Thiamethoxam is a neonicotinoid precursor converted to clothianidin in insects and plants

Nauen, Ralf; Ebbinghaus‐Kintscher, Ulrich; Salgado, Vincent L.; Kaussmann, Martin

doi:10.1016/s0048-3575(03)00065-8

Cited by 413 publications

(333 citation statements)

References 19 publications

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“…It is well known that some neonicotinoids offer growers additional benefits beyond broad-spectrum insect protection. The effects are evidenced (among others) by increased root mass of treated plants (Nauen et al 2003;Cox et al 2007;Tansey et al 2008). Unfortunately, we did not find any available study which evaluates effects of seed-applied neonicotinoids on the root nodulatin of pea (Pisum sativum).…”

Section: Rootsmentioning

confidence: 96%

Differences between the effects of insecticidal seed and foliar treatments on pea leaf weevils (Sitona lineatus L.) in the field pea (Pisum sativum L.)

Seidenglanz¹,

Poslušná²,

Smékalová³

et al. 2010

Plant Prot. Sci.

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Seidenglanz M., Rotrekl J., Smýkalová I., Poslušná J., Kolařík P. (2010): Differences between the effects of insecticidal seed and foliar treatments on pea leaf weevils (Sitona lineatus L.) in the field pea (Pisum sativum L.). Plant Protect. Sci., 46: 19-27.Tested seed treatments (two doses of thiamethoxam, thiamethoxam + fludioxonil + metalaxyl-M; two doses of clothianidin + beta-cyfluthrin) showed high effects on pea leaf weevils (Sitona lineatus L.) which approved relatively long-lasting and sufficient protection of several bottom nodes of stipules simultaneously. The effects of foliar treatments (chlorpyrifos + cypermethrin; acetamiprid, lambda-cyhalothrin) sometimes were evident only on the node which was determined as the youngest node at the time of spraying. The effects of the compared seed and foliar treatments on the reduction of S. lineauts larvae numbers on roots were not proven as positive. It is possible to conclude that the foliar application had no real effect in this sense at all. However, positive significant effects of thiamethoxam and clothianidin + beta-cyfluthrin on root nodulation in general were recorded. Especially higher doses of the seed treatments increased overall nodulation from 43% till 363%.

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Section: Rootsmentioning

confidence: 96%

Differences between the effects of insecticidal seed and foliar treatments on pea leaf weevils (Sitona lineatus L.) in the field pea (Pisum sativum L.)

Seidenglanz¹,

Poslušná²,

Smékalová³

et al. 2010

Plant Prot. Sci.

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“…It is known that the extent of SA-responsive transcriptional changes varies depending upon the concentration of SA or SA analog, the timeframe for analyzing the response, and the assay system (10,12). Therefore, to determine whether the IMI-exclusive gene set of 3,508 is also associated with SA-dependent responses not identified in the parallel SA treatment, we compared our findings with those characterizing the early response to SA (13), obtained after treatment with the functional SA-analog S-methyl benzo [1,2,3] thiadiazole-7-carbothioate (BTH) (14), or identified as SAdependent in response to infection with powdery mildew using the Arabidopsis SA biosynthetic mutant ics1 (15). Thirty percent of the IMI-exclusive set were previously associated with SAdependent responses as ascertained by these studies.…”

Section: Neonicotinoids Induce Global Transcriptional Response Similamentioning

confidence: 99%

“…Imidacloprid (IMI), with a chloropyridinyl (Cl-pyr) substituent, is the most important neonicotinoid, used primarily as a systemic compound absorbed and translocated by plants to control sucking insect pests (1). The neonicotinoids clothianidin (2) (CLO) and a metabolic precursor, the oxadiazine compound thiamethoxam (3,4), which have chlorothiazolyl (Cl-thia) substituents, are also extensively used as systemic insecticides in plants. The neonicotinoids IMI and CLO are oxidatively cleaved in planta to 6-chloropyridinyl-3-carboxylic acid (CPA) and 2-chlorothiazolyl-5-carboxylic acid (CTA), respectively, among other metabolites (5).…”

mentioning

confidence: 99%

Neonicotinoid insecticides induce salicylate-associated plant defense responses

Ford

Casida²,

Chandran³

et al. 2010

Proc. Natl. Acad. Sci. U.S.A.

