153719-38-1

Basic information

• Product Name: 3,6-Dihydro-3-methyl-N-nitro-2H-1,3,5-oxadiazin-4-amine
• Synonyms: 3-METHYL-4-NITROIMINOPERHYDRO 1,3,5 OXADIAZINE;3-Methyl-4-nitroimino-tetrahydro-1,3,5-oxadiazine;3,6-dihydro-3-methyl-n-nitro-2h-1,3,5-oxadiazin-4-amine;3-METHYL-4-NITROIMINOPERHYDRO-1,3,5-OXADIAZIN;Methyl-nitro-oxadiazinamin;3-METHYL-4-NITROIMINO-1,3,5-OXADIAZINE[FOR THIAMETHOXAM];5-methyl-4-N-nitroanimo-[1，3，5]oxadiazin;N-(3-methyl-1,3,5-oxadiazinan-4-ylidene)nitramide
• CAS NO: 153719-38-1
• Molecular Formula: C₄H₈N₄O₃
• Molecular Weight: 160.13
• EINECS: 1533716-785-6
• Mol File: 153719-38-1.mol
• Article Data: 15

Chemical Properties

• Melting Point: 141-143°C
• Boiling Point: 291°C
• Flash Point: 130°C
• Appearance: /
• Density: 1.60
• Vapor Pressure: 0.00201mmHg at 25°C
• Refractive Index: 1.628
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly, Heated), Methanol (Slightly, Heated)
• PKA: 6.53±0.20(Predicted)
• Water Solubility: 16g/L at 25℃
• Stability: Light Sensitive
• CAS DataBase Reference: 3,6-Dihydro-3-methyl-N-nitro-2H-1,3,5-oxadiazin-4-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 3,6-Dihydro-3-methyl-N-nitro-2H-1,3,5-oxadiazin-4-amine(153719-38-1)
• EPA Substance Registry System: 3,6-Dihydro-3-methyl-N-nitro-2H-1,3,5-oxadiazin-4-amine(153719-38-1)

Safety Data

• Hazardous Substances Data: 153719-38-1(Hazardous Substances Data)

Usage

Uses

3-Methyl-4-nitroimino-tetrahydro-1,3,5-oxadiazine is a useful synthetic intermediate in the synthesis of Thiamethoxam (T344180); a neonicotinoid insecticide.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C4H8N4O3/c1-7-3-11-2-5-4(7)6-8(9)10/h2-3H2,1H3,(H,5,6)

Upstream product

• 50-00-0 formaldehyd 
• 64-18-6 formic acid 
• 4245-76-5 N-Methyl-N'-nitroguanidine 
• 4245-76-5 N-methyl-N'-nitroguanidinene 
• 4245-76-5 N-methyl-N'-nitroguanidine 

Downstream Products

• 153719-23-4 thiamethoxam 
• 1237740-64-5 N-{3-[(E)-3-(4-ethoxyphenyl)acryloyl]-5-methyl-1,3,5-oxadiazinan-4-ylidene}nitramide 
• 1237740-61-2 N-{3-[(E)-3-(2,4-dichlorophenyl)acryloyl]-5-methyl-1,3,5-oxadiazinan-4-ylidene}nitramide 
• 1237740-60-1 N-{3-[(E)-3-(4-bromophenyl)acryloyl]-5-methyl-1,3,5-oxadiazinan-4-ylidene}nitramide 
• 1237740-59-8 N-{3-[(E)-3-(4-chlorophenyl)acryloyl]-5-methyl-1,3,5-oxadiazinan-4-ylidene}nitramide 
• 1237740-58-7 N-{3-[(E)-3-(4-fluorophenyl)acryloyl]-5-methyl-1,3,5-oxadiazinan-4-ylidene}nitramide 
• 1237740-65-6 N-[3-methyl-5-((E)-3-m-tolylacryloyl)-1,3,5-oxadiazinan-4-ylidene]nitramide 
• 1237740-63-4 N-{3-[(E)-3-(4-methoxyphenyl)acryloyl]-5-methyl-1,3,5-oxadiazinan-4-ylidene}nitramide 
• 192439-46-6 3-(2-phenylthio-thiazol-5-yl-methyl)-5-methyl-4-nitroimino-perhydro-1,3,5-oxadiazine 
• 192439-46-6 3-(2-phenylthiothiazol-5-ylmethyl)-5-methyl-4-nitroiminoperhydro-1,3,5-oxadiazine 

