DE19918297A1 - New heteroaryloxy and heteroarylthio substituted dithiazole dioxide derivatives useful as microbicides, insecticides, acaricides and nematocides, especially in plant and material protection - Google Patents

Abstract

Heteroaryloxy and heteroarylthio substituted dithiazole dioxide derivatives (I) are new. Heteroaryloxy and heteroarylthio substituted dithiazole dioxide derivatives of formula (I) are new. X<1> = O or S; Y = CHR<7> or CHR<5>CHR<6>; Z<1> = S; O or NR<1>; Z<2> = CR<2> or N; Z<3> = CR<3> or N; Z<4> = CR<4> or N; R<1>-R<4> = H; CN; NO2 or alkyl, alkenyl, alkynyl, alkoxy, haloalkoxy, benzylthio, alkylthio, haloalkylthio, aryl, pyridyl, pyrimidinyl or pyrazinyl (each optionally substituted or optionally bonded via these groups); R<5>-R<7> = H or alkyl, alkenyl, alkynyl, aryl, pyridyl; NO2; CN or halo. An Independent claim is also included for the preparation of (I).

Description

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

5-ring dithiazoles have already been described, a biological effect is not known (cf. K. Dickore, Lieb. Ann. Chem. 1964, 671; US 3,345,374). S-aryl Dithiazole dioxides are known, their range of action does not reach the required level (see DE 195 45 635). In addition, dithiazine oxides (6 rings) with alkyl substituents already described on sulfur, a biological effect is not known (see Nakahashi et al., Bull. Chem Soc. Jpn. 1972, 45, 3217; Hasegawa, K. et al., Bull. Chem. Soc. Jpn. 1972, 45, 1567).

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

in which
X ^{1 represents} oxygen or sulfur,
Y stands for -CHR ⁷ - or -CHR ⁵ CHR ⁶ -,
2 ^{1 represents} sulfur, oxygen, NR ¹ ,
Z ^{2 represents} CR ² or nitrogen,
Z ^{3 represents} CR ³ or nitrogen,
Z ^{4 represents} CR ⁴ or nitrogen,
R ¹ , R ² , R ³ and R ^{4 are the} same or different and are independently hydrogen, cyano, nitro, substituted or unsubstituted alkyl, alkenyl, alkynyl, alkoxy, haloalkoxy, benzylthio, alkylthio, haloalkylthio, aryl, pyridyl, pyrimidyl or pyrazinyl or are optionally connected via one of these substituents and
R ⁵ , R ⁶ and R ^{7 are the} same or different and independently of one another represent hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, pyridyl, nitro, cyano or halogen,
are excellent for protecting plants and materials.

Compounds of the formula (I) in which X ^{1 represents} oxygen or sulfur are preferred,
Y stands for -CHR ⁷ - or -CHR ⁵ CHR ⁶ -,
Z ^{1 represents} sulfur, oxygen, NR ¹ ,
Z ^{2 represents} CR ² or nitrogen,
Z ^{3 represents} CR ³ or nitrogen,
Z ^{4 represents} CR ⁴ or nitrogen, where
R ¹ , R ² , R ³ , R ⁴ independently of one another are hydrogen, cyano, nitro, straight-chain or branched alkyl (C ₁ -C ₆ ), alkenyl (C ₂ -C ₆ ), alkynyl (C ₂ -C ₆ ), which are optionally substituted one or more times, identically or differently, by halogen, nitro, cyano, alkoxy (C ₁ -C ₆ ), haloalkoxy (C ₁ -C ₆ ) with 1 to 9 identical or different halogen atoms, alkylthio (C ₁ -C ₆ ), haloalkylthio (C ₁ -C ₆ ) with 1 to 9 identical or different halogen atoms, phenyl, pyridyl, pyrimidyl, or pyrazinyl; for alkoxy (C ₁ -C ₅ ); for haloalkoxy (C ₁ -C ₅ ) with 1 to 6 identical or different halogen atoms; Benzylthio; Alkylthio (C ₁ -C ₅ ); Haloalkylthio (C ₁ -C ₅ ) with 1 to 6 identical or different halogen atoms; or for phenyl, pyridyl, pyrimidyl or pyrazinyl, which are each optionally mono- to polysubstituted by halogen, alkyl (C ₁ -C ₅ ), haloalkyl (C ₁ -C ₅ ) with 1 to 6 identical or different halogen atoms, alkoxy (C ₁ -C ₅ ), haloalkoxy (C ₁ -C ₅ ) with 1 to 6 identical or different halogen atoms, alkylthio (C ₁ -C ₅ ), haloalkylthio (C ₁ -C ₅ ) with 1 to 6 identical or different halogen atoms, Amino, monoalkylamino with straight-chain or branched alkyl radicals (C ₁ -C ₆ ), dialkylamino with the same or different, straight-chain or branched alkyl radicals (C ₁ -C ₅ ),
or
R ² and R ^{3 are} connected via the group -CH = CH-CH = CH-, which is optionally mono- to tetrasubstituted by halogen, nitro, cyano, alkyl (C ₁ -C ₅ ), haloalkyl (C ₁ -C ₅₎ having 1 to 6 identical or different halogen atoms, alkoxy (C ₁ -C _5), haloalkoxy (C ₁ -C ₅₎ having 1 to 6 identical or different halogen atoms, alkylthio (C ₁ -C _5), haloalkylthio (C ₁ -C ₅ ) with 1 to 6 identical or different halogen atoms, amino, monoalkylamino with straight-chain or branched alkyl radicals (C ₁ -C ₆ ), dialkylamino with identical or different, straight-chain or branched alkyl radicals (C ₁ -C ₅ ), or with one Aryl ring is fused,
R ⁵ _, R ⁶ or R ^{7 are the} same or different and independently of one another are hydrogen, nitro, cyano, halogen, straight-chain or branched alkyl (C ₁ -C ₈ ), alkenyl (C ₂ -C ₈ ) or alkynyl (C ₂ - C ₈ ), which is optionally substituted one or more times, identically or differently, by halogen, optionally substituted phenyl, alkoxy (C ₁ -C ₅ ), haloalkoxy (C ₁ -C ₅ ) with 1 to 6 identical or different halogen atoms, acyl ( C ₁ -C ₅ ) or optionally substituted aryl, pyridyl.

Compounds of the formula (I) in which X ^{1 represents} oxygen or sulfur are particularly preferred,
Y stands for -CHR ⁷ - or -CHR ⁵ CHR ⁶ -,
Z ^{1 represents} sulfur, oxygen, NR ¹ ,
Z ^{2 represents} CR ² or nitrogen,
Z ^{3 represents} CR ³ or nitrogen,
Z ^{4 represents} CR ⁴ or nitrogen, where
R ¹ , R ² , R ³ , R ⁴ independently of one another are hydrogen, cyano, nitro, straight-chain or branched alkyl (C ₁ -C ₅ ), alkenyl (C ₂ -C ₅ ), alkynyl (C ₂ -C ₅ ), which are optionally substituted one or more times, identically or differently, by fluorine, chlorine, nitro, cyano, alkoxy (C ₁ -C ₄ ), haloalkoxy (C ₁ -C ₄ ) with 1 to 5 identical or different fluorine and / or or chlorine atoms, alkylthio (C ₁ -C ₄ ), haloalkylthio (C ₁ -C ₄ ) with 1 to 5 identical or different fluorine and / or chlorine atoms, phenyl, pyridyl, pyrimidyl or pyrazinyl; for alkoxy (C ₁ -C ₄ ); for haloalkoxy (C ₁ -C ₄ ) with 1 to 4 identical different fluorine and / or chlorine atoms; Benzylthio, alkylthio (C ₁ -C ₄ ); Haloalkylthio (C ₁ -C ₄ ) with 1 to 4 identical or different fluorine or chlorine atoms, or for phenyl, pyridyl, pyrimidyl or pyrazinyl, which are each optionally substituted one or more times, identically or differently, by fluorine and / or chlorine, alkyl (C ₁ -C ₄ ), haloalkyl (C ₁ -C ₄ ) with 1 to 4 identical or different fluorine and / or chlorine atoms, alkoxy (C ₁ -C ₄ ), haloalkoxy (C ₁ -C ₄ ) with 1 to 4 identical or different fluorine and / or chlorine atoms, alkylthio (C ₁ -C ₄ ), haloalkylthio (C ₁ -C ₄ ) with 1 to 4 identical or different fluorine or chlorine atoms, amino, monoalkylamino with straight-chain or branched alkyl radicals ( C ₁ -C ₅ ), dialkylamino with the same or different, straight-chain or branched alkyl radicals (C ₁ -C ₄ ), or
R ² and R ^{3 are} connected via the group -CH = CH-CH = CH-, which is optionally substituted one to four times by fluorine, chlorine, nitro, cyano, alkyl (C ₁ -C ₄ ), haloalkyl (C ₁ - C ₄ ) with 1 to 4 identical or different fluorine and / or chlorine atoms, alkoxy (C ₁ -C ₄ ), haloalkoxy (C ₁ -C ₄ ) with 1 to 4 identical or different fluorine and / or chlorine atoms, alkylthio ( C ₁ -C ₄ ), haloalkylthio (C ₁ -C ₄ ) with 1 to 4 identical or different fluorine and / or chlorine atoms, amino, monoalkylamino with straight-chain or branched alkyl radicals (C ₁ -C ₅ ), dialkylamino with identical or different , straight-chain or branched alkyl radicals (C ₁ -C ₄ ), or fused with an aryl ring.
R ⁵ , R ⁶ or R ^{7 are the} same or different and are independently hydrogen, nitro, cyano, fluorine, chlorine, straight-chain or branched alkyl (C ₁ -C ₆ ), alkenyl (C ₂ -C ₆ ) or alkynyl ( C ₂ -C ₆ ), which is optionally substituted one or more times, identically or differently, by fluorine, chlorine, optionally substituted phenyl, alkoxy (C ₁ -C ₄ ), haloalkoxy (C ₁ -C ₄ ) with 1 to 5 of the same or various fluorine and / or chlorine atoms, acyl (C ₁ -C ₅ ) or optionally substituted aryl, pyridyl.

