CN101502262B - Synthesis of Sex pheromone of sod webworm and use thereof - Google Patents
Synthesis of Sex pheromone of sod webworm and use thereof Download PDFInfo
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- CN101502262B CN101502262B CN2009100805762A CN200910080576A CN101502262B CN 101502262 B CN101502262 B CN 101502262B CN 2009100805762 A CN2009100805762 A CN 2009100805762A CN 200910080576 A CN200910080576 A CN 200910080576A CN 101502262 B CN101502262 B CN 101502262B
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Abstract
The present invention discloses a meadow moth gyplure and application thereof. The meadow moth gyplure according to the invention comprises trans-11-tetradecene acetic ester, trans-11-tetradecene aldehyde and n-tetradecanol. The mass ratio of trans-11-tetradecene acetic ester, trans-11-tetradecene aldehyde and n-tetradecanol is (1-7): (1-5): (1-15). The meadow moth gyplure can be applied for luring meadow gyplure and measuring the meadow gyplure pest situation. The gyplure of the invention has the following advantages: artificial synthesizing, simple structure, convenient synthesizing, easy generalizing, extraordinary using dosage, no environment pollution, high specificity, no fastness generation, no energy consumption requirement, and simple, safe and effective use. Compared with the artificial measuring, the method for luring meadow moth according to the invention can reduce the labor intensity and increase the standard property for counting the number of meadow moth. The meadow moth gyplure of the invention has great economic benefit and social benefit.
Description
Technical field
The present invention relates to a kind of synthetic and application of Sex pheromone of sod webworm.
Background technology
Beet webworm (Coxostege sticticalis L.) is a kind of migratory pest of China crops and herbage, intermittently breaks out, and mainly is distributed in northeast, North China, the Northwest, and it takes place, and the oncoming force is violent, density big, harm is serious.At outbreak year, can destroy large stretch of crops and herbage in the short time, cause serious disaster.In recent years, the beet webworm adult broke out greatly in north China, and the degree of breaking out is rare in recent years with the generation area.Starting with from prediction in anti-Zhiduo County to beet webworm, prevents and treats through chemical agent.Because of the economic worth of grassland unit are is lower, use chemical pesticide often to lose more than gain in a large number.Secondly, a large amount of uses of chemical pesticide can cause the deterioration of grassland ecology environment, and jeopardize the grassland agriculture development.Compare with chemical control, biological control has the characteristics low, that bring notable results, be easy to enforcement on a large scale that drop into.
Utilize the pheromones pest control have efficient, nontoxic, do not injure beneficial insect, advantage such as free from environmental pollution, both at home and abroad this Study on Technology is all taken much count of with using.The trace level chemical substance that can have special odor after many insects reach maturity to vitro release is to lure different in nature insect mating of the same race.This chemical substance that in the insect mating process, plays the communication effect is an insect sex pheromone, or sex pheromone.During with the sex pheromone of synthetic or analog pest control, be the insect sex attractant usually, be called for short gyplure.
The main application of gyplure in control of insect is the monitoring insect pest situation, makes detecting and reporting pest information.Since it have highly sensitive, accuracy good, easy to use, do not receive time and advantages such as the circadian restriction of insect, cost, obtaining application more and more widely.Gyplure observes and predicts method and makes the insect pest situation monitoring tool with trapper.Trapper is by luring core and insect trap two parts to form, and luring core is the carrier of gyplure.Small rubber plug, silicone rubber plate or the vinyl tube etc. that contain insect sex attractant lure the core activity good, render a service high, easy to use.For example, a small rubber plug that contains 0.2mg oriental fruit moth gyplure lures core, can trap and kill tens in one day, even one or two hundred male moths, can use more than three months continuously.
Gyplure can observe and predict insect pest situation accurately, helps rationally using agricultural chemicals, reduces production costs, and also helps reducing environmental pollution, ensures people ' s health.For example, Miyun County township in Beijing's adopts fruit tree pest insects such as " medicament blockade " method control oriental fruit moth in the past, whenever once at a distance from 10-15 days laxatives, and annual laxative 10-11 time.And after carrying out detecting and reporting pest information with gyplure, annual laxative 4-5 time is saved expenses for prevention and control 60%, and control efficiency also obviously improves.
