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| 融点 | 150-155°C | | 比旋光度 | D +55.7 ±2° (c = 0.87 in CHCl3) | | 沸点 | 717.52°C (rough estimate) | | 比重(密度) | 1.16 | | 蒸気圧 | <2 x 10-7 Pa | | 屈折率 | 1.6130 (estimate) | | 闪点 | 150 °C | | 貯蔵温度 | Sealed in dry,Store in freezer, under -20°C | | 溶解性 | Soluble in DMSO | | 水溶解度 | 0.007-0.01 mg l-1 (20 °C) | | Merck | 13,2 | | InChIKey | GVWIWZFXCGTSLL-MSTMYQEVSA-N | | CAS データベース | 71751-41-2(CAS DataBase Reference) | | EPAの化学物質情報 | Abamectin (71751-41-2) |
| 主な危険性 | T+,N | | Rフレーズ | 20-28-50 | | Sフレーズ | 36/37/39-45-60-61 | | RIDADR | 2588 | | WGK Germany | 3 | | RTECS 番号 | CL1203000 | | 国連危険物分類 | 6.1(a) | | 容器等級 | II | | 有毒物質データの | 71751-41-2(Hazardous Substances Data) | | 毒性 | LD50 (technical grade) orally in sesame oil in mouse, rat: 13.5, 10.0 mg/kg; dermally in rabbit: >2000 mg/kg; LD50 in mallard duck, bobwhite quail: 84.6, >2000 mg/kg; LC50 (96 hr) in rainbow trout, bluegill: 3.6, 9.6 mg/l; LC50 (48 hr) in Daphnia magna: 0.34 mg/l (Merck Technical Data Sheet) |
| Provider | Language |
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Affirm
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| | エバーメクチン Usage And Synthesis |
| 外観 | 白色〜ほとんど白色, 結晶性粉末 | | 溶解性 | 水7-10ug/L(20℃)トルエン350,アセトン100,イソプロパノール70,クロロホルム25,エタノール20,メタノール19.5,n-ブタノール10,シクロヘキサン6(g/l 21℃)アセトンにやや溶けやすく、水にほとんど溶けない。 | | 解説 | エバーメクチンは，放線菌から放出される化学物質で、感染症を媒介する線虫など寄生虫の活動を抑制するように作用するマクロライド系抗生物質。アベルメクチンともいう。糸状虫など線虫の神経に作用し、麻痺させたり発育を防止したりするはたらきももつ。大村智(おおむらさとし)により1979年（昭和54）に静岡県のゴルフ場の土壌の中から発見され、その後、アメリカの製薬会社によって「イベルメクチン」として製品化され、家畜やイヌなどの寄生虫駆除薬として用いられた。その後ヒトにも効果があることが確認され、オンコセルカ症やリンパ系フィラリア症（象皮病）など、寄生虫による感染症の特効薬として世界的に使われるようになった。一般には疥癬(かいせん)の特効薬としても知られる。大村はこの功績により2015年（平成27）にノーベル医学生理学賞を受賞した。［編集部 2016年5月19日］[参照項目] | イベルメクチン | 大村智 | オンコセルカ症 | 疥癬 | 放線菌 | マクロライド系抗生物質 小学館 日本大百科全書(ニッポニカ) ）
| | 農薬用途 | 動物薬、殺虫剤 | | 使用上の注意 | アルゴン封入 | | 化学的特性 | Off-White to Yellow Crystalline Solid | | 化学的特性 | Abamectin is a colorless to yellowish crystalline powder. It is soluble in acetone, methanol,
toluene, chloroform, and ethanol, but insoluble in water. It is stable, and incompatible with
strong oxidizing agents. Abamectin is a mixture of Abamectins containing about 80%
Abamectin B1a and 20% Abamectin B1b. These two components, B1a and B1b, have very
similar biological and toxicological properties. The Abamectins are insecticidal/miticidal
compounds derived from the soil bacterium
Streptomyces avermitilis.
Abamectin is used to
control insect and mite pests of citrus, pear, and nut tree crops, and is used by homeown-
ers to control fi
re ants. It acts on the nervous system of insects, causing paralyzing effects.
Abamectin is a general use pesticide (GUP). It is grouped as toxicity class IV, meaning
practically non-toxic, requiring no precautionary statement on its label | | Originator | Abamectin,Yellow River
Enterprise Co. (a.k.a
Yelori) | | 使用 | Mixture of Abamectins, containing at least 80% of Abamectin B1a (C48H72O14) and not more than 20% of Abamectin B1b (C47H70O14). Used as acaricide, insecticide | | 使用 | ectoparasiticide, CNS stimuant, mutagen | | 使用 | Acaricide; insecticide. | | 定義 | Any of a group of broad spectrum antiparasitic antibiotics produced by the actinomycete, Streptomyces avermitilis. | | Manufacturing Process | 1. The contents of a lyophilized tube of Streptomyces avermitilis MA-4680 is
transferred aseptically to a 250 ml Erlenmeyer flask containing 305 ml of
Medium 1: Dextrose 20 g, Peptone 5 g, Meat Extract 5 g, Primary Yeast 3 g,
NaCl 5 g, CaCO3 (after pH adjustment) 3 g, Distilled water 1000 ml, pH 7.0.
