Nitromethylene Heterocycles as Insecticides

Soloway, S. B.; Henry, A.; Kollmeyer, Willy D.; Padgett, W. M.; Powell, J.E.; Roman, Steven; Tieman, Charles H.; Corey, R. A.; Horne, C. A.

doi:10.1007/978-1-4615-8834-4_12

Cited by 40 publications

(19 citation statements)

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“…In the 1970s, a group of synthetic nitromethylene compounds was identified which displayed potent insecticidal activity (Soloway et al 1978) and which acted as nAChR agonists (Bai et al 1991;Zwart et al 1992Zwart et al , 1994Buckingham et al 1995). Nithiazine (Fig.…”

Section: Neonicotinoid Insecticidesmentioning

confidence: 99%

Nicotinic acetylcholine receptors: targets for commercially important insecticides

2007

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Nicotinic acetylcholine receptors (nAChRs) are major excitatory neurotransmitter receptors in both vertebrates and invertebrates. In insects, nAChRs are the target site for several naturally occurring and synthetic compounds that exhibit potent insecticidal activity. Several compounds isolated from plants are potent agonists or antagonists of nAChRs, suggesting that these may have evolved as a defence mechanism against insects and other herbivores. Nicotine, isolated from the tobacco plant, has insecticidal activity and has been used extensively as a commercial insecticide. Spinosad, a naturally occurring mixture of two macrocyclic lactones isolated from the microorganism Saccharopolyspora spinosa, acts upon nAChRs and has been developed as a commercial insecticide. Since the early 1990s, one of the most widely used and rapidly growing classes of insecticides has been the neonicotinoids. Neonicotinoid insecticides are potent selective agonists of insect nAChRs and are used extensively in both crop protection and animal health applications. As with other classes of insecticides, there is growing evidence for the evolution of resistance to insecticides that act on nAChRs.

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Section: Neonicotinoid Insecticidesmentioning

confidence: 99%

Nicotinic acetylcholine receptors: targets for commercially important insecticides

2007

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“…Increased knowledge of the MOA of compounds has certainly led to more strategic approaches. Neonicotinoids such as imidacloprid arose from structure activity studies on 3-Pyridylmethylamine (Tomizawa and Casida, 2003) and nithiazine, a compound previously found to be a highly potent insecticide, but unfortunately not stable enough for crop use due to photo-instability (Soloway et al, 1979). Other neonicotinoids were developed again through comparison of different side-chain groups and their insecticidal activity.…”

Section: Enabling the Insecticide Design Processmentioning

confidence: 99%

The biology of insecticidal activity and resistance

Perry

Batterham

Daborn

2011

Insect Biochemistry and Molecular Biology

168

139

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“…However, insecticidally active naturally occurring organophosphorus compounds were discovered decades later from a microbe ( Steptomyces ) and marine sponge that could have been models for the organophosphate insecticides. Likewise, the neonicotinoids resulted from the evolution of an initial chemical hit that first led to nithiazine and then to imidacloprid . In retrospect, nicotine or epibatidine are potential models for the neonicotinoids.…”

Section: Insecticidesmentioning

confidence: 99%

Natural products, their derivatives, mimics and synthetic equivalents: role in agrochemical discovery

Sparks¹,

Hahn²,

Garizi³

2016

Pest Management Science

182

149

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Natural products (NPs) have a long history as a source of, and inspiration for, novel agrochemicals. Many of the existing herbicides, fungicides, and insecticides have their origins in a wide range of NPs from a variety of sources. Owing to the changing needs of agriculture, shifts in pest spectrum, development of resistance, and evolving regulatory requirements, the need for new agrochemical tools remains as critical as ever. As such, NPs continue to be an important source of models and templates for the development of new agrochemicals, demonstrated by the fact that NP models exist for many of the pest control agents that were discovered by other means. Interestingly, there appear to be distinct differences in the success of different NP sources for different pesticide uses. Although a few microbial NPs have been important starting points in recent discoveries of some insecticidal agrochemicals, historically plant sources have contributed the most to the discovery of new insecticides. In contrast, fungi have been the most important NP sources for new fungicides. Like insecticides, plant-sourced NPs have made the largest contribution to herbicide discovery. Available data on 2014 global sales and numbers of compounds in each class of pesticides indicate that the overall impact of NPs to the discovery of herbicides has been relatively modest compared to the impact observed for fungicides and insecticides. However, as new sourcing and approaches to NP discovery evolve, the impact of NPs in all agrochemical arenas will continue to expand. © 2016 Society of Chemical Industry.

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Nitromethylene Heterocycles as Insecticides

Cited by 40 publications

References 0 publications

Nicotinic acetylcholine receptors: targets for commercially important insecticides

Nicotinic acetylcholine receptors: targets for commercially important insecticides

The biology of insecticidal activity and resistance

Natural products, their derivatives, mimics and synthetic equivalents: role in agrochemical discovery

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