 1 to 9 halogen atoms substituted phenyl, phenoxy, phenylthio, phenylsulfonyl, phenylcarbonyl,

Phenylalkylcarbonyl, or phenylalkoxy having 1 to 4 carbon atoms in the alkyl part, and

Y for optionally mono- or disubstituted by phenyl

Alkylene having 1 to 8 carbon atoms, the connection points of the alkylene chain being particularly preferably on the same or on directly adjacent carbon atoms.

3. Compounds of formula (Ia), characterized in that

R ', R ² , R \ R ⁴ and R ^{5 are the} same or different and independently of one another represent the following substituents: halogen, cyano, thiocyano, nitro, amino, formyl, carbamoyl, thiocarbamoyl, hydrogen, hydroxy; each straight-chain or branched alkyl, cyanoalkyl, hydroxyalkyl, alkoxy, alkoxyalkyl, hydroxyalkoxy, alkylthioalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 8 carbon atoms; each straight-chain or branched, optionally mono- or disubstituted by cyano, nitro, phenyl, nitrophenyl, dinitrophenyl, alkoxycarbonylamino, phthalimidyl, bis- (alkoxycarbonylamino) or dioxobenzimidazolyl-substituted alkenyl, alkenyloxy or alkenylcarbonyl, each with 2 to 6 carbon atoms in the alkenyl part; each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms; each straight-chain or branched halogenaikenyl or haloalkenyloxy each having 2 to 6 carbon atoms and 1 to 1 1 identical or different halogen atoms; each straight-chain or branched alkylamino, dialkylamino, alkyl carbonyl, thiocyanoalkylcarbonyl, haloalkylcarbonyl (having 1 to 3 halogen atoms), alkoxycarbonyl, alkoxycarbonyllazoalkyl, Alkylaminocarbonyl, dialkylaminocarbonyl or arylalkylaminocarbonyl with 1 to 6 carbon atoms in the respective hydrocarbon chains or optionally up to four times cycloalkylcarbonylamino or cycloalkyl with 3 to 6 substituted by halogen or alkyl with 1 to 4 carbon atoms

Carbon atoms in the cycloalkyl part;

Cycloalkyl or cycloalkyloxy each having 3 to 6 carbon atoms; each optionally by halogen, alkyl, phenyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl with 1 to 4

Carbon atoms, haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl with 1 to 4 carbon atoms and 1 to 9 halogen atoms substituted phenyl, phenoxy, phenylazo, phenylthio, phenylsulfonyl, phenylcarbonyl, phenylalkylcarbonyl, or phenylalkoxy with 1 to 4 carbon atoms in the alkyl part, in each case optionally by halogen , Oxo, alkyl, alkoxy, alkylthio. Alkylsulfinyl or alkylsulfonyl with 1 to 4 carbon atoms, haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl with 1 to 4 carbon atoms and 1 to 9 halogen atoms or phenyl-substituted heterocyclyl, heterocyclylalkyl with 1 to 4 carbon atoms in the alkyl part, heterocyclyloxy, heteriocylylylylcylylylcylylcylylcylycyllycyllyl, Heterocyclylsulfonyl, heterocyclylcarbonyl, heterocycliclthiocarbonyl, benzoheterocyclyl, benzoheterocyclylaikyl with 1 to 4 carbon atoms in the alkyl part, benzoheterocyclyloxy, benzoheterocyclylthio, benzoheterocyclylsulfinyl,

Benzoheterocyclylsulfonyl, benzoheterocyclylcarbonyl or benzoheterocyclylthiocarbonyl each having 5 or 6 ring members in the heterocyclic part, - 96

A ¹ or a grouping j in which

A ² ^

T represents CH or nitrogen.

A ^ represents hydrogen or alkyl having 1 to 4 carbon atoms,

Cycloalkyl with 3 to 6 carbon atoms, phenyl, heterocyclyl with 5 or 6 ring members, alkoxycarbonyl with 1 to 4 carbon atoms in the alkyl part, benzylaminocarbonyl, benzyloxyaminocarbonyl or aminocarbonyl,

A2 stands for hydroxy, amino, alkyl, phenyl, benzyl, alkoxy, cyanoalkoxy, benzyloxy, alkylamino, dialkylamino, alkoxycarbonylamino, alkoxycarbonylphenyl each having 1 to 4 carbon atoms in the respective alkyl chains or alkyleneoxy having 2 to 4 carbon atoms, and

Y represents optionally mono- or disubstituted by phenyl-substituted alkylene with 1 to 8 carbon atoms, the connection points of the alkylene chain being particularly preferably on the same or on directly adjacent carbon atoms.

