CN103168793A - 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 that contains chlorine fluorine ether chrysanthemum ester.
Background technology
Chlorine fluorine ether chrysanthemum ester, English name (Meperfluthrin) is the new construction pyrethroid compound with independent intellectual property right that the exploitation of agriculture chemical industry joint-stock company is raised in Jiangsu, this compound is mainly used in the domestic hygiene preparation at present.
Again because the acid moieties of chlorine fluorine ether chrysanthemum ester is DV acid, cause its photodissociation speed with at present large Tanaka use as cypermethrin etc. quite, so chlorine fluorine ether chrysanthemum ester has the feasibility of using large Tanaka.Prove through lot of experiments, chlorine fluorine ether chrysanthemum ester single dose is used in the land for growing field crops can prevent and treat the part target, and quick-acting is its characteristics.
It is mainly that the inhibition insect cuticle is chitinous synthetic that chitin suppresses class, in this compounds, most products are slow to the target effect, generally taking effect needs about 10 days, lasting effect is preferably arranged, the mechanism of action is fully different from chlorine fluorine ether chrysanthemum ester, this theoretically with the chlorine fluorine ether chrysanthemum ester of quick-acting exist composite may, we further test and find that chitin suppresses in class that part of compounds and chlorine fluorine ether chrysanthemum ester are composite even certain synergistic effect.If consider to use in the land for growing field crops popularization chlorine fluorine ether chrysanthemum ester single dose kind, can produce very soon resistance, and the single dose use cost is relatively high, so we select complex preparation, so more be of value to delay noval chemical compound chlorine fluorine ether chrysanthemum ester in use resistance generation and reduce the active ingredient usage amount.
Summary of the invention
One of purpose of the present invention is to provide a kind of good disinsection effect, and drug cost is low, the composite complex insecticidal composition that contains chlorine fluorine ether chrysanthemum ester that synergy is arranged and be difficult for developing immunity to drugs.
Another object of the present invention is to provide preparation and the application of above-mentioned Pesticidal combination.
Above-mentioned purpose of the present invention is achieved through the following technical solutions:
A kind of insecticides, it is comprised of former medicine component and auxiliary element, and former medicine component accounts for 1～60% of composition total weight, and former medicine component is pressed the composite formation of weight ratio of 1: 50～50: 1 by component A and B component; Described component A is the pyrethroid compound that structure satisfies 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, the 2-dichloroethylene)-2, any one in all stereoisomers of 2-dimethyl cyclopropane carboxylic acid ester or two or more mixtures, these stereoisomers can be:
The rich dextrorotation 2,3,5 of 1 the effective body burden of R configuration 〉=55% of cyclopropane, 6-tetrafluoro-4-methoxymethyl benzyl base-3-(2,2-dichloroethylene)-2,2-dimethyl cyclopropane carboxylic acid ester;
1 absolute configuration of cyclopropane is 2,3,5 of R configuration, 1,3 dextrorotation of not distinguishing cis-trans isomerism, 6-tetrafluoro-4-methoxymethyl benzyl base-(1R)-3-(2,2-dichloroethylene)-2,2-dimethyl cyclopropane carboxylic acid ester;
1 absolute configuration of cyclopropane is that R configuration, 1,3 are trans-isomeric 2,3,5,6-tetrafluoro-4-methoxymethyl benzyl base-(1R, 3S)-3-(2,2-dichloroethylene)-2,2-dimethyl cyclopropane carboxylic acid ester (ISO called after chlorine fluorine ether chrysanthemum ester; Meperfluthrin);
Perhaps
1 absolute configuration of cyclopropane is that R configuration, 1,3 are 2,3,5 of syn-isomerism, 6-tetrafluoro-4-methoxymethyl benzyl base-(1R, 3R)-3-(2,2-dichloroethylene)-2,2-dimethyl cyclopropane carboxylic acid ester.
The weight ratio of described component A and B component is preferably 1: 50～and 10: 1, further preferred 1: 30～1: 1.
Described chitin synthesis inhibitor, preferred following any one:
Flufenoxuron, fluorine pyridine urea, HEXAFLUMURON, methoxyfenozide, diflubenzuron, young urea or No. II, the young urea of going out go out.
The further preferred HEXAFLUMURON of described chitin synthesis inhibitor.
