NZ202385A - 2-imidazolylmethyl-2-phenyl-1,3-dioxolanes and fungicidal compositions - Google Patents

Abstract

1. 2-Imidazolylmethyl-2-phenyl-1,3-dioxolanes of the formula (I) see diagramm : EP0080071,P9,F12 in which R represents the groupings see diagramm : EP0080071,P9,F1 and see diagramm : EP0080071,P9,F2 R**1 represents hydrogen or alkyl with 1 to 4 carbon atoms ; R**2 represents hydrogen, alkyl with 1 to 4 carbon atoms or halogenoalkyl with 1 to 2 carbon atoms and 1 to 5 identical or different halogen atoms ; X represents hydrogen, fluorine, chlorine, bromine and alkyl or alkoxy with in each case 1 to 4 carbon atoms ; n represents 1 and Y represents substituted phenyl, possible substituents being : halogen or alkyl with 1 to 4 carbon atoms, and their plant-tolerated acid addition salts and metal salt complexes.

Description

New Zealand Paient Spedficaiion for Paient Number £02385 202385 Priority EJateJ#): Can^.h-Pi wpas-sSsatior: Fiiod: f.'Ji".?<? Ctessr: CP??A9?/°.ty. dPW.fflf?.

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NEW ZEALAND Patents Act, 1953 COMPLETE SPECIFICATION "2-Imidazolylmethyl-2-phenyl-l, 3-dioxolanes, a process for their preparation, and their use as fungicides^" We, BAYER AKTIENGESELLSCHAFT, a Company registered under the laws of the Federal Republic of Germany, of Leverkusen, Germany, do hereby declare the invention, for which we pray that a Patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement -1- (Followed by 1A.) -lA- Type la The present invention relates to certain new 2-imidazolylmethyl-2-phenyl-l ,3-dioxolanes, to a process for their production and to their use as fungicides.

It has already been disclosed that certain tri-5 azolylalkanols possess fungicidal properties (see U.K. Patent Specification No. 1464,224). Thus, for example, 4-chlorophenyl-(1,2, 4-triazol-l-yl-methyl)-carbinol can be used for combating fungi. However, the action of this substance is not always adequate, 3_q particularly when low amounts are used.

Furthermore, it has already been disclosed that certain imidazolyl-alkanols exhibit good actions against fungi which are pathogenic to humans (see 7th Med. Chem. 12, 784-791 (1969)). Thus, for example, 4-bromophenyl-25 (imidazol-l-yl-methyl)-carbinol and 2,4-dichlorophenyl-(imidazol-l-yl-methyl)-carbinol can be employed for this indication. However, the action of these compounds against phytopathogenic fungi is not always satisfactory. the 2-imidazolylmethyl-2-phenyl-l,3-dioxolanes of the general formula The present invention now provides, as new compound (I) / in which R represents a grouping the the general formula or 1 R: represents a hydrogen atom or an alkyl group, 2 R represents a hydrogen atom or an alkyl or halogenoalkyl group, Bu A 21—3&3- /C £0238 X represents a hydrogen or. halogen, atom or, an alkyl, alko.xy, nitro or cyano group, n is 1 or 2, and Y represents an optionally substituted phenoxy or substituted phenyl group, and the physiologically acceptable acid addition salts and metal salt complexes thereof.

The compounds of the formula (I) can occur in various stereoisomeric forms; preferably, they occur in the form of stereoisomer mixtures.

According to the present invention we further provide a process for the production of a compound of the present invention characterised in that a 1,3-dioxolane derivative of the general formula - Z (II) in which 1 2 R, R and R have the meanings given above and Z. represents, a halogen, atom or a grouping of the 3 general formula -O-SC^-R , wherein 3 R represents a methyl or p-methylphenyl group, is reacted with an imidazole of the general formula N (III) M - N in which M represents a hydrogen atom or an alkali metal, in the presence of a diluent and, if appropriate, in the presence of an acid-binding agent, and, if desired, an acid or a metal salt is then added onto the resulting compound of the formula (I)... ha A 21 387 Finally, it has been found that the 2-imi.dazolyl-2-pheny1-1,3-dioxolanes according to the invention, of the formula (I), and plant-tolerated acid addition salts and metal salt complexes possess powerful fungicidal properties.

