JP2010018543A - Sexual pheromone substance of platyptilia ignifera, and sex attractant comprising the same - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a sexual pheromone substance of Platyptilia ignifera hopeful of its use for the pest's outbreak prediction, mass luring to death and communication disturbance, and to provide a sex attractant with the same as active ingredient. <P>SOLUTION: The sexual pheromone substance of Platyptilia ignifera comprising (Z)-7-dodecenyl acetate and (Z)-9-dodecenyl acetate is provided. As one of preferable embodiments, the substance containing, in addition, (Z)-5-decenyl acetate described in claim 1 is provided. Besides, the sex attractant comprising (Z)-7-dodecenyl acetate and (Z)-9-dodecenyl acetate is provided. As one of preferable embodiments, the sex attractant containing, in addition, (Z)-5-decenyl acetate described in claim 3 is provided as a preferable embodiment. <P>COPYRIGHT: (C)2010,JPO&INPIT

Description

  The present invention relates to a sex pheromone substance of grape orilyba (scientific name: Platyptilia ignifera) which is a pest of grapes, and an attractant containing the same.

  Grape oribata has become a problem as a pest that harms the fruits of grapes. The larvae feed on the flesh from the skin of the grain to make holes in the flesh, and discharge the feces through the holes. In recent years, it has been pointed out that fruit damage caused by this species greatly affects the yield in cultivated Yama grapes in Gifu Prefecture. Grape oribata is a minor pest in cultivated grapes, so it has not been fully studied and is in a state where it cannot be properly controlled (Non-patent Document 1). In addition, it is desirable to minimize the spraying of the insecticide from the viewpoint of environmental load and food safety. To that end, it is essential to investigate the occurrence and occurrence of this species and to endeavor to prevent it in a timely manner.

  Pheromone traps are widely used to predict the occurrence of moss. In recent years, the chemical structure of sex pheromone substances has been clarified in many mosses, and the occurrence and development of pests have been efficiently investigated using synthetic pheromones that have been chemically synthesized. In general, a sex pheromone substance is a chemical substance secreted by an adult female and exhibits a species-specific attracting action against the same male adult. By elucidating the chemical structure of such a sex pheromone substance and using it as a sex attractant, it is possible to conduct an efficient occurrence and development survey. Predicting the occurrence makes it possible to control in a timely manner, and is expected to prevent excessive spraying of insecticides. Furthermore, it is possible to control pests by using this sex attractant to kill a large number of males, and by using a communication disruption method that disrupts the mating behavior of males and females.

Regarding the genus Pterophoridae Platyptilia, to which Grape Otoriba belongs, two types of sex pheromones, Platyptilia Williamsii and Platyptia carduidactyla, have been investigated overseas. The composition is significantly different from that of the sex pheromone of grape gourd (Non-patent Document 2). In Japan, eight species of Trichogaceae have been described as agricultural pests (Non-patent Document 3), but the first example of the study of sex pheromones was grape giant bird. In addition, (Z) -11-hexadecenyl acetate and (Z) -11-hexadecenal have been reported as attractants of Platyptilia jezoensis which is not an agricultural pest in Japan. The composition differs greatly (Non-Patent Document 2).
Kamio et al. (2005) Gifu Prefectural Agricultural Technology Laboratory Report (5): 21-27 http://www.pherobase.com/database/genus/genus−Platyptilia.php Japan Society for Applied Entomology (2006) Agricultural and Forestry Harmful Animals Insect Directory Augmented Revised Edition 101pp

  The present invention has been made in view of the above circumstances, and is intended to provide a sex pheromone substance of grape oritriba which is expected to be used for occurrence prediction, mass killing, and communication disruption, and a sex attractant containing this as an active ingredient. It is.

In order to solve the above-mentioned problems, the present inventors first extracted a sex pheromone gland from a female adult under a microscope and extracted with n-hexane during the mating time period of grape gossip. The extract was concentrated, and (Z) -7-dodecenyl acetate, (Z) -9-dodecenyl acetate and (Z) -5-decene were analyzed by instrumental analysis using GC-EAD and GC-MS. Three components of senyl acetate were identified.
Furthermore, when the present inventors conducted a field attraction test, the activity as a sex attractant is a two-component of (Z) -7-dodecenyl acetate and (Z) -9-dodecenyl acetate. It was found that this kind of male adult was attracted to the mixture and a ternary mixture to which (Z) -5-decenyl acetate was further added, and the present invention was completed.

