CS241524B2 - Method of new arylphenylethers derivatives production - Google Patents

Description

The present invention relates to novel substituted derivatives of _t ryjlfenyleitherů following general formula I and their acid addition salts and complexes thereof with copper. The novel aryl phenyl ether derivatives are used to combat phytopathogenic fungi in plant protection.

The novel valuable arylphenyl ether derivatives of the invention correspond to the general formula I

U and V are independently C 1 -C 3 alkyl or together are one of the following alkylene bridges

whereas

R 1 and R ₂ are each independently hydrogen, C 1 -C 3 alkyl or -CH ₂ -Z-R ₇ where

Z is oxygen or sulfur, and

R ₇ is hydrogen, C 1 -C 3 alkyl, C 3 -C 4 alkenyl, methoxyethylloyio, phenyl, chloro or wherein:

Y is —CH = or —N =,

R _a and R _b independently of ^one another are hydrogen, halogen, alkyl of 1-3 carbon atoms or methoxy group, methyl substituted phenyl, benzyl, or chloro or methyl-substituted benzyloiVou group,

R ₃ , R ₄ and R ₅ are each independently hydrogen or (C 1 -C 3) alkyl, the total number of carbon atoms in R ₃ , R ₄ and R _{5 being no more} than 6, and

Ar represents a group of the formula

it may be present in the various moths that are assigned to it.

The compounds of formula (I) are stable oils, resins or solids at room temperature and exhibit very valuable fungicidal properties in plant protection. The compounds can therefore be used in agriculture and related fields for the fight against phytopathogenic microorganisms.

A preferred class of agriculturally useful fungicides are compounds of formula I, including their salts and copper complexes, wherein Y is -CH = or -N =, R _a and R _b are each independently hydrogen, halogen or C 1 -C 3 alkyl. and Ar represents a group of formula wherein

R _c , R _d and R _e are each independently hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 3 alkoxy, trifluoromethyl or nitro, and also include acid addition salts of the compounds of formula (I); of the coanple-xy compounds of formula I with copper.

Depending on the number of carbon atoms mentioned, the term "alkyl" alone or as a constituent of another substituent is, for example, the following groups: methyl, ethyl, propyl, butyl, etc., as well as their isomers such as isopropyl, isobutyl, tert-butyl, sec. .butyl atd.

The term "alkenyl" means, for example, 1-propenyl, allyl, 1-butenyl, 2-buteinyl or 3-butenyl.

Halogen is herein to be understood as fluorine, chlorine, bromine or iodine, preferably chlorine or bromine.

The present invention relates to a process for the preparation of the free compounds of the formula I, their addition salts with inorganic and organic acids, as well as their complex copper salts. \

Salts are in particular addition salts with physiologically acceptable inorganic or organic acids.

Suitable physiologically acceptable inorganic and organic acids are, for example, hydrohalic acids, for example hydrochloric acid, hydrobromic acid or hydroiodic acid, sulfuric acid, phosphoric acid, phosphoric acid, nitric acid or halogenated fatty acids, such as acetic acid, trichloroacetic acid. and oxalic acid or sulfonic acids such as benzenesulfonic acid and methanesulfonic acid.

The complexes of copper and the compounds of formula I consist of a basic organic molecule and an inorganic or organic salt of copper, for example halides, nitrate, sulfate, phosphate, tartrate, copper. Copper cation

where

R _c, R _Cl and R _e are independently at Slob hydrogen, halogen, trifluormethylovoou group or an alkyl group having 1-3 carbon atoms, and

U and V have the meanings given in formula I.

This group will be referred to as Group Ib.

Within the subgroup Ib, plant protection fungicides are those compounds of formula I in which U and V are independently C1 -C3 alkyl or together represent one of the following alkylene groups

R _t, 3c / *

W aefeo [%% · in which

Ri, R _2, R _{3 R 4} R ₅ and R are independently hydrogen or alkyl having 1 to 4 carbon atoms, the total number of carbon atoms in R _3, R ₄ and R ₅ does not exceed the number 6.

This group will be referred to as · Ic group.

Another preferred class of agriculturally preferred fungicides are those compounds of formula I wherein Y is 241524 nu —CH = or —N =, Ar has the meanings given below for formula I, R _a , R _b , R _c , R _d and R _e are independently of one another hydrogen, chloro, bromo. fluoro, methyl, methoxy or nitro, U and V are independently an alkyl group having 1-3 carbon atoms or together tvloří al alkylene group indicated under formula I, wherein _Ri, R2, R ₃ , R 4, and R ₅ are each independently hydrogen or an alkyl group having 1 to 3 carbon atoms or R ₁ represents a group -CH ₃ -O-R ₇ , wherein R ₇ represents an alkyl group having 1 to 3 carbon atoms substituted C 2 -C 4 alkyl, C 3 -C 4 alkenyl or phenyl.

This group will hereinafter be referred to as a group, Id.

Among the fungicides of subgroup Id, those compounds in which U and V together form an unsubstituted or singly substituted ethylene or propylene bridge are particularly preferred. This group will hereinafter be referred to as Group Ie.

Thus, for example, the following substances belong to particularly advantageous agriculturally useful individual substances:

2- [p- (phenoxy) phenyl] -2- [1- (1H-1,2,4-triazolyl) methyl] -4-methyl-1,3-dioxane,

2- [p- (phenoxy) phenyl] -2- [1- (1H-1,2,4-triazolylmethyl) -4-ethyl-1,3-dloxane,

2- [p- (phenoxy) phenyl] -2- [1- (1H-1,2,4-trlazolyl) methyl] -4-methyl-1, 3-dioxolane,

- [p - (phenoxy) phenyl] -2- [1- (1H-1,2,4-triazolyl) methyl] -4-ethyl-1,3-dioixoane,

2- [p- (4‘-bromophenoxy) phenyl] -2- [1- (1H-1,2,4-thiriazolyl) methyl] -4-ethyl-1, 3-dioxolane,

2- [p - (phenoxy) -2'-methylphenyl] -2- [1- (1H-1,2,4-triazolyl) methyl] -4-ethyl-1,3-dioxolam,

2- [p- (3R, 4'-Dichlorophenyloxy) phenyl] -2- [1- (1H-1,2,4-itriazalyl] methyl] -4-methoxymethyl-1,3-dioxoilane,

2- [p- (3 ', 4'-dichlorophenoxy) phenyl] -2- [1- (1H-1,2,4-triazoilyl) methyl] -4-ethyl-1,3-dioxolane, complex of 2- [ p- (4'-chlorophenoxy) phenyl] -2- [1- (1H-1,2,4-thiazolyl) methyl] -4-ethyl-1,3-dioxolane with copper (II) sulfate.

2- [p- (4'-chlorophenoxy) -2-methylphenyl] -2-1- (1H-1,2,4-triazollylmethyl) -4-methyl-1,3-dioxolane, nitric acid salt of 2- [p- (phenoxy) -2'-methylphenyl] -2- [1- (1H-1,2,4-triazolyl) methyl] -4-ethyl-1,3-dloixolane,

2- [p- (4‘-chlorophenoxy) phenyl] -2- [1- (1H-1,2,4-triazolyl) methyl] -4-ethyl-1,3-dioxolylin.

According to the invention, the compounds of the formula I and their acid addition salts as well as their copper complexes are prepared by producing a compound of the formula X

in which

Ar, R _a , R _b , U, V and Y are as defined above, intramolecularly decarboxylated, whereupon the optionally obtained free compound is converted by reaction with an organic or inorganic acid into the acid addition salt, the obtained acid addition salt optionally with reaction with the alkali metal carbonate, bicarbonate or hydroxide is converted to the free compound, or the optionally obtained free compound or the acid addition salt obtained is converted to a copper complex by reaction with a copper salt.