The inoculated flask is incubated for 3 days at 28°C on a rotary shaking
machine at a speed of 220 RPM in a 2 inch radius circular orbit. At the end of
this time, a 250 ml Erlenmeyer flask containing 50 ml of Medium 2 [Tomato
Paste 20 g, Modified Starch (CPC) 20 g, Primary Yeast 10 g, CoCl2·6H2O 0.005
g, Distilled water 1000 ml, pH 7.2-7.4] is inoculated with a 2 ml sample from
the first flask. This flask is incubated for 3 days at 28°C on a rotary shaking
machine at a speed of 220 RPM in a 2 inch diameter circular orbit. 50 Ml of
the resulting fermentation broth containing C-076 is effective against an
N.dubius infection in mice.
2. A lyophilized tube of Streptomyces avermitilis MA-4680 is opened
aseptically and the contents suspended in 50 ml of Medium 1 in a 250 ml
Erlenmeyer flask. This flask is shaken for 3 days at 28°C on a rotary shaking
machine 220 RPM with a 2 inch diameter circular orbit. A 0.2 ml portion of
this seed medium is used to inoculate a Slant of Medium 3: Dextrose 10.0 g ,
Bacto Asparagine 0.5 g, K2HPO4 40.5 g, Bacto Agar 15.0 g , Distilled water
1000 ml, pH 7.0. The inoculated slant medium is incubated at 28°C for 10
days and stored at 4°C until used to inoculate 4 more slants of Medium 3.
These slants are incubated in the dark for 8 days. One of these slants is used
to inoculate 3 baffled 250 ml Erlenmeyer flasks containing 50 ml of No. 4
Seed Medium: Soluble Starch 10.0 g, Ardamine 5.0 g, NZ Amine E 5.0 g, Beef
Extract 3.0 g, MgSO4·7H2O 0.5 g, Cerelose 1.0 g, Na2HPO4 0.190 g, KH2PO4
182 g, CaCO3 0.5 g, Distilled water 1000 ml, pH 7.0-7.2. The seed flasks are
shaken for 2 days at 27-28°C on a rotary shaking machine at 220 RPM with a
2 inch diameter circular orbit. The contents of these flasks are pooled and
used to inoculate (5% inoculum) baffled 250 ml Erlenmeyer flasks containing
40 ml of various production media. Flasks containing media 2, 5 and 6 are
incubated for 4 days at 28°C on a rotary shaking machine at 220 RPM with a
2 inch diameter circular orbit. The resulting broth containing C-076 is then
harvested and tested for anthelmintic activity. In all cases 6.2 ml of whole
broth and the solids obtained from centrifuging 25 ml of whole broth are fully
active against N.dubius helminth infections in mice.
3. The one of the four slants of Medium 3 prepared as in Example 2 is used to
inoculate a baffled 250 ml Erlenmeyer flask containing 50 ml of Seed Medium
No. 4. The seed flask is shaken for 1 day at 27- 28°C on a rotary shaking
machine at 220 RPM with a 2 inch diameter circular orbit. The seed flask is
then stored stationary at 4°C until it is ready to be used. The contents of this
flask are then used to inoculate (5% inoculum) 20 unbaffled 250 ml
Erlenmeyer flasks containing 40 ml of Medium No. 2. After 4 days incubation
at 28°C on a rotary shaking machine at 220 RPM with a 2 inch diameter
circular orbit, 19 of the flasks are harvested and pooled. The combined
fermentation broths
containing C-076 are filtered affording 500 ml of filtrate and 84 g of mycelia.
