EP0495955A1 - Von der eiablage abschreckendes pheromon, das mindestens einen fettsäurealkylester enthält und seine verwendung zur bekämpfung von schadinsekten - Google Patents

Von der eiablage abschreckendes pheromon, das mindestens einen fettsäurealkylester enthält und seine verwendung zur bekämpfung von schadinsekten

Info

Publication number
EP0495955A1
EP0495955A1 EP91914378A EP91914378A EP0495955A1 EP 0495955 A1 EP0495955 A1 EP 0495955A1 EP 91914378 A EP91914378 A EP 91914378A EP 91914378 A EP91914378 A EP 91914378A EP 0495955 A1 EP0495955 A1 EP 0495955A1
Authority
EP
European Patent Office
Prior art keywords
methyl
oviposition
parts
preparation
fatty acid
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP91914378A
Other languages
English (en)
French (fr)
Inventor
Denis Thiery
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Centre National de la Recherche Scientifique CNRS
Institut National de la Recherche Agronomique INRA
Original Assignee
Centre National de la Recherche Scientifique CNRS
Institut National de la Recherche Agronomique INRA
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 Centre National de la Recherche Scientifique CNRS, Institut National de la Recherche Agronomique INRA filed Critical Centre National de la Recherche Scientifique CNRS
Publication of EP0495955A1 publication Critical patent/EP0495955A1/de
Withdrawn legal-status Critical Current

Links

Classifications

    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N37/00Biocides, 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
    • A01N37/02Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N37/00Biocides, 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
    • A01N37/06Unsaturated carboxylic acids or thio analogues thereof; Derivatives thereof
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N63/00Biocides, pest repellants or attractants, or plant growth regulators containing microorganisms, viruses, microbial fungi, animals or substances produced by, or obtained from, microorganisms, viruses, microbial fungi or animals, e.g. enzymes or fermentates
    • A01N63/10Animals; Substances produced thereby or obtained therefrom
    • A01N63/14Insects

