A kind of directional composition containing trans-8-dodecene-2,2,3,3,3-pentafluoropropionate and its application

Abstract

The present invention relates to a disorienting composition containing trans-8-dodecene-2,2,3,3,3-pentafluoropropionate and its application. The disorienting composition of the present invention comprises a first component and a second component, wherein the first component comprises trans-8-dodecene-2,2,3,3,3-pentafluoropropionate, trans-8-dodecene-acetate, and cis-8-dodecene-1-ol; and the second component comprises trans-8-trans-10-dodecadiene-1-ol. The disorienting composition of the present invention has an excellent disorienting effect on pear borer and / or codling moth.

Description

Technical Field

[0001] The invention relates to the field of pesticides, and in particular to a composition having a disorienting effect on pear borer and / or codling moth. Background Art

[0002] Pear borer Grapholitha molesta and codling moth Cydia pomonella Both belong to the family of scolopidae in the order Lepidoptera. Their main hosts are apples, peaches, pears and other Rosaceae plants. Their larvae bore into fruits and tender shoots, causing branches to wilt and fruit to fall, resulting in serious economic losses and serious damage to fruit safety. Since the two pests often occur together in the field, aggravating the damage, if the two pests can be controlled at the same time, it will help reduce economic losses or reduce economic investment. Summary of the invention

[0003] One of the present inventions provides a directional composition, which includes a component I and a component II, wherein the component I includes trans-8-dodecene-2,2,3,3,3-pentafluoropropionate, trans-8-dodecene-acetate, and cis-8-dodecene-1-ol; and the component II includes trans-8-trans-10-dodecadien-1-ol.

[0004] In a specific embodiment, based on the total mass of the first component as 100%, the content of the trans-8-dodecene-2,2,3,3,3-pentafluoropropionate is 94%, the content of the trans-8-dodecene-acetate is 5%, and the content of the cis-8-dodecene-1-ol is 1%.

[0005] In a specific embodiment, the mass ratio of the component I to the component II is 1:1 to 1:1.5.

[0006] In a specific embodiment, the mass ratio of the component I to the component II is 1:1.

[0007] The second aspect of the present invention provides a disoriented yarn, which comprises a disoriented composition as described in any one of the present inventions and a capillary, wherein the composition is encapsulated in the capillary.

[0008] In a specific embodiment, the mass of the disorienting composition in the disorienting yarn is 200 to 400 mg.

[0009] The third aspect of the present invention provides the use of the disorienting composition according to any one of the first aspect of the present invention or the disorienting silk according to the second aspect of the present invention in controlling the disorienting pear borer and / or codling moth.

[0010] It should be pointed out that in the present invention, the disorientation rate of the disorienting agent on pests is determined only by using the combination of attractant + disorienting agent and the number of insects trapped by the attractant alone, in order to illustrate the interfering effect of the disorienting agent on the attractant. In actual applications, the disorienting agent does not need to be used in combination with the attractant, that is, it is obvious that the disorienting agent is used alone.

[0011] Beneficial effects of the present invention: The present invention finds that a composition containing trans-8-dodecene-2,2,3,3,3-pentafluoropropionate has an excellent disorienting effect on pear borer and / or codling moth. Making the composition into disorienting silk can effectively prevent and control pear borer and codling moth at the same time, reduce the number of pest offspring, reduce economic losses, and achieve green prevention and control. BRIEF DESCRIPTION OF THE DRAWINGS

[0012] Figure 1 A schematic diagram showing the setting of the disorientation zone and reference control zone in the apple orchard in Aksu, Xinjiang.

[0013] Figure 2 The disorientation rates of each treatment against pear borer and codling moth are shown. DETAILED DESCRIPTION

[0014] The above contents of the present invention are further described in detail below in the form of preferred implementation cases, but they do not constitute a limitation to the present invention.

[0015] Unless otherwise specified, the reagents in the embodiments of the present invention can be purchased through commercial channels.

