CN1853476B - Insect killing composition - Google Patents
Insect killing composition Download PDFInfo
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- CN1853476B CN1853476B CN2006100743796A CN200610074379A CN1853476B CN 1853476 B CN1853476 B CN 1853476B CN 2006100743796 A CN2006100743796 A CN 2006100743796A CN 200610074379 A CN200610074379 A CN 200610074379A CN 1853476 B CN1853476 B CN 1853476B
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- dimethyl
- acrylic
- ester
- cyclopropane
- carboxylic acid
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Abstract
The invention discloses an insecticidal composition, which comprises the following parts: 2, 2-dimethyl-3-(2-methyl-1-allyl) cyclopropane carboxylic acid (2, 3, 5, 6-tetrafluoride-4-methoxymethylated benzyl) ester, 2, 2- dimethyl-3-(2- methyl-1-allyl) cyclopropane carboxylic acid (3-allyl group-2-methyl-4-oxocyclopentyl-2-alkylene) ester and 2(2, 3, 3, 3-tetrachloropropyl) ether.
Description
Technical field
The present invention relates to a kind of new Pesticidal combination and a kind of method of controlling insect.
Background technology
In JP2001-11022A, known by formula (1) provide 2,2-dimethyl-3-(2-methyl isophthalic acid-acrylic) cyclopropane-carboxylic acid (2,3,5,6-tetrafluoro-4-methoxy benzyl) ester:
It is a kind of active insecticidal components.
It is also known that at The Pesticide Manual 13
ThEdition (British Crop ProtectionCouncil, 2003) in, two (2,3,3,3-tetrachloro propyl group) ether (hereinafter referred to as " S421 ") be used to improve by formula (2) provide 2, the insecticidal activity of 2-dimethyl-3-(2-methyl isophthalic acid-acrylic) cyclopropane-carboxylic acid (3-pi-allyl-2-methyl-4-oxo ring penta-2-thiazolinyl) ester (hereinafter referred to as " allethrin "):
Summary of the invention
The invention provides a kind of Pesticidal combination, it comprises 2,2-dimethyl-3-(2-methyl isophthalic acid-acrylic) cyclopropane-carboxylic acid (2,3,5,6-tetrafluoro-4-methoxy benzyl) ester (hereinafter referred to as " compound (1) "), allethrin and S421 are wherein in described Pesticidal combination, the amount of allethrin is 1/3 to 100 times of compound (1) weight, and the amount of S421 is 5 to 500 times of compound (1) weight.Pesticidal combination of the present invention has excellent pesticidal effect by synergistic effect, can reduce the amount of the active component that is used to control insect thus.It is saved cost and environment is caused slight influence insect control is useful.In addition, the present invention also provides a kind of method of controlling insect, this method comprises: use 2 to insect or insect habitat, 2-dimethyl-3-(2-methyl isophthalic acid-acrylic) cyclopropane-carboxylic acid (2,3,5,6-tetrafluoro-4-methoxy benzyl) ester, 2,2-dimethyl-3-(2-methyl isophthalic acid-acrylic) cyclopropane-carboxylic acid (3-pi-allyl-2-methyl-4-oxo ring penta-2-thiazolinyl) ester and two (2,3,3,3-tetrachloro propyl group) ether.
Embodiment
Compound (1) is open in JP2001-11022A, and it can obtain according to specification.Compound (1) has optical isomer based on the asymmetric carbon atom on cyclopropane ring, and the present invention includes any active isomer and their mixture.
Allethrin is well-known compound, and can be on market available from various suppliers Sumitomo Chemical Company for example.Allethrin has various optical isomers and geometric isomer, and the present invention includes any active isomer and their mixture.The representative instance of allethrin comprises: (RS)-and cis, trans-2,2-dimethyl-3-(2-methyl isophthalic acid-acrylic) cyclopropane-carboxylic acid ((RS)-3-acrylic-2-methyl-4-oxo ring penta-2-thiazolinyl) ester (dl-allethrin), (1R)-cis, trans-2,2-dimethyl-3-(2-methyl isophthalic acid-acrylic) cyclopropane-carboxylic acid ((RS)-3-acrylic-2-methyl-4-oxo ring penta-2-thiazolinyl) ester (d-allethrin), (1R)-trans-2,2-dimethyl-3-(2-methyl isophthalic acid-acrylic) cyclopropane-carboxylic acid ((RS)-3-acrylic-2-methyl-4-oxo ring penta-2-thiazolinyl) ester (d-trans-allethrin) and (1R)-trans-2,2-dimethyl-3-(2-methyl isophthalic acid-acrylic) cyclopropane-carboxylic acid ((S)-3-acrylic-2-methyl-4-oxo ring penta-2-thiazolinyl) ester (d-trans-allethrin) (the trans allethrin of S-), and they can be available from Sumitomo ChemicalCompany.
