CN101878776A - Insecticide composition and preparation method and application thereof - Google Patents
Insecticide composition and preparation method and application thereof Download PDFInfo
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- CN101878776A CN101878776A CN2010101917039A CN201010191703A CN101878776A CN 101878776 A CN101878776 A CN 101878776A CN 2010101917039 A CN2010101917039 A CN 2010101917039A CN 201010191703 A CN201010191703 A CN 201010191703A CN 101878776 A CN101878776 A CN 101878776A
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- 239000002917 insecticide Substances 0.000 title claims abstract description 59
- 239000000203 mixture Substances 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 34
- 241000255925 Diptera Species 0.000 claims abstract description 33
- 239000003381 stabilizer Substances 0.000 claims abstract description 16
- 230000000694 effects Effects 0.000 claims abstract description 15
- 239000000463 material Substances 0.000 claims abstract description 15
- 239000004480 active ingredient Substances 0.000 claims abstract description 14
- 241001674044 Blattodea Species 0.000 claims abstract description 11
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 7
- -1 ester compound Chemical class 0.000 claims abstract description 4
- 239000007788 liquid Substances 0.000 claims description 28
- 241000238631 Hexapoda Species 0.000 claims description 24
- 239000003350 kerosene Substances 0.000 claims description 15
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 claims description 12
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical group CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims description 12
- 235000010354 butylated hydroxytoluene Nutrition 0.000 claims description 12
- 229960005235 piperonyl butoxide Drugs 0.000 claims description 12
- WLLGXSLBOPFWQV-UHFFFAOYSA-N MGK 264 Chemical group C1=CC2CC1C1C2C(=O)N(CC(CC)CCCC)C1=O WLLGXSLBOPFWQV-UHFFFAOYSA-N 0.000 claims description 11
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 10
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 8
- 239000000853 adhesive Substances 0.000 claims description 8
- 230000001070 adhesive effect Effects 0.000 claims description 8
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- 239000000843 powder Substances 0.000 claims description 7
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 claims description 6
- 239000002728 pyrethroid Substances 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
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- 241000196324 Embryophyta Species 0.000 claims description 5
- 239000000077 insect repellent Substances 0.000 claims description 5
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- 238000010438 heat treatment Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
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- 150000001345 alkine derivatives Chemical class 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
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- 238000009472 formulation Methods 0.000 description 3
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- 238000011084 recovery Methods 0.000 description 3
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- UYCSRVMHOHFVTN-UHFFFAOYSA-N 1-(2,3,5,6-tetrafluoro-4-methoxyphenyl)ethanol Chemical compound O(C)C1=C(C(=C(C(=C1F)F)C(O)C)F)F UYCSRVMHOHFVTN-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- 241000257159 Musca domestica Species 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
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- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- UBNWPQXLFRMMEI-GQCTYLIASA-N 5-[3-[(e)-3-(3-hydroxy-2-methoxycarbonylphenoxy)prop-1-enyl]phenyl]-1,2-oxazole-3-carboxylic acid Chemical compound COC(=O)C1=C(O)C=CC=C1OC\C=C\C1=CC=CC(C=2ON=C(C=2)C(O)=O)=C1 UBNWPQXLFRMMEI-GQCTYLIASA-N 0.000 description 1
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- 229920002261 Corn starch Polymers 0.000 description 1
- 241000144210 Culex pipiens pallens Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 240000003183 Manihot esculenta Species 0.000 description 1
- 235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 1
- XCUGQTFVQHTFPD-CSKARUKUSA-N [(E)-4-methylhept-4-en-1-yn-3-yl] 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC\C=C(/C)C(C#C)OC(=O)C1C(C=C(Cl)Cl)C1(C)C XCUGQTFVQHTFPD-CSKARUKUSA-N 0.000 description 1
- 229940024113 allethrin Drugs 0.000 description 1
- 229960004217 benzyl alcohol Drugs 0.000 description 1
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- 238000003958 fumigation Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
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- 230000002045 lasting effect Effects 0.000 description 1
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- DDVNRFNDOPPVQJ-HQJQHLMTSA-N transfluthrin Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@H]1C(=O)OCC1=C(F)C(F)=CC(F)=C1F DDVNRFNDOPPVQJ-HQJQHLMTSA-N 0.000 description 1
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- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention provides an insecticide composition and a preparation method and application thereof. An active ingredient of the insecticide composition is an ester compound expressed by the formula (Y) in the specifications, wherein X can be: (1) 3-(2-fluo-1-propenyl)-2,2-dimethyl cyclopropane radical, (2) 3-(2-cyano-1-propenyl)-2,2-dimethyl cyclopropane radical and (3) 3-(2-cyano-2-fluorovinyl)-2,2-dimethyl cyclopropane radical. The insecticide composition is prepared from the active ingredient, a stabilizing agent, a synergistic agent and a base material according to a certain proportion, wherein the compound (Y) accounts for 0.05 to 3.0 weight percent of the insecticide composition. The insecticide of the invention has perfect effect of preventing and controlling mosquitoes, flies, cockroaches, ants and other household pests. The invention also provides the preparation method and the application of the insecticide composition.
