CN104974083B - Dichloro allyl ether series compound, insecticide and its application - Google Patents
Dichloro allyl ether series compound, insecticide and its application Download PDFInfo
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- CN104974083B CN104974083B CN201410138664.4A CN201410138664A CN104974083B CN 104974083 B CN104974083 B CN 104974083B CN 201410138664 A CN201410138664 A CN 201410138664A CN 104974083 B CN104974083 B CN 104974083B
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- 0 CNC(*1)=Nc2c1ccc(*=C)c2N Chemical compound CNC(*1)=Nc2c1ccc(*=C)c2N 0.000 description 3
- BUBAVRDAXHKVAG-UHFFFAOYSA-N ClC(Cl)=CCOc(cc1Cl)cc(Cl)c1OCCCOc1nc(ccc(Cl)c2)c2[s]1 Chemical compound ClC(Cl)=CCOc(cc1Cl)cc(Cl)c1OCCCOc1nc(ccc(Cl)c2)c2[s]1 BUBAVRDAXHKVAG-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
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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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
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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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
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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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/14—Oxygen atoms
- C07D237/16—Two oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
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- General Health & Medical Sciences (AREA)
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- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention discloses a kind of dichloro allyl ether series compound, and it is following formulas（1）The compound of shown structure,
Description
Technical field
The present invention relates to dichloro allyl ether series compound, insecticide and its application.
Background technology
Farmland insect seriously endangers the safety of grain, and traditional part high-toxic organic phosphorus, carbamates kill
Worm agent can not meet the requirement of Modern Green agricultural chemicals.Insect is novel with greater need for mechanism of action to the resistance problem of existing insecticide
Insecticide occur.
SUMITOMO CHEMICAL company develops a kind of dihalo compound, wherein compound K C1Have been developed to commercialization
Insecticide, general entitled pyridalyl（Pyridalyl）,
The compound listed in 2004, because its mechanism of action is unique, with existing insecticide no interactions resistance.Also can be with
Various medicaments mixture is to improve insecticidal effect.
In order to effectively prevent insect, more dihalo compounds with insecticidal activity are also needed at present.
The content of the invention
It is an object of the invention to provide a kind of new dichloro allyl ether series compound with excellent insecticidal activity,
Insecticide containing the compound, and application of the compound in pest control.
To achieve these goals, the present invention provides a kind of dichloro allyl ether series compound, wherein, two chlorallyl
Ether compound is following formulas（1）The compound of shown structure,
Formula（1）
Formula（1）In, R1For selected from following radicals WithIn one
Kind；
N is 0-3 integer.
The present invention also provides a kind of insecticide for containing above-mentioned dichloro allyl ether series compound as active component.
In addition, the present invention also provides a kind of application of above-mentioned insecticide in terms of pest control.
According to the dichloro allyl ether series compound of the present invention, it has excellent insecticidal activity, particularly to Lepidoptera
（Lepidoptera）The insect such as bollworm, diamondback moth, prodenia litura and beet armyworm there is especially excellent killing activity.
Embodiment
The embodiment of the present invention is described in detail below.It is it should be appreciated that described herein specific
Embodiment is merely to illustrate and explain the present invention, and is not intended to limit the invention.
Dichloro allyl ether series compound provided by the invention is following formulas（1）The compound of shown structure,
Formula（1）
Formula（1）In, R1For selected from following radicals WithIn one
Kind；
N is 0-3 integer.
In the present invention, R1Selected from group inRepresent R1The key being connected with oxygen atom.
According to the present invention, above-mentioned n is preferably 1-2.
The dichloro allyl ether series compound of the present invention is more preferably one kind in following compound A1-A7,
Further, dichloro allyl ether series compound of the invention is preferably A1, A2 or A6；More preferably A1 or A6；
Particularly preferably A1.
The dichloro allyl ether series compound of the present invention can be prepared by following synthetic lines, following synthetic threads
Lu Zhong, R1It is same as described above with n definition.
Synthetic line：
1）The synthesis of compound 2
Above-claimed cpd 2 (1,1,3- tri chloropropene) can make compound 1 (1,1,1,3- using ferric trichloride as catalyst
Four chloropropanes) slough a molecule hydrogen chloride and obtain.
The reaction condition includes：Reaction temperature is 80-120 DEG C, preferably 85-95 DEG C；Reaction time is 6-24 hours, excellent
Elect 6-12 hours as.
2）The synthesis of compound 3
Above-claimed cpd 3 can make compound 2 carry out condensation with hydroquinones and form in the presence of acid binding agent and solvent.
The acid binding agent can be with various acid binding agents well known in the art.For example, potassium carbonate, cesium carbonate, hydroxide
One or more in sodium, sodium carbonate, potassium hydroxide, sodium acid carbonate and triethylamine；Preferably potassium carbonate.
The solvent can be acetone, tetrahydrofuran, N,N-dimethylformamide and glycol dimethyl ether in one kind or
It is a variety of；Preferably acetone.
The condition of the reaction includes：Reaction temperature is 30-80 DEG C, preferably 50-60 DEG C；Reaction time is 5-24 hours,
Preferably 6-12 hours.
3）The synthesis of compound 4
Above-claimed cpd 4 can make the ortho position chlorination of phenolic hydroxyl group and obtain by the way that compound 3 is contacted with acyl chlorides.
The chlorination reagent can be sulfonic acid chloride or thionyl chloride；Preferably sulfonic acid chloride.
Contact of the compound 3 with acyl chlorides is preferably carried out in the presence of solvent.The solvent can be toluene and/or benzene；It is excellent
Elect toluene as.
The condition of the reaction includes：The temperature of reaction is 30-90 DEG C, preferably 50-65 DEG C；Reaction time is that 2-12 is small
When, preferably 2-6 hours.
4）The synthesis of compound 5
Compound 5 is by the presence of acid binding agent and solvent forming, the condensation of compound 4 and 3- bromos alkylol.
