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    • 专利摘要:
    Attractant composition of the species Delottococcus aberiae, methods for the detection, monitoring and/or control of the pest The present invention relates to the compound (4,5,5-trimethyl-3-methylenecyclopent-1-en-1-yl) methyl acetate and to an insect attractant composition of the Delottococcus aberiae species comprising said compound. The present invention also relates to a Delottococcus aberiae attracting device comprising said compound or said composition and a method of control and/or monitoring of insect populations of the Delottococcus aberiae species. (Machine-translation by Google Translate, not legally binding)
    公开号:ES2760398A1
    申请号:ES201831098
    申请日:2018-11-13
    公开日:2020-05-13
    发明作者:Fuertes Ismael Navarro；González Sandra Vacas；Llopis Vicente Navarro；Bargués Javier Marzo；Garcia Alejandro Carbonell；Millo Jaime Primo
    申请人:Ecologia Y Proteccion Agricola S L；Universidad Politecnica de Valencia；
    IPC主号:
    专利说明:

    [0001]
    [0002] Field of technique
    [0003]
    [0004] The present invention falls within the technical field of agricultural pest control, in particular relates to an attractive product for insects of the species Delottococcus aberiae.
    [0005]
    [0006] State of the art prior to the invention
    [0007]
    [0008] The Valls cotonet, Delottococcus aberiae (De Lotto) (Hemiptera: Pseudococcidae), is a recently introduced pest in citrus in the Mediterranean area. The first individuals of Delottococcus aberiae were detected in 2009 in the town of Benifairó de les Valls (Valencia), causing very intense deformations observed in sweet and clementine orange fruits that lead to their complete commercial depreciation (Beltrá, A; García Marí, F ; Soto, A.
    [0009] 2013. The Vallone cotonet, Delottococcus aberiae, a new citrus plague. Levante Agrícola 419, 348-352). In addition, like the rest of the pseudococids, it feeds on sap and produces molasses that causes the proliferation of saprophytic fungi, as well as a decrease in the photosynthetic rate and the loss of plant vigor.
    [0010] This species is native to Sub-Saharan Africa and its presence has only been described in some countries of central and southern Africa: Kenya, Mozambique, Swaziland, South Africa, Tanzania and Zimbabwe (Ben-Dov, Y., Miller, DR, Gibson, GAP 2013 ScaleNet, Delottococcus aberiae. 20 May 2013. http://www.sel.barc.usda.gov/catalogs/pseudoco/Delottococcusaberiae.htm), so its introduction in Spain should be related to the importation of plant material from from any of these countries.
    [0011]
    [0012] Delottococcus aberiae is a polyphagous insect cited in crops, both tropical and subtropical and temperate, such as coffee, guava or olive (De Lotto, G. 1961. New Pseudococcidae (Homoptera: Coccoidea) from Africa. Bull. Br. Mus. (Nat. Hist.) Entomol. 10: 211-238), but has never before been described as damaging citrus. It is due to this recent invasion that, unfortunately, there are no specific means of control available, as it is a new pest for the cultivation of citrus fruits worldwide. In addition to the commercial depreciation of the fruit, its presence in them can cause serious quarantine problems for citrus exports as it is a new citrus plague in Europe, restricted to date to Africa.
    [0013]
    [0014] Currently, the active substances recommended against pseudococids are mineral oil, spirotetramat, chlorpyrifos and methyl-chlorpyrifos (Urbaneja A., Catalán J., Tena A., Jacas, J. 2015. Integrated Management of Citrus Pests, http : //gipcitricos.ivia.es.), the last two being the most active against Delottococcus aberíae. Unfortunately, these materials are being restricted in their use, so alternative tools are needed to manage this pest. Regarding biological control, Delottococcus aberíae has been shown to have a strong defensive response and is capable of encapsulating the eggs of several general pseudococcal parasitoids, such as Acerophagus angustifrons (Gahan), Anagyrus sp. near pseudoccoci (Girault), and Leptomastix algíríca Trjapitzin (Hymenoptera: Encyrtidae) (Tena, A., J. García-Bellón, and A. Urbaneja. 2017. Native and naturalized mealybug parasitoids fail to control the new citrus mealybug pest Delottococcus aberiae. J. Pest Sci. 90: 659-667). Considerable efforts are being made to import and release parasitoids from the area of origin, but in the meantime, the only strategy that could be used in the short term is to advance the action of Cryptolaemus montrouzíerí by releasing this predatory coccinellid.
