GB2291872A - Alkyl cyclopentane-carboxylate fungicides - Google Patents

Abstract

A compound of formula (I): <IMAGE> wherein A, B, D, E, G and J are independently, hydrogen, halogen, optionally substitutedalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted heteroaryloxy, optionally substituted alkenyl or optionally substituted alkynyl, or A and B or D and E or G and J together form an exocyclic methylene which is optionally substituted by halogen or optionally substituted alkyl; R<1> is optionally substituted alkyl; R<2> is: <IMAGE> R<3> is optionally substituted alkyl or optionally substituted aryl, can be used to combat fungi, especially fungal infections of plants.

Description

FUNGICIDES The present invention relates to cyclopentane derivatives useful as fungicides, to processes for preparing them, to compositions comprising them and to methods of using them to combat fungi, especially fungal infections of plants.

The present invention provides a compound of formula (I), wherein A, B, D, E, G and J are, independently, hydrogen, halogen, optionally substituted alkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted heteroaryloxy, optionally substituted alkenyl or optionally substituted alkynyl, or A and B or D and E or G and J together form an exocyclic methylene which is optionally substituted by halogen or optionally substituted alkyl; R1 is optionally substituted alkyl; R2 is a group (a) or (b); and R3 is optionally substituted alkyl or optionally substituted aryl.

Alkyl groups, and the alkyl moiety of alkoxy, preferably contain from 1 to 8, such as from 1 to 6, especially from 1 to 4, carbon atoms. The groups are straight or branched chain and are, for example, methyl, ethyl, n-propyl, i-propyl, n-butyl or -butyl. All alkyl groups are optionally substituted and preferred substituents are halgoen, hydroxy, C16 alkoxy, C16 alkoxy(C16)alkoxy, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted aryloxy or optionally substituted heteroaryloxy.

Halogen includes bromine and iodine but is preferably fluorine or chlorine.

Aryl includes naphthyl but is preferably phenyl.

Heteroaryl, which is normally linked by one of its carbon atoms, includes 5- and 6-membered aromatic rings containing one or more heteroatoms selected from the list comprising oxygen, sulphur and nitrogen and can be fused to benzenoid ring systems. Examples of heteroaryl are pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-, 1,2,4- or 1,3,5 -triazinyl, furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3- or 1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, indolinyl, isoindolinyl, 1- or 2-benzofuranyl, 1- or 2-benzothienyl, benzimidazolinyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thia diazolyl, benzisoxazolyl, benzisothiazolyl, benzpyrazolyl, benzoxazolyl, benzthiazolyl, tetrazolyl and thiazolo[5,4-b]pyrid-2-yl, and, where possible S-oxides thereof.

The foregoing aryl and heteroaryl rings are optionally substituted with the following: halogen, hydroxy, mercapto, C1-4 alkyl (especially methyl and ethyl), C2-4 alkenyl (especially allyl), C2-4 alkynyl (especially propargyl), C1-4 alkoxy (especially methoxy), C2-4 alkenyloxy (especially allyloxy), C2-4 alkynyloxy (especially propargyloxy), halo(C1-4)alkyl (especially trifluoromethyl), halo(C14)alkoxy (especially trifluoromethoxy), C1-4 alkylthio (especially methylthio), hydroxy(C1-4)alkyl, C1-4 alkoxy(C1-4)alkyl, C3-6 cycloalkyl, C3-6 cycloalkyl(C1 4)alkyl, optionally substituted methylenedioxy (especially optionally substituted with fluorine or C14 alkyl), acyloxy (including C1 4 alkanoyloxy (especially acetyloxy) and benzoyloxy), cyano, thiocyanato, nitro, -NR'R", -NHCOR', -NHCONR'R", -CONR'R", -COOR', -OSO2R', -SO2R', -COR', -CR'=NR" or -N=CR'R" in which R' and R" are independently hydrogen, C1-4 alkyl, C1 4 alkoxy, C1 4 alkylthio, C3.6 cycloalkyl, C3 6 cycloalkyl(C1 4)alkyl, phenyl or benzyl, the phenyl and benzyl groups being optionally substituted with halogen, C1 4 alkyl or C14 alkoxy; when R' and R" are in CONR'R" they can together form a 5- or 6-membered heterocyclic ring (for example a pyrrolidine, piperidine or morpholine ring); or two substituents, when they are in adjacent positions on the aryl or heteroaryl ring can join to form a fused alphatic ring (especially to form a fused 6-membered carbon aliphatic ring).

