JPH05502045A - Anti-oviposition pheromones containing at least one alkyl ester of fatty acids and their application in the control of destructive insects - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

[Detailed description of the invention] Anti-spawning pheromones containing at least one alkyl ester of fatty acids and ITS APPLICATION IN THE CONTROL OF DESTRUCTIVE INSECTS The present invention uses an anti-ovip pheromone (anti-ovip purification and characterization of the pheromone), Chemical compositions with spawning properties as well as destructive insects (ravaginginsec) Application of the pheromone and the composition to combating ts) related.

Anti-spawning pheromones are placed on and/or near eggs by some female insects after spawning. It is an intra-specific chemical signal attached to

Areas marked in this way will subsequently be rejected as spawning grounds by other females of the same species. Extinct.

Therefore, the deterrent effect of these pheromones ( It has been proposed to use dissuasive effects.

However, the existence of such pheromones has not been described for numerous insects. For reviews, see Roitberg and Procopy (ROITBERG an d PROKOPY) [Bioscience, 37 ．． 400-406 (1987)], but most of them are effective. is not purified and its chemical properties often remain undetermined. It is.

Currently, only two compounds of this type have been chemically characterized. One is Lepidoptera Ephestia kuebniella ) is a kairomone consisting of a mixture of 16 triketones (MUDI). )), J, Ch’em, Soc. Strictly speaking, this is not an anti-spawning pheromone. It is a kairomone present in the mandibular glands of the larvae of these lepidoptera, and Invitation to Venturia canesc’ens exert a negative effect.

The other is a palmityl glucopyranoside derivative (palmity1gluc'op yranoside derivative), a dipteran Lagoretis serassi (R'hagoletis cerasi) is an anti-spawning fuxomon. this synthesis of the four possible stereoisomers of the derivative or the active natural form of the pheromone. have been carried out to determine the corresponding ones (Ernst and Wagner (ER NST and WAGNER), He1v, Chim, Acta, 72 ．． 165-171. , (1989)).

A partially purified preparation of this pheromone obtained from secretions previously collected from the spawning site. The product reduced damage to plants by R, cerasi by 90%. It was shown that (KATSOYANNO3 and B OLLER), Z, Angex anti-spawning pheromone presence and efficacy also It has also been shown in other insects and their chemical composition has not been determined. Not yet. For example, KLIJNSTRA.

Entomol, Exp, Appl, 41.139-146 (1986 )) are Pieris brassicae eggs. The methanol solution obtained by washing the solution is substantially treated with the solution. shown to reduce the number of eggs laid by females of this species on plants .

What is the potential interest of anti-oviposition pheromones in controlling destructive insects? However, their practical application is limited to obtaining them in sufficient quantities. They can only be considered if it is possible to synthesize them chemically.

Among the destructive insects currently causing substantial damage resulting in high economic losses. One of the insects that Ostrinia nubilis (Ostrinia nubilis)).

It is found in the form of plates (ooplat) on the leaf surface of various plants. es)) is a moth that attaches its eggs and covers them with mucus.

This Lepidoptera is divided into several specialized and vulnerable hybrid species. , a corn ravage that effectively reduces yields by as much as 40%. r) (KLENKE et al., Klopp Saie Crop 5ciense, 26. p.

859 (1986)). Furthermore, the damage caused by this insect is now It is expanding into other crops like vegetable crops and cotton.

Current recommendations for controlling this insect include toxic pesticides. cfes), mainly synthetic pyrethrinoids (synthetic pyrethr inoids). However, these pyrethrinoids It promotes the reproduction of insect populations and prevents diseases, especially insects inoculated by sucking and penetrating insects. There is growing suspicion that it promotes viral disease.

Anti-oviposition substances are present in extracts of corn borer larval excrement has been shown (DITTRICK et al., J. In5ect, Physiol, 29. p. 119 (1983)) . However, their chemical composition has not been determined, only that they are polar compounds. It only suggests that it is of high quality. Furthermore, the practical effects performed by these substances Regarding the biological role of g-1aying) It might happen. Previously, substances of plant origin produced from plant wounds have shown anti-oviposition activity. Since it was shown that DITTRICK et al. l) The detected anti-oviposition activity is produced by the plant and transferred to the larval excrement. The hypothesis was that this was caused by a substance that

So far, the existence of anti-oviposition pheromones related to the eggs of the corn borer moth has been investigated. This has not been verified.