The acid binding agent can be various acid binding agents commonly used in this field.Such as can be potassium carbonate, cesium carbonate hydrogen-oxygen
Change the one or more in sodium, sodium carbonate, potassium hydroxide, sodium acid carbonate and triethylamine；Preferably potassium carbonate.
The solvent can be acetone, tetrahydrofuran, N,N-dimethylformamide and glycol dimethyl ether in one kind or
It is a variety of；Preferably acetone.
The reaction condition of the reaction includes：Reaction temperature is 30-70 DEG C, preferably 50-60 DEG C；Reaction time is that 3-12 is small
When, preferably 3-6 hours.
5）(the i.e. formula of compound 6（1）The compound of shown structure) synthesis
Compound 6 can be by the presence of acid binding agent and solvent, making compound 5 and R1- Cl or R1-SO2CH3Contracted
Conjunction forms.
The acid binding agent can be various acid binding agents commonly used in this field.Such as can be potassium carbonate, cesium carbonate hydrogen-oxygen
Change the one or more in sodium, sodium carbonate, potassium hydroxide, sodium acid carbonate and triethylamine；Preferably potassium carbonate.
The solvent can be tetrahydrofuran, N,N-dimethylformamide, acetone and glycol dimethyl ether in one kind or
It is a variety of；Preferably tetrahydrofuran or glycol dimethyl ether.
The reaction condition of the reaction includes：Reaction temperature is 40-120 DEG C, preferably 50-80 DEG C；Reaction time is 3-12
Hour, preferably 3-6 hours.
As above-mentioned R1- Cl can be 2,5- dichloropyridines, 4- chloro-2-methyl -6- trifluoromethyl pyrimidines or 2- (tertiary fourths
Base) -4,5- dichloro pyridazinones.As above-mentioned R1-SO2CH3Can be 2- methylsulfonyl -5- methoxybenzothiazoles, 2- methylsulfonyls -
6- fluoro benzothiazoles, 2- methylsulfonyl -6- chloro benzothiazoles or 2- methylsulfonyl -6,7- difluoro benzothiazoles.These compounds can be with
By commercially available, can also be synthesized according to method well known in the art.
The present invention also provides a kind of insecticide, wherein, the insecticide contains above-mentioned compound as active component.
According to the present invention, by formula（1）, can be by when the dichloro allyl ether series compound of shown structure is prepared into insecticide
Prepared according to method well known in the art.For example, for active component（Formula（1）The dichloro allyl ether series of shown structure
Compound）Content in insecticide can select conventional dosage, this is this without particular/special requirement according to the different dosage forms of insecticide
Well known to art personnel, for example, the gross weight based on insecticide, the content of active component can be 0.5-95 weight %.
In the present invention, for other compositions in insecticide in addition to the active ingredient (s without particular/special requirement, it can select as needed
With composition commonly used in the art, for example, dispersant, wetting agent, antifreezing agent, stabilizer, thickener, emulsifying agent, defoamer, molten
Agent, adsorbent, disintegrant, binding agent, wall material, solid inert carrier, acid adjustment medium, alkali tune medium.Therefore, desinsection of the invention
Agent also containing dispersant, wetting agent, antifreezing agent, stabilizer, thickener, emulsifying agent, defoamer, solvent, adsorbent, disintegrant,
One or more in binding agent, wall material, solid inert carrier, acid adjustment medium and alkali tune medium.These compositions can be according to killing
The conventional dosage of the dosage form selection of worm agent, this is known to those skilled in the art, will not be repeated here.
In the present invention, for mentioned component without particular/special requirement, material commonly used in the art can be used, such as：
Solvent is selected from various aromatic hydrocarbons, aliphatic hydrocarbon, tetrahydrofuran, ketone, ethers etc., as benzene, dimethylbenzene, acetone, cyclohexanone,
One or more in dimethylformamide, methanol, ethanol, naphthalane, machine oil and petroleum ether etc..
Emulsifying agent is selected from agriculture breast 500# (calcium dodecyl benzene sulfonate), OP series phosphate (NPE phosphorus
Acid esters), 600# phosphates (triphenyl vinyl phenol polyoxyethylene ether phosphate), styrene polyoxyethylene ether ammonium sulfate salt, alkyl
Biphenyl Ether disulfonic acid magnesium salts, triethanolamine salt, agriculture breast 400#（Benzyl dimethyl phenol polyoxyethyl ether), agriculture breast 600# (phenyl phenols
APEO), Nongru-700 # (alkylphenol-formaldehyde resin polyoxyethyl ether), agriculture breast 36# (phenethyl phenol formaldehyde resin polyoxy second
Base ether), agriculture breast 1600# (phenethyl phenol polyoxyethanyl polypropylene-base ether), ethylene oxide-propylene oxide block copolymer, OP systems
Arrange (NPE), By serial (castor oil polyoxyethylene ether), Triton X-100 (polyethylene glycol octyl phenyls
Ether), agriculture breast 33# (alkylaryl polyoxyethylene polyoxypropylene ether again), agriculture breast 34# (alkylaryl polyoxyethylene poly-oxygen propylene aether),
Span series (sorbitan monostearate), TWEEN Series (sorbitan fatty acid ester APEO) and EO series
One or more in (AEO).
Dispersant is selected from alkylnaphthalene sulfonate, double (alkyl) naphthalenesulfonate formaldehyde condensation compounds, naphthalene sulfonic acid-formaldehyde condensation product, virtue
Base phenol polyethenoxy succinate sulfonate, octylphenol polyethylene oxyethylene group ether sulfate, polycarboxylate, lignin sulfonic acid sodium salt,
APES formaldehyde condensation products sulfat, alkyl benzene sulfonate calcium salt, naphthalene sulfonic acid-formaldehyde condensation product sodium salt, alkyl phenol gather
One or more in oxygen vinethene, aliphatic amine polyoxyethylene ether, polyoxyethylene carboxylate and ester APEO.
Wetting agent is selected from lauryl sodium sulfate, neopelex, Nekal BX, washing powder, agriculture breast 2000# systems
One or more in row, sldium lauryl sulfate, wetting and penetrating agent F, wetting agent T, spaonin powder, tea seed cake, silkworm excrement and spaonin powder.
