CN107318832A - A kind of sex attractant halogenated analogues for being used to prevent and treat black cutworm - Google Patents
A kind of sex attractant halogenated analogues for being used to prevent and treat black cutworm Download PDFInfo
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- CN107318832A CN107318832A CN201710669409.6A CN201710669409A CN107318832A CN 107318832 A CN107318832 A CN 107318832A CN 201710669409 A CN201710669409 A CN 201710669409A CN 107318832 A CN107318832 A CN 107318832A
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- black cutworm
- cis
- halo
- analog
- sex attractant
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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
- 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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- 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
- A01M1/02—Stationary means for catching or killing insects with devices or substances, e.g. food, pheronones attracting the insects
- A01M1/04—Attracting insects by using illumination or colours
-
- 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
-
- 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
-
- 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
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- 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)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Insects & Arthropods (AREA)
- Agronomy & Crop Science (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention discloses a kind of sex attractant halogenated analogues for being used to prevent and treat black cutworm.Sex attractant halogenated analogues include black cutworm sex pheromone component and its halo parapheromone analog, halo parapheromone analog is selected from along the single ethyl fluoroacetate of 7 dodecenyl succinic 2, along 9 tetradecene bases 2, one or more in 2 dichloroacetic acid esters, the suitable difluoro acetate of 7 dodecenyl succinic 2,2.The lure composition of the present invention can more effectively trap and kill black cutworm male worm, reduce breeding potential, the extinction of pest population progressively be controlled, so as to reach the purpose of pest control.Not only consumption is few and environmentally friendly by the present invention, can also accurately be applied to detecting and reporting pest information, mass trapping, Insect pest suppression, the comprehensive regulation for black cutworm is significant.
Description
Technical field
The invention belongs to technical field of biological control, and in particular to a kind of sex attractant halo for being used to prevent and treat black cutworm
Analog.
Background technology
Black cutworm Agrotisypsilon (Rottemberg), belongs to Lepidoptera, Noctuidae, and alias is " grub ", "
Silkworm " etc..The seedling of the crops such as main harm vegetables, corn, sorghum, cotton, the subaerial stem of cut-out seedling, makes whole strain dead
Die, cause disconnected ridge of being short of seedling, serious even ruins kind.At present, chemical agent is mainly sprayed to the method that black cutworm prevents and treats, lured
Kill adult.Chemical agent has a preventing and treating fast, easily advantage, but its resistance to the action of a drug is the drawbacks of also have very big.On trapping adult, profit
The characteristics of having light with black cutworm, in adult full incidence period, adult is trapped and killed using black light lamp or high-altitude lamp, sugar-vinegar liquid.But,
Black light lamp or high-altitude lamp, sugar-vinegar liquid are killed due to reasons such as weather, using with certain limitation.Black cutworm sex pheromone
Using having become the classical example of usability pheromone control insect in world wide.According to female insects release property information
Element has very strong attracting ability principle to male worm of the same race, continues to optimize pheromones structure and adds micro efficient pheromones class
Like thing, detecting and reporting pest information, Insect pest suppression, mass trapping can be accurately applied to, the ideal effect of comprehensive regulation black cutworm is reached.
The content of the invention
It is an object of the invention to provide a kind of sex attractant halogenated analogues for being used to prevent and treat black cutworm.Pass through addition
The halo pheromone analogue of structure optimization, can make sex pheromone each component more stablize it is slow be released to field and can with originally
Sex pheromone plays a part of Synergistic.
A kind of sex attractant halogenated analogues of the black cutworm provided based on above-mentioned purpose, the present invention include black cutworm
Sex pheromone component and its halo parapheromone analog.Wherein black cutworm sex pheromone component is the cis- carbon acetic acid of 7- 12
Ester, the carbon acetic acid esters of cis- 9- 14, the carbon acetic acid esters of cis- 11- 16, halo parapheromone analog are selected from cis- 7- dodecylenes
Base -2- lists ethyl fluoroacetate, cis- 9- tetradecenes base -2,2- dichloroacetic acid ester, cis- 7- dodecenyl succinics -2,2- difluoro acetates
In one or more.
