Use of 1-methoxyindole in repelling and / or killing pests

Abstract

The present invention provides the use of 1-methoxyindole or its derivatives in repelling and / or killing pests, belonging to the field of pest control technology. The active ingredient provided by the present invention is 1-methoxyindole (1-MOI), which is found in Metarhizium robertsiense. When applied as a repellent, the concentration in a plane is 0.127 μg / cm 2 1-methoxyindole can repel a variety of ants, termites, and ticks, and the higher the 1-methoxyindole content, the stronger the repellent effect; when used as an insecticide, the concentration in the air is 0.14μg / cm 3 The 1-methoxyindole can kill a variety of ants, termites, ticks, thrips, mosquitoes, as well as whiteflies, brown planthoppers, spider mites and other pests, and the higher the concentration of 1-methoxyindole, the stronger the killing effect.

Description

Technical Field

[0001] The invention belongs to the technical field of pest control, and particularly relates to the application of 1-methoxyindole in repelling and / or killing pests. Background Art

[0002] Ants such as the red imported fire ant (Solenopsis invicta Buren), the Pharaoh ant (Monomoriumpharaonis), and the oriental army ant (Doxrylus orientalis), as well as the Formosan white termite (Coptotermes formosanus), are distributed in many countries and regions, seriously endangering agricultural and forestry production, human and animal health, and ecological balance. Public health pests such as the Culex pipienspallens, Anopheles sinensis, Aedes albopictus, Aedes aegypti, Haemaphysalis longicornis, Haemaphysalis concinna, and Cimex lectularius, in addition to affecting people's daily lives, are also important vectors of diseases such as Japanese encephalitis, malaria, dengue fever, and forest encephalitis. Whitefly (Bemisia tabaci), brown planthopper (Nilaparvata lugens), and spider mite (Tetranychus cinnabarinus), among others, are also important vectors of diseases such as the Japanese encephalitis, malaria, dengue fever, and forest encephalitis. cinnabarinus), Bactroceradorsalis, Halyomorpha halys, Megalurothrips usitatus, Frankliniella occidentalis Pergande, Thripsalliorum Priesner, Orosius orientalis, Tuta absoluta, Tribolium castaneum Herbst, and other agricultural and stored-grain pests affect agricultural production and grain storage, causing serious economic losses. Therefore, insect pests have become a global problem that needs to be urgently addressed.

[0003] Current pest control methods primarily include quarantine, physical control, chemical control, and biological control. Chemical control is the primary method due to its significant effectiveness. However, chemical control methods pose challenges such as environmental pollution, biodiversity destruction, and the development of pesticide resistance in pests. Therefore, the development of new, environmentally friendly insecticides is crucial for chemical pest control.

[0004] Furthermore, unlike chemical pesticides, repellents reduce or prevent contact between pests and their targets, thereby alleviating the effects of pests currently infesting or preemptively protecting potential targets. However, the development of pest repellents is still in its infancy, with few known effective repellent ingredients and high concentrations required for effectiveness. The development of new repellents could provide new solutions for pest control. Summary of the Invention

[0005] The present invention aims to provide the use of 1-methoxyindole or its derivatives in repelling and / or killing pests. The 1-methoxyindole or its derivatives can produce repellent and killing effects on a variety of pests at a low concentration of the active ingredient, and can be used as a repellent and / or insecticide.

[0006] The present invention provides the use of 1-methoxyindole or its derivatives in any of the following:

[0007] S1. Repel and / or kill pests;

[0008] S2. preparing a repellent;

[0009] S3, preparing pesticide;

[0010] S4. Preparation of products with both repellent and insecticidal capabilities;

[0011] The 1-methoxyindole has a structure shown in Formula I:

[0012]

[0013] The application objects in the present invention include one or more of the insects of the orders Hymenoptera, Isoptera, Diptera, Acarina, and Thysanoptera.

[0014] The application objects of the present invention also include one or more of the following: temperate zone bed bug, American cockroach, German cockroach, Bemisia tabaci, brown planthopper, cinnabarinus spider mite, citrus fruit fly, brown winged stink bug, red flour beetle, oriental net house leafhopper, and tomato leafminer.

[0015] The present invention also provides a repellent comprising a solvent and the 1-methoxyindole or a derivative thereof.

[0016] The solvent used in the repellent of the present invention is an organic solvent.

[0017] The solvent used in the repellent of the present invention is preferably one of n-hexane, liquid paraffin and anhydrous ethanol.

[0018] In the present invention, for the repellent, the repellent objects include one or more of the insects of the order Hymenoptera, the order Isoptera, and the order Acarina;

[0019] In the present invention, for the repellent, the Hymenoptera insects to be repelled are preferably ants, and the Isoptera insects are preferably termites.

[0020] Preferably, the ants include one or more of the following: red imported fire ants, oriental army ants, Kissimmee ants, grassland paving ants, hairless ant, agile flat-headed ant worker ants, Chinese house ants, Pharaoh ants, and big-headed ants;

[0021] Preferably, the termites include Coptotermes Formosanus;

[0022] Preferably, the ticks include one or more of Haemaphysalis longicornis and Haemaphysalis gregophilus;

[0023] The present invention also provides an insecticide comprising a solvent and the 1-methoxyindole or a derivative thereof.

[0024] The solvent used in the insecticide of the present invention is an organic solvent.

[0025] The solvent used in the insecticide of the present invention is preferably one of acetone and liquid paraffin.

[0026] In the present invention, for the insecticide, the objects to be killed include one or more of the Hymenoptera, Isoptera, Diptera, Acarina, and Thysanoptera; and also include one or more of the temperate zone bed bug, American cockroach, German cockroach, Bemisia tabaci, brown planthopper, cinnabarinus spider mite, citrus fruit fly, brown winged stink bug, red flour beetle, oriental net leafhopper, and tomato leafminer.

[0027] In the present invention, for the insecticide, the Hymenoptera insects to be killed are preferably ants, the Isoptera insects are preferably termites, the Diptera insects are preferably mosquitoes, and the Thysanoptera insects are preferably thrips.