S421 can be available from the market, and for example, it is that (SankyoChemical Industries Ltd.) makes by Pachinko chemical Industrial Co., Ltd.S421 former state on the market can be used for the present invention.
Pesticidal combination inclusion compound (1), allethrin and S421, wherein in Pesticidal combination, the amount of allethrin is 1/3 to 100 times of compound (1) weight, preferred 5 to 40 times, and the amount of S421 is 5 to 500 times of compound (1) weight, preferred 10 to 200 times.
Pesticidal combination of the present invention can be made up of compound (1), allethrin and S421.But, usually, its inclusion compound (1), allethrin and S421, and optional solid carrier, liquid-carrier, carrier gas, surfactant and other preparation used additives, be used to prepare the preparation that becomes gasification usefulness, as rolling up, fill up and have the solution of absorbent core; Liquid preparation is oil solution, emulsifiable concentrate and easy fluid for example; Solid pharmaceutical preparation is wetting powder, granula and pulvis for example; Aerosol; Sootiness preparation and mist formation preparation; Microcapsule formulation; With the ULV preparation.0.01 to 90 weight % of the common inclusion compound of these preparations (1), allethrin and S421 total amount.
The example of solid carrier comprises the fine powder and the particle of particle inorganic mineral, described inorganic mineral such as clay are (for example, kaolinton, diatomite, bentonite, Fubasami clay, carclazyte), talcum, beautiful mica, quartz, sulphur, active carbon, calcium carbonate, aqueous silica, synthetic Silicon dioxide, hydrate and fiber carrier, and the porous carrier that is used for electrical heating pad and desinsection coiled strip.
The representative instance of fiber carrier is natural fiber (for example, paper pulp, velveteen) and synthetic fibers (for example polyester, polyacrylate) body.The representative instance of porous carrier is pottery and ceramic wafer.
Usually, coiled strip is made up of one or more burning supporting agents and one or more adhesives basically.The example of burning supporting agent comprises for example wood powder of dried plant powder, pyrethrins marc, citrus peel meal, palm oil-bound distemper, coconut shell flour and walnut parting; Carbon dust such as charcoal powder, activated carbon powder and coal dust; And their mixture.The example of adhesive comprises polymer such as Tabu powder (dry powder of Matilus sp.), and starch (as tapioca, corn starch, wheaten starch), casein, Siam dough, polymer compound (for example, methylcellulose, carboxymethyl cellulose and polyvinyl alcohol) and their mixture.The weight ratio of burning supporting agent and adhesive is usually in 8: 2 to 6: 4 scope.
The example of liquid-carrier comprises water; Alcohols is methyl alcohol and ethanol for example; Ketone is acetone and ethyl methyl ketone for example; Aromatic hydrocarbons is toluene, dimethylbenzene, ethylbenzene and methyl naphthalene for example; Aliphatic hydrocarbon is hexane, cyclohexane, kerosene and gasoline for example; The ester class is ethyl acetate and butyl acetate for example; Nitrile is acetonitrile and isobutyronitrile for example; Ethers for example diisopropyl ether with diox; Amide-type is N for example, dinethylformamide and N,N-dimethylacetamide; Halogenated hydrocarbons is carrene, trichloroethanes and carbon tetrachloride for example; Methyl-sulfoxide; With vegetable oil for example soya-bean oil and cottonseed oil.
Carrier gas, promptly the example of propellant comprises fluorocarbon, butane gas, LPG (liquefied petroleum gas), dimethyl ether and carbonic acid gas.
The example of surfactant comprises alkyl sulfate salt, alkylsulfonate, alkylaryl sulfonates, polyoxyalkylene alkyl, polyoxyalkylene alkyl aryl ether, polyoxyalkylene styryl phenyl ether, polyvalent ester and sugar alcohol derivant.
The preparation used additives can be sticker, dispersant, stabilizing agent etc., and their example (for example comprises gelatin, polysaccharide, gum Arabic, cellulose derivatives, alginic acid), modified lignin, bentonite, carbohydrate, synthetic water-soluble polymer (for example, polyvinylpyrrolidone, polyacrylate), PAP (acidic isopropyl phosphate), BHT (2,6-two-tert-butyl-4-methylphenol), BHA (mixture of 2-tert-butyl-4-metoxyphenol and 3-tert-butyl-4-metoxyphenol), vegetable oil, mineral oil, fatty acid and fatty acid ester.
