Cyanamide（Alzogur; Amidocyanogen; Carbamonitrile; Carbimide; Cyanoamine; Cyanogen nitride; Cyanogenamide; Deurbraak; Dormex; Hydrogen cyanamide; N-Cyanoamine; NSC 24133;TsAKS; CH2N2）as chemical substance with unique and chemically promiscuous nitrogen-carbon-nitrogen connectivity, have been commonly used as industrial raw materials for pharmaceutical synthesis, pesticide intermediates, agricultural fertilizers, plant regulators and food additives, etc^[1].

Cyanamide with a anucleophilic sp3-aminonitrogen and an electrophilic nitrile unit could be used and applied in synthetic chemistry. In acitivity site of anucleophilic sp3-aminonitrogen, it could occurred nucleophilic reactions for mono and disubstituted cyanamides, such as alkyl and aryl  substituted cyanamides[2]. Then, the activity site of electrophilic nitrile of the substituted organic cyanamides can involve in cycloaddition chemistry, aminocyanation reactions, electrophilic cyanide-transfer agents, radical and coordination chemistry, and obtain multiple chemical intermediates[3]. For example, by utilizing alkyl disubstituted cyanamides as core building block, 1,2,4-oxadiazoles could be synthesized by a cycloaddition protocol, in which zinc-chloride catalyzed reverse nucleophilic addition of N-Boc-hydroxylamine, TFAA and TFA-mediate acylation, deprotection and ring-closure[4]. Thus, cyanamide is an important industrial raw material for pesticide and pharmaceutical intermediates.

Cyanamide have special functions in terminating dormancy, accelerating bud, promoting flower, killing insect and terilizing that was usually worked as an effective plant growth regulator for enhancing production efficiency of vegetable and fruit crops[4]. Metal cyanamide were an important cyanamide derivative for further application. For example, calcium cyanamide could be direct alkylated to prepare mono and disubstituted cyanamide derivatives[5]. It also could be used as a agricultural fertilizer by providing nitrogen nutrients and allows the achievement of higher crop yields[6]. Meanwhile, it is an effective molluscicide against Oncomelania nosophora that can work as pesticides in agricultural industrial[7]. Calcium cyanamide were used in crops of peas and potatoes could reduced the cyst numbers on the roots of the plants, effectively[8].

In conclusion, cyanamide and their derivates as multifunction chemical, have widely application in chemical and agricultural industry.

References

[1] https://www.lookchem.com/CYANAMIDE.
[2] Nekrasov, D.D. Synthesis and Chemical Transformations of Mono- and Disubstituted Cyanamides. Russ. J. Org. Chem. 40 (2004) 1387–1402.
[3] Prabhath, M. R., Williams, L., Bhat, S. V., Sharma, P. Recent advances in cyanamide chemistry: synthesis and applications. Molecules, 22 (2017). 615.
[4] Goldberg, K.; Clarke, D.S.; Scott, J.S. A facile synthesis of 3-trifluoromethyl- 1,2,4-oxadiazoles from cyanamides. Tetrahedron Lett. 55 (2014) 4433–4436.
[5] Lawes, G. S., Woolley, D. J. The commercial use of plant growth regulators to regulate fruit development. In IV International Conference on Postharvest Science 553 (2000),149-150.