Synthesis and bioefficacy evaluation of new 3-substituted-3,4-dihydro-1,3-benzoxazines

Abstract

A new series of 1, 3-Benzoxazines were synthesized, characterized (¹H NMR and ¹³C NMR) and evaluated for their pesticidal activity. Six new 3-alkyl-3, 4-dihydro-4-methyl-2H-1, 3-benzoxazines (1-6) were prepared by hydroxymethylation of secondary amines with formaldehyde in 65–68% yields. These compounds were screened for there IGR activity against Spodoptera litura and for antifungal fungal activity in vitro against Sclerotium rolfsii ITCC 6181 by poisoned food technique. Insect Growth Regulatory (IGR) activity against Spodoptera litura showed that compound 3-Nonyl-3,4-dihydro-4-methyl-2H-1,3-benzoxazines was most effective as IGR with larval GI₅₀ of 1.863 μ g/Insect. Compounds 3-Octyl-3,4-dihydro-4-methyl-2H-1,3-benzoxazines and 3-Decyl-3,4-dihydro-4-methyl-2H-1,3-benzoxazines were effective IGRs. Antifungal screening revealed that compound 3-Dodecyl-3, 4-dihydro-4-methyl-2H-1,3-benzoxazines, was highly effective against Sclerotium rolfsii with LC₅₀ value 31.7 mg L⁻¹ comparable with commercial fungicide Hexaconazole (LC₅₀ 1.27 mg L⁻¹). Also compounds 3-Nonyl-3, 4-dihydro-4-methyl-2H-1,3-benzoxazines and 3-Decyl-3,4-dihydro-4-methyl-2H-1,3-benzoxazines displayed promising fungitoxicity. The results described in this paper are promising and provides new array of synthetic chemicals to be utilized as pesticides.

Keywords:

• 1, 3-Benzoxazines
• pesticidal activity
• hydroxymethylation
• insect growth regulatory activity
• Spodoptera litura
• Sclerotium rolfsii
• poisoned food technique

A part of this paper was presented in the 13th ISCB (Indian Society of Chemists and Biologist) International Conference on Interplay of Chemical and Biological Sciences: Impact on Health and Environment 26th Feb-1st Mar 2009 held in New Delhi, India.