[0016] trans-8-dodecene-acetate, cis-8-dodecene-acetate, cis-8-dodecen-1-ol and trans-8-trans-10-dodecadien-1-ol were purchased from Jiangsu Ninglu Biotechnology Co., Ltd.

[0017] Example 1: Synthesis of trans-8-dodecene-2,2,3,3,3-pentafluoropropionate

[0018] Pentafluoropropionic anhydride solution was prepared by dissolving 1.345 g of pentafluoropropionic anhydride in 5 mL of dichloromethane.

[0019] 0.500 g of trans-8-dodecene-1-ol was dissolved in 20 mL of anhydrous dichloromethane, 0.415 g of triethylamine was added, and then 0.01 g of 4-dimethylaminopyridine was added, and stirred in an ice-salt bath to maintain the reaction temperature at about -20 degrees Celsius, and then the pentafluoropropionic anhydride solution prepared above was gradually added dropwise. To ensure that the reaction was carried out thoroughly, the pentafluoropropionic anhydride solution was divided into 5 portions and added successively. After each dropwise addition, the reaction was continued for 30 minutes, and then placed at room temperature and stirred overnight. After the reaction was complete, 10 mL of deionized water was added to the reaction bottle to terminate the reaction to obtain a reaction solution. The reaction solution was washed with a saturated sodium chloride aqueous solution, the upper oil phase was taken, and then the oil phase was dried with anhydrous magnesium sulfate to remove water, and finally the solvent was removed by vacuum rotary evaporation, and 0.665 g of an oily substance was obtained by purification and separation by silica gel column chromatography, with a yield of 75.4%.

[0020] The purified and separated oil was detected by high-resolution mass spectrometry, and the results were as follows: HR-MS (ESI) m / z: Calcd for C 15 H 24 F5O2{[M+H] +}331.1618, found 331.1724.

[0021] The purified and separated oily substance was detected by H NMR spectrum, and the results were as follows: 1 H NMR (500 MHz, CDCl3) δ5.37 – 5.33 (m, 2H), 4.37 (t, J = 6.7 Hz, 2H), 2.05 – 1.96 (m, 4H), 1.74 (m, J = 8.0, 6.4 Hz, 2H), 1.41 – 1.33 (m, 4H), 1.36 – 1.28 (m, 6H), 0.90 (t, J =7.4 Hz, 3H).

[0022] The purified and separated oily substance was detected by NMR C spectrum, and the results were as follows: 13 C NMR (101 MHz, CDCl3) δ158.98, 131.15, 130.50 -130.45 (2C), 116.24, 68.71, 34.85, 32.64, 31.75,29.57, 28.97 - 28.24 (2C), 25.54, 22.81, 14.26.

[0023] The purified and separated oily substance was finally determined to be trans-8-dodecene-2,2,3,3,3-pentafluoropropionate.

[0024] Example 2: Activity Test

[0025] Using chlorinated paraffin as solvent, trans-8-dodecene-2,2,3,3,3-pentafluoropropionate, trans-8-dodecene-acetate, cis-8-dodecene-acetate, cis-8-dodecene-1-ol and trans-8-trans-10-dodecadien-1-ol were prepared into stock solutions with a concentration of 1 μg / μl.

[0026] Using chlorinated paraffin as solvent, trans-8-dodecene-2,2,3,3,3-pentafluoropropionate, trans-8-dodecene-acetate, cis-8-dodecene-acetate, cis-8-dodecene-1-ol and trans-8-trans-10-dodecadien-1-ol were prepared into stock solutions with a concentration of 1 mg / μl.

[0027] A formula of the sex pheromone of the pear borer was used as an attractant: 94 μl of the above-mentioned 1 μg / μl mother liquor of cis-8-dodecene-acetate, 5 μl of the above-mentioned 1 μg / μl mother liquor of trans-8-dodecene-acetate, 1 μl of the above-mentioned 1 μg / μl mother liquor of cis-8-dodecen-1-ol, and 100 μl of chlorinated paraffin were mixed thoroughly, and then dropped onto a green rubber stopper of 240 mm × 340 mm in size to make an attractant core, so that the total volume added to the attractant core is 200 μl, recorded as G-CK.

