Inhibition of nitrification in soil by heterocyclic nitrogen compounds was written by McCarty, G. W.;Bremner, J. M.. And the article was included in Biology and Fertility of Soils in 1989.Synthetic Route of C6H9N3O This article mentions the following:
The relationship between the structures of diverse heterocyclic nitrogen (N) compounds and the effectiveness of these compounds for the inhibition of nitrification in soil was studied by determining the effects of different amounts of 12 unsubstituted and 33 substituted heterocyclic N compounds on the production of (NO2– + NO3–)-N in soils incubated at 25° for 21 days after treatment with ammonium sulfate. Unsubstituted heterocyclic N compounds containing 2 adjacent ring N atoms inhibited nitrification in soil and 2 of these compounds, pyrazole and 1,2,4-triazole, were potent inhibitors. Also, several substituted pyrazoles and thiadiazoles were good inhibitors of nitrification in soil (e.g., 3-methylpyrazole and 3,4-dichloro-1,2,5-thiadiazole). In the experiment, the researchers used many compounds, for example, 3,5-Dimethyl-1H-pyrazole-1-carboxamide (cas: 934-48-5Synthetic Route of C6H9N3O).
3,5-Dimethyl-1H-pyrazole-1-carboxamide (cas: 934-48-5) belongs to pyrazole derivatives. Pyrazoles, a five-membered heterocycle containing two adjacent nitrogen atoms, are the core structures found in a number of molecules that possess a wide range of pharmaceutical and agricultural activities. The presence of both electronegative nitrogen atoms in the pyrazole ring reduces the electron density of the C3- and C5-positions leaving electron density of C4-position unaltered. Thus the C4-position is vulnerable to electrophilic attack. The C3 electrophilic-position may undergo deprotonation in the presence of a strong base leading to ring opening.Synthetic Route of C6H9N3O
Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics