CN114315551B - Compound and preparation method and application thereof - Google Patents
Compound and preparation method and application thereof Download PDFInfo
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- CN114315551B CN114315551B CN202210035181.6A CN202210035181A CN114315551B CN 114315551 B CN114315551 B CN 114315551B CN 202210035181 A CN202210035181 A CN 202210035181A CN 114315551 B CN114315551 B CN 114315551B
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Abstract
The application discloses a structural formula of a novel compound (3Z, 6Z) -nineteen-carbon diene-9-ketone, a preparation method and application thereof. In the application, (3Z, 6Z) -nineteen-carbon diene-9-ketone is used as a repellent to efficiently repel ulna moth pests, especially male grifola frondosa, in a forest, the density of the male insects and the female insects in the forest is reduced, the proportion between the male and the female is not coordinated, the mating between the male and the female is interfered, and the harm to host plants such as white birch is reduced. The compound has high biological activity as a repellent, can be matched with an attractant for use, and can be used for repelling the ulnar pests such as the grifola frondosa geometrid in the areas where the conditions of forest lands are complex and chemical pesticides are not suitable for use, so that the aim of prevention and control is fulfilled.
Description
Technical Field
The application relates to the technical field of pest control, in particular to a compound and a preparation method and application thereof.
Background
The general ulna is taken as the third major family of lepidoptera insects, and the pheromone component of the total 93 kinds of 158 ulna is identified at present. The ulnara insect pheromone component mainly comprises unsaturated hydrocarbon and corresponding epoxy derivative or hydrocarbon compound (C) with methyl side chain 17 -C 23 ) Small amount of the components are alcohol, aldehyde, acetate, butyric acid and ketone compounds. The prior art reports on the application of the sex pheromone of the insects in the family of the ulnaraceae in a concentrated attracting aspect, but reports on the sex pheromone repelling aspectFew applications are practical.
Lepidoptera griseus Larerannis orthogrammaria (wehrli) is Lepidopteplera, insects of the ulnara family geodetidae, the subfamily ulnariae, ennominae. The insects grow 1 generation per year, overwintering with eggs in bark cracks. Hatching the larvae in the middle and late 5 months of the second year, putting the mature larvae in the late 6 months into the soil for pupation, and starting the eclosion of the pupae in the upper 10 months of the year, mating and spawning. The host comprises a plurality of broad-leaved trees such as white birch, red birch, white birch, aspen, red willow and the like, the larva food quantity is large, the tender buds of the host can be completely eaten, and the influence on the growth of the forest is great. The insects have an upward trend in recent years, and the insects pose a serious threat to the production of natural forests.
At present, chemical agents are the most important means for controlling the inchworm of the grifola frondosa, and in the larva stage, 50% of insecticidal absolute oil agent and 1:1 (V/V) diesel oil are mixed and sprayed, and the killing rate is more than 95%; in addition, biological agents can be adopted for prevention and treatment, and the bacillus thuringiensis emulsion and 50% of insecticidal absolute oil are mixed and sprayed according to the ratio of 11:1, and the effect can reach 87%. At present, although chemical pesticides have quick effect, the method has high control cost, and is easy to generate pesticide residues, environmental pollution, drug resistance of pests and the like.
The insect's own information chemical substance is used to control the harm of insect pest or to interfere with and prevent insect pest, so as to achieve the purpose of directly or indirectly controlling insect pest. The product has the advantages of environmental friendliness, no residue, safety and no toxicity to human and livestock, and has wide application prospect.
Disclosure of Invention
The application provides a compound, the structural formula of which is shown as formula I,
the preparation method of the compound comprises the steps of dissolving (3Z, 6Z) -nondienenitrile in tetrahydrofuran, then reacting with decyl magnesium bromide, and purifying to obtain (3Z, 6Z) -nineteen-carbon diene-9-ketone, namely the compound.