[0028] Further preferably, the ants include one or more of the following: red imported fire ants, oriental army ants, Kissimmee ants, grassland paving ants, hairless ant, agile flat-headed ant worker ants, Chinese house ants, Pharaoh ants, and big-headed ants;

[0029] Preferably, the termites include Coptotermes Formosanus;

[0030] Preferably, the mosquito includes one or more of Culex pipiens pallens, Anopheles sinensis, Aedes albopictus, and Aedes aegypti;

[0031] Preferably, the ticks include one or more of Haemaphysalis longicornis and Haemaphysalis gregophilus.

[0032] Preferably, the thrips include one or more of Thrips leucophylla, Thrips occidentalis, and Thrips citrinum.

[0033] The present invention also provides a product with both repellent and insecticidal capabilities, comprising a solvent and the 1-methoxyindole or a derivative thereof.

[0034] The present invention also provides a method for controlling pests, which uses the 1-methoxyindole or its derivatives to control pests.

[0035] In the method of the present invention, pests include sanitary pests, social pests, and agricultural and stored-grain pests. Preferably, the sanitary pests include one or more of Culex pipiens pallens, Anopheles sinensis, Aedes albopictus, Aedes aegypti, Haemaphysalis longicornis, Haemaphysalis gregariphila, Cimex lectularius, American cockroaches, and German cockroaches; preferably, the social pests include one or more of Oriental army ant workers, Gnatia kei workers, Meadow paving ant workers, Hairless sulphur-headed ant workers, Agile flat-headed ant workers, Chinese house ant workers, Pharaoh ant workers, Big-headed ant workers, and Formosan termite workers; preferably, the agricultural and stored-grain pests include one or more of Bemisia tabaci, Nilaparvata lugens, Tetranychus cinnabarinus, Bactrocera dorsalis, Brown stink bug, Thrips leucophylla, Western flower thrips, Thrips cucurbitae, Red flour beetle, Oriental net leafhopper, and Tomato leafminer.

[0036] In the method for controlling pests of the present invention, when the 1-methoxyindole is applied as a repellent, the concentration of 1-methoxyindole in a plane is 0.127 μg / cm 2 When the 1-methoxyindole is applied as an insecticide, the concentration of 1-methoxyindole in the space is 0.14 μg / cm 3 above.

[0037] Compared with the prior art, the present invention has the following beneficial effects:

[0038] The present invention provides the use of 1-methoxyindole or its derivatives for repelling and / or killing pests. Specifically, the present invention provides a new repellent that can repel ants, termites, and ticks at a low active ingredient content. The present invention also provides a new insecticide that can kill a variety of pests at a low active ingredient concentration, providing a new means for preventing and controlling pests. When the 1-methoxyindole of the present invention is applied as a repellent, the 1-methoxyindole concentration in a plane is 0.127 μg / cm 2 When 1-methoxyindole is applied as an insecticide, the concentration of 1-methoxyindole in the air is 0.14 μg / cm 3 above. BRIEF DESCRIPTION OF THE DRAWINGS

[0039] Figure 1 The upper middle figure is the TIC graph of volatile compounds of mycelium in Example 1; the lower figure is the TIC graph of the mixed standard of C7-C40 normal alkanes in Example 1.

[0040] Figure 2 This is the mass spectrum of 1-MOI in the mycelium volatile compounds in Example 1.

[0041] Figure 3 Schematic diagrams of part of the apparatus used to test the repellent effect and duration of the repellent against pests in Example 2; A is a schematic diagram of the apparatus used in Example 2 for two-way-choice detection of the response index of pests to repellents of different concentrations; B is a schematic diagram of the apparatus used in Example 2 for barrier method detection of the repellent effect and duration of the repellent against red imported fire ants; C is a schematic diagram of the apparatus used in Example 2 for sand dredging method detection of the repellent effect against red imported fire ants. The left figure is a top view of the apparatus, and the right figure is a side view of the apparatus. Figure 3 In the figure, 1-release point, 2-unselected area, 3-1 cm filter paper, 4-9 cm plastic Petri dish, 5-ham sausage, 6-test tube, 7-open plastic container, 8-petri dish, 9-centrifuge tube.

[0042] Figure 4 The following are the repellent effects and duration tests of the 1-MOI repellent on red imported fire ants in Example 2, as well as the perception mechanism of red imported fire ants to 1-MOI; wherein A is the response index of red imported fire ant workers to repellents of different concentrations detected by Two-way-choice; B is the effect of repellents of different concentrations on the foraging behavior of red imported fire ants detected by the field feeding method; C is the effect of repellents of different concentrations on the sand digging and nesting behavior of red imported fire ants detected by the sand digging method; D is the effect of repellents of different concentrations on the attack behavior of red imported fire ants detected by the barrier method; E is the effect of repellents of different concentrations on the foraging behavior of red imported fire ants detected by the barrier method; F is the antennal potential response of red imported fire ants to repellents of different 1-MOI concentrations; G is the duration of the repellent effect detected by the barrier method after 5 minutes of volatilization at room temperature; H is the duration of the repellent effect detected by the barrier method after 6 hours of volatilization at room temperature; I is the duration of the repellent effect on the foraging behavior of red imported fire ants detected by the flat filter paper method. Different letters indicate significant differences (P<0.05, Mann-Whitney test).

[0043] Figure 5 Figure 3 shows the killing efficacy of the 1-MOI insecticide against fire ants (RIFA). Figure A shows the killing efficacy of different concentrations of the insecticide against RIFA workers using the film method; Figure B shows the killing efficacy of different concentrations of the insecticide against RIFA workers using the spot method. Different letters indicate significant differences (P < 0.05, Mann-Whitney test).

[0044] Figure 6The figures show the repellent effect of the 1-MOI repellent on Coptotermes formosanus in Example 4 and the perception mechanism of Coptotermes formosanus to 1-MOI; A is the response index of Coptotermes formosanus workers to different concentrations of repellent in the two-way-choice test; B is the electroantennal response of Coptotermes formosanus workers to different concentrations of repellent, and different letters indicate significant differences (P<0.05, Mann-Whitney test).

[0045] Figure 7 The two-way-choice test of the response index of various ants to different concentrations of 1-MOI repellent in Example 5; A to H are the response indexes of oriental army ant workers, Keegan's fine-gnathed ant workers, grassland pavement ant workers, hairless ant workers, agile flat-headed ant workers, Chinese house ant workers, Pharaoh ant workers, and big-headed ant workers to different concentrations of 1-MOI repellent, respectively. Different letters indicate significant differences (P<0.05, Mann-Whitney test).

