Title of Invention	"FUNGICIDES"
Abstract	The compound of the invention has activity as a fungicide, especially against Phycomycete diseases of plants, e.g vine downy mildew (Plasmopara viticola), various Phytophthora blights e.g late tomato or potato blight (Phytophthora ;n/esfans), Pythium spp , Aphanomyces spp., Bremia spp., Perenospora spp. and Pseudoperenospora spp

Full Text

Title Fungicides This invention relates to a new compound having fungicidal activity in one aspect, the invention provides the compound, dimethyl-[3-(propoxycarbonylamino)propyl]ammonium O-ethyiphosphonate, having the structure (Figure Remove) VThe compound of the invention has activity as a fungicide, especially against Phycomycete diseases of plants, e.g vine downy mildew (Plasmopara viticola), various Phytophthora blights e.g late tomato or potato blight (Phytophthora mfastans), Pythium spp , Aphanomyces spp., Bremia spp., Perenospora spp. and Pseudoperenospora sppj The invention thus also provides a method of combating fungi at a locus infested or liable to be infested therewith, which comprises applying to the locus the compound of formula I Tne invention also provides an agricultural composition comprising the compound of formula I in admixture with an agriculturally acceptable diluent or carrier. The composition can comprise one or more additional active ingredients, for example compounds known to possess plant-growth regulant, herbicidal, fungicidal, insecticidal or acancidal properties Alternatively the compound of the invention can be used in sequence with the other active ingredient SUBSTITUTE SHEET (RULE 26) Fungicides witn which tne compouna can Pe mixed include acylanilines. such as metalaxyl, oxadixyl ofurace, benalaxyl and furalaxyl; cymoxanil: mancozeb; chiorothaloni! foipet captan. famoxadone fenamidone, spiroxamine, fiuazmam, dirnethomorph strobilurins, such as kresoxim-methyl, azoxystrobm and trifloxystrobin pyrimethanil cyprodinil, mepanipyrim and iprodione The names quoted for these compounds are the non-proprietary common names and the chemical structure can be found for example by reference to the "Pesticide Manual", eleventh edition, 1997, published by the British Crop Protection Council. Of the compounds whose common names are not mentioned in the Pesticide Manual the full chemical names are as follows trifloxystrobin - methyl (E,E)-methoxyimino-{2-[1-(3-trifluoromethylphenyl)- ethylideneammooxymethyl]phenyl}acetate spiroxamine 8-tert-butyM 4-dioxaspiro(4.5]decan-2-ylmethyl(ethyl)- (propyl)amme fenamidone - (S)-1-anilino-4-methyl-2-methylthio-4-phenylimidazolin-5-one The composition of the invention may include for example a dispersing agent, emulsifying agent or wetting agent Usually they are in the form of an aqueous concentrate. The concentration of the active ingredient in the composition of the present invention, as applied to plants is preferably within the range of 0.0001 to 1 0 per cent by weight, especially 0 0001 to 001 per cent by weight In a primary composition, the amount of active ingredient can vary widely and can be, for example, from 5 to 95 per cent by weight of the composition In the method of the invention the compound is generally applied to seeds, plants or their habitat Thus, the compound can be applied directly to the soil before, at or after drilling so that the presence of active compound in the soil can control the growth of fungi which may attack seeds When the soil is treated directly the active compound can be applied in any manner which allows it to be intimately mixed with the soil such as by spraying, by broadcasting a solid form of granules, or by applying the active ingredient at the same time as drilling by inserting it in the same drill as the seeds. A suitable application rate is within the range of from 5 to 1000 g per hectare, more preferably from 10 to 500 g per hectare Alternatively trie active compouna can be applied directly to the plant by. for example spraying or dusting either at the time when the fungus has begun to appear on the plant or before the appearance c* fungus as a protective measure In both such cases the preferred mode of application is by fohar spraying _ It is generally important to obtain gooc control of fungi in tne early stages of plant growth as this is the time when the plan' can be most severely damaged The spray or dust can conveniently contain a pre- or post-emergence herbicide if this is thought necessary Sometimes, it is practicable to treat the roots of a plant before or during planting, for example, by dipping the roots in a suitable liquid or solid composition When the active compound is applied directly to the plant a suitable rate of application is from 0.025 to 5 kg per hectare, preferably from 0.05 to 1 kg per hectare, Tne compounds of formula I may be obtained by reacting an amine of formula II witn ethyl hydrogen phosphonate Tms reaction can be carried out in aqueous solution Trie invention s illustrated in the following Example Example_ 1 A solution of the sodium salt of ethyl hydrogen phosphonate (13.2 g in water (25 ml)) was added to a an aqueous solution of propyl 3-(dimethylamino)propylcarbamate hydro-chloride (31 0 ml of concentration 722 g/l 0 1 moles) The solution was evaporated to dryness to leave an oil containing sodium chloride as a white solid. The crude product was triturated with dichlorornethane (ca 100 ml) and the insoluble white solid (sodium chloride) filtered off and washed with several portions of dichlorornethane The filtrates were combined and evaporated to leave the dimethyl-[3-(propoxycarbonyiamino)propyl]ammonium O-ethylphosphonate, as a viscous colourless oil Nmr spectroscopy confirmed that the product was a salt by observation of the chemical shifts relative to propyl 3-(dimethylamino)propylcarbamate The starting material was prepared by alkaline hydrolysis of diethyl phosphite by a known procedure See for example Synthesis 134 1978 Exampje_ 2 Aqueous solutions of the compound of Example 1 were sprayed at various concentrations onto vines to run off using a hand-sprayer Plants were then inoculated by hand spraying with a spore suspension of 100,000 spores per ml of Plasmopara v/ticola For the purposes of comparison the vines were sprayed also with the commercially available propamocarb hydrochlonde Plants were assessed for degree of disease control compared with untreated plants. The results are as follows (Table Remove) CLAIMS 1 Dime thy l[3-(propoxycarbonylamino)propyl]ammonium O-ethylphosphonate having the structure

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