Surprisingly, the substances according to the invention exhibit a better fungicidal activity than the compounds 4-chlorophenyl-(1,2,4-triazol-l-yl-methyl)-carbinol, 4-bromophenyl-(imidazol-l-yl-methyl)-carbinol and 2,4-dichlorophenyl-(imidazol-l-yl-methyl)-carbinol, which are known from the prior art and which are constitutionally similar substances with the same direction of action.

Preferred 2-imidazolyl-2-phenyl-l,3-dioxolanes of formula (I) according to the present invention are those in which R represents a grouping of the general formula cf3 y x3§>- or 1 n R represents, a hydrogen., atom or, an, alkyl group having 1 to 4 carbon atoms; 2 R represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or a halogenoalkyl group having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms (such as fluorine atoms and chlorine atoms); X represents a hydrogen, fluorine, chlorine or bromine atom or an alkyl or alkoxy group, each having 1 to 4 carbon atoms; n : is 1; and Y represents an optionally substituted phenoxy or substituted phenyl group, the following being suitable substituents: halogen or alkyl having 1 to 4 carbon atoms. r i /■ Particularly preferred:compounds of the formula (I) are those in which R represents a grouping of the general formula CF 3 ^ Y- or X ^ ' ' n R^" represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, 2 R represents a hydrogen atom or an unsubstituted alkyl group having 1 to 4 carbon atoms, and a 10 methyl group which is substituted by fluorine, or chlorine; X represents a hydrogen, fluorine or chlorine atom or a methyl group; n is 1; and Y represents an optionally substituted phenoxy or substituted phenyl group (fluorine, chlorine and methyl being mentioned as substituents).

Preferred substances according to the invention are also, acid addition salts of. 2-imidazolylmethyl-2-phenyl- 1,3-dioxolanes of the formula (I), in which R, R^" and 2 R have the meanings mentioned as being preferred. Amongst these substances, particularly preferred acid addition salts are those which are formed by the addition of hydrohalic acid (such as hydrobromic acid, and especially, hydrochloric 25 acid), phosphoric acid, nitric acid, sulphuric acid, monofunctional and bifunctional carboxylic acids and hydroxycarboxylic acids (such as acetic acid, maleic acid, succinic acid, fumaric acid, tartaric acid, citric acid, salicyclic acid, sorbic acid and lactic acid) and sulphonic 30 acids (such as p-toluenesulphonic acid and naphthalene-1,5-disulphonic acid)^ Metal salt complexes of 2-imidazolylmethyl-2-phenyl-iioxolan Lu A 21 1 2 1,3-dioxolanes of the formula (I) ,. m whi.ch R,. R and R 2023 85 have the meanings mentioned"as being preferred, are. also preferred substances according to the invention. Amongst these substances/ particularly preferred metal salt complexes are those which contain, as cations, metals of 5 main groups II to IV or sub-groups I and II or IV to VIII of the periodic table of elements, copper, zinc, manganese, magnesium, tin, iron and nickel being mentioned as examples Anions of these metal salt complexes are preferably those which are derived from hydrohalic acids, in 10 particular hydrochloric acid and hydrobromic acid, and also phosphoric acid, nitric acid and sulphuric acid.

If, for example, 2-bromoethyl-2-(4-chloro-2-tri-fluoromethyl-phenyl)-1,3-dioxolane and imidazole are used as starting materials, the course of the reaction in the 15 process according to the invention can be represented by the following equation: H2B r H-N CI Base -HBr Preferred 1,3-dioxolane derivatives of formula (II) required as starting materials in carrying out the process 1 2 according to the invention are those in which R, R and R have the meanings which have already been mentioned for these radicals in the description of the preferred and particularly preferred compounds according to the invention and Z represents a chlorine or bromine atom or a grouping 25 of the general formula -O-SC^-R^, wherein R"^ represents a methyl or p-methylphenyl group.