[0046] Figure 8 These are the tick response indices to different concentrations of 1-MOI repellent detected by the two-way-choice method in Example 6; A represents the response index of Haemaphysalis longicornis to different concentrations of 1-MOI repellent; B represents the response index of Haemaphysalis gregophilus to different concentrations of 1-MOI repellent. Different letters indicate significant differences (P<0.05, Mann-Whitney test).

[0047] Figure 9 This is the efficacy of the 1-MOI insecticide tested against sanitary pests using the medicated film method in Example 7. A to I represent, in order, the mortality rates of Culex pipiens pallens, Anopheles sinensis, Aedes albopictus, Aedes aegypti, Haemaphysalis longicornis, Haemaphysalis gregophilus, Cimex lectularius, Periplaneta americana, and Blattella germanica after 12 hours of treatment with the 1-MOI insecticide. Different letters indicate significant differences (P < 0.05, Mann-Whitney test).

[0048] Figure 10 This is the efficacy of a 1-MOI insecticide against social pests tested using the Chinese herbal film method in Example 7. A to I represent, in order, the mortality rates of workers of the oriental army ant, the worker of the slender-gnathed ant, the worker of the sward-paving ant, the worker of the hairless smelt ant, the worker of the agile flat-headed ant, the worker of the Chinese house ant, the worker of the pharaoh ant, the worker of the big-headed ant, and the worker of the Formosan termite after 12 hours of treatment with the 1-MOI insecticide. Different letters indicate significant differences (P < 0.05, Mann-Whitney test).

[0049] Figure 11This is the efficacy of a 1-MOI insecticide against agricultural and stored-grain pests, as measured by the medicated film method in Example 7. A through K show, in order, the mortality rates of Bemisia tabaci, Nilaparvata lugens, Tetranychus cinnabarinus, Bactrocera dorsalis, Chaenomeles sinensis, Thrips occidentalis, Thrips cucurbitae, Tribolium castaneum, Oriental leafhopper, and Tomato leafminer after treatment with 1-MOI of the insecticide. Different letters indicate significant differences (P < 0.05, Mann-Whitney test). DETAILED DESCRIPTION

[0050] The present invention provides the use of 1-methoxyindole or its derivatives in any of the following:

[0051] S1. Repel and / or kill pests;

[0052] S2. preparing a repellent;

[0053] S3, preparing pesticide;

[0054] S4. Preparation of products with both repellent and insecticidal capabilities;

[0055] The 1-methoxyindole (1-MOI) has a structure shown in Formula I;

[0056]

[0057] The 1-MOI of the present invention is produced by fungi and has certain biosafety. The 1-MOI of the present invention is found in the volatile compound components produced by the mycelium of the wild-type Roberts' Metarhizium robertsii (Metarhizium robertsii ARSEF 2575), and the wild-type Roberts' Metarhizium ARSEF 2575 strain is described in the reference Xu C, Zhang X, Qian Y, Chen X, Liu R, Zeng G, et al. (2014) A High-Throughput Gene Disruption Methodology for the Entomopathogenic Fungus Metarhizium robertsii. PLoS ONE 9(9): e107657. The present invention has no particular restrictions on the source of the 1-MOI, and the 1-MOI can be prepared using conventional methods in the art or obtained from commercial sources.

[0058] 1-Methoxyindole, English name 1-methoxyindole, abbreviated as 1-MOI, English alias 1-Methoxy-1H-indole, MFCD18971292.

[0059] In the present invention, the repellent targets include one or more of Hymenoptera, Isoptera, and Acarina. Preferably, the Hymenoptera is an ant, and the Isoptera is a termite. The ant is preferably one or more of the following: fire ant, eastern army ant, scutellaria scutellaria, scutellaria scutellaria, hairless scutellaria, agile flat-headed scutellaria worker ant, Chinese house ant, Pharaoh ant, and big-headed ant; the termite is preferably Coptotermes formosanus; and the tick is preferably Haemaphysalis longicornis and / or Haemaphysalis quorum.

[0060] In the present invention, the objects to be killed include one or more of Hymenoptera, Isoptera, Diptera, Acarina, and Thysanoptera. Preferably, the Hymenoptera is an ant, the Isoptera is a termite, the Diptera is a mosquito, and the Thysanoptera is a thrips. The ants are preferably one or more of the following: fire ants, oriental army ants, slender ants, grass paving ants, hairless ant, agile flat-headed ant worker ants, Chinese house ants, Pharaoh ants, and big-headed ants; the termites are preferably Coptotermes formosanus; the mosquitoes are preferably one or more of the following: Culex pipiens pallens, Anopheles sinensis, Aedes albopictus, and Aedes aegypti; the ticks are preferably one or more of the longicorn tick and / or the quorum tick; and the thrips are preferably one or more of the bean thrips, western flower thrips, and melon thrips. Preferably, the insecticide of the present invention is also targeted at one or more of the following: temperate bed bug, American cockroach, German cockroach, Bemisia tabaci, brown planthopper, cinnabarinus spider mite, citrus fruit fly, brown stink bug, red flour beetle, oriental leafhopper, and tomato leafminer.

[0061] The repellent provided by the present invention comprises a solvent and the above-mentioned 1-methoxyindole or a derivative thereof; when used as the repellent, the solvent used is an organic solvent, preferably one of n-hexane, liquid paraffin, and anhydrous ethanol.

[0062] The insecticide provided by the present invention comprises a solvent and the above-mentioned 1-methoxyindole or its derivatives; when used as the insecticide, the solvent used is an organic solvent, preferably one of acetone and liquid paraffin.

