Thiamethoxam

Last updated
Thiamethoxam
Thiamethoxam E isomer.svg
E isomer
Thiamethoxam Z isomer.svg
Z isomer
Names
Preferred IUPAC name
{3-[(2-Chloro-1,3-thiazol-5-yl)methyl]-5-methyl-1,3,5-oxadiazinan-4-ylidene}nitramide
Other names
CGA293343
Identifiers
  • Compounds
  • EZ: Thiamethoxam
  • E: E-isomer
  • Z: Z-isomer
3D model (JSmol)
8555232
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.102.703 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • EZ:428-650-4
  • E:604-921-4
KEGG
PubChem CID
UNII
  • InChI=1S/C8H10ClN5O3S/c1-12-4-17-5-13(8(12)11-14(15)16)3-6-2-10-7(9)18-6/h2H,3-5H2,1H3 Yes check.svgY
    Key: NWWZPOKUUAIXIW-UHFFFAOYSA-N Yes check.svgY
  • E:InChI=1S/C8H10ClN5O3S/c1-12-4-17-5-13(8(12)11-14(15)16)3-6-2-10-7(9)18-6/h2H,3-5H2,1H3/b11-8+
    Key: NWWZPOKUUAIXIW-DHZHZOJOSA-N
  • Z:InChI=1S/C8H10ClN5O3S/c1-12-4-17-5-13(8(12)11-14(15)16)3-6-2-10-7(9)18-6/h2H,3-5H2,1H3/b11-8-
    Key: NWWZPOKUUAIXIW-FLIBITNWSA-N
  • Z:Clc1ncc(s1)CN2/C(=N\[N+]([O-])=O)N(C)COC2
Properties [1]
C8H10ClN5O3S
Molar mass 291.71 g·mol−1
Density 1.57 g/cm3
Melting point 139.1 °C (282.4 °F; 412.2 K)
4.1 g/L
log P -0.13
Hazards [2]
GHS labelling:
GHS-pictogram-exclam.svg GHS-pictogram-pollu.svg
Warning
H302, H410
P264, P270, P273, P301+P312, P330, P391, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Thiamethoxam is the ISO common name [3] for a mixture of cis-trans isomers used as a systemic insecticide of the neonicotinoid class. It has a broad spectrum of activity against many types of insects and can be used as a seed dressing.

Contents

A 2018 review by the European Food Safety Authority (EFSA) concluded that most uses of neonicotinoid pesticides such as Thiamethoxam represent a risk to wild bees and honeybees. [4] [5] In 2022 the United States Environmental Protection Agency (EPA) concluded that Thiamethoxam is likely to adversely affect 77 percent of federally listed endangered or threatened species and 81 percent of critical habitats. [6] The pesticide has been banned for all outdoor use in the entire European Union since 2018, but has a partial approval in the U.S. and other parts of the world, where it is widely used. [7] [8]

History

Thiamethoxam was developed by Ciba-Geigy (now Syngenta) in 1991 [9] and launched in 1998; [10] a patent dispute arose with Bayer which already had patents covering other neonicotinoids including imidacloprid and clothianidin. In 2002 the dispute was settled, with Syngenta paying Bayer $120 million in exchange for worldwide rights to thiamethoxam. [11]

Synthesis

Thiamethoxam was first prepared by chemists at Ciba Geigy in 1991. S-Methyl-N-nitro-isothiourea is treated with methylamine to give N-methyl nitroguanidine. This intermediate is used in a Mannich reaction with formaldehyde in formic acid to give 3-methyl-4-nitroimino-1,3,5-oxadiazinane. In the final step, the heterocycle is N-alkylated with a thiazole derivative to give a mixture of E and Z isomers of the final product. [12]

Thiamethoxam synthesis v2.svg

Mechanisms of action

Thiamethoxam is a broad-spectrum, systemic insecticide, which means it is absorbed quickly by plants and transported to all of its parts, including pollen, where it acts to deter insect feeding.[ citation needed ] An insect can absorb it in its stomach after feeding, or through direct contact, including through its tracheal system. The compound gets in the way of information transfer between nerve cells by interfering with nicotinic acetylcholine receptors in the central nervous system, and eventually paralyzes the muscles of the insects. [13] : 17 