Summary of the invention
The purpose of this invention is to provide a kind of synthetic and application of Sex pheromone of sod webworm.
Sex pheromone of sod webworm provided by the invention comprises anti-11-tetradecene acetate, anti-11-tetradecene aldehyde and positive tetradecyl alchohol; The mass ratio of said anti-11-tetradecene acetate, anti-11-tetradecene aldehyde and positive tetradecyl alchohol can be (1-7): (1-5): (1-15).
Sex pheromone of sod webworm provided by the invention also can only be made up of anti-11-tetradecene acetate, anti-11-tetradecene aldehyde and positive tetradecyl alchohol, and the mass ratio of said anti-11-tetradecene acetate, anti-11-tetradecene aldehyde and positive tetradecyl alchohol can be (1-7): (1-5): (1-15).In the said Sex pheromone of sod webworm, the mass ratio of said anti-11-tetradecene acetate, anti-11-tetradecene aldehyde and positive tetradecyl alchohol specifically can be 5: 3: 12.
The present invention also provides a kind of beet webworm to lure core, comprises carrier and is carried on the said Sex pheromone of sod webworm on this carrier.The commercially available carrier of any carrying insect sex attractant all can adopt, like rubber stopper, silicone rubber plate or vinyl tube.
Said beet webworm lures the core specifically can be through the said carrier of Sex pheromone of sod webworm solution impregnation is obtained.
Said Sex pheromone of sod webworm, said beet webworm lure core all to can be applicable to trap beet webworm.
Said Sex pheromone of sod webworm, said beet webworm lure core all to can be applicable in the beet webworm detecting and reporting pest information.
When using said beet webworm to lure core; Can start overwinter generation meadow snout moth and emit before the phase, up to the last reign of a dynasty moth till the disappearance of field, a generation that lures core can use beet webworm; Must not emit every day and regain, upgrade once luring the core better effects if with 30～40 days.
Sex pheromone of sod webworm of the present invention has following advantage: 1. adopt synthetic, and simple in structure, synthetic convenient, be convenient to promote.2. using dosage is atomic, can lure insect collection in very little scope, to handle.3. preparation not necessarily contacts soil and crop, even contact is free from environmental pollution also very soon by biological degradation.4. make apparatus height specificity, do not accidentally injure other beneficial organism.5. do not produce resistance, and when reducing fertility, reduce its population quantity, thereby obtain integrated control effect.6. need not electricity consumption, can save equipment such as electric energy and electric wire, in the non-transformer pastoral area or there are the artificially sown pastures of power supply all can use.7. use simple, safety, effective.
Test oneself with manual work and to compare, use Sex pheromone of sod webworm of the present invention or beet webworm and lure core that beet webworm is traped, can reduce labour intensity; Improve the standard of beet webworm quantity statistics; Take place thereby prediction is big, judge harmful economically critical point, and can directly reduce progeny size.So, make observe and predict and instruct control more accurately, convenient, effectively.The present invention has great economic benefit and social effect.
Description of drawings
Fig. 1 is the infrared spectrogram of anti--11-tetradecene alcohol.
Fig. 2 is the infrared spectrogram of anti--11-tetradecene aldehyde.
Fig. 3 is that Sex pheromone of sod webworm G and black light lamp lure the effect of moth to compare.
Embodiment
Following embodiment is convenient to understand better the present invention, but does not limit the present invention.Experimental technique among the following embodiment like no specified otherwise, is conventional method.Used test material among the following embodiment like no specified otherwise, is to buy from routine biochemistry reagent shop and obtains.
Anti-11-tetradecene acetate: available from Sigma-Aldrich company, catalog number: T-2143.
Positive tetradecyl alchohol: available from Sigma-Aldrich company, catalog number: 185388.
