関: calcium carbimide

WordNet

a weak soluble dibasic acid (the parent acid of cyanamide salts) (同)cyanamid
a compound used as a fertilizer and as a source of nitrogen compounds (同)cyanamide

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/12/24 12:38:54」(JST)

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Cyanamide is an organic compound with the formula CN₂H₂. This white solid is widely used in agriculture and the production of pharmaceuticals and other organic compounds. It is also used as an alcohol deterrent drug in Canada, Europe and Japan.^{[citation needed]} The molecule features a nitrile group attached to an amino group. Although it is similar in structure to hydrogen cyanide, it is not as toxic. Derivatives of this compound are also referred to as cyanamides, the most common being calcium cyanamide (CaCN₂).

Tautomers and self-condensations

Containing both a nucleophilic and electrophilic site within the same molecule, cyanamide undergoes various reactions with itself. Cyanamide exists as two tautomers, one with the connectivity NCNH₂ and the other with the formula HNCNH ("diimide" tautomer). The NCNH₂ form dominates, but in a few reactions (e.g. silylation) the diimide form appears to be important.

Cyanamide dimerizes to give 2-cyanoguanidine (dicyandiamide). This decomposition process is disfavored by acids and is inhibited by low temperatures. The cyclic trimer is called melamine.

Production, reactions, uses

Cyanamide is produced by hydrolysis of calcium cyanamide, which in turn is prepared from calcium carbide via the Frank-Caro process.

CaCN₂ + H₂O + CO₂ → CaCO₃ + H₂NCN

The conversion is conducted on slurries. Consequently, most commercial cyanamide is sold as an aqueous solution.

The main reaction exhibited by cyanamide involves additions of compounds containing an acidic proton. Water, hydrogen sulfide, and hydrogen selenide react with cyanamide to give urea, thiourea, and selenourea, respectively:

H₂NCN + H₂E → H₂NC(E)NH₂ (E = O, S, Se)

In this way, cyanamide behaves as a dehydration agent and thus can induce condensation reactions. Alcohols, thiols, and amines react analogously to give alkylisoureas, "pseudothioureas," and guanidines. The anti-ulcer drug cimetidine is generated using such reactivity. Related reactions exploit the bifunctionality of cyanamide to give heterocycles, and this latter reactivity is the basis of several pharmaceutical syntheses such as the aminopyrimidine imatinib) and agrichemicals Amitrol (3-Amino-1,2,4-triazole) and Hexazinone. The hair-loss treatment Minoxidil and the anthelmintic (worm-killing) drugs Albendazole, Flubendazole, and Mebendazole feature 2-aminoimidazole substructures derived from cyanamide.^[2]

Cyanamide is a common agricultural rest-breaking agent applied in spring to stimulate uniform opening of buds, early foliation and bloom. Cyanamide can effectively compensate for the moderate lack of chilling units accumulated in the previous autumn and save the harvest that would otherwise be lost. It is particularly effective for woody plants such as berries, grapes, apples, peaches and kiwifruit. Overdosage, high concentration and error in timing of application can damage the buds (especially of peach trees).^[3]

Environmental aspects

Cyanamide degrades via hydrolysis to urea, an excellent fertilizer. Fungi, like Myrothecium verrucaria, accelerate this process utilizing the enzyme cyanamide hydratase.^[4]

Safety

Cyanamide has a modest toxicity in humans.^[5] Workplace exposure to hydrogen cyanamide sprays or exposure in people living in the vicinity of spraying have been reported as causing respiratory irritation, contact dermatitis, headache, and gastrointestinal symptoms of nausea, vomiting, or diarrhea.^[5]

References

^ ^a ^b "NIOSH Pocket Guide to Chemical Hazards #0160". National Institute for Occupational Safety and Health (NIOSH).
^ Thomas Güthner; Bernd Mertschenk (2006). "Cyanamides". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_139.pub2.
^ Powell, A. (1999). Action Program for Dormex Application on Peaches. Auburn University. Retrieved 2010-05-24.
^ Stransky H and Amberger A (1973). "Isolation and properties of a cyanamide hydratase (EC 4.2.1) from Myrothecium verrucaria". Z. Pflanzenphysiol. 70: 74–87.
^ ^a ^b Schep L, Temple W, Beasley M (January 2009). "The adverse effects of hydrogen cyanamide on human health: an evaluation of inquiries to the New Zealand National Poisons Centre". Clinical Toxicology (Philadelphia, PA) 472 (1): 58–60. doi:10.1080/15563650802459254. PMID 18951270.

External links

International Chemical Safety Card 0424
"NIOSH Pocket Guide to Chemical Hazards #0160". National Institute for Occupational Safety and Health (NIOSH).
OSHA guideline for cyanamide

English Journal

An acid catalyzed reversible ring-opening/ring-closure reaction involving a cyano-rhodamine spirolactam.

Li H, Guan H, Duan X, Hu J, Wang G, Wang Q.SourceDepartment of Chemistry and Biochemistry, University of South Carolina, 631 Sumter Street, Columbia, SC 29208, USA. wang263@mailbox.sc.edu.
Organic & biomolecular chemistry.Org Biomol Chem.2013 Mar 21;11(11):1805-9. doi: 10.1039/c3ob27356c. Epub 2013 Feb 5.
Cyanamide was introduced into the rhodamine spirolactam framework to produce a colorless and non-fluorescent compound RBCN. It shows a reversible ring-opening/ring-closure process in response to the solution pH, which exhibits an "ON/OFF" switching in its fluorescence. Different from other rhodamine
PMID 23381503

Inhibition of tomato (Solanum lycopersicum L.) root growth by cyanamide is not always accompanied with enhancement of ROS production.