In one aspect the present invention provides a compound of formula (I) wherein A, B, D, E, G and J are, independently, hydrogen, halogen (such as fluorine), C1-6 alkyl (such as methyl or ethyl) or C1 6 haloalkyl (such as CF3 or CCl3), or A and B or D and E or G and J join together to form an exocyclic methylene which is optionally substituted by halogen (such as fluorine) or unsubstituted C1-6 6 alkyl; R1 is unsubstituted C16 alkyl; R2 is a group (a) or (b); and R is optionally substituted phenyl.

In another aspect the present invention provides a compound of formula (I) wherein A, B, D, E, G and J are all hydrogen; R1 is methyl; R2 is the group (a) or (b); and R3 is phenyl optionally substituted by C14 alkoxy (especially methoxy).

Illustrative compounds of formula (I) follow in Tables I and II.

TABLE I All compounds in Table I are of formula (II).

Compound A B D E G J R1 R3 No.

1 H H H H H H CH3 C6H5 2 CH3 H H H H H CH3 C6H5 3 H CH3 H H H H CH3 C6H5 4 H H CH3 H H H CH3 C6H5 5 H H H CH3 H H CH3 C6H5 6 H H H H CH3 H CH3 C6H5 7 H H H H H CH3 CH3 C6H5 8 CH3 H H H H H CH3 4-CH3O-C6H4 9 H CH3 H H H H C@ CH3 4-CH30-C6H4 10 H H CH3 H H H CH3 4-CH3O-C6H4 11 H H H CH3 H H CH3 4-CH3o-C6H4 12 H H H H CH3 H CH3 4-CH30-C6H4 13 H H H H H CH3 CH3 4-CH30-C6H4 14 CH3 H H H H H CH3 4-Cl-C6H4 15 H CH3 H H H H CH3 4-Cl-C6H4 16 H H CH3 H H H CH3 4-Cl-C6H4 17 H H H CH3 H H CH3 4-Cl-C6H4 18 H H H H CH3 H CH3 4-Cl-C6H4 19 H H H H H CH3 CH3 4-Cl-C6H4 20 H H H H CH3 H CH3 4-C2H5O-C6H4 21 H H H H H CH3 CH3 4-C2H50-C6H4 22 H H H H CH3 H C2H5 4-CH30-C6H4 23 H H H H H CH3 C2H5 4-CH3O-C6H4 24 H H H H H H C2H5 4-CH30-C6H4 25 H H H H H H CH3 4-CH30-C6H4 26 H H H H H H CH3 4-Cl-C6H4 27 H H H H H H C2H5 4-Cl-C6H4 28 H H H H H H C2H5 4-C2H50-C6H4 29 H H H H H H CH3 4-C2H5O-C6H4 TABLE I (Continued) Compound A B D E G J R1 R3 No.

