57538-27-9

Usage

Uses

Used in Pesticide and Herbicide Applications:
O-Methyl-N-nitroisourea is used as a pesticide and herbicide due to its ability to inhibit the enzyme acetolactate synthase, which is essential for the growth of plants. This makes it an effective agent for controlling plant growth and eliminating unwanted vegetation.
Used in Chemical Research:
Although its use is limited due to its hazardous nature, O-Methyl-N-nitroisourea may be utilized in chemical research for studying its properties and potential applications in various fields. Researchers may explore its reactivity and decomposition characteristics to develop safer and more effective alternatives.

InChI:InChI=1/C2H6N3O3/c1-8-2(3)4-5(6)7/h1H3,(H2,3,4)(H,6,7)/q+1

Upstream product

• 57-13-6 urea 
• 77-78-1 dimethyl sulfate 
• 29427-58-5 O-methylisourea hemisulfate 
• 2440-60-0 2-methyl-isourea 
• 24285-39-0 O-methylisourea hydrosulfate 
• 616-38-6 carbonic acid dimethyl ester 
• 24285-39-0 O-methylisourea hemisulfate 

Downstream Products

• 2149-70-4 N^ω-nitro-L-arginine 
• 67396-06-9 C₁₄H₂₁N₅O₆S 
• 187149-02-6 N-(2-chlorothiazol-5-ylmethyl)-O-methyl-N'-nitroisourea 
• 255708-80-6 N,O-dimethyl-N'-nitroisourea 
• 132718-70-8 Boc-D-Har(NO2)-OH 
• 210880-92-5 clothianidine 
• 255708-80-6 N,O-dimethyl-N'-nitroisourea 
• 4245-76-5 N-methyl-N'-nitroguanidine 

Relevant academic research and scientific papers

A novel and practical method for the synthesis of dinotefuran through Michael addition of nitromethane to diethyl maleate

A novel and practical synthesis of dinotefuran 1, featuring a new access to it from known key intermediate (tetrahydrofuran-3-yl)-methanamine 5, has been achieved through Michael addition reaction of nitromethane to diethyl maleate in 6 steps with 45.5% total yield. This synthesis is scalable and hence has high potential for application to further synthetic elaboration on such new neonicotinoid insecticide dinotefuran 1.

A synthetic method of the dinotefuran (by machine translation)

The invention discloses a method for synthesis of dinotefuran, to γ - butyrolactone as raw materials, by Aldol condensation, also the original two-step by the reaction of 3 - hydroxy methyl tetrahydrofuran, then by the Gabriel synthesis of 3 - tetrahydrofuran methyl amine, dimethyl carbonate (DMC) as methylation reagent with the urea synthesis O - methyl isourea, re-nitration synthetic O - methyl - N - nitro-isourea, then with the methylamine reaction synthesis of 1, 3 - dimethyl - 2 - nitro-isourea, final 3 - tetrahydrofuran methylamine with 1, 3 - dimethyl - 2 - nitro-isourea through SN2 Bimolecular nucleophilic substitution reaction, one-step synthesis of dinotefuran. The present invention uses non of dimethyl carbonate as the methylating reagent, the methylation reaction yield ≥ 95%, O - methyl isourea content ≥ 96%, the by-product is carbon dioxide and methanol, process and environmental protection, the overall yield of the dinotefuran ≥ 50%. Synthetic method of this invention to reduce the production cost at the same time, with three wastes, after treatment is simple, the advantages of the environment friendly, and is suitable for industrial production, bring about significant economic benefits. (by machine translation)

Production of compounds

Provided is a method for producing a compound represented by formula (2), or a salt thereof, by reacting ammonia with formaldehyde so as to obtain a mixture that contains a compound represented by formula (8), and then mixing the obtained mixture that contains the compound represented by formula (8) with a compound represented by formula (1), or a salt thereof, in the presence of a base.

METHOD FOR PRODUCING 5-(AMINOMETHYL)-2-CHLOROTHIAZOLE

A method for producing 5-(aminomethyl)-2-chlorothiazole, which comprises the step of mixing a compound represented by formula (2): a mineral acid and a nitrite salt together.

METHOD FOR NITRATING ISOUREA

An object of the present invention is to industrially advantageously produce N-nitroisoureas or a salt thereof which is useful as a synthetic intermediate for pharmaceuticals and pesticides. The present invention relates to a process for producing a compound represented by the formula (2): wherein R1, R2 and R3 are as defined below, or a salt thereof, which comprises reacting a compound represented by the formula (1): wherein R1 represents an optionally substituted straight-chain or branched C1 to C6 alkyl group, R2 and R3 are the same or different and represent an optionally substituted straight-chain or branched C1 to C6 alkyl group, a cycloalkyl group or a substituted aryl group, or R2 and R3 simultaneously represent a hydrogen atom, or a salt thereof with a nitrating agent in the presence of sulfur trioxide.

PROCESS FOR PRODUCTION OF O-METHYL-N-NITROISOUREA

Disclosed is an industrially advantageous process for producing O-methyl-N-nitroisourea. Disclosed is a process for obtaining O-methyl-N-nitroisourea represented by the following chemical formula (1) or a salt thereof in a high yield by performing the nitration of O-methylisourea represented by the following chemical formula (2) or a salt thereof with nitrating agents in the presence of fuming sulfuric acid.

Immunoassay for neonicotinyl insecticides

The present invention provides immunogens for generating anti-neonicotinoid antibodies as well as antibodies, methods, reagents and kits for determining the presence of one or more neonicotinoid insecticides in a sample by immunoassay. The present invention has particular application to determination of the concentration of neonicotinoid insecticides applied to a plant propagation materials such as seed.

Method for producing isoureas

The present invention relates to a method for producing a compound of the formula: wherein R1is an optionally substituted hydrocarbon group; R2is H or an optionally substituted hydrocarbon group; and Q is an optionally substituted heterocyclic group, or a salt thereof which comprises subjecting a compound of the formula: wherein R1has the same meaning as defined above, or a salt thereof to a nitration reaction (a), and further subjecting the resulting mixture without isolating/purifying the resulting compound of the formula: wherein R1has the same meaning as defined above, or a salt thereof to a reaction (b) with a compound of the formula: Q—CH2—NH—R2??[III] wherein each symbol has the same meaning as defined above, or a salt thereof. According to the production method of the present invention, a compound [IV] as an intermediate of a guanidine derivative having an excellent insecticidal activity, or a salt thereof can be mass-produced, industrially.

Process for producing guanidine derivatives, intermediates therefor and their production

A process for producing the compound [I] or a salt thereof having excellent pesticidal activity as shown in the following schema. STR1