Spirodiclofen and Spiromesifen – Novel Acaricidal and Insecticidal Tetronic Acid Derivatives with a New Mode of Action

Abstract

The broad spectrum acaricides spirodiclofen (BAJ2740, trade name: Envidor®) and spiromesifen (BSN2060, trade name: Oberon®) with an additional excellent activity against whiteflies, both belong to the new chemical class of tetronic acid derivatives discovered at Bayer CropScience during the 1990s. The discovery process starting from herbicidal PPO (protoporphyrinogen oxidase) chemistry, the synthetic routes leading to the products, and some insight into process development of central intermediates is given. Spirodiclofen and spiromesifen have a new mode of action (interference with lipid biosynthesis), show no cross-resistance to any resistant mite or whitefly field population and are therefore valuable tools for resistance management.

Persistence and Dissipation Kinetics of Spiromesifen in Chili and Cotton

“…at very low dosage of 100-150 g a.i. ha −1 (Bretschneider, Buchhol, Fischer, & Nauen, 2003). It is a lipid biosynthesis inhibitor (Dekeyser, 2005) and owing to its unique structure it is a useful tool in resistance management in many cropping systems including cotton, tea, vegetables, fruits and ornamentals (Nauen et al, 2002).…”

Management of Bemisia tabaci Whiteflies

“…It acts as an inhibitor of lipid biosynthesis that interferes with development of the egg and immature stages and reduces adult female fecundity (Bretschneider et al 2003;). Spiromesifen acts effectively on the egg and early nymphal stages of B. tabaci (both biotypes B and Q) but adults and late nymphal stages are only moderately affected (Prabhaker et al 2008;Kontsedalov et al 2009).…”

Spirodiclofen Analogues as Potential Lipid Biosynthesis Inhibitors: A Convenient Synthesis, Biological Evaluation, and Structure-Activity Relationship

“…27,28 Meanwhile, this synthetic route leads to a convenient access to spirodiclofen analogues compared the reported traditional methods, [29][30][31][32][33][34] which may be propitious to large scale production. The structures of all newly synthesized compounds were characterized as 3-(substituted-phenyl)-1-oxaspiro [4.5]dec-3-en-2-one derivatives 6a-t on the basis of satisfactory analytical and spectral data including 1 H NMR, 13 C NMR and ESI-MS. Biological activity evaluation.…”

“…at all stages of growth and has a unique mode of action differed from other acaricides, 7,8 which interferes the lipid biosynthesis and blocks the enzyme acetyl-coenzyme A carboxylase that allows mites to form important fatty acids. [9][10][11][12] Bayer Company has already developed the three tetronic acids analogues as acaricides and insecticides named spirodiclofen, 5,6 spiromesifen, [13][14][15][16] and spirotetramat (Figure 1), [17][18][19][20][21] respectively. However, both the mode of action and the structure of receptor for these compounds are not yet sure, and the systemic and detailed structure-activity relationships are unreported, which restrict the creation and optimization for these kinds of novel acaricides to some extent.…”