DD261304A5 - PESTICIDES AND METHODS FOR THE CONTROL OF PAHTOGENIC FUNGI SCHAEDLINGES U./O. weeds - Google Patents

Abstract

The invention relates to a pesticidal agent and a method for controlling pathogenic fungi and / or weeds. According to the invention, the agent contains as active ingredient at least one azomethine derivative of the general formula (I) in which X1 is hydrogen or nitro, X2 is C1-18 alkyl, with the proviso that if X1 is nitro, X2 is C7-18 alkyl, or X 2 is furthermore C 2-6 hydroxyalkyl, or C 2-6 mercaptoalkyl, or C 2-6 aminoalkyl, or C 3-6 alkenyl or C 3-6 alkynyl or phenyl, or a certain substituted phenyl or aralkyl, C 1-6 alkylphenyl or further, in the claim means specified groups. Formula I

Description

Field of application of the invention

The invention relates to a pesticidal composition and a method for controlling pathogenic fungi pests and / or weeds.

Characteristic of the known state of the art

Unwanted plants (weeds) and fungi pests of crops cause serious damage in agriculture by reducing crop yield. To increase the efficacy of agricultural production, pesticides are used against the weeds and fungi pests which destroy these pests or at least reduce their growth. Although such agents are already known in very large numbers, there is still a need for improved, especially the environment as little as possible polluting pesticides.

Object of the invention

The invention should now provide improved pesticidal agents.

Explanation of the essence of the invention

It has been found that novel compounds of general formula (I) wherein X _{1 is} hydrogen or nitro;

X _{2 is} Ci_i8-alkyl, with the proviso that when X _{1 is} nitro, X _{2 is} C ₇ _i 8 -alkyl, or else X _{2 is} further

C ₂ -6-hydroxyalkyl, or

C ₂ _6-mercaptoalkyl, or

C ₂ _e-aminoalkyi, or

C3_e-Alkenyl or

C ₃ ^ alkynyl, or

Phenyl, or

represents substituted phenyl of the general formula V, in which X _{3 is} identical or different and represents C 1-5 -alkylTrifluoromethyl, hydroxyl, mercapto, nitro, amino or halogen,

preferably chlorine, and η is 1,2 or 3; or

Aralkyl, Ci_6-alkyl-phenyl or a group of the general sub-formula (Vl), wherein X _{1 has} the above meaning and m is 2,3,4,5 or 6,

have valuable pesticidal (herbicidal and / or fungicidal) properties.

The invention thus relates to a pesticidal composition containing as active ingredient at least one new compound of general formula (I) wherein X ₁ and X _{2 are} as defined above, and suitable solid and / or liquid and, if desired, other known pesticidal active compounds.

The novel compounds of general formula (I) are azomethine derivatives. They can be prepared by reacting a substituted benzaldehyde of the general formula (II) in which Xi has the above meaning, or an acetal or acetate thereof, optionally in the presence of an inert solvent and / or a catalyst, at a temperature between ⁰ ° C. and the boiling point of the reaction mixture with a primary amine of the general formula (II), wherein X _{2 is} as defined above, and then the resulting novel compound of the general formula (I) from the reaction mixture in a known manner.

The condensation of primary amines with carbonyl compounds was first investigated by H.Schiff (Ann. Chem., 131, 118 [1964]). In general, the condensation products Schiff bases are called. A detailed composition of this condensation reaction has been described by M. M. Sprung (Chem. Rev. 26, 297 [1940]) and R.W. Rev. 63,489 [1963]).

The phenoxybenzaldehydes of the general formula (II) used in the preparation of the novel compounds of the general formula (I) are known (US Pat. No. 4,306,900; DE-OS 3,017,795). The primary amines of the general formula (II) used as starting material are likewise known.

Starting from the substituted 5-phenoxy-2-nitrobenzaldehydes, several new types of compounds have already been prepared, e.g. substituted phenoxy-benzaldehydacetale (EP-PS 0064658) and diacetates (DE-OS 3044810), substituted phenoxycinnamic acid derivatives (EP-PS 0053321) and substituted phenoxy-benzaldehyde oxime and -carboxime (DE-OS 3017795).

EP-PA 0034012 discloses compounds having herbicidal activity, which may also be 5 - [(2-chloro-or-2,6-dichloro-4-trifluoromethyl) -phenoxy] -2-nitro-benzaldehyde-Ci_g-alkylimines , However, only the 5 - [(2-chloro-4-trifluoromethyl) phenoxy] -2-nitrobenzaldehyde tert.-butylimine is described from these compounds, but nothing has been disclosed about its herbicidal action.

It has already been found that the novel compounds of the general formula (I) show very effective pesticidal activity.

The compounds of general formula (I) can be prepared by reacting 3 - [(2-chloro-4-trifluoromethyl) phenoxy] benzaldehyde or 5 - [(2-chloro-4-trifluoromethyl) phenoxy] -2-nitrobenzaldehyde (Compounds of the general formula II) and primary amines of the general formula (III) are produced

 The compounds of the general formula (I) can be prepared by methods known per se.

a) An acetal or an acetate of a phenoxy-benzaldehyde of the general formula (II) is reacted with a primary amine in the presence of an inert solvent at the boiling point of the reaction mixture. The reaction may also be carried out in the absence of a solvent while distilling off the alkanol or carboxylic acid formed.

b) It is advantageous to proceed by reacting a phenoxy-benzaldehyde of the general formula (II) in the presence or absence of an inert solvent, preferably in the presence of a catalyst, at a temperature between ^{0 0} C and the boiling point of the reaction mixture with a primary amine of the general formula (III).

As the reaction medium, suitable inert solvents (e.g., methanol, ethanol, propanols, benzene, toluene, dichloromethane, chloroform, carbon tetrachloride, etc.) can be used. Optionally, the water formed in the reaction may be removed using an azeotroping solvent.

The condensation reaction can be carried out in the presence of a mineral acid or Lewis acid as a catalyst. For this purpose, e.g. Sulfuric acid, hydrogen chloride, boron trifluoride etherate, zinc chloride, phosphorus oxychloride, etc. However, the reaction can be successfully carried out even in the absence of a catalyst.

In the process, the aldehyde and the primary amine can be used in an equimolar amount, however, one of the reaction components (preferably the primary amine) can also be used in an excess.

The novel compounds of the general formula (I) can be isolated from the reaction mixture by methods known per se. The reaction mixture may, for. B. cooled and filtered. The product obtained may, if desired, be purified by recrystallization from a suitable solvent (e.g., methanol, ethanol, isopropanol, petroleum ether, etc.).

One group of the new compounds of general formula (I) has herbicidal and another group fungicidal properties. Some compounds of the general formula (I) exert both effects and are at the same time herbicidal and fungicidal (pesticidal action).

The compounds of general formula (I) are not phytotoxic to crops (eg corn, sunflower, pea, etc.). This absence of phytotoxicity (selectivity) is particularly important in the case of pesticidal (herbicidal and fungicidal) compounds, because the fungicidal active ingredients, which also have herbicidal activity, are generally phytotoxic to crop plants. In the new compounds according to the invention, these disadvantages do not occur

The following compounds of general formula (I) exert particularly strong herbicidal activity:

{5 - [(2-chloro-4-trifluoromethyl) -phenoxy] -2-nitrobenzylidene} -aniline and

{5 - [(2-chloro-4-trifluoromethyl) phenoxy] -2-nitro-benzylidene} -3-nitro-aniline.

The following compounds of the general formula (I) are particularly active herbicidally active compounds:

{5 - [(2-Chloro-4-trifluoromethyl) -phenoxy] -2-nitro-benzylidene} -3-trifluoromethyl-aniline, {5 - [(2-chloro-4-trifluoromethyl) -phenoxy] -2-nitro benzylidene-3,4-dichloroaniline, {5 - [(2-chloro-4-trifluoromethyl) -phenoxy] -2-nitro-benzylidene} -2-chloro-5-trifluoromethyl-aniline.

From the compounds of the general formula (I), the following derivatives are distinguished by their fungicidal activity:

bis {5- [2- (chloro-4-trifluoromethyl) phenoxy] -2-nitrobenzaldehyde} -ethylenediimine, {5 - [(2-chloro-4-trifluoromethyl) phenoxy] -2-nitrobenzylidene }-aniline,

{5 - [(2-Chloro-4-trifluoromethyl) -phenoxy] -2-nitro-benzylidene} -2-chloro-5-trifluoromethyl-aniline, {5 - [(2-chloro-4-trifluoromethyl) -phenoxy] 2-nitrobenzylidene} -2-hydroxyaniline and {3 - [(2-chloro-4-trifluoromethyl) phenoxy] benzylidene} -3,4-dichloroaniline.

The following compounds of the general formula (I) are particularly valuable fungicidal active compounds:

{3 - [(2-chloro-4-trifluoromethyl) -phenoxy] -benzylidene} -3-trifluoromethyl-aniline,

{3 - [(2-Chloro-4-trifluoromethyl) -phenoxy] -benzylidene} -2-chloro-5-trifluoromethyl-aniline, 5 - [(2-chloro-4-trifluoromethyl) -phenoxy] -2-nitro benzaldehydpropargylimin,

{5 - [(2-Chloro-4-trifluoromethyl) -phenoxy] -2-nitro-benzylidene} -4-hydroxy-aniline, {5 - [(2-chloro-4-trifluoromethyl) -phenoxy] -2-nitro benzylidene} -3,4-dichloro-aniline.

The following compounds of general formula (I) are distinguished by their pesticidal (herbicidal and fungicidal) action

{5 - [(2-chloro-4-trifluoromethyl) phenoxy] -2-nitro-benzylidene} aniline,

{5 - [(2-Chloro-4-trifluoromethyl) -phenoxy] -2-nitro-benzylidene} -2-chloro-5-trifluorometh-aniline and {5 - [(2-chloro-4-trifluoromethyl) - phenoxy] -2-nitro-benzylidene} -3,4-dichloro-aniline.

The herbicidal compositions of the invention may be used in the pre-seed, pre-emergence and post-emergence processes. The drug box can be varied within wide limits depending on various factors (eg, the mode of application, the degree of weed formation, the genus and species of the crop, the soil type, the meteorological conditions, etc.). Care must be taken that the phytotoxic limit shown against crops should not be exceeded. After our experiments, the active substance dose is generally 0.1-10.0 kg · ha ^-1 , preferably 0.2-3.0 kg · ha ^-1 .

The active compounds of the general formula (I) according to the invention can advantageously be sprayed in the form of a spray mixture in a can of 100-1 200 l ha ^-1 , preferably 300-6001 l ha ^-1 , at a pressure of 2.5-3.5 bar ,

In agriculture and horticulture, pickling, spraying and dusts are most commonly used to control plant pests and fungi infections. The pesticidal agents of the invention - e.g. Pickling agents, spray liquors, dusts, etc. - can of course be applied to the plant or a part thereof or to the environment of the same, where the source of infection develops or the pest spreads.

