ロテノン 化学特性,用途語,生産方法
外観
白色～うすい黄色～うすい黄赤色粉末～結晶
溶解性
Soluble to 100 mM in DMSO and to 5 mM in Ethanol
解説
ロテノン，基源植物のデリス属に殺虫成分があることはヨーロッパでは19世紀中ごろに知られており，またマレーシア地域から太平洋諸島では昔から毒流し漁法の重要な魚毒植物でもあった。トバ，タチトバ，ハイトバなどがデリスの殺虫有効成分であるロテノンを多量に含み，栽培もされる。トバD.elliptica Benth.（イラスト）はフジに似た木本性つる植物で，葉は奇数羽状複葉で4～6対の小葉を有する。
株式会社平凡社 世界大百科事典 第２版について 情報
用途
農薬(殺虫剤)
製造
ロテノン，殺虫や魚毒に使用される薬剤で，マメ科デリス属Derris植物の根や地下茎部の茎から作られる。
説明
The principal source of rotenone is the tuber root of
Derris elliptica; however, it is also extracted from the
roots of Derris mallaccensis, Lonchocarpus utilis, and
Lonchocarpus uruca. Rotenone is both a stomach and
contact poison for arthropods. Its fast knockdown action
is attributed to decreasing the availability of nicotinamide
adenine dinucleotide to serve as a cofactor in various
biochemical pathways including the Krebs cycle, thereby
inhibiting the mitochondrial respiratory enzymes.
化学的特性
Rotenone is a colorless to red odorless crystalline solid; a white crystalline solid when pure; oxidation will cause yellowing to bright red coloring. Odorless.
Rotenone is related to isoflavonoid compounds derived from the roots of Derris spp., Lonchocarpus spp., and Tephrosia spp., found primarily in Southeast Asia, South America, and East Africa. The isolated compound is an odorless, colorless to red crystalline solid. It is insoluble in water and has a very low vapor pressure (U.S. EPA, 2007; HSDB, 2012a).
使用
Rotenone is an broad spectrum insecticide that occurs naturally in seeds and stems of several plants. Rotenone was first registered in 1947 and is currently used exclusively to kill fish (U.S. EPA, 2007). In 2006, registrants voluntarily canceled all livestock, residential and home owner uses, domestic pet uses, and all other uses except for piscicide uses. Currently the main uses include fish management strategies to remove nonnative fish species from lakes, ponds, or streams and in catfish aquaculture prior to stocking ponds with with fry to remove undesirable fish species (U.S. EPA, 2006d).
Rotenone has been historically used by native people to paralyze fish for capture and consumption. Outside the United States, the compound is still used to control insects in fruit and vegetable cultivation and for control of fire ants and mosquito larvae in pond water (HSDB, 2012a).
定義
ChEBI: A member of the class of rotenones that consists of 1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one substituted at position 2 by a prop-1-en-2-yl group and at positions 8 and 9 by methoxy group
(the 2R,6aS,12aS-isomer). A non-systemic insecticide, it is the principal insecticidal constituent of derris (the dried rhizome and root of Derris elliptica).
一般的な説明
Colorless to brownish crystals or a white to brownish-white crystalline powder. Has neither odor nor taste.
空気と水の反応
ROTENONE decomposes upon exposure to light or air. Insoluble in water.
反応プロフィール
ROTENONE is readily oxidized in the presence of alkalis. ROTENONE is incompatible with oxidizers. .
危険性
Toxic by ingestion, overexposure can be
fatal, irritant to skin, eyes and upper respiratory
tract. Central nervous system impairment. Ques-
tionable carcinogen.
健康ハザード
Rotenone is an irritant and affects
the nervous system, causing convulsions.
火災危険
Flash point data for ROTENONE are not available; however, ROTENONE is probably combustible.
农业用途
Insecticide, Acaracide, Veterinary medicine: The use of rotenone as a pesticide to kill invasive fish species is currently the only allowable use of this pesticide. Rotenone is a selective, nonspecific botanical insecticide with some acaricidal properties, and has been used in agriculture to control insects on vine fruit, flowers and vegetables. Registered for use in the U.S.A U.S. EPA restricted Use Pesticide (RUP) due to acute inhalation, acute oral, and aquatic toxicity. Agricultural and residential uses and all food uses were voluntarily cancelled in 2006[83]. In 2006, registrants requested voluntarily cancellation of all livestock, residential and home owner uses, domestic pet uses, and all other uses except for pesticide uses. In 2011 the use of this pesticide chemical was linked to Parkinson’s disease. Not listed for use in EU countries.
