CN106417329B - A kind of crossocosmia tibialis disease prevention and treatment compound and application method - Google Patents
A kind of crossocosmia tibialis disease prevention and treatment compound and application method Download PDFInfo
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- CN106417329B CN106417329B CN201610851600.8A CN201610851600A CN106417329B CN 106417329 B CN106417329 B CN 106417329B CN 201610851600 A CN201610851600 A CN 201610851600A CN 106417329 B CN106417329 B CN 106417329B
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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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
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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
- A01N25/02—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 containing liquids as carriers, diluents or solvents
- A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
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- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
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Abstract
The present invention provides one kind to prevent and treat compound and its application method based on the crossocosmia tibialis disease of N- Phenylpyrazole amide derivatives structure.N- Phenylpyrazole amide derivative compounds of the present invention have the characteristics that selective desinsection, it is i.e. comparatively safe to tussah, it is higher that decorations abdomen intracorporal to parasitic silkworm posts fly larvae killing activity, alternative existing organic phosphates crossocosmia tibialis disease pesticide control, is used for sericultural production.
Description
Technical field
The present invention relates to crossocosmia tibialis disease prevention and control fields.
Background technique
Crossocosmia tibialis disease is to endanger one of Major Diseases of tussah, is by crossocosmia tibialis (Blepharipa
Tibialis Chao) parasitism causes: crossocosmia tibialis adult lays eggs in mongolian oak leaf face, ovum by tussah food it is lower and in silkworm body
Hatch into parasitized larvae in silkworm body, feeding silkworm body tissue, until deviating to pupate from tussah body when mature larva.Tussah decorations abdomen is posted
A generation occurs every year for fly, and each silkworm area silkworm in spring in Liaoning Province is 20~90% by parasitic rate.In recent years with crossocosmia tibialis constantly by
Liaoning northwards migrates, and each silkworm area silkworm in spring in Jilin Province is also growing day by day by parasitic rate.
Chemical prevention for crossocosmia tibialis disease, current methods still are based on the pleasure of the sixties in last century foundation
Fruit insecticide sprays mongolian oak leaf face using dilution and is administered by tussah foraging pattern.Due to the development of drug resistance, Rogor uses dense
Degree is promoted to 1500~2000mg/L by 800mg/L, and times for spraying is multiple by being once promoted to more than twice, or with Synergistic Phosphorus
With application, 80% or more can be reached by posting fly control efficiency.2012 old to increase and good etc. developed biological information element prevention and treatment tussah and post
Fly method, method advantage in terms of the prediction for posting fly adult occurrence quantity is significant, but there is not been reported for sericultural production application.
Fipronil is made by the Phenylpyrazole insecticides of first commercialization of Rhone-Poulenc Company's invention
It is to inhibit γ-aminobutyric acid (GABA) receptor chloride channel with mechanism.The insecticide is to a series of pests such as Lepidoptera, flies
With very high insecticidal activity, and with existing insecticide no interactions resistance.It carries out posting the test of fly control efficiency using Fipronil,
As a result (table 1) shows that the dilution that its effective content is 50mg/L is administered in a manner of leaf to spray, reachable to the control efficiency for posting fly~
90%, but the Cocooning rate of tussah is with respect to blank control decline~50%, relatively existing Rogor chemical control method, Cocooning rate decline
48.5%.Further decrease Fipronil using concentration to 30mg/L when its preventive effect be reduced to 80%, and Cocooning rate is increased slightly, but
It is still below Rogor and compares 26 percentage points, this illustrates that Fipronil is higher to tussah toxicity.
1 Fipronil of table posts fly control efficiency and Cocooning rate to tussah
Note: 1, Test Data Collecting was in 2012；2, test is in field silkworm, using 500 3~6 age in days, five ages tussahs,
Cocoon investigation is plucked in chemicals treatment, raising to tussah cocooning；3, calculation formula: Cocooning rate %=(number/500 of cocooing) * 100；It is parasitic
Rate %=(maggot cocoon number/number of cocooing) * 100；Control efficiency %=((blank parasitic rate-processing parasitic rate)/blank parasitic rate) *
100
Initial stage explores work and shows that Fipronil amide derivatives can reduce the toxicity to tussah, in Cocooning rate and blank space
Manage in comparable situation, compound to post the control efficiency of fly up to 69% (Niu Xionglei, Yang Jinchen, Zhang Huichun etc. " pesticide ",
2014,53 (4): 245-247), but not up to 80% or more produces acceptable preventive effect, thus fail to form patent.Further exhibition
It opens and closes into and bioactivity screening, part of compounds shows ideal prevention and treatment activity, correlated results of the present invention set forth below.