Compounds of the formula (I) in which
X ^{1 represents} oxygen or sulfur,
Y stands for -CHR ⁷ - or -CHR ⁵ CHR ⁶ -,
Z ^{1 represents} sulfur, oxygen, NR ¹ ,
Z ^{2 represents} CR ² or nitrogen,
Z ^{3 represents} CR ³ or nitrogen,
Z ^{4 represents} CR ⁴ or nitrogen, where
R ¹ , R ² , R ³ , R ^{4 are the} same or different and independently of one another are hydrogen, cyano, nitro, straight-chain or branched alkyl, alkenyl, alkynyl, in particular methyl, ethyl, n-propyl, i-propyl, n-butyl , i-butyl, s-butyl, t-butyl, cyclohexyl, cyclopentyl, allyl, propargyl, which are in each case optionally substituted one to three times, identically or differently, by fluorine, chlorine, nitro, cyano, alkoxy, in particular methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, haloalkoxy, especially difluoromethoxy, trifluoromethoxy, dichlorofluoromethoxy, difluorochloromethoxy, pentafluoroethoxy, benzylthio, alkylthio, in particular methylthio, ethylthio, n -Propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio, t-butylthio, haloalkylthio, in particular difluoromethylthio, trifluoromethylthio, dichlorofluoromethylthio, difluorochloromethylthio, pentafluoroethylthio, phenyl, pyrylylpyryl, pyryl; for alkoxy, in particular methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy; for haloalkoxy, especially difluoromethoxy, trifluoromethoxy, dichlorofluoromethoxy, difluorochloromethoxy, pentafluoroethoxy; for benzylthio; for alkylthio, in particular methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio, t-butylthio; for haloalkylthio, especially difluoromethylthio, trifluoromethylthio, di chlorofluoromethylthio, difluorochloromethylthio, pentafluoroethylthio; or for phenyl, pyridyl, pyrimidyl, pyrazinyl, which are optionally substituted one to three times, identically or differently, by fluorine, chlorine, alkyl, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s- Butyl, t-butyl, haloalkyl, especially difluoromethyl, trifluoromethyl, dichlorofluoromethyl, difluorochloromethyl, pentafluoroethyl, alkoxy, especially methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t- Butoxy, haloalkoxy, especially difluoromethoxy, trifluoromethoxy, dichlorofluoromethoxy, di fluorochloromethoxy, pentafluoroethoxy, alkylthio, especially methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio, especially halogeno Difluoromethylthio, trifluoromethylthio, dichlorofluoromethylthio, difluorochloromethylthio, pentafluoroethylthio, amino, monoalkylamino or dialkylamino with the same or different, straight-chain or branched alkyl radicals, in particular methyl, ethyl, n-propyl, i-propy l, n-butyl, i-butyl, s-butyl, t-butyl, stand,
or
R ² and R ^{3 are} connected via the group -CH = CH-CH = CH-, which is optionally substituted one to three times by fluorine and / or chlorine, nitro, cyano, alkyl, in particular methyl, ethyl, n-propyl, i Propyl, n-butyl, i-butyl, s-butyl, t-butyl, haloalkyl, especially difluoromethyl, trifluoromethyl, dichlorofluoromethyl, difluorochloromethyl, pentafluoroethyl, alkoxy, especially methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy , i-butoxy, s-butoxy, t-butoxy, haloalkoxy, in particular difluoromethoxy, trifluoromethoxy, dichlorofluoromethoxy, difluorochloromethoxy, pentafluoroethoxy, alkylthio, such as methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio, t-butylthio, haloalkylthio, especially difluoromethylthio, trifluoromethylthio, dichlorofluoromethylthio, difluorochloromethylthio, pentafluoroethylthio, amino, monoalkylamino or dialkylamino with the same or different, straight-chain or branched alkyl radicals, especially methyl, especially propyl, especially methyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl,
R ⁵ , R ⁶ or R ^{7 are} identical or different and, independently of one another, are hydrogen, nitro, cyano, fluorine, chlorine, straight-chain or branched alkyl, alkenyl, alkynyl, in particular methyl, ethyl, n-propyl, i-propyl, n- Butyl, i-butyl, s-butyl, t-butyl, allyl, propargyl, which is optionally substituted by fluorine and / or chlorine, optionally substituted phenyl, alkoxy, in particular methoxy, ethoxy, n-propoxy, i-propoxy, n- Butoxy, i-butoxy, s-butoxy, t-butoxy, haloalkoxy, especially difluoromethoxy, trifluoromethoxy, dichlorofluoromethoxy, difluorochloromethoxy, pentafluoroethoxy, acyl, especially formyl, acetyl, n-propionyl, i-propionyl, n-butyryl, i-butyryl , s-butyryl, or optionally substituted aryl, pyridyl.

Compounds in which
X ^{1 represents} sulfur.
Y represents -CH ₂ - or -CH ₂ CH ₂ -, in particular CH ₂ .
Z ^{1 represents} sulfur or NR ¹ .
Z ^{2 represents} CR ² or nitrogen.
Z ^{3 represents} CR ³ or nitrogen.
Z ^{4 represents} CH or nitrogen.

Those in the respective combinations or preferred combinations of residues radical definitions given in detail for these radicals are independent of the combination specified in each case, optionally also by means of residual definitions  other combinations replaced. In addition, residue definitions can also be from any Preferred area does not apply.

The compounds of the formula (I) are obtained if (process a) compounds of the general formula (II)

in which
Y has the meaning given above and X ^{2 represents} bromine or chlorine,
with compounds of the general formula (III),

in which
X ¹ , Z ¹ , Z ² , Z ³ and Z ^{4 have} the meanings given above,
if appropriate in the presence of a base and if appropriate in the presence of a diluent.

The reaction temperatures in this process can be at a higher temperature range can be varied. Generally one works between -30 ° C and + 100 ° C, preferably between -10 ° C and + 60 ° C.

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

Possible diluents that can be used are both water and also all organic solvents in question. This preferably includes coals Hydrogen such as toluene, xylene or hexane, chlorinated hydrocarbons such as Chlorobenzene and chloroform, ketones such as acetone, ethers such as tetrahydrofuran, Diethyl ether, methyl tert-butyl ether and dioxane, nitriles such as acetonitrile, and DMSO, DMF and NMP.

The compounds of formula (II) are known (cf. WO 98/52945) or can be Manufacture according to analog processes.

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

It has also been found that the compounds of the formula (I) with X ¹ in its meaning as sulfur, in many cases, are also obtained (process b) if the salts of the general formula (IV)

in which
Y has the meaning given above and
M ^{+ stands} for an alkali or alkaline earth metal, in particular for Na ⁺ or K ⁺ , with diazonium salts of the general formula (V)

in which
Z ¹ _, Z ² , Z ³ and Z ^{4 have} the meanings given above and
A ^{- represents} the anion of a mineral acid,
in aqueous / alkaline solution, optionally in the presence of a catalyst.

A base and, if appropriate, are preferably added to a solution of (IV) a catalyst and then the diazonium salt solution (V). As bases preferably alkali metal hydroxides such as potassium hydroxide or sodium hydroxide used. As catalysts you can use all catalysts that promotes the exchange of the diazonium function for sulfur-containing residues.

Cu (I) salts or copper powder are preferably used. The temperature during the addition of the diazonium salt solution can be over a wide range can be varied. In general, you work between -30 ° C and + 60 ° C, preferably  Way between -20 ° C and + 40 ° C. The diazonium salt solution is prepared according to literary methods.

The compounds of the formula (IV) are known (cf. DE 195 45 635; WO-98/29400) or can be produced analogously.

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

in which
Y and M ^{+ have} the meanings given above,
with compounds of the general formula (VI)

in which
Z ¹ , Z ² , 2 ³ and Z ^{4 have} the meanings given above and
X ^{3 represents} a leaving group, in particular mesyl, tosyl, fluorine, chlorine or bromine,
if appropriate in the presence of a base and if appropriate in the presence of diluents.

The reaction temperatures can be larger in this process Temperature range can be varied. Generally one works between -30 ° C and + 150 ° C, preferably between -10 ° C and + 100 ° C.

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

Possible diluents that can be used are both water and also all organic solvents in question. These preferably include Koh Hydrogen oils such as toluene, xylene or hexane, chlorinated hydrocarbons such as Chlorobenzene and chloroform, ketones such as acetone, ethers such as tetrahydrofuran, Diethyl ether, methyl tert-butyl ether and dioxane, nitriles such as acetonitrile, and DMSO, DMF and NMP.

All methods of the invention are generally under normal pressure carried out. It is also possible, however, under increased or reduced pressure - generally between 0.1 bar and 10 bar - to work.

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

Fungicides can be used in crop protection to combat plasmodiophoro mycetes, oomycetes, chytridiomycetes, zygomycetes, ascomycetes, basidiomy Use cetes and Deuteromycetes.  

Bactericides can be used in plant protection to combat Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae put.