For the production of infection-free seeds, the pickling process is used whereby the fungi, which infect the seed from the direction of the soil, are fought.

Against Fungi, which endanger the foliage and the fruits of the plants, the plant is sprayed and pollinated.

The active compounds used according to the invention can be used in an amount of 0.5-3.0 kg.t- ^1, preferably 1.0-2.0 kg, t- ¹ for seed dressing. For spraying and dusting an active substance dose of 0.1-5.0 kg ha " ¹ - preferably 0.5-3.0 kg ·" ¹ - used.

The active compounds of the general formula (I) according to the invention can be completed in conventional forms, for. In the form of wettable sprayable powders (WP), suspension concentrates (SC), water-mixable solution concentrates (SL), emulsifiable concentrates (EC), water-insoluble granules (S) or dusts (DP), oily suspension concentrates (FO), Foils, preferably seed foils. The active ingredients can also be used in the form of ULV compositions. In these pesticidal compositions according to the invention, the active ingredient is mixed with solid or liquid inert carriers or diluents and optionally with excipients.

The above adjuvants may, for. Surfactants, such as wetting, suspending, dispersing, emulsifying, coagulation or anti-coagulants, adhesives, anti-drainage and anti-penetration agents, biological effectiveness maintaining or enhancing agents, antifoaming agents, etc.

As suitable solid carriers and diluents, inactive minerals, e.g. B. various kaolin species, kaolin, attapulgite, montmorillonite, mica schist, pyrofillite, bentonite, diatomaceous earth or fumed synthetic silica, calcium carbonate, calsinated magnesia, dolomite, gypsum, tricalcium phosphate, Fuller's earth, etc. are used. As other suitable carriers, ground tobacco leaf stalks, wood flour, etc. may be mentioned.

Suitable liquid diluents and solvents are e.g. the following liquids: water, organic solvents, mixtures of organic solvents and / or water, such as methanol, ethanol, n-propanol, isopropanol, diacetone alcohol, benzyl alcohol, and esters thereof, such as methyl cellosolve; Ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclopentanone, cyclohexanone, etc .; Esters such as ethyl acetate, n-butyl acetate, isobutyl acetate, amyl acetate, isopropylmiristate, dioctyl phthalate, dihexyl phthalate, etc .; aromatic aliphatic and alicyclic hydrocarbons, such as paraffin hydrocarbons, cyclohexane, kerosene, gasoline, benzene, toluene, xylenes, tetralin, decalin, mixtures of alkylbenzenes; chlorinated hydrocarbons such as trichloroethane, dichloromethane, perchlorethylene, dichloropropane, chlorobenzene, etc .; Lactones such as γ-butyrolactone, etc .; Lactams, such as N-methylpyrrolidone, N-cyclohexylpyrrolidone; Acid amides, e.g. Dimethylformamide, etc .; vegetable and animal oils, such as sunflower seed oil, linseed oil, rapeseed oil, olive oil, soybean oil, castor oil, whale oil, etc.

The suitable wetting, dispersing, emulsifying, adhesive, anti-aggregating and anti-drainage agents may be ionic or non-ionic in nature. As ionic surfactants, for. For example, the following compounds find use: salts of various saturated and unsaturated carboxylic acids; Sulfonates of aliphatic, aromatic or araliphatic hydrocarbons; Sulfates of alkyl, aryl or aralkyl alcohols; Sulfonates of alkyl, aryl or aralkyl acids, esters or ethers; Sulfonates of condensation products of phenol, cresol or naphthalene; sulfated vegetable or animal oils; Alkyl, aryl or Aralkylphosphatester or formed with alkali or alkaline earth metals or organic bases salts of the above compounds, for. B. formed with different amines or alkanolamines salts. The following compounds are particularly suitable for this purpose: sodium lauryl sulfate, sodium 2-ethylhexyl sulfate, the sodium, ethanolamine, diethanolamine, triethanolamine, isopropylamine salt of dodecylbenzenesulfonic acid; Sodium mono- and diisopropylaphthalenesulfonate; sodium naphthalene; Sodium diisooctyl sulfosuccinate, sodium xylene sulfonate, sodium or calcium salt of petroleum sulfonic acid; Potassium soaps; Potassium, sodium, calcium, aluminum or magnesium stearate, etc. The phosphate esters may be polyglycol-derived ethers of phosphated alkylphenols or fatty alcohols, or the forms thereof completely or partially neutralized with the above cations or organic bases. Disodium N-octadecylsulfosuccinate, sodium N-oleyl-N-methyl-tauride and the various lignosulfonates can furthermore be used as anionic surface-active agents. ·

Suitable nonionic wetting, dispersing and emulsifying agents are, for. As the following compounds: ether of ethylene oxide formed with Cio-2o-alcohols, such as. Stearyl-poly (oxyethylene), oleyl-poly (oxyethylene); Aethers formed with alkylphenols, e.g. tert.butyl, octyl or nonylphenol-formed poly (glycol ether); esters formed with various organic acids, e.g. B. formed with stearic acid or miristic acid esters of polyethylene glycol or Polyäthylenglykololeats etc .; Ethylene oxide and propylene oxide block polymers; with hexane anhydrides formed partial esters of oleic acids, eg. B. esters of sorbitol formed with oleic acid or stearic acid; ethylene oxide-formed condensation products of the above compounds; tertiary glycols z. 3,6-dimethyl-4-octyne-3,6-diol or 4,7-dimethyl-5-decyne-4,7-diol; Polyethylene glycol thioether, e.g. B. formed with polyethylene glycol ether of Dodecylmercaptans etc.

As an aid z. As alkaline earth metal soaps, Sulfobernsteinsäureestersalze, natural or synthetic water-soluble macromolecules, such as casein, starch, cellulose ethers, methyl cellulose, hydroxy cellulose, poly (vinyl pyrrolidone), poly (vinyl alcohol), etc. find use. Suitable foam control agents are in the first place low poly (oxyethylene) -, poly (oxypropylene) -, block polymers, wherein the number of octyl, nonyl and phenyl-poly (oxyäthylen) Äthylenoxyd units> 5, long-chain alcohols, eg. As octyl alcohol, special silicone oils, etc.

Using suitable additives, the compositions of the invention with various fertilizers can be made colloid-chemically compatible.

The agents of the invention may, if necessary, contain known pesticidal agents and / or nutrients. The wettable powders (WP) can be prepared by mixing the active agent (s), auxiliary agent (s) and surfactant (s) with the carriers, and finally grinding the resulting mixture homogenized. Liquid surfactants may be applied to the solid organic or inorganic carriers or to the solid drug-containing powder mix e.g. be applied by spraying. In the case of liquid active substances one can proceed in a similar way. In the case of liquid surfactants, by another method, the pre-ground solid components may be suspended in an organic solvent containing the liquid surfactant (s). In this way, the surfactant may be applied to the surface of the solid active or solid support.

A suitable for the formation of aqueous emulsions, self-emuigating liquid so-called. Emulsifiable concentrate (EC) - can be prepared by dissolving the active ingredient or the active ingredient mixture in the presence of one of the surfactants listed above in a water-immiscible solvent. The emulsifiable concentrate thus obtained forms, either spontaneously or under slight mechanical action, a spray emulsion which remains unchanged even after prolonged storage.

A water-miscible solution concentrate (SL) can be prepared by dissolving the active ingredient and the appropriate water-soluble excipients in water and / or a water-miscible organic solvent. By dilution with water, spray liquors of the desired concentration can be prepared. By suitable selection of the emulsifier, the aqueous solution concentrate of the active ingredient can be dispersed in a water-immiscible liquid: in this way, a so-called "reverse emulsion" is obtained Mixing with water or liquids immiscible with water, forming such - if necessary, molecular - dispersed phases, which do not change even after prolonged storage.

For the preparation of the suspension concentrates (SC), the wetting and dispersing agents, if necessary with heating, are dissolved in a mixture of water (expediently ion-exchanged water) and an antifreeze component (advantageously ethylene glycol or glycerol). The solid (powdered or crystalline) active ingredients and, if necessary, the anti-aggregating agents (eg Aerosil 200) are added to the resulting solution while stirring continuously.

The liquid phase (suspension) containing solid particles thus obtained is comminuted to the desired particle size by means of a wet grinding device (for example in a closed Dyno mill). The particle size is at most 5 pm in order to ensure good storage stability. After comminution, if necessary, the foam control agent or compaction agent (e.g., Kelzan S) is blended during the homogenization. The order of addition of the components can also be changed or, if necessary, further components (eg dyes) can also be added.

In addition to the solid active ingredient can also be used as a combination partner liquid, water-immiscible or water-miscible agents. Low-melting solid agents may also be introduced in the form of a melt in the absence or presence of emulsifying agents.

ULV preparations can be prepared in a manner similar to the EC or SC agents.

Granules (G) suitable for immediate use can be prepared by extrusion or coating using self-granular carriers (e.g., ground limestone) or by absorbing a liquid component on a high sorption capacity support.

The granules (WG) which can be used for spraying can be prepared from WP and / or SC preparations by means of an agglomeration technology, e.g. B. in a coating vessel using binders can be prepared.

The spray liquors or dusts suitable for immediate use can be prepared from the above compositions by dilution with water or an inert solid diluent in a manner known per se. The active ingredient content of these spray liquors or dusting powders is generally below 5% by weight and is advantageously 0.01-3% by weight. It is also possible to proceed by mixing a plurality of sprays each containing one active ingredient before use.

Further details of the present invention can be found in the following examples, without limiting the scope of protection to these examples.

embodiments

The preparation of the compound according to the invention is described in Examples 1-24. Examples AD disclose the preparation of reference compounds of similar structure (Table 1). The ¹ H NMR spectroscopic values given in some examples use the name given on the general formula IV. The designation of the position of some protons differs from that of nomenclature; However, the method used here allows a uniform spectroscopic evaluation.

The spectroscopic ¹ H-NMR data appearing in the examples relate to the X ₂ -TeU of the general formula (I). The protons of the diphenyl ether scaffold appear due to the weakly inductive effect of X ₂ -TeUs at an identical chemical shift _value : δ _Η3 = 7.75 (d, J ₃₅ = 3Hz), 5 _Hs = 7.55 (dd, J ₅₆ = 9Hz) , δ _Ηβ = 7.12 (d, J ₆ 5 = 9Hz), 5h ₂ = 7.60 (d, J _{2, 6.} = 3Hz), δ _Ηβ . = 8.05 (d, J ₅ ^ = 8 Hz), 5 _Hr = 6.95ppm (dd, J ₆ ^ = 8Hz, J ₆ ^ = 3Hz).

In the spectrum of compounds disappears the characteristic for the formyl group vC = O = 1700cm " ¹ band, for which appears the ^ C = N = 1 580cm"'band. The characteristic of the diphenyl ethers is 1Z ₃₃ COC = 1 270 cm " ¹ band appears at about V ₅ COC = 1120 cm ^-1 .