30 =CH2 H H H H CH3 4-C2H50-C6H4 31 =CH2 H H H H C2H5 4-C2H5O-C6H4 32 =CH2 H H H H CH3 C6H5 33 =CH2 H H H H C2H5 C6H5 34 =CH2 H H H H CH3 4-Cl-C6H4 35 =CH2 H H H H C2H5 4-C1-C6H4 36 =CH2 H H H H CH3 4-CH3o-C6H4 37 =CH2 H H H H C2H5 4-CH30-C6H4 38 =CF2 H H H H CH3 C6H5 39 =CF2 H H H H CH3 4-CH3O-C6H4 40 =CF2 H H H H CH3 4-Cl-C6H4 41 =CF2 H H H H CH3 4-C2H50-C6H4 42 =CF2 H H H H C2H5 C6H5 43 =CF2 H H H H C2H5 4-CH30-C6H4 44 =CF2 H H H H C2H5 4-Cl-C6H4 45 =CF2 H H H H C2H5 4-C2H50-C6H4 46 H H =CH2 H H CH3 C6H5 47 H H =CH2 H H CH3 4-CH3o-C6H4 48 H H =CH2 H H CH3 4-Cl-C6H4 49 H H =CH2 H H CH3 4-C2H50-C6H4 50 H H =CH2 H H C2H5 C6H5 51 H H =CH2 H H C2H5 4-CH3O-C6H4 52 H H =CH2 H H C2H5 4-Cl-C6H4 53 H H =CH2 H H C2H5 4-C2H50-C6H4 54 H H =CF2 H H CH3 C6H5 55 H H =CF2 H H CH3 4-Cl-C6H4 56 H H =CF2 H H CH3 4-CH30-C6H4 57 H H =CF2 H H CH3 4=C2H5O-C6H4 58 H H =CF2 H H C2H5 C6H5 59 H H =CF2 H H C2H5 4-Cl-C6H4 TABLE I (Continued) Compound A B D E G J R1 R3 No.

60 H H =CF2 H H C2H5 4-CH30-C6H4 61 H H =CF2 H H C2H5 4-C2H5O-C6H4 62 H H H H =CH2 CH3 C6H5 63 H H H H =CH2 CH3 4-Cl-C6H4 64 H H H H =CH2 CH3 4-CH30-C6H4 65 H H H H =CH2 CH3 4-C2H5O-C6H4 66 H H H H =CH2 C2H5 C6H5 67 H H H H =CH2 C2H5 4-C1-C6H4 68 H H H H =CH2 C2H5 4-CH30-C6H4 69 H H H H =CH2 C2H5 4-C2H5O-C6H4 70 H H H H CF2 CH3 C6H5 71 H H H H =CF2 CH3 4-Cl-C6H4 72 H H H H =CF2 CH3 4-CH30-C6H4 73 H H H H =CF2 CH3 4-C2H50-C6H4 74 H H H H =CF2 C2H5 C6H5 75 H H H H =CF2 C2H5 4-C1-C6H4 76 H H H H =CF2 C2H5 4-CH30-C6H4 77 H H H H CF2 C2H5 4-C2H50-C6H4 78 H H H H =CHCH3 CH3 C6H5 79 H H H H =CHCH3 CH3 4-Cl-C6H4 80 H H H H =CHCH3 CH3 4-CH30-C6H4 81 H H H H =CHCH3 CH3 4-C2H50-C6H4 82 H H H H =C(CH3)2 CH3 C6H5 83 H H H H =C(CH3)2 CH3 4-Cl-C6H4 84 H H H H =C(CH3)2 CH3 4-CH3O-C6H4 85 H H H H =C(CH3)2 CH3 4-C2H5O-C6H4 86 H H =CHCH3 H H CH3 C6H5 87 H H =CHCH3 H H CH3 4-Cl-C6H4 88 H H =CHCH3 H H CH3 4-CH30-C6H4 89 H H =CHCH3 H H CH3 4-C2H50-C6H4 TABLE I (Continued) Compound A B D E G J R1 R3 No.

90 H H =C(CH3)2 H H CH3 C6H5 91 H H =C(CH3)2 H H CH3 4-Cl-C6H4 92 H H =C(CH3)2 H H CH3 4-CH3O-C6H4 93 H H =C(CH3)2 H H CH3 4-C2H30-C6H4 94 H H H H H H C2H5 C6H5 TABLE II Table II comprises 94 compounds of formula (III) wherein the variables A, B, D, E, G, J, R1 and R3 have the values listed for the correspondingly numbered compound in Table I.

A compound of formula (II) can be prepared by reacting a compound of formula (IV) (wherein A, B, D, E, G, J and R1 are as previously defined) with an aldehyde of formula R3CHO (wherein R3 is as previously defined) in the presence of a suitable solvent (such as an aromatic hydrocarbon, for example a xylene, toluene or benzene) and preferably at a temperature in the range 50-150"C (such as at the boiling point of the solvent).

