Discovery of the Nitromethylene Heterocycle Insecticides

Kollmeyer, Willy D.; Flattum, Roger F.; Foster, James P.; Powell, James E.; Schroeder, Mark E.; Soloway, Saul

doi:10.1007/978-4-431-67933-2_3

Cited by 49 publications

(37 citation statements)

References 9 publications

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“…Adding the CP or CT substituent to nithiazine-type molecules greatly increases the insecticidal activity (Kagabu, 1997(Kagabu, , 1999Kollmeyer et al, 1999;Maienfisch et al, 1999) and the nAChR binding affinity relative to those of IMI (present study). In Myzus and Drosophila CP and CT analogues compete for the same site based on Scatchard analyses with clothianidin and desmethylthiamethoxam in [ 3 H]IMI binding assays (present study).…”

Section: First-generation (Cp) and Second-generation (Ct) Neonicotinomentioning

confidence: 63%

Insect Nicotinic Acetylcholine Receptor: Conserved Neonicotinoid Specificity of [³H]Imidacloprid Binding Site

Zhang

Kayser

Maienfisch

et al. 2000

Journal of Neurochemistry

144

121

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Abstract:The insect nicotinic acetylcholine receptor (nAChR) is a major target for insecticide action. The rapidly expanding use of neonicotinoid insecticides of varied structures makes it increasingly important to define similarities and differences in their action, particularly for the first-generation chloropyridinyl compounds versus the second-generation chlorothiazolyl derivatives. We have shown with Musca domestica that a convenient and relevant determination of the neonicotinoid insecticide target is a binding site assay with. This study uses membranes from the aphids Myzus persicae and Aphis craccivora and from heads of the flies Drosophila melanogaster and Musca domestica to characterize the [ 3 H]IMI binding sites relative to their number and possible species variation in structure-activity relationships. With emphasis on commercial neonicotinoids, six potent chloropyridinyl compounds are compared with the corresponding six chlorothiazolyl analogues (syntheses are given for chemicals prepared differently than previously described). The preference for chloropyridinyl versus chlorothiazolyl is not dependent on the insect species examined but instead on other structural features of the molecule. The chlorothiazolyl substituent generally confers higher potency in the clothianidin and desmethylthiamethoxam series and the chloropyridinyl moiety in the imidacloprid, thiacloprid, acetamiprid, and nitenpyram series. Two chlorothiazolyl compounds compete directly with the chloropyridinyl [ 3 H]IMI for the same binding sites in Myzus and Drosophila membranes. This study shows conserved neonicotinoid specificity of the [ 3 H]IMI binding site in each of the four insect species examined.

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Section: First-generation (Cp) and Second-generation (Ct) Neonicotinomentioning

confidence: 63%

Insect Nicotinic Acetylcholine Receptor: Conserved Neonicotinoid Specificity of [³H]Imidacloprid Binding Site

Zhang

Kayser

Maienfisch

et al. 2000

Journal of Neurochemistry

144

121

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“…3), suggesting that a combination of two stresses impairs the insect's ability to cope with virus accumulation. The insecticides used in this study are neonicotinoids, a class of neuroactive insecticides that specifically bind to acetylcholine receptors in the insect's central nervous system, leading to overstimulation and blocked activity (50). Aside from general stress, this class of insecticides activates molecular responses, such as detoxification responses of P450 enzymes (51), and it has been shown to accelerate combination on whitefly fecundity.…”

Section: Discussionmentioning

confidence: 99%

Replication of Tomato Yellow Leaf Curl Virus in Its Whitefly Vector, Bemisia tabaci