The inventor first extracted such a substance from the eggs of the corn borer. . By analyzing the extract obtained in this way, the chromatographs shown in Figures 1 and 2 were found. Regarding complex mixtures such as those shown in ram It became clear that it would.

The inventor further discovered that in this mixture, surprisingly, the anti-spawning activity of the total extract was We succeeded in selecting and identifying components with anti-spawning activity comparable to sex.

The present invention relates to an anti-spawning pheromone preparation. The product is methanol of corn maizepyralid eggs. It can be obtained from methanolic extract. Methylated mitoleic acid, palmitic acid, linoleic acid, oleic acid and stearic acid It is characterized by containing a mixture of esters.

According to a preferred embodiment of the invention, the preparation contains 10 to 20 parts of methane palmitoleate. chill, 10-20 parts methyl palmitate, 10-20 parts methyl linoleate, Contains 10-20 parts methyl oleate and 1-2 parts methyl stearate .

Identification of active ingredients reduces the number of eggs laid by the corn borer moth A simple method capable of reproducing the effects of the anti-spawning pheromone preparation of the present invention in reducing It has become possible to prepare a composition that is

The present invention further provides an anti-spawning composition ( anti-oviposition composition), with active Contains as a component at least one 01-3 alkyl ester of C fatty acid It also relates to a composition characterized in that.

According to one of the preferred embodiments of the anti-spawning composition of the invention, it contains C as an active ingredient. The straight chain fatty acid methyl yellow 18 Contains at least one type of ster.

According to one particularly advantageous feature of this embodiment, the methyl ester of the linear fatty acid is , methyl palmitoleate, methyl palmitate, methyl linoleate, olein selected from the group consisting of methyl acid, methyl stearate and mixtures thereof.

According to a preferred embodiment of this feature, the anti-spawning composition of the invention comprises 10 to 20 parts of Methyl lumitoleate, 10-20 parts methyl palmitate, 10-20 parts lysate Methyl oleate, 10-20 parts methyl oleate and 1-2 parts stearic acid Contains methyl.

According to another preferred embodiment of this feature, the composition contains at least 0.08 g/l Methyl palmitoleate, 0.1 g/l Methyl palmitate, 0.08 g/I of methyl linoleate, 0.1 g/l of methyl oleate and 0.008 g/l of Contains methyl stearate.

These values indicate the concentrations of active ingredients at which anti-spawning activity can be observed. Naturally, The concentration of methyl esters of these fatty acids may be higher. maximum concentration that can be used The degree is limited only by the solubility of the active ingredient in the solvent used. optimum density The intensity depends on the treatment conditions in the field, the number and frequency of applications, the overall treatment of the plant or It varies depending on whether it is a partial process, etc.

The composition of the invention comprises 0.3-2 g/l methyl palmitoleate, 0.3-2 g/l /l methyl palmitate, 0.3-2 g/l methyl linoleate, 0.3-2 g/l methyl oleate and 0.03-0.2 g/l methyl stearate. It is advantageous to contain.

As an example, 1.1 g/l methyl palmitoleate, 1.45 g/l palmitoleate, Methyl oleate, 1.1 g/l methyl linoleate, 1.3 g/l methyl oleate and 0.1 g/l methyl stearate in 1 volume of methanol and 9 volumes of water. For treating corn with an anti-spawning composition containing in dissolved form in a mixture , Ni used under the following conditions. - Single application One row of each two rows of corn is sprayed with the composition.

Under these conditions, 1 liter of this solution is used to treat approximately 50 m2 of crop.

The anti-spawning composition of the present invention is composed of commercially widely available alkyl esters of fatty acids. It can be obtained by a simple and inexpensive method. Therefore, they are of great importance in crop processing. Can be used on any scale.