Some pathogens of fungal and bacterial diseases that fall under the generic names listed above may be mentioned as examples, but not by way of limitation:
Xanthomonas species, such as, for example, Xanthomonas campestris pv. Oryzae;
Pseudomonas species, such as, for example, Pseudomonas syringae pv. Lachrymans;
Erwinia species, such as, for example, Erwinia amylovora;
Pythium species, such as, for example, Pythium ultimum;
Phytophthora species, such as, for example, Phytophthora infestans;
Pseudoperonospora species, such as, for example, Pseudoperonospora humuli or Pseudoperonospora cubensis;
Plasmopara species, such as, for example, Plasmopara viticola;
Bremia species, such as, for example, Bremia lactucae;
Peronospora species, such as, for example, Peronospora pisi or P. brassicae;
Erysiphe species, such as, for example, Erysiphe graminis;
Sphaerotheca species, such as, for example, Sphaerotheca fuliginea;
Podosphaera species, such as, for example, Podosphaera leucotricha;
Venturia species, such as, for example, Venturia inaequalis;
Pyrenophora species, such as, for example, Pyrenophora teres or P. graminea
(Conidial form: Drechslera, Syn: Helminthosporium);
Cochliobolus species, such as, for example, Cochliobolus sativus (conidial form: Drechslera, Syn: Helminthosporium);
Uromyces species, such as, for example, Uromyces appendiculatus;
Puccinia species, such as, for example, Puccinia recondita;
Sclerotinia species, such as, for example, Sclerotinia sclerotiorum;
Tilletia species, such as, for example, Tilletia caries;
Ustilago species, such as, for example, Ustilago nuda or Ustilago avenae;
Pellicularia species, such as, for example, Pellicularia sasakii;
Pyricularia species, such as, for example, Pyricularia oryzae;
Fusarium species, such as, for example, Fusarium culmorum;
Botrytis species, such as, for example, Botrytis cinerea;
Septoria species, such as, for example, Septoria nodorum;
Leptosphaeria species, such as, for example, Leptosphaeria nodorum;
Cercospora species, such as, for example, Cercospora canescens;
Alternaria species, such as, for example, Alternaria brassicae;
Pseudocercosporella species, such as, for example, Pseudocercosporella herpotrichoides.

The good plant tolerance of the active ingredients in the fight against Concentrations necessary for plant diseases allow treatment of above-ground parts of plants, planting and seeds, and the soil.

The active compounds according to the invention can be particularly successful Control of cereal diseases, such as against Erysiphe species, or diseases in wine, fruit and vegetable growing, such as against Use Plasmopara species.

Other diseases in wine, fruit and Vegetable cultivation, such as Phytophtora species, fought. The fiction Active ingredients are also suitable for increasing crop yield. they are also less toxic and have good plant tolerance.

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

In the present context, technical materials include non-living ones Understand materials that have been prepared for use in engineering are. For example, technical materials made by the invention  Active substances are to be protected against microbial change or destruction, Adhesives, glue, paper and cardboard, textiles, leather, wood, paints and Plastic items, coolants and other materials may be those of Microorganisms can be attacked or decomposed. As part of the Protective materials are also parts of production facilities, for example Cooling water circuits, called by multiplication of microorganisms can be affected. In the context of the present invention as technical materials preferably adhesives, glues, papers and boxes, leather, Wood, paints, coolants and heat transfer fluids called.

As microorganisms that break down or change the technical Materials can cause, for example, bacteria, fungi, yeast, algae and called mucus organisms. The ones according to the invention preferably act Active ingredients against fungi, in particular mold, wood-staining and wood destructive fungi (Basidiomycetes) and against mucous organisms and algae.

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

The active ingredients can depend on their respective physical and / or chemical properties converted into the usual formulations such as solutions, emulsions, suspensions, powders, foams, pastes, Granules, aerosols, very fine encapsulations in polymeric substances and in coating compositions for seeds, as well as ULV cold and warm mist formulations.

These formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, that is to say liquid solvents, under pressure, the liquefied gases and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents. In the case of the use of water as an extender, e.g. B. organic solvents can also be used as auxiliary solvents. The following are essentially suitable as liquid solvents:
Aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. B. petroleum fractions, alcohols, such as butanol or glycol and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexa non, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water. Liquefied gaseous extenders or carriers mean those liquids which are gaseous at normal temperature and pressure, e.g. B. aerosol propellants, such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide. As solid carriers come into question: B. natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock flours, such as highly disperse silica, aluminum oxide and silicates. Possible solid carriers for granules are: B. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours and granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks.

Possible emulsifiers and / or foam-generating agents are: B. non-iono gene and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxy ethylene fatty alcohol ether, e.g. B. alkylaryl polyglycol ether, alkyl sulfonates, alkyl sulfa te, aryl sulfonates and protein hydrolyzates. Possible dispersants are: e.g. B. lignin sulfite and methyl cellulose.

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

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

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

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

The following compounds can be considered as mixing partners for crop protection applications:
Fungicides:
Aldimorph, ampropylfos, ampropylfos potassium, andoprim, anilazine, azaconazole, azoxystrobin,
Benalaxyl, Benodanil, Benomyl, Benzamacril, Benzamacryl-Isobutyl, Bialaphos, Binapacryl, Biphenyl, Bitertanol, Blasticidin-S. Bromuconazole, bupirimate, buthiobate,
Calcium polysulfide, capsimycin, captafol, captan, carbendazim, carboxin, carvone, quinomethionate (quinomethionate), chlobenthiazone, chlorfenazole, chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon, cufraneb, cymoxanil, cyphodaminazol, cypodaminazol, cypodinconol
Debacarb, dichlorophene, diclobutrazole, diclofluanide, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, diniconazol-M, dinocap, diphenylamine, dipyrithione, ditalimfos, dithorphoxinodonine, dithorphononodine
Ediphenphos, Epoxiconazole, Etaconazole, Ethirimol, Etridiazole,
Famoxadone, fenapanil, fenarimol, fenbuconazole, fenfuram, fenitropan, fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam, ferimzon, fluazinam, flumetover, fluoromid, fluquinconazole, flurprimolol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusilazolutol, flusulfazolutol, flusulfazolutol, flusilazolutol, flusilazolutol, flusilazolutolol Fosetyl sodium, fthalide, fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole, furconazole-cis, furmecyclox,
Guazatin,
Hexachlorobenzene, hexaconazole, hymexazole,
Imazalil, Imibenconazol, Iminoctadin, Iminoctadinealbesilat, Iminoctadinetriacetat, Iodocarb, Ipconazol, Iprobefos (IBP), Iprodione, Irumamycin, Isoprothiolan, Isovaledione,
Kasugamycin, Kresoxim-methyl, copper preparations, such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxine-copper and Bordeaux mixture,
Mancopper, Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Metrifuroxam, Metiram, Metomeclam, Metsulfovax, Mildiomycin, Myclobutanil, Myclozolin,
Nickel dimethyldithiocarbamate, nitrothal isopropyl, Nuarimol,
Ofurace, Oxadixyl, Oxamocarb, Oxolinicacid, Oxycarboxim, Oxyfenthiin,
Paclobutrazol, Pefürazoat, Penconazol, Pencycuron, Phosdiphen, Pimaricin, Piperalin, Polyoxin, Polyoxorim, Probenazole, Prochloraz, Procymidon, Propamocarb, Propanosine-Sodium, Propiconazole, Propineb, Pyrazophos, Pyrifen, Pyifenox, Pyroyfurilonil
Quinconazole, quintozen (PCNB),
Sulfur and sulfur preparations,
Tebuconazole, tecloftalam, tecnazene, Tetcyclacis, tetraconazole, thiabendazole, Thicyofen, Thifluzamide, thiophanate-methyl, thiram, Tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, Triazbutil, triazoxide, Trichlamid, tricyclazole, tridemorph, triflumizole, triforine, triticonazole,
Uniconazole,
Validamycin A, vinclozolin, viniconazole,
Zarilamid, Zineb, Ziram as well
Dagger G,
OK-8705,
OK-8801,
α- (1,1-dimethylethyl) -β- (2-phenoxyethyl) -1H-1,2,4-triazole-1-ethanol,
α- (2,4-dichlorophenyl) -β-fluoro-b-propyl-1H-1,2,4-triazole-1-ethanol,
α- (2,4-dichlorophenyl) -β-methoxy-a-methyl-1H-1,2,4-triazole-1-ethanol,
α- (5-methyl-1,3-dioxan-5-yl) -β - [[4- (trifluoromethyl) phenyl] methylene] -1H-1,2,4-triazol-1-ethanol,
(5RS, 6RS) -6-Hydroxy-2,2,7,7-tetramethyl-5- (1H-1,2,4-triazol-1-yl) -3-octanone, (E) -a- (methoxyimino ) -N-methyl-2-phenoxy-phenylacetamide,
{2-Methyl-1 - [[[1- (4-methylphenyl) ethyl] amino] carbonyl] propyl} carbamic acid 1-isopropyl ester
1- (2,4-dichlorophenyl) -2- (1H-1,2,4-triazol-1-yl) -ethanone-O- (phenylmethyl) oxime,
1- (2-methyl-1-naphthalenyl) -1H-pyrrole-2,5-dione,
1- (3,5-dichlorophenyl) -3- (2-propenyl) -2,5-pyrrolidinedione,
1 - [(diiodomethyl) sulfonyl] -4-methyl-benzene,
1 - [[2- (2,4-dichlorophenyl) -1,3-dioxolan-2-yl] methyl] -1H-imidazole,
1 - [[2- (4-chlorophenyl) -3-phenyloxiranyl] methyl] -1H-1,2,4-triazole,
1 [1- [2 - [(2,4-dichlorophenyl) methoxy] phenyl] ethenyl] -1H-imidazole,
1-methyl-5-nonyl-2- (phenylmethyl) -3-pyrrolidinol,
2 ', 6'-dibromo-2-methyl-4'-trifluoromethoxy-4'-trifluoromethyl-1,3-thiazole-5-carboxanilide,
2,2-dichloro-N- [1- (4-chlorophenyl) ethyl] -1-ethyl-3-methylcyclopropanecarboxamide,
2,6-dichloro-5- (methylthio) -4-pyrimidinyl-thiocyanate,
2,6-dichloro-N- (4-trifluoromethylbenzyl) benzamide,
2,6-dichloro-N - [[4- (trifluoromethyl) phenyl] methyl] benzamide,
2- (2,3,3-triiodo-2-propenyl) -2H-tetrazole,
2 - [(1-methylethyl) sulfonyl] -5- (trichloromethyl) -1,3,4-thiadiazole,
2 - [[6-Deoxy-4-O- (4-O-methyl-β-D-glycopyranosyl) -aD-glucopyranosyl] amino] -4- methoxy-1H-pyrrolo [2,3-d] pyrimidine- 5-carbonitrile,
2-aminobutane,
2-bromo-2- (bromomethyl) pentandinitrile,
2-chloro-N- (2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl) -3-pyridinecarboxamide,
2-chloro-N- (2,6-dimethylphenyl) -N- (isothiocyanatomethyl) acetamide,
2-phenylphenol (OPP),
3,4-dichloro-1- [4- (difluoromethoxy) phenyl] -1H-pyrrole-2,5-dione,
3,5-dichloro-N- [cyan [(1-methyl-2-propynyl) oxy] methyl] benzamide,
3- (1,1-dimethylpropyl-1-oxo-1H-indene-2-carbonitrile,
3- [2- (4-chlorophenyl) -5-ethoxy-3-isoxazolidinyl] pyridine,
4-chloro-2-cyan-N, N-dimethyl-5- (4-methylphenyl) -1H-imidazole-1-sulfonamide,
4-methyl-tetrazolo [1,5-a] quinazolin-5 (4H) -one,
8- (1,1-dimethylethyl) -N-ethyl-N-propy 1-1,4-dioxaspiro [4.5] decane-2-methanamine, 8-hydroxyquinoline sulfate,
9H-xanthene-9-carboxylic acid 2 - [(phenylamino) carbonyl] hydrazide,
bis- (1-methylethyl) -3-methyl-4 - [(3-methylbenzoyl) -oxy] -2,5-thiophene dicarboxylate,
cis-1- (4-chlorophenyl) -2- (1H-1,2,4-triazol-1-yl) cycloheptanol,
cis-4- [3- [4- (1,1-dimethylpropyl) phenyl-2-methylpropyl] -2,6-dimethylmorpholine hydrochloride,
Ethyl - [(4-chlorophenyl) azo] cyanoacetate,
Potassium hydrogen carbonate,
Methane tetrathiol sodium salt,
Methyl 1- (2,3-dihydro-2,2-dimethyl-1-H-inden-1-yl) -1H-imidazole-5-carboxylate,
Methyl N- (2,6-dimethylphenyl) -N- (5-isoxazolylcarbonyl) -DL-alaninate,
Methyl N- (chloroacetyl) -N- (2,6-dimethylphenyl) -DL-alaninate,
N- (2,3-dichloro-4-hydroxyphenyl) -1-methyl-cyclohexane carboxamide.
N- (2,6-dimethylphenyl) -2-methoxy-N- (tetrahydro-2-oxo-3-furanyl) acetamide,
N- (2,6-dimethylphenyl) -2-methoxy-N- (tetrahydro-2-oxo-3-thienyl) acetamide,
N- (2-chloro-4-nitrophenyl) -4-methyl-3-nitro-benzenesulfonamide,
N- (4-cyclohexylphenyl) -1,4,5,6-tetrahydro-2-pyrimidinamine,
N- (4-hexylphenyl) -1,4,5,6-tetrahydro-2-pyrimidinamine,
N- (5-chloro-2-methylphenyl) -2-methoxy-N- (2-oxo-3-oxazolidinyl) acetamide,
N- (6-methoxy) -3-pyridinyl) cyclopropanecarboxamide,
N- [2,2,2-trichloro-1 - [(chloroacetyl) amino] ethyl] benzamide,
N- [3-chloro-4,5-bis (2-propynyloxy) phenyl] -N'-methoxymanimidamide,
N-formyl-N-hydroxy-DL-alanine sodium salt,
O, O-diethyl- [2- (dipropylamino) -2-oxoethyl] ethylphosphoramidothioate,
O-methyl-S-phenyl-phenylpropylphosphoramidothioate,
S-methyl-1,2,3-benzothiadiazole-7-carbothioate,
spiro [2H] -1-benzopyran-2,1 '(3'H) -isobenzofuran] -3'-one,