The 1,.3-dioxolane derivatives of. the formula (II) are ?1 1H7 0 n o 7 C \ novel and form a further subject of the present invention.

The present invention thus provides, as new compounds, the compounds of formula (II), as defined above.

According to the present invention we further provide 5 a process for the production of compounds of formula (II) characterised in that a keto derivative of the general formula R-C-CH,-Z (IV) II ^ 0 in which R and Z have the meanings given above, is reacted with a diol of.the general formula ho oh (v) R2 in which R-*- and R^ have the meaning given above, ;15 in the present of an inert organic solvent (such as toluene) , and in the. presence of, a strong, acid, as the catalyst (such as p-toluenesulphonic acid) at a temperature between 80 and 100°C, if appropriate under elevated pressure. ;20 The keto derivatives of the formula .(IV) a,re known ;(see, for example, U.K. Patent Specification No.1464,224), ;or are obtained in a generally known manner, by reacting the corresponding ketones, for example, with chlorine, or bromine in the presence of an inert organic 25 solvent (such as an ether or a chlorinated or unchlorinated hydrocarbon) at room temperature, or reacting them with customary chlorinating agents (such as sulphuryl chloride) at 20 to 60°C. The sulphonic acid derivatives of the compounds of the formula (IV) can likewise be prepared 30 according to known methods. ;-tii ft ?1. 107 ;K\d /• • - ' >_ ,• ;-7- ;The diola of the formula (V) . are generally known compounds of organic chemistry; they are obtained in a generally known manner. ;Preferred imidazoles of formula (III) additionally 5 to be used as starting materials for the process according to the invention are those in which M represents a hydrogen atom, sodium or potassium. ;The imidazoles of the formula (III) are generally known compounds of organic chemistry. ;10 Suitable diluents for the process according to the invention are inert organic solvents. These preferably include amides, such as dimethylformamide or dimethylacetamide; and also dimethylsulphoxide or hexa-methylphosphoric acid triamide. ;15 The process according to the invention is carried out, if appropriate, in the presence of an acid-binding agent. It is possible to add- all the customarily usable inorganic or organic.acid-binding agents, such as alkali metal carbonates (for example sodium carbonate, 20 potassium carbonate and sodium bicarbonate), or such as lower tertiary, alkylamines, cyclp.alk.ylamin.es, or aralkyl-amines (for example triethylamine, N,N-dimethylcyclo-hexylamine, dicyclohexylamine and N,N-dimethylbenzylamine, and furthermore pyridine and diazabicyclooctane). Pre-25 ferably, an appropriate excess of imidazole is used. ;In carrying out the process according to the invention, the reaction temperatures can be varied within a relatively wide range. In general, the reaction is carried out at a temperature between 20 and 150°C, 30 preferably between 60 and 150°C. ;In carrying out the process according to the invention 1 to 2 mol of the imidazole of the formula (III) and, if appropriate, 1 to 2 mol of an acid-binding agent are,preferably employed per mol of the compounds of the 35 formula (II) . The compounds of. the formula (I) are ;21 307 ;20238 ;-8- ;isolated in a customary manner. In some cases, it is advantageous to prepare the compounds of the formula (I) in pure form via their salts. ;Those acids which have already been mentioned in 5 connection with the description of the acid addition salts according to the invention as being preferred acids are preferred for the preparation of plant-tolerated acid addition salts of the compounds of the formula (I). ;These acid addition salts of the compounds of the 10 formula (I) can be obtained in a simple manner by customary methods of salt formation for example by dissolving a compound of the formula (I) in a suitable inert solvent and adding the acid,for example hydrochloric acid, and they can be isolated in a known manner, for example by 15 filtration, and if appropriate purified by washing with an inert organic solvent. ;Salts of those anions and cations which have already been mentioned in connection with the description of the metal salt complexes according to the invention as being 20 preferred are preferred for the preparation of metal salt complexes of compounds of the formula (I). ;The metal salt complexes of compounds of the formula (I) can be obtained in a simple manner by customary processes, thus, for example, by dissolving the metal 25 salt in an alcohol, for example ethanol, and adding the solution to the compound of the formula (I). The metal salt complexes can be isolated in a known manner, for example by filtration, and if appropriate purified by reerystallisation. ;30 The active compounds according to the invention exhibit a powerful microbicidal action and can be employed in practice for combating undesired micro-organisms. The active compounds are suitable for use as plant protection agents. ;35 Fungicidal agents in plant protection are employed ;for combating Plasmodiophorc>mycetes, Oomycetes, Chytridio-mycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes. ;The good toleration by plants, of the active ocmpounds, 5 at the concentrations required for combating plant diseases, permits treatment of above-ground parts of