    [0015]
    [0016] The detection and monitoring of pseudococcal populations is key to improving their control in both agricultural and ornamental ecosystems, but sometimes it consists of a laborious visual inspection of plant material for living forms and the count of all stages of the insect. . Alternatively, corrugated cardboard traps can be used for seasonal sampling of live forms and / or sticky traps to track the flight of males (Martínez-Blay, V., Pérez-Rodríguez, J., Tena, A., & Soto, A. (2018). Density and phenology of the invasive mealybug Delottococcus aberiae on citrus: implications for integrated pest management. Journal of Pest Science, 91 (2), 625-637). The latter technique requires the availability of species-specific attractants, such as sex pheromones, hitherto not available for Delottococcus aberiae.
    [0017]
    [0018] On the other hand, the use of these sexual pheromones in commercial treatments for the control of coccoid pests ( Aonidiella aurantii Maskell) is known. (Scalebur®, Ecologia y Protección Agrícola, Valencia) and Planococcus ficus Signoret (CheckMate® VMB-XL, Suterra, Bend, USA)) by using techniques such as sexual confusion, where the male is not able to find the female by means of the action of diverse mechanisms causing the interruption of the copula. However, none of the existing compounds has an effect on Delottococcus aberiae.
    [0019]
    [0020] There is therefore a need to provide a compound that allows the control and monitoring of the Delottococcus aberiae population specifically, and that in addition to being effective allows its use in control methods that are environmentally sustainable.
    [0021]
    [0022] Brief description of the invention
    [0023]
    [0024] The present invention solves the problems described in the state of the art since it provides an attractant compound for insects of the species Delottococcus aberiae.
    [0025]
    [0026] Thus, in a first aspect, the present invention relates to a compound of formula I (hereinafter compound of the present invention):
    [0027]
    [0028]
    [0029]
    [0030]
    [0031]
    [0032]
    [0033] its stereoisomers and mixtures.
    [0034]
    [0035] In the present invention, by the compound of formula I, it refers to (4,5,5-trimethyl-3-methylenecyclopent-1-en-1-yl) methyl acetate, its stereoisomers and mixtures
    [0036]
    [0037] The compound of the present invention can exist as stereoisomers or mixtures of stereoisomers in any proportion, for example, the compound of the present invention, can have an L-, D- configuration, or can be in racemic form.
    [0038] In a second aspect, the present invention relates to an attractant composition for insects of the species Delottococcus aberíae (hereinafter the composition of the present invention) comprising the compound of the present invention.
    [0039]
    [0040] In a more particular aspect, the composition of the present invention comprises an amount of the compound of the present invention comprised between 0.001 to 1000 mg. Preferably, the effective amount is in the range of from 0.001 to 200 mg.
    [0041]
    [0042] As a person skilled in the art knows, the amount of compound is variable depending on the type of area, zone or object to be treated, the environmental conditions and the number of days of attraction required, as well as the proportion of particular enantiomers present in the (4,5,5-trimethyl-3-methylenecyclopent-1-en-1-yl) methyl acetate used.
    [0043]
    [0044] In a more particular aspect, the composition of the present invention comprises at least one ingredient.
    [0045]
    [0046] In the present invention, "ingredient" refers to any active substance that is incorporated into the composition to perform at least one specific function.
    [0047]
    [0048] More particularly, the ingredient is selected from among antioxidants, radiation protectors, insect control agents, pheromones, and mixtures thereof.
    [0049] In the present invention, antioxidant refers to any substance capable of retarding or preventing the oxidation of one or more components of the composition of the present invention. Preferably, the antioxidant agent in the composition of the present invention is selected from: ascorbic acid, erythorbic acid, sodium ascorbate, calcium ascorbate, butylhydroxyanisole (BHA), butylhydroxytoluene (BHT), sulfur dioxide, sodium erythorbate, ascorbyl stearate , propyl gallate, octyl gallate, dodecyl gallate, sodium hydrosulfite, lecticine, ascorbyl palmitate, tert-butylhydroquinone (TBHQ) and natural and / or synthetic tocopherols and any combination of the above antioxidants.