Definitions

  • the invention relates to the purification and characterization of an anti-oviposition pheromone, as well as to a chemical composition having the anti-oviposition properties of said pheromone, and to the application of said pheromone and said compound. ⁇ the fight against insect pests.
  • Anti-oviposition pheromones are intra-specific chemical signals deposited by certain female insects on and / or in the vicinity of their eggs after laying. The locations thus marked are then rejected by the other females of the same species as nesting sites.
  • the other is the anti-oviposition pheromone of the dipteran Rhagoletis cerasi, which is a derivative of palmityl glucopyranoside; the synthesis of the four possible stereoisomers of this derivative has been carried out [ERNST and WAGNER, Helv. Chim. Acta, 22, 165-171, (1989)], in order to determine
  • REPLACEMENT SHEET ner which corresponded to the active natural form of the pheromone.
  • KLIJNSTRA Entomol. exp.appl., &, 139-146, (1986)
  • pesticides essentially synthetic pyrethroids.
  • these pyrethrinoids are increasingly suspected of promoting the spread of aphid populations, and of diseases, in particular viral, inoculated by sucking biting insects.
  • the Inventor is the first to extract such a substance from the eggs of the corn borer. Analysis of the extract thus obtained revealed that it was a complex mixture, as shown by the chromatographies of Figures 1 and 2.
  • the inventor has also managed to select and identify in this mixture, constituents which, surprisingly, have a anti-oviposition activity comparable to that of the total extract.
  • the present invention relates to a prepa ⁇ ration of anti-oviposition pheromone, which preparation is characterized in that it is suscep ⁇ tible to be obtained from a methanolic extract of the eggs of the corn borer, and in what it includes a mixture of the methyl esters of palmitoleic, palmitic, linoleic, oleic and stearic acids.
  • said preparation comprises: between 10 and 20 parts of methyl palmitoleate, between 10 and 20 parts of methyl palmitate, between 10 and 20 parts of methyl linoleate, between 10 and 20 parts methyl oleate, for 1 to 2 parts of methyl stearate.
  • the identification of active components has enabled the formulation of simple compositions reproducing the effect, on the reduction of the laying of the corn borer, of the preparation of anti-oviposition pheromone in accordance with the invention.
  • the present invention further relates to an anti-oviposition composition, active in particular on the corn borer, and characterized in that it comprises as active ingredient, at least one alkyl ester in and C-j_4_20 fatty acid *
  • an anti-oviposition composition in accordance with the invention, it comprises, as active principle, at least one methyl ester of a fatty acid with a straight chain C- j ⁇ g-
  • said methyl ester of fatty acid with a straight chain is chosen from the group which comprises: methyl palmitoleate, methyl palmitate, methyl linoleate, oleate of methyl, methyl stearate, and mixtures thereof.
  • an anti-oviposition composition in accordance with the invention comprises: between 10 and 20 parts of methyl palmitoleate, between 10 and 20 parts of methyl palmitate, between 10 and 20 parts of methyl linoleate, between 10 and 20 parts of methyl oleate, for 1 to 2 parts of methyl stearate.
  • said composition comprises at least 0.08 g / l of methyl palmitoleate, 0.1 g / l of ⁇ -methyl palmitate, 0.08 g / l of methyl linoleate, 0 , lg / l of methyl oleate, 0.008 g / 1 of methyl stearate
  • a composition in accordance with the invention comprises: between 0.3 and 2 g / 1 of methyl palmitoleate, between 0.3 and 2 g / 1 of methyl palmitate, between 0.3 and 2 g / 1 of methyl linoleate, between 0.3 and 2 g / 1 of methyl oleate and between 0.03 and 0.2 g / 1 of methyl stearate.
  • an anti-oviposition composition comprising 1.1 g / l of methyl palmitoleate, 1.45 g / l of methyl palmitate, 1.1 g / l of methyl linoleate, 1.3 g / 1 methyl oleate and 0.1 g / 1 methyl stearate, dissolved in a mixture comprising 1 volume of methanol for 9 volumes of water, can be used for the treatment of corn plants under the following conditions: - single application - spraying of the composition on one row of corn on two.
  • 1'Invention can be obtained in a simple and inexpensive, from alkyl esters of fatty acids which are readily available commercially. They can therefore be used on a large scale in the treatment of crops.
  • the present invention therefore also relates to the application of a composition, or a purified preparation of an anti-oviposition pheromone, as defined above, to the protection of plants against insect pests, particularly European moth. But.
  • the subject of the present invention is a process for protecting plants against insect pests, particularly the European corn borer, which process is characterized in that the plants to be treated are brought into contact with a composition or a preparation of pheromone. anti-oviposition according to the invention.
  • FIG. 1 represents the profile obtained on a CPWAX58 column.
  • FIG. 2 represents the profile obtained on a DB5 column.
  • the compounds thus identified by each of these methods were compared, on the basis of their retention time, to standards.
  • the dosage of the constituents was obtained by gas chromatography.
  • the selected components were identified by infrared spectrometry, coupled with FOURIER transform analysis
  • Methyl palmitoleate, methyl palmitate, methyl linoleate, methyl oleate, and methyl stearate are mixed in the proportions indicated in Table I above. The mixture is dissolved in methanol EXAMPLE 4 - COMPARISON OF THE EFFICIENCY OF THE COMPOSITIONS
  • Each oviposition substrate has been divided into two zones: one is impregnated with the test solution (egg extract prepared according to the procedure described in Example 1, composition prepared according to the procedure described in Example 3, or solvent alone) at the desired concentration, the other is not impregnated.
  • the test solution egg extract prepared according to the procedure described in Example 1, composition prepared according to the procedure described in Example 3, or solvent alone
  • the deposit is made using a precision syringe. 90 drops of 2.5 ⁇ l each are deposited on the test area.
  • the concentrations used are expressed in opaque / drop equivalent, and are 0.7, 2, and 4.
  • the anti-oviposition composition prepared according to the procedure described in Example 3 is used at a concentration of 1.616 g / ml of the mixture of methyl esters of fatty acids, which corresponds to 4 opaque equivalents / drop.
  • the treated oviposition supports were placed in the cages. 2-day-old borer females were left in the presence of supports, for 2 consecutive nights, at the end of which the ooplaques deposited on the treated areas, on the one hand, and on the untreated control areas, d on the other hand, were enumerated.
  • FIG. 3 represents the results obtained with the preparation of egg extract: on the ordinate, the number of opoplates deposited on the treated area ( as a% of the total number of opoplates deposited on the support), and, on the abscissa, the concentration of the extract in ooplate equivalents / drop.
  • Figure 4 shows the comparison of the effectiveness of the preparation of egg extract of and the composition prepared as described in Example 3, on the reduction of the laying of the corn borer.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Environmental Sciences (AREA)
  • Insects & Arthropods (AREA)
  • Biotechnology (AREA)
  • Microbiology (AREA)
  • Virology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Catching Or Destruction (AREA)
EP91914378A 1990-08-10 1991-08-02 Von der eiablage abschreckendes pheromon, das mindestens einen fettsäurealkylester enthält und seine verwendung zur bekämpfung von schadinsekten Withdrawn EP0495955A1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR9010253A FR2665610B1 (fr) 1990-08-10 1990-08-10 Pheromone anti-oviposition comprenant au moins un alkyl ester d'acide gras, et son application a la lutte contre les insectes ravageurs.
FR9010253 1990-08-10