plants, of vegetative propagation stock and seeds, and of the soil. ;As plant protection agents, the active compounds according to the invention can be used with particularly ]_q good success for combating Podosphaera species, such as against the powdery mildew of apple causative organism (Podosphaera leucotricha), and for combating cereal diseases, such as against the powdery mildew of cereals causative organism (Erysiphe graminis) and against the 15 stripe disease of barley (Helminthosporium gramineum). The compounds according to the invention also exhibit a good in vitro action, in particular against pathogens in rice plants. ;When used in appropriate concentrations, the substances 20 according to the invention also exhibit plant growth-regulating properties. ;The active compounds can be converted to the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, foams, 25 pastes, soluble powders, granules, aerosols, suspension-emulsion concentrates, seed-treatment powders, natural and synthetic materials impregnated with active compound, very fine capsules in polymeric substances and in coating compositions for seed, and formulations used with burning 30 equipment, such as fumigating cartridges, fumigating cans and fumigating coils as well as ULV cold mist and warm mist formulations. ;-10- ;0: / ;These formulations may -be produced in known manner, for example by mixing the active compounds with extenders, that is to say liquid or liquefied gaseous or solid diluents or carriers, optionally with the use of surface-active 5 agents, that is to say emulsifying agents and/or dispersing agents and/or foam-forming agents. In the case of the use of water as an extender, organic solvents can, for example, also be used as auxiliary solvents. ;As liquid diluents or carriers, especially solvents, 10 there are suitable in the main, aromatic hydrocarbons, ;such as xylene, toluene or alkyl naphthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic or alicyclic hydrocarbons, such as cyclohexane 15 or paraffins, for example mineral oil fractions, alcohols, such as butanol or glycol as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, ;methyl isobutyl ketone or cyclohexanone, or strongly polar solvents, such as dimethyIformamide and dimethyl-20 sulphoxide, as well as water. ;By liquefied gaseous diluents or carriers are meant liquids which would be gaseous at normal temperature and under normal pressure, for example aerosol propellants, ;such as halogenated hydrocarbons as well as butane, propane, 25 nitrogen and carbon dioxide. ;As solid carriers there may be used ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as highly-dispersed silicic 30 acid, alumina and silicates. As solid carriers for granules there may be used crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, 35 coconut shells, maize cobs and tobacco stalks. ;le, a 21 ;07' ;20238 ;-11- ;As emulsifying and/or foam-forming agents there may be used non-ionic and anionic emulsifiers, such as polyoxy ethylene-fatty acid esters, polyoxyethylene-fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulphonates, alkyl sulphates, aryl sulphonates as well as albumin hydrolysis products. Dispersing agents include for example, lignin sulphite waste liquors and methyl-cellulose . ;Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, can be used in the formulations. ;It is possible, to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs or metal phthalocyanine dyestuffs and trace nutrients, such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc. ;The formulations in general contain from 0.1 to 95 per cent by weight of active compound, preferably from 0.5 to 90 per cent by weight. ;The active compounds according to the invention can be present in the formulations or in the various use forms as a mixture with other known active compounds, such as fungicides, bactericides, insecticides, acaricides, nematicides, herbicides, bird repellants, growth factors, plant nutrients and agents for improving soil structure. ;The active compounds can be used as such or in the form of their formulations or the use forms prepared therefrom by further dilution, such as ready-to-use solutions, emulsions, suspensions, powders, pastes and granules. They are used in the customary manner, for example by watering, immersion, spraying, atomising, misting, vaporising, injecting, forming a slurry, brushing on, dusting, scattering, dry dressing, moist dressing, wet Lu-A ;202 CiB j ;10 ;-12- ;dressing, slurry dressing or encusting. ;Especially in the treatment of parts of plants, the active compound concentrations in the use forms can be varied within a substantial range. They are, in general, between 1 and 0.0001% by weight, preferably between 0.5 and 0.001%. ;In the treatment of seed, amounts of active compound of 0.001 to 50 g per kilogram of seed, preferably 0.01 to 10 g are generally required. ;For the treatment of soil, active compound concentrations of 0.00001 to 0.1% by weight, preferably 0.0001 to 0.02% by weight are generally required at the place of action. ;The present invention also provides fungicidal composition containing as active ingredient a compound -*■5 of the present invention in admixture with a solid or liquefied gaseous diluent or carrier or in admixture with a liquid diluent or carrier containing a surface-active agent.

