153719-23-4

Usage

Uses

Used in Agricultural Industry:
Thiamethoxam is used as a broad-spectrum insecticide for controlling a wide range of sucking and chewing insect pests. It is applied through foliar, soil, or seed treatments and is effective against various pests that feed on roots, leaves, and other plant tissues. Thiamethoxam is utilized in the production of most row and vegetable crops, such as corn, soybeans, snap beans, and potatoes.
Used in Livestock and Poultry Industry:
Thiamethoxam is also used to control insects in livestock pens and poultry houses, helping to maintain a healthy environment for animals and reduce the impact of insect-borne diseases.
Used in Turf and Landscape Management:
The insecticide is employed in sod farms, golf courses, lawns, household plants, and tree nurseries to protect plants from insect damage and ensure their healthy growth.
Environmental Concerns:
Reports have shown that exposure to neonicotinoid pesticides, such as Thiamethoxam, can cause honeybees to have problems returning home after foraging, and bumblebee colonies to grow poorly and produce fewer queens. This highlights the need for responsible use and ongoing research into the environmental impact of Thiamethoxam and other neonicotinoid insecticides.

Flammability and Explosibility

Flammable

Metabolic pathway

All 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).

Degradation

Thiamethoxam 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 action

Thiamethoxam 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).

InChI:InChI=1/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+

Upstream product

• 105827-91-6 α-Cl-β-thiazolyl chloride 
• 153719-38-1 3,6-dihydro-3-methyl-N-nitro-2H-1,3,5-oxadiazin-4-amine 
• 74-88-4 methyl iodide 
• 153719-38-1 3,6-dihydro-3-methyl-N-nitro-2H-1,3,5-oxadiazine-4-amine 
• 192439-46-6 3-(2-phenylthiothiazol-5-ylmethyl)-5-methyl-4-nitroiminoperhydro-1,3,5-oxadiazine 
• 135018-15-4 N-(2-chlorothiazol-5-ylmethyl)-N'-nitroguanidine 

Relevant academic research and scientific papers

Experimental and DFT studies on the vibrational, electronic spectra and NBO analysis of thiamethoxam

Vibrational and electronic spectral measurements were performed for 3-(2-chloro-1,3-thiazol-5-ylmethyl)-5-methyl-1,3,5-oxadiazinan-4-ylidene(nitro) amine (thiamethoxam). Optimized geometrical structure and harmonic vibrational frequencies were calculated

Thiamethoxam and uses thereof

A crystalline form of 3-(2-chloro-1,3-thiazol-5-ylmethyl)-5-methyl 1,3,5-oxadiazinan-yledene (nitro)amine (thiamethoxam) is provided. The crystalline form exhibits an X-ray powder diffraction pattern having characteristic peaks (expressed in degrees 2?? +/- 0.2?° ??) at one or more of the following positions: 6.09, 15.37, 17.83, 18.43, 20.86, 22.01, 26.95 and 27.84, and an Infrared (IR) spectrum having characteristic peaks at about 2933.62, 2161.78 and 1593.88 cm-1. A method of preparing the crystalline form comprises crystallizing 3-(2-chloro-1,3-thiazol-5-ylmethyl)-5-methyl-1,3,5-oxadiazinan -4-yledene (nitro)amine (thiamethoxam) from a solvent system comprising a solvent selected from an alcohol, a glycol, an ether, a ketone, an ester, an amide, a nitrile, an aliphatic or aromatic hydrocarbon, or mixtures thereof; and isolating the resulting crystals. The exemplified solvents are methanol, ethanol, 1-propanol, ethylene glycol, toluene and xylene.

Thiamethoxam production method and extractant

The invention provides a thiamethoxam production method and an extractant, belongs to the technical field of pesticides, particularly provides an extractant taking ethylene glycol salicylate as a complexing agent, and also provides a composite extractant. The extractant comprises a complexing agent and a diluent, and the complexing agent comprises the ethylene glycol salicylate and P204, wherein the extraction ratio of ethylene glycol salicylate to P204 is 1:1.5 to 1:2. The ethylene glycol salicylate used as the complexing agent and -N- of thiamethoxam have strong ion association to generate an ion extract with the same structure, so that the distribution ratio is increased; and when the extractant and the P204 are used for composite extraction, hydrogen bond association of the strong electron withdrawing group nitro -NO2 of thiamethoxam and -OH of P204 can be promoted, and when the extraction ratio of ethylene glycol salicylate to the P204 extractant is 1:(1.5-2), the distribution ratio can be synergistically increased, and the extraction rate is increased.

