DD229013A5 - FUNGICIDAL AGENTS - Google Patents

Abstract

The invention relates to fungicidal compositions containing as active ingredient substituted phenoxybenzaldehydes of the general formula I. In formula I, X represents hydrogen or a chlorine atom, while Y may be hydrogen or nitro. In addition to the active ingredient, the funds contain common auxiliaries and Traegerstoffe. The invention further relates to a method for combating phytotoxic fungi. Preferred active ingredients are: 3- (2-chloro-4-trifluoromethyl-phenoxy) -benzaldehyde, 3- (2,6-dichloro-4-trifluoromethyl-phenoxy) -benzaldehyde, 5- (2-chloro-4-trifluoromethyl-phenoxy ) -2-nitro-benzaldehyde and 5- (2,6-dichloro-4-trifluoromethyl-phenoxy) -2-nitro-benzaldehyde. Formula I

Description

CF ₃

X 7 "Cl

(I

Field of application of the invention

The invention relates to fungicidal agents and to a method for controlling phytotoxic fungi.

Characteristic of the known technical solutions

There are already known certain substituted Phenoxybenzaldehyde the general formula I, wherein X is hydrogen or a chlorine atom and

Y is hydrogen or nitro.

Formula I comprises the following four compounds:

5- (2-chloro-4-trifluoromethyl-phenoxy) -2-nitro-benzaldehyde (hereinafter referred to as compound 1),

- 5- (2,6-dichloro-4-trifluoromethyl-phenoxy) -2-nitro-benzaldehyde, (hereinafter referred to as compound 2),

- 3- (2-chloro-4-trifluoromethyl-phenoxy) -benzaldehyde (hereinafter called compound: 3) and

- 3- (2,6-dichloro-4-trifluoromethyl-phenoxy) -benzaldehyde (hereinafter referred to as compound 4).

The abovementioned four compounds of the formula I are either already known as herbicidal active compounds, or it is assumed that their herbicidal activity.

US Pat. No. 4,309,600 describes novel nitrodiphenyl ether derivatives as herbicidal active substances. Here, among others, the compounds 1 and 2 have been described.

In the cited patent example 4 shows the preparation of 2-chloro-4-trifluoromethyl-3'-formyl-4'-nitrodiphenyl ether (according to another nomenclature of 5- (2-chloro-4-trifluoromethyl-phenoxy) - 2-nitro-benzaldehyde, ie identical to the compound 1) with yield, pour point and Elementaranalyseangaben, and described in Table II whose herbicidal activity. The physical data or details of the herbicidal activity of compound 2 are not apparent from the PS.

DE-OS 3017795 describes (Formula II of the OS) new substituted phenoxypenylcarboxyoxyimines as herbicidal active ingredients.

The compounds occurring as intermediates are also described as herbicidal active ingredients. The preparation of the intermediate compounds was shown, but the physical data and the extent of the herbicidal activity were not indicated.

Compound 1 and 2 fall under the compounds described in DE-OS 3017795 (formula II).

The compounds mentioned (formula II) were prepared in DE-OS 3017795 by formation of intermediates without nitro group and their subsequent nitration. Physical data of the intermediates without nitro group were not given, their herbicidal activity was not mentioned.

The compounds 3 and 4 fall under the intermediates described in DE-OS 3017795 without nitro group.

EP-PS 0053321 describes novel herbicidal phenoxycinnamic acid derivatives, both substituted phenoxy-2-nitrobenzaldehydes (compounds 1 and 2) and also substituted phenoxybenzaldehydes (compounds 3 and 4). However, the herbicidal activity of the intermediates was not mentioned.

In EP-PS 0064658 new Phenoxybenzaldehydacetate be described with herbicidal and plant growth regulating effect. As a starting material, among others, 5- (2-chloro-4-trifluoromethyl-phenoxy) -2-nitro-benzaldehyde (compound 1) and 5- (2,6-dichloro-4-trifluoromethyl-phenoxy) -2-nitro- benzaldehyde (compound 2) described. Her herbicidal activity was not mentioned.

