CS248732B2 - Fungicide agent - Google Patents

Abstract

According to the present invention there are provided fungicidal compositions comprising as active ingredient an effective amount of at least one compound of the general Formula I <IMAGE> wherein X stands for hydrogen or chlorine and Y represents hydrogen or nitro.

Description

The present invention relates to novel fungicidal compositions which contain, as active ingredient, substituted phenoxybenzaldehydes of the formula I

where

X is hydrogen or chlorine; and

Y is hydrogen or nitro.

Formula I includes the following four compounds:

5- (2-chloro-4-trifluoromethylphenoxy) -2-nitrobenzaldehyde (hereinafter referred to as Compound 1),

5- (2,6-dichloro-4-trifluoromethylphenoxy) -2-nitrobenzaldehyde (hereinafter referred to as Compound 2),

3- (2-chloro-4-trifluoromethylphenoxy) -benzaldehyde (hereinafter referred to as compound 3); and

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

The active compounds of the formula I according to the invention are known as herbicidally active substances, or their herbicidal activity is believed to be reliable despite the lack of biological data.

U.S. Pat. No. 4,306,900 discloses novel nitrodiphenyl ether derivatives as herbicidally active agents. Among others, compounds 1 and 2 have been described herein.

In this patent, Example 4 describes the preparation of 2-chloro-4-trifluoromethyl-3'-formyl-4'-nitrodiphenyl ether [according to another nomenclature of 5- (2-chloro-4-trifluoromethylTenoxy) -2-nitrobenzaldehyde; identical to compound 1j, the yield, melting point and elemental analysis are given and the herbicidal activity of this compound is given in Table II. Physical data or herbicidal activity of compound 2 has not been reported.

DE-OS 3 017 795 describes novel substituted phenoxyphenylcarboxyimines as herbicidally active substances. The compounds of formula II used as intermediates are also referred to as herbicidally active compounds. The preparation of the compounds of formula II is given, physical data and herbicidal activity not shown.

Compounds 1 and 2 fall within the compounds described in DE-OS 3 017 795 of the general formula II.

The compounds of the formula II were prepared in DE-OS 3 017 795 as intermediates without nitro groups and their subsequent nitration. Physical data of the nitro-free intermediates are not given, and there is no mention of their herbicidal activity.

Compounds 3 and 4 fall under the nitro-free intermediates described in DE-OS no. 3,017,795.

EP-PS 0 053 321 describes novel herbicidally active phenoxycinnamic acid derivatives. Both the substituted phenoxy-2-nitrobenzaldehydes (compounds 1 and 2) and the substituted phenoxybenzaldehydes (compounds 3 and 4) are mentioned as intermediates in this synthesis. There is no mention of the herbicidal activity of the intermediates.

EP-PS 0 064 658 describes novel phenoxybenzaldehyde acetals which are herbicidally active and control the growth of plants. They are also described as starting materials, among others

5- (2-chloro-4-trifluoromethylphenoxy) -2-nitro-benzaldehyde (compound 1) and 5- (2,6-dichloro-4-trifluoromethylphenoxy) -2-nitrobenzaldehyde (compound 2). however, there is no mention of effectiveness.

Thus, the compounds 1 to 4 used according to the invention are known, even the herbicidal activity of the compounds 1 and 2 is described (although this is only demonstrated for the compound 1).

It has now been found that the compounds of formula I exhibit excellent fungicidal activity.

This finding is quite unexpected since only the herbicidal activity of these compounds is described in the literature. Also according to the Handbook of R. Wegler: Chemie der Pflanzenschutzund Schadlingsbekampfungsmittel Band 5, Springer-Verlag Berlin, Heidelberg, New York 1977, dienylether derivatives (substituted phenoxybenzolderivatives) can be used as herbicidally active substances in soy, corn and rice crops.

Accordingly, the present invention provides fungicidally effective compositions comprising substituted phenoxybenzaldehydes of formula I

-4-trifluoromethylphenoxy) benzaldehyde (compound 3).

when

X is hydrogen or chlorine;

Y is hydrogen or nitro, in addition to conventional carriers and excipients.

