WO2002039815A1 - Compositions et methodes pour exterminer des insectes ou animaux nuisibles au moyen d'alkylesters d'acide benzene-propionique - Google Patents

Compositions et methodes pour exterminer des insectes ou animaux nuisibles au moyen d'alkylesters d'acide benzene-propionique Download PDF

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Publication number
WO2002039815A1
WO2002039815A1 PCT/GB2001/005067 GB0105067W WO0239815A1 WO 2002039815 A1 WO2002039815 A1 WO 2002039815A1 GB 0105067 W GB0105067 W GB 0105067W WO 0239815 A1 WO0239815 A1 WO 0239815A1
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WO
WIPO (PCT)
Prior art keywords
composition
pests
mites
hydrogen
exterminating
Prior art date
Application number
PCT/GB2001/005067
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English (en)
Inventor
David John Garnett
Original Assignee
Lovesgrove Research Limited
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Lovesgrove Research Limited filed Critical Lovesgrove Research Limited
Priority to AU2002223818A priority Critical patent/AU2002223818A1/en
Publication of WO2002039815A1 publication Critical patent/WO2002039815A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/10—Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing within the same carbon skeleton a carboxylic group or a thio analogue, or a derivative thereof, and a carbon atom having only two bonds to hetero atoms with at the most one bond to halogen, e.g. keto-carboxylic acids