A compound of formula (III) can be prepared by reacting a compound of formula (II) with a suitable oxidising agent (such as a peroxy acid or salt thereof, for example magnesium monoperoxyphthalate) in a suitable solvent or solvent mixture (such as a mixture of methanol and water).

In a further aspect the present invention provides a process for preparing a compound of formula (I).

The compounds of formula (I) show fungicidal activity across a range of plant diseases. They are, however, particularly active against the class of pathogens known as the phycomycetes (equivalent to the oomycetes).

These include species of Phytophthora, Plasmopara, Peronospora and Pseudoperonospora. Examples of pathogens which the invention compounds are particularly useful for controlling are: Plasmopara viticola on vines; other downy mildews such as Bremia lactucae on lettuce; Peronospora spp. on soybeans, tobacco, onions and other hosts; Pseudoperonospora humuli on hops and PseudoDeronospora cubensis on cucurbits; Phvtophthora infestans on potatoes and tomatoes and other Phytophthora spp. on vegetables, strawberries, avocado, pepper, ornamentals, tobacco, cocoa and other hosts; and Pvthium sp on rice, horticultural plants, vegetables and turf.

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

The invention therefore provides a method of combating fungi which comprises applying to a plant, to a seed of a plant or to the locus of the plant or seed a fungicidally effective amount of a compound as hereinbefore defined, or a composition containing the same.

The compounds may be used directly for agricultural purposes but are more conveniently formulated into compositions using a carrier or diluent.

The invention thus provides fungicidal compositions comprising a compound as hereinbefore defined and an acceptable carrier or diluent therefor. It is preferred that all compositions, both solid and liquid formulations, comprise 0.0001 to 95%, more preferably 1 to 85%, for example 1 to 25% or 25 to 60%, of a compound as hereinbefore defined.

When applied the foliage of plants, the compounds of the invention are applied at rates of 0.lg to 10Kg, preferably lg to 8Kg, more preferably 10g to 4Kg, of active ingredient (invention compound) per hectare.

When used as seed dressings, the compounds of the invention are used at rates of 0.0001g (for example 0.001g or 0.059) to 10g, preferably 0.0059 to 89, more preferably 0.0059 to 49, of active ingredient (invention compound) per kilogram of seed.

The compounds can be applied in a number of ways. For example, they can be applied, formulated or unformulated, directly to the foliage of a plant, to seeds or to other medium in which plants 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 including 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 sprayed onto vegetation using electrodynamic spraying techniques or other low volume methods.

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

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 dustable powders or granules comprising the active ingredient (invention compound) and a solid diluent or carrier, for example, fillers such as kaolin, bentonite, kieselguhr, dolomite, calcium carbonate, talc, powdered magnesia, fuller's earth, gypsum, 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 may include 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 using an organic solvent (for example, fi-methylpyrrol- idone, propylene glycol or N,N-dimethylformamide). The compositions may also be in the form of wettable powders or water dispersible granules comprising wetting or dispersing agents to facilitate the dispersion in liquids. The powders and granules may also contain fillers and suspending agents.

The compositions may also be in the form of soluble powders or granules, or in the form of solutions in polar solvents.

Soluble powders may be prepared by mixing the active ingredient with a water-soluble salt such as sodium bicarbonate, sodium carbonate, magnesium sulphate or a polysaccharide, and a wetting or dispersing agent to improve water dispersibility/solubility. The mixture may then be ground to a fine powder. Similar compositions may also be granulated to form water-soluble granules. Solutions may be prepared by dissolving the active ingredient in polar solvents such as ketones, alcohols and glycol ethers. These solutions may contain surface active agents to improve water dilution and prevent crystallisation in a spray tank.

Emulsifiable concentrates or emulsions may be prepared by dissolving the active ingredient in an organic solvent optionally containing a wetting or emulsifying agent and then adding the mixture to water which may also contain a wetting or emulsifying agent. Suitable organic solvents are aromatic solvents such as alkylbenzenes and alkylnaphthalenes, ketones such as cyclohexanone and methylcyclohexanone, chlorinated hydrocarbons such as chlorobenzene and trichlorethane, and alcohols such as benzyl alcohol, furfuryl alcohol, butanol and glycol ethers.