The present invention also provides a method of 20 combating fungi which comprises applying to the fungi or to a habitat thereof, a compound of the present invention alone or in the form of a composition containing as active ingredient a compound of the present invention in admixture with a diluent or carrier.

The present invention further provides crops protected from damage by fungi by being grown in areas in which immediately prior to and/or during the time of the growing a compound of the present invention was applied alone or in admixture with a diluent or carrier. 50 It will be seen that the usual methods of providing a harvested crop may be improved by the present invention.

The preparation and the use of the active compounds according to the invention are illustrated by the Examples which follow. 55 jfrA'Jl 7%T Preparative Examples Example 1 cf3 /=N CH2 - N 0 0 x HC1 1 1 3.9 g (0.0116 mol) of 2-bromomethyl-2-(4-chloro-2-5 trifluoeomethyl-phenyl)-1,3-dioxolane and 2.4 g (0.0348 mol) of imidazole in 50 ml of dimethylacetamide were heated under reflux for 4 days. After the reaction mixture had cooled, it was dissolved in water and the solution was extracted with ether. The ether phase was washed with ]_g water, dried over sodium sulphate and concentrated.

Ethereal hydrochloric acid was added to the residual oil, and the latter was brought to crystallisation by trituration . 2-(4-Chloro-2-trifluoromethyl-phenyl)-2-(imidazol-l-yl-methyl) -1 , 3-dioxolane hydrochloride of melting point 15 174 to 83°C was obtained.

Preparation of the starting material g (0.12mol) of 4-chloro-2-trifluoromethyl-phenacyl bromide and 9 g (0.15 mol) of glycol were heated 20 in a water separator for 24 hours with 1.5 g of p-toluene-sulphonic acid in 80 ml of toluene, in the presence of 20 ml of butanol. After the reaction mixture had cooled, it was washed successively with dilute aqueous sodium hydroxide solution and with water, dried over 25 -irti A 21 3 s 1 cf3 0 0 202385 sodium sulphate and concentrated. 29.6 g (74% of theory) of crude 2-bromomethyl-2-(4-chloro-2-trifluoromethyl-phenyl)-1,3-dioxolane were obtained as an oil, which was directly reacted further. 1 ml of acetic acid was added to 22.3 g (0.1 mol) of 4-chloro-2-trifluoromethyl-acetophenone in 200 ml of chloroform, and the mixture was warmed to 40°C. 5.1 ml (0.1 mol)- of bromine in 50 ml of chloroform were added 10 dropwise at this temperature. The reaction mixture was stirred until the evolution of gas had ceased. After the mixture had cooled, it was washed successively with water and aqueous sodium bicarbonate solution, dried over sodium sulphate and concentrated. 29.4 g (97% of theory) 15 of crude 4-chloro-2-trifluoromethyl-phenacyl bromide were obtained as an oil, which is directly reacted further.