Specifically, the preparation method of the compound comprises the following steps:
(1) At N 2 Under protection, each 2.70g of (3Z, 6Z) -nondienenitrile was dissolved in 30ml of tetrahydrofuran to give solution I;
(2) 20mg of CuI and 30ml of 1M decyl magnesium bromide are added to the solution I in sequence, reacted for 24 hours at-20 ℃, then saturated NH is used 4 Terminating the reaction by Cl to obtain a reaction solution;
(3) The reaction was extracted with n-hexane, the organic phases were combined, and dried over anhydrous MgSO 4 Drying;
(4) Removing the organic phase by reduced pressure distillation to obtain a crude product;
(5) Petroleum ether/ethyl acetate 20-10:1 is used as a mobile phase, and a silica gel column is used for purifying and treating the crude product to obtain (3Z, 6Z) -nineteen carbon diene-9-ketone.
The application also provides application of the compound (3Z, 6Z) -nineteen-carbon diene-9-ketone in repelling insects of the ulnara family.
Specifically, the insect is Gray pseudobulb.
The application also provides a ulnara insect repellent, which comprises the compound.
The application also provides a method for preventing and controlling the ulnaraceae insects, which is to adopt the repellent to prevent and control the ulnaraceae insects.
Specifically, the dosage of the repellent is 100-5000 ug/site, the number of the suspension in the forests is 1-5 sites/mu, and 3 sites are preferred; the distance between every two repellent is 30-50m. The insect is Gray pseudonymph.
Further, the control method further comprises the step of arranging an attractant on the periphery of the area where the repellent is arranged. Specifically, the attractant comprises 2500ug of (3Z, 6Z, 9Z) -eicosatriene and 2500ug of (3Z, 6Z, 9Z) -nineteen-carbon triene; the distance between the attractant and the repellent is 50-100m; the repellent is directly fixed on the tree; the repellent is arranged at a height of 1.5-3m from the ground; the attractant is fixed between two trees; the attractant is arranged at a height of 1.5-3m from the ground.
The beneficial effects of the application include:
the novel compound (3Z, 6Z) -nineteen-carbon diene-9-one provided by the application can be used as a repellent to effectively repel ulna moth pests, in particular to the male worm of the strongylocentrotus griseus, reduce the density of the male worm mouth in forests, lead the proportion between male and female to be inconsistent, interfere mating between male and female, and reduce the harm to host plants such as white birch. The compound has high biological activity as a repellent, can be matched with an attractant for use, and can be used for repelling the ulnar pests such as the grifola frondosa geometrid in the areas where the conditions of forest lands are complex and chemical pesticides are not suitable for use, so that the aim of prevention and control is fulfilled.
The repellent provides a new thought for the research and development of pest repellents and mating disruptors, has important application value and economic value in pollution-free control of the inchworm griseus, and has remarkable social benefit and ecological benefit.
Drawings
FIG. 1 is a graph showing the results of a test of a repellent (100 ug) against male adults of Graptopetalum album;
FIG. 2 is a graph showing the results of a test of a repellent (250 ug) against male adults of Graptopetalum album;
FIG. 3 is a graph showing the results of a test of the repellent (1000 ug) against male adults of Graptopetalum album;
FIG. 4 is a graph showing the results of a test of the repellent (2500 ug) against male adults of Graptopetalum album;
FIG. 5 is a graph showing the results of a test of a repellent (5000 ug) against male adults of Graptopetalum album;
FIG. 6 is a graph showing the trapping effect of repellent (5000 ug)/attractant, attractant on male adults of Graptopetalum album;
FIG. 7 is a schematic view of a green-pseudonymph repellent and attractant woodland suspension;
FIG. 8 is a synthetic scheme for the compound (3Z, 6Z) -nonadecadien-9-one of the present application.
Detailed Description
The present application is further illustrated and described below with reference to the following examples, which are but some, but not all, examples of the application. All other applications and embodiments, based on this application and described herein, which would be apparent to one of ordinary skill in the art without undue burden are within the scope of this application.
The experimental methods used in the following examples are conventional methods unless otherwise specified.
Materials, reagents and the like used in the examples described below are commercially available unless otherwise specified.