Description
Technical field
The present invention relates to a kind of insecticides, and its production and application, specifically a kind of a kind of insecticides that forms by special pyrethroid compound (Y) formulated.
Background technology
Pyrethroid coumpound can be used to prevent and treat sanitary insect pests such as mosquito, fly, cockroach, and has higher insecticidal activity, this is the commonly known fact, simultaneously for insects such as mosquito, fly, cockroach in the fishing village, aquatic product manufactory, destructor plant and peripheries such as animal house, pouity dwelling place grow vexing all the time.As the countermeasure of eliminating these insects, except using insecticide formulation such as emulsion, finish, pulvis and novel pesticide, still exist the characteristics that lack a continuation effect, therefore wish exploitation some good product and formulations, promptly as the spatial manipulation agent, and the lasting effect time is long, and then diffusibility is good, even also have the product of good effect to come out in open place.
Sell in the market with Es-allethrin, transfluthrin, cholrempenthrins etc. are easy to use as the insecticide of main active ingredient, can keep spatial manipulation for a long time after lighting, until after-flame, volatilization is stable, and effect is obvious, is a kind of fast effective insecticidal mode.But this series products sanitary insect pest has generally been had certain pesticide resistance, and effect is relatively poor, even improve the active ingredient concentration in the formulation, also can not do comparatively suitable insecticide, and the active ingredient of therefore selecting suitable insecticide is an important link.
Based on above-mentioned background, the present invention proposes a kind of new insecticides, adopts the compound that mosquito, fly, cockroach etc. are had better preventive effect as active ingredient, has improved the control efficiency of insecticide.
Summary of the invention
The objective of the invention is to: (1) provides a kind of new insecticides, and mosquito, fly, cockroach are had higher preventive effect.(2) provide a kind of processing and preparation method of insecticides.
Purpose of the present invention is achieved through the following technical solutions:
A kind of new insecticides is provided, it formulated by a certain percentage by active ingredient, stabilizing agent, synergist and base material, the active ingredient of indication is the ester compounds of following formula (Y), this compound is shared content 0.05～3.0w/w% in insecticides, the shared content 0.05～3.0w/w% of stabilizing agent, the shared content 0.05～3.0w/w% of synergist, the shared content 91.0～99.85w/w% of base material
Represented (X) is selected from (1) 3-(2-fluoro-1-acrylic)-2,2-dimethylcyclopropane base in the formula (Y); (2) 3-(2-cyano group-1-acrylic)-2,2-dimethylcyclopropane base; (3) 3-(2-cyano group-2-is fluoride-based)-2, the mixture of one or more in the 2-dimethylcyclopropane base.The insecticides active component is selected from one or more the mixture in (1)-(3); The indication stabilizing agent is the phenol stabilizing agent; The indication synergist is Octacide 264 or Butacide; The indication base material comprises solid substrate and liquid base, and solid substrate is meant various so plant drymeals of property, and liquid base is meant some liquid flux.
Asymmetric carbon atom has R, S optically-active isomer on the cyclopropane, also has cis, trans geometric isomer on two keys, cyclopropane; Each compound comprises all optical isomers with control of insect activity, geometric isomer and composition thereof.
When X is (1) 3-(2-fluoro-1-acrylic)-2, during 2-dimethylcyclopropane base, structural formula of compound and chemical name are as follows:
Chemical name is: 2,3,5, and 6-tetrafluoro-4-methoxyl methyl benzyl-3-(2-fluoro-1-acrylic)-2,2-dimethyl cyclopropane carboxylic acid ester.
When X is (2) 3-(2-cyano group-1-acrylic)-2, during 2-dimethylcyclopropane base, structural formula of compound and chemical name are as follows:
Chemical name is: 2,3,5, and 6-tetrafluoro-4-methoxyl methyl benzyl-3-(2-cyano group-1-acrylic)-2,2-dimethyl cyclopropane carboxylic acid ester.
When X is (3) 3-(2-cyano group-2-is fluoride-based)-2, during 2-dimethylcyclopropane base, structural formula of compound and chemical name are as follows:
Chemical name is: 2,3,5, and 6-tetrafluoro-4-methoxyl methyl benzyl-3-(2-cyano group-2-is fluoride-based)-2,2-dimethyl cyclopropane carboxylic acid ester.
Described carboxylate prepares in accordance with the following methods:
With general formula (A) expression carboxylic acid
With general formula (B) expression carboxylic acid chloride
General formula (A) or general formula (B) and 2,3,5, the alcohol that the 6-tetrafluoro-4-methoxy benzylalcohol is represented just can obtain formula (Y) series compound by esterification.
