GB2158823A - Fungicidal amino alcohol compounds - Google Patents

Abstract

Compounds of formula: <IMAGE> and stereoisomers thereof, wherein R<1>, R<2>, R<3> and R<4> each represent a hydrogen atom or an alkyl group containing 1 to 4 carbon atoms, R<3> and R<4> can together form a heterocyclic ring other than a morpholine or piperidine ring, X and Y each represent a hydrogen or a halogen atom, or an alkyl, cycloalkyl, alkenyl, alkynyl, aryl, aralkyl, alkoxy, or aryloxy group; and including ester and ether derivatives of the alcohol function; and acid addition salts; have fungicidal activity.

Description

SPECIFICATION Amino alcohol compounds This invention relates to amino compounds useful as fungicides, to a process for preparing them, to fungicidal compositions containing them, and to methods of using them to combact fungi, especially fungal infections in plants.

The invention provides compounds having the general formula (I):

and stereoisomers thereof, wherein R1, R2, R3 and R4 each represent a hydrogen atom or an alkyl group containing 1 to 4 carbon atoms, R3 and R4 can together form a heterocyclic ring other than a morpholine or piperidine ring, X and Y each represent a hydrogen or a halogen atom or an alkyl, cycloalkyl, alkenyl, alkynyl, aryl, aralkyl, alkoxy, or aryloxy group; and ester and ether derivatives of the alcohol function; and acid addition salts thereof.

The compounds have fungicidal activity.

The compounds of the invention contain at least one chiral centre. Such compounds are generally obtained in the form of isomeric mixtures. However, these and other mixtures can be separated into the individual isomers by methods known in the art.

The alkyl and alkoxy groups may be straight or branched chain groups having 1 to 6, eg. 1 to 4, carbon atoms; examples are methyl, ethyl, propyl (n- or iso- propyl) and butyl (n-, sec-, iso or t- butyl). Cycloalkyl groups may be cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.

The alkenyl and alkynyl groups may contain up to 6 carbon atoms.

Examples of suitable substituents for the aryl, aralkyl, and aryloxy, which are preferably phenyl, benzyl and phenoxy, are halogen (eg. fluorine, chlorine, or bromine), C, 5 alkyl [eg. methyl, ethyl, propyl (n-or iso-propyl) and butyl (n-, sec-, iso-, or butyl)1, C1.4 alkoxy (eg. methoxy and ethoxy), haloalkoxy (eg.

trifluoromethoxy), haloalkyl (eg. trifluoromethyl), nitro, phenyl and phenoxy. The phenyl ring may be, for example, unsubstituted or substituted with 1, 2 or 3 ring substituents as defined above. The phenyl may have a single ring substituent in the 2-, 3-or 4-position.

Examples of suitable heterocyclic rings are pyrrolidine, 1,3-imidazole, and 1,2,4-triazole.

The salts can be salts with inorganic or organic acids eg. hydrochloric, nitric, sulphuric, acetic, 4-toluenesulphonic or oxalic acid.

The ester derivatives of the alcohol may be for example acetyl, propionyl, benzoyl and substituted benzoyl; the ether derivative may be, for example, a methyl, ethyl, propyl, butyl, benzyl, or substituted benzyl derivative.

Examples of the compounds of the invention are shown in Table 1. These conform to formula I.