    [0050]
    [0051] In a more particular embodiment, in the attractant composition of the present invention, the antioxidant agent is comprised in a ratio of 1: 1000 and 1:20 by weight with respect to the weight content of (4,5,5-trimethyl acetate -3-methylenecyclopent-1-en-1-yl) methyl. Preferably the antioxidant agent is in a ratio of 1: 100 by weight with respect to the content by weight of (4,5,5-trimethyl-3-methylenecyclopent-1-en-1-yl) methyl acetate.
    [0052] In the present invention, UV radiation protectors refers to any compound capable of protecting and preserving one or more components of the composition of the present invention from solar degradation. Preferably the UV radiation protectors of the present invention refer to PABA derivatives, salicylates, cinnamates, benzophenones, benzimidazoles, anthralinates, terpenic derivatives, inorganic oxides and any combination of the above UV protectors. They preferably refer to 4-aminobenzoic acid, 4-hydroxybenzophenone, 2-ethylhexyl salicylate, 2-ethylhexyl trans-4-methoxycinnamate, ethylhexyl 2-cyano-3,3-diphenylacrylate, titanium oxide and / or zinc oxide and a combination any of the above UV protectors.
    [0053]
    [0054] In a more particular embodiment, in the attractant composition of the present invention, the UV radiation protector is comprised between a ratio of 1: 200 and 1:20 by weight with respect to the weight content of acetate of (4,5, 5-trimethyl-3-methylenecyclopent-1-en-1-yl) methyl. Preferably the UV radiation protector is in a 1:50 weight ratio with respect to the weight content of (4,5,5-trimethyl-3-methylenecyclopent-1-en-1-yl) methyl acetate.
    [0055]
    [0056] In the present invention, "insect control agent" refers to a chemical that causes the death of the insect. More in particular, it refers to insecticides, more in particular it refers to organochlorine, organophosphate, carbamates, pyrethroids, neonicotinoids, tetramic acids, biorationals and combinations thereof.
    [0057]
    [0058] In the present invention, a pheromone is defined as any substance that an animal secretes and that causes a specific reaction or behavior in a member of the same species, and particularly, a sexual pheromone is defined as one that secretes one of the genera of the species and causes one attraction response and copulate on the other. On the other hand, by kairomona it refers to any substance that an organism secretes and intervenes in the communication between individuals of different species, benefiting the organism that receives it.
    [0059]
    [0060] In a more particular aspect, the composition of the present invention comprises at least one chemically acceptable excipient.
    [0061]
    [0062] In the present invention, "chemically acceptable excipient" refers to any substance that is incorporated into the composition of the present invention to provide shape, consistency, flavor, odor, color, etc. More particularly, the excipient is selected from binders, diluents, solvents, disintegrants, lubricants, colorants, sweeteners, flavors, preservatives, and mixtures thereof.
    [0063] In a more particular aspect, the composition of the present invention is presented in a formulation selected from, emulsion, solution, dispersion, aerosol, liquid, gel, powder, granule, paste and tablet.
    [0064]
    [0065] In a more particular aspect, the composition of the present invention is incorporated into a carrier.
    [0066]
    [0067] In the present invention, "carrier" refers to a substrate or matrix capable of carrying or containing the compound of the present invention or the composition of the present invention. More particularly, the carrier is selected from among a polymeric matrix, wood, ceramic, metal, leather, nylon, rubber, paraffin, wax, cotton, foam, textile material, granules, polymers, silicas, resins and adhesive tapes, among others. .
    [0068]
    [0069] In a more particular aspect, the compound of the present invention or the composition of the present invention, is deposited, absorbed, adsorbed, pulverized or coated or in any physical or chemical form that allows it in the carrier, based on the nature of compound, composition and carrier.
    [0070]
    [0071] In a third aspect, the present invention relates to a Delottococcus aberiae attractant device comprising a carrier containing the compound of the present invention or the composition of the present invention. In a particular embodiment, the device of the present invention comprises a trap.