[0063] The pest control method of the present invention uses the above-mentioned 1-methoxyindole or its derivatives to control pests. The pests in the method of the present invention include sanitary pests, social pests, agricultural and stored-grain pests. Specifically, the sanitary pests are preferably one or more of Culex pipiens pallens, Anopheles sinensis, Aedes albopictus, Aedes aegypti, Haemaphysalis longicornis, Haemaphysalis quorum, Cimex lectularius, American cockroaches, and German cockroaches; the social pests are preferably one or more of Oriental army ant workers, Keefe's fine-jawed ant workers, meadow paving ant workers, hairless concave stink ant workers, agile flat-headed ant workers, Chinese small house ant workers, Pharaoh ant workers, big-headed ant workers, and Formosan termite workers; the agricultural and stored-grain pests are preferably one or more of Bemisia tabaci, Nilaparvata lugens, Tetranychus cinnabarinus, Bactrocera dorsalis, Brown stink bugs, Macrothrips leucopsis, Western flower thrips, Thrips melanocarpus, Red flour beetle, Oriental leafhopper, and Tomato leafminer.

[0064] In the method for controlling pests of the present invention, when the 1-methoxyindole is applied as a repellent, the concentration of 1-methoxyindole in the plane is 0.127 μg / cm 2 When the 1-methoxyindole is applied as an insecticide, the concentration of 1-methoxyindole in the space is 0.14 μg / cm 3 above.

[0065] In the present invention, the wild type Metarhizium robertsii ARSEF 2575 is referenced as follows: Xu C, Zhang X, Qian Y, Chen X, Liu R, Zeng G, et al. (2014) A High-Throughput Gene Disruption Methodology for the Entomopathogenic Fungus Metarhizium robertsii. PLoS ONE 9(9): e107657.

[0066] The red imported fire ants described in the present invention were kindly provided by Professor Jiang Mingxing of Zhejiang University, the long-horned blood ticks were kindly provided by Professor Wang Jingwen of Fudan University, the temperate bed bugs were kindly provided by Professor Wang Desen of South China Agricultural University, the whitefly was kindly provided by Professor Wang Xiaowei of Zhejiang University, the brown planthopper was kindly provided by Professor Xu Haijun of Zhejiang University, the haemaphysalis tick and the Aedes aegypti were kindly provided by Researcher Tang Xiaotian of Zhejiang University, the oriental leafhopper was kindly provided by Professor Xu Yi of Nanjing Agricultural University, and the tomato leafminer was kindly provided by Professor Zhang Jin of Nanjing Agricultural University; other pests were either laboratory-reared or commercially available.

[0067] In the following examples, except for the larvae of the tomato leafminer, all other test pests used were adults.

[0068] Unless otherwise specified, the experimental methods used in the following examples are conventional experimental methods; the materials and reagents used are commercially available reagents and materials unless otherwise specified.

[0069] The technical solutions of the present invention will be described clearly and completely below in conjunction with the embodiments of the present invention.

[0070] Example 1

[0071] Discovery of 1-MOI

[0072] 1. Detection Method

[0073] (1) Solid phase microextraction method

[0074] Weigh 0.1 g of fresh wild-type mycelium of Metarhizium robertsii ARSEF 2575, which was preserved in the laboratory, and place it in a 20 mL glass injection vial. After closing the lid, insert a 50 / 30 μm DVB / CAR / PDMS solid phase microextraction tip into the injection vial and extract at 40°C for 50 min.

[0075] (2) SPME-GC-MS analysis method

[0076] After the above solid phase microextraction, the sample was manually injected into the instrument injection port at the injection port temperature of 250℃, and the solution was analyzed for 3 minutes using a DB-5MS (30m×0.25mm, 0.25μm) column. The GC-MS program was as follows: the starting temperature was 40℃, maintained for 2 minutes; the temperature was increased at 5℃ / min to 180℃, then increased at 10℃ / min to 270℃, and maintained for 10 minutes. Figure 1 The total ion current (TIC) diagram in the figure above was combined with the mass spectrum data of the chromatographic peak and compared with the mass spectrum library NIST05 to preliminarily predict the chromatographic peak compound. According to the CAS number of the compound provided by the mass spectrum library, a chemically synthesized standard product was purchased and compared with the C7-C 40 The normal alkane mixed standard was analyzed by GC-MS, and the results were as follows Figure 1 As shown in the figure above, according to the linear retention index (LRI) calculation formula: RI x =100×z+100×(RT x -RT z ) / (RT z+1 -RT z ) Calculate the linear retention index and confirm that the compound and the standard are the same substance based on the retention index.

[0077] 2. Results

[0078] The results of GC-MS analysis showed that among the volatile compounds produced by the mycelium of wild-type Metarhizium Robertsii, Figure 1 The mass spectrum of the substance at retention time (RT) = 19.24 min shown in the upper figure is as follows Figure 2 As shown, the compound is predicted to be 1-methoxyindole (1-MOI) in the NIST05 database. Based on the CAS number given in the database (CAS: 54698-11-2), a chemically synthesized standard of the substance was purchased. The RT of the substance in the standard was 19.24 min, which is the same as the RT of the substance in wild-type Metarhizium Robertsii mycelium and is between the RT of n-dodecane and n-tridecane. Therefore, the LRI was calculated to be 100×12+100×(19.24-17.35) / (20.18-17.35)=1266, thus identifying the substance as 1-MOI.

[0079] Table 1 Retention index of 1-MOI produced by mycelium and 1-MOI standard

[0080]

[0081]

[0082] Example 2

[0083] Repellent effect and duration of the red imported fire ant repellent and antennal potential response of the red imported fire ant to 1-MOI

[0084] 1. Detection method

[0085] (1) Two-way-choice test of the repellent effect of repellents on red imported fire ants (RIFA) workers

[0086] Use n-hexane as solvent and prepare 1-MOI concentration of 10 -3 g / mL, 10 -4 g / mL, 10 -5 g / mL, 10 -6 g / mL, 10 -7 g / mL, 10 -8 g / mL, 10 -9 g / mL repellent was used in Two-way choice test. Figure 3In the apparatus shown in Figure A, a 1-cm-diameter circular filter paper was placed at each end of a 9-cm-diameter plastic petri dish. 10 μL of repellent at different concentrations and the solvent n-hexane were added, respectively. The n-hexane solution served as a control. The mixture was then left to evaporate at room temperature for 2 minutes. Twenty healthy fire ant workers were placed at the center of the petri dish. After 10 minutes, their choices were recorded, and the response index was calculated as (number of workers who chose the filter paper with the repellent - number of workers who chose the filter paper with the n-hexane) / total number of workers. The repellent effect of each repellent concentration on fire ant workers was tested at least six times.