Example 1 structural formula of novel Compound (3Z, 6Z) -nineteen carbon diene-9-one and Synthesis method
1. The structural formula of the (3Z, 6Z) -nineteen carbon diene-9-ketone is shown as formula I:
2. preparation of (3Z, 6Z) -nonadecadien-9-one
The preparation is carried out according to the synthetic route in fig. 8, and the specific steps are as follows:
(1) At N 2 2.70g of (3Z, 6Z) -nondienenitrile was dissolved, with protection, in 30ml of tetrahydrofuran to give solution I.
(2) 20mg of copper iodide (CuI) and 30ml of 1M decyl magnesium bromide are added to the solution I in sequence, reacted for 24 hours at-20 ℃, and then saturated NH is used 4 The reaction was terminated with Cl to obtain a reaction solution.
(3) The reaction was extracted with n-hexane, the organic phases were combined, and dried over anhydrous MgSO 4 And (5) drying.
(4) After the organic phase was removed by distillation under the reduced pressure, a crude product was obtained.
(5) The crude product was purified by column chromatography on silica gel using petroleum ether/ethyl acetate 20:1 as mobile phase to give (3Z, 6Z) -nonadecadien-9-one (3.34 g, 60% yield).
3. Structure confirmation of novel compound (3Z, 6Z) -nineteen carbon diene-9-ketone
(1) Nuclear magnetic data: 1 H-NMR(500MHz,CDCl 3 )δ0.87(3H,t,J＝7.5Hz),0.97(3H,t,J＝7.5Hz),1.25–1.35(14H,m),1.54(2H,m),2.05(2H,m),2.40(2H,m),2.80(2H,m),2.94(2H,m),5.29–5.52(4H,m).。
(2) Mass spectrometry data: GC-MS (70 eV, EI) 278.
The identified structure is correct.
Example 2, repellent effect test of 100ug (3Z, 6Z) -nonadecadien-9-one
In the embodiment, the inchworm of Gray-simulated flower is taken as a repellent object, and the repellent effect of (3Z, 6Z) -nineteen-carbon diene-9-ketone on insects of the ulnara family is studied.
1. Material preparation:
(1) Preparation of the grifola frondosa inchworm repellent: 100ug of (3Z, 6Z) -nineteen-carbon diene-9-one prepared in example 1 is added into a polyethylene plastic tube (purchased in the market), and the grifola frondosa inchworm repellent is prepared.
(2) Preparation of an inchworm attractant lure: 2500ug of (3Z, 6Z, 9Z) -eicosatriene and 2500ug of (3Z, 6Z, 9Z) -nineteen-carbon triene are added into a polyethylene plastic tube (purchased in the market), and the grifola frondosa geometrid attractant lure is prepared.
(3) The trap is a small-sized ship-shaped trap (purchased in the market), and is internally provided with a mythimna separata plate.
2. And (3) test design:
(1) 1 blank carrier (blank), 1 repellent (repellent), 1 repellent and attractant attracting cores (repellent/attractant) and 1 attractant attracting core (attractant) are respectively fixed in the traps of different boats by fine iron wires to prepare 4 traps as 4 groups of test treatments.
(2) The test site is the lignum sappan mountain of inner Mongolia, 4 kinds of traps are respectively arranged in the woodland, namely 4 groups of test treatments are respectively arranged, 3 repeats are arranged in each group of test treatments, the interval between traps in a group is about 50 meters, and the interval between traps in a group is 500 meters. The trap is fixed between the two trees and is 150cm above the ground.
(3) Data investigation: the investigator recorded the number of trapped male adults every 3-4 days and replaced the armyworm plate. The average trapping number of single traps of the Gray pseudobulb inchworm is counted from 9 months in 2020 to 29 months in 10 months, and the result is shown in FIG. 1.
From the data analysis in fig. 1, the inchworm grifola frondosa attractant lure has very good lure effect (comparison blank group); 100ug (3Z, 6Z) -nineteen-dien-9-one has strong repellent capability to male adults of the grifola frondosa geometrid, and can reduce the trapping amount of the lure of the grifola frondosa geometrid attractant by 42.7 percent.