Publications (1)

Publication Number Publication Date
EP0495955A1 true EP0495955A1 (de) 1992-07-29

Family

ID=9399610

Family Applications (1)

Application Number Title Priority Date Filing Date
EP91914378A Withdrawn EP0495955A1 (de) 1990-08-10 1991-08-02 Von der eiablage abschreckendes pheromon, das mindestens einen fettsäurealkylester enthält und seine verwendung zur bekämpfung von schadinsekten

Country Status (6)

Country Link
EP (1) EP0495955A1 (de)
JP (1) JPH05502045A (de)
CA (1) CA2066589A1 (de)
FR (1) FR2665610B1 (de)
IL (1) IL99105A0 (de)
WO (1) WO1992002138A1 (de)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4206090C2 (de) * 1992-02-27 1998-02-05 Perycut Chemie Ag Insektenabwehrmittel
FR2720229B1 (fr) * 1994-05-30 2001-08-31 Agronomique Inst Nat Rech Utilisation d'au moins un acide gras éventuellement associé à au moins un ester d'acide gras, contre la ponte des lepidoptères tortricides.
DE19804638C2 (de) * 1998-02-06 2001-05-17 Geesthacht Gkss Forschung Antifouling-Membranen
US20080069785A1 (en) * 2004-12-14 2008-03-20 Jones Allen L Pest-control compositions, and methods and products utilizing same
US20240041036A1 (en) * 2020-12-07 2024-02-08 Fertis India Pvt. Ltd. Bio pesticidal composition contains novel nonanoate esters of sugars and sugar alcohols to control lepidoptera, hemiptera and thysanoptera insects

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS60185702A (ja) * 1984-01-25 1985-09-21 Japan Tobacco Inc タバコシバンムシの忌避剤
FR2638326B1 (fr) * 1988-11-03 1991-01-25 Agronomique Inst Nat Rech Procede pour la lutte biologique contre la varroatose et dispositifs pour la mise en oeuvre de ce procede

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9202138A1 *

Also Published As

Publication number Publication date
FR2665610A1 (fr) 1992-02-14
CA2066589A1 (fr) 1992-02-11
IL99105A0 (en) 1992-07-15
JPH05502045A (ja) 1993-04-15
FR2665610B1 (fr) 1994-03-11
WO1992002138A1 (fr) 1992-02-20

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