The fungicidal active compounds according to the invention are known per se and can be prepared by known methods. They can be prepared, for example, as follows:

3- (2,6-Dichloro-4-trifluoromethylphenoxy) benzaldehyde (compound 4J

6.1 g (0.05 mol) of 3-hydroxybenzaldehyde are converted into 150 ml of dry methanol by treatment with 2.8 g (0.06 mol) of potassium hydroxide in an inert atmosphere to 3-hydroxybenzaldehyde-potassium. a vacuum pump and the residue is treated with 2.5 g of potassium carbonate, 50 ml of dimethylsulfoxide and 13.75 g (0.055 mol, 10% excess) of 3,4,5-richlorobenzotrifluoride. 144 DEG C., dimethylsulfoxide is distilled off, the residue is diluted with 150 ml of benzene and the suspension is stirred for 1 hour, the benzene insoluble solids are filtered off with suction and the benzene is distilled off from the filtrate under water pump vacuum. This gave 9 g (60% of theory) of white crystals, molecular weight 335 (C14H7Cl2F3O2).

M / e (i.e.) =

336 (580) = F5Cl2Cl2Cl2CO2H2O4

335 (370) = F5Cl2Cl2CH2Cl2Cl2 •CHO

334 (1000) = F3C (C1) 2C6H2OC6H4CHO

333 (370) = F3C (C1) 2C6H2OC6H4CHO

271 (520) = F3C (Cl) C6H10OC6H5

236 (560) = F 3 C 5 H 2 OC 5 H 5

5- (2,6-Dichloro-4-trifluoromethyl-thenoxy) -2-nitrobenzaldehyde (compound 2)

3.75 g (0.011 mol) of 3- (2,6-dichloro-4-trifluoromethylphenoxy) benzaldehyde are dissolved in a mixture of 8.6 ml of dichloromethane and 5.3 ml of acetic anhydride, to which a nitrating acid composed of 2.4 ml is added. 65% (0.034 mol) nitric acid and 2.4 ml of 98% sulfuric acid are added dropwise with stirring at a rate such that the temperature does not exceed 10 DEG C. After the addition is complete, the reaction mixture is stirred at room temperature for 3 hours. The resulting white powder was filtered off with suction and dried to give 2.7 g of white crystals (64% of theory), melting point 117-119 ° C, molecular weight: 379 (C14H6O4Cl2F: 3) .

M / e (i.e.) =

381 (720) = F 3 C (C 12 H 6 O 2 O 6 H 3 '(NO) CHO

379 (1,000) = F3C (C1) (C5H2OC6Hs3NO2) CHO ··

349 (650) = F3C (C1) 2CeH2OC6H3 (O) 1 CHO

285. (320) = F2C (Cl) C1H2OC6H4

230 (220) = F3C (C1) 2CeH2OH

NMR: δ = 9.6 - 10.5 (aromatic aldehyde) (aldehyde-H starting material at δ = 9.85, nitro derivative at δ = 10.35 ppm)

IR: · 1690 · cm-1 (formyl-CO)

Under the conditions described, there is no oxidation of the formyl group. to the carboxylic acid, as can be seen from the above data.

Analogously, 5- (2-chloro-4-trifluoromethylphenoxy) -2-nitrobenzaldehyde (compound 1) can be prepared.

For use, the active compounds according to the invention are formulated in known manner into appropriate preparations, such as wettable powders (WP), suspension concentrates (SC), water-dilutable concentrates (SL), emulsifiable concentrates (EC), ULV preparations (ultra low volume) or mordants, preferably seed mordants. For this purpose, the active compounds are mixed with known solid or liquid inert carriers and, if appropriate, with other excipients.

Suitable excipients are, for example, surfactants such as wetting agents, suspending, dispersing and emulsifying agents, anti-caking agents, spreader agents, foam agents and stabilizers.

Possible solid carriers are inactive minerals such as kaolin, alumina, attapulgite, montmorillonite, clam, pyrophillite, bentonite, diatomaceous earth or highly dispersible synthetic silica, calcium carbonate, calcined magnesium oxide, dolomite, gypsum, tricalciumphosphate, fuller aluminum. and graIR: 1690 cm @ -1 (formyl-CO).

3- (2-Chloro-248,732) can be prepared analogously

organic materials such as tobacco stalks and sawdust.