[0087] (2) Field feeding method to test the repellent effect of repellent on red imported fire ants (RIFA) workers

[0088] Liquid paraffin was used as a solvent to prepare repellents with different 1-MOI concentrations (the total amount of 1-MOI in the sponge was 3 μg, 30 μg, and 300 μg). When the external temperature was about 26°C, 1 g of ham sausage and a piece of 1 cm2 of water were placed in two transparent plastic bottles with a volume of 50 mL. 3 Add 300 μL of repellent to the sponge in one plastic bottle, and add the same volume of liquid paraffin to the sponge in the other plastic bottle as a control. Place the bottle opening toward the red imported fire ant mound. After 30 minutes, count the number of worker ants in both plastic bottles that have consumed the ham sausage.

[0089] (3) Sand digging method to test the repellent effect of repellent on red imported fire ants

[0090] Liquid paraffin was used as solvent to prepare repellents with different 1-MOI concentrations. Figure 3 In the C device, three round holes for 50 mL centrifuge tubes were evenly punched on the bottom of a 15 cm diameter round culture dish. The three centrifuge tubes were filled with 40 mesh fine sand mixed with 10 mL of different solutions (sterile water, liquid paraffin, 1-MOI repellent) as different treatments (the 1-MOI concentration in the fine sand was set to 2 × 10 -4 g / kg, 2×10 -3 g / kg, 2×10 -2 g / kg, 2×10 -1 g / kg), with the weight of fine sand uniformly 50g (W1). Centrifuge tubes were inserted into circular petri dishes, with the tube openings flush with the bottom of the dish. Two hundred red imported fire ant workers were placed in the center of the dish. After 12 hours, the weight of the remaining fine sand in each centrifuge tube was weighed (W2). The sand transfer rate (%) was calculated as (W1 - W2) / W1 × 100%. The repellent efficacy of each repellent concentration on imported imported fire ant workers was tested in duplicate at least six times.

[0091] (4) Barrier method to detect the repellent effect of repellent on red imported fire ants

[0092] Based on the attack and foraging behavior of red imported fire ants, a barrier method was designed to detect the repellent effect of repellents on red imported fire ants. The device used is as follows: Figure 3 As shown in B. Liquid paraffin is used as solvent and the concentration is 10 -1 g / mL, 10 -2 g / mL, 10 -3 g / mL, 10 -4 g / mL, 10 -5 g / mL, 10 -6 g / mL of repellent is used for repellent effect detection. In order to compare the repellent effect of the repellent provided by the present invention with the widely used broad-spectrum insect repellent DEET (N, N-diethyl-trimethyl-benzamide) on red imported fire ants, a 40% DEET solution was prepared for standby use. 500 μL of liquid paraffin, 40% DEET solution, and the above-mentioned repellents with different concentrations of 1-MOI were evenly sprayed on a clean round white filter paper with a diameter of 9 cm, so that the 1-MOI concentration in the filter paper was 0.00786 μg / cm 2 , 0.0786μg / cm 2 , 0.786μg / cm 2 , 7.86μg / cm 2 , 78.6μg / cm 2 , 786μg / cm 2 After 5 minutes of stagnation, the tubes were coated onto the outer wall of 8 mL glass test tubes. A whole red imported fire ant mound dug from the wild was placed in an open plastic container measuring 45 cm × 32 cm × 15 cm. Three of the tubes were inserted into the mound at intervals of 12 cm to a depth of approximately 2 cm. Within 1 minute of insertion, the number of worker ants that climbed onto the tubes and attacked was counted.

[0093] After 30 minutes, the ant colony stabilized and no longer attacked. 1g of ham sausage was placed on the top of the glass test tube. After 30 minutes, the number of worker ants that crossed the repellent barrier to eat the ham sausage was counted.

[0094] (5) Detection of antennal potential response of fire ant workers to 1-MOI

[0095] Use n-hexane as solvent and prepare 1-MOI concentration of 10 -2 g / mL, 10 -3 g / mL, 10 -4 g / mL, 10 -5 g / mL, 10 -6 g / mL, 10 -7 g / mL of repellent is ready for use. 2The filter paper was placed in a clean 1000 μL pipette tip, and 10 μL of the above repellents of different concentrations were dripped onto the filter paper so that the total amount of 1-MOI in the filter paper was 10 -4 g, 10 -5 g, 10 -6 g, 10 - 7 g, 10 -8 g, 10 -9 g. Use pointed tweezers to pinch off the antennae of red imported fire ants from the middle and rupture the tips with pointed tweezers to facilitate proper conduction of electrical signals. Use conductive glue to secure the ends of the antennae to the electrodes of the potentioantenometer. After the baseline of the antennae stabilizes, stimulate the antennae with airflow of the repellents listed above at increasing concentrations at 15-second intervals, and record the neural impulse signals generated. A negative control, n-hexane, was tested at the beginning and end of each repetition, and the signal values ​​were recorded. Ten antennae of different worker ants were tested consecutively with each repellent concentration.

[0096] (6) Detection of the duration of repellent effect of repellent on red imported fire ants based on the barrier method

[0097] Based on the above barrier method, anhydrous ethanol was used as the solvent to prepare a 100 mg / mL 1-MOI repellent and a 100 mg / mL DEET solution. 500 μL of anhydrous ethanol, 1-MOI repellent, and DEET solution were evenly sprayed on a clean round white filter paper with a diameter of 9 cm. After evaporation at room temperature for 5 minutes and 6 hours, respectively, they were wrapped around an 8 mL glass test tube. Three test tubes were inserted into the anthill at a depth of about 2 cm with a distance of 12 cm. 1 g of ham sausage was placed on the top of the test tube. The number of worker ants that crossed the repellent barrier to eat the ham sausage was counted every 1 hour.

[0098] (7) Place the filter paper flat to test the duration of the repellent's effect on fire ants

[0099] Use anhydrous ethanol as the solvent to prepare a 100 mg / mL 1-MOI repellent and a 100 mg / mL DEET solution. Spray 500 μL of anhydrous ethanol, repellent, and DEET solution evenly on a clean round white filter paper with a diameter of 9 cm. After evaporation at room temperature for 5 minutes, place 1 g of ham sausage in the center of the filter paper. Place 3 filter papers 10 cm apart on the surface of the anthill. After 2 hours, count the number of worker ants eating the ham sausage on the 3 filter papers.

