555-37-3

Usage

Uses

Used in Agriculture:
NEBURON is used as a herbicide for preemergence control of grasses and broad-leaved weeds in various crops, including peas, beans, lucerne, garlic, beets, cereals, strawberries, ornamentals, and forestry. Its effectiveness in controlling unwanted vegetation helps to improve crop yield and quality.
Used in Chemical Industry:
NEBURON's chemical properties, such as its solubility and melting point, make it a potential candidate for use in the chemical industry for various applications, including the synthesis of other compounds or as an intermediate in chemical processes.

Health Hazard

Acute oral toxicity is of very low order;moderately toxic by intravenous route.LD50 oral (rat): 11,000 mg/kgLD50 intravenous (mouse): 180 mg/kg.

Environmental Fate

Soil. Neburon undergoes dealkylation of the terminal nitrogen atom, ring hydroxylation and degradation to dichlorodihydroxyaniline (Hartley and Kidd, 1987). Residual activity in soil is limited to approximately 3 to 4 months (Hartley and Kidd, 1987).Chemical/Physical. Neburon hydrolyzes under basic conditions forming aniline derivatives. The half-life of neburon in 0.50 N sodium hydroxide at 20°C is 167 days (El-Dib and Aly, 1976).

InChI:InChI=1/C12H16Cl2N2O/c1-3-4-7-16(2)12(17)15-9-5-6-10(13)11(14)8-9/h5-6,8H,3-4,7H2,1-2H3,(H,15,17)

Upstream product

• 110-68-9 N-n-butyl-N-methylamine 
• 112-18-5 N,N-dimethylaminododecane 
• 1918-18-9 methyl N-(3,4-dichlorophenyl)carbamate 
• 99-54-7 3,4-dichloronitrobenzene 
• 13939-06-5 molybdenum hexacarbonyl 
• 590-28-3 potassium cyanate 
• 18282-59-2 4-bromo-1,2-dichlorobenzene 
• 201230-82-2 carbon monoxide 
• 95-76-1 m,p-dichloroaniline 

Downstream Products

• 110-68-9 N-n-butyl-N-methylamine 
• 102-36-3 3,4-dichlorophenylisocyanate 
• 74-89-5 methylamine 

Relevant academic research and scientific papers

Method for preparing asymmetric urea compound (by machine translation)

The invention provides a vehicle CO. 2 A method. for synthesizing an asymmetric urea compound by carbonylation coupling reaction of the carbonylation reagent is: and the aromatic, aliphatic primary amine compound and the aliphatic secondary amine compound and the normal pressure (100 °C, diglyme), can be efficiently prepared by using a common Lewis base and a hydrogen silane as the accelerator/CO under mild conditions. 2 The reaction produces a corresponding asymmetric urea compound. containing different functional groups, the process being operated at atmospheric pressure CO. 2 The use of an inexpensive Lewis base and, industrial silicon waste PMHS( for the green non-toxic carbonylation reagent) avoids toxic carbonylation reagents, high pressure, as an accelerator CO. 2 , The use, of the expensive dehydrating agent and the noble metal does not need to purify and separate the intermediate, and the pure product, is obtained by simple suction filtration separation after the reaction is ended . is a high efficiency, novel synthetic method . The commercial herbicide NEBURON. is successfully prepared by using the method. (by machine translation)

Pd/C-catalyzed reductive carbonylation of nitroaromatics for the synthesis of unsymmetrical ureas: One-step synthesis of neburon

A Pd/C catalyzed reductive carbonylation of nitroarenes for the synthesis of unsymmetrical ureas has been developed. Using inexpensive and stable nitroarenes as the substrates, a series of unsymmetrical ureas were produced in moderate to good yields. A range of functional groups including thioethers, halides and vinyl were compatible with this reaction. As a heterogeneous catalyst, Pd/C was recycled and reused four times without losing activity. Notably, urea-based herbicide neburon was prepared in 64% yield under our standard conditions.

Assembly of N,N-disubstituted-N′-arylureas via a copper-catalyzed one-pot three-component reaction of aryl bromides, potassium cyanate, and secondary amines

A three-component reaction of aryl bromides, potassium cyanate, and secondary amines takes place at 110 C in MeCN under the catalysis of Cu 2O and 2-(2,6-dimethylphenylamino)-2-oxoacetic acid potassium salt, giving N,N-disubstituted-N′-arylurea

Synthesis of unsymmetrical ureas by sulfur-assisted carbonylation with carbon monoxide and oxidation with molecular oxygen under mild conditions

With ambient pressure of carbon monoxide and oxygen at room temperature, N,N-dialkyl-N′-arylureas were selectively accessible from secondary amines, aromatic amines, and sulfur in good to excellent yields. For example, N-butyl-N-methyl-N′-(3,4-dichlorophenyl)urea, which is used as a herbicide (neburon), was afforded successfully from butylmethylamine (2 equiv), 3,4-dichloroaniline (1 equiv) and sulfur (1 equiv) in 79% (21.8 g) yield using carbon monoxide (0.1 MPa) and oxygen (0.1 MPa) at 20°C in DMF. Georg Thieme Verlag Stuttgart.

