ベノミル

外観

白色～うすい黄色, 結晶性粉末～粉末

溶解性

水3.6（pH 5）、2.9（pH 7）、1.9（pH 9）（mg/ℓ、室温）。クロロホルム94、DMF 53、アセトン18、キシレン10、エタノール4、ヘプタン0.4（g/ ㎏、25℃）(和光純薬時報 Vol.82, No.3(2014), p12)(ANALYTICAL CIRCLE 2014.9/No.74, p14)アセトンに溶け、水及びエタノールにほとんど溶けない。

解説

ベノミル．ベンレートともいう．2-メチルイソチオ尿素と2モル量のクロロギ酸メチルとを水酸化ナトリウムの存在下で反応させ，2-メチル-1,3-ビス(メトキシカルボニル)イソチオ尿素とし，ついでo-フェニレンジアミンと反応させて，N-(ベンズイミダゾール-2-イル)カルバミン酸メチル(MBC)とし，引き続きイソシアン酸ブチルを反応させると得られる．無色の結晶．分解点140 ℃．水溶解度2.9 mg L－1(pH 7，20 ℃)．通常の有機溶媒に難溶．ベノミルは広範囲の植物病原菌に卓効を示す農業用殺菌剤で，植物体内でMBCに変換されて，チューブリンに結合して核分裂を阻害する．LD50 5000 mg/kg(ラット，経口)．

用途

農薬(殺虫殺菌剤)

使用上の注意

アルゴン封入

説明

Benomyl, a tan-coloured crystalline solid/powder, is a systemic fungicide with a characteristic odour. It belongs to the benzimidazole family. Benomyl decomposes at high temperature. Benomyl is essentially insoluble in water. It is stable under normal storage conditions but will decompose to carbendazim in water. On decomposition by heat, benomyl produces toxic fumes including nitrogen oxides. Benomyl is a systemic and broad-spectrum fungicide that is currently registered for use in more than 50 countries on more than 70 crops for the control of diseases in fruit trees, nut crops, vegetables, cereals, tropical crops and ornamentals, turf, and many field crops. Benomyl is marketed as a wettable powder and as a dry flowable formulation (dispersible granules).

化学的特性

Benomyl is a white crystalline solid. Faint acrid odor.

使用

Benomyl is a systemic fungicide with both protective and curative activities. It is effective against more than 190 different fungal diseases in stone fruits, pome fruits, tropical and subtropical fruit crops, grapes, fruiting vegetables, cereals, etc. It is effective against fungal diseases caused by Ascomycetes and Basidiomycetes spp., including leaf spots, blotches and blights; fruit spots and rots; sooty mould; scabs, bulb, corm and tuber decays; blossom blights; powdery mildew; certain rusts; common soil borne crown and root rots.

定義

ChEBI: A member of the class of benzimidazoles that is the methyl ester of [1-(butylcarbamoyl)-1H-benzimidazol-2-yl]carbamic acid. A foliar fungicide used to control a wide range of Ascomycetes and Fungi Imperfecti in a wide range of crops.

一般的な説明

Colorless to white crystals or off-white powder. Faint acrid odor.

空気と水の反応

Insoluble in water.

反応プロフィール

Benomyl is incompatible with strong acids, peroxides and strong oxidizers. Decomposed by strong alkalis. Also decomposes on storage with water .

危険性

High toxicity by ingestion. Upper respira- tory tract irritant, male reproductive, testicular, and embryo/fetal damage. Possible carcinogen.

健康ハザード

Mildly toxic in rodent by ingestion, inhalation, and absorption through skin; large dosescan produce effects of carbamate poisoning;teratogenic and mutagenic effects reported;carcinogenic potential not known; mild skinirritant.
LD50 oral (rat): 10,000 mg/kg
LD50 skin (mouse): 5600 mg/kg
LD50 skin (wild bird): 100 mg/kg
Benomyl metabolizes to carbendazim(MBC) and 5-HBC. Animal studies indicatedthat benomyl and its metabolites rapidlyeliminated out within 24 hours of exposure.They do not accumulate in tissues over longterm exposure..

火災危険

Literature sources indicate that Benomyl is nonflammable.

农业用途

Fungicide: Used as a pre-harvest systemic fungicide and as a post-harvest dip. Used on arable and vegetable crops, apples, soft fruit, nuts, mushrooms, lettuce, tomatoes and turf. In California, the top five crops for which benomyl is used are pistachios, table and raisin grapes, almonds, strawberries and wine grapes. All uses of benomyl products in the United States was phased out with a deadline of December 31, 2003. Not approved for use in EU countries.

製品名

ABORTRINE®; AGROCITE®; ARILATE®; BBC 6597®; BENEX®; BENLAT®[C]; BENLATE®, withdrawn 5/7/01; BENLATE 50®; BENLATE 50 W®; BENLATE 50WP®; BENOMYL® 50 W; BENOSAN®; D 1991®[C]; F 1991®; FUNDAZOL®; FUNGICIDE 1991®; FUNGACIDE D-1991®; FUNGOCHROM®; TARSAN®; TERSAN®; TERSAN 1991®; UZGN®

接触アレルゲン

Benomyl is a fungicide, derived from benzimidazole. Cases of sensitization were reported in horticulturists and florists. It is however, at most, a weak sensitizer, with possible false-positive patch reactions, or with crossreactions after previous exposure to other fungicides.

安全性プロファイル

Poison by ingestion. Mildly toxic by inhalation. Experimental teratogenic and reproductive effects. Human mutation data reported. A human skin irritant. When heated to decomposition it emits toxic fumes of NO,. See also CARB AMATES.

職業ばく露

Benomyl is used as an agricultural chemical and pesticide, pharmaceutical, and veterinary drug.

発がん性

Benomyl was genotoxic, causing chromosome aberrations in vitro and in vivo, but it does not directly act with DNA.

代謝経路

When benlate is degraded by the singlet oxygen photoreaction either in methanol or in aqueous hydrochloric solutions, carbendazim is identified as a major degradation product with the other nine degradation products from both reactions, including 2-guanidinobenzimidazole, benzimidazole, and 2,4'-and 2,5'-bibenzimidazoles which are identical to the photodegradation products of carbendazim by the singlet oxygen photoreaction in aqueous hydrochloric acid solution.

輸送方法

UN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9—Miscellaneous hazardous material, Technical Name Required.

不和合性

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides (forms toxic oxides of nitrogen). Decomposed in water or otherwise moist conditions.

廃棄物の処理

In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. Must be disposed properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office.