One or more of the disintegrant in bentonite, urea, ammonium sulfate, aluminium chloride and glucose.
Thickener is selected from synthesis（Such as carbonyl methylol alcohol, polyvinyl alcohol, polyvinyl acetate）Or natural water-soluble polymeric
Thing（As xanthans, gelatin, Arabic gum, polyvinylpyrrolidone, aluminium-magnesium silicate, polyvinyl alcohol, polyethylene glycol, phenolic resin,
Shellac, carboxymethyl cellulose and sodium alginate etc.）, added with powder, particle or latex form in preparation.
One or more of the antifreezing agent in ethylene glycol, propane diols, glycerine and polyethylene glycol.
Defoamer is selected from silicone, C8-10Aliphatic alcohols, C10-20Saturated fat acids (such as capric acid) and acid amides, silicone oil and silicon
One or more in ketone compounds.
Wall material be selected from polyureas, polyurethane, melmac and polyureas/polyamide of mixing, gelatin/Ah
Draw primary glue, polyamide, urea/formaldehyde, nylon（Nylon）, one or more in polyethylene/paraffin.
One or more of the solid inert carrier in natural or synthesis clay and silicate, suitable for pulvis
Solid carrier includes rock dust, chalk, quartz, clay, montmorillonite, silica, diatomite, float stone, the stone naturally occurred
Cream, talcum, bentonite, kaolin, clay and the mineral matter ground of synthesis（It is such as scattered silicic acid or aluminum oxide）.It is applied to
The solid carrier of particle includes broken and classification natural rock such as calcite, marble, float stone, sepiolite and dolomite
And synthesis particle made of the powder of organic matter and inorganic matter.
One or more of the acid adjustment medium in ammonium chloride, hydrochloric acid, citric acid, ammonium sulfate, ammonium nitrate, acetic acid.
One or more of the alkali tune medium in sodium hydroxide, triethanolamine, triethylamine, ammoniacal liquor, caustic alcohol.
One or more of the adsorbent in white carbon, bentonite, diatomite.
Stabilizer, binding agent etc. also use material commonly used in the art, and this is known to those skilled in the art, herein
Repeat no more.
The insecticide of the present invention can be prepared into various formulations commonly used in the art, can be missible oil, water and milk specifically
Agent, aqueous suspension agent, oil-suspending agent, microcapsule suspending agent, wettable powder, water-dispersible granules, soluble powder, soluble grain
Agent or microemulsion, above-mentioned formulation can be prepared by the conventional method of this area.
Under preferable case, the composition of the cream preparation weight percent is active component 0.5~95%, cosolvent 0-
20%th, emulsifying agent 1~30%, solvent complement to 100%.
The above-mentioned preparation method for stating cream preparation can for example include each active component, solvent, cosolvent and emulsifying agent
Mixing, makes its property into homogeneous oil phase, you can obtain cream preparation.
Under preferable case, the composition of aqueous emulsion or the microemulsion weight percent is active component 0.5~95%, breast
Agent 1~30%, cosolvent 0~30%, solvent 1~30%, antifreezing agent 0~10%, thickener 0~10%, water complement to 100%.
Under preferable case, the preparation method of the aqueous emulsion or microemulsion can for example include by active component, emulsifying agent,
Cosolvent and solvent mixing, become homogeneous oil phase；Water, thickener, antifreezing agent etc. are mixed, make it into homogeneous aqueous phase.
Under high-speed stirred, aqueous phase is added to oil phase or oil phase is added to aqueous phase, form the aqueous emulsion or microemulsion of favorable dispersibility.
Wherein, microemulsion appearance transparent, aqueous emulsion are then suspension.
Under preferable case, the composition of the aqueous suspension agent weight percent is active component 0.5~95%, surface-active
Agent 1~30%, antifreezing agent 1~10%, thickener 0.1~5%, water complement to 100%.
Under preferable case, the composition of the oil-suspending agent weight percent is active component 0.5~95%, emulsifying agent 1~
30%th, thickener 0.1~5%, oil complement to 100%.
The preparation method of water/oil-suspending agent：With water or oil for medium, active component, surfactant, thickener etc. are helped
Agent is added in sand milling kettle, and progress is finely ground, and oil-suspending agent or aqueous suspension agent is made.
Under preferable case, the soluble granula, soluble powder, water dispersible granules or wettable powder percentage by weight
Several compositions is active component 0.5~95%, surfactant 1~30%, other carriers complement to 100%.
Wherein, the preparation method of water-dispersible granules and soluble granula is：Each active component and other carriers etc. are entered
Row co-grinding, spray-dried or fluidized drying produce；Or add water to mediate after co-grinding, add in comminutor and carry out
It is granulated, is then produced again through drying, 5~60 mesh sieves point.
The preparation method of soluble powder and wettable powder is：By each active component, various auxiliary agents and other carriers etc.
Filler is sufficiently mixed, and uses ultra-fine pulverizer disintegrating.
Under preferable case, the composition of above-mentioned microcapsule suspending agent weight percent is active component 0.5~95%, solvent 1~
30%th, protective agent 0.1~5.0%, defoamer 0.05~1.0%, capsule material 1~30%, dispersant 1~30%, wetting agent 0~30%, prevent
Jelly agent 0~10%, thickener 0.1~5%, water complement to 100%.
Preparation method：Solvent, capsule material are mixed, then add active component；Be added into again by protective agent, antifreezing agent,
Emulsified in the mixture of defoamer and water composition, stirring is until polymerisation is completed；Add thickener, dispersant and wetting
Agent, the microcapsule suspending agent stablized.
The present invention also provides application of the above-mentioned insecticide in terms of pest control.
According to the present invention, the insect is Lepidoptera（Lepidoptera）, coleoptera（Coleoptera）Insect.It is excellent
Selection of land, the insect are Lepidoptera（Lepidoptera）Insect；It is highly preferred that the insect is Lepidoptera（Lepidoptera）
Insect be bollworm, diamondback moth, prodenia litura and beet armyworm.
