CN107467021A - A kind of lure composition for being used to prevent and treat the deep and remote noctuid of rotation - Google Patents

A kind of lure composition for being used to prevent and treat the deep and remote noctuid of rotation Download PDF

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Publication number
CN107467021A
CN107467021A CN201710565928.8A CN201710565928A CN107467021A CN 107467021 A CN107467021 A CN 107467021A CN 201710565928 A CN201710565928 A CN 201710565928A CN 107467021 A CN107467021 A CN 107467021A
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cis
hexadecenes
base
noctuid
deep
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CN107467021B (en
Inventor
张云慧
翁爱珍
张智
祁俊峰
王安佳
王留洋
梅向东
折冬梅
宁君
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Institute of Plant Protection of Chinese Academy of Agricultural Sciences
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Institute of Plant Protection of Chinese Academy of Agricultural Sciences
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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
    • 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
    • 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)
  • Engineering & Computer Science (AREA)
  • Environmental Sciences (AREA)
  • Zoology (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Insects & Arthropods (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
  • Toxicology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Catching Or Destruction (AREA)

Abstract

The invention discloses a kind of lure composition for being used to prevent and treat the deep and remote noctuid of rotation.Described lure composition includes the deep and remote noctuid sex pheromone component of rotation and its halo parapheromone analog, and the wherein formula of halo parapheromone analog is ROCOCnHaXb.The lure composition of the present invention can more effectively trap and kill the deep and remote noctuid male worm of rotation, reduce breeding potential, the extinction of pest population is progressively controlled, so as to reach the purpose of 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, mass trapping, Insect pest suppression, and the comprehensive regulation that noctuid is imprisoned for revolving is significant.