The invention therefore protects plants from destructive insects, especially the corn borer moth. of a composition or purified anti-spawning pheromone preparation as defined above for It also concerns application.

In particular, the present invention provides methods for protecting plants from destructive insects, especially the corn borer moth. With respect to the method, the method comprises treating the plants to be treated with a composition of the invention or with an anti-oviposition pheromone preparation. It is characterized by bringing it into contact with a product.

The invention is further described below with reference to the Examples of Preparation and Use of Compositions of the Invention. would be better understood by However, these examples merely represent the present invention. This is intended to be illustrative of, and in no way limited to, the subject matter of It's no good.

To the female Ostrinia nubilalis, Eggs are laid on a chemically inert substrate (a glass plate rinsed in methanol). I set it. Thus 1580 ooplates were obtained. O Dissolve the plate containing the plate in 200 ml of cold methanol ( purity >99.9%) for 12 hours. The resulting extract is then used as Dufton Kara. Concentrated to a volume of 20 ml by evaporation on a Dufton column. .

The various concentrations used subsequently do not require diluting the thus concentrated extract. It is obtained by

10 μl of the extract obtained in Example 1 was used for each analysis.

1/Gas phase chromatography The characteristics of the equipment used are as follows. On-column injector, gear , Pillary column, phase: D B 5 i, d, 0.53 (SE52 equi iv, ) and CPWAX58 i, d, 0.32 (carbowax equi v, (Carbowax equiv, )) (i, d, = inner diameter) One initial temperature is increased linearly from 70°C to 240°C.

The chromatographic profiles obtained under these conditions are shown in Figures 1 and 2. show.

Figure 1 shows the profile obtained with the CPWAX58 column. Figure 2 is DB The profile obtained in 5 columns is shown.

Each of such compounds identified by these methods is characterized by their retention times ( compared to the standard based on the retention time).

Component assays were obtained by gas phase chromatography.

Selected components were analyzed using infrared spectrometry (infrared spectrometry) coupled with Fourier transform analysis. frared spectrometry).

Table 1 below provides a list of these ingredients, the amounts assayed, and their chemical properties. .

Table 1 Methyl palmitoleate 0.22 268.44 Methyl palmitate 0.　 29 270. 46 Methyl linoleate 0.22 294.48 Methyl oleate Chill 0.26 296.49 Methyl stearate 0. 02 298. 5 Measured at 1*μg/oplate equivalent (average obtained from 1,580 oplates) ) Example 3: Preparation of anti-spawning composition of the present invention Methyl palmitoleate, palmitic acid Methyl, methyl linoleate, methyl oleate and methyl stearate (Sigma (manufactured by Co., Ltd.) in the proportions shown in Table 1 above. Dissolve the mixture in methanol .

To investigate spawning behavior, a spawning substrate capable of laying eggs is placed and a wax paper sheet ( From a plastic grid with waxed 5 sheets of paper The experiment was carried out in a cage made of altugrass.

Each spawning substrate was divided into two zones. One is a test solution of the desired concentration (as in Example 1). Egg extract prepared according to the method described in Example 3 (or only solvent); It's a good thing.

In each solution tested, deposition is performed using a precision syringe. 2.5μl each Apply 90 drops to the test zone.

In the case of extracts, the concentrations used are ooplate equivalents/drop. equivalents/drop) and are 0, 7.2 and 4. .

The anti-spawning composition prepared according to the method described in Example 3 was added to the fatty acid methyl ester. 1 of the mixture of esters, used at a concentration of 616 mg/ml. This is a 4-op Corresponds to letto equivalent/drop.

After evaporation of the solvent, the treated spawning support was placed in a cage. 2 day old Meiriki Females were left in the presence of the support for two consecutive nights, after which one was placed in the treatment zone and the other counted the giant plates attached to the untreated control zone.

The results obtained are shown in FIGS. 3 and 4, representing the average of three experiments.

Figure 3 shows the results obtained using the egg oil extract preparation.

The ordinate is the number of OOPs deposited on the treatment zone (OOPs deposited on the support). (expressed as % of the total number of samples), the abscissa is the extraction in ooplate equivalents/droplet Indicates the concentration of a substance.