The sex attractant halogenated analogues for being used to prevent and treat black cutworm, it is characterised in that alternatively, the small ground is old
The mass ratio of brave sex pheromone and halo parapheromone analog is 1:0.1~2.5.
More preferably, the mass ratio of the black cutworm sex pheromone and halo parapheromone analog is 1:0.1~1.
Most preferably, the mass ratio of the black cutworm sex pheromone and halo parapheromone analog is 1:0.5~0.75.
The cis- carbon acetic acid esters of 7- 12 of described black cutworm sex pheromone component, the carbon acetic acid esters of cis- 9- 14, cis- 11-
16 carbon acetic acid esters mass ratioes are 3:1.3:0.8.
Described halo parapheromone analog is selected from the single ethyl fluoroacetates of cis- 7- dodecenyl succinics -2-, the carbon of cis- 9- 14
One or more in alkenyl -2,2- dichloroacetic acid ester, cis- 7- dodecenyl succinics -2,2- difluoro acetates.
Optionally, the single ethyl fluoroacetates of cis- 7- dodecenyl succinics -2-：Cis- 9- tetradecenes base -2,2- dichloroacetic acid esters：
Cis- 7- dodecenyl succinics -2,2- difluoro acetate=0.1~1:0.5~1.5:0.45~1.5.
Preferably, the single ethyl fluoroacetates of cis- 7- dodecenyl succinics -2-：Cis- 9- tetradecenes base -2,2- dichloroacetic acid esters：
Cis- 7- dodecenyl succinics -2,2- difluoro acetate=0.2~0.75:0.5~1:0.65~1.
Optimal, the single ethyl fluoroacetates of cis- 7- dodecenyl succinics -2-：Cis- 9- tetradecenes base -2,2- dichloroacetic acid esters：
Cis- 7- dodecenyl succinics -2,2- difluoro acetate=0.5:0.75:0.75.
The above-mentioned preparation method for being used to prevent and treat the sex attractant halogenated analogues of black cutworm, is carried 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) it is sex pheromone component in sex attractant halogenated analogues described in claim 1 is similar with halo parapheromone
Thing is diluted to the solution that concentration is 0.01~1 μ g/ μ L with n-hexane, draws 50~150 μ L and adds to the recess of rubber stopper；
(3) stand to solution completely into rubber stopper；
(4) 100 μ L n-hexanes are added, treats that n-hexane natural evaporation volatilization is complete, is placed in -20 DEG C of refrigerators standby.
Above-mentioned lure composition is applied in terms of black cutworm biological control.
Draw present invention also offers a kind of method prevented and treated or monitor black cutworm, including by the black cutworm property of the present invention
Lure halogenated analogues lure is positioned over the habitat of black cutworm.The black cutworm sex attractant halo class for being used to prevent and treat
Like thing consumption be 5~15 micro- grams/m.The consumption of the sex attractant halogenated analogues of the black cutworm for being used to monitor
For 0.5~2 micro- gram/m.
Beneficial effects of the present invention：The present invention sex attractant halogenated analogues can with mass trapping black cutworm male worm from
Few with consumption and physics is killed, the characteristics of environmentally friendly, and the sex attractant halogenated analogues of the black cutworm are prepared simply,
With very strong trapping capability, stability is good；Meanwhile, the sex attractant halogenated analogues selectivity of the black cutworm is strong, does not produce
Raw resistance, is not injured to natural enemy, nontoxic to people and animals, environment-friendly.The lure composition for the black cutworm that the present invention is provided can
Black cutworm detecting and reporting pest information, mass trapping, Insect pest suppression are accurately applied to, there is important meaning for comprehensive regulation black cutworm
Justice.
