Cyclic Ketoenols – Acaricides and Insecticides with a Novel Mode of Action

Abstract

Modern crop protection industry puts great efforts into the investigation and development of pesticides (insecticides, acaricides) with a novel mode of action, primarily because of increasingly important problem of resistance of pest organisms to pesticides. Resistance of many pest arthropod species (insects and mites) to insecticides and/or acaricides became a global phenomenon in the last decades. Therefore, pest management heavily relies on constant introduction of novel active ingredients in use, i.e. on the alternative use of a number of compounds with different modes of action in order to save the longevity of newly developed products. Among pest arthropods, according to the potential for resistance development and a number of documented cases, spider mites (Acari: Tetranychidae), especially species Tetranychus urticae and Panonychus ulmi, as well as certain species of whiteflies and leaf aphids (Homoptra: Aleyrodidae, Aphididae) stand out. In 2002, the company Bayer CropScience introduced spirodiclofen, a tetronic acid derivative and the first cyclic ketoenol, acaricide with a wide spectrum and a novel mode of action – inhibition of acetyl-CoA-carboxylase. Soon after, spiromesifen was introduced, also a derivative of tetronic acid, acaricide and insecticide intended for control of phytophagus mites and whiteflies. Spirotetramat, a tetramic acid derivative, and the third member of the ketoenol group, was recently commercialised as an insecticide efficient against whiteflies, leaf aphids and other harmful Homoptera. In this paper are presented the most significant properties of cyclic ketoenols, aiming at pointing to the possibilities and prospects of their use, but also to potential problems and limitations.

Moderna hemijska industrija u oblasti zaštite bilja ulaže velike napore u istraživanje i razvoj pesticida (insekticida, akaricida) novih mehanizama delovanja, pre svega zbog sve ozbiljnijeg problema rezistentnosti štetnih organizama na pesticide. Rezistentnost mnogih štetnih vrsta artropoda (insekata i grinja) na insekticide i/ili akaricide postala je poslednjih decenija globalni fenomen. Otuda se praksa zaštite bilja u velikoj meri oslanja na stalno uvođenje u primenu novih aktivnih materija, odnosno na alternativnu primenu što većeg broja jedinjenja različitih mehanizama delovanja radi produžavanja vremena upotrebe novouvedenih proizvoda. Među štetnim artropodama, po svom prirodnom potencijalu za razvoj rezistentnosti i broju dokumentovanih slučajeva izdvajaju se grinje paučinari (Acari: Tetranychidae) – posebno vrste Tetranychus urticae i Panonychus ulmi – kao i pojedine vrste leptirastih (Aleyrodidae) i lusnih vaši (Aphididae). Godine 2002, kompanija Bayer CropScience uvela je u primenu spirodiklofen, derivat tetronske kiseline i prvi ciklični ketoenol, akaricid širokog spektra i novog mehanizma delovanja – inhibicije acetil-koenzim A-karboksilaze. Ubrzo je u primenu uveden spiromesifen, takođe derivat tetronske kiseline, akaricid i insekticid namenjen suzbijanju fitofagnih grinja i leptirastih vaši. Nedavno je komercijalizovan i treći ketoenol, spirotetramat, derivat tetramske kiseline, insekticid efikasan protiv leptirastih vaši, lisnih vaši i drugih štetnih hemiptera. U ovom radu su predstavljene najznačajnije osobine cikličnih ketoenola, sa ciljem da se ukaže na mogućnosti i perspektive njihove primene, ali i na potencijalne probleme i ograničenja.