The compounds 1 to 4 are therefore known, and the herbicidal activity of the compound 1 and 2 is known, although this is only proven in the compound 1.

Object of the invention

The invention is intended to provide novel fungicidal compositions and a method of controlling phytotoxic fungi. _ '.

Explanation of the essence of the invention

It has been found that the compounds of general formula I have excellent fungicidal activity.

• - -3-

This was certainly not to be expected since in the literature only the herbicidal activity of these compounds is described. Also according to the handbook by R. Wegler: "Chemistry of Crop Protection and Pest Control", Volume 5, Springer-Verlag Berlin, Heidelberg, New York, 1977, the diphenyl ether derivatives) in soybean, maize and rice crops can be used as herbicidal active ingredients.

The invention therefore fungicidal agents which are characterized by a content of substituted phenoxybenzaldehydes of the general formula I as an active ingredient. In addition to the active ingredient, the agents contain at least one carrier.

In the general formula I, X is hydrogen or a chlorine atom and Y is hydrogen or nitro.

The fungicidal active compounds which can be used according to the invention are known per se and can be prepared by known processes. They can be prepared, for example, as follows: 3- (2,6-dichloro-4-trifluoromethyl-phenoxy) -benzaldehyde (compound 4)

6.1 g (0.05 mol) of 3-hydroxybenzaldehyde are reacted in 150 ml of dry methanol with 2.8 g (0.06 mol) of potassium hydroxide under inert atmosphere to 3-hydroxybenzaldehyde potassium. The methanol is distilled off in a water-jet vacuum, and the residue is mixed with 2.5 g of potassium carbonate, 50 ml of dimethyl sulfoxide and 13.75 g (0.055 mol, 10% excess) of 3,4,5-trichloro-benzotrifluoride. The batch is kept for 8 hours at 140 to 144 ° C, distilled off the dimethyl sulfoxide, the residue diluted with 150ml of benzene and the suspension stirred for 1 hour. The benzene-insoluble solid portions are filtered off with suction, and the benzene is distilled off from the filtrate in a water-jet vacuum. The residue is recrystallized from methanol / isopropanol 1: 1. This gives 9 g (60% of theory) of white crystals, molecular weight: 335 (C ₁₄ H ₇ Cl ₂ F ₃ O ₂ ). M / e (ri) = 336/580 / = F ₃ CZClZ ₂ C ₆ H ₂ OC ₆ H ₄ CHO

335/370 / = F ₃ C / CI / ₂ C ₆ H ₂ OC ₆ H ₄ CHO

334Z1000Z = F ₃ CZCIZ ₂ H ₂ OC ₆ H ₄ CHo

333Z370Z = F ₃ CZCIZ ₂ C ₆ H ₂ Oc ₆ H ₄ CHO

271 / 520Z = F ₃ CZCIZC ₆ H ₂ OC ₆ H ₅

236Z560Z = F ₃ CC ₆ H ₂ OC ₆ H ₅ IR: 1 690cm ^-1 (Formula CO).

Analogously, the 3- (2-chloro-4-trifluoromethyl-phenoxy) -benzaldehyde (compound 3) can be prepared. 5- (2,6-dichloro-4-trifluoromethyl-phenoxy) -2-nitro-benzaldehyde (Compound 2).

3.75 g (0.011 mol) of 3- (2,6-dichloro-4-trifluoromethyl-phenoxy) -benzaldehyde are dissolved in a mixture of 8.6 ml of dichloromethyne and 5.3 ml of acetic anhydride. To this solution, a nitrating acid, consisting of 2.4 ml of 65% (0.034 NoI) nitric acid and 2.4 ml of 98% sulfuric acid, added dropwise with stirring at such a rate that the temperature remains below 10 ° C. After completion of the addition, the mixture is stirred for 3 hours at room temperature, the dichloromethane removed in a water-jet vacuum and the residue poured into ice-water. The precipitated white powder is obtained by suction and dried. This gives 2.7 g of white crystals (64% of theory), mp 117-119 ° C, molecular weight: 379 (C ₁₄ H ₆ O ₄ Cl ₂ F ₃ )

