JPS60231602A - Fungicidal composition and use - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a fungicide and a method for controlling fungal plant diseases. More particularly, the invention relates to fungicides comprising phenoxybenzaldehyde derivatives as active ingredients and the use of said phenoxybenzaldehydes for combating fungal plant diseases.

According to the invention, an effective amount of at least one compound represented by the following general formula (1) (wherein X is hydrogen or chlorine, and Y is hydrogen or a nitro group) is used as an active ingredient. A disinfectant comprising:

General formula (1) contains the following four types of compounds, namely, 5-
((2-chloro-4-trifluoromethyl)-phenoxy-2-nitro-benzaldehyde (compound A1): 5-[(2,6-dichloro-4-trifluoromethyl)-phenoxy]-2-nitrobenzaldehyde (Compound 2): 3-((2-chloro-4-trifluoromethyl)-phenoxy]-benzaldehyde (compound A 3 ): and 34(2,6-dichloro-4-trifluoromethyl)-
phenoxif-benzaldehyde (compound A4);

The above four compounds of general formula (I) are known as herbicides, or may have herbicidal effects although no biological data exist.

U.S. Patent No. 4,306,900 (priority mill: 19
May 5, 1979, United States, AI 82,372), novel nitro-diphenyl ether derivatives are protected as herbicides. Compounds A1 and A2 are within the scope of the claims.

Example 4 of the US patent specification contains 2-chloro-4-trifluoromethyl-3'-formyl-4'-nitro-diphenyl-ether (this compound is identical to compound 1 but given a different name). The preparation, yield, melting point and elemental analysis of the compound (as described in Table 2) are disclosed, and Table 2 describes the herbicidal efficacy of this compound. The biological activity and physical constants of compound A2 are not described in the patent.

German Published Application No. 3,017,795 [US priority = 1
May 11, 1979 (38,043) and April 1980
14th (136, 171): Published on November 13, 1980, West Germany] describes a new herbicidal phenoxyphenylucardoxyoxyiminca. The intermediate of general formula (n) used in the synthesis is described as a new compound with herbicidal activity (page 18), and the method for its production is also described, but physical constants and biological data are not disclosed. Not yet. Compounds A1 and A2 fall within the scope of the general formula (II) of the German published application. General formula (I
The intermediate f) is obtained by first forming an intermediate without a nitro group and then nitrating the compound thus obtained. The physical constants of intermediates without nitro groups are not disclosed, and there are no biological effects based on these compounds (page 34).

Compounds A3 and A4 belong to said intermediates without a nitro group.

Yoyotsu/4' Patent Application Publication No. 0.053,321 and priority date: November 28, 1980 (DE3,044,8
10): Publication date in West Germany: June 9, 1982 (Noyaten Brass. 82/23)] discloses novel herbicidal phenoxycinnamic acid derivatives. Phenoxy-2-nitro-benzaldehyde derivatives A1 and A
2. Parallelly substituted phenoxybenzaldehyde derivative A3
and 4 are described as synthetic intermediates, but herbicidal activity is not based on them.

Euronose Patent Application Publication No. 0.064,658 (priority date: May 9, 1981 (DE3118371): Publication date in West Germany: November 17, 1982 (Patent Black) 82/46)) A novel phenoxybenzaldehyde with efficacy and plant growth inhibitory effect is disclosed. In these syntheses, 1 e.g. 5-[
(2-chloro-4-trifluoromethyl)-7enoxy]-2-nitrobenzaldehyde and 5-[(2,
Although the herbicidal effect is not based on these compounds (U.S. Pat.
．． 306,900). These two intermediates are the same as compounds A1 and A2.

From these patent specifications, among the four types of compounds belonging to general formula (1), compound A1 and ni-2 (substituted phenoxy-4
-Nitro-benzaldehyde) has a herbicidal effect, but it is clear that biological data are disclosed only for compound A1.

Surprisingly, when substituted phenoxybenzaldehydes were tested, compounds 1-4 were found to have bactericidal activity. The most recent prior art (including U.S. Pat. No. 4,306,900 and German Published Application No. 3,017,
795), said finding is very surprising since a person skilled in the art could only draw the conclusion that substituted phenoxybenzaldehydes and their nitro derivatives have herbicidal properties.