    [0072]
    [0073] In the present invention, by trap we refer to any device that traps and / or affects insects and / or retains them. In a particular embodiment the trap comprises a toxic or pathogenic substance for the target insect. In a more particular embodiment, the trap is a surface that comprises an adhesive.
    [0074]
    [0075] In a particular embodiment, the holder of the device of the present invention is contained in the trap.
    [0076]
    [0077] In a particular embodiment, the holder of the device of the present invention is separated from the trap.
    [0078]
    [0079] In a fourth aspect, the present invention refers to a method of control and / or monitoring of Delottococcus aberiae populations (hereinafter, the method of the present invention) comprising the use of the compound of the present invention or the composition of the present invention. More particularly, the method of the present invention comprises the use of the device of the present invention.
    [0080] In a particular embodiment, the control and / or monitoring method is carried out by attracting male individuals belonging to the Delottococcus aberiae species .
    [0081]
    [0082] In another particular embodiment, the control and / or monitoring method is carried out through the sexual confusion of male individuals belonging to the Delottococcus aberiae species .
    [0083]
    [0084] In another particular embodiment, the control and / or monitoring method is performed by killing male individuals belonging to the Delottococcus aberiae species .
    [0085]
    [0086] Brief description of the Figures
    [0087]
    [0088] Figure 1: Figure 1 depicts Detection of (4,5,5-trimethyl-3-methylenecyclopent-1-en-1-yl) methyl acetate in samples of volatiles from laboratory-reared Delottococcus aberiae individuals on lemons. Shown are: (A) synthetic (4,5,5-trimethyl-3-methylenecyclopent-1-en-1-yl) methyl acetate as racemate, (B) sample of volatiles from virgin females, (C) sample of volatiles of copulated females. It is observed that the peak with retention time 24.24 min detected in the samples of virgin females (B), does not appear in the samples of copulated females (C), and that it coincides with the synthetic acetate sample of (4.5 , 5-trimethyl-3-methylenecyclopent-1-en-1-yl) methyl (A).
    [0089]
    [0090] Figure 2: Figure 2 depicts the response of males of Delottococcus aberiae to (4,5,5-trimethyl-3-methylenecyclopent-1-en-1-yl) methyl acetate in test of choice under laboratory conditions. : negative control vs. (4,5,5-Trimethyl-3-methylenecyclopent-1-en-1-yl) methyl acetate. Percentages with respect to the total of individuals who showed activity. The negative control was pentane solvent in all cases. There are significant differences (test x2, P <0.05).
    [0091]
    [0092] Figure 3: Figure 3 represents the Mean (± standard error) of the number of Delottococcus aberiae males captured per trap and day in the field attraction response test to (4,5,5-trimethyl-3 acetate -methylenecyclopent-1-en-1-yl) methyl. There are significant differences (ANOVA, LSD test at P <0.05).
    [0093] Example 1: Detection of ( 4,5,5-trimethyl-3-methylenecyclopent-1-en-1-yl) methyl acetate in samples from virgin Delottococcus aberiae females using volatiles uptake techniques
    [0094]
    [0095] For the capture of the volatiles emitted by females of Delottococcus aberiae in different sexual states, individuals from laboratory breeding kept on organically grown lemons were used at the Center for Agricultural Chemical Ecology (Universitat Politécnica de Valéncia, Valencia). The brood is kept in a chamber under controlled conditions, at 23 ± 2 ° C and 60-70% relative humidity.