Bactericides

Bronopol, dichlorophene, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, Octhilinone, furan carboxylic acid, oxytetracycline, probenazole, streptomycin, Teclofta lam, 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, Butocarboximos, Butocarboximos
Cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan, cartap, Chloethocarb, chlorethoxyfos, chlorfenapyr, chlorfenvinphos, chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos M, Chlovaporthrin, cis-resmethrin, Cispermethrin, Clocythrin, cloethocarb, clofentezine, cyanophos, Cycloprene, cycloprothrin, cyfluthrin , Cyhalothrin, cyhexatin, cypermethrin, cyromazine,
Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Diazinon, Dichlorvos, Diflubenzuron, Dimethoat, Dimethylvinphos, Diofenolan, Disulfoton, Docusat-sodium, Dofenapyn,
Eflusilanate, Emamectin, Empenthrin, Endosulfan, Entomopfthora spp., Esfenvalerate, Ethiofencarb, Ethion, Ethoprophos, Etofenprox, Etoxazole, Etrimfos,
Fenamiphos, Fenazaquin, Fenbutatin oxide, Fenitrothion, Fenothiocarb, Fenoxacrim, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyrithrin, Fenpyroximate, Fenvalerate, Fipronil, Fluazinam, Fluazuron, Flubrocythrinate, Flucycloxoxinon, Flutoxinoxuron, Fluutinoxuron, Fluutinoxuron, Fluutinoxuron, , Furathiocarb,
Granulosis viruses
Halofenozide, HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene,
Imidacloprid, isazofos, isofenphos, isoxathion, ivermectin,
Nuclear polyhedron viruses
Lambda cyhalothrin, lufenuron
Malathion, Mecarbam, Metaldehyde, Methamidophos, Metharhician anisopliae, Metharhician flavoviride, Methidathione, Methiocarb, Methomyl, Methoxyfenozide, Metolcarb, Metoxadiazone, Mevinphos, Milbemectin, Monocrotophos,
Naled, Nitenpyram, Nithiazine, Novaluron
Omethoate, Oxamyl, Oxydemethon M
Paecilomyces fumosoroseus, Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos A, Pirimiphos M, Profenofos, Promecarb, Propoxur, Prothiofos, Prothoat, Pyromhrhridosine, Pymmethrofinos, Pymmethrofinos , Pyridathione, pyrimidifen, pyriproxyfen,
Quinalphos,
Ribavirin
Salithion, Sebufos, Silafluofen, Spinosad, Sulfotep, Sulprofos,
Tau-fluvalinate, oxalate hydrogen tebufenozide, tebufenpyrad, Tebupirimiphos, teflubenzuron, tefluthrin, temephos, Temivinphos, terbufos, tetrachlorvinphos, theta cypermethrin, thiamethoxam, Thiapronil, Thiatriphos, thiocyclam, thiodicarb, thiofanox, thuringiensin, Tralocythrin, tralomethrin, triarathene, Triazamate, triazophos , Triazuron, trichlophenidine, trichlorfon, triflumuron, trimethacarb,
Vamidothion, Vaniliprole, Verticillium lecanii
YI 5302
Zeta-cypermethrin, zolaprofos
(1R-cis) - [5- (phenylmethyl) -3-furanyl] methyl-3 - [(dihydro-2-oxo-3 (2H) - furanylidene) methyl] -2,2-dimethylcyclopropane carboxylate
(3-phenoxyphenyl) methyl 2,2,3,3-tetramethylcyclopropane decarboxylate
1 - [(2-Chloro-5-thiazolyl) methyl] tetrahydro-3,5-dimethyl-N-nitro-1,3,5-triazine-2 (1 H) - imine
2- (2-chloro-6-fluorophenyl) -4- [4- (1,1-dimethylethyl) phenyl] -4,5-dihydro-oxazole
2- (acetyloxy) -3-dodecyl-1,4-naphthalenedione
2-Chloro-N - [[[4- (1-phenylethoxy) phenyl] amino] carbonyl] benzamide
2-Chloro-N - [[[4- (2,2-dichloro-1,1-difluoroethoxy) phenyl] amino] carbonyl] benzamide
3-methylphenyl propyl carbamate
4- [4- (4-ethoxyphenyl) -4-methylpentyl] -1-fluoro-2-phenoxy-benzene
4-chloro-2- (1,1-dimethylethyl) -5 - [[2- (2,6-dimethyl-4-phenoxyphenoxy) ethyl] thio] - 3 (2H) pyridazinone
4-chloro-2- (2-chloro-2-methylpropyl) -5 - [(6-iodo-3-pyridinyl) methoxy] -3 (2H) - pyridazinone
4-chloro-5 - [(6-chloro-3-pyridinyl) methoxy] -2- (3,4-dichlorophenyl) -3 (2H) pyridazinone
Bacillus thuringiensis strain EG-2348
Benzoic acid [2-benzoyl-1- (1,1-dimethylethyl) hydrazide
Butanoic acid 2,2-dimethyl-3- (2,4-dichlorophenyl) -2-oxo-1-oxaspiro [4.5] dec-3-en-4-yl ester
[3 - [(6-chloro-3-pyridinyl) methyl) -2-thiazolidinylidene] cyanamide
Dihydro-2- (nitromethylene) -2H-1,3-thiazine-3 (4H) carboxaldehyde
Ethyl [2 - [[1,6-dihydro-6-oxo-1- (phenylmethyl) -4-pyridazinyl] oxy] ethyl] carbamate
N- (3,4,4-trifluoro-1-oxo-3-butenyl) glycine
N- (4-chlorophenyl) -3- [4- (difluoromethoxy) phenyl] -4,5-dihydro-4-phenyl-1H-pyrazole-1-carboxamide
N - [(2-chloro-5-thiazolyl) methyl] -N'-methyl-N "-nitro-guanidine
N-methyl-N '- (1-methyl-2-propenyl) -1,2-hydrazinedicarbothioamide
N-methyl-N'-2-propenyl-1,2-hydrazinedicarbothioamide
O, O-Diethyl- [2- (dipropylamino) -2-oxoethyl] ethyl phosphoramidothioate.