Instead-synthetic route of 11-tetradecene aldehyde is following:
The first step: synthesize anti--11-tetradecene alcohol by anti-11-tetradecene acetate
In 50 milliliters of round-bottomed bottles, add 0.436g (0.011mol) sodium hydroxide, 4mL water and 4mL methyl alcohol, fully stir with magnetic stirring apparatus, add again after the dissolving 0.288g (0.0011mol) anti--11-tetradecene acetate, stirring at room 2.5 hours.Reaction finishes the back with the neutralization of 5% watery hydrochloric acid, 25mL extracted with diethyl ether three times, and combined ether layer is successively with 25mL water, the washing of 25mL saturated common salt, anhydrous sodium sulfate drying.Ether is removed in distillation, and residue separates through silica gel column chromatography.The infrared spectrogram of product is seen Fig. 1, and infrared spectrogram shows that product is anti--11-tetradecene alcohol.Obtain 0.223g anti--11-tetradecene alcohol, colourless liquid, productive rate 92.9%.
Second step: by instead-11-tetradecene alcohol synthetic anti--11-tetradecene aldehyde
(magnetic stirring apparatus, thermometer, drying tube, triangular flask are washed with the concentrated sulfuric acid, saturated sodium bicarbonate solution before using successively in 100 milliliters of there-necked flasks that magnetic stirring apparatus, thermometer, anhydrous calcium chloride drying tube are housed, to add the 25mL carrene; Distill after the anhydrous calcium chloride drying), 0.8g (0.01mol) pyridine.Stir, be cooled to 5 ℃, once add 0.477g (0.0048mol) chromium trioxide with ice-water bath.Continuation was stirred 10 minutes down in cooling, in 1 hour, temperature was risen to 20 ℃ then, add rapidly 0.169g (0.0008mol) anti--the pure dichloromethane solution 1mL of 11-tetradecene.Stir hypsokinesis in 15 minutes and go out dichloromethane solution, solid residue is at every turn with 20mL ether washing 3 times in the reaction bulb.Combined dichloromethane, diethyl ether solution are used 50mL ice-cold 5% sodium hydroxide solution, 50mL ice-cold 5% hydrochloric acid, 50ml ice-cold 5% sodium bicarbonate solution and the water washing of 50mL saturated common salt successively.Anhydrous magnesium sulfate drying, decompress(ion) removes and desolvates, and residue separates through silica gel column chromatography.The infrared spectrogram of product is seen Fig. 2, and infrared spectrogram shows that product is anti--11-tetradecene aldehyde.Obtain 0.145g anti--11-tetradecene aldehyde, colourless liquid, productive rate 86.3%.
The preparation of embodiment 1, Sex pheromone of sod webworm
Following Sex pheromone of sod webworm A forms by anti-11-tetradecene acetate, anti-11-tetradecene aldehyde and positive tetradecyl alchohol to Sex pheromone of sod webworm G, and the mass ratio of three kinds of components is following:
Sex pheromone of sod webworm A: anti-11-tetradecene acetate: anti-11-tetradecene aldehyde: positive tetradecyl alchohol=1: 1: 1.
Sex pheromone of sod webworm B: anti-11-tetradecene acetate: anti-11-tetradecene aldehyde: positive tetradecyl alchohol=1: 4: 5.
Sex pheromone of sod webworm C: anti-11-tetradecene acetate: anti-11-tetradecene aldehyde: positive tetradecyl alchohol=3: 3: 1.
Sex pheromone of sod webworm D: anti-11-tetradecene acetate: anti-11-tetradecene aldehyde: positive tetradecyl alchohol=7: 5: 9.
Sex pheromone of sod webworm E: anti-11-tetradecene acetate: anti-11-tetradecene aldehyde: positive tetradecyl alchohol=5: 1: 1.
Sex pheromone of sod webworm F: anti-11-tetradecene acetate: anti-11-tetradecene aldehyde: positive tetradecyl alchohol=5: 3: 15.
Sex pheromone of sod webworm G: anti-11-tetradecene acetate: anti-11-tetradecene aldehyde: positive tetradecyl alchohol=5: 3: 12.
Sex pheromone of sod webworm A to G all is mixed with the mother liquor (be about to 100mg gyplure be dissolved in 100ml acetone) of 1mg/mL, carries out the test of embodiment 2 with the mother liquor of each Sex pheromone of sod webworm.