MZe (ri) = F ₃ = 381Z720Z CZCIZ ₂ C ₆ H ₂ OC ₆ H ₃ ZNOZCHO

379/1000 / = F ₃ CZCIZ ₂ C ₅ H ₂ Oc ₆ H ₃ ZNO ₂ ZCHO

349Z650Z = F ₃ CZCIZ ₂ C ₆ H ₂ OC ₆ H ₃ ZOZCHo

285Z320Z = F ₂ CZCIZ ₂ C ₆ H ₂ OC ₆ H ₄

230/220 / = F ₃ C / CI / ₂ C ₆ H ₂ OH NMR: δ = 9.6-10.5 (aromatic aldehyde)

(Aldehyde-Η of the starting material at δ = 9.85, of the nitro derivative at δ = 10.35 ppm) IR: 1 690 cm x ¹ (formula CO)

The above data show no oxidation of the formyl group in carboxyl under the conditions described. Analogously, the 5- (2-chloro-4-trifluoromethyl-phenoxy) -2-nitro-benzaldehyde (compound 1) can be prepared. For use, the active ingredients are in known manner in appropriate formulations, such as wettable dusts (WP), suspension concentrates (SC), water-mixable concentrates (SL), emulsifiable concentrates (EC), ULV preparations (ultra low volume) or mordants, preferably Seed treatment agent further processed. For this purpose, the active compounds are mixed with known solid or liquid inert carriers and optionally with other excipients. As auxiliaries, for example, surface-active substances, such as wetting agents, suspending agents, dispersants and emulsifiers, anti-caking agents. Spreaders, penetrants and stabilizers. Suitable solid carriers are: inactive minerals, such as kaolin, alumina, attapulgite, montmorillonite, mica schist, pirofillite, bentonite, diatomaceous earth or highly dispersed synthetic cleistic acid, furthermore calcium carbonate, calcined magnesia, dolomite, gypsum, tricalcium phosphate, filler earth and granules of organic material, like tobacco stems and sawdust.

Suitable liquid carriers are: solvents and diluents, such as water, organic and aqueous-organic solvent mixtures of, for. Methanol, ethanol, n- and iso-propanol, diacetone alcohol, benzyl alcohol, glycols such as ethylene, triethylene and propylene glycol, and their esters such as methyl cellosolve and butyl diglycol; ketones such as demethyl ketone, methyl ethyl ketone, methyl isobutyl ketone, cyclopentanone, cyclohexanone; Esters such as ethyl acetate, n- and iso-butyl acetate, amyl acetate, isopropyl miristate, dioctyl phthalate; Aromatics, aliphatic and alicyclic hydrocarbons, such as paraffins, cyclohexane. Kerosenes, gasoline, benzene, toluene, xylene, tetralin, decalin, alkylbenzenes, chlorinated hydrocarbons such as trichloromethane, dichloromethane, perchlorethylene, dichloropropane, chlorobenzene; Lactones, wiey-butyrolactone; Lactams, like N-

Methyl pyrrolidone, N-cyclohexylpyrrolidone; Acid amides, such as dimethylformamide; continue to use vegetable and animal oils, such as

Sunflower oil, linseed oil, olive oil, soybean oil, castor oil and sperm oil ^

Suitable wetting, dispersing and emulsifying agents are: ionic and nonionic substances, such as salts of saturated and unsaturated carboxylic acids, aliphatic, aromatic and aliphatic-aromatic hydrocarbon sulfonates, alkyl, aryl and aralkylcarboxylic acids, their esters and ethersulfonates, sulfonic acids Condensation products of phenol, cresol and naphthalene, sulfated vegetable and animal oils, alkyl, aryl and aralkyl phosphate esters, and their salts with alkali,

Alkaline earth or organic bases such as amines, alkanolamines ^ e.g. Sodium lauryl sulfate, sodium 2-ethylhexylsulfate, sodium, ethanolamine, diethanolamine, triethanolamine or isopropylamine salts of dodecylbenzenesulfonic acid, sodium mono- and diisopropylnaphthalenesulfonate, naphthalenesulfonic acid sodium salt, sodium diisooctylsulfosuccinate, sodium xylenesulfonate, sodium and calcium salts of petroleum sulfonic acid, potassium soap, potassium, sodium , Calcium, aluminum and magnesium stearates, furthermore phosphate esters, such as phosphated alkylphenols, fatty alcohol polyglcol ethers, or partially or wholly neutralized derivatives with cations or organic bases, finally disodium N-octadecylsulphosuccinate, sodium N-oleil- N-methyl-tauride and lignosulfonates.

