Synthesis and Insecticidal Activity of Ureas and Amides with Bicyclic Monoterpenyl Derivatives (Mites)

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  • NOMURA Masato
    Department of Industrial Chemistry, Faculty of Engineering, Kinki University
  • KASEMURA Kazuo
    Department of Industrial Chemistry, Faculty of Engineering, Kinki University
  • OBANA Mitsuhiko
    Research Laboratory, Kounan Process Co., Ltd.
  • SAKURANO Masaru
    Department of Industrial Chemistry, Faculty of Engineering, Kinki University
  • FUJIHARA Yoshihito
    Department of Industrial Chemistry, Faculty of Engineering, Kinki University

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Other Title
  • 二環性モノテルペニル基を含有する尿素およびアミド系化合物の合成と殺虫活性 (ダニ類)
  • 2カンセイ モノテルペニルキ オ ガンユウ スル ニョウソ オヨビ アミドケイ
  • 生理活性物質の合成に関する研究 (第19報)

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Abstract

Synthesis and Insecticidal activity of ureas and amides with an bicyclic monoterpenyl derivatives was examined.<BR>2-Carene (1), 3-carene (2), thujone (3) and d-menthol (4) were converted to secondary amines (5) (8) by hydroboration, Jones oxidation, oximation (N, N-dimethylhydrazonation, methylation and elimination reaction) or reduction with LiAlH4. The secondary amine derivatives were condensed with six chlorides to obtain urea (5a) (8e) and amide compounds (5f) (8f).<BR>Twenty-four monoterpene derivatives obtained were tested for insecticidal activity toward Tyrophagus putrescentiae (T. putrescentiae) and Dermatophagoides farinae (D. farinae).<BR>On filter paper, compounds (5a), (5d), (5e) and (6b) (6d) from (1) and (2) showed higher insecticidal activity than N, N-diethyl-m-toluamide (DEET) for D. farinae. In air dusting for D. farinae, these compounds (5d) and (6b) (6d) at 0.2g/m2 had exterminative effects for a long time, and were more active than DEET.

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