Table 2

~~~~ l Compound X Y R1 R2 R3 R4 Melting No. ~ Point ('C) 1 I t-C4119 II C113 ii -(cff2)4- Oil 2 t-C4219 If C113 It c2ii5 | C2115 oil 3 t-C4Hg ii C113 II C112-jC3111 CI12-iC3H7 Oil 4 t-C4119 H Cull3 II -CH=CH-N=CH- 122-124 5 1-C3lS7 ii Cll3 H C2ll5 1 c2115 6 i-C3H7 ii Clef 3 ii -(CH2)4 7 t-c4119 H C113 if -CH=N-CH=N- Oil O C1 H C113 H C2H5 | C2H5 9 C1 fi Cull3 II -(CH2)4 10 C1 II Cl!3 fl -CH=N-CH=N Compounds of general formula (I):

can be prepared by treatment of an epoxide of general formula (all):

wherein X, Y, R1 and R2 are as defined above, with an amine of general formula (III):

wherein R3 and R4 are as defined above, in the presence of a convenient solvent such as ethanol or tetrahydrofuran, or, preferably, in the absence of a solvent at a temperature of 20 -100 C.

The epoxides (II) can be prepared by treating an aldehyde of general formula (1V):

with dimethyl oxosulphonium methylide (Corey and Chaykovsky,J.Amer. Chem. Soc, 1965,87,1353) or dimethyl sulphonium methylide (Corey and Chaykovski, J. Amer. Chem. Soc., 1962,843782) using methods set out in the literature.

The aldehydes of general formula (IV) can be prepared by methods set out in the literature.

The esters and ethers can be prepared from the parent alcohol compound (I) by successive treatment with a base (preferably sodium hydride) and a suitable alkyl, alkenyl, alkynyl, or acyl halide (preferably chloride, bromide, or iodide) in a suitable solvent such as dimethyl formamide or tetrahydrofuran.

The salts of the compounds ofthe general formula (I) can be prepared from the latter by known methods.

The compounds, salts and metal complexes are active fungicides, particularly against the diseases: The compounds, salts and metal complexes are active fungicides, particularly against the diseases: Piricularia oryzeae on rice Puccinia recondita, Puccinia striiformis and other rusts on wheat, Puccinia hordei, Puccinia striiformis and other rusts on barley, and rusts on other hosts eg. coffee, apples, apples, vegetables and ornamental plants Erysiphe graminis (powdery mildew) on barley and wheat and other powdery mildews on various hosts such as Sphaerotheca fuliginea on cucurbits (eg. cucumber), Podosphaera leucotricha on apples and Uncinula necatoron vines, Helminthosporium spp. and Rhynchosporium spp. on cereals Cercospora arachidicola on peanuts and other Cercospora species on for example sugar beet, bananas and soya beans Botrytis cinerea (grey mould) on tomatoes, strawberries, vines and other hosts, Venturia inaequalis (scab) on apples.

Some of the compounds have also shown a broad range of activities against fungi in vitro. They have activity against various post-harvest diseases on fruit (eg. Penicillium digatatum and italicum on oranges and Gloeosporium musarum on bananas). Further some of the compounds are active as seed dressings against: Fusarium spp., Septoria spp., Tilletia spp. (ie. bunt, a seed borne disease of wheat), Ustilago spp., Helminthosporium spp. on cereals, Rhizoctonia solanion cotton and Corticium sasakiion rice.

The compounds can move acropetally in the plant tissue. Moreover, the compounds can be volatile enough to be active in the vapour phase against fungi on the plant.

The compounds are also useful for the treatment of candidiasis and human dermatophyte infections. The compounds are also active against bacterial diseases of plants, especially bacterial blight of rice caused by Xanthomonas campestris oryzae.

The compounds may also be useful in preventing frost damage in countries where there s significant snow cover in the winter since then the treated plants would remain below snow cover during the cold weather.

The compounds may be used as such for fungicidal purposes but are more conveniently formulated into compositions for such usage. The invention thus provides a fungicidal composition comprising a compound of general formula (I) as hereinbefore defined, or a salt, metal complex, ether or ester thereof; and, optionally, a carrier or diluent.

The invention also provides a method of combating fungi, which comprises applying to a plant, to seed of a plant, or to the locus of the plant or seed, a compound, or salt, metal complex, ether or ester thereof, as hereinbefore defined.