These results are based on the number of plates deposited on the treatment zone or the number of plates deposited on the support. Increasing the concentration of the prepared preparation shows a very significant decrease.

Figure 4 shows the effects of the corn borer on reducing the number of eggs laid by the corn borer. Comparison of the effectiveness of the egg extract preparation and the composition prepared as described in Example 3. It shows.

The % reduction of ooplates on the treated zone relative to the untreated zone is expressed on the ordinate. It will be done. From this, the effect of the anti-spawning composition obtained according to Example 3 is It has been shown that the effectiveness of anti-spawning pheromone preparations obtained from eggs of It is clear.

As is clear from the above description, the present invention is based on the embodiments and embodiments more clearly described above. It is not limited in any way to the type or application. On the contrary, the present invention It encompasses all variations that come to the mind of experts in this field, without departing from the structure or scope. Contains.

FrGURE 3 8 0.7 2 4 Concentration of extract (1 per plate FIGURE 4 Concentration in Oplate equivalent abstract The present invention can be obtained from the methanol extract of corn borer eggs, and palmitoleic acid, palmitic acid, linoleic acid, oleic acid and stearic acid. anti-spawning pheromone preparation characterized in that it contains a mixture of methyl esters of phosphoric acids; 01-3 alkyl ester of at least one C fatty acid as active ingredient. Antibiotics that are particularly active against corn borer moths, characterized by containing ster Egg compositions and their application for controlling destructive insects.

international search report Wml^e””””PCT/FR91100641

Claims (10)

[Claims] 1. An anti-spawning pheromone preparation, the preparation comprising: , methanol extract of maize pyralid eggs palmitoleic acid, palmitic acid, linoleic acid, characterized by containing a mixture of methyl esters of leic acid and stearic acid preparation. 2. 2. The anti-spawning pheromone preparation according to claim 1, wherein the preparation contains 10 to 2 0 parts methyl palmitoleate, 10-20 parts methyl palmitate, 10-2 0 parts methyl linoleate, 10-20 parts methyl oleate and 1-2 parts ste Preparation characterized in that it contains methyl allynate. 3. Particularly active against corn borer moth, and contains only a small amount of active ingredient. Contains at least one C1-3 alkyl ester of C14-20 fatty acid. Characteristic anti-spawning composition. 4. As an active ingredient, at least methyl esters of C16-18 straight chain fatty acids The anti-spawning composition according to claim 3, characterized in that it contains one species. 5. Methyl palmitoleate, methyl palmitate, methyl linoleate, olei selected from the group consisting of methyl stearate, methyl stearate and mixtures thereof. Antibiotics according to claim 4, characterized in that it contains a methyl ester of a straight chain fatty acid. egg composition. 6. 10-20 parts methyl palmitoleate, 10-20 parts methyl palmitate 10-20 parts of methyl linoleate, 10-20 parts of methyl oleate and 1 Antibiotics according to claim 5, characterized in that it contains ~2 parts of methyl stearate. egg composition. 7. At least 0.08 g/1 methyl palmitoleate, 0.1 g/1 pal Methyl mitate, 0.08g/1 methyl linoleate, 0.1g/1 olein methyl stearate and 0.008 g/1 methyl stearate. The anti-spawning composition according to claim 5 or 6. 8.0.3-2g/1 methyl palmitoleate, 0.3-2g/1 palmiti Methyl phosphate, 0.3-2g/1 Methyl linoleate, 0.3-2g/1 Olay methyl stearate and 0.03 to 0.2 g/1 of methyl stearate. The anti-spawning composition according to claim 7, characterized in that: 9. Claim 1 for the protection of plants from destructive insects, in particular the corn borer moth Application of the composition or anti-spawning pheromone preparation according to any of claims 1 to 8. 10. A method of protecting plants from destructive insects, in particular the corn borer, comprising: The plants to be treated are treated with the composition or the anti-oviposition pheromone according to any one of claims 1 to 8. A method characterized in that the method is characterized in that the method is characterized in that: