CN103168793B - Meperfluthrin-containing compound insecticidal composition and application thereof - Google Patents
Meperfluthrin-containing compound insecticidal composition and application thereof Download PDFInfo
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Abstract
The invention provides an insecticide composition which is composed of an active compound component and an auxiliary component, wherein the active compound component accounts for 1-60 wt% of the insecticide composition, and is compounded from a component A and a component B in a weight ratio of 1:50-50:1; the component A is a pyrethroid compound of which the structure satisfies the following formula; and the component B is a chitin synthesis inhibitor. By compounding, the insecticidal composition provided by the invention can widen the insecticidal spectrum and have certain synergistic action in application.
Description
Technical field
The present invention relates to a kind of insecticides, be specifically related to a kind of complex insecticidal composition containing chlorine fluorine ether chrysanthemum ester.
Background technology
Chlorine fluorine ether chrysanthemum ester, English name (Meperfluthrin), be the new construction pyrethroid compound with independent intellectual property right that the exploitation of agrochemical work joint-stock company is raised in Jiangsu, this compound is mainly used in domestic hygiene preparation at present.
Again because the acid moieties of chlorine fluorine ether chrysanthemum ester is DV acid, cause its water splitting with at present large Tanaka use as cypermethrin etc. quite, therefore chlorine fluorine ether chrysanthemum ester has the feasibility applied large Tanaka.Prove through lot of experiments, chlorine fluorine ether chrysanthemum ester single dose uses in land for growing field crops can prevent and treat part target, and quick-acting is its feature.
Chitin suppresses class mainly to suppress the chitinous synthesis of insect cuticle, in this compounds, most product is slow to target effect, generally take effect needs about 10 days, there is good lasting effect, the mechanism of action is completely different from chlorine fluorine ether chrysanthemum ester, this exist with the chlorine fluorine ether chrysanthemum ester of quick-acting theoretically composite may, we test further and find that chitin to suppress in class part of compounds and chlorine fluorine ether chrysanthemum ester is composite and even have certain synergistic effect.Chlorine fluorine ether chrysanthemum ester single dose kind is promoted if consider to use in land for growing field crops, resistance can be produced very soon, and single dose use cost is relatively high, therefore we select complex preparation, be so more of value to delay noval chemical compound chlorine fluorine ether chrysanthemum ester in use resistance generation and reduce active ingredient usage amount.
Summary of the invention
An object of the present invention is to provide a kind of good disinsection effect, and drug cost is low, and composite have synergy and the complex insecticidal composition containing chlorine fluorine ether chrysanthemum ester not easily developed immunity to drugs.
Another object of the present invention is to the Synthesis and applications that above-mentioned Pesticidal combination is provided.
Above-mentioned purpose of the present invention is achieved through the following technical solutions:
A kind of insecticides, it is made up of former medicine component and auxiliary element, and former medicine component accounts for 1 ~ 60% of composition total weight, former medicine component by component A and B component by 1: 50 ~ 50: 1 weight ratio compositely to form; Described component A is the pyrethroid compound that structure meets following formula; Described B component is chitin synthesis inhibitor.
Component A described in the present invention can be 2,3,5,6-tetrafluoro-4-methoxymethyl benzyl base-3-(2,2-dichloroethylene)-2,2-dimethyl cyclopropane carboxylic acid's esters all stereoisomers in any one or two or more mixtures, these stereoisomers can be:
Rich dextrorotation 2,3,5,6-tetrafluoro-4-methoxymethyl benzyl base-3-(2,2-dichloroethylene)-2,2-dimethyl cyclopropane carboxylic acid's ester of cyclopropane 1 effective body burden >=55% of R configuration;
Cyclopropane 1 absolute configuration is R configuration, 1,32,3,5,6-tetrafluoro-4-methoxymethyl benzyl bases-(1R)-3-(2,2-dichloroethylene)-2,2-dimethyl cyclopropane carboxylic acid's esters not distinguishing the dextrorotation of cis-trans isomerism;
Cyclopropane 1 absolute configuration is R configuration, 1, and 3 is trans-isomeric 2,3,5,6-tetrafluoro-4-methoxymethyl benzyl base-(1R, 3S)-3-(2,2-dichloroethylene)-2,2-dimethyl cyclopropane carboxylic acid's esters (ISO called after chlorine fluorine ether chrysanthemum ester; Meperfluthrin);
Or
Cyclopropane 1 absolute configuration is R configuration, 1, and 3 is 2,3,5,6-tetrafluoro-4-methoxymethyl benzyl bases-(1R, 3R)-3-(2,2-dichloroethylene)-2,2-dimethyl cyclopropane carboxylic acid's ester of syn-isomerism.
The weight ratio of described component A and B component is preferably 1: 50 ~ 10: 1, and further preferably 1: 30 ~ 1: 1.
Described chitin synthesis inhibitor, preferably following any one:
No. II, flufenoxuron, chlorfluazuron, HEXAFLUMURON, methoxyfenozide, diflubenzuron, d ichlorbenzuron or d ichlorbenzuron.
Described chitin synthesis inhibitor is preferred HEXAFLUMURON further.
Described auxiliary element can be one or more the mixture in emulsifier, wetting agent, dispersant, disintegrant, antifreezing agent, thickener, defoamer, binding agent, filler, solvent or water.
Described emulsifier can be selected from alkyl benzene calcium sulfonate, OP series phosphate, phenyl phenol polyoxyethanyl ether phosphate, styrene polyoxyethylene ether ammonium sulfate salt, alkyl biphenyl ether disulfonic acid magnesium salts, triethanolamine salt, benzyl dimethyl phenol polyoxyethyl ether, peaceful newborn 36#, phenethyl phenol polyoxyethanyl polypropylene-base ether, ethylene oxide-propylene oxide block copolymer, polyoxyethylene nonylphenol ether, castor oil polyoxyethylene ether, alkylaryl polyoxyethylene polyoxypropylene ether, alkylaryl polyoxyethylene poly-oxygen propylene aether, Span series, one or more in TWEEN Series or fat alcohol alcohol APEO,
Optional one or more in polycarboxylate, lignosulfonates, alkylphenol polyoxyethylene formaldehyde condensation products sulphate, alkyl benzene sulfonate calcium salt, naphthalene sulfonic acid-formaldehyde condensation product sodium salt, alkylphenol polyoxyethylene, aliphatic amine polyoxyethylene ether, polyoxyethylene carboxylate or fatty acid glyceride APEO of described dispersant;
Described wetting agent can be selected from alkylphenol-polyethenoxy base ether formaldehyde condensation products sulphate, alkylbenzene polyoxyethylene ether phosphate, phenethyl phenol polyethenoxy base ether phosphate, alkyl sulfate, alkylsulfonate, naphthalene sulfonate, lauryl sodium sulfate, Nekal BX, wetting and penetrating agent F or DBSA one or more;
Optional one or more in ammonium sulfate, bentonite, urea, succinic acid, sodium bicarbonate, aluminium chloride or citric acid of described disintegrant;
Described antifreezing agent can be selected from ethylene glycol, propane diols, glycerine, glycerine or urea one or more;
Described thickener can be selected from xanthans, CMC, hydroxyethylcellulose, methylcellulose, Magnesiumaluminumsilicate or polyvinyl alcohol one or more;
Described defoamer can be selected from silicone compound, silicone oil, C8-10 aliphatic alcohols compound or C10-20 saturated fat acid compounds one or more;
Optional one or more in polyvinyl alcohol, dextrin, CMC, polyvinylpyrrolidone, sodium alginate or wooden calcium sulfonate of described binding agent;
Described filler can be selected from kaolin, potter's clay, diatomite, bentonite, white carbon, attapulgite, starch or precipitated calcium carbonate one or more;
The solvent stated can be selected from methyl alcohol, ethanol, isopropyl alcohol, n-butanol, isobutanol, amylalcohol, toluene, dimethylbenzene, methyl how, in solvent naphtha 100#, solvent naphtha 150#, solvent naphtha 200#, benzinum, gasoline, kerosene, turpentine oil, cyclohexanone, methylisobutylketone one or more.
