CN101322496A - Joss-stick for repelling fly and preparation thereof - Google Patents
Joss-stick for repelling fly and preparation thereof Download PDFInfo
- Publication number
- CN101322496A CN101322496A CNA2008101325077A CN200810132507A CN101322496A CN 101322496 A CN101322496 A CN 101322496A CN A2008101325077 A CNA2008101325077 A CN A2008101325077A CN 200810132507 A CN200810132507 A CN 200810132507A CN 101322496 A CN101322496 A CN 101322496A
- Authority
- CN
- China
- Prior art keywords
- trans
- cholrempenthrin
- joss stick
- shoofly joss
- shoofly
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention provides a fly expelling line incense with the active compound is trans-chlorempenthrin, the structure of which is the following formula (A). The content of the compound is the fly expelling line incense is 0.1-3.0 w/w%. Compared with the prior art, the fly expelling line incense of the invention has better control efficiency. The invention further provides a method for preparing the fly expelling line incense.
Description
Technical field
The present invention relates to a kind of insecticide, relate in particular to a kind of Shoofly joss stick, and preparation method thereof.
Background technology
Pyrethroid coumpound can be used to prevent and treat sanitary insect pests such as mosquitos and flies, and has higher insecticidal activity, and this is widely known by the people.On the other hand for fly in the fishing village, the appearance of aquatic product manufactory, destructor plant and peripheries such as animal house, pouity dwelling place is vexing all the time.Countermeasure when producing as fly, except using insecticides such as emulsion, finish, pulvis, general family generally uses insect aerosol, is the shortcoming of disposable shortage continuation effect but there is what is called.Therefore wish a kind of Shoofly joss stick of exploitation, promptly as the spatial manipulation agent, and lasting effect a few hours, and then diffusibility will get well, though in open place also effective line spices type.
At present commercially available with the Es-allethrin, transfluthrin etc. are easy to use as the mosquito repellent line spices of main active ingredient, can keep spatial manipulation for a long time after lighting, and until after-flame, volatilization is stable, render a service stablely, are a kind of very reasonably desinsection modes.But this class mosquito-repellent incense is generally a little less than the effectiveness to fly, even improve the active ingredient concentration in the line spices, also is not suitable for being used as Shoofly joss stick.The active ingredient of therefore selected optimal Shoofly joss stick is an important problem.Disclose in Japan Patent JP10-203905 with 2-pi-allyl-3-methyl-ring penta-2-alkene-1-ketone-4-base-2,2,3, the 3-4-methyl cyclopropane carboxylic acid ester is as the Shoofly joss stick of active ingredient, but effect and unsatisfactory.
Based on above-mentioned background, the present invention proposes a kind of new Shoofly joss stick, adopts the compound that fly is had better preventive effect as active ingredient, has improved the control efficiency of Shoofly joss stick.
Summary of the invention
The objective of the invention is to: a kind of new Shoofly joss stick is provided, fly is had higher preventive effect.
Purpose of the present invention is achieved through the following technical solutions:
A kind of Shoofly joss stick is provided, its active ingredient is the trans cholrempenthrin of structure as shown in the formula (A), the chemical name of this compound is: 2,2-dimethyl-3-trans-(2, the 2-dichloroethylene) cyclopropane-carboxylic acid-1-acetenyl-2-methylpent-2-alkenyl esters, the isomer that comprises these all biologically actives of compound among the present invention, the content in Shoofly joss stick are 0.1～3.0w/w%.
Described trans cholrempenthrin is preferably the trans cholrempenthrin of dextrorotation of acid moieties single optical activity isomery.