EXAMPLE 3 repellent effect test of 250ug (3Z, 6Z) -nonadecadien-9-one
The average trapping number results of the ash-removed geometrid in this example are shown in FIG. 2, except that the (3Z, 6Z) -nonadecadien-9-one content in the ash-removed geometrid repellent is 250ug, and the rest is the same as in example 2.
From the data analysis in FIG. 2, (3Z, 6Z) -nonadecadien-9-one showed strong repellency to male adults of Graptopetalum album, the trapping amount of the lure of the grifola frondosa geometrid attractant can be reduced by 45.9 percent.
EXAMPLE 4 repellent effect test of 1000ug (3Z, 6Z) -nonadecadien-9-one
The average trapping number results of the ash-removed geometrid in this example are shown in FIG. 3, except that the (3Z, 6Z) -nonadecadien-9-one content in the ash-removed geometrid repellent is 1000ug, and the rest is the same as in example 2.
From the data analysis in fig. 3, the (3Z, 6Z) -nineteen-dien-9-one shows strong repellent capability to male adults of the grifola frondosa geometrid, so that the trapping amount of the lure of the grifola frondosa geometrid attractant can be reduced by 51.7%.
EXAMPLE 5 2500ug (3Z, 6Z) -nonadecadien-9-one repellent effect test
The average trapping number results of the dust-removed geometrid in this example are shown in FIG. 4, except that the (3Z, 6Z) -nonadecadien-9-one content in the repellent is 2500ug, and the rest is the same as in example 2.
From the data analysis in fig. 4, the (3 z,6 z) -nonadecadien-9-one shows strong repellent capability to male adults of the grifola frondosa geometrid, and the trapping amount of the lure of the grifola frondosa geometrid attractant can be reduced by 69.2%.
EXAMPLE 6 5000ug (3Z, 6Z) -nineteen carbon dien-9-one repellent effect test
The average trapping number of the dust-removed inchworm pseudolaricis in this example is shown in FIG. 5, and the trapping effect of the dust-removed inchworm pseudolaricis is shown in FIG. 6, except that the (3Z, 6Z) -nineteen-carbon-diene-9-one content in the repellent is 5000ug, and the rest is the same as in example 2.
From the data analysis in fig. 5, it is shown that (3 z,6 z) -nonadecadien-9-one shows strong repellent ability to male adults of the grifola frondosa geometrid, and the trapping amount of the lure of the grifola frondosa geometrid attractant can be reduced by 71.5%.
As can be found from the repellent effect tests of the above examples 2 to 6, when the repellent for the grifola frondosa and the attractant are used simultaneously, the trapping amount of the male insects of the grifola frondosa can be obviously inhibited and reduced by 42.7 to 71.5%, and the grifola frondosa is not trapped by the repellent for the grifola frondosa alone in each example, which indicates that (3Z, 6Z) -nineteen-carbon diene-9-one can be used as the repellent for the grifola frondosa in forests and the content of (3Z, 6Z) -nineteen-carbon diene-9-one is preferably 100 to 5000ug.
Example 7 test of Effect of use of repellent and attractant in coordination
The embodiment is used for evaluating the effect of the repellent (3Z, 6Z) -nineteen-carbon diene-9-ketone and the attractant for controlling the grifola frondosa inchworm in a coordinated manner, and the experimental design is as follows:
(1) 2 treatments were added, treatment 1 was the grifola frondosa looper repellent ((3 z,6 z) -nonadecadien-9-one 5000 ug) +the grifola frondosa looper attractant ((3 z,6z,9 z) -eicosatrien 2500ug, (3 z,6z,9 z) -nonatrien 2500 ug), treatment 2 was the blank carrier + the grifola frondosa looper attractant ((3 z,6z,9 z) -eicosatrien 2500ug, (3 z,6z,9 z) -nonatrien 2500ug.
(2) In the birch forest in North mountain forest farm of Qinghai mutually-assisted county, 6 areas are selected, each area is 300m apart, each area is provided with one treatment, each treatment is provided with 3 repetitions, and the specific settings are as follows:
treatment 1: 9 grifola frondosa looper repellents are hung in each area (areas 1,3 and 5) and distributed in square, are separated by 30m, and are directly fixed on white birch, and have a height of 150cm from the ground. 4 traps carrying the grifola frondosa geometrid attractants are respectively hung on the periphery of the square repellent (as shown in figure 7A), the attractant traps are fixed between two trees, the distance between the traps and the repellent is 50m, and the height of the traps from the ground is 1.5m.
