メチルカルバミン酸1-ナフチル

外観

白色～ほとんど白色, 結晶～粉末

溶解性

アセトンに溶けやすく、水にほとんど溶けない。

解説

メチルカルバミン酸1-ナフチル，C12H11NO2(201.23)．デナポンともいう．カルバメート系殺虫剤の一つ．α-ナフトールにメチルイソシアナートを第三級アミン触媒の存在下で反応させると得られる．白色の結晶．融点142 ℃．水に不溶，極性有機溶媒に可溶．アルカリに不安定，弱酸に比較的安定である．接触性殺虫剤として，果樹，森林，家禽，農業用に広く用いられている．LD50 438 mg/kg(マウス，経口)．

用途

農薬

効能

殺虫薬

説明

Carbaryl is a colourless to light tan or white or grey solid crystal depending on the purity of the compound. The crystals are essentially odourless and stable to heat, light, and acids but are not stable under alkaline conditions. It is non-corrosive to metals, packaging materials, and application equipment. Carbaryl is classified as a general use pesticide (GUP). It is sparingly soluble in water, but soluble in dimethylformamide, dimethyl sulfoxide, acetone, cyclohexanone, isopropanol, and xylene. Carbaryl is a wide-spectrum carbamate insecticide, which controls over 100 species of insects on citrus, fruit, cotton, forests, lawns, nuts, ornamentals, shade trees, and other crops, as well as on poultry, livestock, and pets. It is also used as a molluscicide and an acaricide. Carbaryl works whether it is ingested into the stomach of the pest or absorbed through direct contact. It is available as bait, dusts, wettable powders, granules, dispersions, and suspensions.

化学的特性

Carbaryl is a colorless to light tan or white or gray, solid crystals depending on the purity of the compound. The crystals are essentially odorless, and stable to heat, light, and acids, but are not stable under alkaline conditions. It is non-corrosive to metals, packaging materials, and application equipment. Carbaryl is classifi ed as a GUP. It is sparingly soluble in water, but soluble in dimethylformamide, DMSO, acetone, cyclohexanone, isopropanol, and xylene. Carbaryl is a wide-spectrum carbamate insecticide that controls over 100 species of insects on citrus, fruit, cotton, forests, lawns, nuts, ornamentals, shade trees, and other crops, as well as on poultry, livestock, and pets. It is also used as a molluscicide and an acaricide. Carbaryl works whether it is ingested into the stomach of the pest or absorbed through direct contact. It is available as bait, dusts, wettable powders, granules, dispersions, and suspensions

物理的性質

White to light tan crystals with a bleach-like type odor. At 40 °C, the average odor threshold concentration and the lowest concentration at which an odor was detected were 280 and 37 μg/L, respectively. At 25 °C, the average taste threshold concentration and the lowest concentration at which a taste was detected were 140 and 44 μg/L, respectively (Young et al., 1996).

使用

Carbaryl is a pesticide, an insecticide of the carbamate group. It induced sensitization in a farmer.

適応症

Carbaryl (Sevin), a cholinesterase inhibitor insecticide, is used as a pediculicide in the form of a shampoo. This product has an objectionable odor, but has some ovicidal activity. It is an effective medication available in England and some other countries but not in the United States.

定義

ChEBI: A carbamate ester obtained by the formal condensation of 1-naphthol with methylcarbamic acid.

一般的な説明

A white crystalline solid. Insoluble in water. Combustible, although difficult to ignite. Toxic by inhalation (dust, etc.). Produces toxic oxides of nitrogen during combustion.

空気と水の反応

Slightly soluble in water.

反応プロフィール

Carbaryl is a carbamate ester. Carbamates are chemically similar to, but more reactive than amides. Like amides they form polymers such as polyurethane resins. Carbamates are incompatible with strong acids and bases, and especially incompatible with strong reducing agents such as hydrides. Flammable gaseous hydrogen is produced by the combination of active metals or nitrides with carbamates. Strongly oxidizing acids, peroxides, and hydroperoxides are incompatible with carbamates. Carbaryl is unstable in an alkaline media. . Carbaryl is incompatible with the following: Strong oxidizers, strongly alkaline pesticides .

危険性

Toxic by ingestion, inhalation, and skin absorption; irritant. A reversible cholinesterase inhibitor. Use may be restricted. Questionable car- cinogen. Male reproductive and embryo damage.

健康ハザード

Acute oral toxicity — moderate in rats; dermal toxicity low to very low; oral LD50 value(rats); 250 mg/kg, skin LD50 value (rats);4000 mg/kg; toxic symptoms in humans —nausea, vomiting, diarrhea, abdominal cramps,miosis, lachrimation, excessive salivation,nasal discharge, sweating, cyanosis, muscletwitching, convulsions, and coma; acetylcholinesterase inhibitor; exposure limit: TLVTWA 5 mg/m³ (ACGIH, OSHA, and MSHA).
The poisoning effects from carbaryl takeplace very quickly, but lasts only for a shorttime. It is readily hydrolyzed to 1-naphtholwhich is excreted. Although its toxicity inhumans is relatively low, the compound canproduce strong effect on bees and aquaticspecies even in small quantities.