The compounds of this invention is a kind of insect is had fabulous preventive and therapeutic effect and has suitable saturated vapor pressure, under normal temperature and high temperature, still can stablize and continue volatilization, drug effect is better, simultaneously can effectively reduce pyrethroid toxicity and biotic resistance, stable to light, the activity of pyrethroid there is the compound of humidification structural safety, people and animals is stimulated little.
Described a kind of insecticides, the weight percent proportioning of each composition is:
Ester compounds 0.05～the 3.0W/W% of general structure (Y)
Phenol stabilizing agent 0.05～3.0W/W%
Synergist 0.05～3.0W/W%
Base material 91.0～99.85W/W%
The phenol stabilizing agent that also preferably contains the 0.05～3.0w/w% that accounts for the insecticide total amount in the described insecticide.This class stabilizing agent can improve fumigation, and the stability during spraying guarantees the continual and steady of drug effect.
Described phenol stabilizing agent can be selected from 2,6 di tert butyl 4 methyl phenol (BHT), α-Jia Bianji phenol or the tert-butyl phenol one or more mixture.
The missible oil of the liquid form that described carboxylate is mixed with or be the solution of solvent with the hydro carbons, described varsol is kerosene, have the saturated hydrocarbons solvent of 150～350 ℃ of boiling points or their mixture.
Described base material is made up of one or more adhesives of one or more inflammable substances, and wherein the weight ratio of inflammable substance and adhesive is 90: 10 to 99.9: 0.1.
Described inflammable substance can be to be selected from plant drymeals such as wood powder, coconut shell powder or walnut parting, or be selected from charcoal powder, activated carbon powder or their mixture, described adhesive can be the Tabu powder, be selected from tapioca, corn starch or wheaten starch, casein, methylcellulose, the polymer of carboxymethyl cellulose or polyvinyl alcohol and composition thereof.
Described insecticide base material normally by mixing inflammable substance and adhesive, is mediated in water, moulding and oven dry preparation.The shape of insecticide base material can be disc type or line formula without limits.
Described insecticide preferred manufacturing procedure is that (1) is made the special pyrethroid coumpound (Y) of indication the missible oil of liquid form or made solution with the footpath kind solvent with water, the indication varsol is meant kerosene, have the saturated hydrocarbon of 150～350 ℃ of boiling points or their mixture, in solution, add stabilizing agent again, the synergist mixing; (2) base material is cooperated with adhesive, it is kneaded and formed as line formula mosquito-repellent incense to add water, and section bar is made in oven dry, and the adhesive of indication is various starch, casein, carboxymethyl cellulose or polyvinyl alcohol; Binder dosage is 0.1～1.0% of a solid substrate weight; (3) the solution drop that step (1) is prepared is to the section bar of step (2).
The utilization of pesticides mode that more than obtains is to light insecticide of the present invention near habitat (for example dwelling house, soot, shed for animals) insect or its.The burning of insecticide can make compound (Y) volatilization, and after airborne active ingredient reached certain concentration, sanitary insect pest produced to be stimulated, drive, benumb, knock down and lethal effect, thereby reaches the control to insect.
Present inventors advanced research contrast, filtered out (Y1), chemical name is: 2,3,5, and 6-tetrafluoro-4-methoxyl methyl benzyl-3-(2-fluoro-1-acrylic)-2,2-dimethyl cyclopropane carboxylic acid ester; (Y2), chemical name is: 2,3,5,6-tetrafluoro-4-methoxyl methyl benzyl-3-(2-cyano group-1-acrylic)-2,2-dimethyl cyclopropane carboxylic acid ester; (Y3) chemical name is: 2,3,5, and 6-tetrafluoro-4-methoxyl methyl benzyl-3-(2-cyano group-2-is fluoride-based)-2,2-dimethyl cyclopropane carboxylic acid ester.Active ingredient as insecticide.By experimental results demonstrate, with this compound is that the insecticide that active ingredient prepares has very good control efficiency to sanitary insect pest, and drug effect is played stably, for example and cholrempenthrin (Chlorempenthrin) carry out the drug effect contrast test for the insecticide of active ingredient, the result shows that the drug effect of insecticide of the present invention is respectively shown in the back, in addition for the various optical isomers and the cis-trans-isomer that exist in the product.
Embodiment
Explain technical scheme of the present invention and effect in detail with the form of embodiment below.But the present invention is not limited to following examples.