Treatment 2: the group replaced the repellent with a blank carrier and the suspension method was identical to treatment 1 (corresponding to zones 2,4,6 as shown in fig. 7B).
Data investigation: the investigator recorded the number of trapped male adults every 3-4 days and replaced the armyworm plate. The average number of lures of individual traps of the Gray pseudobulb inchworms was counted from 10 months 8 to 21 months 2021, and the results are shown in Table 1. As can be seen from the amounts of insects adhered to the insect sticking plates in table 1 and fig. 7, the coordination of the repellent and the attractant for the inchworm of the grifola frondosa significantly increases the trapping amount of the male insects of the inchworm of the grifola frondosa.
TABLE 1 evaluation of trapping Effect of the treatments 1-2 of the present example
Claims (7)
1. A compound has a structural formula shown in formula I,
2. a process for the preparation of a compound as claimed in claim 1, which comprises dissolving (3 z,6 z) -nonedienenitrile in tetrahydrofuran, then reacting with decyl magnesium bromide, purifying to obtain (3 z,6 z) -nonadecadien-9-one, which is the compound as claimed in claim 1.
3. The preparation method according to claim 2, characterized in that the preparation method comprises the steps of:
(1) At N 2 2.70g of (3Z, 6Z) -nondienenitrile was dissolved in 30ml of tetrahydrofuran under protection to give solution I;
(2) 20mg of CuI and 30ml of 1M decyl magnesium bromide are added to the solution I in sequence, reacted for 24 hours at-20 ℃, then saturated NH is used 4 Terminating the reaction by Cl to obtain a reaction solution;
(3) The reaction was extracted with n-hexane, the organic phases were combined, and dried over anhydrous MgSO 4 Drying;
(4) Removing the organic solvent by reduced pressure distillation to obtain a crude product;
(5) Petroleum ether/ethyl acetate 20-10:1 is used as a mobile phase, and a silica gel column is used for purifying and treating the crude product to obtain (3Z, 6Z) -nineteen carbon diene-9-ketone.
4. The use of a compound as claimed in claim 1 for repelling pseudoinchworm griseus.
5. An inchworm repellent, characterized in that it comprises the compound of claim 1.
6. A method for preventing and controlling the inchworm of grifola frondosa is characterized in that the repellent is adopted according to claim 5, the consumption of the repellent is 100-5000 ug/position, the number of hanging woods is 1-5 places/mu, the distance between every two places of the repellent is 30-50m, and attractants comprising 2500ug of (3Z, 6Z, 9Z) -eicosatriene and 2500ug of (3Z, 6Z, 9Z) -nineteen-carbon triene are further arranged on the periphery of a region where the repellent is arranged.
7. The control method according to claim 6, wherein the attractant comprises 2500ug of (3 z,6z,9 z) -eicosatriene, (3 z,6z,9 z) -nineteen-carbon triene; the distance between the attractant and the repellent is 50-100m; the repellent is directly fixed on the tree; the repellent is arranged at a height of 1.5-3m from the ground; the attractant is fixed between two trees; the attractant is arranged at a height of 1.5-3m from the ground.
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| CN109970534A (en) * | 2019-04-24 | 2019-07-05 | 中国农业大学 | A method of synthesis sex pheromone of Carposina niponensis |
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2022
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|---|---|---|---|---|
| EP0183922A2 (en) * | 1984-09-05 | 1986-06-11 | BASF Aktiengesellschaft | Process and agent for combating the rhomboid looper Boarmia rhomboidaria |
| CA2041529A1 (en) * | 1991-04-30 | 1992-10-31 | Gerhard Johannes Gries | Method and composition for attracting and controlling hemlock loopers |
| CN102823590A (en) * | 2011-06-17 | 2012-12-19 | 信越化学工业株式会社 | Sex pheromone composition of peach fruit moth and attractant comprising the same |
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