According to the present invention, using the present invention insecticide when, the active component of effective dose can be applied to insect or evil
The habitat of worm.The amount of application of its active component, generally, every mu is applied 10-1000g, preferably 20-500g, more excellent
Elect 50-400g as.100-400mg/L administrations are preferably diluted to during use, are more preferably diluted to 200-400mg/L administrations.Separately
Outside, diluent is preferably water.
The present invention will be described in detail by way of examples below.
Preparation example 1
This preparation example is used for the synthesis for illustrating A1 compounds
1）1,1,3- tri chloropropenes（Compound 2）Synthesis
By the chloropropanes of 1,1,1,3- tetra-（Compound 1,54.60g）And iron chloride（0.16g）Round-bottomed flask is put into, and is passed through
Condenser pipe connects device for absorbing tail gas (high alkali liquid) with drying tube, is stirred vigorously, and is heated to 90-100 DEG C, after reacting 8 hours,
The ratio of product and raw material no longer changes, and is evaporated under reduced pressure, obtains the tri chloropropene of product 1,1,3-（Compound 2）, it is colourless
Prescribed liquid.
2）4- (chloroallyloxyaminos of 3,3- bis-) phenol（Compound 3）Synthesis
Toward hydroquinones（16.50g）With 1,1,3- tri chloropropenes（4.37g）Acetone soln in add potassium carbonate
（6.21g）, back flow reaction is overnight, filters, and after filtrate desolventizing, passes through silica gel column chromatography（Eluant, eluent is petroleum ether：Acetone（Body
Product ratio）=20：1）4- (chloroallyloxyaminos of the 3,3- bis-) phenol obtained（Compound 3）, it is light brown liquid.
Nuclear magnetic data is：1H NMR(400MHz,CDCl3)δ:4.60(d,J=6.4Hz,2H, OCH2),6.14(t,J=
6.4Hz,1H,HC=CCl2),6.78(s,4H,ArH).
3）Bis- chloro- 1- of 2,6- (chloroallyloxyaminos of 3,3- bis-) -4- phenol（Compound 4）Synthesis
Toward dissolved with 4- (chloroallyloxyaminos of 3,3- bis-) phenol（4.10g）Toluene solution in, add diethylamine（0.028g）,
It is slowly added dropwise at 60-65 DEG C dissolved with sulfonic acid chloride（5.17g）Toluene solution 30ml, drip off within about 3 hours, it is 1.5 small to continue reaction
When after stop reaction, add saturation NaHCO3Solution, toluene layer is isolated after cooling, water layer is extracted with toluene, merges organic phase,
Anhydrous Na2SO4Dry, then desolventizing carries out silica gel column chromatography (eluant, eluent is pure petroleum ether), obtains the chloro- 4- (3,3- of 2,6- bis-
Two chloroallyloxyaminos) phenol（Compound 4）, it is pale solid.
Nuclear magnetic data is：1H NMR(400MHz,CDCl3)δ:4.57(d,J=6.0Hz,2H, OCH2),5.51(s,1H,
PhOH),6.11(t,J=6.0Hz,1H,C=CCl2),6.85(s,2H,ArH).
4）The synthesis of compound 5
By 10mmol bis- chloro- 1- of intermediate 2,6- (chloroallyloxyaminos of 3,3- bis-) -4- phenol (compound 4) and 20mmol
3- bromopropyl alcohols be dissolved in 20mL acetone soln, add the potassium carbonate newly fried of 15mmol, be heated to 45 DEG C of reactions, TLC tracking
Detection, raw material, which disappears, stops reaction, filtering, sloughs acetone, silica gel column chromatography（VAcetone/VPetroleum ether=1/20）Obtain faint yellow solid production
Product, yield 79%.
Nuclear magnetic data is：1H NMR(400MHz,CDCl3)δ:2.07(m,2H,C-CH2-C),3.97(t, J=6.0Hz,
2H,CH2O),4.12(t,J=6.0Hz,2H,ArOCH2),4.59(d,J=6.0Hz,2H, OCH2-C=CCl2),6.12(t,J=
6.0Hz,1H,CH=CCl2),6.85(s,2H,ArH).
5）Compound A2-A8 synthesis
By the heterocycle of 1mmol compound 5,2mmol NaH and 0.8mmol 2- halos or methylsulfonyl be dissolved in 10mL without
In water tetrahydrofuran, heating reflux reaction, TLC tracing detections, raw material, which disappears, stops reaction.Silica gel column chromatography（（VAcetone/VPetroleum ether
=1/50）Obtain compound A1-A7.Wherein, the structure of the heterocycle of 2- halos or methylsulfonyl is shown in Table 1.
Yield:32%.State：Colourless oil liquid.1H NMR(400MHz,CDCl3):δ6.88(s, 1H),6.84(s,
2H),6.12(t,J=6.4Hz,1H),4.71(t,J=6.0Hz,2H),4.58(d,J= 6.4Hz,2H),4.12(t,J=6.4Hz,
2H),2.69(s,3H),2.32–2.28(m,2H).13C NMR (100MHz,CDCl3):δ170.13,169.68,156.21,
155.86,154.10,145.82,129.72, 125.07,124.50,121.96,119.23,115.66,102.27,69.82,
65.57,63.96,29.38,25.89. HRMS calcd for[M+H+]:504.9867,found:504.9883.
Yield:68%.State：Colourless oil liquid.1H NMR(400MHz,CDCl3):δ7.48(d, J=5.6Hz,1H),
6.86(d,J=6.0Hz,1H),6.83(s,2H),6.10(t,J=4.0Hz,1H), 4.84(t,J=4.0Hz,2H),4.57(d,J
=4.0Hz,2H),4.14(t,J=4.0Hz,2H),3.85(s, 3H),2.36–2.34(m,2H).13C NMR(100MHz,
CDCl3):δ173.82,158.71,153.89, 150.32,145.56,129.61,124.76,124.46,123.07,
121.38,115.08,112.17,104.78, 69.43,68.34,65.33,55.38,29.44.HRMS calcd for[M+H+]:507.9711,found: 507.9738.