    [0096]
    [0097] Sampling of the volatiles emitted by the insects was carried out by aerating the individuals and capturing the effluvia in glass cartridges filled with the Porapak-Q adsorbent matrix. Groups of 200-300 individuals were placed on the rearing substrate in 5 l glass containers, through which a filtered air stream of 0.4 l / min was passed. Every 7-8 days, the adsorbent material was washed with 20 ml of pentane to elute the captured substances. Eluents were analyzed by gas chromatography coupled to mass spectrometry (GC-MS). Chromatographic analysis was performed on a Clarus 600 GC-MS (PerkinElmer Inc.), equipped with a ZB-5MS capillary column (30 m * 0.25 mm id * 0.25 pm; Phenomenex Inc.) and the following temperature program: 40 ° C for 2 min; 5 ° C / min to 180 ° C and then increase to 280 ° C at 10 ° C / min, holding at 280 ° C for 1 min. Helium was used as the carrier gas with a flow of 1 ml / min. Detection was performed in electronic impact mode (70 eV) and the temperature of the ionization source and the transfer line was 200 ° C and 250 ° C, respectively. Once a unique peak of the samples from virgin females was detected, it was isolated from the eluted mixture by the following procedure: (1) gravity chromatography of the total extract with mixtures pentane: diethyl ether (100: 0, 95: 5, 80 : 20, 0: 100) as eluents; (2) localization of the peak in the corresponding fraction by GC-MS; (3) isolation of the substance in the fraction by preparative GC. Preparative gas chromatography was carried out using a Clarus 500 GC kit (Perkin Elmer) equipped with a flame ionization detector and a TRB-1 capillary column (30 m * 0.53 mm id * 0.5 pm; Teknokroma Analítica SA, Sant Cugat del Vallés, Barcelona, Spain). The oven temperature was programmed at 40 ° C for 2 min, then rising at 3 ° C / min up to 100 ° C and at 30 ° C / min up to 280 ° C, which are finally maintained for 12 min. Once isolated, the structural elucidation was performed with the data provided by the CG-MS spectrum and the nuclear magnetic resonance (NMR) spectrum in a 600 MHz equipment from the Bruker brand. Finally, the spectra of the natural substance with those of a sample synthesized by Ecología y Protección Agrícola SL (Carlet, Valencia).
    [0098]
    [0099] Chromatographic analysis revealed a peak that appeared exclusively in samples of volatiles emitted by virgin females and not in those of females that had copulated or from immature individuals, as can be seen in Figure 1. This peak corresponded to the acetate of ( 4,5,5-Trimethyl-3-methylenecyclopent-1-en-1-yl) methyl, identified by spectrometric data, and subsequently confirmed by comparison with a laboratory produced synthetic sample as described in Example 2.
    [0100]
    [0101] Example 2: Synthesis of ( 4,5,5-trimethyl-3-methylenecyclopent-1-en-1-yl) methyl acetate
    [0102] The synthesis of the same has been carried out according to scheme 1 shown below:
    [0103]
    [0104]
    [0105]
    [0106]
    [0107] Scheme 1
    [0108]
    [0109] As can be seen in scheme 1, 500 mg of ketone 2 (Leviredend, ML; Conia, Sur JM Sur the preparation of cyclopenténones par action de l'acide phosphorique sur les esters d'acides éthyléniques, Bulletin de la societé quimique de france , 8-9, 1970), was subjected to an allylic bromination reaction using 1.2 mg of N-bromosuccinimide in carbon tetrachloride catalyzed by irradiation of visible light with a 400 W power lamp for 6 hours at room temperature. After this time, the solution was filtered and the solvent was evaporated in vacuo. The obtained residue is dissolved in 5 ml of DMSO and 1.5 equivalents of potassium acetate are added portionwise with stirring. After 2 h and after checking the end of the reaction by thin layer chromatography or gas chromatography, the mixture is poured into 40 ml of ethyl acetate and washed with water (15 ml X 3) and brine (15 ml). The resulting solution is dried with anhydrous magnesium sulfate, and the solvent is evaporated in vacuo. The residue is purified by column obtaining 400 mg (54% yield) of ketone 4 . Ketone spectroscopic data 4: 5 h (300 MHz, Chloroform-d) 5.99 (1 H, t, J 1.8 Hz), 4.91 (2 H, d, J 1.8 Hz), 2.36 (2 H, s), 2.15 (3H, s), 1.28 (6H), s). 13 C NMR (75 MHz, CDC h ) 5 206.72, 181.22, 170.49, 127.55, 60.28, 52.19, 41.94, 27.35, 20.85. MS (70 eV) m / z: 43 (100), 67 (23), 79 (42), 95 (12), 110 (18), 125 (63), 140 (52), 167 (10), 182 (12, M +).