The trans cholrempenthrin of described dextrorotation prepares in accordance with the following methods:
1) utilize chemical resolving agent to split the trans dichlor chrysanthemic acid of racemization, obtain the trans dichlor chrysanthemic acid of dextrorotation, the mol ratio of described chemical resolving agent and racemization trans-chrysanthemate is 0.2: 1～4: 1;
2) with chloride reagent with the trans dichlor chrysanthemic acid chloride of dextrorotation that step 1) obtains, obtain the trans dichloro acyl chlorides of dextrorotation; Wherein, the mol ratio of described chloride reagent and the trans dichlor chrysanthemic acid of dextrorotation is 0.2: 1～4: 1;
3) with step 2) the trans dichloro acyl chlorides of dextrorotation and the 4-methyl isophthalic acid-alkynes-4-alkene-3-enanthol that obtain carry out esterification, obtains the pyrethroid compound that described structure is formula A; Wherein, the mol ratio of the trans dichloro acyl chlorides of described dextrorotation and 4-methyl isophthalic acid-alkynes-4-alkene-3-enanthol is 0.2: 1～4: 1.
Concrete grammar can be:
1) the trans dichlor chrysanthemic acid of fractionation racemization
In the four-hole bottle of a 1000ml, drop into trans dichlor chrysanthemic acid 100.0g, dextrorotation PTE 125.0g, be dissolved in 400ml toluene, throw to finish and stir, be warming up to 110 ℃ of back flow reaction 1 hour, in 3 hours, be cooled to 60 ℃ then, be incubated 1 hour, be cooled to 20 ℃ again in 2 hours, be incubated 1 hour, have a large amount of crystal to separate out this moment, filtration obtains crystal, the hcl acidifying that adds 200g 5% adds the extraction of 400ml toluene, layering simultaneously, oil-reservoir water is washed till nearly neutrality, be heated to 100 ℃ and purify solvent toluene under the 10mmHg negative pressure, obtain (R)-2,2-dimethyl-3-trans-(2, the 2-dichloroethylene) cyclopropane-carboxylic acid 45.2g, the effective body ee of dextrorotation value 96%.
2) chloride of the trans dichlor chrysanthemic acid of dextrorotation
In the four-hole bottle of a 1000ml, drop into above-mentioned steps 1) the middle trans dichlor chrysanthemic acid 209g of dextrorotation (1molee value 97%) that obtains that splits, be dissolved in 600ml toluene, throw to finish and stir, be warming up to 50 ℃, drip the toluene solution 200ml that contains triphosgene 118.7g (0.4mol), drip in 2 hours and finish, be warming up to 60 ℃ again, insulation reaction.Reaction is finished be heated to 80 ℃ of desolventizing toluene under the 30mmHg negative pressure, and 60 ℃～75 ℃ cuts are received in rectifying under the 10mmHg negative pressure again, obtaining (R)-2,2-dimethyl-3-is trans-(2, the 2-dichloroethylene) cyclopropane carboxylic acid isoxazolecarboxylic acid 214.1g, yield 94.3%, the effective body ee of dextrorotation value 97%.
3) the trans cholrempenthrin of preparation dextrorotation
In the four-hole bottle of a 2000ml, drop into 4-methyl isophthalic acid-alkynes-4-alkene-3-enanthol 62.0g, pyridine 50.0g, be dissolved in 600ml toluene, throw to finish stir, 0～5 ℃ drips above-mentioned steps 2 down) (R)-2 that prepare, 2-dimethyl-3-trans-(2, the 2-dichloroethylene) cyclopropane carboxylic acid isoxazolecarboxylic acid 114.0g drips 20 ℃ of reactions of Bi Shengzhi 4 hours.With 400ml 5% salt acid elution, again with 400ml 5%NaHCO3 washing, divide oil-yielding stratum under the 10mmHg negative pressure, to be heated to 100 ℃ and purify solvent toluene, obtain compound (1R, 3S)-2,2-dimethyl-3-(2, the 2-dichloroethylene) cyclopropane-carboxylic acid-1-acetenyl-2-methylpent-2-alkenyl esters, weight 150.3g, content are 98.0%, yield 93.3%.The molecular formula of this compound: C
16H
20Cl
2O
2Molecular weight: 315.1 optically-actives [α]=-8.32, infrared signature absworption peak are 3280,3040,1720,1160,850cm
-1Nuclear magnetic resoance spectrum (1H (ppm) CDCl
3) 5.79 (d, 1H); 5.70 (t, 1H); 5.14 (d, 1H); 2.52 (d, 1H); 2.24 (dd, 1H); 1.64 (d, 1H); 2.08 (m, 2H); 1.75 (m, 3H); 1.20-1.30 (s, 6H); 1.15 (t, 3H).
