A series of furan derivatives tebufenozide analogues comprising five compounds (2, 3, 4, 5, and 6) have been designed and synthesized via reaction of N'-phenylfuran-2-carbohydrazide (1) with different acid chlorides. The structures of the synthesized compounds were identified by elemental analyses and spectroscopic data. The analogues compounds have the active center of tebufenozide (mimic) with change of tertiary butylhydrazine by phenylhydrazine. Studying the effect of this change on the toxicological activity against Spodoptera littoralis larvae was performed for three compounds of the synthesized ones. Toxicological activity data showed that compound (3) is more active than compounds (2) and (5)

Many of mimic analogues synthesized before depending on the change in the structure of aromatic rings. In this work, the carbonyl group in the structure of compounds 1-4 converted to thiocarbonyl group, and then studying the toxicological activity due to chemical change in the active center of mimic analogues was performed for compounds N-tert-butyl-2,4-dichloro-N'-(2,4-dichlorobenzoyl)benzohydrazide (2) and N-tert-butyl-2,4-dichloro-N'-[(2,4-dichlorophenyl)carbonothioyl]benzenecarbothiohydrazide (6). The toxicological study was done by using 2nd and 4th instar larvae of the cotton leaf worm, Spodoptera littoralis (Boisd.). Five concentration levels (600, 300, 150, 75 and 37.5 ppm) of compounds (2) and (6) were applied on the fresh plant food to the newly grown (2^nd and 4^th) instar larvae.

Reaction of N-cyanoguanidine with acid chlorides and aroylisothiocyanates gave the respective; N-(N-cyanocarbamimidoyl)aryl-2-carboxamides 1-5 and N-[(N-cyanocarbamimidoyl)carbamothioyl]benzamides 6-10, which have a Neonictinoid insecticide’s active group moiety (=N–CN). They have more toxicological activity against wheat Aphid (Schizaphis graminum) than Spodoptera littoralis.