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

Chemistry of Plant defense keeps the guide "Chemie der Pflanzenschutz- und Schadlingsbekampfungsmittel", edited by means of R. Wegler. Volumes four and five of the sequence give you the first entire and extensive evaluation of artificial pyrethroid pesticides . quantity five provides an in depth survey of the various artificial equipment (270 response schemes) and of stereochemical points of alternate items, and a compilation of just about each patent on pyrethroids (2700 references evaluated).

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These reactions are explained in Sect. 5. 2 Synthesis of N or-Chlorochrysanthemic Acid CI0cooH CH 3 B5 In terms of structure, chemical and biological properties nor-chlorochrysanthemic acid 85, the acid in which one methylgroup of chrysanthemic acid is exchanged for a chlorine atom, takes an intermediate position between chrysanthemic acid and permethric acid. This acid, particularly the l-R-cis isomer, could become of interest in the future, if a much cheaper synthesis can be found than for permethric acid.

QQ. $ H 0 ) CI0 CI ):: Reaction scheme 59 At high temperatures pyrolysis of trichloroethylene and isobutene gives the same isomer 100 [160] (Reaction scheme 59). The addition of isobutyrylchloride to vinylidene chloride catalyzed by Lewis acid in Reaction scheme 60 yields a ketone 101 for reduction and acidic dehydration to the diene 93 with a high yield [161, 162]. 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.

The carbonyl oxygen is involved, leading to the formation of the immoniolactone 114 [184]. ill.. 1 H20 tJ C8r3 The stereochemical control in the formation of the final product (Reaction scheme 65) is complex. The product can be obtained by different routes starting with the CCl 4 -adduct 112. Bases, solvents and solvent mixtures are involved in shifting the cis/trans ratio at will between predominant trans- and high cis-content up to 90%. 3 Synthesis of Permethric Acid Na-t-butylate in hexane plus some hexamethyl phosphoric triamide yields the high cis-product quite independent of temperature [185], in contrast to the usually cis/trans 40/60 mixture, which is the trade-product for permethrin, cypermethrin and cyfluthrin.

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