The compounds of the formula /=N which are listed in Table 1 below were also prepared according to the method given in Example 1: La A 21 3 0 7 2 3 4 6 7 8 9 11 12 13 14 202385 r R- R' Physical constants CI cl- cf cf CI CI ^0- ci Cl CI Cl Cl -€H> cf ch3 ch2ci c2hs h ch3 h ch2ci h c2h5 h ch3 h ch2ci h c2h5 h ch3 ch3 ch.-t ch- ch- viscous oil viscous oil viscous oil ra. p . : 2 2 0 ° C (xHCl) viscous oil (xHCl) viscous oil viscous oil viscous oil viscous oil viscous oil viscous oil viscous oil viscous oil ch3 viscous oil /r,"^ The fungicidal activity of the compounds of this invention is illustrated by the following biotest Examples, In these Examples, the compounds according to the present invention are each identified by the number (given in brackets) of the corresponding preparative Example, which will be found later in this specification.

The known comparison compounds are identified as follows: un (a) = - ch2 - n OH ^rN N"= 0H 8) =8t-<^)-(1:h-ch2-n _ Cl OH (C) =C1-<|0) iH-CH2-N -N Example A Erysiphe test (barley)/protective/ Solvent: 100 parts by weight of dimethylformamide Emulsifier :. 0.25 part by weight of. alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound was mixed with the stated amounts of solvent and emulsifier, and the concentrate was diluted with water to the desired concentration .

To test for protective activity, young plants were sprayed with the preparation of active compound until dew-moist. After the spray coating had dried on, the Ll A 21 3Q7' 3 % 5 ~ .17 plants were dusted with spores of Erysiphe graminis f.sp. hordei.

The plants were placed in a greenhouse at a temperature of about 20°C and a relative atmospheric 5 humidity of about 80%, in order to promote the development of powdery mildew pustules.

Evaluation was carried out 7 days after the inoculation.

In this test, a clearly superior activity compared 10 with the prior art was shown, for example, by the compounds (2) and (4).

Example B Drechslera graminea test (barley) / seed treatment (syn. Helminthosporium gramineum) The active compounds were used as dry dressings.

These were prepared by extending the particular active compound with a ground mineral to give a finely pulverulent mixture, which ensured uniform distribution on the seed surface.

To apply the dressing, the infected seed was shaken with the dressing in a closed glass flask for 3 minutes.

The seed was embedded in sieved, moist standard soil and was exposed to a temperature of 4°C in closed 25 Petri dishes in a refrigerator for 10 days. Germination of. the barle'y, and possibly also of. the fungus spores, was thereby initiated. 2 batches of 50 grains of the pregerminated barley were subsequently sown 3 cm deep in standard soil and were cultivated in a greenhouse at a 30 temperature of about 18°C, in seedboxes which were exposed to light for 15 hours daily.

About 3 weeks after sowing, the plants were evaluated for symptoms of stripe disease.

In this test, a clearly superior activity 35 compared with the prior art was shown, for example, by the

Claims (18)

202385 - 18 - compounds (.1 ). and (;2) . Example C Podosphaera test (apple) / protective Solvent: 4.7 parts by weight of acetone 5 Emulsifier: 0.3 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound was mixed with the stated amounts of solvent and emulsifier, and the 10 concentrate was diluted with water to the desired concentration. To test for protective activity, young plants were sprayed with the preparation of active compound until dripping wet. After the spray coating had dried on, 15 the plants were inoculated by dusting with conidia of the powdery mildew of apple causative organism (Podosphaera leucotr icha). The plants were then placed in a greenhouse at 23°C and a relative atmospheric humidity of about 70%. 20 Evaluation was carried out 9 days after the inoculation. In this test, a clearly superior activity compared with the prior art was shown, for example, by the compounds (2), (4) and (1). - 19 - 202335 WHAT V7E CLAIM IS:

1. Compounds which are 2-iniidazolylmethyl-2-phenyl-l,3-dioxolanes of the general formula ch? - n (I) in which 5 R represents a grouping of the general formula cf3 JP- or 1 Xfl R represents a hydrogen atom or an alkyl group, 2 R represents a hydrogen atom or an alkyl or halogenoalkyl group, 10 X represents a hydrogen or halogen atom or an alkyl, alkoxy, nitro or cyano group, n is 1 or 2,or 4 when X is hydrogen, and Y represents an optionally substituted phenoxy or substituted phenyl group, 15 and their physiologically acceptable acid addition salts and metal salt complexes.

