New PDF release: Synthetic Pyrethroid Insecticides: Chemistry and Patents

By Dr. Klaus Naumann (auth.), Dr. G. Haug, Prof. Dr. H. Hoffmann (eds.)

ISBN-10: 364274852X

ISBN-13: 9783642748523

ISBN-10: 3642748546

ISBN-13: 9783642748547

Chemistry of Plant safety maintains the guide "Chemie der Pflanzenschutz- und Schadlingsbekampfungsmittel", edited via R. Wegler. Volumes four and five of the sequence give you the first whole and extensive evaluate of man-made pyrethroid pesticides . quantity five provides a close survey of the various artificial equipment (270 response schemes) and of stereochemical features of exchange items, and a compilation of virtually each patent on pyrethroids (2700 references evaluated).

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Additional resources for Synthetic Pyrethroid Insecticides: Chemistry and Patents

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KHS04 101 CI, ) CII d ' 93 The reduction of the unsaturated ketone succeeds with boranate, or by the Meerwein-Pondorf method. Dehydration with acidic clay catalyst [163], or more conventionally with acids, acidic salts or FeCl 3 [165] leads to the product. Reaction scheme 61 describes another trichloromethyl radical-addition to isoprenol [165] for the synthesis ofthe same unsaturated ketone 101 via an epoxide 102 [166]. Reaction scheme 61 ~OH + CCI 4 peroxide ;} C1r>-< CI ~Cid 101 A more unusual sequence to the diene 93 starts with the cross-aldol reaction of acetaldehyde and isobytyraldehyde which leads to a highly versatile unsaturated alcohol 103 suitable for radical additions of carbon tetrachloride.

Y CI 131 CI 128 40 1 Synthesis of Pyrethroid Acids Reaction scheme 84 °2 )-{NR )(,0yO ~~OCid [218] C1V CI 128 In Reaction scheme 84 an isomeric cyclobutanone 133 is made from very different precursors, an IX-chloroenamine 171 and the diene. But all these very different building blocks merge predominantly into the same trans permethric acid 91. A more classical sequence [220], involving no rearrangement, utilizing diketene and isoprenol via the unsaturated acetic ester 134 produces the y-Iactone 135 (Reaction scheme 85) for permethric acid.

Thus, the stereochemistry in the halo ketone 136 is preserved in the final product 91. The same argument explains the cis-product later on in Reaction scheme 89. 42 1 Synthesis of Pyrethroid Acids Often the halogenation of cydobutanones occurs less smoothly than desired and demands the trial of many methods to find the best one for the cases under investigation. g. 139 are very much suited for 2 + 2-cydoadditions [223, 224, 225] (Reaction scheme 88) to give the desired cydobutanone systems 139.

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Synthetic Pyrethroid Insecticides: Chemistry and Patents by Dr. Klaus Naumann (auth.), Dr. G. Haug, Prof. Dr. H. Hoffmann (eds.)


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