CN106749134B - Application of the benzofuran compounds in excitation crop Induced insect resistance - Google Patents

Application of the benzofuran compounds in excitation crop Induced insect resistance Download PDF

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CN106749134B
CN106749134B CN201611147148.3A CN201611147148A CN106749134B CN 106749134 B CN106749134 B CN 106749134B CN 201611147148 A CN201611147148 A CN 201611147148A CN 106749134 B CN106749134 B CN 106749134B
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crop
benzofuran
application
rice
plant
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CN106749134A (en
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娄永根
陈夏
吴军
何兴瑞
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Zhejiang University ZJU
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Zhejiang University ZJU
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D307/00Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/12Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings condensed with a carbocyclic ring
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D493/00Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/04Ortho-condensed systems

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

The present invention relates to application of the benzofuran compounds in control crop pest.The application is to be applied to benzofuran compounds to make object, and excitation crop is pest-resistant, survival rate of the Hemipteran pest on crop is substantially reduced, to mitigate harm of the pest to crop.

Description

Application of the benzofuran compounds in excitation crop Induced insect resistance
Technical field
The present invention relates to plant Induced insect resistance fields, exactly, are related to benzofuran compounds in excitation crop Application in Induced insect resistance.
Background technique
With the increase of population in the world and the reduction of cultivated area, requirement of the people to crop yield is higher and higher.Insect pest Caused by crop yield loss account for about the 10-30% of total output, then No kernels or seeds are gathered, as in a year of scarcity for Serious year part, therefore how to reduce insect pest to increase Add crop yield, is the pressing issues that people face.For example, damage caused by the pests such as brown paddy plant hopper is huge on rice 's.Brown paddy plant hopper belongs to Semiptera, and oviposition has fulminant and destructiveness, in recent years, even more every year in the stem position of rice It breaks out greatly, serious harm is caused to China's rice grain-production.
As one of control harmful organism most efficient method, always high-quality, safe, the highly efficient and productive agricultural of pesticide is raw It is indispensable to produce institute.But for a long time due in pest management, exceedingly having used toxic or even high-toxic pesticide, and And use single variety, therefore result in Pest organism drug resistance enhancing, second rice crop season it is serious.Bring vicious circle has been therefrom Crop securify production, ecological environment, human health, export trade etc. are caused and seriously threatened.Therefore, development is efficient, pacifies Entirely, green pesticide have become control the Harmful Biohazard there is an urgent need to.
During the long-term evolution with plant-feed insect, plant forms two kinds of defense mechanisms of composing type and induction type. Composing type defence refers to plant before being caused harm by plant-feed insect with regard to already present pest-resistant characteristic, such as plant epidermal hair;It lures Conductivity type defence refer to plant when being attacked by plant-feed insect, generated some pest-resistant characteristics.By to plant inducer impedance Property molecule mechanism studies have shown that the induction of resistance of plant originates in plant to from plant-feed insect exciton (elicitor) identification, then by changing a variety of defence such as jasmonic, salicylic acid, ethylene, MAPK, GA, ABA and growth phase The signal transduction pathway activity of pass, causes transcript profile, metabolism group etc. to reconstruct, finally results in the change of plant resistance to insect.? During this, the signaling molecule of some low molecular weights in plant, such as jasmonic, salicylic acid, ethylene play it is extremely important Effect.By synthesis with using these natural small molecules and the like, played in the prevention and treatment of plant disease important Effect.But it also studies seldom at present in plant insect prevention and treatment, is not applied in production more.Studying at present more is Jasmonic, methyl jasmonate and the like Coronalon.These research discovery exogenous applications JA, MeJA or Coronalon energy Enough induction plants generate the substances such as protease inhibitors, nicotine, polyphenol oxidase, have an adverse effect to pest, and can lure It leads Plant emission volatile matter and attracts natural enemy.