2. Compounds according to claim 1, characterised in that R represents a grouping cf3 20 °r X 1 n R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; 2 R represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or. a halogenoalkyl group -&C-A—21 387 J12N0VI984 2D2325 - 20 - having 1 or 2 carbon"atoms, and 1 to 5 identical or different halogen atoms, X represents a hydrogen, fluorine, chlorine or bromine atom, or an alkyl or alkoxy group each 5 having 1 to 4 carbon atoms; n is l,,or .4 when X is hydrogen; and Y represents an optionally substituted phenoxy or substituted phenyl group, the substituents being selected from halogen and alkyl having 1 to 4 10 carbon atoms.

3. Compounds according to claim 1, characterised in that R represents a grouping of the general formula CF3>^ Y' X or 1 Xf1 R represents a hydrogen atom or an alkyl group 15 having 1 to 4 carbon atoms, 2 R represents a hydrogen atom or an unsubstituted alkyl group having 1 to 4 carbon atoms, or a methyl group which is substituted by fluorine or chlorine; 20 X represents a hydrogen, fluorine or chlorine atom or a methyl group; n is l,or 4 when X is hydrogen; and Y represents an optionally substituted phenoxy or substituted phenyl group, the substituents being 25 selected from fluorine, chlorine and methyl.

4. Any one of the compounds according to claim 1 which are hereinbefore specifically identified.

5. A process for the production of a compound according to any of claims 1 to 4, characterised in that a 30 1,3-dioxolane derivative of the general formula ch2 - z (II) J—k ' Lij. A 21 30 7 W4 202385 - 21 - in which 1 2 R, R and R have the same meanings as in claim 1 and Z represents a halogen atom or a grouping of the 3 general formula -O-SC^-R t wherein 3 R represents a methyl or p-methylphenyl group, is reacted with an imidazole of the general formula N| (III) m - n 1 in which M represents a hydrogen atom or an alkali metal, in the presence of a diluent and, if desired, an acid or a metal salt is then added onto the resulting compounds of the formula (I).

6. A process according to claim 5, characterised in that the diluent is an inert organic solvent.

7. A process according to claim 5 or 6, characterised in that the reaction is carried out in the presence of an acid-binding agent. .one

8. A process according to any/o? claims 5 to 7, characterised in that the reaction is carried out at a temperature between 20 and 150°C.

9. A process for the production of a compound according to claim 1, substantially as described in any one of Examples 1 to 15.

10. A compound according to claim 1, whenever produced by a process of any one of claims 5 to 9.

11. A fungicidal composition, characterised in that'it contains as active ingredient a compound according to any of claims 1 to 4 and 10 in admixture with a solid or liquefied gaseous diluent or carrier or in admixture with a liquid diluent or carrier containing a surface-active agent. -/-V L, 21 30" ' > O '"i f: n 22

12. A composition according to claim 11, characterised in that it contains from 0.1 to 95% of the active compound, by weight.

13. A method of combating fungi, characterised in that there is applied to the fungi, or to a habitat thereof, a compound according to any of claims 1 to 4 and 10 alone or in the form of a composition containing as active ingredient a compound according to any of claims 1 to 4 and 10, in admixture with a diluent or carrier.

14. A method according to claim 13, characterised in that a composition is used containing from 1 to 0.0001% of the active compound, by weight.

15. A method according to claim 14, characterised in that a composition is used containing from 0.5 to 0.001% of the active compound by weight.

16. A method according to claim 13, characterised in that the active compound is applied to seed in an amount of 0.001 to 50 g per kg of seed.

17. A method according to claim 16, characterised in that the active compound is applied to seed in an amount of 0.01 to 10 g per kg of seed.

18. A compound according to any one of claims 1 to 4 and 10 when in contact with a crop and/or crop growing area, alone or in admixture with a diluent or carrier. BAYER AKTIENGESELLSCHAFT By Their Attorneys HENRY HUGHES LIMITED