Di-t-butyl-phenol stabilizing agent of the fragrant total amount 0.1～1w/w% that contains preferably also in the described Shoofly joss stick that the line is busy.Stability when this class stabilizing agent can improve fumigation guarantees the continual and steady of drug effect.
Described di-t-butyl-phenol stabilizing agent can be selected from 2,6-di-tert-butyl-4-methy phenol (BHT), 2,2-methylene two (4-methyl-6-tert butyl phenol), 2,2-methylene two (4-ethyl-6-tert-butyl phenol), 4,4-butylidene two (3 methy 6 tert butyl phenol) or 4, the mixture of one or more in the 4-sulfo-two (3 methy 6 tert butyl phenol).
The present invention also provides the preparation method of described Shoofly joss stick, is to join in the base material after described trans cholrempenthrin is mixed with liquid form, makes the described Shoofly joss stick that trans cholrempenthrin content is 0.1～3.0w/w%.
The preferred manufacturing procedure of described Shoofly joss stick can be after described trans cholrempenthrin is mixed with liquid form, adds described di-t-butyl-phenol stabilizing agent again in this solution, joins in the base material again, makes the Shoofly joss stick that contains stabilizing agent; Wherein make trans cholrempenthrin content reach 0.1～3.0w/w%, make the content of stabilizing agent reach 0.1～1w/w%.
The liquid form that described trans cholrempenthrin is mixed with is missible oil or is 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 inflammable substances and one or more adhesives, and wherein the weight ratio of inflammable substance and adhesive is 90: 10 to 99.9: 0.1.
Described inflammable substance can be the plant drymeal that is selected from wood powder, Dalmatian chrysanthemum extraction powder, citrus peel meal, palm oil-bound distemper, coconut shell powder or walnut parting, or is selected from the carbon dust of charcoal powder, activated carbon powder or coal dust, or their mixture; Described adhesive can be the Tabu powder, is selected from the starch of tapioca, corn starch or wheaten starch, casein, methylcellulose, the polymer of carboxymethyl cellulose or polyvinyl alcohol and composition thereof.
Described Shoofly joss stick base material normally by mixing inflammable substance and adhesive, is mediated with water, moulding and oven dry preparation.The shape of Shoofly joss stick base material can be plate-like or strip without limits.The present invention uses about 12cm of diameter and thickness usually in two line spices of a cover be the conventional coil shape base material of 3～5mm.
The Shoofly joss stick that more than obtains can conventional method use.That is, light Shoofly joss stick of the present invention near (for example dwelling house, stock barn) or its in the habitat of fly.The burning of Shoofly joss stick can make the volatilization of trans cholrempenthrin, and after airborne active ingredient reached certain concentration, housefly produced to be stimulated, drive, benumb, knock down and lethal effect, thereby reaches the control to housefly.
Present inventors filter out 2 through research contrast, and 2-dimethyl-3-is trans-and (2, the 2-dichloroethylene) cyclopropane-carboxylic acid-1-acetenyl-2-methylpent-2-alkenyl esters (trans cholrempenthrin) is as the active ingredient of Shoofly joss stick.By experimental results demonstrate, with this compound is that the Shoofly joss stick that active ingredient prepares has very good control efficiency to housefly, and the drug effect volatilization is stable, for example with tetrafluoro ether chrysanthemum ester (dimefluthrin) for the Shoofly joss stick of active ingredient carries out the drug effect contrast test, the result shows that the drug effect of line spices of the present invention is 1.3 times of tetrafluoro ether chrysanthemum ester line spices.The inventor also finds in addition, it should be noted that especially if with acid moieties be the trans cholrempenthrin of dextrorotation of single optical isomer as active ingredient, the relative raceme of its drug effect will improve 0.5 times.