Suspension concentrates of largely insoluble solids may be prepared by ball or bead milling with a dispersing agent with a suspending agent included to stop the solid settling.

Compositions to be used as sprays may be in the form of aerosols wherein the formulation is held in a container under pressure of a propellant, e.g. fluorotrichloromethane or dichlorodifluoromethane.

The invention 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 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 uptake, distribution, adhesive power and resistance to rain on treated surfaces, the different compositions can be better adapted for various utilities. Other additives may be included to improve the biological efficacy of the various formulations. Such additives can be surface active materials to improve the wetting and retention on surfaces treated with the formulation and also the uptake and mobility of the active material, or additionally can include oil based spray additives, for example, certain mineral oil and natural plant oil (such as soya bean and rape seed oil) additives, or blends of them with other adjuvants.

The invention compounds can be used as mixtures with fertilisers (e.g. nitrogen-, potassium- or phosphorus-containing fertilisers).

Compositions comprising only granules of fertiliser incorporating, for example coated with, a compound of formula (I) are preferred. Such granules suitably contain up to 25% by weight of the compound. The invention therefore also provides a fertiliser composition comprising a fertiliser and the compound of general formula (I) or a salt or metal complex thereof.

Wettable powders, emulsifiable concentrates and suspension concentrates will normally contain surfactants, e.g. a wetting agent, dispersing agent, emulsifying agent or suspending agent. These agents can be cationic, anionic or non-ionic agents.

Suitable cationic agents are quaternary ammonium compounds, for example, cetyltrimethylammonium 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 triisopropylnaphthalene 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 nonylphenol 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 swelling clays such as bentonite or attapulgite.

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, the concentrate being diluted with water before use. These concentrates should preferably be able to withstand storage for prolonged periods and after 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 spray equipment. The concentrates may conveniently contain up to 95%, suitably 1-85%, for example 1-25% or 25-60%, by weight of the active ingredient.After dilution to form aqueous preparations, such preparations may contain varying amounts of the active ingredient depending upon the intended purpose, but an aqueous preparation containing 0.0001 to 10%, for example 0.005 to 10%, by weight of active ingredient may be used.

The compositions of this invention may contain other compounds having biological activity, e.g. compounds having similar or complementary fungicidal activity or which possess plant growth regulating, herbicidal or insecticidal activity.