Pesticidal combination of the present invention can prepare by mixing cpd (1), allethrin, S421 and optional solid carrier, liquid-carrier, carrier gas, surfactant and other formulation auxiliary agents according to traditional program.
In addition, the Pesticidal combination of the present invention preparation that can also contain compound (1) mixes with the another kind of preparation that contains allethrin and S421 and prepares.
The Pesticidal combination that contains solid carrier can also be by following method (A) or (B) production.(A) a kind of method is by dissolved compound in organic solvent (1), allethrin and S421 and optional surfactant and/or auxiliary agent, with dissolving dipping solid carrier, optionally drying then.(B) a kind of method, by mixing cpd (1), allethrin and S421, solid carrier and optional surfactant and and/or auxiliary agent, randomly mediate moulding and drying with water.
Pesticidal combination of the present invention can be controlled for example Culex (CulexSPP) (Culex pipiens pallens (Culex pipiens pallens) for example of dipteral insect effectively, Culex quinquefasciatus (Culex pipiensquinquefaciatus), Culex tritaeniorhynchus (Culex tritaeniorhynchus)), Aedes (Aedesspp.) (Aedes aegypti (Aedes aegypti) for example, aedes albopictus (Aedes albopictus)), (Armigeressubalbatus), Anopheles (Anopheles spp.) (for example Anopheles sinensis (Anopheles sinensis)), Nuscidae (Muscidae) (housefly (Musca domestica) for example, false stable fly (Muscina stabulans), little Mao latrine fly (Fannia canicularis)), Calliphoridae (Calliphoridae), Flesh flies (Sarcophagidae), Moth files (Psychodidae) and Phorodae; And Dictyoptera (Dictyoptera) insect such as Groton bug (Blattella germanica), Peroplaneta fluligginosa (Periplaneta fuliginosa), American cockroach (Periplaneta Americana), the big Lian of foxiness (Periplaneta brunnea) and oriental cockroach (Blattaorientalis).
The method according to this invention can be by controlling insect to insect or insect habitat administered compound (1), allethrin and S421.
The amount of application of allethrin is 1/3 to 100 times of compound (1) weight, preferred 5 to 40 times, and the amount of application of S421 is 5 to 500 times of weight of compound (1), preferred 10 to 200 times.Easily Pesticidal combination of the present invention is used for said method, but for using, can be respectively with use every kind of component simultaneously.
Usually, to use for the space be 0.001 to 100mg/m to the total amount consumption of compound (1), allethrin and S421
3With using for aircraft is 0.01 to 1000mg/m
2But Pesticidal combination emulsifiable concentrate of the present invention, wetting powder fluid etc. are dilute with water usually, so that compound (1), allethrin and S421 total concentration are 0.01 to 10000ppm, and uses.Oil solution, aerosol, mist agent and poison bait are used under not diluting usually.When Pesticidal combination of the present invention is insecticidal mat, it is placed on the insect habitat, and on electric hot plate, heats to 120 to 180 ℃ approximately, evaporate active component then, with the control insect.When Pesticidal combination of the present invention is the desinsection volume, it is placed on the insect habitat and lights, evaporate active component then, with the control insect.
Embodiment
Below explain in detail the present invention; But it is not limited to the following examples.In the following embodiments, (1R, trans) isomer is used as compound (1).
Preparation embodiment 1
The d-of preparation 0.6w/v% is trans-each of the acetone soln of the acetone soln of the acetone soln of allethrin, the S421 of 0.6w/v% and (1) compound of 0.06w/v%.These acetone solns that mix equal volume.The mixture of 0.25ml is placed on the desinsection coiled strip of 0.5g, and dry to obtain the desinsection volume.
Preparation embodiment 2
Each of the acetone soln of the acetone soln of the d-allethrin of preparation 0.6w/v%, the S421 of 2.4w/v% and the acetone soln of 0.06w/v% compound (1).These acetone solns that mix equal volume.The mixture of 0.25ml is placed on the desinsection coiled strip of 0.5g, and dry to obtain the desinsection volume.
Preparation embodiment 3
Each of the acetone soln of the acetone soln of the trans allethrin of S-of preparation 0.3w/v%, the S421 of 3.0w/v% and the acetone soln of 0.06w/v% compound (1).These acetone solns that mix equal volume.The mixture of 0.25ml is placed on the desinsection coiled strip of 0.5g, and dry to obtain the desinsection volume.