Yield:57%.State：Colourless oil liquid.1H NMR(400MHz,CDCl3):δ7.62 -7.59(m,2H),
7.33-7.26(m,1H),6.83(s,1H),6.11(t,J=4.4Hz,1H),4.85(t, J=4.4Hz,2H),4.58(d,J=
4.4Hz,2H),4.14(t,J=4.0Hz,2H),2.37-2.35(m, 2H).13C NMR(100MHz,CDCl3):δ172.87,
154.05,147.94,145.67,133.03, 129.73,128.85,126.52,124.99,124.48,121.59,
120.90,115.25,69.45,68.81, 65.49,29.48.HRMS calcd for[M+H+]:511.9215,found:
511.9239.
Yield:43%.State：Colourless oil liquid.mp:58-59℃.1H NMR(400MHz, CDCl3):δ7.63–7.61
(m,1H),7.35–7.33(m,1H),7.10–7.07(m,1H),6.83(s, 2H),6.11(t,J=4.4Hz,1H),4.84(t,
J=4.0Hz,2H),4.58(d,J=4.0Hz,2H), 4.14(t,J=4.0Hz,2H),2.38–2.34(m,2H).13C NMR
(100MHz,CDCl3):δ 160.42,158.02,154,145.71,145.65,129.71,124.92,124.48,121.53,
121.44, 115.19,113.96,113.72,107.96,107.69,69.46,68.64,65.43,29.48.HRMS calcd
for[M+H+]:495.9511,found:495.9525.
Yield:49%.State：White solid.mp:62-63℃.1H NMR(400MHz,CDCl3): δ7.42–7.39(m,
1H),7.22–7.15(m,1H),6.84(s,2H),6.11(t,J=6.0Hz,1H), 4.86(t,J=6.0Hz,2H),4.58(d,
J=6.4Hz,2H),4.14(t,J=6.0Hz,2H),2.39– 2.33(m,2H).13C NMR(100MHz,CDCl3):δ172.54,
154.04,147.80,146.94, 145.79,145.59,145.39,143.13,129.69,124.95,124.47,
116.17,115.20,115.02, 69.32,69.26,65.45,29.42.HRMS calcd for[M+H+]:513.9417,
found:513.9417.
Yield:58%. states：Colourless oil liquid.1H NMR(400MHz,CDCl3):δ7.64(s, 1H),6.83(s,
2H),6.11(t,J=6.0Hz,1H),4.74(t,J=6.0Hz,2H),4.58(d,J= 6.4Hz,2H),4.17(t,J=6.0Hz,
2H),2.30–2.25(m,2H),1.66(s,9H).13C NMR (100MHz,CDCl3):δ157.81,153.79,150.97,
145.69,134.85,129.58,124.73, 124.45,123.48,115.04,69.87,69.34,65.57,65.33,
30.87.27.71.HRMS calcd for[M+Na+]:550.9842,found:550.9822.
Yield：32%.State：Colourless oil liquid.1H NMR(400MHz,CDCl3):δ8.10(s, 1H),7.51(d,J=
8.4z,1H),6.83(s,2H),6.70(d,J=8.4Hz,1H),6.11(t,J=6.0 Hz,1H),4.58-4.52(m,4H),
4.12(t,J=6.0Hz,2H),2.29-2.26(m,2H).
Preparation example 2
Carried out according to the method for preparation example 1, the difference is that in step 4）The middle 4- methaforms with same molar replace 3-
Bromopropyl alcohol, obtain compound A1.Wherein, step 5）In 2- halos heterocycle structure it is as shown in table 1.
1H NMR(400Mz,CDCl3)δ:1.96-2.06(m,4H),4.01(t,J=6.4Hz,2H), 4.36(t,J=
6.0Hz,2H),4.58(d,J=6.4Hz,2H),6.11(t,J=6.4Hz,1H),6.70 (d,J=8.8Hz,1H),6.84(s,
2H),7.52(dd,J1=2.8Hz,J2=2.8Hz),8.09(d,J =2.4Hz,1H).HRMS(M+H)+Calculated value：469.9651
Measured value：469.9660.
Table 1
In table 1,2,5- dichloropyridines are purchased from Aladdin Reagent Company；The synthesis of 4- chloro-2-methyl -6- trifluoromethyl pyrimidines
Synthesized according to the method described in WO2010/134478A1；2- methylsulfonyl -5- methoxybenzothiazoles, 2- methylsulfonyls -6-
The synthesis of fluoro benzothiazole, 2- methylsulfonyl -6- chloro benzothiazoles, 2- methylsulfonyl -6,7- difluoro benzothiazoles is according to document
Org.Biomol.Chem.2012,10,1225-1234. the method described in is synthesized；2- (tert-butyl group) -4,5- dichloros are rattled away
The preparation of piperazine ketone is synthesized according to the method described in WO2009/142732A2.
Test case 1
This test case is used for insecticidal activity of the dichloro allyl ether series compound to prodenia litura for illustrating the present invention.
Reagent agent：Compound A1-A7 and pyridalyl.
For trying insect：Prodenia litura（Prodenia litura(Fabricius)）In May, 2009 is by Jiangsu's agriculture science
Institute presents, and is the sensitive strain in indoor feeding more generations.
Drug solution preparing：Use assay balance（0.0001g）The active compound of certain mass is weighed, with acetone solution and is configured to 1 weight
Measure % solution（Mother liquor）.The mother liquor of measured amounts, add the distilled water containing 0.1 weight % Tween-80s（Hereinafter referred to as 0.1%
Triton）Dilution is configured to determine the decoction of required concentration, standby.
Test method：Dried in the shade naturally after the soya bean blade sheared is fully infiltrated in the decoction prepared, be put into and be lined with filter
In the culture dish of paper, prodenia litura 2 age mid-term larva, 10/ware is connect, observation indoor feeding and observation are placed in after capping mark.