By including another fungicide, the resulting composition can have a broader spectrum of activity or a greater level of intrinsic activity than the compound of general formula (I) alone. Further the other fungicide can have a synergistic effect on the fungicidal activity of the compound of general formula (I).Examples of fungicidal compounds which may be included in the composition of the invention are (RS)-1-aminopropyl- phosphonic acid, (RS)-4-(4-chlorophenyl)-2-phenyl-2-(lH-1,2,4-triazol-1-yl- methyl)butyronitrile, (Z)-N-but-2-enyloxymethyl-2-chloro-2',6'-diethylacetanilide, 1-(2-cyano-2-methoxyiminoacetyl)-3-ethyl urea, 4-(2,2-difluoro .1,3-benzodioxol-4-yl)pyrrole-3-carbonitrile, 4-bromo-2-cyano-N,N-dimethyl -6-tri fluoromethylbenzimidazole-1-sulphonamide, 5-ethyl-5,8-dihydro-8 -oxo(1,3)-dioxol-(4,5-a)quinoline-7-carboxylic acid, a-[-(3-chloro-2,6- -xylyl)-2-methoxyacetamido]-g-butyrolactone, N-(2-methoxy-5-pyridyl)-cyclo- propane carboxamide, alanycarb, aldimorph, ampropylfos, anilazine, azaconazole, BAS 490F, benalaxyl, benomyl, biloxazol, binapacryl, bitertanol, blasticidin S, bromuconazole, bupirimate, butenachlor, buthiobate, captafol, captan, carbendazim, carbendazim chlorhydrate, carboxin, chinomethionate, chlorbenzthiazone, chloroneb, chlorothalonil, chlorozolinate, clozylacon, copper containing compounds such as copper oxychloride, copper oxyquinolate, copper sulphate, copper tallate, and Bordeaux mixture, cycloheximide, cymoxanil, cyproconazole, cyprodinyl, cyprofuram, debacarb, di-2-pyridyl disulphide 1,1'-dioxide, dichlofluanid, dichlone, diclobutrazol, diclomezine, dicloran, didecyl dimethyl ammonium chloride, diethofencarb, difenoconazole, Q,Q-di-iso-propyl-S-benzyl thiophosphate, dimefluazole, dimetconazole, dimethomorph, dimethirimol, diniconazole, dinocap, dipyrithione, ditalimfos, dithianon, dodemorph, dodine, doguadine, edifenphos, epoxiconazole, etaconazole, ethirimol, ethoxyquin, ethyl (Z)-N-benzyl-N-t[methyl(methylthioethylideneamino-oxy- carbonyl)amino]thio)-p-alaninate, etridiazole, fenaminosulph, fenapanil, fenarimol, fenbuconazole, fenfuram, fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam, ferimzone, fluazinam, fludioxonil, fluoroimide, fluquinconazole, flusilazole, flutolanil, flutriafol, folpet, fuberidazole, furametpyr, furalaxyl, furconazole-cis, guazatine, hexaconazole, hydroxyisoxazole, hymexazole, ICIA5504, imazalil, imibenconazole, ipconazole, iprobenfos, iprodione, isopropanyl butyl carbamate, isoprothiolane, kasugamycin, mancozeb, maneb, mepanipyrim, mepronil, metalaxyl, metconazole, methfuroxam, metiram, metiram-zinc, metsulfovax, myclobutanil, NTN0301, neoasozin, nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol, ofurace, organomercury compounds, oxadixyl, oxolinic acid, oxycarboxin, pefurazoate, penconazole, pencycuron, phenazin oxide, phosetyl-Al, phosphorus acids, phthalide, polyoxin D, polyram, probenazole, prochloraz, procymidone, propamocarb, propamocarb hydrochloride, propiconazole, propineb, propionic acid, prothiocarb, pyracarbolid, pyrazophos, pyrifenox, pyrimethanil, pyroquilon, pyroxyfur, pyrrolnitrin, quaternary ammonium compounds, quinconazole, quinomethionate, quintozene, rabenazole, sodium pentachlorophenate, streptomycin, sulphur, tebuconazole, techlofthalam, tecnazene, tetraconazole, thiabendazole, thicyofen, thifluzamide, 2-(thiocyanomethylthio)benzothiazole, thiophanate-methyl, thiram, timibenconazole, tolclofos -methyl, tolylfluanid, triacetate salt of 1,1'-iminodi(octamethylene)diguanidine, triadimefon, triadimenol, triazbutyl, triazoxide, tricyclazole, tridemorph, triforine, triflumizole, triticonazole, validamycin A, vapam, vinclozolin, XRD-563, zineb and ziram. 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 or foliar fungal diseases.

The following Examples illustrate the invention. All reactions were performed under an atmosphere of nitrogen and solvents were dried before use, where appropriate. Selected proton NMR data were obtained at 270MHz.

Chemical shifts are measured at 20 C in ppm from tetramethylsilane. The following abbreviations are used: s = singlet m = multiplet d = doublet br = broad t = triplet ppm = parts per million q = quintet EXAMPLE 1 This Example describes the preparation of methyl cis-N-(4-methoxy- benzylidene)-2-aminocyclopentane-1-carboxylate (Compound No. 25 of Table I).

Cis-2-aminocyclopentanecarboxylic acid (3.0g, 0.021mol) was dissolved in dry toluene (100ml) and 4-methoxybenzaldehyde (2.889, 0.021mol) added.

The resulting mixture was stirred and refluxed (Dean and Stark apparatus fitted) for 2 hours. The mixture was cooled and then evaporated in vacuo to leave a yellow oil. The oil was distilled at water pump pressure (15mm Hg approximately) and 220"C to give the title compopund as a very pale yellow oil (1.0729, 20%).

1H NMR(CDCl3); 8 8.17(1H,s); 7.64(2H,d); 6.88(2H,d); 4.02(1H,br q); 3.82(3H,s); 3.53(3H,s); 3.01(1H,q); 2.43-2.25(1H,m); 2.18-1.60(5H,m)ppm.