火災危険

Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Containers may explode when heated. Runoff may pollute waterways.

农业用途

Insecticide, Nematicide, Plant growth regulator: Carbaryl is one of the most widely used insecticides in agriculture, professional turf management and ornamental production, as well as in residential pet, lawn, and garden markets. It controls over 100 species of insects that infect citrus, cotton, nuts, and forest and ornaments trees, as well as poultry and livestock. Carbaryl also is used as a mosquito adulticide. It is available in a variety of formulations bait, dust, wettable powders, granules, dispersions and suspensions. Washington State, for example, has a Special Local Needs registration to control burrowing shrimp in oyster beds. A U.S. EPA restricted Use Pesticide (RUP). Banned for use in EU countries.

製品名

ADIOS®; ARILAT®; ARILATE®; ARYLAM®; BERCEMA NMC50®; BUGMASTER®[C]; CAPROLIN®; CARBAMEC®; CARBAMINE®; CARBATOX®; CARBAVUR®; CARBOMATE®; CARPOLIN®; COMPOUND 7744®; CARYLDERM®; CRAG SEVIN®; CRUNCH®; DENAPON®; DICARBAM®; DYNA-CARBYL®; EXPERIMENTAL INSECTICIDE 7744®; GAMONIL®; GERMAIN'S®; HEXAVIN®; KARBASPRAY®; KARBATOX®; KARBOSEP®; MENAPHAM®; MICROCARB®; MUGAN®; MURVIN®; NAC®; NMC® 50; OMS29®; OMS 629®; OLTITOX®; PANAM®; POMEX®; PROSEVOR® 85; RAVYON®; SAVIT®[C]; SEPTENE®; SEFFEIN®; SEVIMOL®; SEVIN®; SEWIN®; SOK®; TERCYL®; THINSEC®; TORNADO®; TRICAR®; UNION CARBIDE 7,744®; VIOXAN®

接触アレルゲン

Carbaryl is a pesticide and insecticide of the carbonate group. It induced sensitization in a farmer.

安全性プロファイル

Poison by ingestion, intravenous, intraperitoneal, and possibly other routes. Human systemic effects by ingestion: sensory change involving peripheral nerves and muscle weakness. Experimental teratogenic and reproductive effects. Questionable carcinogen with experimental carcinogenic and tumorigenic data. Human mutation data reported. An eye and severe skin irritant. Absorbed by all routes, although skin absorption is slow. No accumulation in tissue. Symptoms include blurred vision, headache, stomachache, vomiting. Symptoms sirmlar to but less severe than those due to parathion. A reversible cholinesterase inhibitor. See also CARBAMATES and ESTERS. When heated to decomposition it emits toxic fumes of NOx

職業ばく露

Carbaryl is a white or grayish, odorless, crystalline solid; or various other forms including liquid and paste. Molecular weight 5 201.24; boiling point 5 (decomposes below BP); freezing/melting point 5 142C; vapor pressure 5, 4 3 1025 mmHg @ 25C; flash point 5B200C. Hazard identification (based on NFPA- 704 M Rating System): Health 3, flammability 1, reactivity 0. Practically insoluble in water; solubility 5 0.02 g/L @ 30C

発がん性

Carbaryl is not considered to be genotoxic.

代謝経路

The metabolism of carbaryl has been extensively reviewed many times and so original research papers are not generally quoted. Pathways for carbaryl include hydroxylation of the aromatic ring and the methyl group, carbamate ester hydrolysis and conjugation. The metabolism of carbaryl has been extensively reviewed by Schlagbauer and Schlagbauer (1972), Fukuto (1972), Kuhr and Dorough (1976), Mount and Oehme (1981) and by the WHO (1994). Metabolism in man was reviewed by Hutson (1981) and in economic animals by Akhtar (1985).

代謝

Carbaryl undergoes hydrolysis and ring oxidation in soils. The major metabolite in a number of studies was 1-naphthol. Metabolites also included 4-hydroxycarbaryl and 5-hydroxycarbaryl. In mammals, the major metabolite is 1-naphthol. This is eliminated in urine and feces, together with the glucuronic acid conjugate. Aromatic ring hydroxylation at the 3-, 4-, 5-, or 6- positions also occurs as does hydroxylation at the N-methyl group.

輸送方法

UN2757 Carbamate pesticides, solid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials. UN 2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required

不和合性

Contact with strong oxidizers can cause fire and explosions.

廃棄物の処理

Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed. Submit to alkaline hydrolysis before disposal.