    [0110]
    [0111] Ketone 4 (400 mg, 2.2 mmol) dissolved in THF (2. ml) is added dropwise over a LDA solution (1.25 eq) at -78 ° C. After 30 min, 1 ml of methyl iodide is added and the solution is allowed to warm to room temperature for 2 h, and is kept at this temperature for an additional 3 h. After this time, the reaction mixture is poured into water and extracted with diethyl ether (2 X 50 ml). The organic phase is washed with brine (2 X 10 ml), dried with magnesium sulfate and the solvent is removed in vacuo. The reaction crude is purified by column chromatography and obtaining 110 mg (25% yield) of methyl ketone 5 . Ketones spectroscopic data 5: 5 H (300 MHz, Chloroform-d) 6.00 (1 H, t, J 1.8 Hz), 4.92 (1 H, d, J 1.8 Hz), 2.23 (1 H, q, J 7.5 Hz), 2.14 (3 H, s), 1.25 (3 H, s), 1.09 (3 H, s), 1.08 (3 H, d, J 7.5 Hz). 13 C NMR (75 MHz, CDCh) 5209.01, 179.73, 170.51, 126.26, 60.59, 53.73, 44.90, 26.17, 23.91, 20.85, 9.73. MS (70 eV) m / z: 43 (100), 55 (23), 67 (33), 77 (14), 93 (38), 108 (20), 121 (14), 139 (57), 154 (32), 181 (22), 196 (8, M +).
    [0112]
    [0113] 300 milligrams (2.5 eq.) Of bisdiclopentadienyl titanium (II) dichloride in 10 ml toluene is suspended in a round-bottom flask and cooled to 0 ° C. and on these are added 0.85 ml (2 eq.) of a solution of 3M methyl magnesium chloride in THF. After 20 min, it is allowed to warm to rt and is kept at this temperature for 1 h. 110 mg (0.56 mmol) of ketone 5 dissolved in 1 ml of toluene are added to the above mixture. The resulting solution is heated at 70 ° C for 24 hours, after which it is cooled and poured into water. The mixture is extracted with diethyl ether (2 X 30 ml) and the combined organic phases are washed successively with a 5% bicarbonate solution (2 X 15 ml) and brine (2 X 10 ml). Finally, the organic phase is dried with anhydrous magnesium sulfate and the solvent is removed in vacuo. The obtained product is purified by column chromatography, obtaining 16 mg of diene 1 (15% yield). Ketone spectroscopic data 5: 5 h (300 MHz, Benzene-0 6 ) 6.06 (1 H, s), 4.94 (1 H, d, J 2.5 Hz), 4.74 (1 H, d, J 2.4 Hz), 4.70 - 4.55 (2 H, m), 2.36 (1 H, qt, J 7.1, 2.5 Hz), 1.69 (3 H, s), 0.93 (3 H, d, J 7.1 Hz), 0.88 (3 H, s ), 0.75 (3H, s). 13 C NMR (75 MHz, C to D a ) 5 169.76, 156.66, 153.41, 129.24, 103.10, 60.76, 49.43, 47.55, 25.92, 22.09, 20.44, 12.42. MS (70 eV) m / z: 43 (72), 53 (12), 65 (14), 77 (21), 79 (19), 91 (40), 105 (20), 119 (100), 121 (72), 134 (22), 194 (10, M +).
    [0114] The enantiomers that make up the synthetic sample were separated by preparative chiral liquid chromatography, in a VWR LP-1100 kit using a DAICEL 19335 AD-H chiral column (1 X 25 cm) with a mixture of hexane: isopropanol 99: 1 as eluent. The assignment of the sign of the specific optical rotation (left-handed or right-handed) of each of them was carried out in a Perkin-Elmer polarimeter using a sodium lamp (line D, 589 nm) and a cell of 1 dm in length. The comparison by chiral gas chromatography allowed the allocation of the left-handed isomer to the natural compound isolated from the females (Clarus 500 GC Kit (Perkin Elmer) equipped with a flame ionization detector and an InertCap CHIRAMIX capillary column (30 m * 0.25 mm id * 0.25 pm; GL Sciences Inc., Tokyo, Japan).
    [0115]
    [0116] Example 3: Biological assays of activity of ( 4,5,5-trimethyl-3-methylenecyclopent-1-en-1-yl) methyl acetate under laboratory conditions
    [0117]
    [0118] The response of the male Delottococcus aberiae to (4,5,5-trimethyl-3-methylenecyclopent-1-en-1-yl) methyl acetate was evaluated at the Center for Agricultural Chemical Ecology (UPV, Valencia), using a Activity test in a glass Petri dish. The tests were carried out with light and under the same rearing conditions, at 23 ± 2 ° C and 60-70% relative humidity.