Syngenta asserts that thiamethoxam improves plant vigor by triggering physiological reactions within the plant, which induce the expression of specific "functional proteins" involved in various stress defense mechanisms of the plant allowing it to better cope under tough growing conditions, such as "drought and heat stress leading to protein degradation, low pH, high soil salinity, free radicals from UV radiation, toxic levels of aluminum, wounding from pests, wind, hail, etc, virus attack". [14] : 16 

Toxicity

The selective toxicity of neonicotinoids like thiamethoxam for insects versus mammals is due to the higher sensitivity of insects' acetylcholine receptors. [15] The Food and Agriculture Organization (FAO) of the U.N. assessed thiamethoxam as "moderately hazardous to humans (WHO class III)", because it is harmful if swallowed. It found it to be no skin or eye irritant, and not mutagenic in any in vitro and in vivo toxicology tests. [13] : 20 

FAO described thiamethoxam as non-toxic to fish, daphnia and algae, mildly toxic for birds, highly toxic to midges and acutely toxic for bees. [13] : 20  The Globally Harmonized System of Classification and Labelling of Chemicals (GHS) classification is: "Harmful if swallowed. Very toxic to aquatic life with long lasting effects". [13] : 20  Thiamethoxam at sublethal concentrations can increase aggressiveness and cannibalism in commercially harvested shrimp such as Procambarus clarkii [16] In bioassays of aquatic organisms, fish, aquatic primary producers, mollusks, worms, and rotifers are often largely insensitive to thiamethoxam concentrations found in surface waters, but insects, such as chironomid larvae are especially susceptible. [17] [18]

Sublethal doses of thiamethoxam metabolite clothianidin (0.05–2 ng/bee) have been known to cause reduced foraging activity since at least 1999, but this was quantified in 2012 by RFID tagged honeybees. [19] Doses of equal or more than 0.5 ng/bee caused longer foraging flights. [19]

Regulation and use

United States

Thiamethoxam has been approved for use in the US as an antimicrobial pesticide, wood preservative and as a insecticide; it was first approved in 1999. [20] : 4 & 14  It is still approved for use in a wide range of crops. [21] [22]

On September 5, 2014 Syngenta petitioned the EPA to increase the legal tolerance for thiamethoxam residue in numerous crops. [23] It wanted to use thiamethoxam as a leaf spray, rather than just a seed treatment, to treat late to midseason insect pests. [24]

Thiamethoxam use in the US to 2019 Thiamethoxam use USA.png
Thiamethoxam use in the US to 2019

The estimated annual use of the compound in US agriculture is mapped by the US Geological Service and showed an increasing trend from its introduction in 2001 to 2014 when it reached 1,420,000 pounds (640,000 kg). [25] However, use from 2015 to 2019 dropped sharply following concerns about the effect of neonicotinoid chemicals on pollinating insects. [26] In May 2019, the Environmental Protection Agency revoked approval for a number of products containing thiamethoxam as part of a legal settlement. [27] However, certain formulations continue to be available. [22]

Neonicotinoids banned by the European Union

In 2012, several peer reviewed independent studies were published showing that several neonicotinoids had previously undetected routes of exposure affecting bees including through dust, pollen, and nectar; that sub-nanogram toxicity resulted in failure to return to the hive without immediate lethality, the primary symptom of colony collapse disorder; and showing environmental persistence in agricultural irrigation channels and soil. However, not all earlier studies carried out before 2014 have found significant effects. [28] These reports prompted a formal peer review by the European Food Safety Authority, which stated in January 2013 that neonicotinoids pose an unacceptably high risk to bees, and that the industry-sponsored science upon which regulatory agencies' claims of safety have relied on may be flawed and contain several data gaps not previously considered. [29] In April 2013, the European Union voted for a two-year restriction on neonicotinoid insecticides. The ban restricts the use of imidacloprid, clothianidin, and thiamethoxam on crops that attract bees. [30]