The compounds, salts, metal complexes, ethers and esters can be applied in a number of ways, for example they can be applied, formulated or unformulated, directly to the foliage of a plant, or they can be applied also to bushes and trees, to seeds or to other medium in which plants, bushes or trees are growing or are to be planted, or they can be sprayed on, dusted on or applied as a cream or paste formulation, or they can be applied as a vapour; or as slow release granules. Application can be to any part of the plant, bush or tree, for example to the foliage, stems, branches or roots, or to soil surrounding the roots, or to the seed before it is planted; or to the soil generally, to paddy water or to hydroponic culture systems. The invention compounds may also be injected into plants or trees and they may also be sprayed onto vegetation using electrodynamic spraying techniques.

The term "plant" as used herein includes seedlings, bushes and trees. Furthermore, the fungicidal method of the invention includes preventative, protectant, prophylactic and eradicant treatment.

The compounds are preferably used for agricultural and horticultural purposes in the form of a composition. The type of composition used in any instance will depend upon the particular purpose envisaged.

The compositions may be in the form of dusting powders or granules comprising the active ingredient and a solid diluent or carrier, for example fillers such as kaolin, bentonite, kieselguhr, dolomite, calcium carbonate, talc, powdered magnesia, Fuller's earth, gypsum, Hewitt's earth, diatomaceous earth and China clay. Such granules can be preformed granules suitable for application to the soil without further treatment.

These granules can be made either by impregnating pellets of filler with the active ingredient or by pelleting a mixture of the active ingredient and powdered filler. Compositions for dressing seed, for example, may comprise an agent (for example a mineral oil) for assisting the adhesion of the composition to the seed; alternatively the active ingredient can be formulated for seed dressing purposes susing an organic solvent (for example N-methylpyrrolidone or dimethylformamide).

The compositions may also be in the form of dispersible powders, granules or grains comprising a wetting agent to facilitate the dispersion in liquids of the powder or grains which may contain also fillers and suspending agents.

The aqueous dispersions of emulsions may be prepared by dissolving the active ingredient(s) in an organic solvent optionally containing wetting, dispersing or emulsifying agent(s) and then adding the mixture to water which may also contain wetting, dispersing or emulsifying agent(s). Suitable organic solvents are ethylene dichloride, isopropyl alcohol, propylene glycol, diacetone alcohol, toluene, kerosene, methylnaphthalene, the xylenes, trichloroethylene, furfuryl alcohol, tetrahydrofurfuryl alcohol, and glycol ethers (eg. 2-ethoxyethanol and 2-butoxyethanol).

The compositions to be used as sprays may also be in the form of aerosols wherein the formulation is held in a container under pressure in the presence of a propellant, eg. fluorotrichloromethane or dichlorodifluoromethane.

The compounds can be mixed in the dry state with a pyrotechnic mixture to form a composition suitable for generating in enclosed spaces a smoke containing the compounds.

Alternatively, the compounds may be used in a micro-encapsulated form. They may also be formulated in biodegradable polymeric formulations to obtain a slow, controlled release of the active substance.

By including suitable additives, for example additives for improving the distribution, adhesive power and resistance to rain on treated surfaces, the different compositions can be better adapted for various utilities.

The compounds can be used as mixtures with fertilisers (eg. nitrogen-, potassium- or phosphoruscontaining fertilisers). Compositions comprising only granules of fertiliser incorporating, for example coated with, the compound are preferred. Such granules suitably contain up to 25% by weight of the compound.

The invention therefore also provides a fertiliser composition comprising the compound of general formula (I) or a salt or metal complex thereof.

