CN109315398A - A kind of pheromone structural analog that enhances the attracting effect of sex attractant - Google Patents
A kind of pheromone structural analog that enhances the attracting effect of sex attractant Download PDFInfo
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- CN109315398A CN109315398A CN201710644105.4A CN201710644105A CN109315398A CN 109315398 A CN109315398 A CN 109315398A CN 201710644105 A CN201710644105 A CN 201710644105A CN 109315398 A CN109315398 A CN 109315398A
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- cis
- pheromone
- xestia
- nigrum
- acetate
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- 239000003016 pheromone Substances 0.000 title claims abstract description 40
- 230000000694 effects Effects 0.000 title claims abstract description 16
- 239000000877 Sex Attractant Substances 0.000 title claims abstract description 14
- -1 cis- 7- tetradecene acetic acid esters Chemical class 0.000 claims abstract description 23
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 6
- 150000002148 esters Chemical class 0.000 claims abstract description 4
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims abstract 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 4
- 241000289763 Dasygaster padockina Species 0.000 claims description 2
- 241000256259 Noctuidae Species 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 5
- IOUUIFSIQMVYKP-UHFFFAOYSA-N Tetradecyl acetate Chemical compound CCCCCCCCCCCCCCOC(C)=O IOUUIFSIQMVYKP-UHFFFAOYSA-N 0.000 claims 2
- 229940095068 tetradecene Drugs 0.000 claims 2
- ZYTGEAXLNDKCTI-MDZDMXLPSA-N (e)-tetradec-5-en-1-ol Chemical compound CCCCCCCC\C=C\CCCCO ZYTGEAXLNDKCTI-MDZDMXLPSA-N 0.000 claims 1
- SNIFAVVHRQZYGO-LUAWRHEFSA-N (z)-tetradec-5-ene Chemical compound CCCCCCCC\C=C/CCCC SNIFAVVHRQZYGO-LUAWRHEFSA-N 0.000 claims 1
- UBDIXSAEHLOROW-YPKPFQOOSA-N (z)-tetradec-7-ene Chemical compound CCCCCC\C=C/CCCCCC UBDIXSAEHLOROW-YPKPFQOOSA-N 0.000 claims 1
- 241000143060 Americamysis bahia Species 0.000 claims 1
- 240000006322 Sambucus chinensis Species 0.000 claims 1
- YSSVMXHKWSNHLH-UHFFFAOYSA-N octadecenal Natural products CCCCCCC=CCCCCCCCCCC=O YSSVMXHKWSNHLH-UHFFFAOYSA-N 0.000 claims 1
- 241000484432 Xestia c-nigrum Species 0.000 abstract description 34
- 241000607479 Yersinia pestis Species 0.000 abstract description 16
- YKPQYKBIAFGWBT-KAMYIIQDSA-N [(Z)-18-hydroxyoctadec-9-en-7-yl] acetate Chemical compound CCCCCCC(C\C=C/CCCCCCCCO)OC(C)=O YKPQYKBIAFGWBT-KAMYIIQDSA-N 0.000 abstract description 9
- 239000005667 attractant Substances 0.000 abstract description 6
- 230000031902 chemoattractant activity Effects 0.000 abstract description 6
- 241000238631 Hexapoda Species 0.000 abstract description 3
- 125000003158 alcohol group Chemical group 0.000 abstract description 3
- 230000008033 biological extinction Effects 0.000 abstract description 2
- 238000009395 breeding Methods 0.000 abstract description 2
- 230000001488 breeding effect Effects 0.000 abstract description 2
- 230000001629 suppression Effects 0.000 abstract 2
- 238000010586 diagram Methods 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- POQKXAGEBNZGTF-UHFFFAOYSA-N [C].CC(O)=O Chemical class [C].CC(O)=O POQKXAGEBNZGTF-UHFFFAOYSA-N 0.000 description 7
- 241000196324 Embryophyta Species 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- SNIFAVVHRQZYGO-PKNBQFBNSA-N (e)-tetradec-5-ene Chemical compound CCCCCCCC\C=C\CCCC SNIFAVVHRQZYGO-PKNBQFBNSA-N 0.000 description 2
- 244000061176 Nicotiana tabacum Species 0.000 description 2
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 235000006008 Brassica napus var napus Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- 241001674939 Caulanthus Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 206010059866 Drug resistance Diseases 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000013043 chemical agent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/02—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01M—CATCHING, TRAPPING OR SCARING OF ANIMALS; APPARATUS FOR THE DESTRUCTION OF NOXIOUS ANIMALS OR NOXIOUS PLANTS
- A01M1/00—Stationary means for catching or killing insects
- A01M1/02—Stationary means for catching or killing insects with devices or substances, e.g. food, pheronones attracting the insects
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/02—Acyclic compounds
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aliphatically bound aldehyde or keto groups, or thio analogues thereof; Derivatives thereof, e.g. acetals
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Insects & Arthropods (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Catching Or Destruction (AREA)