Pesticidal combination of the present invention can conventionally make various formulation, preferred missible oil, can wet-milling, suspending agent, water dispersible granules, and conventional formulation and the preparation method of these formulations are as follows:
Missible oil: the former medicine B component of former medicine component A+ totally 1% ~ 30%, emulsifier 6% ~ 12%, solvent supply 100%;
Missible oil preparation method: by former medicine dissolution solvent, then add emulsifier, mixed dissolution under stirring, form single-phase transparent liquid;
Can wet-milling: the former medicine B component of former medicine component A+ totally 1% ~ 60%, wetting agent 1% ~ 4%, dispersant 1% ~ 8%, filler supply 100%;
Can wet-milling preparation method: former medicine and wetting agent, dispersant, filler are mixed, pulverizes through airslide disintegrating mill one or many;
Suspending agent: the former medicine B component of former medicine component A+ totally 1% ~ 50%, wetting agent 1% ~ 4%, dispersant 1% ~ 10%, antifreezing agent 1% ~ 8%, thickener 0.1% ~ 1%, defoamer 0.1% ~ 0.5%, water supplies 100%;
Suspending agent preparation method: former medicine, wetting agent, dispersant, antifreeze and water are dropped into ball mill in proportion and is pulverized and mixed, then add thickener, defoamer and water and carry out ball milling, after ball milling, particle diameter is generally less than 5 microns, then adds residue water and carry out modulating;
Water dispersible granules: the former medicine B component of former medicine component A+ totally 1% ~ 50%, wetting agent 1% ~ 4%, dispersant 1% ~ 10%, disintegrant 1% ~ 4%, binding agent 0.5% ~ 8%, filler supply 100%;
Water dispersible granules preparation method: former medicine, wetting agent, dispersant, disintegrant, filler are mixed, pulverizes with micro jet, adding binding agent through mediating, then adding after carrying out granulation, drying, screening in fluidized-bed granulation dryer.
The present invention also provides the described application of Pesticidal combination in control agricultural pests.
Described agricultural pests comprises the insect of Lepidoptera, thrips, Homoptera, diptera and mite class, further illustrate, pest control comprises Thripidae, Miridae, Pentatomiddae, Cicadellidae, Delphacidae, Aleyrodidae, Aphidiadae, Mian Jie section, diamond-back moth section, Pyralidae, Noctuidae, Lymantriidae, Sulfur butterfly, Carposinidae, Chrysomelidae, Culculionidae, Cecidomyiidae, Tephritidae, Agromyzidae, Anthomyiidae, Tetranychidae, leeched line mite section, Ye Zhao mite section, Eriophyidae etc.
Embodiment
Example of formulations 1:
Chlorine fluorine ether chrysanthemum ester and hexaflumuron compounded ratio are 1: 1, actual feed intake into 3g chlorine fluorine ether chrysanthemum ester, 3g HEXAFLUMURON, alkyl benzene calcium sulfonate 6g, alkylaryl polyoxyethylene polyoxypropylene ether 5g, solvent naphtha 150# mend to 100g, throw and finish the i.e. obtained 6% chlorine fluorine ether chrysanthemum ester 5 percent of hexaflumuron emulsifiable concentrate that stirs, be example of formulations 1.
Example of formulations 2 ~ 5
According to the compound proportion of chlorine fluorine ether chrysanthemum ester and HEXAFLUMURON in table 1, auxiliary element is alkyl benzene calcium sulfonate 6g, alkylaryl polyoxyethylene polyoxypropylene ether 5g, solvent naphtha 150# mend to 100g, throws respectively and finishes the i.e. obtained example of formulations 2 ~ 5 that stirs.