The compositions may also be in the form of liquid preparations for use as dips or sprays which are generally aqueous dispersions or emulsions containing the active ingredient in the presence of one or more surfactants eg. wetting agent(s), dispersing agents), emulsifying agent(s) or suspending agent(s); or which are spray formulations of the kind suitable for use in electrodynamic spraying techniques. The foregoing agents can be cationic, anionic or non-ionic agents. Suitable cationic agents are quaternary ammonium compounds, for example cetyltrimethyl-ammonium bromide.

Suitable anionic agents are soaps, salts of aliphatic monoesters of sulphuric acid (for example sodium lauryl sulphate), and salts of sulphonated aromatic compounds (for example sodium dodecylbenzenesulphonate, sodium, calcium or ammonium lignosulphonate, butylnaphthalene sulphonate, and a mixture of sodium diisopropyl- and triisopropyl- naphthalene sulphonates).

Suitable non-ionic agents are the condensation products of ethylene oxide with fatty alcohols such as oleyl or cetyl alcohol, or with alkyl phenols such as octyl- or nonyl-phenol and octylcresol. Other non-ionic agents are the partial esters derived from long chain fatty acids and hexitol anhydrides, the condensation products of the said partial esters with ethylene oxide, and the lecithins. Suitable suspending agents are hydrophilic colloids (for example polyvinylpyrrolidone and sodium carboxymethylcellulose), and the vegetable gums (for example gum acacia and gum tragacanth).

The compositions for use as aqueous dispersions or emulsions are generally supplied in the form of a concentrate containing a high proportion of the active ingredient(s), and the concentrate is to be diluted with water before use. These concentrates often should be able to withstand storage for prolonged periods and ater such storage be capable of dilution with water in order to form aqueous preparations which remain homogeneous for a sufficient time to enable them to be applied by conventional and electrodynamic spray equipment. The concentrates may conveniently contain up to 95%, suitably 10-85%, for example 25-60%, by weight of the active ingredient(s).These concentrates suitably contain organic acids (eg. alkaryl or aryl sulphonic acids such as xylenesulphonic acid or dodecyl benzenesulphonic acid) since the presence of such acids can increase the solubility of the active ingredient(s) in the polar solvents often used in the concentrates. The concentrates suitably contain also a high proportion of surfactants so that sufficiently stable emulsions in water can be obtained. After dilution to form aqueous preparations, such preparations may contain varying amounts of the active ingredient(s) depending upon the intended purpose, but an aqueous preparation containing 0.0005% or 0.01% to 10% by weight of active ingredient(s) may be used.

The compositions of this invention can comprise also other compound(s) having biological activity, eg.

compounds having similar or complementary fungicidal activity or compounds having plant growth regulating, herbicidal or insecticidal activity.

The other fungicidal compound can be, for example, one which is capable of combating ear diseases of cereals (eg. wheat) such as Septoria, Gibberella and Helminthosporium spp., seed and soil borne diseases and downy and powdery mildews on grapes and powdery mildew and scab on apple etc. These mixtures of fungicides can have a broader spectrum of activity than the compound of general formula (I) alone; further the other fungicide can have a synergistic effect on thefungicidal activity of the compound of general formula (I).Examples of the other fungicidal compound are imazalil, benomyl, carbendazim, thiophanatemethyl, captafol, captan, sulphur, triforine, dodemorph, tridemorph, pyrazophos, furaiaxyl, ethirimol, tecnazene, dimethirimol, bupirimate, chlorothalonil, vinclozolin, procymidone, iprodione, metalaxyl, forsetyl-aluminium, carboxin, oxycarboxin, fenarimol, nuarimol, fenfuram, methfuroxam, nitrothalisopropyl, triadimefon, thiabendazole, etridiazole, triadimenol, biloxazol, dithianon, binapacryl, quinomethionate, guazitine, dodine, fentin acetate, fentin hydroxide, dinocap, folpet, diclofluanid, ditalimphos, kitazin, cycloheximide, dichlobutrazol, a dithiocarbamate, a copper compound, a mercury compound, 1-(2-cyano-2-methoxyiminoacetyl)-3-ethyl urea, fenapanil, ofurace, propiconazole, etaconazole and fenpropemorph.