Pakkianathan

Kontsedalov

Lebedev

et al. 2015

J Virol

100

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Tomato yellow leaf curl virus (TYLCV) is a begomovirus transmitted exclusively by the whitefly Bemisia tabaci in a persistent, circulative manner. Replication of TYLCV in its vector remains controversial, and thus far, the virus has been considered to be nonpropagative. Following 8 h of acquisition on TYLCV-infected tomato plants or purified virions and then transfer to non-TYLCV-host cotton plants, the amounts of virus inside whitefly adults significantly increased (>2-fold) during the first few days and then continuously decreased, as measured by the amounts of genes on both virus DNA strands. Reported alterations in insect immune and defense responses upon virus retention led us to hypothesize a role for the immune response in suppressing virus replication. After virus acquisition, stress conditions were imposed on whiteflies, and the levels of three viral gene sequences were measured over time. When whiteflies were exposed to TYLCV and treatment with two different pesticides, the virus levels continuously increased. Upon exposure to heat stress, the virus levels gradually decreased, without any initial accumulation. Switching of whiteflies between pesticide, heat stress, and control treatments caused fluctuating increases and decreases in virus levels. Fluorescence in situ hybridization analysis confirmed these results and showed virus signals inside midgut epithelial cell nuclei. Combining the pesticide and heat treatments with virus acquisition had significant effects on fecundity. Altogether, our results demonstrate for the first time that a single-stranded DNA plant virus can replicate in its hemipteran vector. IMPORTANCEPlant viruses in agricultural crops are of great concern worldwide. Many of them are transmitted from infected to healthy plants by insects. Persistently transmitted viruses often have a complex association with their vectors; however, most are believed not to replicate within these vectors. Such replication is important, as it contributes to the virus's spread and can impact vector biology. Tomato yellow leaf curl virus (TYLCV) is a devastating begomovirus that infects tomatoes. It is persistently transmitted by the whitefly Bemisia tabaci but is believed not to replicate in the insect. To demonstrate that TYLCV is, in fact, propagative (i.e., it replicates in its insect host), we hypothesized that insect defenses play a role in suppressing virus replication. We thus exposed whitefly to pesticide and heat stress conditions to manipulate its physiology, and we showed that under such conditions, the virus is able to replicate and significantly influence the insect's fecundity. (Begomovirus, Geminiviridae) is the name given to a complex of single-stranded DNA (ssDNA) plant viruses that cause tremendous losses of tomato crops worldwide (1). Begomoviruses are transmitted by several biotypes of the whitefly Bemisia tabaci (2, 3). Begomoviruses have either a single (monopartite) or two (bipartite) circular ssDNA genomes of ϳ2,700 nucleotides each. Each genome is encapsidated in an ϳ25...

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“…Nithiazine (Fig. 4), developed by Shell in the late 1970s, is a potent insecticide but was not used extensively as a commercial product, due in part to its photoinstability (Kollmeyer et al 1999). Nevertheless, nithiazine was a lead compound for the development of novel neonicotinoid insecticides (Kagabu 1999;Nauen et al 2001).…”

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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Discovery of the Nitromethylene Heterocycle Insecticides

Cited by 49 publications

References 9 publications

Insect Nicotinic Acetylcholine Receptor: Conserved Neonicotinoid Specificity of [³H]Imidacloprid Binding Site

Insect Nicotinic Acetylcholine Receptor: Conserved Neonicotinoid Specificity of [³H]Imidacloprid Binding Site

Replication of Tomato Yellow Leaf Curl Virus in Its Whitefly Vector, Bemisia tabaci

Nicotinic acetylcholine receptors: targets for commercially important insecticides

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Discovery of the Nitromethylene Heterocycle Insecticides

Cited by 49 publications

References 9 publications

Insect Nicotinic Acetylcholine Receptor: Conserved Neonicotinoid Specificity of [3H]Imidacloprid Binding Site

Insect Nicotinic Acetylcholine Receptor: Conserved Neonicotinoid Specificity of [3H]Imidacloprid Binding Site

Replication of Tomato Yellow Leaf Curl Virus in Its Whitefly Vector, Bemisia tabaci

Nicotinic acetylcholine receptors: targets for commercially important insecticides

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Product

Resources

About

Insect Nicotinic Acetylcholine Receptor: Conserved Neonicotinoid Specificity of [³H]Imidacloprid Binding Site

Insect Nicotinic Acetylcholine Receptor: Conserved Neonicotinoid Specificity of [³H]Imidacloprid Binding Site