製品名
ACME® Rotenone; AROL GORDON DUST®; BARBASCO®; BONIDE CUKE AND MELON DUST®; CENOL GARDEN DUST®; CHEM FISH®; CHEM-MITE®; CUBE®; CUBE EXTRACT®; CUBEPULVER®; CUBEROL®; CUBE ROOT®; CUBOR®; CUREX FLEA DUSTER®; DACTINOL®; DERIL®; DERRIN®; DERRIS®; DRI-KIL®; ENT-133®; EXTRAX®; FISH-TOX®; GREEN CROSS WARBLE POWDER®; HAIARI®; LIQUID DERRIS®; MEXIDE®; NICOULINE®; NOXFIRE®; NOXFISH®; PARADERIL®; POWDER AND ROOT®; PRENTOX®; PRO-NOX FISH®; RO-KO®; RONONE®; ROTACIDE®; ROTEFIVE®; ROTEFOUR®; ROTESSENOL®; SINID®; TOX-R®; TUBATOXIN®
生物活性
Mitochondrial electron transport chain inhibitor (IC 50 = 1.7 - 2.2 μ M at complex I). Inhibits NADH oxidation by cardiac sarcoplasmic reticulum (IC 50 = 3.4 nM). Commonly used pesticide and induces Parkinsonism in animal models. Cell-permeable and brain penetrant.
職業ばく露
A potential danger to those involved
in extraction from derris root, formulation or application of
this insecticide. Rotenone is used as a pharmaceutical and
veterinary drug.
発がん性
In human lymphocyte culture assays
rotenone did not increase the frequency of
chromosomal aberrations or sister chromatid
exchanges but did cause an increase in the frequency
of binucleated micronuclei and a delay
in cell cycle.
環境運命予測
Rotenone released to the atmosphere will exist as particulates due to the extremely low vapor pressure. Particulate-phase rotenone will be removed from the atmosphere by wet and dry deposition and may be degraded by direct photolysis. It is mobile to moderately mobile in soil and sediment and volatilization from soil surfaces is not expected to occur to any extent. If released to water, rotenone generally degrades quickly through abiotic (hydrolytic and photolytic) mechanisms, with half-lives of a few days to several weeks or longer depending on water temperature (U.S. EPA, 2007; HSDB, 2012a).
Rotenone has a relatively low potential for bioconcentration in aquatic organisms (Bioconcentration Factor (BCF) < 30X) (U.S. EPA, 2007).
代謝経路
By hepatic microsomal incubations from rainbow trout
with 14C-rotenone, three major and several minor
metabolites of rotenone are observed, the major ones
being identified as rotenolone and two epimeric forms
of 6' ,7' -dihydroxyrotenone.
輸送方法
UN2811 Toxic solids, organic, n.o.s., Hazard
Class: 6.1; Labels: 6.1-Poisonous materials, Technical
Name Required. UN2588 Pesticides, solid, toxic, Hazard
Class: 6.1; Labels: 6.1-Poisonous materials, Technical
Name Required.
不和合性
Incompatible with oxidizers (chlorates,
nitrates, peroxides, permanganates, perchlorates, chlorine,
bromine, fluorine, etc.); contact may cause fires or explo-
sions. Keep away from alkaline materials, strong bases,
strong acids, oxoacids, epoxides, and alkalies.
廃棄物の処理
Rotenone is decomposed by
light and alkali to less insecticidal products. It is readily
detoxified by the action of light and air. It is also detoxified
by heating; 2 hours @ 100 ? C results in 76% decomposition.
Oxidation products are probably nontoxic. Incineration has
been recommended as a disposal procedure. Burial with
lime would also present minimal danger to the environ-
ment . In accordance with 40CFR165, follow recommen-
dations for the disposal of pesticides and pesticide
containers. Must be disposed properly by following pack-
age label directions or by contacting your local or federal
environmental control agency, or by contacting your
regional EPA office.
ロテノン 上流と下流の製品情報
原材料
準備製品