Relevant articles and documents

Development of an enzyme-linked immunosorbent assay for the insecticide thiamethoxam

An enzyme-linked immunosorbent assay (ELISA) was developed for the neonicotinoid insecticide thiamethoxam, 3-(2-chlorothiazol-5-ylmethyl)-5-methyl-4-nitroimino-1,3,5-oxadiazinane. Three antisera were raised from rabbits immunized with the hapten - KLH conjugate. On the basis of the computational analysis of hapten candidates, the hapten with a spacer arm on the thiazolyl ring of thiamethoxam was synthesized to elicit thiamethoxam-specific antisera. The hapten was 3-[2-(2-carboxyethylthio)-5-ylmethyl]-5-methyl-4-nitroimino-1,3, 5-oxadiazinane. Antisera were characterized with indirect competitive ELISA. Cross-reactivity and effects of organic solvents, pH, and ionic strengths were evaluated. The antiserum was specific for thiamethoxam and tolerant of up to 5% acetonitrile and 5% acetone. Various ionic strengths and pH values in the tested ranges had negligible effect on the assay performance. Under the optimized conditions, the half-maximal inhibition concentration (IC50) and the limit of detection were approximately 9.0 and 0.1 μg/L of thiamethoxam, respectively. ELISA analysis of stream and tap water samples showed an excellent correlation with the fortification levels.

Azido-neonicotinoids as candidate photoaffinity probes for insect nicotinic acetylcholine receptors [1]

The neonicotinoids are the most successful chemical class of insecticides reaching sales of more than 630 Mio $ in 2001, mainly due to the excellent market performance of imidacloprid and thiamethoxam. The insect nicotinic acetylcholine receptors (nAChRs) are the targets for these compounds, which are highly effective against a variety of sucking and chewing insects. Compared with the other neonicotinoid sales products, thiamethoxam binds in a different way, possibly to a different site of nAChRs in aphids. To gain further insight into the different modes of binding, a research program applying the photoaffinity labeling technique was started. A series of novel candidate photoaffinity probes containing a 5-azido-6-chloropyridin-3-ylmethyl group were prepared from 5-azido-6-chloropyridin-3-ylmethyl chloride, which was obtained in three steps from 6-chloropyridin-3-ylmethyl chloride. These probes showed good to excellent contact/feeding and systemic activity against Myzus persicae, however, they were at least 4- to 16-fold less effective against Aphis craccivora, Nilaparvata lugens, Spodoptera littoralis, and Diabrotica balteata than the neonicotinoid sales products. In general, the introduction of an azide group at C(5) of the 6-chloropyridin-3-ylmethyl substituent resulted in reduced potency as well as in a narrower pest spectrum. In competition binding assays with [3H]imidacloprid, analogues of imidacloprid, clothianidin, thiacloprid and thiamethoxam containing a 5-azido-6-chloropyridin- 3-ylmethyl group showed high displacing potency with nAChRs from Aphis and Myzus (Ki values: 2 to 27 nM) suggesting that these compounds are valuable candidate photoaffinity probes. Taking into account the biological screening activity as well as the receptor binding potency, 1-(5-azido-6- chloropyridin-3-ylmethyl)-2-nitroimino-imidazolidine N-(5-azido-6-chloropyridin- 3-ylmethyl)-N′-methyl-N″-nitroguanidine and 3-(5-azido-6- chloropyridin-3-ylmethyl)-2-cyanoimino-thiazolidine were identified as the preferred candidate neonicotinoid photoaffinity probes to study the imidacloprid binding site.

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.

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.

3-methyl-4-nitro imine base entire hydrogen -1, 3, 5- [...] method for the synthesis of (by machine translation)

The invention discloses 3-methyl-4-nitro imine base entire hydrogen -1, 3, 5- [...] (abbrebyted [...] ) synthesis method, characterized in that to methyl nitroguanideine with poly formaldehyde as the starting material, the formic acid and dilute sulfuric acid in the mixed acid system, direct ring adnation into 3-methyl-4-nitro imine base entire hydrogen -1, 3, 5- [...]. Reaction of this invention is the principle is simple, the process route is scientific and reasonable design, using formic acid and dilute sulfuric acid mixed reaction system, improves the conversion rate of the reaction. Initial easy availability of raw materials, intermediate stable performance, production cost saving, high product yield, high purity, strong competition product market. Easy to control in the production process, small pollution to the environment. With great market and social development value. (by machine translation)