Suitable liquid carriers are solvents and diluents such as water, organic and aqueous-organic solvent mixtures, for example of methanol, ethanol, n- and iso -propanol, diacetone alcohol, benzyl alcohol, glycols such as ethylene, triethylene and propylene glycol and their esters such as methylcellosolv and butyldiglycol; or ketones such as dimethyl ketone, methyl ethyl ketone, methyl isobutyl ketone, cyclopentanone, cyclohexanone; esters such as ethyl acetate, n- and iso-butyl acetate, amyl acetate, isopropyl myristate, dioctyl phthalate; aromatics, aliphatic and alicyclic hydrocarbons such as paraffins, cyclohexane, kerosene, light naphtha, benzene, toluene, decalin, alkylbenzene, chlorinated hydrocarbons such as trichloroethane, dichloromethane, perchlorethylene, dichloropropane, chlorobenzene; lactones such as γ-butyrolactone; lactams such as N-methylpyrrolidone, N-cyclohexylpyrrolidone; acid amides such as dimethylformamide; and 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, for example, ionic and non-ionic substances, such as salts of saturated and unsaturated carboxylic acids, sulfonates of aliphatic aromatic and aliphatic-aromatic hydrocarbons, alkyl-, aryl-aralkyl-carboxylic acids, their esters and ether-sulfonates. sulfonates of phenol, cresol and naphthalene condensation products, sulfated vegetable and animal oils, alkyl, aryl and aralkyl phosphate esters, as well as their salts with alkali metal bases, alkaline earth metal bases or organic bases such as amines, alkanolamines such as sodium lauryl sulfate, 2- sodium ethylhexyl sulfate, dodecylbenzenesulfonic acid sodium salt, dodecylbenzenesulfonic acid sodium salt with ethanolamine, diethanolamine, triethanolamine or isopropalamine, sodium mono- and diisopropylnaphthalenesulfonate, sodium naphthalenesulfonic acid, sodium diisoctylsulfosulfonate, sodium sodium xisoctyl sulfosuccinate, sodium xisoctyl sulfosuccinate, sodium, calcium, aluminum and magnesium stearate; phosphoric acid esters such as phosphated alkylphenols, fatty alcohol polyglycol ether, or partially; fully neutralized derivatives with cations or organic bases, finally disodium N-octadecylsulfosuccinate, sodium N-oleil-N-methyl-tauride and lignin sulfonate.

Suitable non-ionic substances are: ethylene oxide ether with C С-Сг ^ ^ ^, such as stearylpolyoxyethylene, oleylpolyoxyethylene; alkylphenol ether such as tert-butyl-, octyl- and nonylphenol polyglycol ether; organic acid esters such as polyethylene glycol ester of stearic acid and acid. myrist or polyethylene glycol oleate; partially saponified esters of fatty or oleic acids with hexanhydride, such as sorbitol oleic or stearic acid esters, and the like, and condensation products of these with ethylene oxide; as well as tertiary glycols such as 3,6-dimethyl-4-octin-3,6-diol or 4,7-dimethyl-5-decine-4,7-diol; polyethylene glycol thioether such as. is an ether of dodecyl mercaptan with polyethylene glycol.

The compositions according to the invention may contain as adhesion promoters: alkaline earth metal soaps, salts of sulfosuccinic acid esters, natural and synthetic water-soluble macromolecules! substances such as casein, starch, vegetable rubber, acacia, cellulose ether, methylcellulose, hydroxyethylcellulose, polyvinylpyrrolidone, polyvinyl alcohol etc. Anti-foaming agents such as low molecular weight polyoxyethylene, polyoxypropylene, block polymers, octyl-, nonyl- and phenylpolyoxyethylene may also be used. - degree higher than 5), long chain alcohols such as octyl alcohol, as well as special silicone oils.

Other additives may also be used to render the compositions colloidal with different fertilizers.

Other pesticidally active and / or nutrient substances may also be used.

In the preparation of wettable powder formulations (WP), the active ingredient, excipients and surfactants are mixed together, ground and homogenized. When liquid surfactants are used, they are sprayed onto the solid mixture of organic and inorganic excipients and, if appropriate, the active ingredient. The same procedure is applied when working with liquid active substances. When surfactants are used, the solids may also be suspended in an organic solvent containing liquid surfactants. After drying the suspension, a mixture of surfactant-coated particles is obtained.

To produce emulsifiable concentrates (EC), the components are dissolved in a water-immiscible solvent. The resulting mixture forms an emulsion with water without further processing, which is stable over a longer period of time.

In the preparation of water-dilutable concentrates (SL), a solution of the active ingredients and water-soluble excipients in water and / or a water-miscible solvent is prepared. The concentrate thus obtained is then diluted with water to the desired concentration.

