Synthesis and pesticidal activity of new N-alkyl-N-[1-(2-hydroxyphenyl) ethyl]amines.
A series of novel N-alkyl-N-[1-(2-hydroxyphenyl) ethyl]amines were synthesized as potential new agents to control pests. Their structures were confirmed on the basis of IR, NMR and elemental analyses. Six new N-alkyl-N-[1-(2-hydroxyphenyl) ethyl]amines were prepared by reduction of corresponding Schiff bases using sodium borohydride in 80-87 % yields. These compounds were tested for their antifungal activity against two pathogenic fungi viz., Rhizoctonia bataticola ITCC 0482 and Sclerotium rolfsii ITCC 5226 and for insecticidal activity against insects of stored grain pest Callosobruchus analis. Fungicidal bioassay revealed that compound N-Decyl-N-[1-(2-hydroxyphenyl)ethyl]amine, was highly effective against R. bataticola (ED(50) 6.86 mg L(-1)) which was comparable with that of commercial fungicide hexaconazole (ED(50) 6.35 mg L(-1)). Also compounds N-Heptyl-N-[1-(2-hydroxyphenyl)ethyl]amine, N-Octyl-N-[1-(2-hydroxyphenyl)ethyl]amine and N-Nonyl-N-[1-(2-hydroxyphenyl)ethyl]amine displayed promising fungitoxicity against same pathogen. However, compound N-Heptyl-N-[1-(2-hydroxyphenyl)ethyl]amine was also found to be effective against S. rolfsii (ED(50) 4.92 mg L(-1) as against 1.27 mg L(-1) for hexaconazole). Compound N-Hexyl-N-[1-(2-hydroxyphenyl)ethyl]amine was most effective as insecticide followed by compound N-Octyl-N-[1-(2-hydroxyphenyl)ethyl]amine. LC(50) values for these compounds were 155.0 and 275.0 mg L(-1) respectively as against 36.70 mg L(-1) for commercial insecticide dichlorovos. The results obtained from bioassays indicate that this class of compounds can be utilized for the design of new substances endowed with pesticidal activities.
Division of Agricultural Chemicals, Indian Agricultural Research Institute, New Delhi, India. iamshakil@gmail.com
Najam Akhtar
NA
Shakil
Jitendra
J
Kumar
Alka
A
Pandey
Vivek
V
Ahluwalia
Manish K
MK
Singh
Chitra
C
Srivastava
D000588:Amines / Q000138:chemical synthesis* / Q000494:pharmacology*; D000818:Animals; D001517:Coleoptera / Q000187:drug effects; D005658:Fungi / Q000187:drug effects; D005659:Fungicides, Industrial / Q000138:chemical synthesis* / Q000494:pharmacology*; D007306:Insecticides / Q000138:chemical synthesis* / Q000494:pharmacology*; D015394:Molecular Structure
D000588:Amines; D005659:Fungicides, Industrial; D007306:Insecticides