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 polyoxy ethyl ether phosphate, styrene polyoxyethylene ether ammonium sulfate salt, alkyl biphenyl ether disulfonic acid magnesium salts, triethanolamine salt, benzyl dimethyl phenol polyoxy ethyl ether, peaceful newborn 36#, phenethyl phenol polyoxy ethyl polypropylene-base ether, ethylene oxide-propylene oxide block copolymer, polyoxyethylene nonylphenol ether, castor oil polyoxyethylene ether, alkylaryl polyoxyethylene polyoxypropylene ether, the alkylaryl polyoxyethylene poly-oxygen propylene aether, sapn series, one or more in the pure APEO of tween series or fat,
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 one or more in 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;
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 one or more in ethylene glycol, propane diols, glycerine, glycerine or urea;
Described thickener can be selected from one or more in xanthans, CMC, hydroxyethylcellulose, methylcellulose, Magnesiumaluminumsilicate or polyvinyl alcohol;
Described defoamer can be selected from one or more in silicone compound, silicone oil, C8-10 aliphatic alcohols compound or C10-20 saturated fat acid compounds;
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 one or more in kaolin, potter's clay, diatomite, bentonite, white carbon, attapulgite, starch or precipitated calcium carbonate;
How the solvent of stating can be selected from methyl alcohol, ethanol, isopropyl alcohol, n-butanol, isobutanol, amylalcohol, toluene, dimethylbenzene, methyl, 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 be made various formulations according to conventional method, but preferred missible oil 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%;
The missible oil preparation method: in former medicine dissolution solvent, then add emulsifier, mixed dissolution under stirring action forms single-phase transparent liquid and gets final product;
But 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%;
But wet-milling preparation method: former medicine and wetting agent, dispersant, filler are mixed, get final product through the pulverizing of 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 supply 100%;
The suspending agent preparation method: former medicine, wetting agent, dispersant, antifreeze and water are dropped into ball mill in proportion be pulverized and mixed, then add thickener, defoamer and water to carry out ball milling, after ball milling, particle diameter is generally less than 5 microns, then adds residue water to modulate and get final product;
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, pulverize with micro jet, add binding agent through mediating, then add and carry out in the fluidized bed prilling dryer getting final product after granulation, drying, screening.
The present invention also provides the application of described Pesticidal combination aspect the 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, cotton a red-spotted lizard section, diamond-back moth section, Pyralidae, Noctuidae, Lymantriidae, Sulfur butterfly, Carposinidae, Chrysomelidae, Culculionidae, Cecidomyiidae, Tephritidae, Agromyzidae, Anthomyiidae, Tetranychidae, leeched line mite section, leaf pawl mite section, Eriophyidae etc.
Embodiment
FORMULATION EXAMPLE 1:
Chlorine fluorine ether chrysanthemum ester and hexaflumuron compounded ratio are 1: 1, actual feeding intake mended to 100g for 3g chlorine fluorine ether chrysanthemum ester, 3g HEXAFLUMURON, alkyl benzene calcium sulfonate 6g, alkylaryl polyoxyethylene polyoxypropylene ether 5g, solvent naphtha 150#, throw complete stirring and namely make 6% chlorine fluorine ether chrysanthemum ester 5 percent of hexaflumuron emulsifiable concentrate, be FORMULATION EXAMPLE 1.
FORMULATION EXAMPLE 2～5
According to the compound proportion of chlorine fluorine ether chrysanthemum ester and HEXAFLUMURON in table 1, auxiliary element is that alkyl benzene calcium sulfonate 6g, alkylaryl polyoxyethylene polyoxypropylene ether 5g, solvent naphtha 150# mend to 100g, throws respectively complete stirring and namely makes FORMULATION EXAMPLE 2～5.
Table 1
| The embodiment numbering | 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 |
FORMULATION EXAMPLE 6
Chlorine fluorine ether chrysanthemum ester and fluorine pyridine urea compound proportion are 1: 5, actual feeding intake mended to 100g for 0.5g chlorine fluorine ether chrysanthemum ester, 2.5g fluorine pyridine urea, alkyl benzene calcium sulfonate 6g, alkylaryl polyoxyethylene polyoxypropylene ether 5g, solvent naphtha 150#, throw complete stirring and namely make 3% chlorine fluorine ether chrysanthemum ester 5 percent of hexaflumuron emulsifiable concentrate, be FORMULATION EXAMPLE 6.