Table 1

Substituent definition and melting point of the active ingredients described in the examples

Active ingredient X ₂ Χι melting point

Example No. (boiling point) ⁰ C

55-56 38-41 63 136-138

142-144

81-83

62-66

48-52

91-93

92-94 102-103

88-89 139-142

1 - (CH ₂ J ₇ CH ₃ NO ₂ NO ₂ 2 - (CH ₂ CH = CH ₂ NO ₂ NO ₂ 3 -CH ₂ C = CH NO ₂ NO ₂ 4 -CH ₂ CH ₂ N = CH (NO ₂ ) C ₆ H ₃ I DC ₆ H ₃ -NO ₂ NO ₂ 2-CM-CF ₃ NO ₂ "5 - (CH ₂ J ₆ N = CH (NO ₂ ) C ₆ H ₃ OC ₆ H ₃ - NO ₂ NO ₂ 2-CI-4-CF ₃ NO ₂ 6 - (CH ₂ J ₂ OH NO ₂ 7 -CH ₂ C ₆ Hg 8th -CH (CH ₃ ) C ₆ H ₅ 9 -C ₆ H ₅ 10 -C ₆ H ₄ -3-CF ₃ 11 -C ₆ Hr-3,4-CI ₂ 12 -C6H3-2-Cl-5-CF3 13 C ₆ H ₄ -2-OH

active substance X ₂ xl melting point Example no. (Boiling point) ⁰ C 14 -C6H4-4-OH NO ₂ 91-93 15 C ₆ H ₄ -3-NO ₂ NO ₂ 122-114 16 -C ₆ H ₃ ^ -CH ₃ -S- (C ₂ H ₅ ) NO ₂ 93-94 17 C ₆ H ₃ -2,6- {C ₂ H ₅ ) ₂ NO ₂ 64-65 18 -CH (CH ₃ I ₂ H (135-150 / 1) 19 -CH2CH-CH2 H (105-135 / 1) 20 - CqH ^ H oil 21 -CqH 4-3 ~ - CF3 H 94-96 22 -C6H3-2-Cl-5-CF3 H 85-90 23 -C ₆ H ₃ -3,4-CI ₂ H oil 24 -CH ₂ CH ₂ N = CHC ₆ H ₄ OC ₆ H ₃ - H oil 2-CI-H-CF ₃ A -CH ₂ CH ₃ NO ₂ 61-63 B - (CH ₂ ) ₂ CH ₃ NO ₂ 60-63 C - (CH (CH ₃ J ₂ NO ₂ 41 ^ 14 D - (CH ₂ J ₃ CH ₃ NO ₂ 42-43

example 1

5 - [(2-Chloro-4-trifluoromethyl) -phenoxy] -2-nitrobenzaldehyde-octylimine (Compound No. 1) 5 g (0.0145 mol) of 5 - [(2-chloro-4-trifluoromethyl) -phenoxy ] -2-nitro-benzaldehyde and 1.9 g (0.0145 mol) of n-octylamine are dissolved in 15 ml of isopropanol. The solution is refluxed for half an hour and then cooled. There are obtained 4.6 g of the title compounds, yield 69%, molecular weight 456. The dull yellow crystals melt at 55-56 ⁰ C.

Characteristic fragments of the mass spectrum: m / e (ri) = 456 (520) ^ F ₃ C (CI) C ₆ H ₃ OC ₆ H ₃ (NO ₂ (CHN (CH ₂ ) ₇ CH ₃

- 439 (820) = F ₃ C (CI) C ₆ H ₃ OC ₆ H ₃ (NO) CN (CH ₂ ) ₇ CH ₃

327 (900) = F ₃ C (CI) C ₆ H ₃ OC ₆ H ₃ NO ₂

323 (92o) = F ₃ C (CI) C ₆ H ₃ ¹ H-NMR (CDCI _3): 5 _CH = 8.62, 5 _HC h ₂ = 3.6 (tr, J = 7 Hz), 5 _C h ₂ = 1.23-1.88, 5 _C h ₃ = 0.7 ppm (tr. J = 7Hz).

Example 2

5 - [(2-Chloro-4-trifluoromethyl) -phenoxy] -2-nitro-benzaldehyde allylimine (Compound No. 2) To 6.9 g (0.02 mol) of 5 - [(2-chloro-4-trifluoromethyl ) -phenoxy] -2-nitro-benzaldehyde, 1.14g (0.02 mole) of allylamine are added and the reaction is heated for one hour on a hot water bath. After cooling, the oily residue is crystallized in 10 ml of ethanol. There are 4.84 g of the title compounds, yield 63%, molecular weight 384. The yellowish brown photosensitive crystals melt at 38-41 ° C.

Characteristic fragments of the measurement spectrum:

m / s (ri) = 384 (20O) = F ₃ C (CI) C ₆ H ₃ OC ₆ H ₃ (NO ₂ ) CHNCh ₂ CHCH ₂

367 (370) = F ₃ C (CI) C ₆ H ₃ OC ₆ H ₃ (NO) CNCH ₂ CHCh ₂

343 (570) = F ₃ C (CI) C ₆ H ₃ OC ₆ H ₃ (NO ₂ ) CHN 41 (100O) = CH ₂ CHCH ₂ ¹ H-NMR (CDCl ₃ ): 5 _CH = 8.7 5 _CHl = 4.25 (mp) 5 _NC h ₂ = 5-5.27 (mp), Ö _CH = 6.0ppm (mp).

Example 3

5 - [(2-Chloro-4-trifluoromethyl) -phenoxy] -2-nitrobenzaldehyde-propargylimine (Compound No. 3) The procedure is as in Example 2, with the difference that the propargylamine is used instead of allylamine. There are obtained 8.9 g of the title compound, yield 78%, molecular weight 382. The body-colored crystals melt

63 ° C. ·

Characteristic fragments of the mass spectrum:

m / e (ri) = 382 (330) = F ₃ C (CI) C ₆ H ₃ OC ₆ H ₃ (NO ₂ ) CHNCh ₂ CCH

365 (410) = F ₃ C (CI) C ₆ H ₃ OC ₆ H ₃ (NO) CNCH ₂ CCh

343 (150) = F ₃ C (CI) C ₆ H ₃ OC ₆ H ₃ (NO ₂ ) CHN

261 (260) = F ₃ C (CI) C ₆ H ₃ OC ₆ H ₃ CN

223 (44O) = C ₆ H ₃ OC ₆ H ₂ NO

54 (100O) = HNCH ₂ CCH ¹ H-NMR (CDCl ₃ ): 5 _CH = 8.0 5 _NC h ₂ = 4.45 (d, J = 4Hz), 5 _CH = 2.48 ppm.

Example 4

bis - {[(2-chloro-4-trifluoromethyl) -phenoxy] -2-nitro-benzaldehyde} -ethylenediimine (Compound No. 4) 5.2 g (0.0151 mol) 5 - [(2-chloro-4-) trifluoromethyl) phenoxy] -2-nitrobenzaldehyde and 0.45 g (0.0076 mol) of ethylenediamine are dissolved in 15 ml of isopropanol. The solution is refluxed for half an hour and then cooled. The title compound is obtained in 84% yield, molecular weight 714.

The dull yellow crystals melt at 136-138 ° C.

Characteristic fragments of the mass spectrum:

m / e (ri) = 714 (700) = [F ₃ C (CI) C ₆ H3OC ₆ H3 (NO2) CHN] _{2 (CH2) 2}

356 (750) = F ₃ C (CI) C ₆ H ₃ OC ₆ H ₃ C (NO) NCH ₂ CH 327 (56O) = F ₃ C (CI) C ₆ H ₃ OC ₆ H ₃ NO ₂ 223 (100O ) = F ₃ C (CI) C ₆ H ₃

¹ H-NMR (CDCl ₃ ): 5 _CH = 8.62, 5 _C h ₂ = 3.97 ppm.

Example 5

bis {5 - [(2-chloro-4-trifluoromethyl) -phenoxy] -2-nitro-benzaldehyde} -hexamethylenediinnine (Compound No. 5) The procedure is as in Example 4, with the difference that instead of ethylenediamine, the hexamethylenediamine used. There are 4.82 g of the title compound, yield 83%. Molecular weight 770. The pale yellow crystals melt at 142-144T.

Characteristic fragments of the mass spectrum:

m / e (ri) = 770 (380) = [F ₃ C (CI) C ₆ H ₃ OC ₆ H ₃ (NO ₂ ) CHN] (CH ₂ ^

327 (470) = F ₃ C (CI) C ₆ H ₃ OC ₆ H ₄ NO ₂

223 (72O) = F ₃ C (CI) C ₆ H ₃ ¹ H NMR (CDCl ₃ ) 5ch = 8.62, 5 _NC h ₂ = 3.60 (tr, J = 7Hz), 5 _C h ₂ = 1,25-1,75ppm.

Example 6

5 - [(2-Chloro-4-trifluoromethyl) -phenoxy] -2-nitro-benzaldehyde-ethanolamine (Compound No. 6) The procedure is as in Example 2, with the difference that instead of allylamine the ethanolamine is used. There are 4.94 g of the compounds mentioned in the title. Yield 82%. Molecular weight 388. The drappfarbigen crystals melt at 81-83 ⁰ C.

Characteristic fragments of the mass spectrum: m / e (ri) = 371 (100O) = F ₃ C (CI) C ₆ H ₃ OC ₆ H ₃ (NO) ₂ CH ₂ CNCH

370 (800) = F ₃ C (CI) C ₆ H ₃ OC ₆ H ₃ (NO _{2) 2} CH ₂ CNCH

357 (210) = F ₃ C (CI) C ₆ H ₃ OC ₆ H ₃ (NO ₂ ) CHNCh ₂ 340 (300) = F ₃ C (CI) C ₆ H ₃ OC ₆ H ₃ (NO) CNCH ₂

¹ H-NMR (CDCl ₃ ): 5 _CH = 8.73, δ _εΗ , = 3.80 ppm.

Example 7

5 - [(2-Chloro-4-trifluoromethyl) -phenoxy] -2-nitrobenzaldehyde-benzylimine (Compound No. 7) The procedure is as in Example 2, with the difference that the allylamine is replaced by benzylamine. There are obtained 6.94 g of the title compound, yield 80%, molecular weight 434. The yellowish brown crystals melt at 62-66 ⁰ C.

Characteristic fragments of the mass spectrum: m / e (ri) = 434 (160) F ₃ C (CI) C ₆ H ₃ OC ₆ H ₃ (NO ₂ ) CHNCh ₂ C ₆ H ₅

417 (220) = F ₃ C (CI) C ₆ H ₃ OC ₆ H ₃ (NO) CNCH ₂ C ₆ H ₅

91 (100O) = CH ₂ C ₆ H ₅ ¹ H NMR (CDCl ₃ ): 5 _CH = 8.80, 5 _C h ₂ = 4.80 ppm.

