Thiacloprid

Last updated
Thiacloprid
Thiacloprid structure.svg
Names
IUPAC name
{(2Z)-3-[(6-Chloropyridin-3-yl)methyl]-1,3-thiazolidin-2-ylidene}cyanamide
Other names
[3-[(6-Chloro-3-pyridinyl)methyl]-2-thiazolidinylidene]cyanamide
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.129.728 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C10H9ClN4S/c11-9-2-1-8(5-13-9)6-15-3-4-16-10(15)14-7-12/h1-2,5H,3-4,6H2/b14-10- Yes check.svgY
    Key: HOKKPVIRMVDYPB-UVTDQMKNSA-N Yes check.svgY
  • Clc1ncc(cc1)CN2C(=N\C#N)\SCC2
Properties [1]
C10H9ClN4S
Molar mass 252.72 g·mol−1
AppearanceYellowish crystalline solid
Density 1.46 g·cm−3 at 20 °C
Melting point 136 °C (277 °F; 409 K)
185 mg/L at 20°C [2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Thiacloprid is an insecticide of the neonicotinoid class. Its mechanism of action is similar to other neonicotinoids and involves disruption of the insect's nervous system by stimulating nicotinic acetylcholine receptors. Thiacloprid was developed by Bayer CropScience for use on agricultural crops to control of a variety of sucking and chewing insects, primarily aphids and whiteflies. [1] [3]

Contents

Regulation

Thiacloprid has been banned in France since September 1, 2018. [4] The 5 neonicotinoids banned in France are Acetamiprid, Clothianidin, Imidacloprid, Thiacloprid and Thiamethoxam. [5]

Related Research Articles

Honey bee Eusocial flying insect of genus Apis, producing surplus honey

A honey bee is a eusocial flying insect within the genus Apis of the bee clade, all native to Afro-Eurasia. After bees spread naturally throughout Africa and Eurasia, humans became responsible for the current cosmopolitan distribution of honey bees, introducing multiple subspecies into South America, North America, and Australia.

Insecticide Pesticide used against insects

Insecticides are substances used to kill insects. They include ovicides and larvicides used against insect eggs and larvae, respectively. Insecticides are used in agriculture, medicine, industry and by consumers. 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.

Imidacloprid 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.

Caucasian honey bee Subspecies of western honey bee

The Caucasian honey bee is a subspecies of the western honey bee.

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.

Fipronil 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 to the GABAA receptors of insects, than to those of mammals, and to its action on GluCl channels, which do not exist in mammals. As of 2017, there did not appear to be significant resistance among fleas to fipronil.

Cape honey bee Subspecies of honey bee

The Cape honey bee or Cape bee is a southern South African subspecies of the western honey bee. They play a major role in South African agriculture and the economy of the Western Cape by pollinating crops and producing honey in the Western Cape region of South Africa.

Bees and toxic chemicals

Bees can suffer serious effects from toxic chemicals in their environments. These include various synthetic chemicals, particularly insecticides, as well as a variety of naturally occurring chemicals from plants, such as ethanol resulting from the fermentation of organic materials. Bee intoxication can result from exposure to ethanol from fermented nectar, ripe fruits, and manmade and natural chemicals in the environment.

Nosema ceranae is a microsporidian, a small, unicellular parasite that mainly affects Apis cerana, the Asiatic honey bee. Along with Nosema apis, it causes the disease nosemosis, the most widespread of the diseases of adult honey bees. N. ceranae can remain dormant as a long-lived spore which is resistant to temperature extremes and dehydration. This fungus has been shown to act in a synergistic fashion with diverse insecticides such as fipronil or neonicotinoids, by increasing the toxicity of pesticides for bees, leading to higher bee mortality. It may thus play an indirect role in colony collapse disorder. In addition, the interaction between fipronil and N. ceranae induces changes in male physiology leading to sterility.

Neonicotinoids are a class of neuro-active insecticides chemically similar to nicotine. In the 1980s Shell and in the 1990s Bayer started work on their development.

Nitenpyram 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.

Clothianidin 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. However, studies published in 2012 show that neonicotinoid dust released at planting time may persist in nearby fields for several years and be taken up into non-target plants, which are then foraged by bees and other insects.

Western honey bee European honey bee

The western honey bee or European honey bee is the most common of the 7–12 species of honey bees worldwide. The genus name Apis is Latin for "bee", and mellifera is the Latin for "honey-bearing" or "honey carrying", referring to the species' production of honey.

Colony collapse disorder Aspect of apiculture

Colony collapse disorder (CCD) is an abnormal phenomenon that occurs when the majority of worker bees in a honey bee colony disappear, leaving behind a queen, plenty of food, and a few nurse bees to care for the remaining immature bees. While such disappearances have occurred sporadically throughout the history of apiculture, and have been known by various names, the syndrome was renamed colony collapse disorder in early 2007 in conjunction with a drastic rise in reports of disappearances of western honey bee colonies in North America. Beekeepers in most European countries had observed a similar phenomenon since 1998, especially in Southern and Western Europe; the Northern Ireland Assembly received reports of a decline greater than 50%. The phenomenon became more global when it affected some Asian and African countries as well.

