Pyrethroids: From Chrysanthemum to Modern Industrial by Yoshio Katsuda (auth.), Noritada Matsuo, Tatsuya Mori (eds.)

By Yoshio Katsuda (auth.), Noritada Matsuo, Tatsuya Mori (eds.)

Progress and way forward for Pyrethroids, by way of Yoshio Katsuda Pyrethrin Biosynthesis and Its rules in Chrysanthemum cinerariaefolium, by means of Kazuhiko Matsuda fresh Advances of Pyrethroids for loved ones Use, through Kazuya Ujihara, Tatsuya Mori and Noritada Matsuo The organic task of a singular Pyrethroid: Metofluthrin, through Masayo Sugano and Takao Ishiwatari Advances within the Mode of motion of Pyrethroids, J. Marshall Clark and Steven B. Symington Mammal Toxicology of man-made Pyrethroids, via Ryozo Tsuji, Tomoya Yamada and Satoshi Kawamura Biotransformation and Enzymatic Reactions of man-made Pyrethroids in Mammals, via Kazuki Mikata, Naohiko Isobe and Hideo Kaneko Environmental habit of artificial Pyrethroids, through Toshiyuki Katagi Ecotoxicology of artificial Pyrethroids, via S. J. Maund, P. J. Campbell, J. M. Giddings, M. J. Hamer, ok. Henry, E. D. Pilling, J. S. Warinton and J. R. Wheeler

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38 41 42 43 43 44 44 47 1 Introduction The study of structural modification of natural pyrethrins has lasted for more than 60 years. Especially, the invention of allethrin, 2-methyl-4-oxo-3-allylcyclopent-2-enyl chrysanthemate, prompted chemists to make structural modifications of the pyrethroid alcohol and acid moieties. As a result, a number of pyrethroids with diversified characteristics have been invented not only for the control of household insect pests but also for agricultural use.

5 Synthetic Studies of Norchrysanthemic Acid . . . . . . . . . . . . . . . . . . . . . . . . 1 Synthesis of (Z)-(1R)-trans-Norchrysanthemic Acid by the Wittig Reaction . . . . 2 Synthesis of (Z)-(1R)-trans-Norchrysanthemic Acid by Pyrolytic Reaction of Chrysanthemum Dicaroboxylic Acid Monomethyl Ester with a New Catalyst . . . 3 Synthesis of (Z)-(1R)-trans-Norchrysanthemic Acid by the Claisen Rearrangement . . . . .

The relative toxicity reaches the maximum between two and three carbon atoms at the 4-position (41 ~ 43). Unsaturation (43) or incorporation of an oxygen atom 40 K. Ujihara et al. Table 1 Insecticidal activities of metofuthrin and its analogus against Curex pipiens pallens by the standard topical application method F O F O F R F Compound 38 39 40 41 42 43 44 45a Empenthrin(9) d-Allethrin(4) R H F Me Et Pr Allyl OMe CH2OMe Relative toxicity 30 100 200 490 250 500 360 2,500 10 100 Table 2 Efficiency of metofluthrin in a non-heating vapor formulation with a fan and mosquito coil formulations aganinst various mosquito species Formulation Species Conc.

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