Description

A kind of lure composition for being used to prevent and treat the deep and remote noctuid of rotation
Technical field
The invention belongs to technical field of biological control, and in particular to a kind of lure composition for being used to prevent and treat the deep and remote noctuid of rotation.
Background technology
The deep and remote noctuid (Scotogramma trifolii Rottemberg) of rotation, belongs to Lepidoptera (Lepidoptera), night Moth section (Noctuidae), it is the agricultural pests that northern China agriculture and animal husbandry area Local primitive exponent is caused harm, harm in recent years is gradually presented The trend of liter.Larva has a characteristics such as disguised, explosive, migration harmfulness, and host crop has cotton, wheat, corn etc. totally 8 Section's kind more than 40, wherein crop kind more than 20, weeds kind more than 20, saved in Xinjiang of China, Tibet, Qinghai, Hebei etc., autonomous region has Distribution.At present, the method prevented and treated it mainly sprays chemical agent, light trap.Long-term use of Agro-chemicals control rotation is deep and remote Insect may be made to develop immunity to drugs, kill natural enemy, pollute environment and the destruction ecosystem for noctuid and prevention effect is unstable, There is no the effective ways for fundamentally controlling it still.
In nature, deep and remote noctuid female adult pest is revolved after sexal maturity, can discharge a kind of compound for being used for breeding communication i.e. Sex pheromone, male worm lure male worm to be flown to its orientation by discharging sex pheromone, complete mating so as to produce offspring.Rotation is deep and remote Noctuid sex pheromone main component is cis- 11- hexadecenes acetic acid esters, cis- 11- hexadecenols and 16 carbon acetic acid esters, is weighed Amount is than being 83:16:1.Insect pheromone class product is bionical high-tech product, and artificial synthesized property information is discharged by lure Plain compound, and be sustained to field, male moth is lured to trapper, and male moth is killed with Physical, so as to destroy its mating, also Detecting and reporting pest information, Insect pest suppression, mass trapping can be accurately applied to, reach the ideal effect of the deep and remote noctuid of comprehensive regulation rotation.Rotation deep and remote night Moth sex pheromone has attracting action to male worm, but because the difference of different component nature, caused volatilization time differ Cause its in field trap effect less stable.
The content of the invention
It is an object of the invention to provide a kind of lure composition for being used to prevent and treat the deep and remote noctuid of rotation.It is excellent by adding structure The pheromone analogue of change, it can make sex pheromone each component is more stable to be slowly released to field and can be with script sex pheromone Play a part of Synergistic.
A kind of lure composition for being used to prevent and treat the deep and remote noctuid of rotation, described lure composition include the deep and remote noctuid property information of rotation Plain component and its halo parapheromone analog, wherein the deep and remote noctuid sex pheromone component of rotation is cis- 11- hexadecenes acetic acid esters, Cis- 11- hexadecenols and 16 carbon acetic acid esters, the formula of halo parapheromone analog is ROCOCnHaXb；Described is logical In formula, R is cis- 11- hexadecenes base, 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.
The mass ratio of the cis- 11- hexadecenes acetic acid esters, cis- 11- hexadecenols and 16 carbon acetic acid esters is 83: 16:1。
Preferably, it is single to be selected from cis- 11- hexadecenes base -2- to halo parapheromone analog contained in lure composition Chloracetate, cis- 11- hexadecenes base -2- lists bromacetate, cis- 11- hexadecenes base -4- list fluorine butyrate, cis- 11- Hexadecene base -2,2- dichloroacetic acid ester, cis- 11- hexadecenes base -2,2- difluoro acetates, cis- 11- hexadecenes base - 3,3- dibromo-propionic acids ester, cis- 11- hexadecenes base -2,2,2- trifluoro-acetates, cis- 11- hexadecenes base -2,2,3,3,3- Five fluorine propionic esters, the cis- fluorine butyrates of 11- hexadecenes base -2,2,3,3,4- five, cis- 11- hexadecenes base -2,3,4,4,4- One or more in five fluorine butyrates.
The above-mentioned preparation method for being used to prevent and treat the lure composition of the deep and remote noctuid of rotation, 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 lure composition described in claim 1 and pheromone analogue is dilute with n-hexane The solution that concentration is 0.01~1 μ g/ μ L is interpreted into, 50~200 μ L is drawn and adds to the recess of rubber stopper；
(3) natural evaporation is complete to n-hexane volatilization, is placed in -20Case is standby.
Above-mentioned lure composition is applied in terms of the deep and remote noctuid biological control of rotation.
Beneficial effects of the present invention：The lure composition of the present invention can revolve deep and remote noctuid male worm so as to physics with mass trapping Kill, applied to field mass control insect, there is the characteristics of dosage is few, environmentally friendly and laborsaving.The lure composition of the present invention By mass trapping male worm, breeding potential is reduced, progressively controls the extinction of pest population, can so as to reach the purpose of pest control Accurately it is applied to detecting and reporting pest information, Insect pest suppression, mass trapping, reaches the ideal effect of the deep and remote noctuid of comprehensive regulation rotation.
Brief description of the drawings
Fig. 1 is cis- 11- hexadecenes base -2- monochloro acetic acid ester chemical structural formula schematic diagrames.
Fig. 2 is cis- 11- hexadecenes base -2- list bromacetate chemical structural formula schematic diagrames.
Fig. 3 is cis- 11- hexadecenes base -4- lists fluorine butyrate chemical structural formula schematic diagram.
Fig. 4 is cis- 11- hexadecenes base -2,2- dichloroacetic acid ester chemical structural formula schematic diagrames.
Fig. 5 is cis- 11- hexadecenes base -2,2- difluoro acetate chemical structural formula schematic diagrames.
Fig. 6 is cis- 11- hexadecenes base -3,3- dibromo-propionic acid ester chemical structural formula schematic diagrames.
Fig. 7 is cis- 11- hexadecenes base -2,2,2- trifluoro-acetate chemical structural formula schematic diagrames.