[0028] A formula of sex pheromone of codling moth was used as an attractant: 100 μl of the above-mentioned 1 μg / μl mother liquor of trans-8-trans-10-dodecadien-1-ol was taken, and 100 μl of chlorinated paraffin was taken, the two were thoroughly mixed, and then dropped onto a green rubber stopper of 240 mm × 340 mm in size to make an attractant core, so that the total volume added to the attractant core was 200 μl, recorded as C-CK.

[0029] Take 94 μl from the above-mentioned 1 mg / μl mother liquor of trans-8-dodecene-2,2,3,3,3-pentafluoropropionate, take 5 μl from the above-mentioned 1 mg / μl mother liquor of trans-8-dodecene-acetate, take 1 μl from the above-mentioned 1 mg / μl mother liquor of cis-8-dodecen-1-ol, take 100 μl from the above-mentioned 1 mg / μl mother liquor of trans-8-trans-10-dodecadien-1-ol, mix the four thoroughly to prepare a disorienting agent, then add the mixed liquid into the capillary with a pipette, and heat-seal both ends of the capillary to prepare a sustained-release disorienting thread, recorded as W1.

[0030] Take 94 μl from the above-mentioned 1 mg / μl mother liquor of cis-8-dodecene-acetate, take 5 μl from the above-mentioned 1 mg / μl mother liquor of trans-8-dodecene-acetate, take 1 μl from the above-mentioned 1 mg / μl mother liquor of cis-8-dodecen-1-ol, take 100 μl from the above-mentioned 1 mg / μl mother liquor of trans-8-trans-10-dodecadien-1-ol, mix the four thoroughly to prepare a disorienting agent, then add the mixed liquid into the capillary with a pipette, and heat-seal both ends of the capillary to prepare a sustained-release disorienting thread, recorded as W2.

[0031] Take 5 μl from the above-mentioned 1 mg / μl mother liquor of cis-8-dodecene-acetate, take 94 μl from the above-mentioned 1 mg / μl mother liquor of trans-8-dodecene-acetate, take 1 μl from the above-mentioned 1 mg / μl mother liquor of cis-8-dodecen-1-ol, take 100 μl from the above-mentioned 1 mg / μl mother liquor of trans-8-trans-10-dodecadien-1-ol, mix the four thoroughly to prepare a disorienting agent, then add the mixed liquid into the capillary with a pipette, and heat-seal both ends of the capillary to prepare a sustained-release disorienting thread, recorded as W3.

[0032] Take 99 μl from the above-mentioned 1 mg / μl mother liquor of cis-8-dodecene-acetate, take 1 μl from the above-mentioned 1 mg / μl mother liquor of cis-8-dodecen-1-ol, take 100 μl from the above-mentioned 1 mg / μl mother liquor of trans-8-trans-10-dodecadien-1-ol, mix the four thoroughly to prepare a disorienting agent, then add the mixed liquid into the capillary with a pipette, and heat-seal both ends of the capillary to prepare a sustained-release disorienting thread, recorded as W4.

[0033] Take 99 μl from the above-mentioned 1 mg / μl mother liquor of trans-8-dodecene-acetate, take 1 μl from the above-mentioned 1 mg / μl mother liquor of cis-8-dodecen-1-ol, take 100 μl from the above-mentioned 1 mg / μl mother liquor of trans-8-trans-10-dodecadien-1-ol, mix the four thoroughly to prepare a disorienting agent, then add the mixed liquid into the capillary with a pipette, and heat-seal both ends of the capillary to prepare a sustained-release disorienting thread, recorded as W5.