A novel synthesis of isocyanates and ureas via β-elimination of haloform

A novel synthesis of isocyanates via base-induced β-elimination of haloform from N-monosubstituted trihaloacetamides is described. The rate of reaction exhibits a strong dependence on the nature of the trihalomethyl group. Thus, while the reaction of tribromoacetamides proceeds at room temperature and the reaction of trichloroacetamides requires heating in polar solvents, no reaction could be observed for any of the corresponding trifluoro derivatives. This novel β-elimination of haloform from stable and readily available trihaloacetamides was applied to a 'one-pot' synthesis of ureas which avoids the use of phosgene and isolation of isocyanates.

Halopyridyl triazolinone herbicides and herbicidal use thereof

Disclosed are herbicidal halopyridyl triazolinones, herbicidal compositions comprising the halopyridyl triazolinones, and herbicidal use of the compounds and compositions. Such compounds and compositions are useful as both preemergence and postemergence herbicides in a variety of crops.

Herbicidal composition for upland farming and weeding method

A herbicidal composition for upland farming which can control weeds that have been difficult to control, for example, cleavers, chickweed, birdseye speedwell and violet, said composition containing as active ingredients a 3-substituted phenylpyrazole derivative represented by the general formula (I): STR1 (wherein R is a hydrogen atom, a C1-6 alkyl group, a C3-6 cycloalkyl group, a C1-6 haloalkyl group, a C2-6 alkenyl group or a C2-6 alkynyl group, R1 is a C1-6 alkyl group, X1 and X2, which may be the same or different, are halogen atoms, and Y is an oxygen atom or a sulfur atom) and at least one compound selected from the group consisting of sulfonylurea derivatives, phenylurea derivatives and phenoxy fatty acid derivatives; and a weeding method using said composition.

Process of improving activity of herbicides and fertilizers using N-(2-hydroxyethyl)-acetamide or -propanamide

The invention is related to the use of certain water-soluble compounds known as such and having the Formula for the modulation of membrane dependent metabolism processes within living cells, in particular with relation to transport phenomena and cell procedures which are induced or influenced by active agents supplied from outside the cell, products containing these substances for the above described uses and processes using these products.

Process for preparation of substituted phenylureas

Process for preparing a substituted phenylurea. A suitably substituted aniline, excess urea in a mole ratio of at least 1.1 with respect to the aniline, and a secondary amine are reacted simultaneously in a non-hydroxyl-containing organic solvent at a temperature of 130° to 250° C., with removal of ammonia as it forms. The phenylureas obtained are used as herbicides.

Composition for defoliating plants

New compositions for defoliating plants possessed of synergistic activity comprising (A) a compound of formula I STR1 in which R1 is hydrogen or C1 -C4 -alkyl, R2 is hydrogen, C1 -C4 -alkyl, C1 -C4 -alkoxy or C1 -C4 -alkylthio, R3 is hydrogen, C1 -C4 -alkyl, C1 -C4 -alkoxy, C1 -C4 -alkylthio or C3 -C8 -cycloalkyl, wherein R2 and R3 taken together with the nitrogen atom to which they are attached is a morpholino- piperidino- or pyrrolidino-group, X is oxygen or sulfur, Y can be the same or different and is hydrogen, halogen, C1 -C4 -alkyl, C1 -C4 -alkoxy, C1 -C4 -alkoxy-C1 -C2 -alkyl, C1 -C4 -alkylthio, trifluoromethyl or nitro, and n is the number 1, 2, 3, 4 or 5, in combination with (B) a defoliant for plants in a proportion of 1 to 99 parts by weight of component (A) to 99 to 1 parts by weight of component (B). As the defoliant there can be employed 1,2,3-thiadiazole-5-yl-urea derivatives, 1,2,3-thiadiazole-5-carboxylic acid derivatives, benzylaminopurine derivatives, 2,3-dihydro-5,6-dimethyl-1,4-dithiine-1,1,4,4-tetroxide, 1,1'-dimethyl-4,4'-bipyridilium-dichloride, sodium chlorate and S,S,S-tributylphosphortrithioate. The compositions of the invention are especially suitable for use in the defoliation of cotton plants.