CS249535B2 - Fungicide and method of its efficient substances production - Google Patents

Abstract

The invention provides compounds of formula I <IMAGE> wherein R1 and R3 stand for trifluoromethyl or nitro with the proviso that R1 and R3 are different; R2 is hydrogen or 3-formyl-phenoxy: X represents hydrogen or chlorine and Y stands for hydrogen or nitro/ and fungicidal compositions comprising the same. These compounds can be prepared by reacting 3-hydroxy-benzaldehyde or an alkali metal salt thereof with a compound of Formula II <IMAGE> and if desired nitrating the compound of Formula I/a <IMAGE> thus obtained into the corresponding compound of Formula I/b <IMAGE>

Description

The present invention relates to novel phenoxybenzaldehyde derivatives of the general formula I, to a process for their preparation, to fungicidal compositions containing the compounds and to their use as fungicidally active substances.

Substituted phenoxybenzene derivatives, also called diphenyl ethers, have been known for over 20 years as herbicidally active compounds, especially in rice, cotton and soybean cultivation. These compounds are described by R. Wegler in Chemie der Pflanzenschutz- und Schadlingsbekampcungsmittel, Vol. 5 (Springer-Verlag, Berlin, Heidelberg New York, 1977) on pages 73-80 and 401-407. From diphenylether derivatives, the following compounds exhibit potent herbicidal activity:

2-methyl-1- (4-nitrophenoxy) -4-trifluoromethylbenzene (Fluorodiphen);

2-chloro-1- [4-nitrophenoxy) -4-trifluoromethylbenzene (Nitrofluorophen),

2-chloro-1- [3-ethoxy-4-nitrophenoxy) -4-trifluoromethylbenzene (OxyHorphen),

Sodium 5- (2-chloro-4-trifluoromethylphenoxy) -2-nitrobenzoate [Acilfluoropheneatrium], ethyl 5- [2-chloro-4-trifluoromethylphenoxy) -2-nitrobenzoate [Acil Orphen-E] 1) [US-PS 3 798 276, US-PS 4 031 131, US-PS 4 164 408, GB-PS 1 390 295, DE-OS 2 333 848].

The closest compounds of the invention are those disclosed in US-PS 4,306,900 and DE-OS 3,017,795 as herbicidally active agents. However, these substances are structurally different from the compounds of the invention. The fungicidal activity of the compounds disclosed in the aforementioned patents is described in the applicant's earlier application [No. 157/84 - Hungarian, which is not a prior art.

However, the efficacy of the known compounds is not always satisfactory.

It has now been found that the new phenoxybenzaldehyde derivatives exhibit excellent fungicidal activity.

Accordingly, the present invention provides a phenoxybenzaldehyde derivative of the formula I wherein

R1 and R3 are trifluoromethyl or nitro, and R1 and R3 do not simultaneously represent the same group,

R2 is hydrogen or 3-formylphenoxy,

X is hydrogen or chlorine;

Y is hydrogen or nitro.

The invention also relates to fungicidal compositions comprising as active ingredient novel phenoxybenzaldehyde derivatives of the general formula I, in which R1, R2, R5, X and Y are as defined above.

Furthermore, it has been found that novel phenoxybenzaldehyde derivatives can be prepared by reacting 3-hydroxybenzaldehyde or its alkali salts with a substituted benzene derivative of formula II

(I!) Where

R1, R2, R3, X and Y are as defined above and

Hal represents halogen, preferably chlorine, in the presence of an inert diluent, the phenoxybenzaldehyde of the formula Ia obtained

H

C-0 /

[+) where

R1, R2, R3 and X are as defined above, isolated and optionally nitrated, and finally the phenoxybenzaldehyde derivative of general formula Ib obtained

SS ^v

O .... _> ^{B B} 3 \>

AND

H!

L ~ O — K - h

In _______>

(!)

H and C = V (O) .....

(Ib) \ -Ά

IN

AND,':·'

3,

4 9 5 3 5 Where

R1, R2, R3 and X are as defined above, isolates.