R. Wegler's manual "Chemie der"
Pflanzenachuz-und Schudli
ngsbekanpfungs-mittel”V
ol 5. Ser[nger, Berlin, Heilperg, New York 1977 (pp. 73-82 and 401
~407N) diphenyl ethers” (
Substituted phenoxybenzene derivatives) are taught for use as herbicides in the cultivation of soybean, corn and rice.

The fungicidal compositions of this invention contain as an active ingredient an effective amount (generally 0.00001-99) of at least one compound of the general formula (11) in a suitable inert solid or liquid carrier, diluent and/or It further contains an auxiliary agent.

The known compound of general formula (1) can be produced by a method known per se.

Item 4) 150 yen of anhydrous methanol 96.1.10.05 mol)
of 3-hydroxy-benzaldehyde and 2.8 g (0
0.06 mol) of potassium hydroxide under an inert atmosphere.
-Preparing the potassium salt of hydroxy-benzaldehyde. The methanol was distilled off from the homogeneous solution under water pump vacuum, leaving a residue of 2.5 g of potassium carbonate, 50-dimethyl sulfoxide and 13.7510.055 mol of 1
0 molar excess) 3.4.5-) Add lichloropenzotrifluoride. The reaction mixture was heated to 140-144°C.
The dimethyl sulfoxide is distilled off, 1507 of benzene is added to the residue, and the suspension is stirred for 1 hour. The solids insoluble in benzene are removed and the liquid f is evaporated under a water jet vacuum. The residue was diluted with methanol and isozolo-yanol.
1. Crystallize from the mixture.

In this way, 9 g of the target compound are obtained. Yield 60% + melting point 4
9-50°C, white crystals.

Empirical formula: C14H7C12F302 Molecular weight: 335 (calculated value) The mass spectrum contains fragments characteristic of compounds containing two base atoms.

Below margin M/e (r, 1.) = 336 C580) = F3C (C
1) 2C6H2QC6H4CHO335(370)=F
, C(Ct)2C6H2QC6H4CHO334(10
00)=F3C(Ct)2C6H2QC6H4CHO3
33(370);F3C(Ct)2C6H20C6H4
CH0271(520)=F3C(Ct)C6H2QC
6H5236 (560) to F3CC6H20C6H5I
In the R spectrum, the band appearing at 1690 cm-' is characteristic of the vibration of νCO of the formyl group.

This compound is prepared in a manner similar to that described above.

3.75.9 (0,011 mol) of 3-[(2,6-
dichloro-4-trifluoromethyl)-7enoxy]-
Benzaldehyde was dissolved in 8.6-dichloromethane and 5
．． 37! of acetic anhydride to which 2.4
m (0,034 mol) of 65% nitric acid and 2.4-98
The nitrated acid prepared from sulfuric acid and
Add dropwise while stirring thoroughly. Stirring is continued for 3 hours at room temperature after the addition has stopped, then the dichloromethane is removed under a water jet vacuum and the residue is poured into ice-cold water. The precipitated white powder material is filtered and dried. The dry compound of 2.7I is thus obtained in the form of white crystals. Yield 64%, melting point 117°C-119°C.

Empirical formula: C14H604Ct2F5 Molecular weight: 379 (calculated value) The mass spectrum of the product is as follows in each fragment:
The ratio of isotopes characteristic of compounds containing two chlorine atoms is shown.

m/e(r,i,) =381 (720)=F3C(
Ct)2C6H2QC6H3Q'JO)CHO379(
1000)=F3C(C4)2C5H2QC6H, (N
o) CHO349(650)=F3C(C4)2C6H
2QC6H, (0) CHO285 (320) = F2C (
Ct)2C6H20C6H4230(220)=F3C
(C4)2C6H20H Under the effect of internal circulation flow, aromatic aldehyde signatures appear at large δ values between 95 and 10.5 pprn. The aldehyde protons of the starting material are 9.85 ppm and the nitrated derivative gives a signature of 10.35 ppm due to the inductive effect.