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.
Preparation embodiment 1.
With the trans cholrempenthrin of 0.28g, 0.08g BHT is dissolved in 1g kerosene, and drop to the blank line spices base of 35g is made Shoofly joss stick I, wherein contains trans cholrempenthrin 0.8w/w%, contains BHT 0.2w/w%.
Preparation embodiment 2.
With the trans cholrempenthrin of 0.28g, 0.04gBHT, 0.04g4,4-sulfo-two (3 methy 6 tert butyl phenol) is dissolved in 1g kerosene, drop to the blank line spices base of 35g is made Shoofly joss stick II, wherein contains trans cholrempenthrin 0.8w/w%, contains BHT 0.1w/w%, contain 4,4-sulfo-two (3 methy 6 tert butyl phenol) 0.1w/w%.
Preparation embodiment 3.
With the trans cholrempenthrin of 0.14g, 0.08g BHT is dissolved in 1g kerosene, and drop to the blank line spices base of 35g is made Shoofly joss stick III, wherein contains trans cholrempenthrin 0.4w/w%, contains BHT0.2w/w%.
Preparation embodiment 4.
With the trans cholrempenthrin of 0.28g dextrorotation, 0.08gBHT is dissolved in 1g kerosene, and drop to the blank line spices base of 35g is made Shoofly joss stick IV, wherein contains the trans cholrempenthrin 0.8w/w% of dextrorotation, contains BHT0.2w/w%.
Reference example 1.
With 0.28g tetrafluoro ether chrysanthemum ester, 0.08gBHT is dissolved in 1g kerosene, and drop to the blank line spices base of 35g is made Shoofly joss stick V, wherein contains tetrafluoro ether chrysanthemum ester 0.8w/w%, contains BHT 0.2w/w% tetrafluoro ether chrysanthemum ester.
Detect embodiment 1
The present invention is prepared embodiment 1,2,3,4 and reference example 1 carry out indoor harmacological effect test housefly with reference to GB13917.4-92.Examination worm housefly, the 4th day adult in back that sprout wings, male and female half and half.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; appoint and get fragrant one section of tested fly; put to fragrant frame; light the fragrant timing of fly, remove fly perfume (or spice) behind the 1min, write down down and out examination fly 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 housefly.
The control efficiency of the above-mentioned Shoofly joss stick of table 1.
| Line spices | KT50(min) | 24h lethality (%) |
| Shoofly joss stick I | 3.82 | 100 |
| Shoofly joss stick II | 3.95 | 100 |
| Shoofly joss stick III | 5.70 | 100 |
| Shoofly joss stick IV | 2.59 | 100 |
| Shoofly joss stick V | 4.90 | 100 |
The result shows: the trans cholrempenthrin Shoofly joss stick of the present invention's preparation has good insect killing effect to housefly, its drug effect is about 1.3 times of tetrafluoro ether chrysanthemum ester line spices at present commonly used, and the trans cholrempenthrin of the dextrorotation of single optical siomerism is 1.5 times of its raceme drug effect in addition.
Claims (10)
1. Shoofly joss stick, it is characterized in that: its active ingredient is the trans cholrempenthrin of structure as shown in the formula (A), and the content of this compound in Shoofly joss stick is 0.1～3.0w/w%.
2. the described Shoofly joss stick of claim 1, it is characterized in that: described trans cholrempenthrin is the trans cholrempenthrin of dextrorotation of acid moieties single optical activity isomery.
3. claim 1 or 2 described any one Shoofly joss sticks is characterized in that: di-t-butyl-phenol stabilizing agent of the fragrant total amount 0.1～1w/w% that contains also in the described Shoofly joss stick that the line is busy.