[0034] Take 141 μL from the above-mentioned 1 mg / μL mother liquor of trans-8-dodecene-2,2,3,3,3-pentafluoropropionate, take 7.5 μL from the above-mentioned 1 mg / μL mother liquor of trans-8-dodecene-acetate, take 1.5 μL from the above-mentioned 1 mg / μL mother liquor of cis-8-dodecen-1-ol, take 150 μL from the above-mentioned 1 mg / μL mother liquor of trans-8-trans-10-dodecadien-1-ol, mix the four thoroughly to prepare a disorienting agent, then add the mixed liquid into the capillary with a pipette, and heat-seal both ends of the capillary to prepare a sustained-release disorienting thread, recorded as W6.

[0035] Take 141 μl from the above-mentioned 1 mg / μl mother liquor of cis-8-dodecene-acetate, take 7.5 μl from the above-mentioned 1 mg / μl mother liquor of trans-8-dodecene-acetate, take 1.5 μl from the above-mentioned 1 mg / μl mother liquor of cis-8-dodecen-1-ol, take 150 μl from the above-mentioned 1 mg / μl mother liquor of trans-8-trans-10-dodecadien-1-ol, mix the four thoroughly to prepare a disorienting agent, then add the mixed liquid into the capillary with a pipette, and heat-seal both ends of the capillary to prepare a sustained-release disorienting thread, recorded as W7.

[0036] Take 7.5 μl from the above-mentioned 1 mg / μl mother liquor of cis-8-dodecene-acetate, take 141 μl from the above-mentioned 1 mg / μl mother liquor of trans-8-dodecene-acetate, take 1.5 μl from the above-mentioned 1 mg / μl mother liquor of cis-8-dodecen-1-ol, take 150 μl from the above-mentioned 1 mg / μl mother liquor of trans-8-trans-10-dodecadien-1-ol, mix the four thoroughly to prepare a disorienting agent, then add the mixed liquid into the capillary with a pipette, and heat-seal both ends of the capillary to prepare a sustained-release disorienting thread, recorded as W8.

[0037] Take 148.5 μL from the above-mentioned 1 mg / μL mother liquor of cis-8-dodecene-acetate, take 1.5 μL from the above-mentioned 1 mg / μL mother liquor of cis-8-dodecen-1-ol, take 150 μL from the above-mentioned 1 mg / μL mother liquor of trans-8-trans-10-dodecadien-1-ol, mix the four thoroughly to prepare a disorienting agent, then add the mixed liquid into the capillary with a pipette, and heat-seal both ends of the capillary to prepare a sustained-release disorienting thread, recorded as W9.

[0038] Take 148.5 μL from the above-mentioned 1 mg / μL mother liquor of trans-8-dodecene-acetate, take 1.5 μL from the above-mentioned 1 mg / μL mother liquor of cis-8-dodecen-1-ol, take 150 μL from the above-mentioned 1 mg / μL mother liquor of trans-8-trans-10-dodecadien-1-ol, mix the four thoroughly to prepare a disorienting agent, then add the mixed liquid into the capillary with a pipette, and heat-seal both ends of the capillary to prepare a sustained-release disorienting thread, recorded as W10.

[0039] Take 188 μl from the above-mentioned 1 mg / μl mother liquor of trans-8-dodecene-2,2,3,3,3-pentafluoropropionate, take 10 μl from the above-mentioned 1 mg / μl mother liquor of trans-8-dodecene-acetate, take 2 μl from the above-mentioned 1 mg / μl mother liquor of cis-8-dodecen-1-ol, take 200 μl from the above-mentioned 1 mg / μl mother liquor of trans-8-trans-10-dodecadien-1-ol, mix the four thoroughly to prepare a disorienting agent, then add the mixed liquid into the capillary with a pipette, and heat-seal both ends of the capillary to prepare a sustained-release disorienting thread, recorded as W11.

