CN107279141A - A kind of halo parapheromone antagonist for being used to prevent and treat prodenia litura - Google Patents
A kind of halo parapheromone antagonist for being used to prevent and treat prodenia litura Download PDFInfo
- Publication number
- CN107279141A CN107279141A CN201710600729.6A CN201710600729A CN107279141A CN 107279141 A CN107279141 A CN 107279141A CN 201710600729 A CN201710600729 A CN 201710600729A CN 107279141 A CN107279141 A CN 107279141A
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- Prior art keywords
- parapheromone
- antagonist
- halo
- prodenia litura
- tetradecene
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- 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
- A01N37/06—Unsaturated 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
- 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
- A01M1/10—Catching insects by using Traps
- A01M1/106—Catching insects by using Traps for flying 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/18—Vapour or smoke emitting compositions with delayed or sustained release
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/62—Halogen-containing esters
- C07C69/63—Halogen-containing esters of saturated acids
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/09—Geometrical isomers
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- Life Sciences & Earth Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- Insects & Arthropods (AREA)
- Toxicology (AREA)
- Catching Or Destruction (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention discloses a kind of halo parapheromone antagonist for being used to prevent and treat prodenia litura.The formula of the halo parapheromone antagonist is ROCOCnHaXb.The halo parapheromone antagonist of the present invention may interfere with orientation of the prodenia litura male worm to female adult, make male worm isotropic, so as to reduce female male worm collision probability, Insect pest suppression reduces breeding potential, the extinction of pest population is progressively controlled, so as to reach the purpose of pest control.Consumption of the present invention is few, can significantly mitigate harm of the prodenia litura to brassicaceous vegetable, while environmentally friendly.
Description
Technical field
The invention belongs to technical field of biological control, and in particular to a kind of halo parapheromone for being used to prevent and treat prodenia litura
Antagonist.
Background technology
Prodenia litura (Spodoptera litura Fabricius) is Lepidoptera Noctuidae, a kind of feeding habits are miscellaneous, be distributed compared with
Extensively, agriculture and forestry are endangered with the serious intermittent worldwide insect occurred.Its larva feeding habits is miscellaneous, and its host plant includes 109 sections
389 kinds (including mutation), it is one of current agriculture important pests that can take food 99 section, 293 kinds of plants.Occur 8-11 generations within 1 year, it is eaten
Measure greatly, fecundity is strong, breeding is rapid, crops of causing harm often are migrated in groups, and have stronger disguise, breaking out property, summer
Autumn high temperature and drought it is multiple the features such as.And prodenia litura is to organochlorine, organophosphor, carbamate, pyrethroid
And a variety of insecticides such as Dipel produce resistances.It is on the verge of almost to can not find the ground that insecticide is available for preventing and treating prodenia litura
Step, especially high instar larvae.
In nature, prodenia litura female adult pest can discharge a kind of compound for being sex pheromone, lure after sexal maturity
Male worm mates to produce offspring to release source orientation flight, and with release female adult pest.Sex pheromones of Spodoptera litura Fabricius composition for (Z,
E) the carbon diene -1- acetic acid esters of -9,11- 14, the carbon diene -1- acetic acid esters of (Z, E) -9,12- 14, (Z) -9- tetradecenes -1-
Acetic acid esters and (E) -11- tetradecene -1- acetic acid esters, mass ratio is 100:27:20:27.Insect sex attractant product is bionical height
Sci-tech product, artificial synthesized sex pheromone compound is discharged by lure, and is sustained to field, lures male moth to trapper,
And male moth is killed with Physical, so as to destroy its mating, it is finally reached the purpose of preventing and treating.
Field large-scale application sex pheromone has certain effect to preventing and treating prodenia litura, but needs to expend many times, people
Power or medicament kill the adult traped.Therefore, to carry out large-scale control of insect using sex pheromone cumbersome.Letter
The plain antagonist of breath is a kind of material for being used for disturbing sex pheromone to propagate, and it may interfere with positioning of the male worm to female adult, makes male worm " fan
To ", so as to reduce female male worm collision probability, Insect pest suppression reduces breeding potential, the extinction of pest population is progressively controlled, so as to reach
To the purpose of pest control.It is few that Field information pheromones antagonist carrys out mass control insect consumption, environmentally friendly and laborsaving.But at present
Not yet find the pheromones antagonist that superpower interference effect is played to sex pheromones of Spodoptera litura Fabricius.
The content of the invention
It is an object of the invention to provide a kind of halo parapheromone antagonist and its application for being used to prevent and treat prodenia litura.
A kind of halo parapheromone antagonist for being used to prevent and treat prodenia litura, it is characterised in that the halo parapheromone
Antagonist formula is ROCOCnHaXb；
In described formula, R is (Z) -9- tetradecene bases, and X is halogen atom, n, a, b ∈ N*, wherein 1≤n≤5, a+b
=2n+1,0≤a ＜ 2n+1,0 ＜ b≤2n+1.