Example 8

5 - [(2-Chloro-4-trifluoromethyl) -phenoxy] -2-nitrobenzaldehyde (α-methyl) -benzylimine (Compound No. 8) The procedure is as in Example 2, with the difference that the allylamine replaced by (a-methyl) -benzylamine. There are obtained 6.72 g of the title compounds, yield 75%, molecular weight 448. The light brown crystals melt

Characteristic fragments of the mass spectrum:

m / e (ri) = 448 (30) = F ₃ C (CI) C ₆ H ₃ OC ₆ H ₃ (NO ₂₎ CHNCH (CH ₃₎ C ₆ H ₅

344 (720) = F ₃ C (CI) C ₆ H ₃ OC ₆ H ₃ (NO ₂ ) CHNH

105 (100O) = CH (CH ₃ ) C ₆ H ₅ ¹ H-NMR (CDCl ₃ ): 5ch = 8.77, ScH ₃ = 1.55 (d, J = 7Hz), 5 _CH = 4.57ppm ( q, J = 7Hz).

Example 9

5 - [(2-Chloro-4-trifluoromethyl) -phenoxy] -2-nitrobenzylidene-aniline (compound no. 9) The procedure is as in Example 2, with the difference that the allylamine is replaced by aniline. There are obtained 6.8 g of the title compound, yield 81%, molecular weight 420. The lemon yellow crystals melt at 91-92X.

Characteristic fragments of the mass spectrum:

m / e (ri) = 420 (22O) = F ₃ C (CI) C ₆ H ₃ OC ₆ H ₃ (NO _{2) 6} H ₅ CHNC

403 (100O) = F ₃ C (CI) C ₆ H ₃ OC ₆ H ₃ (NO) CNC ₆ H ₅

180 (55O) = C ₆ H ₄ CHNC ₆ H ₅ 77 (920) = C ₆ H ₅ ¹ H-NMR (CDCl ₃ ): Sch = 8.92 ppm.

example

{5 - [(2-Chloro-4-trifluoromethyl) phenoxy] -2-nitro-b'enzylidene} -3-trifluoromethyl-aniline (Compound No. 10) The procedure is as in Example 2, with the difference that the allylamine replaced by 3-trifluoromethylaniline. There are 9.17 g of the title compound, yield 94%, molecular weight 488. The yellow crystals melt at 92-94 ° C. - '

Characteristic fragments of the mass spectrum:

m / e (ri) = 488 (70) = F ₃ C (CI) CeH ₃ OC ₆ H ₃ (NO ₂ ) CHNC ₆ H ₄ CF ₃

471 (1000) = F ₃ C (CI) C ₆ H ₃ OC ₆ H ₃ (NO) CNC ₆ H ₄ Cf ₃

145 (82O) = F ₃ CC ₆ H ₄ ¹ H NMR (CDCl ₃ ): 5 _CH = 8.98 ppm.

Example 11

{5 - [(2-Chloro-4-trifluoromethyl) -phenoxy] -2-nitro-benzylidene} -3,4-dichloroaniline (Compound No. 11) The procedure is as in Example 2, with the difference that the allylamine replaced by 3,4-dichloroaniline. There are obtained 6.64 g of the title compound, yield 68%, molecular weight 488. The drappfarbigen crystals melt

Characteristic fragments of the mass spectrum:

m / e (ri) = 488 (300) = F ₃ C (CI) C ₆ H ₃ OC ₆ H ₃ (NO ₂ ) CHNC ₆ H ₃ Ci ₂

471 (1000) = F ₃ C (CI) C ₆ H ₃ OC ₆ H ₃ (NO) CNC ₆ H ₃ Ci ₂

145 (22O) = C ₆ H ₃ Cl ₂ ¹ H-NMR (CDCl ₃ ): 5ch = 8.92 ppm.

Example 12

{5 - [(2-Chloro-4-trifluoromethyl) -phenoxy] -2-nitro-benzylidene} -2-chloro-5-trifluoromethyl-aniline (Compound No. 12) The procedure is as in Example 2, with the difference that the allylamine is replaced by 2-chloro-trifluoromethyl-aniline and the product crystallized from isopropanol. There are obtained 8.14 g of the title compound, yield 78%, molecular weight 522. The pale yellow crystals melt at 88-89 ⁰ C,

Characteristic fragments of the mass spectrum:

m / e (ri) = 522 (5O) = F ₃ C (CI) C ₆ H ₃ OC ₆ H ₃ (NO ₂₎ CHNC ₆ H ₃ (Cl) CF ₃

505 (100O) = F ₃ C (CI) C ₆ H ₃ OCH (NO) CNC ₆ H ₃ (Cl) CF ₃

328 (12O) = F ₃ C (CI) C ₆ H ₃ H ₄ NO ₂ NCHC ₆

298 (200) = F ₃ C (CI) C ₆ H ₃ H ₄ O ₆ NCHC

179 (95O) = F ₃ C (CI) C ₆ H ₃ ¹ H-NMR (CDCI _3): 5ch = 8,95ppm.

Example 13

{5 - [(2-Chloro-4-trifluoromethyl) -phenoxy] -2-nitro-benzylidene} -2-hydroxy-aniline (Compound No. 13) 5g (0.0145 mol) of 5 - [(2-chloro) 4-trifluoromethyl) -phenoxy] -2-nitro-benzaldehyde and 1.58 g (0.0145 mol) of 2-hydroxy-aniline are dissolved in 15 ml of isopropanol. The solution is refluxed for half an hour. After cooling, 5.5 g of the title compound are obtained in crystalline form, yield 87%. Molecular weight 436.

The yellow crystals melt at 139-142 ⁰ C.

Characteristic fragments of the mass spectrum:

m / e (ri) = 436 (55O) = F ₃ C (C) C ₆ H ₃ OC ₆ H ₃ (NO _{2) 6} H ₄ OH CHNC

418 (38O) = F ₃ C (CI) C ₆ H ₃ OC ₆ H ₃ (NO ₂₎ CNC ₆ H ₄

223 (100O) = C ₆ H ₃ (NO ₂₎ CNC ₆ H ₄ ¹ H-NMR (CDCI _3): 5ch = 9.1 ppm.

Example 14

{[(2-Chloro-4-trifluoromethyl) -phenoxy] -2-nitro-benzylidene} -4-hydroxy-aniline (Compound No. 14) The procedure is as in Example 13, except that the 2-hydroxy-aniline replaced by 4-hydroxyaniline. There are obtained 6.0 g of the title compound, yield 95%, molecular weight 436. The lemon yellow crystals melt at 91-93 ⁰ C. Characteristic fragments of the mass spectrum:

m / e (ri) = 436 (710 = F ₃ C (CI) C ₆ H ₃ OC ₆ H ₃ (NO ₂ ) CHNC ₆ H ₄ Oh

419 (92o) = F ₃ C (CI) C ₆ H ₃ OC ₆ H ₃ (NO) CNC ₆ H ₄ OH

196 (100 °) = C ₆ H ₃ OC ₆ H ₃ NO

Example 15

{5 - [(2-Chloro-4-trifluoromethyl-phenoxy] -2-nitrobenzylidene} -3-nitro-aniline (Compound No. 15) The procedure is as in Example 13, with the difference that the 2- Hydroxy-aniline is replaced by 3-nitro-aniline to give 5.80 g of the title compound, yield 86%, molecular weight 465. The matte yellow K-all melts at 112-114 ° C. Characteristic fragments of the mass spectrum: m / e (ri) = 465 (5O) = F ₃ C (CI) C ₆ H ₃ OC ₆ H ₃ (NO _{2) 6} H ₄ NO ₂ CHNC

448 (100O) = F ₃ C (C) C ₆ H ₃ OC ₆ H ₃ (NO) CNC ₆ H ₄ NO ₂

Example 16

{5 - [(2-Chloro-4-trifluoromethyl) phenoxy] -2-nitrobenzylidene} -2-ethyl-6-methylaniline (Compound No. 16) The procedure is as in Example 13, with the difference to replace 2-hydroxyaniline with 2-ethyl-6-methylaniline. 5.63 g of the title compound are obtained. Yield 84%, molecular weight 462. The lemon yellow crystals melt at 92.5-93.5 ° C. Characteristic fragments of the mass spectrum:

m / e (ri) = 462 (80O) = F ₃ C (CI) C ₆ H ₃ OC ₆ H ₃ (NO ₂ ) CHNC ₆ H ₃ (Ch ₃ ) C ₂ H ₅

445 (1000) = F ₃ C (CI) C ₆ H ₃ OC ₆ H ₃ (NO) CNC ₆ H ₃ (CH ₃ ) C ₂ H ₅

229 (22O) = F ₃ C (CI) C ₆ H ₃ OC ₆ H ₃ (N) CNC ₆ H ₃ (CH ₃₎ C ₆ H ₅

133 (330) = NC ₆ H ₃ (CH ₃ ) C ₂ H ₅ ¹ H-NMR (CDCl ₃ ) 5ch = 8.63, 5 _C h ₃ = 1.05 (tr, J = 7Hz), 5 _C h ₃ = 2.1, δ _0Ηϊ = 2.45ppm (q, J = 7Hz).

Example 17

{5 - [(2-Chloro-4-trifluoromethyl) phenoxy] -2-nitrobenzylidene} -2,6-diethylaniline (Compound No. 17) The procedure is as in Example 13, with the difference that replaced 2-hydroxyaniline with 2,6-diethylaniline. There are obtained 5.11 g of the title compound. Yield 74%, molecular weight 476. The lemon yellow crystals melt

Characteristic fragments of the mass spectrum:

m / e (ri) = 476 (800) = F ₃ C (CI) C ₆ H ₃ OC ₆ H ₃ (NO ₂ ) CHNC ₆ H ₃ (C ₂ H ₅ );

459 (100O) = F ₃ C (CI) C ₆ H ₃ OC ₆ H ₃ (NO) CNC ₆ H ₃ (C ₂ Hb) ₂ 147 (43O) = NC ₆ H ₃ (C ₂ H ₅ J ₂ 132 ( 70O) = NC ₆ H ₃ (CH ₂ ) CH ₂

117 (65O) = NC ₆ H ₃ (CH ₂ ) CH ₂ ¹ H-NMR (CDCl ₃ ): 5cH = 8.63, OCH ₃ = 1.05 (tr, J = 7Hz), 5 _C h ₂ = 2 , 45ppm (q, J = 7Hz)

Example 18

3 - [(2-Chloro-4-trifluoromethyl) -phenoxy] -benzaldehyde-isopropylimine (Compound No. 18) To 6 g (0.02 mol) of 3 - [(2-chloro-4-trifluoromethyl) -phenoxy] -benzaldehyde 6 g (0.02 mol) of isopropylamine are added. During the addition, a gentle exothermic reaction takes place with intensive stirring. The solution is allowed to stand for one hour and diluted with ether. The ethereal solution is dried over magnesium sulfate and concentrated. The residue is distilled under reduced pressure. There are obtained 5.4 g of the title compound, yield 79%, molecular weight 342. The yellow liquid boils at 135-150 ° C / l Hgmm.

¹ H-NMR (CDCl ₃ ): 5cH = N = 8.15, 5 _C h ₃ = 1.14 (d, J = 7Hz), 5 _CH = 3.42ppm (oct, J = 7Hz).