The compound of formula X, which serves as a starting material for decarboxylation by the process of the invention, can be obtained by kitalization of a compound of formula XI

in which

Ar, R _a , R b and Y have the meanings given above, which can be obtained by reaction of a compound of the general formula XII

Ar — OH (XII) wherein

Ar is as defined above, with a difunctional carbonic acid derivative, for example, foegene, lower alkyl haloformate or di (lower) allyl carbonate or diphenyl carbonate, and further reacting with a compound of formula XIII

Ii / = · Λ)

C-CH ₂ - / f I (xw) wherein

R _a , R _b and Y are as hereinbefore defined by heating in a dry state or in a high boiling solvent such as a high boiling ether, for example diphenyl ether or methylene glycol dimethyl ether, to a temperature of about 120 to 220 ° C.

The compounds obtained by the process according to the invention can be converted by methods known per se and other compounds of formula I.

For example, in the compounds of formula I in which U and V are the same and are optionally substituted alkyl radicals of 1 to 12 carbon atoms, the obtained compounds can be recalculated to other compounds of formula I. By reaction with 1 mol of another optionally substituted alkanol having 1 to 12 carbon atoms of formula Vc

V-OH (Vc) group U by one group V or by reaction with a diol of formula Vb both groups U by a divalent radical. Recrystallization is carried out in a conventional manner, for example in the presence of an acidic condensing agent, such as mineral acid, sultanoic acid or a strong carboxylic acid, for example hydrochloric or hydrobromic acid, sulfuric acid, p-toluenesulfonic acid or trifluoroacetic acid, preferably under distillation or azeotropic distillation boiling reaction products.

In addition, optionally additional substituents may be introduced into the carbo-cyclic aryl moieties of the compounds obtained by the process of the invention into the radical Ar and / or R _and optionally R _b . Thus, for example, halogen can be introduced by reaction with a halogen in the presence of a Lewls acid such as iron (III), zinc, boron or antimony (III) halide or N-chlorosuccinimide.

Further, nitro groups can be reduced, for example by means of suitable complex hydrides, for example lithium aluminum hydride, to amines, these amines then diazotized, for example by treatment with nitrous acid, and the resulting diazoinium group is then replaced in conventional manner by halogen or alkoxy. Likewise, halogen can be replaced by an alkyl group by reaction with a metal alkyl derivative, for example an alkyl lithium or an alkylmagnesium halide.

When the compounds of the formula I are obtained in the form of bases, they can be converted into the corresponding salts by treatment with inorganic or organic acids or they can be converted into metal complexes of the formula I by treatment with preferably equimolar amounts of metal salts. Conversely, the salts of formula I can be converted, for example, by reaction with an alkali metal carbonate or bicarbonate or an alkali metal hydroxide into the free bases of formula I.

All ketalization reactions of a ketone with a substituted .alpha.-.alpha., .Alpha., .Alpha.-diol mainly result in mixtures of the diastereomers of the resulting ketal. Correspondingly, starting ketones are generally formed of mixtures of diastereomers of the end products of formula I. The compounds of formula I may exist, for example, in the following both diastereomeric forms.

(xvi) (xvti) iypes

The type A configuration is referred to herein as the "trans" -isomer.

Λ

CfyZR? 'H

Rb

ΑΓ-0

(xi x)

The symbols in the spatially represented patterns have the following meanings:

............... = after ► - in front of the plane shown

The type B configuration is correspondingly referred to herein as the " cis " isomer.

Separation of the two diastereomers can be performed, for example, by fractional crystallization or by chromatography (thin layer chromatography, dilution chromatography, column chromatography, high pressure liquid chromatography, etc.) Both of these isomers exhibit different biological activity.

1- (β-aryl) ethylimidazolyl ketals in which aryl is substituted phenyl or naphthyl are cited as fungicides and bactericides in the following publications:

U.S. Patent Nos. 3,575,999,

936 470,

101 664,

101,666 and 4,156,008.

Surprisingly, it has been found that the compounds of formula I have a very favorable spectrum of microbicidal activity against phytopathogenic fungi and bacteria for practical requirements and further possess antimycotic and / or anticinvulsive properties which establish their utility as drug active ingredients. Thus, these compounds have very advantageous curative, preventive and systemic properties in plant protection and can be used to protect crop plants. By means of the active compounds of the formula I, the plants or other parts of the plants (such as fruits, flowers, leaves, stems, tubers and roots) of various useful plants can be suppressed or destroyed by the microorganisms occurring while remaining protected from such microorganisms. later grown parts of plants.

The active substances are particularly active against phytopathogenic fungi belonging to the following groups:

Ascomycetes, such as

Out of here and,

Podosphaera,

Erysiphe,

Momillnia,

Un-tinula,

Basidiiomycetes, such as

Hemileia,

Rbizoctonia,

Puccinia,

Fuingi impoirfecti, such as

Boitrytis,

Helrninthnsporiumi,

Fusarium,

Septoria,

Corcospora a

Alternaria.

In addition, the compounds of formula I are also effective systemically. They can also be used as mordants for the treatment of seed (fruits, tubers, grains) and plant seedlings for protection against fungal infections, as well as for phytopathogenic fungi occurring in the soil.

The active compounds according to the invention are characterized by particularly good compatibility with crop plants.

The invention therefore also relates to microbicidal compositions as well as to the use of the compounds of the formula I for combating phytopathogenic microorganisms, in particular fungi which are harmful to plants or to prevent the attack of plants.

In addition, the present invention also encompasses the production of agrochemical compositions which consist in mixing the active ingredient thoroughly with one or more of the substances described herein or a group of substances.

The invention also relates to a process for the treatment of plants, characterized by the application of the compounds of the formula I or of novel compositions.

Suitable crop plants for the areas of indication described herein include, for example, the following plant species:

cereals such as wheat, barley, rye, oats, rice, sorghum and related plants, beets such as sugar beet, fodder beet, fruit trees bearing fruit with seeds, seeds and berries, such as apple, pear, plum, peach, almond, cherry, strawberry, raspberry, blackberry, legumes such as beans, lentils, peas, soybean, oilseeds such as rape, mustard, poppy, olive tree, sunflower, coconut, castor, cocoa, underground oilseed, pumpkin plants such as pumpkins, cucumbers, melons, fibrous plants such as havlnlk, flax, hemp, jute, citrus fruit trees such as orange, lemon, tangerine, various vegetables such as spinach, lettuce, asparagus, cabbage , carrots, onions, tomatoes, potatoes, peppers, laurel plants such as avocados (Porsea gratissima J, gallbladder, camphor, or other plants such as corn, tobacco, butternut, coffee, sugarcane, tea plant, grapevine, hops, banana and rubber, as well as ornamental plants (Compositae).

The active compounds of the formula I are used in agriculture usually in the form of compositions and can be applied simultaneously or sequentially together with other active compounds, either to the area to be treated, to the plants or to a part of the plants. These other active substances in the case of plant protection products are represented as fertilizers, trace elements or other preparations which influence the growth of the plants. However, they may also be selective herbicides, insecticides, fungicides, bactericides, nematocides, moluscicides or mixtures of several of these preparations, together with, if appropriate, other carriers, surfactants or other additives which improve the application possibilities.

In all of these compositions, suitable carriers and additives may be solid or liquid substances and correspond to non-toxic substances serving in their respective formulations, such as regenerated minerals, solvents, dispersants, wetting agents, adhesives, thickeners or binders.

One preferred method used in agriculture to apply an active compound of formula I or an agrochemical composition to an infected plant is by application to the leaves of the plants. The number of applications and the amount used depend on the state of attack for the respective disease agent (fungus species). However, the active compounds of the formula I can also be fed to the plant via soil via the root system (systemic effect) by watering the place where the plant grows or by incorporating the substances in solid form into the soil, for example in the form of granules (soil). However, the compounds of formula I may also be applied to plant seeds (Coaiing) by either impregnating the seeds with a liquid preparation of the active substance or by coating them with a solid preparation. treatment of plant stems or buds.