Definitions

  • the present invention relates to compositions for exterminating pests and to a method of exterminating pests, in particular mites.
  • cinnamates such as ethyl cinnamate
  • the compounds may be provided in a variety of formulations, for example, as an oil preparation, spray, aerosol or fumigant.
  • these compounds are relatively effective against certain types of mites, such as house dust mites, the compounds have a strong smell and are often difficult to handle.
  • some cinnamates have been found to be an irritant to the skin. Accordingly, the use of such compounds, particularly in domestic envuOnments, is not ideal.
  • compositions for exterminating pests in particular mites, that aim to overcome, or at least alleviate, the abovementioned drawbacks.
  • a further obj ect of the present invention is to provide an improved method of exterminating pests, such as mites, that aims to overcome, or at least alleviate, the abovementioned drawbacks.
  • a first aspect of the present invention provides a composition for exterminating pests, the composition comprising one or a combination of allcyl esters of a carboxylic acid of the general formula:-
  • A, B, C and D are all hydrogen, or
  • a and B together form a carbonyl group and C and D are both hydrogen; and R is an alkyl group having between 1 and 10 carbon atoms.
  • a second aspect of the present invention provides a method for exterminating pests, the method comprising the steps of applying a composition containing one or a combination of alkyl esters of a carboxylic acid of the general formula:-
  • A, B, C and D are all hydrogen, or
  • a and B together form a carbonyl group and C and D are both hydrogen; and R is an alkyl group having between 1 and 10 carbon atoms, to an area infested with pests thereby exterminating the pests.
  • a preferred composition according to the present invention has the forrnula:-
  • the compound may have the following formula:-
  • the compounds of the present invention are inactive and innocuous and therefore particularly suitable for use in domestic situations for exterminating pests. It is beheved that the compounds become converted by metabolic reactions that occur within the pest into active cinnamate compounds. Such reactions involve the action of enzymes, such as reductases, on the compound followed by an acid or base dehydration that results in the production of the active cinnamate which causes death of the pest.
  • enzymes such as reductases
  • the compounds are particularly active against mites, such as house dust mites, mites that infest wood, paper and leather products and mites that infest plants and animals, such as the Narroa mite, sheep scab mite and various poultry mites . This is due to the mites possessing the necessary enzymes to convert the compounds into an active form. Not all organisms would have sufficiently available enzymes to metabolize the compound.
  • One or a combination of compounds according to the present invention may be included with a suitable carrier material for assisting in the application of the compounds to the pest.
  • the compounds may be incorporated into cleaning agents, such as fabric conditioners or polishes, or may be applied as a fumigant or aerosol.
  • Example 1 investigates the toxicity of ethyibenzoylacetate on the ⁇ carus siro mite and Example 2 compares the toxicity of ethyibenzoylacetate, ethylnitrocinnamate and ethylcinnamate to the Dermatophagoides pteronyssinus mite and with reference to the accompanying drawings in which:-
  • Figure 1 is a graph illustrating the Acarus siro mortality at various concentrations of ethyibenzoylacetate.
  • Figure 2 is a graph of the toxicity of ethylcinnamate, ehtylbenzoylacetate and ethylnitrocinnamate to the Dermatophagoides pteronyssinus mite.
  • Example 1
  • Working concentrations of ethyibenzoylacetate were prepared by dilution with ethyl alcohol. The concentrations were chosen on the basis of an initial dose finding experiment. Triplicate filter papers (42.5mm diameter) were impregnated with 150 ⁇ l of four concentrations and pure ethyl alcohol acted as a control. The filter papers were dried at room temperature for a six hour period.
  • Acarus siro The vulnerability of Acarus siro to ethyibenzoylacetate was. determined using 6- cell well plates. A separate filter paper was pressed into each well and cell plates were humidified for 18 hours at 20° C, 90% RH prior to addition of the mites. This helped to ensure mite viability throughout the test period. Acarus siro were added to cell plates, ten in each cell, and the chambers were sealed separately using parafilm. The mites were exposed for a 24 hour period at 20°C, 90% RH, after which mortality was recorded. Mites were recorded as dead if they show no movement in response to touch of a fine paintbrush.
  • the accompanying figure illustrates Acarus siro mortality at the various concentrations of ethyibenzoylacetate. Pure ethyibenzoylacetate was found to be lethal to the mite. In order to calculate ED 50 value more accurately, the value for pure ethyibenzoylacetate is not shown in the figure. The ED50 value was determined to be at approximately 0.0042 mg ⁇ l *1 ethyibenzoylacetate i.e. at 44 ⁇ g cm "2 filter.
  • the compound ethyibenzoylacetate has an oral mouse LD50 of 6800mg/kg with no toxic effects. This is better than the prior art compound ethyl cinnamate because it does not cause sensitization of the skin. Additionally, the compound is not incompatible with polystyrene and other plastics materials which are often used in horticultural environments where pesticides may be employed.
  • An additional innocuous compound that have been found to be active against pests, such as mites, includes the following:-
  • Duplicate filter papers (42.5mm diameter) were impregnated with 150 ⁇ l of the following:
  • Filter papers were dried at room temperature for a six hour period. Vulnerability of Dermatophagoides pteronyssinus to the above was determined using well plates (6- cell). A separate filter paper was pressed into each well and cell plates were humidified for 18 hours at 20°C, 90% RH prior to the addition of mites. This helped to ensure mite viability throughout the test period. Dermatophagoides pteronyssinus were added to cell plates, ten in each cell, and chambers were sealed separately using parafilm. Exposure took place for a 24 hour period at 20°C. 90% RH, after which mortality was recorded. Mites were recorded as dead if they showed no movement in respone to the touch of a fine paintbrush.
  • FIG. 2 of the accompanying drawings illustrates the results of the investigation.
  • Ethyibenzoylacetate and ethylcinnamate displayed some toxicity to the Dermatophagoides pteronyssinus mite.
  • the ED 50 value for ethyibenzoylacetate was determined to be approximately 0.004 mg ⁇ l "1 ethyibenzoylacetate i.e. at 42 ⁇ g cm '2 filter.
  • the ED 50 value for ethycimiamate was found to be slightly lower at approximately 0.002 mg ⁇ l "1 ethylcinnamate i.e. at 21 ⁇ g cm "2 filter.
  • Ethylnitrocinnamate by contrast, was not found to display significant toxicity to the Dermatophagoides pteronyssinus mite at the test concentrations. This clearly illustrates that not all inactive derivatives of ethylcinnamate are converted to the active ingredient by enzymes present in the pest to cause death thereof.
  • the compounds of the present invention may be used against a number of different pests, such as house dust mites and those that infest wood, paper and leather products.
  • the compounds may also be used against mites that infest plants (agricultural and horticultural) and those that infest the living animals such as the Narroa mite, sheep scab mite and various poultry mites.
  • Such organisms are readily treatable by the claimed compounds due to their innocuous nature.
  • the pests must have the necessary enzymes available to convert the compounds into an active form.
  • the compounds are an improvement over the pesticides of the prior art in that they do not have a strong smell, are at least as potent as the earlier compounds and do not irritate the skin. Additionally, due to the required enzymes only being present in certain organisms, the compounds will only become active in particular organisms which should result in a reduction in toxicity in some environments.