Fig. 8 is the cis- fluorine propionic ester chemical structural formula schematic diagrames of 11- hexadecenes base -2,2,3,3,3- five.
Fig. 9 is the cis- fluorine butyrate chemical structural formula schematic diagrames of 11- hexadecenes base -2,2,3,3,4- five
Figure 10 is the cis- fluorine butyrate chemical structural formula schematic diagrames of 11- hexadecenes base -2,3,4,4,4- five
Figure 11 is the synthetic route schematic diagram of cis- 11- hexadecenes base -2- monochloro acetic acid esters.
Embodiment
Below in conjunction with the accompanying drawings, the embodiment of 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 cis- 11- hexadecenes base -2- monochloro acetic acid esters of embodiment 1
Compound in the present invention can be synthesized by route as described below, and cis- 11- hexadecenes base -2- is single The synthetic route of chloracetate is shown in Figure 11.
The cis- 11- hexadecenols of 2.00g (8.32mmol) are dissolved in 30mL anhydrous methylene chloride, addition 7.30 × 10-2G DMAP, ice bath, reaction temperature is maintained 0 DEG C or so, and the dichloromethane of chloroacetic anhydride is gradually added dropwise Alkane solution, it is added dropwise after rear ice bath continues for some time, room temperature reaction overnight, saturated aqueous common salt and nothing is used after reacting completely Water magnesium sulfate extraction removes impurity and excess anhydride, and last vacuum rotary steam removes solvent, the isolated faint yellow oily of chromatographic column Thing 2.13g (6.74mmol), yield 80.9%.
The preparation of the cis- 11- hexadecenes base -2,2- difluoro acetates of embodiment 2
The preparation method of cis- 11- hexadecenes base -2,2- difluoro acetate is similar to embodiment 1, only need to be by embodiment 1 In chloroacetic anhydride change difluoroacetic acid acid anhydride into, and synthesized according to the step in embodiment 1 and can obtain pale yellow oil 2.17g (6.81mmol), yield 81.9%.
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 cis- 11- hexadecenes acetic acid esters by the deep and remote noctuid sex pheromone composition of rotation, cis- 11- hexadecenols and ten Six carbon acetic acid esters, with 83:16:1 mass ratio mixing, the solution that concentration is 1 μ g/ μ L is diluted to n-hexane.
(3) draw the deep and remote noctuid sex pheromone solution of 100 μ L (1 μ g/ μ L) above-mentioned rotation and add to Rubber end bottom, revolve deep and remote noctuid Sex pheromone solution can be penetrated into inside rubber with solvent (n-hexane).After solvent (n-hexane) volatilization, obtain 100 μ g's The deep and remote noctuid sex pheromone of rotation.
(4) by cis- 11- hexadecenes base -2- monochloro acetic acids ester, cis- 11- hexadecenes base -2- lists bromacetate, cis- 11- hexadecene base -4- list fluorine butyrate, cis- 11- hexadecenes base -2,2- dichloroacetic acid ester, cis- 11- hexadecenes base - 2,2- difluoro acetates, cis- 11- hexadecenes base -3,3- dibromo-propionic acids ester, cis- 11- hexadecenes base -2,2,2- trifluoro second Acid esters, the cis- fluorine propionic esters of 11- hexadecenes base -2,2,3,3,3- five, the cis- fluorine fourths of 11- hexadecenes base -2,2,3,3,4- five Acid esters, cis- 11- hexadecenes base -2,3,4,4,4- five fluorine butyrate one or more are diluted with n-hexane respectively, dense Spend for 0.1 μ g/ μ L.Shown in the structural formula of above-mentioned ten compounds such as Figure of description (Fig. 1-10).
(5) noctuid property letter is imprisoned in the step of drawing 100 μ L (0.1 μ g/ μ L) (4) solution, the rotation that oneself prepares with step (3) Cease in plain lure so as to which mixing lure be made.Therefore, revolve in deep and remote noctuid lure, revolve deep and remote noctuid sex pheromone and halo category information The mass ratio of plain analog is 100:10.It is standby that lure is placed in -20 DEG C of refrigerators before experiment.
The more serious plot of the deep and remote noctuid hazard ratio of selection rotation, trapper is the universal trapper of moth class, and trapper is placed 20cm or so above crop, the average headway between trapper is in more than 10m.Above-mentioned each mixing lure processing is respectively provided with 5 Individual repetition.Noctuid sex pheromone (cis- 11- hexadecenes acetic acid esters is imprisoned in rotation as control：Cis- 11- hexadecenols：16 Carbon acetic acid esters=83:16:1) lure and space management are respectively 5 repetitions.
Recording method：
The trapping quantity of every two days record once each trappers, polypide is pulled out random between rear different treatment group Position is exchanged, to eliminate the test error that position effect is brought, Continuous Observation 30 days.Result of the test is as shown in table 1.(in table 1 Same column difference lowercase letter significant difference in the levels of P ＜ 0.05 in Duncan method tests of significance)
The lure composition of table 1 imprisons the trapping experiments result of noctuid to revolving
As seen from the results in Table 1, lure composition of the invention has preferable trap effect to revolving deep and remote noctuid.By conspicuousness Compare and understand, the trapping amount that the analog of parapheromone containing halo is handled difference compared with revolving the trapping amount of deep and remote noctuid sex pheromone Significantly (P ＜ 0.05), illustrate that halo parapheromone analog there is synergy to make the trapping activity for revolving deep and remote noctuid sex pheromone With wherein the trapping amount of cis- 11- hexadecenes base -4- list fluorine butyrates is most aobvious with revolving deep and remote noctuid sex pheromone contrast difference Write, illustrate its synergistic activity highest.
The lure composition of the deep and remote noctuid of rotation provided by the invention is prepared simply, and raw material is easy to get；Traped than script sex pheromone Activity is higher, and stability is good, and lasting period length, prevention effect can maintain more than 30 days；Selectivity is strong, and rotation will not be made to imprison noctuid production Raw 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, interference Mating, mass trapping, it is significant to revolve deep and remote noctuid for the comprehensive regulation.
Disclosed above is only the specific embodiment of the present invention, and still, the present invention is not limited to this, any this area Technical staff can think change should all fall into protection scope of the present invention.

