Preparation of N‐Alkoxyureas and Their Use as Selective Herbicides

Scherer, Otto J.; Hörlein, Gerhard; Härtel, K.

doi:10.1002/anie.196306701

Cited by 4 publications

(2 citation statements)

References 4 publications

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“…[638] However, no yields are reported. Alkylation of N-hydroxyor N-alkoxyureas smoothly gives 1-alkoxy-1-alkylureas 454, [614,[640][641][642][643][644][645][646] which are cleaved by alkaline hydrolysis to provide O,N-dialkylhydroxylamines 455 in moderate to good yields (Scheme 183). [647] Alternatively, the O,N-dialkylhydroxylamines 455 are also accessible from 1-alkoxy-1-alkyl-3-arylureas 454 (R 1 = aryl) by reaction with an arylamine, the yields being somewhat higher in this case.…”

Section: Bno H N Phmentioning

confidence: 99%

Product Class 5: Hydroxylamines

Enders¹,

Schaumann²

2009

Category 5, Compounds With One Saturated Carbon Heteroatom Bond

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Section: Bno H N Phmentioning

confidence: 99%

Product Class 5: Hydroxylamines

Enders¹,

Schaumann²

2009

Category 5, Compounds With One Saturated Carbon Heteroatom Bond

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“…In comparison, the latter three were gradually eliminated due to their toxicity, harmfulness and sewage pollution, and only the catalytic hydrogenation gradually prevail due to its clean reaction process [5–8]. Halogenated aromatic amines are important classifications of aniline compounds especially in pesticides, such as, p -chloroaniline used to prepare Monolinuron [9], m -chloroaniline used to prepare Barban [10], and 3-chloro-4-methylaniline used to prepare Chlorotoluron [11]. However, when the halogenated aromatic amines are prepared by catalytic hydrogenation reduction of halogenated aromatic nitro compounds, the side reactions of dehalogenation [12] or C–N coupling [13] are easy to occur.…”

Section: Introductionmentioning

confidence: 99%

Preparation of sub-microspherical Fe3O4@PDA-Pd NPs catalyst and application in catalytic hydroreduction reaction of halogenated aromatic nitro compounds to prepare halogenated aromatic amines

et al. 2019

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BackgroundThe side reactions of dehalogenation or C–N coupling tend to occur when halogenated aromatic amines are prepared by catalytic hydrogenation reduction of halogenated aromatic nitro compounds. In this paper, we prepared the sub-microspherical Fe3O4@PDA-Pd NPs catalyst apply it efficiently in the hydrogenation reduction of halogenated aromatic nitro compounds to prepare the halogenated aromatic amines under atmospheric pressure. The catalyst shows a high selectivity of greater than 96% and can effectively inhibit the occurrence of the side reactions of dehalogenation and C–N coupling.ResultsThe optimum condition of the hydroreduction reaction is when tetrahydrofuran is used as solvent and the reaction happens at 50 °C for 5 h. The selectivity of the chlorinated aromatic amine and the fluorinated aromatic amine products exceed 99% and the yield exceeds 90%. Only a small amount of dehalogenated products and C–N coupling by-products were produced in the brominated aromatic compound and the iodinated aromatic compound.ConclusionWe developed a promising method for preparing the superparamagnetic and strongly magnetic Fe3O4@PDA core–shell sub-microsphere-supported nano-palladium catalyst for catalyzing the hydrogenation reduction of halogenated aromatic nitro compounds. The halogenated aromatic amines were efficiently and highly selectively prepared under atmospheric pressure, with the side reactions of dehalogenation and C–N coupling effectively inhabited simultaneously.

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Notiz über die Darstellung von O.N‐Dialkyl‐hydroxylaminen

Kreutzkamp

Messinger

1967

Chem. Ber.

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Die Darstellung von 0.N-Dialkyl-hydroxylaminen (4) erfolgte bisher durch Alkylierung von N-Hydroxy-urethanen und anschlieBende Hydrolyse der Reaktionsprodukte durch z. TI. langes Erhitzen mit Saure oder Lauge, meist im Autoklavenl-4). Einfacher und schneller gelangt man zu 4, wenn man von N-Hydroxy-N'-phenyl-harnstoff (1) oder von N-Hydroxyharnstoff (2) ausgeht. Diese Verbindungen sind aus Hydroxylamin durch Umsetzung mit Phenylisocyanats) oder Urethanens) leicht zuganglich.

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Preparation of N‐Alkoxyureas and Their Use as Selective Herbicides

Abstract: N-(3,4-dichlorophenyI)-Nmethoxy-N-methylurea (Ajalon @) are two new herbicides with characteristic selective activity. A simple and convenient method for their preparation is described.

Cited by 4 publications

References 4 publications

Product Class 5: Hydroxylamines

Product Class 5: Hydroxylamines

Preparation of sub-microspherical Fe3O4@PDA-Pd NPs catalyst and application in catalytic hydroreduction reaction of halogenated aromatic nitro compounds to prepare halogenated aromatic amines

Notiz über die Darstellung von O.N‐Dialkyl‐hydroxylaminen

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