In the process according to the invention, 3-hydroxybenzaldehyde or an alkali metal salt thereof, preferably a sodium or potassium salt, is reacted with a substituted benzene halide derivative of the formula II in the presence of an inert solvent.

Chlorobenzene is preferably used as the substituted benzene halide of formula II.

3-Hydroxybenzaldehyde and a substituted benzene halide used as starting materials are generally known in organic chemistry.

The reaction is preferably carried out in the presence of an acid binding agent. Suitable such as: alkali metal carbonates such as sodium or potassium carbonate or alkali metal bicarbonates such as sodium or potassium hydrogen, furthermore rare earth metal oxides such as magnesium oxide and alkali metal alcoholates such as methylate sodium.

Preferably, inert organic solvents are used as diluents. To facilitate the processing of the batch, solvents with a boiling point below 150 ° C are used, and to accelerate the reaction, aprotic, preferably dipolar and aprotic solvents such as dimethylformamide, dimethylacetamide, sulfolane, dimethylsulfoxide and acetone.

The reaction temperature can be varied over a wide range. Generally, between 20 and 120 degrees Celsius, preferably between 25 and 100 degrees centigrade, is employed.

The reaction time is several hours or several days and can be influenced by temperature and / or solvent.

The working up of the reaction mixture is carried out in a known manner, for example by removing the solvent, aspirating, washing and drying the product.

The 2-nitro compounds of formula Ib are preferably obtained from compounds of formula Ia by direct nitration. The nitration can be carried out in a known manner. The reaction is preferably carried out in inert organic solvents such as chlorinated hydrocarbons, in particular chlorinated aliphatic hydrocarbons, such as dichloromethane or dichloroethane, in the presence of acetic anhydride and nitrating acid at a temperature below 25 ° C. The reaction mixture is worked up by pouring the reaction mixture on ice or water, separating the precipitate and purifying, for example, by recrystallization.

For use, the compounds of the invention are formulated as a powder formulation (WP), suspension concentrate (SC), water dilutable concentrate (SL), emulsifiable concentrate (ECj, ultra low volume) or mordants, preferably seed mordants. The active compounds are mixed with known solid or liquid inert carriers and, if desired, with other excipients.

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

Suitable 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, full earth clay. as well as granules of organic material such as tobacco stalks and sawdust.

Suitable liquid carriers are solvents and diluents such as water, organic and aqueous-organic solvent mixtures, for example from methanol, ethanol, n- and iso -propanol, diacetone alcohol, benzyl alcohol; glycol and such as ethylene, triethylene and propylene glycol, and esters thereof such as methylcellosolv and butyldiglycol; or ketones thereof dimethyl ketone, methyl ethyl ketone, methyl isobutyl ketone, cyclopentanone, cyclohexanone; esters such as ethyl acetate, n- and iso-propyl 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, xylene, tetralin, decalin, alkylbenzene, chlorinated hydrocarbons such as trichloroethane, dichloromethane, perchlorethylene, dichloropropane, chlorobenzene; lactones such as χ-butyrolactone; lactams such as N-methylpyrrolidine, 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 semen oil.

Suitable wetting, dispersing and emulsifying agents are ionic and non-ionic substances, such as salts of saturated and unsaturated carboxylic acids, sulfonates of aliphatic, aromatic and aliphatic-aromatic hydrocarbons, alkyl-, aryl- and aralkylcarboxylic acids, their esters and ether-sulfonates, sulfonates of condensation products phenol, cresol and naphthalene, sulfated vegetable and animal oils, alkyl, aryl and aralkyl phosphate esters, and their salts with alkali metal, alkaline earth metal or organic bases such as amines, alkanolamines such as sodium lauryl sulfate, sodium 2-ethylhexyl sulfate, sodium dodecyl-benzenesulfonic acid, dodecyl-benzenesulfoic acid and ethanolamine, diethanolamine, triethanolamine or isopropylamine, sodium mono- and diisopropylnaphthalenesulfonate, sodium naphthalenesulfonic acid, sodium dnsoctylsulfosuccinate, sodium xylenesulfonate, sodium sulfonate acids from petroleum, dra''И λ 0 5 3