Embodiment 1.1R-cis (Z)-2,2-dimethyl-3-(2-fluoro-1-acrylic)-cyclopropane-carboxylic acid or acyl chlorides
The preparation of 1R-cis (Z) 2`2-dimethyl-3-(2-fluoro-1-acrylic) cyclopropane-carboxylic acid
0.5g p-methyl benzenesulfonic acid (PTSA) join and dissolved 5.78g 1R-dis (Z)-2,2-dimethyl-3-(2-fluoro-1-acrylic) cyclopropane carboxylic acid-1, the toluene of 1-dimethyl ethyl ester and 50ml.Reaction is till being heated to 120 ℃ of backflows.And then cool to 20 degree, and adopt the isopropyl ether dilution, washing, drying is filtered and is concentrated and obtains 4.40g 1R-cis (Z)-2,2-dimethyl-3-(2-fluoro-1-acrylic) cyclopropane-carboxylic acid.
The preparation of 1R-cis (Z) 2`2-dimethyl-3-(2-fluoro-1-acrylic)-cyclopropane carboxylic acid isoxazolecarboxylic acid
1ml DMF and 4.5ml (COCl)
2Be added into and be dissolved into 4.40g 1R-cis (Z)-2 in 0 ℃, 2-dimethyl-3-(2-fluoro-1-acrylic) cyclopropane-carboxylic acid and 50ml carrene, react 135min down at 20 ℃ again behind the stirring 45min down at 0 ℃, concentrate and reclaim methylene chloride, again distillation is dissolved into concentrate drying in the toluene, then adds 35ml formation acyl chlorides toluene liquid and be used for the back preparation.
Embodiment 2.1R-trans (E)-2,2-dimethyl-3-(2-fluoro-1-acrylic)-cyclopropane-carboxylic acid or acyl chlorides
1.2g APTS add the 1R-trans (E)-2 be dissolved in 13.86g, 2-dimethyl-3-(2-fluoro-1-acrylic) cyclopropane carboxylic acid-1, the toluene of 1-dimethyl ethyl ester and 140ml.Reaction is till being heated to 120 ℃ of backflows.And then cool to 20 ℃, and adopt the dilution of 250ml isopropyl ether, washing, drying is filtered and the concentrated 11g 1R-trans (E)-2,2-dimethyl-3-(2-fluoro-1-acrylic) cyclopropane-carboxylic acid of obtaining.
(COCl) of 3ml DMF and 10ml
2Be added into and be dissolved into 10g1R-trans (E) 2 in 0 ℃, 2-dimethyl-3-(2-fluoro-1-acrylic) cyclopropane-carboxylic acid and 100ml carrene.React 135min down at 20 ℃ again behind the stirring 45min down at 0 ℃, 40 ℃ concentrate the recovery methylene chloride down, distillation are dissolved into concentrate drying in the toluene again, then add 55ml and form acyl chlorides toluene liquid, and the acyl chlorides toluene liquid of 1M/L prepares like this.
(preparation method of other carboxylic acids or acyl chlorides isomer is identical)
Embodiment 3
In the four-hole reaction bulb of a 500ml, drop into 2,3,5,6-tetrafluoro-4-methoxyl group benzylalcohol 52.5g, pyridine 25.0g, be dissolved in 200ml toluene, stir, 5～10 ℃ drip 3-(2-fluoro-1-acrylic)-2 down, 2-dimethyl cyclopropane carboxylic acid acyl chlorides 48g is warming up to 25 ℃ of reactions 2 hours after dropwising.Wash at twice with 150ml 10% hydrochloric acid, use 150ml10%NaHCO again
3Washing is at twice told toluene layer and is purified solvent toluene in the 0.08Mpa heating, obtains 2,3,5,6-tetrafluoro-4-methoxy-benzyl-3-(2-fluoro-1-acrylic)-2,2-dimethyl cyclopropane carboxylic acid ester, weight is 85.7g, and content is 91.5.0%, and yield is 86.2%.
The IR spectrogram shows υ-c=o 1750cm
-1The strong absworption peak and the υ-c-o-c-1180cm at place
-1And 1160cm
-1Two strong spikes explanation products in have the existence of ester group; υ-c=o is at 1720cm
-1About the explanation of strong broad peak the existence of carbonyl is arranged; At 2900cm
-1About with 1400cm
-1About characteristic peak explanation υ-
CH3, υ-
CH2-existence; 1600cm
-1With 1500cm
-1There is υ-Ar-phenyl ring characteristic absorption peak at the place; The GC/MS spectrogram shows that this compound molecular weight is 364.1; The NMR spectrogram prove in this compound H in the position in the structure shown in above-mentioned structural formula.NMR(
1H，CDCl
3)δ：5.35(s，2H)；4.60(d，1H)；3.80(s，3H)；1.71(s，3H)；1.54(d，1H)；1.10(d，1H)；1.01(s，6H)。More than three kinds of spectrograms prove that jointly this compound is: 2,3,5,6-tetrafluoro-4-methoxy-benzyl-3-(2-fluoro-1-acrylic)-2,2-dimethyl cyclopropane carboxylic acid ester, molecular formula C
17H
17F
5O
3, product is a buff liquid.