Example 19

3 - [(2-Chloro-4-trifluoromethyl) -phenoxy] -benzaldehyde-allylimine (Compound No. 19) The procedure is as in Example 18, with the difference that the isopropylamine by 2.284 g (0.04 mol) of allylamine replaced. There are obtained 5.6 g of the title compound, yield 83%, molecular weight 339. The yellow liquid boils at 105-135 ° C / I Hgmm.

¹ H-NMR (CDCl ₃ ): 5 _ch = n = 8.16 5 _CHj = 4.12 (mp.), 5 _NCH! = 4.95-5.20 (mp.), 5 _CH = 5.94ppm (mp.).

Example 20

3 - [(2-Chloro-4-trifluoromethyl) -phenoxy] -benzylideneaniline (Compound No. 20) To 16.5 g (0.055 mol) of [(2-chloro-4-trifluoromethyl) -phenoxy] -benzaldehyde are added 5.1 g (0.055 mol) of aniline. The reaction mixture is stirred for one hour and the water formed is removed under reduced pressure. There are obtained 18.2 g of the title compound, yield 88%. Brown oil, molecular weight 375. ¹ H-NMR (CDCl ₃ ): 5cH = N = 8.30 ppm.

Example 21

{3 - [(2-Chloro-4-trifluoromethyl) -phenoxy] -benzylidene} -3-trifluoromethyl-aniline (Compound No. 21) To 15 g (0.05 mol) of [(2-chloro-4-trifluoromethyl) -] phenoxy] -benzaldehyde, 8.1 g (0.05 mol) of 3-trifluoromethyl-aniline are added dropwise. The resulting yellow emulsion-like reaction mixture is stirred on a water bath (65-70 ⁰ C) for 2 hours. After cooling, the product is crystallized from methanol. There are obtained 14.2 g of the title compound, yield 64%. Molecular weight 443. The crystals of crystals melt at 94-86 ° C.

Characteristic fragments of the mass spectrum:

m / e (ri) = 445 (330) = F ₃ CC ₆ H ₃ (CI) OC ₆ H ₄ CHNc ₆ H ₄ CF ₃

443 (1000) = F ₃ CC ₆ H ₃ (CI) OC ₆ H ₄ CHNc ₆ H ₄ CF ₃ 283 (150) = F ₃ CC ₆ H ₃ (CI) OC ₆ H ₄ C 172 (52O) = CHNC ₆ H ₄ CF ₃

145 (85O) = C ₆ H ₄ CF ₃ ¹ H-NMR (CDCI _3): 5 _ch = n = 8,63ppm.

Example 22

{- [(2-Chloro-4-trifluoromethyl) -phenoxy] -benzylidene} -2-chloro-5-trifluoromethyl-aniline (Compound No. 22) The procedure is as in Example 21, with the difference that the 3- Trifluoromethyl-aniline replaced by 9.8 g (0.05 mol) of 2-chloro-5-trifluoromethyl-aniline and the product crystallized from petroleum ether (40-70). There are obtained 16.6 g of the title compound, yield 70%, molecular weight 478. The white crystals melt at 85-9O ⁰ C.

Characteristic fragments of the mass spectrum:

m / e (ri): 479 (630) = F ₃ CC ₆ H ₃ (CI) OC ₆ H ₄ CHNC ₆ H ₃ (Ci) CF ₃

477 (890) = F ₃ CC ₆ H ₃ (CI) OC ₆ H ₄ CHNC ₆ H ₃ (CI) CF ₃ 442 (240) = F ₃ CC ₆ H ₃ (CI) Oc ₆ H ₄ CHNC ₆ H ₃ CF ₃ 329 (100O) = F ₃ CC ₆ H ₃ (CI) OC ₆ H ₄ CHNCf 299 (700) = F ₃ CC ₆ H ₃ (CI) OC ₆ H ₄ CHNH 206 (44O) = CHN (CI) C ₆ H ₃ CF ₃ 179 (30O) = CIC ₆ H ₃ CF ₃

Example 23

{3 - [(2-Chloro-trifluoromethyl) -phenoxy] -benzylidene} -3,4-dichloro-aniline (Compound No. 23) To 6.0 g (0.02 mol) of 3 - [(2-chloro-4 -trifluoro-methyl) -phenoxy] -benzaldehyde are added 4.5 g (0.028 mol) of 3,4-dichloroaniline. The reaction mixture is stirred for 3 hours on a water bath (80-85 ⁰ C) and diluted after cooling with ether. The precipitated yellow product is filtered and dried over magnesium sulfate. There are obtained 8.2 g of the title compound, yield 92%. 443 molecular weight. Brown scoring oil.

¹ H-NMR (CDCl ₃ ): 5ch = n = 8.25ppm.

Example 24

bis- {3 - [(2-chloro-4-trifluoromethyl) -phenoxy] -benzaldehyde} -ethylenediimine (compound no. 24) The procedure is as in Example 18, with the difference that the isopropylamine is replaced by 1.2 g ( 0.02 Moi) Äthyiendiamin replaced.

There are obtained 6.0 g of the title compound. Yield 96%, molecular weight 624. Yellow liquid.

¹ H-NMR (CDCl ₃ ): 5ch = h = 8.12, 5ch ₂ = 3.83ppm.

The compounds used in the biological experiments as references, but falling within the scope of European Patent No. 0034012, but not specifically described there compounds can be prepared according to the following Examples A-D.

Example A

5 - [(2-Chloro-4-trifluoromethyl) -phenoxy] -2-nitrobenzaldehyde ethylimine (Reference Compound A) 6.9 g (0.02 mol) of 5 - [(2-chloro-4-trifluoromethyl) -phenoxy ] -2-nitro-benzaldehyde are dissolved in 15 ml of anhydrous ethanol. Through the solution, ethylamine is passed within half an hour. During the implementation, the temperature of the reaction mixture rises to 60 ° C. The reaction mixture is stirred for a further 2 hours and then cooled. The precipitated light brown crystals are filtered. There are obtained 6.6 g of the title compound, yield 88%. Molecular weight 372. The light brown crystals melt at 61-63 ° C. Characteristic fragments of the mass spectrum:

m / e (ri) = 327 (250) = F ₃ C (CI) C ₆ H ₃ Oc ₆ H ₃ (NO ₂ ) CHNCH ₂ CH ₃

355 (330) = F ₃ C (CI) C ₆ H ₃ OC ₆ H ₃ (NO) CNCH ₂ Ch ₃

327 (460) = F ₃ C (CI) C ₆ H ₃ (NO) CHN ¹ H NMR (CDCl ₃ ): 5 _CH = 8.77, 5 _C h ₃ = 1.23 (tr, J = 7Hz) , 5 _CHa = 3.60ppm (q, J = 7Hz).

Example B

5 - [(2-Chloro-4-trifluoromethyl) -phenoxy] -2-nitrobenzaldehyde-propylimine (Reference Compound B) To 6.9 g (0.02 mol) of 5 - [(2-chloro-4-trifluoromethyl] - 1.18 g (0.02 mol) of propylamine are added to phenoxy] -2-nitrobenzaldehyde, and the reaction mixture is heated for one hour on a hot water bath.After cooling, the oily residue is crystallized from 10 ml of ethanol. 4 g of the title compound, yield 83%, molecular weight 386. The matte yellow crystals melt at 60-63 ⁰ C. Characteristic fragments of the mass spectrum: m / e (ri) = 386 (40O) = F ₃ C (CI) CeH ₃ OC ₆ H ₃ (NO ₂ ) CHN (CH ₂ J ₂ CH ₃

369 (320) = F ₃ C (CI) C ₆ H ₃ OC ₆ H ₃ (NO) CN (CH ₂ ) ₂ CH ₃

327 (100O) = F ₃ C (CI) C ₆ H ₃ OC ₆ H ₃ (NO) CHN

297 (31o) = F ₃ C (CI) C ₆ H ₃ OC ₆ H ₃ O ¹ H-NMR (CDCI _3): 5ch = 8.68, _SCH3 = 0.90 (tr, J = 7Hz), 5 _C h ₂ = 1.68 (sec., J = 7Hz), 5 _NC h ₂ = 3.57ppm (tr, J = 7Hz).

Example C

5 - [(2-Chloro-4-trifluoromethyl) -phenoxy] -2-nitrobenzaldehyde-isopropylamine (Reference compound C) The procedure is as in Example B), with the difference that the propylamine is replaced by isopropylamine. The title compound is obtained in 85% yield. Molecular weight 386. The yellow light-sensitive crystals melt at 44-45 ⁰ C. Characteristic fragments of the mass spectrum:

m / e (ri) = 386 (130) = F ₃ C (CI) C ₆ H ₃ OC ₆ H ₃ (NO ₂₎ CHNCH (CH _{3) 2}

344 (82o) = F ₃ C (CI) C ₆ H ₃ OC ₆ H ₃ (NO ₂₎ CHNH

227 (100O) = F ₃ C (CI) C ₆ H ₃ OC ₆ H ₃ (NO) CHN

43 (350) = CH (CH ₃ ) ₂ ¹ H-NMR (CDCl ₃ ): 5 _CH = 8.7, 5 _C h ₃ = 1.20 (d, J = 7 Hz), 5 _CH = 3.57 ppm ( oct., J = 7Hz).

Example D

5 - [(2-Chloro-4-trifluoromethyl) -phenoxy] -2-nitrobenzaldehyde-n-butylimine (Reference compound D) The procedure is as in Example C, with the difference that the isopropylamine is replaced by n-butylamine. The title compound is obtained in 86% yield, molecular weight 400. The yellow crystals melt

Characteristic fragments of the mass spectrum:

m / e (ri) = 400 (50) = F ₃ C (CI) C ₆ H ₃ OC ₆ H ₃ (NO ₂ ) CHN (CH ₂ ) ₃ CH ₃

383 (29O) = F ₃ C (CI) CeH ₃ OC ₆ H ₃ (NO) CN (CH ₂ J ₃ CH ₃

327 (100O) = F ₃ C (CI) C ₆ H ₃ OC ₆ H ₃ (NO) CHN ¹ H-NMR (CDCI _3): 5ch = 8.69, 5CH ₃ = 0.95 (d, J = 7Hz ) 5CH ₂ = 1.1 to 1.77 (mp), 5 _N cH ₂ = 3,65ppm (tr, J = 7Hz).

Example 25

Water-dispersible granules with an active ingredient content of 45% by weight (WG)

Component amount, wt.%

Compound No. 9 49

Cab-O-SilM5 5

Atlox4862 3

PolifonO 6

GeroponlN 5

Kaolin 32

123 g of compound no. 9 are in a mortar with 12.5 g of Cab-O-Sil M 5 (amorphous silica), 7.5 g of Atlox 4862 dispersant (condensation product of naphthalenesulfonate and formaldehyde), 12.5 g of Geropon IN wetting agent (isopropylnaphthalene sulfonate) and 80 g of kaolin mixed. The mixture is in an eddy current mill (type JMRS-80) to a

ground such fineness that the ratio of the fraction having a particle diameter over 44μιη is at most 0.5 wt .-%. To the millbase, a binder solution prepared from 15g Polifon O and 35g water are added in a kneader (type Werner), whereupon the mixture is extruded by means of an extruder device (type Alexanderwerke) using an insert with a circular opening of 1 mm. The extruded granules are dried at 60 ° C in a stream of air.