The concentrate may also be dispersed with the appropriate emulsifier in a water-immiscible solvent. A so-called reversible emulsion is obtained which contains the components, even at molecular scales, in dispersed form and which is stored for a longer period of time.

In the manufacture of suspension concentrates. (SC)

Granulate:

5.0 wt.

69.0 wt.

3.0 wt.

3.0 wt.

5.0 wt. 15.0 wt.

is dissolved with optional heating of the wetting and dispersing agent in a mixture of water [preferably deionized water] and an antifreeze agent (preferably ethylene glycol or glycerin). To this solution is added a solid active ingredient and optionally an anti-caking ingredient (such as Aerosil 200) with stirring, and the sludge obtained is ground by grinding (e.g. a Dyno mill) to a particle size of up to 5 μΐη for adequate storage stability. If desired, an anti-foaming agent or thickening component (such as Kelzan S) is then added The procedure for adding the components may be varied or other active ingredients may also be used, in addition to solid active substances, water-miscible or water-immiscible liquid active substances and other Low melting point solids can be used in the form of a melt with or without an emulsifier.

ULV compositions can be prepared analogously to EC compositions.

Ready-to-use granules can be made by extrusion and application to granular carriers (limestone flour) or from carriers coated with liquid components.

Suspension concentrates (SC) and / or wettable powders (WP) may be granulated by agglomeration, such as by dragging with adherence enhancers.

The formulations are prepared by diluting with water or an inert solid diluent an appropriate form suitable for use, such as applicable solutions or powders, which contain the active ingredient in a concentration of from 0.0001 to 10% by weight, preferably 0.01 to 5% by weight.

The compositions of the invention may be used in the form of a seed film. For this purpose, either the foil or the seed is provided with a composition according to the invention.

Examples of resources

Suspension concentrate (SC):

Compound 4 ethylene glycol nonylphenyl polyglycol ether (OE 10) polysaccharide (xanthan gum) silicone oil water

40.0 wt.

10.0 wt.

5.0 wt.

0.1 wt.

1.0% w / w

43.9 wt.

Wettable Powder (WP):

Compound 1 highly dispersible silica kaolin sodium lignin sulphonate diatomaceous earth dispersant

30.0 wt.

15.0 wt.

20.0 wt.

5.0 wt.

25.0 wt.

5.0 wt.

compound 3 limestone flour ethylene glycol calcium lignin sulphonate highly dispersible silica water

Loose · Granulate (WG):

Compound 4 emulsifier (anionic and nonionic dispersant kaolin water

80.0 wt.

2.0 wt.

7.0% wt.

8.0 wt.

3.0 wt.

Emulsifiable concentrate (EC):

Compound 2 xylene cyclohexanone isophorone polyoxyethylene sorbitol monooleate sodium lignin sulfonate

Foil with seed

20.0 wt.

50.0 wt.

12.0 wt.

10.0 wt.

5.0 wt.

3.0 wt.

a) Film production g Rhodoviol 4/125 polyvinyl alcohol (viscosity of 4% aqueous solution at 20 ^° C 4 cP, 89% hydrolyzability) was dissolved in 615 g of water with stirring at 60 ° C. After dissolution, 20 g of Rhodoviol 30/20 polyvinyl alcohol (viscosity of 4% aqueous solution at 20 ° C 30 cP, 98% hydrolyzability) and 20 g of glycerin are added and mixed until a homogeneous solution is obtained. Allow to stand for 24 hours to remove bubbles. The solution is then applied to a glass plate of 0.50 mm thickness and dried at room temperature. The film obtained is separated from the glass plate and has a thickness of 0.05 to 0.06 mm.

b) Production of a film containing the active substance

To the solution produced in a) was added a suspension of 0.120 g of compound 2 in 5 ml of water. After de-bubbling, the films are prepared in the same manner as in a). A film with an active substance concentration of 1000 ppm is thus obtained.

When a suspension of 0.0120 g of compound 4 in 5 ml of water is used instead of compound 2. a film with an active compound concentration of 100 ppm is obtained.