Summary of the invention
Crossocosmia tibialis disease the object of the present invention is to provide one kind based on N- Phenylpyrazole amide derivatives structure is anti-
Control compound and its application method.
The present invention prepares Fipronil amide derivatives using derivative synthesis method, and then Fipronil amide derivatives are made
Dispersing agent measures its prevention and treatment activity to crossocosmia tibialis, filters out relatively low to tussah toxicity (to cocoon in the present invention
Rate is evaluated, and it is lower to be considered as toxicity to handle gained Cocooning rate not less than 0.9 times of space management Cocooning rate) it is anti-to fly is posted
Control the compound of active high (preventive effect is not less than 80%).
Present invention has the main advantage that
1, its prevent and treat tussah post fly insecticidal mechanism it is novel, to inhibit GABA receptor, with existing pesticide control Rogor etc.
Organophosphorus insecticide no interactions resistance.
2, insecticide dosage is low.Compared with Rogor, Fipronil amides are posted fly prevention and treatment compound and are generally below using concentration
500mg/L, insufficient Rogor use the one third of concentration (generally greater than 1500mg/L).
3, insecticide service efficiency is high.Entire silkworm in spring prevents and treats crossocosmia tibialis during putting in a suitable place to breed, Fipronil amides are derivative
Object only needs to be administered primary reachable 80% or more preventive effect, and Rogor needs to reuse twice, the serious silkworm of part Rogor resistance
Area needs times for spraying to reach 3 times or more.
N- Phenylpyrazole amide derivative compounds of the present invention have the characteristics that selective desinsection, i.e., opposite to tussah
Safety, it is higher that decorations abdomen intracorporal to parasitic silkworm posts fly larvae killing activity, and alternative existing organic phosphates crossocosmia tibialis is sick
Pesticide control is used for sericultural production.
The invention will be further described with reference to embodiments, it should be appreciated that not further limitation is of the invention.
The compound synthesis yield does not carry out synthesis optimizing；Fusing point detects thermometer used and does not carry out temperature correction.
Specific embodiment
One, the preparation method of compound
Embodiment 1
The synthesis of compound XA01: three with condenser pipe and magnetic agitation are added in Fipronil 0.03mol, THF 40mL
It in mouth flask, under the conditions of ice-water bath, is added portionwise NaH (0.036mol), after stirring 0.5h, then is added dropwise and is dissolved in 10mL THF's
Butyl chloride 0.03mol is warming up to 85 DEG C of back flow reactions and stays overnight, and stops reaction, and revolving removes solvent, and Na is added2CO3Solution is adjusted
PH to 7.0~8.0 removes acid impurities.It adopts and is extracted with ethyl acetate 3 times, organic phase merges, the mistake after anhydrous magnesium sulfate is dry
Filter, is adsorbed in activated silica gel, using dry column-packing, obtains 4.92g through column chromatography (V (petroleum ether): V (ethyl acetate)=4:1)
Product, yield 32.3%.Melting point compound is measured, is carried out using Bruker Avance III 4001H NMR test, confirms its knot
(2) XA01 is shown in Table structure.
Embodiment 2
The synthesis of compound XA13: using operating procedure similar to Example 1, unlike: by raw material butyryl when reaction
Chlorine is substituted for trichloro-acetic chloride, and column is chromatographed mixed solvent V (petroleum ether) when separation: V (ethyl acetate) is adjusted to 3:1.It can make
For 7.01g product is obtained, (2) XA13, structure are shown in Table, yield 40.1%.
According to 1,2 similar method of embodiment, all compounds in table 2 can be prepared；Unlike: by raw material butyryl when reaction
Chlorine be substituted for isobutyryl chloride, caproyl chloride, oenanthyl chloro, caprylyl chloride, crotonyl chloride, methacrylic chloride, cinnamoyl chloride, furoyl chloride,
Monochloro-acetyl chloride, dichloroacetyl chloride, 2- chlorpromazine chloride, 3- chlorpromazine chloride, phenyllacetyl chloride, can be prepared product XA02-12,
14-16.Wherein compound WX-1 and WX-2 is that document (" pesticide ", 2014,53 (4): 245-247) have disclosed compound；XA01
~16 synthesize compound for present invention expansion.