Abstract
The invention discloses a kind of pheromones analogues for improving Xestia c nigrum gyplure attractant effect.The pheromones analogue is alcohol, aldehyde or the esters along (anti-) formula, the number of carbon is N, position of double bond is 2n+1 or without double bond, the Xestia c nigrum sex attractant are as follows: cis- 7- tetradecene acetic acid esters, cis- 5- tetradecene acetic acid esters and trans- 5- tetradecene acetic acid esters, mass ratio 90:8:2.Pheromones analogue of the invention can more effectively trap and kill Xestia c nigrum male worm, to reduce female male worm collision probability, Insect pest suppression reduces breeding potential, the extinction of pest population gradually be controlled, to achieve the purpose that pest control.Not only dosage is few and environmentally friendly by the present invention, can also accurately be applied to detecting and reporting pest information, Insect pest suppression, mass trapping, be of great significance for the comprehensive treatment of Xestia c nigrum.
Description
Technical field
The invention belongs to technical field of biological control, and in particular to a kind of to improve Xestia c nigrum gyplure attractant effect
Pheromones analogue.
Background technique
Xestia c nigrum belongs to Lepidoptera Noctuidae, is that root important pests are cut on main agricultural, grassland.Larva tool
Seemingly-dead property, hides by day and comes out at night and concealment is stronger.Be distributed in all over the world, the feeding habits such as tobacco, tomato, wild cabbage, grape that can cause harm compared with
Extensively, mainly cause harm 100 various plants such as cereal crops, cotton, tobacco, vegetables, medicinal plant in China, with the various plants that cause harm
Seedling and it is famous, distribution geographical location it is throughout the country.Currently, the method prevented and treated it mainly sprays chemical agent, lures
Kill adult.Agro-chemicals control Xestia c nigrum, which is used for a long time, may make pest develop drug resistance, kill natural enemy, polluting environment
With destroy the ecosystem and control efficiency it is unstable, do not have still fundamentally to control its effective ways.
In nature, Xestia c nigrum female adult pest can discharge sex pheromone after sexal maturity to lure male worm, make its to
Source orientation flight is discharged, and is mated with the female adult pest of release sex pheromone to produce offspring.Xestia c nigrum sex pheromone is main
Ingredient is cis- 7- tetradecene acetic acid esters, and cis- 5- tetradecene acetic acid esters and trans- 5- tetradecene acetic acid esters, weight ratio are
90:8:2.The application study of insect infochemical is increasingly paid attention to both at home and abroad, the infochemical of more pests is not
Disconnected identified, synthesis and Field information.Although sex pheromone has many advantages, such as that selectivity is strong, micro efficient, environmentally friendly,
Male of the same race can only be trapped and killed, better effects could be obtained for the type of single virgin queen, it is close in wild female moth population
It is ineffective when spending higher.
Summary of the invention
The purpose of the present invention is to provide a kind of pheromones structure for improving Xestia c nigrum gyplure attractant effect is similar
Object.
A kind of pheromones analogue improving Xestia c nigrum gyplure attractant effect, the pheromones structure are similar
Object is alcohol, aldehyde or the esters along (anti-) formula, and the number of carbon is N (N is the positive integer more than or equal to 12), and position of double bond is 2n+1 (n
For any positive integer less than N) or without double bond.
The gyplure group is divided into the sex pheromone of Xestia c nigrum: cis- 7- tetradecene acetic acid esters, cis- 5- 14
Carbene acetic acid esters and trans- 5- tetradecene acetic acid esters.
Preferably, the weight ratio of the Xestia c nigrum gyplure and pheromones analogue is 1:(0.05-10), institute
Stating pheromones analogue is alcohol, aldehyde or the esters along (anti-) formula, and it is 3~8 or unparalleled that carbon number, which is 12~18 position of double bond,
Key.
The pheromones analogue is selected from cis- 3- dodecylene yl acetate, and cis- 9- tetradecene acetic acid esters is cis-
14 carbon acetic acid esters of 11-, cis- 13- hexadecene acetic acid esters, cis- 7- hexadecenol, cis- 5- octadecene aldehyde, trans- 5- ten
Four carbene alcohol, trans- 7- hexadecene acetic acid esters, one of 14 carbon acetic acid esters or more than one.
