Benzoxazoles as novel herbicidal agents.
benzoxazoles
cucumber
herbicide
onion
sorghum
synthesis
tomato
Journal
Pest management science
ISSN: 1526-4998
Titre abrégé: Pest Manag Sci
Pays: England
ID NLM: 100898744
Informations de publication
Date de publication:
Jan 2019
Jan 2019
Historique:
received:
29
03
2018
revised:
22
05
2018
accepted:
04
06
2018
pubmed:
10
6
2018
medline:
3
1
2019
entrez:
10
6
2018
Statut:
ppublish
Résumé
Despite the need to develop new herbicides with different modes of action, due to weed resistance, many important classes of compounds have been studied poorly for this purpose. Benzoxazoles are considered privileged structures because of their biological activities, but their phytotoxic activities have not received a lot of attention until now. Double vinylic substitution reactions were carried out to furnish four 2-nitromethylbenzoxazoles and one oxazolidine. Benzoxazol-2-ylmethanamine was obtained by reduction of compound 3a. These compounds were evaluated for their phytotoxicity in Allium cepa (onion), Solanum lycopersicum (tomato), Cucumis sativus (cucumber) and Sorghum bicolor (sorghum). Comparison with oxazolidine analogue allowed us to understand that the benzoxazolic structure is very important for the herbicidal activity. All the synthesized compounds exhibited biological activity on seed germination. The four 2-nitromethylbenzoxazoles showed phytotoxic activity and the 5-chloro-2-(nitromethyl)benzo[d]oxazole (3b) exhibited higher inhibition than the commercial herbicide against all four plant species tested. © 2018 Society of Chemical Industry.
Sections du résumé
BACKGROUND
BACKGROUND
Despite the need to develop new herbicides with different modes of action, due to weed resistance, many important classes of compounds have been studied poorly for this purpose. Benzoxazoles are considered privileged structures because of their biological activities, but their phytotoxic activities have not received a lot of attention until now.
RESULTS
RESULTS
Double vinylic substitution reactions were carried out to furnish four 2-nitromethylbenzoxazoles and one oxazolidine. Benzoxazol-2-ylmethanamine was obtained by reduction of compound 3a. These compounds were evaluated for their phytotoxicity in Allium cepa (onion), Solanum lycopersicum (tomato), Cucumis sativus (cucumber) and Sorghum bicolor (sorghum). Comparison with oxazolidine analogue allowed us to understand that the benzoxazolic structure is very important for the herbicidal activity.
CONCLUSION
CONCLUSIONS
All the synthesized compounds exhibited biological activity on seed germination. The four 2-nitromethylbenzoxazoles showed phytotoxic activity and the 5-chloro-2-(nitromethyl)benzo[d]oxazole (3b) exhibited higher inhibition than the commercial herbicide against all four plant species tested. © 2018 Society of Chemical Industry.
Substances chimiques
Benzoxazoles
0
Herbicides
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
262-269Subventions
Organisme : PROPPI-UFF
Organisme : RQ-MG
Organisme : FAPEMIG
Organisme : FAPERJ
Organisme : CNPq
Informations de copyright
© 2018 Society of Chemical Industry.