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

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

Triazoles such as:
Azaconazole, azocyclotin, bitertanol, bromuconazole, cyproconazole, diclobutrazole, difenoconazole, diniconazole, epoxyconazole, etaconazole, fenbuconazole, fenchlorazole, fenethanil, fluquinconazole, flusilazole, flutriafolacazazone Propioconazole, (±) -cis-1- (4-chlorophenyl) -2- (1H-1,2,4-triazol-1-yl) -cycloheptanol, 2- (1-tert-butyl) -1- ( 2-chlorophenyl) - 3- (1,2,4-triazol-1-yl) propan-2-ol, tebuconazole, tetraconazole, triadimefon, triadimenol, triapenthenol, triflumizole, triticonazole, uniconazole and their metal salts and acid adducts;

Imidazoles such as:
Clotrimazole, Bifonazole, Climbazole, Econazole, Fenapamil, Imazalil, Isoconazole, Ketoconazole, Lombazole, Miconazole, Oxpoconazole, Pefurazoate, Prochloraz, Tri flumizole, Thiazolcar 1-imidazolyl-1- (4'-chlorophen) -ethyl -on and their metal salts and acid adducts;

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

Succinate dehydrogenase inhibitors such as:
Benodanil, Carboxim, Carboximsulfoxid, Cyclafluramid, Fenfuram, Flutanil, Furcarbonil, Furmecyclox, Mebenil, Mepronil, Metrifuroxam, Metsulfovax, Pyrocarbolid, Oxycarboxin, Shirlan, Seedvax;

Naphthalene derivatives such as:
Terbinafine, naftifine, butenafine, 3-chloro-7- (2-aza-2,7,7-trimethyl-oct-3-en-5-in);

Sulfenamides such as:
Dichlorfluanide, tolylfluanid, folpet, fluorfolpet; Captan, Captofol;

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

Morpholine derivatives such as:
Aldimorph, Dimethomorph, Dodemorph, Falimorph, Fenpropidin Fenpropimorph, Tridemorph, Trimorphamid and their arylsulfonic acid salts, such as. B. p-toluenesulfonic acid and p-dodecylphenyl sulfonic acid;

Benzthiazoles such as:
2-mercaptobenzothiazole;

Benzothiophene dioxides such as:
Benzo [b] thiophene-S, S-dioxidcarboxylic acid cyclohexylamide;

Benzamides such as:
2,6-dichloro-N- (4-trifluoromethylbenzyl) benzamide, tecloftalam;

Boron compounds such as:
Boric acid, boric acid ester, borax;

Formaldehyde and formaldehyde releasing compounds such as:
Benzyl alcohol mono- (poly) hemiformal, n-butanol hemiformal, Dazomet, ethylene glycol hemiformal, hexa-hydro-S-triazine, hexamethylenetetramine, N-hydroxy methyl-N'-methylthiourea, N-methylolchloroacetamide, oxazolidine, paraform aldehyde, Tauroline, tetrahydro-1,3-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-octylisothiazolin-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, benzyldimethyl dodecylammonium chloride, dichlorobenzyl-dimethyl-alkyl-ammonium chloride, di decyldimethylammonium chloride, dioctyl-dimethyl-ammonium chloride, N-hexadecyl-trimethyl-ammonium chloride, 1-hexadecyl-pyridine

Iodine derivatives such as:
Diiodomethyl-p-tolyl sulfone, 3-iodo-2-propynyl alcohol, 4-chlorophenyl-3-iodo-propargyl formal, 3-bromo-2,3-diiodo-2-propenylethyl carbamate, 2,3,3-triiodallyl alcohol, 3 -Bromine-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-pro pinyl phenyl carbamate;

Phenols such as:
Tribromophenol, tetrachlorophenol, 3-methyl-4-chlorophenol, 3,5-dimethyl-4-chlorophenol, phenoxyethanol, dichlorophen, 2-benzyl-4-chlorophenol, 5-chloro-2- (2,4-dichlorophenoxy) phenol, Hexachlorophene, p-hydroxybenzoic acid ester, o-phenyl phenol, 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-1,3-propanediol, 2-bromo-4'-hydroxy-acetophe non, 1-bromo-3-chloro-4,4,5,5-tetramethyl-2- imidazoldinone, β-bromo-β-nitrostyrene, chloroacetamide, chloramine T, 1,3-dibromo-4,4,5,5-tetrametyl-2-imidazoldinone, dichloramine T, 3,4-dichloro- (3H) -1, 2-dithiol-3-one, 2,2-dibromo-3-nitrile-propionamide, 1,2-dibromo-2,4-dicyanobutane, halanes, halazones, mucochloric acid, phenyl- (2-chloro-cyan-vinyl) sulfone, Phenyl- (1,2-dichloro-2-cyanovinyl) sulfone, trichloroisocyanuric acid;

Pyridines such as:
1-Hydroxy-2-pyridinthione (and its Na, Fe, Mn, Zn salts), tetrachloro-4-methylsulfonylpyridine, pyrimethanol, mepanipyrim, dipyrithione, 1-hydroxy-4-methyl-6- (2,4 , 4-trimethylpentyl) -2 (1 H) pyridine;

Methoxyacrylates or similar like:
Methyl (E) methoximino [alpha- (o-tolyloxy) -o-tolyl] acetate,
(E) -2-methoxyimino-N-methyl-2- (2-phenoxyphenyl) acetamide,
(E) -2- {2- [6- (2-cyanophenoxy) pyrimidin-4-yloxy] phenyl} -3-methoxyacrylate,
O-methyl-2 - [([3-methoximino-2-butyl) imino] oxy) o-tolyl] -2-methoximinoacet imidate,
2 - [[[[1- (2,5-dimethylphenyl) ethylidene] amino] oxy] methyl] -. Alpha .- (methoximino) - N-methyl-benzeneacetamide,
alpha- (methoxyimino) -N-methyl-2 - [[[[[[1- [3- (trifluoromethyl) phenyl] ethylidene] amino] oxy) methyl] benzene acetamides,
alpha- (methoxyimino) -2 - [[[[1- [3- (trifluoromethyl) phenyl] ethylidene] amino] oxy] methyl] -benzeneaceticacid methyl ester,
alpha- (methoxymethylene) -2 - [[[[1- [3- (trifluoromethyl) phenyl] ethylidene] amino] oxy] methyl] -benzeneaceticacid methyl ester,
2 - [[[5-chloro-3- (trifluoromethyl) -2-pyridinyl] oxy] methyl] -. Alpha .- (methoxyimino) -N-methyl-benzeneacetamide,
2 - [[[cyclopropyl [(4-ethoxyphenyl) imino] methyl] thiojmethyl] -. Alpha.- (methoxyimino) -benzeneaceticacid-methyl ester,
alpha- (methoxyimino) -N-methyl-2- (4-methyl-5-phenyl-2,7-dioxa-3,6-diazaocta-3,5-dien-1-yl) -benzeneacetamide,
alpha- (methoxymethylene) -2- (4-methyl-5-phenyl-2,7-dioxa-3,6-diazaocta-3,5-dien-1-yl) -benzeneaceticacid-methyl ester,
alpha- (methoxyimino) -N-methyl-2 - [[[[[1- [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-morpholinyl) -2,7-dioxa-3,6-diazanona-3,5-dien-1-yl] -alpha.- (methoxymethylene) -benzeneaceticacid-methyl ester ;

Metal soaps like:
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, Cu ₂ O, CuO, ZnO;

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

Nitriles such as:
2,4,5,6-tetrachloroisophthalonitrile, disodium cyano-dithioimidocarbamate;

Quinolines such as:
8-hydroxyquinoline and its Cu salts;

other fungicides and bactericides such as:
5-hydroxy-2 (5H) furanone; 4,5-benzdithiazolinone, 4,5-trimethylene dithiazolinone, N- (2-p-chlorobenzoylethyl) hexaminium chloride, 2-oxo-2- (4-hydroxyphenyl) acethydr oximic acid chloride, tris-N- (cyclohexyldiazenium dioxy) 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 are very particularly preferred
Azaconazole, bromuconazole, cyproconazole, dichlobutrazole, diniconazole, hexa conazole, metaconazole, penconazole, propiconazole, tebuconazole, dichlofluanid, tolylfluanid, fluorofolpet, metrifuroxam, carboxin, benzo [b] -thiodophenyl-2-carboxyl-2-carboxamide (2) , 2-difluoro-1,3-benzodioxol-4-yl) -1H-pyrrole-3-carbonitrile, butenafine, imazalil, N-methylisothiazolin-3-one, 5-chloro-N-methylisothiazolin-3-one, N- Octylisothiazolin-3-one, dichloro-N-octylisozhiazolinon, mercaptobenthiazole, thiocyanatomethylthiobenzothiazol, benzisothiazolinone, Nn-butylisothiazolinone, N- (2-hydroxypropyl) amino-methanol, benzyl alcohol- (hemi) - formal, N-methylolchloroacetam -Hydroxypropyl) amine methanol, glutar aldehyde, omadine, dimethyl dicarbonate, and / or 3-iodo-2-propynyl-n-butyl carbamate.