The preparation method of the lure of above-mentioned pheromones analogue carries out in accordance with the following steps:
(1) cylindrical indent rubber stopper, high 0.5~2cm, bottom 0.5~2cm of diameter are chosen；
(2) pheromones analogue described in claim 1 is diluted to concentration with just oneself burning is 0.01~1 μ g/ μ L's
Solution is drawn 50~200 μ L and is added to the recess portion of rubber stopper；
(3) natural evaporation is complete to n-hexane volatilization, and it is spare to be placed in -20 DEG C of refrigerators.
Purposes of the above-mentioned pheromones analogue in terms of Xestia c nigrum biological control.
It compared with prior art, can be with the invention has the following beneficial effects: pheromones analogue 1) of the invention
Mass trapping Xestia c nigrum male worm kills to physics；2) production of this pheromones analogue is simple and raw material is easy to get；3)
This pheromones analogue applies to field mass control pest, with few, the environmentally friendly and laborsaving feature of dosage.The present invention
Pheromones analogue by mass trapping, reduce breeding potential, the extinction of pest population gradually controlled, to reach prevention and treatment
The purpose of pest can accurately be applied to detecting and reporting pest information, pest quarantine, mass trapping, reach the reason of comprehensive treatment Xestia c nigrum
Think effect.
Detailed description of the invention
Fig. 1 is cis- 3- dodecenyl succinic acetic acid esters chemical structural formula schematic diagram.
Fig. 2 is cis- 9- tetradecene acetic acid esters chemical structural formula schematic diagram.
Fig. 3 is cis- 14 carbon acetic acid esters chemical structural formula schematic diagram of 11-.
Fig. 4 is cis- 13- hexadecene acetic acid esters chemical structural formula schematic diagram.
Fig. 5 is cis- 7- hexadecenol chemical structural formula schematic diagram.
Fig. 6 is cis- 5- octadecene aldehyde chemical structural formula schematic diagram.
Fig. 7 is trans- 5- tetradecene alcohol chemical structural formula schematic diagram
Fig. 8 is trans- 7- hexadecene acetic acid esters chemical structural formula schematic diagram
Fig. 9 is 14 carbon acetic acid esters chemical structural formula schematic diagrames.
Specific embodiment
With reference to the accompanying drawing, specific embodiments of the present invention will be described in detail, it is to be understood that guarantor of the invention
Shield range is not limited by the specific implementation.
The test of 1 field biological activity determination of embodiment
Lure preparation:
(1) lure carrier is using cylindrical green indent rubber stopper, high 1cm, bottom diameter 1cm.
(2) by the cis- 7- tetradecene acetic acid esters of Xestia c nigrum pheromone component, cis- 5- tetradecene acetic acid esters and trans-
5- tetradecene acetic acid esters is mixed with the mass ratio of 90:8:2, is diluted to the solution that concentration is 1 μ g/ μ L with n-hexane.
(3) 100 μ L (1 μ g/ μ L) above-mentioned Xestia c nigrum pheromones solution is drawn to be added to Rubber end bottom, eight words it is old
Brave pheromones solution can penetrate into inside rubber with solvent (n-hexane).After solvent (n-hexane) volatilization, the eight of 100 μ g are obtained
Word cutworm pheromones.
(4) by cis- 3- dodecylene yl acetate, cis- 9- tetradecene acetic acid esters, cis- 14 carbon acetic acid esters of 11- is cis-
13- hexadecene acetic acid esters, cis- 7- hexadecenol, cis- 5- octadecene aldehyde, trans- 5- tetradecene alcohol, trans- 16 carbon of 7-
Alkene acetic acid esters, 14 carbon acetic acid esters are diluted with n-hexane respectively, and concentration is 0.1 μ g/ μ L.The structural formula of above-mentioned eight compounds is such as
Shown in Figure of description (Fig. 1-9).
(5) the step of drawing 50 μ L (0.1 μ g/ μ L) (4) solution is added to step (3) oneself Xestia c nigrum for preparing and lures
To which mixing lure be made in core.Therefore, in Xestia c nigrum lure, Xestia c nigrum sex pheromone is similar with pheromones structure
The mass ratio of object is 100:5.It is spare that lure is placed in -20 DEG C of refrigerators before test.