    [0119]
    [0120] For these tests, males from the rearing were also used, separated in Petri dishes just when the cottony cocoon began to form. After pupating and finally emerging from the cocoon, the insects are observed under the binocular to confirm their status before being selected for the trial.
    [0121]
    [0122] The procedure used is described below: During each test, a sample of (4,5,5-trimethyl-3-methylenecyclopent-1-en-1-yl) methyl acetate and a negative control (pentane solvent without activity), placed on 1 cm2 filter paper in an amount of 10 pl. Immediately, groups of males are carefully deposited with the help of a very fine brush on the test plate. Then, the behavior of the individuals towards the stimulus sources is recorded for 10 min. Once the test is finished, the insects are discarded, in such a way that each insect is exposed to the olfactory stimuli only once. The data obtained was analyzed using the Chi square test (x2 test, P <0.05).
    [0123]
    [0124] The results shown in Figure 2 indicate that there is a significant attractive response from males to pieces of filter paper impregnated with the synthetic pheromone.
    [0125] Example 4: Male attraction response tests for Delottococcus aberiae in the field
    [0126]
    [0127] The response of the Delottococcus aberiae males to (4,5,5-trimethyl-3-methylenecyclopent-1-en-1-yl) methyl acetate was evaluated in two field trials conducted on a citrus plot of var. Marisol, located in the town of Sagunto (Valencia), during the months of May-June 2018. In a first trial, 3 blocks of 2 devices were installed: (A) a device with a carrier, without an attractive substance and with a trap consisting of a white sheet with adhesive, (B) a carrier device primed with 500 pg of (4,5,5-trimethyl-3-methylenecyclopent-1-en-1-yl) methyl acetate and a trap consisting of a white sheet with adhesive (95 x 150 mm) (Within each block the devices were placed at a distance of 20 m from each other, while the distance between blocks was at least 30 m. Carriers loaded with acetate of (4, 5,5-trimethyl-3-methylenecyclopent-1-en-1-yl) methyl were septa type and inserted inserted in the center of the trap.
    [0128]
    [0129] The captures obtained in each of the traps were reviewed weekly and the captured individuals were taken to the laboratory to be identified and counted. Each week the rotation of intrablock traps was performed.
    [0130]
    [0131] The number of males captured per trap and day was compared by means of an analysis of variance (ANOVA; LSD test for comparison of means, P <0.05), after transformation (ln (x + 1)) of the data in order to homogenize variance.
    [0132]
    [0133] The results show that devices primed with (4,5,5-trimethyl-3-methylenecyclopent-1-en-1-yl) methyl acetate have a significantly higher power of attraction than traps without an attractant, as shown in Figure 3. The load of (4,5,5-trimethyl-3-methylenecyclopent-1-en-1-yl) methyl acetate tested was 300 pg per septa.
    [0134] The results of the analyzes of the content in attractant after 20 days show that the final content of the substance was 109 pg. Therefore, the average emission during those 20 days is 9.45 ± 2.13 pg / day. Regarding the level of catches obtained, the results can be seen in the following table 1:
    [0135]
    [0136]
    [0137] On average, 57.22 catches per trap and day were obtained in the pheromone-baited traps compared to 0.11 catches in the controls, which means a significant difference in the analysis of variance (F = 553.47; Gl: 1 , 5; P <0.001).
    [0138]
    [0139] In a second test it was performed in the same way as Test 1, but Device B was primed with 100 pg of (4,5,5-trimethyl-3-methylenecyclopent-1-en-1-yl) methyl acetate
    [0140]
    [0141] The results of the analysis of the content in attractant after 20 days show that the final content of the substance is 91 pg. Therefore, the average emission during those 20 days is 0.55 ± 0.42 pg / day.
    [0142]
    [0143] On average, 9.14 captures per trap and day were obtained in the pheromone baited traps compared to 0.06 captures in the controls, which implies a significant difference in the analysis of variance (F = 5.22 Gl: 1, 16; P <0.036)
    [0144] Regarding the level of catches, the results obtained can be seen in Table 2:
    [0145]
    [0146]
    [0147]
    [0148]
    [0149] Therefore, catches with emissions between 0.55 ± 0.42 and 9.45 ± 2.13 micrograms per day capture significantly.