[0100] 2. Results

[0101] (1) The results of the Two-way-choice method showed that after applying the repellent, when the total amount of 1-MOI was 10 -8 g~10 -3g, showed a repellent effect on fire ant workers, and the higher the 1-MOI concentration, the stronger the repellent effect ( Figure 4 A).

[0102] (2) The results of the field feeding method showed that when the total amount of 1-MOI in the sponge was 3μg, 30μg, and 300μg, the number of red fire ant workers in the plastic bottle was significantly lower than that in the control group. The higher the content, the stronger the inhibitory effect on the foraging behavior of the worker ants, achieving the goal of repelling the worker ants ( Figure 4 B) in.

[0103] (3) The results of the sand excavation method showed that when the 1-MOI concentration in the fine sand was 2×10 -4 g / kg, 2×10 -3 g / kg, 2×10 -2 g / kg, 2×10 -1 g / kg, the sand moving rate of red imported fire ants was significantly lower than that of the other two treatments, and the higher the concentration, the stronger the inhibitory effect on the worker ants' sand digging and nesting behavior, achieving the goal of repelling the worker ants ( Figure 4 C).

[0104] (4) The results of the barrier method showed that compared with the control group, when the 1-MOI concentration in the filter paper was 7.86 μg / cm 2 , 78.6μg / cm 2 , 786μg / cm 2 When the concentration of 7.86μg / cm 2 The repellent effect of 1-MOI was 3145.4μg / cm 2 There was no significant difference in DEET ( Figure 4 D in

[0105] When the 1-MOI concentration in the filter paper was 7.86 μg / cm 2 , 78.6μg / cm 2 , 786μg / cm 2 When the number of red imported fire ant workers crossing the barrier to eat ham sausage decreased significantly, among which 7.86μg / cm 2 The repellent effect of 1-MOI was 3145.4μg / cm 2 There was no significant difference in DEET ( Figure 4 The above shows that the required 1-MOI concentration is 1 / 400 of DEET to achieve the same repellent effect.

[0106] (5) The antennal potential test results show that when the total amount of 1-MOI in the repellent is 10 -4 g, 10 -5 g, 10 -6g, 10 -7 g, 10 -8 g, 10 -9 g, all of them could induce antennal potential response of fire ant workers, and as the total amount of 1-MOI increased, the antennal potential response increased accordingly, indicating that 1-MOI was perceived by fire ant workers through the olfactory system and affected their behavior ( Figure 4 F in.

[0107] (6) The results of the repellent duration test based on the barrier method showed that when the 1-MOI repellent was volatilized at room temperature for 5 minutes before being applied to the anthill, the number of worker ants that crossed the barrier to eat the ham sausage within 4 hours was significantly lower than that of the blank control group, and significantly lower than that of the experimental group with DEET; at the 5th hour, there was no significant difference in the number of worker ants that ate the ham sausage between the experimental group with 1-MOI and the DEET group, and both were significantly lower than the control group. This shows that when the 1-MOI repellent is applied by this method, the repellent effect is better retained within 5 hours, and the repellent effect is better than that of DEET within 4 hours. Figure 4 G in );

[0108] When the 1-MOI repellent was allowed to volatilize at room temperature for 6 hours before being applied to the anthill, the number of worker ants that crossed the barrier to eat the ham sausage was significantly lower than that of the control group within 4 hours. Among them, within 2 hours, the number of worker ants that ate the ham sausage in the experimental group with 1-MOI repellent was significantly lower than that in the DEET experimental group. There was no significant difference after 2 hours, indicating that when the 1-MOI repellent is applied in this way, the repellent effect is better retained within 4 hours, and the repellent effect within 2 hours is better than that of DEET ( Figure 4 H in.

[0109] (7) The results of the repellent duration test using the flat filter paper method showed that within 2 hours, the number of worker ants eating ham sausage on the filter paper with 1-MOI repellent was significantly lower than that in the control group and the experimental group with DEET. This indicates that when 1-MOI repellent is applied using this method, the repellent effect on red imported fire ants is better retained within 2 hours, and the effect is better than that of DEET ( Figure 4 I in ).

[0110] Example 3

[0111] The effectiveness of insecticides in killing red imported fire ants

[0112] 1. Detection Method

[0113] (1) Testing the killing effect of insecticides on red imported fire ants using the drug film method

[0114] Acetone was used as a solvent to prepare insecticides with different 1-MOI concentrations (the 1-MOI concentrations in the space were 0.14 μg / cm 3 , 0.28μg / cm 3 , 1.4 μg / cm3 ) A cotton ball with 0.5 mL of 2.5% sucrose solution was placed in a 350 mL tissue culture flask as a water and food source for the ants. Talcum powder was applied to the flask mouth to prevent the ants from escaping. 1 mL of repellent was added dropwise to the side of the flask. The flask was rotated to evenly distribute the insecticide. After the acetone completely evaporated, 20 healthy RIFA workers were placed in the flask and sealed. After 12 hours, the number of dead RIFA workers was counted and the mortality rate (%) was calculated: mortality rate (%) = number of dead RIFA workers / total number of RIFA workers × 100%. The contact efficacy test of each repellent concentration was repeated at least six times.

[0115] (2) Spot test of the insecticide's killing effect on fire ant workers

[0116] Insecticides were prepared using liquid paraffin as a solvent at different 1-MOI concentrations (1-MOI total: 0.01 μg, 0.1 μg, 1 μg, and 10 μg). 1 μL of the repellent was applied to the pronotum of red imported fire ant workers, who were then transferred to plastic insect boxes. Each concentration of repellent was applied to 15 workers. A cotton ball containing 0.5 mL of 2.5% sucrose solution was placed in the box as both a water source and food. After 48 hours, the number of dead red imported fire ant workers was counted, and the mortality rate (%) was calculated as: number of dead red imported fire ant workers / total number of red imported fire ant workers × 100%. A control group consisted of red imported fire ant workers treated with liquid paraffin. Six replicates were performed for each insecticide concentration.