The plot for selecting Xestia c nigrum hazard ratio more serious, trapper are the universal trapper of moth class, and trapper is put
20cm or so above crop is set, the average headway between trapper is in 10m or more.Above-mentioned each mixing lure processing is respectively provided with
5 repetitions.As control Xestia c nigrum sex pheromone (cis- 7- tetradecene acetic acid esters: cis- 5- tetradecene acetic acid esters:
Trans- 5- tetradecene acetic acid esters=90:8:2) lure and space management be respectively 5 repetitions.
Recording method:
The trapping quantity for recording primary each trapper for every two days, polypide is pulled out and is handed at random between rear different processing group
Change place is observed continuously 30 days with eliminating position effect bring test error.Test result is as shown in table 1.
Trapping experiments result of the 1 pheromones analogue of table to Xestia c nigrum
As seen from the results in Table 1, pheromones analogue of the invention has preferable control efficiency to Xestia c nigrum.Contain
The trapping amount of the Xestia c nigrum mixing gyplure of pheromones analogue is above the trapping of Xestia c nigrum sex pheromone
Amount illustrates that this few parapheromone analogue has certain attractive activity to Xestia c nigrum, and wherein Xestia c nigrum is believed
Breath element: cis- 5- octadecene aldehyde: cis- 7- hexadecenol: 14 carbon acetic acid esters: cis- 13- hexadecene acetic acid esters, mass ratio
For 100:2:0.5:0.5:2, the mixing gyplure attractive activity highest of this formula rate.
It also can be seen that by table 1, the trap effect of pheromones analogue cis and trans is different, trans- pheromones structure
The attractant effect of analog is weaker than the attractive activity of cis- pheromones analogue.The position of double bond, the number of carbon and information
The different formulations ratio of plain analogue has different degrees of influence to Xestia c nigrum attractive activity.
The pheromones analogue preparation of Xestia c nigrum provided by the invention is simple, and raw material is easy to get；With very strong
Trapping capability, stability is good, and the lasting period is long, and control efficiency can maintain 30 days or more；Specificity is strong, Xestia c nigrum will not be made to produce
Raw resistance；It is environmental-friendly to person poultry harmless；Resistance is strong, easy to use.The present invention can accurately be applied to detecting and reporting pest information, a large amount of
Trapping, is of great significance for comprehensive treatment Xestia c nigrum.
Disclosed above is only specific embodiments of the present invention, and still, the present invention is not limited to this, any this field
What technical staff can think variation should all fall into protection scope of the present invention.
Claims (5)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710644105.4A CN109315398A (en) | 2017-07-31 | 2017-07-31 | A kind of pheromone structural analog that enhances the attracting effect of sex attractant |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710644105.4A CN109315398A (en) | 2017-07-31 | 2017-07-31 | A kind of pheromone structural analog that enhances the attracting effect of sex attractant |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN109315398A true CN109315398A (en) | 2019-02-12 |
Family
ID=65245767
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710644105.4A Pending CN109315398A (en) | 2017-07-31 | 2017-07-31 | A kind of pheromone structural analog that enhances the attracting effect of sex attractant |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109315398A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115812712A (en) * | 2022-12-06 | 2023-03-21 | 黑龙江省森林保护研究所 | Sex attractant analogue for preventing and controlling moths in pine tips of camphor trees |
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| US6264939B1 (en) * | 1999-10-21 | 2001-07-24 | The United States Of America, As Represented By The Secretary Of Agriculture | Bisexual attractants, aggregants and arrestants for adults and larvae of codling moth and other species of lepidoptera |
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2017
- 2017-07-31 CN CN201710644105.4A patent/CN109315398A/en active Pending
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| Title |
|---|
| GH.STAN ET AL.: "Xestia (Amathes) c-nigrum L. ("Lepidoptera-Noctuidae): field response to synthetic pheromonal compounds and influence of trap design and trap maintenance on capture of males", 《REV.ROUM.BIOL.-BIOL.ANIM.》 * |
| OSAMU SAITO ET AL.: "Field Trapping Test of the Spotted Cutworm,Xestia c- nigrum (L.),by Synthetic Sex Pheromones", 《ANN.REPT.PLANT PROT.NORTH JAPAN》 * |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115812712A (en) * | 2022-12-06 | 2023-03-21 | 黑龙江省森林保护研究所 | Sex attractant analogue for preventing and controlling moths in pine tips of camphor trees |
| CN115812712B (en) * | 2022-12-06 | 2024-05-28 | 黑龙江省森林保护研究所 | Sex attractant analogue for preventing and controlling pinus sylvestris |
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Application publication date: 20190212 |