Preparation embodiment 4
Each of the acetone soln of the acetone soln of the dl-allethrin of preparation 1.2w/v%, the S421 of 1.2w/v% and the acetone soln of 0.06w/v% compound (1).These acetone solns that mix equal volume.The mixture of 0.25ml is placed on the desinsection coiled strip of 0.5g, and dry to obtain the desinsection volume.
Preparation embodiment 5
The d-of preparation 2.4w/v% is trans-each of the acetone soln of the acetone soln of allethrin, the S421 of 12w/v% and the acetone soln of 0.06w/v% compound (1).These acetone solns that mix equal volume.The mixture of 0.25ml is placed on the desinsection coiled strip of 0.5g, and dry to obtain the desinsection volume.
Be the reference example that is used to provide with reference to the desinsection volume below.
Reference example 1
The acetone soln of the compound (1) of preparation 0.02w/v%.These acetone solns that mix equal volume.The acetone soln of 0.25ml is placed on the desinsection coiled strip of 0.5g, and dry to obtain the desinsection volume of reference.
Reference example 2
The d-of preparation 0.4w/v% is trans-each of the acetone soln of the acetone soln of allethrin and the S421 of 0.4w/v%.These acetone solns that mix equal volume.The mixture of 0.25ml is placed on the desinsection coiled strip of 0.5g, and dry to obtain the desinsection volume.
Reference example 3
Each of the acetone soln of the acetone soln of the d-allethrin of preparation 0.4w/v% and the S421 of 1.6w/v%.These acetone solns that mix equal volume.The mixture of 0.25ml is placed on the desinsection coiled strip of 0.5g, and dry to obtain the desinsection volume.
Reference example 4
Each of the acetone soln of the acetone soln of the trans allethrin of S-of preparation 0.2w/v% and the S421 of 2.0w/v%.These acetone solns that mix equal volume.The mixture of 0.25ml is placed on the desinsection coiled strip of 0.5g, and dry to obtain the desinsection volume.
Reference example 5
Each of the acetone soln of the acetone soln of the dl-allethrin of preparation 0.8w/v% and the S421 of 0.8w/v%.These acetone solns that mix equal volume.The mixture of 0.25ml is placed on the desinsection coiled strip of 0.5g, and dry to obtain the desinsection volume.
Reference example 6
The d-of preparation 1.6w/v% is trans-each of the acetone soln of the acetone soln of allethrin and the S421 of 8.0w/v%.These acetone solns that mix equal volume.The mixture of 0.25ml is placed on the desinsection coiled strip of 0.5g, and dry to obtain the desinsection volume.
The effect of Pesticidal combination of the present invention is described by following embodiment.
Experimental example 1
At cube chamber (70cm
3) in, place each of the desinsection volume that obtains by above-mentioned preparation embodiment and reference example in centre bottom.
Light the desinsection volume, and by little electric fan diffusion smog.Behind burning-out desinsection volume, the electric fan of moving away, and in this chamber, put 20 adult houseflies (10 male houseflies and 10 female houseflies, housefly Muscadomestica) into.
After 20 minutes, respectively the housefly of knocking down is counted, and calculate rate of knockdown.To every kind of desinsection volume, repeat 2 tests, and average.The result awards in the table 1.
Table 1
Experimental example 2
At cube chamber (70cm
3) in, place each of the desinsection volume that obtains by above-mentioned preparation embodiment and reference example in centre bottom.
Light the desinsection volume, and by little electric fan diffusion smog.Behind burning-out desinsection volume, the electric fan of moving away, and in this chamber, put 20 adult houseflies (10 male houseflies and 10 female houseflies, housefly (Muscadomestica)) into.
After 5 minutes, respectively the housefly of knocking down is counted, and calculate rate of knockdown.To every kind of desinsection volume, repeat 2 tests, and average.The result awards in the table 2.
Claims (2)
1. Pesticidal combination, it comprises 2,2-dimethyl-3-(2-methyl isophthalic acid-acrylic) cyclopropane-carboxylic acid (2,3,5,6-tetrafluoro-4-methoxy benzyl) ester, 2,2-dimethyl-3-(2-methyl isophthalic acid-acrylic) cyclopropane-carboxylic acid (3-pi-allyl-2-methyl-4-oxo ring penta-2-thiazolinyl) ester and two (2,3,3,3-tetrachloro propyl group) ether, wherein in described Pesticidal combination, 2, the amount of 2-dimethyl-3-(2-methyl isophthalic acid-acrylic) cyclopropane-carboxylic acid (3-pi-allyl-2-methyl-4-oxo ring penta-2-thiazolinyl) ester is 2,2-dimethyl-3-(2-methyl isophthalic acid-acrylic) cyclopropane-carboxylic acid (2,3,5,6-tetrafluoro-4-methoxy benzyl) 5 to 40 times of ester weight, and two (2,3,3,3-tetrachloro propyl group) amount of ether is 2,2-dimethyl-3-(2-methyl isophthalic acid-acrylic) cyclopropane-carboxylic acid (2,3,5,6-tetrafluoro-4-methoxy benzyl) 10 to 200 times of ester weight.