Abstract

L'invention concerne une composition servant à exterminer des insectes ou animaux nuisibles. La composition comprend un alkylester d'un acide carboxylique ou combinaison d'alkylesters de la formule générale (I) dans laquelle l'un quelconque de A, B, C et D est hydrogène, ou bien A et B forment ensemble un groupe carbonyle et C et D sont tous deux hydrogène; et R est un groupe alkyle comprenant 1 à 20 atomes de carbone. Cette composition est particulièrement efficace contre les acariens. L'invention concerne en outre une méthode qui permet d'exterminer des insectes ou animaux nuisibles par application de la composition sur une zone attaquée par des insectes ou animaux nuisibles. Ces composés sans danger pour l'environnement sont convertis en composés de cinnamate actifs par des enzymes présentes chez l'insecte ou l'animal nuisible et provoquent la mort de ce dernier.
PCT/GB2001/005067 2000-11-18 2001-11-19 Compositions et methodes pour exterminer des insectes ou animaux nuisibles au moyen d'alkylesters d'acide benzene-propionique WO2002039815A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2002223818A AU2002223818A1 (en) 2000-11-18 2001-11-19 Compositions for, and a method of, exterminating pests using alkyl esters of benzenepropionic acid

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB0028164A GB0028164D0 (en) 2000-11-18 2000-11-18 Compositions for, and a method of, exterminating pests
GB0028164.2 2000-11-18

Publications (1)

Publication Number Publication Date
WO2002039815A1 true WO2002039815A1 (fr) 2002-05-23

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AU (1) AU2002223818A1 (fr)
GB (1) GB0028164D0 (fr)
WO (1) WO2002039815A1 (fr)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3267102A (en) * 1965-10-23 1966-08-16 American Home Prod Reaction products of 4, 6-diamino-5-nitrosopyrimidines with alkyl benzoylacetates, and process of obtaining the same
JPS63287745A (ja) * 1987-05-20 1988-11-24 Nippon Petrochem Co Ltd ２−（置換アリ−ル）プロピオン酸またはエステルの製造方法
US4802913A (en) * 1985-08-22 1989-02-07 Imperial Chemical Industries Plc Fungicidal alpha-substituted acrylates
EP0839447A1 (fr) * 1996-11-01 1998-05-06 Sumitomo Chemical Company, Limited Concentré émulsifiable pesticide

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3267102A (en) * 1965-10-23 1966-08-16 American Home Prod Reaction products of 4, 6-diamino-5-nitrosopyrimidines with alkyl benzoylacetates, and process of obtaining the same
US4802913A (en) * 1985-08-22 1989-02-07 Imperial Chemical Industries Plc Fungicidal alpha-substituted acrylates
JPS63287745A (ja) * 1987-05-20 1988-11-24 Nippon Petrochem Co Ltd ２−（置換アリ−ル）プロピオン酸またはエステルの製造方法
EP0839447A1 (fr) * 1996-11-01 1998-05-06 Sumitomo Chemical Company, Limited Concentré émulsifiable pesticide

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
DATABASE BIOSIS [online] BIOSCIENCES INFORMATION SERVICE, PHILADELPHIA, PA, US; 1995, MOIO L., ETIEVANT P.X.: "Ethyl anthranilate, ethyl cinnamate, 2,3-dihydrocinnamate, and methyl anthranilate: Four important odorants identified in Pinot noit wines of Burgundy", XP002188809, Database accession no. PREV199598450894 *
PATENT ABSTRACTS OF JAPAN vol. 013, no. 115 (C - 578) 20 March 1989 (1989-03-20) *

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AU2002223818A1 (en) 2002-05-27

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