For the fight against fungal attack on plants, the following forms are most commonly used: mordants, dusts and sprays. The fungicidal active substance is preferably allowed to act in the vicinity of the attack, for example its spread or in the environment.

no

Pickling is used to safely store seeds and prevent infections with soil fungi. Seeds and seedlings are primarily endangered by fungal conidic fungi. Examples include: Fusarium graminearium and Fusarium moniliforme, as well as Nigrospora oryzae in maize cultures, Rhizoctonia, Penicilium and Helmlthosporium.

Dusting and spraying are used to combat fungi that attack leaves and fruits. Examples include: 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 M. fructigena

Aspergillus, such as A. niger Penicillium, such as P. crustaceum Botrytis, such as B. cinerea Verticillium, such as V. albo-atrum Trichothecium, such as T. roseum Cercosporella, such as C. herpotrichoides

Dematiaceae:

Thielaviopsis, such as T. basicola Nigrospora, such as N. oryzae Spilocea, such as S. pomi (Fusicladium dendriticum) Cladosporium, such as C. fulvum Helminthosporium, such as H. turcicum Cercorpora, such as C beticola Alternaria such as A. solani Stemhylium such as S. radicinum

Tuberculariaceae:

Fusarium such as F. graminearum a

F. oxysporum.

The known 1,2,5,6-tetrahydro-N-trichloromethylthiophthalimide (Captan) was used as a comparative compound in the following examples of use.

Example 1

Fungicidal activity

Prepare agar broth in 100 mm Petri dishes (diameter) from potato agar with 2% dextrose.

An emulsifiable concentrate containing 20 why, the active ingredients is diluted to the desired concentration. From the spores of the test fungi, suspensions are prepared at a concentration at which 25 to 30 spores are observed in a drop in the field of view of the microscope at 100 to 160 times. Add 1 ml of the spore suspension to a 1 ml solution of the active substance by pipette, allow to stand for 30 minutes, and finally apply to agar broth. The fungi are inoculated until vigorous development, then evaluated in a control test on the following scale:

= no development (0% control) = weak development (10% control) = moderate development (50% control) = strong development (100% control)

The evaluation values obtained, their mean and percentage values as well as the fungicidal efficacy are given in Table 1.

Claims (1)