The compounds of general formula (I) can be mixed with soil, peat or other rooting media for the protection of plants against seed-borne, soil-borne orfoliarfungal diseases.

Suitable insecticides are Pirimor, Croneton, dimethoate, Metasystox and formothion.

The plant growth regulating compound can be one which controls weeds or seedhead formation, improves the level or longevity of the plant growth regulating activity of the compounds of general formula (I), selectively controls the growth of the less desirable plants (eg. grasses). Some of these other agents can be herbicides.

Examples of suitable plant growth regulating compounds, whcih can display synergy in admixture, or use, with the invention compounds are the gibberellins (eg. GA3, GA4 or GA7), the auxins (eg. indoleacetic acid, indolebutyric acid, naphthoxyacetic acid or naphthylacetic acid), the cytokinins (eg. kinetin, diphenylurea, benzimidazole, benzyladenine or benzylaminopurine), phenoxyacetic acids (eg. 2,4-D or MCPA), substituted benzoic acids (eg. triiodobenzoic acid), morphactins (eg. chlorfluorecol), maleic hydrazide, glyphosate, glyphosine, long chain fatty alcohols and acids, dikegulac, fluoridamid, mefluidide, substituted quaternary ammonium and phosphonium compounds (eg. chlormequat chlorphonium or mepiquatchloride), ethephon, carbetamide, methyl-3,6-dichloroanisate, daminozide, asulam, abscisic acid, isopyrimol, 1 -(4-chlorophenyl) 4,6-dimethyl-2-oxo-1 ,2-dihydropyridine-3-carboxylic acid, hydroxybenzonitriles (eg. bromoxynil), difenzoquat, benzoylprop-ethyl 3,6-dichloropicolinic acid, and tecnazene.

The following Examples illustrate the invention; the temperatures are given in degrees Centigrade ("C) Example 1 This Example illustrates the preparation of 1 -N,N-diethylamino-3-methyl-4-(p-tert.butyl-phenyl)-butan-2-ol (Compound No. 2 of Table 1).

A solution of sodium hydride (0.67g, 0.028 mol) and dry dimethylsulphoxide (30 ml) was warmed at 70"C in a nitrogen atmosphere for 2 hours. The solution was cooled to room temperature; dry tetrahydrofuran (50 ml) added and the mixture cooled to OOC. Trimethylsulphonium iodide (5.79, 0.028 mol) in dry dimethyl sulphoxide (50 ml) was added dropwise at 0 C and the solution stirred at this temperature for two minutes.

To this mixture was added a solution of 3-(p-pert-butyl-phenyl)-2-methyl-propionaldehyde (5g, 0.025 mol) in dry tetrahydrofuran (25 ml). The resulting mixture was stirred at room temperature for 2 hours, poured into water (200 ml) and extracted with diethyl ether (2 x 100 ml). The ethereal extracts were washed with water and dried over anhydrous magnesium sulphate. Removal of the solvent gave 4-(p-tert.butyl-phenyl)-3 methyl-I ,2-epoxybutane (95%) as a pale yellow oil.

A solution of 4-(p-tert.butyl-phenyl)-3-methyl-1 2-epoxybutane (49, 0.018 mol) and diethylamine (3.75 ml, 0.036 mol) in methanol (50 ml) was warmed at 40"C for 9 hours. The mixture was poured into water, extracted with diethyl ether (2 x 100 mol). The ethereal extracts were treated with 2N HCI (50 ml); the aqueous layer was neutralised with saturated sodium bicarbonate solution, re-extracted with diethyl ether and the ethereal solution dried over an hydros magnesium sulphate. Removal of the solvent gave the title compound (0.189) as an oil.

Example 2 This Example illustrates the preparation of 1-imidazole-1-yl-3-methyl-4-(p-tert.butyl-phenyl)-butan-2-ol (Compound No. of Table 1).

A solution of 4-(p-tert.butyl-phenyl)-3-methyl-1 ,2-epoxybutane (5.49, 0.024 mol) and imidazole (6.52g, 0.048 mol) in methanol (50 ml) was heated at 80 C for 24 hours. The mixture was poured into water (100 ml) and extracted with diethyl ether (2 x 100 ml). The ethereal extracts were washed with water (4 x 100 ml), dried over anhydrous magnesium sulphate, and the solvent removed in vacuo to give a white solid.

Recrystallisation from petroleum ether (60:80)/chloroform gave the title compound (2.3g) mp. 122-124"C.

Example 3 An emulsifible concentrate was made up by mixing the ingredients, and stirring the mixture until all the constituents were dissolved.