Benzofuran compounds are widely used in field of medicine and chemical technology, are a kind of important chemical intermediates, are usually used in Synthesize the intermediate of amiodarone and cumarone resin.In recent years, have been reported that discovery benzofuran compounds have antihistamine, A variety of biopharmacology activity such as antitumor and anti-arrhythmia, lose in prevention and treatment Alzheimer disease, osteoporosis, the rhythm of the heart Often, Parkinson's disease and tumour etc. play booster action.
Summary of the invention
In view of the above-mentioned deficiencies in the prior art, it is an object of the present invention to provide benzofuran compounds in excitation crop induction Application in insect resistace.
The purpose of the present invention is achieved through the following technical solutions: benzofuran compounds are in excitation crop induction Application in insect resistace, the application are as follows: benzofuran compounds are used to trigger crop to the resistance of Hemipteran pest.
Further, the structural formula of the benzofuran compounds are as follows:
Further, described to make rice, barley, wheat, the crop in cruciferae, Solanaceae that object be gramineous crop Crop or tealeaves.
Further, the Induced insect resistance is excited before by the pest damage.
Further, the application specifically: benzofuran compounds are added in crop nutrient solution or water system, Crop is cultivated, the benzofuran compounds concentration is 20mg/L.
The invention has the advantages that seven kinds of benzofuran compounds activation crop provided by the invention is to Semiptera evil Pest survival rate can be reduced to 50% by the insect resistace of worm.According to planted in different ecological areas pest, a situation arises, and the present invention can Using the induction insect resistant agent as crop, crop is made to generate insect resistace, to achieve the purpose that safely, effectively to control pest.
Detailed description of the invention
Figure 1A-G is that benzofuran compounds 11r, 11d, 11h, 11y, 11k, 12g, 14u of 20mg/L concentration exist respectively To the impact effect figure of brown paddy plant hopper nymph survival rate after rice root absorption processing;
Fig. 2A-G be respectively in brown paddy plant hopper man-made feeds add concentration be 20mg/L benzofuran compounds 11r, The impact effect figure of 11d, 11h, 11y, 11k, 12g, 14u to brown paddy plant hopper nymph survival rate;
Fig. 3 A-G be respectively spray concentration be benzofuran compounds 11r, 11d of 20mg/L concentration, 11h, 11y, The impact effect figure of 11k, 12g, 14u to brown paddy plant hopper nymph survival rate.
Specific embodiment
The present invention relates to a kind of methods for exciting crop Induced insect resistance comprising by the benzofurans of effective concentration It closes object to be applied to make object, Induced insect resistance is excited in vivo after being made object absorption, to improve crop to Hemipteran pest Resistance.
Benzofuran compounds of the present invention have the following structure:
Biologically active benzofuran compounds aqueous solution of the present invention can be applied to the root of plant. Nutrition needed for plant growth can also being added in biologically active benzofuran compounds to the processing of plant Perhaps water system can use liquid in any time in daytime or evening, can generate good insect resistace, be preferentially used for Plant growth active period.It should be noted that, it should 1 to 2 hours use before raining or snowing, in order to avoid influence drug effect.It applies With medicament for a period of time after, if discovery Induced insect resistance weaken (such as number of pest rise), said preparation can be applied again to increase Strong resistance.
The Induced insect resistance of activated plant needs the bioactive ingredients of " effective quantity ", activity one in plant As be 20mg/L;In general, apply per acre 1~50g active constituent can activated plant Induced insect resistance.Optimization Afterwards, the active constituent for about applying 1~10g per acre carrys out activation-inducing insect resistace.
Have with the plant Induced insect resistance that biologically active compound of the present invention is excited to Hemipteran pest Effect.
By following embodiments, a more step is made to the compound of the present invention and synthetic method and is specifically described, can further be managed The solution present invention.But it should declare, these embodiments are merely to illustrate the present invention rather than the limitation scope of the invention.
Embodiment 1: benzofuran derivative rice root absorbs benzofuran derivative reduction brown paddy plant hopper nymph and deposits Motility rate
