フェンバレレート 化学特性,用途語,生産方法
外観
ごくうすい黄色〜黄色, 澄明の液体
溶解性
水に難溶 (0.1mg/100ml, 20℃)。有機溶剤に易溶。水 ＜10μg/l(25℃)。n-ヘキサン53, キシレン ＞200, メタノール84(全てg/l 20℃)。アセトンに溶け、水にほとんど溶けない。
解説
フェンバレレート,黄褐色の粘ちゅうな液体．沸点300 ℃(4.9 kPa)．水溶解度10 μg L－1(25 ℃)以下．フェンバレレートは，ピレスロイドと同様に神経細胞Naチャンネルのブロッカーで，速効的な殺虫効果を示す．天然ピレスロイドの欠点であった光に対する不安定性を克服して，本格的な農薬として使用可能となった最初の合成ピレスロイドである．LD50 451 mg/kg(ラット，経口)．
森北出版「化学辞典（第2版）
製造
フェンバレレート,スミサイジンともいう．水酸化カリウム存在下，p-クロロベンジルシアニドとイソプロピルクロリドとを反応後加水分解し，ついで塩化チオニルと反応させて(RS)-2-(4-クロロフェニル)-イソバレリルクロリドとし，α-シアノ-3-フェノキシベンジルアルコールを塩基の存在下で反応させると得られる．
効能
抗寄生虫薬, 殺虫薬
農薬用途
動物薬、殺虫剤、ダニ駆除剤
説明
Fenvalerate is a yellow-brown viscous liquid that is practically soluble in water. It is stable to moderate heat and light and is rapidly hydrolysed in basic environments (above pH 8). Fenvalerate is a racemic mixture of four stereoisomers in equal proportions owing to the presence of two chiral centres. It is a synthetic type II pyrethroid.
Fenvalerate is registered as an insecticide for a wide array of crop uses, as well as a termiticide and insect repellent.
化学的特性
It is an ester of 2-(4-chlorophenyl)-3-methylbutyric acid and alpha-cyano-3-phenoxybenzyl alcohol but lacks a cyclopropane ring. However, in terms of its insecticidal behaviour, it belongs to the pyrethroid insecticides. Technical grade fenvalerate is a yellow or brown viscous liquid having a specific gravity of 1.175 at 25°C. The vapour pressure is 0.037 mPa at 25°C, and it is relatively non-volatile. It is practically insoluble in water (approximately 2 μg/L) but soluble in organic solvents such as acetone, xylene, and kerosene. It is stable to light, heat, and moisture but unstable in alkaline media.
使用
Fenvalerate controls a wide range of insect pests in fruit, vines,
olives, hops, nuts, vegetables, cotton, oilseed rape, sunflowers, alfalfa,
cereals, maize, sorghum, potatoes, beets, soyabeans, tobacco, sugar cane
and ornamentals. It is also used in public health situations and in animal
houses.
定義
ChEBI: A carboxylic ester obtained by formal condensation between 2-(4-chlorophenyl)-3-methylbutyric acid and cyano(3-phenoxyphenyl)methanol.
一般的な説明
A clear viscious yellow liquid with a mild odor. Used as broad spectrum insecticide.
空気と水の反応
Insoluble in water. Rapidly hydrolyzed by alkaline solution.
反応プロフィール
A pyrethroid. Phenvalerate is an ester and nitrile. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. Nitriles may polymerize in the presence of metals and some metal compounds. They are incompatible with acids; mixing nitriles with strong oxidizing acids can lead to extremely violent reactions. Nitriles are generally incompatible with other oxidizing agents such as peroxides and epoxides. The combination of bases and nitriles can produce hydrogen cyanide. Nitriles are hydrolyzed in both aqueous acid and base to give carboxylic acids (or salts of carboxylic acids).
危険性
Questionable carcinogen.
接触アレルゲン
Fenvalerate is an insecticide of the synthetic pyrethroid
group, which induced sensitization in farmers.
安全性プロファイル
Poison by ingestion,
intravenous, and intracerebral routes.
Moderately toxic by skin contact.Experimental reproductive effects. Mutation
data reported. Highly toxic to fish and bees.
Corrosive, causes eye damage. A skin
irritant. When heated to decomposition it emits toxic fumes of Cl-, NOx, and CN-. See
also CYANIDE.
職業ばく露
Fenvalerate is one of the most versatile
synthetic pyrethroid insecticides. It is mostly used in agriculture and on cattle, but also in homes and gardens. It
acts as a stomach poison against a wide variety of leaf and
fruit eating such as bollworm fruit and shoot borers and
aphids. Crops on which it is used include cotton, cauliflower, okra, vines and fruits. It is also used in public health
and animal husbandry. It is effective against pests whose
strains are resistant to organochlorine, organophosphorus,
and carbamate insecticides. Not used in EU countries
環境運命予測
Soil. Fenvalerate is moderately persistent in soil. The percentage of the initial dosage (1 ppm) remaining after 8 weeks of incubation in an organic and mineral soil were 58 and 12%, respectively, while in sterilized controls 100 and 91% remained, respectively (Chapman et al., 1981).
In a sugarcane runoff plot, fenvalerate was applied at a rate of 0.22 kg/ha 4 times each year in 1980 and 1981. Runoff losses in 1980 and 1981 were 0.08 and 0.56 of the applied amount, respectively (Smith et al., 1983).
Plant. Dislodgable residues of fenvalerate on cotton leaf 0, 24, 48, 72 and 96 hours after application (0.22 kg/ha) were 0.85, 0.36, 0.38, 0.28 and 0.28 μg/m2, respectively (Buck et al., 1980).
Surface Water. In an estuary, the half-life of fenvalerate was 27–42 days (Schimmel et al., 1983).
Chemical/Physical. Undergoes hydrolysis at the ester bond (Hartley and Kidd, 1987). Decomposes gradually at 150–300°C (Windholz et al., 1983) probably releasing toxic fumes of nitrogen and chlorine.
代謝経路
After foliar treatment of 14C-fenvalerate on wheat
plants, the amount of residual radioactivity in the grain
and hull is below the limit of reliable measurement.
Individual degradation products accounting for more
than 1% of the applied radioactivity are not present in
the foliage or straw. Important degradation pathways
include decarboxylation and ester cleavage.
輸送方法
UN3349 Pyrethroid pesticide, solid toxic,
Hazard Class: 6.1; Labels: 6.1-Poisonous material. UN3352
Pyrethroid pesticide, liquid toxic, Hazard Class: 6.1;
Labels: 6.1-Poisonous materials.
不和合性
ncompatible with oxidizers, chlorates
nitrates, peroxides, sulfuric acid, caustics, ammonia, aliphatic amines, alkanolamines, isocyanates, alkylene oxides,
epichlorohydrin. Moisture may cause hydrolysis or other
forms of decomposition. Emulsifiable concentrate is
corrosive
廃棄物の処理
Incineration would 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
参考文献
[1] http://www.toxipedia.org
[2] Y. Xia, Q. Bian, L. Xu, S. Cheng, L. Song, J. Liu, W. Wu, S. Wang and X. Wang, Genotoxic effects on human spermatozoa among pesticide factory workers exposed to fenvalerate, Toxicology, 2004, vol. 203, 49-60
[3] Terry R Roberts, David H Hutson, Philip W Lee, Peter H Nicholls and Jack R Plimmer, Metabolic Pathways of Agrochemicals: Part 2: Insecticides and Fungicides, 1999
フェンバレレート 上流と下流の製品情報
原材料
準備製品