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carbaryl : ウィキペディア英語版
carbaryl

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Carbaryl (1-naphthyl methylcarbamate) is a chemical in the carbamate family used chiefly as an insecticide. It is a white crystalline solid commonly sold under the brand name Sevin, a trademark of the Bayer Company. Union Carbide discovered carbaryl and introduced it commercially in 1958. Bayer purchased Aventis CropScience in 2002, a company that included Union Carbide pesticide operations. It remains the third-most-used insecticide in the United States for home gardens, commercial agriculture, and forestry and rangeland protection. About 11 million kilograms were applied to U.S. farm crops in 1976.〔Robert L. Metcalf “Insect Control” in Ullmann’s Encyclopedia of Industrial Chemistry” Wiley-VCH, Weinheim, 2002. 〕 As a veterinary drug, it is known as carbaril (INN).
==Production==
Carbaryl is produced by treating methyl isocyanate (3) with 1-naphthol (4).
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Alternatively, 1-naphthol (1) is first converted to its chloroformate (3), which is then treated with methylamine to give the desired product (4):〔
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The former process was carried out in Bhopal. In comparison, the latter synthesis uses exactly the same reagents, but in a different sequence. This synthesis avoids the preparation of methyl isocyanate, and the comparison is often used as a case study in green chemistry. However, the second synthesis still uses phosgene, which is toxic and reacts with water, and methylamine, which is a toxic and flammable gas.

抄文引用元・出典: フリー百科事典『 ウィキペディア(Wikipedia)
ウィキペディアで「carbaryl」の詳細全文を読む



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