The band appearing at 1690 cML in the IR spectrum is characteristic of the νCO vibration of the formyl group.

Spectroscopic data clearly demonstrate that no oxidation of formyl groups to carboxy groups occurs under the conditions of nitration.

(Compound AI) This compound is prepared similarly to the method described above.

The germicidal composition of this invention can be produced by a method known per se. Thus, the compositions of the present invention can be used, for example, as wet powder (WP), concentrated suspension (SC), water-miscible concentrated solution (SC), emulsifiable concentrate (EC), raised volume (ULV) compositions, Or foil.

In particular it may be a seed foil.

These compositions can be prepared by mixing the active ingredient(s) with a solid or liquid inert carrier, a solvent, and optionally further auxiliaries.

Said auxiliaries are, for example, surfactants (e.g. wetting agents, suspending agents, dispersing agents, emulsifiers), anti-caking agents, anti-caking agents,
Adhesion promoters, diffusion agents, penetration enhancers, substances that maintain or improve biological effectiveness, antifoaming agents, etc.

Suitable solid carriers and diluents include inert mineral materials such as clay, kaolin, china clay, attapulgite, montmorillonite, mica, pyrophyllite, bentonite, diatomaceous earth, highly dispersed synthetic silicic acid, calcium carbonate, calcined magnesium oxide, dolomite, gypsum, tricalcium phosphate, Fuller's earth, etc.).

Other suitable solid carriers and diluents include ground tobacco stalks, wood flour, and the like.

Suitable liquid carriers, diluents and solvents include water, organic solvents, mixtures of water and organic solvents, such as methanol, ethanol, n- or impropatol, diacetone alcohol, pendyl alcohol, iMJ)
tif ethylene glycol, triethylene glycol and propylene glycol: esters of said compounds, such as methyl cellosolve.

Butyl diglycol; ketones such as dimethyl ketone,
Methyl ethyl ketone, methyl imbutyl ketone, cyclopentanone, cyclohexanone, etc.; esters such as ethyl acetate, n-butyl acetate.

Isobutyl acetate, amyl acetate, isopropyl myristate, dioctyl phthalate, dihexyl phthalate, etc.; organic aliphatic or alicyclic hydrocarbons, such as t! 5-fin hydrocarbon, cyclohexane, kerosene, gasoline, benzene,
Toluene, xylene, tetralin, decalin, alkylbenzene mixtures: chlorinated hydrocarbons, such as trichloroethane, dichloromethane, chlorethylene, dichloromethane, chlorobenzene, etc.; lactones, e.g., tJ
fγ-butyrolactone etc.: lactams such as N-methylpyrrolidone, N-cyclohexylpyrrolidone; acid amides such as dimethylformamide; vegetable or animal oils 1 such as safflower seed oil, linseed oil.

Examples include rapeseed oil, olive oil, soybean oil, castor oil, and whale oil.

Suitable wetting agents, dispersing agents and emulsifying agents, and also reinforcing agents, anti-agglomerating agents and diffusing agents may be ionic or non-ionic. salts; sulfonates of aliphatic, aromatic or aliphatic-aromatic hydrocarbons; sulfates of alkyl, aryl and hyaralkyl alcohols; sulfonates of alkyl, aryl and aralkyl acids, esters and ethers) of phenols, cresols and naphthalenes; sulfonates of condensation products; sulfonated oils of vegetable or animal origin; alkyl, aryl and aralkyl phosphate esters; and salts formed of the above compounds with alkali metals or alkaline earth metals or organic bases (e.g. amines or salts with alkanolamines).