As non-ionic substances can be mentioned:

Ethers of Ethylenoxydes with C ₁₀ -C ₂ o-alcohols such as stearyl polyoxyethylene, oleyl polyoxyethylene; Ethers of alkylphenols, such as tert-butyl, octyl and nonylphenol polyglycol ethers; Esters of organic acids, such as stearic acid and miristinic polyethylene glycol esters or polyethylene glycol oleate; partially saponified esters of fatty and oleic acids with hexytanhydride, such as esters of oleic acid or stearic acid with sorbitol and others, furthermore condensation products of these substances with ethylene oxide; and tertiary glycols such as 3,6-dimethyl-4-octyne-3,6-diol or 4,7-dimethyl-5-decyne-4,7-diol; Polyethylene glycol thioethers, such as ethers of dodecylmercaptan with polyethylene glycol.

The formulations of the invention may contain as adhesives:

Alkaline earth soap, salts or sulfosuccinic acid esters, natural and symmetrical water-soluble macromolecules such as casein, starch, vegetable gum, gum arabic, cellulose ethers, methyl cellulose, hydroxyethyl cellulose, polyvinyl pyrrolides, polyvinyl alcohol and the like. Foaming control agents can also be used, such as low molecular weight polyoxyethylene, polyoxypropylene, block polymers, octyl, nonyl and phenyl polyoxyethylene (OE grade above 5), long chain alcohols such as octyl alcohol, and specialty silicone oils.

Other additives can also be used to make the formulation colloidally compatible with various fertilizers.

Other pesticidal agents and / or nutrients may also be used.

For the preparation of wettable dusts (WP), active ingredient, excipients and surfactants are mixed together, then ground and homogenized. When using liquid surface-active agents, these can be sprayed onto the solid mixture of organic and inorganic auxiliaries and optionally also of active ingredient. Analogously, one can proceed with liquid active substances. When using liquid surfactants, one can also proceed by suspending the solid ingredients in an organic solvent containing the liquid surfactants. After drying the suspension, a mixture of particles coated with the surface-active agents is obtained.

For the preparation of emulsifiable concentrates (EC), the ingredients are dissolved in a water-immiscible solvent. The resulting mixture tends to form an emulsion with water without much action, which is storage stable for a long time.

To prepare water-miscible concentrates (SL), a solution of the active ingredient and the water-soluble excipients in water and / or in a water-miscible solvent is prepared. Later, this concentrate is diluted with water to the desired concentration.

The concentrate can also be dispersed in a water-immiscible solvent with a suitable emulsifier. Thus, a so-called reverse emulsion is obtained, which contains the constituents, even in molecular scales, in dispersed form, which is storage-stable for a long time.

To prepare suspension concentrates (SC), the wetting and dispersing agents are dissolved in a mixture of water (preferably deionized water) and an antifreeze (preferably ethylene glycol or glycerol), optionally by heating). To this solution is added the solid ingredients and optionally the anti-caking component (such as Aerosil 200) with stirring. The sludge obtained is preferably comminuted to a particle size of SMm by subsequent milling (for example in a so-called Dyno mill) in order to achieve a corresponding storage stability. Thereafter, if desired, a suds controlling agent or a "thickening component" (such as Kelzan S) may be added The order of addition of the individual components may be varied Other components such as pigments may also be used, as well as liquid, water-miscible or solid-active ingredients The low melting point solid actives may also be used in the form of melts with or without emulsifiers.

The ULV formulations can be prepared analogously to the EC formulations.

Ready-to-use granules can be produced by extruding and coating granular carriers (limestone powder) by coating carriers with a liquid component.