8 soap, potassium, sodium, calcium, aluminum and magnesium stearate, phosphoric acid esters such as phosphated alkenylphenols, fatty alcohol-polyglycol ether, or partially or totally neutralized derivatives with cations or organic bases, finally disodium-N octadocylsulfosaccinate, sodium-N- oleil-N-methyl-tnuride and lignin sulfonate.

Possible non-ionic substances are:

ethylene oxide ether with C 10 to C 20 alcohols such as stearyl polyoxyethylene, oleyl polyoxyethylene;

alkylphenol ethers such as tert-butyl, octyl and nonylphenolpolyglycolethers;

organic acid esters such as polyethylene glycol ester of stearic acid and myristic acid or polyethylene glycol oleate;

ethylene oxide or propylene oxide block polymers;

partially saponified esters of fatty or oleic acids with hexanhydride, such as an oleic acid or stearic acid ester with sorbitol 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 thioethers such as dodecyl mercaptyne ether with polyethylene glycol.

The compositions of the invention may include as adhesion promoters: alkaline earth metal soaps, sulfosuccinic acid ester salts, natural and synthetic water-soluble macromolecules such as casein, starch, vegetable rubber, acacia, cellulose ethers, methylcellulose, hydroxyethylcellulose, polyvinylpyrrolidone, polyvinyl alcohol etc.

Antifoam agents such as low molecular weight polyoxyethylene, polyoxypropylene, block polymers, octyl, nonyl and phenylpolyoxyethylene (OE grades greater than 5), long chain alcohols such as octanol, as well as special silicone oils may also be used.

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 compositions (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 surfactant liquids are used, it is also possible to suspend the solids in an organic solvent containing liquid surfactants. After drying the suspension, a mixture of surfactant-coated particles is obtained.

In the preparation of emulsifiable concentrates (EG), the components are dissolved in a water-immiscible solvent. The resulting mixture forms with water without further processing an emulsion that is stable for a longer period of storage.

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 with an appropriate emulsifier. dispersed in a water immiscible solvent. A so-called reversible emulsion is obtained which contains the components, even on a molecular scale, in dispersed form and which is stored for a longer period of time.

In the preparation of suspension concentrates (SG), wetting and dispersing agents are dissolved in a mixture of water (preferably deionized water) and an antifreeze agent (preferably ethylene glycol or glycerin), optionally heated. To this solution is added a solid active ingredient and optionally an anti-caking component (such as Aerosil 000) with stirring. The sludge obtained is adjusted by grinding (e.g. a Dyno-mill) to a particle size of up to 5 gm for adequate storage stability. Optionally, an anti-foaming agent or thickening component (such as Kelzan S) is then added. The process of adding the ingredients may be varied or other active ingredients may also be used, in addition to the solid active ingredients, water-miscible or water-immiscible liquid active ingredients or other ingredients such as pigments may also be used. The 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 ECE means.

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 compositions according to the invention contain the active ingredient in a concentration of between 0.001 and 99% by weight. %, preferably between 0.01 to 95 wt. %.

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

The compositions of the invention may be used in the form of seed films. To this end, either the film or the seed is treated with the composition according to the invention.

To combat fungal attack. The most common forms of plants are: mordants, dusts and sprays. The fungicide active substance is preferably allowed to act in the vicinity of the attack, for example its spread, e.g. in the living space.

Pickling is used to safely store the seeds and prevent infection by 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, Penicillium and Helminthosporium.

Dusting and spraying are used to combat fungi that attack leaves and fruits. Examples include: Monika fructigena and Spilocea poml in apples and Botrytis cinerea in grapes.