Brief description of the drawings
Fig. 1 is the single ethyl fluoroacetate chemical structural formula schematic diagrames of cis- 7- dodecenyl succinics -2-.
Fig. 2 is cis- 9- tetradecenes base -2,2- dichloroacetic acid ester chemical structural formula schematic diagrames.
Fig. 3 is cis- 7- dodecenyl succinics -2,2- difluoro acetate chemical structural formula schematic diagrames.
Fig. 4 is the synthetic route schematic diagram of the single ethyl fluoroacetates of cis- 7- dodecenyl succinics -2-.
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 the single ethyl fluoroacetates of the cis- 7- dodecenyl succinics -2- of embodiment 1
Compound in the present invention can be synthesized by route as described below, the single fluorine of cis- 7- dodecenyl succinics -2-
The synthetic route of acetic acid esters is shown in Fig. 4.
The cis- 7- lanolin alcohols of 0.5g (0.002mol) are dissolved in 20mL anhydrous methylene chloride, 0.04g 4- is added
Dimethylamino naphthyridine, then adds 0.31g TEA, and ice bath makes reaction temperature maintain the 0 left DEG C right side, and fluoroacetic acid is gradually added dropwise
After ice bath is continued for some time after the dichloromethane solution of acid anhydride, completion of dropping, point plate determines whether that reaction is complete.After reaction completely
Impurity and excess anhydride are removed with saturated aqueous common salt and anhydrous sodium sulfate extraction, last vacuum rotary steam removes solvent, chromatographic column point
From pale yellow oil 0.61g (1.87mmol) is obtained, yield is 82.3%.
The preparation of the cis- 7- dodecenyl succinics -2,2- difluoro acetates of embodiment 2
The preparation method of cis- 7- dodecenyl succinics -2,2- difluoro acetate is similar to embodiment 1, only need to be by embodiment 1
Chloroacetic anhydride change difluoroacetic acid acid anhydride into, and synthesized according to the step in embodiment 1 and can obtain pale yellow oil
0.57g (1.82mmol), yield is 78.9%.
The field biological activity determination experiment of embodiment 3
It is prepared by lure：
(1) lure carrier is using the green indent rubber stopper of cylinder, high 14mm, openend internal diameter 8mm, openend wall thickness
1mm, opening depth 5mm.
(2) it is the cis- carbon acetic acid esters (Z7-12: Ac) of 7- 12, the carbon second of cis- 9- 14 by black cutworm sex pheromone composition
Acid esters (Z9-14: Ac), the carbon acetic acid esters (Z11-16: Ac) of cis- 11- 16, with 3：1.3：0.8 mass ratio mixing, uses n-hexane
It is diluted to the solution that concentration is 1 μ g/ μ L.
(3) draw 100 μ L (1 μ g/ μ L) above-mentioned black cutworm sex pheromone solution and add to Rubber end bottom, black cutworm property
Pheromones solution can be penetrated into inside rubber with solvent (n-hexane).After solvent (n-hexane) volatilization after, obtain 100 μ g smallly
Tiger sex pheromone.
(4) by single ethyl fluoroacetates of cis- 7- dodecenyl succinics -2-, cis- 9- tetradecenes base -2,2- dichloroacetic acid ester, cis-
7- dodecenyl succinics -2,2- difluoro acetate one or more are diluted with n-hexane respectively, and concentration is 0.1 μ g/ μ L.
Lure is placed in -20 DEG C of refrigerators before experiment standby.
15 specific formulas are provided in the feasibility of the present embodiment, table 1 in order to further illustrate：
Table 1
The plot for selecting black cutworm hazard ratio more serious, trapper is between the universal trapper of moth class, trapper
Average headway is in 8-10m.Above-mentioned each mixing lure processing is respectively provided with 5 repetitions.Randomly place 5 lamp light trapping devices, 5 simultaneously
Individual blank barrel shape trapper and the barrel shape trapper of 5 female black cutworms living not yet mated for 3 days that sprout wings containing three.