Synthesizing of embodiment 4 compounds (Y2)
In the four-hole reaction bulb of a 500ml, drop into 2,3,5,6-tetrafluoro-4-methoxyl methyl benzylalcohol 45.0g, pyridine 25.0g, be dissolved in 200ml toluene, stir, 5～10 ℃ drip 3-(2-cyano group-1-acrylic)-2 down, 2-dimethyl cyclopropane carboxylic acid acyl chlorides 42g is warming up to 25 ℃ of reactions 2 hours after dropwising.Wash at twice with 150ml 10% hydrochloric acid, use 150ml10%NaHCO again
3Washing is at twice told toluene layer and is purified solvent toluene in the 0.08Mpa heating, obtains 2,3,5,6-tetrafluoro-4-methoxyl methyl benzyl-3-(2-cyano group-1-acrylic)-2,2-dimethyl cyclopropane carboxylic acid ester, weight is 73.6g, and content is 90.4%, and yield is 86.0%.
The IR spectrogram shows υ-c=o 1750cm
-1The strong absworption peak and the υ-c-o-c-1180cm at place
-1And 1160cm
-1Two strong spikes explanation products in have the existence of ester group; υ-c=o is at 1720cm
-1About the explanation of strong broad peak the existence of carbonyl is arranged; At 2900cm
-1About with 1400cm
-1About characteristic peak explanation υ-
CH3, υ-
CH2-existence; 1600cm
-1With 1500cm
-1There are υ-Ar-phenyl ring characteristic absorption peak, 2250cm in the place
-1Having the moderate strength absworption peak to show has-existence of C ≡ N.The GC/MS spectrogram shows that this compound molecular weight is 385.3; The NMR spectrogram prove in this compound H in the position in the structure shown in above-mentioned structural formula.NMR(
1H，CDCl
3)δ：5.82(d，1H)；5.35(s，2H)；4.80(s，2H)；3.25(s，3H)；1.71(s，3H)；1.54(d，1H)；1.10(d，1H)；1.01(s，6H)。More than three kinds of spectrograms prove that jointly this compound is: 2,3,5,6-tetrafluoro-4-methoxyl methyl benzyl-3-(2-cyano group-1-acrylic)-2,2-dimethyl cyclopropane carboxylic acid ester, molecular formula C
19H
19F
4NO
3, product is a weak yellow liquid.
Synthesizing of embodiment 5 compounds (Y3)
In the four-hole reaction bulb of a 500ml, drop into 2,3,5,6-tetrafluoro-4-methoxyl methyl benzylalcohol 45.0g, pyridine 25.0g, be dissolved in 200ml toluene, stir, 5～10 ℃ drip 3-(2-cyano group-2-is fluoride-based)-2 down, 2-dimethyl cyclopropane carboxylic acid acyl chlorides 42g is warming up to 25 ℃ of reactions 2 hours after dropwising.Wash at twice with 150ml 10% hydrochloric acid, use 150ml10%NaHCO again
3Washing is at twice told toluene layer and is purified solvent toluene in the 0.08Mpa heating, obtains 2,3,5,6-tetrafluoro-4-methoxyl methyl benzyl-3-(2-cyano group-2-is fluoride-based)-2,2-dimethyl cyclopropane carboxylic acid ester, weight is 72.4g, and content is 91.3%, and yield is 84.4%.
The IR spectrogram shows υ-c=o 1750cm
-1The strong absworption peak and the υ-c-o-c-1180cm at place
-1And 1160cm
-1Two strong spikes explanation products in have the existence of ester group; υ-c=o is at 1720cm
-1About the explanation of strong broad peak the existence of carbonyl is arranged; At 2900cm
-1About with 1400cm
-1About characteristic peak explanation υ-CH
3, υ-CH
2-existence; 1600cm
-1With 1500cm
-1There are υ-Ar-phenyl ring characteristic absorption peak, 2250cm in the place
-1Having the moderate strength absworption peak to show has-existence of C ≡ N.The GC/MS spectrogram shows that this compound molecular weight is 389.3; The NMR spectrogram prove in this compound H in the position in the structure shown in above-mentioned structural formula.NMR(1H，CDCl3)δ：5.35(s，2H)；5.00(d，1H)；4.80(s，2H)；3.25(s，3H)；1.54(d，1H)；1.10(d，1H)；1.01(s，6H)。More than three kinds of spectrograms prove that jointly this compound is: 2,3,5,6-tetrafluoro-4-methoxyl methyl benzyl-3-(2-cyano group-2-is fluoride-based)-2,2-dimethyl cyclopropane carboxylic acid ester, molecular formula C
18H
16F
5NO
3, product is a weak yellow liquid.