Table 2 is for trying N- Phenylpyrazole amide derivatives
Two, the preparation of missible oil
Embodiment 3
The missible oil dispersing agent of prepare compound by taking XA01 as an example
It is matched according to calculating, 10.10g compound XA01 (purity is calculated with 99%) is dissolved in 84.90g solvent ethylene glycol
Methyl ether adds 5.00g agricultural emulsifier except B3, high-speed stirred 0.5h, the uniform cream that XA01 mass concentration is 5.00% is made
Oil, when use, are diluted with water to required concentration.
Remaining compound is prepared into the missible oil dispersing agent of compound using the process of being same as above.
Three, biological evaluation
Test method: the silkworm in Liaoning Fengcheng City, silkworm toothed oak tree is based on 2~triennial Mongolia toothed oak and Mongolian oak toothed oak.With tussah
Kind Dasanyuan is test worm, using 500 3~6 age in days, five ages tussahs of every processing, is scattered in 6~10 Dun toothed oak trees, fine day is selected to adopt
The medical fluid for uniformly spraying various concentration after mongolian oak leaf face is without dew with agricultural 15L watering can, is sprayed onto blade face and is covered with drop, do benefit
Reason number and label guarantee that tussah eats drug containing leaf 3 days, can carry out moving silkworm, and carry out trace labelling, after raising~15 days
Tussah cocooning plucks cocoon investigation.
Comparative example 1
Document discloses compound to the control efficiency of crossocosmia tibialis
The data processing method marked using table 1 is obtained document and discloses the highest two compound (document reports of preventive effect
WX-1 and WX-2 respectively reached in 160mg/L 69% and 56%)) concentration for the treatment of be 200mg/L and 500mg/L when to tussah
Decorations abdomen posts the control efficiency (table 3) of fly.Test blank control cell crossocosmia tibialis parasitic rate in 2016 is 20.63%, knot
Cocoon rate (calculates 0.9 times of its value, that is, 62.8%) meeting the processing Cocooning rate that screening requires should be not less than for 69.8%.By table 3
Data are it is found that increase to 500mg/L from 200mg/L for concentration for the treatment of, although the control efficiency of two compounds increased,
Middle WX-2 control efficiency reaches 81%, but Cocooning rate declines, and is below Cocooning rate screening criteria.
3 document of table discloses compound to the control efficiency of crossocosmia tibialis
Embodiment 4
The compounds of this invention different disposal concentration tests the control efficiency of crossocosmia tibialis.
Using 1 labeled data processing method of table, the compounds of this invention XA01~16 are obtained under various concentration to tussah
Decorations abdomen posts the control efficiency (table 4-1~4) of fly.Test blank control crossocosmia tibialis parasitic rate in 2016 is 20.63%, knot
Cocoon rate is 69.8%, and 62.8% should be not less than by meeting the processing Cocooning rate that screening requires, and control efficiency is not less than 80%.
When 500mg/L processing, by table 3-1 it is found that removing compound XA05, outside XA07, the compounds of this invention is prevented and treated fly is posted
Effect reaches 80% or more；XA01~04, X07, XA16 processing processing Cocooning rate are higher than 60%；Meet Cocooning rate screening simultaneously
The compound of index and preventive effect screening index is XA01, XA04, X16.
When reducing compound concentration for the treatment of, part of compounds activity data is listed (in higher first order concentration processing prevention and treatment effect
Fruit no longer lists related data in the test of low first order concentration less than 80% compound).
When 200mg/L processing, by table 3-2 it is found that test compound treated that Cocooning rate is above 62.8%, it is full simultaneously
The compound of sufficient Cocooning rate screening index and preventive effect screening index is XA01, XA06, XA08, XA09, XA13.
When 100mg/L processing, by table 3-3 it is found that meeting the chemical combination of Cocooning rate screening index and preventive effect screening index simultaneously
Object is compound XA06, XA08, XA09, XA13.
When 50mg/L processing, by table 3-4 it is found that meeting the compound of Cocooning rate screening index and preventive effect screening index simultaneously
It is compound XA08.
In conclusion removing compound XA05, outside XA07, chemical combination of the present invention is above 80% to fly control efficiency is posted, suitable
It is handled when under concentration, XA01~04, X07~09, X13, XA16 Cocooning rate is higher.There are the chemical combination of multiple suitable sericultural productions
Object and concentration processing combination, number is XA01-500, XA04-500, XA16-500, XA01-200, XA06-200, XA08-
200, XA09-200, XA10-200, XA13-200, A06-100, XA08-100, XA09-100, XA13-100 and XA08-50.Its
In, particularly preferred compound is XA01, XA06, XA08, XA09, XA13.