EXAMPLE 2 This Example describes the preparation of methyl cis-2-[3-(4-methoxy phenyl)oxaziridin-2-yl]cyclopentane-1-carboxylate (Compound No. 25 of Table II).

Methyl cis-N-(4-methoxybenzylidene)-2-aminocyclopentane-1-carboxylate (1.59, 0.0058mol; prepared as described in EXAMPLE 1) was dissolved in methanol (25ml) at 20"C with stirring. A solution of magnesium monoperoxyphthalate (5.199, 0.Ollmol) in water (30ml) was added slowly with stirring. The resulting mixture was stirred for 60 hours, drowned into water and the aqueous extracted twice with dichloromethane. The organic extracts were combined, washed with sodium bicarbonate solution, dried over anhydrous magnesium sulphate and concentrated in vacuo to give the title compound as a yellow oil (1.1879, 71%).

1H NMR(CDC13); 3 8.22(2H,d); 7.42(1H,s); 6.92(2H,d); 4.74-4.61(1H,m); 3.84(3H,s); 3.57(3H,s); 3.09-2.95(1H,m); 2.55-2.32(2H,m); 2.27-1.94(3H,m); 1.69-1.51(1H,m)ppm.

EXAMPLE 3 The compounds were tested against the diseases Plasmooora viticola on vine and Phvtophthora infestans lvcooersici on tomato. The technique employed was as follows.

The plants were grown in John Innes Potting Compost (No. 1 or 2) in 4cm diameter minipots. 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. The formulations (100 ppm active ingredient) were sprayed onto the foliage of the plants or to the roots of the plants in the soil. The sprays were applied to maximum retention and the root drenches to a final concentration equivalent to approximately 40 ppm in dry soil.

For most of the tests the compounds were applied to the soil (roots) or to the foliage (by spraying) one or two days before the plant was inoculated with the disease. When applying the pathogens to the leaves of test plants, the pathogens were applied by spray as a spore suspension. After inoculation, the plants were put into 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 seven days according to the disease and environment.

The disease control was assessed by visual assessment of the percentage leaf area covered by actively sporulating disease. Assessments were performed on a single leaf of each of the two replicate plants, and the mean value of these two recordings was calculated for each treatment. The mean value for each treatment was then expressed as a percentage of the level of disease present on the untreated control plants. This calculated value is referred to as a POCO (Percentage of Control) value. An example of a typical calculation is as follows: Mean disease level on untreated Control = 90 Mean disease level on treatment A = 30 POCO Mean disease level on treatment A for treatment A = ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ x 100 Mean disease level on untreated Control 30 = ~ x 100 = 33.3 90 Thus a POCO value of 0 indicates complete disease control.

The results for certain compounds in Tables I and II are shown in Table III.

TABLE III COMPOUND Pv prot&num; Pv syst Pil prot* Pil syst (Table No.) 25(I) 96 0 40 25(II) 39 0 23 0 Pv = Plasmooara viticola Pil = Phytophthora infestans lvcopersici prot = foliar spray syst = root drench &num; = test carried out at 50ppm * = test carried out at 200ppm CHEMICAL FORMULAE (IN DESCRIPTION)

Claims (4)

1. CLAIMS 1. A compound of formula (I) :

   wherein A, B, D, E, G, and J are independently, hydrogen, halogen, optionally substituted alkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted heteroaryloxy, optionally substituted alkenyl or optionally substituted alkynyl, or A and B or D and E or G and J together form an exocyclic methylene which is optionally substituted by halogen or optionally substituted alkyl; R1 is optionally substituted alkyl; R2 is:

   N=CHR2 (b) R3 is optionally substituted alkyl or optionally substituted aryl.
2. 2. A process for preparing a compound according to claim 1 as herein described.
3. 3. A fungicidal composition comprising a fungicidally effective amount of a compound according to claim 1 and a fungicidally acceptable carrier or diluent therefor.
4. 4. A method of combating fungi which comprises applying to plants, to the seeds of plants or to the locus of the plants or seeds a compound according to claim 1 or a composition according to claim 3.