[0117] 2. Results

[0118] (1) The results of the drug film method showed that when the 1-MOI concentration in the space was 0.14 μg / cm 3 When the concentration is 0.28μg / cm 3 The killing effect on red imported fire ants was 65%; the concentration was 1.4μg / cm 3 The killing effect on the red imported fire ants is 100% ( Figure 5 A).

[0119] (2) The results of the spot test showed that when the total amount of 1-MOI of the insecticide dropped onto the pronotum of red imported fire ants was 0.01 μg, the mortality rate of the red imported fire ants was 6%; when the total amount was 0.1 μg, the mortality rate was 28%; when the total amount was 1 μg and 10 μg, the mortality rate was greater than 60% ( Figure 5 B) in.

[0120] Example 4

[0121] The repellent effect of the repellent on Coptotermes formosanus and the electroantennographic response of Coptotermes formosanus to 1-MOI

[0122] 1. Detection Method

[0123] (1) Two-way-choice test of the repellent effect of repellents on Formosan termites workers:

[0124] The detection method is the same as the detection method (1) in Example 2, except that the red imported fire ant workers are replaced with Formosan termite workers.

[0125] (2) Detection of antennal potential response of Formosan termites to 1-MOI

[0126] The detection method is the same as the detection method (5) in Example 2, except that the red imported fire ant workers are replaced with Formosan termite workers.

[0127] 2. Results

[0128] (1) The results of the Two-way-choice method showed that after applying the repellent, when the total amount of 1-MOI was 10 -7 g~10 -3 g, showed a repellent effect on Formosan termites workers, and the higher the total amount of 1-MOI, the stronger the repellent effect ( Figure 6 A).

[0129] (2) The antenna potential test results showed that when the total amount of 1-MOI in the repellent was 10 -4 g, 10 -5 g, 10 -6 g, 10 -7 g, 10 -8 g, 10 -9 g, all of them could induce antennal potential response of Formosan termite workers, and as the total amount of 1-MOI increased, the antennal potential response increased accordingly, indicating that 1-MOI was perceived by Formosan termite workers through the olfactory system and affected their behavior ( Figure 6 B) in.

[0130] Example 5

[0131] The repellent has a repellent effect on oriental army ants, Ki's fine-jawed ants, grassland paving ants, hairless ant, agile flat-headed ant worker ants, Chinese small house ants, Pharaoh ants, and big-headed ant worker ants.

[0132] 1. Detection method:

[0133] The specific implementation method of the two-way-choice method for detecting the repellent effect of the repellent on oriental army ants, Kissler's fine-jawed ants, grassland pavement ants, hairless ant, agile flat-headed ant worker ants, Chinese house ants, Pharaoh ants, and big-headed ant worker ants is the same as the detection method (1) in Example 2.

[0134] 2. Results

[0135] (1) After applying the repellent, when the 1-MOI concentration is 10 -8 g~10 -3 g, showed a repellent effect on oriental army ant workers, and the higher the 1-MOI concentration, the stronger the repellent effect ( Figure 7 A).

[0136] (2) Figure 7 The B~H in the figure are the response indexes of oriental army ant workers, Keegan fine-jawed ant workers, grassland pavement ant workers, hairless stinking ant workers, agile flat-headed ant workers, Chinese small house ant workers, pharaoh ant workers, and big-headed ant workers to different concentrations of 1-MOI repellent; when the 1-MOI concentration is 10 -7 g~10 -3 g, it showed a repellent effect on the workers of the fine-jawed ants, the workers of the meadow ants, the workers of the hairless ant, the workers of the agile flat-headed ants, the workers of the Chinese house ants, the workers of the pharaoh ants, and the workers of the big-headed ants, and the higher the 1-MOI concentration, the stronger the repellent effect.

[0137] Example 6

[0138] The repellent's effect on repelling Haemaphysalis longicornis and Haemaphysalis gregophilus

[0139] 1. Detection Method

[0140] The specific implementation method of the two-way-choice method for detecting the repellent effect of the repellent on Haemaphysalis longicornis and Haemaphysalis gregophilus is the same as the detection method (1) in Example 2.

[0141] 2. Results

[0142] After applying the repellent, when the 1-MOI content is 10 -7 g~10 -3 g, showed a repellent effect on longhorn ticks, and the higher the 1-MOI content, the stronger the repellent effect ( Figure 8 A); when 1-MOI content is 10 -5 g~10 -3 g, showed a repellent effect on Haemaphysalis gregaris, and the higher the 1-MOI content, the stronger the repellent effect ( Figure 8 B) in.

[0143] Example 7

[0144] Pest-killing effect of insecticides

[0145] 1. The killing effect of insecticides on sanitary pests

[0146] (1) Detection method

[0147] The insecticide film method was used to detect the killing effect of the insecticide on Culex pipiens pallens, Anopheles sinensis, Aedes albopictus, Aedes aegypti, Haemaphysalis longicornis, Haemaphysalis gregariphila, Cimex lectularius, Periplaneta americana, and Blattella germanica. The specific implementation method was the same as the detection method (1) in Example 3.

[0148] (2) Results

[0149] The results of the drug film method are as follows Figure 9 As shown in A to I, Figure 9 A to I in the table represent the mortality rates of Culex pipiens pallens, Anopheles sinensis, Aedes albopictus, Aedes aegypti, Haemaphysalis longicornis, Haemaphysalis gregarivorus, Cimex lectularius, Periplaneta americana, and Blattella germanica 12 hours after treatment with 1-MOI of insecticide. After insecticide application, the 1-MOI concentration in the air was 0.14 μg / cm 3 The killing effects on Culex pipiens pallens, Anopheles sinensis, Aedes albopictus, Aedes aegypti and Haemaphysalis longicornis were 17%, 18%, 39%, 67% and 49% respectively; the concentration was 0.28μg / cm 3 The killing effects on Culex pipiens pallens, Anopheles sinensis, Aedes albopictus, Aedes aegypti, Haemaphysalis longicornis and Haemaphysalis gregarivora were 55%, 78%, 63%, 93%, 67% and 13% respectively; the concentration was 1.4μg / cm 3 When the concentration of 1-MOI in the air is 2.8μg / cm3, the killing effect on Culex pipiens pallens, Anopheles sinensis, Aedes albopictus, Aedes aegypti, Haemaphysalis longicornis and Haemaphysalis swarmingii is 100%. 3 The killing effects on the temperate zone bed bug and German cockroach were 68% and 30% respectively; the concentration was 28μg / cm 3 When the product is used for 4 hours, the killing effect on the temperate zone bed bug and German cockroach is 100%, and the killing effect on the American cockroach is 36%.