Preparation method of thiamethoxam

The invention discloses a preparation method of thiamethoxam. The method comprises the following steps: reacting a raw material 2-chloro-5-chloromethylthiazole with 3-methyl-4-nitroiminoperhydro-1,3,5-oxadiazine, carrying out a reaction with dimethyl carbonate as a reaction solvent and N,N-diisopropylethylamine as an acid binding agent, decolorizing the obtained solution with ozone after the reaction is finished, adding water to cool and crystallize, and filtering and drying the obtained solution to obtain high-quality pure white thiamethoxam. The method of the invention has the advantages ofeasy availability of raw materials, mild reaction conditions, few three wastes, simplicity in operation, short time, and easiness in industrial production, and the finished product has the advantagesof high yield and high content.

PROCESS FOR THE PREPARATION OF THIAMETHOXAM

There is disclosed the use of a solvent system comprising a C1 to C4 alcohol, a substituted benzene derivative bearing two or more C1 to C4 alkyl substituents, or a mixture thereof in the preparation of a crystalline form of 3-(2-chloro-1, 3-thiazol-5-yl methyl)-5-methyl-1, 3, 5-oxadiazinan-4-yledene (nitro) amine (thiamethoxam). Crystalline thiamethoxam prepared in this way exhibits a significantly improved stability, in particular a resistance to photolysis, compared with crystalline thiamethoxam prepared using other solvents.

Preparation method of thiamethoxam

The invention discloses a preparation method of thiamethoxam. The preparation method of the thiamethoxam comprises the following steps: taking methylnitroguanidine as a starting material, preparing 3-methyl-4-nitroimine-1,3,5-oxadiazine (compound II), and then preparing the thiamethoxam. The method provided by the invention is simple in process, the finally synthesized thiamethoxam does not need recrystallization, the content of the final product is up to 98% or above, and the yield reaches 84% or above.

Synthesis method of thiamethoxam

The invention relates to the field of compound synthesis, in particular to a synthesis method of an agricultural insecticide thiamethoxam. According to the preparation method of the thiamethoxam provided by the invention, through selecting appropriate reaction raw materials, a new synthetic route is designed, and an intermediate 2-chlorine-5-chloromethyl-thiazole can be prepared at room temperature, so that a cooling device is not needed, the energy is saved, and the reaction yield can be improved.

Preparation method of thiamethazide

The invention discloses a preparation method of thiamethazide. The preparation method comprises the following steps of sequentially adding the measured solvent, 3-methyl-4-nitrocarbamide-1,3,5-oxadiazine, potassium carbonate and catalyst, stirring, uniformly mixing, and heating to 25 to 35 DEG C; dripping a mixture of 2-chloro-5-chloromethylthiazole and solvent into a reaction system at the speedof 40 to 60ml/h, controlling the temperature to be lower than 35 DEG C, stirring to react for 8 to 16h after the mixture of 2-chloro-5-chloromethylthiazole and solvent is dripped, and completely reacting; heating to 65 to 70 DEG C, and filtering coarse salt under the heat condition; cooling to 0 to 5 DEG C, crystallizing, filtering to obtain filtrate and filter cake, treating the filtrate for recycling, spraying the filter cake by methanol twice, and drying under the vacuum condition, so as to obtain the crude drug of the thiamethazide. The preparation method has the advantages that a large amount of subsequent workload is reduced, the highest reaction yield rate of thiamethazide can reach 92% or above, the content is about 98%, and the production of a large amount of wastewater is reduced.

Preparation method for high-purity thiamethoxam

The invention discloses a preparation method for high-purity thiamethoxam. Thiamethoxam has a structure shown as formula (I). The method comprises the following steps: reacting the compound with the structure as shown in a formula (II) with the compound with a structure as shown in a formula (III) in a polar aprotic solvent in the presence of a catalyst and inorganic base, and then filtering, decolorizing, desolventizing and crystallizing, thereby acquiring a thiamethoxam product with a purity above 99% and a yield of 90%. The method disclosed by the invention is short in reaction time, low in reaction temperature, easy to operate, environment-friendly, capable of increasing product purity and yield and suitable for industrial production.

Thiamethoxam production method

The invention provides a thiamethoxam production method. The thiamethoxam production method is used for producing thiamethoxam, and comprises a first-step reaction, a second-step reaction and crude product processing to obtain the end product of thiamethoxam, wherein 1-methyl-3-nitroguanidine and paraformaldehyde are taken as reaction raw materials to perform the first-step reaction under the condition that a mixed acid is a solvent; and an obtained competitive product (3-methyl-4-nitroimino-1,3,5-oxadiazine) and 2-chloro-5-chloromethylthiazole performs the second-step reaction to obtain a crude product (thiamethoxam). The thiamethoxam production method has the advantages of environmental friendliness and low production cost.