FORMULATION EXAMPLE 7
Chlorine fluorine ether chrysanthemum ester and urea compounded ratio are 1: 9, actual feeding intake mended to 100g for 6g chlorine fluorine ether chrysanthemum ester, 54g diflubenzuron, 3g naphthalene sulfonate, 4g lignosulfonates, kaolin, namely make 60% chlorine fluorine ether chrysanthemum ester diflubenzuron wet-milling but mix to pulverize by airslide disintegrating mill, be FORMULATION EXAMPLE 7.
FORMULATION EXAMPLE 8
Chlorine fluorine ether chrysanthemum ester and flufenoxuron compound proportion are 1: 9, and actual feeding intake mended to 100g for the efficient chlorine fluorine of 0.5g cyanogen, 4.5g flufenoxuron, 6g neopelex, 4g alkylnaphthalene sulfonate formaldehyde condensation products, 1g modified starch, 15g ammonium sulfate, diatomite.Co-grinding is granulated becomes 5% chlorine fluorine ether chrysanthemum ester flufenoxuron water dispersible granules, is FORMULATION EXAMPLE 8.
FORMULATION EXAMPLE 9
Chlorine fluorine ether chrysanthemum ester and methoxyfenozide compound proportion are 1: 9, and actual feeding intake mended to 100g for 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.Mixed grinding is made 10% chlorine fluorine ether chrysanthemum ester methoxyfenozide suspending agent, is FORMULATION EXAMPLE 9.
FORMULATION EXAMPLE 10
Chlorine fluorine ether chrysanthemum ester is 1: 15 with the young urea compound proportion that goes out, and actual feeding intake mended to 100g for go out young urea, 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 of 2g chlorine fluorine ether chrysanthemum ester, 30g.Mixed grinding is made 32% chlorine fluorine ether chrysanthemum ester Chlorbenzuron deflocculant, is FORMULATION EXAMPLE 10.
FORMULATION EXAMPLE 11
Cis chlorine fluorine ether chrysanthemum ester (2,3,5,6-tetrafluoro-4-methoxymethyl benzyl base-(1R, 3R)-3-(2, the 2-dichloroethylene) be-2,2-dimethyl cyclopropane carboxylic acid ester) 1: 10 with the young urea II compound proportion that goes out, actual feeding intake mended to 100g for go out No. II, young urea, 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 of 1g chlorine fluorine ether chrysanthemum ester, 10g.Mixed grinding is made the 11% chlorine fluorine ether chrysanthemum ester young urea II suspending agent that goes out, and is FORMULATION EXAMPLE 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# mended to 100g, throws that finishing stirs namely makes 5% chlorine fluorine ether chrysanthemum emulsifiable concentrate, is comparing embodiment 1.
Comparing embodiment 2
Feed intake 5g HEXAFLUMURON, alkyl benzene calcium sulfonate 6g, alkylaryl polyoxyethylene polyoxypropylene ether 5g, solvent naphtha 150# mended to 100g, throws that finishing stirs namely makes 5% Aphox missible oil, is comparing embodiment 2.
Comparing embodiment 3
Feed intake 5g Cyhalothrin, alkyl benzene calcium sulfonate 6g, alkylaryl polyoxyethylene polyoxypropylene ether 5g, solvent naphtha 150# mended to 100g, throws that finishing stirs namely makes 5% Cyhalothrin missible oil, is comparing embodiment 3.
Application Example one: control brassicaceous vegetable (wild cabbage) insect gives birth to test and tests
Target: lepidoptera pest diamond-back moth
Method: just embodiment 1～5 and comparing embodiment 1～3 are respectively with 7 gradient concentrations of clear water dilution, process with clear water and make blank, the employing leaf dipping method is measured, with diameter 2cm cabbage leaves soak take out after into the liquid 10 seconds air-dry, place 3 in each culture dish, if 3 repetitions, picking diamondback moth larvae in three ages, in each culture dish, picking is 10, then put into 25 ℃ of illumination boxs, investigation survival borer population respectively after 72 hours calculates lethality, the lethality data by 7 concentration gradients, calculate virulence regression equation, finally obtain LC50.Measurement result following (table 2):
Table 2 Application Example one test result
| FORMULATION EXAMPLE | Active ingredient | Formulation | Proportionate relationship | LC50(mg/L) |
| FORMULATION EXAMPLE 1 | Chlorine fluorine ether chrysanthemum ester+HEXAFLUMURON | Missible oil | 1∶1 | 19.6 |
| FORMULATION EXAMPLE 2 | Chlorine fluorine ether chrysanthemum ester+HEXAFLUMURON | Missible oil | 1∶50 | 47.8 |
| FORMULATION EXAMPLE 3 | Chlorine fluorine ether chrysanthemum ester+HEXAFLUMURON | Missible oil | 1∶30 | 25.3 |
| FORMULATION EXAMPLE 4 | Chlorine fluorine ether chrysanthemum ester+HEXAFLUMURON | Missible oil | 1∶5 | 16.9 |
| FORMULATION EXAMPLE 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 the LC50 of each composite embodiment in Application Example one and the LC50 of single dose comparing embodiment, computational methods are calculated the method for mixture co-toxicity with reference to Sun Yunpei's by toxicity index, calculate co-toxicity coefficient.