Compound of Example 1 10% Ethylene dichloride 40% Calcium dodecylbenzenesulphate 5% "Lubrol"L 10% "Aromasol" H 35% Example 4 A composition in the form of grains readily dispersible in a liquid, eg. water, was prepared by grinding together the first three ingredients in the presence of added water and then mixing in the sodium acetate.

The resultant mixture was dried and passed through a British Standard mesh sieve, size 44-100, to obtain the desired size of grains.

Compound of Example 2 50% "Dispersol" T 25% "Lubrol" APN5 1.5% Sodium acetate 23.5% Example 5 The ingredients were all ground together to produce a powder formulation readily dispersible in liquids.

Compound of Example 1 45% "Dispersol" T 5% "Lissapol" NX 0.5% "Cellofas" B600 2% Sodium acetate 47.5% Example 6 The active ingredient was dissolved in a solvent and the resultant liquid was sprayed on to the granules of China clay. The solvent was then allowed to evaporate to produce a granular composition.

Compound of Example 2 5% China clay granules 95% Example 7 A composition suitable for use as a seed dressing was prepared by mixing the three ingredients.

Compound of Example 1 50% Mineral oil 2% China clay 48% Example 8 A dusting powder was prepared by mixing the active ingredient with talc.

Compound of Example 2 5% Talc 95% Example 9 A Col formulation was prepared by ball-milling the constituents set out below and then forming an aqueous suspension of the ground mixture with water.

Compound of Example 1 40% "Dispersol"T 10% "Lubrol" APN5 1% Water Example 10 A dispersible powder formulation was made by mixing together the ingredients set out below and then grinding the mixture until all were thoroughly mixed.

Compound of Example 2 25% "Aerosol" OT/B 2% "Dispersol" A.C. 5% China clay 28% Silica 40% Example ii This Example illustrates the preparation of a dispersible powder formulation. The ingredients were mixed and the mixture then ground in a comminution mill.

Compound of Example 1 25% "Perminal" BX 1% "Disparsol" T 5% Polyvinylpyrrolidone 10% Silica 25% China clay 34% Example 12 The ingredients set out below were formulated into a dispersible powder by mixing then grinding the ingredients.

Compound of Example 2 25% "Aerosol" OT/B 2% "Dispersol" A 5% China clay 68% In Examples 3 to 12 the proportions of the ingredients given are by weight. The remaining compounds of Table 1 were all similarly formulated as per Examples 3 to 12.

There now follows an explanation of the compositions or substances represented by the various Trade Marks and Trade Names mentioned above.

LUBROL L: a condensate on nonyl phenol (1 mole) with ethylene oxide (13 moles) AROMASOL H : a solvent mixture of alkylbenzenes DISPERSOL T & AC: a a mixture of sodium sulphate and a conde- nsate of formaldehyde with sodium naph thalene sulphonate LUBROLAPN5: a condensate ofnonyl phenol (1 mole) with naphthalene oxide (5.5 moles) CELLOFAS B600: a sodium carboxymethyl cellulose thickener LISSAPOL NX: a condensate of nonyl phenol (1 mole) with ethylene oxide (8 moles) AEROSOL OT/B: dioctyl sodium sulphosuccinate PERMINAL BX : a sodium alkyl naphthalene sulphonate Example 13 The compounds were tested against a variety of mainly foliar fungal diseases of plants. The techniques employed were as follows.

For all tests the plants were grown in John Innes Potting Compost (No. 1 or 2) in 4 cm diameter minipots. A layer of fine sand was placed at the bottom of the pots containing the dicotyledonous plants to facilitate uptake of test compounds by the roots. The test compounds were formulated either by bead milling with aqueous Dispersol T or as a solution in acetone or acetone/ethanol which was diluted to the required concentration immediately before use. For the foliage diseases, solutions and suspensions (100 ppm ai.) were sprayed on the foliage and applied to the roots of the plant via the soil. The sprays were applied to maximum retention and the root drenches to a final concentration equivalent to approximately 40 ppm ai./dry soil.Tween 20, to give a final concentration of 0.10%, was added when the sprays were applied to cereals. (ai. means "active ingredient").

