Olefin-imidacloprid is a highly active metabolite of imidacloprid. To solve the problem of high bee toxicity of olefin-imidacloprid, according to the bioisosterism, a series of novel olefin-imidacloprid mimics containing 1,3-disubstituted- 1,2,4-triazoline were designed and synthesized. The insecticidal activity of these compounds against A. craccivora, Nilaparvata lugens and F. occidentalis and in vitro antifungal activity were determined. The results showed that these compounds showed certain insecticidal activity at 400 μg/mL and 100% lethal rate was obtained from compound Ⅱ-7 at 100 μg/mL against F. occidentalis. The toxicity of some compounds to bees was predicted by admetSAR, and they showed low level of toxicity. On the other hand, the target compounds showed different degrees of antifungal activity against 9 plant pathogenic fungi at the concentration of 50 μg/mL. Compound I-15 exhibited the highest activity with the inhibition rate higher or equal to hymexazol against five pathogens. The structure-activity relationship analysis showed that the compounds bearing alkyl substituent at site 3 in triazoline unit displayed higher insecticidal activity than that of an aryl substitution, meanwhile, the more lipophilic groups, the higher fungicidal activity. The substitution of pyridine ring or thiazole ring at site 1 in triazoline unit had little effect on their antifungal activity. The molecular docking results showed that the binding pattern of compound Ⅱ-7 to acetylcholine binding protein (AChBP) was similar to that of imidacloprid (IMI), indicating that these compounds also had the potential to bind to AChBP, which provided a new reference for further molecular optimization.