[0040] Take 188 μl from the above-mentioned 1 mg / μl mother liquor of cis-8-dodecene-acetate, take 10 μl from the above-mentioned 1 mg / μl mother liquor of trans-8-dodecene-acetate, take 2 μl from the above-mentioned 1 mg / μl mother liquor of cis-8-dodecen-1-ol, take 200 μl from the above-mentioned 1 mg / μl mother liquor of trans-8-trans-10-dodecadien-1-ol, mix the four thoroughly to prepare a disorienting agent, then add the mixed liquid into the capillary with a pipette, and heat-seal both ends of the capillary to prepare a sustained-release disorienting thread, recorded as W12.

[0041] Take 10 μl from the above-mentioned 1 mg / μl mother liquor of cis-8-dodecene-acetate, take 188 μl from the above-mentioned 1 mg / μl mother liquor of trans-8-dodecene-acetate, take 2 μl from the above-mentioned 1 mg / μl mother liquor of cis-8-dodecen-1-ol, take 200 μl from the above-mentioned 1 mg / μl mother liquor of trans-8-trans-10-dodecadien-1-ol, mix the four thoroughly to prepare a disorienting agent, then add the mixed liquid into the capillary with a pipette, and heat-seal both ends of the capillary to prepare a sustained-release disorienting thread, recorded as W13.

[0042] Take 198 μL from the above-mentioned 1 mg / μL mother liquor of cis-8-dodecene-acetate, take 2 μL from the above-mentioned 1 mg / μL mother liquor of cis-8-dodecen-1-ol, take 200 μL from the above-mentioned 1 mg / μL mother liquor of trans-8-trans-10-dodecadien-1-ol, mix the four thoroughly to prepare a disorienting agent, then add the mixed liquid into the capillary with a pipette, and heat-seal both ends of the capillary to prepare a sustained-release disorienting thread, recorded as W14.

[0043] Take 198 μL from the above-mentioned 1 mg / μL mother liquor of trans-8-dodecene-acetate, take 2 μL from the above-mentioned 1 mg / μL mother liquor of cis-8-dodecen-1-ol, take 200 μL from the above-mentioned 1 mg / μL mother liquor of trans-8-trans-10-dodecadien-1-ol, mix the four thoroughly to prepare a disorienting agent, then add the mixed liquid into the capillary with a pipette, and heat-seal both ends of the capillary to prepare a sustained-release disorienting thread, recorded as W15.

[0044] The test period is from July 15, 2024 to August 14, 2024. The test site is the apple orchard in Aksu, Xinjiang. The apple orchard is divided into small plots, each with 2 mu. Figure 1 As shown, adjacent disorientation areas (2 mu) and luring control areas (2 mu) were set up, with each group no less than 50 meters apart. Traps for pear borer and codling moth were placed in both the disorientation areas and the luring control areas. Disorientation wires were placed in the disorientation areas, but no disorientation wires were placed in the luring control areas. The hanging height of the traps and disorientation wires was about 1.5 meters.

[0045] The lures and the lures used in the disorientation zone and the corresponding attractant control zone are as follows: attractants G-CK and C-CK are combined, and the lures used are W1 to W15. For the lures, taking the lures W1 as an example, it is subdivided into five treatments, wherein 10 lures are evenly placed in the W1-1 disorientation zone, 20 lures are evenly placed in the W1-2 disorientation zone, 30 lures are evenly placed in the W1-3 disorientation zone, 40 lures are evenly placed in the W1-4 disorientation zone, and 50 lures are evenly placed in the W1-5 disorientation zone. W2 to W15 are also subdivided into five treatments with 10 to 50 lures evenly placed. A total of 75 treatments.

