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  • Synthesis of [3-(3-chloro-4-fluorophenyl)-2-oxo-3,4-dihydro-2H-2lambda5- benzo[e][1,3,2]oxazaphosphinin-2-yl]-(aryl/alkyl) methanols and their bioactivity on sugarcane smut.

Synthesis of [3-(3-chloro-4-fluorophenyl)-2-oxo-3,4-dihydro-2H-2lambda5- benzo[e][1,3,2]oxazaphosphinin-2-yl]-(aryl/alkyl) methanols and their bioactivity on sugarcane smut.

Journal of agricultural and food chemistry (2007-07-31)
Y B Kiran, P Vasu Govardhana Reddy, C Devendranath Reddy, D Gunasekar, N P Eswara Reddy
ABSTRACT

Synthesis of some new substituted [3-(3-chloro-4-fluorophenyl)-2-oxo-3,4-dihydro-2H-2lambda(5)-benzo[e][1,3,2]oxazaphosphinin-2-yl]-(aryl/alkyl)methanols (7a-k) based on the Pudovick reaction was accomplished in the presence of niobium pentoxide (Nb(2)O(5)) without using an external chiral ligand. Nb(2)O(5) appears to form the metal complex intermediate catalyst system (6) by reacting with 3-(3-chloro-4-fluoro-phenyl)-3,4-dihydrobenzo[e][1,3,2]oxazaphosphinine-2-oxide (4), which not only directs the Pudovick addition reactions of aldehyde but also increases the yields and purity of the products. These compounds exhibited a lethal effect on whip smut of sugarcane and were degraded in the environment in the presence of bacteria and fungi to nontoxic phosphate residues that act as possible plant nutrients. Thus, a new class of benzooxazaphosphininyl methanol derivatives that act in synergy both as antipathogens and as plant nutrients in the environment have been discovered.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Niobium(V) oxide, 99.99% trace metals basis
Sigma-Aldrich
Niobium(V) oxide, −325 mesh, 99.9% trace metals basis