The compounds of the formula I are used in unchanged form or preferably together with auxiliaries customary in the preparation of agrochemical preparations and are therefore processed into emulsion concentrates, paint pastes, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granules by encapsulation into, for example, polymeric substances in a known manner. Application procedures, such as spraying, fogging, dusting, sprinkling, coating or watering, as well as the type of compositions, are selected appropriately according to the desired objectives and proportions. A favorable application rate is generally between 50 g to 5 kg of active ingredient per hectare, preferably from 100 g to 2 kg of active ingredient per hectare, in particular 200 g to 600 g of active ingredient per hectare.

Agrochemical compositions which contain the active compound of the formula I and optionally a solid or liquid additive and concentrates or other preparations of this type are prepared in a known manner, for example by thoroughly mixing and / or grinding: active substances with fillers, such as solvents, solid carriers and optionally surfactants (surfactants).

Suitable solvents include aromatic hydrocarbons, preferably fractions containing from 1 to 12 carbon atoms, such as mixtures of xylenes or substituted naphthalenes, phthalic acid esters such as dibutyl phthalate or dioctyl phthalate, aliphatic hydrocarbons such as cyclohexane or paraffinic hydrocarbons, alcohols and glycols, and their ethers and esters, such as ethanol, ethylene glycol, ethylene glycol monoethyl ether or ethylene glycol monoethyl ether, ketones such as cyclohexanone, strongly polar solvents such as N-methyl-2-pyrrolidone, dimethylsulfoxide or dimethylformamide, and optionally epoxidized coconut oil or soybean oil or water.

As solid carriers, for example for dusts and dispersible powders, natural stone flours such as limestone, talc, kaolin, montmorillonite or attapulgite are generally used. Highly dispersed absorbent polymers may also be added to improve physical properties. Suitable granular adsorptive carriers for the granulates are porous types, such as pumice, brick pulp, sepiolite or bentonite; non-sorptive carrier materials, for example limestone or sand. In addition, a large number of pre-granulated materials of inorganic or organic origin, such as in particular dolomite or pulverized plant residues, can be used.

Suitable surface-active compounds are nonionic, cationic and / or antanactive surfactants having good emulsifying properties, dispersing properties and wetting properties.

Surfactants are also understood as meaning mixtures of surfactants.

Suitable anionic surfactants can be both water-soluble soaps and water-soluble synthetic surfactants.

Soaps include alkali metal, alkaline earth metal, or the corresponding optionally substituted ammonium salts of higher fatty acids (C 10 -C 22), such as sodium or potassium salts of oleic acid or stearic acid, or mixtures of natural fatty acids, which are obtained, for example, from coconut oil or tallow oil, and the fatty acid salts of methyitaurine.

However, so-called synthetic surfactants are more frequently used, in particular fatty sulfonates, fatty sulfates, sulfonated benzimidazole derivatives or alkyl, aryl sulfonates.

Fatty sulfonates or fatty sulfates are generally present as alkali metal, alkaline earth metal or optionally substituted ammonium salts and contain an alkyl radical of 8 to 22 carbon atoms, the alkyl also including an alkyl portion of the acyl radicals, such as sodium or calcium a salt of ligninsulfoic acid, dodecylsulfuric acid ester, or a mixture of sulfated fatty alcohols made from natural fatty acids. This also includes salts of sulfuric acid esters and sulfonic acids of fatty alcohol adducts with ethylene oxide. The sulfomoyl benzimidazole derivatives preferably contain 2 sulfo groups and a C 8 -C 22 fatty acid residue. Alkylarylsulfonates are, for example, sodium, calcium or thiriethanolammonium salts of dodecylhenzenesulfonic acid, dibutylnaphthalenesulfonic acid, or a naphthalenesulfonic acid-formaldehyde condensation product.

Also suitable are the corresponding phosphates, such as the salts of the foisphosphoric ester of the p-noinylphenoic adduct with ethylene oxide (4 to 14%).

Suitable non-ionic surfactants are, in particular, polyglycol ether derivatives of aliphatic or cycloaliphatic alcohols, saturated or unsaturated fatty acids and alkylphenols, which may contain 3 to 30 glycol ether groups and 8 to 20 carbon atoms in the (aliphatic 2413 -24) hydrocarbon radical of 6 to 18 atoms. in the alkyl radical of the alkylphenols.

Other suitable non-ionic surfactants are the water-soluble adducts of polyethylene oxide with polypropylene glycol, ethylenediaminopolypropylene glycol and C1-C10 alkylpolypropylene glycols containing 20 to 250 ethylene glycol ether groups and 10 to 100 propylene glycoilother groups. Said compounds usually contain from 1 to 5 units of ethylene glycol per propylene glycol unit.

Examples of non-ionic surfactants include nonylphenoilpolyethoxyethanols, castor oil polyglycoletbeirs, polypropylene-polyethylene oxide adducts, tributylphenoxypolyyeethoxyethanol, polyethylene glycol and octylphinoxypolyethoxyethanol.

Also suitable are fatty acid esters derived from polyoxyethylene sorbitan, such as polyoxyethylene sorbitam trioleate.

The cationic surfactants are in particular quaternary ammonium salts containing, as a substituent on the nitrogen atom, at least one alkyl radical of 8 to 22 carbon atoms and containing, as further substituents, lower or halogenated alkyl radicals, benzyl radicals or lower hydroxy, alkyl radicals remnants. These pigments are preferably in the form of halides, methylsulfates or ethylsulfates, and for example, stearyltrimethylammonium chloride or benzyl di- (2-chloroethyl) ethylammonium bromide.

Surfactants useful in the manufacture of the agrochemical compositions of the present invention are described, inter alia, in the following publications: Mc Cutcheons Detergents and Emuils. , Inc. New York, 1980.

Agrochemical preparations generally contain from 0.1 to 99% of active compound of the formula I, in particular from 0.1 to 95% of active compound of the formula I, from 99.9 to 1%, in particular from 99.8 to 5% of solid or liquid additives, and 0 to 25%, in particular 0.1 to 25% of surfactants.

While concentrated formulations are preferred as commercial products, s-e typically uses dilute formulations for final use.

The agrochemical compositions may also contain other additives such as stabilizers, anti-foaming agents, visco regulators, sinters, binders, adhesives, as well as fertilizers or other active ingredients to achieve particular effects.

The following examples serve to illustrate the invention in greater detail without restricting it. Percentages and parts refer to weight.

Example 1

Preparation of 2- [p- (phenoxy) phenyl] -2- [1- (1H-1,2,4-triazolyl) methyl] -1,3-dioxolane

z = w ^CH rA (1.1)

N parts of 2- [p- (phenoxycarbonyloxyphenyl) -2- [1- (1H-1,2,4-triazolyl) methyl] -1,3-dioxolane was heated in 200 ml ethylene glycol diethyl ether for about 10 hours. After cooling to room temperature, the oily crude product is taken up in 500 ml of diethylethe.ru, washed twice with 100 ml of water each time, dried over sodium sulphate. The remaining crystals were purified by recrystallization from a mixture of ethyl acetate and cyclohexane in the presence of activated carbon to give white crystals having a melting point of -100 to 102 degrees Celsius.

The following reaction products can also be prepared in an analogous manner (unless otherwise stated, mixtures of diastereomers with different ratios) of formula I are obtained:

In the following tables, A is a type A diastereomer and B is a type B diastereomer.