  Specifically, the present invention relates to a sex pheromone substance (composition) of grape tribe comprising at least (Z) -7-dodecenyl acetate and (Z) -9-dodecenyl acetate. provide. As one of the preferred embodiments, there is further provided the grape pheasant pheromone substance according to claim 1, further comprising (Z) -5-decenyl acetate. Further, the present invention provides a sex attractant for grape mantle which comprises at least (Z) -7-dodecenyl acetate and (Z) -9-dodecenyl acetate. As one of the preferred embodiments, a grape attractant sex attractant according to claim 3, further comprising (Z) -5-decenyl acetate is provided.

  ADVANTAGE OF THE INVENTION According to this invention, the sex attractant which is effective in attracting | sucking the adult male of a grape giant bird specifically and knowing the generation | occurrence | production situation can be obtained. In addition, this species can be controlled directly by mass killing or communication disruption.

(Z) -7-dodecenyl acetate, (Z) -9-dodecenyl acetate, and (Z) -5-decenyl acetate, which are the sex pheromone substances of grape tribe, were synthesized as follows. did.
First, as a synthesis example of (Z) -7-dodecenyl acetate, first, a Grignard reagent obtained by reacting (Z) -3-octenyl chloride, which is a known alkenyl chloride, with metal magnesium in tetrahydrofuran, A method similar to a known method is applied (Japanese Patent Publication No. 6-29219), and a cross-coupling reaction with 1-bromo-4-chlorobutane, which is an α-bromo-ω-chloroalkane, is performed as (Z) -7. -Dodecenyl chloride is produced. Subsequently, a substitution reaction is performed with sodium acetate in an acetic acid solvent, and after the reaction, distillation and purification are performed to obtain (Z) -7-dodecenyl acetate.

  (Z) -9-dodecenyl acetate can be synthesized by a known method (for example, Japanese Examined Patent Publication No. 6-29219).

  As a synthesis example of (Z) -5-decenyl acetate, a Grignard reagent obtained by reacting (Z) -3-octenyl chloride, which is a known alkenyl chloride, with metal magnesium in tetrahydrofuran, and ethylene oxide are known. (Z) -5-decen-1-ol, and then esterified with acetic anhydride to give (Z) -5-decenyl acetate. To prepare.

A sex attractant for grape oativa comprising at least (Z) -7-dodecenyl acetate and (Z) -9-dodecenyl acetate comprises (Z) -7-dodecenyl acetate and The mixing ratio with (Z) -9-dodecenyl acetate is preferably 1000: 1 to 1000: 200 (mass ratio), more preferably 1000: 50 to 1000: 150 (mass ratio). If the amount of (Z) -7-dodecenyl acetate is outside the above preferred range, the attractiveness may be lowered.
The sex pheromone material of grape tribe comprising (Z) -7-dodecenyl acetate and (Z) -9-dodecenyl acetate is (Z) -7-dodecenyl acetate and ( The content ratio with Z) -9-dodecenyl acetate is preferably 1000: 1 to 1000: 200 (mass ratio), more preferably 1000: 50 to 1000: 150 (mass ratio). If the amount of (Z) -7-dodecenyl acetate is outside the above preferred range, the function as a sex pheromone may be reduced.

The sex attractant comprising (Z) -7-dodecenyl acetate and (Z) -9-dodecenyl acetate preferably further comprises (Z) -5-decenyl acetate. be able to. Inclusion can be increased by including (Z) -5-decenyl acetate. The mixing ratio of (Z) -5-decenyl acetate is preferably 1 to 50% by mass, more preferably 20 to 30% by mass with respect to (Z) -7-dodecenyl acetate. .
The grape tiger tribe sex pheromone substance comprising (Z) -7-dodecenyl acetate and (Z) -9-dodecenyl acetate is a derivative of (Z) -7-dodecenyl acetate. Preferably, 1-50 mass%, More preferably, 20-30 mass% (Z) -5-decenyl acetate can further be included.

Examples of the sex attractant containing the sex pheromone substance of grape gourd of the present invention include antioxidants such as butylhydroxytoluene, butylhydroxyanisole, hydroquinone, vitamin E, and ultraviolet absorbers such as 2-hydroxy-4-octoxybenzophenone An appropriate amount may be added.
For example, with respect to the total amount of (Z) -7-dodecenyl acetate, (Z) -9-dodecenyl acetate and (Z) -5-decenyl acetate, for example, the antioxidant is 1 -5% by weight, and UV absorber is 1-5% by weight.

The attractant of the present invention is made from a substance having a release amount control function such as rubber, polyethylene, polypropylene, ethylene-vinyl acetate copolymer, polyvinyl chloride, etc. in order to maintain a certain amount of release of the active ingredient over a long period of time. It is used by filling a container such as a cap, a thin tube, a laminated bag, or a capsule.
The amount of the sex pheromone substance carried in the container is preferably in the range of 0.1 mg to 5.0 mg.