In February 2018, the European Food Safety Authority published a new report indicating that neonicotinoids pose a serious danger to both honey bees and wild bees. [31] In April 2018, the member states of the European Union decided to ban the three main neonicotinoids (clothianidin, imidacloprid and thiamethoxam) for all outdoor uses. [32]

Other countries

Thiamethoxam is approved for a wide range of agricultural, viticultural(vineyard), and horticultural uses. [13] : 17 

Emergency use

In January 2021 the UK allowed this pesticide to be used to save sugar beet plants in danger of damage from beet yellows virus which is transmitted by aphids. [33] However, due to lower levels of this disease than was expected, it was announced in March 2021 that the conditions for emergency use had not been met. The UK made similar decisions in 2022, 2023, and 2024 but in these three years the predicted incidence level of yellow virus was met, and in March 2024 it was announced that the use of Crusier SB (a pesticide which contains thiamethoxam) would be allowed for a third consecutive year. [34] [35]

Related Research Articles

<span class="mw-page-title-main">Pesticide</span> Substance used to destroy pests

Pesticides are substances that are used to control pests. They include herbicides, insecticides, nematicides, fungicides, and many others. The most common of these are herbicides, which account for approximately 50% of all pesticide use globally. Most pesticides are used as plant protection products, which in general protect plants from weeds, fungi, or insects. In general, a pesticide is a chemical or biological agent that deters, incapacitates, kills, or otherwise discourages pests. Target pests can include insects, plant pathogens, weeds, molluscs, birds, mammals, fish, nematodes (roundworms), and microbes that destroy property, cause nuisance, or spread disease, or are disease vectors. Along with these benefits, pesticides also have drawbacks, such as potential toxicity to humans and other species.

<span class="mw-page-title-main">Insecticide</span> Pesticide used against insects

Insecticides are pesticides used to kill insects. They include ovicides and larvicides used against insect eggs and larvae, respectively. Acaricides, which kill mites and ticks, are not strictly insecticides, but are usually classified together with insecticides. The major use of Insecticides is agriculture, but they are also used in home and garden, industrial buildings, vector control and control of insect parasites of animals and humans. Insecticides are claimed to be a major factor behind the increase in the 20th-century's agricultural productivity. Nearly all insecticides have the potential to significantly alter ecosystems; many are toxic to humans and/or animals; some become concentrated as they spread along the food chain.

Under United States law, pesticide misuse is considered to be the use of a pesticide in a way that violates laws regulating their use or endangers humans or the environment; many of these regulations are laid out in the Federal Insecticide, Fungicide, and Rodenticide Act (FIFRA). Pesticide misuse encompasses a range of practices, including overapplication, incorrect timing, and the use of banned substances. This global issue not only threatens environmental safety but also undermines efforts towards sustainability. The risk of pesticide pollution at a global scale necessitates a concerted effort to understand and mitigate misuse. The most common instances of pesticide misuse are applications inconsistent with the labeling, which can include the use of a material in any way not described on the label, changing dosage rates, or violating specific safety instructions. Pesticide labels have been criticized as a poor risk communication vehicle, leading some officials and researchers to question whether "misuse" is an appropriate term for what are often "unintended uses" resulting from a poor understanding of safety and application instructions. Other kinds of pesticide misuse include the sale or use of an unregistered pesticide or one whose registration has been revoked and the sale or use of an adulterated or misbranded pesticide. Under most jurisdictions, it is illegal to alter or remove pesticide labels, to sell restricted pesticides to an uncertified applicator, or to fail to maintain sales and use records of restricted pesticides.

<span class="mw-page-title-main">Bifenthrin</span> Chemical compound

Bifenthrin is a pyrethroid insecticide. It is widely used against ant infestations.

<span class="mw-page-title-main">Carbaryl</span> Chemical compound

Carbaryl is a chemical in the carbamate family used chiefly as an insecticide. It is a white crystalline solid previously sold under the brand name Sevin, which was a trademark of the Bayer Company. The Sevin trademark has since been acquired by GardenTech, which has eliminated carbaryl from most Sevin formulations. Union Carbide discovered carbaryl and introduced it commercially in 1958. Bayer purchased Aventis CropScience in 2002, a company that included Union Carbide pesticide operations. Carbaryl was the third-most-used insecticide in the United States for home gardens, commercial agriculture, and forestry and rangeland protection. As a veterinary drug, it is known as carbaril (INN).