The composite co-toxicity coefficient of table 3 the present invention is measured
Test result shows, when chlorine fluorine ether chrysanthemum ester and fluorine tinkling of pieces of jade urea proportionate relationship were between 1: 50～10: 1, its co-toxicity coefficient was all greater than 100, is especially between 1: 1～1: 30 the time in proportionate relationship, and its co-toxicity coefficient shows obvious synergistic effect all greater than 120.
Data with the contrast of comparing embodiment 3 show in addition, and the formula activity after composite is unlike existing market single dose chrysanthemum commonly used ester weak effect.
Claims (9)
1. insecticides, it is characterized in that: it is comprised 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: 50～50: 1 is composite by component A and B component; Described component A is the pyrethroid compound that structure satisfies following formula; Described B component is chitin synthesis inhibitor
2. insecticides claimed in claim 1 is characterized in that: described component A is selected from one or more the mixture in following pyrethroid compound:
The rich dextrorotation 2,3,5 of 1 the effective body burden of R configuration 〉=55% of cyclopropane, 6-tetrafluoro-4-methoxymethyl benzyl base-3-(2,2-dichloroethylene)-2,2-dimethyl cyclopropane carboxylic acid ester;
1 absolute configuration of cyclopropane is 2,3,5 of R configuration, 1,3 dextrorotation of not distinguishing cis-trans isomerism, 6-tetrafluoro-4-methoxymethyl benzyl base-(1R)-3-(2,2-dichloroethylene)-2,2-dimethyl cyclopropane carboxylic acid ester;
1 absolute configuration of cyclopropane is that R configuration, 1,3 are trans-isomeric 2,3,5,6-tetrafluoro-4-methoxymethyl benzyl base-(1R, 3S)-3-(2,2-dichloroethylene)-2,2-dimethyl cyclopropane carboxylic acid ester;
Perhaps
1 absolute configuration of cyclopropane is that R configuration, 1,3 are 2,3,5 of syn-isomerism, 6-tetrafluoro-4-methoxymethyl benzyl base-(1R, 3R)-3-(2,2-dichloroethylene)-2,2-dimethyl cyclopropane carboxylic acid ester.
3. insecticides claimed in claim 1, it is characterized in that: the part by weight of described component A and B component is 1: 50～10: 1.
4. insecticides claimed in claim 1, it is characterized in that: the part by weight of described component A and B component is 1: 30～1: 1.
5. insecticides claimed in claim 1 is characterized in that: described chitin synthesis inhibitor is selected from flufenoxuron, fluorine pyridine urea, HEXAFLUMURON, methoxyfenozide, diflubenzuron, one or more the mixture in go out young urea or No. II, the young urea of going out.
6. insecticides claimed in claim 5, it is characterized in that: described chitin synthesis inhibitor is fluorine tinkling of pieces of jade urea.
Insecticides claimed in claim 1 as pesticidal preparations in the application of killing in getting rid of insects.
8. application claimed in claim 7 is characterized in that: but the formulation of described pesticidal preparations is missible oil wet-milling, suspending agent or water dispersible granules.
9. application claimed in claim 7 is characterized in that: described insect comprises the insect of Lepidoptera, thrips, Homoptera, diptera or mite class.
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| 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 |
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| CN101632378A (en) * | 2009-06-04 | 2010-01-27 | 江苏扬农化工股份有限公司 | Electrothermal pesticide tablet |
| CN101632379A (en) * | 2009-06-04 | 2010-01-27 | 江苏扬农化工股份有限公司 | Electrothermal pesticide liquid |
| 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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Patent Citations (6)
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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 |
| CN101632378A (en) * | 2009-06-04 | 2010-01-27 | 江苏扬农化工股份有限公司 | Electrothermal pesticide tablet |
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