167

136

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Neonicotinoid insecticides control crop pests based on their action as agonists at the insect nicotinic acetylcholine receptor, which accepts chloropyridinyl-and chlorothiazolyl-analogs almost equally well. In some cases, these compounds have also been reported to enhance plant vigor and (a)biotic stress tolerance, independent of their insecticidal function. However, this mode of action has not been defined. Using Arabidopsis thaliana, we show that the neonicotinoid compounds, imidacloprid (IMI) and clothianidin (CLO), via their 6-chloropyridinyl-3-carboxylic acid and 2-chlorothiazolyl-5-carboxylic acid metabolites, respectively, induce salicylic acid (SA)-associated plant responses. SA is a phytohormone best known for its role in plant defense against pathogens and as an inducer of systemic acquired resistance; however, it can also modulate abiotic stress responses. These neonicotinoids effect a similar global transcriptional response to that of SA, including genes involved in (a)biotic stress response. Furthermore, similar to SA, IMI and CLO induce systemic acquired resistance, resulting in reduced growth of a powdery mildew pathogen. The action of CLO induces the endogenous synthesis of SA via the SA biosynthetic enzyme ICS1, with ICS1 required for CLO-induced accumulation of SA, expression of the SA marker PR1, and fully enhanced resistance to powdery mildew. In contrast, the action of IMI does not induce endogenous synthesis of SA. Instead, IMI is further bioactivated to 6-chloro-2-hydroxypyridinyl-3-carboxylic acid, which is shown here to be a potent inducer of PR1 and inhibitor of SA-sensitive enzymes. Thus, via different mechanisms, these chloropyridinyl-and chlorothiazolylneonicotinoids induce SA responses associated with enhanced stress tolerance.N eonicotinoids are the newest of the three major classes of insecticides, which also include the organophosphorus compounds and pyrethroids. Imidacloprid (IMI), with a chloropyridinyl (Cl-pyr) substituent, is the most important neonicotinoid, used primarily as a systemic compound absorbed and translocated by plants to control sucking insect pests (1). The neonicotinoids clothianidin (2) (CLO) and a metabolic precursor, the oxadiazine compound thiamethoxam (3, 4), which have chlorothiazolyl (Cl-thia) substituents, are also extensively used as systemic insecticides in plants. The neonicotinoids IMI and CLO are oxidatively cleaved in planta to 6-chloropyridinyl-3-carboxylic acid (CPA) and 2-chlorothiazolyl-5-carboxylic acid (CTA), respectively, among other metabolites (5). In studying metabolism of neonicotinoids in spinach (5) under insect-free conditions, we sometimes observed enhancement of foliage growth, plant vigor, and drought-tolerance. These remarkable effects of neonicotinoids directly on plants, independent of controlling insect pests, have also been noted by many researchers and farmers and documented in both research publications and patent disclosures, especially for IMI (6-8) and the CLO precursor, thiamethoxam (9). In addition, treatment with IMI...

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“…Indeed, it has been suggested that in insects, cleavage of the oxadiazine residue generates clothianidin and that TMX is a pro-drug of clothianidin. 101,102) However, the rate and degree of clothianidin production in vivo from TMX treated insects does not correlate with its rapid toxicological symptoms, suggesting that TMX must be neuroactive in its own right. 72 71,104,105) demonstrating that the oxadiazine residue itself does not select for different nAChR forms.…”

Section: Thiamethoxammentioning

confidence: 99%

The invertebrate pharmacology of insecticides acting at nicotinic acetylcholine receptors

Crossthwaite

Bigot

Camblin

et al. 2017

Journal of Pesticide Science

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The nicotinic acetylcholine receptor (nAChR) is a ligand-gated ion channel composed of 5 protein subunits arranged around a central cation selective pore. Several classes of natural and synthetic insecticides mediate their effect through interacting at nAChRs. This review examines the basic pharmacology of the neonicotinoids and related chemistry, with an emphasis on sapfeeding insects from the order Hemiptera, the principle pest target for such insecticides. Although the receptor subunit stoichiometry for endogenous invertebrate nAChRs is unknown, there is clear evidence for the existence of distinct neonicotinoid binding sites in native insect preparations, which reflects the predicted wide repertoire of nAChRs and differing pharmacology within this insecticide class. The spinosyns are principally used to control chewing pests such as Lepidoptera, whilst nereistoxin analogues are used on pests of rice and vegetables through contact and systemic action, the pharmacology of both these insecticides is unique and different to that of the neonicotinoids.

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Thiamethoxam is a neonicotinoid precursor converted to clothianidin in insects and plants

Cited by 413 publications

References 19 publications

Differences between the effects of insecticidal seed and foliar treatments on pea leaf weevils (Sitona lineatus L.) in the field pea (Pisum sativum L.)

Differences between the effects of insecticidal seed and foliar treatments on pea leaf weevils (Sitona lineatus L.) in the field pea (Pisum sativum L.)

Neonicotinoid insecticides induce salicylate-associated plant defense responses

The invertebrate pharmacology of insecticides acting at nicotinic acetylcholine receptors

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