Table 1

Compounds of formula XXI

b— <

(xxt) including isomeric forms:

compound number Rio Y salt physical daita 1.1 H N - mp 100-102 ° C 1.2 H N HNO3 1.3 H CH - 1.4 CH, N - mp 85-92 ° C 1.5 CH, N HCl 1.6 CH, N Strange? 1.7 CH, CH - 1.8 CH, N Mn _{(NO3) 2} 1.9 c ₂ h ₅ N - mp 81.5-83.5 ° C 1.10 c ₂ h ₅ N hno ₃ 1.11 c ₂ h ₅ N ZnCl 2 1.12 C ₂ H ₅ N M n (NO _{3) 2} 1.13 c ₂ h ₅ N FeCl ₃ 1.14 C ₂ H ₅ CH - light brown oil 1.15 c _2: h ₅ CH CuCl ₂ 1.16 C ₃ H ₇ -n CH - 1.17 C3H7-I1 N - mp 68.5-71 ° C 1.18 C ₃ H ₇ -n N ZnCl ₂ 1.19 C, H ₇ -n Ni HCl 1.20 C ₄ H ₉ -n N - 1.21 C ₄ H ₉ -n CH - 1.22 CH ₂ C1 N - 1.23 ch ₃ oh N - mp 111-122 ° C 1.24 CH ₂ OCH ₂ - N -. viscous oil n ₀ ²⁶ = 1.58 1.25 c ^ and ₂ - @ - « N - mp 83-85 ° C B 1.26 ^c ^ O ^H3 N - mp 107-109 ° C A 1.27 N - mp 90-94 ° C B 1.28 ch ₂ oh CH _ mp 118-1123 ° C 1.29 ch ₂ and ₃ CH - 1.30 c ₂ h ₅ N 1/2 CuSO ₄ 1.31 ch ₂ oc ₂ h ₅ N - 1.32 ch ₂ och, N - 1.33 ch ₂ and ₂ ch ₂ óch ₃ N -

Table 2 Compounds of formula XXII

isomeric forms

compound number ^R u ^r i ₂ Y salt 2.1 ch ₃ c ₂ h ₅ CH - 2.2 gh ₃ c ₂ h ₅ N - 2.3 ch ₃ C ₂ H ₅ CH HNO3 2.4 ch ₃ c ₂ h ₅ N HNO ₃ 2.5 ch ₃ C3H7-II CH - 2.6 ch ₃ c3H7-.nl N - 2.7 ch ₃ C ₃ H ₇ -n N HNO3 2.8 ch ₃ C ₃ H ₇ -n N Mn (NO ₃ ) ₂ 2.9 ch ₃ ch ₃ CH - 2.10 ch ₃ ch ₃ CH CuCl ₂ 2.11 ch ₃ C ₂ H ₅ CH Mn (NO ₃ ) ₂ 2.12 ch ₃ c ₂ h ₅ CH CuCl ₂ 2.13 ch ₃ c ₂ h ₅ N CuCl ₂ 2.14 ch ₃ c ₂ h ₅ N ZnCl ₂ 2.15 ch ₃ c ₂ h ₅ N Mn _{(NO3) 2} 2.16 ch ₃ c ₂ h ₅ N FeCl ₃ 2.17 ch ₃ ch ₃ N - 2.18 ch ₃ ch ₃ . N hno ₃ 2.19 c ₂ h ₅ ch ₃ CH MnCla 2.20 c ₂ h ₅ ch ₃ '' · N MnCl ₂ · 2.21 c ₂ h ₅ gh ₃ CH H ₂ SO ₄ 2.22 C ₂ h ₅ ch ₃ CH ZnCl ₂ 2.23 c ₂ H ₅ CaHg CH - 2 ... 24 c ₂ h ₅ c ₂ h ₅ CH h ₂ so ₄ .. 2.25 c ₂ h ₅ c ₃ h ₅ N - 2.26 c ₂ h ₅ c ₂ h ₅ N HNO3 2.27 c ₂ h ₅ c ₂ h ₅ N HCl 2.28 c ₂ h ₅ C3H7-J1 N - 2.29 c ₂ h ₅ C ₃ H ₇ -i N - 2.30 c ₂ h ₅ C ₃ H ₇ -, n CH - 2.3Ϊ c ₂ h ₅ C3H7-II N HCl 2.32 C ₂ H ₅ C ₂ H ₅ N Mn _{(NO3) 2} 2.33 ch ₃ c ₂ h ₅ N (COOH) ₂ 2.34 ch ₃ c ₂ h ₅ CH (COOH) ₂ 2.35 ch ₃ C ₃ H ₇ -i N - 2.36 ch ₃ C ₃ H ₇ -i N H ₂ SO ₄ 2.37 - (CH ₂ ) ₄ - CH - 2.38 _ (ch ₂ ) ₄ - CH hno ₃ 2.39 - (ch ₂ ) ₄ - N ' - 2.40 - (CH ₂ ) ₄ - N Mni JNU3 2.41 - (CH ₂ ) ₄ - N (COOH) ₂ 2.42 - (CH ₂ ) ₄ - N ZnCl ₂ 2.43 - (CH ₂ ) ₄ - N HCl 2.44 - (ch ₂ ) ₄ - CH ZnCl ₂

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including isomeric forms compound number Rn R12 ^R17 RlS Y salt physical data

5.1 ch ₃ c ₂ h ₅ 2-C1 H CH - 5.2 ch ₃ c ₂ h ₅ 2-C1 H N - 5.3 ch ₃ c ₂ h ₅ 2-C1 6-C1 CH HNO ₃ 5.4 ch ₃ c ₂ h _{5 2-CH3} H N HNO ₃ 5.5 ch ₃ C ₃ H ₇ -n 2-C1 H CH - 5.6 : · · CH ₃ C ₃ H ₇ -n 2-C1 H N - 5.7 ch ₃ C ₃ H ₇ -n 3-C1 H N HNO3 5.8 ch ₃ C ₃ H ₇ -n 3-C1 6-C.l N Mn _{(NO3) 2} 5.9 ch ₃ ch ₃ 2-C1 H CH - 5.10 ch ₃ ch ₃ 2-C1 6-C1 CH CuCl ₂ 5.11 ch ₃ c ₂ h ₅ 2-C1 H CH Mn _{(NO3) 2} 5.12 ch ₃ c ₂ h _{5 2-CH3} 6-CH3 CH CuCls 5.13 ch ₃ ch _{3 2-CH3} 11 N HNO3 5.14 gh ₃ gh _{3 2-CH3} H N HBr 5.15 ch ₃ c ₂ h _{5 2-CH3} H N Mn _{(NO3) 2} 5.16 ch ₃ c ₂ h ₅ 2-NO ₂ H N FeCl ₃ 5.17 ch ₃ ch ₃ 2-C.l H N - 5.18 ch ₃ ch ₃ 2-C1 5-C1 N HN0 ₃ 5.19 c ₂ h ₅ ch ₃ 3-C1 H CH MnCl ₂ 5.20 c ₂ h ₅ ch _{3 2-CH3} H N MnCl ₂ 5.21 c ₃ h ₅ ch _{3 2-CH3} H N CuCl ₂ 5.22 c ₂ h ₅ ch ₃ 2-C1 5-C1 H ZnCl ₂ 5.23 c ₂ h ₅ c ₂ h ₅ 2-Br H CH - 5.24 H c ₂ h ₅ 2-0CH ₃ 6-OCH 3 CH - 5.25 H H 2-C1 H N - 5.26 H H 2-C1 H CH - 5.27 H H 2-C1 6-C1 CH - 5.28 H H 2-C1 H N Mn _{(NO3) 2} 5.29 .... H H 2-C1 6-C1 N - 5.30 H ch ₃ 2-C1 H N - 5.31 H gh ₃ 2-C1 H N hno ₃ 5.32 H ch ₃ 2-C1 6-C1 N - 5.33 H ch ₃ 2-C1 H CH - 5.34 H ch ₃ 2-OCH ₃ 6-OCH 3 CH - 5.35 H ch ₃ 3-C1 H N - 5.36 H ch _{3 2-CH3} H N HNO3 5.37 H ch ₃ 3-CH _p H N - 5.38 H c ₂ h ₅ 3-CH ₃ H CH CuCl2 5.39 H c ₂ h ₅ 2-CH3 6-CH3 N - 5.40 H C ₂ H ₅ 2-CHg H N hno ₃ 5.41 H c ₂ h ₅ 2-Br 5-Br N - 5.42 H c ₂ h ₅ 2-C1 H N - 5.43 H C ₃ H ₇ -n 2-C1 H N - 5.44 H C ₃ H ₇ -n 2-C1 6-C1 N - 5.45 H C ₃ H _{7 -} 2-CH3 H N - 5.46 H C ₃ H _{7 -} 2-CH3 H CH -

