Improved microwave-mediated synthesis of 3-(3-aryl-1,2,4-oxadiazol-5-yl)propionic acids and their larvicidal and fungal growth inhibitory properties.
The synthesis of 3-(3-aryl-1,2,4-oxadiazol-5-yl)propionic acids from arylamidoximes and succinic anhydride under focused microwave irradiation conditions is described. The new synthetic method furnished the desired products in 2-3 min and good yields. Furthermore, the previously complicated purification procedure has been simplified in a manner which is quick, eco-friendly and cost-effective. Larvicidal bioassay and fungal growth inhibitory tests were performed using several 3-(3-aryl-1,2,4-oxadiazol-5-yl)propionic acids. These acids presented strong larvicidal activity against L4 larvae of Aedes aegypti. The results suggest that larvicidal activity might be correlated with the presence of electron-withdrawing substituents in the para position of the phenyl ring except the fluorine atom. The alterations observed in the larvae spiracular valves of the siphon and anal papillae by 1,2,4-oxadiazoles in the larvicidal bioassay are responsible for larvae's death. Furthermore, all acids inhibited the fungal growth of five different types of fungi, viz., Fusarium solani, F. oxysporum, F. moniliforme, F. decemcellulare and F. lateritium in a preliminary evaluation. Both of these activities are being disclosed for the first time for 1,2,4-oxadiazole-5-yl ring linked at C-3 of propionic acid.
Neves Filho
Ricardo Antonio Wanderley
RA
Departamento de Química Fundamental, Universidade Federal de Pernambuco, Recife, PE, Brazil.
da Silva
Cecília Aguiar
CA
da Silva
Clécia Sipriano Borges
CS
Brustein
Vanessa Passos
VP
do Amaral Ferraz Navarro
Daniela Maria
DM
dos Santos
Fábio André Brayner
FA
Alves
Luiz Carlos
LC
dos Santos Cavalcanti
Marília Gabriela
MG
Srivastava
Rajendra Mohan
RM
das Graças Carneiro-Da-Cunha
Maria
M
D000330:Aedes / Q000187:drug effects; D000818:Animals; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D005670:Fusarium / Q000187:drug effects* / Q000254:growth & development; D007306:Insecticides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D007814:Larva / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D008872:Microwaves; D015394:Molecular Structure; D010069:Oxadiazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D011422:Propionates / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000935:Antifungal Agents; D007306:Insecticides; D010069:Oxadiazoles; D011422:Propionates