Chemical Structure of Neonicotinoids

As a result of the efficient MoA given by the nAChR as target there is no cross-resistance to conventional long-established insecticide classes, such as chlorinated hydrocarbons, organophosphates, carbamates, pyrethroids and several other chemical classes of insecticides used to control insect pests on major crops. Since the introduction of imidacloprid in 1991, neonicotinoids represent a fairly new class of chemistry classified in the same MoA class (nAChR agonists, group 4A) by IRAC.1

Abbreviation Cyclic Chemistry

Figure 4.1 Commercial neonicotinoid insecticides: ring systems (a-c) versus non-cyclic neonicotinoids (d-g). Abbreviations: CPM (chloropyridyl), CTM (chlorothiazolyl) and TFM (tetrahydrofuryl), * mixture or (R)- and (S)-enantiomers.

Today, seven neonicotinoid insecticides are on the market: three cyclic compounds [neonicotinoids with five-membered ring systems, such as imida-cloprid8,9 and thiacloprid (Bayer CropScience),10 and the six-membered ring neonicotinoid thiamethoxam (Syngenta)]11 and four non-cyclic compounds [nitenpyram (Sumitomo Chemical Takeda Agro Company),12 acetamiprid (Nippon Soda),13 clothianidin (Sumitomo Chemical Takeda Agro Company/ Bayer CropScience)14 and dinotefuran (Mitsui Chemicals)].15

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