This invention relates to a new compound having fungicidal activity.
It is known that certain salts of N-(3-dimethylaminopropyl)-carbamic
acid propyl ester (US 4,108,885) and that certain salts of monoesters of
phosphonic acids (GB 1 449 394) had fungicidal actions.
It is also known in COUCH H B ET AL: 'Synergistic and antagonistic interactions
of fungicides against pythium aphanidermatum on perennial ryegrass' (Crop Protection,
vol.10, n°5, October 1991, p.386-390) that fosetyl
and propamocarb could be mixed. Patents GB 1 449 394 and FR 2 489
332 disclose with compositions based on monoesters of phosphonic acids and certain
In one aspect, the invention provides the compound, dimethyl-[3-(propoxycarbonylamino)propyl]ammonium
having the structure
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
infestans), Pythium spp., Aphanomyces spp., Bremia spp., Perenospora spp. and
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.
The invention also provides an agricultural composition comprising
the compound of formula I in admixture with an agriculturally acceptable diluent
The composition can comprise one or more additional active ingredients,
for example compounds known to possess plant-growth regulant, herbicidal, fungicidal,
insecticidal or acaricidal properties. Alternatively the compound of the invention
can be used in sequence with the other active ingredient.
Fungicides with which the compound can be mixed include acylanilines,
such as metalaxyl, oxadixyl, ofurace, benalaxyl and furalaxyl; cymoxanil; mancozeb;
chlorothalonil; folpet; captan; famoxadone; fenamidone; spiroxamine; fluazinam;
dimethomorph; strobilurins, such as kresoxim-methyl, azoxystrobin 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:
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
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 0.01 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 the active compound 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 of fungus as a protective measure. In both such
cases the preferred mode of application is by foliar spraying. It is generally
important to obtain good control of fungi in the early stages of plant growth as
this is the time when the plant 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.
The compounds of formula I may be obtained by reacting an amine of
with ethyl hydrogen phosphonate.
This reaction can be carried out in aqueous solution
The invention is illustrated in the following Example.
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
hydrochloride (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 dichloromethane (ca. 100 ml) and the insoluble white
solid (sodium chloride) filtered off and washed with several portions of dichloromethane.
The filtrates were combined and evaporated to leave the dimethyl-[3-(propoxycarbonylamino)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.
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 viticola. For the purposes of comparison the vines were sprayed
also with the commercially available propamocarb hydrochloride.
Plants were assessed for degree of disease control compared with untreated
The results are as follows:
Treatment Rate (ppm) % Control Compound of invention80081.5 Compound of invention40027.6 propamocarb hydrochloride80014.6 propamocarb hydrochloride4004.2
Dimethyl[3-(propoxycarbonylamino)propyl]ammonium-Oethylphosphonat mit der Struktur:
Fungizide Zusammensetzung, die eine Verbindung nach Anspruch 1 im Gemisch mit
einem landwirtschaftlich akzeptablen Verdünnungsmittel oder Träger enthält.
Fungizide Zusammensetzung nach Anspruch 2, die einen oder mehrere aktive(n)
Bestandteil(e) enthält, der/die Eigenschaften wie pflanzenwachstumsregulierende,
herbizide, insektizide, akarizide oder fungizide Eigenschaften besitzt/besitzen.
Verfahren zur Bekämpfung von Pflanzenschädlingen auf einer Örtlichkeit, die
von diesen befallen ist oder gefährdet ist, von diesen befallen zu werden, bei
dem auf die Örtlichkeit eine Verbindung nach Anspruch 1 ausgebracht wird.
Verfahren zur Herstellung einer Verbindung nach Anspruch 1, bei dem ein Amin
mit Ethylwasserstoffphosphonat umgesetzt wird.
Dimethyl[3-(propoxycarbonylamino)propyl]ammonium O-ethylphosphonate having
A fungicidal composition comprising a compound as claimed in claim 1 in admixture
with an agriculturally acceptable diluent or carrier.
A fungicidal composition as claimed in claim 2, comprising one or more active
ingredients possessing properties such as plant-growth regulant, herbicidal, insecticidal,
acaricidal or fungicidal properties.
A method of combating plant pests at a locus infested or liable to be infested
therewith, which comprises applying to the locus a compound as claimed in claim
A process for preparing a compound as claimed in claim 1 comprising reacting
an amine of formula
with ethyl hydrogen phosphonate.
O-Ethylphosphonate de diméthyl[3-(propoxycarbonylamino)propyl]ammonium de structure
Composition fongicide comprenant un composé selon la revendication 1 en mélange
avec un diluant ou un support acceptable du point de vue agricole.
Composition fongicide selon la revendication 2, comprenant un ou plusieurs
ingrédients actifs possédant des propriétés telles que des propriétés régulatrices
de la croissance des plantes, herbicides, insecticides, acaricides ou fongicides.
Méthode de lutte contre des parasites de plantes en un site infesté ou susceptible
d'être infesté par ceux-ci, lequel comprend l'application sur le site d'un composé
selon la revendication 1.
Procédé de préparation d'un composé selon la revendication 1, comprenant la
réaction d'une amine de formule
avec l'hydrogénophosphonate d'éthyle.