Claims (5)

1. a kind of lure composition for being used to prevent and treat the deep and remote noctuid of rotation, it is characterised in that described lure composition includes rotation deep and remote night Moth sex pheromone component and its halo parapheromone analog, wherein the deep and remote noctuid sex pheromone component of rotation is cis- 11- hexadecenes Acetic acid esters, cis- 11- hexadecenols and 16 carbon acetic acid esters, the formula of halo parapheromone analog is ROCOCnHaXb；Institute In the formula stated, R is cis- 11- hexadecenes base, 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.
2. it is used for the lure composition for preventing and treating the deep and remote noctuid of rotation according to claim 1, it is characterised in that the cis- 11- 16 The mass ratio of carbene acetic acid esters, cis- 11- hexadecenols and 16 carbon acetic acid esters is 83:16:1.
3. it is used for the lure composition for preventing and treating the deep and remote noctuid of rotation according to claim 1, it is characterised in that institute in lure composition It is single that the halo parapheromone analog contained is selected from cis- 11- hexadecenes base -2- monochloro acetic acids ester, cis- 11- hexadecenes base -2- Bromacetate, cis- 11- hexadecenes base -4- list fluorine butyrate, cis- 11- hexadecenes base -2,2- dichloroacetic acid ester, cis- 11- Hexadecene base -2,2- difluoro acetates, cis- 11- hexadecenes base -3,3- dibromo-propionic acids ester, cis- 11- hexadecenes base -2, 2,2- trifluoro-acetates, the cis- fluorine propionic esters of 11- hexadecenes base -2,2,3,3,3- five, cis- 11- hexadecenes base -2,2,3, One or more in the fluorine butyrates of 3,4- five, the cis- fluorine butyrates of 11- hexadecenes base -2,3,4,4,4- five.
4. it is used for the preparation method for preventing and treating the lure composition of the deep and remote noctuid of rotation described in claim 1, it is characterised in that according to as follows Step is carried out：
（1）Choose cylindrical indent rubber stopper, high 0.5 ~ 2 cm, the cm of bottom diameter 0.5 ~ 2；
（2）Sex pheromone component in lure composition described in claim 1 and pheromone analogue are diluted to n-hexane Concentration is 0.01 ~ 1 μ g/ μ L solution, draws 50 ~ 200 μ L and adds to the recess of rubber stopper；
（3）Natural evaporation is complete to n-hexane volatilization, and it is standby to be placed in -20 DEG C of refrigerators.
5. the lure composition described in claim 1 is applied in terms of the deep and remote noctuid biological control of rotation.
CN201710565928.8A 2017-07-12 2017-07-12 Attractant composition for preventing and treating helicoverpa clarkii Active CN107467021B (en)

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CN108812664A (en) * 2018-08-25 2018-11-16 中国农业科学院植物保护研究所 A kind of footpath between fields noctuid lure composition and application thereof
CN108812666A (en) * 2018-08-25 2018-11-16 中国农业科学院植物保护研究所 A kind of footpath between fields noctuid traps composition and its application
CN108925559A (en) * 2018-08-25 2018-12-04 中国农业科学院植物保护研究所 A kind of lettuce winter noctuid lure composition and its preparation and application
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
CN110934140A (en) * 2019-12-13 2020-03-31 中国农业科学院植物保护研究所 Sex pheromone analogue disorientation technology for preventing and treating Spodoptera litura
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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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108812664A (en) * 2018-08-25 2018-11-16 中国农业科学院植物保护研究所 A kind of footpath between fields noctuid lure composition and application thereof
CN108812666A (en) * 2018-08-25 2018-11-16 中国农业科学院植物保护研究所 A kind of footpath between fields noctuid traps composition and its application
CN108925559A (en) * 2018-08-25 2018-12-04 中国农业科学院植物保护研究所 A kind of lettuce winter noctuid lure composition and its preparation and application
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
CN110934140A (en) * 2019-12-13 2020-03-31 中国农业科学院植物保护研究所 Sex pheromone analogue disorientation technology for preventing and treating Spodoptera litura
CN110934140B (en) * 2019-12-13 2021-04-30 中国农业科学院植物保护研究所 Sex pheromone analogue disorientation technology for preventing and treating Spodoptera litura

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