Hereinafter, specific embodiments of the present invention will be described with reference to examples and comparative examples, but the present invention is not limited to the examples.
<Identification of active ingredient>
Grape oribatae collected from the field were grown up to adults in the laboratory, and pheromone glands were extracted from the unmature female adults (2 to 3 days old) under a microscope and immersed in n-hexane for 1 hour. Then, what removed the parasite structure | tissue by filtration from the extract was made into the grape mantle extract.
The GC-EAG chart of the grape mantle extract is shown in FIG. In the crude extract, components (peaks A to C) to which the male antennae responded clearly were found. Components in this extract were analyzed by GC-MS and identified by comparison with retention times and mass spectra with various synthetic products. As a result, peaks A to C which are present in the female pheromone and cause EAG reaction are (Z) -5-decenyl acetate, (Z) -7-dodecenyl acetate and (Z) -9-, respectively. It was dodecenyl acetate and the mixing ratio was found to be 14: 55: 5 (mass ratio), respectively. FIG. 2 shows a three-component mass spectrum showing EAG activity in the extract, and FIG. 3 shows a synthetic product mass spectrum.

<Adhesive trap>
As shown in FIG. 4, the adhesive trap is composed of a roof and a bottom plate, and has a narrow insect entrance. And an adhesive substance is stuck on the upper surface of the bottom plate, and an attractant is directly placed on the adhesive surface for use. That is, it has a structure that captures only insects that have approached the attractant, and has a structure that eliminates as much as possible non-target insects. This sticky trap was hung in a vineyard.

Examples 1-2 and Comparative Examples 1-4
A synthetic compound of (Z) -7-dodecenyl acetate, (Z) -9-dodecenyl acetate and (Z) -5-decenyl acetate was mixed in a predetermined ratio, and the total mass was Butyl hydroxytoluene to 2.0% by weight was added. And these mixtures are three components of (Z) -7-dodecenyl acetate, (Z) -9-dodecenyl acetate, (Z) -5-decenyl acetate, or (Z) -7. The attractant of Examples 1 and 2 was prepared by supporting two components of -dodecenyl acetate and (Z) -9-dodecenyl acetate on rubber caps made of isoprene. (Z) -7-dodecenyl acetate, (Z) -5-decenyl acetate, or (Z) -9-dodecenyl acetate and (Z) -5-decenyl acetate The mixture which added the butylhydroxytoluene to the component and (Z) -7-dodecenyl acetate one component was made into Comparative Examples 1-3. Further, a rubber cap made of isoprene that does not contain (Z) -7-dodecenyl acetate, (Z) -9-dodecenyl acetate, (Z) -5-decenyl acetate, and butylhydroxytoluene is used in Comparative Example 4. As an attractant. The attractant was left overnight and then attached to a white adhesive trap. The synthetic compounds supported on each trap are shown in Table 1.
A trap with each attractant set was attached to each of the four sections of the vineyard where the grape giant was generated. The number of adult males killed by each trap was counted every 3-6 days and continued for 17 days. The results are shown in Table 2.

  Only one animal was killed in Comparative Example 1, and none was killed in Comparative Examples 2-4. On the other hand, in Example 1 and Example 2, 6 and 11 attractions were observed, and (Z) -7-dodecenyl acetate and (Z) -9-dodecenyl acetate were attracted to this species. I understand that it is essential.

Fig. 2 shows a GC-EAD chart of a pheromone extract extracted from a female grape tribe adult. The upper side shows the EAG chart and the lower side shows the GC-FID chart. The peaks A to C in the figure indicate the components in which EAG activity was recognized among the components separated by GC. The mass spectrum of the component by which EAG activity was recognized among the components obtained from the grape mantle extract was shown. The mass spectrum of (Z) -5-decenyl acetate, (Z) -7-dodecenyl acetate, (Z) -9-dodecenyl acetate is shown. It is a figure which shows an adhesion type trap.

Claims (4)

  A sex pheromone substance of grape mantle which comprises at least (Z) -7-dodecenyl acetate and (Z) -9-dodecenyl acetate.   Furthermore, the sex pheromone substance of the grape gossip bird of Claim 1 which comprises (Z) -5-decenyl acetate.   A sex attractant for grape mantle which comprises at least (Z) -7-dodecenyl acetate and (Z) -9-dodecenyl acetate.   The grape attractant sex attractant according to claim 3, further comprising (Z) -5-decenyl acetate.

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