[0046] Trap setting: 3 pear borer traps and 3 codling moth traps were set in each plot. The lure cores of pear borer or codling moth were placed at the fixed position of the lure core of their respective boat-shaped traps (the two lure cores do not share the same trap), and the sticky board was placed under the trap. Each trap was at least 15 meters apart, and the traps were arranged in a random chessboard pattern. The number of traps was counted every 3 days, and the number was counted continuously for a total of 10 times. After that, the sticky boards were replaced in sequence and the positions of the traps were randomly swapped. Each treatment was repeated 3 times, and the average of the 3 repetitions of each statistics was taken, and the average of the 10 averages was further calculated to obtain the number of traps in the lured control area or the number of traps in the disorientation area of ​​each treatment.

[0047] The isotropic rate is calculated according to formula (1) and formula (2).

[0048] The disorientation rate of pear borer = (the number of pear borer trapped in the lured control area - the number of pear borer trapped in the disorientation area) × 100% / the number of pear borer trapped in the lured control area Formula (1)

[0049] Codling moth disorientation rate = (number of codling moths trapped in the luring control area - number of codling moths trapped in the disorienting area) × 100% / number of codling moths trapped in the luring control area Formula (2)

[0050] All data were analyzed using SPSS 22.0 software and independent sample t-test.

[0051] See the result of disorientation Figure 2 .

[0052] The results of the test analysis showed that the disorienting effect of W1-1 was significantly better than that of W2-1, W3-1, W4-1 and W5-1; the disorienting effect of W1-2 was significantly better than that of W2-2, W3-2, W4-2 and W5-2; the disorienting effect of W1-3 was significantly better than that of W2-3, W3-3, W4-3 and W5-3; the disorienting effect of W1-4 was significantly better than that of W2-4, W3-4, W4-4 and W5-4; the disorienting effect of W1-5 was significantly better than that of W2-5, W3-5, W4-5 and W5-5; the disorienting effect of W6-1 was significantly better than that of W7-1, W8-1, W9-1 and W10-1; the disorienting effect of W6-2 was significantly better than that of W7-2, W8-2, W9-2 and W10-2; the disorienting effect of W6-3 was significantly better than that of W7-3, W8-3, W9 -3 and W10-3; the disorienting effect of W6-4 is significantly better than that of W7-4, W8-4, W9-4 and W10-4; the disorienting effect of W6-1 is significantly better than that of W7-5, W8-5, W9-5 and W10-5; the disorienting effect of W11-1 is significantly better than that of W12-1, W13-1, W14-1 and W15-1; the disorienting effect of W11-2 is significantly better than that of W12- 2, W13-2, W14-2 and W15-2; the disorienting effect of W11-3 is significantly better than that of W12-3, W13-3, W14-3 and W15-3; the disorienting effect of W11-4 is significantly better than that of W12-4, W13-4, W14-4 and W15-4; the disorienting effect of W11-5 is significantly better than that of W12-5, W13-5, W14-5 and W15-5. These results further indicate that the combination containing trans-8-dodecene-2,2,3,3,3-pentafluoropropionate has a better disorienting effect.

Claims

1. A composition comprising a first component and a second component, wherein the first component is trans-8-dodecene-2,2,3,3,3-pentafluoropropionate, trans-8-dodecene-acetate, cis-8-dodecene-1-ol; and the second component is trans-8-trans-10-dodecadiene-1-ol; Taking the total mass of the first component as 100%, the content of the trans-8-dodecene-2,2,3,3,3-pentafluoropropionate is 94%, the content of the trans-8-dodecene-acetate is 5%, and the content of the cis-8-dodecene-1-ol is 1%; The mass ratio of the component I to the component II is 1:1 to 1:1.

5.

2. The disorienting composition according to claim 1, characterized in that: The mass ratio of the component I to the component II is 1:

1.

3. A disorienting yarn, comprising the disorienting composition according to claim 1 or 2 and a capillary, wherein: The composition is encapsulated in the capillary.

4. The disorienting yarn according to claim 3, characterized in that: The mass of the disorienting composition in the disorienting yarn is 200 to 400 mg.

5. Use of the disorienting composition according to claim 1 or 2 or the disorienting silk according to claim 3 or 4 in controlling the disorienting pear borer and / or codling moth.

Images