The discovery of pyridalyl: a novel insecticidal agent for controlling lepidopterous pests

Abstract

Synthesis of analogues of two compounds with known insecticidal activity, both of which contain a 3,3-dichloro-2-propenyloxy group, produced 2-(trifluoromethyl)-4-phenoxyphenyl 3,3-dichloro-2-propenyl ether, which had weak activity against lepidopterous larvae. Structural modifications around this lead compound led to the development of pyridalyl [Pleo, S-1812; 2,6-dichloro-4-(3,3-dichloroallyloxy)phenyl 3-[5-(trifluoromethyl)-2-pyridyloxy]propyl ether], which belongs to a new class of insecticides. Pyridalyl gives very good control of various lepidopterous and thysanopterous pests on cotton and vegetables, without phytotoxicity. It controls populations of Heliothis virescens F and Plutella xylostella (L) which are resistant to various currently used insecticides. It also produces unique insecticidal symptoms, so it may have a different mode of action from other existing insecticides. Pyridalyl is also less harmful than existing insecticides to various beneficial arthropods, so it should provide an important tool in IPM and insecticidal management programmes for the control of lepidopterous and thysanopterous pests. The first market introduction is expected in Japan and some Asian countries in the years between 2004 and 2005.

Effects of Pyridalyl, a Novel Insecticidal Agent, on Cultured Sf9 Cells

“…1), which is highly active against lepidopterous larvae. [1][2][3][4] In a previous study, we observed that Spodoptera litura larvae treated with lethal dosages of pyridalyl lost their vigor, mobile activity and body elasticity, dying within several hours of treatment. In contrast, the topical application of pyridalyl at sub-lethal dosages induced a unique symptom similar to a burn scar at the treated site.…”

Design, Synthesis and Bioactivities of Novel Dichloro-Allyloxy-Phenol-Containing Pyrazole Oxime Derivatives

“…Pyridalyl (Figure 1), a novel dichloro-allyloxy-phenol insecticide, was discovered by Sumitomo Chemical Co., Ltd. and marketed in 2004 [12]. It displays good insecticidal activity against different lepidopterous pests on various crops such as cotton and vegetables, and exhibits no cross-resistance with other existing insecticides including synthetic pyrethroids, organic phosphates, benzoylureas and nicotinic insecticides [13,14].…”

Residue patterns of indoxacarb and pyridalyl in treated cauliflower

“…It is also effective on pests that have developed a resistance to existing insecticides, indicating a different mode of action from any other conventional insecticide [5,6].…”