Studies On The Synthesis Of Chlorfenapyr And Bis(1,4-diacylthiosemicarbazide)Compounds

(Chlorfenapyr)(1), is a novel green pesticide with broad spectrum and highly effective insecticidal activity. In this paper, two reaction routes were designed for the synthesis of Chlorfenapyr in good yields from the original materials p-chlorobenzaldehyde via a series of reactions: Strecker reaction to prepare amino acid (2), (1'); 1,3 -dipolar addition reaction of acrylonitrile with trifluoroacetyl amino acid (3), (2') to synthesize the important intermediate pyrroline (4), (3'); oxidation elimination of hydrogen to get pyrrole (5), (4'); and bromination, substitution reaction of pyrrole (5), (4') etc. to reach our final product (1). The influence factors in the synthesis of intermediates and Chlorfenapyr were meticulously investigated and the reaction conditions were bettered. Finally, some satisfactory results have been obtained. The structures of intermediates and Chlorfenapyr were confirmed by IR, NMR, MS.Acylthiosemicarbazide compounds often exhibit various kinds of biological activities. In this paper, eleven new bis(1,4-diacylthiosemicarbazide) compounds (1a-f), (1'd-h) were designed and synthesized in good yields by the condensation reaction of bis(carbonyl isothiocyanate) (3a-f) with benzoic hydrazide or dicarbonyl dihydrazide (5d-h) with benzoic isothiocyanate. And the intermediates (3a-f), (5d-h) can be easily prepared from the original dicarboxyl acids. The structures of the target compounds were confirmed by IR, NMR, MS.