The application of embodiment 2, Sex pheromone of sod webworm and effect assessment
One, indoor biometrics
The activity of gyplure is mainly reacted according to a series of sexual behavior of male worm and is measured, if gyplure has activity, then male worm has the swing feeler, flutters its wings up and down perk belly even stretch out reactions such as clasper again and again.This experiment has been chosen following index and has been carried out indoor biometrics: excited (male moth feeler is swung again and again, the continuous combing feeler of front foot); (along sex pheromone gas mark headwind flight) takes off; Search plain source of release (around the source of release orbit, source of release or near landing); Pre-pay tail (male moth spreads the wings, the perk belly).Calculate reactivity at last.Reactivity (%)=(reaction male worm number/testing total borer population) * 100; Reaction male worm number is meant the quantity summation of the male worm of at least one behavior in " excitement ", " taking off ", " searching plain source of release ", " pre-paying tail ".
The male worm that the back raised 1 day that select to sprout wings gives birth to survey, and male worm is divided into 7 groups, and 100 every group, detect the action effect of different Sex pheromone of sod webworm respectively, specific as follows:
Lure core: carrier is that (15mm * 10mm), each rubber stopper carries the mother liquor (or mother liquor of the mother liquor of the mother liquor of the mother liquor of the mother liquor of the mother liquor of gyplure B or gyplure C or gyplure D or gyplure E or gyplure F or gyplure G) of the gyplure A of 100 μ l embodiment, 1 preparation to rubber stopper.Lure the core preparation method: the mother liquor of the Sex pheromone of sod webworm of 100 μ l embodiment 1 preparation is dripped on rubber stopper, invade profit, for use behind the natural air drying.
Male worm put into give birth to survey the box (air outlet of 50cm * 20cm * 20cm); Fix through what aforesaid operations obtained and lure core, make the medicine position vertically downward, put into the active window place of air blast end; Dry (wind speed is suitable) with electric fan at the air blast end then, continue to observe 20min.Test is carried out 5 times and is repeated results averaged.The result sees table 1.
The male moth of table 1 beet webworm is to the behavior reaction of different gyplures
The result shows: in indoor biometrics test, more than seven kinds of Sex pheromone of sod webworm can all can bring out male moth sexual behavior reaction, wherein Sex pheromone of sod webworm G best results take place.
Two, the field is screened and is lured the moth activity test
Lure core: carrier is that (15mm * 10mm), each rubber stopper carries the mother liquor (or mother liquor of the mother liquor of the mother liquor of the mother liquor of the mother liquor of gyplure B or gyplure C or gyplure D or gyplure E or gyplure F) of the gyplure A of 100 μ l embodiment, 1 preparation to rubber stopper.Lure the core preparation method: the mother liquor of the Sex pheromone of sod webworm of 100 μ l embodiment 1 preparation is dripped on rubber stopper, invade profit, for use behind the natural air drying.
Adopt triangle cardboard trapper to lure the moth activity test.Lure core to cross triangle cardboard central authorities with thin wire, the triangle cardboard is made lures core to cover on mid point to link to each other and cover with thin wire and lure core, and preventing to expose to the sun and rain to lower lures effect.Triangle cardboard trapper apart from ground 1.5m about, the mythimna separata film is put in the bottom, lures the core should be apart from mythimna separata film 1-2cm.Inspection trapping every day result, per 15 days replacing mythimna separata films.
The core that lures with each Sex pheromone of sod webworm preparation carries out the field trapping test respectively.During each the test; 10 triangle cardboard trappers are placed on suburb, Huhehaote grassland research institute, China Agriculture academy of sciences test site; Triangle cardboard trapper makes it a little more than crop with the height of the aufwuchsplate adjusting trapper of feed, and the diameter distance between the trapper is not less than 30 meters; Add up after 15 days, calculate the beet webworm total quantity (property lures total amount) that average each triangle cardboard trapper is traped.Per average daily amt=property lures total amount/15.Maximum amount: in 15 days, traped beet webworm maximum one day, on average each triangle cardboard trapper beet webworm quantity of traping.Minimum flow: in 15 days, traped beet webworm minimum one day, on average each triangle cardboard trapper beet webworm quantity of traping.Test all is provided with three repetitions, results averaged.The result sees table 2.