4. Compounds of formula (I-a) according to claim 3, characterized in that

R ', R ² , R ³ , R ⁴ and R ^{5 are the} same or different and independently of one another represent the following substituents:

Fluorine, chlorine, bromine, cyano, thiocyano, nitro, amino, formyl, carbamoyl, thiocarbamoyl, hydrogen, hydroxy, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, Methoxymethyl, cyanomethyl, hydroxymethyl, Ilydroxyethyl, hydroxypropyl. Hydroxybutyl, hydroxypentyl, hydroxyhexyl, methoxy, ethoxy. n- or i-propoxy, hydroxyethoxy. Methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl,

Methylaminomethyl, dimethylaminomethyl, each optionally mono- or disubstituted by cyano, nitro, phenyl, nitrophenyl, dinitrophenyl, methoxycarbonylamino, phthalimidyl, bis- (methoxycarbonylamino) or dioxobenzimidazolyl-substituted vinyl, allyl, 2-methylallyl,

Propen-1-yl, crotonyl, propargyl, vinyloxy, allyloxy, 2-methylallyloxy, propen-1-yloxy, crotonyloxy, propargyloxy. Vinylcarbonyl, allylcarbonyl, 2-methylallylcarbonyl, propen-1 -ylcarbonyl, crotonylcarbonyl, propargylcarbonyl; Trifluoromethyl, trifluoroethyl,

Difluoromethoxy, trifluoromethoxy, difluorochloromethoxy,

Trifluoroethoxy, pentafluoroethoxy, 2-chloro-l, l, 2-trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio. Trifluoromethylsulfinyl or trifluoromethylsulfonyl. Methylamino, ethylamino, n- or i-propylamino, dimethylamino.

Diethylamino,

Methylcarbonyl, acetyl, propionyl, thiocyanomethylcarbonyl, chloro-t-butylcarbonyl, methoxycarbonyl, ethoxycarbonyl, ethoxycarbonylazomethyl, methylaminocarbonyl, ethylaminocarbonyl, dimethylaminocarbonyl, optionally mono- to tetrasubstituted by chlorine, bromine, methyl or ethylentylcyclylyl, cyclopropyl, cyclopylyl cyclyl, cyclopropyl, cyclopylyl, cyclopropyl, cyclopylyl, cyclopropyl, cyclopylyl, cyclopropyl, cyclopyl, cyclopropyl, cyclopethyl, cyclopyl, cyclopyl, cyclopropyl, cyclopropyl, cyclopyl, cyclopropyl, cyclopyl substituted, cyclopropyl, cyclopyl, cyclopyl, cyclopyl, cyclopyl, substituted by chlorine, bromine, methyl or ethyl or cyclohexyl, cyclopentyl, cyclohexyl, cyclopentyloxy, cyclohexyloxy, cyclohexylcarbonylamino, in each case optionally through nitro, fluorine, chlorine, methyl, Trifluoromethyl, phenyl or methoxy substituted phenyl, phenoxy, phenylazo, phenylthio, phenylsulfonyl, phenylcarbonyl. Benzylcarbonyl or benzyl, for dithiazole, dithiazoloxy, optionally mono- to trisubstituted by methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, oxo, fluorine, chlorine, bromine, trifluoromethyl or phenyl, Oxadiazole, benzofuranyl, benzofuranylcarbonyl, pyridazine, benzoxazole, pyrimidyl, morpholinyl, morpholinylthiocarbonyl, thienyl, imidazolyl, thiadiazolyl, pyridyl, pyridazinone, furyl, piperazinyl, pyrimidylthio, thiazolylio, benzolazoleyl Dioxazinyl,

Thiadiazolylsulfonyl;

A ^ or a grouping _j , in which

- ^

T represents CH or nitrogen,

A 'for hydrogen, methyl, ethyl, n- or i-propyl, n-. i-, s- or t-butyl, cyclopentyl, cyclohexyl, phenyl, dioxazinyl, methoxycarbonyl, ethoxycarbonyl, benzylaminocarbonyl, benzyloxyaminocarbonyl or aminocarbonyl.

A ^ for hydroxy, amino, methyl, ethyl, phenyl, benzyl, methoxy,

Ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, cyano-methoxy, benzyloxy, methylamino, ethylamino, dimethylamino, diethylamino, methoxycarbonylamino, ethoxycarbonylamino, methoxycarbonylphenyl, ethoxycarbonylphenyl or Allyloxy stands, and

for optionally mono- or disubstituted by phenyl

Methylene, 1,1-ethylene, 1,2-ethylene, 1,1-, 1,2-, 1,3- or 2,2-propylene, - 99 -

1, 1-, 1,2-, 1,3-, 1,4-, 2,2-, 2,3-butylene or 1, 1-, 1, 2- or l, 3- (2-methyl- propylene).