Most were protectant tests where the compound was applied to the soil and roots and to the foliage one or two days before the plant was inoculated with the pathogen. However, in the case of the test against Erysiphe graminis hordei, the treatment was eradicative and the compounds were applied one day after inoculation. The foliar pathogens were applied by spraying as spore suspensions onto the leaves of the test plant.

After inoculation, the plants were placed in an appropriate environment to allow infection to proceed and then incubated until the disease was ready for assessment. The period between inoculation and assessment varied from four to fourteen days according to the disease and the environment.

Disease control was recorded using the following grading system: 4 = no disease 3 = trace to 5% of disease on untreated plants 2 = 6-25% of disease on untreated plants 1 = 26-59% of disease on untreated plants 0 = 60-100% of disease on untreated plants The results are shown in Table II below. The compounds were also tested against the bacterial disease bacterial blight of rice caused byXanthomonas campestris oryzae. The technique used was as follows: The plants were grown in John Innes Potting Compost No. 1 in 4 cm diameter minipots. The compounds were formulated as described above. A solution or suspension was applied to each plant as a root drench to the soil, giving a final concentration of approximately 40 ppm ai (ai means "active ingredient").A solution or suspension was also applied as a spray to the foliage of each plant at a concentration of 100 ppm ai. The surfactantTween 20, to give a trial concentration of 0.1% was added before spraying. The foliage was sprayed to maximum retention.

The plants were inoculated 2 days after the compounds were applied. Inoculation was achieved by dipping a pair of sharp scissors into a nutrient broth of x. Campestris oryzae and then cutting off a length of 1.5 cm of leaf tissue from the leaf tips. The plants were placed in an appropriate environment to allow infection to proceed and after an incubation period of approximately 7 days the disease was assessed.

Disease control was recorded using the grading system described in Example 13, and the results are shown in Table II.

Table 2

COMPOUND PUCCINIA ERYSIPHE PIRICULARIA XANTHOMONAS CERCOSPORA VENTURIA NUMBER RECONDITA GRAMINIS ORYZAE CAHPESTRIS ARACHIDICOLA INAEOUALl (WHEAT) (BARLEY) (RICE) ORYZAE (PEANUT) (APPLE) (RICE) 1 4 4 0 . 4 0 2 4 4 0 - 1 0 3 0 4 0 - 0 0 4 4 4 3 4 0 2 7 0 4 0 0 3 3 - = no data available

Claims (6)

1. A compound having the general formula (I):

and stereoisomers thereof, wherein R1, R2, R3 and R4 each represent a hydrogen atom or an alkyl group containing 1 to 4 carbon atoms and R3 and R4 can together form a heterocyclic ring other than a morpholine or piperidine ring, X and Y each represent a hydrogen or a halogen atom, or an alkyl, cycloalkyi, alkenyl, alkynyl, aryl, aralkyl, alkoxy, or aryloxy group; and ester and ether derivatives of the alcohol function; and acid addition salts thereof.

2. Acompound as claimed in claim 1 wherein R' is methyl, R2 is H; R3and R4arealkyl ortogetherform an alkylene or alkenylene bridging group which may contain one or two nitrogen atoms; Y is H; and X is C1 4 alkyl group or chlorine.

3. A process for preparing a compound as defined in claim 1 or claim 2 which comprises treating an epoxide of general formula (II):

wherein X, Y, R1 and R2 are as defined above, with an amine of general formula (III):

wherein R3 and R4 are as defined above, in the presence of a convenient solvent such as ethanol or tetrahydrofuran, or, preferably, in the absence of a solvent at a temperature of 20 C-100 C.

4. A process as claimed in claim 3 wherein the epoxides (II) are prepared by treating an aldehyde of general formula (IV):

with dimethyl oxosulphonium methylide, or dimethyl sulphonium methylide.

5. Fungicidal composition comprising a compound of general formula (I) as defined in claim 1 or claim 2, our a salt, metal complex, ether or ester thereof; and a carrier or diluenttherefor.

6. A method of combating fungi, which comprises applying to a plant, to seed of a plant, or to the locus of the plant or seed, a compound, or salt, metal complex, ether or ester thereof, as defined in claim 1 or claim 2, or a composition as defined in claim 5.