In the above process, other compounds of the general formula I can also be used as the active ingredient (for example compound No. 21).

Example 26

Wettable powder (WP)

Component amount, wt.%

Compound No. 11 96

Cab-O-SilM5 1

Dispersant 1494 3

240g of Compound No. 11 (previously ground in a mill fitted with a rotating knife) is rubbed with 2.5g of Cab-O-Sil M 5 silica support and 7.5g of 1494 dispersant (sodium salt of the condensation product of sulfonated Cresol and formaldehyde). The pulverulent mixture is ground in an eddy current mill (type Al pine J MRS-80) under an injector air pressure of 5 bar and a grinding air pressure of 4.5 bar at a feed rate of 250 g / hour. Although the wettable powder thus obtained contains no separate wetting agent, it is easily wettable, has a maximum particle diameter of 20 μιτι and shows a floating capacity in the form of a spray mixture with a concentration of 10g / l after 30 minutes at 30 ⁰ C in CIPAC Standard D water 84% and in CIPAC Standard A water 91%.

In the above method, other compounds of general formula I (e.g., compound No. 22) may be used as the active ingredient.

Example 27 component Amount,% by weight ULV agent Connection No. 10 27.5 isophorone 30 2-ethoxyethanol 10 soybean oil 32.5 (or sunflower oil)

In an anhydrous enameled autoclave 7500g isophorone and 2500g 2-Äthoxyäthanol be weighed. The solvent mixture 6875 g, added to a pre-milled in a hammer mill compound No. 10, the mixture is stirred and the temperature increased by switching on the jacket heating to 45-50 ⁰ C. After one hour - when the active ingredient has completely gone into the solution - 8125g of soybean oil (or sunflower oil) are weighed into the autoclave. Stirring is continued for a further 20 minutes and the mixture is cooled back to 20 ^° C. The resulting ULV preparation can be applied in undiluted form without adding water to the plants.

In the above method, other compounds of the general formula I can be used as the active ingredient (for example, the compound No. 22).

Example 28

Oily suspension concentrate (FO)

Component Quantity, wt.%

Compound of Formula 15 32.7

Cosmetic Vaseline Oil 48,8 TensiofixAS 4

SapogenatT-08ü 4,5

Ethylene Glycol 10 Silicon SRE 0.5

13,5gbei80 ° CgeschmolzenesSapogenatT-080Emulgierungsmittel (äthoxyliertesTributylphenol) and 12 g, not exceeding at 60 ⁰ C temperature molten homogenized Tensiofix AS emulsifying agent (one formed with n-butanol solution of calcium dodecylbenzenesulfonate and ethoxylated nonylphenol) are in a bead mill (type MOLINEX 075) added to 145g of a heated to 6O ⁰ C cosmetic Vaseiinöllösung. To the surfactant oil mixture is added 30 g of ethylene glycol and the components are homogenized by stirring for 10 minutes. 98.1 g finely ground compound No. 15 in a mortar is added to the liquid mixture. After stirring for 5 minutes (1500 revolutions per minute), the mixture is milled for 2 hours (using 350g grinding media consisting of glass beads with a diameter of 1 mm). In the oily suspension, 1.5 g of silicone SRE antifoaming agent are dispensed by stirring for 3 minutes (a 30% emulsion of dimethylsilicone oil).

In the above method, other compounds of the general formula I can be used as the active ingredient (for example, the compound No. 23).

Example 29

Emulsifiable concentrate (20EC)

component Amount,% by weight Connection No. 12 20.4 2-ethoxyethanol 10 cyclohexanone 35 Emuisogen EL360 7 TensiofixCD5 3 xylene 24.6

37 kg of 2-ethoxyethanol, 129.5 kg of cyclohexanone and 91 kg of xylene are weighed into a 500 l enameled autoclave equipped with a stirrer. In this solvent mixture 26kg Emuisogen EL360 (ethoxylated castor oil) and 11.1 kg Tensiofix CD5 (ethoxylated coconut oil) emulsifier are dissolved. The above emulsifying agent be added in a molten state (at 60-70 ⁰ C). As a final step, 75.5 kg of compound no. 12 are added and the mixture is stirred for 2 hours. It will contain a clear transparent solution.

In the above method, other compounds of the general formula I (for example, the compound No. 10 or 23) may be used as the active ingredient.

Example 30

Emulsifiable concentrate (35EC)

component Amount,% by weight Connection No. 11 35.7 cyclohexanone 10 Tensiofix CG 21 2 Tensiofix B 7453 8th xylene 44.3

In a mixture of 30 g of cyclohexanone and 133 g of xylene are added 6 hours of Tensiofix CG 21 (mixture of ethoxylated fatty alcohol, ethoxylated nonylphenol and its phosphates) and 24 g of Tensiofix B7453 (a solution of calcium dodecylbenzenesulfonate and ethoxylated nonylphenol and ethoxylated-propoxylated nonylphenol formed with n-butanol), Emulsifier dissolved. As a final step, 107 g of Compound No. 107 are added and dissolved in the liquid containing the surfactants.

In the above process, other compounds of the general formula I (for example, the compounds Nos. 9,10,12, 21, 22 and 23) may be used as the active ingredient.

Example 31

1% active substance dust powder (DP)

component Quantity, weight% Connection No. 21 1.0 UltrasilVN3 3.0 kaolin 16.0 talc 80.0

9510 g of kaolin are mixed with 1 800 g of Ultrasul VN 3 (synthetic sodium aluminum silicate) in a 5 l belt mixer. To the mixture is added 600 g of the hammer-milled compound No. 21, and the mixture is stirred for 30 minutes. The premix thus obtained is milled in a Müh Ie (type Ultraplex 250) at a feed rate of 20 kg / hour to such a fineness that the ratio of the coarse fraction having a particle diameter of 44μΓΠ is not more than 0.5 wt .-% , The millbase is mixed in a vortex mixer (Lödige 300 type) with talc in a ratio of 1: 4 within 10 minutes

 In the above manner, a dusting agent can be prepared also other fungicidal active ingredients.

Example 32

Granules which can be applied without water and 0.01 wt .-% active ingredient

Component amount, wt.%

Compound No. 11 0.01

Diaperl 51 99.99

From the active ingredient, a 2.0Gew .-% solution is prepared in methylene chloride. In an eddy-current stirrer (Lödige 20), 4000 g of bead silica carrier (particle size 0.5-2.0 mm) prepared from calcined diatomaceous earth are weighed. On this carrier are at a speed of 5g / min. 20 g of the above 2.0Gew .-% solution sprayed through a nozzle of the type Tee-Jet 10080, wherein the Lödige stirrer is rotated at 50 revolutions per minute. The sorption-type granules thus obtained are packed.

The Diaperl S1 is a granular carrier of the pearosilicic type with a high sorption capacity.

According to the above method, other fungicidal compounds of general formula I can be used as active ingredient.

Example 33

Determination of herbicidal activity

In a cultivation vessel 30 seeds are sown at a depth of 0.5 cm. After sowing, the soil is watered. The pre-emergent treatments are performed after sowing and watering and post-emergent treatments 10 days after planting out. The experiments use sprays prepared from 20% emulsifiable concentrates of the active ingredients, and the active ingredients are used in doses of 0.33-1.3-9 kg.ha.sup.- ¹ .

The soil surface is watered regularly on a daily basis. The pre-emergent treatments are expressed 10 days after outgrowth and the post-emergence treatments 10 days after the treatment as a percentage of the destroyed plants.

The results obtained are summarized in Table 2. The title headers of the table use the following abbreviations:

I = pre-emergent treatment

II = post-emergent treatment D.S. = the black rot (Digitariasanguinalis) S.V. = the Fennich (Setariaviridis)

E.C. = Echinochloacrus galli

S. H. = the carrot millet (Sorgum halepense)

CS. = theWind (Calistegiasepium)

A. T. = the velvetleaf (Abutilonthreophrasti)

M. A. = the Schutbingelkraut (Mercurialisannua)

S.A. = the common mustard (Sinapisarvensis)

Z. M. = the corn (Zea mays)

HA. = the sunflower (Helianthusannuus)

P.S. = the pea (Pisumacsativum)

A.C. = the onion (Alliumcepa)

Table 2

Toxic effects of treatments, in%

No. of the can D.S. 20 plant species S. V. 20 I Il 25 and treatment method Il 20 S. H. 0 Il 0 CS. 30 Il 0 AT. 0 M.A. 30 S.A. 20 crops II. Z.M. 0 Il 0 HA. 0 Il 0 P.S. 0 A.C.: 0 agent kg / ha I. 50 i. 40 50 weeds 40 I 30 20 I 50 20 I 0 Il 40 I 50 20 I 0 0 I 0 0 Il 0 Il 0 70 60 60 E.C. 55 50 40 60 40 0 60 70 40 10 10 0 10 0 0 90 II. 100 60 I. * 65 80 60 70 60 0 90 80 50 30 20 0 20 10 10 D 3.1 10 0 20 0 20 0 0 0 0 0 0 0 0 50 0 0 0 0 0 0 1 20 0 30 10 30 15 20 20 30 30 0 40 20 0 0 0 0 0 0 0 3 70 0 60 40 50 35 40 60 60 70 0 80 70 10 0 10 0 10 0 0 9 100 0 100 70 95 60 70 100 80 100 0 100 100 30 30 20 0 20 10 10 2) 3.11 45 0 20 10 20 0 0 20 10 15 0 0 30 70 0 0 0 0 0 0 1 70 0 50 30 30 20 20 40 30 30 0 15 60 0 0 20 0 20 0 0 3 80 0 75 60 55 40 30 70 80 45 0 30 75 30 10 30 0 30 0 0 9 100 0 100 100 95 95 100 70 100 95 0 80 100 50 30 40 0 40 10 10 3) 3.1 40 0 40 30 20 20 0 0 10 10 0 20 20 80 0 0 0 0 0 0 3 80 0 80 90 30 40 20 15 20 30 0 30 40 0 0 0 0 0 0 0 3 95 0 100 90 50 80 50 30 40 50 0 50 60 20 0 20 0 20 0 0 9 " ' 100 0 100 90 100 90 85 90 85 90 0 80 80 20 30 30 0 30 10 10 4) 3.1 40 0 40 10 20 0 0 20 20 0 0 0 20 30 0 0 0 0 0 0 1 80 0 60 30 40 40 20 40 40 25 0 30 40 0 0 0 0 0 0 0 3 85 0 SO 50 95 60 40 60 50 30 0 45 60 20 0 0 0 0 0 0 9 90 0 95 60 100 80 60 80 70 45 0 55 70 20 20 20 0 0 10 10 5) 3.1 30 0 30 20 20 0 0 20 10 0 0 10 10 50 0 0 0 0 0 0 1 60 0 60 40 40 20 20 30 20 30 0 20 40 10 0 0 0 .0 0 0 3 90 0 90 60 60 50 60 55 60 50 0 40 70 25 10 20 0 20 10 10 9 30 0 30 10 80 0 0 30 20 25 0 25 - 40 0 0 0 0 0 0 6) 1 60 0 60 30 20 20 20 40 40 35 0 30 - 20 0 10 0 10 0 0 3 100 0 90 60 40 50 55 50 60 55 0 40 60 30 10 20 0 20 10 10 9 30 0 30 20 80 0 0 15 20 0 0 0 30 40 0 10 0 0 0 0 7) 1 60 0 60 40 20 20 25 20 40 30 0 20 55 20 0 20 0 0 0 0 3 100 0 90 90 40 60 80 55 60 45 0 30 70 50 10 20 0 0 10 10 9 50 0 30 0 70 10 0 10 10 0 0 20 25 80 0 0 0 0 0 0 8th) 1 100 0 90 45 20 35 50 40 30 30 0 45 55 45 0 30 0 30 0 10 3 100 0 100 50 40 50 80 80 70 80 0 85 80 70 20 50 0 60 20 10 9 100 0 100 100 80 100 100 95 90 95 0 100 100 80 40 70 10 80 40 25 9) 3.1 0 20 95 1 0 80 3 0 100 9 0 100