<span class="mw-page-title-main">Imidacloprid</span> Chemical compound

Imidacloprid is a systemic insecticide belonging to a class of chemicals called the neonicotinoids which act on the central nervous system of insects. The chemical works by interfering with the transmission of stimuli in the insect nervous system. Specifically, it causes a blockage of the nicotinergic neuronal pathway. By blocking nicotinic acetylcholine receptors, imidacloprid prevents acetylcholine from transmitting impulses between nerves, resulting in the insect's paralysis and eventual death. It is effective on contact and via stomach action. Because imidacloprid binds much more strongly to insect neuron receptors than to mammal neuron receptors, this insecticide is more toxic to insects than to mammals.

Pesticides vary in their effects on bees. Contact pesticides are usually sprayed on plants and can kill bees when they crawl over sprayed surfaces of plants or other areas around it. Systemic pesticides, on the other hand, are usually incorporated into the soil or onto seeds and move up into the stem, leaves, nectar, and pollen of plants.

<span class="mw-page-title-main">Fipronil</span> Chemical compound

Fipronil is a broad-spectrum insecticide that belongs to the phenylpyrazole chemical family. Fipronil disrupts the insect central nervous system by blocking the ligand-gated ion channel of the GABAA receptor and glutamate-gated chloride (GluCl) channels. This causes hyperexcitation of contaminated insects' nerves and muscles. Fipronil's specificity towards insects is believed to be due to its greater binding affinity for the GABAA receptors of insects than to those of mammals, and for its action on GluCl channels, which do not exist in mammals. As of 2017, there does not appear to be significant resistance among fleas to fipronil.

<span class="mw-page-title-main">Fenthion</span> Chemical compound

Fenthion is an organothiophosphate insecticide, avicide, and acaricide. Like most other organophosphates, its mode of action is via cholinesterase inhibition. Due to its relatively low toxicity towards humans and mammals, fenthion is listed as moderately toxic compound in U.S. Environmental Protection Agency and World Health Organization toxicity class.

Neonicotinoids are a class of neuro-active insecticides chemically similar to nicotine, developed by scientists at Shell and Bayer in the 1980s.

<span class="mw-page-title-main">Nitenpyram</span> Insecticide

Nitenpyram is a chemical frequently used as an insecticide in agriculture and veterinary medicine. The compound is an insect neurotoxin belonging to the class of neonicotinoids which works by blocking neural signaling of the central nervous system. It does so by binding irreversibly to the nicotinic acetylcholine receptor (nACHr) causing a stop of the flow of ions in the postsynaptic membrane of neurons leading to paralysis and death. Nitenpyram is highly selective towards the variation of the nACHr which insects possess, and has seen extensive use in targeted, insecticide applications.

<span class="mw-page-title-main">Cyhalothrin</span> Synthetic pyrethroid used as insecticide

Cyhalothrin is the ISO common name for an organic compound that, in specific isomeric forms, is used as a pesticide. It is a pyrethroid, a class of synthetic insecticides that mimic the structure and properties of the naturally occurring insecticide pyrethrin which is present in the flowers of Chrysanthemum cinerariifolium. Pyrethroids such as cyhalothrin are often preferred as an active ingredient in agricultural insecticides because they are more cost-effective and longer acting than natural pyrethrins. λ-and γ-cyhalothrin are now used to control insects and spider mites in crops including cotton, cereals, potatoes and vegetables.

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<span class="mw-page-title-main">Clothianidin</span> Chemical compound

Clothianidin is an insecticide developed by Takeda Chemical Industries and Bayer AG. Similar to thiamethoxam and imidacloprid, it is a neonicotinoid. Neonicotinoids are a class of insecticides that are chemically similar to nicotine, which has been used as a pesticide since the late 1700s. Clothianidin and other neonicotinoids act on the central nervous system of insects as an agonist of nAChR, the same receptor as acetylcholine, the neurotransmitter that stimulates and activating post-synaptic acetylcholine receptors but not inhibiting AChE. Clothianidin and other neonicotinoids were developed to last longer than nicotine, which is more toxic and which breaks down too quickly in the environment.