Furthermore, in addition to the above-mentioned fungicides and bactericides for Material protection applications also have effective mixtures with other active ingredients fen manufactured:

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-chlorophenyl) -1- (ethoxymethyl) -5- (trifluoromethyl) -1H-pyrrole-3-carbonitrile, Bendiocarb, Benfuracarb, Bensultap, Betacyfluthrin, Bifenthrin, Bioresmethrin, Bioallethrin Bromophos A, Bromophos M, Bufencarb, Buprofezin, Butathiophos, Butocarboxin, Butoxycarboxim,
Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, Chinomethionate, Cloethocarb, Chlordane, Chlorethoxyfos, Chlorfenvinphos, Chlorfluazuron, Chlormephos, N - [(6-Chloro-3-pyridinyl) -methyl] -N'-cyano-N-methyl -ethanimidamide, chlorpicrin, chlorpyrifos A, chlorpyrifos 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, 1,2-Dibenzoyl-1 (1,1-dimethyl) -hydrazine, DNOC, Dichlofenthion, Dichlorvos, Dicliphos, Dicrotophos, Diflubenzuron , Dimethoate, dimethyl- (phenyl) -silylmethyl-3-phenoxybenzylether, dimethyl- (4-ethoxyphenyl) -silylmethyl-3-phenoxybenzylether, 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, Flxthroxinphonate, Floxethrinifurinate, Flucythrinolanate, Flucythrininone, Flucythrininate, Flucythrininone, Flucythrininate, Flucythrininate, Flucythrininate, Flucythrininate, Flucythrininone, Fosthiazat, Fubfenprox, Furathiocarb,
HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydramethylnon, Hydroprene,
Imidacloprid, Iodfenfos, Iprobefos, Isazophos, Isoamidophos, Isofenphos, Isoprocarb, Isoprothiolane, Isoxathion, Ivermectin, Lama-cyhalothrin, Lufenuron,
Kadedrin
Lambda-cyhalothrin, lufenuron,
Malathion, Mecarbam, Mervinphos, Mesulfenphos, Metaldehyde, Methacrifos, Methamidophos, Methidathion, Methiocarb, Methomyl, Metalcarb, Milbemectin, Monocrotophos, Moxiectin,
Naled, NC184, NI 125, Nicotine, Nitenpyram,
Omethoate, Oxamyl, Oxydemethon M, Oxydeprofos,
Parathion A, Parathion M, Penfluron, Permethrin, 2- (4-phenoxyphenoxy) ethyl ethyl carbamate, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos M, Pirimiphos A, Prallethrin, Profenophos, Promecarb, Propaphos , Prothiophos, F'rothoat, Pymetrozin, Pyrachlophos, Pyridaphenthion, Pyresmethrin, Pyrethrum, Pyridaben, Pyrimidifen, Pyriproxifen,
Quinalphos,
Resmethrin, RH-7988, Rotenone,
Salithion, Sebufos, Silafluofen, Sulfotep, Sulprofos,
Tau fluvalinate, Taroils, Tebufenozide, Tebufenpyrad, Tebupirimphos, Teflubenzuron, Tefluihrin, Temephos, Terbam, Terbufos, Tetrachlorvinphos, Tetramethrin, Tetramethacarb, Thiacloprid, Thiafenox, Thiamethoxiloxamoxiamoxiliamoxi Tralomethrin, triarathes, triazophos, triazamates, triazuron, trichlorfon, triflumuron, trimethacarb,
Vamidothione, XMC, xylylcarb, zetamethrin;

Molluscicides:
Fentin acetates, metaldehydes, methiocarb. Niclosamide;

Herbicides and algicides
Acetochlor, Acifluorfen, Aclonifen, Acrolein, Alachlor, Alloxydim, Ametryn, Amidosuliron, Amitrole, Ammonium sulfamate, Anilofos, Asulam, Atrazine, Aziptrotryne, Azimsulfuron,
Benazolin, Benfluralin, Benfuresate, Bensulfuron, Bensulfide, Bentazone, Benzofencap, Benzthiazuron, Bifenox, Borax, Bromacil, Bromobutide, Bromofenoxim, Bromoxynil, Butachlor, Butamifos, Butralin, Butylate, Bialaphos, Benzoyl-prop, Bromobutide
Carbetamide, chlomethoxyfen, chloramben, chlorbromuron, chlorflurenol, chloridazon, chlorimuron, chlornitrofen, Chloroacetic acid, chlorotoluron, chloroxuron, chlorpropham, chlorsulfuron, chlorthal, chlorthiamid, cinmethylin, Cinofulsuron, clethodim, clomazone, Chlomeprop, clopyralid, cyanamide, cyanazine, Cycloate, Cycloxydim , Chloroxynil, clodinafop-propargyl, cumyluron, CGA 248757, clometoxyfen, cyhalofop, clopyrasuluron, cyclosulfamuron,
Dichlorprop, Dichlorprop-P, Diclofop, Diethatyl, Difenoxuron, Difenzoquat, Diflufenican, Dimefuron, Dimepiperate, Dimethachlor, Dimethipin, Dinitramine, Dinoseb, Dinoseb Acetate, Dinoterb, Diphenamid, Dipropetryn, Diquat, Dithiopyr, Dithiopyr, Dithiopyr -D, Dairnuron, Dalapon, Dazomet, 2,4-DB, Desmedipham, Desmetryn, Dicamba, Dichlobenil, Dimethamid, Dithiopyr, Dimethametryn,
Eglinazine, Endothal, EPTC, Esprocarb, Ethalfluralin, Ethidimuron, Ethofumesate, Ethobenzanid, Ethoxyfen, ET751, Ethamelaulfuron,
Fenoxaprop, Fenoxaprop-P, Fenuron, Flamprop, Flamprop-M, Flazasulfuron, Fluazifop, Fluazifop-P, Fuenachlor, Fluchloralin, Flumeturon, Fluorocglycofen, Fluoronitrofen, Flupropanate, Flurenol, Fluridone, Flurochloridone, Flomesoxamines, Flomesoxamines Flamprop-isopropyl-L, Flumiclorac pentyl, Flumipropyn, Flumioxzim, Flurtatone, Flumioxzim,
Glyphosate, glufosinate-ammonium
Haloxyfop, hexazinones,
Imazamethabenz, isoproturon, isoxaben, isoxapyrifop, imazapyr, imazaquin, imazethapyr, ioxynil, isopropalin, imazosulfuron,
KUH 911, 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, Metriburononin, Metriburonon, MStrate 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, propisulfachlor, propynam, propynamam, propynamam, , 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, triallate, triasulfuron, tribenuron, triclopyrietidin, trifurl trifurididonium, triclopural, tri-sulfonidium, triclopural, tri-sulfonidium, triclopural, tri-sulfonid, triclopural, tri-sulfonid, triclopural, tri-sulfonid, triclopyrietin
Vemolate.

The active substances can be used as such, in the form of their formulations or in the form thereof rode application forms, such as ready-made solutions, suspensions, spray powders, pastes, soluble powders, dusts and granules can be used. The Application happens in the usual way, e.g. B. by pouring, spraying, spraying hen, scattering, dusting, foaming, brushing, etc. It is also possible apply the active ingredients according to the ultra-low-volume process or the Active ingredient preparation or inject the active ingredient itself into the soil. It can also the seeds of the plants are treated.

When using the active compounds according to the invention as fungicides, the effort can be reduced quantities can be varied within a wide range depending on the type of application. When treating parts of plants, the active compound application rates are in the generally in the range from 0.1 to 10,000 g / ha, preferably from 10 to 1,000 g / ha. In the case of seed treatment, the active compound application rates are in general in the range of 0.001 to 50 g per kilogram of seed, preferably from 0.01 to 10 g per kilogram of seed. When treating the floor, there are problems wall amounts of active ingredient generally in the range from 0.1 to 10,000 g / ha, preferably from 1 to 5,000 g / ha.

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

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

With good plant tolerance and favorable warm-blood toxicity, the active ingredients are suitable for controlling animal pests, in particular insects, arachnids and nematodes, which occur in agriculture, in forests, in the protection of stored products and materials, and in the hygiene sector. They can preferably be used as pesticides. They are effective against normally sensitive and resistant species as well as against all or individual stages of development. The pests mentioned above include:
From the order of the Isopoda z. B. Oniscus asellus, Armadillidium vulgare, Porcellio scaber.
From the order of the Diplopoda z. B. Blaniulus guttulatus.
From the order of the Chilopoda z. B. Geophilus carpophagus, Scutigera spp.
From the order of the Symphyla z. B. Scutigerella immaculata.
From the order of the Thysanura z. B. Lepisma saccharina.
From the order of the Collembola z. B. Onychiurus armatus.
From the order of Orthoptera z. B. Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp., Schistocerca gregaria.
From the order of the Blattaria z. B. Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica.
From the order of the Dermaptera z. B. Auricular Forficula.
From the order of the Isoptera z. B. Reticulitermes spp.
From the order of the Phthiraptera z. B. Pediculus humanus corporis, Haematopinus spp., Linognathus spp., Trichodectes spp., Damalinia spp.
From the order of the Thysanoptera z. B. Hercinothrips femoralis, Thrips tabaci, Thrips palmi, Frankliniella accidentalis.
From the order of Heteroptera z. B. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.
From the order of Homoptera z. B. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus sppe, Phrosiphumumonpp., Macrosiphumum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp.
From the order of the Lepidoptera z. B. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella xylostella, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiisppella, Fpp., Phylloc , Heliothis spp., Mamestra brassicae, Panolis flammea, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Hofeamannodellailaella, Hofeamannellaellaella, Tinea pellionella Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana, Cnaphalocerus spp.
From the order of the Coleoptera z. B. Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephppis, Orphusus spp. , Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Giptusibbium psol. Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica.
From the order of the Hymenoptera z. B. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
From the order of the Diptera z. B. Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomox ., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa, Hylemyia spp., Liriomyza spp.
From the order of the Siphonaptera z. B. Xenopsylla cheopis, Ceratophyllus spp.
From the class of the Arachnida z. B. Scorpio maurus, Latrodectus mactans, Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalommodes spp., I ., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Hemitarsonemus spp., Brevipalpus spp.

