Synthesis and herbicidal activity of new imidazolidinedione derivatives

Citation
T. Yano et al., Synthesis and herbicidal activity of new imidazolidinedione derivatives, J PESTIC S, 26(1), 2001, pp. 67-75
Citations number
17
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Entomology/Pest Control
Journal title
JOURNAL OF PESTICIDE SCIENCE
ISSN journal
0385-1559 → ACNP
Volume
26
Issue
1
Year of publication
2001
Pages
67 - 75
Database
ISI
SICI code
0385-1559(2001)26:1<67:SAHAON>2.0.ZU;2-Q
Abstract
A series of new 3-(5-alkoxy-2,4-dihalophenyl)-5-alkylidene-1,3-imidazolidin e-2,4-dione derivatives was synthesized and their herbicidal activities aga inst various weeds were examined. The herbicidal activities varied with the substituents on the benzene ring and the compounds having a 5-alkynyloxy-4 -chloro-2-fluorophenyl group exhibited relatively higher herbicidal activit ies. In the case of monocyclic imidazolidinedione derivatives, introduction of an isopropylidene group at the 5-position and a lower alkyl group at th e I-position of the imidazolidinedione ring was most effective in enhancing the activity. In the case of bicyclic imidazolidinedione derivatives, 5,6- dihydroimidazo [1,5-a] pyridine derivatives gave a higher selectivity than tetrahydroimidazo[1,5-a] pyridine derivatives, therefore, it was thought th at the presence of a double bond was important for the crop safety. Among t he compounds synthesized, a bicyclic imidazolidinedione compound, 2-(4-chlo ro-2-fluoro-5-propargyloxyphenyl)-5,6-dihydroimidazo [1,5-a]pyridine-1,3 [2 H,7H]-dione is considered to be the most promising candidate as a corn herb icide.