Preferred examples of the ionic surfactants are sodium lauryl sulfate, sodium 2-ethyl-hexyl sulfate: sodium salt of dodecylbenzenesulfonic acid, ethanolamine salt, jetanolamine salt, triethanolamine salt, and isozolobylamine salt: Sodium mono- and di-isopropyl naphthalene sulfonate: sodium naphthalene sulfonate, sodium salt of diisooctylsulfosuccinate; sodium xylene sulfonate: sodium and calcium salts of petroleum sulfonic acids: potash soap, potassium stearate, sodium stearate. , calcium stearate, aluminum stearate and magnesium stearate. The phosphoric esters may be in the form of ethers of polyglycols with phosphorylated alkylphenols or fatty alcohols and partially or completely neutralized forms of the above compounds with the abovementioned cations or organic bases. Anionic surfactants other than those mentioned above include disodium N-octadecyl-sulfosuccinate, sodium-N-
Oleyl-N-methyl-tauride and various polymer sulfonates.

Suitable nonionic wetting agents, dispersants and emulsifiers include 01G-
Ethers of ethylene oxide formed with 2° alcohols, e.g. stearyl? lyoxyethylene, oleylpolyoxyethylene: ethers formed with alkylphenols, e.g. tert-butylphenol,
polyglycol ethers formed with octylphenol or hanonylphenol; esters formed with organic acids, such as esters of stearic or myristic acid or hapholyethylene glycol oleate formed with polyethylene glycol; block polymers of ethylene oxide and propylene oxide. partial esters of fatty acids and oleic acid formed with hexitol anhydride, such as esters of sorbitol formed with oleic acid or stearic acid; condensation products of these compounds formed with ethylene oxide: t@
rt-glycols, e.g. 3,6-nomethyl-4-octyne-3,6-diol or 4,7-dimethyl-5-decyne-4,7-thiol: thioethers of polyethylene glycols, e.g. of dodecyl mercaptan formed with polyethylene glycol. It is ether.

Suitable adhesion improvers are alkaline earth metal soaps; salts of sulfosuccinates; natural and artificial water-soluble macromolecular substances such as casein, starch, vegetable gums, gum arabic, cellulose ethers, methylcellulose, hydroxyethylcellulose.

These include polyvinylpyrrolidone and polyvinyl alcohol. Suitable antifoaming agents are low molecular weight polyoxyethylene or polyoxypropylene block polymers (where the number of octyl, nonyl and phenyl polyoxyethylene/ethylene oxide units is 75); long chain alcohols, e.g. octyl Alcohol, etc.; special silicone oil, etc.

Suitable additives may further enhance the composition formed by colloidal
It can be added to make it compatible with various fertilizer systems from a chemical point of view.

The fungicidal composition of this invention may further contain known insecticides and/or nutritional ingredients.

Wet powders (wp) can be produced by mixing the active ingredients, auxiliaries and surfactants with carriers, milling and finally homogenizing. If liquid surfactants are used, they can also be applied by spraying onto solid organic or inorganic carriers or onto powder mixtures containing solid active ingredients. This method also applies to liquid active ingredients.

When using a liquid surfactant, it is also possible to suspend the previously ground solid component in an organic solvent containing the liquid surfactant. The suspension thus obtained can be dried, for example by spraying. Thus, emulsifying concentrates (EC), in which a surfactant is applied onto the surface of a solid active ingredient or solid element, incorporate the active ingredient or mixture thereof into a water-immiscible solvent in the presence of said surfactant. It can be produced by dissolving.

The emulsifiable concentrate thus obtained forms, together with water, a ready-to-use propellant that does not change spontaneously or under small mechanical effects during long-term storage. Water-miscible concentrated solutions can be prepared by dissolving the active ingredient in water or a water-miscible solvent in the presence of suitable water-miscible auxiliaries.

The desired concentration can be obtained by diluting with water.

Concentrated aqueous solutions of active ingredients can also be dispersed in water-immiscible solvents by appropriate selection of emulsifiers to obtain so-called phase inversion emulsions. By appropriate selection of solvents and surfactants, it is possible to produce compositions that form long-lasting dispersions (possibly molecular dispersions) when mixed with water or water-immiscible liquids. .