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

Moniliacae:

Monilia such as M. fructigena Aspergillus such as A. niger Penicilium 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;

úematiaceae:

Thielaviopsis, such as T. basicola Nigrospora, such as N. oryzae

Spilocea, such as S. pomi (Fusicladium dendriticum)

Cladosporium, such as .C. Helmithosporium fulvum, such as H. turcicum Cercorpora, such as C. beticola Alternaria, such as A. solani Stelphylium, such as S. radicinum

Tuberculariaceae:

Fusarium such as F. graminearum and F. oxysporum.

The invention is illustrated by the following non-limiting examples.

Example 1

3- (5-Chloro-4-trifluoromethyl-12-nitro-phenox) -beozaldehyde

A suspension of 7.8 g (0.03 mol) of 2-oxo-5-nitrobenzotrifluroide, 4.4 g (0.036 mol)

Of 3-hydroxybenzaldehyde and 4.97 g (0.036 mol) of anhydrous calcium carbonate in 50 ml of acetone are stirred at room temperature for 16 hours. It is then filtered off with suction and the filtrate is freed from acetone under a water pump vacuum. Oily. the residue is recrystallized from isopropanol. 8.0 g (77% of theory) of beige-colored crystals are obtained, m.p. 80-83 [deg.] C., molecular weight for C14H7O4NCIF3: 345.

M / e (o.i) -

345 (800) = FzC (Cl ((NO22nHH2OC6H4CHO

300 (300) = F ^ 3C (ClC ^ 6 ^ ^: ^ C ^ C ^ (JF ^ 4CHO)

328 (150): == F3C (C1) (NO)) C6HcOC6H4C

224 (1000) = F3C (C1) P1 (22C366 ^ 2)

121 (6200 = OC 6 H 4 CHO)

1 H-NMR: 9.92 ppm (formyl-H)

IR: 1680 (formyl-CC), 0830 and 0730 (foomyl CH) cm ^"4.

Example 0

3- (1-Trifluoromethyl-2,6-dinitrophetyl) was zaldehyde

The procedure was as in Example 1 except that, instead of 2,4-dichloro-5-nitrobenzotrifluoride, 2-methyl-4-chloro was used, 9.5 g (89% of theory) of yellow crystals were obtained.

Melting point: 130-131 ° C, molecular weight for C 14 H 7 O 6 N 2 F 3: 336.

M / e (%) =

356 (8770 = ΡΒ ^ ΝΟφϋβΗοΟύβΗ ^ ΗΟ 337 (1000 = F2C (NO2)) 2C6H2OC6H4CHO 035 (1800 = F3C (NC22 22C6H2

101 (Ю000 '= OC6H4CHO)

1H-NMR:

8.40 (phenoxy-H),

9.85 (form 1 H) ppm

IR:

685 (tomyl-CC),

830 and 2940 (forms-CH) cm ⁴ .

Example 3

3- (1-Trifluuromethylib, 6-dimtrophenooyl-β-zaldehyde)

The procedure was as in Example 1, except that 2-chloro-3,5-dinobenzotrifluoride was used in place of 2,4-dichloro-5-nitrreenzene (trifluoride) to give 8.1 g (76% of theory) of pale yellow crystals.

Melting point: 104 ° C, molecular weight for C 14 H 7 O 6 N 2 F 3: 356.

M / e [r. i.) =

356 (880) = F 3 C (NO 2) 2 C 6 H 2 OC 4 H 4 CHO

235 (570) = F3C (NO) 12C6H)

121 (1000) '= ^X OCeHáCHO H-NMR:

9.85 (formyl-H) ppm

IR:

695 (formyl-CO)

750 and 2855 (formyl-CH) cm ^-1 .