In the present embodiment, used benzofuran derivative concentration is 20mg/L.Rice used is nutrient solution cultivation Train rice, single-strain planting;Processing method is that benzofuran derivative is added in rice nutrition liquid, until final concentration of 20mg/ Benzofuran derivative is not added as control using nutrient solution in L.After benzofuran derivative is handled 24 hours, in every plant of water A special glass cover (diameter 4cm, high 8cm, barrel uniformly promulgate the aperture of 48 diameter 0.8mm) is put on rice stem, is connect Upper just to incubate brown paddy plant hopper nymph 11, the top of cloche is sealed using round sponge.It tests in 28 ± 2 DEG C of temperature, humidity 70- 80%, it is carried out in the artificial climate room of illumination 14h, records the survival borer population of nymph daily, each processing is repeated 10 times.From Fig. 1 As it can be seen that seven kinds of benzofuran derivatives reduce nymph survival rate to some extent.The result shows that this seven kinds of benzofurans Derivative root absorption handles the direct resistance for improving rice significantly to brown paddy plant hopper nymph.
From the seven kinds of benzofuran derivatives induction insect resistant effect measured it is found that having the compound 1 of chalcone structure, 2,3,4 have a better bioactivity, and after this 4 kinds of compounds of rice application, brown paddy plant hopper nymph survival rate is decreased obviously all exists 40% or more.The bioactivity of compound 5 with flavonols structure and the compound 7 with flavones structure no 1,2,3, 4 bioactivity is good.Illustrate that chalcone structure is the essential elements of inducing paddy rice brown planthopper resistant nymph.When chalcone structure occurs After cyclization generates flavonols or flavones structure, the ability of inducing paddy rice brown planthopper resistant nymph can decline.Therefore, from now on Rice induce in pest-resistant MOLECULE DESIGN, can be optimized based on chalcone structure.
Embodiment 2: benzofuran derivative itself does not have an impact the survival of brown paddy plant hopper nymph
It is influenced to exclude this seven kinds of benzofuran derivatives itself to the possibility of brown paddy plant hopper nymph survival rate, the present embodiment In determine different concentrations of benzo furan derivative itself to the stomach toxicity of planthopper nymph, tag the effects of.In measurement benzo Furan derivative is put into 11 in every glass two-way pipe (diameter 4cm, high 8cm) in the experiment of brown paddy plant hopper stomach poison function Brown paddy plant hopper nymph is just incubated, man-made feeds are wrapped up with parafilm in double-way pipe both ends, and the benzofurans that concentration is 20mg/L are spread out Biology is added in man-made feeds;Using the man-made feeds without benzofuran derivative as control.Double-way pipe moves into people In work climate box (28 DEG C of temperature, illumination 12h), a man-made feeds are replaced daily, and record the survival number of nymph.Experiment repeats 6 times.The result shows that the benzofuran derivative for adding test concentrations in man-made feeds does not influence the nymph survival of brown paddy plant hopper Rate (Fig. 2) shows this seven kinds of benzofuran derivatives itself to brown paddy plant hopper without stomach poison function.
In measuring the experiment whether this seven kinds of benzofuran derivatives have action of contace poison to brown paddy plant hopper nymph, directly With the benzofuran derivative of 20mg/L to just incubating brown paddy plant hopper nymph carries out spraying treatment, compare as with without benzofurans The distillation water spray of derivative.Then it raises on the rice seedlings at 25 day length of time rice seedlings grow, 11 is raised on every seedling;Rice is placed in temperature 28 ± 2 DEG C, humidity 70-80%, illumination 14h artificial climate room in.Each processing is repeated 6 times.Observation is remembered daily in 6 days after processing Record the survival condition of brown paddy plant hopper nymph.The results show that control group and the nymph survival rate of benzofuran derivative processing group do not have There were significant differences (Fig. 3), shows this seven kinds of benzofuran derivatives to brown paddy plant hopper without action of contace poison.

Claims (3)

1. benzofuran compounds are exciting the application in resistance of the rice to brown paddy plant hopper nymph, which is characterized in that the application Are as follows: benzofuran compounds are added in rice nutrition liquid or water system, rice is cultivated, the benzofuran The structural formula of class compound are as follows:
2. application as described in claim 1, which is characterized in that the rice is by brown paddy plant hopper to the resistance of brown paddy plant hopper nymph It is excited before nymph harm.
3. application according to claim 1, which is characterized in that in nutrient solution or water system, benzofuran compounds Concentration is 20mg/L.
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Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106243121A (en) * 2016-08-02 2016-12-21 浙江大学 Substituted furan-flavone alcohol derivatives and preparation method thereof

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106243121A (en) * 2016-08-02 2016-12-21 浙江大学 Substituted furan-flavone alcohol derivatives and preparation method thereof

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
植物诱导抗虫反应的研究现状;娄永根;《中国生态学会2006学术年会》;20060831;141 *
水稻害虫化学生态调控研究进展;莫晓畅等;《应用昆虫学报》;20160531;第53卷(第3期);435-445 *

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