Inspection result after 96h, make control comparisons, 2 repetitions using 0.1%Triton as blank control and with pyridalyl.It the results are shown in Table 2.
Table 2
By table 2, dichloro allyl ether series compound A1-A7 of the invention is respectively provided with to prodenia litura preferably to be killed
The activity of worm activity, particularly A1, A2 and A6 is suitable with pyridalyl.
Test case 2
This test case is used for insecticidal activity of the dichloro allyl ether series compound to bollworm for illustrating the present invention.
Reagent agent：Compound A1, A2 and A8.
For trying insect：Bollworm（Helicoverpa armigera(Hübner)）, Henan Yanshi is picked up within 1991, it is indoor
Raised for more than 20 years and from the sensitive strain not in contact with medicament.
Drug solution preparing：Use assay balance（0.0001g）The active compound of certain mass is weighed, with acetone solution and is configured to 1 weight
Measure % solution（Mother liquor）.The mother liquor of measured amounts, add the distilled water containing 0.1 weight % Tween-80s（Hereinafter referred to as 0.1%
Triton）Dilution is configured to the decoction of series concentration gradient, standby.
Test method：After diameter 3cm cabbage leaf dish is impregnated into 20s in above-mentioned decoction respectively, naturally dry is taken out extremely
Without bright water, using 0.1%Triton as control.Bollworm often handles 6, is repeated 5 times.Cotton bollworm larvae is obtained after processing and is put into temperature
For 27 ± 1 DEG C, photoperiod 16:8h(L:D), RH is to be cultivated in 60~80% constant incubator, connects worm and knot is checked after 5 days
Fruit, polypide is touched with writing brush during inspection, the coordinated movement of various economic factors is unable to as death standard using larva.Its result is as shown in table 3.
Table 3
Data processing：Toxicity regression line, LC50 values and its 95% confidence limit are calculated using U.S. EPA software.According to chemical combination
Whether 95% confidence limit of thing LC50 values is overlapping to differentiate whether Virulence Difference is notable.Its result is as shown in table 4.
Table 4
| Test compound | Toxicity regression line | LC50Value and 95% confidence limit (mg/L) | Relative virus force index |
| A1 | 3.4681+2.4175X | 4.302 (3.480~5.414) | 11.6 |
| A2 | 3.6620+1.8825X | 5.138 (3.682~6.682) | 9.7 |
| A8 | 2.4191+3.1881X | 6.450 (5.263~7.805) | 7.7 |
By table 4, A1, A2 and A8 have preferable insecticidal activity to the insecticidal activity of bollworm, and A1, A2 are killed
Bollworm is better than A8.
Test case 3
This test case is used for insecticidal activity of the dichloro allyl ether series compound to beet armyworm for illustrating the present invention.
Reagent agent：Compound A1, A6 and pyridalyl.
For trying insect：Beet armyworm（Spodoptera exigua(Hübner)）In May, 2001 is by Wuhan section promise biology skill
Art Co., Ltd provides, and is the sensitive strain in indoor feeding more generations.
Drug solution preparing：Use assay balance（0.0001g）The active compound of certain mass is weighed, with acetone solution and is configured to 1 weight
Measure % solution（Mother liquor）.The mother liquor of measured amounts, add the distilled water containing 0.1 weight % Tween-80s（Hereinafter referred to as 0.1%
Triton）Dilution is configured to the decoction of series concentration gradient, standby.
Test method：Diameter 5cm cabbage leaf butterfly is impregnated into 20s in above-mentioned decoction respectively, naturally dry is extremely after taking-up
Without bright water, using 0.1%Triton as control.10 first 3 age mid-term larvas of each processing, totally 4 repetitions.Beet armyworm after processing
It is 27 ± 1 DEG C, photoperiod 16 that larva, which is put into temperature,:8h (L:D), RH is to be cultivated in 60~80% constant incubator, connects worm 5
Inspection result after it, polypide is touched with writing brush during inspection, the coordinated movement of various economic factors is unable to as death standard using larva.Its result such as institute of table 5
Show.
Table 5
Data processing：Toxicity regression line, LC are calculated using U.S. EPA software50Value and its 95% confidence limit.According to chemical combination
Thing LC50Whether 95% confidence limit of value is overlapping to differentiate whether Virulence Difference is notable.Its result is as shown in table 6.
Table 6
| Test compound | Toxicity regression line | LC50Value and 95% confidence limit（mg/L） | Relative virus force index |
| A6 | 1.4534+3.1161X | 13.745（11.240~16.373） | 0.42 |
| A1 | 2.1912+2.6387X | 11.600（9.128~14.072） | 0.50 |
| Pyridalyl | 3.0517+2.5597X | 5.769（4.525~7.017） | 1.0 |
By table 6, A1 and A6 also have preferable insecticidal activity to beet armyworm.
Test case 4
This test case is used for insecticidal activity of the dichloro allyl ether series compound to prodenia litura for illustrating the present invention.
Reagent agent：Compound A1, A6 and pyridalyl.
For trying insect：Prodenia litura（Prodenia litura(Fabricius)）In May, 2009 is by Jiangsu's agriculture science
Institute presents, and is the sensitive strain in indoor feeding more generations.
Drug solution preparing：Use assay balance（0.0001g）The active compound of certain mass is weighed, with acetone solution and is configured to 1 weight
Measure % solution（Mother liquor）.The mother liquor of measured amounts, add the distilled water containing 0.1 weight % Tween-80s（Hereinafter referred to as 0.1%
Triton）Dilution is configured to the decoction of series concentration gradient, standby.
Test method：Diameter 5cm cabbage leaf butterfly is impregnated into 20s in above-mentioned decoction respectively, naturally dry is extremely after taking-up
Without bright water, using the 0.1%Triton aqueous solution as control.10 first 3 age mid-term larvas of each processing, totally 4 repetitions.It is oblique after processing
It is 27 ± 1 DEG C, photoperiod 16 that Autographa spp larva, which is put into temperature,:8h(L:D), RH is to be trained in 60~80% constant incubator
Support, connect worm inspection result after 5 days, touch polypide with writing brush during inspection, the coordinated movement of various economic factors is unable to as death standard using larva.Its result
As shown in table 7.