Table 1
| Embodiment is numbered | Chlorine fluorine ether chrysanthemum ester (g) | HEXAFLUMURON (g) | Compound proportion |
| 2 | 0.1 | 5 | 1∶50 |
| 3 | 0.1 | 3 | 1∶30 |
| 4 | 0.5 | 2.5 | 1∶5 |
| 5 | 5 | 0.5 | 10∶1 |
Example of formulations 6
Chlorine fluorine ether chrysanthemum ester and chlorfluazuron compound proportion are 1: 5, actual feed intake into 0.5g chlorine fluorine ether chrysanthemum ester, 2.5g chlorfluazuron, alkyl benzene calcium sulfonate 6g, alkylaryl polyoxyethylene polyoxypropylene ether 5g, solvent naphtha 150# mend to 100g, throw and finish the i.e. obtained 3% chlorine fluorine ether chrysanthemum ester 5 percent of hexaflumuron emulsifiable concentrate that stirs, be example of formulations 6.
Example of formulations 7
Chlorine fluorine ether chrysanthemum ester and urea compounded ratio are 1: 9, actual feed intake into 6g chlorine fluorine ether chrysanthemum ester, 54g diflubenzuron, 3g naphthalene sulfonate, 4g lignosulfonates, kaolin mend to 100g, pulverizing i.e. obtained 60% chlorine fluorine ether chrysanthemum ester diflubenzuron through airslide disintegrating mill after mixing can wet-milling, is example of formulations 7.
Example of formulations 8
Chlorine fluorine ether chrysanthemum ester and flufenoxuron compound proportion are 1: 9, actual feed intake into 0.5g efficient chlorine fluorine cyanogen, 4.5g flufenoxuron, 6g neopelex, 4g alkylnaphthalene sulfonate formaldehyde condensation products, 1g modified starch, 15g ammonium sulfate, diatomite mend to 100g.Co-grinding is granulated becomes 5% chlorine fluorine ether chrysanthemum ester flufenoxuron water dispersible granules, is example of formulations 8.
Example of formulations 9
Chlorine fluorine ether chrysanthemum ester and methoxyfenozide compound proportion are 1: 9, actual feed intake into 1g chlorine fluorine ether chrysanthemum ester, 9g methoxyfenozide, 5g fatty acid glyceride APEO, 3g polycarboxylate, 5g propane diols, 0.1g xanthans, 0.5g silicone compound, water mend to 100g.Mixed grinding makes 10% chlorine fluorine ether chrysanthemum ester methoxyfenozide suspending agent, is example of formulations 9.
Example of formulations 10
Chlorine fluorine ether chrysanthemum ester and d ichlorbenzuron compound proportion are 1: 15, actual feed intake into 2g chlorine fluorine ether chrysanthemum ester, 30g d ichlorbenzuron, 4g polyoxyethylene carboxylate, 3g naphthalene sulfonic acid-formaldehyde condensation product sodium salt, 5g ethylene glycol, 0.1g xanthans, 1g Magnesiumaluminumsilicate, 0.5g silicone compound, water mend to 100g.Mixed grinding makes 32% chlorine fluorine ether chrysanthemum ester Chlorbenzuron deflocculant, is example of formulations 10.
Example of formulations 11
Cis chlorine fluorine ether chrysanthemum ester (2,3,5,6-tetrafluoro-4-methoxymethyl benzyl base-(1R, 3R)-3-(2,2-dichloroethylene)-2,2-dimethyl cyclopropane carboxylic acid's esters) with d ichlorbenzuron II compound proportion be 1: 10, actual feed intake into 1g chlorine fluorine ether chrysanthemum ester, No. II, 10g d ichlorbenzuron, 3.5g polyoxyethylene carboxylate, 3g naphthalene sulfonic acid-formaldehyde condensation product sodium salt, 5g ethylene glycol, 0.2g xanthans, 1g Magnesiumaluminumsilicate, 0.5g silicone compound, water mend to 100g.Mixed grinding makes 11% chlorine fluorine ether chrysanthemum ester d ichlorbenzuron II suspending agent, is example of formulations 11.
Comparing embodiment 1
Feed intake 5g chlorine fluorine ether chrysanthemum ester, alkyl benzene calcium sulfonate 6g, alkylaryl polyoxyethylene polyoxypropylene ether 5g, solvent naphtha 150# benefit to 100g, throws and finish the i.e. obtained 5% chlorine fluorine ether chrysanthemum emulsifiable concentrate that stirs, be comparing embodiment 1.