Example 4

2,4-Bis- (3-formylphenoxy) -1-trifluoromethyl-3,5-dinitrobenzene

3.66 g (0.03 mol) of 3-hydroxybenzaldehyde, 5.06 g (0.0175 mol) of 2,4-dichloro-3,5-dinitrobenzotrifluoride and 4.55 g (0.033 mol) of anhydrous calcium carbonate are stirred in 50 ml of anhydrous acetone at room temperature for 6 hours, then left to stand for one day. Finally, it is filtered off with suction, washed with acetone, the filtrate is concentrated under a water pump vacuum and the residue is crystallized from 60 ml of isopropanol. 5.3 g (85% of theory) of pale yellow crystals are obtained.

Melting point: 137-138 ° C, molecular weight for C 21 H 11 O 8 N 2 F 3: 476.

M / e (i.e.) =

476 (551)

459 (1000)

367 (220)

121 (320) (560) = F3C (NO2) 2CSH4 (CHO) 2 = F3C (NO2) 2C6H (OC6H4CHO) OC6H4C = F3CC6H (OC6H4CHO) OC6H4O OC6H4CHO = ^X = OC6H4 H-NMR:

9.87 (formyl-H),

8.55 (benzene-H) ppm

IR:

of 1.8 ml (0.027 mol) of 65% nitric acid and 1.8 ml of 98% sulfuric acid. After the addition, the temperature of the reaction mixture was allowed to rise to room temperature and stirred at this temperature for 3 hours. The dichloromethane is removed under a water pump vacuum, the residue is poured into 200 ml of ice water, the precipitate is filtered off with suction and dried. The product is recrystallized from isopropanol. Thus 4.1 g (60% of theory) of yellow crystals are obtained.

Melting point: 129-130 ° C, molecular weight for C 14 H 60 O 3 N 3 F 3: 401.

M / e (i.e.) =

401 (180) = F3C (NO2) 2C6H2OC6H (NO2) CHO

382 (130) = F2C (NO2) 2C6H2OC6H4 (NO2) CHO

235 (400) = F 3 C (NO 2) 2 C 6 H 2

166 (1,000) = OC 6 H 3 (NO 2) CHO

1 H-NMR:

10.255 (formyl-H) ppm

IR:.

700 (formyl-CO)

520 to 1550 (nitro),

320 (nitro and C-O-C) cm -1.

Example 6

5- (2-Trifluoromethyl-4,6-dinitrophenoxy) -2-nitrobenzaldehyde

8.4 g (0.022 mol) of 3- (2-trifluoromethyl-4,6-dinitrophenoxy) benzaldehyde (Example 4) were nitrated as in Example 5. 6.0 g (64% of theory) of yellow crystals were obtained.

Melting point: 112-122 ° C, molecular weight for C14H6O8N3F3: 401.

M / e (i.e.) =

401 (110) = FzC (NO)) 2C6H2OC6Hz (NOtCHO

251 (2200 = FsClNO 4 CemO)

235 (1,002) =

166 (? 5? 00 = OC 6 H 3 (NO 2) CHO)

1 H-NMR:

10.25 (formyl-H),

9.05 (phenoxy-H),

8.82 (j = 3 Hz, phenoxy-H) ppm

IR:

1700 (formyl-CO) cm -1.

1700 (formyl-CO)

740, 2,820 and 2,860 (formyl-CH) cm ^-1 .

Example 5

5- (4-Trifluoromethyl-2,6-dinitrophenoxy) -2-nitrobenzaldehyde

6.05 g (0.017 mol) of 3- (4-trifluoromethyl-2,6-dinitrophenoxy) benzaldehyde (example

2) is dissolved in a mixture of 12.5 ml of dichloromethane and 7.6 g of acetic anhydride, cooled to ° C and the nitrating acid composed of

243535

Examples of resources:

Suspension concentrate (SC):

% wt.