The plant parasitic nematodes include z. B. Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp., Bursaphelenchus spp.

The compounds of the formula (I) according to the invention can be used in particular good success for controlling plant-damaging insects, such as wise against the caterpillars caterpillars (Plutella maculipennis).

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

The active ingredient content of the prepared from the commercially available formulations Application forms can vary widely. The active substance concentration of the Application forms can range from 0.0000001 to 95% by weight Active ingredient, preferably from 0.0001 to 1 wt .-%.

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

When used against hygiene and storage pests, the stands out Active ingredient through an excellent residual effect on wood and clay as well as through good stability to alkali on limed substrates.  

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

Manufacturing examples

example 1

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

Example 2

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

Analogously to Example 1 and Example 2 and the general description, the example compounds mentioned in Table 1 are obtained.

Examples of use

The minimal inhibitory concentrations are used to demonstrate the effectiveness against fungi trations (MIC) determined by agents according to the invention:

Example A

An agar made using malt extract is also invented active ingredients according to the invention in concentrations of 0.1 mg / l to 5000 mg / l. After the agar has solidified, it is contaminated with pure cultures of those in the table 2 listed test organisms. After 2 weeks of storage at 28 ° C and 60 to The MIC is determined at 70% relative air humidity. MIC is the lowest Concentration of active substances with no growth due to the micro used benart takes place, it is given in Table A below.  

Table A

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

Example B

Plasmopara test (vine) / protective
Solvent:
24.5 parts by weight of acetone
24.5 parts by weight of dimethylacetamide
Emulsifier:
1.0 part by weight of alkylaryl polyglycol ether

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

To test for protective effectiveness, young plants are treated with the active ingredient sprayed substance preparation in the specified application rate. After the The plants are sprayed with an aqueous spore suspension of Plasmopara viticola inoculated and then remain in an incubation cabin for 1 day at approx. 20 ° C and 100% relative humidity. Then the plants 5 Days in a greenhouse at about 21 ° C and about 90% relative humidity. The plants are then moistened and placed in an incubation cabin for 1 day.

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

In this test, those in Examples 1, 3, 4, 5, 6, 7, 8, 9, 10, 12, 13, 15, 18, 20, 22, 25, 26 and 42 listed substances according to the invention at an application rate of 250 g / ha an efficiency of 90% or more.  

Example C

Erysiphe test (barley) / protective
Solvent: 50 parts by weight of N, N-dimethylformamide
Emulsifier: 1.2 parts by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amounts of solvent and emulsifier and dilute the concentrate with water to the desired concentration.

To test for protective effectiveness, young plants are sprayed with the Active ingredient preparation in the specified application rate. A day after The plants are treated with spores of Erysiphe graminis fsp. hordei inoculated. Then the plants in a greenhouse at 70% relative Humidity and a temperature of 18 ° C set up.

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

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

Example D

Plutella test / artificial feed
Solvent: 100 parts by weight of acetone
Emulsifier: 1900 parts by weight of methanol

To produce a suitable preparation of active compound, it is mixed 1 part by weight of active ingredient with the specified amount of solvent and dilute that Concentrate with methanol to the desired concentration.

A specified amount of active ingredient is added to a standardized amount of synthetic feed pipetted preparation of the desired concentration. After the methanol has evaporated, one is filled with approx. 100 plutella eggs per cavity Film can lid attached. The newly hatched larvae migrate to the treated artificial food.

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

In this test, e.g. B. the connection of the manufacturing example (14) in a exemplary drug concentration of 0.1%, a kill of 95% after 7 Days.

Claims (9)