Application Example 1
With 0.15gY1,0.08gBHT, the 0.08g Octacide 264 is dissolved in 1g kerosene, and drop is made the disinsecting mosquito repellant incense made I to the blank line spices Pi of 35g, wherein contain the about 0.4w/w% of Y1, contains the about 0.2w/w% of BHT, contains the about 0.2w/w% of Octacide 264.
Application Example 2
With 0.075gY1+0.075gY2,0.04gBHT, the 0.04g Butacide is dissolved in 1g kerosene, and drop is made the disinsecting mosquito repellant incense made II to the blank line spices Pi of 35g, wherein contain (Y1+Y2) about 0.4w/w%, contains the about 0.1w/w% of BHT, contains the about 0.1w/w% of synergist.
Application Example 3
With 0.05gY1+0.05Y2+0.05Y3,0.08g tert-butyl phenol, 0.06g Butacide, be dissolved in 1g kerosene, drop is made the disinsecting mosquito repellant incense made III to the blank line spices Pi of 35g, wherein contain (Y1+Y2+Y3) about 0.4w/w%, contain the about 0.2w/w% of tert-butyl phenol, contain the about 0.3w/w% of Butacide.
Application Example 4
With 0.075gY2+0.075Y3,0.08g α-Jia Bianji phenol, the 0.08g Octacide 264 is dissolved in 1g kerosene, drop is made the disinsecting mosquito repellant incense made IV to the blank line spices Pi of 35g, wherein contain (Y2+Y3) about 0.4w/w%, contain the about 0.2w/w% of α-Jia Bianji phenol, contain the about 0.2w/w% of Octacide 264.
Application Example 5
With 0.15gY3,0.08gBHT, the 0.15g Butacide is dissolved in 1g kerosene, and drop is made the disinsecting mosquito repellant incense made V to the blank line spices Pi of 35g, wherein contain the about 0.4w/w% of Y3, contains the about 0.2w/w% of BHT, contains the about 0.4w/w% of Butacide.
Application Example 6
With the 0.75g high efficiency cholrempenthrin, 0.08gBHT, 0.15 Butacide is dissolved in 1g kerosene, and drop is made the disinsecting mosquito repellant incense made VI to the blank line spices Pi of 35g, wherein contain the about 2w/w% of high efficiency cholrempenthrin, contains the about 0.2w/w% of BHT, contains the about 0.4w/w% of Butacide.
Application Example 7
With the trans Y1 of 0.15g dextrorotation, 0.08gBHT, the 0.08g Octacide 264 is dissolved in 1g kerosene, and drop is made the disinsecting mosquito repellant incense made VII to the blank line spices Pi of 35g, wherein contain the about 0.4w/w% of the trans Y1 of dextrorotation, contains the about 0.2w/w% of BHT, contains Octacide 264 0.2w/w%.
Application Example 8
With 0.02gY1,0.02gBHT, 0.02 Butacide is dissolved in 1g kerosene, and drop is made the disinsecting mosquito repellant incense made VIII to the blank line spices Pi of 35g, wherein contain the about 0.05w/w% of Y1, contains the about 0.05w/w% of BHT, contains the about 0.05w/w% of Butacide.
Application Example 9
With 1.0gY1, the 1.0g tert-butyl phenol, the 1.0g Octacide 264 is dissolved in 6.0g kerosene, and drop is made the disinsecting mosquito repellant incense made IX to the blank line spices Pi of 28g, wherein contain the about 2.9w/w% of Y1, contains the about 2.9w/w% of tert-butyl phenol, contains the about 2.9w/w% of Octacide 264.
Application Example 1,2,3,4,5,7,8,9 of the present invention and reference example 6 are carried out the indoor harmacological effect of mosquito is tested with reference to GB13917.4-2009.Examination worm housefly, the 4th day adult in back that sprout wings, male and female individual half.Adopt airtight drum device.Detailed process is as follows: will put into airtight drum for the examination mosquito; after waiting to try worm recovery normal activity; appoint and get one section of tested mosquito-repellent incense; put to fragrant frame; mosquito-repellent incense is removed in the igniting mosquito-repellent incense timing behind the 1min, write down down and out examination mosquito number at set intervals; to all be transferred in the dependent insect cage of cleaning behind the 20min, check dead examination borer population behind the 24hr for the examination mosquito.
The control efficiency of the above-mentioned insecticides of table 1.
| Line spices | ??KT 50(min) | 24h lethality (%) |
| The insecticide I | ??4′46″ | ??100 |
| The insecticide II | ??4′19″ | ??100 |
| The insecticide III | ??3′13″ | ??100 |
| The insecticide IV | ??4′38″ | ??100 |
| Insecticide V | ??4′55″ | ??100 |
| The insecticide VI | ??5′21″ | ??100 |
| The insecticide VII | ??4′03″ | ??100 |
| The insecticide VIII | ??10′55″ | ??40 |
| The insecticide IX | ??3′27″ | ??100 |
The result shows: the Shoofly joss stick of the Y of the present invention's preparation has good killing effect to housefly, its effect with use at present about 5 times of more high efficiency cholrempenthrin line spices, wherein the activity of the trans single optical isomer of Y1 dextrorotation is again 1.5 times of its racemic modification drug effect.