<span class="mw-page-title-main">Colony collapse disorder</span> Aspect of apiculture

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<span class="mw-page-title-main">Propoxur</span> Chemical compound

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<span class="mw-page-title-main">Acetamiprid</span> Chemical compound

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<span class="mw-page-title-main">Sulfoxaflor</span> Chemical compound

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References

  1. ↑ Pesticide Properties Database. "Thiamethoxam". University of Hertfordshire. Retrieved 2022-01-22.
  2. ↑ PubChem Database (2022-01-15). "N-[3-[(2-chloro-1,3-thiazol-5-yl)methyl]-5-methyl-1,3,5-oxadiazinan-4-ylidene]nitramide" . Retrieved 2022-01-22.
  3. ↑ "Compendium of Pesticide Common Names". BCPC.
  4. ↑ "Neonicotinoids: risks to bees confirmed | EFSA". www.efsa.europa.eu. 2018-02-28. Retrieved 2023-06-23.
  5. ↑ "Conclusion on the peer review of the pesticide risk assessment for bees for the active substance clothianidin". EFSA Journal. 11: 3066. 2013. doi:10.2903/j.efsa.2013.3066.
  6. ↑ US EPA O (2022-06-16). "EPA Finalizes Biological Evaluations Assessing Potential Effects of Three Neonicotinoid Pesticides on Endangered Species". www.epa.gov. Retrieved 2023-06-23.
  7. ↑ Carrington D (2018-04-27). "EU agrees total ban on bee-harming pesticides". The Guardian. ISSN   0261-3077 . Retrieved 2023-06-23.
  8. ↑ Milman O (2022-03-08). "Fears for bees as US set to extend use of toxic pesticides that paralyse insects". The Guardian. ISSN   0261-3077 . Retrieved 2023-06-23.
  9. ↑ Peter Maienfisch, Max Angst, Franz Brandl, et al. (October 2001). "Chemistry and biology of thiamethoxam: a second generation neonicotinoid". Pest Management Science. 57 (10): 906–913. doi:10.1002/ps.365. PMID   11695183.
  10. ↑ Peter Maienfisch, Hanspeter Huerlimann, Alfred Rindlisbacher, et al. (February 2001). "The discovery of thiamethoxam: a second-generation neonicotinoid". Pest Management Science. 57 (2): 165–176. doi:10.1002/1526-4998(200102)57:2<165::AID-PS289>3.0.CO;2-G. PMID   11455647.
  11. ↑ West B (13 February 2002). "Syngenta Settles Patent Dispute with Bayer". lawnandlandscape.com. Retrieved 23 January 2022.
  12. ↑ Maienfisch P (2006). "Synthesis and Properties of Thiamethoxam and Related Compounds". Zeitschrift für Naturforschung B. 61 (4): 353–359. doi: 10.1515/znb-2006-0401 . S2CID   8031781.
  13. 1 2 3 4 5 "FAO Specifications and Evaluations for Agricultural Pesticides: Thiamethoxam" (PDF). 21 June 2000.
  14. ↑ Syngenta (2006). "Thiamethoxam Vigor Effect" (PDF). Retrieved 2011-10-11.
  15. ↑ Patrick H Rose (2012). "6.3.2.Selective Toxicity of Nicotine and Neonicotinoids". In Marrs TC (ed.). Mammalian Toxicology of Insecticides. The Royal Society of Chemistry. p. 186. ISBN   978-1849731911.
  16. ↑ Butcherine P, Benkendorff K, Kelaher B, Barkla BJ (February 2019). "The risk of neonicotinoid exposure to shrimp aquaculture". Chemosphere. 217: 329–348. Bibcode:2019Chmsp.217..329B. doi:10.1016/j.chemosphere.2018.10.197. PMID   30419387. S2CID   53294069.