10) B) 3.1 60 0 50 60 50 50 40 20 30 10 0 10 30 40 0 0 0 0 0 0 (Control) 1 100 0 95 85 80 85 60 45 50 35 0 50 60 80 0 10 0 10 0 10 3 100 0 100 90 95 100 80 75 80 70 0 90 80 90 0 20 0 30 20 20 C) 9 100 0 100 100 100 100 100 100 90 100 100 0 100 95 15 30 0 60 40 30 11) (Control) 3.1 50 0 50 60 40 60 30 10 20 0 0 0 25 45 0 0 0 0 0 0 1 100 0 95 95 80 80 60 30 40 30 0 35 55 85 0 10 0 10 0 0 3 100 0 100 100 95 95 80 40 80 60 0 55 80 90 0 20 0 30 20 20 D) 9 100 0 100 100 100 100 100 90 90 90 0 85 100 95 20 30th 0 60 40 40 12) (Control) 3.1 50 0 50 70 40 60 30 20 20 20 0 20 30 50 0 10 0 20 0 0 1 100 0 95 90 80 80 60 50 40 40 0 40 60 95 0 20 0 40 10 20 3 100 0 100 95 95 90 85 80 80 80 0 85 85 100 0 30 0 80 20 30 9 100 0 100 100 100 100 100 100 90 100 0 100 100 100 20 60 0 80 30 30 13) 1 40 0 40 20 30 20 30 0 10 0 0 0 30 20 0 0 0 0 0 0 3 60 0 55 40 40 40 40 30 30 40 0 20 60 30 0 20 0 20 0 0 9 90 0 95 80 80 70 60 50 60 60 0 40 90 40 0 30 0 30 15 20 14) 3.1 15 0 20 10 20 0 30 0 10 20 0 10 15 10 0 0 0 0 10 0 1 30 0 40 20 30 15 40 20 40 30 0 15 30 20 0 0 0 0 10 0 3 75 0 80 55 60 35 60 40 50 60 0 30 60 40 0 10 0 10 15 0 9 100 0 100 100 95 95 80 80 70 80 0 55 90 80 10 30 0 30 30 10 15) 3.1 40 0 30 25 30 20 30 30 50 20 0 20 30 40 0 10 0 10 10 10 1 80 0 60 50 60 40 40 40 50 40 0 30 70 80 0 20 0 10 10 0 3 90 0 90 75 80 80 60 50 50 50 0 40 , 85 85 0  40 0 25 10 10 9 100 0 100 100 95 100 80 80 70 60 0 80 100 90 10 60 0 50 20 20 16) 1 60 0 40 40 30 20 20 0 10 0 0 10 60 50 0 0 0 10 0 0 3 80 0 70 45 60 40 40 20 30 30 0 20 80 60 0 10 0 20 0 0 9 100 0 100 70 95 80 J55 40 50 60 0 50 100 80 10 20 0 40 10 10 17) 1 30 0 40 0 30 0 20 20 10 30 0 20 40 30 0 0 0 0 20 0 3 50 0 60 10 60 0 40 40 ' 30 40 0 30 55 40 0 10 0 10 20 10 9 70 0 80 20 85 20 65 60 70 50 0 50 70 40 0 20 0 20 40 15 A) 1 20 0 0 10 0 0 0 0 10 0 0 10 20 10 0 0 0 io 0 0 (Control) 3 70 0 60 40 30 25 30 0 20 0 0 20 40 30 0 25 0 15 0 0 9 100 0 100 60 80 75 70 30 60 30 0 40 60 50 20 50 0 30 15 5 1 20 0 0 10 0 10 0 0 0 0 0 0 20 10 0 0 0 10 0 0 3 50 0 50 50 40 40 30 0 50 0 0 20 40 50 0 20 0 25 0 0 9 90 0 95 90 80 85 70 30 100 30 0 40 70 100 20 40 0 65 10 10 3.1 20 0 10 0 0 0 0 0 30 0 0 0 30 20 0 0 0 10 0 0 1 50 0 20 50 0 , 25 0 0 50 10 0 10 60 60 0 15 0 30 0 0 3 80 0 70 75 40 45 30 30 90 30 0 40 80 80 10 30 .0 60 0 0 9 100 0 100 100 90 95 70 60 90 60 0 80 100 100 30 60 0 80 10 15 3.1 10 0 20 0 0 0 0 0 10 0 15 20 0 0 0 0 0 10 0 0 1 20 0 40 20 40 20 30 20 30 0 30 30 10 20 0 15 0 20 0 0 3 60 0 60 45 60 40 50 40 50 20 50 50 45 40 10 20 0 30 0 0 9 100 0 100 70 100 70 80 60 60 40 70 80 90 70 30 40 0 50 10 10

Example 34

Determination of fungicidal activity

Agar plates are prepared by pouring into petri dishes (diameter 100 mm) a 2 wt .-% dextrose containing potato agar medium and allowed to solidify.

From the test compounds, 20 wt .-% emulsifiable emulsions are prepared, which to stock solutions of a concentration of 0.18; 0.06; 0.0033; 0.0066; and 0.0011 wt% (1800, 600, 100, 66 and 11 ppm).

From the test fungi isolates, suspensions containing the desired number of spores are prepared at a dilution such that when a drop of the water-dispersed spore suspension is placed on the microscope slide at 100-160X magnification and Averages of 5-10 visual fields in the field of view 25-30 spores are visible.

1 ml each of the prepared spore suspensions is added with the aid of a pipette to, e 1 ml of the individual members of the dilution series. The solutions thus obtained contain 0.1; 0.03; 0.01; 0.0033; and 0.0011 wt% (900, 300, 100, 33, and 11 ppm) of drug concentrates + spore suspensions. The solutions will be 1 800sec. let stand for a long time. The bottom of a sterile test tube is immersed in the mixture of the fungicidal agent and the spore suspension. This test tube is used to draw a strip onto the prepared agar plate, after which the culture is inoculated.

If in the. Control treatments the fungi have grown well, the fixed test is evaluated. The growth in the treated group is compared with the control group. The results are expressed on the basis of the following rating scale:

1 = no colony growth (0% for comparison with the control);

2 = weak colony growth (10% compared to the control);

3 = mediocre colony growth (50% compared to the control);

4 = high colony growth (100% compared to the control).

The intermediate values in% have the following meaning: 1.5 = 5%; 2.5 = 30%; 3.5 = 75%. (Growth compared to control, 100%)

In the test experiments, the effectiveness of the fungicidal composition according to the invention with the untreated control on the one hand and with the very effective fungicidal commercial product Captan on the other hand compared.

The results are shown in Table 3. In Table 3, the fungicidal activity is given as an average of 4 repetitions. The title headers of the table use the following abbreviations:

St.R. Stemphylium radicinum St.R. He.t. Activity against the fungi species, ^c Bo.c. Fu. G. 0 Co.I. Tr.r. Di.h. Vo Old. He.t. Helminthosporum turcicum 100 As.n. Bo.c. Botritiscinerea 100 - - 45.6 47.1 - - - - Fu. G. 77.3 - - 14.6 36.0 - - - 48.4 - Co.I. Fusarium graminearum 28.6 - - 0 25.5 - - - 15.6 - Tr.r. 5 - - - 16.8 - - - 0 - Di.h. 0 - - - - - - - - - As.n. = 60.7 - - 78.8 - - - - - - Old. 32.3 - - 41.3 - - - - 75.6 - Table 3 Colletotrichum lindomuthiarum 26.8 - - 30.3, - - - - 23.3 - active substance Trichotecium roseum 10.5 - - 12.7 ° - - , - - 11.2 - No. Diaportehelianthi 5 - - 0 100 - - - 5 - Aspergillus niger 100 100 100 89.3 60 100 100 100 0 100 Alternariatenuis 75.7 89.4 69.4 52.7 100 89.4 100 100 81.2 65.1 70.4 41.1 5 86.6 82.8 75.3 74.3 44.3 1 44.4 39.8 26.3 0 77.5 60.3 38.4 54.3 24.2 concentration 29.6 19.5 14.4 - 48.3 46.6 29.9 33.3 14.4 (Ppm) 100 - - 100 - - - 16.8 - 900 80.2 - - 81.4 - - - 100 - 300 54.3 - , - 63.4 - '- - 75.9 - 2 100 16.8 - - 35.6 - - - 60.3 - 33 10 - - 25.2 - - - 42.7 - 11 46.4 - - 100 - - - 23.6 - 900 31.6 - - 85.2 - - - 44.4 - 300 20.5 - - 14.5 - - - 24.4 - 3 100 5 - - 5 - - 5 33 0 - - 0 - - - 0 11 63.3 - - 64.6 - - - - 900 28.2 - - 27.6 - - - 65.9 - 300 5.5 - - 10.4 - - - 29.2 - 4th 100 0 - - 5 - - - 10.3 - 33 - - - 0 - - - 5 11 72.5 - - 70.7 - - - - 900 19.8 - - 21.8 - - - 75.7 300 0 - - 10.3 - - - 22.3 - .5 100 - - - 0 - - 3.6 33 - - - - - - - 0 11 74.1 - - 70.6 - - - - - 900 21.2 - - 14.6 - - - 75.6 - 300 10.3 - - 10.4 - - - 23.3 6 100 5 - - 5 - - - 11.2 - 33 0 - - - - - 5 - 11 90.5 100 100 100 100 100 0 96.6 900 56.8 71.4 49.4 73.6 82.8 100 78.9 64.2 300 41.5 66.4 47.2 54.6 58.7 58.4 54.3 42.4 7 100 29.9 48.3 35.4 43.2 39.4 43.2 34.3 34.3 33 16.3 33.6 29.3 21.3 25.6 29.9 21.4 26.2 11 28.9 - 39.4 - - - 16.8 900 0 0 - 26.8 300 - - - - - - 0 8th 100 - - - - - - , - 33 - - - - - - 11 100 100 100 100 100 100 100 900 89.2 100 100 100 79.4 100 100 87.6 300 51.2 9 100 33 11 900 300 10 100 33 11 900 300 100 33 11 900 300

active substance

Activity against the fungi species,%

Concentration (ppm)

St.