Optionally, X is F, Cl, Br or I, and n is 1,2,3,4,5；
It is preferred that, X is F, Cl, and n is 1,2,3；
Preferably, X is F, n is 1,2.
Optimal, the halo parapheromone antagonist is selected from (Z) -9- tetradecene bases -2,2,2- trifluoro-acetates,
(Z)-9- tetradecenes base-2,2,2-trichloroacetic esters, (Z)-9- tetradecene base-2,2- difluoro propionic esters, (Z)-9- 14
Carbene base -2,2,3- trifluoropropyl acid esters, (Z) -9- tetradecene bases -2,2,3,3- tetrafluoro propionic esters, (Z) -9- tetradecenes base -
One or more in the fluorine propionic esters of 2,2,3,3,3- five.
The preparation method of the lure of above-mentioned halo parapheromone antagonist, is carried out in accordance with the following steps：
(1) cylindrical indent rubber stopper, high 0.5-2cm, bottom diameter 0.5-2cm are chosen；
(2) it is 0.01-1 μ g/ μ L with just oneself burning is diluted to concentration by halo parapheromone antagonist described in claim 1
Solution, draws 50-200 μ L and adds to the recess of rubber stopper；
(3) natural evaporation is complete to n-hexane volatilization, is placed in -20 DEG C of refrigerators standby.
Application of the above-mentioned halo parapheromone antagonist in prodenia litura biological control.
Compared with prior art, the present invention has the advantages that：The halo parapheromone antagonist of the present invention can be done
Orientation of the prodenia litura male worm to female adult is disturbed, makes male worm isotropic, so as to reduce female male worm collision probability, Insect pest suppression is reduced numerous
Rate is grown, the extinction of pest population is progressively controlled, so as to reach the purpose of pest control.Field information pheromones antagonist is advised greatly
Mould pest control consumption is few, can significantly mitigate harm of the prodenia litura to brassicaceous vegetable, environmentally friendly and laborsaving.
Brief description of the drawings
Fig. 1 is (Z) -9- tetradecene base -2,2,2- trifluoro-acetate chemical structural drawings.
Fig. 2 is (Z)-9- tetradecene base-2,2,2-trichloroacetic esters chemical structural drawings.
Fig. 3 is (Z) -9- tetradecene base -2,2- difluoro propionic ester chemical structural drawings.
Fig. 4 is (Z) -9- tetradecene base -2,2,3- trifluoroacetic acid ester chemical structural drawings.
Fig. 5 is (Z) -9- tetradecene base -2,2,3,3- tetrafluoro propionic ester chemical structural drawings.
Fig. 6 is the fluorine propionic ester chemical structural drawings of (Z) -9- tetradecene bases -2,2,3,3,3- five.
Fig. 7 is the synthetic method schematic diagram of (Z) -9- tetradecene base -2,2,2- trifluoro-acetates.
Embodiment
Below in conjunction with the accompanying drawings, the embodiment to the present invention is described in detail, it is to be understood that the guarantor of the present invention
Shield scope is not limited by embodiment.
The preparation of embodiment 1 (Z) -9- tetradecene base -2,2,2- trifluoro-acetates
Compound in the present invention can be synthesized by same route, and Fig. 7 is shown with (Z) -9- tetradecenes base -2,
Synthetic method exemplified by 2,2- trifluoro-acetates.
2.00g (9.42mmol) (Z) -9- tetradecene alcohol is dissolved in 27mL anhydrous methylene chloride, adds 58mg's
DMAP, ice bath makes temperature maintain 0 DEG C or so, and the dichloromethane solution of TFAA is gradually added dropwise, and is added dropwise
Rear ice bath 30min is finished, room temperature reaction is stayed overnight, vacuum rotary steam removes solvent, the isolated yellow oil 2.54g of chromatographic column
(8.24mmol), yield 87.6%.
The field biological activity determination experiment of embodiment 2
It is prepared by lure：
(1) lure carrier is using the green indent rubber stopper of cylinder, high 1cm, bottom diameter 1cm.
(2) by the carbon diene -1- acetic acid esters of prodenia litura pheromone component (Z, E) -9,11- 14, (Z, E) -9,12- 14
Carbon diene -1- acetic acid esters and (E) -11- tetradecene -1- acetic acid esters, with 100:27:27 mass ratio mixing, it is dilute with n-hexane
It is interpreted into the solution that concentration is 1 μ g/ μ L.