Table 2 field trapping test result
The result shows: above seven kinds of Sex pheromone of sod webworm all have and lure the moth effect significantly, wherein Sex pheromone of sod webworm G best results.
Three, Sex pheromone of sod webworm and black light lamp effect are relatively
Test period: May 31 was to September 31.
Test place: suburb, Huhehaote grassland research institute, China Agriculture academy of sciences test site.
That adopts that triangle cardboard trapper carries out Sex pheromone of sod webworm G lures the moth activity test.The same step 2 of triangle cardboard trapper.During each the test, 10 triangle cardboard trappers are placed in the test site, the diameter distance between the trapper equals 30 meters, the beet webworm quantity that every day, statistics lured.
Adopt black light lamp to carry out trapping test, the diameter distance between the black light lamp equals 30 meters, and every day, statistics lured beet webworm quantity.
Test all is provided with three repetitions, results averaged.The result sees Fig. 3.Sex pheromone of sod webworm G just can lure 2 of beet webworm adults in late May, and black light lamp can only lure in mid-June; Mid-June, Sex pheromone of sod webworm G reaches and lures moth top (a day induced moth number reaches 37), black light lamp to reach the 3rd peak (7 of day induced moth numbers) that lures moth; Mid-August, Sex pheromone of sod webworm G induced moth number was 6, and black light lamp is 3; August 22 and August 24, black light lamp reaches second peak and top (being respectively 8 and 9) that lures moth; By the end of August, Sex pheromone of sod webworm G induced moth number reaches second peak (32 of day induced moth numbers), and black light lamp lures less than moth.Both have similar luring the moth peak phase basically, but Sex pheromone of sod webworm G lures moth early than black light lamp, and induced moth number exceeds 5.2 times of black light lamps.
Claims (8)
1. Sex pheromone of sod webworm; It is characterized in that: said Sex pheromone of sod webworm is made up of anti-11-tetradecene acetate, anti-11-tetradecene aldehyde and positive tetradecyl alchohol, and the mass ratio of said anti-11-tetradecene acetate, anti-11-tetradecene aldehyde and positive tetradecyl alchohol is 5: 3: 12.
2. a beet webworm lures core, comprises carrier and is carried on the described Sex pheromone of sod webworm of claim 1 on this carrier.
3. beet webworm as claimed in claim 2 lures core, it is characterized in that: said carrier is rubber stopper, silicone rubber plate or vinyl tube.
4. lure core like claim 2 or 3 described beet webworm, it is characterized in that: it is to obtain with the said carrier of solution impregnation that contains said Sex pheromone of sod webworm that said beet webworm lures core.
5. the application of the described Sex pheromone of sod webworm of claim 1 in the trapping beet webworm.
6. arbitrary described beet webworm lures the application of core in the trapping beet webworm in the claim 2 to 4.
7. the application of the described Sex pheromone of sod webworm of claim 1 in the beet webworm detecting and reporting pest information.
8. arbitrary described beet webworm lures the application of core in the beet webworm detecting and reporting pest information in the claim 2 to 4.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4059689A (en) * | 1976-02-05 | 1977-11-22 | Canadian Patents And Development Limited | Attractant for beet webworm moths |
| CN1423629A (en) * | 1999-11-18 | 2003-06-11 | R·L·佩德森 | Metathesis synthesis of pheromones or their components |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4059689A (en) * | 1976-02-05 | 1977-11-22 | Canadian Patents And Development Limited | Attractant for beet webworm moths |
| CN1423629A (en) * | 1999-11-18 | 2003-06-11 | R·L·佩德森 | Metathesis synthesis of pheromones or their components |
Non-Patent Citations (2)
| Title |
|---|
| G.G.Grant et al..Effect of Additional Components on a Sex attractant for the Oak Leaf Shredder,Croesia Semipurpurana(Lepidoptera:Tortricidae).《The Canadian Entomologist》.1981,第113卷(第5期),449-451. * |
| G.G.Grantetal..EffectofAdditionalComponentsonaSexattractantfortheOakLeafShredder Croesia Semipurpurana(Lepidoptera:Tortricidae).《The Canadian Entomologist》.1981 |
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