2. method of controlling insect, this method comprises: use 2 to insect or insect habitat, 2-dimethyl-3-(2-methyl isophthalic acid-acrylic) cyclopropane-carboxylic acid (2,3,5,6-tetrafluoro-4-methoxy benzyl) ester, 2,2-dimethyl-3-(2-methyl isophthalic acid-acrylic) cyclopropane-carboxylic acid (3-pi-allyl-2-methyl-4-oxo ring penta-2-thiazolinyl) ester and two (2,3,3,3-tetrachloro propyl group) ether, wherein 2, the amount of 2-dimethyl-3-(2-methyl isophthalic acid-acrylic) cyclopropane-carboxylic acid (3-pi-allyl-2-methyl-4-oxo ring penta-2-thiazolinyl) ester is 2,2-dimethyl-3-(2-methyl isophthalic acid-acrylic) cyclopropane-carboxylic acid (2,3,5,6-tetrafluoro-4-methoxy benzyl) 5 to 40 times of ester weight, and two (2,3,3,3-tetrachloro propyl group) amount of ether is 2,2-dimethyl-3-(2-methyl isophthalic acid-acrylic) cyclopropane-carboxylic acid (2,3,5,6-tetrafluoro-4-methoxy benzyl) 10 to 200 times of ester weight.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2005-119369 | 2005-04-18 | ||
| JP2005119369A JP2006298789A (en) | 2005-04-18 | 2005-04-18 | Vermin controlling agent |
| JP2005119369 | 2005-04-18 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1853476A CN1853476A (en) | 2006-11-01 |
| CN1853476B true CN1853476B (en) | 2011-04-13 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2006100743796A Expired - Fee Related CN1853476B (en) | 2005-04-18 | 2006-04-14 | Insect killing composition |
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| Country | Link |
|---|---|
| JP (1) | JP2006298789A (en) |
| CN (1) | CN1853476B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011116737A (en) * | 2009-10-30 | 2011-06-16 | Sumitomo Chemical Co Ltd | Harmful organism-controlling composition and method for controlling harmful organism |
| JP5589712B2 (en) * | 2009-10-30 | 2014-09-17 | 住友化学株式会社 | Pest control composition and pest control method |
| CN105613529A (en) * | 2016-02-16 | 2016-06-01 | 烟台米罗卡化工科技有限公司 | Insecticide for aedes albopictus |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5626834A (en) * | 1991-10-17 | 1997-05-06 | Sumitomo Chemical Company, Limited | Snake-controlling agent |
| CN1240107A (en) * | 1998-04-27 | 2000-01-05 | 蔡荣昌 | Hygienic biocide composition |
| CN1358430A (en) * | 2002-01-14 | 2002-07-17 | 杭州潘山实业集团有限公司 | Smoke free mosquito-repellent incense |
| CN1596639A (en) * | 2004-07-19 | 2005-03-23 | 常坤 | Triple-effect mosquito repellent incense |
-
2005
- 2005-04-18 JP JP2005119369A patent/JP2006298789A/en active Pending
-
2006
- 2006-04-14 CN CN2006100743796A patent/CN1853476B/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5626834A (en) * | 1991-10-17 | 1997-05-06 | Sumitomo Chemical Company, Limited | Snake-controlling agent |
| CN1240107A (en) * | 1998-04-27 | 2000-01-05 | 蔡荣昌 | Hygienic biocide composition |
| CN1358430A (en) * | 2002-01-14 | 2002-07-17 | 杭州潘山实业集团有限公司 | Smoke free mosquito-repellent incense |
| CN1596639A (en) * | 2004-07-19 | 2005-03-23 | 常坤 | Triple-effect mosquito repellent incense |
Non-Patent Citations (2)
| Title |
|---|
| JP特开2002-220303A 2002.08.09 |
| JP特开2003-183107A 2003.07.03 |
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| Publication number | Publication date |
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| CN1853476A (en) | 2006-11-01 |
| JP2006298789A (en) | 2006-11-02 |
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