Compound 4 ethylene glycol nonylphenyl polyglycol- ether (OE 10) polysaccharide silicone oil water Wettable powder composition 50.0 8, ® 5.0 0.1 1.5 35.4 (WP): % wt. Compound 1 90.0 highly dispersible acid siliceous 5.0 dispersing agent 5.0 Granulate: % wt. Compound 6 5.0 limestone meal 69.0 ethylene glycol 3.0 sodium lignin sulphonate 3.0 highly dispersible acid siliceous 5.0 water 15.0 Loose granulate (WG): % wt. Compound 2 80.0 sodium lauryl sulfate 2,0 sodium lignin sulphonate 7.0 kaolin 8.0 water 3.0 Emulsifiable concentrate (EC): % wt. (a) Compound 3 40.0 xylene 12.0 cyclohexanone 20.0 isophorone 20.0 polyoxyethylenesorbit- monooleate 5.0 nonylphenylpolyglycol- ether (OE 10) 3.0 % wt. (b) Compound 1 20.0 xylene 60.0 isophorone 8.0 polyoxyethylenesorbit- Trioleate 5.0 tributylphenylpolyglycol- ether (OE 10) 7.0

Foil with seed

a) Film production g Rhodoviol 4/125 polyvinyl alcohol (viscosity of 4% aqueous solution at 20 ° C 4cP, 89% hydrolyzability) is dissolved with stirring at: 60 ° C in 615 g of water. 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 6 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 3 in 5 ml of water is used instead of compound 6, a film with a concentration of 100 ppm of active substance is obtained.

Examples of use

The known 5- (2,6-dichloro-4-trifluoromethylphenoxy) -2-nitrobenzaldehyde (A) is used as a comparative compound in the following examples of use.

Example A

Fungicidal activity

Prepare agar broth in 100 mm potato agar dishes with 2% dextrose.

The emulsifiable concentrate containing 20% active ingredient is diluted to the desired concentration. A suspension is prepared from the spores of the test fungi at a concentration such that 25 to 30 spores are observed in a drop in the field of view of the microscope at a magnification of 100 to 160 times. Add 1 ml of the spore suspension by pipette to 1 ml of the active substance solution, 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:

1. = no development (0% control)

2. = poor development (10% control)

3. = medium development (50% control)

4. = strong development (100% control)

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

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effective concentration (A) active substance development (B) average development in% efficiency (ppm) 1 2 3 4 average 1 2 3 4 (A (Bj (A

they plant 30 seeds of Sinapsis arvensis and Setaria glauce at a depth of 0.5 cm. The pre-emergence treatment was carried out directly on planting, the post-emergence treatment 10 days after germination with an emulsifiable concentrate containing 10% active ingredient. The ED50 values obtained (medien efficient yet) are given in Table B.

Example В

Herbicidal activity

This example serves to demonstrate that the compounds of the invention do not exhibit herbicidal but only fungicidal activity as in Example A.

The pots with a surface area of 1.64 dm ² are filled

249335 effective dose of Sinapsis arvensis Setaria glauca substance (kg. Ha ¹ ) preemer- ED50 postemer- ED50 preemer- ED50 postemer- EDso gentle gentle (° / o) gentle (%) gentle (° / o)

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Claims (2)

A fungicidal composition, characterized in that it comprises, as active ingredient, phenoxybenzaldehyde derivatives of the general formula (I): R 1, R 2, R 5, X and Y · are as defined above, Hal represents halogen, preferably chlorine, in the presence of an inert diluent, obtained by the phenoxybenzaldehyde of the general formula Ia / 7 wherein: R 1 and R 5 are trifluoromethyl or nitro, wherein R 1 and R 3 cannot simultaneously represent the same group, R @ 2 denotes hydrogen or 3-formylphenoxyskin, X is hydrogen or chlorine; Y is hydrogen or nitro. 2. A process for the preparation of a phenoxybenzaldehyde of the formula I according to claim 1, characterized in that the 3-hydroxybenzaldehyde or its alkali metal salt is reacted with a substituted benzene derivative of the formula II: R 1, R 2, R 5, X and Y are as defined above, is isolated and optionally nitrated, and the phenoxybenzaldehyde of formula (1b) obtained '....... / r, · - / O' X X 'where R 1, R 2, R 5, X and Y are as defined above, are isolated.