In the production of concentrated suspensions (SC), wetting agents and dispersing agents are combined with water (preferably ion-exchanged water) and anti-freeze components (
(preferably ethylene glycol or glycerin) with heating if necessary. To the solution thus obtained is added the solid (powdered or crystalline) active ingredient and optionally an anti-caking ingredient (eg Aerosil 200) under constant stirring. The particle-liquid phase system obtained in this way (
Adequate storage stability is obtained by milling the slurry in a wet mill (eg, a closed dyno mill) to the desired particle size, preferably 5 micrometers or less. After grinding, antifoaming agents or thickening agents (eg Kelden S) can be added under homogenizing conditions if desired. Additionally, the order of addition of the components can be varied or other components (eg, dyes) can be added as desired. In addition to the solid active ingredients,
It is also possible to use liquid water-immiscible or water-miscible active ingredients. Active ingredients with a low melting point can also be added in the melt in the presence or absence of emulsifiers.

The ULV condensate can be prepared in the same manner as the EC composition and, if so, in the same manner as the SC form.

Granules CG) suitable for direct use can be produced by extrusion, overlaying with granular carriers (for example crushed limestone) or by adsorption of the liquid component by carriers with adsorption capacity.

Granules (WC) suitable for atomization can be produced starting from the cast and/or SC forms by agglomeration techniques (for example in a dragino tank with a binder).

The active ingredient content of the fungicidal compositions of this invention is generally 0.00
It is 01 to 99 years old, preferably 0.01 to 95 years old.

Sprays or powders which can be used as such can be prepared by diluting the compositions described above with water or inert solid diluents in a known manner. The active ingredient content of ready-to-use compositions is generally 0.
．． 0001 to 10 weight ratio, preferably 0.01 to 5 weight ratio. Furthermore, before use, it is possible to use a plurality of propellants, each composition containing one active ingredient.

Seed foil is a preferred embodiment of the composition of this invention. Seed foils can be produced by incorporating the active ingredient into the foil or seed meal.

According to other features of the invention, there is provided a method for combating fungal plant diseases, which method comprises the general formula (1
Compositions of the main types of fungicides of this invention are disclosed below, in which an effective amount of at least one compound of the following is applied to plants, or fungal pests thereof, or the environment. Amounts are given in % by weight.

Concentrated Suspension (SC) Compound 16.4 40.0 Ethylene Glycol 10. Oqb Nonylphenyl polyglycol ether (to EO)
5.0% polysaccharide (xanthan gum) 0
．． 1% silicone oil 1.0% Water 43.9% Wet powder (wp) Compound AI 30.0% Highly dispersed silicic acid 15.0% White clay 20.0% Sodium lignosulfonate 5.0 Diatom ± 25.
0% Dispersant 5.0% Granules (G) Compound A3 5.0 powder limestone 69.0% Ethylene glycol 3.0% Calcium lignosulfonate 3.0% Highly dispersed silicic acid 5
, 0 water 15. θ% Dry powdered granules (WG) suitable for cough mist Compound A4 80.0 20% mixture of anionic emulsifier and nonionic emulsifier
Dispersant 7.0% White clay 8.0% Water 3.0% Compound A2 20.0% Xylene 50.0% Cyclohexanone 12.0% In'holon 1000% Poly(oxyethylene)sorbitol monooleate)
5.04 Sodium Ligrosulfonate 3.0 Multi-seeded foil (a) Manufacture of foil 80% RHODOVIOL 4/125 Polyvinyl alcohol of P type (4 viscosity of aqueous solution at 20°C
eP: 89 molar hydrolysis), 615I water (60°C
) while stirring. After dissolving, add 2(
l of R1 (ODOVIOL 30/20 m type polyvinyl alcohol (concentration of 4-width aqueous solution 30 cP:98 molar hydrolysis at 20 °C) and 20.9 g of glycerin are added and the mixture is stirred until a homogeneous solution is obtained. Stir vigorously. The solution is allowed to stand for 24 hours, thus removing bubbles. The solution is spread on a glass plate in a layer 0.5 mm thick by the stripping blade method and dried at room temperature.

The foil thus obtained is separated from the glass plate.

Thickness 0.05-0.06 mm (control foil).

Perform the method described in (a). However, 0.120.1i' of Compound A is added to the solution used to form the foil.
2 is suspended in 5- water and added. After removing the foam, shape the foil and dry it.

The foil thus obtained is the foil of (a) and 1(E
It contains 1000 ppm of Compound 2 as an active ingredient.