78 G of mycelia are extracted with 150 ml of acetone for ? hour with stirring
and the mixture filtered. The filter cake is washed with 50 ml of acetone and
the filtrate and washings are combined and concentrated to 46.5 ml 30 Ml of
the concentrate is adjusted to pH 4 with dilute hydrochloric acid and extracted
3 times with 30 ml portions of chloroform. The extracts are dried by filtering
through dry Infusorial Earth (Super-Cel) combined and concentrated to
dryness in vacuum. The oily residue of C-076 weighing 91.4 mg is dissolved in
chloroform sufficient to make 3 ml of solution which represents 1% of broth
volume. The C-076 (Abamectin) obtained in this recovery procedure is fully
active against N.dubius infections in mice. In addition, the chloroform
extraction achieved a 70 fold purification of C-076 from the whole broth. | | brand name | (Merck)Avomec [Veterinary] (Merial); Bovitin
[Veterinary] (Merial); Doratect [Veterinary] (Merial);
Duomectin [Veterinary] (Merial); Duotin [Veterinary]
(Merial); Endecto (Merck); Enzec (Merck); Enzek
(Merck); Parafoil (Merck); Vertimil (Zectin
(Merck). | | Therapeutic Function | Antiparasitic | | 一般的な説明 | Odorless off-white to yellow crystals from methanol. Does not hydrolyze in water at pH 3, 5, 7. Used as an acaricide and insecticide. | | 反応プロフィール | A lactone. | | 危険性 | A poison by ingestion. Moderately toxic by
inhalation and skin contact. | | 健康ハザード | Abamectin is an insecticide and miticide. It is very toxic and causes adverse health effects
if swallowed and/or inhaled. Emulsifi
able concentrate formulations of Abamectin cause
slight to moderate eye irritation and mild skin irritation. The symptoms of poisoning
observed in laboratory animals include pupil dilation, vomiting, convulsions and/or trem-
ors, and coma. Abamectin acts on insects by interfering with the nervous system. At very
high doses, laboratory mammals develop symptoms of nervous system depression, inco-
ordination, tremors, lethargy, excitation, and pupil dilation. Very high doses have caused
death from respiratory failure in animals. Additionally, Abamectin has been reported to
cause reproductive effects. Abamectin blocks the nerval conduct system in insects, caus-
ing paralysis and death. Laboratory studies have indicated that abamectin may affect the
nervous system in experimental animals. A 1-year study with dogs given oral doses of
abamectin (0.5 and 1 mg/kg/day) caused adverse health effects, such as pupil dilation,
weight loss, lethargy, tremors, and recumbency. | | 农业用途 | Acaricide, Miticide, Insecticide, Anthelmentic: Used on fruit, vegetable and ornamental crops; pears,
citrus fruits, and nut crops; to control mite and insect pests,
and also to control household and lawn insects, including fire
ants. Approved by the EPA for use in ash trees for control of
emerald ash borer. A U.S. EPA restricted Use Pesticide (RUP). | | 製品名 | ABACIDE®; AFFIRM®; AVID®,
AVID-EC®; AVOMEC®; DYNAMEC®; INJECT-A-
CIDE AV®; MK 936®(B 1A ); BOVITIN®; DORATECT®;
DUOMECTIN®; DUOTIN®; ENDECTO®; ENZEC®; L
676,863® (B 1A ); MK 0936®; MK 936®; PARAFOIL®;
VERTIMEC®, VERTIMIL®; VIVID®; ZECTIN®;
ZEPHEYR®; ZEPHYR® | | 代謝経路 | Abamectin contains the closely related avermectin B1a and B1b as the
active ingredients. Avermectin B1a contains a sec-butyl moiety whereas
avermectin B1b contains an isopropyl moiety. Chemical degradation and
metabolism studies were conducted with avermectin B1a radiolabelled
with 3H or 14C at various positions of this large molecule. The overall fates
of avermectin B1a and B1b are similar since transformations at the butyl or
propyl moiety were not observed.
Avermectin B1a is stable to hydrolytic degradation, but it is readily
degraded to numerous products in aqueous solutions, soil, glass and
plant foliage/fruit surfaces after light irradiation. Isomerisation and
O-demethylation appear to the primary degradation reactions. In addition,
hydroxylation is a major metabolic reaction in animals. Significant
amounts of the residues in plants and animals were characterised as
unidentified polar components. | | Degradation | [3H]Avermectin B1a(1) was stable at 25 °C in pH 5,7 and 9 solutions up to
28 days. Less than 5% degradation was observed (PSD, 1992).
[14C]Avermectin B1a degraded rapidly in aqueous solution when
exposed to sunlight with an observed DT50 of 3.5-12 hours. The △8,9 geometric
isomer of avermectin B1a (2) was tentatively identified in aqueous
solution (containing 2% acetone as photosensitiser) after irradiation
under artificial light. Crouch et al. (1991) reported the photodegradation of
avermectin B1a, as a thin film on glass surfaces under artificial light (>260
nm). At least 10 photodegradation products were characterised including
the geometric isomers (2, 3), hydroxylated (4-7) and O-demethylated
products (8) shown in Scheme 1. | | 予防処置 | During use of Abamectin, occupational workers should use safety glasses, gloves, and
protective clothing to prevent prolonged skin contact, and work in good ventilation. |
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