He.t.

Bo.c.

Fu.g.

Tr. r.

Di.h.

As.n.

Old.

100 62.6 100 79.6 33.7 77.8 65.6 75.0 40.0 72.2 33 52.4 94 54.3 29.4 43.9 48.6 68.4 31.2 43.3 11 48.6 63.5 38.6 16.8 31.2 30.3 44.7 18.3 32.4 900 100 100 100 100 100 100 100 94.3 96.5 300 74.2 81.3 90.4 77.6 82.4 76.6 83.3 46.4 46.6 100 36.5 49.3 77.8 49.9 73.4 70.0 68.6 39.7 34.8 33 22.1 36.4 50.2 36.4 40.6 38.5 50.4 30.0 21.5 11 10.1 22.3 40.0 25.5 33.3 20.4 25.6 10.4 15.6 900 100 100 100 100 100 100 100 100 100 300 80.2 90.9 90.5 100 77.9 96.4 88.8 87.6 88.8 100 46.3 43.8 56.7 72.4 63.2 75.2 75.4 55.3 74.5 33 39.4 32.2 33.8 41.6 41.5 56.6 64.6 19.8 37.6 11 29.6 28.7 25.5 30.8 26.3 43.9 51.3 5 18.9 900 100 100 100 100 100 100 100 100 100 300 77.4 83.8 90.0 100 100 72.0 95.0 93.7 94.8 100 60.3 74.2 82.2 73.4 90.1 40.4 88.6 79.8 79.6 33 31.5 40.3 51.3 40.3 66.6 30.3 73.4 54.6 46.3 11 27.7 23.0 30.6 29.9 33.3 18.3 70.2 39.7 40.7 900 100 - - 51.2 - - - 54.4 - 300 82.3 - 33.4 - - - 32.4 - 100 41.4 - - 12.6 - - - 10 - 33 25.6 - - 5 - 0 11 10 - - 0 - 900 22.3 - 24.3 - - 24.8 300 0 - 0 - - 0 100 - - - - - 33 - - - - - 11 - 900 35.5 - - 28.6 - - 23.4 300 10.5 - - 0 - 0 100 0 - - - - 33 - - - - - - 11 - - - - - j 900 48.5 59.6 - 33.9 54.5 58.7 59.2 39.5 300 33.3 41.2 - 28.3 42.1 40.3 - 1.3 27.6 100 10.3 10.4 " - 0 0 20.9 0 5 33 0 0 - - - 5 - 0 11 - - - - - 0 - - - 900 55.7 86.4 - 73.8 35.6 66.4 - 89.8 58.3 300 40.5 66.6 - 56.2 22.2 42 62.3 40.5 100 22.3 50.4 - 34.4 5 27 - 26.6 17.4 33 10.4 34.3 - 18.6 0 10 - 0 5 11 0 20.2 - 5 - 0 0 900 100 92.4 100 85.6 100 77.4 100 68.4 79.6 300 74.1 66.7 73.5 33.4 72.8 44.9 77.1 40.0 39.6 100 35.2 40.1 42.9 13.5 36.4 34.5 50.0 14.3 20.4 33 18.5 33.4 29.8 5 17.3 17.7 33.4 7.4 16.6 11 5 16.6 18.8 0 9.8 5 18.3 5 5 900 100 100 100 100 100 100 100 100 100 300 81.1 100 87.8 63.4 100 100 100 74.3 89.9 100 48.7 44.1 38.9 30.0 100 42.3 60.5 40 73.4 33 40.2 28.3 24.4 25.6 90.5 29.1 40.4 19.9 39.5 11 25.3 16.6 19.3 18.8 73.4 12.2 30.0 5 21.6 900 100 100 100 100 100 100 100 100 100 300 83.4 98.6 79.4 77.7 95.5 100 100 85.4 82.1 100 56.3 83.5 43.6 63.2 85.3 51.2 64.4 39.6 63.4 33 28.2 58.8 40.3 43.8 65.4 29.4 35.4 24.4 44.5 11 15.5 43.2 20.6 19.9 39.6 10.2 18.6 14.4 36.8 900 100 100 - 100 100 100 - 100 100 300 76.4 95.5 - 76.6 90.0 60.7 - 88.5 74.3 100 62.3 68.4 - 64.3 81.6 38.8 - 70.5 31.5 33 38.3 41.3 - 39.2 45.2 18.0 - 63.1 24.6 11 24.9 27.8 - 25.5 30.2 10.7 - 42.2 18.8 900 44.3 33.6 - 62.4 48 51.2 - 64.7 69.2 300 35.6 29.5 - 51.5 33 40.3 50.1 52.2

active substance concentration Activity against the fungi species,% He.t. Bo.c. Fu. G. Co.l. Tr.r. Di.h. As.n. Old. No. (Ppm) St.R. 100 9.3 - 33.4 10 19.4 - 24.3 34.7 _ 33 10.2 0 - 10.3 0 5 - 10.3 10.1 11 0 - - 5 - 0 - 0 0 900 - 100 100 100 100 100 100 100 100 300 100 81.5 73.8 66.6 100 55.2 100 100 100 Cäptan 100 75.7 70.4 83.6 60.0 100 41.4 100 85.4 74.4 (Control) 33 59.5 39.9 48.8 40.4 67.8 29.4 85.3 40.2 38.6 900 30.6 - - 74.9 - - - 76.6 - 300 74.6 - - 45.6 - - - 48.6 - A 100 52.5 - - 32.3 - - - 28.4 - (Control) 33 30.0 - - 11.7 - - - 19.0 - 11 20.2 - - 5 - - - 5 - 900 10.1 - - 72.3 - - - 70.7 - 300 73.7 - - 12.2 - - - 15.3 - Β ' 100 16.6 - - 5 - - - 5 - (Control) 33 5 - - 0 - - 0 - 900 0 - - 78.8 - - - 82.3 - 300 80.8 - - 41.3 - - - 43.2 - C. 100 52.3 - - 30.3 - - - 20.7 - (Control) 33 27.7 - - 12.7 - - - 5 - 11 5.3 - - 0 - - - 0 - 900 0 - - 62.8 - - - 59.3 - 300 62.3 - - 22.5 - - - 34,4- - D .: 100 28.6 - - 5 - - - 16.1 - (Control) 33 14.2 - - - 0 - - - 5 - 11 0 - - - - - - , -   - -

Claims (15)

1. A pesticidal composition, characterized in that it contains as active ingredient at least one new compound of general formula (I), wherein X _{1 is} hydrogen or nitro; ' X _{2 is} C ₁ -I ₈ -alkyl group, with the proviso that, if X ₁ is nitro, X ₂ is C ₇ _ ₁₈ alkyl or ₂ further worin.X _C2 _6 hydroxyalkyl, or C ₂ _6-mercaptoalkyl, or C ₂ _6-aminoalkyl, or C3_ ₆ or -AIkenyl C 3-6 alkynyl, or Phenyl, or substituted phenyl of the general formula (V),
means, in which
X _{3 is the} same or different and represents C 1-10 -alkyl L-trifluoromethyl, hydroxy, mercapto, nitro, Amino or halogen, preferably chlorine, and
η is 1,2 or 3; or Aralkyl, C-i_6-alkyl-phenyl or a group of the general formula (Vl), wherein XI has the above meaning and
m is 2,3,4,5 or 6, and suitable solid and / or liquid carriers - and, if desired, other known pesticidal active substances. 2. A pesticidal composition according to claim 1, characterized in that it contains as active ingredient {5 - [(2-chloro-4-trifluoromethyl) phenoxy] -2-nitrobenzylidene} aniline. 3. A pesticidal composition according to claim 1, characterized in that it contains as active ingredient {5 - [(2-chloro-4-trifluoromethyl) phenoxy] -2-nitrobenzylidene} -3-nitro-aniline. 4. A pesticidal composition according to claim 1, characterized in that it contains as active ingredient {5 - [(2-chloro-4-trifluoromethyl) phenoxy] -2-nitrobenzyliden} -3-trifluoromethyl-aniline. 5. A pesticidal composition according to claim 1, characterized in that it contains as active ingredient {5 - [(2-chloro-4-trifluoromethyl) phenoxy] -2-nitrobenzylidene} -3,4-dichloroaniline. 6. A pesticidal composition according to claim 1, characterized in that it contains as active ingredient {5 - [(2-chloro-4-trifluoromethyl) phenoxy] -2-nitrobenzyliden} -2-chloro-5-trifluoromethyl-aniline. 7. A pesticidal composition according to claim 1, characterized in that it contains as active ingredient bis- {5 - [(2-chloro-4-trifluoromethyl) phenoxy] -2-nitro-benzaldehyde} -äthylendiimin. 8. A pesticidal composition according to claim 1, characterized in that it contains as active ingredient {5 - [(2-chloro-4-trifluoromethyl) phenoxy] -2-nitrobenzylidene} -2-hydroxy-aniline. 9. A pesticidal composition according to claim 1, characterized in that it contains as active ingredient {3 - [(2-chloro-4-trifluoromethyl) phenoxy] benzylidene} -3,4-dichloroaniline. 10. A pesticidal composition according to claim 1, characterized in that it contains as active ingredient {3 - [(2-chloro-4-trifluoromethyl) phenoxy] benzylidene} -3-trifluoromethyl-aniline. 11. A pesticidal composition according to claim 1, characterized in that it contains as active ingredient {3 - [(2-chloro-4-trifluoromethyl) phenoxy] benzylidene} -2-chloro-5-trifluoromethyl-aniline. 12. A pesticidal composition according to claim 1, characterized in that it contains as active ingredient 5 - [(2-chloro-4-trifluoromethyl) phenoxy] -2-nitro-benzaldehyde-propargylimin. 13. A pesticidal composition according to claim 1, characterized in that it contains as active ingredient {5 - [(2-chloro-4-trifluoromethyl) phenoxy] -2-nitrobenzyliden} -4-hydroxy-aniline. 14. A method for controlling pathogenic fungi pests and / or weeds, characterized in that the active ingredient is a compound of general formula (I) (wherein X ₁ and X _{2 have} the meaning given in claim 1) in a can of 0 , 1-10, Okg · ha ~ ¹ - preferably 0.2-5.0 kg · ha ^-1 . 15. The method according to claim 14, characterized in that a spray mixture, a mordant or a dust powder having a content of a compound of general formula (I) of 0.01 to5.0 wt .-% - preferably 0.1-3, 0% by weight - used. For this 2 pages drawings