キャプタン 化学特性,用途語,生産方法
外観
白色～わずかにうすい褐色, 結晶～粉末
種類
キャプタンは使用する成分量で次のような殺菌剤に分けられて、使用されています。
1. オーソサイド水和剤80
2. オキシラン水和剤
3. キャプレート水和剤
溶解性
水に難溶 (0.00033g/100ml, 25℃)。クロロホルム, キシレンに可溶。水3.3mg/l(25℃)。キシレン20, クロロホルム70,アセトン21, シクロヘキサン23, ジオキサン47, ベンゼン21, トルエン6.9,イソプロパノール1.7, エタノール2.9, ジエチルエーテル2.5(全てg/kg26℃)。アセトンに溶け、水にほとんど溶けない。
解説
キャプタン (化学式: C9H8Cl3NO2S) とは、殺菌剤に分類され、糸状菌や細菌など植物病原菌の有害作用から農作物等を守る用途で使用される農薬の1種です。
特徴として、多作用点阻害の特性を持つことが挙げられます。他の殺菌剤は、菌糸の呼吸阻害や細胞壁阻害など特定の作用により殺菌効果を得ますが、キャプタンは、これらの複数の阻害作用を持っています。
農薬の作用機構による分類ではコード、M (多作用点接触活性) のグループに分類されています。複数の作用により菌糸の成長を阻害するため、菌に耐性がつきにくいことです。
常温常圧では無臭で、白色粉末状の個体として存在し、水に溶かして使用することが多いです。
用途
殺菌剤。石けんの殺菌剤(多量に摂取すると嘔吐、下痢を起こす)。使用濃度は0.5%で、セッケンやシャンプー中では、殺菌に対し静菌的に作用する
農薬用途
殺菌剤
説明
Captane is a pesticide belonging to the thiophtalimide
group, mainly affecting agricultural workers. As a
sensitizer and photosensitizer, it can induce contact
urticaria. Its is used as a fungicide and a bacteriostatic
agent in cosmetics and toiletries, particularily in
shampoos. Cases of contact dermatitis were reoprted
in painters, polishers and varnishers.
化学的特性
Captan, when pure, is a colorless crystalline
solid. The technical grade is a cream to yellow powder
with a strong odor. It is commonly dissolved in a “carrier”
which may be combustible.
使用
Captan is used to control a wide range of fungal diseases on many
crops.
定義
ChEBI: A dicarboximide that is 3a,4,7,7a-tetrahydrophthalimide in which the hydrogen attached to the nitrogen is replaced by a trichloromethyl group. A non-systemic fungicide introduced in the 1950s, it is widely used for the control of fungal diseases in fruits,
vegetables, and ornamental crops.
一般的な説明
Captan is a white solid dissolved in a liquid carrier. Captan is a water emulsifiable liquid. Captan can cause illness by inhalation, skin absorption and/or ingestion. The primary hazard of Captan is that Captan poses a threat to the environment. In case of release immediate steps should be taken to limit its spread to the environment. Since Captan is a liquid Captan can easily penetrate the soil to contaminate groundwater. Captan is used as a fungicide.
空気と水の反応
Slowly hydrolyzed in aqueous neutral and acidic media. Rapidly hydrolyzed in alkaline media. Insoluble in water.
反応プロフィール
Captan decomposes at or near the melting point. Captan is incompatible with strong alkaline and oxidizing materials, sulfur and (sulfur + moisture).
危険性
A questionable carcinogen. A skin irritant.
Avoid inhalation of dust or spray mist. Avoid con-
tamination of feed and foodstuffs.
健康ハザード
Vapor irritates eyes. Ingestion causes depression, lachrymation, labored respiration, diarrhea.
火災危険
Special Hazards of Combustion Products: Irritating and toxic gases are produced in a fire; they may include sulfur dioxide, hydrogen chloride, phosgene, and oxides of nitrogen.
注意点
使用上の注意
- 使用の際は、手袋、マスク、防護メガネを着用し、目や鼻や皮膚に直接かからないように注意が必要です。
- 1日摂取許容量が定められているので、その数値以上の量を摂取しないことが求められます。
- 蚕やミツバチ、天敵生物に一定量以上で障害がでる可能性があるため、近くにいる環境での使用は注意が必要です。
作用机制
酵素などのSH基を非特異的にブロックし，菌類の呼吸を阻害する
使用用途
キャプタンは、殺菌剤として野菜・果樹の病気予防・治療を目的として使用されます。
农业用途
Fungicide: Most uses of captan on food crops in the United States have been canceled since 1989. It is still used in apple production, almonds and strawberries. It is often applied to packing and shipping boxes for fruits and vegetables. Captan is rapidly degraded in natural soil by chemical as well as biologic means (estimated half-life, days to weeks). It is also used as a preservative for awnings, draperies and leather, as a root dip and seed treatment. It is also added to paints, wallpaper paste, plastic and leather goods. There are over 320 federally registered pesticide products that contain captan.