4. the described Shoofly joss stick of claim 3, it is characterized in that: described di-t-butyl-phenol stabilizing agent is selected from 2,6-di-tert-butyl-4-methy phenol (BHT), 2,2-methylene two (4-methyl-6-tert butyl phenol), 2,2-methylene two (4-ethyl-6-tert-butyl phenol), 4,4-butylidene two (3 methy 6 tert butyl phenol) or 4, the mixture of one or more in the 4-sulfo-two (3 methy 6 tert butyl phenol).
5. the preparation method of the described Shoofly joss stick of claim 1 is to join in the base material after described trans cholrempenthrin is mixed with liquid form, makes the described Shoofly joss stick that trans cholrempenthrin content is 0.1～3.0w/w%.
6. the preparation method of the described Shoofly joss stick of claim 3, be after described trans cholrempenthrin is mixed with liquid form, in this solution, add described di-t-butyl-phenol stabilizing agent again, join again in the base material, make the Shoofly joss stick that contains stabilizing agent; Wherein make trans cholrempenthrin content reach 0.1～3.0w/w%, make the content of stabilizing agent reach 0.1～1w/w%.
7. the preparation method of claim 5 or 6 described any one Shoofly joss sticks is characterized in that: the liquid form that described trans cholrempenthrin is mixed with is missible oil or is the solution of solvent with the hydro carbons.
8. the preparation method of the described Shoofly joss stick of claim 7 is characterized in that: described varsol is kerosene, have the saturated hydrocarbons solvent of 150～350 ℃ of boiling points or their mixture.
9. the preparation method of claim 5 or 6 described any one Shoofly joss sticks, it is characterized in that: described base material is made up of one or more inflammable substances and one or more adhesives, and wherein the weight ratio of inflammable substance and adhesive is 90: 10 to 99.9: 0.1.
10. the preparation method of the described Shoofly joss stick of claim 9, it is characterized in that: described inflammable substance is the plant drymeal that is selected from wood powder, Dalmatian chrysanthemum extraction powder, citrus peel meal, palm oil-bound distemper, coconut shell powder or walnut parting, or be selected from the carbon dust of charcoal powder, activated carbon powder or coal dust or their mixture; Described adhesive is the Tabu powder, is selected from the starch of tapioca, corn starch or wheaten starch, casein, methylcellulose, the polymer of carboxymethyl cellulose or polyvinyl alcohol and composition thereof.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2008101325077A CN101322496A (en) | 2008-07-15 | 2008-07-15 | Joss-stick for repelling fly and preparation thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2008101325077A CN101322496A (en) | 2008-07-15 | 2008-07-15 | Joss-stick for repelling fly and preparation thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101322496A true CN101322496A (en) | 2008-12-17 |
Family
ID=40186334
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA2008101325077A Pending CN101322496A (en) | 2008-07-15 | 2008-07-15 | Joss-stick for repelling fly and preparation thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101322496A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101785454A (en) * | 2010-04-08 | 2010-07-28 | 徐建成 | Improved type fly-killing incense and manufacturing method thereof |
| CN101785472A (en) * | 2010-04-08 | 2010-07-28 | 徐建成 | Improved type fly-killing incense liquor and manufacturing method thereof |
| CN104430318A (en) * | 2014-11-25 | 2015-03-25 | 贵阳中精科技有限公司 | Pyrethroid incense stick |
| CN104430319A (en) * | 2014-11-25 | 2015-03-25 | 贵阳中精科技有限公司 | Pyrethroid incense stick |
| CN105052987A (en) * | 2015-08-10 | 2015-11-18 | 广西柳州昊邦日化有限公司 | Ignition type fly eradication incense |