Instead of compound Haruka 2 as the active ingredient, 0,01201 suspended in water of 5-! Compound A4 can also be used.

The active ingredient content of the foil amounts to 100 ppm.

Seed coating, spraying and powder application are the most widely used methods for chemical protection of plants to eliminate or control fungal diseases. The compositions of the invention comprising fungicidally active ingredients are preferably applied to infected parts of the host plant or to the environment.

The epithelium can be used to prepare seeds that are not susceptible to infection and to control soil fungi that infect the seeds. Seeds and seedlings are produced in the first case by filamentous conidial fungi [e.g. Fusarium 6 Chlaminearum (F
ugarium graminearum), Fusarium moniliforme (Fugarium monili-
forme ), and Nlgroipora eryz in maize cultivation.
ae ), as well as Rhizoctonia (Rjzoctoni
a), P+nicillum and Helminthioaporu
m) strains belonging to the genus].

The fungicidal composition of this invention can be used against the following fungi.

(a) Family Monliaceae (b) Family Dsmatiaceae (szinonim) (e) Family Tuberculari
In the following example, the effectiveness of the composition of the invention is compared with that of the known fungicide 1,2,5,6-titrahydro N-(trichloromethylthio)-phthalimide (cabutane).

A potato nutrient agar medium containing part 2 glucose was injected into a vetriglate (i]! diameter 100 m+).

Then, an agar plate is prepared by solidifying the medium.

An emulsifiable concentrate containing 20 parts of the active ingredient is diluted to the desired concentration. A suspension containing a large number of spores of the test organism is prepared at the following concentration: That is, when a drop of spore suspension is placed on a microscope slide, at 100-160x magnification, 925 spores per field are averaged over 5-10 fields.
Bring to a concentration where ~30 spores appear.

The spore suspension 1- thus obtained is transferred to a pipet) 1
- and the mixture is allowed to stand for 30 minutes and applied to the agar plate. Inoculate the bacteria until vigorous growth begins. Results are evaluated by comparing the growth of treated samples to that of controls. According to the following scale.

1; No colony growth, 0% vs. control) 2 = Colony grower (10% vs. control) 3 = Moderate colony growth (50% vs. control) 4; Colony grower ( 100% vs. control) The results are summarized in Table 1.

Blank Example 2 Sterilization test in liquid culture The active ingredient is diluted to a desired concentration in a 20-coat malt nutrient medium, and the medium is first inoculated with test bacteria.

The degree of inhibition of colony growth is determined after 7 days of incubation. The concentrations required for complete growth inhibition are shown in Table 2.

Below is a blank example 3 Plant toxicity test in a glass room A growth plate with a surface area of 1.64 dm2 is filled with sandy soil, and 20 to 30 plants are placed in duplicate at a depth of 0.5 to 1.0 mm (plant types). Ten days after the plants germinate, a ready-to-use spray prepared from an emulsifying 0 degree product with an active ingredient concentration of 20% is applied using a laboratory sprayer to It is applied to seedlings at a concentration of 9 klil/ha of active ingredient. The extent of plant damage (C%) is determined 10 days after spraying.

The results are summarized in Table 3.

Seed coating is carried out using a 400 #/* concentrated suspension of the protective active ingredient as per the margin below and cabtan of type 5CIWP as standard.
0.1.0.25, 0.5.1.0, and 2.0IAe
The active ingredients of Merit 5oya
Use type of seeds KM. Germination and fungal infection rates are determined in the laboratory 10 days after seed coating.

In the farm experiment, on April 20th, the depth of 4-5 cm,
Sow at a plant spacing of 5 cIIL and a row spacing of 50 cR.

When the soybean plant height reaches 10-12 cIrL, the budded plants are counted and expressed as a negative relative to the untreated control.

The results are shown in Table 4.

Below is a blank example 5. In the small membrane compartment (10 mm) against 7delium infection of autumn wheat ears, autumn wheat [Jubilesinage 7 (
Four series of experiments were conducted with Jublejnaja) K. A ready-to-use spray was prepared from a 20-inch concentrated emulsion of compounds A1-4.