Suspension concentrates (SC) and / or wettable dusts (WP) may be granulated by agglomeration, such as coating with adhesives.

The formulations are prepared by diluting with water or with an inert solid diluent the appropriate forms of use, such as ready-to-use solutions or powders having an active ingredient concentration of 0.0001-10% by weight, preferably 0.01-5% by weight.

The compositions according to the invention can also be used in the form of seed foil. For this purpose, either the film or the seed is combined with the agents according to the invention.

J ^ ojTTTuljemngsbeispiele

Suspension concentrates (SC):

Compound 4 40.0% by weight

Ethylene glycol 10.0% by weight

Nonylphenyl polyglycol ester (OE) 10) 5.0% by weight

Polysaccharide (xantangum) 0.1% by weight

Silicone oil 1.0Gew%

Water 43.9% by weight

Meshable Dust (WP):

Compound 1 30.0% by weight

highly dispersed silica 15.0% by weight

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Caolin 20.0% by weight Sodium ligninsulfonate 5.0% by weight

Diatomaceous earth 25.0% by weight Dispersant 5.0% by weight

granules:

Compound 3 5.0% by weight -%

Limestone flour 69.0% by weight of ethylene glycol 3.0% by weight

Calcium lignosulfonate 3.0% by weight

highly dispersed silicic acid 5.0% by weight

Water 15.0% by weight Dry flowable granules (WG):

Compound 4 80.0% by weight emulsifier (anionic and nonionic) 2.0% by weight

Dispersant 7.0% by weight

Caolin 8.0% by weight

Water 3.0% by weight

Emulsifiable Concentrates (EC):

Compound 2 20.0% by weight

Xylene 50.0% by weight

Cyclohexanone 12.0% by weight

Isoforon 10.0% by weight of polyoxyethylene sorbitan monoleate 5.0% by weight

Sodium lignosulfonate 3.0% by weight

Seed film:

a) Preparation of the film itself

80 g Rhodoviol 4 / 125P polyvinyl alcohol (viscosity in 4% water solution at 20 ⁰ C, 4cP, 89 mol%, hydrolyzed) are dissolved with stirring at 60 ° C in 615g of water. After dissolving 20 g of Rhodoviol 30/20 polyvinyl alcohol (viscosity in 4% water solution at 2O ⁰ C, 3OcP, 98Mol-%, hydrolyzed) and 20g glycerol are added and stirred until a homogeneous solution. This is then allowed to stand for 24 hours to remove the bubbles. The solution is applied to a glass plate in a thickness of 0.50 mm and dried at room temperature. The resulting film separates from the glass plate and has a thickness of Ο, Οδ-Ο, ΟδηΊΓΤΐ.

b) Preparation of an active substance-containing film

To the solution prepared in section a) is added a suspension of 0.120 g of compound 2 in 5 ml of water. After the disappearance of the bubbles, the foam is poured as in section a). This gives a film with an active ingredient concentration of

If, instead of compound 2, a suspension of 0.0120 g of compound 4 in 5 ml of water is used, a film is obtained having an active ingredient concentration of 100 ppm.

To combat fungal attack of plants, the most commonly used forms of application are pickling, dusting and spraying. The fungicidal active ingredient is preferably in the vicinity of the infestation or in its distribution or

Habitat brought to action.

For pickling-free storage of seeds and to prevent infection by soil fungi pickling is used. The seeds and seedlings are primarily endangered by the moldy conidic fungi. As examples may be mentioned: Fusarium graminearium and Fusarium moniliforme and Nigrospora oryzae in maize cultures, furthermore the genus Rhizoctonia, Penicillium and Helminthosporium.

Dusting and spraying is used to control such fungi that infect the leaves and fruits.

As an example may be mentioned: Monilia fructigena and Spilocea pomi in apples and Botrytis cinerea in grapes.

