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Synthesis and insecticidal/acaricidal activity of novel 3‐(2,4,6‐trisubstituted phenyl)uracil derivatives
Author(s) -
Yagi Kazuo,
Akimoto Kazuhiko,
Mimori Norihiko,
Miyake Toshiro,
Kudo Masaki,
Arai Kazutaka,
Ishii Shigeru
Publication year - 2000
Publication title -
pest management science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.296
H-Index - 125
eISSN - 1526-4998
pISSN - 1526-498X
DOI - 10.1002/(sici)1526-4998(200001)56:1<65::aid-ps90>3.0.co;2-s
Subject(s) - uracil , substituent , ring (chemistry) , chemistry , stereochemistry , tetranychus urticae , polar effect , medicinal chemistry , organic chemistry , biology , biochemistry , pest analysis , dna , botany
A series of novel 3‐(2,4,6‐trisubstituted phenyl)uracil derivatives has been synthesised and assayed for insecticidal/acaricidal activity. The assay indicated certain requirements for optimal insecticidal activity, which can be summarised as follows: (a) the substituents on the phenyl ring should possess hydrophobicity and electron‐withdrawing properties, and the sum of their volumes determines the level of activity; (b) the substituent at the 6‐position on the uracil ring should also possess electron‐withdrawing properties and hydrophobicity, together with the correct volume; (c) the 1‐position on the uracil ring should be unsubstituted for activity against Nephotettix cincticeps and Epilachna vigintioctopunctata , but substituents with length C3 to C4 may be optimal for activity against Tetranychus urticae ; (d) certain substituents at the 5‐position of the uracil ring give activity against E vigintioctopunctata and T urticae , but not against N cincticeps ; (e) a thiocarbonyl group at the 2‐position of the uracil ring is less effective than a carbonyl group. Of the compounds assayed, 3‐(2,6‐dichloro‐4‐trifluoromethylphenyl)‐6‐trifluoromethyluracil showed high activity against all the species assayed. © 2000 Society of Chemical Industry