| CN114181079A (en) * | 2020-09-11 | 2022-03-15 | 江苏优嘉植物保护有限公司 | Preparation method of efficient chlorenthrin |
-
2008
- 2008-07-15 CN CNA2008101325077A patent/CN101322496A/en active Pending
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101785454A (en) * | 2010-04-08 | 2010-07-28 | 徐建成 | Improved type fly-killing incense and manufacturing method thereof |
| CN101785472A (en) * | 2010-04-08 | 2010-07-28 | 徐建成 | Improved type fly-killing incense liquor and manufacturing method thereof |
| CN101785472B (en) * | 2010-04-08 | 2012-12-05 | 徐建成 | Improved type fly-killing incense liquor and manufacturing method thereof |
| CN101785454B (en) * | 2010-04-08 | 2013-01-23 | 徐建成 | Improved type fly-killing incense and manufacturing method thereof |
| CN104430318A (en) * | 2014-11-25 | 2015-03-25 | 贵阳中精科技有限公司 | Pyrethroid incense stick |
| CN104430319A (en) * | 2014-11-25 | 2015-03-25 | 贵阳中精科技有限公司 | Pyrethroid incense stick |
| CN105052987A (en) * | 2015-08-10 | 2015-11-18 | 广西柳州昊邦日化有限公司 | Ignition type fly eradication incense |
| CN114181079A (en) * | 2020-09-11 | 2022-03-15 | 江苏优嘉植物保护有限公司 | Preparation method of efficient chlorenthrin |
| CN114181079B (en) * | 2020-09-11 | 2023-10-31 | 江苏优嘉植物保护有限公司 | Preparation method of high-efficiency permethrin |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN100545144C (en) | A kind of optically active pyrethroid coumpound and its production and application | |
| ES2338983T3 (en) | NEW SUBSTANCES THAT ATTRACT, ADD AND STOP LARVA AND ADULTS OF THE TWO SEXES OF APPLE MothS AND OTHER LEPIDOPTER SPECIES. | |
| CN101323571B (en) | Pyrethroid compounds, preparation and use thereof | |
| CN101473842B (en) | Insecticidal composition | |
| CN100584817C (en) | Pyrethroid compound and uses | |
| CN101524084B (en) | Muscicide incense and preparation method and application thereof | |
| CN101322496A (en) | Joss-stick for repelling fly and preparation thereof | |
| CN107467021B (en) | Attractant composition for preventing and treating helicoverpa clarkii | |
| CN103109808B (en) | Apolygus lucorum Meyer-Dur and Adelphocoris suturalis jakovlev attractant and application thereof | |
| Carlos et al. | Scientific and technological developments in mating disruption of scale insects | |
| CN101880243A (en) | Fluorocyanogen-containing pyrethroid compound and synthesis method and application thereof | |
| CN101297642A (en) | Insecticidal aerosol and preparation and use thereof | |
| CN101792392B (en) | Optically active pyrethroid and preparation method and application thereof | |
| CN101671251B (en) | Pyrethroid compound as well as preparation method and application thereof | |
| CN101348437B (en) | Pyrethroid compounds, preparation and use thereof | |
| CN102584592B (en) | Deuterated pyrethroid compound and preparation method and application thereof | |
| CN101492393B (en) | Pyrethroid compounds, preparation and use thereof | |
| CN101830805A (en) | Fluoropyrethroid containing compound as well as synthesis method and application thereof | |
| CN101878776A (en) | Insecticide composition and preparation method and application thereof | |
| JP2007284400A (en) | Sex attractant of planococcus kraunhiae | |
| CN102976944A (en) | Pyrethroid compound as well as preparation method and application thereof | |
| CN104430482A (en) | Pyrethroid incense coil | |
| CN101845020B (en) | Fluorinated pyrethroid compound and application thereof | |
| CN102584710B (en) | Chloric perfluorocyclopropane carboxylic ester type compound as well as preparation and application thereof | |
| CN102633684B (en) | Pyrethroid compound, preparation method and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C12 | Rejection of a patent application after its publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20081217 |