Antifeedant and phytotoxic activity of hydroxyperezone and related molecules.
The insect antifeedant and toxic activity of hydroxyperezone (1), its derivatives 2-9, along with 3-hydroxy- (10) and 6-hydroxythymoquinone (11) were studied against Spodoptera littoralis, Leptinotarsa decemlineata, and Myzus persicae. The antifeedant tests showed that L. decemlineata was the most sensitive insect, followed by M. persicae, while S. littoralis was not deterred by compounds 1-11. Leucohydroxyperezone tetraacetate (3), oxoperezinone (6), dihydroleucoperezinone diacetate (7), 3-hydroxy- (10) and 6-hydroxythymoquinone (11) showed strong activity against L. decemlineata. 1 and 7 exhibited moderate deterrent activity against M. persicae, while 1 and dihydroleucohydroxyperezone tetraacetate (4) acted as post-ingestive antifeedants to S. littoralis. The phytotoxic activity of compounds 1-11 was also evaluated. Hydroxyperezone (1) strongly inhibited seed germination at 24 h, while the activity of 3-8 and 10 was moderate. The level of radicle growth inhibition obtained with compounds 1-5 and 8-11 was significant (< 50%).
Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional, Prolongación de Carpio y Plan de Ayala, Col. Santo Thomás, México D. F., 11340 Mexico.
Eleuterio
E
Burgueño-Tapia
Azucena
A
González-Coloma
Lucía
L
Castillo
Pedro
P
Joseph-Nathan
D000821:Animal Feed; D000818:Animals; D001042:Aphids / Q000187:drug effects*; D001066:Appetite / Q000187:drug effects; D053138:Cyclohexenes / Q000737:chemistry / Q000494:pharmacology*; D018525:Germination / Q000187:drug effects; D007306:Insecticides / Q000737:chemistry / Q000494:pharmacology*; D007814:Larva / Q000187:drug effects; D012639:Seeds / Q000187:drug effects*; D012717:Sesquiterpenes / Q000737:chemistry / Q000494:pharmacology*; D018411:Spodoptera / Q000187:drug effects*; D013329:Structure-Activity Relationship
D053138:Cyclohexenes; D007306:Insecticides; D012717:Sesquiterpenes; C061612:hydroxyperezone