Application Example 10
With (0.1Y1+0.1Y2+0.1Y3) part compound (as active component) and 0.3 part of BHT, 0.3 part Butacide, the aliphatic hydrocarbon Hybrid Heating of the C12 of surplus～14 is prepared into vaporizer mosquito liquid.This vaporizer mosquito liquid can be become electric liquid device, wherein containing active compound component is 0.3w/w%.
Application Example 11
With (0.15Y1+0.15Y3) part compound (as active component) and 0.3 part of BHT, 0.3 part of Octacide 264, the aliphatic hydrocarbon Hybrid Heating of the C12 of surplus～14 is prepared into vaporizer mosquito liquid.This vaporizer mosquito liquid can be become electric liquid device, wherein containing active compound component is 0.3w/w%.
The alkynes third chrysanthemum ester vaporizer mosquito liquid of Application Example 10,11 of the present invention and 1% is carried out evaluation of pesticide effectiveness contrast according to GB13917.6-2009, adopt airtight drum device.With vaporizer mosquito liquid sample energising 2h, 36h, 84h, 168h, draw 20 female Culex pipiens pallens with mosquito sucking tube, put into device, accurate smoked kill 1min, timing simultaneously, smoked object for appreciation is complete cuts off the electricity supply, and removes the vaporizer mosquito liquid device, and record is at regular intervals gone down to such an extent that be examination mosquito number.The results are shown in Table c:
The vaporizer mosquito liquid of table c. insecticides preparation of the present invention and the alkynes third chrysanthemum ester vaporizer mosquito liquid effect are relatively
The result shows: insecticides of the present invention is that the relative effectivenes of vaporizer mosquito liquid of former medicine preparation is about 5 times of the alkynes third chrysanthemum ester vaporizer mosquito liquid.
Application Example 12
Kerosene, propellant, casting resin with 0.15 weight portion Y1 (active component) and 48.85 weight portions under heating mix, it is inserted in the aerosol jar that control valve is housed, and inject 950 weight portions, third butane by this control valve and obtain insect aerosol adding to depress, wherein contain the about 0.02w/w% of active compound component.
Application Example 13
Kerosene, propellant, casting resin with (0.05Y1+0.05Y2+0.05Y3) weight portion insecticides (active component) and 48.85 weight portions under heating mix, it is inserted in the aerosol jar that control valve is housed, and inject 950 weight portions, third butane by this control valve and obtain insect aerosol adding to depress, wherein contain the about 0.02w/w% of active compound component.
Application Example 12 of the present invention and 13 is carried out efficacy testing to insect according to GB13917.2-2009, adopt airtight drum device.Detailed process is as follows: will put into cylinder for the examination insect; after waiting to try worm recovery normal activity; metered injection from insect aerosol jar of the present invention; extracting baffle plate behind the 1min out makes the examination worm contact with medicament; timing immediately; and opening entry, writing down down and out examination borer population at regular intervals, will all be transferred in the dependent insect cage of cleaning behind the 20min for the examination worm.Display list d as a result.
The insect aerosol of table d The compounds of this invention preparation is to the insect killing effect of fly, cockroach
| Numbering | Insect | ??KT 50(fly/cockroach) |
| Embodiment 12 | Cockroach | ??4′52″ |
| Embodiment 13 | Cockroach | ??3′47″ |
The result shows: the aerosol of insecticides preparation of the present invention has good insect killing effect to cockroach.
The above results shows, herein Fa Ming chemicals (Y) be have structural safety, former medicine toxicity is low, usage amount is low, is to be applied to the lower raw insecticide medicine of insecticide consumption, dosage is also lacked than traditional old kind.These compound tests of pesticide effectiveness show to have excellent insecticidal activity, knock down soon, and the lethality rate height, vapour pressure is suitable, KT under low concentration
50(min) at 2～4 minutes, lethality 100% in 24 hours, can stablize to continue volatilization under normal temperature or heated condition, helped being used in enormous quantities the application of domestic hygiene preparation.
