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| 化学名: | メトプレン | | 英語化学名: | METHOPRENE | | 别名: | 11-METHOXY-3,7,11-TRIMETHYL-2E,4E-DODECADIENOIC ACID, ISOPROPYL ESTER;METHOPRENE (TM);METHOPRENE;ALTOSID(R);ISOPROPYL (2E,4E)-11-METHOXY-3,7,11-TRIMETHYL-2,4-DODECADIENOATE;PRECOR;ZR-515;2,4-dodecadienoicacid,11-methoxy-3,7,11-trimethyl-,1-methylethylester,(e,e | | CAS番号: | 40596-69-8 | | 分子式: | C19H34O3 | | 分子量: | 310.47 | | EINECS: | 254-993-2 | | カテゴリ情報: | Veterinary drugs;Growth regulatorsAlphabetic;Insecticides;M;META - METH;Pesticides;Alpha sort;Growth regulatorsPesticides&Metabolites;H-MAlphabetic;INSECT HORMONE | | Mol File: | 40596-69-8.mol |  |
| 融点 | <25℃ | | 沸点 | bp0.06 135-136° | | 比重(密度) | 0.9261 g/cm3 (20℃) | | 蒸気圧 | 3.15 x l0-3 Pa (25 °C) | | 屈折率 | 1.4200 (estimate) | | 貯蔵温度 | 0-6°C | | 溶解性 | Chloroform (Slightly), Methanol (Sparingly) | | 水溶解度 | 1.4 mg l-1 (room temperature) | | BRN | 1913191 | | InChIKey | NFGXHKASABOEEW-LDRANXPESA-N | | CAS データベース | 40596-69-8 | | EPAの化学物質情報 | Methoprene (40596-69-8) |
| | メトプレン Usage And Synthesis |
| 外観 | ごくうすい黄色～うすい黄色, 澄明の液体 | | 溶解性 | アセトンに溶ける。 | | 効能 | 殺虫薬, 殺シラミ薬 | | 農薬用途 | 殺虫剤 | | 使用上の注意 | アルゴン封入 | | 説明 | Methoprene is the common name for a racemic mixture of two
enantiomers (R and S in a ratio of 1:1). The activity of the
compound as a juvenile hormone (JH) mimic is restricted to
the S enantiomer. Methoprene was the first insect growth
regulator approved in the 1970s by the US Environmental
Protection Agency after extensive studies showing low toxicity
to vertebrates and rapid natural chemical degradation in the
environment and through organism metabolism. Nowadays, it
is one of the most widely used and successful insect growth
regulators. Different products containing methoprene (e.g.,
pesticides, veterinary drugs) are commercially available in
different forms (emulsifiable concentrates, granules, pellets,
briquettes, aerosols, or sustained-release formulations). Some
of these are applied to water for mosquito control whereas
others are sprayed in areas where foods are stored to prevent
insect infestations. Methoprene may be used in combination
with other active insecticides to optimize pest control. | | 化学的特性 | Amber colored liquid. Faint fruity odor. | | 使用 | ectoparasiticide | | 使用 | Methoprene is a broad-spectrum synthetic JH mimic, which
acts as an insect growth regulator (insecticide). It prevents
larval insect stages from undergoing metamorphosis to viable
adults and thus acts as a larvicide. Methoprene is considered
a biochemical pesticide because rather than controlling target
pests through direct toxicity, methoprene interferes with the
insect life cycle, preventing the insect from reaching maturity
or reproducing.
It is useful for control of a variety of insect pests including
ants, mosquitoes, flies, fleas, beetles, lice, and moths, but is
only effective against larvae, not adults or pupae. In order to
control some of these insects, methoprene is used in the
production of a number of foods including meat, milk,
mushrooms, peanuts, rice, and cereals. Many different products
(e.g., pesticides, veterinary drugs) and formulations containing
methoprene are commercially available. Methoprene products
used for protecting pets such as cats and dogs include capsules
administered orally and flea collars used externally. Production
animals (e.g., cattle) typically receive methoprene in the diet as
a food additive. Other formulations of methoprene include
emulsifiable concentrates, pellets and tablets, granules, and
aerosols. Some of these are applied to water for mosquito
control whereas others are sprayed in areas where foods are
stored to prevent insect infestations. A potential therapeutic use
of methoprene was proposed in the context of African sleeping
sickness, since it was observed that this compound killed
Trypanosoma brucei in culture. However, methoprene acid,
resulting from the insecticide metabolism, exhibited no efficiency
as trypanocide. Consistently, methoprene administered
to infected mice showed to be unable to eliminate trypanosomes
from the blood. | | 使用 | Methoprene controls many insect pests (Diptera, Pharaoh’s ants,
and also Coleoptera, Homoptera and Siphonaptera) in public health,
stored commodities, food handling, processing and storage establishments,
mushroom houses, on animals and on plants (including glasshouse
plants). | | 定義 | An insecticidal
preparation said to act in the manner of a juvenile hormone, which arrests development of insects
in the larval stage. | | 农业用途 | Insect growth hormone: Methoprene is an insect growth regulator (IGR) used
against a variety of insects including horn flies, mosquitoes,
beetles, tobacco moths, sciarid flies, fleas (eggs and larvae), fire ants, pharoah ants, midge flies and Indian meal moths.