Comparing embodiment 2
Feed intake 5g HEXAFLUMURON, alkyl benzene calcium sulfonate 6g, alkylaryl polyoxyethylene polyoxypropylene ether 5g, solvent naphtha 150# benefit to 100g, throws and finish the i.e. obtained 5% Aphox missible oil that stirs, be comparing embodiment 2.
Comparing embodiment 3
Feed intake 5g Cyhalothrin, alkyl benzene calcium sulfonate 6g, alkylaryl polyoxyethylene polyoxypropylene ether 5g, solvent naphtha 150# benefit to 100g, throws and finish the i.e. obtained 5% Cyhalothrin missible oil that stirs, be comparing embodiment 3.
Application Example one: the raw test of control brassicaceous vegetable (wild cabbage) insect is tested
Target: lepidoptera pest diamond-back moth
Method: just embodiment 1 ~ 5 and comparing embodiment 1 ~ 3 dilute 7 gradient concentrations with clear water respectively, blank is made with clear water process, employing leaf dipping method measures, the leaching of diameter 2cm cabbage leaves is taken out air-dry after into the liquid 10 seconds, 3 are placed in each culture dish, if 3 repetitions, picking three diamondback moth larvae in age, picking 10 in each culture dish, then put into 25 DEG C of illumination boxs, investigation survival borer population respectively after 72 hours, calculates lethality, Mortality data by 7 concentration gradients, calculate virulence regression equation, finally obtain LC50.Measurement result following (table 2):
Table 2 Application Example one test result
| Example of formulations | Active ingredient | Formulation | Proportionate relationship | LC50(mg/L) |
| Example of formulations 1 | Chlorine fluorine ether chrysanthemum ester+HEXAFLUMURON | Missible oil | 1∶1 | 19.6 |
| Example of formulations 2 | Chlorine fluorine ether chrysanthemum ester+HEXAFLUMURON | Missible oil | 1∶50 | 47.8 |
| Example of formulations 3 | Chlorine fluorine ether chrysanthemum ester+HEXAFLUMURON | Missible oil | 1∶30 | 25.3 |
| Example of formulations 4 | Chlorine fluorine ether chrysanthemum ester+HEXAFLUMURON | Missible oil | 1∶5 | 16.9 |
| Example of formulations 5 | Chlorine fluorine ether chrysanthemum ester+HEXAFLUMURON | Missible oil | 10∶1 | 14.8 |
| Comparing embodiment 1 | Chlorine fluorine ether chrysanthemum ester | Missible oil | 12.0 | |
| Comparing embodiment 2 | HEXAFLUMURON | Missible oil | 54.2 | |
| Comparing embodiment 3 | Cyhalothrin | Missible oil | 29.8 |
By LC50 of composite embodiment each in the Application Example one and LC50 of single dose comparing embodiment, computational methods, with reference to the method being calculated mixture co-toxicity by toxicity index of Sun Yunpei, calculate co-toxicity coefficient.
The composite co-toxicity coefficient of table 3 the present invention measures
Test result shows, when chlorine fluorine ether chrysanthemum ester and fluorine tinkling of pieces of jade urea proportionate relationship are between 1: 50 ~ 10: 1, its co-toxicity coefficient is all greater than 100, and especially when proportionate relationship is between 1: 1 ~ 1: 30, its co-toxicity coefficient is all greater than 120, shows obvious synergistic effect.
Show with the data of the contrast of comparing embodiment 3 in addition, the formula activity after composite commonly uses single dose chrysanthemum ester weak effect unlike existing market.
