Effect of Cl-substitution on rooting-or cytokinin-like activity of diphenylurea derivatives

Ricci, Ada; Carra, Angela; Rolli, Enrico; Bertoletti, Cristina; Morini, Giuseppina; Incerti, Matteo; Vicini, Paola

doi:10.1007/bf02637249

Cited by 12 publications

(13 citation statements)

References 26 publications

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“…For the medical and biological activities of urea derivatives, see: Abad et al (2004); Chen et al (2005); Batra et al (2006). For cytokinin activity, see: Wang et al (2001); Ricci et al (2005) Symmetry codes: (i) Àx; Ày þ 1; Àz þ 2; (ii) x; Ày þ 1 2 ; z þ 1 2 .…”

Section: Related Literaturementioning

confidence: 99%

Crystal stucture of methyl 2-({[2-(methoxycarbonyl)phenyl]carbamoyl}amino)benzoate

Yassine

Khouili

Ammari³

et al. 2015

Acta Cryst E

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In the title compound, C17H16N2O5, the dihedral angles between the central urea [N—C(=O)—N] fragment and its attached benzene rings are 20.20 (14) and 24.24 (13)°; the dihedral angle between the aromatic rings is 42.1 (1)°. The molecular conformation is consolidated by two intramolecular N—H⋯O hydrogen bonds, which both generate S(6) rings. In the crystal, inversion dimers linked by pairs of C—H⋯O interactions generate R 2 2(14) loops. The dimers are linked by further C—H⋯O interactions into (011) sheets.

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Section: Related Literaturementioning

confidence: 99%

Crystal stucture of methyl 2-({[2-(methoxycarbonyl)phenyl]carbamoyl}amino)benzoate

Yassine

Khouili

Ammari³

et al. 2015

Acta Cryst E

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“…N,N 0 -Diphenylureas are an interesting family of molecules that have been explored for a variety of purposes. Some have been studied for their regulatory effects on plant growth (Takahashi et al, 1978;Mok & Mok, 1994;Ricci et al, 2005). Others are of interest for their potential nonlinear optical (NLO) properties (Huang et al, 1995;George et al, 2004).…”

Section: Introductionmentioning

confidence: 99%

Concomitant polymorphs of 1,3-bis(3-fluorophenyl)urea

Capacci-Daniel

Bertke

Dehghan

et al. 2016

Acta Crystallogr C Struct Chem

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Hydrogen bonding between urea functionalities is a common structural motif employed in crystal-engineering studies. Crystallization of 1,3-bis(3-fluorophenyl)urea, C13H10F2N2O, from many solvents yielded concomitant mixtures of at least two polymorphs. In the monoclinic form, one-dimensional chains of hydrogen-bonded urea molecules align in an antiparallel orientation, as is typical of many diphenylureas. In the orthorhombic form, one-dimensional chains of hydrogen-bonded urea molecules have a parallel orientation rarely observed in symmetrically substituted diphenylureas.

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“…Ureas are a very important class of carbonyl compounds which find extensive application as agrochemicals, dyes for cellulose fibers, antioxidants in gasoline, resin precursors, and pharmaceuticals [1][2][3][4][5][6][7][8].…”

Section: Introductionmentioning

confidence: 99%

Phosgene-free synthesis of 1,3-diphenylurea via catalyzed reductive carbonylation of nitrobenzene

Vavasori

Ronchin

2012

Pure and Applied Chemistry

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1,3-Diphenylurea (DPU) has been proposed as a synthetic intermediate for phosgene-free synthesis of methyl N-phenylcarbamate and phenyl isocyanate, which are easily obtained from the urea by reaction with methanol. Such an alternative route to synthesis of carbamates and isocyanates necessitates an improved phosgene-free synthesis of the corresponding urea. In this work, it is reported that Pd(II)-diphosphine catalyzed reductive carbonylation of nitrobenzene in acetic acid (AcOH)-methanol proceeds in high yield and selectivity as a one-step synthesis of DPU. We have found that the catalytic activity and selectivity of this process depends on solvent composition and on the bite angle of the diphosphine ligands. Under optimum reaction conditions, yields in excess of 90 molar % and near-quantitative selectivity can be achieved.

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Effect of Cl-substitution on rooting-or cytokinin-like activity of diphenylurea derivatives

Cited by 12 publications

References 26 publications

Crystal stucture of methyl 2-({[2-(methoxycarbonyl)phenyl]carbamoyl}amino)benzoate

Crystal stucture of methyl 2-({[2-(methoxycarbonyl)phenyl]carbamoyl}amino)benzoate

Concomitant polymorphs of 1,3-bis(3-fluorophenyl)urea

Phosgene-free synthesis of 1,3-diphenylurea via catalyzed reductive carbonylation of nitrobenzene

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