5. Compounds of formula (I-b), characterized in that

Ar 'represents one of the following groups:

which are each bonded via the phenyl ring and in turn can be monosubstituted or substituted six times, the possible substituents preferably being selected from the following list: halogen, cyano, thiocyano, nitro, amino, formyl, carboxy, carbamoyl, thiocarbamoyl; in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 8 carbon atoms; each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms; each straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl or arylalkylaminocarbonyl having 1 to 6 carbon atoms in the respective hydrocarbon chains or optionally cycloalkylcarbonylamino or cycloalkyl having 3 to 6 substituted by up to four times by halogen or alkyl having 1 to 4 carbon atoms Carbon atoms in the cycloalkyl part; Cycloalkyl or cycloalkyloxy each having 3 to 6 carbon atoms; each optionally substituted by nitro, halogen, alkyl, phenyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl with 1 to 4 carbon atoms, haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl with 1 to 4 carbon atoms and 1 to 9 ^' halogen atoms, phenyl, phenoxy, phenylthio , Phenylsulfonyl, phenylcarbonyl,

Phenylalkylcarbonyl, or phenylalkoxy having 1 to 4 carbon atoms in the alkyl part, and 101 -

Y for optionally mono- or disubstituted by phenyl

Alkylene having 1 to 8 carbon atoms, the connection points of the alkylene chain being particularly preferably on the same or on directly adjacent carbon atoms.

6. Compounds of formula (I-b) according to claim 5, characterized in that

Ar 'represents one of the following groups:

which are each bonded via the phenyl ring and in turn can be substituted up to six times, the possible substituents preferably being selected from the following list:

Fluorine, chlorine, bromine, cyano, thiocyano, nitro, amino, formyl,

Carboxy, carbamoyl, thiocarbamoyl,

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, pentafluoroethoxy, 2-chloro-1,1,2-trifluoroethoxy, difluoromethylthio, trifluoromethylthio, chloromethylthio difluoro-, trifluoromethylsulfinyl or trifluoromethylsulfonyl, methylamino, ethylamino, n- or i-propylamino, dimethylamino ,

Diethylamino,

Acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl,

Methylaminocarbonyl, ethylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, optionally up to four times cyclopropyl substituted by chlorine, bromine, methyl or ethyl,

Cyclobutyl, cyclopentyl or cyclohexyl, cyclopentyl, cyclohexyl, cyclopentyloxy, cyclohexyloxy, each optionally substituted by nitro, fluorine, chlorine, methyl, trifluoromethyl, phenyl or methoxy, phenyl, phenoxy, phenylthio, phenylsulfonyl, phenylcarbonyl or benzylcarbonyl or

Benzyl, and

for optionally mono- or disubstituted by phenyl

Methylene, 1,1-ethylene, 1,2-ethylene 1,1-, 1,2-, 1,3- or 2,2-propylene, 1,1-, 1,2-, 1,3-, 1 , 4-, 2,2-, 2,3-butylene or 1,1-, 1,2- or l, 3- (2-

Methyl propylene).

. Compounds of formula (Il-a), characterized in that

Y ¹ for mono- or disubstituted by phenyl or 1,2-ethylene or for optionally mono- or disubstituted by phenyl 1,1-ethylene, 1,1-, 1,2- or 2,2-propylene, 1, 1 -, 1,2-, 2,2-, 2,3-butylene or 1,1- or 1,2- (2-methyl-propylene) and

X ^{1 represents} halogen, preferably chlorine or bromine.

8. agents containing extenders and / or carriers and optionally surface-active substances, characterized by a content of at least one compound as defined in claims 1 to 6.

9. A method for controlling pests, characterized in that compounds as defined in claims 1 to 6 or agents as defined in claim 8 are allowed to act on pests and / or their habitat.

10. Use of compounds as in claims 1 to 6 or agents as defined in claim 8 for controlling pests.

11. A process for the preparation of compounds of formula (I) according to claim

1, characterized in that compounds of the general formula (II) - 104 -

in which

Y has the meaning given in claim 1 and

X represents halogen, alkyl or arylsulfonyl,

with phenols of the general formula (III),

Ar-OH (III) in which

Ar has the meaning given in claim 1

optionally in the presence of a diluent, optionally in

Presence of an acid acceptor and optionally in the presence of a catalyst.

12. A process for the preparation of compounds of the formula (II-a) as defined in claim 7, characterized in that compounds of the general formula (IV),

in which

Y ^{1 has} the meaning given in claim 7 and - 105 -

Alk stands for alkyl,

with a halogenating agent, preferably a conventional chlorination, bromination or iodination agent, such as chlorine, bromine, iodine,

Sulfuryl chloride, chlorosuccinimide, bromosuccinimide, 1,3-dibromo-5,5-dimethylhydantoin or iodosuccinimide, optionally in the presence of a diluent.

13. A process for the preparation of agents, characterized in that

Compounds as defined in claims 1 to 6 mixed with extenders and / or carriers and / or surface-active agents.