The active compounds according to the invention can furthermore be used, for example, for combating the following fungi:

Moniliaceae: Monilia, such as B. M. fructigena

Aspergillus, as B. P. crustaceum Botrytis, such as. B. cinerea Verticillium, such as. B. V. albo-atrum trichothecium, such as. B. T. roseum

Cersosporella, Wiez. B. C. herpotrichoides Dematiaceae: Thielaviopsis, such. B. T. basicola

Nigrospora, wiez. B. N. oryzae Spiloceam such. S. pomi / Fusicladium / dendriticum /

Cladosporium, wiez. B. C.fulvum Helminthosporium, such as. B. H. turcicum Cercorpora, wiez. B. dbeticola Alternaria, wiez. B. solani

Stemphylium, Wiez. B. S. radicinium Tuberculariaceae: Fusarium, wiez. B. F. * graminearum and F. oxysporum

Embodiments:

As a comparative compound in the following application examples, the known 1,2,5,6-tetrahydro-N-trichloromethylthio-phthalimide (Captan) was used.

example 1

Fungicidal activity

An agar medium of potato agar with 2% dextrose is provided in a 100 mm diameter petri dish. An emulsifiable concentrate with 20% active ingredient content is diluted to the desired concentration. From spores of the test fungi suspensions are prepared with such concentrates, can be seen by the 25-30 spores per drop in a field of the microscope slide at a 100- to 160-fold magnification. 1 ml spore suspension is pipetted to 1 ml of drug solution, allowed to stand for 30 minutes and finally applied to the agar base. The fungi are inoculated until vigorous development, then rated relative to the control test based on the value scale below.

1 = no development (0% of control)

2 = low development (10% of control)

3 = mean development (50% of control)

4 = strong development (100% of control)

The evaluation numbers obtained, their mean and percentage value and the fungicidal activity are given in Table 1.

Table 1

connection active substance develop 2 3 4 mg (B) 2 3 4 average development (B) effectiveness (B) concentration (A) 1 1 1 1 1 1 1 1 in% 0 in% 100 (Ppm) 1 1 1 1 average 1 1 1 1 1 (A) 0 (A) 100 1. 10000 1 2 2 2 1 2 2 2 2 0 10 100 90 2,000 1 3 2 3 1 2 3 2 2 2.5 0 30 100 70 400 2 3 4 4 2 3 3 4 3 3.5 10 75 90 25 80 · 2 1 1 1 2.5 4 1 1 1 1 30 0 70 100, 16 4 1 1 1 3.75 1 1 1 1 1 82-83 0 17-18 100 Second 10000 1 3 2 3 1 1 2 2 2 2 0 10 100 90 2,000 1 3 3 2 1 2 3 3 2 2.5 0 30 100 70 400 2 4 4 4 2.5 2 3 4 4 3.5 30 75 70 25 80 3 2 2 2 2.75 3 3 2 3 2.5 40 30 60 70 16 3 3 3 3 3.75 2 3 3 3 3 82-83 50 17-18 50 Third 10000 2 4 4 4 2 3 4 4 4 4 10 100 90 0 2000 3 2 2 3 3 4 2 2 2 2 50 10 50 0 400 4 3 4 4 4 2 3 3 4 3.25 100 62-63 0 0 80 3 2 3 3 2.5 3 3 3 3 3 30 30 0 70 16 3 4 3 4 3.5 3 3 3 4 3.5 75 75 0 25 4th 10000 2 4 4 4 2.5 4 4 4 4 4 30 100 70 0 2,000 3 4 4 4 3.5 4 4 4 4 4 75 100 25 0 400 4 4 4 4 4 4 4 4 4 4 100 100 0 0 80 4 1 1 1 4 4 1 1 1 1 100 0 0 100 16 4 1 1 1 4 1 1 1 1 1 100 0 0 100 captan 10000 1 2 2 2 1 1 2 2 2 2 0 10 100 90 /known/ 2000 1 3 2 3 1 2 2 3 2 2.5 0 30 100 70 400 2 3 4 4 2 3 3 4 3 3.5 10 75 90 25 80 2 4 4 4 2.5 4 4 4 4 4 30 100 70 0 16 3 3.5 4 75 25 control - 4 4 100 0 (A) = Aspergillus niger (B) = Botrytii 5 cinerea

Example 2

fungitoxicity

In 20 ml of a 2% Malznährlösung the active ingredients are emulsified in the desired concentration and inoculated with the mushrooms. After 7 days of incubation, prevention of development is checked. Table 2 shows the concentrations required to prevent 100% development.