  17. ↑ Zhang X, Huang Y, Chen WJ, Wu S, Lei Q, Zhou Z, Zhang W, Mishra S, Bhatt P, Chen S (February 2023). "Environmental occurrence, toxicity concerns, and biodegradation of neonicotinoid insecticides". Environmental Research. 218: 114953. Bibcode:2023ER....218k4953Z. doi:10.1016/j.envres.2022.114953. PMID   36504008. S2CID   255468562.
  18. ↑ Finnegan MC, Baxter LR, Maul JD, Hanson ML, Hoekstra PF (October 2017). "Comprehensive characterization of the acute and chronic toxicity of the neonicotinoid insecticide thiamethoxam to a suite of aquatic primary producers, invertebrates, and fish: Thiamethoxam acute and chronic aquatic toxicity". Environmental Toxicology and Chemistry. 36 (10): 2838–2848. doi: 10.1002/etc.3846 . PMID   28493485.
  19. 1 2 Christof W. Schneider, Jürgen Tautz, Bernd Grünewald, Stefan Fuchs (11 January 2012). "RFID Tracking of Sublethal Effects of Two Neonicotinoid Insecticides on the Foraging Behavior of Apis mellifera". PLOS ONE. 7 (1): e30023. Bibcode:2012PLoSO...730023S. doi: 10.1371/journal.pone.0030023 . PMC   3256199 . PMID   22253863.
  20. ↑ EPA Dec 21, 2011 Thiamethoxam Summary Document Registration Review Initial Docket Entire docket is available here
  21. ↑ §180.565 Thiamethoxam; tolerances for residues.
  22. 1 2 Syngenta. "Actara Insecticide" . Retrieved 24 January 2022.
  23. ↑ Environmental Protection Agency (EPA) (5 September 2014). "Receipt of Several Pesticide Petitions Filed for Residues of Pesticide Chemicals in or on Various Commodities" (PDF). Federal Register. 79 (172): 53009–530013. Retrieved 24 January 2022.
  24. ↑ Britt E. Erickson (15 September 2014). "Syngenta Stands Firm On Neonicotinoids". Chemical & Engineering News. 92 (37). American Chemical Society: 7. doi:10.1021/cen-09237-notw1 . Retrieved 13 September 2014.
  25. 1 2 US Geological Survey (2021-10-12). "Estimated Annual Agricultural Pesticide Use for thiamethoxam, 2019" . Retrieved 2022-01-24.
  26. ↑ "EPA Actions to Protect Pollinators". US EPA. 3 September 2013. Retrieved 24 January 2022.
  27. ↑ Allington A (21 May 2019). "EPA Curbs Use of 12 Bee-Harming Pesticides". Bloomberg . Retrieved 24 January 2022.
  28. ↑ "Scientific opinions differ on bee pesticide ban". BBC News. 29 April 2013. Retrieved 22 November 2013.
  29. ↑ EFSA (2012). "Assessment of the scientific information from the Italian project 'APENET' investigating effects on honeybees of coated maize seeds with some neonicotinoids and fipronil". EFSA Journal. 10 (6): 2792. doi: 10.2903/j.efsa.2012.2792 .
  30. ↑ "Bees & Pesticides: Commission goes ahead with plan to better protect bees" . Retrieved 22 November 2013.
  31. ↑ Damian Carrington, "Total ban on bee-harming pesticides likely after major new EU analysis", The Guardian , 28 February 2018 (page visited on 29 April 2018).
  32. ↑ Damian Carrington, "EU agrees total ban on bee-harming pesticides ", The Guardian , 27 April 2018 (page visited on 29 April 2018).
  33. ↑ "BBC News - UK allows emergency use of bee-harming pesticide". BBC News. 3 March 2021.
  34. ↑ "Emergency pesticide authorisation to protect sugar beet crop conditionally approved" . Retrieved 3 April 2024.
  35. ↑ "Defra's Chief Scientific Adviser's advice on the use of Cruiser SB for sugar beet in 2024" . Retrieved 3 April 2024.
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