The active ingredient is emulsified to the desired concentration and inoculated with fungi. 7 days after incubation, suppression of development was assessed. Table 2 shows the concentrations required for 100% suppression. In 20 ml of 2% malt nutrient solution Example 2 Fungitoxicity TABLE 2 · Oxysporum Fusarium nivale Fusarium solani - Aspergillus niger Botrytis cinerea Botrytis fabae Stemphylium radicinum Trithothecium roseum Thielaviopsis basicola Nigrospora oryzae Cladosporium cucumerrnum Penicillium crustaceum Verticillium alboatrum Fusicladium dendriticum Monilia fructigena Fungitoxicity Captan compound (known) 1 2 3 4 300 300 300 1000 1000 300 300 300 1000 1000 300 300 300 1 000 1000 100—300 300 300 1 000 1000 100—300 100—300 300 1000 1000 100—300 100—300 100—300 1000 300 100—300 100—300 100—300 1000 300 100—300 100—300 100—300 1000 300 100—300 100—300 100—300 1000 300 100—300 100—300 30—100 300 300 100—300 30—100 30—100 100—300 100—300 30—100 30—100 30—100 100—300 100—300 30—100 30—100 30—100 100—300 100—300 30—100 30—100 30—100 100—300 100—300 30—100 30—100 30—100 100— 300 100—300 30 30 30—100 100-300 100—300 30 30 30 100—300 100—300 Example 3 Phytotoxicity The pots with a surface of 1.64 dm2 were filled with sandy soil. 20-30 seeds were planted twice in parallel in the soil. 10 days after germination, the germs were sprayed with 20% emulsion of active ingredient at a rate of 1, 3 and 9 kg / ha. 10 days after treatment, germ damage was expressed as a percentage of control. The following plants were tested: A - Soya (Glycine soya) B - Oim wheat (Trittcum aestivum) C - (Džinm jeemmn (Hoodeum vulgare)) D - (kRknic (Zea mays) E - Prooo (Setaria italica) F - cotton (Gossypium hirsutum) G - white mustard (Sinapsis alba) H - Bean (Phaseolus vulgaris) I - peas (Plsum sativum) K - lupine (Lupinus albus) L - Vetch (Vicia faba) M - alfalfa (Medicago sativa) N - carrot (Daucus carota) O - sugar beet (Beta vulgaris) P - sunflower (Helianthus annuus) control TABLE 3 Phytotoxicity Compound 1 dose 1 3 9 1 3 9 1 3 9 1 3 9 AND 0 5 10 0 5 15 Dec 0 0 10 0 0 15 Dec 0 (B) 5 10 30 0 10 30 0 0 20 May 0 5 25 0 C 10 35 50 15 Dec 25 50 10 20 May 40 10 20 May 40 0 D 10 40 60 30 50 70 15 Dec 20 May 45 20 May 30 50 0 E 60 80 100 ALIGN! 50 75 100 ALIGN! 30 60 100 ALIGN! 30 70 100 ALIGN! 0 F 80 95 98 30 65 90 30 40 70 30 50 75 0 G 40 60 90 50 80 95 30 50 100 ALIGN! 35 60 95 0 H 50 80 80 45 65 85 0 10 50 5 15 Dec 40 0 AND 15 Dec 30 50 10 40 60 10 30 40 20 May 30 40 0 TO 40 50 70 50 60 70 10 15 Dec 20 May 10 20 May 25 0 L 70 80 90 80 90 100 ALIGN! 25 50 75 20 May 35 55 0 M 60 90 100 ALIGN! 70 80 95 30 50 90 30 60 95 0 N 10 20 May 70 30 70 90 30 50 80 20 May 40 65 0 O 10 10 20 May 15 Dec 25 30 20 May 40 60 25 50 75 0 P 40 50 75 10 35 60 20 May 40 80 30 50 75 0 Example 4 tanu. It was i used benefits 0.1; 0.25; 0.5; 1,0 a 2,0 effectively substances per kg seeds SicknessDefection against fungal barn gods by pickling. a suspension con- centration was used with a test compound centrate at a concentration of 400 g / l and a 50% WP formulation of the known Capj bean of the Merit species. 10 days after pickling, the seeds are planted in a greenhouse and in open soil to a depth of 4 to 5 cm and at a distance of 5 x 50 cm. At a key length of 10 to 12 cm, germs and damage are measured. listed in Table 4. The values are TABLE 4 Soybean dressing infestation in% Compound dose (g / kg) Alternaria sp. Penicillium sp. Fusarium sp. Greenhouse germination in% Germination in the wild in% 1 0.1 28.1 5.0 2.2 85 105 0.25 14.2 3.2 1.3 90 118 0.5 7.0 - 0.5 80 120 1 4.3 - - 70 94 2 1.5 - - 64 92 2 0.1 22.3 5.8 3.1 80 102 0.25 14.1 4.4 1,2 85 104 0.5 6.6 0.2 - 92 122 1 4.2 - - 78 96 2 0.5 - - 66 90 3 0.1 58.2 8.9 6.2 82 100 ALIGN! 0.25 49.5 7.6 5.0 82 105 0.5 13.4 3.8 1,8 86 107 1 6.6 2,0 0.2 90 105 2 4.3 0.5 - 82 98 4 0.1 54.2 9.1 5.0 80 101 0.25 39.8 6.8 4.4 82 102 0.5 16.3 2.2 2.3 86 109 1 9.8 1.5 - 91 102 2 6.7 - 84 102 Compound dose (g / kg) Altema-ra sp. i Penicillium properties Sp. Fusarium sp. Greenhouse germination in% Germination in the wild in% Captan 0.1 26.4 3.2 3.0 82 102 (known) 0.25 13.6 2.2 1.5 90 116 0.5 7.5 0.2 0.5 94 121 1 2.6 - - 90 114 2 0.8 - - 90 105 Control - 75.0 12.0 6.0 78 100 ALIGN! Example 5 and after the ears are expelled, No plants in quantities of 500 1 / ha. Damage Fight against fusariose ears of winter wheat up evaluates u ears 12 days after ear treatment and seed trolls, and as a percentage is given in Table 5. Dilute 20% of the active substance emulsion concentrate to the desired concentration with water, TABLE 5 Fusariosa ears Compound Dose (kg. ha '1) ear % Damage to Fusarium spp. with <im immer seeds total inside Harvest (kg / 10 m2) 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 OF THE INVENTION characterized by A fungicidal composition, comprising as active ingredient substituted phenoxybenzaldehydes of the general formula I wherein: X is hydrogen or chlorine, Y is hydrogen or a nitro group, in addition to conventional carriers and excipients;