1. Compounds of the general formula (I)
in which
X ^{1 represents} oxygen or sulfur,
Y stands for -CHR ⁷ - or -CHR ⁵ CHR ⁶ -,
Z ^{1 represents} sulfur, oxygen, NR ¹ ,
Z ^{2 represents} CR ² or nitrogen,
Z ^{3 represents} CR ³ or nitrogen,
Z ^{4 represents} CR ⁴ or nitrogen,
R ¹ , R ² , R ³ and R ^{4 are the} same or different and are independently hydrogen, cyano, nitro, substituted or unsubstituted alkyl, alkenyl, alkynyl, alkoxy, haloalkoxy, benzylthio, alkylthio, haloalkylthio, aryl, pyridyl, pyrimidyl or pyrazinyl or are optionally connected via one of these substituents and
R ⁵ , R ⁶ and R ^{7 are the} same or different and independently of one another represent hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, pyridyl, nitro, cyano or halogen. 2. Compounds according to claim 1, characterized in that
X ^{1 represents} oxygen or sulfur,
Y stands for -CHR ⁷ - or -CHR ⁵ CHR ⁶ -,
Z ^{1 represents} sulfur, oxygen, NR ¹ ,
Z ^{2 represents} CR ² or nitrogen,
Z ^{3 represents} CR ³ or nitrogen,
Z ^{4 represents} CR ⁴ or nitrogen, where
R ¹ , R ² , R ³ , R ⁴ independently of one another for hydrogen, cyano, nitro, straight-chain or branched alkyl (C ₁ -C ₆ ), alkenyl (C ₂ -C ₆ ), alkynyl (C ₂ -C ₆ ) , which are optionally substituted one or more times, identically or differently, by halogen, nitro, cyano, alkoxy (C ₁ -C ₆ ), haloalkoxy (C ₁ -C ₆ ) with 1 to 9 identical or different halogen atoms, alkylthio ( C ₁ -C ₆ ), haloalkylthio (C ₁ -C ₆ ) with 1 to 9 identical or different halogen atoms, phenyl, pyridyl, pyrimidyl, or pyrazinyl; for alkoxy (C ₁ -C ₅ ); for haloalkoxy (C ₁ -C ₅ ) with 1 to 6 identical or different halogen atoms, benzylthio; Alkylthio (C ₁ -C ₅ ); Haloalkylthio (C ₁ -C ₅ ) with 1 to 6 identical or different halogen atoms; or for phenyl, pyridyl, pyrimidyl or pyrazinyl, which are each optionally one to more times substituted by halogen, alkyl (C ₁ -C ₅ ), haloalkyl (C ₁ -C ₅ ) with 1 to 6 identical or different halogen atoms, alkoxy ( C ₁ -C ₅ ), haloalkoxy (C ₁ -C ₅ ) with 1 to 6 identical or different halogen atoms, alkylthio (C ₁ -C ₅ ), haloalkylthio (C ₁ -C ₅ ) with 1 to 6 identical or different halogen atoms, Amino, monoalkylamino with straight-chain or ver branched alkyl radicals (C1 -C ₆ ), dialkylamino with identical or different, straight-chain or branched alkyl radicals (C ₁ -C ₅ ), or
R ² and R ³ -CH = CH-CH = CH- are connected, which is optionally mono- to tetrasubstituted by halogen, nitro, cyano, alkyl (C ₁ -C ₅ ), haloalkyl (C ₁ -C ₅ ) with 1 to 6 identical or different halogen atoms, alkoxy (C ₁ -C _5), haloalkoxy (C ₁ -C ₅₎ having 1 to 6 identical or different halogen atoms, alkylthio (C ₁ -C _5), haloalkylthio (C ₁ -C ₅₎ with 1 to 6 identical or different halogen atoms, amino, monoalkylamino with straight-chain or branched alkyl radicals (C ₁ -C ₆ ), dialkylamino with the same or different, straight-chain or branched alkyl radicals (C ₁ -C ₅ ), or fused with an aryl ring ,
R ⁵ , R ⁶ or R ^{7 are the} same or different and independently of one another are hydrogen, nitro, cyano, halogen, straight-chain or branched alkyl (C ₁ -C ₈ ), alkenyl (C ₂ -C ₈ ) or alkynyl (C ₂ - C ₈ ), which is optionally substituted one or more times, identically or differently, by halogen, optionally substituted phenyl, alkoxy (C ₁ -C ₅ ), haloalkoxy (C ₁ -C ₅ ) having 1 to 6 identical or different halogen atoms, Acyl (C ₁ -C ₅ ) or optionally substituted aryl, pyridyl. 3. Compounds according to claim 1, characterized in that
X ^{1 represents} oxygen or sulfur,
Y stands for -CHR ⁷ - or -CHR ⁵ CHR ⁶ -,
Z ^{1 represents} sulfur, oxygen, NR ¹ ,
Z ^{2 represents} CR ² or nitrogen,
Z ^{3 represents} CR ³ or nitrogen,
Z ^{4 represents} CR ⁴ or nitrogen, where
R ¹ , R ² , R ³ , R4 independently of one another for hydrogen, cyano, nitro, straight-chain or branched alkyl (C ₁ -C ₅ ), alkenyl (C ₂ -C ₅ ), alkynyl (C ₂ -C ₅ ), which each optionally substituted one to more times, identically or differently, by fluorine, chlorine, nitro, cyano, alkoxy (C ₁ -C ₄ ), haloalkoxy (C ₁ -C ₄ ) with 1 to 5 identical or different fluorine and / or Chlorine atoms, alkylthio (C ₁ -C ₄ ), haloalkylthio (C ₁ -C ₄ ) with 1 to 5 identical or different fluorine and / or chlorine atoms, phenyl, pyridyl, pyrimidyl or pyrazinyl; for alkoxy (C ₁ -C ₄ ); for haloalkoxy (C ₁ -C ₄ ) with 1 to 4 identical different fluorine and / or chlorine atoms; Benzylthio, alkylthio (C ₁ -C ₄ ); Haloalkylthio (C ₁ -C ₄ ) with 1 to 4 identical or different fluorine or chlorine atoms, or for phenyl, pyridyl, pyrimidyl or pyrazinyl, which are each optionally substituted one to more times, identically or differently, by fluorine and / or chlorine, Alkyl (C ₁ -C ₄ ), haloalkyl (C ₁ -C ₄ ) with 1 to 4 identical or different fluorine and / or chlorine atoms, alkoxy (C ₁ -C ₄ ), haloalkoxy (C ₁ -C ₄ ) with 1 up to 4 identical or different fluorine and / or chlorine atoms, alkylthio (C ₁ -C ₄ ), haloalkylthio (C ₁ -C ₄ ) with 1 to 4 identical or different fluorine or chlorine atoms, amino, monoalkylamino with straight-chain or branched alkyl radicals (C ₁ -C ₅ ), dialkylamino with the same or different, straight-chain or branched alkyl radicals (C ₁ -C ₄ ), or
R ² and R ^{3 are} connected via the group -CH = CH-CH = CH-, which is optionally substituted one to four times by fluorine, chlorine, nitro, cyano, alkyl (C ₁ -C ₄ ), haloalkyl (C ₁ - C ₄ ) with 1 to 4 identical or different fluorine and / or chlorine atoms, alkoxy (C ₁ -C ₄ ), haloalkoxy (C ₁ -C ₄ ) with 1 to 4 identical or different fluorine and / or chlorine atoms, alkylthio (C ₁ -C ₄ ), haloalkylthio (C ₁ -C ₄ ) with 1 to 4 identical or different fluorine and / or chlorine atoms, amino, monoalkylamino with straight-chain or branched alkyl radicals (C ₁ -C ₅ ), dialkylamino with the same or various, straight-chain or branched alkyl radicals (C ₁ -C ₄ ), or fused with an aryl ring.
R ⁵ , R ⁶ or R ^{7 are the} same or different and are independently hydrogen, nitro, cyano, fluorine, chlorine, straight-chain or branched alkyl (C ₁ -C ₆ ), alkenyl (C ₂ -C ₆ ) or alkynyl ( C ₂ -C ₆ ), which is optionally substituted one or more times, identically or differently, by fluorine, chlorine, optionally substituted phenyl, alkoxy (C ₁ -C ₄ ), haloalkoxy (C ₁ -C ₄ ) with 1 to 5 of the same or different fluorine and / or chlorine atoms, acyl (C ₁ -C ₅ ) or for optionally substituted aryl, pyridyl. 4. Compounds according to claim 1, characterized in that
X ^{1 represents} oxygen or sulfur,
Y stands for -CHR ⁷ - or -CHR ⁵ CHR ⁶ -,
Z ^{1 represents} sulfur, oxygen, NR ¹ ,
Z ^{2 represents} CR ² or nitrogen,
Z ^{3 represents} CR ³ or nitrogen,
Z ^{4 represents} CR ⁴ or nitrogen, where
R ¹ , R ² , R ³ , R ^{4 are the} same or different and, independently of one another, are hydrogen, cyano, nitro, straight-chain or branched alkyl, alkenyl, alkynyl, in particular methyl, ethyl, n-propyl, i-propyl, n-butyl , i-butyl, s-butyl, t-butyl, cyclohexyl, cyclopentyl, allyl, propargyl, which are in each case optionally substituted one to three times, identically or differently, by fluorine, chlorine, nitro, cyano, alkoxy, in particular methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, haloalkoxy, especially difluoromethoxy, trifluoromethoxy, dichlorofluoromethoxy, difluorochloromethoxy, pentafluoroethoxy, benzylthio, alkylthio, especially methylthio, ethylthio, n-propyl , i-propylthio, n-butylthio, i-butylthio, s-butylthio, t-butylthio, haloalkylthio, especially difluoromethylthio, trifluoromethylthio, dichlorofluoromethylthio, di fluorochloromethylthio, pentafluoroethylthio, phenyl, pyridyl, pyrimidyl, pyrazole for alkoxy, in particular methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy; for haloalkoxy, in particular difluoromethoxy, trifluoromethoxy, dichlorofluoromethoxy, difluorochloromethoxy, pentafluoroethoxy; for benzylthio; for alkylthio, especially methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio, t-butylthio; for haloalkylthio, in particular difluoromethylthio, trifluoromethylthio, dichlorofluoromethylthio, difluorochloromethylthio, pentafluoroethylthio; or for phenyl, pyridyl, pyrimidyl, pyrazinyl, which are optionally substituted one to three times, identically or differently, by fluorine, chlorine, alkyl, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s- Butyl, t-butyl, haloalkyl, especially difluoromethyl, trifluoromethyl, dichlorofluoromethyl, difluorochloromethyl, pentafluoroethyl, alkoxy, especially methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, Haloalkoxy, especially difluoromethoxy, trifluoromethoxy, dichlorofluoromethoxy, difluorochloromethoxy, pentafluoroethoxy, alkylthio, especially methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio, especially di-fluoroethyl, t-butylthio , Trifluoromethylthio, dichlorofluoromethylthio, difluorochloromethylthio, pentafluoroethylthio, amino, monoalkylamino or dialkylamino with the same or different, straight-chain or branched alkyl radicals, in particular methyl, ethyl, n-propyl, i-propy l, n-butyl, i-butyl, s-butyl, t-butyl, stand, or
R ² and R ^{3 are} connected via the groups -CH = CH-CH = CH-, which is optionally substituted one to three times by fluorine and / or chlorine, nitro, cyano, alkyl, in particular methyl, ethyl, n-propyl, i - Propyl, n-butyl, i-butyl, s-butyl, t-butyl, haloalkyl, in particular special difluoromethyl, trifluoromethyl, dichlorofluoromethyl, difluorochloromethyl, pentafluoroethyl, alkoxy, in particular methoxy, ethoxy, n-propoxy, i-propoxy, n -Butoxy, i-butoxy, s-butoxy, t-butoxy, haloalkoxy, such as difluoromethoxy, trifluoromethoxy, dichlorofluoromethoxy, difluorochloromethoxy, pentafluoroethoxy, alkylthio, especially methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio butylthio, s-butylthio, t-butylthio, halogenoalkylthio, in particular difluoromethylthio, trifluoromethylthio, dichlorofluoromethylthio, difluorochloromethylthio, pentafluoroethylthio, amino, monoalkylamino or dialkylamino having identical or different straight-chain or branched alkyl radicals, in particular methyl, ethyl, n-Prop yl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl,
R ⁵ , R ⁶ or R ^{7 are the} same or different and independently of one another for hydrogen, nitro, cyano, fluorine, chlorine, straight-chain or branched alkyl, alkenyl, alkynyl, in particular methyl, ethyl, n-propyl, i-propyl, n -Butyl, i-butyl, s-butyl, t-butyl, allyl, propargyl, which is optionally substituted by fluorine and / or chlorine, optionally substituted phenyl, alkoxy, in particular methoxy, ethoxy, n-propoxy, i-propoxy, n -Butoxy, i-butoxy, s-butoxy, t-butoxy, haloalkoxy, especially difluoromethoxy, trifluoromethoxy, dichlorofluoromethoxy, difluorochloromethoxy, pentafluoroethoxy, acyl, especially formyl, acetyl, n-propionyl, i-propionyl, n-butyryl, i -Butyryl, s-butyryl, or optionally substituted aryl, pyridyl. 5. A process for the preparation of compounds of formula (I) as defined in claim 1, characterized in that

• a) compounds of the general formula (II),
  in which
  Y has the meaning given above and
  X ^{2 represents} bromine or chlorine, with compounds of the general formula (III),
  in which
  X ¹ , Z ¹ , Z ² , Z ³ and Z ^{4 have} the meanings given above, optionally in the presence of a base and optionally in the presence of a diluent, or
• b) compounds of the general formula (IV),
  in which
  Y and M ^{+ have} the meanings given above, with compounds of the general formula (VI)
  in which
  Z ¹ , Z ² , Z ³ and Z ^{4 have} the meanings given above and
  X ^{3 represents} a leaving group, in particular mesyl, tosyl, fluorine, chlorine or bromine,
  if appropriate in the presence of a base and if appropriate in the presence of diluents or
• c) for the preparation of compounds as defined in claim 1 with X ¹ in its meaning as sulfur, the salts of the general formula (IV)
  in which
  Y has the meaning given above and
  M ^{+ represents} an alkali or alkaline earth metal ion, in particular Na ⁺ or K ⁺ ,
  with diazonium salts of the general formula (V)
  in which
  Z ¹ , Z ² , Z ³ and Z ^{4 have} the meanings given above and
  represents the anion of a mineral acid,
  in aqueous / alkaline solution, optionally in the presence of a catalyst.

6. A process for the preparation of agents, characterized in that Compounds as defined in claims 1 to 4 with extenders and / or carriers and / or surfactants mixed. 7. agents containing extenders and / or carriers and optionally surface-active substances, characterized by a content of at least a compound as defined in claims 1 to 4. 8. A method for controlling pests, characterized in that compounds as in claims 1 to 4 or agents as in Claim 7 defined to act on pests and / or their habitat leaves.   9. Use of compounds as in claims 1 to 4 and of Agents as defined in claim 7 for controlling pests.