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Nicotinoid Insecticides and the Nicotinic Acetylcholine Receptor (Paperback, Softcover reprint of the original 1st ed. 1999)
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Nicotinoid Insecticides and the Nicotinic Acetylcholine Receptor (Paperback, Softcover reprint of the original 1st ed. 1999)
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Insect pest control has continuously evolved from inorganics to
botanicals, to chlo- rinated hydrocarbons, to organophosphorus
compounds and methylcarbamates, then synthetic pyrethroids and most
recently synthetic nicotinoids as the major classes. These
insecticides allowed high standards of crop protection at minimal
cost. A limitation in each new class of compounds is the selection
of resistant strains and ultimate control failures and this serves
as a driving force to discover and develop replacement compounds to
circumvent resistance and overcome problem areas. The nicotinoids
now play a critical role in meeting this need. Three generations of
chemicals are involved in the history of nicotinoid insecti- cides.
The first generation was the botanical nicotine used for at least
three centuries to control sucking insect pests but largely
replaced in the 1940s and 1950s by the more effective
organophosphorus compounds and methylcarbamates, some with systemic
properties. Synthesis programs based on nicotine as a prototype did
not yield compounds that could compete with other synthetic
insecticides. The second generation was the nitromethylene type
such as nithiazine, discovered by Shell sci- entists in a
screening/optimization program. The nitromethylenes had the
potency, selectivity, and systemic properties but lacked the field
effectiveness largely because of photolability (so close yet so far
from a major commercial product). The third generation required a
series of advances made by Bayer researchers starting from
nithiazine as the model and enhancing its photostability and
potency with a nitroimine and chloropyridyl moiety, respectively,
to give imidacloprid, the subject of much of this monograph.
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