製品名
AACAPTAN®; AGROSOL S®[C]; AGROX® 2-WAY and 3-WAY[C]; AMERCIDE®; APRON®[C]; BEISTERGARD®; BANGTON®; BEAN SEED PROTECTANT®; CAPTANCAPTENEET® 26,538; CAPTAF®; CAPTAF®; CAPTAN® 50 W; CAPTAN SC®; CAPTEX®; CRIPTAN®; ESSO® FUNGICIDE 406; FLIT® 406; FUNGUS BAN® TYPE II; FUNGICIDE 406®; GLYODEX® 37-22; GRANOX PFM®; GUSTAFSON CAPTAN 30-DD; HEXACAP®; ISOTOX SEED TREATER® “D” and “F”; KAPTAN®; MALIPUR®; MERPAN®; MICRO-CHECK® 12; MIOSTAT®; NERACID®; ORTHOCIDE®; OSOCIDE®; POTATO SEED PIECE PROTECTANT®; SR 406®; STAUFFER CAPTAN®; TRIMEGOL®; VANICIDE®; VANICIDE® P-75; VANICIDE® 89; VANICIDE® 89RE; VANGARD® K; VANGUARD® K; VONDCAPTAN®
接触アレルゲン
A pesticide, belonging to the thiophthalimide group, mainly
affects agricultural workers. Being sensitizer and photosensitizer,
it can induce contact urticaria. It is used as a
fungicide and a bacteriostatic agent in cosmetics and toiletries,
particularly in shampoos. Cases of contact dermatitis
were reported in painters, polishers, and varnishers
安全性プロファイル
Poison by
intraperitoneal route. Moderately toxic to
humans by ingestion. Moderately toxic
experimentally by ingestion and inhalation
routes. Experimental teratogenic and
reproductive effects. Questionable
carcinogen with experimental tumorigenic
and neoplastigenic data. Human mutation
data reported. When heated to
decomposition it emits toxic fumes of Cl-,
SOx, and NOx.
職業ばく露
Captan is a thiophthalimide compound
used as an agricultural fungicide for field crops and storage
of produce and also as a preservative in cosmetics; an overthe-counter-drug.
環境運命予測
Biological. In water, captan reacted with the fungicide L-cysteine forming a compound
with an absorption maximum of 272 μm which was identified as 2-thiazolidinethione-4-
carboxylic acid. In addition, tetrahydrophthalimide also formed (Lukens and Sisler, 1958).
Soil. The half-lives of captan in soil ranged from 3.5 days (pH 6.4, moisture content
17.5%) to >50 days (pH 6.2, moisture content 1.6%) (Burchfield, 1959). The half-lives of
captan in a sandy loam, clay loam and an organic amended soil under non-sterile conditions
were 10–354, 3.4–587 and 7.0–213 days, respectively, while under sterile conditions the
half-lives were 9.4–373, 2.8–303 and 4.3–191 days, respectively (Schoen and Winterlin,
1987).
Chemical/Physical. Captan undergoes hydrolysis under neutral or alkaline conditions
yielding 4-cyclohexene-1,2-dicarboximide, carbon dioxide, hydrogen chloride and sulfur
(Wolfe et al., 1976a). The estimated hydrolysis half-life of captan in a phosphate buffer
solution at pH 7.07 and 28–29°C is 2.96 hours. Between the pH range 2 to 6, the estimated
hydrolysis half-life is 10.70 hours (Wolfe et al., 1976a). Worthing and Hance (1991)reported hydrolysis half-lives of 8.3–32.4 hours and <2 minutes at pH values 7 and 10,
respectively.
Decomposes at or near the melting point (Hartley and Kidd, 1987).
代謝経路
Captan contains an unstable trichloromethylthio (sulfenyl) moiety that
has been shown to undergo rapid hydrolytic and metabolic degradation
to tetrahydrophthalimide (2).
Studies of the decomposition of [
35S]captanw ith conidia of Neurospora
crassa (Richmond and Somers, 1968) showed that the trichloromethythio
moiety can be transferred to the sulfur atoms of thiols such as cysteine
and glutathione (Richmond and Somers, 1966). Thus, in the presence of
thiols such as glutathione, captan is cleaved at the N-S bond to form
thiophosgene (3) and other gaseous products such as hydrogen sulfide,
hydrogen chloride and carbonyl sulfide (see Scheme 2). Thiophosgene is
rapidly hydrolysed by water. The trichlormethythio group and thiophosgene
are believed to be intermediates in the formation of thiazolidine-2-
thione-4-carboxylic acid (4) which is an addition product with cysteine. A
thiazolidine derivative of glutathione is also formed (5). Biotransformation
of captan in mammals generates primarily thiophosgene (3) and
tetrahydrophthalimide (2). Tetrahydrophthalimide (2) and various of its
hydroxylated derivatives are excreted in the urine. The thiophosgeneglutathione
adduct (5) subsequently degrades and is eventually excreted
in the urine as 2-thiazolidinethione-4-carboxylic acid (4).
輸送方法
UN2773 Phthalimide derivative pesticides, solid,
toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials,
Technical Name Required. UN2811 Toxic solids, organic,
n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials,
Technical Name Required.
不和合性
Incompatible with tetraethyl pyrophosphate, parathion. Keep away from strong alkaline materials(e.g., hydrated lime) as captan may become unstable. May
react with water releasing hydrogen chloride gas. Corrosive
to metals in the presence of moisture.
廃棄物の処理
Captan decomposes fairly
readily in alkaline media (pH ＞8). It is hydrolytically
stable at neutral or acid pH but decomposes when heated
alone at its freezing/melting point. Alkaline hydrolysis is
recommended
キャプタン 上流と下流の製品情報
原材料
準備製品