Claims (5)
1. an insecticides, is characterized in that: it is made up of former medicine component and auxiliary element, and former medicine component accounts for 1 ~ 60% of insecticides gross weight, and former medicine component is formed by the weight ratio of 1:30 ~ 1:1 is composite by component A and B component; Described component A is the pyrethroid compound that structure meets following formula; Described B component is chitin synthesis inhibitor; Described chitin synthesis inhibitor is HEXAFLUMURON;
2. insecticides according to claim 1, is characterized in that: described component A is selected from one or more the mixture in following pyrethroid compound:
Rich dextrorotation 2,3,5,6-tetrafluoro-4-methoxymethyl benzyl base-3-(2,2-dichloroethylene)-2,2-dimethyl cyclopropane carboxylic acid's ester of cyclopropane 1 effective body burden >=55% of R configuration;
Cyclopropane 1 absolute configuration is R configuration, 1,32,3,5,6-tetrafluoro-4-methoxymethyl benzyl bases-(1R)-3-(2,2-dichloroethylene)-2,2-dimethyl cyclopropane carboxylic acid's esters not distinguishing the dextrorotation of cis-trans isomerism;
Cyclopropane 1 absolute configuration is R configuration, 1, and 3 is trans-isomeric 2,3,5,6-tetrafluoro-4-methoxymethyl benzyl bases-(1R, 3S)-3-(2,2-dichloroethylene)-2,2-dimethyl cyclopropane carboxylic acid's ester;
Or
Cyclopropane 1 absolute configuration is R configuration, 1, and 3 is 2,3,5,6-tetrafluoro-4-methoxymethyl benzyl bases-(1R, 3R)-3-(2,2-dichloroethylene)-2,2-dimethyl cyclopropane carboxylic acid's ester of syn-isomerism.
3. insecticides according to claim 1 is killing the application in getting rid of insects as pesticidal preparations.
4. application according to claim 3, is characterized in that: the formulation of described pesticidal preparations be missible oil, can wet-milling, suspending agent or water dispersible granules.
5. application according to claim 3, is characterized in that: described insect comprises the insect of Lepidoptera, thrips, Homoptera, diptera or mite class.
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| EP0031199A1 (en) * | 1979-12-21 | 1981-07-01 | Imperial Chemical Industries Plc | Substituted benzyl esters of cyclopropane carboxylic acids and their preparation, compositions containing them and methods of combating insect pests therewith, and substituted benzyl alcohols |
| CN101306997A (en) * | 2008-04-29 | 2008-11-19 | 江苏扬农化工股份有限公司 | Optically active pyrethroid compounds, method for preparing same and applications |
| CN101543225A (en) * | 2009-05-15 | 2009-09-30 | 江苏扬农化工股份有限公司 | Insecticide mother liquor and use thereof |
| CN101632379A (en) * | 2009-06-04 | 2010-01-27 | 江苏扬农化工股份有限公司 | Electrothermal pesticide liquid |
| CN101632378A (en) * | 2009-06-04 | 2010-01-27 | 江苏扬农化工股份有限公司 | Electrothermal pesticide tablet |
| CN101953364A (en) * | 2010-11-12 | 2011-01-26 | 江苏扬农化工股份有限公司 | Electric heating sanitary perfumed slice and application thereof |
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2011
- 2011-12-26 CN CN201110442679.6A patent/CN103168793B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0031199A1 (en) * | 1979-12-21 | 1981-07-01 | Imperial Chemical Industries Plc | Substituted benzyl esters of cyclopropane carboxylic acids and their preparation, compositions containing them and methods of combating insect pests therewith, and substituted benzyl alcohols |
| CN101306997A (en) * | 2008-04-29 | 2008-11-19 | 江苏扬农化工股份有限公司 | Optically active pyrethroid compounds, method for preparing same and applications |
| CN101543225A (en) * | 2009-05-15 | 2009-09-30 | 江苏扬农化工股份有限公司 | Insecticide mother liquor and use thereof |
| CN101632379A (en) * | 2009-06-04 | 2010-01-27 | 江苏扬农化工股份有限公司 | Electrothermal pesticide liquid |
| CN101632378A (en) * | 2009-06-04 | 2010-01-27 | 江苏扬农化工股份有限公司 | Electrothermal pesticide tablet |
| CN101953364A (en) * | 2010-11-12 | 2011-01-26 | 江苏扬农化工股份有限公司 | Electric heating sanitary perfumed slice and application thereof |
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