Controlling some of these insects, methoprene is used in
the production of a number of foods including meat, milk,
mushrooms, peanuts, rice and cereals. It also has several
uses on domestic animals (pets) for controlling fleas and to
control insects in wastewater, sludge beds and ponds. For
oral use in dogs, 9 weeks of age and older and 4 pounds
body weight or greater, for the prevention and control of
flea populations [21 CFR 520.1390]. Not approved for use
in EU countries
. Registered for use in the U.S. | | 製品名 | ALTOSID®; APEX®; DIACON®;
DIANEX®; ENT 70,460®; EXTINGUISH®;
FLEATROL®; KABAT®; MANTA®; MOORMAN’S®
IGR CATTLE CONCENTRATE; OVITROL®;
PHARORID®; PRECOR®; ZR-515® | | 職業ばく露 | Methoprene is a natural insect growth
regulator (IGR) that mimics juvenile hormone(s) and is
used against a variety of insects including horn flies, mosquitoes, beetles, tobacco moths, sciarid flies, fleas (eggs
and larvae), fire ants, pharoah ants, midge flies and Indian
meal moths. Controlling some of these insects, methoprene
is used in the production of a number of foods including
meat, milk, mushrooms, peanuts, rice and cereals. It also
has several uses on domestic animals (pets) for controlling
fleas and to control insects in wastewater, sludge beds and
ponds. For oral use in dogs, 9 weeks of age and older and
4 lb body weight or greater, for the prevention and control
of flea populations | | 環境運命予測 | Methoprene may be degraded by demethylation, hydrolysis,
oxidative cleavage, and photodegradation, resulting in the
formation of a series of metabolites that include methoprene
acid and citronellic acid. The primary modes of degradation are
photodegradation and degradation by aquatic microorganisms.
It is metabolized rapidly in soil under both aerobic and
anaerobic conditions (half-life = 10–14 days). The major
microbial degradation product is carbon dioxide. Degradation
in both freshwater and saltwater is also quite rapid with a halflife
of 10–35 days at 20 ℃. Methoprene is not very soluble in
water (<2 ppm) and as a result is not highly mobile in soil.
Because of this and its rapid biodegradation, methoprene does
not persist for long periods in soil and is unlikely to contaminate
groundwater. When released into water, methoprene is
expected to adsorb to suspended solids and sediment. A high
potential for bioconcentration in aquatic organisms has been
suggested, with an estimated bioconcentration factor of 3400.
However, studies with bluegill sunfish, showed no significant
bioconcentration of methoprene in fish tissues as a result of
aquatic exposure.
Methoprene rapidly degrades in plants, with a half-life of
1–2 days in alfalfa when applied at a rate of 1 pound per acre.
In rice, the half-life is less than 1 day. In wheat, its half-life was
reported to be 3–7 weeks, depending on the level of moisture
in the plant. | | 代謝経路 | Methoprene is readily degraded biologically by hydrolysis of the ester
group, O-demethylation and oxidative cleavage of the bond at the
4-position. | | 輸送方法 | UN3082 Environmentally hazardous substances,
liquid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required | | Toxicity evaluation | Acute oral LD50 for rats: >34,600 mg/kg | | Degradation | Methoprene (1) is stable in water and in the presence of aqueous acids and
alkalis. It is sensitive to UV light. Isomerisation of the double bond is
facile. In sunlight (S)-methoprene decomposes to a number of products.
These include trans,trans-( S)-methoprenic acid, 2-cis,4-trans-( S)-methoprenic
acid, and 2-cis,4-trans-(S)-methoprene.
When [5-14C]methoprene was irradiated in direct sunlight in Pyrex
vessels in aqueous solutions (0.01 ppm and 0.50 ppm) the DT50 was less
than one day. Initially decomposition was rapid, but after one week 12%
and 5% 1 remained in the 0.5 and 0.01 ppm solutions, respectively.
Carbon dioxide was collected and total 14C recovered was not less than
94% during a 21-day experiment. Five products were characterised as
oxygenated products but could not be positively identified. For product
identification, an aqueous emulsion of methoprene was irradiated in
sunlight and four photoproducts (24% yield) were characterised as methoxycitronellal
dimethyl acetal(3,3.9%), methoxycitronellic acid (4,4.7%),
an epoxide of methoprene (5,4%) and a methyl ketone (6,4%). In addition
to unreacted methoprene there were at least 46 other photoproducts
of which none represented more than 2% yield. Rose Bengal and
anthraquinone increased the rate of photocatalysed breakdown of
methoprene and the profile of products was similar to that obtained by
irradiation of a thin film. The extent of decomposition in the presence
of anthraquinone was 86% after 6 hours and the predominant product
was methoxycitronellal (2, l0-14%). Photosensitised oxidation was slow
and 47% of the original was unreacted and a single major product
(12%) was identified as the dihydrofuranol (7) (Quistad et al., 1975a)
(see Scheme 1). | | 廃棄物の処理 | It is the responsibility of chemical waste generators to
determine if a discarded chemical is classified as a hazardous waste. See 40 CFR Parts 261.3 for United States
Environmental Protection Agency guidelines for the classification determination. In addition, in order to ensure complete and accurate classification, waste generators must
consult state and local hazardous waste regulations.
Incineration might be an effective disposal procedure
where permitted. If an efficient incinerator is not available, the product should be mixed with large amounts of
combustible material and contact with the smoke should
be avoided. In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide
containers |
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