Sevin

A contact insecticide with the trade name Sevin . White solid, m.p. 142 C. It is prepared by reaction of I-naphthol with methyl isocyanate or with phosgene and a base. 

Naphthalene Acetic Acid and Naphthalene Acetamide. Naphthalene acetic acid [26445-01-2] (38) is historicaHy one of the first plant growth regulators. Reports concerning its activity in crops and plants have been a subject in much of the eady Hterature (57). Consequently, it has been used as a starting matedal for other compounds, eg, vide infra Sevin. Naphthaleneacetamide [31093-43-3] (39) has been used as a standard matedal to evaluate abscission pnor to 1953 and its effect on apple drop was reported in 1953 (58). The substance is used as an internal standard in the abscission bioassay (59). 

Sevin. 1-Naphthalenol methylcarbanate [63-25-2] (Sevin) (44) was developed as an insecticide. However, the conception of the molecule, in the mid-1950s, was as a possible herbicide. The compound ultimately was useless as a herbicide, but in routine testing it was discovered to be an excellent insecticide. Sevin was active in the oat mesocotyl assay and demonstrated weak auxin-like activity. During the development of Sevin, it caused massive apple drop in the western United States in an orchard being treated for insects. It is used (ca 1993) as an abscising agent to thin apples. 

Another large use of naphthalene is as a raw material for the manufacture of 1-naphthyl-A/-methylcarbamate [63-25-2] (carbaryl, Sevin). Cmde or semirefined coal-tar or petroleum naphthalene can be used for carbaryl manufacture. Carbaryl is used extensively as a replacement for DDT and other products that have become environmentally unacceptable (see InsectcontrolTECHNOLOGY). 

Naphthol is mainly used in the manufacture of the insecticide carbaryl (59), l-naphthyl A/-methyicarbamate/ iJ-2j5 - (Sevin) (22), which is produced by the reaction of 1-naphthol with methyl isocyanate. Methyl isocyanate is usually prepared by treating methylamine with phosgene. Methyl isocyanate is a very toxic Hquid, boiling at 38°C, and should not be stored for long periods of time (Bhopal accident, India). India has developed a process for the preparation of aryl esters of A/-alkyl carbamic acids. Thus l-naphthyl methylcarbamate is prepared by refluxing 1-naphthol with ethyl methylcarbamate and POCl in toluene (60). In 1992, carbaryl production totaled > 11.4 x 10 t(35). Rhc ne-Poulenc, at its Institute, W. Va., facihty is the only carbaryl producer in United States. 

Monoethylamine is used in the synthesis of Sevin, an important insecticide. Trimethylamine has only one major use, the synthesis of choline, a high-energy additive for poultry feed. 

A. Sevin, D. Masure, G. Giessncr-Prettrc. M. Plau, Helv. Chim. Acta 73. 552 (1990). 

The course of the reaction has not been fully clarified. Hydrolytic and aromatization processes are probably responsible for the formation of colored or fluorescent deriva4 tives (cf. Potassium Hydroxide Reagent). For instance, sevin is converted to a-naphthalkali metal salt of the o-hydroxycinnamic acid pro- duced by hydrolytic cleavage of the pyrone ring is converted from the non-fluorescent cis- to the fluorescent trans-form by the action of long-wavelength UV light (X = 365 nm) [2]. 

Separation methods, multichromato-graphic la 56 Serine la 246,356 lb 132 Serotonin la 70,76,239,240,262,355, 380 lb 37-39,231,243,348 Serotonin metabolites lb 327 Serum lipids la 89 Serum proteins la 74 Sesquiterpene derivatives lb 239,446 Sesquiterpene esters lb 239 Sesquiterpene glucosides la 327 Sesquiterpene lactones lb 448 Sevin lb 387-389 Si 50 000, specific surface area la 91 Silica gel, caffeine-impregnated la 85 -, surface modified la 3 Silica gel 60, specific surface area la 91... 

Calcium arsenate Calcium oxide Camphor Carbaryl (Sevin)... 

The line drawing and chemical formula of Sevin, a common insecticide, appear in the margin. Determine the molar mass of Sevin. 

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