36614-21-8Relevant academic research and scientific papers
Process for preparing herbicidal ureas and insecticidal carbamates and carbamate derivatives
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, (2008/06/13)
The present invention provides a process for preparing herbicidal ureas and insecticidal carbamates and carbamate derivatives comprising reacting an amine, alcohol, or oxime nucleophile with a urea in an inert organic solvent.
Process for preparing ureas
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, (2008/06/13)
The present invention provides a novel process for preparing herbicidal and insecticidal ureas, carbamates and carbamate derivatives of the formula E is -O- or -C(R4)2- ;, R is C1-C7 alkyl;, R1 is H, C1-C7 alkyl, C3-C7 cycloalkyl, phenyl, or C1-C4 alkylphenyl;, R2 is H, C1-C7 alkyl, C3-C7 cycloalkyl, C2-C7 alkenyl, C2-C7 alkynyl, or phenyl optionally substituted with Cl, Br, -NO2, -CF3, C1-C4 alkyl, C1-C4 alkoxy, or -N(C1-C4 alkyl)2;, R3 is H, F, Cl, Br, -CF3, C1-C7 alkyl option-ally substituted with F, Cl, or Br, -S(O)nC1-C7 alkyl, C1-C7 alkoxy, C3-C7 cycloalkyl optionally substituted with F, Cl, or Br, or phenyl optionally substituted with F, Cl, Br, -NO2, -CF3, or C1-C4 alkyl;, R4 is H or C1-C4 alkyl;, R5 is C1-C7 alkoxy or -S(O)nC1-C7 alkyl;, R6 is C1-C5 alkyl optionally substituted with F, Cl, or Br, C3-C5 cycloalkyl, phenyl, or, , - X is R3, -N=CH-N(C1-C4 alkyl)2, -N(C1-C4 alkyl)2 or -N(C2-C4 alkenyl)2, Y is H or S(O)nC1-C7 alkyl;, Z is H, C1-C4 alkyl, Cl, F, Br, haloalkyl, -NO2, -N(C1-C4 alkyl)2, -C≡N, phenyl, -S(C1-C4 alkyl), or C1-C4 alkoxy;, n is 0, 1, or 2; and, m is 1, 2 or 3,comprising reacting a nucleophile of the formula A-H, wherein A is as defined above, with a urea of the formula wherein each R is independently chosen from R as set forth above and each R1 is independently chosen from R1 as set forth above.
Conformational Preferences in Alkylnitrosoureas
Snyder, John K.,Stock, Leon M.
, p. 886 - 891 (2007/10/02)
The spectroscopic properties of several N-alkyl-N-nitrosoureas, N,N'-dialkyl-N-nitrosoureas, and N,N',N'-trialkyl-N-nitrosoureas have been studied in carbon disulfide and chloroform solutions.The NH stretching frequencies in the IR spectra have been observed in both concentrated and dilute solution and in the presence of added dioxane.The results indicate that there is a strong intramolecular hydrogen bond in the mono- and dialkylnitrosoureas.The chemical shifts and line widths of the NMR spectra have also been studied in these solvents.The large chemical shift differences, about 1.3 ppm, for the NH protons in the monoalkylnitrosoureas and other spectroscopic features in the monoalkyl- and dialkylnitrosoureas also indicate that an intramolecular hydrogen bond contributes to a strong conformational preference.The temperature dependence of the NMR spectra of several N,N',N'-trialkyl-N-nitrosoureas establishes that the energy barrier for rotation about the carbon dialkylamide bond is about 13 kcal mol-1.Dipolar resonance interactions are primarily responsible for this barrier.This interaction is augmented by a strong, 8-10 kcal mol-1, hydrogen bond in the mono- and dialkylnitrosoureas.