Table 2

fungitoxicity

captan connection 2 3 4 (known) 1 300 1000 1000 Fusarium oxysporum 300 300 300 1000 1000 Fusariumnivale 300 300 300 1000 1000 Fusarium solani 300 300 300 1000 1000 Altemariasolani 100-300 300 300 1000 1000 Aspergillus niger 100-300 100-300 100-300 1000 300 Botrytis cinerea 100-300 100-300 100-300 1000 300 Botrytisfabae 100-300 100-300 Cercospora beticola 100-300 1000 300 Stempylium 100-300 100-300 100-300 1000 300 radicinum 100-300 100-300 Trithothecium 30-100 300 300 roseum 100-300 100-300 Thielaviopsis 30-100 100-300 100-300 basicola 100-300 30-100 30-100 100-300 100-300 Nigrosporaoryzae 30-100 30-100 Cladosporium 30-100 100-300 100-300 cucumerinum 30-100 30-100 Penicillium 30-100 100-300 100-300 crustaceum 30-100 30-100 Verticillium 30-100 100-300 100-300 alboatrum 30-100 30-100 Fusicladium 30-100 100-300 " 100-300 dentriticum 30 30 30 100-300 100-300 Moniliafructigena 30 30

Example 3

phytotoxicity

Pots with a surface of 1.64dm ² are filled with sandy soil. In the soil in each case 20-30 seed seeds are sown in two parallel rows. 10 days after germination, the seedlings are sprayed with 20% active ingredient emulsion in a dose of 1.3 and 9 kg / ha. 10 days after the treatment, the damage of the seedlings, calculated as a percentage of the control, is measured.

The results are shown in Table 3.

The following test plants were investigated:

A - Soy (Glycine soja) B - Autumn wheat (Triticumaestivum) C - Autumn barley (Hordeum vulgare) D - Corn (Zea mays) E - Black billed millet (Setaria italica) F - Cotton (Gossypiumhirsutum) G - White fen (Sinapisalba) H - Bean ( Phaseolusvulgaris) I - Pea (Pisumsativum) K - Lupine (Lupinusbus) L - Horse bean (Viciafaba) M - Alfalfa (Medicagosativa) N - Carrot (Daucuscarota) O - Sugarbeet (Beta vulgaris) P - Sunflower (Helianthusannuus)

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Table 3

phytotoxicity

1 0 3 4 9 10 Verbindu 0 ! a ' ¹ ) 5 ng 9 15 3 0 3 0 9 10 4 0 3 0 9 15 control dose ul 10 30 2 0 3 10 30 0 0 20 0 5 25 1 10 35 50 , ICG f 15 25 50 1 10 20 40 1 10 20 40 10 40 60 1 30 50 70 15 20 45 20 30 50 A 60 80 100 50 75 100 30 60 100 30 70 100 0 B 80 95 98 30 65 90 30 40 70 30 50 75 0 C 40 60 90 50 80 95 30 50 100 35 60 95 0 D 50 80 80 45 65 85 0 10 50 CJL 15 40 0 e 15 30 50 10 40 60 10 30 40 20 30 40 0 F 40 50 70 50 60 70 10 15 20 10 20 25 0 G 70 80 90 80 90 100 25 50 75 20 35 55 0 H 60 90 100 70 80 95 30 50 '90 30 60 95 0 I 10 20 70 30 70 90 30 50 80 20 40 65 0 K 10 10 20 15 25 30 20 40 60 · 25 50 75 0 L 40 50 75 10 35 60 20 40 80 30 50 75 0 M 0 N 0 O 0 P 0

Example 4

Pickling soybeans against fungal diseases

For pickling, suspension concentrates of the compounds tested at a concentration of 400 g / l and a 50% WP formulation of the known captan were used, with 5 ml / kg seed seeds 0.1; 0.25; 0.5; 1.0 and 2.0 g of active ingredient per kg seed of soybean of the species Merit was applied.