, t. mp 158-160 ° C mp 192-204 ° C

mp 132-134 ° C

mp 108-110 ° C oil, n _D ²² = 1.5620

compound number Ru Rj2 ^R 17 R18 Y salt physical data 5.47 H C3H7-I 2-OCH ·, 6-OCH ₃ N MnCl ₂ 5.48 C, H, C, H _; 2-C1 H N - 5.49 c ₂ h _e c ₂ H ₅ 2-C1 H N HNO3 5.50 C ₂ H _r ic ₂ H ₅ 2-C1 6-C1 N HCl 5.51 H H 2-OCH ₃ 6-OCH 3 CH - 5.52 C ₂ H _e . C ₃ H ₇ -i 2-CH ·, H N - 5.53 H c ₂ h ₅ 2-OCH ·, 6-OCH ₃ N - 5.54 H c ₂ h ₅ 2-OCH 3 6-OCH ₃ N - 5.55 H H 2-OCH ·, 6-OCH 3 N - 5.56 ch ₃ c ₂ h ₅ 3-C1 H N (COOHb 5.57 ch ₃ c ₂ h ₅ 2-CH ·, 6-CH3 CH (COOHh 5.58 CH ·, C ₃ H _{7 -} 2-C1 H N - 5.59 CH ·, C ₃ H _{7 -} 2-C1 6-C1 N h ₂ Sat ₄ 5.60 - (CH ₂ ) ₄ 2-C1 H CH - 5.61 - (CH _{2) 4} - 2-C1 H CH HJNU3 5.62 - (CH ₂ ) ₄ - 2-C1 H N - 5.63 - (CH _{2) 4} - 3-C1 H N Mn (NO ₃ b 5.64 - (CH ₂ ) ₄ - 3-C1 6-C1 N (COOHb 5.65 - (CH ₂ ) ₄ - 3-C1 5-C1 N ZnC Í2 5.66 - (CH ₂ ) ₄ - 3-C1 6-C1 N HCl 5.67 - (CH _{2) 4} - 2-C1 H CH ZnCl ₂ 5.68 H H 2-CH ·, H CH - mp 103-106 ° C 5.69 CH ·, ch _{3 2-CH3} H CH - · 5.70 H C ₃ H ₇ -n 2-CH3 H CH yellow resin n _D ⁵⁰ = 1.5476 5.71 H CH9OCH ·, 2-CH ·, H CH - resin 5.72 H CH ·, 2-CH ·, H CH - 5.73 H c ₂ h ₅ 2-CH ·, H CH resins, n _D 50 = 1.5557 5.74 H ch ₂ oh 2-CH ·, H CH - oil, n ^₅₀ = 1.5482 5.75 H ch ₂ och ·, 2-CH3 H N -. : 5.76 H c ₂ h ₅ 2-CH3 H N resins, n _D ⁵⁰ = 1.5502 5.77 H H 2-CH ·, H N - mp 103-105 ° C 5.78 H C3H7-I1 2-CH3 H N —— resins, n _D ⁵⁰ = 1.5467 5.79 H CH9OH 2-C1 H CH - 5.80 H C2H5 2-Br H CH - 5.81 H C2H5 2-C1 H CH resin, n _D ²² ₌ 1.5765 5.82 H CH ₂ OCH ₃ 2-C1 H CH - 5.83 H ch ₂ and ₃ 2-C1 H N - 5.84 H ch ₂ oh 2-Br H CH - 5.85 H CHqOCH ·, 2-Br H CH - 5.86 ch ₃ ch ₃ 2-Br H N - 5.87 H ch ₂ and ₃ 2-Br H N - 5.88 H ch ₂ oh 3-NO ₂ H CH - 5.89 H C ₃ H ₇ -n 3-NO9 H N - 5.90 H C ₂ H ₅ 2-Br H N - 5.91 H C ₂ H ₅ 3-NO ₂ H CH - 5.92 H CH-, 3-NO ₂ H CH - 5.93 H c ₂ h ₅ 3-NO ₂ H N - 5.94 H ch ₃ 3-NO ₂ H N - 5.95 H ch ₂ oh 3-CH ·, H CH - 5.96 H ch ₂ and ₃ 3-CH ₃ H N - 5.97 H c ₂ h ₅ 2-NO ₂ H CH - 5.98 H ch ₂ and ₃ 2-NO ₂ H N - 5.99 H ch ₂ and ₃ 2-NOa H CH - 5.100 H C ₂ H ₅ 3-CH3 H N - n _D 20.5 _{= 1 (} 5692 5.101 H CH2OCH3 3-CH ·, H CH - 5.102 H C9H ₅ 3-CH, H N - n _D 22 == 1.5577 5.103 H ch ₂ oh 2-NO ₂ H CH - 5.104 H c ₂ h ₅ 2-NO _b H N —-

compound number Rn Rj2 R17 R18 Y salt physical data 5.105 _2-CH3 H 2-CH3 _5-CH3 CH - viscous product, n _D = 1.5463 with 5.106 H C ₃ H ₇ -n 2-CH3 H N - oil, n _D ²² = 1.5461, A 5.107 H C ₃ H ₇ -n 2-CH3 H N - viscous oil, n _D ²² = 1.5468, B 5.108 H c ₂ h ₅ 3-CH3 H N - resin, no ⁵⁰ = 1.5638 5.109 H c ₂ h ₅ 3-CH ₃ H CH - resins, n _D ⁵⁰ = 1.5732 5.110 H c ₂ h ₅ 2-C ₂ H ₅ H N HNO ·, mp 132-134 ° C 5.111 H c ₂ h ₅ 2-CH ·, H CH (COOH) ₂ mp 115-118 ° C 5.112 H c ₂ h ₅ 2-C ₂ H ₅ H Ν ' - oil, n _D ²² = 1.5642 5.113 H c ₂ h ₅ 3-CH ·, H N - oil, n _D ²² = 1.5 6 31, A 5.114 H c ₂ h ₅ 3-CH ·, H N - oil, n _D ²² = 1.5633 5.115 H c ₂ h ₅ 2-C ₂ H ₅ H CH - brown resin 5.116 H CHo 2-C ₂ H ₅ H CH HNO ·, mp 105-119 ° C 5.117 H CH ·, 2-C ₂ H ₅ H CH - viscous oil 5.118 H CH ·, 2-C ₂ H ₅ H N HNO ·, mp 136-138 ° C 5.119 H C ₂ H ₅ 2-CH ·, H CH HCl mp 166-171 ° C 5.120 H c ₂ h ₅ 2-CH ·, H CH h ₂ Sat ₄ mp 136-138 ° C 5.121 H c ₂ h ₅ 2-CH, H CH CH3SO3H mp 98-106 ° C 5.122 H c ₂ h ₅ 2-CH ·, H CH HNO ·, mp 96-98 ° C 5.123 H C ₂ H ₅ 2-C H _2, H CH HNO ₃ mp 134-137 ° C 5.124 H c ₂ h ₅ 2-CH ·, H CH - oil, 5.125 H c ₂ h ₅ 2-CH ·, H CH -. oil, B 5.126 H C3H7-11 2-CH ·, _5-CH3 N - n _D ²³ = 1.5580 5.127 H c ₂ H _{5 2-CH3} 5-CHg N - mp 73-75 ° C 5.128 H CH ·, 2-CH ·, 5-CH3 N - mp 93-95 ° C 5.129 ch ₃ CH ·, 2-CH, _5-CH3 N - mp 59-62 ° C 5.130 H CH ·, 2-CH3 5-CH3 CH - n _D ²³ = 1.5751 5.131 H c ₂ h ₅ 2-CH3 3-CH ·, N HNO3 mp 103-105 ° C 5.132 H C ₂ H ₅ 2-CH3 3-CH ·, CH HNO ₃ mp 126-128 ° C

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Examples of fungicidal compositions which contain liquid active compounds of the formula I (0 / o =% by weight):

fr

2. Emulsion concentrate

and) (b) C) the active substance of Tables 1 to 10 25% 40% 50% calcium salt of dodecylbenzene- sulfonic acids 5% 8% 6% ric ino- polyethylene glycol ether oil (36 moles of ethylene oxide). du) 5% - - tributylphenoylpolyethylene-gly- Collether (30 moles of ethylene oxide) - 12% 4% cyclohexanone - 15% 20% mixture of xylenes 65% 25% 20% Of such concentrates, can be diluted with water prepare emulsions every

required concentration.