Claims (8)
1. insecticides, it is characterized in that: it formulated by a certain percentage by active ingredient, stabilizing agent, synergist and base material, the active ingredient of indication is the ester compounds of following formula (Y), this compound is shared content 0.05～3.0w/w% in insecticides, the shared content 0.05～3.0w/w% of stabilizing agent, the shared content 0.05～3.0w/w% of synergist, the shared content 91.0～99.85w/w% of base material
2. a kind of insecticides according to claim 1 is characterized in that: represented (X) is selected from (1) 3-(2-fluoro-1-acrylic)-2,2-dimethylcyclopropane base in the formula (Y); (2) 3-(2-cyano group-1-acrylic)-2,2-dimethylcyclopropane base; (3) 3-(2-cyano group-2-is fluoride-based)-2, the mixture of one or more in the 2-dimethylcyclopropane base, insecticides active component are selected from one or more the mixture in (1)-(3); The indication stabilizing agent is the phenol stabilizing agent; The indication synergist is Octacide 264 or Butacide; The indication base material comprises solid substrate and liquid base, and solid substrate is meant various flammable plant drymeals, and liquid base is meant some liquid flux.
3. according to the structure of X in a kind of insecticides described in the claim 2, it is characterized in that: asymmetric carbon atom has R, S optically-active isomer on the cyclopropane, also has cis, trans geometric isomer on two keys, cyclopropane; Each compound comprises all optical isomers with control of insect activity, geometric isomer and composition thereof.
4. according to claim 1 or 2 or 3 described a kind of insecticides, it is characterized in that the phenol stabilizing agent is selected from 2,6 di tert butyl 4 methyl phenol (BHT), α-Jia Bianji phenol or the tert-butyl phenol one or more mixture.
5. a kind of insecticides according to claim 1 and 2 is characterized in that the various flammable plant drymeal of base material indication is selected from wood powder, coconut shell powder or walnut parting, charcoal powder, activated carbon powder or their mixture.
6. a kind of insecticides according to claim 1 and 2 is characterized in that it being that the base material solvent of indication is water, kerosene or saturated hydrocarbon with 150～350 ℃ of boiling points or their mixture.
7. the processing and preparation method of a kind of insecticides according to claim 1 and 2, it is characterized in that (1) make the special pyrethroid coumpound (Y) of indication and water the missible oil of liquid form or make solution with the footpath kind solvent, the indication varsol is meant kerosene, have the saturated hydrocarbon of 150～350 ℃ of boiling points or their mixture, in solution, add stabilizing agent again, the synergist mixing; (2) base material is cooperated with adhesive, it is kneaded and formed as line formula mosquito-repellent incense to add water, and section bar is made in oven dry, and the adhesive of indication is various starch, casein, carboxymethyl cellulose or polyvinyl alcohol; Binder dosage is 0.1～1.0% of a solid substrate weight; (3) the solution drop that step (1) is prepared is to the section bar of step (2).
According to the described a kind of insecticides of claim 1 in the application that prevents and treats aspect the household sanitary insect pest, it is characterized in that: described sanitary insect pest comprises mosquito, fly, cockroach, louse, acarid.
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| CN2010101917039A CN101878776A (en) | 2010-06-04 | 2010-06-04 | Insecticide composition and preparation method and application thereof |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104398126A (en) * | 2014-12-04 | 2015-03-11 | 苏华隆 | Incense stick formula and preparation technique for incense stick |
| CN109988068A (en) * | 2017-12-29 | 2019-07-09 | 江苏扬农化工股份有限公司 | A kind of pyrethroid compound of single spatial configuration |
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| US5135951A (en) * | 1990-02-27 | 1992-08-04 | Roussel Uclaf | 3-(2-cyano-2-halo-ethenyl)-2,2-dimethyl-cyclopropanecarboxylates |
| CN1284055A (en) * | 1997-12-22 | 2001-02-14 | 阿温提斯作物科学有限公司 | Derivatives of 2,2-dimethyl 3-(2-fluoro vinyl) cyclopropane carboxylic acid, their prepn process and use as pesticides |
| CN1451650A (en) * | 2002-04-12 | 2003-10-29 | 住友化学工业株式会社 | Ester compound and use thereof |
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2010
- 2010-06-04 CN CN2010101917039A patent/CN101878776A/en active Pending
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5135951A (en) * | 1990-02-27 | 1992-08-04 | Roussel Uclaf | 3-(2-cyano-2-halo-ethenyl)-2,2-dimethyl-cyclopropanecarboxylates |
| CN1284055A (en) * | 1997-12-22 | 2001-02-14 | 阿温提斯作物科学有限公司 | Derivatives of 2,2-dimethyl 3-(2-fluoro vinyl) cyclopropane carboxylic acid, their prepn process and use as pesticides |
| CN1451650A (en) * | 2002-04-12 | 2003-10-29 | 住友化学工业株式会社 | Ester compound and use thereof |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104398126A (en) * | 2014-12-04 | 2015-03-11 | 苏华隆 | Incense stick formula and preparation technique for incense stick |
| CN104398126B (en) * | 2014-12-04 | 2016-10-26 | 苏华隆 | A kind of preparation technology of line spices |
| CN109988068A (en) * | 2017-12-29 | 2019-07-09 | 江苏扬农化工股份有限公司 | A kind of pyrethroid compound of single spatial configuration |
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Application publication date: 20101110 |