(3) 88 μ L (1 μ g/ μ L) above-mentioned prodenia litura pheromones solution is drawn to add to Rubber end bottom, prodenia litura letter
The plain solution of breath can be penetrated into inside rubber with solvent (n-hexane).After after solvent (n-hexane) volatilization, 88 μ g twill night is obtained
Moth pheromones.
(4) by (Z)-9- tetradecene base-2,2,2- trifluoro-acetates, the chloroethene of (Z)-9- tetradecenes base-2,2,2-three
Acid esters, (Z) -9- tetradecene base -2,2- difluoros propionic ester, (Z) -9- tetradecene base -2,2,3- trifluoropropyls acid esters, (Z) -9-
Tetradecene base -2,2,3,3- tetrafluoros propionic ester and the fluorine propionic esters of (Z) -9- tetradecene bases -2,2,3,3,3- five are respectively with just
Hexane dilutes, and concentration is 0.1 μ g/ μ L.Shown in the structural formula such as Figure of description (Fig. 1-6) of above-mentioned six compounds.
(5) in the step of drawing 12 μ L (0.1 μ g/ μ L) (4) solution, the prodenia litura lure that oneself prepares with step (3)
So as to which mixing lure is made.Therefore, in prodenia litura lure, the carbon diene -1- acetic acid esters of (Z, E) -9,11- 14, (Z, E) -9,
Carbon diene -1- the acetic acid esters of 12- 14 and (E) -11- tetradecene -1- acetic acid esters and the mass ratio of directional jamming agent are 100:27:
27:20.Lure is placed in -20 DEG C of refrigerators before experiment standby.
The plot for selecting prodenia litura hazard ratio more serious, trapper is the universal trapper of moth class, and trapper is placed
Average headway between 20cm or so above crop, trapper is in more than 10m.Above-mentioned each mixing lure processing is respectively provided with 5
Individual repetition.It is respectively 5 repetitions as the sex pheromones of Spodoptera litura Fabricius lure and space management of control.
Recording method：
The trapping quantity for recording once each trapper in every two days, is handed at random between pulling polypide out rear different treatment group
Change place, to eliminate the test error that position effect is brought.Result of the test is as shown in table 1.
As seen from the results in Table 1, pheromones antagonist of the invention has preferable prevention effect to prodenia litura.Wherein information
The plain fluorine propionic esters of analog (Z) -9- tetradecene bases -2,2,3,3,3- five, the fluorine of (Z) -9- tetradecene bases -2,2,3,3,3- five
Propionic ester：(Z) -9- tetradecenes base -2,2,2- trifluoro-acetate=1:1st, (Z) -9- tetradecene base -2,2,3,3- tetrafluoros third
Acid esters, the fluorine propionic esters of (Z) -9- tetradecene bases -2,2,3,3,3- five：(Z) -9- tetradecenes base -2,2,2- trichloroacetic esters
=1:1 Insect pest suppression rate is higher, and this method consumption is few, can significantly mitigate harm of the prodenia litura to brassicaceous vegetable, together
When it is environmentally friendly.
Each halo parapheromone antagonist of table 1 is to prodenia litura pheromones interference experiment result
Inhibitory action of the pheromones of embodiment 3 and the like to insect chemical communication
Test process has blank control, pheromones processing, pheromone analogue (directional jamming agent) processing.Wherein orient dry
Disturb good three kinds of agent effect in embodiment 2：(Z) the fluorine propionic esters (A) of -9- tetradecenes base -2,2,3,3,3- five, (Z) -9-
The fluorine propionic esters of tetradecene base -2,2,3,3,3- five：(Z) -9- tetradecenes base -2,2,2- trifluoro-acetate=1:1 (B) and
(Z) -9- tetradecenes base -2,2,3,3- tetrafluoro propionic esters, respective 0.5mg and 1mg.Equal usability information in every piece of experimental plot
Plain trapper carries out adult detection, and trapper is placed in field with five-spot.The insect pest generating capacity difference in the experimental plot of selection is little,
Area is consistent, and the Rubber end of carrying information element or pheromone analogue is distributed consistent, each two rubber in each processing field
Adjacent 5m between head processing.Result of the test see the table below 2：
Isotropic effect of the different disposal of table 2 to prodenia litura
As shown in Table 2, pheromone concentration has isotropic effect when reaching certain value.By contrast, determining with dose
The isotropic rate of pheromones, and the isotropic effect of low dosage and high dose of three kinds of directional jamming agent are above to the isotropic rate of agent interfering
The isotropic effect of pheromones it is similar.As a result show pheromones antagonist disclosed by the invention at lower doses to prodenia litura
There is preferable isotropic effect.
Control effect of the directional jamming agent of embodiment 4 to insect offspring
Trapper is positioned in blank test field and the treated experimental plot of the best pheromone analogue of isotropic effect,
Pheromone analogue is screened from embodiment 3.The laying method of trapper is consistent with embodiment 3, by inquiry field before and after the processing
Larva quantity calculates Revision insect recluced rate, so as to obtain prevention effect.