3. Solutions

and) (b) C) (d) the active substance of Tables 1 to 10 80% 10% 5% 95 «/ o ethylene monomethylether glycol 20% - - - polyethylene glycol (molecular weight 400) - 70% - - N-methyl-2-pyrrolidone - 15 ° / o - - epoxidized coconut oil - - 1% 5% petrol (boiling point 160—190 degrees Celsius) - - 94 o / o - These solutions are suitable for application in the form minimal drops. 4. Granulate and) (b)

the active substance of Tables 1 to 10 5% 10% kaolin 94% - highly dispersed acid siliceous 1% - attapulgit - 90% The active substance is dissolved in methylene chloride, sprayed on layman and roz the solvent is then evaporated in vacuo. 5. Dust and) (b)

the active substance of Tables 1 to 10 2 «/ o 5 o / o highly dispersed acid siliceous 1 o / o 5% talc 97% - kaolin - 90%

By thoroughly mixing the carrier substances with the active substance, a directly usable dust is obtained.

Examples of fungicidal compositions containing solids of formula I (% =% / weight)

6. Wettable powder

and) (b) C) the active substance of Tables 1 to 10 25% 50% 75% ligninsulfon sodium acid 5% 5% -. sodium lauryl sulfate 3% -. 5% natriumdiisobutylnaftalen- sulfonate - 8 ° / o 8 ° / o octylfemotpolyethylengly- ether (7 to 8 moles of ethyl lenoxide) - 2% - highly dispersed acid siliceous 5% 10% 10% kaolin 62 27% - The active ingredient is well mixed with others- calcium dodecylbenzenesulfonic acid the ingredients and the mixture is well-ground in acid 3% suitable mill. A wettable powder is obtained. castor oil polyglycol ether check that can be diluted with water to suspension (35 mol of ethylene oxide) 4% of each desired concentration. cyclohexanone 30% mixture of xylenes 50% 7. Emulsion concentrate From this concentrate, can by dilution the active substance of Tables 1 to 10 10% with water to prepare emulsions each octylphenolpolyethylene glycol ether 3% concentration.

(4 to 5 moles of ethylene oxide)

8. Dust and (b) the active substance in Tables 1 to 10 5% 8% talc 95% - kaolin - 92%

The active ingredient is mixed with the carrier and ground in a suitable mill. A dust is obtained which can be directly applied.

9. Granulate obtained by extrusion or evenly applied to the kaolin moistened with polyethylene glycol. In this way a non-dusted coated granulate is obtained.

active ingredient from Tables 1 to 10 10% sodium lignin sulfonate 2% carboxymethylcellulose 1% kaolin 87%

The active ingredient is mixed with the ingredients, milled and moistened with water. This mixture is extruded on an extruder and then dried in an air stream.

10. Coated granulate active substance of Tables 1 to 10 3% polyethylene glycol (molecular weight 200 µl 3% kaolin 94%

The finely divided active ingredient is mixed in a mixture11. Suspension concentrate

the active substance of Tables 1 to 10 40 % ethylene glycol 10 % nonylphenolpolyethylene glycol ether (15 mel ethylene oxide ¹ ) 6 % ligninsulfonic acid sodium salt 10 % carboxyrnethylcellulose 1 % 37% aqueous formaldehyde solution 0.2% silicone oil in the form of 75% aqueous emulsions 0.8% water 32 % The finely divided active substance is thorough-

mixed with the remaining ingredients. A suspension concentrate is obtained from which suspensions of each desired concentration can be prepared by dilution with water.

Examples illustrating biological activity:

In all of the examples described below that illustrate biological activity (Examples 18-22 J), the following products A to D, which are known on the market, were simultaneously tested for comparison:

A = "Maneb" = manganese ethylene bis-dithiocarbarate

B - 'Mancozeb' - rnangaoato-zinc ethylene bis-dithiocarbamate

C - 'Fentin Acetate' - triphenyltin acetate

D = "Forpet" = N-trichloromethylthiophthalimide.

Example 18

Effect against rust (Puccinia graminisj on wheat)

(a) Residual protective effect

Wheat plants are sprayed with a suspension made of wettable powder (active ingredient concentrate) 6 days after sowing, with the active ingredient concentration in the spray suspension being 0.06%. After 24 hours, the treated plants are infected with a uredospo suspension of the fungus. After incubation for 48 hours at 95-100% relative humidity and at a temperature of about 20 ° C, the infected plants are placed in a greenhouse at a temperature of about 22 ° C. Assessment of rust development is performed 12 days after infection.

b) Systemic effect

Wheat plants are covered 5 days after sowing with a suspension made from a wettable powder of active ingredient (concentration 0.006% active ingredient based on soil volume). After 48 hours, the treated plants are infected with a fungal uredospore suspension. After incubation for 48 hours at 95-100% relative humidity at about 20 ° C, the infected plants are placed in a greenhouse at about 22 ° C. Assessment of rust development is performed 12 days after infection.

The compounds of Tables 1 to 10 show good activity against Puccinia. Untreated but infected control plants are 100% infected with Puccinia.

The results are shown in the following table:

(a) Residual protective action against Puccinia gramini-s

compound number attack% compound number attack 1.9 0—5 3.212 0—4 1.17 0—1 3.213 0—3 1.24 0—1 3.220 0—4 1.26 0-4 3.226 0—4 2.17 0—5 3.227 0-3 3.1 0—1 3.231 0 3.2 0 3.232 0 3.6 0 3.233 0 3.7 0 3.234 0 3.8 0—4 3.263 0—1 3.12 0—1 3.267 0 3.26 0—5 3.274 0 3.51 0—2 3.279 0—2 3.52 0—2 3.287 0-5 3.54 0—2 3.292 0—4 3.55 0—3 3.311 0—3 3.70 0-4 3.314 0 3.75 0—4 3.340 0—2 3.78 0-3 3.348 0—1 3.83 0-2 3.373 0—2 3.85 5—7 3.376 0—4 3.86 0—2 4.2 1—3 3.127 0—1 4.15 5—12 3.133 0 4.23 5—7 3.155 0 4.50 0—5 3.156 0 4.55 0—4 3.160 4—7 4.57 0—3 3.162 0—1 4.66 0—5 3.164 0 4.70 3—5 3.168 0 4.77 0—4 3.171 0—4 4.78 0—4 3.172 0-4 4.81 0 3.176 0—3 4.89 2—4 3.177 0—4 4.90 0—2 3.193 0—5

compound number attack% compound number attack% 4.91 0—2 5.78 4—5 4.92 0—4 6.8 0—5 4.93 0 7.7 0—1 4.94 4-5 7.33 5—7 4.113 0—5 8.66 0-2 4.116 0-4 5.13 0—2 AND 90—95 5.14 0 (B) 92—97 5.36 0 C 90—95 5.40 0—2 D 90—93 5.70 0—1 control 100 ALIGN!

5.71 4-7

5.76 3-5

In addition, compound 6.8 has an excellent systemic effect, among other things. The attack on Puccinia was completely suppressed (0% attack). This effect could also be seen with a considerably reduced application rate of 0.006%.