Recording method：
The trapping quantity for recording once each trapper in every three 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, Continuous Observation 30 days.Result of the test is as shown in table 2.
Table 2
As seen from the results in Table 2, sex pheromone of the invention has preferably with halo parapheromone analog to black cutworm
Trap effect, containing the single ethyl fluoroacetates of cis- 7- dodecenyl succinics -2-, cis- 9- tetradecenes base -2,2- dichloroacetic acid ester, cis- 7-
The trapping amount of dodecenyl succinic -2,2- difluoro acetates processing significant difference (P compared with the trapping amount of black cutworm sex pheromone
＜ 0.05), illustrate the single ethyl fluoroacetates of cis- 7- dodecenyl succinics -2-, cis- 9- tetradecenes base -2,2- dichloroacetic acid ester, cis- 7-
Dodecenyl succinic -2,2- difluoro acetate has synergistic effect to the trapping activity of black cutworm sex pheromone, wherein being formulated 1-
(containing the single μ L of ethyl fluoroacetate 125 of cis- 7- dodecenyl succinics -2-, the cis- μ of 9- tetradecenes base -2,2- dichloroacetic acid ester 187.5 in 13
L, the cis- μ L of 7- dodecenyl succinics -2,2- difluoro acetates 187.5) trapping amount and black cutworm sex pheromone contrast difference most
Significantly, its synergistic activity highest is illustrated.
The black cutworm sex attractant halogenated analogues that the present invention is provided are prepared simply, and raw material is easy to get；Than script information
Element trapping activity is higher, and stability is good, and the lasting period is long, and prevention effect can be maintained more than 30 days；Selectivity is strong, and small ground will not be made old
Tiger produces resistance；It is environment-friendly to person poultry harmless；Strong stress resistance, it is easy to use.The present invention can accurately be applied to detecting and reporting pest information,
Insect pest suppression, mass trapping, it is significant for comprehensive regulation black cutworm.
The present invention is using the single ethyl fluoroacetates of cis- 7- dodecenyl succinics -2-, cis- 9- tetradecenes base -2,2- dichloroacetic acid
The analogue of ester, cis- 7- dodecenyl succinics -2,2- difluoro acetates：Cis- 7- dodecenyl succinics -2,2- difluoro acid esters,
Cis- 9- tetradecenes base -2- monochloro acetic acids ester, trans- 7- dodecenyl succinics -2,2- difluoro acetate repeat above-mentioned experiment, find
There is no synergistic activity, it was demonstrated that above-mentioned synergist has selectivity, can not be replaced using other structures analog.
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 (6)
1. a kind of sex attractant halogenated analogues for being used to prevent and treat black cutworm, it is characterised in that including black cutworm property information
Element and halo parapheromone analog, described halo parapheromone analog are selected from the single fluoroacetic acids of cis- 7- dodecenyl succinics -2-
Ester, cis- 9- tetradecenes base -2,2- dichloroacetic acid ester, one kind in cis- 7- dodecenyl succinics -2,2- difluoro acetates or
More than one.
2. it is used for the sex attractant halogenated analogues for preventing and treating black cutworm according to claim 1, it is characterised in that described small
The mass ratio of cutworm sex pheromone and halo parapheromone analog is 1:0.5~0.75.
3. it is used for the sex attractant halogenated analogues for preventing and treating black cutworm according to claim 1, it is characterised in that described small
Cutworm sex pheromone is made up of following components according to respective parts by weight：The cis- carbon acetic acid esters 59% of 7- 12, the cis- carbon second of 9- 14
Acid esters 25%, the cis- carbon acetic acid esters 16% of 11- 16；The black cutworm halo parapheromone analog is by following components according to each
From parts by weight composition：The single ethyl fluoroacetates 14% ~ 80% of cis- 7- dodecenyl succinics -2-, the cis- chloroethenes of 9- tetradecenes base -2,2- two
Acid esters 15% ~ 70%, cis- 7- dodecenyl succinics -2,2- difluoro acetates 5% ~ 70%.