Table 4-1 500mg/L handles test compound to the control efficiency of crossocosmia tibialis
Table 4-2 200mg/L handles test compound to the control efficiency of crossocosmia tibialis
| Compound number | Handle code name | Cocooning rate/% | Control efficiency/% |
| XA01 | XA01-200 | 64.4 | 80.4 |
| XA02 | XA02-200 | 66.8 | 79.7 |
| XA03 | XA03-200 | 63.2 | 58.6 |
| XA04 | XA04-200 | 66.0 | 53.0 |
| XA06 | XA06-200 | 68.2 | 91.5 |
| XA08 | XA08-200 | 65.0 | 91.1 |
| XA09 | XA09-200 | 67.8 | 90.0 |
| XA10 | XA10-200 | 68.0 | 87.2 |
| XA11 | XA11-200 | 64.0 | 65.2 |
| XA12 | XA12-200 | 63.2 | 69.3 |
| XA13 | XA13-200 | 64.6 | 91.0 |
| XA14 | XA14-200 | 63.2 | 73.9 |
| XA15 | XA15-200 | 63.0 | 76.9 |
| XA16 | XA16-200 | 69.8 | 70.8 |
Table 4-3 100mg/L handles test compound to the control efficiency of crossocosmia tibialis
| Compound number | Handle code name | Cocooning rate/% | Control efficiency/% |
| XA01 | XA01-100 | 67.2 | 72.8 |
| XA06 | XA06-100 | 69.4 | 84.6 |
| XA08 | XA08-100 | 68.4 | 88.7 |
| XA09 | XA09-100 | 67.8 | 84.3 |
| XA10 | XA10-100 | 67.6 | 62.7 |
| XA13 | XA13-100 | 65.2 | 88.1 |
Table 4-4 50mg/L handles test compound to the control efficiency of crossocosmia tibialis
| Compound number | Handle code name | Cocooning rate/% | Control efficiency/% |
| XA06 | XA06-50 | 70.2 | 57.2 |
| XA08 | XA08-50 | 65.4 | 82.2 |
| XA09 | XA09-50 | 68.6 | 56.2 |
| XA13 | XA13-50 | 66.4 | 63.5 |
Embodiment 5
Influence after the compounds of this invention processing to tussah breeding performance is tested.
Spring tussah is mainly used for the production of hybrid seeds, for putting in a suitable place to breed for autumn tussah.It tests every processing and randomly selects 20 female moths, investigate it
Single moth egg amount, hatching ovum amount, hatching rate calculate average value.Statistical check shows single moth egg amount, egg hatching amount after processing
And hatching rate is not significant with space management difference.After this illustrates the compounds of this invention processing, it is not influenced and breeds performance, can be used
In sericultural production.
Tussah cocoon list moth egg amount and hatching rate are compared with blank control is handled after the processing of table 5
Note: same letter shows that statistical discrepancy is not significant after every column of figure, different letters show statistical discrepancy it is significant (p <
0.05)。
Claims (3)
1. a kind of compound is used to prepare to post for preventing and/or treat tussah as active ingredient adorns the insecticide of abdomen fly disease
Purposes, it is characterised in that:, using following compounds as active ingredient, the compound has the following structure general formula for it:
2. purposes described in accordance with the claim 1, which is characterized in that by any compound of claim 1 with organic solution
For solvent prepared composition powder, being diluted with water to compound effective content is 50-500 mg/L, to impregnate in a manner of silkworm body or blade face
Freshen food mode drug administration preventing and controlling tussah endobiosis fly larvae.
3. purposes according to claim 2, which is characterized in that be by any compound effective content of claim 1
50 ~ 500 mg/L water diluents are sprayed on mongolian oak leaf face, guarantee tussah feeding drug containing leaf 3 days or more.
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| CN109651379B (en) * | 2019-01-31 | 2020-08-28 | 中南民族大学 | Pentaaza and/or oxo-dithio-dicyclo-dienone-containing compound and microwave solvent thermal synthesis method and application thereof |
| CN113261541A (en) * | 2021-05-19 | 2021-08-17 | 辽宁省蚕业科学研究所 | Method for preventing and controlling pests in tussah garden |
| CN115299456A (en) * | 2022-08-25 | 2022-11-08 | 辽宁省蚕业科学研究所 | Medicament for preventing and controlling parasitoid fly at decorated abdomen of tussah in tussah garden by spray method and application thereof |
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