Example 19

Activity against Cercospora arachidicola on groundnut plants Up to 15 cm high groundnut plants are sprayed with a spray suspension (0.02% active ingredient) which was made from a wettable powder of the active ingredient. After 48 hours, the plants are infected with a suspension of Cercospora arachidicola:

compound number of infestation% fungus iridia. The infected plants are incubated at about 21 ° C and high humidity for 72 hours and then placed in a greenhouse until typical spots on the leaves are present. The fungicidal effect is assessed 12 days after infection, based on the number and size of the spots occurring.

Compared to untreated but infected control plants (number and size of spots = 100%), peanut plants treated with the active substances of Tables 1 to 10 show a significantly reduced Cercospora attack. The results are shown in the following table:

Compound number%

1.1 0—4 3.171 0—3 1.4 2—5 3.172 0 1.9 0 3.176 0 1.14 7-10 3.177 0-1 1.17 0 3.212 0—5 1.24 0 3.213 2—3 1.25 0 3.220 4—5 1.26 0—2 3.221 0 1.27 0-1 3.226 0—3 2.17 0 3.231 0 3.1 0 3.232 0 3.2 5—10 3.233 0 3.6 0—4 3.234 0 3.7 0 3.267 3-4 3.11 0 3.292 0—4 3.51 0—4 3.314 0 3.52 0—3 3.348 0—2 3.54 0—3 4.15 0 3.55 0 4.23 1 3.75 5—10 4.50 0 3.78 0 4.57 0—3 3.85 0 4.59 0-2 3.86 0 4.66 0—2 3.127 0—1 4.89 0 3.133 0—4 4.90 0 3.155 5—9 4.91 0 3.156 0 4.92 0 3.162 0—5 4.93 0

compound number · attack% compound number attack% 4.94 5—7 5.77 0—1 4.113 0 5.78 0 4.116 5—7 6.1 0 5.13 0 6.8 0 5.14 0 7.3 7—9 5.36 0 7.34 3—5 5.40 0 8.72 7—10 5.70 0—2 AND 93—98 5.71 0—2 (B) 95—100 5.73 0 C 93—96 5.75 0 D 94—98 5.76 0 control 100 ALIGN!

Example 1 a d 20 of a suspension (concentration 0.006% of active substance based on soil volume), which was

Action against powdery mildew (Erysiphe gra- made of a wettable powder you mean) on barley ky. Pay attention to this to ensure that the suspension does not came into contact with overground parts r .st- (a) Residual causative effect tench. After 48 hours, the treated plants were dusting conidia mushrooms. Infected plants About 8 cm high barley plants are eaten barley is placed into the greenhouse at temperature spray with suspension (c ) concentration of 0.02% about 22 ^° C and after 10 days the active substance], which was made of sponge. of a readable powder of the active ingredient. After 3 to 4 hours The compounds of formula I show good treated plants dust conidia- dual protective anti-powdery mildew effect ml mushrooms. Infected barley plants are Erysiphe graminis]. then placed in a greenhouse at about 22 ° C however, infected control plants show degrees Celsius and after 10 days to assess 100% attack by grass powdery mildew. sponge. The test results are summarized in the following table: (b) Systemic effect: About 8 cm high barley barley Action against powdery mildew (Erysiphe graminis) compound number attack% compound number attack% 1.1 0—4 3.103 5—9 1.4 4—7 3.127 0—5 1.9 0 3.133 0—1 1.14 30 3.156 0 1.17 0 3.160 0 1.23 0 3.162 0-2 1.24 0—5 3.164 0 1.25 0 3.168 0 1.26 0 3.171 2—5 1.27 0—3 3.172 0—3 2.17 0—4 3.174 7—9 3.1 0 3.176 5—6 3.2 0 3.177 0—3 3.6 0 3.193 0 3.7 0 3.212 0—5 3.8 0 3.213 4—5 3.11 0 3.2: 20 10 3.12 0—4 3.221 5—8 3.26 2—5 3.226 0 3.51 0 3.227 0—3 3.52 0—3 3.231 4—5 3.54 0—3 3.232 5 3.55 0 3.233 3—5 3.70 0 3.234 7—9 3.75 0 3.263 0—4 3.78 0 3.267 0—2 3.85 7-8 3.274 0 3.86 0

compound number attack% compound number attack% 3.279 11 5.70 2—5 3.287 5—7 5.71 0 3.292 5—8 5.73 0 3.311 0 5.75 0 3.314 0 5.76 0 3.340 10 5.77 3—6 3.348 10—15 5.78 0 3.373 0—3 5.106 0 4.2 5-7 5.107 7—10 4.15 0 6.1 0 4.23 2—5 6.8 0 4.50 0 6.17 0 4.57 0 6.79 0—3 4.59 0 6.80 5—8 4.6Θ 2-5 7.3 0 4.77 0 7.7 0 4.78 0 7.21 0—2 4.81 0 7.33 0 4.89 0 7.34 4-5 4.90 0 8.66 0 4.91 0 8.69 0—5 4.92 0 8.72 5—7 4.93 0 10.7 0 4.94 0 4.113 3—5 AND 98—100 4.116 2—3 (B) 100 ALIGN! 5.13 0 C 97-100 5.14 0 D 96—100 5.36 0 control 100 ALIGN! 5.40 0 Example 21 active substance. Pio · 24 hours Plants infect fungi with conidia suspension. Residual protective effect against scab- The plants are then incubated for 5 days of apple trees (Venturia inaequalisj at 90 to 100% relative humidity and chasing apple trees for another 10 days is placed in glass temperature at 20 to 24 Deň: 32 ° C. The attack- Apple seedlings with 10 up to 20 cm long- The sags are counted 15 days after infection. You- be full of fresh shoots Spray suis- the results of the test are evident from the following table- pensions (concentration 0.06% active substance), ky: which was made of wettable powder.

Effect against Venituriia imaequalis

compound number attack% compound number  attack% 1.4 5—7 4.59 11—15 1.9 7—10 4.66 7—15 1.17 5—8 4.78 0 1.24 5—8 4.81 0—5 1.28 9—13 4.89 5—10 2.17 7—9 4.90 0—3 3.1 8—11 4.91 8 3.6 10 4.92 0—3 3.7 5—10 4.93 Í4—16 3.11 7—10 4.94 13—14 3.52 5—12 4.113 0 3.55 0 4.116 0 3.85 5—10 5.13 0—5 3.86 0 5.14 5—7 3.156 5—9 5.36 5—10 3.160 8—13 5.40 5—10 3.164 8—13 5.70 8—10 3.172 7—13 5.73 8—11 3.176 8—14 5.75 8—11 3.177 5—9 5.76 10—15 3.213 5—10 6.1 5—10 3.221 5—9 6.8 0—5 3.233 6—11 10.7 7—9 3.314 14—15 AND 100 ALIGN! 4.15 8—9 (B) 100 ALIGN! 4.23 7—10 G 100 ALIGN! 4.50 0 D 100 ALIGN!

Untreated but infected shoots show 100% infestation with Venturia iniaequalis.

Example 22

Effect against gray mold (Botrytis cinerea) on bean

Residual protec tive effect

About 10 cm tall bean plants have effects against Botrytis cinerea:

Compound number% sprayed with a suspension (at a concentration of 0.02% active ingredient) which was made from a wettable powder of the active ingredient. After 48 hours, the treated plants are infected with a conidia suspension of the fungus. After incubating the infected plants for 3 days at 95-100% relative humidity and 21 ° C, the fungal infestation is assessed. In many cases, the compounds of Tables 1 to 10 suppress fungal infection very potently. The results are shown in the following table:

Compound number%

1.1 2—5 1.4 0 1.9 2—5 1.17 2—5 3.6 4—5 3.7 0 3.12 5—10 3.51 5—15 3.55 5—10 3.86 0 3.226 5-7 3.231 5—10 3.267 8—12 3.311 5—10 4.15 0—3 4.50 5—7 4.59 0 4.66 0 4.78 5-7

4.90 10—12 4.91 10—12 4.92 9—11 4.93 0 4.113 0—5 5.13 0—3 5.36 0 5.40 5—10 5.70 7—10 5.71 0—5 5.73 2—5 5.75 0 5.76 15—20 5.78 25 6.1 8—10 6.8 5—10 7.3 5—11 7.33 0 8.72 0

»

Plants that have been treated with compounds A, B, C or D, as well as untreated control plants, show 100% fungal attack, Botrytis cinerea.

