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Merck
CN

37924

Thiamethoxam

PESTANAL®, analytical standard

Synonym(s):

3-(2-Chloro-5-thiazolylmethyl)tetrahydro-5-methyl-N-nitro-4H-1,3,5-oxadiazin-4-imine

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About This Item

Empirical Formula (Hill Notation):
C8H10ClN5O3S
CAS Number:
153719-23-4
Molecular Weight:
291.71
UNSPSC Code:
41116107
NACRES:
NA.24
PubChem Substance ID:
329755732
MDL number:
MFCD03792862
Beilstein/REAXYS Number:
8491021

Key Documents

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Product Name

Thiamethoxam, PESTANAL®, analytical standard

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+

SMILES string

CN1COCN(Cc2cnc(Cl)s2)\C1=N\[N+]([O-])=O

InChI key

NWWZPOKUUAIXIW-DHZHZOJOSA-N

grade

analytical standard

product line

PESTANAL®

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

application(s)

agriculture
environmental

format

neat

Quality Level

100

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Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

General description

Find more information here: Neonicotinoids
Thiamethoxam is a neonicotinoid broad spectrumand systemic insecticide, which belongs to the subclass of thianicotinyls. It can find applications in controlling the growth of sucking insects like aphids, whiteflies, and rice hoppers by acting on the acetylcholine nicotinic receptors.

Legal Information

PESTANAL is a registered trademark of Merck KGaA, Darmstadt, Germany

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Danger

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Flam. Sol. 1 - Repr. 2

Storage Class

4.1B - Flammable solid hazardous materials

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Regulatory Information

农药列管产品
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Certificates of Analysis (COA)

Lot/Batch Number
BCCJ0458
BCCG5825
BCBT8326
BCBT3749
BCBR7172V

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Nourddine Ajermoun et al.
Journal of the science of food and agriculture, 99(9), 4407-4413 (2019-03-13)
Thiamethoxam (3-[(2-chloro-5-thiazolyl)methyl]tetrahydro-5-methyl-N-nitro-4H-1,3,5-oxadiazin-4-imine) belongs to a relatively new class of insecticides known as neonicotinoids, which can block irreversibly nicotinic acetylcholine receptors of the nervous system of insects. Its determination at trace levels is an acute analytical problem. Therefore, chromatography, spectroscopy, and
Dara A Stanley et al.
Scientific reports, 7(1), 8005-8005 (2017-08-16)
Neonicotinoid pesticides are used in agriculture to reduce damage from crop pests. However, beneficial insects such as bees can come into contact with these pesticides when foraging in treated areas, with potential consequences for bee declines and pollination service delivery.
Characterization of nicotinic acetylcholine receptors from the insects Aphis craccivora, Myzus persicae, and Locusta migratoria by radioligand binding assays: relation to thiamethoxam action
Wiesner P and Kayser H
Journal of Biochemical and Molecular Toxicology, 14, 221-230 (2000)
P Maienfisch et al.
Pest management science, 57(10), 906-913 (2001-11-07)
Thiamethoxam is the first commercial neonicotinoid insecticide from the thianicotinyl subclass. It was discovered in the course of our optimisation program on neonicotinoids started in 1985. Novel variations of the nitroimino-heterocycle of imidacloprid led to 4-nitroimino-1,3,5-oxadiazinanes exhibiting high insecticidal activity.
P R Whitehorn et al.
Scientific reports, 7(1), 15562-15562 (2017-11-16)
Neonicotinoid pesticides have been linked to global declines of beneficial insects such as bumblebees. Exposure to trace levels of these chemicals causes sub-lethal effects, such as reduced learning and foraging efficiency. Complex behaviours may be particularly vulnerable to the neurotoxic
View All Related Papers

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Analysis of banned neonicotinoid insecticides from dandelion blossoms using QuEChERS and LC-MS.

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