Acetamiprid Chemical compound

Acetamiprid is an organic compound with the chemical formula C10H11ClN4. It is an odorless neonicotinoid insecticide produced under the trade names Assail, and Chipco by Aventis CropSciences. It is systemic and intended to control sucking insects (Thysanoptera, Hemiptera, mainly aphids) on crops such as leafy vegetables, citrus fruits, pome fruits, grapes, cotton, cole crops, and ornamental plants. It is also a key pesticide in commercial cherry farming due to its effectiveness against the larvae of the cherry fruit fly.

Thiamethoxam Chemical compound

Thiamethoxam is the ISO common name 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.

Carbophenothion Chemical compound

Carbophenothion also known as Stauffer R 1303 as for the manufacturer, Stauffer Chemical, is an organophosphorus chemical compound. It was used as a pesticide for citrus fruits under the name of Trithion. Carbophenothion was used as an insecticide and acaricide. Although not used anymore it is still a restricted use pesticide in the United States. The chemical is identified in the US as an extremely hazardous substance according to the Emergency Planning and Community Right-to-Know Act.

Jeffery Stuart Pettis is an American-born biologist and entomologist known for his extensive research on honeybee behavior. He is currently head of Apimondia. He was the research leader at the United States Department of Agriculture's Beltsville Bee Laboratory (BBL). His research has led to significant breakthroughs in understanding and managing CCD, a primary cause of North American bee population decline. He is also known for discovering with Dennis vanEngelsdorp, then at Pennsylvania State University, the ability of bees to detect pesticides and harmful fungi in collected pollen and subsequently quarantine the harmful substances from the rest of the hive. His research has also studied the synergistic effects of Imidacloprid on bees, an insecticide derived from nicotine which has been shown to contribute to CCD.

Flupyradifurone Chemical compound

Flupyradifurone is an organic heterocyclic compound. It is used as a novel butenolide insecticide. Flupyradifurone shows efficient protection to crops and is much safer for non-target organisms compared to other commercial insecticides. Flupyradifurone was developed by Bayer CropScience under the name Sivanto. Sivanto was launched in 2014 since it obtained its first commercial registration in central America. Insecticide Resistance Action Committee (IRAC) classified Flupyradifurone as 4D subset (butenolide) and it is the first pesticide in the butenolide category. In 2015, it was approved by EU.

References

  1. 1 2 Thiacloprid Pesticide Fact Sheet, United States Environmental Protection Agency Archived 2012-06-27 at the Wayback Machine
  2. "Thiacloprid". Bayer CropScience Crop Compendium. Bayer CropScience. Archived from the original on 23 October 2011. Retrieved 30 November 2011. (June 2019, website structure changed; site search gives 16 search results for thiacloprid, all apparently under 'Crop Science', none in the compendium)
  3. Schuld M, Schmuck R (2000). "Effects of Thiacloprid, a New Chloronicotinyl Insecticide, On the Egg Parasitoid Trichogramma cacaoeciae". Ecotoxicology. 9 (3): 197–205. doi:10.1023/A:1008994705074. ISSN   0963-9292.
  4. LOI No. 2016-1087 du 8 août 2016 pour la reconquête de la biodiversité, de la nature et des paysages, article 125, accessed 3 July 2019
  5. Décret n° 2018-675 du 30 juillet 2018 relatif à la définition des substances actives de la famille des néonicotinoïdes présentes dans les produits phytopharmaceutiques, accessed 3 July 2019

Thiacloprid listing at pubchem pubchem.ncbi.nlm.nih.gov

Thiacloprid listing at toxnet toxnet.nlm.nih.gov (Reviewed 3/28/2019)[ dead link ]

Thiacloprid, as active substance and as formulation, poses a substantial risk to honey bees by disrupting learning and memory functions. Honey bees (Apis mellifera carnica) were exposed chronically to thiacloprid in the field for several weeks at a sublethal concentration. Foraging behavior, homing success, navigation performance, and social communication were impaired, and thiacloprid residue levels increased both in the foragers and the nest mates over time. Thiacloprid exposed free-flying bumblebee colonies were more likely to die prematurely, and those that survived reached a lower final weight and produced 46% fewer reproductives than colonies placed at control farms.

Thiacloprid; Pesticide Tolerances: A Rule by the Environmental Protection Agency on 02/06/2013 federalregister.gov

Pesticide Fact Sheet Name of Chemical: ThiaclopridReason for Issuance: Conditional RegistrationDate Issued: September 26, 2003 www3.epa.gov

D. Beneficial Insects:. Based upon the results of core bee toxicity tests, it is predicted that thiacloprid will not adversely affect bees. In addition, thiacloprid toxicity is unlike other neonicotinoid insecticides (i.e.: imidacloprid, and clothianidin) which have demonstrated very high to high acute toxicity to bees. (p. 10)

PPDB: Pesticide Properties DataBase at University of Hertfordshire Describes Toxicity to Apis mellifera as 'Moderate' Briefing: Thiacloprid: A bee harming pesticide friendsoftheearth.uk (ca. 2014)

Conclusion ...Evidence from independent scientific research indicates that thiacloprid is harmful to bees especially when its use is combined with other pressures on these insects. Thiacloprid has been approved for use on the basis of an inadequate testing regime which does not look for impacts on wild bees, does not assess sub lethal effects of longer term exposure or the interaction between the active ingredient and other substances or even other pressures on bees...