None of the comparative products A to D that are commercially available achieved a remarkable fungicidal effect at the low test concentrations used in these tests. In all the tests, more than 90% of the infections were achieved and thus practically did not differ from the untreated control plants.

Claims (7)

SUBJECT A process for the preparation of novel arylphenyl ethers derivatives of general formula I wherein: Y is —CH = or —N—, R _a and R _b are each independently hydrogen, hialloigen, C 1 -C 3 alkyl or methoxy, U and V are independently C 1 -C 3 alkyl or together form one of the following alkylene groups of the invention wherein: R 1 and R ₂ are each independently hydrogen, C 1 -C 3 alkyl or -CH ₂ -Z-R ₇ where Z is oxygen or sulfur; and R ₇ is hydrogen, C 1 -C 3 alkyl, C 3 -C 4 alkenyl, methoxyethyl, phenyl, chloro-methyl-substituted phenyl, benzyl or chloro or methyl-substituted benzyl, R ₄ , R ₄ and R ₅ are each independently hydrogen or C 1 -C 3 alkyl, the total number of carbon atoms in the R 5 substituents _; , R ₄ and R _{s shall} not exceed 6 a Ar represents a group wherein R _c , R d and R _c are each independently hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 3 alkoxy, trifluoromethyl or nitro, as well as their acid addition salts and copper complexes thereof, characterized in that the compound of formula X is CH 2 -n. / (X) v v nemz Ar, R _a , R b, U, V and Y are as defined above, intramolecularly decarboxylated, whereupon optionally the free compound obtained above. by conversion with torgauic acid or an inorganic acid and the acid addition salt, the acid addition salt obtained is optionally converted with the carbonate, bicarbonate or alkali metal hydroxide into the free compound, or the free compound obtained (optionally the acid addition salt obtained is converted by reaction with copper salts to complex with copper. 2. A process according to claim 1, wherein the corresponding compounds of formula X are used as starting materials to form compounds of formula I in which: Y represents —CH = or · -, N =, R _a and R _b independently represent a hydrogen atom, a halogen atom (or an alkyl group having 1 to 3 carbon atoms, Ar represents a group of the formula wherein R _c , R _d and R _e are each independently hydrogen, halogen or C 1 -C 3 alkyl, and U and V have the meaning given in point 1. 3. A process according to claim 1, wherein the corresponding compounds of formula (X) are used as starting materials to give compounds of formula (I) in which: U and V are, independently of one another, an alkyl group having 1 to 3 carbon atoms, or together form one of the following alkylenium groups. whereas R _t, R _2, R _{3 R 4} R and R, are independently hydrogen or alkyl of 1 to 3 carbon atoms and the total carbon atoms in počeit substitueniteeh _{R i,} R ₄ and R ₅ does not exceed the number 6. Ar represents a group of the formula wherein R _c , R i and R _k independently represent a hydrogen atom, a halogen atom, or an alkyl group having 1 to 3 carbon atoms, and Y represents —CH-- or —N—. 4. A process according to claim 1, wherein the corresponding compounds of formula (X) are used as starting materials to give compounds of formula (I) in which: Y is —CH = or - —N—, Ar is as defined in point 1, R ", R _b, R., R | and R _e are independently of each other an atom, hydrogen, chlorine, bromine, fluorine, methyl, methoxy or nipro, U and V are, independently of one another, a (C 1 -C 3) alkyl group or together form one of the alkylene groups defined in (1), wherein R _b R ₂ , R ₃ and R ₄ , R ₅ are (independently of one another hydrogen or alkyl) C 1 -C 3 or R ₍ is -CH ₂ -O-R ₇ , wherein R ₇ is hydrogen, C 1 -C 3 alkyl, C 3 -C 4 alkenyl or phonyl). 5. A process according to claim 1, wherein the corresponding compounds of formula X are used as starting materials to form 2- [p- (phenoxy) phenyl] -, 2- [1- (1H-1,2,4-triazolyl) methyl] -4-ethyl-1,3-dioxolane, 2- [p- (phenoxy) phenyl] -2- [1- (1H-1,2,4-triazolyl) methyl] -4-methyl-1,3-dioxane, 2- [p- (4'-chlorophenoxy) phenyl] -2- [1- (1H-1,2,4-triazolyl) methyl] -4-ethyl-1,3-dioxolane, 2- [p- (phenoxy) -2-chlorophenyl] -2- [1- (1H-1,2,4-triazolyl) methyl] -4-ethyl-1,3-dioxolane. 6. A process according to claim 1, wherein the corresponding compounds of formula X are used as starting materials to form 2- [p- (3‘, 4‘-dichlorophenoxy) phenyl] -2- [1- (1H-1,2,4-triazolyl) methyl] -4-methoxymethyl-1,3-dioxoilane, 2- [p- (3 ', 4'-dichlorophenoxy) phenyl] -2- [1- (1H-1,2,4-triazolyl) methyl] -4-ethyl-1,3-dioxolane, the complex of 2- [ p- (4'-chlorophenoxy) phenyl] -2- [1- (1H-1,2,4-itriazolylimethyl) -4-ethyl-1,3-dioixolane with copper (II) sulfate, 2- [[2-methyl-4-feinoxy) phenyl] -2- ^{(1-imidazolyl!} Metliyl) -4-ethyl-3-dioixiolanu, 2- [p- (phenoxy) -2-methylphenyl] -2- [1- (1H-1,2,4-triazolylmethyl) -4-ethyl-1,3-dioxolane, 2- [p- (chloro-phenoxy) -2-one-ethylphenyl] -2- [1- (1H-1,2,4-triazolyl) methyl] -4-methyl-1,3-diioxolain, 2- [p- (4‘-chlorophenoxy) phenyl] -2- [1- (1H-1,2,4-thiriazolylimethyl) -3,4-diimethyl-1,3-dioxolane, 2- [p- (4‘-Brophophenoxy) phenyl] -2- [1- (1H-1,2,4-thiriazolyl) methyl] -4-ethyl-1,3-diioxolane, 2- [p- (phenoxy) -2-chlorophenyl] -2- [1- (1H-1,2,4-triazolilyl) methyl] -4-methyl-1, 3-dioxane, 2- [p- (4'-Bromo-phenoxy) phenyl] -2- [1- (1H-1,2,4-triazolyl) methyl] -4-n-piropropyl-1,3-dioxoilane, 2- [p- (4'-trifluorophenoxy] phenyl] -2- [1- (1H-1,2,4-triazolyl) methyl] -4-ethyl-1,3-dioxolane, 2- [1 '- (4'-chlorophenoxy) -2-imethylphenyl] -2- [1- (1H-1,2,4-thiazollyl) methyl] -4-ethyl-1,3-dioxolane, 2- [p- (4'-chlorophenoxy) -2-mnthylf phenyl] -2- (1H-ámidazolylimethylj -4-ethyl-e ^and l, 3-dioxolane. 7. A process according to claim 1, wherein the corresponding compounds of formula (X) are used as starting materials 2- [1 - (4'-chlorophenoxy) -2-chlorophenyl] -2- [1- (1H-1,2,4-triazoilylmethyl) -4-ethyl-1,3-dioxolane, 2- (2-ethyl-4-phenoxy) phenyl] -2- [1- (1H-1,2,4-triazolyl) methyl] -4-methyl-1,3-dioxolane with nitric acid.