Synthesis and Insecticidal Activities and SAR Studies of Novel Benzoheterocyclic Diacylhydrazine Derivatives

Abstract

Two series of novel N′-tert-butyl-N′-substituted benzoyl-N-2,3-dihydrobenzofuran-5-carbohydrazide derivatives were synthesized, their activities and different insecticidal action modes for different Lepidopteral larvicidal assays were evaluated carefully. The results of larvicidal activities against oriental armyworm and mosquito indicate that different benzoheterocyclic analogues of diacylhydrazide have different structure-activity relationships according to the types and patterns of substitution on the benzene, and 3,5-dimethyl is the most efficient substituent for benzoheterocyclic diacylhydrazine. Among them, N′-tert-butyl-N′-(3,5-dimethylbenzoyl)-N-2,4-dimethyl-2,3-dihydrobenzofuran-5-carbohydrazide (Ii) stood out as the best compound with high activity. Compound Ii and N′-tert-butyl-N′-(3,5-dimethylbenzoyl)-N-5-chloro-6-chromanecarbohydrazide (F) have higher contact activities against diamond-back moth and stomach toxicities against cotton bollworm than ANS-118 and JS-118. Compound F has higher contact toxicity against beet armyworm than ANS-118 and JS-118. These results indicate that different heterocycles and substitutents on the benzene rings of benzoheterocyle moiety not only influence the larvicidal activities strongly but also are very sensitive to the insecticidal action modes for different Lepidopteran larvicidal insects.

Chemical Composition of Taxus baccata L. Leaves and Male Cones Water:Methanol Extracts

“…2,3-dihydrobenzofuran has shown effective results against cancer, tuberculosis, malaria, and cataracts [26]. Moreover, some plant species that are reach in 2,3-dihydrobenzofuran possess antioxidant and/or cytoprotective characteristics and insecticidal features [27,28]. Some of the common uses of oleic acid are in the food, pharmaceutical, cosmetic, and biodiesel industries [29].…”

Synthesis of Phenostereum A and Related Diol and Attempted Assignment of Relative Configurations of Remote Stereocenters by13C NMR

“…The unsubstituted 2,3‐dihydrobenzofuran (coumaran) is also a secondary metabolite of Cyperus nipponicus with antifeeding activity against polyphagous insects . To date, the number of identified natural 2,3‐dihydrobenzofurans has exceeded 500, a substantial part of which were reported to have various bioactivities (including anticancer,– anti HIV, antimalarial, antituboculosis, enzyme inhibition– and insecticidal activities), promoting many synthetic studies into this class of heterocycles …”

Thiosemicarbazones as Aedes aegypti larvicidal

“…Culex quinquefasciatus [45][46][47]) or about the repellence for adult A. aegypti [48][49][50][51]. They will not be discussed here, however, since they are out of the scope of the present work.…”