Table 7
Data processing：Toxicity regression line, LC are calculated using U.S. EPA software50Value and its 95% confidence limit.According to chemical combination
Thing LC50Whether 95% confidence limit of value is overlapping to differentiate whether Virulence Difference is notable.Its result is as shown in table 8.
Table 8
| Test compound | Toxicity regression line | LC50Value and 95% confidence limit（mg/L） | Relative virus force index |
| A6 | 2.1024+2.0743X | 24.941（18.659~31.773） | 0.86 |
| A1 | 1.3940+2.3886X | 32.338（25.257~40.059） | 0.67 |
| Pyridalyl | 0.7506+3.1877X | 21.531（17.454~25.435） | 1.0 |
By table 8, A1 and A6 also have preferable insecticidal activity to prodenia litura.
Test case 5
This test case is used for insecticidal activity of the dichloro allyl ether series compound to diamondback moth for illustrating the present invention.
Reagent agent：Compound A1, A6 and pyridalyl.
For trying insect：Diamondback moth（Plutella xyllostella(Linnaeus)）In March, 2012 is by northwest agricultural section
Plant protection institute of skill university presents, and is the sensitive strain in indoor feeding more generations.
Drug solution preparing：Use assay balance（0.0001g）The active compound of certain mass is weighed, with acetone solution and is configured to 1 weight
Measure % solution（Mother liquor）.The mother liquor of measured amounts, add the distilled water containing 0.1 weight % Tween-80s（Hereinafter referred to as 0.1%
Triton）Dilution is configured to the decoction of series concentration gradient, standby.
Test method：Diameter 5cm cabbage leaf butterfly is impregnated into 20s in above-mentioned decoction respectively, naturally dry is extremely after taking-up
Without bright water, using 0.1%Triton as control.10 first 3 age mid-term larvas of each processing, totally 4 repetitions.Beet armyworm after processing
It is 25 ± 1 DEG C, photoperiod 16 that larva, which is put into temperature,:8h (L:D), RH is to be cultivated in 60~80% constant incubator, connects worm 3
Inspection result after it, polypide is touched with writing brush during inspection, the coordinated movement of various economic factors is unable to as death standard using larva.Its result such as institute of table 9
Show.
Table 9
Data processing：Toxicity regression line, LC are calculated using U.S. EPA software50Value and its 95% confidence limit.According to chemical combination
Thing LC50Whether 95% confidence limit of value is overlapping to differentiate whether Virulence Difference is notable.Its result is as shown in table 10.
Table 10
| Test compound | Toxicity regression line | LC50Value and 95% confidence limit（mg/L） | Relative virus force index |
| A6 | 1.9546+3.0298X | 10.119（8.582~11.722） | 0.31 |
| A1 | 3.6745+2.8978X | 2.867（2.460~3.446） | 1.1 |
| Pyridalyl | 3.5877+2.8756X | 3.098（2.649~3.780） | 1.0 |
By table 10, A1 and A6 also have preferable insecticidal activity to diamondback moth, and A1 insecticidal activity is better than
Pyridalyl.
Test case 6
This test case is used for insecticidal activity of the dichloro allyl ether series compound to prodenia litura for illustrating the present invention.
Prevent and treat prodenia litura field test：According to medicine inspecting institute of the Ministry of Agriculture, " GB-T17980.13-2000 agricultural chemicals field efficacy tries
Test the lepidopterous larvae of criterion (one)-insecticide control brassicaceous vegetable " regulation, carry out the field efficacy of prodenia litura
Experiment.
Subjects：Prodenia litura（Prodenia litura（Fabricius）；
Trial crops：Asparagus
Arable farming and environmental condition：Experimental plot is located at academy of agricultural sciences of Shaoxing, Zhejiang Province city, and experimental field water and fertilizer condition is preferable, plants
Training management is consistent, Pass Test requirement.
Medicament：A1 is 5 weight % missible oil（Referred to as：5%A1EC）, A8 be 5 weight % missible oil（Referred to as：5%A8EC）And pyridine
Worm propyl ether is 5 weight % missible oil（Referred to as：5% pyridalyl EC）.
Cultivate cell arrangement（Cell distribution see the table below）：
| 1 | 2 | 3 | 4 |
| 5 | 6 | 7 | 8 |
Plot area：10 square metres.
Application method：By above-mentioned medicament with active ingredient, after being diluted with water to each concentration, Taizhou City of Zhejiang Province Guangfeng is used
The 3Wbs-16 type hand sprayers of Su Ye Co., Ltds production（Operating pressure is 0.2mPa.）Spraying treatment is carried out to asparagus（This
Experiment amounts to dispenser 1 time）, medicament usage amount is 40 liters/mu.Investigated respectively in dispenser after 4 days and 9 days, investigation method is
Investigate per experimental plot at 3 points, every 1 plant of asparagus, record borer population living.
Drug effect computational methods：According to investigation result, preventive effect is calculated according to formula below.Test data is newly multiple using Deng Kenshi
Range method（DMRT）Carry out statistical analysis.Its result is as shown in table 11.
Table 11
Note：Blank column data are prodenia litura worm amount.
By table 11, the processing of 5%A6EC400mg/L and 5%A6EC200mg/L dosage was to 4 days and 9 after prodenia litura medicine
It preventive effect is respectively 91.16%, 90.48% and 100%, 100%, anti-with the pyridalyl EC200mg/L of comparison medicament 5% processing
It is close to imitate (91.16% and 100%).In addition, do not found in this test case to having harmful effect for studying thing.
Test case 6
This test case is used for insecticidal activity of the dichloro allyl ether series compound to diamondback moth for illustrating the present invention.
Prevent and treat diamondback moth field test
Subjects：Wild cabbage diamondback moth Plutella xylostella (L.)；
Trial crops and kind：Greenhouse cultivation wild cabbage, kind are strength 50.