    权利要求:
    Claims (16)
    [1]
    1. Compound of formula I,

    [2]
    2. Attractant composition for insects of the species Delottococcus aberíae comprising a compound according to any one of claim 1.
    [3]
    3. Composition according to claim 2, comprising at least one ingredient.
    [4]
    4. Composition according to claim 3, wherein the ingredient is selected from among attractants, antioxidants, radiation protectors, insect control agents, pheromones, kairomones, and mixtures thereof.
    [5]
    5. Composition according to any of claims 2-4, comprising at least one chemically acceptable excipient.
    [6]
    6. Composition according to claim 5, wherein the excipient is selected from binders, diluents, disintegrants, lubricants, colorants, sweeteners, flavors, preservatives and mixtures thereof.
    [7]
    7. Composition according to any of the preceding claims, characterized in that the composition is presented in a formulation selected from emulsion, solution, dispersion, aerosol, liquid, gel, powder, granule, paste and tablet.
    [8]
    Composition according to any of the preceding claims, characterized in that it is incorporated into a carrier.
    [9]
    9. Composition according to claim 8, wherein the carrier is a matrix.
    [10]
    10. Delottococcus aberiae attractant device comprising a carrier containing the compound according to claim 1 or a composition according to any of claims 2-8.
    [11]
    11. The Delottococcus aberie attractant device according to claim 10, comprising a trap.
    [12]
    12. A method of controlling and / or monitoring populations of Delottococcus aberiae, comprising the use of a compound according to claim 1 or a composition according to any of claims 2-8.
    [13]
    13. Method of control and / or monitoring of Delottococcus aberiae populations according to claim 12, comprising the use of a device according to any of claims 10-11.
    [14]
    14. Method of control and / or monitoring of Delottococcus aberiae populations according to any of claims 12-13, where the control is carried out by attracting male individuals belonging to the Delottococcus aberiae species .
    [15]
    15. Method of control and / or monitoring of Delottococcus aberiae populations according to any of claims 12-13, where the control is carried out by sexual confusion of male individuals belonging to the Delottococcus aberiae species .
    [16]
    16. Method of control and / or monitoring of Delottococcus aberiae populations according to any of claims 12-13, where the control is carried out by killing male individuals belonging to the Delottococcus aberiae species .
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    同族专利:
    公开号 | 公开日
    US20220002222A1|2022-01-06|
    ES2760398B2|2020-11-06|
    IL283157D0|2021-06-30|
    EP3882232A1|2021-09-22|
    WO2020099705A1|2020-05-22|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    WO2014115172A1|2013-01-24|2014-07-31|Council Of Scientific And Industrial Research|Enantioselective process for the preparation of enantiomers of sex pheromones|
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    ES201831098A|ES2760398B2|2018-11-13|2018-11-13|ATTRACTIVE COMPOSITION OF THE SPECIES DELOTTOCOCCUS ABERIAE, METHODS FOR THE DETECTION, MONITORING AND / OR CONTROL OF THE PEST|ES201831098A| ES2760398B2|2018-11-13|2018-11-13|ATTRACTIVE COMPOSITION OF THE SPECIES DELOTTOCOCCUS ABERIAE, METHODS FOR THE DETECTION, MONITORING AND / OR CONTROL OF THE PEST|
    EP19829663.4A| EP3882232A1|2018-11-13|2019-11-11|Composition that attracts the species delottococcus aberiae and methods for detecting, monitoring and/or controlling the pest|
    US17/293,495| US20220002222A1|2018-11-13|2019-11-11|Attractant composition for the species delottococcus aberiae, methods for the monitoring, detection and/or control of the pest|
    PCT/ES2019/070770| WO2020099705A1|2018-11-13|2019-11-11|Composition that attracts the species delottococcus aberiae and methods for detecting, monitoring and/or controlling the pest|
    IL283157A| IL283157D0|2018-11-13|2021-05-12|Composition that attracts the species delottococcus aberiae and methods for detecting, monitoring and/or controlling the pest|
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