フェノトリン、フェノスリン
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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2015/01/29 17:37:00」(JST)
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Phenothrin |
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IUPAC name
(3-Phenoxyphenyl)methyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate
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Other names
Sumithrin
Phenothrine
Phenoxythrin
Sumitrin
Wellcide
Pibutin
Anvil
Duet
Anchimanaito 20S
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Identifiers |
CAS number |
26002-80-2 Y |
PubChem |
4767 |
ChemSpider |
4603 Y |
EC number |
247-404-5 |
KEGG |
D08357 N |
MeSH |
Phenothrin |
ChEBI |
CHEBI:34916 Y |
ChEMBL |
CHEMBL1322884 N |
ATC code |
P03AC03,QP53AC03 |
Jmol-3D images |
Image 1 |
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O=C(OCc2cccc(Oc1ccccc1)c2)C3C(/C=C(/C)C)C3(C)C
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InChI=1S/C23H26O3/c1-16(2)13-20-21(23(20,3)4)22(24)25-15-17-9-8-12-19(14-17)26-18-10-6-5-7-11-18/h5-14,20-21H,15H2,1-4H3 Y
Key: SBNFWQZLDJGRLK-UHFFFAOYSA-N Y
InChI=1/C23H26O3/c1-16(2)13-20-21(23(20,3)4)22(24)25-15-17-9-8-12-19(14-17)26-18-10-6-5-7-11-18/h5-14,20-21H,15H2,1-4H3
Key: SBNFWQZLDJGRLK-UHFFFAOYAY
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Properties |
Molecular formula |
C23H26O3 |
Molar mass |
350.451 g/mol |
Melting point |
<25 °C |
Boiling point |
>290 °C |
Hazards |
R-phrases |
R36 R38 |
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) |
N (verify) (what is: Y/N?) |
Infobox references |
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Phenothrin, also called sumithrin, is a synthetic pyrethroid that kills adult fleas and ticks. It has also been used to kill head lice in humans. D-Phenothrin is used as a component of aerosol insecticides for domestic use. Phenothrin is often used with methoprene, an insect growth regulator that interrupts the insect's biological life cycle by killing the eggs.
Contents
- 1 Effects
- 2 EPA action
- 3 References
- 4 External links
Effects
Phenothrin is primarily used to kill fleas and ticks.[1] It is also used to kill head lice in humans, but studies conducted in Paris, France and the United Kingdom have shown widespread resistance to phenothrin.[1]
It is extremely toxic to bees. A U.S. Environmental Protection Agency (EPA) study found that 0.07 micrograms was enough to kill honey bees.[1] It is also extremely toxic to aquatic life with a study showing concentrations of 0.03 ppb killing mysid shrimp.[1] It has increased risk of liver cancer in rats and mice in long term exposure.[1] It is poisonous to cats and dogs, with seizures and deaths being reported due to poisoning.[1] Specific data on concentrations or exposure is lacking.
The EPA has not assessed its effect on cancer in humans. However, one study performed by the Mt. Sinai School of Medicine links sumithrin with breast cancer; the link made by sumithrin's affect on increasing the expression of a gene responsible for mammary tissue proliferation.[1]
EPA action
In 2005, the U.S. EPA canceled permission to use phenothrin in several flea and tick products, at the request of the manufacturer, Hartz Mountain Industries.[2][3] The products were linked to a range of adverse reactions, including hair loss, salivation, tremors, and numerous deaths in cats and kittens. In the short term, the agreement called for new warning labels on the products.
As of March 31, 2006, the sale and distribution of Hartz's phenothrin-containing flea and tick products for cats has been terminated. However, EPA's product cancellation order did not apply to Hartz flea and tick products for dogs, and Hartz continues to produce many of its flea and tick products for dogs.[4]
References
- ^ a b c d e f g JOURNAL OF PESTICIDE REFORM/ SUMMER 2003 • VOL. 23, NO. 2 http://www.pesticide.org/get-the-facts/pesticide-factsheets/factsheets/sumithrin
- ^ Phenothrin and s-Methoprene; Product Cancellation Order, US Environmental Protection Agency[dead link]
- ^ Phenothrin; Amendment to Terminate Use, US Environmental Protection Agency[dead link]
- ^ [1] See also "dog" in the following EPA ruling: "Insect Growth Regulators: S-Hydroprene (128966), S-Kinoprene (107502), Methoprene (105401), S-Methoprene (105402) Fact Sheet". U.S. Environmental Protection Agency.