Test medicine：5%A1EC, 5% pyridalyl EC and cypermethrin are 4.5 weight % missible oil（Referred to as 4.5% chlorine cyanogen
Chrysanthemum ester EC, is purchased from Weierda Chemical Co., Ltd., Zhejiang）；
Dosing see the table below with numbering：
Cell arrangement：Cell is distributed according to completely random district's groups, south-north direction, and specific cell distribution see the table below：
| A | I | D | C |
| B | H | F | H |
| C | G | B | E |
| D | E | I | A |
| E | F | C | G |
| F | D | H | I |
| G | C | A | D |
| H | B | G | B |
| I | A | E | F |
Plot area or plant number：15 square metres.
Number of repetition：4 times.
Application method：Plant leaf positive and negative even spraying, first handles test medicine, is sprayed successively from low concentration to high concentration
Mist, then handles comparison medicament, cleans sprayer during dressing agent.
Spraying equipment：Use and " close beautiful " HM-16A type knapsack electric sprayers, 0.2~0.4MPa of operating pressure position, purchase
In Zhongshan Hemei Electric Appliance Co., Ltd..
Spraying times：Test dispenser once, be the wild cabbage heading stage during dispenser, each age worm state of diamondback moth has.
Medicament usage amount：750 kilograms/hectare.
Investigation method：According to " GB-T17980.13-2000 pesticide field efficacy medicine tests criterion (one)-insecticide control ten
The regulation of the lepidopterous larvae of Zi Hua sections vegetables " is carried out.2 plants are investigated using 5 points of samplings, at every, investigate 10 altogether per experimental plot
Strain wild cabbage, investigate every plant of upper all borer populations living.
Drug effect computational methods：
According to investigation result, preventive effect is calculated according to formula below.Test data uses Deng Kenshi duncan's new multiple range methods（DMRT）
Carry out statistical analysis.Its result is as shown in table 12.
Table 12
In table, " kg " in " dosage (mg/kg) " represents the weight of missible oil.
By table 13,5%A1EC has anti-well under 50~400 mg/kg dosage to wild cabbage diamondback moth
Effect, the preventing and treating available for wild cabbage diamondback moth.The medicament quick-acting is preferable, after medicine the preventive effect of 1 day be 59.8%~80.8%, higher than pair
At the preventive effect handled according to the pyridalyl EC of medicament 5%, the preventive effect of the mg/kg of medicament 200 and 4.5% effective cypermethrin EC
The preventive effect of reason is suitable；4 days after medicine, the preventive effect of the medicament 69.2%~90.9%, higher than same dosage pyridalyl handle it is anti-
Imitate, preventive effect significant difference under high dose, the preventive effect phase that the preventive effect of the mg/kg of medicament 200 is handled with 4.5% cypermethrin EC
When；8 days after medicine, the preventive effect of the medicament reaches highest, is 67.9%~99.3%, 50, the preventive effect of 100 mg/kgs processing and pyridine
Worm propyl ether preventive effect is suitable, and the preventive effect of its 100 mg/kg processing is suitable with the preventive effect that the mg/kg of cypermethrin 50 is handled, its
200th, the preventive effect of 400 mg/kgs processing is higher than the preventive effect for carrying out that comparison medicament, and difference is extremely notable；14 days after medicine, the medicament
Preventive effect still 70.2%~98.6%, be better than the preventive effect of comparison medicament, the lasting period was longer, at 14 days or so.In addition, experimental period
Between, do not find that medicament produces the harmful effects such as observable poisoning to crop.
The preferred embodiment of the present invention described in detail above, still, the present invention are not limited in above-mentioned embodiment
Detail, in the range of the technology design of the present invention, a variety of simple variants can be carried out to technical scheme, this
A little simple variants belong to protection scope of the present invention.
The preferred embodiment of the present invention described in detail above, still, the present invention are not limited in above-mentioned embodiment
Detail, in the range of the technology design of the present invention, a variety of simple variants can be carried out to technical scheme, this
A little simple variants belong to protection scope of the present invention.
It is further to note that each particular technique feature described in above-mentioned embodiment, in not lance
In the case of shield, can be combined by any suitable means, in order to avoid unnecessary repetition, the present invention to it is various can
The combination of energy no longer separately illustrates.
In addition, various embodiments of the present invention can be combined randomly, as long as it is without prejudice to originally
The thought of invention, it should equally be considered as content disclosed in this invention.
Claims (9)
1. a kind of dichloro allyl ether series compound, it is characterised in that the dichloro allyl ether series compound is following formulas (1)
The compound of shown structure,
In formula (1), R1For selected from following radicals In one kind；
N is 0-3 integer.
2. compound according to claim 1, wherein, the dichloro allyl ether series compound is following compound A1-
One kind in A3 and A5-A6,
3. compound according to claim 2, wherein, the dichloro allyl ether series compound be compound A1, A2 or
A6。
4. compound according to claim 3, wherein, the dichloro allyl ether series compound is compound A1 or A6.
5. a kind of insecticide, it is characterised in that the compound that the insecticide contains in claim 1-4 described in any one is made
For active component.
6. application of the insecticide described in claim 5 in terms of pest control.
7. application according to claim 6, wherein, the insect is Lepidoptera (Lepidoptera) or coleoptera
(Coleoptera) insect.
8. application according to claim 7, wherein, the insect is Lepidoptera (Lepidoptera) insect.
9. application according to claim 8, wherein, the insect of the Lepidoptera (Lepidoptera) is bollworm, pickles
Moth, prodenia litura and beet armyworm.
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| CN109384713B (en) * | 2017-08-14 | 2021-01-01 | 华中师范大学 | Dichloropropylene ether compound containing azido pyridine, preparation method and application thereof, and pesticide |
| CN111454204B (en) * | 2019-01-22 | 2023-10-17 | 华中师范大学 | Cyanopyridine-containing dichloropropene ether compound, preparation method and application thereof, and pesticide |
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