4. a kind of be used to trap the lure of black cutworm, it is characterised in that prevent and treat small containing being used for described in claim 1
The sex attractant halogenated analogues of tiger.
5. the method that the lure described in claim 4 traps black cutworm, similar by the sex attractant halo of the black cutworm
Thing lure is placed in Doliform trapper, and 100 ~ 2000 μ g are inserted in each anti-mouth Rubber end lure to be used to prevent and treat black cutworm
Sex attractant halogenated analogues, be positioned over the spot of black cutworm.
6. a kind of method for preventing and treating or monitoring black cutworm, it is characterised in that the property of the black cutworm for being used to prevent and treat
The consumption of attractant halogenated analogues is 5 ~ 15 micro- grams/m；The sex attractant halogen of the black cutworm for being used to monitor
Consumption for analog is 0.5 ~ 2 micro- gram/m.
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| CN201710669409.6A CN107318832A (en) | 2017-08-08 | 2017-08-08 | A kind of sex attractant halogenated analogues for being used to prevent and treat black cutworm |
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| CN201710669409.6A CN107318832A (en) | 2017-08-08 | 2017-08-08 | A kind of sex attractant halogenated analogues for being used to prevent and treat black cutworm |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109221119A (en) * | 2018-11-09 | 2019-01-18 | 中国农业科学院植物保护研究所 | It is a kind of for preventing and treating the sex pheromone composition and application of three-spotted plusia |
| CN112021310A (en) * | 2019-06-03 | 2020-12-04 | 中国农业科学院植物保护研究所 | Sex pheromone composition for preventing and treating panopneumonia armyworm |
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| CN1250597A (en) * | 1998-10-14 | 2000-04-19 | 中国科学院动物研究所 | Insect exohormone attractant using compound rubber as its carrier and application thereof |
| CN106070293A (en) * | 2016-06-13 | 2016-11-09 | 漳州市英格尔农业科技有限公司 | Black cutworm sex pheromone and preparation method thereof and lure |
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2017
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1250597A (en) * | 1998-10-14 | 2000-04-19 | 中国科学院动物研究所 | Insect exohormone attractant using compound rubber as its carrier and application thereof |
| CN106070293A (en) * | 2016-06-13 | 2016-11-09 | 漳州市英格尔农业科技有限公司 | Black cutworm sex pheromone and preparation method thereof and lure |
Non-Patent Citations (5)
| Title |
|---|
| A.S. HILL AND W. L. ROELOFS: "SEX PHEROMONE COMPONENTS OF THE OBLIQUEBANDED LEAFROLLER MOTH,Choristoneura rosaceana", 《JOURNAL OF CHEMICAL ECOLOGY》 * |
| J. F. PICIMBON ET AL.: "SEX PHEROMONE OF THE FRENCH BLACK CUTWORM MOTH, Agrotis ipsilon (LEPIDOPTERA: NOCTUIDAE): IDENTIFICATION AND REGULATION OF A MULTICOMPONENT BLEND", 《JOURNAL OF CHEMICAL ECOLOGY》 * |
| SADAO WAKAMURA ET AL.: "SEX PHEROMONE of the black cutworm moth，Agrotis ipsilon hufnagel(Lepidotera:Noctuidae):Attractant Synergist and Improved Formulation", 《APPL.ENT.ZOOL》 * |
| 向玉勇 等: "交配和温度对小地老虎雌蛾性信息素产生的影响", 《四川动物》 * |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109221119A (en) * | 2018-11-09 | 2019-01-18 | 中国农业科学院植物保护研究所 | It is a kind of for preventing and treating the sex pheromone composition and application of three-spotted plusia |
| CN112021310A (en) * | 2019-06-03 | 2020-12-04 | 中国农业科学院植物保护研究所 | Sex pheromone composition for preventing and treating panopneumonia armyworm |
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Application publication date: 20171107 |