Ten days after pickling, the seeds were sown in the greenhouse and outdoors at a depth of 4-5 cm and at a distance of 5 χ 50cm. At a seedling height of 10-12 cm, germination and infestation were measured and expressed as a percentage of the control in Table 4.

Example 4

Pickling of soybeans

connection Dose (g / kg) Infestation in% Penicillium Fusarium Germination in the Germination outdoors Alternaria sp. sp. Glasshouse in% sp. 5.0 2.2 in% 1 0.1 28.1 3.2 1.3 85 105 0.25 14.2 - 0.5 90 118 0.5 7.0 - - 80 120 1 4.3 - - 70 94 2 1.5 5.8 3.1 64 92 2 0.1 22.3 4.4 1.2 80th 102 0.25 14.1 0.2 - 85 104 0.5 6.6 - - 92 122 1 4.2 - - 78 96 2 0.5 8.9 6.2 66 90 3 0.1 58.2 7.6 5.0 82 100 0.25 49.5 3.8 1.8 82 105 0.5 13.4 2.0 0.2 86 107 1 6.6 0.5 - 90 105 2 4.3 9.1 5.0 82 98 4 0.1 54.2 6.8 4.4 80 101 0.25 39.8 2.2 2.3 82 102 0.5 16.3 1.5 - 86 109 1 9.8 - - 91 102 2 6.7 3.2 3.0 84 102 captan 0.1 26.4 2.2 1.5 82 102 /known/ 0.25 13.6 0.2 0.5 90 116 0.5 7.5 - - 94 121 1 2.6 - - 90 114 2 0.8 12.0 6.0 90 105 control - 75.0 78 100

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Example 5

Control of ear fusariosis of autumn wheat

A 20% emulsion concentrate of the active ingredients was diluted with water to the desired concentration, and sprayed after expelling the ears in an amount of 500 l / ha on the test plants. Infestation was measured 12 days after treatment on the ears and after harvest on the seeds and expressed as a percentage of the control in Table 5.

Table 5 Ear fusariasis Dose (kg-ha " ¹ ) Infestation in% Fusariumspp. Total seeds Seeds inside Harvest (kg / 10 m ² ) connection ears

1 1 0.86 12.2 8.8 5.67 2 '0.54 9.6 7.6 5.88 3 0.48 5.4 4.4 6.03 2 1 0.63 13.4 10.2 6.11 2 0.33 10.2 8.1 5.87 3 0.20 6.0 5.4 5.84 3 1 1.09 11.4 9.4 5.62 2 0.84 10.6 8.0 5.66 3 0.67 9.8 7.2 5.73 4 1 0.98 9.9 6.8 5.78 2 0.68 9.2 6.4 5.82 3 0.52 8.0 6.1 5.87 control 0 10,80 36,45 30,25 4.84

Claims (6)

claims: 1. Fungicidal agent, characterized in that it contains, in addition to customary excipients and carriers as active ingredient at least one substituted phenoxybenzaldehyde of the general formula I, wherein X is hydrogen or a chlorine atom and
Y is hydrogen or nitro
contain. 2. Fungicidal agent according to claim 1, characterized in that they contain as active ingredient 3- (2-chloro-4-trifluoromethyl-phenoxy) benzaldehyde. 3. Fungicidal agent according to claim 1, characterized in that they contain as active ingredient 3- (2-dichloro-4-trifluoromethyl-phenoxy) -benzaldehyde. 4. A fungicidal composition according to claim 1, characterized in that they contain as active ingredient 5- (2-chloro-4-trifluoromethyl-phenoxyl) -2-nitro-benzaldehyde. 5. A fungicidal composition according to claim 1, characterized in that they contain as active ingredient 5- (2-dichloro-4-trifluoromethyl-phenoxy) -2-nitro-benzaldehyde. 6. A method for controlling phytotoxic fungi, characterized by allowing substituted phenoxybenzaldehydes of the general formula I or a fungicidal composition according to claim 1 to 5 act on the fungi or their habitat. For this a page formulas