External links
- Pyrethrins and Pyrethroids Fact Sheet - National Pesticide Information Center
- Pyrethrins and Pyrethroids Pesticide Information Profile - Extension Toxicology Network
- Pesticide Properties Database (PPDB) record for Phenothrin
Ectoparasiticides / arthropod (P03A)
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Insecticide/pediculicide |
Chlorine-containing products
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Chloride channel
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Organophosphate
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Acaricide/miticide/scabicide |
Pyrethrines
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- Permethrin#
- Pyrethrum
- Phenothrin
- Bioallethrin
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Chloride channel
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Sulfur-containing products
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- Disulfiram
- Dixanthogen
- Mesulfen
- Thiram
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Chlorine-containing products
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Benzoate
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Organophosphate
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Other/ungrouped
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- Dimethicone
- Quassia
- toluidine (Crotamiton)
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
Index of parasites and pests
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Description |
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Disease |
- Arthropod
- lice
- tick- and mite-born diseases
- flea
- Worms
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Treatment |
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Human lice and pediculosis
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Species |
- Head louse
- Crab louse
- Body louse
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Infestation |
- Pediculosis
- Pediculosis corporis
- Phthiriasis
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Treatment |
- Nitpicking
- Pediculicide
- Lindane
- Permethrin
- Phenothrin
- Delphinium
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Other terms of interest |
- Cooties
- Sucking louse
- Louse
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Index of parasites and pests
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Description |
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Disease |
- Arthropod
- lice
- tick- and mite-born diseases
- flea
- Worms
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Treatment |
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UpToDate Contents
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English Journal
- Kinetic and product study of the heterogeneous reactions of NO(3) radicals with suspended resmethrin, phenothrin, and fenvalerate particles.
- Wang Y, Zhang P, Yang B, Liu C, Shu J.SourceResearch Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, China.
- Chemosphere.Chemosphere.2012 Oct 24. pii: S0045-6535(12)01237-4. doi: 10.1016/j.chemosphere.2012.09.096. [Epub ahead of print]
- Resmethrin, phenothrin, and fenvalerate are the synthetic pyrethroids that have been used widely against groundling or flying insect pests both indoors and outdoors. In this study, the heterogeneous reactions of the three pyrethroid particles with NO(3) radicals are investigated with a mixed-phase r
- PMID 23102722
- Group-selective enrichment and determination of pyrethroid insecticides in aquaculture seawater via molecularly imprinted solid phase extraction coupled with gas chromatography-electron capture detection.
- Shi X, Liu J, Sun A, Li D, Chen J.SourceKey Laboratory of Applied Technology of Marine Biology, Ministry of Education, Ningbo University, 818 Fenghua Road, Ningbo 315211, China. sxzsal78@yahoo.com.cn
- Journal of chromatography. A.J Chromatogr A.2012 Mar 2;1227:60-6. Epub 2012 Jan 11.
- Two types of molecularly imprinted polymers (MIPs) for the simultaneous determination of six pyrethroid insecticides have been developed using deltamethrin (D-MIPs) and cypermethrin (C-MIPs) as template molecules. A comparison of the performance of D-MIPs, C-MIPs, and the corresponding non-imprinted
- PMID 22265776
Japanese Journal
- 緒方 一喜,渡辺 登志也,宮本 和代 [他],川口 正将,豊田 耕治,小曽根 努,松岡 宏明,白石 啓吾,森岡 健志,吉岡 照太,鈴木 雅也,千保 聡,美馬 伸治,中村 友三,足立 雅也,芝生 圭吾,池田 文明,玉田 昭男,田中 生男,石原 雅典
- ペストロジー 27(2), 51-58, 2012-11-25
- ヒトスジシマカ成虫に対する殺虫剤による防除実地試験を東京の寺院の庭で2010年の夏に実施した.5%ペルメトリン,10%フェノトリン,7%エトフェンプロックス水性乳剤の50倍希釈液を背負式噴霧機によって50ml/m^2の量で草むら,植木,空地に噴霧した.スイーピング法,ドライアイストラップによる捕集密度の変化,配置した成虫の死亡率から効果を評価した.結果として,ペルメトリンでは約10日間,他の2剤で …
- NAID 110009553897
- アタマジラミのアンケート調査とアタマジラミ用コームの性能評価
- 色摩 操,福田 安住,川上 裕司
- 都市有害生物管理 1(1), 13-21, 2011-06-20
- 近年,子供たちの間でアタマジラミの寄生が増加していることが報告されている。また,ピレスロイド系殺虫剤フェノトリンを有効成分とするシャンプーを駆除のために多用した結果,抵抗性のアタマジラミの増加が報告されている。このような背景を踏まえて,アタマジラミの被害状況についてアンケート調査を実施するとともに,駆除用コームによる除去効果についても実験を行った。アンケート調査によって,フェノトリンシャンプーと駆 …
- NAID 110008724147
- 食肉中のオキサベトリニル,トリチコナゾール,フェノトリン,フルフェナセットおよびプロメトリンにおける残留農薬一斉分析法の適用性
Related Links
- ChemicalBook あなたのためにPHENOTHRIN(188023-86-1)の化学的性質を提供して、融点、価格、蒸気圧、沸点、毒性、比重、沸点、密度、分子式、分子量、物理的な性質、毒性 税関のコードなどの情報、同時にあなたは更に ...
- Phenothrin (Phenothrine, Phenoxythrin, (3-Phenoxyphenyl)methyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate, CAS#26002-80-2) is a common synthetic chemical, widely used as an insecticide, acaricide, and ...
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