Soltys D, Bogatek R, Gniazdowska A.SourceDepartment of Plant Physiology; Warsaw University of Life Sciences-SGGW; Nowoursynowska; Warsaw, Poland.
Plant signaling & behavior.Plant Signal Behav.2013 Feb 21;8(5). pii: e23994. [Epub ahead of print]
Mode of action of allelochemicals in target plants is currently widely studied. Cyanamide is one of the newly discovered allelochemical, biosynthesized in hairy vetch. Recently, it has been recognized that cyanamide is plant growth inhibitor, which affects mitosis in root tip cells and causes,e.g.,
PMID 23428892

Phenylcyanamidoruthenium scorpionate complexes.

Harb C, Kravtsov P, Choudhuri M, Sirianni ER, Yap GP, Lever AB, Crutchley RJ.SourceDepartment of Chemistry, Carleton University , Ottawa, Ontario K1S 5B6, Canada.
Inorganic chemistry.Inorg Chem.2013 Feb 4;52(3):1621-30. doi: 10.1021/ic302535h. Epub 2013 Jan 22.
Nine [Ru(Tp)(dppe)L] complexes, where Tp is hydrotris(pyrazol-1-yl)borate, dppe is ethylenebis(diphenylphosphine), and L is (4-nitrophenyl)cyanamide (NO(2)pcyd(-)), (2-chlorophenyl)cyanamide (2-Clpcyd(-)), (3-chlorophenyl)cyanamide (3-Clpcyd(-)), (2,4-dichlorophenyl)cyanamide (2,4-Cl(2)pcyd(-)), (2,
PMID 23339541

Japanese Journal

東北日本海側地域における水稲収穫後の圃場への石灰窒素散布が漏生イネの出芽・苗立ちに及ぼす影響

大平陽一,白土宏之,山口弘道 [他],福田あかり
日本作物学会紀事 84(1), 22-33, 2015
ホールクロップサイレージ（WCS）用水稲品種および飼料米用等の多収性水稲品種の種子を秋田県大仙市の水田圃場に秋季に散播して擬似的に種子が脱落した状態を作出し，石灰窒素の散布によって漏生イネの出芽・苗立ちの抑制が可能か検討した．秋季から春季にかけて圃場表面で種子が越冬する条件では，秋季，冬季および春季の石灰窒素散布（50 g m-2）は，いずれも無処理と比較して漏生イネの出芽率を低下させ，特に …
NAID 130004829742

重粘土転換畑の秋播コムギ栽培における石灰窒素の深層施肥効果

金田吉弘,後藤紗布子,佐藤孝 [他],高階史章,保田謙太郎,野坂佳史,坂下普志,浦野保徳,大山卓爾
日本土壌肥料學雜誌 85(5), 446-452, 2014-10-05
重粘土転換畑の秋播コムギ栽培において,石灰窒素の深層施肥効果を,基肥と追肥5回による慣行施肥体系と比較した.試験は,水田後転換畑において実施した.2012年度の試験では,試験区として,(1)硫酸アンモニウムによる基肥(N6gm^<-2>)と硫酸アンモニウムによる5回の追肥(計N14gm^<-2>)を組み合わせた追肥区(合計N20gm^<-2>),(2)種子直下1 …
NAID 110009909578

アルコール依存症の薬物療法(アカンプロサートを含めて) (特集アルコール依存症の基礎と臨床)

植松直道
精神科 24(5), 548-550, 2014-05
NAID 40020062362

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リンク元	「シアナミド」「calcium carbimide」
拡張検索	「calcium cyanamide」

「シアナミド」

Cyanamide
Names
	IUPAC names Cyanamide,; aminomethanenitrile
	Other names Amidocyanogen, carbamonitrile, carbimide, carbodiimide, cyanoamine, cyanoazane, N-cyanoamine, cyanogenamide, cyanogen amide, cyanogen nitride, diiminomethane, hydrogen cyanamide, methane diimide
Identifiers
CAS Number	420-04-2
ChEBI	CHEBI:16698
ChEMBL	ChEMBL56279
ChemSpider	9480
DrugBank	DB02679
EC Number	206-992-3
Jmol interactive 3D	Image
KEGG	D00123
PubChem	9864
RTECS number	GS5950000
UNII	21CP7826LC
UN number	2811
	InChI InChI=1S/CH2N2/c2-1-3/h2H2 Key: XZMCDFZZKTWFGF-UHFFFAOYSA-N ; InChI=1/CH2N2/c2-1-3/h2H2 Key: XZMCDFZZKTWFGF-UHFFFAOYAW ;
	SMILES N#CN ;
Properties
Chemical formula	CH2N2
Molar mass	42.040 g/mol
Appearance	Crystalline solid
Density	1.28 g/cm3
Melting point	44 °C (111 °F; 317 K)
Boiling point	260 °C (500 °F; 533 K) (decomposes); 83 °C at 6.7 Pa; 140 °C at 2.5 kPa
Solubility in water	85 g/100 ml (25 °C)
Solubility in organic solvents	soluble
Hazards
Safety data sheet	ICSC 0424
EU classification (DSD)	Toxic (T)
R-phrases	R20, R25, R27, R36/38, R43
S-phrases	(S1/2), S3, S22, S36/37, S45
NFPA 704	1 4 3
Flash point	141 °C (286 °F; 414 K)
	US health exposure limits (NIOSH):
PEL (Permissible)	none
REL (Recommended)	TWA 2 mg/m3
IDLH (Immediate danger	N.D.
Related compounds
Related compounds	Calcium cyanamide
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references