[0150] 2. The effectiveness of insecticides against social pests

[0151] (1) Detection method

[0152] The insecticide film method was used to detect the killing effect of the insecticide on oriental army ants, slender-jawed ants, grassland paving ants, hairless ant, agile flat-headed ant workers, Chinese house ants, pharaoh ants, big-headed ant workers, and Formosan termite workers. The specific implementation method was the same as the detection method (1) in Example 3.

[0153] (2) Results

[0154] The results of the drug film method are as follows Figure 10 As shown in A to I, Figure 10A to I in the table correspond to the mortality rates of Oriental Army Ant workers, Keegan's Slender-Natured Ant workers, Grassland Paving Ant workers, Hairless Odor Ant workers, Agile Flat-headed Ant workers, Chinese Small House Ant workers, Pharaoh Ant workers, Big-headed Ant workers, and Formosan Coptotermes workers 12 hours after treatment with 1-MOI of insecticide. After insecticide application, the 1-MOI concentration in the air was 0.14 μg / cm 3 The killing effects on oriental army ants, Ki's fine-jawed ants, grassland paving ants, hairless stinking ants, agile flat-headed ants, Chinese house ants, pharaoh ants, big-headed ants, and Formosan termites were 27%, 13%, 7%, 7%, 3%, 7%, 7%, 19%, and 10% respectively; the concentration was 0.28μg / cm 3 The killing effects on the above ants and termites were 64%, 81%, 54%, 48%, 67%, 29%, 34%, 44% and 41% respectively; the concentration was 1.4μg / cm 3 When the above ants and termites are killed, the killing effect is 100%.

[0155] 3. The killing effect of pesticides on agricultural pests

[0156] (1) Detection method

[0157] The insecticide film method was used to detect the killing effect of the insecticide on Bemisia tabaci, Nilaparvata lugens, Tetranychus cinnabarinus, Bactrocera dorsalis, Brown stink bug, Thrips leucophylla, Western flower thrips, Thrips occidentalis, Tribolium castaneum, Oriental leafhopper, and Tomato leafminer. The specific implementation method was the same as the detection method (1) in Example 3.

[0158] (2) Results

[0159] The results of the drug film method are as follows Figure 11 As shown in A to K, Figure 11 A to K correspond, in order, to the mortality rates of Bemisia tabaci, Nilaparvata lugens, Tetranychus cinnabarinus, Bactrocera dorsalis, Chaenomeles indica, Thrips leucophylla, Thrips occidentalis, Thrips cucurbitae, Tribolium castaneum, Oriental leafhopper, and Tomato leafminer after treatment with 1-MOI of insecticide. After insecticide application, the 1-MOI concentration in the air was 0.14 μg / cm 3 The killing effects on Bemisia tabaci, Nilaparvata lugens, Tetranychus cinnabarinus, Thrips leucoderma, Thrips occidentalis and Thrips cucurbitae were 29%, 39%, 21%, 16%, 5% and 16% respectively; the concentration was 0.28μg / cm 3 The killing effects on Bemisia tabaci, Nilaparvata lugens, Tetranychus cinnabarinus, Bactrocera dorsalis, Thrips occidentalis, Thrips cucurbitae, and Tomato leafminer were 61%, 100%, 60%, 12%, 39%, 33%, 40%, and 15% respectively; the concentration was 1.4 μg / cm 3When the concentration is 2.8μg / cm2, the killing effect on Bemisia tabaci, Nilaparvata lugens, Tetranychus cinnabarinus, Bactrocera dorsalis, Thrips occidentalis, Thrips occidentalis and Thrips citrinum is 100%, and the killing effect on Oriental leafhopper and Tomato leafminer is 89% and 93% respectively. 3 When the concentration is 28μg / cm 3 When the mixture is added, the killing effect on red flour beetle is 100%, and the killing effect on brown winged stink bug is 70%.

[0160] Based on the above results, the present invention established a 1-MOI concentration gradient in the two-way choice method for testing the repellent effect of 1-MOI repellent on pests. The results used the total amount of 1-MOI contained in the filter paper as an indicator of the repellent effect on pests. For example, the minimum effective amount of 1-MOI, 0.1 μg, was used as an example. The filter paper area was: 0.5 × 0.5 × 3.14 = 0.785 cm 2 , the calculated 1-MOI concentration in the plane = 0.1 / 0.785 = 0.127 μg / cm 2 When the total amount of 1-MOI is 1 μg, the 1-MOI concentration in the plane is 1.27 μg / cm 2 In the present invention, in the test of the insecticide film method for detecting the insecticide effect of 1-MOI insecticide on pests, the volume of the container tissue culture bottle used is 350mL, that is, 350cm 3 Taking the total amount of 500 μg applied at 1-MOI as an example, the concentration in the space = 500 / 350 = 0.14 μg / cm 3 , and so on.

[0161] Although the above embodiment provides a detailed description of the present invention, it is only a part of the embodiments of the present invention, not all of the embodiments. People can also obtain other embodiments based on this embodiment without creativity, and these embodiments all fall within the scope of protection of the present invention.

Claims

1. The use of 1-methoxyindole in any of the following, characterized in that: S1. Repel and / or kill pests; S2. preparing a repellent; S3, preparing pesticide; S4. Preparation of products with both repellent and insecticidal capabilities; The 1-methoxyindole has a structure shown in Formula I: Formula I.

2. The application according to claim 1, characterized in that The objects of application include one or more of the insects of the orders Hymenoptera, Isoptera, Diptera, Acarina, and Thysanoptera.

3. The application according to claim 2, characterized in that: The objects of application also include one or more of the following: temperate zone bed bug, American cockroach, German cockroach, Bemisia tabaci, brown planthopper, cinnabarinus spider mite, citrus fruit fly, brown winged stink bug, red flour beetle, oriental net house leafhopper, and tomato leafminer.

4. A method for controlling pests, characterized in that: The 1-methoxyindole according to claim 1 is used for pest control.

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