Thiamethoxam

Thiamethoxam Basic information
Product Name:Thiamethoxam
Synonyms:Adage;Cruiser;cruiser350fs;THIAMETHOXAM;3-(2-Chloro-1,3-thiazol-5-ylmethyl)-5-methyl-1,3,5-oxadiazinan-4-ylidene(nitro)amine;4H-1,3,5-Oxadiazin-4-imine, 3-(2-chloro-5-thiazolyl)methyltetrahydro-5-methyl-N-nitro-;thiamethoxam(bsi,iso);cruiser 600 fs
CAS:153719-23-4
MF:C8H10ClN5O3S
MW:291.71
EINECS:428-650-4
Product Categories:Agro-Products;Heterocycles;Sulfur & Selenium Compounds;pesticide
Mol File:153719-23-4.mol
Thiamethoxam Structure
Thiamethoxam Chemical Properties
Melting point 139.1°
Boiling point 485.8±55.0 °C(Predicted)
density 1.71±0.1 g/cm3(Predicted)
vapor pressure 6.6 x 10-9 Pa (25 °C)
storage temp. Inert atmosphere,2-8°C
solubility DMSO: 250 mg/mL (857.02 mM)
Water Solubility 4.1 x 103 mg l-1 (25 °C)
pka0.99±0.10(Predicted)
form neat
BRN 8491021
InChIInChI=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
InChIKeyNWWZPOKUUAIXIW-DHZHZOJOSA-N
SMILESO1CN(C)C(=N[N+]([O-])=O)N(CC2SC(Cl)=NC=2)C1
LogP-0.13 at 25℃
EPA Substance Registry SystemThiamethoxam (153719-23-4)
Safety Information
Hazard Codes Xn
Risk Statements 22-50/53
Safety Statements 22-61-60
RIDADR UN 3077 9 / PGIII
WGK Germany 2
HS Code 29341000
Hazardous Substances Data153719-23-4(Hazardous Substances Data)
ToxicityLD50 in rats (mg/kg): 1563 orally, >2000 dermally; LD50 in bobwhite quail, mallard duck (mg/kg): 1552, 576 orally. LC50 (96hr) in rainbow trout, bluegill (mg/l): >100, >114 (Senn).
MSDS Information
Thiamethoxam Usage And Synthesis
Chemical PropertiesOff-White to Pale Yellow Solid
UsesThiamethoxam is a broad spectrum insecticide active against a wide spectrum of sucking and chewing insect pests after foliar, soil or seed treatment.
DefinitionChEBI: Thiamethoxam is an oxadiazane that is tetrahydro-N-nitro-4H-1,3,5-oxadiazin-4-imine bearing (2-chloro-1,3-thiazol-5-yl)methyl and methyl substituents at positions 3 and 5 respectively. It has a role as an antifeedant, a carcinogenic agent, an environmental contaminant, a xenobiotic and a neonicotinoid insectide. It is an oxadiazane, a member of 1,3-thiazoles, an organochlorine compound and a 2-nitroguanidine derivative. It derives from a 2-chlorothiazole.
ApplicationThiamethoxam is a neonicotinoid insecticide that is used widely in Wisconsin. Thiamethoxam is the active ingredient in a variety of products used in agriculture to kill sucking and chewing insects that feed on roots, leaves, and other plant tissues. Agricultural uses include soil and seed treatments as well as leaf spraying for most row and vegetable crops like corn, soybeans, snap beans, and potatoes. It is also used to control insects in livestock pens, poultry houses, sod farms, golf courses, lawns, household plants, and tree nurseries. It was first registered by the U.S. Environmental Protection Agency in 1999. Reports show that when exposed to neonicotinid pesticides honeybees have probelms returnign home after foraging and bumblebee colonies grow poorly and produce fewer queens.
Flammability and ExplosibilityFlammable
Metabolic pathwayAll the information on thiamethoxam is taken from a summary of the proceedings of meeting published by the manufacturer. Full experimental details are not given in the report and the identity of metabolites is not disclosed (Novartis, 1997).
DegradationThiamethoxam is hydrolytically stable at pH 5 (half-life about 200-300 days). The compound is more labile at pH 9 where the half-life is a few days. It is rapidly photodegraded with a half-life of about 1 hour. In aquatic systems, degradation occurs under alkaline conditions and the insecticide is rapidly photodegraded but not readily biodegraded (Novartis, 1997).
Mode of actionThiamethoxam interferes with nicotinic acetylcholine receptors in the insect’s nervous system, which are essential for proper functioning of the nerves. Within hours of contact or ingestion of thiamethoxam, insects stop feeding. Death usually occurs within 24 to 48 hours.
The activity of thiamethoxam, or any insecticide, at the target site is just one factor in its efficacy. When comparing insecticides, other variables – including how the compound interacts with the environment, the plant and the insect – also contribute to its insecticidal mode of action.
The Insecticide Resistance Action Committee (IRAC) has organized insecticides into 28 groups, plus sub-groups, based on their modes of action. Thiamethoxam is a Group 4A insecticide (neonicotinoids).
Thiamethoxam Preparation Products And Raw materials
Raw materials3,6-Dihydro-3-methyl-N-nitro-2H-1,3,5-oxadiazin-4-amine-->2-Chloro-5-chloromethylthiazole
Thidiazuron 2-CHLORO-5-(CHLOROMETHYL)-1,3-THIAZOLE[FOR THIAMETHOXAM] Methyl Thiamethoxam95%Tg25%Wdg THIAMETHOXAM SOLUTION 100UG/ML IN METHANOL 1ML Thiamethoxam 25WG 2-[(2,6-DICHLOROBENZYLIDENE)AMINO]-3-([(2,4-DICHLORO-1,3-THIAZOL-5-YL)METHYL]AMINO)BUT-2-ENEDINITRILE 2,4-DICHLORO-1,3-THIAZOLE-5-CARBOXALDEHYDE OXIME Buprofezin 2-[(4-CHLOROBENZYLIDENE)AMINO]-3-([(2,4-DICHLORO-1,3-THIAZOL-5-YL)METHYL]AMINO)BUT-2-ENEDINITRILE thiazoline Kresoxim-methyl 2-(BENZYLIDENEAMINO)-3-([(2,4-DICHLORO-1,3-THIAZOL-5-YL)METHYL]AMINO)BUT-2-ENEDINITRILE 3-METHYL-4-NITROIMINO-1,3,5-OXADIAZINE[FOR THIAMETHOXAM] 2,4-DICHLORO-5-[(([(3-CHLOROANILINO)CARBONYL]OXY)IMINO)METHYL]-1,3-THIAZOLE 2-AMINO-3-([(2,4-DICHLORO-1,3-THIAZOL-5-YL)METHYL]AMINO)BUT-2-ENEDINITRILE 2-Amino-5-mercapto-1,3,4-thiadiazole zinc 2,4-DICHLORO-5-[(([(4-CHLOROANILINO)CARBONYL]OXY)IMINO)METHYL]-1,3-THIAZOLE

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