And 1.2. and 3kf/ha active ingredient amount and 50
Spray at the end of the harvest at a water supply rate of 0 J/ha. Evaluate 200 panicles per plot 12 days after spraying
Determine Fusarium infection in the panicles.

After harvesting, measure the wheat yield (heavy harvest) of each plot, and
Determine the total and internal Fusarium infection of the seedlings as an average of 00 seeds/plot samples. Table 5 summarizes the results as the average of four replicate experiments.

Margin below Table 5 1 0.86 12.2 8.8 5.67] 2 0
．． 54 9.6 7.6 5.883 0.48 5.
4 4.4 6.031 0.63 13.4 10.
2 6.112 2 0.33 10.2 8.1 5
．． 873 0.20 6.0 5.4 5.841 1
．． 09 11.4 9.4 5.623 2 0.84
10.6 8.0 5.663 0.67 9.8
7.2 5.731 0.98 9.9 6.8 5.
784 2 0.68 9.2 6.4 5.823
0.52 8.0 6.1. 5.87 Continuation of page 1 @ Inventor Felenk Bihari 0 Inventor Mihalyi Pretojak @ Inventor Anti Dourko 0 Inventor Istvan Cyronya 0 Inventor Istvan Majyary 0 Inventor Shudit Timar @ Inventor Peter Bohus O Inventor Ras-Utsa Wolgarhi, Dounaharasti, Duna Uzza 9 Hungarian State, Romai Titzenhalom, Bypest, Rayuk Ras-Utsa (9) Hungarian IJ-Country,
Eldo, Diosdi Uzza 27 Hungary,
Romai Fukkatto, Budapest, Adei Yi,
Utsa 119-121 Hungarian State, Romai Tičenęci, Budapest, Bitpar Utsa,
7/English - Hungary, Godr, Strömfeldny, Cetany 16 Hungary, Romai Titzengatto, Budapest, Zsolna Utsza 25 Hungary, Romai Kirenc, Budapest, Napfęnyi Utsa n Hungary, Romai Egyi,... budapest, sena
Chill 1/Technical procedure amendment (method) May 1985 β' Commissioner of the Japan Patent Office Gakudono Shiga 1, Indication of the case H 1985 Patent Application No. 5130 2, Name of the invention Sterilizing composition and its How to use 3, Relationship with the case of the person making the amendment Patent applicant name Pudavesti Beziimbek 4, agent 6, subject of amendment (1) Application Address of Mar, Peter Bohus and Gilaslowal)
Column (2) Specification 7, Contents of amendment (1) As attached (2) Engraving of the description (no change in content) 8, List of attached documents (1) Request for correction 1 copy (2) Engraving of the specification 1 letter

Claims (1)

[Claims] 1. At least one of the N4 forms of phenoxybenzaldehyde represented by the following general formula (1) (wherein, X is hydrogen or chlorine, and Y is hydrogen or a nitro group) 1. A fungicidal composition comprising an effective amount of active ingredients of the following types together with at least one auxiliary agent or diluent. 2. The fungicidal composition according to claim 1, comprising 3 [(2-chloro-4-aldehyde) as an active ingredient. 3. 3-CC2,6-dichloro-4-trifluoro- as an active ingredient. 2. A fungicidal composition according to claim 1, comprising methyl)-phenoxy]-pensaldehyde. 4. The fungicidal composition according to claim 1, comprising 5-[(2-chloro-4-trifluoromethyl)-7enoxy]-2-nitrobenzaldehyde as the active ingredient. 5. 5-C(2,6-dichloro-4-
2. A fungicidal composition as claimed in claim 1, comprising 2-nitrobenzaldehyde (trifluoromethyl)-phenoxycou-2-nitrobenzaldehyde. 6. Effectiveness of an active ingredient consisting of at least one phenoxybenzaldehyde derivative represented by the following general formula (1) Y (wherein X is hydrogen or chlorine, and Y is hydrogen or a nitro group) 1. A method for exterminating fungal plant diseases, which comprises applying a large amount to plants, their growth spaces or environments.