Influence of the different disposal of table 3 to insect density of future generation
As shown in Table 3, directional jamming agent not only influences prodenia litura male worm to the orientation of female adult, and greatly reduces next
The insect density in generation, preventive effect is much better than isotropic the reached effect of pheromones.
Disclosed above is only the specific embodiment of the present invention, and still, the present invention is not limited to this, any this area
What technical staff can think change should all fall into protection scope of the present invention.
Claims (4)
1. a kind of halo parapheromone antagonist for being used to prevent and treat prodenia litura, it is characterised in that the halo parapheromone is short of money
Anti-agent formula is ROCOCnHaXb, in described formula, and R is (Z) -9- tetradecene bases, and X is halogen atom, n, a, b ∈ N*, its
In 1≤n≤5, a+b=2n+1,0≤a ＜ 2n+1,0 ＜ b≤2n+1.
2. it is used for the halo parapheromone antagonist for preventing and treating prodenia litura according to claim 1, it is characterised in that the halogen
(Z) -9- tetradecene bases -2,2,2- trifluoro-acetates, (Z) -9- tetradecene bases -2,2,2 are selected from for parapheromone antagonist
- trichloroacetic esters, (Z) -9- tetradecene base -2,2- difluoro propionic esters, (Z) -9- tetradecene bases -2,2,3- trifluoroacetic acids
Ester, (Z) -9- tetradecene bases -2,2,3,3- tetrafluoro propionic esters, (Z) -9- tetradecene bases -2,2,3,3,3- five fluorine propionic esters
In one or more.
3. the preparation method of the lure of the halo parapheromone antagonist described in claim 1, it is characterised in that according to following step
It is rapid to carry out：
（1）Choose cylindrical indent rubber stopper, high 0.5-2 cm, bottom diameter 0.5-2 cm；
（2）It is the molten of 0.01-1 μ g/ μ L that halo parapheromone antagonist described in claim 1 is diluted into concentration with just own burning
Liquid, draws 50-200 μ L and adds to the recess of rubber stopper；
（3）Natural evaporation is complete to n-hexane volatilization, is placed in -20 DEG C of refrigerators standby.
4. application of the halo parapheromone antagonist in prodenia litura biological control described in claim 1.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201710600729.6A CN107279141A (en) | 2017-07-21 | 2017-07-21 | A kind of halo parapheromone antagonist for being used to prevent and treat prodenia litura |
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| Application Number | Priority Date | Filing Date | Title |
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| CN201710600729.6A CN107279141A (en) | 2017-07-21 | 2017-07-21 | A kind of halo parapheromone antagonist for being used to prevent and treat prodenia litura |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112006020A (en) * | 2020-09-08 | 2020-12-01 | 中国农业科学院植物保护研究所 | Efficient attractant for spodoptera frugiperda and application of efficient attractant |
| CN112385656A (en) * | 2019-08-19 | 2021-02-23 | 中国农业科学院植物保护研究所 | Efficient attractant for athetis lepigone and application of efficient attractant |
| CN113940347A (en) * | 2021-11-19 | 2022-01-18 | 中捷四方生物科技股份有限公司 | Application of cis-9, trans-12-tetradecene acetate analogue |
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| CN105123718A (en) * | 2015-08-21 | 2015-12-09 | 中国农业科学院植物保护研究所 | Reverse sex pheromone for prevention and control of plutella xylostella l. |
| CN105145564A (en) * | 2015-09-25 | 2015-12-16 | 福建省农业科学院植物保护研究所 | Amphiphilic block copolymer micelle containing lepidopteron sex pheromone |
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2017
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| CN105123718A (en) * | 2015-08-21 | 2015-12-09 | 中国农业科学院植物保护研究所 | Reverse sex pheromone for prevention and control of plutella xylostella l. |
| CN105145564A (en) * | 2015-09-25 | 2015-12-16 | 福建省农业科学院植物保护研究所 | Amphiphilic block copolymer micelle containing lepidopteron sex pheromone |
Non-Patent Citations (2)
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112385656A (en) * | 2019-08-19 | 2021-02-23 | 中国农业科学院植物保护研究所 | Efficient attractant for athetis lepigone and application of efficient attractant |
| CN112006020A (en) * | 2020-09-08 | 2020-12-01 | 中国农业科学院植物保护研究所 | Efficient attractant for spodoptera frugiperda and application of efficient attractant |
| CN113940347A (en) * | 2021-11-19 | 2022-01-18 | 中捷四方生物科技股份有限公司 | Application of cis-9, trans-12-tetradecene acetate analogue |
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Application publication date: 20171024 |